3-[4-Amino-3-(4-methyl-phen-yl)-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(24)H(21)ClN(4)OS, 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 inter-molecular N-H⋯S hydrogen bonds link the mol-ecules 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 = 448.96

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.145

S = 1.11

4989 reflections

289 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.93 e Å−3

Δρmin = −0.76 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/S1600536811023993/cv5109sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811023993/cv5109Isup3.cml

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

C24H21ClN4OS	F(000) = 936
Mr = 448.96	Dx = 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

Rigaku Saturn CCD area-detector diffractometer	4989 independent reflections
Radiation source: rotating anode	3972 reflections with I > 2σ(I)
multilayer	Rint = 0.065
Detector resolution: 14.63 pixels mm-1	θmax = 27.2°, θmin = 2.1°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
Tmin = 0.919, Tmax = 0.978	l = −20→22
22007 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)] = 0.060	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(Fo2) + (0.058P)2 + 0.3265P] where P = (Fo2 + 2Fc2)/3
4989 reflections	(Δ/σ)max = 0.002
289 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.76 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	0.02423 (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)*

	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)

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)

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)

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) .