1-(2-Chloro-benzo-yl)-3-(2,3-dimethyl-phen-yl)thio-urea.

The dihedral angle between the two phenyl groups in the title compound, C16H15ClN2OS, is 14.88 (4)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, pairs of N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For background and a related structure, see: Rauf et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen et al. (2002 ▶).

Experimental

Crystal data

C16H15ClN2OS

M = 318.81

Triclinic,

a = 7.489 (3) Å

b = 9.338 (4) Å

c = 13.274 (5) Å

α = 65.674 (13)°

β = 69.975 (16)°

γ = 73.639 (17)°

V = 783.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 123 K

0.50 × 0.35 × 0.28 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

6180 measured reflections

3506 independent reflections

3373 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.08

3506 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.31 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/S1600536812048209/hg5274sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048209/hg5274Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048209/hg5274Isup3.cml

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

C16H15ClN2OS	Z = 2
Mr = 318.81	F(000) = 332
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.489 (3) Å	Cell parameters from 2732 reflections
b = 9.338 (4) Å	θ = 3.0–27.5°
c = 13.274 (5) Å	µ = 0.38 mm−1
α = 65.674 (13)°	T = 123 K
β = 69.975 (16)°	Prism, colorless
γ = 73.639 (17)°	0.50 × 0.35 × 0.28 mm
V = 783.9 (5) Å3

Rigaku/MSC Mercury CCD diffractometer	3373 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.062
Graphite Monochromator monochromator	θmax = 27.5°, θmin = 3.5°
Detector resolution: 14.62 pixels mm-1	h = −6→9
ω scans	k = −9→12
6180 measured reflections	l = −10→17
3506 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.4197P] where P = (Fo2 + 2Fc2)/3
3506 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.31 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	0.38592 (19)	0.07516 (15)	0.27734 (11)	0.0162 (3)
O1	0.44634 (15)	0.17028 (13)	0.18262 (9)	0.0245 (2)
N1	0.20232 (16)	0.09731 (13)	0.34511 (9)	0.0170 (2)
H1	0.1791	0.0275	0.4152	0.020*
C2	0.04854 (19)	0.21635 (15)	0.31664 (11)	0.0151 (2)
S1	−0.15915 (5)	0.22091 (4)	0.41821 (3)	0.01758 (10)
N2	0.07877 (16)	0.31921 (13)	0.20967 (9)	0.0172 (2)
H2	0.1972	0.3159	0.1655	0.021*
C3	0.51000 (18)	−0.07725 (15)	0.32976 (11)	0.0157 (3)
C4	0.48935 (19)	−0.22203 (16)	0.33182 (11)	0.0175 (3)
C5	0.6119 (2)	−0.36192 (17)	0.37358 (12)	0.0234 (3)
H5	0.5988	−0.4597	0.3728	0.028*
C6	0.7535 (2)	−0.35614 (18)	0.41627 (13)	0.0269 (3)
H6	0.8371	−0.4512	0.4460	0.032*
C7	0.7751 (2)	−0.21271 (19)	0.41617 (13)	0.0258 (3)
H7	0.8721	−0.2102	0.4462	0.031*
C8	0.6538 (2)	−0.07287 (17)	0.37186 (12)	0.0211 (3)
H8	0.6695	0.0255	0.3704	0.025*
Cl1	0.30905 (5)	−0.22869 (5)	0.28008 (3)	0.02652 (11)
C9	−0.07073 (18)	0.43554 (16)	0.16191 (10)	0.0155 (3)
C10	−0.06255 (19)	0.59756 (16)	0.12305 (11)	0.0166 (3)
C11	−0.2070 (2)	0.70696 (16)	0.07143 (11)	0.0188 (3)
C12	−0.3533 (2)	0.65092 (18)	0.06365 (11)	0.0206 (3)
H12	−0.4519	0.7251	0.0304	0.025*
C13	−0.3589 (2)	0.48910 (18)	0.10335 (11)	0.0213 (3)
H13	−0.4604	0.4533	0.0973	0.026*
C14	−0.2158 (2)	0.38012 (17)	0.15185 (11)	0.0191 (3)
H14	−0.2166	0.2690	0.1779	0.023*
C15	0.0930 (2)	0.65647 (18)	0.13585 (13)	0.0236 (3)
H15C	0.1687	0.5671	0.1833	0.035*
H15A	0.0342	0.7369	0.1724	0.035*
H15B	0.1773	0.7038	0.0602	0.035*
C16	−0.2044 (2)	0.88359 (18)	0.02548 (14)	0.0299 (3)
H16C	−0.3084	0.9405	−0.0127	0.045*
H16A	−0.0802	0.9059	−0.0295	0.045*
H16B	−0.2229	0.9192	0.0888	0.045*

