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5 Benzyl 4 phenyl 2,4 di­hydro 1,2,4 triazole 3 thione

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Acta Cryst.(2004). E60, o1507±o1509 DOI: 10.1107/S1600536804019099 Mehmet Akkurtet al. C15H13N3S

o1507

Acta Crystallographica Section E

Structure 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.

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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

2‡x;12ÿy;12‡z; (iii) 1ÿx;ÿy;1ÿz; (iv) xÿ1

2;12ÿy;12‡z.

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±o1509

Figure 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

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References

AydogÄan, F., Turgut, Z., Olcay, N. & Erdem, S. S. (2002).Turk. J. Chem.26, 159±169.

Cansõz, A., Koparõr, M. & DemirdagÄ, A. (2004).Molecules,9, 204±212. Cansõz, A., Servi, S., Koparõr, M., AltõntasË, M. & DõgÄrak, M. (2001).J. Chem.

Soc. Pak.23, 237±239.

Charistos, D. D., Vagenes, G. V., Tzavellas, L. C., Tsoleridis, C. A. & Rodios, N. A. (1994).J. Heterocycl. Chem.31, 1593±1598.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837±838.

Jones, D. H., Slack, R., Squires, S. & Wooldridge, K. R. H. (1965).J. Med. Chem.8, 676±680.

Kane, J. M., Dudley, M. W., Sorensen, S. M. & Miller, F. P. (1988).J. Med. Chem.31, 1253±1258.

Misato, T., Ko, K., Honma, Y., Konno, K. & Taniyama, E. (1977).Chem. Abst.

87, 147054a; Japanese Patent 77 25028(A01N 9/12).

Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993).J. Med. Chem.36, 1090±1099.

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.

Zamani, K., Faghihi, K., Sangi, M. R. & Zolgharnein, J. (2003).Turk. J. Chem.

27, 119±125.

organic papers

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supporting information

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 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

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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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supporting information

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

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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)

(8)

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

References

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