organic papers
Acta Cryst.(2004). E60, o1507±o1509 DOI: 10.1107/S1600536804019099 Mehmet Akkurtet al. C15H13N3S
o1507
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
5-Benzyl-4-phenyl-2,4-dihydro-1,2,4-triazole-3-thione
Mehmet Akkurt,aSema
OÈ ztuÈrk,a* SuÈleyman Servi,b Ahmet Cansõz,bMemet SËekercib and Canan Kazakc
aDepartment of Physics, Faculty of Arts and
Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, Faculty of
Arts and Sciences, Fõrat University, 23119 ElazõgÆ, Turkey, andcDepartment of Physics,
Faculty of Arts and Sciences, Ondokuz Mayõs University, 55139 Kurupelit, Samsun, Turkey
Correspondence e-mail: ozturk@erciyes.edu.tr
Key indicators
Single-crystal X-ray study
T= 296 K
Mean(C±C) = 0.003 AÊ
Rfactor = 0.039
wRfactor = 0.096
Data-to-parameter ratio = 17.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
As part of structural studies of 1,2,4-triazole derivatives, the crystal structure of the title compound, C15H13N3S, has been
investigated. The structure shows a V-shape in the molecular skeleton, as found for similar compounds. The crystal structure is stabilized by an NÐH S and three CÐH
intermolecular interactions.
Comment
Derivatives of 1,2,4-triazole are known to exhibit anti-in¯ammatory (Unangst et al., 1992; Mullican et al., 1993), antiviral (Jones et al., 1965), analgesic (Sughen & Yoloye, 1978), antimicrobial (Shams El-Dine & Hazzaa, 1974; Misato
et al., 1977; Cansõzet al., 2001), anticonvulsant (Stillingset al., 1986) and antidepressant activities (Kaneet al., 1988), the last of these usually being explored by the forced swim test (Porsolt et al., 1977; Vamvakides, 1990). Among the pharma-cological pro®les of 1,2,4-triazoles, their antimicrobial, anti-convulsant and antidepressant properties seem to be the best documented. The derivatives of 4,5-disubstituted 1,2,4-triazole are synthesized by intramolecular cyclization of 1,4-disub-stitued thiosemicarbazides (Zamaniet al., 2003; Cansõzet al., 2004). In addition, there are some studies on electronic structures and the thiol±thione tautomeric equilibrium of heterocyclic thione derivatives (AydogÄan et al., 2002; Char-istoset al., 1994). In this context, we have synthesized several new compounds, including the title compound, (I) (Fig. 1).
The N C [1.296 (2) AÊ] and S C distances [1.6717 (15) AÊ] are comparable to those observed in related structures (OÈztuÈrk et al., 2004a,b). The title compound contains three planar rings. One is the triazole ring (ringA; N1, C7, N2, N3 and C8); the others are ringsB(C1±C6) andC(C10±C15). The dihedral angles between these rings are 69.7 (1) for A/B,
82.0 (1) forA/Cand 34.5 (1)forB/C.
In the crystal structure of (I), the molecules are linked by NÐH S and CÐH interactions, resulting in a network structure (Fig. 2); details of these interactions are listed in Table 2.
Experimental
A stirred mixture of 1-benzyl-4-phenylthiosemicarbazide (1 mmol) and sodium hydroxide (40 mg, 1 mmol, as a 2Nsolution) was re¯uxed for 4 h. After cooling, the solution was acidi®ed with hydrochloric acid and the precipitate was ®ltered off and crystallized from an ethanol±dioxane mixture (yield 79%; m.p. 470 K). IR (cmÿ1): 2560
(SH), 1606 (C N), 1535, 1260, 1050, 950 (NÐC S, amide I, II, III and IV bands);1H NMR:3.80 (s, 2H, ±CH
2), 7.45±7.10 (m, 10H,
Ar-H), 13.92 (s, 1H, SH or NH).
