4-Amino-1-(2-benzoyl-1-phenyl­eth­yl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione

Song, X.; Ye, L.; Wang, H.

doi:10.1107/S1600536810054553

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o347

doi:10.1107/S1600536810054553

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4-Amino-1-(2-benzoyl-1-phenylethyl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione

Xiao-qiu Song,^a Lin Ye ^a and He-wen Wang ^b ^*

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bCollege of Chemistry and Applied Chemistry, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 18 December 2010; accepted 28 December 2010; online 12 January 2011)

In the title compound, C₂₃H₂₀N₄OS, the two phenyl rings of the diphenylpropanone fragment form a dihedral angle of 86.8 (1)°, and the third phenyl ring attached to the triazole ring is twisted from the latter at 40.1 (1)°. In the crystal, molecules are paired into centrosymmetric dimers via pairs of intermolecular N—H⋯O and N—H⋯S hydrogen bonds.

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 ); Tan et al. (2010 ); Wang et al. (2011 ).

Experimental

Crystal data

C₂₃H₂₀N₄OS
M_r = 400.49
Triclinic, $[P \overline 1]$
a = 9.4625 (19) Å
b = 11.340 (2) Å
c = 11.655 (2) Å
α = 111.80 (3)°
β = 111.01 (3)°
γ = 98.91 (3)°
V = 1022.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.965, T_max = 0.982
9308 measured reflections
3590 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.121
S = 1.04
3590 reflections
271 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.91 (2)	2.39 (2)	2.873 (3)	114 (2)
N4—H4B⋯S1ⁱ	0.91 (2)	2.66 (2)	3.490 (2)	151 (2)
Symmetry code: (i) -x+1, -y, -z.

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054553/cv5022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054553/cv5022Isup2.hkl

checkCIF report

Comment top

In continuation of structural study of 1,2,4-triazole-5(4H)-thione derivatives in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are found to have normal values comparable with those observed 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). There are three phenyl rings in the molecule. Phenyl ring A (C1—C6) attached in the triazole ring makes the dihedral angles of 61.0 (1) and 70.9 (1)° with the phenyl ring B (C10—C15) and C (C18—C23), respectively. Rings B and C form a dihedral angle of 86.8 (1)°.

Intermolecular N—H···S and N—H···O hydrogen bonds (Table 1) link the adjacent molecules into centrosymmetric dimers.

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); Tan et al. (2010); Wang et al. (2011).

Experimental top

The title compound was synthesized by the reaction of the chalcone (2.0 mmol) with 4-amino-3-phenyl-4H-1,2,4-triazole-5-thiol (2.0 mmol) by refluxing in ethanol for 24 h. 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 colorless solid in 87% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Computing details top

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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

4-Amino-1-(2-benzoyl-1-phenylethyl)-3-phenyl-1H-1,2,4-triazol- 5(4H)-thione top

Crystal data top

C₂₃H₂₀N₄OS	Z = 2
M_r = 400.49	F(000) = 420
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4625 (19) Å	Cell parameters from 3363 reflections
b = 11.340 (2) Å	θ = 2.1–27.8°
c = 11.655 (2) Å	µ = 0.18 mm⁻¹
α = 111.80 (3)°	T = 113 K
β = 111.01 (3)°	Prism, colourless
γ = 98.91 (3)°	0.20 × 0.18 × 0.10 mm
V = 1022.4 (4) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3590 independent reflections
Radiation source: rotating anode	2686 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
T_min = 0.965, T_max = 0.982	l = −13→12
9308 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.071P)² + 0.1941P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3590 reflections	Δρ_max = 0.35 e Å⁻³
271 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.107 (8)

