3-(4-Amino-3-ethyl-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(19)H(19)ClN(4)OS, the 1,2,4-triazole ring forms dihedral angles of 86.0 (2) and 65.6 (2)° with the phenyl and chloro-phenyl rings, respectively. In the crystal, inter-molecular N-H⋯S and N-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers, which are further linked into chains in [001] via weak C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C19H19ClN4OS

M = 386.89

Monoclinic,

a = 29.023 (10) Å

b = 7.561 (2) Å

c = 18.286 (6) Å

β = 109.606 (6)°

V = 3780 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.937, T max = 0.962

22962 measured reflections

4441 independent reflections

3430 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.02

4441 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.23 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/S1600536811025803/cv5121sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025803/cv5121Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025803/cv5121Isup3.cml

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

C19H19ClN4OS	F(000) = 1616
Mr = 386.89	Dx = 1.360 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6659 reflections
a = 29.023 (10) Å	θ = 1.5–27.9°
b = 7.561 (2) Å	µ = 0.33 mm−1
c = 18.286 (6) Å	T = 113 K
β = 109.606 (6)°	Prism, colourless
V = 3780 (2) Å3	0.20 × 0.18 × 0.12 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	4441 independent reflections
Radiation source: rotating anode	3430 reflections with I > 2σ(I)
multilayer	Rint = 0.036
Detector resolution: 14.22 pixels mm-1	θmax = 27.8°, θmin = 1.5°
φ and ω scans	h = −38→38
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −9→9
Tmin = 0.937, Tmax = 0.962	l = −23→23
22962 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0519P)2] where P = (Fo2 + 2Fc2)/3
4441 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.23 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	0.190030 (13)	0.38390 (4)	0.542685 (19)	0.02176 (10)
Cl1	0.019191 (13)	0.34916 (5)	0.39368 (3)	0.03607 (12)
O1	0.15205 (3)	0.13842 (11)	0.34074 (5)	0.0218 (2)
N1	0.16509 (4)	0.51514 (13)	0.39437 (6)	0.0155 (2)
N2	0.18602 (4)	0.59175 (14)	0.34375 (6)	0.0168 (2)
N3	0.24120 (4)	0.53762 (13)	0.45809 (6)	0.0157 (2)
N4	0.28746 (4)	0.53417 (16)	0.51708 (7)	0.0214 (3)
C1	0.19819 (5)	0.47776 (16)	0.46471 (7)	0.0155 (3)
C2	0.23249 (5)	0.60456 (15)	0.38496 (7)	0.0159 (3)
C3	0.11395 (4)	0.45895 (16)	0.36740 (7)	0.0158 (3)
H3	0.1105	0.3619	0.4024	0.019*
C4	0.10039 (5)	0.38305 (16)	0.28491 (7)	0.0175 (3)
H4C	0.0647	0.3617	0.2643	0.021*
H4D	0.1083	0.4716	0.2510	0.021*
C5	0.12692 (4)	0.21139 (16)	0.28159 (7)	0.0159 (3)
C6	0.11887 (4)	0.13029 (16)	0.20350 (7)	0.0159 (3)
C7	0.12856 (4)	−0.05123 (17)	0.20020 (8)	0.0188 (3)
H7	0.1405	−0.1181	0.2468	0.023*
C8	0.12069 (5)	−0.13266 (17)	0.12925 (8)	0.0217 (3)
H8	0.1269	−0.2557	0.1273	0.026*
C9	0.10383 (5)	−0.03574 (19)	0.06100 (8)	0.0255 (3)