Crystal data
C15H13N3S
Mr= 267.35 Monoclinic,P21=n
a= 7.0467 (5) AÊ
b= 17.6802 (13) AÊ
c= 11.2725 (7) AÊ
= 104.355 (5) V= 1360.56 (17) AÊ3
Z= 4
Dx= 1.305 Mg mÿ3 MoKradiation Cell parameters from 2998
re¯ections
= 2.2±27.2
= 0.23 mmÿ1
T= 296 K Prism, colorless 0.450.350.25 mm
Data collection
Stoe IPDS-II diffractometer
!scans
21 276 measured re¯ections 2998 independent re¯ections 2023 re¯ections withI> 2(I)
Rint= 0.109
max= 27.1
h=ÿ8!9
k=ÿ22!22
l=ÿ14!14
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.039
wR(F2) = 0.096
S= 0.89 2998 re¯ections 173 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0538P)2] whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.33 e AÊÿ3
min=ÿ0.20 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.012 (2)
Table 1
Selected geometric parameters (AÊ,).
S1ÐC7 1.6717 (15) N1ÐC1 1.439 (2) N1ÐC7 1.379 (2) N1ÐC8 1.381 (2)
N2ÐN3 1.372 (2) N2ÐC7 1.338 (2) N3ÐC8 1.296 (2)
C1ÐN1ÐC7 125.22 (13) C1ÐN1ÐC8 126.65 (13) C7ÐN1ÐC8 108.11 (13) N3ÐN2ÐC7 114.01 (13) N2ÐN3ÐC8 104.21 (13) N1ÐC1ÐC2 119.66 (14) N1ÐC1ÐC6 119.33 (14)
N1ÐC7ÐN2 102.86 (13) S1ÐC7ÐN2 128.90 (12) S1ÐC7ÐN1 128.23 (12) N1ÐC8ÐC9 124.56 (16) N1ÐC8ÐN3 110.81 (14) N3ÐC8ÐC9 124.63 (16)
C7ÐN1ÐC1ÐC6 110.66 (18) C8ÐN1ÐC1ÐC6 ÿ70.4 (2) C1ÐN1ÐC8ÐC9 0.7 (3) C7ÐN1ÐC8ÐC9 179.79 (16) C8ÐN1ÐC7ÐS1 178.35 (12)
C1ÐN1ÐC7ÐS1 ÿ2.6 (2) N2ÐN3ÐC8ÐC9 ÿ179.59 (16) C8ÐC9ÐC10ÐC15 120.92 (19) C8ÐC9ÐC10ÐC11 ÿ61.2 (2)
Table 2
Hydrogen-bonding geometry (AÊ,).
Cg1 andCg2 denote the centroids of the triazole and benzyl rings.
DÐH A DÐH H A D A DÐH A
N2ÐH22 S1i 0.86 2.45 3.293 (2) 166
C4ÐH4 Cg1ii 0.93 2.95 3.715 (2) 141
C12ÐH12 Cg1iii 0.93 2.98 3.796 (2) 147
C14ÐH14 Cg2iv 0.93 2.99 3.603 (2) 125
Symmetry codes: (i) 1ÿx;ÿy;ÿz; (ii)1
2x;12ÿy;12z; (iii) 1ÿx;ÿy;1ÿz; (iv) xÿ1
2;12ÿy;12z.
All H atoms were positioned geometrically and re®ned using a riding model, with aromatic CÐH distances of 0.93 AÊ, methylene CÐ H distances of 0.97 AÊ and a triazole NÐH distance of 0.86 AÊ.Uiso(H)
values were set at 1.2Ueqof the carrier atom.
Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:
X-AREA; data reduction:X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s)
used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular
graphics: ORTEP-3 (Farrugia, 1997); software used to prepare
material for publication:WinGX(Farrugia, 1999).
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayõs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant F.279 of the University Research Fund).
organic papers
o1508
Mehmet Akkurtet al. C15H13N3S Acta Cryst.(2004). E60, o1507±o1509Figure 2
A view of the hydrogen-bonded dimer in the crystal structure of (I).
Dashed lines indicate hydrogen bonds. [Symmetry code: (i) 1ÿx,ÿy,
ÿz].