Crystal data top

C₂₃H₂₀N₄OS	γ = 98.91 (3)°
M_r = 400.49	V = 1022.4 (4) Å³
Triclinic, P1	Z = 2
a = 9.4625 (19) Å	Mo Kα radiation
b = 11.340 (2) Å	µ = 0.18 mm⁻¹
c = 11.655 (2) Å	T = 113 K
α = 111.80 (3)°	0.20 × 0.18 × 0.10 mm
β = 111.01 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3590 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2686 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.982	R_int = 0.039
9308 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.35 e Å⁻³
3590 reflections	Δρ_min = −0.29 e Å⁻³
271 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	0.54562 (6)	−0.11721 (5)	0.13685 (5)	0.02158 (19)
O1	0.45937 (17)	0.25822 (14)	0.24735 (14)	0.0237 (4)
N1	0.82240 (19)	0.25821 (16)	0.32190 (16)	0.0182 (4)
N2	0.72008 (19)	0.15086 (16)	0.31246 (16)	0.0163 (4)
N3	0.75632 (19)	0.07328 (15)	0.13230 (15)	0.0159 (4)
N4	0.7447 (2)	−0.01242 (17)	0.00269 (17)	0.0213 (4)
H4A	0.703 (2)	−0.0962 (13)	−0.010 (2)	0.036 (7)*
H4B	0.675 (2)	0.005 (2)	−0.062 (2)	0.055 (9)*
C1	0.9302 (2)	0.4216 (2)	0.2059 (2)	0.0231 (5)
H1	0.8614	0.4514	0.2443	0.028*
C2	1.0231 (3)	0.5072 (2)	0.1812 (2)	0.0252 (5)
H2	1.0168	0.5949	0.2010	0.030*
C3	1.1260 (2)	0.4637 (2)	0.1269 (2)	0.0257 (5)
H3	1.1913	0.5223	0.1111	0.031*
C4	1.1330 (3)	0.3347 (2)	0.0962 (2)	0.0260 (5)
H4	1.2038	0.3059	0.0600	0.031*
C5	1.0376 (2)	0.2475 (2)	0.1179 (2)	0.0221 (5)
H5	1.0408	0.1586	0.0943	0.026*
C6	0.9371 (2)	0.2915 (2)	0.17470 (19)	0.0176 (4)
C7	0.8422 (2)	0.20849 (19)	0.21041 (19)	0.0176 (5)
C8	0.6737 (2)	0.03559 (19)	0.19571 (19)	0.0160 (4)
C9	0.6600 (2)	0.17172 (19)	0.41591 (19)	0.0178 (5)
H9	0.5473	0.1088	0.3687	0.021*
C10	0.7610 (2)	0.14453 (18)	0.53269 (19)	0.0176 (4)
C11	0.9151 (2)	0.1418 (2)	0.5597 (2)	0.0222 (5)
H11	0.9606	0.1555	0.5032	0.027*
C12	1.0040 (3)	0.1191 (2)	0.6688 (2)	0.0245 (5)
H12	1.1093	0.1169	0.6861	0.029*
C13	0.9392 (3)	0.0995 (2)	0.7523 (2)	0.0237 (5)
H13	0.9991	0.0824	0.8259	0.028*
C14	0.7863 (3)	0.1051 (2)	0.7281 (2)	0.0250 (5)
H14	0.7426	0.0939	0.7866	0.030*
C15	0.6970 (2)	0.1268 (2)	0.6188 (2)	0.0215 (5)
H15	0.5921	0.1297	0.6023	0.026*
C16	0.6580 (2)	0.31677 (19)	0.47288 (19)	0.0187 (5)
H16A	0.6083	0.3303	0.5364	0.022*
H16B	0.7697	0.3799	0.5269	0.022*
C17	0.5659 (2)	0.3486 (2)	0.35832 (19)	0.0174 (4)
C18	0.6095 (2)	0.4905 (2)	0.3827 (2)	0.0188 (5)
C19	0.6976 (2)	0.5982 (2)	0.5161 (2)	0.0229 (5)
H19	0.7328	0.5816	0.5941	0.028*
C20	0.7336 (3)	0.7291 (2)	0.5348 (2)	0.0278 (5)
