3-[4-(2-Chloro-benzyl-idene-amino)-3-methyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenyl-propan-1-one.

In the title mol-ecule, C(25)H(21)ClN(4)OS, the triazole ring forms dihedral angles of 47.9 (2), 84.5 (2) and 3.9 (2)° with the two phenyl rings and the chloro-phenyl ring, respectively. The chloro-phenyl ring, the triazole ring and the conjugative linker between the two aromatic rings are nearly coplanar with an r.m.s. deviation of 0.0483 (2) Å and a maximum deviation of 0.0911 (2) Å.

Related literature

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

Experimental

Crystal data

C25H21ClN4OS

M = 460.97

Triclinic,

a = 8.3347 (9) Å

b = 10.6029 (12) Å

c = 13.4262 (16) Å

α = 87.907 (19)°

β = 81.026 (18)°

γ = 82.024 (17)°

V = 1160.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 113 K

0.18 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.951, T max = 0.973

14988 measured reflections

5478 independent reflections

3741 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.127

S = 1.02

5478 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.35 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/S1600536811032983/zk2023sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032983/zk2023Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032983/zk2023Isup3.cml

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

C25H21ClN4OS	Z = 2
Mr = 460.97	F(000) = 480
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3347 (9) Å	Cell parameters from 3699 reflections
b = 10.6029 (12) Å	θ = 1.5–27.9°
c = 13.4262 (16) Å	µ = 0.28 mm−1
α = 87.907 (19)°	T = 113 K
β = 81.026 (18)°	Prism, colorless
γ = 82.024 (17)°	0.18 × 0.16 × 0.10 mm
V = 1160.5 (2) Å3

