1-(4-Chloro-phen-yl)-3-{5-[(E)-2-phenyl-ethen-yl]-1,3,4-thia-diazol-2-yl}urea.

In the title compound, C(17)H(13)ClN(4)OS, the 1,3,4-thia-diazole ring makes dihedral angles of 9.70 (15) and 7.22 (10)° with the benzene and phenyl rings, respectively; the dihedral angle between these two rings is 6.37 (19)°. In the crystal, pairs of N-H⋯N and C-H⋯O hydrogen bonds between inversion-related mol-ecules result in supra-molecular ribbons displaying alternate R(2) (2)(8) and R(2) (2)(14) graph-set ring motifs.

Related literature

For the biological activity of urea derivatives, see: n class="Gene">Abad et al. (2004 ▶); Chen et al. (2005 ▶); Yonova & Stoilkova (2005 ▶). For the biological activity of 1,3,4-thia­diazole derivatives, see: Guzeldemirci & Kucukbasmaci (2010 ▶); Song & Tan (2008 ▶); Zou et al. (2002 ▶). For the synthesis, see: Song et al. (2007 ▶).

Experimental

Crystal data

C17H13ClN4OS

M = 356.82

Monoclinic,

a = 11.2399 (6) Å

b = 4.1032 (2) Å

c = 35.2497 (16) Å

β = 91.525 (4)°

V = 1625.12 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 298 K

0.40 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer

10860 measured reflections

3708 independent reflections

2081 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.154

S = 1.01

3708 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536811002479/is2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002479/is2664Isup2.hkl

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

C17H13ClN4OS	F(000) = 736
Mr = 356.82	Dx = 1.458 Mg m−3Dm = 1.459 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Melting point > 573 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.2399 (6) Å	Cell parameters from 1521 reflections
b = 4.1032 (2) Å	θ = 2.9–23.2°
c = 35.2497 (16) Å	µ = 0.38 mm−1
β = 91.525 (4)°	T = 298 K
V = 1625.12 (14) Å3	Block, colorless
Z = 4	0.40 × 0.06 × 0.02 mm

Bruker SMART CCD area-detector diffractometer	2081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.091
graphite	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −14→14
10860 measured reflections	k = −5→5
3708 independent reflections	l = −45→35

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
3708 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.9546 (3)	−0.0487 (8)	−0.10673 (10)	0.0517 (9)
C2	0.9869 (3)	0.0032 (9)	−0.06905 (10)	0.0559 (10)
H2	1.0585	−0.0780	−0.0592	0.067*
C3	0.9118 (3)	0.1766 (8)	−0.04629 (10)	0.0519 (9)
H3	0.9330	0.2130	−0.0210	0.062*
C4	0.8049 (3)	0.2972 (8)	−0.06083 (10)	0.0440 (8)
C5	0.7739 (3)	0.2341 (9)	−0.09865 (10)	0.0536 (9)
H5	0.7012	0.3078	−0.1085	0.064*
C6	0.8486 (3)	0.0657 (9)	−0.12150 (10)	0.0565 (10)
H6	0.8277	0.0291	−0.1468	0.068*
C7	0.7271 (3)	0.5485 (8)	−0.00213 (10)	0.0468 (8)
C8	0.6130 (3)	0.8377 (8)	0.04418 (10)	0.0458 (8)
C9	0.5972 (3)	0.9536 (8)	0.10951 (9)	0.0470 (8)
C10	0.6089 (3)	0.9901 (8)	0.15047 (10)	0.0499 (9)
H10	0.5513	1.1121	0.1626	0.060*
C11	0.6956 (3)	0.8619 (8)	0.17178 (10)	0.0491 (9)
H11	0.7501	0.7342	0.1591	0.059*
C12	0.7170 (3)	0.8949 (8)	0.21285 (10)	0.0505 (9)
C13	0.6371 (4)	1.0434 (9)	0.23675 (11)	0.0639 (10)
H13	0.5660	1.1267	0.2268	0.077*
C14	0.6625 (5)	1.0679 (11)	0.27489 (12)	0.0839 (13)
H14	0.6079	1.1654	0.2907	0.101*
C15	0.7677 (5)	0.9501 (11)	0.28999 (12)	0.0881 (15)
H15	0.7843	0.9683	0.3159	0.106*
C16	0.8480 (4)	0.8058 (11)	0.26689 (13)	0.0810 (13)
H16	0.9197	0.7273	0.2770	0.097*
C17	0.8222 (4)	0.7772 (9)	0.22848 (11)	0.0656 (11)
H17	0.8768	0.6767	0.2129	0.079*
Cl1	1.05145 (9)	−0.2566 (3)	−0.13606 (3)	0.0742 (4)
N1	0.7246 (2)	0.4851 (7)	−0.04021 (8)	0.0500 (8)
H1A	0.670 (3)	0.583 (8)	−0.0530 (9)	0.060*
N2	0.6343 (3)	0.7450 (8)	0.00788 (9)	0.0540 (8)
H2A	0.588 (3)	0.822 (8)	−0.0081 (10)	0.065*
N3	0.5194 (2)	1.0175 (7)	0.05141 (8)	0.0548 (8)
N4	0.5103 (2)	1.0847 (7)	0.08984 (8)	0.0539 (8)
O1	0.7993 (2)	0.4425 (6)	0.02092 (6)	0.0620 (7)
S1	0.69949 (7)	0.7370 (2)	0.08328 (2)	0.0497 (3)

