| N-[2-(4-Bromo-phen-yl)-5-methyl-4-oxo-1,3-thia-zolidin-3-yl]pyridine-3-carboxamide. | |
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PMID: 21754186 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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In the title compound, C(16)H(14)BrN(3)O(2)S, the atoms of the 1,3-thia-zolidine group, except for the N and the C atoms attached to the bromo-benzene ring, are disordered over two sets of sites with occupancies of 0.605 (13) and 0.395 (13). The benzene and pyridine rings make a dihedral angle of 86.2 (2)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a three-dimensional network. Furthermore, there is a π-π stacking inter-action [centroid-centroid distance = 3.758 (2) Å] between the pyridine and benzene rings. |
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Authors:
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Mehmet Akkurt; Ismail Celik; Hale Demir; Sumru Ozkırımlı; Orhan Büyükgüngör |
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Publication Detail:
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Type: Journal Article Date: 2011-03-19 |
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Title: Acta crystallographica. Section E, Structure reports online Volume: 67 ISSN: 1600-5368 ISO Abbreviation: Acta Crystallogr Sect E Struct Rep Online Publication Date: 2011 Apr |
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Created Date: 2011-07-14 Completed Date: 2011-07-14 Revised Date: 2011-12-09 |
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Nlm Unique ID: 101089178 Medline TA: Acta Crystallogr Sect E Struct Rep Online Country: England |
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Languages: eng Pagination: o914-5 Citation Subset: - |
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Journal Information Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online Journal ID (publisher-id): Acta Cryst. E ISSN: 1600-5368 Publisher: International Union of Crystallography |
Article Information Download PDF  A full version of this article is available from Crystallography Journals Online.© Akkurt et al. 2011 open-access: Received Day: 07 Month: 3 Year: 2011 Accepted Day: 14 Month: 3 Year: 2011 collection publication date: Day: 01 Month: 4 Year: 2011 Electronic publication date: Day: 19 Month: 3 Year: 2011 pmc-release publication date: Day: 19 Month: 3 Year: 2011 Volume: 67 Issue: Pt 4 First Page: o914 Last Page: o915 ID: 3100075 PubMed Id: 21754186 Publisher Id: om2414 DOI: 10.1107/S1600536811009603 Coden: ACSEBH Publisher Item Identifier: S1600536811009603 |
| N-[2-(4-Bromophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide Alternate Title:C16H14BrN3O2S | |
| Mehmet Akkurta* | |
| Ísmail Çelikb | |
| Hale Demirc | |
| Sumru Özkırımlıc | |
| Orhan Büyükgüngörd | |
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aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey |
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bDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey |
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cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey |
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dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey |
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| Correspondence: Correspondence e-mail: akkurt@erciyes.edu.tr |
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For the diverse pharmacological properties of pyridine-3-carboxamides, see: Abdel-Alim et al. (2005 ▶); Girgis et al. (2006 ▶); Slominska et al. (2008 ▶); Spanka et al. (2010 ▶); activities. For the pharmacological properties of 4-thiazolidinone derivatives, see: Vigorita et al. (1992 ▶); Barreca et al. (2003 ▶); Rao et al. (2004 ▶); Jacop & Kutty (2004 ▶); Kalia et al. (2007 ▶).[Chemical Structure ID: scheme1]
- C16H14BrN3O2S
- Mr = 392.27
- Tetragonal,
- a = 24.5799 (8) Å
- c = 10.9601 (6) Å
- V = 6621.8 (5) Å3
- Z = 16
- Mo Kα radiation
- μ = 2.62 mm−1
- T = 296 K
- 0.37 × 0.30 × 0.28 mm
- Stoe IPDS 2 diffractometer
- Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) Tmin = 0.444, Tmax = 0.527
- 13377 measured reflections
- 3644 independent reflections
- 1834 reflections with I > 2σ(I)
- Rint = 0.055
- R[F2 > 2σ(F2)] = 0.058
- wR(F2) = 0.119
- S = 1.02
- 3644 reflections
- 259 parameters
- 13 restraints
- H atoms treated by a mixture of independent and constrained refinement
- Δρmax = 0.39 e Å−3
- Δρmin = −0.34 e Å−3
Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).
Notes
fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2414).
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Scientific Research Projects Coordination Unit of Istanbul University (project No. T-3691).