Rigaku Saturn CCD area-detector diffractometer	5478 independent reflections
Radiation source: rotating anode	3741 reflections with I > 2σ(I)
multilayer	Rint = 0.047
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 1.5°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→12
Tmin = 0.951, Tmax = 0.973	l = −17→17
14988 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
5478 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.35 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	0.29774 (8)	0.61784 (5)	0.10454 (4)	0.04087 (18)
Cl1	0.20199 (11)	0.93846 (6)	−0.11093 (5)	0.0681 (3)
O1	0.3085 (2)	0.22648 (14)	0.34675 (11)	0.0456 (4)
N1	0.4144 (2)	0.59915 (15)	0.28411 (12)	0.0313 (4)
N2	0.4657 (2)	0.66988 (15)	0.35541 (12)	0.0340 (4)
N3	0.3976 (2)	0.79060 (15)	0.22639 (12)	0.0309 (4)
N4	0.3676 (2)	0.90997 (15)	0.18009 (13)	0.0340 (4)
C1	0.3707 (3)	0.66863 (19)	0.20309 (15)	0.0309 (5)
C2	0.4535 (3)	0.78623 (19)	0.31822 (15)	0.0318 (5)
C3	0.4152 (3)	0.46078 (18)	0.30128 (15)	0.0313 (5)
H3	0.3646	0.4275	0.2465	0.038*
C4	0.3078 (3)	0.43869 (18)	0.40126 (15)	0.0353 (5)
H4A	0.2043	0.4980	0.4053	0.042*
H4B	0.3646	0.4583	0.4571	0.042*
C5	0.2675 (3)	0.3027 (2)	0.41478 (16)	0.0352 (5)
C6	0.1735 (3)	0.26640 (19)	0.51340 (16)	0.0332 (5)
C7	0.1321 (3)	0.1420 (2)	0.52621 (17)	0.0414 (6)
H7	0.1621	0.0838	0.4722	0.050*
C8	0.0481 (3)	0.1038 (2)	0.61687 (19)	0.0459 (6)
H8	0.0223	0.0193	0.6254	0.055*
C9	0.0018 (3)	0.1891 (2)	0.69522 (18)	0.0445 (6)
H9	−0.0565	0.1629	0.7573	0.053*
C10	0.0399 (3)	0.3124 (2)	0.68346 (17)	0.0424 (6)
H10	0.0071	0.3707	0.7372	0.051*
C11	0.1257 (3)	0.3505 (2)	0.59356 (16)	0.0375 (5)
H11	0.1525	0.4349	0.5862	0.045*
C12	0.5930 (3)	0.39735 (18)	0.29147 (15)	0.0327 (5)
C13	0.6642 (3)	0.34362 (19)	0.37317 (17)	0.0400 (6)
H13	0.6004	0.3426	0.4383	0.048*
C14	0.8284 (3)	0.2916 (2)	0.3594 (2)	0.0516 (7)
H14	0.8759	0.2543	0.4153	0.062*
C15	0.9234 (3)	0.2933 (2)	0.2655 (2)	0.0551 (7)
H15	1.0360	0.2586	0.2571	0.066*
C16	0.8540 (3)	0.3458 (2)	0.1841 (2)	0.0543 (7)
H16	0.9188	0.3470	0.1193	0.065*
C17	0.6896 (3)	0.3970 (2)	0.19660 (17)	0.0429 (6)
H17	0.6423	0.4322	0.1400	0.051*
C18	0.3300 (3)	0.91863 (19)	0.09206 (15)	0.0341 (5)
H18	0.3212	0.8449	0.0562	0.041*
C19	0.3002 (3)	1.04705 (19)	0.04715 (15)	0.0318 (5)
C20	0.2424 (3)	1.0664 (2)	−0.04535 (16)	0.0405 (6)
C21	0.2152 (3)	1.1880 (2)	−0.08722 (18)	0.0469 (6)
H21	0.1754	1.1999	−0.1499	0.056*
C22	0.2463 (3)	1.2909 (2)	−0.03757 (18)	0.0473 (6)
H22	0.2267	1.3740	−0.0658	0.057*
C23	0.3057 (3)	1.2743 (2)	0.05313 (18)	0.0479 (6)
H23	0.3284	1.3458	0.0865	0.057*
C24	0.3322 (3)	1.1538 (2)	0.09534 (17)	0.0412 (6)
H24	0.3728	1.1432	0.1579	0.049*
