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

Wang, W.; Liu, Q.; Jia, X.; Zhang, J.; Gao, Y.

doi:10.1107/S1600536811023993

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1793

doi:10.1107/S1600536811023993

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

Wei Wang,^a,^b Qing-lei Liu,^a Xiao-yu Jia,^b Jing-jing Zhang ^b and Yan Gao ^b ^*

^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 29 May 2011; accepted 19 June 2011; online 25 June 2011)

In the title molecule, C₂₄H₂₁ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 37.2 (2), 71.9 (2) and 84.9 (2) ° with the three benzene rings. In the crystal, weak intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers.

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

C₂₄H₂₁ClN₄OS
M_r = 448.96
Monoclinic, P 2₁ /n
a = 10.9873 (12) Å
b = 11.8220 (14) Å
c = 17.438 (3) Å
β = 94.828 (7)°
V = 2257.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 K
0.30 × 0.08 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.919, T_max = 0.978
22007 measured reflections
4989 independent reflections
3972 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.145
S = 1.11
4989 reflections
289 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯S1ⁱ	0.93 (3)	2.77 (3)	3.526 (3)	139 (2)
Symmetry code: (i) -x, -y+1, -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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023993/cv5109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023993/cv5109Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023993/cv5109Isup3.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), we present here the crystal structure of the title compound, (I).

In (I) (Fig.1), all bond lengths and angles are normal and comparable with those observed in related structures (Al-Tamimi et al., 2010; Fun et al., 2009; Tan et al., 2010; Wang et al., 2011). The C1 atom in the triazole ring deviates from the normal C_sp² hybridization state having the bond angles of 102.49 (19)° (N1—C1—N3) and 129.67 (18)° (N1—C1—S1). The three benzene rings in the molecule are inclined with respect to the 1,2,4-triazole ring [dihedral angles of 37.7 (2)° (C18—C23), 71.9 (2)° (C6—C11) and 84.9 (2)% (C12—C17)]. Benzene ring A (C18—C23) attached to the triazole ring makes the dihedral angles of 97.3 (2) and 84.7 (2)° with the benzene rings B (C6—C11) and C (C12—C17), respectively. Rings B and C form a dihedral angle of 60.4 (2)°.

In the crystal structure, intermolecular N—H···S 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 derivates, 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 3-(2-chlorophenyl)-1- (4-methylphenyl)-2-propen-1-one (2.0 mmol) with 4-amino-3-phenyl-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 colourless solid in 75% 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-(4-methylphenyl)-5-sulfanylidene-4,5-dihydro-1H- 1,2,4-triazol-1-yl]-3-(2-chlorophenyl)-1-phenylpropan-1-one top

Crystal data top

C₂₄H₂₁ClN₄OS	F(000) = 936
M_r = 448.96	D_x = 1.321 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6624 reflections
a = 10.9873 (12) Å	θ = 1.7–27.2°
b = 11.8220 (14) Å	µ = 0.29 mm⁻¹
c = 17.438 (3) Å	T = 113 K
β = 94.828 (7)°	Prism, colourless
V = 2257.1 (5) Å³	0.30 × 0.08 × 0.08 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4989 independent reflections
Radiation source: rotating anode	3972 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.065
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.2°, θ_min = 2.1°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
T_min = 0.919, T_max = 0.978	l = −20→22
22007 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.058P)² + 0.3265P] where P = (F_o² + 2F_c²)/3
4989 reflections	(Δ/σ)_max = 0.002
289 parameters	Δρ_max = 0.93 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

