N-(3-Chloro-4-eth-oxy-benzo-yl)-N'-(2-meth-oxy-phen-yl)thio-urea.

In the title compound, C(17)H(17)ClN(2)O(3)S, the central carbonyl-thio-urea unit is nearly planar [maximum atomic deviation = 0.019 (3) Å] and makes dihedral angles of 2.47 (7) and 17.76 (6)° with the terminal benzene rings. An intra-molecular N-H⋯O hydrogen bond occurs. Weak inter-molecular C-H⋯S and C-H⋯Cl hydrogen bonding is observed in the crystal structure.

Related literature

For applications of thio­urea derivatives, see: Antholine & Taketa (1982 ▶); Schroeder (1955 ▶). For related structures, see: Yusof & Yamin (2004a ▶,b ▶); Ali et al. (2004 ▶). For related acyl­thio­urea derivatives, see: Zhang et al. (2003 ▶, 2006 ▶).

Experimental

Crystal data

C17H17ClN2O3S

M = 364.84

Triclinic,

a = 7.8238 (8) Å

b = 8.4791 (11) Å

c = 14.9867 (13) Å

α = 76.365 (7)°

β = 89.384 (5)°

γ = 62.647 (4)°

V = 852.65 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.38 × 0.35 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.874, T max = 0.908

4903 measured reflections

3314 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.216

S = 1.06

3314 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.85 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054644/xu5125sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054644/xu5125Isup2.hkl

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

C17H17ClN2O3S	Z = 2
Mr = 364.84	F(000) = 380
Triclinic, P1	Dx = 1.421 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8238 (8) Å	Cell parameters from 2087 reflections
b = 8.4791 (11) Å	θ = 2.8–29.3°
c = 14.9867 (13) Å	µ = 0.36 mm−1
α = 76.365 (7)°	T = 296 K
β = 89.384 (5)°	Block, yellow
γ = 62.647 (4)°	0.38 × 0.35 × 0.27 mm
V = 852.65 (16) Å3