C25	0.4944 (3)	0.9002 (2)	0.36488 (17)	0.0429 (6)
H25A	0.5084	0.8804	0.4351	0.064*
H25B	0.4054	0.9706	0.3628	0.064*
H25C	0.5964	0.9248	0.3275	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.0663 (4)	0.0293 (3)	0.0291 (3)	−0.0053 (3)	−0.0155 (3)	0.0028 (2)
Cl1	0.1153 (7)	0.0498 (4)	0.0527 (4)	−0.0258 (4)	−0.0429 (4)	0.0075 (3)
O1	0.0627 (12)	0.0358 (9)	0.0392 (9)	−0.0074 (8)	−0.0097 (8)	−0.0028 (7)
N1	0.0427 (11)	0.0253 (9)	0.0255 (9)	0.0001 (8)	−0.0093 (8)	0.0029 (7)
N2	0.0422 (11)	0.0294 (10)	0.0318 (10)	−0.0014 (8)	−0.0130 (8)	0.0007 (8)
N3	0.0379 (11)	0.0245 (9)	0.0297 (9)	−0.0008 (7)	−0.0074 (8)	0.0052 (7)
N4	0.0413 (11)	0.0263 (10)	0.0343 (10)	−0.0025 (8)	−0.0097 (8)	0.0074 (8)
C1	0.0385 (13)	0.0263 (11)	0.0258 (10)	0.0000 (9)	−0.0030 (9)	0.0036 (9)
C2	0.0366 (13)	0.0297 (12)	0.0300 (11)	0.0001 (9)	−0.0118 (9)	0.0014 (9)
C3	0.0427 (13)	0.0225 (11)	0.0287 (11)	−0.0015 (9)	−0.0087 (10)	0.0035 (8)
C4	0.0417 (14)	0.0294 (12)	0.0329 (12)	0.0003 (9)	−0.0056 (10)	0.0040 (9)
C5	0.0415 (14)	0.0311 (12)	0.0346 (12)	−0.0022 (10)	−0.0140 (10)	0.0053 (10)
C6	0.0352 (12)	0.0317 (12)	0.0344 (12)	−0.0033 (9)	−0.0133 (10)	0.0069 (9)
C7	0.0438 (14)	0.0366 (13)	0.0469 (14)	−0.0085 (10)	−0.0153 (11)	0.0054 (11)
C8	0.0456 (15)	0.0404 (14)	0.0563 (16)	−0.0148 (11)	−0.0179 (12)	0.0178 (12)
C9	0.0339 (13)	0.0569 (16)	0.0442 (14)	−0.0119 (11)	−0.0106 (11)	0.0193 (12)
C10	0.0413 (14)	0.0456 (14)	0.0389 (13)	−0.0035 (11)	−0.0061 (11)	0.0070 (11)
C11	0.0390 (14)	0.0346 (13)	0.0395 (13)	−0.0049 (10)	−0.0096 (10)	0.0070 (10)
C12	0.0417 (13)	0.0235 (11)	0.0324 (11)	−0.0001 (9)	−0.0088 (10)	0.0003 (9)
C13	0.0473 (15)	0.0352 (13)	0.0373 (12)	0.0020 (10)	−0.0122 (11)	−0.0012 (10)
C14	0.0530 (17)	0.0395 (14)	0.0663 (18)	0.0049 (12)	−0.0305 (14)	−0.0033 (12)
C15	0.0390 (15)	0.0451 (15)	0.081 (2)	0.0027 (11)	−0.0110 (15)	−0.0169 (14)
C16	0.0486 (17)	0.0509 (16)	0.0592 (17)	−0.0033 (12)	0.0038 (14)	−0.0092 (13)
C17	0.0487 (16)	0.0398 (14)	0.0388 (13)	−0.0036 (11)	−0.0046 (12)	0.0002 (10)
C18	0.0429 (14)	0.0274 (12)	0.0313 (11)	−0.0033 (9)	−0.0056 (10)	0.0025 (9)
C19	0.0354 (12)	0.0270 (11)	0.0321 (11)	−0.0044 (9)	−0.0034 (9)	0.0033 (9)
C20	0.0521 (15)	0.0367 (13)	0.0352 (12)	−0.0093 (11)	−0.0127 (11)	0.0065 (10)
C21	0.0556 (16)	0.0444 (15)	0.0423 (14)	−0.0065 (12)	−0.0158 (12)	0.0130 (12)
C22	0.0564 (17)	0.0329 (14)	0.0504 (15)	−0.0003 (11)	−0.0097 (13)	0.0121 (11)
C23	0.0701 (19)	0.0294 (13)	0.0453 (14)	−0.0085 (11)	−0.0115 (13)	0.0023 (11)
C24	0.0535 (16)	0.0344 (13)	0.0352 (12)	−0.0054 (11)	−0.0066 (11)	0.0025 (10)
C25	0.0532 (16)	0.0343 (13)	0.0450 (13)	−0.0036 (11)	−0.0219 (12)	0.0005 (10)

