1-(2-Chloro-benzo-yl)-3-(3-meth-oxy-phen-yl)thio-urea.

The title compound, C15H13ClN2O2S, exists in the solid state in its thione form with typical thio-urea C-S and C-O bonds lengths as well as shortened C-N bonds. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For previous work on N,N′-disubstituted thio­ureas, see: Rauf et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C15H13ClN2O2S

M = 320.78

Triclinic,

a = 6.276 (3) Å

b = 10.202 (5) Å

c = 11.411 (5) Å

α = 94.541 (7)°

β = 93.305 (6)°

γ = 96.918 (7)°

V = 721.3 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 123 K

0.45 × 0.36 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

5698 measured reflections

3222 independent reflections

3071 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.09

3222 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: Yadokari-XG (Wakita, 2001 ▶; Kabuto et al., 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048830/mw2100sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048830/mw2100Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048830/mw2100Isup3.cml

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

C15H13ClN2O2S	Z = 2
Mr = 320.78	F(000) = 332
Triclinic, P1	Dx = 1.477 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 6.276 (3) Å	Cell parameters from 2546 reflections
b = 10.202 (5) Å	θ = 3.3–27.5°
c = 11.411 (5) Å	µ = 0.41 mm−1
α = 94.541 (7)°	T = 123 K
β = 93.305 (6)°	Block, colorless
γ = 96.918 (7)°	0.45 × 0.36 × 0.20 mm
V = 721.3 (6) Å3

Rigaku/MSC Mercury CCD diffractometer	3071 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.052
Graphite Monochromator monochromator	θmax = 27.5°, θmin = 3.3°
Detector resolution: 14.62 pixels mm-1	h = −8→5
ω scans	k = −13→13
5698 measured reflections	l = −14→14
3222 independent 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0309P)2 + 0.5054P] where P = (Fo2 + 2Fc2)/3
3222 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.34 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	0.6542 (2)	0.57142 (13)	0.79707 (12)	0.0144 (3)
O1	0.58303 (17)	0.56062 (10)	0.89370 (9)	0.0186 (2)
N1	0.56572 (19)	0.49567 (12)	0.69582 (11)	0.0155 (2)
H1	0.6364	0.5052	0.6320	0.019*
C2	0.3774 (2)	0.40595 (13)	0.68314 (13)	0.0147 (3)
S1	0.28505 (7)	0.34880 (4)	0.54559 (3)	0.02392 (12)
N2	0.28727 (18)	0.37856 (12)	0.78283 (10)	0.0148 (2)
H2	0.3660	0.4085	0.8479	0.018*
C3	0.8470 (2)	0.66726 (14)	0.77733 (12)	0.0149 (3)
C4	0.8823 (2)	0.79519 (14)	0.83489 (13)	0.0168 (3)
C5	1.0642 (3)	0.88129 (15)	0.81696 (14)	0.0217 (3)
H5	1.0863	0.9678	0.8566	0.026*
C6	1.2135 (2)	0.84109 (16)	0.74122 (15)	0.0236 (3)
H6	1.3379	0.9001	0.7292	0.028*
C7	1.1816 (2)	0.71488 (16)	0.68298 (14)	0.0219 (3)
H7	1.2837	0.6875	0.6309	0.026*
C8	0.9996 (2)	0.62846 (15)	0.70116 (13)	0.0179 (3)
H8	0.9787	0.5420	0.6614	0.021*
Cl1	0.69817 (6)	0.85411 (4)	0.92737 (3)	0.02243 (11)
C9	0.0829 (2)	0.30814 (13)	0.79995 (12)	0.0141 (3)
C10	−0.0238 (2)	0.20764 (14)	0.72013 (13)	0.0166 (3)
H10	0.0399	0.1801	0.6503	0.020*
C11	−0.2262 (2)	0.14852 (14)	0.74534 (13)	0.0164 (3)
C12	−0.3209 (2)	0.18776 (14)	0.84774 (13)	0.0181 (3)
H12	−0.4605	0.1482	0.8627	0.022*
C13	−0.2092 (2)	0.28502 (15)	0.92748 (13)	0.0186 (3)
H13	−0.2712	0.3107	0.9984	0.022*
C14	−0.0068 (2)	0.34540 (14)	0.90434 (13)	0.0169 (3)
H14	0.0697	0.4116	0.9595	0.020*
O2	−0.34498 (17)	0.04884 (11)	0.67328 (10)	0.0236 (3)
C15	−0.2488 (3)	0.00094 (16)	0.57046 (14)	0.0243 (3)
H15C	−0.2194	0.0732	0.5197	0.037*
H15A	−0.3473	−0.0710	0.5274	0.037*
H15B	−0.1138	−0.0322	0.5937	0.037*