Pyridine-3-carboxamides have gained attention because of their diverse pharmacological properties such as anti-inflammatory (Abdel-Alim et al., 2005), anticancer (Girgis et al. 2006), cytoprotective (Slominska et al., 2008), and anxiolytic (Spanka et al., 2010) activities. 4-Thiazolidinone derivatives have antineoplastic (Vigorita et al., 1992), HIV-1 RT inhibitory (Barreca et al., 2003; Rao et al., 2004), hypolipidemic (Jacop & Kutty, 2004), and anti-inflammatory (Kalia et al., 2007) activities. In an effort to evaluate bioactive molecules bearing both 4-thiazolidinone and pyridine-3-carboxamide scaffolds together, we synthesized N-(thiazolidin-3-yl)pyridine-3-carboxamide derivatives to examine their antiviral and anticancer properties.
In the 1,3-thiazolidine group of the title molecule (Fig. 1), all except the N1 and C7 atoms are disordered. The dihedral angle between the ring planes (S1A/N1/C7/C8A/C9A and S1B/N1/C7/C8B/C9B) formed by the major and minor disorder components is 18.5 (8) °.
The benzene (C1–C6) and pyridine (N3/C12–C16) rings make a dihedral angle of 86.21 (19) ° with each other. The N1—N2—C11—C12, N1—N2—C11—O2, N2—C11—C12—C13 and O2—C11—C12—C13 torsion angles are 180.0 (3), 1.2 (6), 172.2 (3) and -9.0 (6)°, respectively.
The molecular structure has two weak intramolecular C—H···N interactions (Table 1), generating S(5) ring motifs, and the crystal structure is stabilized by intermolecular N—H···N and C—H···O hydrogen bonds (Table 1 and Fig. 2). In addition, a π-π stacking interaction is observed [Cg3···Cg4(1/4 + y, 1/4 - x, 1/4 + z) = 3.758 (2) Å, where Cg3 and Cg4 are the centroids of the pyridine N3/C12–C16 and benzene C1–C6 rings, respectively].
N'-(4-bromobenzylidine)pyridine-3-carbohydrazide (0.01 mol) was reacted with 0.028 mol of 2-mercaptopropanoic acid in anhydrous benzene for 7 h using a Dean-Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The separated solid was filtered, washed with water and crystallized from methanol to yield white crystalline N-[5-methyl-2-(4-bromophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide. Yield: 58.92%; m.p.: 466.0–470.0 K. UV (EtOH) λ max: 203.0, 220.6, 262.0 nm. IR (KBr) υ: 1674 (amide C=O), 1727 (thia C=O) cm-1; 1H-NMR (DMSO-d6, 500 MHz): 1.54, 1.55 (3H, 2 d, J=7.0 Hz, 6.8 Hz, CH3-thia.), 4.12, 4.22 (1H, 2q, J=6.8 Hz, 6.8 Hz, H5-thia.), 5.90 (1H, s, H2-thia), 7.44–7.46 (2H, m, 2-C6H4-(H2,6)-thia.), 7.49–7.56 (1H, m, H5-pyridine), 7.57–7.60 (2H, m, 2-C6H4-(H3,5)-thia.), 8.05–8.09 (1H, m, H4-pyridine), 8.72–8.73 (1H, m, H6-pyridine), 8.86 (1H, 2 t, J=1 Hz, H2-pyridine), 10.94, 10.95 (1H, 2 s, CONH) p.p.m.; ESI– (m/z, relative abundance): 392.0 ([M—H+2]-, 100), 390.01 ([M—H]-, 79.69). Analysis calculated for C16H14BrN3O2S: C 48.99, H 3.60, N 10.71%. Found: C 49.03, H 3.54, N 10.58%.
The C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2 or 1.5Ueq(C). The N-bound H atom was located from the Fourier synthesis and restrained to 0.86 (2) Å, and refined with Uiso(H) = 1.2Ueq(N). The 1,3-thiazolidine group, except for the N1 and C7 atoms, is disordered over two sites with site occupancies of 0.605 (13) and 0.395 (13). In the last cycles of the refinement, the following values are used for the distance restraints (DFIX): 1.80 (1) Å for the S—C bond, 1.25 (1) Å for C—O, 1.39 (1) Å for C—N and 1.50 (1) Å for C—C
Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) −x+1/2, −y+1/2, −z+1/2; (iii) −x+1, −y+1/2, z; (iv) y+1/4, −x+3/4, −z+3/4; (v) −x+1/2, −y+1/2, −z+3/2; (vi) −y+3/4, x−1/4, −z+3/4; (vii) y+1/4, −x+1/4, z+1/4; (viii) y−1/4, −x+3/4, z−1/4; (ix) −y+3/4, x+1/4, z+1/4.
