rac-3-{4-[(4-Nitro­benzyl­idene)amino]-3-phenyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl­propan-1-one

Wang, W.; Gao, Y.; Xu, C.; Wu, W.; Liu, Q.

doi:10.1107/S1600536811035197

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2727

https://doi.org/10.1107/S1600536811035197

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rac-3-{4-[(4-Nitrobenzylidene)amino]-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenylpropan-1-one

Wei Wang,^a,^b ^* Yan Gao,^b Chao Xu,^b Wen-peng Wu ^b and Qing-lei Liu ^a

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 6 August 2011; accepted 29 August 2011; online 30 September 2011)

In the title molecule, C₃₀H₂₃N₅O₃S, the 1,2,4-triazole ring is approximately planar (r.m.s. deviation = 0.006 Å), and forms dihedral angles of 66.0 (2), 65.1 (2), 30.1 (2) and 28.1 (2)° with the four phenyl rings. The phenyl ring of the benzyl group directly attached to the triazole ring is almost perpendicular to the nitrophenyl ring, making a dihedral angle of 84.9 (2)°.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ); Fun et al. (2009 ); Gao et al. (2011 ); Tan et al. (2010 ); Wang et al. (2011 ); Zhao et al. (2010 ).

Experimental

Crystal data

C₃₀H₂₃N₅O₃S
M_r = 533.59
Monoclinic, P 2₁ /c
a = 13.3303 (13) Å
b = 21.832 (2) Å
c = 9.2773 (9) Å
β = 98.213 (3)°
V = 2672.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.968, T_max = 0.981
27241 measured reflections
6372 independent reflections
5124 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.131
S = 1.10
6372 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035197/zs2140sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035197/zs2140Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035197/zs2140Isup3.cml

checkCIF report

Comment top

In a continuation of the structural study by our group of Mannich base derivatives synthesized by the reaction of amino heterocycles and aromatic aldehydes (Wang et al., 2011), we present here the crystal structure of the title compound, C₃₀H₂₃N₅O₃S.

In this compound the bond lengths and angles are comparable with those reported in the related 1,2,4-triazole-5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). The 1,2,4-triazole ring is planar with an r.m.s 0.0055 (2) Å and a maximium deviation of 0.0083 (2) Å for atom N3. The C1 and C2 atoms of the 1,2,4-triazole ring show distorted C_sp² hybridization states with bond angles of 102.69 (13)° (N1—C1—N3); 131.16 (12)° (N3—C1—S1); 110.38 (13)° (N2—C2—N3) and 126.98 (14)° (N3—C2—C25), which are similar to those in the other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 114.0 (2), 114.9 (2), 151.9 (2)° and 149.9 (2)° with the phenyl rings C6—C11, C12—C17 and C25—C30 and the nitrophenyl ring C19—C24. The phenyl ring of the benzyl group attached to atom N1 of the triazole ring (C12—C17) is almost perpendicular to the nitrophenyl ring, with a dihedral angle of 95.1 (2)°.

Related literature top

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010); Fun et al. (2009); Gao et al. (2011); Tan et al. (2010); Wang et al. (2011); Zhao et al. (2010).

Experimental top

The title compound was synthesized in the reaction of 4-nitrobenzaldehyde (2.0 mmol) and 3-(4-amino-3-phenyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one (2.0 mmol), by refluxing in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 66% yield. Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform–ethanol (1:1).

Structure description top

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010); Fun et al. (2009); Gao et al. (2011); Tan et al. (2010); Wang et al. (2011); Zhao et al. (2010).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of a molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

rac-3-{4-[(4-Nitrobenzylidene)amino]-3-phenyl-5-sulfanylidene- 4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenylpropan-1-one top

Crystal data top

C₃₀H₂₃N₅O₃S	F(000) = 1112
M_r = 533.59	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8592 reflections
a = 13.3303 (13) Å	θ = 1.5–27.9°
b = 21.832 (2) Å	µ = 0.16 mm⁻¹
c = 9.2773 (9) Å	T = 113 K
β = 98.213 (3)°	Prism, colorless
V = 2672.2 (4) Å³	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	6372 independent reflections
Radiation source: rotating anode	5124 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.040
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.5°
φ and ω scans	h = −15→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −27→28
T_min = 0.968, T_max = 0.981	l = −12→12
27241 measured reflections

