3-(4-Amino-3-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chloro-phen-yl)-1-phenyl-propan-1-one.

In the title mol-ecule, C(23)H(19)ClN(4)OS, 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 inter-molecular 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 = 434.93

Triclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.079

S = 0.95

5111 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.29 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023750/cv5107sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811023750/cv5107Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19ClN4OS	Z = 2
Mr = 434.93	F(000) = 452
Triclinic, P1	Dx = 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

Rigaku Saturn CCD area-detector diffractometer	5111 independent reflections
Radiation source: rotating anode	3433 reflections with I > 2σ(I)
multilayer	Rint = 0.038
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.0°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −14→14
Tmin = 0.943, Tmax = 0.960	l = −14→14
13931 measured reflections

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(Fo2) + (0.0349P)2] where P = (Fo2 + 2Fc2)/3
5111 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) .