Symmetry codes: (iv) y+1/4, −x+3/4, −z+3/4; (v) −x+1/2, −y+1/2, −z+3/2; (iii) −x+1, −y+1/2, z.
References
| Abdel-Alim, A. M., El-Shorbagi, A. A., Abdel-Mothy, S. G. & Abdel-Allah, H. H. M. (2005). Arch. Pharm. Res.28, 637–647. | |
| Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119. | |
| Barreca, M. L., Chimirri, A., De Clercq, E., De Luca, L., Monforte, A. M., Monforte, P., Rao, A. & Zappala, M. (2003). Farmaco, 58, 259–263. | |
| Farrugia, L. J. (1997). J. Appl. Cryst.30, 565. | |
| Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838. | |
| Girgis, A. S., Hosni, H. M. & Barsoum, F. F. (2006). Bioorg. Med. Chem.14, 4466–4476. | |
| Jacop, J. & Kutty, G. N. (2004). Indian Drugs, 41, 76–79. | |
| Kalia, R., Rao, C. M. & Kutty, N. G. (2007). Arzneim. Forsch. (Drug Res.), 57, 616–622. | |
| Rao, A., Balzarini, J., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2004). Antiviral Res.63, 79–84. | |
| Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. | |
| Slominska, E. M., Yuen, A., Osman, L., Gebicki, J., Yacoub, M. H. & Smolenski, R. T. (2008). Nucleoside Nucleotides Nucleic Acids, 27, 863-866. | |
| Spanka, C., Glatthar, R., Desrayaud, S., Fendt, M., Orain, D., Troxler, T. & Vranesic, I. (2010). Bioorg. Med. Chem. Lett.20, 184–188. | |
| Stoe & Cie (2002). X-AREA and X-RED32 Stoe & Cie, Darmstadt, Germany. | |
| Vigorita, M. G., Basile, M., Zappala, C., Gabbrielli, G. & Pizzimenti, F. (1992). Farmaco, 47, 893–906. |
Figures
[Figure ID: Fap1] |
Fig. 1.
The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only the major component of the disorder is shown. |
[Figure ID: Fap2] |
Fig. 2.
The packing and hydrogen bonding interactions viewed down the c axis. All hydrogen atoms not involved in hydrogen bonding and the minor component of the disorder have been omitted for clarity. |
Tables
| C16H14BrN3O2S | Dx = 1.574 Mg m−3 |
| Mr = 392.27 | Mo Kα radiation, λ = 0.71073 Å |
| Tetragonal, I41/a | Cell parameters from 9828 reflections |
| Hall symbol: -I 4ad | θ = 1.7–27.6° |
| a = 24.5799 (8) Å | µ = 2.62 mm−1 |
| c = 10.9601 (6) Å | T = 296 K |
| V = 6621.8 (5) Å3 | Block, colourless |
| Z = 16 | 0.37 × 0.30 × 0.28 mm |
| F(000) = 3168 |
| Stoe IPDS 2 diffractometer | 3644 independent reflections |
| Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1834 reflections with I > 2σ(I) |
| plane graphite | Rint = 0.055 |
| Detector resolution: 6.67 pixels mm-1 | θmax = 27.1°, θmin = 1.7° |
| ω scans | h = −31→21 |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −31→31 |
| Tmin = 0.444, Tmax = 0.527 | l = −14→9 |
| 13377 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3 |