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0667P)² + 0.1147P] where P = (F_o² + 2F_c²)/3
6372 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₃₀H₂₃N₅O₃S	V = 2672.2 (4) Å³
M_r = 533.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3303 (13) Å	µ = 0.16 mm⁻¹
b = 21.832 (2) Å	T = 113 K
c = 9.2773 (9) Å	0.20 × 0.18 × 0.12 mm
β = 98.213 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	6372 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	5124 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.981	R_int = 0.040
27241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.10	Δρ_max = 0.33 e Å⁻³
6372 reflections	Δρ_min = −0.25 e Å⁻³
352 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.40778 (3)	0.258871 (19)	0.46718 (5)	0.03324 (14)
O1	0.33880 (9)	0.08657 (5)	0.76721 (14)	0.0346 (3)
O2	−0.05157 (12)	0.41949 (7)	−0.22517 (19)	0.0649 (5)
O3	−0.07948 (10)	0.33342 (7)	−0.34027 (17)	0.0545 (4)
N1	0.41855 (9)	0.13669 (6)	0.49993 (14)	0.0250 (3)
N2	0.37677 (10)	0.08227 (6)	0.44644 (15)	0.0273 (3)
N3	0.30586 (9)	0.16063 (6)	0.32011 (14)	0.0265 (3)
N4	0.23159 (10)	0.18795 (7)	0.22006 (15)	0.0305 (3)
N5	−0.03993 (11)	0.36460 (8)	−0.23724 (19)	0.0440 (4)
C1	0.37777 (12)	0.18629 (7)	0.42770 (17)	0.0258 (3)
C2	0.30761 (12)	0.09772 (7)	0.33837 (18)	0.0268 (4)
C3	0.49357 (11)	0.13916 (7)	0.63312 (17)	0.0244 (3)
H3	0.4677	0.1679	0.7033	0.029*
C4	0.50513 (11)	0.07593 (7)	0.70349 (17)	0.0252 (3)
H4A	0.5231	0.0462	0.6307	0.030*
H4B	0.5621	0.0772	0.7846	0.030*
C5	0.41174 (12)	0.05325 (7)	0.76135 (17)	0.0255 (3)
C6	0.41222 (11)	−0.01130 (7)	0.81389 (16)	0.0246 (3)
C7	0.50162 (12)	−0.04455 (7)	0.84342 (17)	0.0264 (3)
H7	0.5640	−0.0265	0.8279	0.032*
C8	0.50025 (13)	−0.10395 (7)	0.89538 (18)	0.0306 (4)
H8	0.5617	−0.1265	0.9151	0.037*
C9	0.40986 (13)	−0.13060 (8)	0.91858 (19)	0.0332 (4)
H9	0.4091	−0.1715	0.9534	0.040*
C10	0.32011 (14)	−0.09748 (8)	0.89083 (19)	0.0342 (4)
H10	0.2580	−0.1155	0.9079	0.041*
C11	0.32128 (12)	−0.03833 (8)	0.83847 (18)	0.0305 (4)
H11	0.2598	−0.0159	0.8190	0.037*
C12	0.59542 (11)	0.16257 (7)	0.60266 (17)	0.0244 (3)
C13	0.64074 (12)	0.14022 (8)	0.48742 (18)	0.0305 (4)
H13	0.6057	0.1114	0.4219	0.037*
C14	0.73711 (13)	0.15985 (8)	0.4674 (2)	0.0363 (4)
H14	0.7679	0.1442	0.3888	0.044*
C15	0.78809 (13)	0.20224 (8)	0.5621 (2)	0.0358 (4)
H15	0.8536	0.2160	0.5482	0.043*
C16	0.74310 (13)	0.22440 (8)	0.67691 (19)	0.0335 (4)
H16	0.7783	0.2532	0.7424	0.040*
C17	0.64733 (12)	0.20516 (7)	0.69740 (18)	0.0291 (4)
H17	0.6169	0.2210	0.7761	0.035*
C18	0.23453 (13)	0.24544 (9)	0.1994 (2)	0.0375 (4)
H18	0.2862	0.2696	0.2532	0.045*
C19	0.15729 (12)	0.27428 (9)	0.0914 (2)	0.0363 (4)
C20	0.09104 (13)	0.24006 (8)	−0.0091 (2)	0.0359 (4)
H20	0.0912	0.1966	−0.0037	0.043*
C21	0.02564 (13)	0.26954 (9)	−0.1159 (2)	0.0368 (4)
H21	−0.0185	0.2469	−0.1858	0.044*
C22	0.02605 (12)	0.33251 (8)	−0.1185 (2)	0.0356 (4)
C23	0.08666 (13)	0.36786 (9)	−0.0181 (2)	0.0427 (5)
H23	0.0828	0.4113	−0.0206	0.051*
C24	0.15371 (13)	0.33767 (9)	0.0872 (2)	0.0422 (5)
H24	0.1974	0.3608	0.1568	0.051*
C25	0.24185 (12)	0.05265 (8)	0.25380 (19)	0.0321 (4)
C26	0.22312 (14)	−0.00168 (8)	0.3235 (2)	0.0435 (5)
H26	0.2505	−0.0077	0.4227	0.052*