C₂₄H₂₁ClN₄OS	V = 2257.1 (5) Å³
M_r = 448.96	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9873 (12) Å	µ = 0.29 mm⁻¹
b = 11.8220 (14) Å	T = 113 K
c = 17.438 (3) Å	0.30 × 0.08 × 0.08 mm
β = 94.828 (7)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4989 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3972 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.978	R_int = 0.065
22007 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.93 e Å⁻³
4989 reflections	Δρ_min = −0.76 e Å⁻³
289 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	0.02423 (6)	0.49557 (5)	0.11191 (4)	0.03397 (19)
Cl1	−0.32308 (8)	0.64505 (9)	0.19347 (5)	0.0734 (3)
O1	0.05692 (16)	0.81675 (14)	0.24353 (10)	0.0345 (4)
N1	0.00694 (16)	0.72168 (16)	0.08127 (10)	0.0235 (4)
N2	0.06436 (17)	0.80772 (15)	0.04491 (11)	0.0248 (4)
N3	0.15533 (16)	0.64405 (16)	0.03124 (11)	0.0260 (4)
N4	0.2416 (2)	0.5653 (2)	0.00864 (18)	0.0378 (6)
C1	0.0594 (2)	0.61979 (19)	0.07433 (13)	0.0253 (5)
C2	0.15630 (19)	0.75776 (19)	0.01521 (13)	0.0234 (5)
C3	−0.1037 (2)	0.7430 (2)	0.12081 (13)	0.0254 (5)
H3	−0.1025	0.6921	0.1667	0.030*
C4	−0.1022 (2)	0.86520 (19)	0.14850 (13)	0.0265 (5)
H4C	−0.1026	0.9162	0.1034	0.032*
H4D	−0.1772	0.8801	0.1745	0.032*
C5	0.0087 (2)	0.8918 (2)	0.20371 (13)	0.0248 (5)
C6	0.05468 (19)	1.01009 (19)	0.20922 (12)	0.0238 (5)
C7	0.1565 (2)	1.0353 (2)	0.25923 (15)	0.0358 (6)
H7	0.1963	0.9764	0.2888	0.043*
C8	0.2006 (3)	1.1444 (2)	0.26661 (16)	0.0448 (7)
H8	0.2718	1.1598	0.2998	0.054*
C9	0.1412 (2)	1.2315 (2)	0.22572 (16)	0.0422 (7)
H9	0.1695	1.3071	0.2320	0.051*
C10	0.0406 (2)	1.2074 (2)	0.17581 (16)	0.0412 (7)
H10	−0.0002	1.2667	0.1473	0.049*
C11	−0.0015 (2)	1.0977 (2)	0.16691 (14)	0.0321 (6)
H11	−0.0698	1.0821	0.1314	0.038*
C12	−0.2167 (2)	0.7165 (2)	0.06798 (14)	0.0276 (5)
C13	−0.3211 (2)	0.6709 (2)	0.09597 (16)	0.0413 (7)
C14	−0.4247 (2)	0.6455 (2)	0.0482 (2)	0.0495 (8)
H14	−0.4943	0.6136	0.0689	0.059*
C15	−0.4263 (3)	0.6667 (2)	−0.02916 (19)	0.0473 (8)
H15	−0.4967	0.6487	−0.0623	0.057*
C16	−0.3258 (3)	0.7140 (2)	−0.05900 (16)	0.0416 (7)
H16	−0.3274	0.7299	−0.1125	0.050*
C17	−0.2220 (2)	0.7383 (2)	−0.01052 (15)	0.0337 (6)
H17	−0.1530	0.7706	−0.0316	0.040*
C18	0.24385 (19)	0.8188 (2)	−0.02880 (13)	0.0249 (5)
C19	0.2891 (2)	0.7736 (2)	−0.09446 (14)	0.0320 (6)
H19	0.2670	0.6993	−0.1110	0.038*
C20	0.3669 (2)	0.8382 (2)	−0.13548 (14)	0.0361 (6)
H20	0.3978	0.8068	−0.1801	0.043*
C21	0.4010 (2)	0.9470 (2)	−0.11339 (14)	0.0345 (6)
C22	0.3555 (2)	0.9906 (2)	−0.04791 (15)	0.0317 (6)
H22	0.3780	1.0649	−0.0314	0.038*
C23	0.2777 (2)	0.9280 (2)	−0.00594 (14)	0.0279 (5)
H23	0.2472	0.9598	0.0387	0.033*