| 3644 reflections | (Δ/σ)max < 0.001 |
| 259 parameters | Δρmax = 0.39 e Å−3 |
| 13 restraints | Δρmin = −0.34 e Å−3 |
| Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
| Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Br1 | 0.16970 (2) | 0.06678 (2) | 0.30959 (7) | 0.1147 (3) | |
| S1A | 0.2142 (3) | 0.3258 (3) | 0.5735 (10) | 0.112 (3) | 0.605 (13) |
| O1A | 0.3622 (6) | 0.3685 (8) | 0.529 (2) | 0.106 (7) | 0.605 (13) |
| O2 | 0.36844 (13) | 0.25700 (14) | 0.7196 (3) | 0.0950 (14) | |
| N1 | 0.31204 (11) | 0.29058 (12) | 0.5238 (3) | 0.0623 (13) | |
| N2 | 0.35645 (13) | 0.25553 (13) | 0.5165 (3) | 0.0595 (11) | |
| N3 | 0.48519 (14) | 0.14473 (13) | 0.4828 (4) | 0.0707 (14) | |
| C1 | 0.20330 (14) | 0.18614 (15) | 0.5608 (4) | 0.0640 (14) | |
| C2 | 0.18240 (16) | 0.14118 (16) | 0.5027 (5) | 0.0730 (16) | |
| C3 | 0.19861 (16) | 0.12919 (15) | 0.3869 (5) | 0.0673 (18) | |
| C4 | 0.23459 (18) | 0.16225 (18) | 0.3269 (4) | 0.0763 (17) | |
| C5 | 0.25484 (16) | 0.20793 (16) | 0.3847 (4) | 0.0653 (16) | |
| C6 | 0.23981 (14) | 0.22004 (14) | 0.5022 (4) | 0.0560 (14) | |
| C7 | 0.26058 (14) | 0.26964 (15) | 0.5686 (4) | 0.0703 (16) | |
| C8A | 0.2692 (4) | 0.3725 (3) | 0.5910 (13) | 0.075 (4) | 0.605 (13) |
| C9A | 0.3197 (5) | 0.3447 (3) | 0.548 (2) | 0.079 (8) | 0.605 (13) |
| C10A | 0.2598 (5) | 0.4271 (4) | 0.5333 (15) | 0.125 (7) | 0.605 (13) |
| C11 | 0.38243 (15) | 0.24133 (15) | 0.6199 (5) | 0.0603 (14) | |
| C12 | 0.42975 (14) | 0.20345 (14) | 0.6039 (4) | 0.0510 (14) | |
| C13 | 0.46220 (17) | 0.19258 (16) | 0.7037 (4) | 0.0673 (16) | |
| C14 | 0.50564 (16) | 0.15811 (16) | 0.6913 (5) | 0.0713 (18) | |
| C15 | 0.51542 (16) | 0.13554 (16) | 0.5804 (5) | 0.0663 (16) | |
| C16 | 0.44267 (16) | 0.17785 (16) | 0.4962 (4) | 0.0630 (14) | |
| O1B | 0.3661 (9) | 0.3633 (10) | 0.482 (3) | 0.077 (6) | 0.395 (13) |
| C8B | 0.2702 (5) | 0.3783 (5) | 0.5205 (14) | 0.063 (5) | 0.395 (13) |
| S1B | 0.2171 (4) | 0.3287 (4) | 0.5249 (11) | 0.078 (2) | 0.395 (13) |
| C10B | 0.2737 (7) | 0.4152 (8) | 0.6288 (16) | 0.100 (7) | 0.395 (13) |
| C9B | 0.3209 (8) | 0.3454 (4) | 0.508 (3) | 0.059 (7) | 0.395 (13) |
| H5 | 0.27890 | 0.23070 | 0.34360 | 0.0780* | |
| H7 | 0.26680 | 0.25850 | 0.65330 | 0.0840* | |
| H4 | 0.24530 | 0.15400 | 0.24770 | 0.0910* | |
| H10A | 0.22620 | 0.44200 | 0.56260 | 0.1870* | 0.605 (13) |
| H10B | 0.25810 | 0.42300 | 0.44630 | 0.1870* | 0.605 (13) |
| H8A | 0.27360 | 0.37870 | 0.67870 | 0.07 (2)* | 0.605 (13) |
| H13 | 0.45460 | 0.20850 | 0.77870 | 0.0810* | |
| H14 | 0.52800 | 0.15030 | 0.75750 | 0.0850* | |
