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

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

doi:10.1107/S1600536811035185

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2728

https://doi.org/10.1107/S1600536811035185

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

Wei Wang,^a,^b ^* Yan Gao,^b Wen-peng Wu,^b Chao Xu ^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, C₂₃H₂₀N₄O₂S, the triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)°, respectively, with the furan ring and the phenyl rings. The furan ring is almost perpendicular to the central phenyl ring, making a dihedral angle of 86.0 (3)°.

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

C₂₃H₂₀N₄O₂S
M_r = 416.50
Monoclinic, P 2₁ /c
a = 8.154 (3) Å
b = 21.194 (6) Å
c = 12.878 (4) Å
β = 107.965 (5)°
V = 2117.0 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.958, T_max = 0.979
26979 measured reflections
5030 independent reflections
4229 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.07
5030 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 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/S1600536811035185/zs2141sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035185/zs2141Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035185/zs2141Isup3.cml

checkCIF report

Comment top

In a continuation of structural studies by our group (Wang et al., 2011) of Mannich base derivatives synthesized by reactions of amino heterocycles and aromatic aldehydes, we present here the crystal structure of the title compound, C₂₃H₂₀N₄O₂S.

The bond lengths and angles in this compound are found to have values comparable with those reported in 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 C1 and C2 atoms in the 1,2,4-triazole ring show distorted C_sp² hybridization states with bond angles of 102.03 (10)° (N1—C1—N3), 131.01 (9)° (N3—C1—S1), 110.81 (11)° (N2—C2—N3) and 125.29 (12) ° (N2—C2—C23), which are similar to those in other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)° with the furan ring and the phenyl rings, respectively. The furan ring is almost perpendicular to the C12—C17 phenyl ring, with a dihedral angle of 94.0 (3)°.

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 2-furfural (2.0 mmol) with 3-(4-amino-3-methyl-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 75% 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 the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