H20	0.7929	0.8020	0.6258	0.033*
C21	0.6842 (3)	0.7544 (2)	0.4223 (3)	0.0298 (6)
H21	0.7084	0.8445	0.4361	0.036*
C22	0.5990 (3)	0.6483 (2)	0.2889 (2)	0.0317 (6)
H22	0.5672	0.6657	0.2114	0.038*
C23	0.5603 (3)	0.5168 (2)	0.2688 (2)	0.0261 (5)
H23	0.5003	0.4443	0.1775	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0236 (3)	0.0133 (3)	0.0240 (3)	0.0040 (2)	0.0089 (2)	0.0076 (2)
O1	0.0232 (8)	0.0199 (8)	0.0169 (7)	0.0047 (6)	0.0019 (6)	0.0057 (6)
N1	0.0185 (9)	0.0149 (9)	0.0190 (9)	0.0036 (7)	0.0084 (7)	0.0066 (7)
N2	0.0188 (9)	0.0134 (8)	0.0154 (8)	0.0037 (7)	0.0078 (7)	0.0061 (7)
N3	0.0171 (9)	0.0136 (8)	0.0144 (8)	0.0062 (7)	0.0056 (7)	0.0049 (7)
N4	0.0235 (10)	0.0178 (9)	0.0152 (9)	0.0066 (8)	0.0075 (8)	0.0017 (7)
C1	0.0231 (11)	0.0187 (11)	0.0211 (11)	0.0038 (9)	0.0079 (9)	0.0061 (9)
C2	0.0282 (12)	0.0217 (11)	0.0192 (11)	0.0033 (10)	0.0051 (10)	0.0106 (9)
C3	0.0215 (11)	0.0267 (12)	0.0212 (11)	−0.0007 (9)	0.0052 (9)	0.0114 (9)
C4	0.0206 (11)	0.0295 (12)	0.0226 (11)	0.0032 (10)	0.0104 (10)	0.0084 (10)
C5	0.0217 (11)	0.0198 (11)	0.0170 (10)	0.0039 (9)	0.0057 (9)	0.0052 (9)
C6	0.0154 (10)	0.0195 (10)	0.0105 (9)	0.0006 (8)	0.0029 (8)	0.0049 (8)
C7	0.0161 (10)	0.0146 (10)	0.0158 (10)	0.0026 (8)	0.0045 (8)	0.0046 (8)
C8	0.0166 (10)	0.0142 (10)	0.0161 (10)	0.0064 (8)	0.0057 (9)	0.0070 (8)
C9	0.0185 (10)	0.0168 (10)	0.0156 (10)	0.0038 (8)	0.0075 (9)	0.0062 (8)
C10	0.0200 (10)	0.0105 (9)	0.0166 (10)	0.0027 (8)	0.0068 (9)	0.0032 (8)
C11	0.0235 (11)	0.0216 (11)	0.0215 (11)	0.0076 (9)	0.0106 (9)	0.0096 (9)
C12	0.0238 (11)	0.0226 (11)	0.0225 (11)	0.0090 (9)	0.0078 (10)	0.0080 (9)
C13	0.0308 (12)	0.0195 (11)	0.0153 (10)	0.0067 (9)	0.0053 (10)	0.0082 (9)
C14	0.0314 (12)	0.0247 (11)	0.0183 (11)	0.0041 (10)	0.0130 (10)	0.0098 (9)
C15	0.0206 (11)	0.0191 (10)	0.0216 (11)	0.0032 (9)	0.0090 (9)	0.0081 (9)
C16	0.0213 (10)	0.0152 (10)	0.0158 (10)	0.0036 (8)	0.0079 (9)	0.0048 (8)
C17	0.0177 (10)	0.0196 (10)	0.0142 (10)	0.0065 (9)	0.0074 (9)	0.0069 (8)
C18	0.0143 (10)	0.0194 (11)	0.0241 (11)	0.0062 (8)	0.0097 (9)	0.0103 (9)
C19	0.0196 (11)	0.0195 (11)	0.0253 (11)	0.0043 (9)	0.0094 (9)	0.0077 (9)
C20	0.0234 (11)	0.0180 (11)	0.0388 (13)	0.0067 (9)	0.0149 (10)	0.0094 (10)
C21	0.0252 (12)	0.0222 (12)	0.0519 (15)	0.0120 (10)	0.0196 (11)	0.0232 (11)
C22	0.0323 (13)	0.0343 (13)	0.0386 (13)	0.0124 (11)	0.0151 (11)	0.0273 (11)
C23	0.0238 (11)	0.0267 (12)	0.0271 (12)	0.0071 (10)	0.0089 (10)	0.0149 (10)