| H15 | 0.54510 | 0.11230 | 0.57270 | 0.0800* | |
| H16 | 0.42050 | 0.18400 | 0.42880 | 0.0760* | |
| H1 | 0.19280 | 0.19380 | 0.64040 | 0.0770* | |
| HN2 | 0.3657 (17) | 0.2533 (17) | 0.4409 (14) | 0.0810* | |
| H10C | 0.28920 | 0.45110 | 0.55420 | 0.1870* | 0.605 (13) |
| H2A | 0.15730 | 0.11910 | 0.54230 | 0.0870* | |
| H8B | 0.26570 | 0.40050 | 0.44690 | 0.0750* | 0.395 (13) |
| H10D | 0.24060 | 0.43570 | 0.63580 | 0.1500* | 0.395 (13) |
| H10E | 0.30370 | 0.43980 | 0.61860 | 0.1500* | 0.395 (13) |
| H10F | 0.27900 | 0.39400 | 0.70120 | 0.1500* | 0.395 (13) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.1245 (5) | 0.0791 (3) | 0.1405 (6) | −0.0194 (3) | −0.0237 (4) | −0.0275 (3) |
| S1A | 0.0607 (18) | 0.092 (3) | 0.183 (8) | −0.0045 (15) | 0.027 (3) | −0.069 (3) |
| O1A | 0.066 (5) | 0.084 (5) | 0.167 (19) | −0.012 (4) | 0.003 (7) | −0.028 (8) |
| O2 | 0.094 (2) | 0.131 (3) | 0.060 (2) | 0.0395 (19) | 0.0025 (17) | −0.029 (2) |
| N1 | 0.0498 (17) | 0.0572 (18) | 0.080 (3) | 0.0016 (14) | 0.0006 (16) | −0.0031 (17) |
| N2 | 0.0555 (18) | 0.071 (2) | 0.052 (2) | 0.0053 (15) | 0.0044 (18) | −0.0008 (19) |
| N3 | 0.076 (2) | 0.074 (2) | 0.062 (3) | 0.0162 (18) | 0.013 (2) | 0.0013 (19) |
| C1 | 0.060 (2) | 0.070 (2) | 0.062 (3) | 0.0051 (19) | 0.014 (2) | −0.001 (2) |
| C2 | 0.061 (2) | 0.059 (2) | 0.099 (4) | −0.0032 (19) | 0.004 (3) | 0.009 (2) |
| C3 | 0.069 (3) | 0.055 (2) | 0.078 (4) | 0.0041 (19) | −0.010 (2) | −0.005 (2) |
| C4 | 0.090 (3) | 0.082 (3) | 0.057 (3) | −0.004 (2) | 0.002 (2) | −0.010 (3) |
| C5 | 0.070 (3) | 0.068 (2) | 0.058 (3) | −0.0105 (19) | 0.004 (2) | 0.003 (2) |
| C6 | 0.051 (2) | 0.057 (2) | 0.060 (3) | 0.0035 (17) | 0.003 (2) | −0.005 (2) |
| C7 | 0.059 (2) | 0.077 (3) | 0.075 (3) | −0.0095 (18) | 0.009 (2) | −0.016 (2) |
| C8A | 0.083 (6) | 0.065 (6) | 0.076 (10) | 0.000 (4) | 0.005 (7) | −0.012 (6) |
| C9A | 0.050 (7) | 0.076 (8) | 0.11 (2) | −0.008 (5) | −0.009 (6) | −0.003 (5) |
| C10A | 0.139 (9) | 0.073 (7) | 0.162 (16) | 0.020 (6) | −0.004 (9) | −0.001 (8) |
| C11 | 0.061 (2) | 0.067 (2) | 0.053 (3) | 0.0035 (18) | 0.004 (2) | −0.007 (2) |
| C12 | 0.057 (2) | 0.053 (2) | 0.043 (3) | −0.0029 (16) | 0.0041 (19) | −0.0006 (18) |
| C13 | 0.082 (3) | 0.069 (2) | 0.051 (3) | 0.004 (2) | −0.006 (2) | −0.007 (2) |
| C14 | 0.070 (3) | 0.066 (2) | 0.078 (4) | 0.008 (2) | −0.017 (2) | 0.000 (3) |
| C15 | 0.061 (2) | 0.060 (2) | 0.078 (4) | 0.0060 (18) | 0.007 (2) | 0.002 (2) |
| C16 | 0.070 (2) | 0.070 (2) | 0.049 (3) | 0.012 (2) | 0.003 (2) | −0.002 (2) |
| O1B | 0.073 (8) | 0.063 (9) | 0.096 (14) | −0.008 (6) | 0.006 (7) | 0.010 (9) |