	U11	U22	U33	U12	U13	U23
C1	0.045 (2)	0.051 (2)	0.060 (2)	−0.0060 (17)	−0.0008 (18)	0.0119 (18)
C2	0.0382 (19)	0.064 (2)	0.065 (3)	0.0002 (18)	−0.0084 (18)	0.019 (2)
C3	0.042 (2)	0.065 (2)	0.047 (2)	−0.0022 (17)	−0.0103 (16)	0.0139 (18)
C4	0.0360 (17)	0.046 (2)	0.050 (2)	−0.0055 (15)	−0.0075 (15)	0.0151 (17)
C5	0.043 (2)	0.064 (2)	0.052 (2)	−0.0041 (18)	−0.0138 (17)	0.012 (2)
C6	0.057 (2)	0.065 (2)	0.047 (2)	−0.0064 (19)	−0.0108 (19)	0.0081 (19)
C7	0.0388 (19)	0.051 (2)	0.050 (2)	−0.0031 (16)	−0.0126 (16)	0.0128 (18)
C8	0.0393 (19)	0.050 (2)	0.048 (2)	−0.0026 (15)	−0.0126 (15)	0.0128 (17)
C9	0.0367 (18)	0.052 (2)	0.052 (2)	−0.0047 (15)	−0.0042 (16)	0.0126 (17)
C10	0.0432 (19)	0.054 (2)	0.053 (2)	−0.0010 (17)	0.0034 (17)	0.0024 (18)
C11	0.048 (2)	0.049 (2)	0.051 (2)	−0.0004 (16)	−0.0034 (17)	0.0044 (17)
C12	0.057 (2)	0.050 (2)	0.044 (2)	−0.0060 (17)	−0.0064 (18)	0.0063 (17)
C13	0.071 (3)	0.068 (3)	0.053 (3)	0.007 (2)	−0.001 (2)	0.001 (2)
C14	0.120 (4)	0.074 (3)	0.059 (3)	0.007 (3)	0.012 (3)	−0.009 (2)
C15	0.142 (5)	0.071 (3)	0.051 (3)	−0.006 (3)	−0.023 (3)	−0.001 (2)
C16	0.099 (4)	0.076 (3)	0.066 (3)	0.003 (3)	−0.025 (3)	0.003 (3)
C17	0.070 (3)	0.072 (3)	0.054 (2)	0.007 (2)	−0.011 (2)	0.004 (2)
Cl1	0.0655 (7)	0.0789 (7)	0.0785 (8)	0.0047 (5)	0.0083 (5)	0.0018 (6)
N1	0.0393 (16)	0.060 (2)	0.0493 (19)	0.0041 (14)	−0.0180 (14)	0.0090 (15)
N2	0.0420 (17)	0.070 (2)	0.049 (2)	0.0067 (15)	−0.0162 (13)	0.0101 (17)
N3	0.0385 (16)	0.071 (2)	0.0543 (19)	0.0026 (15)	−0.0145 (14)	0.0089 (16)
N4	0.0385 (16)	0.066 (2)	0.057 (2)	−0.0004 (14)	−0.0077 (14)	0.0098 (16)
O1	0.0511 (15)	0.0825 (18)	0.0513 (15)	0.0170 (13)	−0.0186 (12)	0.0107 (14)
S1	0.0397 (5)	0.0609 (6)	0.0479 (5)	0.0024 (4)	−0.0117 (4)	0.0111 (5)