	U11	U22	U33	U12	U13	U23
C1	0.0126 (6)	0.0132 (6)	0.0166 (7)	−0.0001 (5)	−0.0020 (5)	0.0008 (5)
O1	0.0193 (5)	0.0203 (5)	0.0144 (5)	−0.0045 (4)	0.0003 (4)	0.0006 (4)
N1	0.0148 (6)	0.0161 (6)	0.0139 (6)	−0.0037 (4)	0.0018 (4)	−0.0010 (4)
C2	0.0147 (6)	0.0110 (6)	0.0176 (7)	−0.0007 (5)	0.0001 (5)	−0.0003 (5)
S1	0.0298 (2)	0.0236 (2)	0.01342 (19)	−0.01405 (15)	0.00077 (14)	−0.00207 (14)
N2	0.0127 (5)	0.0153 (6)	0.0147 (6)	−0.0028 (4)	−0.0013 (4)	−0.0005 (4)
C3	0.0137 (6)	0.0156 (6)	0.0141 (6)	−0.0021 (5)	−0.0029 (5)	0.0029 (5)
C4	0.0175 (7)	0.0171 (7)	0.0147 (6)	−0.0009 (5)	−0.0030 (5)	0.0017 (5)
C5	0.0230 (7)	0.0183 (7)	0.0207 (7)	−0.0069 (6)	−0.0058 (6)	0.0030 (6)
C6	0.0161 (7)	0.0268 (8)	0.0260 (8)	−0.0070 (6)	−0.0048 (6)	0.0099 (6)
C7	0.0136 (7)	0.0283 (8)	0.0239 (8)	0.0003 (6)	0.0003 (5)	0.0071 (6)
C8	0.0148 (6)	0.0184 (7)	0.0197 (7)	0.0001 (5)	−0.0022 (5)	0.0026 (5)
Cl1	0.0263 (2)	0.01867 (18)	0.02099 (19)	0.00013 (14)	0.00284 (14)	−0.00308 (13)
C9	0.0124 (6)	0.0128 (6)	0.0164 (7)	−0.0008 (5)	−0.0007 (5)	0.0031 (5)
C10	0.0163 (7)	0.0162 (7)	0.0163 (7)	−0.0011 (5)	0.0027 (5)	−0.0015 (5)
C11	0.0152 (6)	0.0144 (6)	0.0183 (7)	−0.0021 (5)	−0.0003 (5)	−0.0002 (5)
C12	0.0144 (6)	0.0178 (7)	0.0220 (7)	−0.0003 (5)	0.0042 (5)	0.0033 (5)
C13	0.0204 (7)	0.0188 (7)	0.0168 (7)	0.0020 (5)	0.0047 (5)	0.0009 (5)
C14	0.0186 (7)	0.0150 (6)	0.0159 (7)	−0.0002 (5)	−0.0004 (5)	−0.0005 (5)
O2	0.0190 (5)	0.0236 (6)	0.0239 (6)	−0.0095 (4)	0.0047 (4)	−0.0077 (4)
C15	0.0230 (7)	0.0252 (8)	0.0220 (8)	−0.0020 (6)	0.0012 (6)	−0.0074 (6)