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

Crystal data top

C₂₃H₂₀N₄O₂S	F(000) = 872
M_r = 416.50	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7435 reflections
a = 8.154 (3) Å	θ = 1.7–27.9°
b = 21.194 (6) Å	µ = 0.18 mm⁻¹
c = 12.878 (4) Å	T = 113 K
β = 107.965 (5)°	Prism, colorless
V = 2117.0 (12) Å³	0.24 × 0.20 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5030 independent reflections
Radiation source: rotating anode	4229 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.043
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −27→27
T_min = 0.958, T_max = 0.979	l = −16→16
26979 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0597P)² + 0.0507P] where P = (F_o² + 2F_c²)/3
5030 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₀N₄O₂S	V = 2117.0 (12) Å³
M_r = 416.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.154 (3) Å	µ = 0.18 mm⁻¹
b = 21.194 (6) Å	T = 113 K
c = 12.878 (4) Å	0.24 × 0.20 × 0.12 mm
β = 107.965 (5)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5030 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4229 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.979	R_int = 0.043
26979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
5030 reflections	Δρ_min = −0.18 e Å⁻³
272 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	1.09278 (4)	0.678722 (17)	0.64588 (3)	0.03095 (11)
O1	0.74128 (14)	0.76825 (5)	0.75402 (7)	0.0366 (2)
O2	0.80256 (13)	0.49556 (5)	0.33988 (7)	0.0370 (2)
N1	0.89702 (13)	0.64352 (5)	0.77200 (8)	0.0210 (2)
N2	0.76948 (13)	0.60222 (5)	0.77821 (8)	0.0258 (2)
N3	0.82733 (13)	0.59160 (5)	0.62302 (8)	0.0231 (2)
N4	0.81208 (14)	0.55961 (5)	0.52572 (8)	0.0287 (3)
C1	0.93901 (15)	0.63862 (6)	0.67870 (9)	0.0215 (3)
C2	0.73025 (17)	0.57115 (6)	0.68692 (10)	0.0265 (3)
C3	0.98664 (16)	0.68280 (6)	0.86642 (9)	0.0231 (3)
H3	1.0421	0.7187	0.8396	0.028*
C4	0.85808 (17)	0.71013 (6)	0.91857 (10)	0.0272 (3)
H4A	0.7942	0.6751	0.9394	0.033*
H4B	0.9219	0.7329	0.9861	0.033*
C5	0.73023 (17)	0.75493 (6)	0.84367 (10)	0.0265 (3)
C6	0.59252 (16)	0.78340 (6)	0.88329 (10)	0.0254 (3)
C7	0.45618 (19)	0.81411 (6)	0.80761 (12)	0.0339 (3)
H7	0.4509	0.8154	0.7329	0.041*
C8	0.3287 (2)	0.84270 (7)	0.84094 (13)	0.0431 (4)
H8	0.2349	0.8630	0.7889	0.052*
C9	0.3374 (2)	0.84195 (7)	0.95004 (13)	0.0414 (4)
H9	0.2509	0.8625	0.9729	0.050*
C10	0.47170 (19)	0.81126 (6)	1.02590 (12)	0.0327 (3)
H10	0.4766	0.8104	1.1005	0.039*
C11	0.59897 (17)	0.78178 (6)	0.99299 (10)	0.0275 (3)
H11	0.6907	0.7605	1.0450	0.033*
C12	1.12820 (16)	0.64429 (6)	0.94503 (9)	0.0234 (3)
C13	1.08906 (17)	0.59523 (6)	1.00540 (10)	0.0288 (3)
H13	0.9722	0.5870	1.0001	0.035*
C14	1.21854 (18)	0.55835 (7)	1.07314 (11)	0.0325 (3)
H14	1.1904	0.5249	1.1137	0.039*
C15	1.38920 (18)	0.57036 (7)	1.08172 (11)	0.0373 (3)
H15	1.4783	0.5452	1.1281	0.045*
C16	1.42945 (18)	0.61911 (7)	1.02258 (12)	0.0401 (4)
