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

Gao, Y.; Zhang, L.; Wang, H.

doi:10.1107/S1600536811023750

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1794

doi:10.1107/S1600536811023750

Open

access

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

Yan Gao,^a Li-hua Zhang ^a and He-wen Wang ^b ^*

^aSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, 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 29 May 2011; accepted 17 June 2011; online 25 June 2011)

In the title molecule, C₂₃H₁₉ClN₄OS, the 1,2,4-triazole ring forms dihedral angles of 46.5 (2), 87.4 (2) and 80.9 (2) Å with the three six-membered rings. Weak intermolecular N—H⋯S and C—H⋯O hydrogen bonds consolidate the crystal packing.

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

C₂₃H₁₉ClN₄OS
M_r = 434.93
Triclinic, $[P \overline 1]$
a = 10.559 (3) Å
b = 10.787 (4) Å
c = 10.835 (3) Å
α = 99.582 (2)°
β = 96.638 (4)°
γ = 115.267 (3)°
V = 1076.2 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 113 K
0.20 × 0.20 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.943, T_max = 0.960
13931 measured reflections
5111 independent reflections
3433 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.079
S = 0.95
5111 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 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—H4B⋯S1ⁱ	0.945 (18)	2.714 (17)	3.4928 (17)	140.2 (12)
C7—H7⋯O1ⁱⁱ	0.95	2.52	3.436 (2)	161
C21—H21⋯O1ⁱⁱⁱ	0.95	2.53	3.415 (2)	156
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y, -z; (iii) 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/S1600536811023750/cv5107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023750/cv5107Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023750/cv5107Isup3.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 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.002 (2) Å. The C1 atom in the triazole ring deviates from the normal C_sp² hybridization state having the bond angles of 102.56 (10)° (N1—C1—N3) and 129.94 (10)° (N1—C1—S1). There are three benzene rings in the molecule. The three benzene rings are inclined with respect to the 1,2,4-triazole ring [dihedral angles of 46.5 (2)° (C18—C23), 87.4 (2)° (C6—C11) and 80.9 (2)% (C12—C17)]. Benzene ring A (C18—C23) attached to the triazole ring makes the dihedral angle of 90.6 (2) and 126.9 (2)° with the benzene rings B (C6—C11) and C (C12—C17), respectively. Ring B and ring C form a dihedral angle 93.6 (2)°.

In the crystal structure, weak intermolecular N—H···S and C—H···O hydrogen bonds (Table 1) consolidate the crystal packing.