| C8B | 0.072 (7) | 0.063 (8) | 0.053 (10) | 0.008 (5) | 0.001 (8) | 0.012 (8) |
| S1B | 0.049 (3) | 0.069 (3) | 0.115 (6) | 0.0113 (17) | 0.007 (3) | −0.030 (3) |
| C10B | 0.110 (11) | 0.078 (11) | 0.112 (15) | −0.013 (8) | −0.001 (10) | −0.020 (11) |
| C9B | 0.069 (12) | 0.057 (10) | 0.052 (14) | 0.006 (8) | −0.001 (7) | −0.004 (6) |
| Br1—C3 | 1.891 (4) | C8B—C9B | 1.49 (2) |
| S1A—C7 | 1.791 (8) | C8B—C10B | 1.50 (2) |
| S1A—C8A | 1.784 (12) | C11—C12 | 1.500 (5) |
| S1B—C7 | 1.865 (11) | C12—C13 | 1.380 (6) |
| S1B—C8B | 1.787 (16) | C12—C16 | 1.375 (6) |
| O1A—C9A | 1.22 (2) | C13—C14 | 1.370 (6) |
| O1B—C9B | 1.23 (3) | C14—C15 | 1.358 (7) |
| O2—C11 | 1.209 (6) | C1—H1 | 0.9300 |
| N1—C9A | 1.370 (9) | C2—H2A | 0.9300 |
| N1—N2 | 1.393 (4) | C4—H4 | 0.9300 |
| N1—C7 | 1.451 (5) | C5—H5 | 0.9300 |
| N1—C9B | 1.376 (11) | C7—H7 | 0.9800 |
| N2—C11 | 1.347 (6) | C8A—H8A | 0.9800 |
| N3—C15 | 1.322 (6) | C8B—H8B | 0.9800 |
| N3—C16 | 1.333 (5) | C10A—H10B | 0.9600 |
| N2—HN2 | 0.861 (19) | C10A—H10C | 0.9600 |
| C1—C6 | 1.383 (5) | C10A—H10A | 0.9600 |
| C1—C2 | 1.375 (6) | C10B—H10F | 0.9600 |
| C2—C3 | 1.363 (7) | C10B—H10D | 0.9600 |
| C3—C4 | 1.369 (6) | C10B—H10E | 0.9600 |
| C4—C5 | 1.382 (6) | C13—H13 | 0.9300 |
| C5—C6 | 1.372 (6) | C14—H14 | 0.9300 |
| C6—C7 | 1.509 (5) | C15—H15 | 0.9300 |
| C8A—C9A | 1.493 (16) | C16—H16 | 0.9300 |
| C8A—C10A | 1.502 (14) | ||
| Br1···C2i | 3.679 (4) | C14···C1vii | 3.483 (6) |
| Br1···C3i | 3.669 (4) | C15···O1Aiii | 3.062 (16) |
| S1B···C15i | 3.651 (12) | C15···O1Biii | 3.11 (2) |
| S1B···C14i | 3.679 (11) | C15···S1Bvii | 3.651 (12) |
| S1A···H14i | 3.1300 | C16···O1Bvi | 3.23 (3) |
| S1B···H15i | 3.0700 | C5···H5ii | 3.0400 |
| S1B···H14i | 3.1500 | C5···HN2 | 3.01 (4) |
| S1B···H4ii | 3.1600 | C8B···H10Eviii | 3.0800 |
| O1A···N2 | 2.78 (2) | C8B···H4ii | 3.0700 |
| O1A···C15iii | 3.062 (16) | C10A···H10Cviii | 3.0100 |
| O1A···C11 | 3.32 (2) | C11···H7 | 2.9000 |
| O1B···N2 | 2.69 (2) | C15···HN2vi | 3.048 (18) |
| O1B···C11 | 3.38 (3) | C16···HN2 | 2.72 (4) |
| O1B···C16iv | 3.23 (3) | C16···HN2vi | 2.88 (3) |
| O1B···C15iii | 3.11 (2) | H1···O2v | 2.4700 |
| O2···N1 | 2.685 (5) | H1···H7 | 2.4200 |
| O2···C7 | 3.141 (5) | HN2···C16 | 2.72 (4) |
| O2···C9A | 3.102 (15) | HN2···H16 | 2.1800 |
| O2···C1v | 3.295 (5) | HN2···C5 | 3.01 (4) |
| O2···C9B | 3.39 (2) | HN2···N3iv | 2.05 (2) |
| O1A···H15iii | 2.3800 | HN2···C15iv | 3.048 (18) |
| O1A···H10C | 2.7200 | HN2···O1B | 2.74 (5) |
| O1B···H10E | 2.8500 | HN2···C16iv | 2.88 (3) |
| O1B···H15iii | 2.4700 | HN2···H5 | 2.4500 |