C27	0.16458 (16)	−0.04698 (9)	0.2484 (3)	0.0564 (6)
H27	0.1526	−0.0843	0.2959	0.068*
C28	0.12366 (15)	−0.03807 (10)	0.1051 (3)	0.0564 (6)
H28	0.0829	−0.0691	0.0544	0.068*
C29	0.14132 (14)	0.01515 (10)	0.0354 (2)	0.0497 (6)
H29	0.1124	0.0210	−0.0633	0.060*
C30	0.20157 (13)	0.06087 (9)	0.1082 (2)	0.0394 (5)
H30	0.2151	0.0974	0.0589	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0366 (3)	0.0258 (2)	0.0356 (3)	0.00011 (17)	−0.00091 (18)	0.00255 (18)
O1	0.0319 (6)	0.0328 (6)	0.0388 (7)	0.0046 (5)	0.0042 (5)	0.0019 (5)
O2	0.0617 (10)	0.0478 (9)	0.0783 (12)	0.0076 (8)	−0.0139 (8)	0.0202 (8)
O3	0.0449 (8)	0.0643 (10)	0.0487 (9)	0.0034 (7)	−0.0129 (7)	0.0094 (7)
N1	0.0259 (7)	0.0233 (7)	0.0240 (7)	0.0000 (5)	−0.0030 (5)	−0.0019 (5)
N2	0.0260 (7)	0.0266 (7)	0.0273 (7)	−0.0003 (5)	−0.0034 (5)	−0.0049 (6)
N3	0.0228 (7)	0.0326 (8)	0.0226 (7)	0.0029 (5)	−0.0017 (5)	0.0005 (6)
N4	0.0257 (7)	0.0405 (8)	0.0237 (7)	0.0052 (6)	−0.0020 (5)	0.0046 (6)
N5	0.0315 (8)	0.0484 (10)	0.0501 (11)	0.0016 (7)	−0.0006 (7)	0.0160 (8)
C1	0.0236 (8)	0.0310 (9)	0.0221 (8)	0.0022 (6)	0.0015 (6)	0.0023 (6)
C2	0.0232 (8)	0.0315 (9)	0.0251 (8)	0.0021 (6)	0.0010 (6)	−0.0042 (7)
C3	0.0258 (8)	0.0240 (8)	0.0217 (8)	−0.0005 (6)	−0.0020 (6)	−0.0011 (6)
C4	0.0259 (8)	0.0253 (8)	0.0230 (8)	−0.0001 (6)	−0.0017 (6)	0.0005 (6)
C5	0.0275 (8)	0.0259 (8)	0.0213 (8)	0.0014 (6)	−0.0027 (6)	−0.0023 (6)
C6	0.0281 (8)	0.0258 (8)	0.0191 (8)	−0.0018 (6)	0.0009 (6)	−0.0032 (6)
C7	0.0287 (8)	0.0267 (8)	0.0232 (8)	−0.0023 (6)	0.0018 (6)	−0.0020 (6)
C8	0.0348 (9)	0.0290 (8)	0.0274 (9)	0.0017 (7)	0.0026 (7)	−0.0002 (7)
C9	0.0447 (10)	0.0267 (8)	0.0278 (9)	−0.0052 (7)	0.0041 (7)	0.0005 (7)
C10	0.0352 (9)	0.0357 (9)	0.0321 (10)	−0.0100 (7)	0.0055 (7)	−0.0012 (8)
C11	0.0273 (8)	0.0347 (9)	0.0288 (9)	−0.0013 (7)	0.0019 (7)	−0.0030 (7)
C12	0.0269 (8)	0.0221 (8)	0.0225 (8)	0.0005 (6)	−0.0026 (6)	0.0025 (6)
C13	0.0334 (9)	0.0311 (9)	0.0255 (9)	−0.0055 (7)	−0.0004 (7)	−0.0050 (7)
C14	0.0378 (10)	0.0422 (10)	0.0298 (9)	−0.0041 (8)	0.0085 (7)	−0.0060 (8)
C15	0.0314 (9)	0.0401 (10)	0.0359 (10)	−0.0073 (8)	0.0049 (7)	0.0011 (8)
C16	0.0332 (9)	0.0298 (9)	0.0360 (10)	−0.0072 (7)	−0.0003 (7)	−0.0045 (7)
C17	0.0316 (9)	0.0283 (8)	0.0268 (8)	−0.0016 (7)	0.0015 (7)	−0.0048 (7)
C18	0.0290 (9)	0.0465 (11)	0.0358 (10)	0.0001 (8)	0.0003 (7)	0.0075 (8)
C19	0.0250 (9)	0.0456 (11)	0.0376 (10)	0.0017 (7)	0.0023 (7)	0.0116 (8)
C20	0.0309 (9)	0.0395 (10)	0.0368 (10)	0.0007 (7)	0.0029 (7)	0.0073 (8)
C21	0.0254 (9)	0.0463 (11)	0.0384 (10)	0.0004 (8)	0.0034 (7)	0.0045 (8)
C22	0.0217 (8)	0.0459 (11)	0.0384 (10)	0.0008 (7)	0.0014 (7)	0.0124 (8)
C23	0.0324 (10)	0.0420 (11)	0.0523 (12)	−0.0025 (8)	0.0010 (8)	0.0139 (9)
C24	0.0327 (10)	0.0443 (11)	0.0464 (12)	−0.0056 (8)	−0.0054 (8)	0.0087 (9)
C25	0.0236 (8)	0.0375 (10)	0.0331 (9)	0.0050 (7)	−0.0031 (7)	−0.0122 (8)
C26	0.0400 (11)	0.0356 (10)	0.0498 (12)	0.0003 (8)	−0.0109 (9)	−0.0092 (9)
C27	0.0500 (13)	0.0375 (11)	0.0750 (16)	−0.0032 (9)	−0.0141 (11)	−0.0136 (11)
C28	0.0390 (11)	0.0530 (13)	0.0705 (16)	0.0023 (10)	−0.0148 (10)	−0.0310 (12)
C29	0.0320 (10)	0.0686 (15)	0.0441 (12)	0.0096 (10)	−0.0092 (8)	−0.0259 (11)
C30	0.0292 (9)	0.0521 (11)	0.0348 (10)	0.0064 (8)	−0.0034 (7)	−0.0142 (9)