H16	1.5466	0.6274	1.0287	0.048*
C17	1.30023 (17)	0.65601 (7)	0.95437 (11)	0.0314 (3)
H17	1.3291	0.6894	0.9139	0.038*
C18	0.86294 (17)	0.58860 (7)	0.45364 (10)	0.0296 (3)
H18	0.9078	0.6302	0.4672	0.036*
C19	0.85153 (17)	0.55772 (7)	0.35217 (10)	0.0309 (3)
C20	0.87864 (18)	0.57953 (8)	0.26002 (11)	0.0385 (3)
H20	0.9137	0.6209	0.2477	0.046*
C21	0.84408 (19)	0.52813 (8)	0.18528 (12)	0.0420 (4)
H21	0.8514	0.5284	0.1131	0.050*
C22	0.79925 (19)	0.47929 (8)	0.23657 (11)	0.0410 (4)
H22	0.7691	0.4387	0.2053	0.049*
C23	0.5960 (2)	0.52161 (7)	0.65264 (11)	0.0430 (4)
H23A	0.5505	0.5122	0.7130	0.064*
H23B	0.6465	0.4833	0.6326	0.064*
H23C	0.5023	0.5366	0.5896	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02698 (19)	0.0442 (2)	0.02233 (18)	−0.00676 (14)	0.00865 (14)	0.00319 (14)
O1	0.0485 (6)	0.0389 (5)	0.0253 (5)	0.0118 (5)	0.0157 (5)	0.0049 (4)
O2	0.0429 (6)	0.0387 (5)	0.0242 (5)	0.0133 (5)	0.0029 (4)	−0.0078 (4)
N1	0.0226 (5)	0.0225 (5)	0.0178 (5)	−0.0028 (4)	0.0064 (4)	−0.0018 (4)
N2	0.0259 (6)	0.0297 (6)	0.0211 (5)	−0.0072 (4)	0.0063 (4)	0.0013 (4)
N3	0.0281 (6)	0.0235 (5)	0.0160 (5)	−0.0001 (4)	0.0043 (4)	−0.0017 (4)
N4	0.0341 (6)	0.0309 (6)	0.0172 (5)	0.0061 (5)	0.0023 (4)	−0.0055 (4)
C1	0.0229 (6)	0.0241 (6)	0.0166 (6)	0.0029 (5)	0.0046 (5)	0.0011 (5)
C2	0.0301 (7)	0.0274 (6)	0.0192 (6)	−0.0050 (5)	0.0035 (5)	0.0027 (5)
C3	0.0271 (7)	0.0229 (6)	0.0183 (6)	−0.0037 (5)	0.0055 (5)	−0.0036 (5)
C4	0.0339 (7)	0.0273 (7)	0.0195 (6)	0.0040 (6)	0.0069 (5)	−0.0033 (5)
C5	0.0323 (7)	0.0236 (6)	0.0222 (6)	−0.0004 (5)	0.0063 (5)	−0.0041 (5)
C6	0.0275 (7)	0.0218 (6)	0.0263 (6)	−0.0025 (5)	0.0074 (5)	−0.0016 (5)
C7	0.0347 (8)	0.0358 (7)	0.0308 (7)	0.0035 (6)	0.0097 (6)	0.0065 (6)
C8	0.0360 (8)	0.0490 (9)	0.0460 (9)	0.0126 (7)	0.0153 (7)	0.0151 (7)
C9	0.0392 (9)	0.0420 (8)	0.0509 (9)	0.0085 (7)	0.0255 (8)	0.0075 (7)
C10	0.0379 (8)	0.0320 (7)	0.0327 (7)	−0.0012 (6)	0.0175 (6)	−0.0010 (6)
C11	0.0304 (7)	0.0251 (6)	0.0263 (6)	−0.0038 (5)	0.0078 (5)	−0.0023 (5)
C12	0.0257 (6)	0.0235 (6)	0.0197 (6)	−0.0018 (5)	0.0051 (5)	−0.0053 (5)
C13	0.0259 (7)	0.0316 (7)	0.0276 (7)	−0.0014 (5)	0.0064 (5)	0.0006 (5)
C14	0.0349 (8)	0.0333 (7)	0.0270 (7)	0.0004 (6)	0.0059 (6)	0.0043 (6)
C15	0.0300 (7)	0.0457 (8)	0.0307 (7)	0.0070 (6)	0.0013 (6)	0.0049 (6)
C16	0.0231 (7)	0.0558 (10)	0.0374 (8)	−0.0030 (7)	0.0035 (6)	0.0030 (7)
C17	0.0293 (7)	0.0355 (7)	0.0268 (7)	−0.0071 (6)	0.0052 (6)	−0.0001 (6)
C18	0.0312 (7)	0.0346 (7)	0.0203 (6)	0.0082 (6)	0.0038 (5)	−0.0023 (5)
C19	0.0271 (7)	0.0390 (7)	0.0233 (6)	0.0104 (6)	0.0026 (5)	−0.0044 (6)
C20	0.0343 (8)	0.0556 (9)	0.0252 (7)	0.0017 (7)	0.0086 (6)	−0.0073 (6)
C21	0.0342 (8)	0.0678 (11)	0.0231 (7)	0.0116 (8)	0.0073 (6)	−0.0102 (7)
C22	0.0372 (8)	0.0515 (9)	0.0266 (7)	0.0192 (7)	−0.0012 (6)	−0.0157 (7)
C23	0.0523 (10)	0.0433 (9)	0.0259 (7)	−0.0241 (7)	0.0012 (7)	0.0018 (6)