H9	0.0985	−0.0924	0.0125	0.031*
C10	0.09476 (5)	0.14466 (19)	0.06362 (8)	0.0255 (3)
H10	0.0837	0.2115	0.0170	0.031*
C11	0.10196 (5)	0.22674 (18)	0.13465 (8)	0.0206 (3)
H11	0.0953	0.3494	0.1363	0.025*
C12	0.07870 (5)	0.60609 (16)	0.36975 (7)	0.0163 (3)
C13	0.03355 (5)	0.56770 (17)	0.37776 (8)	0.0216 (3)
C14	−0.00095 (5)	0.69742 (19)	0.37456 (9)	0.0270 (3)
H14	−0.0313	0.6667	0.3801	0.032*
C15	0.00937 (5)	0.87208 (18)	0.36319 (8)	0.0249 (3)
H15	−0.0141	0.9619	0.3602	0.030*
C16	0.05417 (5)	0.91481 (18)	0.35614 (8)	0.0227 (3)
H16	0.0614	1.0345	0.3485	0.027*
C17	0.08856 (5)	0.78348 (17)	0.36023 (7)	0.0196 (3)
H17	0.1194	0.8153	0.3565	0.024*
C18	0.27199 (5)	0.67570 (18)	0.35804 (8)	0.0203 (3)
H18A	0.2920	0.5760	0.3503	0.024*
H18B	0.2936	0.7530	0.3990	0.024*
C19	0.25249 (5)	0.7808 (2)	0.28262 (9)	0.0284 (3)
H19A	0.2305	0.7060	0.2420	0.043*
H19B	0.2799	0.8195	0.2666	0.043*
H19C	0.2345	0.8845	0.2908	0.043*
H4A	0.3003 (6)	0.425 (2)	0.5136 (10)	0.040 (5)*
H4B	0.2814 (6)	0.522 (2)	0.5616 (10)	0.035 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.02654 (19)	0.02354 (19)	0.01549 (17)	−0.00294 (14)	0.00745 (13)	0.00238 (13)
Cl1	0.02154 (19)	0.01854 (19)	0.0719 (3)	−0.00307 (14)	0.02069 (19)	−0.00139 (18)
O1	0.0255 (5)	0.0209 (5)	0.0170 (5)	0.0044 (4)	0.0045 (4)	0.0016 (4)
N1	0.0157 (5)	0.0170 (5)	0.0144 (5)	0.0003 (4)	0.0059 (4)	0.0017 (4)
N2	0.0180 (5)	0.0179 (6)	0.0162 (5)	0.0003 (4)	0.0081 (4)	0.0016 (4)
N3	0.0140 (5)	0.0153 (5)	0.0161 (5)	0.0004 (4)	0.0028 (4)	0.0008 (4)
N4	0.0163 (6)	0.0235 (7)	0.0192 (6)	0.0007 (5)	−0.0010 (5)	0.0016 (5)
C1	0.0179 (6)	0.0130 (6)	0.0152 (6)	0.0001 (5)	0.0049 (5)	−0.0023 (5)
C2	0.0174 (6)	0.0132 (6)	0.0170 (6)	0.0026 (5)	0.0057 (5)	−0.0003 (5)
C3	0.0150 (6)	0.0163 (6)	0.0156 (6)	−0.0007 (5)	0.0045 (5)	−0.0018 (5)
C4	0.0169 (6)	0.0188 (7)	0.0152 (6)	0.0018 (5)	0.0034 (5)	−0.0019 (5)
C5	0.0126 (6)	0.0175 (6)	0.0182 (6)	−0.0024 (5)	0.0060 (5)	−0.0015 (5)
C6	0.0116 (6)	0.0195 (7)	0.0170 (6)	−0.0001 (5)	0.0052 (5)	−0.0017 (5)
C7	0.0173 (7)	0.0196 (7)	0.0219 (7)	−0.0008 (5)	0.0097 (5)	0.0001 (5)
C8	0.0200 (7)	0.0199 (7)	0.0285 (7)	−0.0024 (5)	0.0124 (6)	−0.0054 (6)
C9	0.0231 (7)	0.0336 (8)	0.0204 (7)	0.0000 (6)	0.0081 (6)	−0.0092 (6)
C10	0.0251 (7)	0.0329 (8)	0.0162 (6)	0.0063 (6)	0.0039 (6)	0.0012 (6)
C11	0.0199 (7)	0.0205 (7)	0.0210 (7)	0.0044 (5)	0.0065 (5)	−0.0007 (5)
C12	0.0168 (6)	0.0183 (7)	0.0126 (6)	0.0008 (5)	0.0034 (5)	−0.0026 (5)
C13	0.0182 (7)	0.0168 (7)	0.0282 (7)	−0.0029 (5)	0.0056 (6)	−0.0038 (6)
C14	0.0148 (7)	0.0259 (8)	0.0401 (9)	−0.0008 (6)	0.0087 (6)	−0.0052 (7)
C15	0.0211 (7)	0.0216 (7)	0.0304 (8)	0.0071 (6)	0.0068 (6)	−0.0024 (6)
C16	0.0296 (8)	0.0168 (7)	0.0227 (7)	0.0026 (6)	0.0102 (6)	0.0017 (6)
C17	0.0226 (7)	0.0209 (7)	0.0178 (6)	0.0011 (5)	0.0101 (5)	0.0008 (5)
C18	0.0172 (6)	0.0221 (7)	0.0232 (7)	0.0013 (5)	0.0090 (5)	0.0012 (6)
C19	0.0258 (8)	0.0328 (8)	0.0307 (8)	0.0029 (6)	0.0147 (6)	0.0111 (7)