C1—C6	1.370 (4)	C9—S1	1.739 (3)
C1—C2	1.384 (5)	C10—C11	1.324 (4)
C1—Cl1	1.744 (4)	C10—H10	0.9300
C2—C3	1.378 (5)	C11—C12	1.468 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.385 (4)	C12—C17	1.379 (5)
C3—H3	0.9300	C12—C13	1.388 (5)
C4—C5	1.393 (5)	C13—C14	1.370 (5)
C4—N1	1.404 (4)	C13—H13	0.9300
C5—C6	1.366 (5)	C14—C15	1.372 (6)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.366 (6)
C7—O1	1.214 (4)	C15—H15	0.9300
C7—N1	1.367 (4)	C16—C17	1.382 (5)
C7—N2	1.372 (4)	C16—H16	0.9300
C8—N3	1.316 (4)	C17—H17	0.9300
C8—N2	1.362 (4)	N1—H1A	0.86 (3)
C8—S1	1.716 (3)	N2—H2A	0.82 (4)
C9—N4	1.299 (4)	N3—N4	1.389 (4)
C9—C10	1.454 (4)
C6—C1—C2	121.0 (3)	C10—C11—C12	128.5 (3)
C6—C1—Cl1	119.5 (3)	C10—C11—H11	115.8
C2—C1—Cl1	119.5 (3)	C12—C11—H11	115.8
C3—C2—C1	119.3 (3)	C17—C12—C13	118.2 (3)
C3—C2—H2	120.4	C17—C12—C11	118.6 (3)
C1—C2—H2	120.4	C13—C12—C11	123.2 (3)
C2—C3—C4	120.5 (3)	C14—C13—C12	120.4 (4)
C2—C3—H3	119.7	C14—C13—H13	119.8
C4—C3—H3	119.7	C12—C13—H13	119.8
C3—C4—C5	118.7 (3)	C13—C14—C15	120.6 (4)
C3—C4—N1	124.6 (3)	C13—C14—H14	119.7
C5—C4—N1	116.8 (3)	C15—C14—H14	119.7
C6—C5—C4	121.1 (3)	C16—C15—C14	119.8 (4)
C6—C5—H5	119.4	C16—C15—H15	120.1
C4—C5—H5	119.4	C14—C15—H15	120.1
C5—C6—C1	119.4 (3)	C15—C16—C17	119.7 (4)
C5—C6—H6	120.3	C15—C16—H16	120.1
C1—C6—H6	120.3	C17—C16—H16	120.1
O1—C7—N1	125.8 (3)	C12—C17—C16	121.1 (4)
O1—C7—N2	122.6 (3)	C12—C17—H17	119.4
N1—C7—N2	111.6 (3)	C16—C17—H17	119.4
N3—C8—N2	120.0 (3)	C7—N1—C4	128.1 (3)
N3—C8—S1	114.7 (3)	C7—N1—H1A	115 (2)
N2—C8—S1	125.3 (3)	C4—N1—H1A	117 (2)
N4—C9—C10	122.3 (3)	C8—N2—C7	124.0 (3)
N4—C9—S1	115.2 (3)	C8—N2—H2A	114 (2)
C10—C9—S1	122.5 (2)	C7—N2—H2A	122 (2)
C11—C10—C9	124.6 (3)	C8—N3—N4	112.3 (3)
C11—C10—H10	117.7	C9—N4—N3	111.4 (3)
C9—C10—H10	117.7	C8—S1—C9	86.31 (17)
C6—C1—C2—C3	−0.9 (5)	C13—C12—C17—C16	−0.1 (6)
Cl1—C1—C2—C3	177.9 (2)	C11—C12—C17—C16	179.0 (3)
C1—C2—C3—C4	0.2 (5)	C15—C16—C17—C12	0.7 (6)
C2—C3—C4—C5	1.2 (5)	O1—C7—N1—C4	−2.2 (6)
C2—C3—C4—N1	−177.8 (3)	N2—C7—N1—C4	179.4 (3)
C3—C4—C5—C6	−2.0 (5)	C3—C4—N1—C7	−9.2 (5)
N1—C4—C5—C6	177.1 (3)	C5—C4—N1—C7	171.7 (3)
C4—C5—C6—C1	1.4 (5)	N3—C8—N2—C7	−177.6 (3)
C2—C1—C6—C5	0.1 (5)	S1—C8—N2—C7	2.0 (5)
Cl1—C1—C6—C5	−178.7 (3)	O1—C7—N2—C8	−0.7 (5)
N4—C9—C10—C11	−179.9 (3)	N1—C7—N2—C8	177.8 (3)
S1—C9—C10—C11	−0.9 (5)	N2—C8—N3—N4	179.0 (3)
C9—C10—C11—C12	177.6 (3)	S1—C8—N3—N4	−0.6 (4)
C10—C11—C12—C17	−171.1 (3)	C10—C9—N4—N3	179.5 (3)
C10—C11—C12—C13	7.9 (6)	S1—C9—N4—N3	0.4 (4)
C17—C12—C13—C14	−0.7 (6)	C8—N3—N4—C9	0.1 (4)
C11—C12—C13—C14	−179.7 (4)	N3—C8—S1—C9	0.7 (3)
C12—C13—C14—C15	0.8 (7)	N2—C8—S1—C9	−178.9 (3)
C13—C14—C15—C16	−0.2 (7)	N4—C9—S1—C8	−0.6 (3)
C14—C15—C16—C17	−0.5 (7)	C10—C9—S1—C8	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.55	3.432 (4)	159
N2—H2A···N3ii	0.82 (4)	2.03 (4)	2.848 (4)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.55	3.432 (4)	159
N2—H2A⋯N3ii	0.82 (4)	2.03 (4)	2.848 (4)	174 (3)

Symmetry codes: (i) ; (ii) .