C24	0.4854 (3)	1.0158 (3)	−0.15917 (17)	0.0521 (8)
H24A	0.5002	1.0896	−0.1345	0.078*
H24B	0.4476	1.0268	−0.2116	0.078*
H24C	0.5631	0.9757	−0.1611	0.078*
H4A	0.257 (3)	0.526 (3)	0.0465 (18)	0.046 (10)*
H4B	0.201 (3)	0.518 (2)	−0.0274 (16)	0.040 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0322 (3)	0.0223 (4)	0.0465 (4)	−0.0008 (3)	−0.0020 (3)	0.0056 (3)
Cl1	0.0556 (5)	0.1144 (8)	0.0517 (5)	−0.0340 (5)	0.0137 (4)	0.0089 (5)
O1	0.0406 (10)	0.0255 (10)	0.0351 (10)	0.0017 (8)	−0.0099 (8)	0.0046 (8)
N1	0.0227 (10)	0.0214 (10)	0.0258 (10)	0.0006 (8)	−0.0008 (7)	0.0011 (8)
N2	0.0253 (10)	0.0208 (10)	0.0283 (11)	0.0008 (8)	0.0015 (8)	0.0007 (8)
N3	0.0202 (10)	0.0208 (11)	0.0364 (12)	0.0037 (8)	−0.0021 (8)	−0.0019 (9)
N4	0.0296 (12)	0.0249 (13)	0.0590 (17)	0.0091 (10)	0.0051 (11)	−0.0017 (12)
C1	0.0211 (11)	0.0233 (13)	0.0299 (13)	0.0008 (9)	−0.0067 (9)	−0.0037 (10)
C2	0.0222 (11)	0.0216 (12)	0.0254 (12)	0.0027 (9)	−0.0044 (9)	−0.0011 (9)
C3	0.0259 (12)	0.0256 (13)	0.0247 (12)	−0.0005 (10)	0.0023 (9)	−0.0007 (10)
C4	0.0246 (12)	0.0261 (13)	0.0284 (13)	0.0019 (10)	0.0000 (9)	−0.0029 (10)
C5	0.0246 (12)	0.0273 (13)	0.0226 (12)	0.0033 (10)	0.0017 (9)	−0.0028 (10)
C6	0.0225 (11)	0.0271 (13)	0.0221 (12)	0.0001 (9)	0.0033 (9)	0.0000 (9)
C7	0.0364 (14)	0.0276 (14)	0.0413 (15)	0.0038 (11)	−0.0102 (11)	0.0013 (12)
C8	0.0398 (16)	0.0377 (17)	0.0529 (18)	−0.0070 (13)	−0.0200 (13)	0.0024 (13)
C9	0.0423 (15)	0.0306 (15)	0.0521 (18)	−0.0129 (12)	−0.0046 (13)	0.0048 (13)
C10	0.0408 (15)	0.0325 (15)	0.0476 (17)	−0.0059 (12)	−0.0124 (12)	0.0124 (13)
C11	0.0292 (13)	0.0299 (14)	0.0352 (14)	−0.0032 (10)	−0.0088 (10)	0.0087 (11)
C12	0.0230 (12)	0.0246 (13)	0.0346 (14)	0.0003 (10)	−0.0006 (9)	−0.0075 (11)
C13	0.0343 (14)	0.0441 (17)	0.0453 (16)	−0.0057 (12)	0.0026 (12)	−0.0060 (13)
C14	0.0254 (14)	0.0420 (18)	0.080 (2)	−0.0056 (12)	−0.0003 (14)	−0.0081 (16)
C15	0.0326 (15)	0.0358 (16)	0.069 (2)	0.0100 (12)	−0.0210 (14)	−0.0123 (15)
C16	0.0424 (16)	0.0352 (16)	0.0441 (16)	0.0098 (12)	−0.0157 (12)	−0.0064 (13)
C17	0.0323 (13)	0.0302 (14)	0.0369 (15)	0.0044 (11)	−0.0067 (10)	−0.0023 (11)
C18	0.0188 (11)	0.0264 (13)	0.0290 (12)	0.0058 (9)	−0.0016 (9)	0.0037 (10)
C19	0.0290 (13)	0.0350 (15)	0.0313 (14)	0.0040 (11)	−0.0022 (10)	−0.0027 (11)
C20	0.0304 (13)	0.0516 (18)	0.0265 (13)	0.0094 (12)	0.0028 (10)	0.0013 (12)
C21	0.0227 (12)	0.0462 (17)	0.0339 (14)	0.0019 (11)	−0.0010 (10)	0.0110 (12)
C22	0.0270 (13)	0.0299 (14)	0.0377 (14)	−0.0024 (10)	−0.0001 (10)	0.0065 (11)
C23	0.0264 (12)	0.0278 (14)	0.0293 (13)	0.0043 (10)	0.0016 (9)	0.0013 (10)
C24	0.0441 (17)	0.071 (2)	0.0422 (18)	−0.0056 (15)	0.0100 (13)	0.0162 (15)