Geometric parameters (Å, º) top

S1—C1	1.6734 (13)	C9—H9	0.9500
O1—C5	1.2185 (15)	C10—C11	1.3851 (19)
O2—C22	1.3666 (16)	C10—H10	0.9500
O2—C19	1.3715 (18)	C11—H11	0.9500
N1—C1	1.3511 (15)	C12—C17	1.3927 (18)
N1—N2	1.3803 (14)	C12—C13	1.3930 (18)
N1—C3	1.4688 (15)	C13—C14	1.3852 (19)
N2—C2	1.2984 (16)	C13—H13	0.9500
N3—C2	1.3760 (16)	C14—C15	1.385 (2)
N3—C1	1.3906 (15)	C14—H14	0.9500
N3—N4	1.3961 (14)	C15—C16	1.382 (2)
N4—C18	1.2840 (17)	C15—H15	0.9500
C2—C23	1.4823 (18)	C16—C17	1.387 (2)
C3—C12	1.5174 (17)	C16—H16	0.9500
C3—C4	1.5232 (17)	C17—H17	0.9500
C3—H3	1.0000	C18—C19	1.4386 (18)
C4—C5	1.5160 (18)	C18—H18	0.9500
C4—H4A	0.9900	C19—C20	1.354 (2)
C4—H4B	0.9900	C20—C21	1.423 (2)
C5—C6	1.4961 (18)	C20—H20	0.9500
C6—C7	1.3932 (19)	C21—C22	1.338 (2)
C6—C11	1.3978 (17)	C21—H21	0.9500
C7—C8	1.381 (2)	C22—H22	0.9500
C7—H7	0.9500	C23—H23A	0.9800
C8—C9	1.385 (2)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C9—C10	1.385 (2)

C22—O2—C19	105.81 (11)	C11—C10—H10	120.0
C1—N1—N2	113.88 (10)	C10—C11—C6	120.00 (13)
C1—N1—C3	125.58 (10)	C10—C11—H11	120.0
N2—N1—C3	120.19 (9)	C6—C11—H11	120.0
C2—N2—N1	104.40 (10)	C17—C12—C13	118.88 (12)
C2—N3—C1	108.86 (10)	C17—C12—C3	120.02 (11)
C2—N3—N4	118.39 (10)	C13—C12—C3	121.05 (11)
C1—N3—N4	132.36 (10)	C14—C13—C12	120.76 (13)
C18—N4—N3	117.20 (11)	C14—C13—H13	119.6
N1—C1—N3	102.03 (10)	C12—C13—H13	119.6
N1—C1—S1	126.93 (9)	C15—C14—C13	119.89 (13)
N3—C1—S1	131.01 (9)	C15—C14—H14	120.1
N2—C2—N3	110.81 (11)	C13—C14—H14	120.1
N2—C2—C23	125.59 (12)	C16—C15—C14	119.81 (13)
N3—C2—C23	123.58 (11)	C16—C15—H15	120.1
N1—C3—C12	109.22 (9)	C14—C15—H15	120.1
N1—C3—C4	110.25 (10)	C15—C16—C17	120.51 (13)
C12—C3—C4	113.31 (10)	C15—C16—H16	119.7
N1—C3—H3	108.0	C17—C16—H16	119.7
C12—C3—H3	108.0	C16—C17—C12	120.16 (13)
C4—C3—H3	108.0	C16—C17—H17	119.9
C5—C4—C3	112.91 (10)	C12—C17—H17	119.9
C5—C4—H4A	109.0	N4—C18—C19	119.61 (13)
C3—C4—H4A	109.0	N4—C18—H18	120.2
C5—C4—H4B	109.0	C19—C18—H18	120.2
C3—C4—H4B	109.0	C20—C19—O2	110.32 (12)
H4A—C4—H4B	107.8	C20—C19—C18	131.19 (14)
O1—C5—C6	120.81 (12)	O2—C19—C18	118.48 (12)
O1—C5—C4	120.71 (12)	C19—C20—C21	106.23 (14)
C6—C5—C4	118.47 (11)	C19—C20—H20	126.9
C7—C6—C11	119.45 (12)	C21—C20—H20	126.9
C7—C6—C5	118.08 (11)	C22—C21—C20	106.60 (13)
C11—C6—C5	122.44 (12)	C22—C21—H21	126.7
C8—C7—C6	120.15 (13)	C20—C21—H21	126.7
C8—C7—H7	119.9	C21—C22—O2	111.03 (13)
C6—C7—H7	119.9	C21—C22—H22	124.5
C7—C8—C9	120.18 (14)	O2—C22—H22	124.5
C7—C8—H8	119.9	C2—C23—H23A	109.5
C9—C8—H8	119.9	C2—C23—H23B	109.5
C10—C9—C8	120.17 (13)	H23A—C23—H23B	109.5
C10—C9—H9	119.9	C2—C23—H23C	109.5
C8—C9—H9	119.9	H23A—C23—H23C	109.5
C9—C10—C11	120.03 (13)	H23B—C23—H23C	109.5
C9—C10—H10	120.0