Geometric parameters (Å, º) top

S1—C1	1.6622 (16)	C12—C17	1.394 (2)
O1—C5	1.2218 (18)	C13—C14	1.392 (2)
O2—N5	1.215 (2)	C13—H13	0.9500
O3—N5	1.229 (2)	C14—C15	1.386 (2)
N1—C1	1.3466 (19)	C14—H14	0.9500
N1—N2	1.3745 (17)	C15—C16	1.382 (2)
N1—C3	1.4754 (18)	C15—H15	0.9500
N2—C2	1.3058 (19)	C16—C17	1.383 (2)
N3—C2	1.383 (2)	C16—H16	0.9500
N3—N4	1.3911 (17)	C17—H17	0.9500
N3—C1	1.3984 (19)	C18—C19	1.471 (2)
N4—C18	1.271 (2)	C18—H18	0.9500
N5—C22	1.483 (2)	C19—C24	1.385 (3)
C2—C25	1.468 (2)	C19—C20	1.405 (2)
C3—C12	1.515 (2)	C20—C21	1.382 (2)
C3—C4	1.525 (2)	C20—H20	0.9500
C3—H3	1.0000	C21—C22	1.375 (2)
C4—C5	1.508 (2)	C21—H21	0.9500
C4—H4A	0.9900	C22—C23	1.379 (3)
C4—H4B	0.9900	C23—C24	1.392 (2)
C5—C6	1.491 (2)	C23—H23	0.9500
C6—C7	1.389 (2)	C24—H24	0.9500
C6—C11	1.396 (2)	C25—C26	1.390 (3)
C7—C8	1.385 (2)	C25—C30	1.392 (2)
C7—H7	0.9500	C26—C27	1.384 (3)
C8—C9	1.382 (2)	C26—H26	0.9500
C8—H8	0.9500	C27—C28	1.377 (3)
C9—C10	1.390 (2)	C27—H27	0.9500
C9—H9	0.9500	C28—C29	1.367 (3)
C10—C11	1.381 (2)	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.394 (3)
C11—H11	0.9500	C29—H29	0.9500
C12—C13	1.389 (2)	C30—H30	0.9500

