X-ray single crystal diffraction and structural analysis provides information on the molecular conformation and mutual arrangement of building blocks within the crystal structure. The investigation into supramolecular architectures within crystals remains a highly active and dynamic field. The intricate interplay of various noncovalent interactions governs the formation of these supramolecular architectures. Hydrogen bonding, known for its strength and directionality, emerges as a crucial factor in shaping the solid-state organization of molecular solids. The resulting crystal structure reflects a delicate equilibrium among a diverse range of intermolecular interactions. Crystal engineering typically involves the design and synthesis of crystalline materials by self-assembling molecular building blocks. The functionality of the material is often categorized within the framework of crystal engineering. This approach identifies a compatible arrangement of molecular or ionic components to form into a specific architecture by strategically engineering a network of desired supramolecular interactions (Bernstein et al., 1995;Jeffrey & Saenger, 1991;Desiraju, 1995). In biological systems, pyrimidine and aminopyrimidine derivatives are essential constituents, serving as fundamental building blocks for nucleic acids. The functionality of nucleic acids is dictated by hydrogen bonding patterns crucial for the transfer of genetic information. Various derivatives of pyrimidine demonstrate a range of biological activities such as antibacterial, antimicrobial, anticancer, anti-HIV-1, and anti-rubella virus effects. Moreover, these derivatives play integral roles in energy transduction, act as metabolic cofactors, and contribute to cellular signaling processes (Desiraju,1995;Brown, 1987;Botta et al., 2001).
The cocrystal of a salt of the compound I is built by one 2,4,6-triaminopyrimidinium cation (TAP) one molecule of indole-3-propionate IPA (A) anion and one molecule of indole-3-propionic acid IPA (B) in the asymmetric unit. The ORTEP view of the compound is shown in Fig 1a . The oxygen atoms of the carboxyl group in IPA (A) are deprotonated and the proton transferred to the pyrimidine nitrogen atom (N1) of TAP. Protonation at N1 site is reflected by a slight increase in C2-N1-C6 bond angle (120.78 (12) o ) and for the non protonated ring N3, the C2-N3-C4 bond angle is found to be 116.94 ( 12) o (Schwalbe & Williams, 1982). The carboxylate C-O bond length tend to be (C17A-O1A)/ (C17A-O2A) = 1.2345 (18) Å/1.2809 (17) Å) respectively which also supported the deprotanation of IPA A ion.
The fundamental heterodimeric synthon R 2 2 (8) (Etter et al., 1990) is formed via a pair of N-H•••O hydrogen bonds involving the protonated ring N1 and N5-amino group of the cation and O2A and O1A atom of the carboxylate (A) anion (Table 2). Further R 2 3 (10) motif is formed through a couple of N-H•••O and one O-H•••O hydrogen bonds linking protonated ring N1 and N2-amino group of cation with bifurcated carboxylate O2A atom of anion A and bifurcated carboxylic O2B atom of IPA (B). The R 2 4 (8) ring motif is formed via a couple of N-H•••O hydrogen bonds by linking amino N5 of TAP cation and carboxylate O1A and O1A ii [Symmetry code: -x, -y+1, -z+1] of symmetry related IPA (A) anion.The three ring motifs fused together and thus facilitating the formation of sextruplet hydrogen bonded array (DDDAAA) by the reoccurrence of R 2 2 (8), R 3 2 (10) & R 4 2 (8) fused ring motifs. This arrangement is analogous to crystal structure of 2,4,6-triamnipyrimidinium sulfate monohydrate (Sangavi et al., 2023). A discrete complementary base pairing is formed via N-H•••N hydrogen bond involving amino N2 and N3 i [Symmetry code: -x+1, -y, -z+1] of sy,mmetry related TAP cation. This discrete base pair in turn links amino N4 of TAP with O2B i [Symmetry code: -x+1, -y, -z+1] of carboxylic acid IPA(B) through N-H•••O hydrogen bond to form R 3 2 (8) ring motif resulting a DADA quadruple hydrogen bonded pattern with a ring sequence of R 3 2 (8), R 2 2 (8) and R 3 2 (8). Similar type of complementary base pair is observed in the crystal structure of 2,4,6-triamnipyrimidinium succinate (Pedireddi et al., 1998), 2,4,6-triamnipyrimidinium 3,5-dihydroxybenzoate (Xing et al., 2017), 2,4,6-triamnipyrimidinium 3-nitrobenzoate (Mohana et al., 2023) and 2,4,6-triamnipyrimidinium 6-chloronicotinate dihydrate (Sangavi et al., 2023). This arrangement is observed in the crystal structures of 2,4,6-triamnipyrimidinium 3-nitrobenzoate (Mohana et al., 2023). The alternative occurrence of sextuple and quadruple hydrogen bonded arrays generates the supramolecular hydrogen bonded pattern (Fig 1b) (Schwalbe & Williams, 1982). The deprotonated carboxylate C-O bond length in the IAA (A and B) moities C16A-O1A, C16A-O2A, C16B-O1B, C16B-O2B are found to be 1.259
The primary interaction between the cation and anion leads to the formation of two different heterodimeric R 2 2 (8) ring motifs via pair of N-H•••O hydrogen bonds (Table 3). This hydrogen bond connects the protonated ring N1A and amino N2A of TAP (A) with carboxylate O1A & O2A atoms of IAA(A) and protonated ring N1B and amino N5B of TAP (B) with carboxylate O1B & O2B atoms of IAA(B). Among the two TAP (A & B), the cation B is self assembled centrosymmetrically and exist as a discrete base pair via a pair of N-H•••N hydrogen bonds involving amino N4B and ring N3B v [Symmetry code : 2-x,1-y,-z ] of TAP (B) cation to form homomeric R 2 2 (8) ring. This type of complementary base pair observed in the crystal structure of 2,4,6-triamnipyrimidinium succinate (Pedireddi et al., 1998), 2,4,6triamnipyrimidinium 3,5-dihydroxybenzoate (Xing et al., 2017), 2,4,6-triamnipyrimidinium 3-nitrobenzoate (Mohana et al., 2023) and 2,4,6-triamnipyrimidinium 6-chloronicotinate dihydrate (Sangavi et al., 2023). This discrete base pair hold two centrosymmetric IAA(A) anions on either side by the formation of R 3 2 (8) ring motif through a pair of N-Revision OV3176-31.8.24.cif H•••O hydrogen bonds linking amino N2B & N4B of TAP B cation and O2A of IAA (A) and O2A v [Symmetry code : 2-x,1-y,-z ] of symmetry related IAA (A)anion. The continuous occurrence of fused ring motifs R 3 2 (8), R 2 2 (8) and R 3 2 (8) develop a quadruple DADA hydrogen bonded array. This type of array is observed in the crystal structures of 2,4,6triamnipyrimidinium 3-nitrobenzoate (Mohana et al., 2023) (Shao et al., 2004;Hemamalini et al., 2006;Prior et al., 2013 ) involving R 4 2 ( 16) ring motif at the centre and around which a pair of R 5 4 ( 16 The asymmetric unit of compound III contains two crystallographically independent TAP cations (A and B) and two 5bromothiophene-2-carboxylate an ions BTCA (A & B) (Figure 3a). In both A and B molecules, protonation occurs at N1 positon of TAP which are confirmed by the widening of C-N-C bond angle C2A-N1A-C6A & C2B-N1B-C6B are 120.4 (2) o and 120.24 (2) o respectively where as the N3 position remains as non protonated with C-N-C bond and angle (C2A-N3A-C4A & C2B-N3B-C4B ) of 116.84 (19) o and 116.98 (18) o respectively (Schwalbe & Williams,1982).
The molecule interacts primarily through a pair of N-H
•••O hydrogen bonds leading to the formation of two different R 2 2 (8) ring motifs involving protonated ring N1A & N1B and amino N2A & N5B of cation and carboxylate O1A & O2A and O1B & O2B of anion (Table 4). Among the two BTCA anions, the anion B forms a R 2 1 (6) ring motif via a bifurcated N-H•••O hydrogen bond involving protonated ring N1B, amino N5B of cation B and carboxylate O1B of anion B. Similarly the BTCA anion A form a R 3 2 (8) ring motif by linking TAP (A and B) cations and BTCA (A) anion through a bifurcated N-H•••O by linking amino N5B of TAP (B) and carboxylate O2A vi [Symmetry code: x,y,1+z ] of BTCA (A) anion. This motif also links amino N2A and amino N5B i [Symmetry code: x,y,-1+z ] via N-H•••N hydrogen bonds. Both the TAP cations exhibit a discrete complementary base pairing with the generation of homomeric R 2 2 (8) Revision OV3176-31.8.24.cif ring motifs via a couple of N-H•••N hydrogen bonding.This motif links two centrosymmetric TAP (A) cation through N2A-H2B•••N3A ii [Symmetry code: 1-x,2-y,-z ] and centrosymmetric TAP (B) through N2B-H2C•••N3B iii [Symmetry code: -x,2-y,1-z]. Similar type of complementary base pairing is also observed in compound I. The discrete base pair formed by B cations are interlinked by huge R 4 4 (20) ring motif involving two centrosymmetric BTCA (A) anion via two pair of N-H•••O hydrogen bonds involving amino N4B and N5B and symmetry related carboxylate O1A iv [Symmetry code: -x,1-y,1-z ] & O2A vi [Symmetry code: x,y,1+z] of BTCA (A) anion. The alternate existence of the R 2 2 (8) and R 4 4 (20) ring motifs propagate as a supramolecular layer along c axis as shown in Fig 3b. The discrete base pair formed by TAP (A) cations are interconnected by R 3 2 (6) ring motif in which O1B atom of BTCA (B) acts as a trifurcated hydrogen bonded donor facilitating the formation of three different motifs (R 2 2 (8) , R 2 1 (6) and R 3 2 (6)). The R 3 2 (6) motif links tetrameric supermolecule involving two TAP (A & B) cations and BTCA (A & B) anions through four N-H•••O hydrogen bonds. The existence of R 3 2 (6) ring motif facilitated the generation of huge R 8 6 (26) ring motif and its recurrence in alternative manner along with the acid base interaction (B molecule) leads to the formation of another supramolecular layer which is also extending along the c axis. These two sheets are inter linked by a linear heterotetrameric synthon by holding a base pair formed by TAP (B) cations and two symmetry related BTCA(B) anion. All the interaction generate a supramolecular sheet like architecture which is further stabilized by aromatic face to face π-π stacking interaction observed between five membered ring of BTCA (A) and pyrimidine ring of the TAP (A) molecule [Cg1•••Cg3 vii ; Symmetry code: 1-x,1-y,-z] with centroid to centroid distance of 3.7175 (15) Å, interplanar distance of 3.664 Å and the slip angle of 9.70°. The crystal structure is further strengthened by halogen•••π interaction (symmetry code:x,-1+y,-1+z) with distance 3.6250 (9) Å and angle of 139.86 (8) o . These values are agree with those reported (Shukla et al., 2017) halogen•••π interaction.