S1—C1	1.675 (2)	C10—H10	0.9500
Cl1—C20	1.742 (2)	C11—H11	0.9500
O1—C5	1.218 (2)	C12—C13	1.394 (3)
N1—C1	1.360 (2)	C12—C17	1.396 (3)
N1—N2	1.389 (2)	C13—C14	1.390 (3)
N1—C3	1.476 (2)	C13—H13	0.9500
N2—C2	1.311 (2)	C14—C15	1.381 (3)
N3—C2	1.381 (2)	C14—H14	0.9500
N3—C1	1.397 (2)	C15—C16	1.380 (3)
N3—N4	1.398 (2)	C15—H15	0.9500
N4—C18	1.266 (2)	C16—C17	1.389 (3)
C2—C25	1.485 (3)	C16—H16	0.9500
C3—C4	1.523 (3)	C17—H17	0.9500
C3—C12	1.528 (3)	C18—C19	1.474 (3)
C3—H3	1.0000	C18—H18	0.9500
C4—C5	1.524 (3)	C19—C20	1.399 (3)
C4—H4A	0.9900	C19—C24	1.401 (3)
C4—H4B	0.9900	C20—C21	1.392 (3)
C5—C6	1.496 (3)	C21—C22	1.373 (3)
C6—C11	1.396 (3)	C21—H21	0.9500
C6—C7	1.407 (3)	C22—C23	1.381 (3)
C7—C8	1.383 (3)	C22—H22	0.9500
C7—H7	0.9500	C23—C24	1.383 (3)
C8—C9	1.385 (3)	C23—H23	0.9500
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.385 (3)	C25—H25A	0.9800
C9—H9	0.9500	C25—H25B	0.9800
C10—C11	1.381 (3)	C25—H25C	0.9800
C1—N1—N2	114.03 (16)	C6—C11—H11	119.6
C1—N1—C3	127.05 (17)	C13—C12—C17	118.7 (2)
N2—N1—C3	118.91 (15)	C13—C12—C3	123.07 (19)
C2—N2—N1	104.23 (16)	C17—C12—C3	118.17 (18)
C2—N3—C1	109.24 (16)	C14—C13—C12	120.0 (2)
C2—N3—N4	117.55 (17)	C14—C13—H13	120.0
C1—N3—N4	133.00 (17)	C12—C13—H13	120.0
C18—N4—N3	120.21 (18)	C15—C14—C13	120.8 (2)
N1—C1—N3	101.84 (17)	C15—C14—H14	119.6
N1—C1—S1	127.71 (16)	C13—C14—H14	119.6
N3—C1—S1	130.42 (15)	C16—C15—C14	119.7 (2)
N2—C2—N3	110.66 (18)	C16—C15—H15	120.2
N2—C2—C25	126.39 (19)	C14—C15—H15	120.2
N3—C2—C25	122.95 (18)	C15—C16—C17	120.1 (2)
N1—C3—C4	108.79 (16)	C15—C16—H16	119.9
N1—C3—C12	108.60 (17)	C17—C16—H16	119.9
C4—C3—C12	115.85 (17)	C16—C17—C12	120.7 (2)
N1—C3—H3	107.8	C16—C17—H17	119.7
C4—C3—H3	107.8	C12—C17—H17	119.7
C12—C3—H3	107.8	N4—C18—C19	117.7 (2)
C3—C4—C5	112.93 (17)	N4—C18—H18	121.1
C3—C4—H4A	109.0	C19—C18—H18	121.1
C5—C4—H4A	109.0	C20—C19—C24	117.85 (19)
C3—C4—H4B	109.0	C20—C19—C18	121.47 (19)
C5—C4—H4B	109.0	C24—C19—C18	120.7 (2)
H4A—C4—H4B	107.8	C21—C20—C19	121.0 (2)
O1—C5—C6	121.09 (19)	C21—C20—Cl1	118.29 (18)
O1—C5—C4	120.94 (19)	C19—C20—Cl1	120.74 (16)
C6—C5—C4	117.96 (18)	C22—C21—C20	119.7 (2)
C11—C6—C7	118.5 (2)	C22—C21—H21	120.1