S1—C1	1.6792 (14)	C8—C9	1.387 (2)
Cl1—C13	1.7521 (14)	C8—H8	0.9500
O1—C5	1.2151 (15)	C9—C10	1.393 (2)
N1—C1	1.3519 (16)	C9—H9	0.9500
N1—N2	1.3922 (14)	C10—C11	1.3906 (19)
N1—C3	1.4613 (16)	C10—H10	0.9500
N2—C2	1.3092 (16)	C11—H11	0.9500
N3—C1	1.3709 (16)	C12—C17	1.3945 (17)
N3—C2	1.3716 (16)	C12—C13	1.3970 (19)
N3—N4	1.4123 (15)	C13—C14	1.3886 (19)
N4—H4A	0.914 (18)	C14—C15	1.385 (2)
N4—H4B	0.892 (18)	C14—H14	0.9500
C2—C18	1.4916 (18)	C15—C16	1.3873 (19)
C3—C12	1.5218 (17)	C15—H15	0.9500
C3—C4	1.5366 (17)	C16—C17	1.3920 (19)
C3—H3	1.0000	C16—H16	0.9500
C4—C5	1.5207 (17)	C17—H17	0.9500
C4—H4C	0.9900	C18—C19	1.5265 (19)
C4—H4D	0.9900	C18—H18A	0.9900
C5—C6	1.4987 (17)	C18—H18B	0.9900
C6—C11	1.3939 (18)	C19—H19A	0.9800
C6—C7	1.4062 (18)	C19—H19B	0.9800
C7—C8	1.3840 (18)	C19—H19C	0.9800
C7—H7	0.9500
C1—N1—N2	112.97 (10)	C8—C9—C10	120.00 (13)
C1—N1—C3	125.26 (11)	C8—C9—H9	120.0
N2—N1—C3	121.12 (10)	C10—C9—H9	120.0
C2—N2—N1	104.06 (10)	C11—C10—C9	119.88 (13)
C1—N3—C2	109.41 (10)	C11—C10—H10	120.1
C1—N3—N4	125.93 (11)	C9—C10—H10	120.1
C2—N3—N4	124.65 (11)	C10—C11—C6	120.47 (12)
N3—N4—H4A	105.6 (10)	C10—C11—H11	119.8
N3—N4—H4B	105.7 (10)	C6—C11—H11	119.8
H4A—N4—H4B	100.5 (14)	C17—C12—C13	116.87 (11)
N1—C1—N3	102.97 (11)	C17—C12—C3	122.10 (12)
N1—C1—S1	129.69 (10)	C13—C12—C3	120.95 (11)
N3—C1—S1	127.34 (10)	C14—C13—C12	122.49 (13)
N2—C2—N3	110.57 (11)	C14—C13—Cl1	117.70 (11)
N2—C2—C18	126.44 (12)	C12—C13—Cl1	119.81 (10)
N3—C2—C18	122.97 (11)	C15—C14—C13	119.38 (13)
N1—C3—C12	113.22 (10)	C15—C14—H14	120.3
N1—C3—C4	109.66 (10)	C13—C14—H14	120.3
C12—C3—C4	110.33 (10)	C14—C15—C16	119.51 (12)
N1—C3—H3	107.8	C14—C15—H15	120.2
C12—C3—H3	107.8	C16—C15—H15	120.2
C4—C3—H3	107.8	C15—C16—C17	120.43 (13)
C5—C4—C3	113.05 (10)	C15—C16—H16	119.8
C5—C4—H4C	109.0	C17—C16—H16	119.8
C3—C4—H4C	109.0	C16—C17—C12	121.28 (13)
C5—C4—H4D	109.0	C16—C17—H17	119.4
C3—C4—H4D	109.0	C12—C17—H17	119.4
H4C—C4—H4D	107.8	C2—C18—C19	113.14 (11)
O1—C5—C6	121.16 (11)	C2—C18—H18A	108.9
O1—C5—C4	120.85 (11)	C19—C18—H18A	108.9
C6—C5—C4	117.91 (10)	C2—C18—H18B	109.0
C11—C6—C7	119.13 (12)	C19—C18—H18B	108.9
C11—C6—C5	122.79 (11)	H18A—C18—H18B	107.8
