3-(4-Amino-3-ethyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chloro­phen­yl)-1-phenyl­propan-1-one

Wang, Z.; Jia, W.; Liu, Q.; Wang, W.

doi:10.1107/S1600536811025803

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1922

doi:10.1107/S1600536811025803

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3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chlorophenyl)-1-phenylpropan-1-one

Zhi-jian Wang,^a ^* Wei-min Jia,^a Qing-lei Liu ^a and Wei Wang ^a,^b

^aSchool of Perfume and Aroma Technology, Shanghai Istitute 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 17 June 2011; accepted 30 June 2011; online 6 July 2011)

In the title molecule, C₁₉H₁₉ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 86.0 (2) and 65.6 (2)° with the phenyl and chlorophenyl rings, respectively. In the crystal, intermolecular N—H⋯S and N—H⋯O hydrogen bonds link molecules into centrosymmetric dimers, which are further linked into chains in [001] via weak C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₁₉H₁₉ClN₄OS
M_r = 386.89
Monoclinic, C 2/c
a = 29.023 (10) Å
b = 7.561 (2) Å
c = 18.286 (6) Å
β = 109.606 (6)°
V = 3780 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.33 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 = 0.937, T_max = 0.962
22962 measured reflections
4441 independent reflections
3430 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.02
4441 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A⋯S1ⁱ	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A⋯O1ⁱ	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B⋯O1ⁱ	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10⋯Cgⁱⁱ	0.95	2.62	3.508 (2)	156
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y, -z+{\script{3\over 2}}]$ .

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: 10.1107/S1600536811025803/cv5121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025803/cv5121Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025803/cv5121Isup3.cml

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; Gao et al., 2011), we present here the crystal structure of the title compound, (I).

The bond lengths and angles in compound (I) are found to have normal values 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; Gao et al., 2011). The 1,2,4-triazole ring makes the dihedral angles of 94.0 (2) and 65.6 (2)Å with the phenyl ring and the chlorophenyl ring, respectively. The phenyl ring and the chlorophenyl ring form a dihedral angle of 81.8 (2) Å.

In the crystal structure, intermolecular N—H···S and N—H···O (Table 1) hydrogen bonds link molecules into centrosymmetric dimers, which are further linked into chains in [001] via the weak C—H···π interactions (Table 1).

Related literature top

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

Experimental top

The title compound was synthesized by the reaction of the 3-(2-chlorophenyl) -1-phenyl-2-propen-1-one (2.0 mmol) with 4-amino-3-ethyl-4H-1,2,4-triazole- 5-thiol (2.0 mmol) 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 colorless solid in 74% 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 (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. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 55% probability level.

3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)- 3-(2-chlorophenyl)-1-phenylpropan-1-one top

Crystal data top

C₁₉H₁₉ClN₄OS	F(000) = 1616
M_r = 386.89	D_x = 1.360 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6659 reflections
a = 29.023 (10) Å	θ = 1.5–27.9°
b = 7.561 (2) Å	µ = 0.33 mm⁻¹
c = 18.286 (6) Å	T = 113 K
β = 109.606 (6)°	Prism, colourless
V = 3780 (2) Å³	0.20 × 0.18 × 0.12 mm
Z = 8