C1—N1—N2	113.68 (12)	C12—C13—H13	119.8
C1—N1—C3	124.37 (13)	C14—C13—H13	119.8
N2—N1—C3	121.68 (12)	C15—C14—C13	119.95 (16)
C2—N2—N1	105.02 (12)	C15—C14—H14	120.0
C2—N3—N4	120.35 (12)	C13—C14—H14	120.0
C2—N3—C1	108.21 (12)	C16—C15—C14	119.68 (16)
N4—N3—C1	130.87 (13)	C16—C15—H15	120.2
C18—N4—N3	119.33 (14)	C14—C15—H15	120.2
O2—N5—O3	124.84 (16)	C15—C16—C17	120.68 (15)
O2—N5—C22	117.86 (17)	C15—C16—H16	119.7
O3—N5—C22	117.30 (15)	C17—C16—H16	119.7
N1—C1—N3	102.69 (13)	C16—C17—C12	120.07 (16)
N1—C1—S1	126.13 (12)	C16—C17—H17	120.0
N3—C1—S1	131.16 (12)	C12—C17—H17	120.0
N2—C2—N3	110.38 (13)	N4—C18—C19	119.45 (16)
N2—C2—C25	122.63 (15)	N4—C18—H18	120.3
N3—C2—C25	126.98 (14)	C19—C18—H18	120.3
N1—C3—C12	111.99 (12)	C24—C19—C20	119.79 (16)
N1—C3—C4	109.89 (12)	C24—C19—C18	117.69 (16)
C12—C3—C4	110.29 (12)	C20—C19—C18	122.47 (17)
N1—C3—H3	108.2	C21—C20—C19	120.06 (17)
C12—C3—H3	108.2	C21—C20—H20	120.0
C4—C3—H3	108.2	C19—C20—H20	120.0
C5—C4—C3	114.30 (13)	C22—C21—C20	118.34 (17)
C5—C4—H4A	108.7	C22—C21—H21	120.8
C3—C4—H4A	108.7	C20—C21—H21	120.8
C5—C4—H4B	108.7	C21—C22—C23	123.43 (16)
C3—C4—H4B	108.7	C21—C22—N5	118.82 (16)
H4A—C4—H4B	107.6	C23—C22—N5	117.74 (16)
O1—C5—C6	120.97 (15)	C22—C23—C24	117.70 (18)
O1—C5—C4	121.53 (14)	C22—C23—H23	121.2
C6—C5—C4	117.49 (13)	C24—C23—H23	121.2
C7—C6—C11	119.18 (15)	C19—C24—C23	120.59 (17)
C7—C6—C5	121.46 (14)	C19—C24—H24	119.7
C11—C6—C5	119.33 (14)	C23—C24—H24	119.7
C8—C7—C6	120.30 (15)	C26—C25—C30	119.43 (16)
C8—C7—H7	119.8	C26—C25—C2	117.15 (16)
C6—C7—H7	119.8	C30—C25—C2	123.37 (17)
C9—C8—C7	120.23 (16)	C27—C26—C25	120.1 (2)
C9—C8—H8	119.9	C27—C26—H26	120.0
C7—C8—H8	119.9	C25—C26—H26	120.0
C8—C9—C10	119.91 (16)	C28—C27—C26	120.1 (2)
C8—C9—H9	120.0	C28—C27—H27	119.9
C10—C9—H9	120.0	C26—C27—H27	119.9
C11—C10—C9	119.93 (16)	C29—C28—C27	120.39 (19)
C11—C10—H10	120.0	C29—C28—H28	119.8
C9—C10—H10	120.0	C27—C28—H28	119.8
C10—C11—C6	120.44 (16)	C28—C29—C30	120.36 (19)
C10—C11—H11	119.8	C28—C29—H29	119.8
C6—C11—H11	119.8	C30—C29—H29	119.8
C13—C12—C17	119.23 (15)	C25—C30—C29	119.60 (19)
C13—C12—C3	121.66 (13)	C25—C30—H30	120.2
C17—C12—C3	119.01 (14)	C29—C30—H30	120.2
C12—C13—C14	120.38 (15)