Bruker APEXII CCD diffractometer	3314 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
graphite	Rint = 0.012
φ and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.874, Tmax = 0.908	k = −10→9
4903 measured reflections	l = −18→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1281P)2 + 0.5121P] where P = (Fo2 + 2Fc2)/3
3314 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.85 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	0.7479 (5)	0.3322 (4)	0.6563 (2)	0.0500 (7)
C2	0.9023 (5)	0.1588 (4)	0.6605 (2)	0.0484 (7)
C3	1.0005 (5)	0.1342 (4)	0.5825 (2)	0.0535 (7)
H3	1.1037	0.0201	0.5832	0.064*
C4	0.9454 (5)	0.2778 (4)	0.5048 (2)	0.0507 (7)
H4	1.0123	0.2591	0.4534	0.061*
C5	0.7916 (4)	0.4512 (4)	0.50087 (19)	0.0455 (7)
C6	0.6918 (4)	0.4750 (4)	0.5784 (2)	0.0467 (7)
H6	0.5868	0.5883	0.5772	0.056*
C7	1.0853 (5)	−0.1587 (4)	0.7415 (2)	0.0600 (8)
H7A	1.2106	−0.1668	0.7289	0.072*
H7B	1.0421	−0.1991	0.6950	0.072*
C8	1.0993 (6)	−0.2751 (5)	0.8357 (3)	0.0758 (11)
H8A	1.1418	−0.2333	0.8809	0.114*
H8B	1.1905	−0.4008	0.8396	0.114*
H8C	0.9745	−0.2659	0.8472	0.114*
C9	0.7458 (4)	0.5941 (4)	0.4133 (2)	0.0488 (7)
C10	0.5447 (4)	0.9307 (4)	0.34023 (19)	0.0435 (6)
C11	0.5829 (4)	1.0267 (4)	0.17305 (19)	0.0438 (6)
C12	0.7042 (4)	0.9479 (4)	0.1091 (2)	0.0465 (7)
C13	0.6871 (5)	1.0502 (4)	0.0204 (2)	0.0557 (8)
H13	0.7675	0.9962	−0.0217	0.067*
C14	0.5509 (5)	1.2321 (5)	−0.0058 (2)	0.0607 (8)
H14	0.5390	1.3018	−0.0657	0.073*
C15	0.4325 (5)	1.3110 (4)	0.0562 (2)	0.0624 (9)
H15	0.3413	1.4346	0.0379	0.075*
C16	0.4464 (5)	1.2103 (4)	0.1452 (2)	0.0552 (8)
H16	0.3641	1.2656	0.1863	0.066*
C23	0.9845 (6)	0.6837 (5)	0.0906 (3)	0.0777 (12)
H23A	0.9323	0.6801	0.0339	0.117*
H23B	1.0716	0.5608	0.1254	0.117*
H23C	1.0533	0.7541	0.0770	0.117*
Cl1	0.6221 (2)	0.36762 (17)	0.75042 (8)	0.0918 (4)
N1	0.6147 (4)	0.7725 (3)	0.41304 (16)	0.0461 (6)
H1	0.5705	0.7877	0.4648	0.055*
N2	0.6167 (4)	0.9049 (3)	0.26084 (16)	0.0480 (6)
H2	0.6994	0.7928	0.2638	0.058*
O1	0.9466 (4)	0.0284 (3)	0.74006 (15)	0.0597 (6)