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4441 independent reflections
Radiation source: rotating anode	3430 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.036
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.8°, θ_min = 1.5°
ϕ and ω scans	h = −38→38
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −9→9
T_min = 0.937, T_max = 0.962	l = −23→23
22962 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0519P)²] where P = (F_o² + 2F_c²)/3
4441 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₉ClN₄OS	V = 3780 (2) Å³
M_r = 386.89	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.023 (10) Å	µ = 0.33 mm⁻¹
b = 7.561 (2) Å	T = 113 K
c = 18.286 (6) Å	0.20 × 0.18 × 0.12 mm
β = 109.606 (6)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4441 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3430 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.962	R_int = 0.036
22962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.37 e Å⁻³
4441 reflections	Δρ_min = −0.23 e Å⁻³
244 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	0.190030 (13)	0.38390 (4)	0.542685 (19)	0.02176 (10)
Cl1	0.019191 (13)	0.34916 (5)	0.39368 (3)	0.03607 (12)
O1	0.15205 (3)	0.13842 (11)	0.34074 (5)	0.0218 (2)
N1	0.16509 (4)	0.51514 (13)	0.39437 (6)	0.0155 (2)
N2	0.18602 (4)	0.59175 (14)	0.34375 (6)	0.0168 (2)
N3	0.24120 (4)	0.53762 (13)	0.45809 (6)	0.0157 (2)
N4	0.28746 (4)	0.53417 (16)	0.51708 (7)	0.0214 (3)
C1	0.19819 (5)	0.47776 (16)	0.46471 (7)	0.0155 (3)
C2	0.23249 (5)	0.60456 (15)	0.38496 (7)	0.0159 (3)
C3	0.11395 (4)	0.45895 (16)	0.36740 (7)	0.0158 (3)
H3	0.1105	0.3619	0.4024	0.019*
C4	0.10039 (5)	0.38305 (16)	0.28491 (7)	0.0175 (3)
H4C	0.0647	0.3617	0.2643	0.021*
H4D	0.1083	0.4716	0.2510	0.021*
C5	0.12692 (4)	0.21139 (16)	0.28159 (7)	0.0159 (3)
C6	0.11887 (4)	0.13029 (16)	0.20350 (7)	0.0159 (3)
C7	0.12856 (4)	−0.05123 (17)	0.20020 (8)	0.0188 (3)
H7	0.1405	−0.1181	0.2468	0.023*
C8	0.12069 (5)	−0.13266 (17)	0.12925 (8)	0.0217 (3)
H8	0.1269	−0.2557	0.1273	0.026*
C9	0.10383 (5)	−0.03574 (19)	0.06100 (8)	0.0255 (3)
H9	0.0985	−0.0924	0.0125	0.031*
C10	0.09476 (5)	0.14466 (19)	0.06362 (8)	0.0255 (3)
H10	0.0837	0.2115	0.0170	0.031*
C11	0.10196 (5)	0.22674 (18)	0.13465 (8)	0.0206 (3)
H11	0.0953	0.3494	0.1363	0.025*
C12	0.07870 (5)	0.60609 (16)	0.36975 (7)	0.0163 (3)
C13	0.03355 (5)	0.56770 (17)	0.37776 (8)	0.0216 (3)
C14	−0.00095 (5)	0.69742 (19)	0.37456 (9)	0.0270 (3)
H14	−0.0313	0.6667	0.3801	0.032*
C15	0.00937 (5)	0.87208 (18)	0.36319 (8)	0.0249 (3)