The crystal structure of compound (IV) is the isomorphous with the crystal structure of compound (III). Both the compounds are crystallized in triclinic P-1 space group with similar cell parameters . The asymmetric unit of compound IV consists of two TAP cations (A and B) and two 5-chlorothiophene-2-carboxylate anions (CTCA (A) and (B)) as shown in Fig 4a . The protonation of compound (IV) is similar to compound (III) and the parameters are also closely agree with the compound (III). The supramolecular hydrogen bonded interactions (Table 5) of this compounds are exactly isostructural (Gomathi et al., 2014) with compound (III) except the existence of R 4 2 (10) motif adjacent to R 2 2 (8) instead of R 2 1 (6) in compound (III) (Fig 4b). The values of aromatic stacking and halogen••• π interaction (Riley et al., 2016) of this compound have a very good agreement with the crystal structure of (III).
In the crystal structures (I-IV), there is a consistent protonation at the N1 position of TAP with similar widening of C -N-C bond angles. Compounds (I-IV) exhibit an acid-base interactions to form a robust R 2 2 (8) homomeric and heteromeric synthons involving primary acid base interaction and secondary complementary base pairing.
The compounds ( I and II) develop sextruple (compound I) and quadruple (compounds I & II) hydrogen bonded array. Compound (II) exhibits a rosette like architecture. All compounds develop a supramolecular hydrogen bonded pattern facilitated by several N-H•••O and N-H•••N hydrogen bonds with multiple furcated donors and acceptors. In compounds (II-IV) aromatic π-π stacking plays an additional role in stabilizing the compounds where in compound I, C -H•••π governs the additional stability. Compound (IV) is isostructural and isomorphous with Compound (III), exhibiting identical crystal structure with different composition and identical supramolecular interactions and architectures. In compounds (III & IV), a linear hetero tetrameric motif is fomed and in addition, halogen••• π interactions enhanced the crystal stability. Crystal structure of four TAP salts have been synthesized and characterized by single-crystal X-ray diffraction technique and their non-covalent interactions and supramolecular patterns have been investigated.
Table 1 Experimental details (1) (2) (3) (4) Crystal data Chemical formula C 11 H 10 NO 2 •C 11 H 11 NO 2 •C 4 H 8 N 5 C 10 H 8 NO 2 •C 4 H 8 N 5 C 5 H 2 BrO 2 S•C 4 H 8 N 5 C 5 H 2 ClO 2 S•C 4 H 8 N 5 M r 503.56 300.33 332.19 287.73 Crystal system, space group Monoclinic, P2 1 /c Triclinic, P1 Triclinic, P1 Triclinic, P1 Temperature (K) 120 120 120 120 a, b, c (Å) 5.6392 (3), 13.4963 (7), 31.968 (2) 11.5487 (14), 11.5859 (10), 11.9737 (15) 8.4348 (5), 10.5501 (7), 14.0931 (9) 8.3306 (5), 10.4403 (5), 14.0361 (5) α, β, γ (°) 90, 92.790 (6), 90 69.595 (9), 73.659 (11), 74.862 (9) 77.558 (5), 86.820 (5), 78.896 (5) 78.406 (4), 87.357 (4), 78.608 (4) V (Å 3 ) 2430.2 (2) 1417.0 (3) 1201.61 (14) 1172.28 (10) Z 4 4 4 4 Radiation type Mo Kα Mo Kα Cu Kα Cu Kα µ (mm -1 ) 0.10 0.10 6.34 4.61 Crystal size (mm) 0.47 × 0.43 × 0.10 0.48 × 0.23 × 0.12 0.15 × 0.12 × 0.06 0.36 × 0.15 × 0.12 Data collection Diffractometer SuperNova, Dual, Cu at zero, Atlas SuperNova, Dual, Cu at zero, Atlas SuperNova, Dual, Cu at zero, Atlas XtaLAB Synergy, Dualflex, HyPix Absorption correction Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. T min , T max 0.956, 0.990 0.954, 0.988 0.450, 0.702 0.288, 0.608 No. of measured, independent and observed [I > 2σ(I)] reflections 17370, 6030, 4473 13004, 7007, 4307 10725, 4975, 4697 10298, 4863, 4401 R int 0.045 0.052 0.022 0.026 (sin θ/λ) max (Å -1 ) 0.667 0.667 0.631 0.632 Refinement R[F 2 > 2σ(F 2 )], wR(F 2 ), S 0.047, 0.115, 1.05 0.062, 0.145, 1.03 0.031, 0.083, 1.04 0.038, 0.108, 1.05 No. of reflections 6030 7007 4975 4863 No. of parameters 374 461 382 381 No. of restraints 1 0 0 0 H-atom treatment H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement Revision OV3176-31.8.24.cif Δρ max , Δρ min (e Å -3 ) 0.24, -0.26 0.24, -0.27 1.23, -1.27 0.68, -0.57 Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT 2014/4 (Sheldrick, 2015a), SHELXL2016/6 (Sheldrick, 2015b), SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POVRay (Cason, 2004), publCIF (Westrip, 2010).
Hydrogen-bond geometry (Å, º) for ( 1)
78 (2) 2.7577 (17) 174.8 (19) N2-H2B•••N3 i 0.92 (2) 2.08 (2) 2.9915 (19) 170.5 (17) N2-H2A•••O2B 0.90 (2) 2.03 (2) 2.7825 (18) 139.9 (16) N5-H5A•••O1A ii 0.89 (2) 2.139 (19) 2.9149 (17) 144.7 (16) N5-H5B•••O1A 0.92 (2) 1.89 (2) 2.8166 (19) 177 (2) N4-H4A•••O2B i 0.89 (2) 2.12 (2) 2.9968 (19) 172.5 (18)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1.
Hydrogen-bond geometry (Å, º) for ( 2)
Hydrogen-bond geometry (Å, º) for ( 3)
Revision OV3176-31.8.24.cif supporting information sup-1 Revision OV3176-31.8.24.cif supporting information Structural Insights into Supramolecular Interactions in Isostructural Salts of 2,4,6-Triaminopyrimidinium with Various Heterocyclic Carboxylates Mohana Marimuthu, Gomathi Sundaramoorthy, Thomas Muthiah Packianathan* and Ray J. Butcher Computing details For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT 2014/4 (Sheldrick, 2015a).
Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b) for ( 1), ( 3), (4); SHELXL2018/3 (Sheldrick, 2015b) for (2). For all structures, molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009), publCIF (Westrip, 2010).
(1) T = 120 K Plate, pale yellow 0.47 × 0.43 × 0.10 mm Data collection SuperNova, Dual, Cu at zero, Atlas diffractometer Radiation source: SuperNova (Mo) X-ray Source Detector resolution: 10.6501 pixels mm -1 ω scans Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. T min = 0.956, T max = 0.990 17370 measured reflections 6030 independent reflections 4473 reflections with
115 supporting information sup-2 Revision OV3176-31.8.24.cif S = 1.05 6030 reflections 374 parameters 1 restraint Primary atom site location: dual Secondary atom site location: difference Fourier map Hydrogen site location: mixed H atoms treated by a mixture of independent and constrained refinement w = 1/[σ 2 (F o 2 ) + (0.0357P) 2 + 0.393P]