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

Crystal data top

C₂₃H₁₉ClN₄OS	Z = 2
M_r = 434.93	F(000) = 452
Triclinic, P1	D_x = 1.342 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.559 (3) Å	Cell parameters from 3478 reflections
b = 10.787 (4) Å	θ = 1.9–27.9°
c = 10.835 (3) Å	µ = 0.30 mm⁻¹
α = 99.582 (2)°	T = 113 K
β = 96.638 (4)°	Prism, colourless
γ = 115.267 (3)°	0.20 × 0.20 × 0.14 mm
V = 1076.2 (6) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5111 independent reflections
Radiation source: rotating anode	3433 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.038
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −14→14
T_min = 0.943, T_max = 0.960	l = −14→14
13931 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
5111 reflections	(Δ/σ)_max = 0.001
279 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₁₉ClN₄OS	γ = 115.267 (3)°
M_r = 434.93	V = 1076.2 (6) Å³
Triclinic, P1	Z = 2
a = 10.559 (3) Å	Mo Kα radiation
b = 10.787 (4) Å	µ = 0.30 mm⁻¹
c = 10.835 (3) Å	T = 113 K
α = 99.582 (2)°	0.20 × 0.20 × 0.14 mm
β = 96.638 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5111 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3433 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.960	R_int = 0.038
13931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.40 e Å⁻³
5111 reflections	Δρ_min = −0.29 e Å⁻³
279 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	0.87508 (4)	0.30026 (4)	0.43912 (3)	0.02271 (9)
Cl1	1.14768 (4)	0.15222 (4)	0.21807 (4)	0.04566 (13)
O1	0.70047 (10)	0.13775 (10)	0.05439 (9)	0.0298 (2)
N1	0.90922 (11)	0.39665 (11)	0.22109 (10)	0.0171 (2)
N2	0.88351 (11)	0.48767 (11)	0.15864 (10)	0.0184 (2)
N3	0.81314 (11)	0.49054 (11)	0.34152 (9)	0.0175 (2)
N4	0.75491 (14)	0.52876 (15)	0.44374 (11)	0.0252 (3)
C1	0.86846 (13)	0.39575 (13)	0.33424 (11)	0.0174 (3)
C2	0.82420 (13)	0.54367 (13)	0.23458 (11)	0.0172 (3)
C3	0.98141 (13)	0.31632 (13)	0.17006 (12)	0.0179 (3)
H3	0.9499	0.2301	0.2049	0.021*
C4	0.93753 (13)	0.26682 (13)	0.02470 (11)	0.0183 (3)
H4C	0.9598	0.3500	−0.0121	0.022*
H4D	0.9946	0.2203	−0.0067	0.022*
C5	0.77970 (14)	0.16486 (13)	−0.02188 (12)	0.0201 (3)
C6	0.72490 (13)	0.09573 (13)	−0.16117 (12)	0.0191 (3)
C7	0.58247 (14)	−0.00620 (14)	−0.20344 (13)	0.0263 (3)
H7	0.5211	−0.0281	−0.1443	0.032*
C8	0.53048 (15)	−0.07543 (16)	−0.33125 (14)	0.0344 (4)
H8	0.4331	−0.1442	−0.3600	0.041*
C9	0.61981 (16)	−0.04485 (16)	−0.41761 (13)	0.0332 (4)
H9	0.5838	−0.0934	−0.5053	0.040*
C10	0.76108 (16)	0.05597 (14)	−0.37670 (13)	0.0266 (3)
H10	0.8221	0.0770	−0.4362	0.032*
C11	0.81364 (14)	0.12638 (13)	−0.24900 (12)	0.0214 (3)
H11	0.9108	0.1960	−0.2210	0.026*
C12	1.14209 (13)	0.40065 (14)	0.21643 (11)	0.0179 (3)
C13	1.22678 (15)	0.33506 (15)	0.24249 (13)	0.0249 (3)
C14	1.37336 (15)	0.41100 (17)	0.28825 (13)	0.0313 (4)
H14	1.4285	0.3635	0.3066	0.038*
C15	1.43893 (15)	0.55614 (17)	0.30705 (13)	0.0311 (3)
H15	1.5393	0.6090	0.3392	0.037*