H15	−0.0141	0.9619	0.3602	0.030*
C16	0.05417 (5)	0.91481 (18)	0.35614 (8)	0.0227 (3)
H16	0.0614	1.0345	0.3485	0.027*
C17	0.08856 (5)	0.78348 (17)	0.36023 (7)	0.0196 (3)
H17	0.1194	0.8153	0.3565	0.024*
C18	0.27199 (5)	0.67570 (18)	0.35804 (8)	0.0203 (3)
H18A	0.2920	0.5760	0.3503	0.024*
H18B	0.2936	0.7530	0.3990	0.024*
C19	0.25249 (5)	0.7808 (2)	0.28262 (9)	0.0284 (3)
H19A	0.2305	0.7060	0.2420	0.043*
H19B	0.2799	0.8195	0.2666	0.043*
H19C	0.2345	0.8845	0.2908	0.043*
H4A	0.3003 (6)	0.425 (2)	0.5136 (10)	0.040 (5)*
H4B	0.2814 (6)	0.522 (2)	0.5616 (10)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02654 (19)	0.02354 (19)	0.01549 (17)	−0.00294 (14)	0.00745 (13)	0.00238 (13)
Cl1	0.02154 (19)	0.01854 (19)	0.0719 (3)	−0.00307 (14)	0.02069 (19)	−0.00139 (18)
O1	0.0255 (5)	0.0209 (5)	0.0170 (5)	0.0044 (4)	0.0045 (4)	0.0016 (4)
N1	0.0157 (5)	0.0170 (5)	0.0144 (5)	0.0003 (4)	0.0059 (4)	0.0017 (4)
N2	0.0180 (5)	0.0179 (6)	0.0162 (5)	0.0003 (4)	0.0081 (4)	0.0016 (4)
N3	0.0140 (5)	0.0153 (5)	0.0161 (5)	0.0004 (4)	0.0028 (4)	0.0008 (4)
N4	0.0163 (6)	0.0235 (7)	0.0192 (6)	0.0007 (5)	−0.0010 (5)	0.0016 (5)
C1	0.0179 (6)	0.0130 (6)	0.0152 (6)	0.0001 (5)	0.0049 (5)	−0.0023 (5)
C2	0.0174 (6)	0.0132 (6)	0.0170 (6)	0.0026 (5)	0.0057 (5)	−0.0003 (5)
C3	0.0150 (6)	0.0163 (6)	0.0156 (6)	−0.0007 (5)	0.0045 (5)	−0.0018 (5)
C4	0.0169 (6)	0.0188 (7)	0.0152 (6)	0.0018 (5)	0.0034 (5)	−0.0019 (5)
C5	0.0126 (6)	0.0175 (6)	0.0182 (6)	−0.0024 (5)	0.0060 (5)	−0.0015 (5)
C6	0.0116 (6)	0.0195 (7)	0.0170 (6)	−0.0001 (5)	0.0052 (5)	−0.0017 (5)
C7	0.0173 (7)	0.0196 (7)	0.0219 (7)	−0.0008 (5)	0.0097 (5)	0.0001 (5)
C8	0.0200 (7)	0.0199 (7)	0.0285 (7)	−0.0024 (5)	0.0124 (6)	−0.0054 (6)
C9	0.0231 (7)	0.0336 (8)	0.0204 (7)	0.0000 (6)	0.0081 (6)	−0.0092 (6)
C10	0.0251 (7)	0.0329 (8)	0.0162 (6)	0.0063 (6)	0.0039 (6)	0.0012 (6)
C11	0.0199 (7)	0.0205 (7)	0.0210 (7)	0.0044 (5)	0.0065 (5)	−0.0007 (5)
C12	0.0168 (6)	0.0183 (7)	0.0126 (6)	0.0008 (5)	0.0034 (5)	−0.0026 (5)
C13	0.0182 (7)	0.0168 (7)	0.0282 (7)	−0.0029 (5)	0.0056 (6)	−0.0038 (6)
C14	0.0148 (7)	0.0259 (8)	0.0401 (9)	−0.0008 (6)	0.0087 (6)	−0.0052 (7)
C15	0.0211 (7)	0.0216 (7)	0.0304 (8)	0.0071 (6)	0.0068 (6)	−0.0024 (6)
C16	0.0296 (8)	0.0168 (7)	0.0227 (7)	0.0026 (6)	0.0102 (6)	0.0017 (6)
C17	0.0226 (7)	0.0209 (7)	0.0178 (6)	0.0011 (5)	0.0101 (5)	0.0008 (5)
C18	0.0172 (6)	0.0221 (7)	0.0232 (7)	0.0013 (5)	0.0090 (5)	0.0012 (6)
C19	0.0258 (8)	0.0328 (8)	0.0307 (8)	0.0029 (6)	0.0147 (6)	0.0111 (7)