C1—N1—N2—C2	−0.32 (18)	N1—C3—C12—C17	136.38 (14)
C3—N1—N2—C2	173.93 (14)	C4—C3—C12—C17	−100.89 (16)
C2—N3—N4—C18	−176.27 (16)	C17—C12—C13—C14	0.4 (2)
C1—N3—N4—C18	13.5 (3)	C3—C12—C13—C14	−176.07 (15)
N2—N1—C1—N3	−0.65 (17)	C12—C13—C14—C15	−0.4 (3)
C3—N1—C1—N3	−174.72 (13)	C13—C14—C15—C16	0.5 (3)
N2—N1—C1—S1	177.81 (12)	C14—C15—C16—C17	−0.6 (3)
C3—N1—C1—S1	3.7 (2)	C15—C16—C17—C12	0.6 (2)
C2—N3—C1—N1	1.33 (17)	C13—C12—C17—C16	−0.5 (2)
N4—N3—C1—N1	172.49 (15)	C3—C12—C17—C16	176.08 (14)
C2—N3—C1—S1	−177.02 (14)	N3—N4—C18—C19	178.74 (15)
N4—N3—C1—S1	−5.9 (3)	N4—C18—C19—C24	170.56 (18)
N1—N2—C2—N3	1.19 (18)	N4—C18—C19—C20	−11.9 (3)
N1—N2—C2—C25	−177.76 (15)	C24—C19—C20—C21	2.9 (3)
N4—N3—C2—N2	−173.91 (13)	C18—C19—C20—C21	−174.62 (17)
C1—N3—C2—N2	−1.65 (19)	C19—C20—C21—C22	−1.3 (3)
N4—N3—C2—C25	5.0 (2)	C20—C21—C22—C23	−1.6 (3)
C1—N3—C2—C25	177.24 (16)	C20—C21—C22—N5	176.85 (16)
C1—N1—C3—C12	−69.61 (19)	O2—N5—C22—C21	168.08 (18)
N2—N1—C3—C12	116.77 (15)	O3—N5—C22—C21	−11.4 (3)
C1—N1—C3—C4	167.44 (14)	O2—N5—C22—C23	−13.4 (3)
N2—N1—C3—C4	−6.2 (2)	O3—N5—C22—C23	167.13 (17)
N1—C3—C4—C5	−65.96 (17)	C21—C22—C23—C24	2.8 (3)
C12—C3—C4—C5	170.10 (12)	N5—C22—C23—C24	−175.60 (17)
C3—C4—C5—O1	−8.9 (2)	C20—C19—C24—C23	−1.6 (3)
C3—C4—C5—C6	172.12 (13)	C18—C19—C24—C23	176.04 (18)
O1—C5—C6—C7	−163.09 (15)	C22—C23—C24—C19	−1.2 (3)
C4—C5—C6—C7	15.9 (2)	N2—C2—C25—C26	26.7 (2)
O1—C5—C6—C11	14.8 (2)	N3—C2—C25—C26	−152.10 (18)
C4—C5—C6—C11	−166.23 (14)	N2—C2—C25—C30	−150.80 (17)
C11—C6—C7—C8	0.6 (2)	N3—C2—C25—C30	30.4 (3)
C5—C6—C7—C8	178.48 (15)	C30—C25—C26—C27	−0.2 (3)
C6—C7—C8—C9	−0.1 (2)	C2—C25—C26—C27	−177.80 (17)
C7—C8—C9—C10	−0.5 (3)	C25—C26—C27—C28	−0.8 (3)
C8—C9—C10—C11	0.8 (3)	C26—C27—C28—C29	0.7 (3)
C9—C10—C11—C6	−0.4 (3)	C27—C28—C29—C30	0.4 (3)
C7—C6—C11—C10	−0.3 (2)	C26—C25—C30—C29	1.4 (3)
C5—C6—C11—C10	−178.26 (15)	C2—C25—C30—C29	178.79 (16)
N1—C3—C12—C13	−47.16 (19)	C28—C29—C30—C25	−1.5 (3)
C4—C3—C12—C13	75.57 (18)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₃N₅O₃S
M_r	533.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	13.3303 (13), 21.832 (2), 9.2773 (9)
β (°)	98.213 (3)
V (Å³)	2672.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.968, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	27241, 6372, 5124
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.131, 1.10
No. of reflections	6372
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge support of this study by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

References

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