C16	1.35845 (15)	0.62377 (16)	0.27904 (13)	0.0292 (3)
H16	1.4036	0.7233	0.2899	0.035*
C17	1.21141 (14)	0.54688 (14)	0.23495 (12)	0.0231 (3)
H17	1.1568	0.5950	0.2170	0.028*
C18	0.77955 (13)	0.65020 (13)	0.20813 (12)	0.0194 (3)
C19	0.70373 (15)	0.63013 (15)	0.08661 (13)	0.0266 (3)
H19	0.6793	0.5474	0.0224	0.032*
C20	0.66390 (17)	0.73115 (18)	0.05937 (15)	0.0378 (4)
H20	0.6110	0.7168	−0.0233	0.045*
C21	0.70075 (18)	0.85272 (17)	0.15195 (16)	0.0407 (4)
H21	0.6734	0.9217	0.1327	0.049*
C22	0.77736 (17)	0.87375 (16)	0.27237 (16)	0.0370 (4)
H22	0.8031	0.9577	0.3356	0.044*
C23	0.81688 (15)	0.77314 (14)	0.30151 (14)	0.0273 (3)
H23	0.8691	0.7877	0.3846	0.033*
H4A	0.7078 (16)	0.4471 (16)	0.4696 (13)	0.031 (4)*
H4B	0.8351 (18)	0.5891 (18)	0.5104 (15)	0.052 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02278 (18)	0.02589 (19)	0.02155 (18)	0.01071 (15)	0.00574 (14)	0.01129 (15)
Cl1	0.0438 (2)	0.0299 (2)	0.0776 (3)	0.02636 (19)	0.0153 (2)	0.0206 (2)
O1	0.0252 (5)	0.0299 (6)	0.0298 (6)	0.0068 (5)	0.0135 (5)	0.0064 (5)
N1	0.0183 (5)	0.0172 (5)	0.0188 (5)	0.0092 (5)	0.0061 (4)	0.0071 (5)
N2	0.0202 (6)	0.0184 (6)	0.0206 (6)	0.0112 (5)	0.0057 (5)	0.0073 (5)
N3	0.0153 (5)	0.0228 (6)	0.0155 (5)	0.0093 (5)	0.0052 (4)	0.0044 (5)
N4	0.0260 (7)	0.0372 (8)	0.0188 (6)	0.0181 (6)	0.0116 (5)	0.0083 (6)
C1	0.0134 (6)	0.0189 (6)	0.0179 (6)	0.0054 (5)	0.0037 (5)	0.0042 (5)
C2	0.0142 (6)	0.0194 (6)	0.0171 (6)	0.0066 (5)	0.0039 (5)	0.0047 (5)
C3	0.0205 (7)	0.0162 (6)	0.0210 (7)	0.0104 (5)	0.0068 (5)	0.0071 (5)
C4	0.0189 (7)	0.0163 (6)	0.0201 (7)	0.0077 (5)	0.0066 (5)	0.0046 (5)
C5	0.0206 (7)	0.0159 (6)	0.0262 (7)	0.0093 (6)	0.0073 (6)	0.0068 (6)
C6	0.0189 (7)	0.0143 (6)	0.0256 (7)	0.0091 (5)	0.0036 (6)	0.0056 (5)
C7	0.0190 (7)	0.0251 (8)	0.0347 (8)	0.0103 (6)	0.0047 (6)	0.0072 (6)
C8	0.0219 (8)	0.0313 (9)	0.0399 (9)	0.0085 (7)	−0.0069 (7)	0.0020 (7)
C9	0.0389 (9)	0.0312 (8)	0.0238 (8)	0.0153 (7)	−0.0066 (7)	0.0029 (7)
C10	0.0355 (8)	0.0227 (7)	0.0230 (7)	0.0131 (6)	0.0053 (6)	0.0096 (6)
C11	0.0231 (7)	0.0153 (6)	0.0247 (7)	0.0077 (6)	0.0028 (6)	0.0060 (6)
C12	0.0202 (7)	0.0224 (7)	0.0143 (6)	0.0116 (6)	0.0060 (5)	0.0053 (5)
C13	0.0285 (8)	0.0271 (8)	0.0273 (7)	0.0177 (6)	0.0100 (6)	0.0107 (6)
C14	0.0275 (8)	0.0485 (10)	0.0308 (8)	0.0271 (8)	0.0091 (7)	0.0132 (7)
C15	0.0189 (7)	0.0444 (10)	0.0271 (8)	0.0124 (7)	0.0048 (6)	0.0069 (7)
C16	0.0223 (7)	0.0271 (8)	0.0317 (8)	0.0064 (6)	0.0059 (6)	0.0037 (6)
C17	0.0212 (7)	0.0234 (7)	0.0261 (7)	0.0115 (6)	0.0042 (6)	0.0061 (6)
C18	0.0182 (6)	0.0215 (7)	0.0242 (7)	0.0108 (6)	0.0123 (6)	0.0100 (6)
C19	0.0310 (8)	0.0337 (8)	0.0255 (7)	0.0206 (7)	0.0130 (6)	0.0120 (6)
C20	0.0488 (10)	0.0559 (11)	0.0347 (9)	0.0396 (9)	0.0199 (8)	0.0254 (8)
C21	0.0553 (11)	0.0414 (10)	0.0577 (11)	0.0382 (9)	0.0363 (10)	0.0324 (9)
C22	0.0443 (10)	0.0237 (8)	0.0515 (11)	0.0181 (7)	0.0276 (9)	0.0114 (8)
C23	0.0256 (8)	0.0253 (8)	0.0320 (8)	0.0111 (6)	0.0122 (6)	0.0069 (6)