Geometric parameters (Å, º) top

S1—C8	1.677 (2)	C10—C11	1.386 (3)
O1—C17	1.225 (2)	C10—C15	1.400 (3)
N1—C7	1.305 (3)	C11—C12	1.391 (3)
N1—N2	1.375 (2)	C11—H11	0.9500
N2—C8	1.351 (2)	C12—C13	1.385 (3)
N2—C9	1.468 (3)	C12—H12	0.9500
N3—C8	1.373 (3)	C13—C14	1.387 (3)
N3—C7	1.374 (3)	C13—H13	0.9500
N3—N4	1.413 (2)	C14—C15	1.387 (3)
N4—H4A	0.91 (2)	C14—H14	0.9500
N4—H4B	0.91 (2)	C15—H15	0.9500
C1—C2	1.387 (3)	C16—C17	1.514 (3)
C1—C6	1.400 (3)	C16—H16A	0.9900
C1—H1	0.9500	C16—H16B	0.9900
C2—C3	1.396 (3)	C17—C18	1.488 (3)
C2—H2	0.9500	C18—C19	1.396 (3)
C3—C4	1.389 (3)	C18—C23	1.400 (3)
C3—H3	0.9500	C19—C20	1.385 (3)
C4—C5	1.389 (3)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.379 (3)
C5—C6	1.395 (3)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.388 (3)
C6—C7	1.471 (3)	C21—H21	0.9500
C9—C10	1.527 (3)	C22—C23	1.386 (3)
C9—C16	1.534 (3)	C22—H22	0.9500
C9—H9	1.0000	C23—H23	0.9500

C7—N1—N2	104.69 (16)	C10—C11—C12	120.6 (2)
C8—N2—N1	113.11 (16)	C10—C11—H11	119.7
C8—N2—C9	126.58 (17)	C12—C11—H11	119.7
N1—N2—C9	120.00 (15)	C13—C12—C11	120.2 (2)
C8—N3—C7	109.01 (16)	C13—C12—H12	119.9
C8—N3—N4	124.81 (16)	C11—C12—H12	119.9
C7—N3—N4	126.05 (17)	C12—C13—C14	119.66 (19)
N3—N4—H4A	104.0 (15)	C12—C13—H13	120.2
N3—N4—H4B	106.7 (17)	C14—C13—H13	120.2
H4A—N4—H4B	111.0 (14)	C15—C14—C13	120.3 (2)
C2—C1—C6	120.4 (2)	C15—C14—H14	119.9
C2—C1—H1	119.8	C13—C14—H14	119.9
C6—C1—H1	119.8	C14—C15—C10	120.3 (2)
C1—C2—C3	119.5 (2)	C14—C15—H15	119.9
C1—C2—H2	120.2	C10—C15—H15	119.9
C3—C2—H2	120.2	C17—C16—C9	112.01 (16)
C4—C3—C2	120.0 (2)	C17—C16—H16A	109.2
C4—C3—H3	120.0	C9—C16—H16A	109.2
C2—C3—H3	120.0	C17—C16—H16B	109.2
C3—C4—C5	120.7 (2)	C9—C16—H16B	109.2
C3—C4—H4	119.6	H16A—C16—H16B	107.9
C5—C4—H4	119.6	O1—C17—C18	121.08 (18)
C4—C5—C6	119.5 (2)	O1—C17—C16	120.19 (18)
C4—C5—H5	120.3	C18—C17—C16	118.73 (17)
C6—C5—H5	120.3	C19—C18—C23	119.19 (19)
C5—C6—C1	119.83 (19)	C19—C18—C17	121.70 (18)
C5—C6—C7	122.41 (19)	C23—C18—C17	119.11 (18)
C1—C6—C7	117.70 (18)	C20—C19—C18	120.1 (2)
N1—C7—N3	110.27 (18)	C20—C19—H19	120.0
N1—C7—C6	122.88 (17)	C18—C19—H19	120.0
N3—C7—C6	126.76 (17)	C21—C20—C19	120.5 (2)
N2—C8—N3	102.87 (16)	C21—C20—H20	119.7
N2—C8—S1	130.11 (16)	C19—C20—H20	119.7
N3—C8—S1	127.01 (14)	C20—C21—C22	120.1 (2)
N2—C9—C10	112.15 (16)	C20—C21—H21	120.0
N2—C9—C16	107.96 (16)	C22—C21—H21	120.0
C10—C9—C16	111.00 (16)	C23—C22—C21	120.0 (2)
N2—C9—H9	108.6	C23—C22—H22	120.0
C10—C9—H9	108.6	C21—C22—H22	120.0
C16—C9—H9	108.6	C22—C23—C18	120.2 (2)
C11—C10—C15	118.93 (18)	C22—C23—H23	119.9
C11—C10—C9	122.58 (18)	C18—C23—H23	119.9
C15—C10—C9	118.44 (18)