O2	0.8217 (4)	0.5561 (3)	0.34440 (15)	0.0700 (7)
O3	0.8333 (4)	0.7658 (3)	0.14238 (16)	0.0636 (7)
S1	0.38700 (13)	1.12797 (11)	0.36170 (5)	0.0603 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0574 (17)	0.0502 (16)	0.0453 (16)	−0.0268 (14)	0.0093 (13)	−0.0143 (13)
C2	0.0594 (18)	0.0439 (15)	0.0419 (15)	−0.0256 (14)	−0.0015 (12)	−0.0080 (12)
C3	0.0589 (18)	0.0428 (15)	0.0447 (16)	−0.0135 (13)	0.0026 (13)	−0.0086 (13)
C4	0.0574 (17)	0.0429 (15)	0.0420 (15)	−0.0150 (13)	0.0073 (12)	−0.0120 (12)
C5	0.0512 (16)	0.0412 (14)	0.0407 (15)	−0.0183 (13)	0.0019 (12)	−0.0115 (12)
C6	0.0514 (16)	0.0394 (14)	0.0470 (16)	−0.0188 (13)	0.0064 (12)	−0.0128 (12)
C7	0.067 (2)	0.0490 (17)	0.0524 (18)	−0.0226 (16)	−0.0052 (15)	−0.0028 (14)
C8	0.087 (3)	0.062 (2)	0.067 (2)	−0.037 (2)	−0.006 (2)	0.0087 (18)
C9	0.0557 (17)	0.0391 (14)	0.0419 (15)	−0.0151 (13)	0.0026 (12)	−0.0086 (12)
C10	0.0443 (15)	0.0400 (14)	0.0414 (14)	−0.0151 (12)	0.0039 (11)	−0.0124 (11)
C11	0.0467 (15)	0.0392 (14)	0.0383 (14)	−0.0154 (12)	0.0033 (11)	−0.0080 (11)
C12	0.0498 (16)	0.0395 (14)	0.0442 (15)	−0.0168 (12)	0.0060 (12)	−0.0091 (12)
C13	0.0631 (19)	0.0518 (17)	0.0456 (16)	−0.0220 (15)	0.0154 (14)	−0.0119 (13)
C14	0.068 (2)	0.0560 (19)	0.0449 (17)	−0.0253 (16)	0.0057 (14)	0.0015 (14)
C15	0.0605 (19)	0.0432 (16)	0.0551 (18)	−0.0080 (14)	0.0061 (15)	0.0023 (14)
C16	0.0524 (17)	0.0445 (16)	0.0475 (16)	−0.0079 (13)	0.0095 (13)	−0.0066 (13)
C23	0.069 (2)	0.053 (2)	0.090 (3)	−0.0121 (17)	0.032 (2)	−0.0168 (19)
Cl1	0.1143 (9)	0.0876 (8)	0.0697 (7)	−0.0445 (7)	0.0403 (6)	−0.0216 (5)
N1	0.0549 (14)	0.0374 (12)	0.0348 (11)	−0.0131 (10)	0.0070 (10)	−0.0083 (9)
N2	0.0556 (14)	0.0361 (12)	0.0380 (12)	−0.0101 (10)	0.0073 (10)	−0.0092 (10)
O1	0.0798 (16)	0.0468 (12)	0.0420 (11)	−0.0253 (11)	0.0027 (10)	−0.0027 (9)
O2	0.0962 (18)	0.0416 (11)	0.0400 (12)	−0.0062 (12)	0.0159 (11)	−0.0103 (9)
O3	0.0711 (15)	0.0417 (11)	0.0552 (13)	−0.0089 (10)	0.0227 (11)	−0.0106 (10)
S1	0.0673 (6)	0.0436 (5)	0.0466 (5)	−0.0055 (4)	0.0105 (4)	−0.0144 (3)