Geometric parameters (Å, º) top

S1—C1	1.667 (2)	C10—C11	1.381 (3)
Cl1—C13	1.730 (3)	C10—H10	0.9500
O1—C5	1.220 (3)	C11—H11	0.9500
N1—C1	1.345 (3)	C12—C17	1.390 (3)
N1—N2	1.379 (2)	C12—C13	1.391 (3)
N1—C3	1.468 (3)	C13—C14	1.387 (4)
N2—C2	1.314 (3)	C14—C15	1.371 (4)
N3—C2	1.373 (3)	C14—H14	0.9500
N3—C1	1.375 (3)	C15—C16	1.378 (4)
N3—N4	1.409 (3)	C15—H15	0.9500
N4—H4A	0.81 (3)	C16—C17	1.392 (3)
N4—H4B	0.93 (3)	C16—H16	0.9500
C2—C18	1.469 (3)	C17—H17	0.9500
C3—C12	1.516 (3)	C18—C23	1.393 (3)
C3—C4	1.523 (3)	C18—C19	1.393 (3)
C3—H3	1.0000	C19—C20	1.388 (3)
C4—C5	1.520 (3)	C19—H19	0.9500
C4—H4C	0.9900	C20—C21	1.385 (4)
C4—H4D	0.9900	C20—H20	0.9500
C5—C6	1.487 (3)	C21—C22	1.384 (3)
C6—C11	1.386 (3)	C21—C24	1.511 (4)
C6—C7	1.392 (3)	C22—C23	1.385 (3)
C7—C8	1.381 (4)	C22—H22	0.9500
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.384 (4)	C24—H24A	0.9800
C8—H8	0.9500	C24—H24B	0.9800
C9—C10	1.378 (4)	C24—H24C	0.9800
C9—H9	0.9500

C1—N1—N2	113.77 (18)	C10—C11—C6	120.8 (2)
C1—N1—C3	124.99 (19)	C10—C11—H11	119.6
N2—N1—C3	121.21 (18)	C6—C11—H11	119.6
C2—N2—N1	104.26 (18)	C17—C12—C13	116.8 (2)
C2—N3—C1	109.56 (18)	C17—C12—C3	121.6 (2)
C2—N3—N4	124.99 (19)	C13—C12—C3	121.6 (2)
C1—N3—N4	125.4 (2)	C14—C13—C12	122.2 (3)
N3—N4—H4A	104 (2)	C14—C13—Cl1	118.3 (2)
N3—N4—H4B	107.0 (17)	C12—C13—Cl1	119.5 (2)
H4A—N4—H4B	105 (3)	C15—C14—C13	119.5 (3)
N1—C1—N3	102.49 (19)	C15—C14—H14	120.2
N1—C1—S1	129.67 (18)	C13—C14—H14	120.2
N3—C1—S1	127.75 (17)	C14—C15—C16	120.1 (3)
N2—C2—N3	109.91 (19)	C14—C15—H15	119.9
N2—C2—C18	123.0 (2)	C16—C15—H15	119.9
N3—C2—C18	127.1 (2)	C15—C16—C17	119.7 (3)
N1—C3—C12	110.34 (18)	C15—C16—H16	120.1
N1—C3—C4	108.91 (18)	C17—C16—H16	120.1
C12—C3—C4	112.02 (18)	C12—C17—C16	121.6 (3)
N1—C3—H3	108.5	C12—C17—H17	119.2
C12—C3—H3	108.5	C16—C17—H17	119.2
C4—C3—H3	108.5	C23—C18—C19	119.0 (2)
C5—C4—C3	112.57 (19)	C23—C18—C2	118.5 (2)
C5—C4—H4C	109.1	C19—C18—C2	122.4 (2)
C3—C4—H4C	109.1	C20—C19—C18	119.4 (2)
C5—C4—H4D	109.1	C20—C19—H19	120.3
C3—C4—H4D	109.1	C18—C19—H19	120.3
H4C—C4—H4D	107.8	C21—C20—C19	122.1 (2)
O1—C5—C6	121.2 (2)	C21—C20—H20	119.0
O1—C5—C4	119.8 (2)	C19—C20—H20	119.0
C6—C5—C4	119.02 (19)	C22—C21—C20	117.9 (2)
C11—C6—C7	118.2 (2)	C22—C21—C24	121.0 (3)
C11—C6—C5	122.3 (2)	C20—C21—C24	121.1 (2)
C7—C6—C5	119.5 (2)	C21—C22—C23	121.2 (2)
C8—C7—C6	121.0 (2)	C21—C22—H22	119.4
C8—C7—H7	119.5	C23—C22—H22	119.4
C6—C7—H7	119.5	C22—C23—C18	120.4 (2)
C7—C8—C9	120.0 (2)	C22—C23—H23	119.8
C7—C8—H8	120.0	C18—C23—H23	119.8
C9—C8—H8	120.0	C21—C24—H24A	109.5
C10—C9—C8	119.4 (3)	C21—C24—H24B	109.5
C10—C9—H9	120.3	H24A—C24—H24B	109.5
C8—C9—H9	120.3	C21—C24—H24C	109.5
C9—C10—C11	120.6 (2)	H24A—C24—H24C	109.5
C9—C10—H10	119.7	H24B—C24—H24C	109.5
C11—C10—H10	119.7