Geometric parameters (Å, º) top

S1—C1	1.6792 (14)	C8—C9	1.387 (2)
Cl1—C13	1.7521 (14)	C8—H8	0.9500
O1—C5	1.2151 (15)	C9—C10	1.393 (2)
N1—C1	1.3519 (16)	C9—H9	0.9500
N1—N2	1.3922 (14)	C10—C11	1.3906 (19)
N1—C3	1.4613 (16)	C10—H10	0.9500
N2—C2	1.3092 (16)	C11—H11	0.9500
N3—C1	1.3709 (16)	C12—C17	1.3945 (17)
N3—C2	1.3716 (16)	C12—C13	1.3970 (19)
N3—N4	1.4123 (15)	C13—C14	1.3886 (19)
N4—H4A	0.914 (18)	C14—C15	1.385 (2)
N4—H4B	0.892 (18)	C14—H14	0.9500
C2—C18	1.4916 (18)	C15—C16	1.3873 (19)
C3—C12	1.5218 (17)	C15—H15	0.9500
C3—C4	1.5366 (17)	C16—C17	1.3920 (19)
C3—H3	1.0000	C16—H16	0.9500
C4—C5	1.5207 (17)	C17—H17	0.9500
C4—H4C	0.9900	C18—C19	1.5265 (19)
C4—H4D	0.9900	C18—H18A	0.9900
C5—C6	1.4987 (17)	C18—H18B	0.9900
C6—C11	1.3939 (18)	C19—H19A	0.9800
C6—C7	1.4062 (18)	C19—H19B	0.9800
C7—C8	1.3840 (18)	C19—H19C	0.9800
C7—H7	0.9500

C1—N1—N2	112.97 (10)	C8—C9—C10	120.00 (13)
C1—N1—C3	125.26 (11)	C8—C9—H9	120.0
N2—N1—C3	121.12 (10)	C10—C9—H9	120.0
C2—N2—N1	104.06 (10)	C11—C10—C9	119.88 (13)
C1—N3—C2	109.41 (10)	C11—C10—H10	120.1
C1—N3—N4	125.93 (11)	C9—C10—H10	120.1
C2—N3—N4	124.65 (11)	C10—C11—C6	120.47 (12)
N3—N4—H4A	105.6 (10)	C10—C11—H11	119.8
N3—N4—H4B	105.7 (10)	C6—C11—H11	119.8
H4A—N4—H4B	100.5 (14)	C17—C12—C13	116.87 (11)
N1—C1—N3	102.97 (11)	C17—C12—C3	122.10 (12)
N1—C1—S1	129.69 (10)	C13—C12—C3	120.95 (11)
N3—C1—S1	127.34 (10)	C14—C13—C12	122.49 (13)
N2—C2—N3	110.57 (11)	C14—C13—Cl1	117.70 (11)
N2—C2—C18	126.44 (12)	C12—C13—Cl1	119.81 (10)
N3—C2—C18	122.97 (11)	C15—C14—C13	119.38 (13)
N1—C3—C12	113.22 (10)	C15—C14—H14	120.3
N1—C3—C4	109.66 (10)	C13—C14—H14	120.3
C12—C3—C4	110.33 (10)	C14—C15—C16	119.51 (12)
N1—C3—H3	107.8	C14—C15—H15	120.2
C12—C3—H3	107.8	C16—C15—H15	120.2
C4—C3—H3	107.8	C15—C16—C17	120.43 (13)
C5—C4—C3	113.05 (10)	C15—C16—H16	119.8
C5—C4—H4C	109.0	C17—C16—H16	119.8
C3—C4—H4C	109.0	C16—C17—C12	121.28 (13)
C5—C4—H4D	109.0	C16—C17—H17	119.4
C3—C4—H4D	109.0	C12—C17—H17	119.4
H4C—C4—H4D	107.8	C2—C18—C19	113.14 (11)
O1—C5—C6	121.16 (11)	C2—C18—H18A	108.9
O1—C5—C4	120.85 (11)	C19—C18—H18A	108.9
C6—C5—C4	117.91 (10)	C2—C18—H18B	109.0
C11—C6—C7	119.13 (12)	C19—C18—H18B	108.9
C11—C6—C5	122.79 (11)	H18A—C18—H18B	107.8
C7—C6—C5	118.08 (11)	C18—C19—H19A	109.5
C8—C7—C6	120.12 (12)	C18—C19—H19B	109.5
C8—C7—H7	119.9	H19A—C19—H19B	109.5
C6—C7—H7	119.9	C18—C19—H19C	109.5
C7—C8—C9	120.39 (13)	H19A—C19—H19C	109.5
C7—C8—H8	119.8	H19B—C19—H19C	109.5
C9—C8—H8	119.8