Figure 1
References
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Cansõz, A., Koparõr, M. & DemirdagÄ, A. (2004).Molecules,9, 204±212. Cansõz, A., Servi, S., Koparõr, M., AltõntasË, M. & DõgÄrak, M. (2001).J. Chem.
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OÈztuÈrk, S., Akkurt, M., Cansõz, A., Koparõr, M., SËekerci, M. & Heinemann, F. W. (2004a).Acta Cryst.E60, o425±o427.
OÈztuÈrk, S., Akkurt, M., Cansõz, A., Koparõr, M., SËekerci, M. & Heinemann, F. W. (2004b).Acta Cryst.E60, o642±o644.
Porsolt, R. D., Bertin, A. & Jalfre, M. (1977).Arch. Int. Pharmacol.229, 327± 336.
Shams El-Dine, S. A. & Hazzaa, A. A. B. (1974). Pharmazie, 29, 761± 768.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Stillings, M. R., Welbourn, A. & Walter, D. S. (1986).J. Med. Chem.29, 2280± 2284.
Stoe & Cie (2002).X-AREA(Version 1.18) andX-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.
Sughen, J. K. & Yoloye, T. (1978).Pharm. Acta Helv.58, 64±68.
Unangst, P. C., Shurum, G. P., Connor, D. T., Dyer, R. D. & Schrier, D. J. (1992).
J. Med. Chem.35, 3691±3698.
Vamvakides, A. (1990).Pharm. Fr.48, 154±159.
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organic papers
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sup-1 Acta Cryst. (2004). E60, o1507–o1509
supporting information
Acta Cryst. (2004). E60, o1507–o1509 [https://doi.org/10.1107/S1600536804019099]
5-Benzyl-4-phenyl-2,4-dihydro-1,2,4-triazole-3-thione
Mehmet Akkurt, Sema
Ö
zt
ü
rk, S
ü
leyman Servi, Ahmet Cans
ı
z, Memet
Ş
ekerci and Canan Kazak
5-Benzyl-4-phenyl-2,4-dihydro-1,2,4-triazole-3-thione
Crystal data
C15H13N3S
Mr = 267.35
Monoclinic, P21/n Hall symbol: -P 2yn
a = 7.0467 (5) Å
b = 17.6802 (13) Å
c = 11.2725 (7) Å
β = 104.355 (5)°
V = 1360.56 (17) Å3
Z = 4
F(000) = 560
Dx = 1.305 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2998 reflections
θ = 2.2–27.2°
µ = 0.23 mm−1
T = 296 K Prism, colorless 0.45 × 0.35 × 0.25 mm
Data collection
Stoe IPDS-II diffractometer
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus
Plane graphite monochromator Detector resolution: 6.67 pixels mm-1
ω scans
21276 measured reflections
2998 independent reflections 2023 reflections with I > 2σ(I)
Rint = 0.109
θmax = 27.1°, θmin = 2.2°
h = −8→9
k = −22→22
l = −14→14
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.039
wR(F2) = 0.096
S = 0.89 2998 reflections 173 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001
Δρmax = 0.33 e Å−3 Δρmin = −0.20 e Å−3
Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 Extinction coefficient: 0.012 (2)
Special details
supporting information
sup-2 Acta Cryst. (2004). E60, o1507–o1509
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. WeightedR-factorswRand all goodnesses of fitSare based on
F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion ofF2 > σ(F2) is used only for calculating
-R-factor-obsetc. and is not relevant to the choice of reflections for refinement.R-factors based onF2 are statistically about twice as large as those based on F, and
R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
S1 0.59031 (6) 0.12047 (2) 0.06279 (4) 0.0448 (2)
N1 0.31980 (18) 0.12316 (7) 0.20129 (12) 0.0361 (4)
N2 0.3003 (2) 0.02542 (8) 0.08932 (13) 0.0450 (5)
N3 0.1540 (2) 0.01749 (8) 0.14915 (14) 0.0487 (5)
C1 0.3819 (2) 0.19360 (9) 0.26258 (14) 0.0367 (5)
C2 0.5575 (2) 0.19735 (10) 0.34849 (15) 0.0435 (5)
C3 0.6167 (3) 0.26540 (11) 0.40688 (17) 0.0522 (6)
C4 0.4989 (3) 0.32831 (11) 0.37930 (19) 0.0581 (7)
C5 0.3236 (3) 0.32383 (11) 0.2937 (2) 0.0598 (7)
C6 0.2637 (3) 0.25627 (10) 0.23384 (17) 0.0482 (6)
C7 0.4051 (2) 0.08890 (9) 0.11751 (13) 0.0358 (5)
C8 0.1685 (2) 0.07759 (10) 0.21668 (15) 0.0413 (5)
C9 0.0410 (3) 0.09483 (12) 0.30001 (17) 0.0504 (6)
C10 0.1453 (2) 0.09751 (10) 0.43353 (16) 0.0431 (5)
C11 0.2409 (3) 0.03485 (11) 0.4927 (2) 0.0571 (7)
C12 0.3288 (3) 0.03720 (14) 0.6163 (2) 0.0672 (8)
C13 0.3211 (3) 0.10145 (15) 0.6827 (2) 0.0684 (9)
C14 0.2284 (3) 0.16446 (14) 0.6246 (2) 0.0684 (8)
C15 0.1426 (3) 0.16243 (11) 0.50140 (18) 0.0555 (7)
H2 0.63610 0.15460 0.36740 0.0520*
H3 0.73620 0.26860 0.46470 0.0630*
H4 0.53850 0.37390 0.41890 0.0700*
H5 0.24410 0.36640 0.27560 0.0720*
H6 0.14520 0.25330 0.17500 0.0580*
H9A −0.06120 0.05680 0.28850 0.0610*
H9B −0.02180 0.14330 0.27690 0.0610*
H11 0.24610 −0.00930 0.44880 0.0690*
H12 0.39400 −0.00530 0.65490 0.0810*
H13 0.37810 0.10240 0.76650 0.0820*
H14 0.22380 0.20850 0.66880 0.0820*
H15 0.08130 0.20560 0.46270 0.0670*
H22 0.32260 −0.00750 0.03820 0.0540*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
S1 0.0532 (3) 0.0388 (2) 0.0459 (3) −0.0015 (2) 0.0187 (2) −0.0084 (2)
N1 0.0423 (7) 0.0319 (7) 0.0337 (7) 0.0009 (5) 0.0087 (5) −0.0056 (5)
N2 0.0608 (9) 0.0335 (8) 0.0432 (8) −0.0031 (6) 0.0177 (7) −0.0110 (6)
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sup-3 Acta Cryst. (2004). E60, o1507–o1509
C1 0.0464 (9) 0.0327 (8) 0.0323 (8) −0.0004 (6) 0.0124 (7) −0.0063 (6)