Geometric parameters (Å, º) top

S1—C1	1.6705 (13)	C9—C10	1.381 (2)
Cl1—C13	1.7397 (16)	C9—H9	0.9500
O1—C5	1.2247 (14)	C10—C11	1.3828 (18)
N1—C1	1.3456 (15)	C10—H10	0.9500
N1—N2	1.3791 (13)	C11—H11	0.9500
N1—C3	1.4628 (15)	C12—C13	1.3886 (17)
N2—C2	1.3080 (15)	C12—C17	1.3926 (18)
N3—C2	1.3712 (16)	C13—C14	1.3847 (19)
N3—C1	1.3736 (16)	C14—C15	1.381 (2)
N3—N4	1.4130 (14)	C14—H14	0.9500
N4—H4A	0.918 (15)	C15—C16	1.375 (2)
N4—H4B	0.945 (18)	C15—H15	0.9500
C2—C18	1.4716 (17)	C16—C17	1.3871 (18)
C3—C12	1.5138 (17)	C16—H16	0.9500
C3—C4	1.5233 (17)	C17—H17	0.9500
C3—H3	1.0000	C18—C19	1.3910 (18)
C4—C5	1.5158 (17)	C18—C23	1.3974 (18)
C4—H4C	0.9900	C19—C20	1.3861 (19)
C4—H4D	0.9900	C19—H19	0.9500
C5—C6	1.4913 (18)	C20—C21	1.383 (2)
C6—C11	1.3926 (17)	C20—H20	0.9500
C6—C7	1.3935 (18)	C21—C22	1.382 (2)
C7—C8	1.3809 (19)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.3865 (19)
C8—C9	1.384 (2)	C22—H22	0.9500
C8—H8	0.9500	C23—H23	0.9500

C1—N1—N2	113.49 (10)	C9—C10—C11	119.92 (13)
C1—N1—C3	124.44 (10)	C9—C10—H10	120.0
N2—N1—C3	121.98 (10)	C11—C10—H10	120.0
C2—N2—N1	104.42 (10)	C10—C11—C6	120.33 (13)
C2—N3—C1	109.50 (10)	C10—C11—H11	119.8
C2—N3—N4	125.04 (11)	C6—C11—H11	119.8
C1—N3—N4	125.45 (10)	C13—C12—C17	117.10 (12)
N3—N4—H4A	105.0 (9)	C13—C12—C3	121.22 (12)
N3—N4—H4B	104.9 (9)	C17—C12—C3	121.68 (11)
H4A—N4—H4B	106.4 (13)	C14—C13—C12	121.95 (13)
N1—C1—N3	102.56 (10)	C14—C13—Cl1	118.52 (11)
N1—C1—S1	129.94 (10)	C12—C13—Cl1	119.53 (11)
N3—C1—S1	127.46 (9)	C15—C14—C13	119.62 (13)
N2—C2—N3	110.02 (11)	C15—C14—H14	120.2
N2—C2—C18	124.06 (11)	C13—C14—H14	120.2
N3—C2—C18	125.91 (10)	C16—C15—C14	119.78 (14)
N1—C3—C12	110.60 (10)	C16—C15—H15	120.1
N1—C3—C4	111.47 (10)	C14—C15—H15	120.1
C12—C3—C4	112.37 (10)	C15—C16—C17	120.11 (14)
N1—C3—H3	107.4	C15—C16—H16	119.9
C12—C3—H3	107.4	C17—C16—H16	119.9
C4—C3—H3	107.4	C16—C17—C12	121.41 (12)
C5—C4—C3	112.76 (10)	C16—C17—H17	119.3
C5—C4—H4C	109.0	C12—C17—H17	119.3
C3—C4—H4C	109.0	C19—C18—C23	119.75 (13)
C5—C4—H4D	109.0	C19—C18—C2	119.19 (12)
C3—C4—H4D	109.0	C23—C18—C2	121.02 (12)
H4C—C4—H4D	107.8	C20—C19—C18	119.86 (14)
O1—C5—C6	121.17 (12)	C20—C19—H19	120.1
O1—C5—C4	120.25 (12)	C18—C19—H19	120.1
C6—C5—C4	118.56 (10)	C21—C20—C19	120.33 (15)
C11—C6—C7	119.30 (12)	C21—C20—H20	119.8
C11—C6—C5	121.73 (12)	C19—C20—H20	119.8
C7—C6—C5	118.92 (11)	C22—C21—C20	120.00 (14)
C8—C7—C6	120.06 (13)	C22—C21—H21	120.0
C8—C7—H7	120.0	C20—C21—H21	120.0
C6—C7—H7	120.0	C21—C22—C23	120.39 (15)
C7—C8—C9	120.19 (14)	C21—C22—H22	119.8
C7—C8—H8	119.9	C23—C22—H22	119.8
C9—C8—H8	119.9	C22—C23—C18	119.67 (14)
C10—C9—C8	120.20 (14)	C22—C23—H23	120.2
C10—C9—H9	119.9	C18—C23—H23	120.2
C8—C9—H9	119.9