C1—N1—N2—C2	−1.44 (13)	C4—C5—C6—C7	−158.52 (11)
C3—N1—N2—C2	−172.66 (10)	C11—C6—C7—C8	−0.87 (18)
N2—N1—C1—N3	1.50 (13)	C5—C6—C7—C8	178.65 (11)
C3—N1—C1—N3	172.29 (10)	C6—C7—C8—C9	0.85 (19)
N2—N1—C1—S1	−179.21 (9)	C7—C8—C9—C10	0.1 (2)
C3—N1—C1—S1	−8.41 (19)	C8—C9—C10—C11	−0.9 (2)
C2—N3—C1—N1	−0.99 (13)	C9—C10—C11—C6	0.9 (2)
N4—N3—C1—N1	178.19 (11)	C7—C6—C11—C10	−0.01 (19)
C2—N3—C1—S1	179.70 (9)	C5—C6—C11—C10	−179.51 (12)
N4—N3—C1—S1	−1.12 (18)	N1—C3—C12—C17	29.90 (17)
N1—N2—C2—N3	0.73 (13)	C4—C3—C12—C17	−93.44 (14)
N1—N2—C2—C18	178.95 (11)	N1—C3—C12—C13	−153.36 (12)
C1—N3—C2—N2	0.16 (14)	C4—C3—C12—C13	83.30 (15)
N4—N3—C2—N2	−179.04 (11)	C17—C12—C13—C14	1.6 (2)
C1—N3—C2—C18	−178.13 (11)	C3—C12—C13—C14	−175.28 (12)
N4—N3—C2—C18	2.68 (18)	C17—C12—C13—Cl1	−177.57 (10)
C1—N1—C3—C12	102.95 (14)	C3—C12—C13—Cl1	5.53 (17)
N2—N1—C3—C12	−86.96 (13)	C12—C13—C14—C15	−0.1 (2)
C1—N1—C3—C4	−133.35 (12)	Cl1—C13—C14—C15	179.07 (11)
N2—N1—C3—C4	36.74 (14)	C13—C14—C15—C16	−0.8 (2)
N1—C3—C4—C5	66.84 (13)	C14—C15—C16—C17	0.2 (2)
C12—C3—C4—C5	−167.78 (10)	C15—C16—C17—C12	1.4 (2)
C3—C4—C5—O1	6.81 (17)	C13—C12—C17—C16	−2.24 (19)
C3—C4—C5—C6	−176.50 (10)	C3—C12—C17—C16	174.63 (12)
O1—C5—C6—C11	−162.34 (12)	N2—C2—C18—C19	15.46 (18)
C4—C5—C6—C11	20.98 (17)	N3—C2—C18—C19	−166.53 (12)
O1—C5—C6—C7	18.16 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A···S1ⁱ	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A···O1ⁱ	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B···O1ⁱ	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10···Cgⁱⁱ	0.95	2.62	3.508 (2)	156

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉ClN₄OS
M_r	386.89
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	29.023 (10), 7.561 (2), 18.286 (6)
β (°)	109.606 (6)
V (Å³)	3780 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.937, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	22962, 4441, 3430
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.02
No. of reflections	4441
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.23

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A···S1ⁱ	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A···O1ⁱ	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B···O1ⁱ	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10···Cgⁱⁱ	0.95	2.62	3.508 (2)	156

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x, y, −z+3/2.

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
Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495–o496. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, o2224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o1922

doi:10.1107/S1600536811025803

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(4-Amino-3-ethyl-5-sulfanyl­­idene-4,5-di­hydro-1H-1,2,4-triazol-1-yl)-3-(2-chloro­phen­yl)-1-phenyl­propan-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chlorophenyl)-1-phenylpropan-1-one