C11—C6—C5	122.84 (19)	C20—C21—H21	120.1
C7—C6—C5	118.63 (19)	C21—C22—C23	120.5 (2)
C8—C7—C6	120.5 (2)	C21—C22—H22	119.8
C8—C7—H7	119.8	C23—C22—H22	119.8
C6—C7—H7	119.8	C22—C23—C24	120.0 (2)
C7—C8—C9	119.9 (2)	C22—C23—H23	120.0
C7—C8—H8	120.0	C24—C23—H23	120.0
C9—C8—H8	120.0	C23—C24—C19	120.9 (2)
C10—C9—C8	120.3 (2)	C23—C24—H24	119.6
C10—C9—H9	119.8	C19—C24—H24	119.6
C8—C9—H9	119.8	C2—C25—H25A	109.5
C11—C10—C9	120.0 (2)	C2—C25—H25B	109.5
C11—C10—H10	120.0	H25A—C25—H25B	109.5
C9—C10—H10	120.0	C2—C25—H25C	109.5
C10—C11—C6	120.7 (2)	H25A—C25—H25C	109.5
C10—C11—H11	119.6	H25B—C25—H25C	109.5
C1—N1—N2—C2	0.1 (2)	C6—C7—C8—C9	1.1 (3)
C3—N1—N2—C2	178.94 (17)	C7—C8—C9—C10	−0.4 (3)
C2—N3—N4—C18	173.88 (19)	C8—C9—C10—C11	−0.5 (3)
C1—N3—N4—C18	−12.1 (3)	C9—C10—C11—C6	0.6 (3)
N2—N1—C1—N3	0.1 (2)	C7—C6—C11—C10	0.1 (3)
C3—N1—C1—N3	−178.57 (17)	C5—C6—C11—C10	−179.6 (2)
N2—N1—C1—S1	−177.92 (15)	N1—C3—C12—C13	110.5 (2)
C3—N1—C1—S1	3.4 (3)	C4—C3—C12—C13	−12.2 (3)
C2—N3—C1—N1	−0.3 (2)	N1—C3—C12—C17	−67.4 (2)
N4—N3—C1—N1	−174.73 (19)	C4—C3—C12—C17	169.86 (18)
C2—N3—C1—S1	177.65 (17)	C17—C12—C13—C14	0.3 (3)
N4—N3—C1—S1	3.3 (3)	C3—C12—C13—C14	−177.7 (2)
N1—N2—C2—N3	−0.3 (2)	C12—C13—C14—C15	0.7 (4)
N1—N2—C2—C25	−179.7 (2)	C13—C14—C15—C16	−0.9 (4)
C1—N3—C2—N2	0.4 (2)	C14—C15—C16—C17	0.2 (4)
N4—N3—C2—N2	175.82 (17)	C15—C16—C17—C12	0.7 (4)
C1—N3—C2—C25	179.84 (19)	C13—C12—C17—C16	−0.9 (3)
N4—N3—C2—C25	−4.8 (3)	C3—C12—C17—C16	177.1 (2)
C1—N1—C3—C4	−123.5 (2)	N3—N4—C18—C19	−179.87 (17)
N2—N1—C3—C4	57.9 (2)	N4—C18—C19—C20	−173.6 (2)
C1—N1—C3—C12	109.6 (2)	N4—C18—C19—C24	7.7 (3)
N2—N1—C3—C12	−69.1 (2)	C24—C19—C20—C21	−1.0 (3)
N1—C3—C4—C5	166.45 (17)	C18—C19—C20—C21	−179.8 (2)
C12—C3—C4—C5	−70.9 (2)	C24—C19—C20—Cl1	179.18 (17)
C3—C4—C5—O1	−5.8 (3)	C18—C19—C20—Cl1	0.4 (3)
C3—C4—C5—C6	175.37 (18)	C19—C20—C21—C22	0.4 (4)
O1—C5—C6—C11	179.3 (2)	Cl1—C20—C21—C22	−179.82 (19)
C4—C5—C6—C11	−1.8 (3)	C20—C21—C22—C23	0.6 (4)
O1—C5—C6—C7	−0.3 (3)	C21—C22—C23—C24	−0.9 (4)
C4—C5—C6—C7	178.57 (19)	C22—C23—C24—C19	0.2 (4)
C11—C6—C7—C8	−0.9 (3)	C20—C19—C24—C23	0.7 (3)
C5—C6—C7—C8	178.70 (19)	C18—C19—C24—C23	179.5 (2)