C2 0.0480 (9) 0.0416 (9) 0.0400 (9) 0.0039 (7) 0.0091 (7) −0.0053 (7)
C3 0.0546 (10) 0.0570 (12) 0.0422 (10) −0.0079 (9) 0.0067 (8) −0.0140 (8)
C4 0.0726 (13) 0.0445 (11) 0.0581 (12) −0.0076 (9) 0.0178 (10) −0.0210 (9)
C5 0.0724 (13) 0.0370 (10) 0.0687 (13) 0.0114 (9) 0.0152 (11) −0.0108 (9)
C6 0.0522 (10) 0.0435 (10) 0.0456 (10) 0.0071 (8) 0.0059 (8) −0.0082 (8)
C7 0.0454 (8) 0.0301 (8) 0.0301 (8) 0.0045 (6) 0.0058 (6) −0.0042 (6)
C8 0.0435 (8) 0.0412 (10) 0.0379 (9) −0.0017 (7) 0.0075 (7) −0.0043 (7)
C9 0.0440 (9) 0.0610 (12) 0.0485 (10) −0.0016 (8) 0.0157 (8) −0.0043 (9)
C10 0.0415 (8) 0.0477 (10) 0.0439 (9) −0.0013 (7) 0.0178 (7) −0.0024 (7)
C11 0.0643 (12) 0.0470 (11) 0.0625 (13) 0.0065 (9) 0.0202 (10) 0.0008 (9)
C12 0.0671 (12) 0.0701 (15) 0.0641 (14) 0.0147 (10) 0.0159 (10) 0.0217 (12)
C13 0.0654 (13) 0.0965 (19) 0.0441 (11) 0.0001 (11) 0.0149 (9) 0.0037 (11)
C14 0.0840 (15) 0.0734 (15) 0.0510 (12) 0.0040 (12) 0.0226 (11) −0.0155 (11)
C15 0.0662 (12) 0.0524 (12) 0.0518 (11) 0.0116 (9) 0.0218 (9) −0.0023 (9)
Geometric parameters (Å, º)
S1—C7 1.6717 (15) C10—C11 1.380 (3)
N1—C1 1.439 (2) C11—C12 1.378 (3)
N1—C7 1.379 (2) C12—C13 1.369 (3)
N1—C8 1.381 (2) C13—C14 1.373 (3)
N2—N3 1.372 (2) C14—C15 1.371 (3)
N2—C7 1.338 (2) C2—H2 0.9300
N3—C8 1.296 (2) C3—H3 0.9300
N2—H22 0.8605 C4—H4 0.9301
C1—C6 1.376 (2) C5—H5 0.9302
C1—C2 1.371 (2) C6—H6 0.9302
C2—C3 1.385 (3) C9—H9A 0.9702
C3—C4 1.377 (3) C9—H9B 0.9700
C4—C5 1.368 (3) C11—H11 0.9298
C5—C6 1.385 (3) C12—H12 0.9305
C8—C9 1.484 (3) C13—H13 0.9305
C9—C10 1.503 (3) C14—H14 0.9293
C10—C15 1.382 (3) C15—H15 0.9306
S1···C2 3.5556 (17) C6···H3iii 3.0239
S1···C9i 3.638 (2) C6···H9B 2.9592
S1···N2ii 3.2928 (15) C7···H12viii 2.9950
S1···H9Bi 3.1919 C7···H4iii 3.0415
S1···H22ii 2.4512 C8···H11 2.9658
S1···H3iii 3.1508 C12···H9Aix 2.9108
N1···N3 2.2046 (19) C13···H5v 2.9592
N2···N1 2.1242 (19) H3···S1v 3.1508
N2···S1ii 3.2928 (15) H3···C6v 3.0239
N3···N1 2.2046 (19) H4···N3x 2.8909
N2···H4iii 2.9163 H4···N2v 2.9163
supporting information
sup-4 Acta Cryst. (2004). E60, o1507–o1509
N3···H5iv 2.8406 H5···N3x 2.8406
C1···C10 3.313 (2) H5···C13iii 2.9592
C1···C15 3.556 (3) H6···C3iii 2.9972
C2···S1 3.5556 (17) H9A···C12ix 2.9108
C3···C6v 3.593 (3) H9B···S1vi 3.1919
C6···C3iii 3.593 (3) H9B···C1 3.0228
C6···C9 3.427 (3) H9B···C6 2.9592
C9···S1vi 3.638 (2) H9B···H15 2.3180
C9···C6 3.427 (3) H11···C8 2.9658
C10···C1 3.313 (2) H12···C7viii 2.9950
C15···C1 3.556 (3) H14···C2xi 3.0699
C1···H9B 3.0228 H14···C3xi 2.9982