C1—N1—N2—C2	−0.35 (13)	C11—C6—C7—C8	0.0 (2)
C3—N1—N2—C2	−173.97 (11)	C5—C6—C7—C8	−178.09 (13)
C2—N3—N4—C18	160.90 (12)	C6—C7—C8—C9	1.1 (2)
C1—N3—N4—C18	−27.24 (19)	C7—C8—C9—C10	−1.5 (2)
N2—N1—C1—N3	0.93 (13)	C8—C9—C10—C11	0.7 (2)
C3—N1—C1—N3	174.15 (10)	C9—C10—C11—C6	0.5 (2)
N2—N1—C1—S1	−177.18 (9)	C7—C6—C11—C10	−0.84 (19)
C3—N1—C1—S1	−3.96 (17)	C5—C6—C11—C10	177.21 (12)
C2—N3—C1—N1	−1.14 (13)	N1—C3—C12—C17	106.97 (13)
N4—N3—C1—N1	−173.59 (11)	C4—C3—C12—C17	−129.70 (12)
C2—N3—C1—S1	176.86 (10)	N1—C3—C12—C13	−70.35 (14)
N4—N3—C1—S1	4.4 (2)	C4—C3—C12—C13	52.98 (15)
N1—N2—C2—N3	−0.43 (14)	C17—C12—C13—C14	−0.41 (18)
N1—N2—C2—C23	−178.64 (13)	C3—C12—C13—C14	176.94 (11)
C1—N3—C2—N2	1.04 (15)	C12—C13—C14—C15	0.3 (2)
N4—N3—C2—N2	174.70 (10)	C13—C14—C15—C16	0.0 (2)
C1—N3—C2—C23	179.29 (12)	C14—C15—C16—C17	−0.2 (2)
N4—N3—C2—C23	−7.05 (18)	C15—C16—C17—C12	0.1 (2)
C1—N1—C3—C12	−90.83 (13)	C13—C12—C17—C16	0.19 (19)
N2—N1—C3—C12	81.99 (13)	C3—C12—C17—C16	−177.19 (12)
C1—N1—C3—C4	144.04 (11)	N3—N4—C18—C19	179.51 (11)
N2—N1—C3—C4	−43.14 (14)	C22—O2—C19—C20	−0.25 (15)
N1—C3—C4—C5	−64.25 (13)	C22—O2—C19—C18	178.72 (11)
C12—C3—C4—C5	172.98 (10)	N4—C18—C19—C20	172.22 (14)
C3—C4—C5—O1	−3.40 (17)	N4—C18—C19—O2	−6.51 (19)
C3—C4—C5—C6	177.83 (11)	O2—C19—C20—C21	0.22 (16)
O1—C5—C6—C7	13.79 (19)	C18—C19—C20—C21	−178.59 (14)
C4—C5—C6—C7	−167.44 (12)	C19—C20—C21—C22	−0.10 (16)
O1—C5—C6—C11	−164.29 (12)	C20—C21—C22—O2	−0.06 (17)
C4—C5—C6—C11	14.49 (18)	C19—O2—C22—C21	0.19 (15)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₄O₂S
M_r	416.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	8.154 (3), 21.194 (6), 12.878 (4)
β (°)	107.965 (5)
V (Å³)	2117.0 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	26979, 5030, 4229
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.07
No. of reflections	5030
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18

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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