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.24 e Å -3 Δρ min = -0.26 e Å -3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) for ( 1) x y z U iso */U eq N1 0.2250 (2) 0.23098 (9) 0.48773 (4) 0.0194 (3) H1A 0.297 (4) 0.2747 (15) 0.4676 (7) 0.042 (6)* N2 0.4890 (2) 0.11276 (10) 0.46916 (5) 0.0234 (3) H2A 0.564 (3) 0.1575 (14) 0.4534 (6) 0.033 (5)* H2B 0.562 (3) 0.0529 (14) 0.4744 (6) 0.036 (5)* N3 0.2286 (2) 0.07378 (9) 0.51961 (4) 0.0200 (3) N4 -0.0371 (3) 0.03859 (10) 0.56903 (5) 0.0238 (3) H4A 0.030 (4) -0.0206 (15) 0.5717 (6) 0.034 (5)* H4B -0.157 (3) 0.0529 (14) 0.5819 (6) 0.030 (5)* N5 -0.0360 (3) 0.35429 (10) 0.50222 (5) 0.0248 (3) H5A -0.139 (4) 0.3828 (13) 0.5189 (6) 0.031 (5)* H5B 0.063 (4) 0.3941 (15) 0.4873 (7) 0.048 (6)* C2 0.3124 (3) 0.13818 (10) 0.49285 (5) 0.0192 (3) C4 0.0415 (3) 0.10331 (11) 0.54137 (5) 0.0192 (3) C5 -0.0613 (3) 0.19655 (11) 0.53671 (5) 0.0209 (3) H5A1 -0.195106 0.214552 0.551972 0.025* C6 0.0361 (3) 0.26194 (11) 0.50940 (5) 0.0202 (3) O1A 0.2704 (2) 0.47885 (8) 0.45922 (4) 0.0286 (3) O2A 0.4543 (2) 0.35032 (8) 0.43252 (4) 0.0276 (3) N6A 0.0571 (3) 0.68220 (10) 0.35278 (5) 0.0245 (3) H6A -0.077 (4) 0.6670 (14) 0.3385 (7) 0.040 (6)* C7A 0.1775 (3) 0.61903 (11) 0.37986 (5) 0.0223 (3) H7A 0.123305 0.555184 0.387478 0.027* C8A 0.3855 (3) 0.66059 (10) 0.39428 (5) 0.0184 (3) C9A 0.3950 (3) 0.75556 (10) 0.37467 (5) 0.0187 (3) C10A 0.5597 (3) 0.83268 (11) 0.37677 (5) 0.0229 (3) H10A 0.701171 0.827100 0.393984 0.028* C11A 0.5141 (3) 0.91720 (12) 0.35349 (6) 0.0290 (4) H11A 0.625187 0.970142 0.354873 0.035* C12A 0.3069 (3) 0.92625 (12) 0.32789 (6) 0.0280 (4) H12A 0.280552 0.985172 0.312084 0.034* C13A 0.1406 (3) 0.85168 (12) 0.32510 (5) 0.0260 (4) H13A 0.000182 0.857701 0.307621 0.031* C14A 0.1868 (3) 0.76702 (11) 0.34899 (5) 0.0201 (3) C15A 0.5703 (3) 0.62031 (11) 0.42464 (5) 0.0208 (3) supporting information sup-3 Revision OV3176-31.8.24.cif H15A 0.521911 0.634835 0.453351 0.025* H15B 0.720956 0.655993 0.420655 0.025* C16A 0.6172 (3) 0.50954 (11) 0.42132 (6) 0.0234 (3) H16A 0.631652 0.492649 0.391414 0.028* H16B 0.771783 0.494804 0.436016 0.028* C17A 0.4308 (3) 0.44322 (11) 0.43899 (5) 0.0228 (3) O1B 0.7773 (3) 0.30849 (9) 0.38377 (5) 0.0410 (4) H1B 0.667 (4) 0.320 (2) 0.4028 (8) 0.085 (10)* O2B 0.8445 (2) 0.16603 (8) 0.41613 (4) 0.0329 (3) N6B 1.5069 (3) 0.23563 (10) 0.24054 (5) 0.0254 (3) H6B 1.632 (4) 0.2564 (15) 0.2260 (7) 0.053 (7)* C7B 1.4121 (3) 0.28776 (12) 0.27251 (6) 0.0258 (4) H7B 1.476118 0.347515 0.283999 0.031* C8B 1.2144 (3) 0.24218 (11) 0.28546 (5) 0.0223 (3) C9B 1.1790 (3) 0.15702 (11) 0.25921 (5) 0.0190 (3) C10B 1.0061 (3) 0.08315 (11) 0.25574 (5) 0.0220 (3) H10B 0.875002 0.083765 0.273318 0.026* C11B 1.0283 (3) 0.00941 (11) 0.22648 (5) 0.0247 (4) H11B 0.911301 -0.041166 0.223992 0.030* C12B 1.2206 (3) 0.00752 (11) 0.20025 (5) 0.0247 (4) H12B 1.232316 -0.044656 0.180504 0.030* C13B 1.3922 (3) 0.07978 (11) 0.20261 (5) 0.0226 (3) H13B 1.522789 0.078503 0.184934 0.027* C14B 1.3676 (3) 0.15469 (11) 0.23178 (5) 0.0209 (3) C15B 1.0615 (3) 0.27346 (11) 0.31986 (5) 0.0242 (4) H15C 0.895401 0.278557 0.308536 0.029* H15D 1.111851 0.340233 0.329542 0.029* C16B 1.0693 (3) 0.20361 (12) 0.35730 (6) 0.0275 (4) H16C 1.047994 0.134890 0.346951 0.033* H16D 1.228523 0.207876 0.371647 0.033* C17B 0.8861 (3) 0.22399 (11) 0.38862 (5) 0.0245 (4) Atomic displacement parameters (Å 2 ) for (1) U 11 U 22 U 33 U 12 U 13 U 23 N1 0.0220 (7) 0.0177 (6) 0.0188 (7) 0.0015 (5) 0.0045 (6) 0.0001 (5) N2 0.0237 (7) 0.0188 (6) 0.0285 (8) 0.0016 (5) 0.0106 (6) 0.0014 (6) N3 0.0242 (7) 0.0176 (6) 0.0185 (7) -0.0011 (5) 0.0052 (6) -0.0013 (5) N4 0.0285 (8) 0.0202 (7) 0.0235 (7) 0.0007 (6) 0.0104 (6) 0.0006 (6) N5 0.0264 (8) 0.0229 (7) 0.0257 (8) 0.0063 (6) 0.0074 (6) 0.0023 (6) C2 0.0212 (8) 0.0185 (7) 0.0180 (8) -0.0023 (6) 0.0014 (6) -0.0034 (6) C4 0.0209 (8) 0.0208 (7) 0.0161 (7) -0.0022 (6) 0.0015 (6) -0.0039 (6) C5 0.0205 (8) 0.0233 (7) 0.0190 (8) 0.0010 (6) 0.0045 (6) -0.0031 (6) C6 0.0216 (8) 0.0215 (7) 0.0175 (8) 0.0009 (6) -0.0002 (6) -0.0032 (6) O1A 0.0335 (7) 0.0203 (5) 0.0334 (7) 0.0040 (5) 0.0163 (6) 0.0031 (5) O2A 0.0349 (7) 0.0181 (5) 0.0309 (7) 0.0039 (5) 0.0143 (6) 0.0016 (5) N6A 0.0210 (7) 0.0269 (7) 0.0252 (8) -0.0016 (6) -0.0026 (6) -0.0015 (6) C7A 0.0257 (8) 0.0206 (7) 0.0208 (8) -0.0005 (6) 0.0030 (7) -0.0011 (6) C8A 0.0209 (8) 0.0187 (7) 0.0159 (7) 0.0020 (6) 0.0034 (6) -0.0013 (6) C9A 0.0217 (8) 0.0186 (7) 0.0161 (7) 0.0033 (6) 0.0030 (6) -0.0017 (6) C10A 0.0232 (8) 0.0220 (7) 0.0236 (8) -0.0003 (6) 0.0008 (7) -0.0004 (7) supporting information sup-4 Revision OV3176-31.8.24.cif C11A 0.0334 (10) 0.0203 (7) 0.0335 (10) -0.0019 (7) 0.0025 (8) 0.0041 (7) C12A 0.0362 (10) 0.0232 (8) 0.0250 (9) 0.0086 (7) 0.0056 (8) 0.0058 (7) C13A 0.0281 (9) 0.0295 (8) 0.0204 (8) 0.0096 (7) 0.0019 (7) 0.0000 (7) C14A 0.0206 (8) 0.0231 (7) 0.0168 (8) 0.0039 (6) 0.0022 (6) -0.0032 (6) C15A 0.0210 (8) 0.0212 (7) 0.0202 (8) 0.0008 (6) 0.0009 (7) 0.0029 (6) C16A 0.0249 (8) 0.0208 (7) 0.0249 (9) 0.0051 (6) 0.0058 (7) 0.0030 (7) C17A 0.0270 (9) 0.0217 (7) 0.0199 (8) 0.0041 (6) 0.0048 (7) 0.0034 (7) O1B 0.0578 (9) 0.0260 (6) 0.0419 (9) 0.0179 (6) 0.0313 (8) 0.0099 (6) O2B 0.0406 (7) 0.0267 (6) 0.0330 (7) 0.0073 (5) 0.0174 (6) 0.0086 (6) N6B 0.0246 (7) 0.0266 (7) 0.0256 (8) -0.0034 (6) 0.0072 (6) -0.0003 (6) C7B 0.0277 (9) 0.0243 (8) 0.0257 (9) -0.0009 (7) 0.0032 (7) -0.0019 (7) C8B 0.0273 (8) 0.0204 (7) 0.0194 (8) 0.0026 (6) 0.0039 (7) 0.0007 (6) C9B 0.0215 (8) 0.0200 (7) 0.0154 (7) 0.0044 (6) 0.0005 (6) 0.0041 (6) C10B 0.0236 (8) 0.0229 (7) 0.0196 (8) 0.0018 (6) 0.0036 (7) 0.0041 (7) C11B 0.0277 (9) 0.0206 (7) 0.0256 (9) -0.0023 (6) -0.0007 (7) 0.0018 (7) C12B 0.0334 (9) 0.0206 (7) 0.0198 (8) 0.0050 (7) 0.0002 (7) -0.0003 (7) C13B 0.0247 (8) 0.0261 (8) 0.0173 (8) 0.0072 (6) 0.0046 (7) 0.0028 (7) C14B 0.0213 (8) 0.0214 (7) 0.0199 (8) 0.0015 (6) 0.0001 (6) 0.0038 (6) C15B 0.0304 (9) 0.0205 (7) 0.0222 (8) 0.0026 (6) 0.0067 (7) -0.0004 (7) C16B 0.0347 (10) 0.0239 (8) 0.0249 (9) 0.0078 (7) 0.0099 (8) 0.0024 (7) C17B 0.0323 (9) 0.0191 (7) 0.0227 (8) 0.0003 (6) 0.0063 (7) -0.0018 (7) Geometric parameters (Å, º) for (1) N1-C2 1.3530 (19) C13A-C14A 1.392 (2) N1-C6 1.364 (2) C13A-H13A 0.9500 N1-H1A 0.98 (2) C15A-C16A 1.523 (2) N2-C2 1.325 (2) C15A-H15A 0.9900 N2-H2A 0.90 (2) C15A-H15B 0.9900 N2-H2B 0.92 (2) C16A-C17A 1.511 (2) N3-C2 1.3230 (19) C16A-H16A 0.9900 N3-C4 1.352 (2) C16A-H16B 0.9900 N4-C4 1.334 (2) O1B-C17B 1.3008 (19) N4-H4A 0.89 (2) O1B-H1B 0.905 (17) N4-H4B 0.83 (2) O2B-C17B 1.2085 (19) N5-C6 1.328 (2) N6B-C14B 1.366 (2) N5-H5A 0.89 (2) N6B-C7B 1.371 (2) N5-H5B 0.92 (2) N6B-H6B 0.91 (2) C4-C5 1.390 (2) C7B-C8B 1.356 (2) C5-C6 1.374 (2) C7B-H7B 0.9500 C5-H5A1 0.9500 C8B-C9B 1.431 (2) O1A-C17A 1.2346 (19) C8B-C15B 1.491 (2) O2A-C17A 1.2788 (18) C9B-C10B 1.395 (2) N6A-C14A 1.367 (2) C9B-C14B 1.411 (2) N6A-C7A 1.371 (2) C10B-C11B 1.376 (2) N6A-H6A 0.89 (2) C10B-H10B 0.9500 C7A-C8A 1.360 (2) C11B-C12B 1.403 (2) C7A-H7A 0.9500 C11B-H11B 0.9500 C8A-C9A 1.429 (2) C12B-C13B 1.373 (2) C8A-C15A 1.492 (2) C12B-H12B 0.9500 C9A-C10A 1.394 (2) C13B-C14B 1.387 (2) supporting information sup-5 Revision OV3176-31.8.24.cif C9A-C14A 1.408 (2) C13B-H13B 0.9500 C10A-C11A 1.379 (2) C15B-C16B 1.523 (2) C10A-H10A 0.9500 C15B-H15C 0.9900 C11A-C12A 1.399 (3) C15B-H15D 0.9900 C11A-H11A 0.9500 C16B-C17B 1.499 (2) C12A-C13A 1.376 (2) C16B-H16C 0.9900 C12A-H12A 0.9500 C16B-H16D 0.9900 C2-N1-C6 120.73 (14) C8A-C15A-H15B 108.4 C2-N1-H1A 118.5 (12) C16A-C15A-H15B 108.4 C6-N1-H1A 120.7 (12) H15A-C15A-H15B 107.5 C2-N2-H2A 122.1 (12) C17A-C16A-C15A 115.41 (13) C2-N2-H2B 117.7 (12) C17A-C16A-H16A 108.4 H2A-N2-H2B 118.1 (17) C15A-C16A-H16A 108.4 C2-N3-C4 116.84 (13) C17A-C16A-H16B 108.4 C4-N4-H4A 120.1 (13) C15A-C16A-H16B 108.4 C4-N4-H4B 118.7 (13) H16A-C16A-H16B 107.5 H4A-N4-H4B 121.0 (18) O1A-C17A-O2A 123.45 (15) C6-N5-H5A 120.3 (12) O1A-C17A-C16A 120.39 (14) C6-N5-H5B 116.7 (13) O2A-C17A-C16A 116.14 (14) H5A-N5-H5B 118.9 (17) C17B-O1B-H1B 113.7 (18) N3-C2-N2 120.11 (14) C14B-N6B-C7B 108.79 (14) N3-C2-N1 123.14 (14) C14B-N6B-H6B 126.5 (14) N2-C2-N1 116.75 (14) C7B-N6B-H6B 124.4 (14) N4-C4-N3 116.16 (14) C8B-C7B-N6B 110.55 (14) N4-C4-C5 120.89 (15) C8B-C7B-H7B 124.7 N3-C4-C5 122.91 (14) N6B-C7B-H7B 124.7 C6-C5-C4 118.16 (14) C7B-C8B-C9B 106.18 (14) C6-C5-H5A1 120.9 C7B-C8B-C15B 127.63 (15) C4-C5-H5A1 120.9 C9B-C8B-C15B 126.19 (14) N5-C6-N1 116.09 (14) C10B-C9B-C14B 118.67 (14) N5-C6-C5 125.75 (15) C10B-C9B-C8B 134.21 (15) N1-C6-C5 118.15 (13) C14B-C9B-C8B 107.12 (13) C14A-N6A-C7A 109.02 (14) C11B-C10B-C9B 118.97 (15) C14A-N6A-H6A 126.4 (13) C11B-C10B-H10B 120.5 C7A-N6A-H6A 124.3 (13) C9B-C10B-H10B 120.5 C8A-C7A-N6A 110.48 (14) C10B-C11B-C12B 121.22 (15) C8A-C7A-H7A 124.8 C10B-C11B-H11B 119.4 N6A-C7A-H7A 124.8 C12B-C11B-H11B 119.4 C7A-C8A-C9A 105.75 (14) C13B-C12B-C11B 121.14 (15) C7A-C8A-C15A 129.33 (14) C13B-C12B-H12B 119.4 C9A-C8A-C15A 124.91 (14) C11B-C12B-H12B 119.4 C10A-C9A-C14A 118.72 (14) C12B-C13B-C14B 117.48 (15) C10A-C9A-C8A 133.44 (15) C12B-C13B-H13B 121.3 C14A-C9A-C8A 107.83 (13) C14B-C13B-H13B 121.3 C11A-C10A-C9A 119.02 (16) N6B-C14B-C13B 130.18 (15) C11A-C10A-H10A 120.5 N6B-C14B-C9B 107.34 (14) C9A-C10A-H10A 120.5 C13B-C14B-C9B 122.48 (14) C10A-C11A-C12A 121.09 (15) C8B-C15B-C16B 114.14 (13) C10A-C11A-H11A 119.5 C8B-C15B-H15C 108.7 C12A-C11A-H11A 119.5 C16B-C15B-H15C 108.7 supporting information sup-6 Revision OV3176-31.8.24.cif C13A-C12A-C11A 121.43 (15) C8B-C15B-H15D 108.7 C13A-C12A-H12A 119.3 C16B-C15B-H15D 108.7 C11A-C12A-H12A 119.3 H15C-C15B-H15D 107.6 C12A-C13A-C14A 117.12 (16) C17B-C16B-C15B 114.66 (14) C12A-C13A-H13A 121.4 C17B-C16B-H16C 108.6 C14A-C13A-H13A 121.4 C15B-C16B-H16C 108.6 N6A-C14A-C13A 130.48 (15) C17B-C16B-H16D 108.6 N6A-C14A-C9A 106.92 (14) C15B-C16B-H16D 108.6 C13A-C14A-C9A 122.60 (15) H16C-C16B-H16D 107.6 C8A-C15A-C16A 115.51 (14) O2B-C17B-O1B 123.17 (16) C8A-C15A-H15A 108.4 O2B-C17B-C16B 122.13 (14) C16A-C15A-H15A 108.4 O1B-C17B-C16B 114.70 (14) C4-N3-C2-N2 -177.11 (15) C8A-C9A-C14A-C13A -179.61 (14) C4-N3-C2-N1 2.3 (2) C7A-C8A-C15A-C16A 37.8 (2) C6-N1-C2-N3 -2.4 (2) C9A-C8A-C15A-C16A -143.28 (15) C6-N1-C2-N2 176.97 (15) C8A-C15A-C16A-C17A -75.62 (19) C2-N3-C4-N4 -178.30 (14) C15A-C16A-C17A-O1A -8.8 (2) C2-N3-C4-C5 -0.3 (2) C15A-C16A-C17A-O2A 172.86 (15) N4-C4-C5-C6 176.40 (15) C14B-N6B-C7B-C8B 0.8 (2) N3-C4-C5-C6 -1.5 (2) N6B-C7B-C8B-C9B -1.48 (19) C2-N1-C6-N5 179.91 (15) N6B-C7B-C8B-C15B 178.81 (15) C2-N1-C6-C5 0.5 (2) C7B-C8B-C9B-C10B -177.52 (18) C4-C5-C6-N5 -178.01 (16) C15B-C8B-C9B-C10B 2.2 (3) C4-C5-C6-N1 1.4 (2) C7B-C8B-C9B-C14B 1.61 (18) C14A-N6A-C7A-C8A 0.16 (19) C15B-C8B-C9B-C14B -178.67 (15) N6A-C7A-C8A-C9A -0.31 (18) C14B-C9B-C10B-C11B 1.6 (2) N6A-C7A-C8A-C15A 178.78 (15) C8B-C9B-C10B-C11B -179.37 (16) C7A-C8A-C9A-C10A 179.54 (17) C9B-C10B-C11B-C12B -0.1 (2) C15A-C8A-C9A-C10A 0.4 (3) C10B-C11B-C12B-C13B -0.6 (2) C7A-C8A-C9A-C14A 0.34 (17) C11B-C12B-C13B-C14B -0.2 (2) C15A-C8A-C9A-C14A -178.80 (14) C7B-N6B-C14B-C13B -179.06 (16) C14A-C9A-C10A-C11A -0.4 (2) C7B-N6B-C14B-C9B 0.27 (18) C8A-C9A-C10A-C11A -179.54 (16) C12B-C13B-C14B-N6B -178.99 (16) C9A-C10A-C11A-C12A -0.3 (3) C12B-C13B-C14B-C9B 1.8 (2) C10A-C11A-C12A-C13A 0.3 (3) C10B-C9B-C14B-N6B 178.13 (14) C11A-C12A-C13A-C14A 0.3 (2) C8B-C9B-C14B-N6B -1.16 (17) C7A-N6A-C14A-C13A 179.36 (16) C10B-C9B-C14B-C13B -2.5 (2) C7A-N6A-C14A-C9A 0.06 (18) C8B-C9B-C14B-C13B 178.24 (14) C12A-C13A-C14A-N6A 179.83 (16) C7B-C8B-C15B-C16B -112.7 (2) C12A-C13A-C14A-C9A -1.0 (2) C9B-C8B-C15B-C16B 67.7 (2) C10A-C9A-C14A-N6A -179.58 (14) C8B-C15B-C16B-C17B -169.81 (15) C8A-C9A-C14A-N6A -0.24 (17) C15B-C16B-C17B-O2B 167.65 (16) C10A-C9A-C14A-C13A 1.1 (2) C15B-C16B-C17B-O1B -12.5 (2)
Hydrogen-bond geometry (Å, º) for ( 1)