C7—N1—N2—C8	−1.1 (2)	C8—N2—C9—C16	−145.64 (18)
C7—N1—N2—C9	−175.02 (17)	N1—N2—C9—C16	27.4 (2)
C6—C1—C2—C3	−1.1 (3)	N2—C9—C10—C11	18.4 (3)
C1—C2—C3—C4	1.0 (3)	C16—C9—C10—C11	−102.5 (2)
C2—C3—C4—C5	0.4 (3)	N2—C9—C10—C15	−164.09 (17)
C3—C4—C5—C6	−1.8 (3)	C16—C9—C10—C15	75.1 (2)
C4—C5—C6—C1	1.6 (3)	C15—C10—C11—C12	1.3 (3)
C4—C5—C6—C7	−175.21 (18)	C9—C10—C11—C12	178.81 (18)
C2—C1—C6—C5	−0.2 (3)	C10—C11—C12—C13	−0.3 (3)
C2—C1—C6—C7	176.77 (18)	C11—C12—C13—C14	−1.1 (3)
N2—N1—C7—N3	−0.5 (2)	C12—C13—C14—C15	1.5 (3)
N2—N1—C7—C6	176.48 (17)	C13—C14—C15—C10	−0.5 (3)
C8—N3—C7—N1	1.8 (2)	C11—C10—C15—C14	−0.9 (3)
N4—N3—C7—N1	177.66 (16)	C9—C10—C15—C14	−178.48 (17)
C8—N3—C7—C6	−175.02 (18)	N2—C9—C16—C17	53.6 (2)
N4—N3—C7—C6	0.9 (3)	C10—C9—C16—C17	176.93 (16)
C5—C6—C7—N1	140.4 (2)	C9—C16—C17—O1	26.2 (3)
C1—C6—C7—N1	−36.5 (3)	C9—C16—C17—C18	−152.79 (18)
C5—C6—C7—N3	−43.1 (3)	O1—C17—C18—C19	162.63 (19)
C1—C6—C7—N3	139.9 (2)	C16—C17—C18—C19	−18.4 (3)
N1—N2—C8—N3	2.1 (2)	O1—C17—C18—C23	−17.1 (3)
C9—N2—C8—N3	175.54 (16)	C16—C17—C18—C23	161.87 (18)
N1—N2—C8—S1	−177.12 (14)	C23—C18—C19—C20	0.8 (3)
C9—N2—C8—S1	−3.6 (3)	C17—C18—C19—C20	−178.92 (18)
C7—N3—C8—N2	−2.2 (2)	C18—C19—C20—C21	−0.5 (3)
N4—N3—C8—N2	−178.20 (15)	C19—C20—C21—C22	−0.7 (3)
C7—N3—C8—S1	176.97 (14)	C20—C21—C22—C23	1.5 (3)
N4—N3—C8—S1	1.0 (3)	C21—C22—C23—C18	−1.2 (3)
C8—N2—C9—C10	91.8 (2)	C19—C18—C23—C22	0.0 (3)
N1—N2—C9—C10	−95.16 (19)	C17—C18—C23—C22	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.91 (2)	2.39 (2)	2.873 (3)	114 (2)
N4—H4A···S1	0.91 (2)	2.69 (2)	3.194 (2)	116 (2)
N4—H4B···S1ⁱ	0.91 (2)	2.66 (2)	3.490 (2)	151 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₄OS
M_r	400.49
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.4625 (19), 11.340 (2), 11.655 (2)
α, β, γ (°)	111.80 (3), 111.01 (3), 98.91 (3)
V (Å³)	1022.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.965, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	9308, 3590, 2686
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.121, 1.04
No. of reflections	3590
No. of parameters	271
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.91 (2)	2.39 (2)	2.873 (3)	113.7 (16)
N4—H4B···S1ⁱ	0.91 (2)	2.662 (15)	3.490 (2)	151 (2)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

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

References

Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. Web of Science CSD CrossRef IUCr Journals Google Scholar
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