C7—C6—C5	118.08 (11)	C18—C19—H19A	109.5
C8—C7—C6	120.12 (12)	C18—C19—H19B	109.5
C8—C7—H7	119.9	H19A—C19—H19B	109.5
C6—C7—H7	119.9	C18—C19—H19C	109.5
C7—C8—C9	120.39 (13)	H19A—C19—H19C	109.5
C7—C8—H8	119.8	H19B—C19—H19C	109.5
C9—C8—H8	119.8
C1—N1—N2—C2	−1.44 (13)	C4—C5—C6—C7	−158.52 (11)
C3—N1—N2—C2	−172.66 (10)	C11—C6—C7—C8	−0.87 (18)
N2—N1—C1—N3	1.50 (13)	C5—C6—C7—C8	178.65 (11)
C3—N1—C1—N3	172.29 (10)	C6—C7—C8—C9	0.85 (19)
N2—N1—C1—S1	−179.21 (9)	C7—C8—C9—C10	0.1 (2)
C3—N1—C1—S1	−8.41 (19)	C8—C9—C10—C11	−0.9 (2)
C2—N3—C1—N1	−0.99 (13)	C9—C10—C11—C6	0.9 (2)
N4—N3—C1—N1	178.19 (11)	C7—C6—C11—C10	−0.01 (19)
C2—N3—C1—S1	179.70 (9)	C5—C6—C11—C10	−179.51 (12)
N4—N3—C1—S1	−1.12 (18)	N1—C3—C12—C17	29.90 (17)
N1—N2—C2—N3	0.73 (13)	C4—C3—C12—C17	−93.44 (14)
N1—N2—C2—C18	178.95 (11)	N1—C3—C12—C13	−153.36 (12)
C1—N3—C2—N2	0.16 (14)	C4—C3—C12—C13	83.30 (15)
N4—N3—C2—N2	−179.04 (11)	C17—C12—C13—C14	1.6 (2)
C1—N3—C2—C18	−178.13 (11)	C3—C12—C13—C14	−175.28 (12)
N4—N3—C2—C18	2.68 (18)	C17—C12—C13—Cl1	−177.57 (10)
C1—N1—C3—C12	102.95 (14)	C3—C12—C13—Cl1	5.53 (17)
N2—N1—C3—C12	−86.96 (13)	C12—C13—C14—C15	−0.1 (2)
C1—N1—C3—C4	−133.35 (12)	Cl1—C13—C14—C15	179.07 (11)
N2—N1—C3—C4	36.74 (14)	C13—C14—C15—C16	−0.8 (2)
N1—C3—C4—C5	66.84 (13)	C14—C15—C16—C17	0.2 (2)
C12—C3—C4—C5	−167.78 (10)	C15—C16—C17—C12	1.4 (2)
C3—C4—C5—O1	6.81 (17)	C13—C12—C17—C16	−2.24 (19)
C3—C4—C5—C6	−176.50 (10)	C3—C12—C17—C16	174.63 (12)
O1—C5—C6—C11	−162.34 (12)	N2—C2—C18—C19	15.46 (18)
C4—C5—C6—C11	20.98 (17)	N3—C2—C18—C19	−166.53 (12)
O1—C5—C6—C7	18.16 (18)

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A···S1i	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A···O1i	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B···O1i	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10···Cgii	0.95	2.62	3.508 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯S1	0.892 (18)	2.763 (16)	3.2239 (16)	113.5 (12)
N4—H4A⋯S1i	0.914 (18)	2.608 (18)	3.4773 (16)	159.2 (14)
N4—H4A⋯O1i	0.914 (18)	2.602 (18)	2.9123 (16)	100.6 (14)
N4—H4B⋯O1i	0.892 (18)	2.466 (15)	2.9123 (16)	111.3 (12)
C10—H10⋯Cgii	0.95	2.62	3.508 (2)	156

Symmetry codes: (i) ; (ii) .