•••O2A 0.91 (2) 1.62 (2) 2.5178 (17) 172 (3) N1-H1A•••O2A 0.98 (2) 1.78 (2) 2.7577 (17) 174.8 (19) N2-H2B•••N3 i 0.92 (2) 2.08 (2) 2.9915 (19) 170.5 (17) supporting information sup-7 Revision OV3176-31.8.24.cif N2-H2A•••O2B 0.90 (2) 2.03 (2) 2.7825 (18) 139.9 (16) N5-H5A•••O1A ii 0.89 (2) 2.139 (19) 2.9149 (17) 144.7 (16) N5-H5B•••O1A 0.92 (2) 1.89 (2) 2.8166 (19) 177 (2) N4-H4A•••O2B i 0.89 (2) 2.12 (2) 2.9968 (19) 172.5 (18) Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1. (2) Crystal data C 10 H 8 NO 2 •C 4 H 8 N 5 M r = 300.33 Triclinic, P1 a = 11.5487 (14) Å b = 11.5859 (10) Å c = 11.9737 (15) Å α = 69.595 (9)°β = 73.659 (11)°γ = 74.862 (9)°V = 1417.0 (3) Å 3 Z = 4 F(000) = 632 D x = 1.408 Mg m -3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 7851 reflections θ = 2.9-31.3°µ = 0.10 mm -1 T = 120 K Block, colourless 0.48 × 0.23 × 0.12 mm Data collection SuperNova, Dual, Cu at zero, Atlas diffractometer Radiation source: SuperNova (Mo) X-ray Source Detector resolution: 10.6501 pixels mm -1 ω scans Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. T min = 0.954, T max = 0.988 13004 measured reflections 7007 independent reflections 4307 reflections with I > 2σ(I) R int = 0.052 θ max = 28.3°, θ min where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.24 e Å -3 Δρ min = -0.27 e Å -3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
supporting information sup-8 Revision OV3176-31.8.24.cif Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) for (2) x y z U iso */U eq N1A 0.63615 (16) 0.30030 (18) 0.62051 (17) 0.0208 (4) H1A 0.644 (3) 0.392 (3) 0.577 (3) 0.061 (9)* N2A 0.63925 (19) 0.2710 (2) 0.43978 (19) 0.0257 (5) H2A 0.629 (2) 0.228 (2) 0.398 (2) 0.031 (7)* H2B 0.660 (2) 0.347 (3) 0.399 (3) 0.043 (8)* N3A 0.60521 (16) 0.10818 (17) 0.61650 (17) 0.0209 (4) N4A 0.5679 (2) -0.04931 (19) 0.7937 (2) 0.0310 (5) H4A 0.548 (3) -0.085 (3) 0.749 (3) 0.050 (9)* H4B 0.559 (3) -0.082 (3) 0.874 (3) 0.070 (11)* N5A 0.64327 (19) 0.3363 (2) 0.7959 (2) 0.0270 (5) H5D 0.665 (3) 0.410 (3) 0.749 (3) 0.056 (10)* H5C 0.642 (2) 0.309 (3) 0.878 (3) 0.048 (8)* C2A 0.62629 (19) 0.2243 (2) 0.5595 (2) 0.0211 (5) C4A 0.5935 (2) 0.0661 (2) 0.7390 (2) 0.0233 (5) C5A 0.6072 (2) 0.1376 (2) 0.8060 (2) 0.0243 (5) H5A 0.601031 0.105141 0.891712 0.029* C6A 0.6300 (2) 0.2565 (2) 0.7435 (2) 0.0220 (5) N1B 0.65132 (18) 0.61064 (17) -0.10067 (16) 0.0211 (4) H1B 0.563 (3) 0.649 (3) -0.085 (3) 0.060 (9)* N2B 0.6484 (2) 0.5680 (2) 0.10206 (18) 0.0258 (5) H2C 0.685 (3) 0.548 (3) 0.167 (3) 0.060 (9)* H2D 0.566 (2) 0.593 (2) 0.113 (2) 0.037 (7)* N3B 0.83497 (16) 0.53634 (17) -0.02755 (16) 0.0225 (4) N4B 1.01985 (18) 0.5148 (2) -0.1620 (2) 0.0297 (5) H4C 1.059 (2) 0.500 (2) -0.101 (2) 0.031 (7)* H4D 1.064 (3) 0.529 (3) -0.238 (3) 0.047 (8)* N5B 0.6422 (2) 0.6387 (2) -0.29810 (19) 0.0262 (5) H5F 0.679 (2) 0.637 (2) -0.377 (3) 0.037 (7)* H5E 0.570 (3) 0.680 (3) -0.285 (3) 0.046 (9)* C2B 0.7144 (2) 0.5707 (2) -0.0094 (2) 0.0213 (5) C4B 0.8970 (2) 0.5428 (2) -0.1444 (2) 0.0229 (5) C5B 0.8378 (2) 0.5737 (2) -0.2402 (2) 0.0248 (5) H5B 0.882802 0.570268 -0.319063 0.030* C6B 0.7124 (2) 0.6094 (2) -0.2174 (2) 0.0226 (5) O1A 0.67827 (15) 0.53560 (14) 0.50482 (14) 0.0267 (4) O2A 0.72548 (14) 0.49730 (14) 0.32602 (14) 0.0264 (4) N6A 0.72289 (18) 0.92150 (18) 0.48589 (18) 0.0260 (5) H6A 0.687 (3) 0.984 (3) 0.520 (3) 0.056 (9)* C7A 0.6674 (2) 0.8778 (2) 0.4250 (2) 0.0246 (5) H7A 0.587994 0.912863 0.407782 0.029* C8A 0.7420 (2) 0.7773 (2) 0.3929 (2) 0.0215 (5) C9A 0.8515 (2) 0.7565 (2) 0.4361 (2) 0.0213 (5) C10A 0.9621 (2) 0.6692 (2) 0.4327 (2) 0.0287 (5) H10A 0.974438 0.604622 0.396544 0.034* C11A 1.0518 (2) 0.6783 (2) 0.4822 (2) 0.0370 (6) H11A 1.126927 0.620103 0.478996 0.044* C12A 1.0347 (2) 0.7718 (3) 0.5372 (2) 0.0396 (7) H12A 1.098518 0.775944 0.570598 0.048* supporting information sup-9 Revision OV3176-31.8.24.cif C13A 0.9274 (2) 0.8579 (2) 0.5438 (2) 0.0332 (6) H13A 0.915715 0.921144 0.581422 0.040* C14A 0.8365 (2) 0.8488 (2) 0.4933 (2) 0.0251 (5) C15A 0.7189 (2) 0.7050 (2) 0.3221 (2) 0.0234 (5) H15B 0.786892 0.706469 0.249761 0.028* H15A 0.642586 0.748720 0.292155 0.028* C16A 0.7070 (2) 0.5694 (2) 0.3902 (2) 0.0211 (5) O1B 0.40872 (14) 0.71706 (16) -0.05616 (15) 0.0301 (4) O2B 0.42128 (15) 0.79833 (15) -0.25663 (14) 0.0294 (4) N6B 0.0357 (2) 0.8516 (2) 0.1637 (2) 0.0315 (5) H6B -0.013 (3) 0.833 (3) 0.233 (3) 0.052 (9)* C7B 0.0746 (2) 0.7887 (2) 0.0777 (2) 0.0286 (6) H7B 0.046635 0.716292 0.083241 0.034* C8B 0.1587 (2) 0.8451 (2) -0.0164 (2) 0.0246 (5) C9B 0.1726 (2) 0.9511 (2) 0.0113 (2) 0.0231 (5) C10B 0.2421 (2) 1.0462 (2) -0.0491 (2) 0.0288 (5) H10B 0.295011 1.048856 -0.126424 0.035* C11B 0.2321 (2) 1.1357 (2) 0.0060 (2) 0.0357 (6) H11B 0.278486 1.200916 -0.034338 0.043* C12B 0.1546 (3) 1.1328 (2) 0.1208 (2) 0.0370 (7) H12B 0.150596 1.195287 0.156885 0.044* C13B 0.0848 (2) 1.0410 (2) 0.1814 (2) 0.0332 (6) H13B 0.031985 1.039132 0.258598 0.040* C14B 0.0942 (2) 0.9514 (2) 0.1258 (2) 0.0257 (5) C15B 0.2217 (2) 0.8090 (2) -0.1297 (2) 0.0298 (6) H15C 0.201125 0.880232 -0.200565 0.036* H15D 0.188453 0.737884 -0.128431 0.036* C16B 0.3608 (2) 0.7721 (2) -0.1485 (2) 0.0241 (5) Atomic displacement parameters (Å 2 ) for (2) U 11 U 22 U 33 U 12 U 13 U 23 N1A 0.0267 (10) 0.0215 (10) 0.0165 (10) -0.0068 (8) -0.0043 (8) -0.0070 (9) N2A 0.0391 (12) 0.0241 (11) 0.0186 (11) -0.0118 (9) -0.0078 (9) -0.0062 (10) N3A 0.0253 (10) 0.0191 (10) 0.0198 (10) -0.0055 (8) -0.0070 (8) -0.0045 (8) N4A 0.0458 (13) 0.0213 (11) 0.0286 (13) -0.0140 (10) -0.0124 (11) -0.0012 (10) N5A 0.0380 (12) 0.0285 (12) 0.0190 (11) -0.0115 (10) -0.0070 (9) -0.0078 (10) C2A 0.0185 (11) 0.0251 (12) 0.0211 (12) -0.0017 (9) -0.0062 (9) -0.0085 (10) C4A 0.0240 (11) 0.0221 (12) 0.0236 (13) -0.0031 (9) -0.0071 (10) -0.0056 (10) C5A 0.0280 (12) 0.0264 (12) 0.0187 (12) -0.0068 (10) -0.0076 (10) -0.0035 (10) C6A 0.0218 (11) 0.0259 (12) 0.0185 (12) -0.0029 (9) -0.0041 (9) -0.0080 (10) N1B 0.0263 (10) 0.0227 (10) 0.0140 (10) -0.0027 (8) -0.0049 (8) -0.0058 (8) N2B 0.0245 (11) 0.0371 (12) 0.0141 (10) -0.0041 (9) -0.0030 (9) -0.0075 (9) N3B 0.0227 (10) 0.0259 (10) 0.0190 (10) -0.0029 (8) -0.0033 (8) -0.0088 (9) N4B 0.0247 (11) 0.0401 (13) 0.0206 (12) -0.0017 (9) -0.0027 (9) -0.0093 (10) N5B 0.0294 (11) 0.0344 (12) 0.0159 (11) -0.0025 (10) -0.0065 (9) -0.0098 (10) C2B 0.0297 (12) 0.0193 (11) 0.0161 (12) -0.0043 (9) -0.0059 (10) -0.0062 (10) C4B 0.0271 (12) 0.0178 (11) 0.0219 (12) -0.0021 (9) -0.0035 (10) -0.0061 (10) C5B 0.0315 (13) 0.0252 (12) 0.0159 (12) -0.0024 (10) -0.0046 (10) -0.0064 (10) C6B 0.0329 (12) 0.0184 (11) 0.0172 (12) -0.0050 (10) -0.0064 (10) -0.0050 (10) O1A 0.0415 (10) 0.0238 (9) 0.0144 (8) -0.0099 (7) -0.0042 (7) -0.0036 (7) supporting information sup-10 Revision OV3176-31.8.24.cif O2A 0.0396 (10) 0.0257 (9) 0.0167 (8) -0.0070 (7) -0.0066 (7) -0.0084 (7) N6A 0.0299 (11) 0.0226 (10) 0.0296 (12) -0.0020 (9) -0.0098 (9) -0.0119 (10) C7A 0.0245 (12) 0.0260 (12) 0.0234 (13) -0.0046 (10) -0.0090 (10) -0.0045 (11) C8A 0.0265 (12) 0.0208 (11) 0.0165 (11) -0.0043 (9) -0.0043 (9) -0.0047 (10) C9A 0.0254 (11) 0.0203 (11) 0.0160 (11) -0.0058 (9) -0.0024 (9) -0.0031 (10) C10A 0.0285 (13) 0.0258 (13) 0.0233 (13) -0.0030 (10) -0.0009 (10) -0.0019 (11) C11A 0.0237 (13) 0.0387 (15) 0.0350 (15) -0.0033 (11) -0.0069 (11) 0.0046 (13) C12A 0.0319 (14) 0.0469 (17) 0.0380 (16) -0.0142 (13) -0.0166 (12) 0.0023 (14) C13A 0.0395 (14) 0.0345 (14) 0.0320 (15) -0.0163 (12) -0.0146 (12) -0.0051 (12) C14A 0.0287 (12) 0.0238 (12) 0.0213 (12) -0.0062 (10) -0.0075 (10) -0.0022 (10) C15A 0.0313 (12) 0.0210 (12) 0.0160 (12) -0.0055 (10) -0.0065 (10) -0.0015 (10) C16A 0.0236 (11) 0.0224 (12) 0.0168 (12) -0.0037 (9) -0.0061 (9) -0.0042 (10) O1B 0.0285 (9) 0.0409 (10) 0.0217 (9) -0.0009 (8) -0.0093 (7) -0.0109 (8) O2B 0.0332 (9) 0.0361 (10) 0.0205 (9) -0.0049 (8) -0.0072 (7) -0.0101 (8) N6B 0.0304 (12) 0.0353 (12) 0.0240 (12) -0.0096 (10) -0.0029 (10) -0.0025 (10) C7B 0.0299 (13) 0.0224 (12) 0.0332 (14) -0.0055 (10) -0.0097 (11) -0.0053 (12) C8B 0.0241 (12) 0.0253 (12) 0.0253 (13) -0.0040 (10) -0.0104 (10) -0.0049 (11) C9B 0.0240 (12) 0.0246 (12) 0.0189 (12) -0.0047 (10) -0.0080 (10) -0.0013 (10) C10B 0.0338 (13) 0.0287 (13) 0.0235 (13) -0.0072 (11) -0.0101 (11) -0.0029 (11) C11B 0.0481 (16) 0.0291 (14) 0.0332 (15) -0.0159 (12) -0.0158 (13) -0.0009 (12) C12B 0.0497 (16) 0.0307 (14) 0.0370 (16) -0.0028 (13) -0.0191 (13) -0.0131 (13) C13B 0.0360 (14) 0.0384 (15) 0.0253 (14) -0.0009 (12) -0.0117 (11) -0.0095 (12) C14B 0.0254 (12) 0.0264 (12) 0.0233 (13) -0.0030 (10) -0.0089 (10) -0.0031 (11) C15B 0.0326 (13) 0.0321 (14) 0.0302 (14) -0.0050 (11) -0.0135 (11) -0.0110 (12) C16B 0.0293 (12) 0.0246 (12) 0.0235 (13) -0.0038 (10) -0.0077 (10) -0.0125 (11) Geometric parameters (Å, º) for (2) N1A-C6A 1.367 (3) C7A-C8A 1.358 (3) N1A-C2A 1.368 (3) C7A-H7A 0.9500 N1A-H1A 1.03 (3) C8A-C9A 1.430 (3) N2A-C2A 1.323 (3) C8A-C15A 1.494 (3) N2A-H2A 0.87 (2) C9A-C10A 1.408 (3) N2A-H2B 0.91 (3) C9A-C14A 1.411 (3) N3A-C2A 1.331 (3) C10A-C11A 1.372 (3) N3A-C4A 1.353 (3) C10A-H10A 0.9500 N4A-C4A 1.338 (3) C11A-C12A 1.400 (4) N4A-H4A 0.88 (3) C11A-H11A 0.9500 N4A-H4B 0.89 (4) C12A-C13A 1.375 (4) N5A-C6A 1.343 (3) C12A-H12A 0.9500 N5A-H5D 0.90 (3) C13A-C14A 1.392 (3) N5A-H5C 0.91 (3) C13A-H13A 0.9500 C4A-C5A 1.401 (3) C15A-C16A 1.519 (3) C5A-C6A 1.373 (3) C15A-H15B 0.9900 C5A-H5A 0.9500 C15A-H15A 0.9900 N1B-C2B 1.363 (3) O1B-C16B 1.266 (3) N1B-C6B 1.380 (3) O2B-C16B 1.259 (3) N1B-H1B 0.99 (3) N6B-C14B 1.368 (3) N2B-C2B 1.332 (3) N6B-C7B 1.373 (3) N2B-H2C 0.92 (3) N6B-H6B 0.86 (3) N2B-H2D 0.90 (3) C7B-C8B 1.357 (3) supporting information sup-11 Revision OV3176-31.8.24.cif N3B-C2B 1.321 (3) C7B-H7B 0.9500 N3B-C4B 1.366 (3) C8B-C9B 1.437 (3) N4B-C4B 1.342 (3) C8B-C15B 1.491 (3) N4B-H4C 0.91 (3) C9B-C10B 1.400 (3) N4B-H4D 0.89 (3) C9B-C14B 1.415 (3) N5B-C6B 1.333 (3) C10B-C11B 1.377 (3) N5B-H5F 0.92 (3) C10B-H10B 0.9500 N5B-H5E 0.85 (3) C11B-C12B 1.407 (4) C4B-C5B 1.393 (3) C11B-H11B 0.9500 C5B-C6B 1.373 (3) C12B-C13B 1.375 (4) C5B-H5B 0.9500 C12B-H12B 0.9500 O1A-C16A 1.258 (3) C13B-C14B 1.383 (3) O2A-C16A 1.264 (2) C13B-H13B 0.9500 N6A-C14A 1.369 (3) C15B-C16B 1.524 (3) N6A-C7A 1.374 (3) C15B-H15C 0.9900 N6A-H6A 0.91 (3) C15B-H15D 0.9900 C6A-N1A-C2A 120.4 (2) C14A-C9A-C8A 107.17 (18) C6A-N1A-H1A 118.2 (16) C11A-C10A-C9A 119.3 (2) C2A-N1A-H1A 121.4 (16) C11A-C10A-H10A 120.4 C2A-N2A-H2A 120.0 (17) C9A-C10A-H10A 120.4 C2A-N2A-H2B 121.5 (17) C10A-C11A-C12A 121.2 (2) H2A-N2A-H2B 118 (2) C10A-C11A-H11A 119.4 C2A-N3A-C4A 117.74 (18) C12A-C11A-H11A 119.4 C4A-N4A-H4A 117 (2) C13A-C12A-C11A 121.3 (2) C4A-N4A-H4B 120 (2) C13A-C12A-H12A 119.4 H4A-N4A-H4B 122 (3) C11A-C12A-H12A 119.4 C6A-N5A-H5D 119.9 (18) C12A-C13A-C14A 117.5 (2) C6A-N5A-H5C 118.6 (17) C12A-C13A-H13A 121.3 H5D-N5A-H5C 121 (2) C14A-C13A-H13A 121.3 N2A-C2A-N3A 120.83 (19) N6A-C14A-C13A 129.9 (2) N2A-C2A-N1A 116.9 (2) N6A-C14A-C9A 107.49 (19) N3A-C2A-N1A 122.2 (2) C13A-C14A-C9A 122.6 (2) N4A-C4A-N3A 116.1 (2) C8A-C15A-C16A 116.09 (19) N4A-C4A-C5A 121.2 (2) C8A-C15A-H15B 108.3 N3A-C4A-C5A 122.7 (2) C16A-C15A-H15B 108.3 C6A-C5A-C4A 117.6 (2) C8A-C15A-H15A 108.3 C6A-C5A-H5A 121.2 C16A-C15A-H15A 108.3 C4A-C5A-H5A 121.2 H15B-C15A-H15A 107.4 N5A-C6A-N1A 116.6 (2) O1A-C16A-O2A 124.0 (2) N5A-C6A-C5A 124.2 (2) O1A-C16A-C15A 119.41 (18) N1A-C6A-C5A 119.25 (19) O2A-C16A-C15A 116.63 (19) C2B-N1B-C6B 120.10 (19) C14B-N6B-C7B 109.2 (2) C2B-N1B-H1B 119.8 (17) C14B-N6B-H6B 122 (2) C6B-N1B-H1B 119.8 (17) C7B-N6B-H6B 129 (2) C2B-N2B-H2C 121.6 (19) C8B-C7B-N6B 110.1 (2) C2B-N2B-H2D 119.6 (16) C8B-C7B-H7B 124.9 H2C-N2B-H2D 119 (2) N6B-C7B-H7B 124.9 C2B-N3B-C4B 117.06 (19) C7B-C8B-C9B 106.56 (19) C4B-N4B-H4C 121.3 (15) C7B-C8B-C15B 127.6 (2) C4B-N4B-H4D 119.0 (18) C9B-C8B-C15B 125.8 (2) Revision OV3176-31.8.24.cif Data collection SuperNova, Dual, Cu at zero, Atlas diffractometer Radiation source: sealed X-ray tube Detector resolution: 10.6501 pixels mm -1 ω scans Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) for ( 3) x y z U iso */U eq Br1 0.02698 (4) 0.06825 (3) -0.14984 (2) 0.03511 (10) S1 0.15487 (7) 0.21229 (5) -0.00622 (4) 0.02401 (13) O1A 0.2619 (2) 0.37579 (16) 0.11715 (11) 0.0246 (3) O2A 0.2815 (2) 0.55073 (17) -0.00169 (12) 0.0270 (4) C11A 0.2507 (3) 0.4364 (2) 0.03004 (16) 0.0207 (4) C7A 0.1964 (3) 0.3697 (2) -0.04261 (16) 0.0208 (4) C8A 0.1677 (4) 0.4164 (2) -0.13938 (18) 0.0316 (5) H8A 0.185221 0.500976 -0.173009 0.038* C9A 0.1096 (4) 0.3277 (2) -0.18526 (18) 0.0319 (5) H9A 0.083391 0.345353 -0.252089 0.038* C10A 0.0965 (3) 0.2144 (2) -0.12113 (16) 0.0231 (4) Br2 1.31377 (3) 0.54736 (3) 0.55182 (2) 0.03121 (9) S2 0.94653 (6) 0.62021 (5) 0.59563 (4) 0.01968 (12) O1B 0.60183 (19) 0.72305 (17) 0.62508 (11) 0.0248 (3) O2B 0.55136 (19) 0.83865 (17) 0.47353 (11) 0.0234 (3) supporting information sup-15 Revision OV3176-31.8.24.cif C11B 0.6436 (3) 0.7657 (2) 0.53808 (15) 0.0181 (4) C7B 0.8162 (3) 0.7265 (2) 0.51181 (15) 0.0186 (4) C8B 0.8949 (3) 0.7699 (2) 0.42654 (16) 0.0211 (4) H8B 0.842271 0.828710 0.371803 0.025* C9B 1.0623 (3) 0.7181 (2) 0.42881 (17) 0.0241 (4) H9B 1.135481 0.737702 0.376391 0.029* C10B 1.1052 (3) 0.6364 (2) 0.51582 (18) 0.0227 (4) N1A 0.3668 (2) 0.70486 (18) 0.11369 (13) 0.0198 (4) C2A 0.4144 (3) 0.8212 (2) 0.07309 (16) 0.0215 (4) N3A 0.4690 (2) 0.89510 (19) 0.12434 (13) 0.0216 (4) C4A 0.4776 (3) 0.8492 (2) 0.22232 (15) 0.0191 (4) C5A 0.4315 (3) 0.7309 (2) 0.26914 (15) 0.0197 (4) H5A 0.438853 0.701501 0.337654 0.024* C6A 0.3746 (2) 0.6576 (2) 0.21230 (15) 0.0187 (4) N2A 0.4055 (3) 0.8609 (2) -0.02342 (15) 0.0285 (4) N4A 0.5342 (3) 0.9261 (2) 0.27279 (14) 0.0242 (4) N5A 0.3245 (2) 0.54320 (19) 0.24493 (15) 0.0234 (4) N1B 0.2956 (2) 0.81688 (18) 0.66917 (13) 0.0179 (3) C2B 0.1767 (3) 0.8884 (2) 0.60620 (15) 0.0169 (4) N3B 0.0212 (2) 0.90751 (17) 0.63179 (13) 0.0174 (3) C4B -0.0183 (2) 0.8431 (2) 0.72132 (15) 0.0169 (4) C5B 0.0972 (3) 0.7664 (2) 0.78848 (15) 0.0186 (4) H5B 0.066027 0.723553 0.851199 0.022* C6B 0.2562 (3) 0.7555 (2) 0.76045 (15) 0.0173 (4) N2B 0.2237 (2) 0.93808 (19) 0.51704 (13) 0.0193 (4) N4B -0.1758 (2) 0.8567 (2) 0.74525 (14) 0.0217 (4) N5B 0.3803 (2) 0.6903 (2) 0.81891 (14) 0.0219 (4) H1A 0.337 (4) 0.660 (3) 0.079 (2) 0.027 (7)* H2A 0.382 (4) 0.806 (3) -0.058 (2) 0.034 (8)* H2B 0.440 (4) 0.933 (3) -0.053 (2) 0.031 (8)* H4A 0.543 (4) 0.897 (3) 0.334 (3) 0.035 (8)* H4B 0.579 (4) 0.990 (3) 0.241 (2) 0.020 (7)* H5C 0.299 (3) 0.497 (3) 0.205 (2) 0.020 (7)* H5D 0.336 (4) 0.505 (3) 0.303 (3) 0.036 (9)* H1B 0.401 (4) 0.791 (3) 0.647 (2) 0.028 (7)* H2D 0.324 (4) 0.916 (3) 0.502 (2) 0.023 (7)* H2C 0.148 (4) 0.986 (3) 0.477 (2) 0.027 (7)* H4D -0.203 (4) 0.803 (3) 0.793 (3) 0.034 (8)* H4C -0.243 (4) 0.900 (3) 0.702 (2) 0.031 (8)* H5E 0.474 (4) 0.677 (3) 0.795 (2) 0.032 (8)* H5F 0.357 (4) 0.631 (3) 0.879 (2) 0.032 (8)* Atomic displacement parameters (Å 2 ) for (3) U 11 U 22 U 33 U 12 U 13 U 23 Br1 0.05728 (19) 0.02952 (15) 0.02619 (14) -0.02413 (13) 0.00237 (11) -0.00887 (10) S1 0.0354 (3) 0.0217 (3) 0.0171 (2) -0.0125 (2) 0.0030 (2) -0.00309 (19) O1A 0.0326 (9) 0.0245 (8) 0.0178 (7) -0.0114 (7) -0.0009 (6) -0.0010 (6) O2A 0.0432 (10) 0.0222 (8) 0.0183 (7) -0.0151 (7) -0.0024 (7) -0.0011 (6) C11A 0.0214 (10) 0.0229 (10) 0.0177 (10) -0.0050 (8) 0.0007 (8) -0.0031 (8) C7A 0.0236 (10) 0.0192 (10) 0.0200 (10) -0.0062 (8) 0.0002 (8) -0.0029 (8) supporting information sup-16 Revision OV3176-31.8.24.cif C8A 0.0532 (16) 0.0197 (11) 0.0231 (11) -0.0125 (11) -0.0091 (10) 0.0005 (9) C9A 0.0508 (16) 0.0237 (12) 0.0231 (11) -0.0102 (11) -0.0111 (10) -0.0032 (9) C10A 0.0276 (11) 0.0227 (11) 0.0218 (10) -0.0084 (9) 0.0014 (8) -0.0077 (8) Br2 0.01766 (13) 0.02918 (15) 0.04900 (18) 0.00050 (9) -0.00452 (10) -0.01627 (11) S2 0.0179 (2) 0.0191 (2) 0.0216 (2) -0.00378 (18) -0.00101 (18) -0.00284 (19) O1B 0.0188 (7) 0.0339 (9) 0.0179 (7) -0.0041 (6) 0.0010 (6) 0.0014 (6) O2B 0.0190 (7) 0.0288 (8) 0.0186 (7) -0.0010 (6) 0.0009 (6) 0.0004 (6) C11B 0.0180 (10) 0.0191 (10) 0.0182 (9) -0.0062 (8) 0.0008 (7) -0.0039 (8) C7B 0.0190 (10) 0.0184 (10) 0.0190 (10) -0.0045 (8) 0.0004 (8) -0.0044 (8) C8B 0.0219 (10) 0.0204 (10) 0.0213 (10) -0.0051 (8) 0.0038 (8) -0.0047 (8) C9B 0.0219 (11) 0.0232 (11) 0.0289 (11) -0.0066 (8) 0.0061 (9) -0.0088 (9) C10B 0.0173 (10) 0.0201 (10) 0.0335 (12) -0.0044 (8) 0.0013 (8) -0.0110 (9) N1A 0.0266 (9) 0.0176 (9) 0.0156 (8) -0.0073 (7) -0.0016 (7) -0.0012 (7) C2A 0.0264 (11) 0.0206 (10) 0.0168 (10) -0.0057 (8) -0.0013 (8) -0.0007 (8) N3A 0.0299 (10) 0.0204 (9) 0.0151 (8) -0.0089 (7) -0.0016 (7) -0.0009 (7) C4A 0.0198 (10) 0.0205 (10) 0.0157 (10) -0.0028 (8) 0.0008 (7) -0.0022 (8) C5A 0.0209 (10) 0.0214 (10) 0.0150 (9) -0.0039 (8) 0.0005 (7) -0.0001 (8) C6A 0.0169 (9) 0.0197 (10) 0.0168 (9) -0.0016 (8) 0.0018 (7) 0.0002 (8) N2A 0.0476 (13) 0.0241 (10) 0.0162 (9) -0.0166 (9) -0.0034 (8) -0.0002 (8) N4A 0.0320 (10) 0.0258 (10) 0.0161 (9) -0.0105 (8) -0.0019 (7) -0.0021 (7) N5A 0.0307 (10) 0.0191 (9) 0.0200 (9) -0.0089 (8) -0.0001 (7) 0.0002 (8) N1B 0.0165 (8) 0.0200 (9) 0.0165 (8) -0.0044 (7) 0.0007 (6) -0.0014 (7) C2B 0.0190 (9) 0.0132 (9) 0.0188 (10) -0.0044 (7) 0.0001 (7) -0.0032 (7) N3B 0.0182 (8) 0.0170 (8) 0.0161 (8) -0.0042 (6) 0.0012 (6) -0.0014 (6) C4B 0.0195 (10) 0.0148 (9) 0.0173 (10) -0.0045 (8) 0.0023 (8) -0.0047 (8) C5B 0.0209 (10) 0.0190 (10) 0.0159 (9) -0.0055 (8) 0.0024 (8) -0.0029 (8) C6B 0.0214 (10) 0.0151 (9) 0.0161 (9) -0.0041 (7) 0.0002 (7) -0.0044 (7) N2B 0.0164 (9) 0.0217 (9) 0.0172 (8) -0.0038 (7) 0.0013 (7) 0.0014 (7) N4B 0.0181 (9) 0.0269 (10) 0.0180 (9) -0.0053 (7) 0.0018 (7) 0.0004 (8) N5B 0.0188 (9) 0.0256 (10) 0.0189 (9) -0.0025 (7) -0.0008 (7) -0.0007 (7) Geometric parameters (Å, º) for (3) Br1-C10A 1.879 (2) N1A-C2A 1.362 (3) S1-C10A 1.713 (2) N1A-C6A 1.372 (3) S1-C7A 1.727 (2) C2A-N3A 1.327 (3) O1A-C11A 1.255 (3) C2A-N2A 1.336 (3) O2A-C11A 1.265 (3) N3A-C4A 1.362 (3) C11A-C7A 1.496 (3) C4A-N4A 1.352 (3) C7A-C8A 1.365 (3) C4A-C5A 1.396 (3) C8A-C9A 1.417 (3) C5A-C6A 1.386 (3) C9A-C10A 1.353 (3) C6A-N5A 1.335 (3) Br2-C10B 1.869 (2) N1B-C6B 1.364 (3) S2-C10B 1.710 (2) N1B-C2B 1.371 (3) S2-C7B 1.720 (2) C2B-N2B 1.324 (3) O1B-C11B 1.267 (3) C2B-N3B 1.330 (3) O2B-C11B 1.254 (3) N3B-C4B 1.355 (3) C11B-C7B 1.484 (3) C4B-N4B 1.340 (3) C7B-C8B 1.373 (3) C4B-C5B 1.403 (3) C8B-C9B 1.412 (3) C5B-C6B 1.367 (3) C9B-C10B 1.361 (3) C6B-N5B 1.350 (3)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) for (4)