C1—N1—N2—C2	−0.53 (14)	C8—C9—C10—C11	0.2 (2)
C3—N1—N2—C2	−177.29 (11)	C9—C10—C11—C6	0.3 (2)
N2—N1—C1—N3	0.61 (13)	C7—C6—C11—C10	−0.26 (19)
C3—N1—C1—N3	177.27 (11)	C5—C6—C11—C10	177.17 (11)
N2—N1—C1—S1	178.26 (9)	N1—C3—C12—C13	145.32 (12)
C3—N1—C1—S1	−5.07 (19)	C4—C3—C12—C13	−89.41 (14)
C2—N3—C1—N1	−0.45 (13)	N1—C3—C12—C17	−34.62 (16)
N4—N3—C1—N1	−179.92 (11)	C4—C3—C12—C17	90.66 (14)
C2—N3—C1—S1	−178.18 (10)	C17—C12—C13—C14	1.71 (19)
N4—N3—C1—S1	2.35 (19)	C3—C12—C13—C14	−178.22 (12)
N1—N2—C2—N3	0.21 (13)	C17—C12—C13—Cl1	−178.59 (9)
N1—N2—C2—C18	179.04 (11)	C3—C12—C13—Cl1	1.47 (17)
C1—N3—C2—N2	0.15 (14)	C12—C13—C14—C15	−1.0 (2)
N4—N3—C2—N2	179.62 (11)	Cl1—C13—C14—C15	179.27 (10)
C1—N3—C2—C18	−178.65 (12)	C13—C14—C15—C16	−0.6 (2)
N4—N3—C2—C18	0.8 (2)	C14—C15—C16—C17	1.5 (2)
C1—N1—C3—C12	−87.95 (14)	C15—C16—C17—C12	−0.8 (2)
N2—N1—C3—C12	88.45 (13)	C13—C12—C17—C16	−0.78 (19)
C1—N1—C3—C4	146.26 (11)	C3—C12—C17—C16	179.15 (11)
N2—N1—C3—C4	−37.34 (15)	N2—C2—C18—C19	45.75 (18)
N1—C3—C4—C5	−63.58 (13)	N3—C2—C18—C19	−135.61 (13)
C12—C3—C4—C5	171.62 (10)	N2—C2—C18—C23	−131.78 (13)
C3—C4—C5—O1	4.68 (17)	N3—C2—C18—C23	46.86 (18)
C3—C4—C5—C6	−173.49 (10)	C23—C18—C19—C20	−0.91 (19)
O1—C5—C6—C11	179.54 (12)	C2—C18—C19—C20	−178.47 (12)
C4—C5—C6—C11	−2.31 (17)	C18—C19—C20—C21	0.8 (2)
O1—C5—C6—C7	−3.03 (18)	C19—C20—C21—C22	−0.1 (2)
C4—C5—C6—C7	175.12 (11)	C20—C21—C22—C23	−0.4 (2)
C11—C6—C7—C8	−0.16 (19)	C21—C22—C23—C18	0.4 (2)
C5—C6—C7—C8	−177.66 (12)	C19—C18—C23—C22	0.32 (19)
C6—C7—C8—C9	0.6 (2)	C2—C18—C23—C22	177.84 (11)
C7—C8—C9—C10	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1ⁱ	0.945 (18)	2.714 (17)	3.4928 (17)	140.2 (12)
C7—H7···O1ⁱⁱ	0.95	2.52	3.436 (2)	161
C21—H21···O1ⁱⁱⁱ	0.95	2.53	3.415 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉ClN₄OS
M_r	434.93
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	10.559 (3), 10.787 (4), 10.835 (3)
α, β, γ (°)	99.582 (2), 96.638 (4), 115.267 (3)
V (Å³)	1076.2 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.20 × 0.14

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.943, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13931, 5111, 3433
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.079, 0.95
No. of reflections	5111
No. of parameters	279
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.29

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	0.945 (18)	2.714 (17)	3.4928 (17)	140.2 (12)
C7—H7···O1ⁱⁱ	0.95	2.52	3.436 (2)	161
C21—H21···O1ⁱⁱⁱ	0.95	2.53	3.415 (2)	156

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1794

doi:10.1107/S1600536811023750

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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