| O1B···HN2 | 2.74 (5) | H4···S1Bii | 3.1600 |
| O1B···H16iv | 2.5700 | H4···H8Bii | 2.5300 |
| O2···H1v | 2.4700 | H4···C8Bii | 3.0700 |
| O2···H7 | 2.6000 | H5···C5ii | 3.0400 |
| O2···H13 | 2.5200 | H5···HN2 | 2.4500 |
| N1···O2 | 2.685 (5) | H5···N1 | 2.5900 |
| N2···N3iv | 2.899 (5) | H5···N2 | 2.7600 |
| N2···O1A | 2.78 (2) | H7···C11 | 2.9000 |
| N2···C5 | 3.113 (5) | H7···H1 | 2.4200 |
| N2···O1B | 2.69 (2) | H7···O2 | 2.6000 |
| N3···N2vi | 2.899 (5) | H7···H7v | 2.3100 |
| N1···H5 | 2.5900 | H8B···H10Eviii | 2.3400 |
| N2···H16 | 2.5500 | H8B···H4ii | 2.5300 |
| N2···H5 | 2.7600 | H10B···H10Cviii | 2.2900 |
| N3···HN2vi | 2.05 (2) | H10C···O1A | 2.7200 |
| N3···H16vi | 2.7400 | H10C···H10Bix | 2.2900 |
| C1···C14i | 3.483 (6) | H10C···C10Aix | 3.0100 |
| C1···O2v | 3.295 (5) | H10E···C8Bix | 3.0800 |
| C2···C13i | 3.574 (6) | H10E···O1B | 2.8500 |
| C2···Br1vii | 3.679 (4) | H10E···H8Bix | 2.3400 |
| C3···Br1vii | 3.669 (4) | H13···O2 | 2.5200 |
| C5···N2 | 3.113 (5) | H14···S1Avii | 3.1300 |
| C7···O2 | 3.141 (5) | H14···S1Bvii | 3.1500 |
| C9A···O2 | 3.102 (15) | H15···O1Biii | 2.4700 |
| C9B···O2 | 3.39 (2) | H15···S1Bvii | 3.0700 |
| C11···O1A | 3.32 (2) | H15···O1Aiii | 2.3800 |
| C11···O1B | 3.38 (3) | H16···N2 | 2.5500 |
| C13···C13iii | 3.380 (6) | H16···N3iv | 2.7400 |
| C13···C2vii | 3.574 (6) | H16···O1Bvi | 2.5700 |
| C14···S1Bvii | 3.679 (11) | H16···HN2 | 2.1800 |
| C7—S1A—C8A | 91.0 (4) | C11—C12—C13 | 118.4 (4) |
| C7—S1B—C8B | 96.9 (6) | C12—C13—C14 | 119.5 (4) |
| N2—N1—C9A | 120.3 (6) | C13—C14—C15 | 118.7 (4) |
| N2—N1—C9B | 118.3 (9) | N3—C15—C14 | 123.7 (4) |
| C7—N1—C9A | 113.5 (7) | N3—C16—C12 | 123.7 (4) |
| C7—N1—C9B | 121.9 (9) | C2—C1—H1 | 120.00 |
| N2—N1—C7 | 118.9 (3) | C6—C1—H1 | 120.00 |
| N1—N2—C11 | 118.9 (3) | C1—C2—H2A | 120.00 |
| C15—N3—C16 | 117.1 (4) | C3—C2—H2A | 120.00 |
| C11—N2—HN2 | 132 (3) | C3—C4—H4 | 120.00 |
| N1—N2—HN2 | 108 (3) | C5—C4—H4 | 120.00 |
| C2—C1—C6 | 120.8 (4) | C4—C5—H5 | 120.00 |
| C1—C2—C3 | 119.7 (4) | C6—C5—H5 | 120.00 |
| Br1—C3—C4 | 120.6 (4) | S1A—C7—H7 | 107.00 |
| Br1—C3—C2 | 118.9 (3) | N1—C7—H7 | 106.00 |
| C2—C3—C4 | 120.5 (4) | C6—C7—H7 | 106.00 |
| C3—C4—C5 | 119.7 (4) | S1B—C7—H7 | 123.00 |
| C4—C5—C6 | 120.6 (4) | S1A—C8A—H8A | 107.00 |
| C1—C6—C7 | 118.9 (4) | C9A—C8A—H8A | 107.00 |
| C1—C6—C5 | 118.7 (4) | C10A—C8A—H8A | 107.00 |
| C5—C6—C7 | 122.5 (3) | C9B—C8B—H8B | 109.00 |
| N1—C7—C6 | 114.7 (3) | C10B—C8B—H8B | 109.00 |
| S1A—C7—C6 | 115.0 (4) | S1B—C8B—H8B | 109.00 |
| S1B—C7—N1 | 97.9 (4) | C8A—C10A—H10C | 109.00 |
| S1B—C7—C6 | 108.1 (4) | H10A—C10A—H10B | 110.00 |