C1—O1	1.2213 (18)	C7—H7	0.9500
C1—N1	1.3862 (18)	C8—H8	0.9500
C1—C3	1.5007 (19)	C9—C14	1.392 (2)
N1—C2	1.3981 (18)	C9—C10	1.3948 (19)
N1—H1	0.8800	C10—C11	1.394 (2)
C2—N2	1.3334 (19)	C10—H10	0.9500
C2—S1	1.6758 (16)	C11—O2	1.3713 (17)
N2—C9	1.4243 (18)	C11—C12	1.394 (2)
N2—H2	0.8800	C12—C13	1.385 (2)
C3—C4	1.401 (2)	C12—H12	0.9500
C3—C8	1.401 (2)	C13—C14	1.393 (2)
C4—C5	1.389 (2)	C13—H13	0.9500
C4—Cl1	1.7370 (16)	C14—H14	0.9500
C5—C6	1.387 (2)	O2—C15	1.4288 (19)
C5—H5	0.9500	C15—H15C	0.9800
C6—C7	1.388 (2)	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—C8	1.392 (2)
O1—C1—N1	123.20 (13)	C7—C8—H8	119.6
O1—C1—C3	122.98 (12)	C3—C8—H8	119.6
N1—C1—C3	113.82 (12)	C14—C9—C10	120.87 (13)
C1—N1—C2	127.64 (12)	C14—C9—N2	115.32 (12)
C1—N1—H1	116.2	C10—C9—N2	123.81 (13)
C2—N1—H1	116.2	C11—C10—C9	118.42 (13)
N2—C2—N1	115.74 (12)	C11—C10—H10	120.8
N2—C2—S1	127.15 (11)	C9—C10—H10	120.8
N1—C2—S1	117.08 (11)	O2—C11—C12	115.39 (13)
C2—N2—C9	129.80 (12)	O2—C11—C10	123.32 (13)
C2—N2—H2	115.1	C12—C11—C10	121.30 (13)
C9—N2—H2	115.1	C13—C12—C11	119.29 (13)
C4—C3—C8	118.29 (13)	C13—C12—H12	120.4
C4—C3—C1	121.86 (13)	C11—C12—H12	120.4
C8—C3—C1	119.84 (13)	C12—C13—C14	120.44 (13)
C5—C4—C3	120.81 (14)	C12—C13—H13	119.8
C5—C4—Cl1	117.49 (12)	C14—C13—H13	119.8
C3—C4—Cl1	121.67 (11)	C9—C14—C13	119.61 (13)
C6—C5—C4	120.05 (14)	C9—C14—H14	120.2
C6—C5—H5	120.0	C13—C14—H14	120.2
C4—C5—H5	120.0	C11—O2—C15	117.13 (12)
C5—C6—C7	120.15 (14)	O2—C15—H15C	109.5
C5—C6—H6	119.9	O2—C15—H15A	109.5
C7—C6—H6	119.9	H15C—C15—H15A	109.5
C6—C7—C8	119.81 (15)	O2—C15—H15B	109.5
C6—C7—H7	120.1	H15C—C15—H15B	109.5
C8—C7—H7	120.1	H15A—C15—H15B	109.5
C7—C8—C3	120.88 (14)
O1—C1—N1—C2	6.0 (2)	C6—C7—C8—C3	0.3 (2)
C3—C1—N1—C2	−174.52 (13)	C4—C3—C8—C7	−0.1 (2)
C1—N1—C2—N2	−8.8 (2)	C1—C3—C8—C7	−178.91 (13)
C1—N1—C2—S1	169.20 (12)	C2—N2—C9—C14	−151.59 (15)
N1—C2—N2—C9	169.91 (13)	C2—N2—C9—C10	28.9 (2)
S1—C2—N2—C9	−7.9 (2)	C14—C9—C10—C11	2.3 (2)
O1—C1—C3—C4	−39.5 (2)	N2—C9—C10—C11	−178.27 (13)
N1—C1—C3—C4	141.05 (14)	C9—C10—C11—O2	−179.88 (14)
O1—C1—C3—C8	139.31 (15)	C9—C10—C11—C12	−0.2 (2)
N1—C1—C3—C8	−40.16 (18)	O2—C11—C12—C13	177.99 (13)
C8—C3—C4—C5	−0.1 (2)	C10—C11—C12—C13	−1.7 (2)
C1—C3—C4—C5	178.72 (13)	C11—C12—C13—C14	1.6 (2)
C8—C3—C4—Cl1	177.95 (11)	C10—C9—C14—C13	−2.4 (2)
C1—C3—C4—Cl1	−3.24 (19)	N2—C9—C14—C13	178.10 (13)
C3—C4—C5—C6	0.1 (2)	C12—C13—C14—C9	0.4 (2)
Cl1—C4—C5—C6	−178.03 (12)	C12—C11—O2—C15	−176.82 (14)
C4—C5—C6—C7	0.1 (2)	C10—C11—O2—C15	2.9 (2)
C5—C6—C7—C8	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	1.95	2.6500 (17)	135
N1—H1···S1i	0.88	2.64	3.4080 (17)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.88	1.95	2.6500 (17)	135
N1—H1⋯S1i	0.88	2.64	3.4080 (17)	146

Symmetry code: (i) .