C1—N1—N2—C2	−0.7 (2)	C9—C10—C11—C6	1.5 (4)
C3—N1—N2—C2	−178.69 (18)	C7—C6—C11—C10	−1.7 (4)
N2—N1—C1—N3	0.1 (2)	C5—C6—C11—C10	177.3 (2)
C3—N1—C1—N3	178.02 (19)	N1—C3—C12—C17	−36.0 (3)
N2—N1—C1—S1	176.98 (16)	C4—C3—C12—C17	85.5 (3)
C3—N1—C1—S1	−5.1 (3)	N1—C3—C12—C13	145.1 (2)
C2—N3—C1—N1	0.5 (2)	C4—C3—C12—C13	−93.4 (3)
N4—N3—C1—N1	178.9 (2)	C17—C12—C13—C14	1.6 (4)
C2—N3—C1—S1	−176.44 (17)	C3—C12—C13—C14	−179.5 (2)
N4—N3—C1—S1	2.0 (3)	C17—C12—C13—Cl1	−178.24 (19)
N1—N2—C2—N3	1.0 (2)	C3—C12—C13—Cl1	0.7 (3)
N1—N2—C2—C18	−179.51 (19)	C12—C13—C14—C15	−0.7 (4)
C1—N3—C2—N2	−1.0 (2)	Cl1—C13—C14—C15	179.1 (2)
N4—N3—C2—N2	−179.4 (2)	C13—C14—C15—C16	−0.7 (4)
C1—N3—C2—C18	179.5 (2)	C14—C15—C16—C17	1.1 (4)
N4—N3—C2—C18	1.1 (4)	C13—C12—C17—C16	−1.1 (4)
C1—N1—C3—C12	−82.3 (3)	C3—C12—C17—C16	180.0 (2)
N2—N1—C3—C12	95.4 (2)	C15—C16—C17—C12	−0.3 (4)
C1—N1—C3—C4	154.4 (2)	N2—C2—C18—C23	36.4 (3)
N2—N1—C3—C4	−27.9 (3)	N3—C2—C18—C23	−144.2 (2)
N1—C3—C4—C5	−59.6 (2)	N2—C2—C18—C19	−140.3 (2)
C12—C3—C4—C5	178.04 (19)	N3—C2—C18—C19	39.1 (3)
C3—C4—C5—O1	−28.0 (3)	C23—C18—C19—C20	0.1 (3)
C3—C4—C5—C6	153.21 (19)	C2—C18—C19—C20	176.8 (2)
O1—C5—C6—C11	−177.3 (2)	C18—C19—C20—C21	−0.3 (4)
C4—C5—C6—C11	1.4 (3)	C19—C20—C21—C22	0.4 (4)
O1—C5—C6—C7	1.7 (3)	C19—C20—C21—C24	−179.8 (2)
C4—C5—C6—C7	−179.6 (2)	C20—C21—C22—C23	−0.4 (4)
C11—C6—C7—C8	0.0 (4)	C24—C21—C22—C23	179.7 (2)
C5—C6—C7—C8	−179.1 (2)	C21—C22—C23—C18	0.3 (4)
C6—C7—C8—C9	2.0 (4)	C19—C18—C23—C22	−0.1 (3)
C7—C8—C9—C10	−2.3 (4)	C2—C18—C23—C22	−176.9 (2)
C8—C9—C10—C11	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1ⁱ	0.93 (3)	2.77 (3)	3.526 (3)	139 (2)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁ClN₄OS
M_r	448.96
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	10.9873 (12), 11.8220 (14), 17.438 (3)
β (°)	94.828 (7)
V (Å³)	2257.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.08 × 0.08

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.919, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	22007, 4989, 3972
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.145, 1.11
No. of reflections	4989
No. of parameters	289
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.93, −0.76

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1ⁱ	0.93 (3)	2.77 (3)	3.526 (3)	139 (2)

Symmetry code: (i) −x, −y+1, −z.

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
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 7| July 2011| Page o1793

doi:10.1107/S1600536811023993

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

3-[4-Amino-3-(4-methyl­phen­yl)-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

References

organic compounds

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