| S1A—C7—N1 | 107.0 (4) | H10B—C10A—H10C | 110.00 |
| S1A—C8A—C9A | 107.6 (7) | C8A—C10A—H10B | 109.00 |
| C9A—C8A—C10A | 113.8 (11) | H10A—C10A—H10C | 109.00 |
| S1A—C8A—C10A | 114.4 (9) | C8A—C10A—H10A | 109.00 |
| S1B—C8B—C10B | 115.7 (11) | H10D—C10B—H10F | 110.00 |
| C9B—C8B—C10B | 110.7 (15) | C8B—C10B—H10D | 109.00 |
| S1B—C8B—C9B | 104.1 (9) | C8B—C10B—H10E | 109.00 |
| N1—C9A—C8A | 113.0 (8) | C8B—C10B—H10F | 110.00 |
| O1A—C9A—C8A | 123.3 (11) | H10D—C10B—H10E | 109.00 |
| O1A—C9A—N1 | 123.6 (14) | H10E—C10B—H10F | 110.00 |
| N1—C9B—C8B | 112.8 (14) | C14—C13—H13 | 120.00 |
| O1B—C9B—C8B | 125.6 (15) | C12—C13—H13 | 120.00 |
| O1B—C9B—N1 | 121.5 (17) | C15—C14—H14 | 121.00 |
| O2—C11—N2 | 122.9 (4) | C13—C14—H14 | 121.00 |
| O2—C11—C12 | 121.6 (4) | N3—C15—H15 | 118.00 |
| N2—C11—C12 | 115.5 (4) | C14—C15—H15 | 118.00 |
| C13—C12—C16 | 117.3 (3) | C12—C16—H16 | 118.00 |
| C11—C12—C16 | 124.3 (4) | N3—C16—H16 | 118.00 |
| C8A—S1A—C7—N1 | −26.3 (7) | C2—C3—C4—C5 | 0.4 (6) |
| C8A—S1A—C7—C6 | −154.9 (6) | Br1—C3—C4—C5 | 179.4 (3) |
| C7—S1A—C8A—C9A | 19.9 (12) | C3—C4—C5—C6 | 0.9 (6) |
| C7—S1A—C8A—C10A | 147.4 (10) | C4—C5—C6—C7 | −179.6 (4) |
| C7—N1—N2—C11 | −75.1 (4) | C4—C5—C6—C1 | −1.1 (6) |
| C9A—N1—N2—C11 | 73.1 (11) | C5—C6—C7—N1 | −24.1 (5) |
| C9A—N1—C7—S1A | 26.8 (10) | C5—C6—C7—S1A | 100.6 (5) |
| N2—N1—C7—C6 | −54.3 (5) | C1—C6—C7—N1 | 157.4 (3) |
| C9A—N1—C7—C6 | 155.5 (9) | C1—C6—C7—S1A | −77.9 (5) |
| C7—N1—C9A—C8A | −12.1 (17) | C10A—C8A—C9A—N1 | −136.2 (13) |
| N2—N1—C9A—O1A | 23 (3) | S1A—C8A—C9A—N1 | −8.3 (18) |
| C7—N1—C9A—O1A | 172.4 (18) | C10A—C8A—C9A—O1A | 39 (3) |
| N2—N1—C9A—C8A | −161.9 (10) | S1A—C8A—C9A—O1A | 167 (2) |
| N2—N1—C7—S1A | 177.0 (4) | N2—C11—C12—C13 | 172.2 (3) |
| N1—N2—C11—O2 | 1.2 (6) | O2—C11—C12—C13 | −9.0 (6) |
| N1—N2—C11—C12 | 180.0 (3) | O2—C11—C12—C16 | 169.8 (4) |
| C16—N3—C15—C14 | −0.5 (6) | N2—C11—C12—C16 | −9.0 (5) |
| C15—N3—C16—C12 | 1.6 (6) | C16—C12—C13—C14 | 1.0 (6) |
| C2—C1—C6—C7 | 178.5 (3) | C11—C12—C16—N3 | 179.2 (4) |
| C2—C1—C6—C5 | 0.0 (6) | C11—C12—C13—C14 | 180.0 (4) |
| C6—C1—C2—C3 | 1.3 (6) | C13—C12—C16—N3 | −1.9 (6) |
| C1—C2—C3—C4 | −1.5 (6) | C12—C13—C14—C15 | −0.1 (6) |
| C1—C2—C3—Br1 | 179.5 (3) | C13—C14—C15—N3 | −0.2 (6) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—HN2···N3iv | 0.861 (19) | 2.05 (2) | 2.899 (5) | 167 (4) |
| C1—H1···O2v | 0.93 | 2.47 | 3.295 (5) | 149 |
| C5—H5···N1 | 0.93 | 2.59 | 2.903 (5) | 100 |
| C15—H15···O1Aiii | 0.93 | 2.38 | 3.062 (16) | 130 |
| C16—H16···N2 | 0.93 | 2.55 | 2.861 (5) | 100 |
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