C2···H14vii 3.0699 H15···H9B 2.3180
C3···H14vii 2.9982 H22···S1ii 2.4512
C3···H6v 2.9972
C1—N1—C7 125.22 (13) C13—C14—C15 120.0 (2)
C1—N1—C8 126.65 (13) C10—C15—C14 121.29 (19)
C7—N1—C8 108.11 (13) C1—C2—H2 120.30
N3—N2—C7 114.01 (13) C3—C2—H2 120.33
N2—N3—C8 104.21 (13) C2—C3—H3 119.97
N3—N2—H22 122.98 C4—C3—H3 119.98
C7—N2—H22 123.01 C3—C4—H4 119.97
N1—C1—C2 119.66 (14) C5—C4—H4 119.97
C2—C1—C6 121.01 (16) C4—C5—H5 119.81
N1—C1—C6 119.33 (14) C6—C5—H5 119.78
C1—C2—C3 119.37 (16) C1—C6—H6 120.43
C2—C3—C4 120.05 (18) C5—C6—H6 120.48
C3—C4—C5 120.06 (18) C8—C9—H9A 108.60
C4—C5—C6 120.41 (19) C8—C9—H9B 108.61
C1—C6—C5 119.09 (18) C10—C9—H9A 108.56
N1—C7—N2 102.86 (13) C10—C9—H9B 108.56
S1—C7—N2 128.90 (12) H9A—C9—H9B 107.59
S1—C7—N1 128.23 (12) C10—C11—H11 119.72
N1—C8—C9 124.56 (16) C12—C11—H11 119.76
N1—C8—N3 110.81 (14) C11—C12—H12 119.64
N3—C8—C9 124.63 (16) C13—C12—H12 119.76
C8—C9—C10 114.71 (16) C12—C13—H13 120.29
C9—C10—C11 121.18 (17) C14—C13—H13 120.28
C11—C10—C15 118.12 (17) C13—C14—H14 119.99
C9—C10—C15 120.67 (17) C15—C14—H14 119.99
C10—C11—C12 120.52 (19) C10—C15—H15 119.35
C11—C12—C13 120.6 (2) C14—C15—H15 119.36
C12—C13—C14 119.4 (2)
C1—N1—C7—N2 178.73 (14) C2—C1—C6—C5 −0.5 (3)
C7—N1—C1—C2 −69.3 (2) C6—C1—C2—C3 −0.2 (3)
supporting information
sup-5 Acta Cryst. (2004). E60, o1507–o1509
C7—N1—C1—C6 110.66 (18) C2—C3—C4—C5 −0.3 (3)
C8—N1—C1—C6 −70.4 (2) C3—C4—C5—C6 −0.3 (3)
C7—N1—C8—N3 0.26 (18) C4—C5—C6—C1 0.7 (3)
C1—N1—C8—C9 0.7 (3) N3—C8—C9—C10 115.7 (2)
C7—N1—C8—C9 179.79 (16) N1—C8—C9—C10 −63.8 (2)
C8—N1—C7—S1 178.35 (12) C8—C9—C10—C15 120.92 (19)
C8—N1—C7—N2 −0.34 (16) C8—C9—C10—C11 −61.2 (2)
C1—N1—C7—S1 −2.6 (2) C9—C10—C15—C14 176.58 (19)
C1—N1—C8—N3 −178.79 (14) C9—C10—C11—C12 −177.24 (19)
C7—N2—N3—C8 −0.17 (19) C15—C10—C11—C12 0.8 (3)
N3—N2—C7—S1 −178.35 (12) C11—C10—C15—C14 −1.4 (3)
N3—N2—C7—N1 0.32 (17) C10—C11—C12—C13 0.7 (3)
N2—N3—C8—N1 −0.06 (18) C11—C12—C13—C14 −1.4 (3)
N2—N3—C8—C9 −179.59 (16) C12—C13—C14—C15 0.8 (3)
N1—C1—C6—C5 179.58 (17) C13—C14—C15—C10 0.7 (3)
N1—C1—C2—C3 179.80 (15)
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x+1/2, −y+1/2, z+1/2; (vi) x−1, y, z; (vii) x+1/2, −y+1/2, z−1/2; (viii) −x+1, −y, −z+1; (ix) −x, −y, −z+1; (x) −x+1/2, y+1/2, −z+1/2; (xi) x−1/2, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N2—H22···S1ii 0.86 2.45 3.293 (2) 166
C4—H4···Cg1v 0.93 2.95 3.715 (2) 141
C12—H12···Cg1viii 0.93 2.98 3.796 (2) 147
C14—H14···Cg2xi 0.93 2.99 3.603 (2) 125