1-(4-Chloro­phen­yl)-3-{5-[(E)-2-phenyl­ethen­yl]-1,3,4-thia­diazol-2-yl}urea

Zhan, X.-H.; Wang, Z.-Y.

doi:10.1107/S1600536811002479

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o510

doi:10.1107/S1600536811002479

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1-(4-Chlorophenyl)-3-{5-[(E)-2-phenylethenyl]-1,3,4-thiadiazol-2-yl}urea

Xiu-Huan Zhan ^a and Zi-Yun Wang ^a ^*

^aDepartment of Chemistry, Zhoukou Normal University, Zhoukou 466000, People's Republic of China
^*Correspondence e-mail: zksywzy@163.com

(Received 7 January 2011; accepted 18 January 2011; online 29 January 2011)

In the title compound, C₁₇H₁₃ClN₄OS, the 1,3,4-thiadiazole 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 molecules result in supramolecular ribbons displaying alternate R₂²(8) and R₂²(14) graph-set ring motifs.

Related literature

For the biological activity of urea derivatives, see: 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_r = 356.82
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.154
S = 1.01
3708 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻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) -x+2, -y, -z; (ii) -x+1, -y+2, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002479/is2664sup1.cif

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

checkCIF report

Comment top

Urea derivatives have attracted much attention on the account of their interesting biological effects, such as insecticidal, fungicidal, herbicidal and plant-growth regulating activities (Abad et al., 2004; Chen et al., 2005), especially cytokinin acyivity (Yonova & Stoilkova, 2005). 1,3,4-Thiadiazole derivatives are known to exhibit a wide range of biological activities (Zou et al., 2002; Song & Tan, 2008; Guzeldemirci & Kucukbasmaci, 2010). In view of our extensive interest and as a continuing search for new urea-type cytokinins, we investigate the urea derivatives incorporating a 1,3,4-thiadiazole nucleus, including the title compound.

The crystal structure (Fig.1) revealed that the title molecule which consists of three rings is approximately planar, the dihedral angles formed by the thiadiazole ring with the chlorophenyl and vinylphenyl rings being only 9.70 (15) and 7.22 (10)°, respectively, and the styryl moiety assumes a trans-configuration about C10═C11 double bond of the vinyl moiety. All bond lengths and angles are as expected. In the crystal structure, intermolecular N—H···N and C—H···O hydrogen bonds occurring between centrosymmetrically related molecules result in the formation of ribbons displaying alternate rings of graph-set motifs R₂²(8) and R₂²(14), as shown in Fig. 2 and Table 1.

Related literature top

For the biological activity of urea derivatives, see: 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 top

The title compound was prepared according to the procedure of Song et al. (2007). Suitable crystals were obtained by vapor diffusion of methanol in DMF at room temperature (m.p. >573 K). Elemental analysis: analysis calculated for C₁₇H₁₃ClN₄OS: C 57.22, H 3.67, N 15.70%; found: C 57.45, H 3.56, N 15.82%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. A partial packing diagram of the title molecule. Hydrogen bonds are indicated by dashed lines.

1-(4-Chlorophenyl)-3-{5-[(E)-2-phenylethenyl]-1,3,4-thiadiazol-2-yl}urea top

Crystal data top

C₁₇H₁₃ClN₄OS	F(000) = 736
M_r = 356.82	D_x = 1.458 Mg m⁻³ D_m = 1.459 Mg m⁻³ D_m 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

Data collection top

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

Refinement top

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(F_o²) + (0.0498P)²] where P = (F_o² + 2F_c²)/3
3708 reflections	(Δ/σ)_max = 0.001
223 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₃ClN₄OS	V = 1625.12 (14) Å³
M_r = 356.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2399 (6) Å	µ = 0.38 mm⁻¹
b = 4.1032 (2) Å	T = 298 K
c = 35.2497 (16) Å	0.40 × 0.06 × 0.02 mm
β = 91.525 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2081 reflections with I > 2σ(I)
10860 measured reflections	R_int = 0.091
3708 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.31 e Å⁻³
3708 reflections	Δρ_min = −0.20 e Å⁻³
223 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃ClN₄OS
M_r	356.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.2399 (6), 4.1032 (2), 35.2497 (16)
β (°)	91.525 (4)
V (Å³)	1625.12 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.40 × 0.06 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10860, 3708, 2081
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.154, 1.01
No. of reflections	3708
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z; (ii) −x+1, −y+2, −z.

Acknowledgements

The authors acknowledge financial support from the Scientific Research Fund of Henan Provincial Education Department, China (grant Nos. 2007150050 and 2009B150030).

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