C1—C6	1.371 (4)	C10—N2	1.333 (4)
C1—C2	1.397 (4)	C10—N1	1.392 (4)
C1—Cl1	1.716 (3)	C10—S1	1.665 (3)
C2—O1	1.341 (4)	C11—C16	1.384 (4)
C2—C3	1.396 (4)	C11—C12	1.402 (4)
C3—C4	1.373 (4)	C11—N2	1.408 (4)
C3—H3	0.9300	C12—O3	1.367 (3)
C4—C5	1.395 (4)	C12—C13	1.375 (4)
C4—H4	0.9300	C13—C14	1.372 (5)
C5—C6	1.395 (4)	C13—H13	0.9300
C5—C9	1.477 (4)	C14—C15	1.369 (5)
C6—H6	0.9300	C14—H14	0.9300
C7—O1	1.448 (4)	C15—C16	1.379 (4)
C7—C8	1.492 (5)	C15—H15	0.9300
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C23—O3	1.402 (4)
C8—H8A	0.9600	C23—H23A	0.9600
C8—H8B	0.9600	C23—H23B	0.9600
C8—H8C	0.9600	C23—H23C	0.9600
C9—O2	1.221 (4)	N1—H1	0.8600
C9—N1	1.383 (4)	N2—H2	0.8600
C6—C1—C2	121.7 (3)	N2—C10—S1	127.6 (2)
C6—C1—Cl1	118.8 (2)	N1—C10—S1	117.5 (2)
C2—C1—Cl1	119.4 (2)	C16—C11—C12	118.5 (3)
O1—C2—C3	124.8 (3)	C16—C11—N2	127.1 (3)
O1—C2—C1	117.2 (3)	C12—C11—N2	114.4 (2)
C3—C2—C1	118.0 (3)	O3—C12—C13	124.7 (3)
C4—C3—C2	120.2 (3)	O3—C12—C11	114.4 (2)
C4—C3—H3	119.9	C13—C12—C11	120.9 (3)
C2—C3—H3	119.9	C14—C13—C12	119.7 (3)
C3—C4—C5	121.7 (3)	C14—C13—H13	120.2
C3—C4—H4	119.1	C12—C13—H13	120.2
C5—C4—H4	119.1	C15—C14—C13	120.0 (3)
C6—C5—C4	118.0 (3)	C15—C14—H14	120.0
C6—C5—C9	125.4 (3)	C13—C14—H14	120.0
C4—C5—C9	116.6 (3)	C14—C15—C16	121.1 (3)
C1—C6—C5	120.3 (3)	C14—C15—H15	119.4
C1—C6—H6	119.9	C16—C15—H15	119.4
C5—C6—H6	119.9	C15—C16—C11	119.8 (3)
O1—C7—C8	106.8 (3)	C15—C16—H16	120.1
O1—C7—H7A	110.4	C11—C16—H16	120.1
C8—C7—H7A	110.4	O3—C23—H23A	109.5
O1—C7—H7B	110.4	O3—C23—H23B	109.5
C8—C7—H7B	110.4	H23A—C23—H23B	109.5
H7A—C7—H7B	108.6	O3—C23—H23C	109.5
C7—C8—H8A	109.5	H23A—C23—H23C	109.5
C7—C8—H8B	109.5	H23B—C23—H23C	109.5
H8A—C8—H8B	109.5	C9—N1—C10	128.7 (2)
C7—C8—H8C	109.5	C9—N1—H1	115.6
H8A—C8—H8C	109.5	C10—N1—H1	115.6
H8B—C8—H8C	109.5	C10—N2—C11	132.1 (2)
O2—C9—N1	121.6 (3)	C10—N2—H2	114.0
O2—C9—C5	121.3 (3)	C11—N2—H2	114.0
N1—C9—C5	117.1 (3)	C2—O1—C7	118.0 (2)
N2—C10—N1	114.8 (2)	C12—O3—C23	118.7 (3)
C6—C1—C2—O1	179.6 (3)	O3—C12—C13—C14	179.5 (3)
Cl1—C1—C2—O1	−1.3 (4)	C11—C12—C13—C14	0.6 (5)
C6—C1—C2—C3	0.4 (5)	C12—C13—C14—C15	−0.1 (6)
Cl1—C1—C2—C3	179.5 (2)	C13—C14—C15—C16	−0.5 (6)
O1—C2—C3—C4	−178.9 (3)	C14—C15—C16—C11	0.6 (6)
C1—C2—C3—C4	0.2 (5)	C12—C11—C16—C15	−0.1 (5)
C2—C3—C4—C5	0.1 (5)	N2—C11—C16—C15	179.8 (3)
C3—C4—C5—C6	−0.9 (5)	O2—C9—N1—C10	1.6 (5)
C3—C4—C5—C9	−179.8 (3)	C5—C9—N1—C10	−178.8 (3)
C2—C1—C6—C5	−1.3 (5)	N2—C10—N1—C9	−0.9 (5)
Cl1—C1—C6—C5	179.6 (2)	S1—C10—N1—C9	−179.7 (3)
C4—C5—C6—C1	1.5 (5)	N1—C10—N2—C11	179.6 (3)
C9—C5—C6—C1	−179.8 (3)	S1—C10—N2—C11	−1.8 (5)
C6—C5—C9—O2	−169.5 (3)	C16—C11—N2—C10	−6.2 (5)
C4—C5—C9—O2	9.2 (5)	C12—C11—N2—C10	173.6 (3)
C6—C5—C9—N1	11.0 (5)	C3—C2—O1—C7	−10.3 (5)
C4—C5—C9—N1	−170.3 (3)	C1—C2—O1—C7	170.6 (3)
C16—C11—C12—O3	−179.5 (3)	C8—C7—O1—C2	−177.0 (3)
N2—C11—C12—O3	0.7 (4)	C13—C12—O3—C23	13.3 (5)
C16—C11—C12—C13	−0.5 (5)	C11—C12—O3—C23	−167.8 (3)
N2—C11—C12—C13	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.88	2.613 (3)	143
C6—H6···S1i	0.93	2.86	3.468 (2)	124
C14—H14···Cl1ii	0.93	2.81	3.680 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.88	2.613 (3)	143
C6—H6⋯S1i	0.93	2.86	3.468 (2)	124
C14—H14⋯Cl1ii	0.93	2.81	3.680 (3)	156

Symmetry codes: (i) ; (ii) .