x y z U iso */U eq Cl1 0.97092 (8) 0.92958 (5) 1.14832 (4) 0.03655 (15) S1 0.84726 (6) 0.79481 (5) 1.00626 (3) 0.02449 (13) O1A 0.74189 (18) 0.62714 (14) 0.88237 (10) 0.0253 (3) O2A 0.72412 (19) 0.45143 (14) 1.00078 (10) 0.0267 (3) C11A 0.7541 (2) 0.56700 (19) 0.96914 (14) 0.0211 (4) C7A 0.8095 (2) 0.63513 (19) 1.04192 (14) 0.0215 (4) C8A 0.8426 (3) 0.5877 (2) 1.13853 (16) 0.0293 (4) H8A 0.828531 0.501787 1.171564 0.035* C9A 0.8999 (3) 0.6785 (2) 1.18457 (16) 0.0309 (4) H9A 0.928577 0.661076 1.251303 0.037* C10A 0.9086 (2) 0.7934 (2) 1.12145 (15) 0.0250 (4) Cl2 -0.31592 (6) 0.44909 (5) 0.45244 (5) 0.03503 (15) S2 0.03987 (5) 0.38673 (4) 0.40489 (3) 0.02099 (12) O1B 0.39270 (16) 0.28712 (15) 0.37649 (10) 0.0243 (3) O2B 0.44317 (16) 0.16724 (14) 0.52650 (10) 0.0237 (3) supporting information sup-19 Revision OV3176-31.8.24.cif C11B 0.3500 (2) 0.24198 (19) 0.46245 (14) 0.0191 (3) C7B 0.1743 (2) 0.27972 (18) 0.48818 (14) 0.0191 (3) C8B 0.0952 (2) 0.2339 (2) 0.57201 (14) 0.0225 (4) H8B 0.149814 0.174212 0.626188 0.027* C9B -0.0752 (2) 0.2838 (2) 0.57023 (16) 0.0257 (4) H9B -0.148465 0.261771 0.622115 0.031* C10B -0.1203 (2) 0.3673 (2) 0.48452 (16) 0.0245 (4) N1A 0.6369 (2) 0.29387 (16) 0.88583 (12) 0.0205 (3) N3A 0.5296 (2) 0.10389 (16) 0.87502 (11) 0.0214 (3) N2A 0.6005 (2) 0.13785 (19) 1.02267 (13) 0.0274 (4) N4A 0.4573 (2) 0.07309 (17) 0.72668 (13) 0.0239 (3) N5A 0.6783 (2) 0.45540 (17) 0.75449 (13) 0.0233 (3) C2A 0.5874 (2) 0.17809 (19) 0.92624 (14) 0.0212 (4) C4A 0.5168 (2) 0.15016 (18) 0.77724 (13) 0.0196 (4) C5A 0.5634 (2) 0.26873 (19) 0.73059 (14) 0.0206 (4) H5A 0.552917 0.298355 0.662196 0.025* C6A 0.6255 (2) 0.34172 (19) 0.78741 (14) 0.0194 (3) N1B 0.70232 (19) 0.18810 (16) 0.32963 (12) 0.0192 (3) N3B 0.97979 (19) 0.08982 (15) 0.36771 (11) 0.0185 (3) N2B 0.7728 (2) 0.06219 (16) 0.48077 (12) 0.0205 (3) N4B 1.1806 (2) 0.13731 (18) 0.25558 (13) 0.0230 (3) N5B 0.6189 (2) 0.31598 (18) 0.17952 (13) 0.0232 (3) C2B 0.8214 (2) 0.11275 (18) 0.39271 (14) 0.0181 (3) C4B 1.0205 (2) 0.15386 (18) 0.27877 (13) 0.0185 (3) C5B 0.9052 (2) 0.23341 (18) 0.21140 (13) 0.0191 (3) H5B 0.937720 0.275665 0.149122 0.023* C6B 0.7431 (2) 0.24803 (18) 0.23886 (13) 0.0186 (3) H1A 0.674 (4) 0.345 (3) 0.922 (2) 0.038 (8)* H2A 0.620 (4) 0.191 (3) 1.057 (2) 0.035 (7)* H2B 0.561 (3) 0.068 (3) 1.051 (2) 0.025 (6)* H4A 0.417 (3) -0.003 (3) 0.7624 (19) 0.025 (6)* H4B 0.436 (3) 0.102 (3) 0.663 (2) 0.026 (6)* H5D 0.710 (3) 0.500 (3) 0.794 (2) 0.025 (6)* H5C 0.660 (3) 0.500 (3) 0.695 (2) 0.026 (6)* H1B 0.600 (4) 0.213 (3) 0.352 (2) 0.040 (8)* H2C 0.672 (4) 0.087 (3) 0.496 (2) 0.035 (7)* H2D 0.846 (3) 0.019 (3) 0.5240 (19) 0.022 (6)* H4C 1.251 (4) 0.095 (3) 0.300 (2) 0.027 (6)* H4D 1.208 (4) 0.192 (3) 0.207 (3) 0.043 (8)* H5F 0.646 (4) 0.377 (3) 0.124 (2) 0.036 (7)* H5E 0.520 (4) 0.332 (3) 0.202 (2) 0.033 (7)* Atomic displacement parameters (Å 2 ) for (4) U 11 U 22 U 33 U 12 U 13 U 23 Cl1 0.0527 (3) 0.0301 (3) 0.0345 (3) -0.0201 (2) -0.0006 (2) -0.0123 (2) S1 0.0321 (3) 0.0223 (2) 0.0213 (2) -0.01014 (18) 0.00240 (18) -0.00517 (17) O1A 0.0296 (7) 0.0261 (7) 0.0211 (7) -0.0092 (6) -0.0009 (5) -0.0029 (5) O2A 0.0374 (8) 0.0247 (7) 0.0209 (6) -0.0132 (6) -0.0016 (6) -0.0041 (5) C11A 0.0199 (8) 0.0226 (9) 0.0213 (9) -0.0045 (7) 0.0011 (7) -0.0054 (7) C7A 0.0201 (8) 0.0220 (9) 0.0228 (9) -0.0038 (7) -0.0001 (7) -0.0055 (7) supporting information sup-20 Revision OV3176-31.8.24.cif C8A 0.0399 (12) 0.0213 (9) 0.0275 (10) -0.0081 (8) -0.0068 (9) -0.0029 (8) C9A 0.0396 (12) 0.0270 (10) 0.0275 (10) -0.0068 (9) -0.0073 (9) -0.0069 (8) C10A 0.0239 (9) 0.0253 (10) 0.0289 (10) -0.0063 (7) 0.0001 (8) -0.0106 (8) Cl2 0.0169 (2) 0.0324 (3) 0.0582 (3) 0.00100 (18) -0.0057 (2) -0.0191 (2) S2 0.0177 (2) 0.0200 (2) 0.0255 (2) -0.00281 (16) -0.00296 (16) -0.00501 (17) O1B 0.0173 (6) 0.0316 (7) 0.0210 (6) -0.0034 (5) 0.0007 (5) 0.0004 (5) O2B 0.0181 (6) 0.0292 (7) 0.0206 (6) -0.0009 (5) -0.0010 (5) -0.0010 (5) C11B 0.0175 (8) 0.0207 (8) 0.0206 (8) -0.0053 (7) -0.0001 (7) -0.0059 (7) C7B 0.0174 (8) 0.0178 (8) 0.0230 (9) -0.0039 (7) 0.0006 (7) -0.0060 (7) C8B 0.0220 (9) 0.0227 (9) 0.0239 (9) -0.0051 (7) 0.0027 (7) -0.0069 (7) C9B 0.0217 (9) 0.0257 (10) 0.0325 (10) -0.0066 (7) 0.0072 (8) -0.0120 (8) C10B 0.0161 (8) 0.0212 (9) 0.0398 (11) -0.0035 (7) 0.0000 (8) -0.0145 (8) N1A 0.0232 (8) 0.0195 (8) 0.0195 (7) -0.0060 (6) -0.0021 (6) -0.0028 (6) N3A 0.0260 (8) 0.0206 (8) 0.0177 (7) -0.0063 (6) -0.0013 (6) -0.0018 (6) N2A 0.0409 (10) 0.0252 (9) 0.0187 (8) -0.0145 (8) -0.0040 (7) -0.0017 (7) N4A 0.0279 (8) 0.0251 (8) 0.0202 (8) -0.0092 (7) -0.0020 (6) -0.0038 (6) N5A 0.0281 (8) 0.0209 (8) 0.0210 (8) -0.0078 (7) -0.0010 (6) -0.0013 (7) C2A 0.0220 (9) 0.0209 (9) 0.0201 (9) -0.0042 (7) -0.0005 (7) -0.0027 (7) C4A 0.0180 (8) 0.0211 (9) 0.0187 (8) -0.0015 (7) -0.0004 (7) -0.0036 (7) C5A 0.0199 (8) 0.0225 (9) 0.0186 (8) -0.0034 (7) -0.0003 (7) -0.0030 (7) C6A 0.0166 (8) 0.0195 (8) 0.0199 (8) -0.0013 (6) 0.0014 (6) -0.0011 (7) N1B 0.0165 (7) 0.0210 (8) 0.0199 (7) -0.0035 (6) -0.0002 (6) -0.0034 (6) N3B 0.0173 (7) 0.0174 (7) 0.0207 (7) -0.0034 (6) -0.0002 (6) -0.0034 (6) N2B 0.0168 (8) 0.0217 (8) 0.0209 (8) -0.0023 (6) 0.0002 (6) -0.0006 (6) N4B 0.0164 (7) 0.0291 (9) 0.0219 (8) -0.0036 (6) 0.0014 (6) -0.0019 (7) N5B 0.0174 (8) 0.0275 (8) 0.0227 (8) -0.0016 (6) -0.0019 (6) -0.0024 (7) C2B 0.0180 (8) 0.0159 (8) 0.0213 (8) -0.0046 (6) -0.0010 (7) -0.0046 (6) C4B 0.0189 (8) 0.0165 (8) 0.0215 (9) -0.0043 (7) 0.0009 (7) -0.0064 (7) C5B 0.0194 (8) 0.0201 (8) 0.0179 (8) -0.0036 (7) 0.0007 (7) -0.0042 (7) C6B 0.0206 (9) 0.0175 (8) 0.0189 (8) -0.0036 (7) -0.0007 (7) -0.0067 (7) Geometric parameters (Å, º) for (4) Cl1-C10A 1.720 (2) N1A-C2A 1.361 (3) S1-C10A 1.714 (2) N1A-C6A 1.372 (2) S1-C7A 1.728 (2) N3A-C2A 1.324 (3) O1A-C11A 1.252 (2) N3A-C4A 1.362 (2) O2A-C11A 1.269 (2) N2A-C2A 1.337 (3) C11A-C7A 1.492 (3) N4A-C4A 1.348 (3) C7A-C8A 1.368 (3) N5A-C6A 1.335 (3) C8A-C9A 1.413 (3) C4A-C5A 1.397 (3) C9A-C10A 1.353 (3) C5A-C6A 1.387 (3) Cl2-C10B 1.718 (2) N1B-C6B 1.362 (2) S2-C10B 1.717 (2) N1B-C2B 1.371 (2) S2-C7B 1.7236 (19) N3B-C2B 1.337 (2) O1B-C11B 1.266 (2) N3B-C4B 1.355 (2) O2B-C11B 1.250 (2) N2B-C2B 1.322 (3) C11B-C7B 1.486 (2) N4B-C4B 1.344 (2) C7B-C8B 1.369 (3) N5B-C6B 1.349 (3) C8B-C9B 1.412 (3) C4B-C5B 1.400 (3) C9B-C10B 1.356 (3) C5B-C6B 1.375 (3)
Revision OV3176-31.8.24.cif