	U11	U22	U33	U12	U13	U23
C1	0.0165 (6)	0.0149 (6)	0.0178 (6)	−0.0008 (5)	−0.0061 (5)	−0.0059 (5)
O1	0.0191 (5)	0.0235 (5)	0.0202 (5)	−0.0012 (4)	−0.0032 (4)	−0.0004 (4)
N1	0.0172 (5)	0.0141 (5)	0.0143 (5)	0.0016 (4)	−0.0037 (4)	−0.0030 (4)
C2	0.0173 (6)	0.0126 (5)	0.0161 (6)	−0.0001 (5)	−0.0061 (5)	−0.0059 (5)
S1	0.01736 (17)	0.01515 (16)	0.01454 (16)	0.00274 (11)	−0.00288 (12)	−0.00425 (12)
N2	0.0138 (5)	0.0177 (5)	0.0152 (5)	0.0010 (4)	−0.0040 (4)	−0.0031 (4)
C3	0.0140 (6)	0.0156 (6)	0.0149 (6)	0.0003 (5)	−0.0025 (5)	−0.0055 (5)
C4	0.0149 (6)	0.0193 (6)	0.0183 (6)	−0.0020 (5)	−0.0018 (5)	−0.0092 (5)
C5	0.0230 (7)	0.0174 (6)	0.0253 (7)	0.0014 (5)	−0.0021 (6)	−0.0095 (5)
C6	0.0234 (7)	0.0227 (7)	0.0270 (7)	0.0076 (6)	−0.0087 (6)	−0.0070 (6)
C7	0.0185 (7)	0.0310 (8)	0.0285 (7)	0.0027 (6)	−0.0112 (6)	−0.0111 (6)
C8	0.0191 (6)	0.0216 (7)	0.0245 (7)	−0.0018 (5)	−0.0078 (5)	−0.0094 (5)
Cl1	0.02276 (19)	0.0319 (2)	0.0347 (2)	−0.00257 (14)	−0.00959 (15)	−0.02058 (16)
C9	0.0147 (6)	0.0169 (6)	0.0111 (5)	0.0013 (5)	−0.0037 (4)	−0.0037 (5)
C10	0.0157 (6)	0.0184 (6)	0.0138 (5)	−0.0011 (5)	−0.0029 (5)	−0.0057 (5)
C11	0.0184 (6)	0.0181 (6)	0.0153 (6)	0.0013 (5)	−0.0038 (5)	−0.0046 (5)
C12	0.0162 (6)	0.0260 (7)	0.0146 (6)	0.0025 (5)	−0.0055 (5)	−0.0048 (5)
C13	0.0167 (6)	0.0297 (7)	0.0170 (6)	−0.0045 (5)	−0.0050 (5)	−0.0069 (5)
C14	0.0206 (6)	0.0184 (6)	0.0160 (6)	−0.0037 (5)	−0.0041 (5)	−0.0040 (5)
C15	0.0229 (7)	0.0225 (7)	0.0283 (7)	−0.0031 (5)	−0.0097 (6)	−0.0096 (6)
C16	0.0303 (8)	0.0173 (7)	0.0344 (8)	0.0012 (6)	−0.0100 (7)	−0.0037 (6)

C1—O1	1.2211 (17)	C8—H8	0.9500
C1—N1	1.3743 (17)	C9—C14	1.392 (2)
C1—C3	1.5017 (18)	C9—C10	1.395 (2)
N1—C2	1.3912 (17)	C10—C11	1.4115 (19)
N1—H1	0.8800	C10—C15	1.504 (2)
C2—N2	1.3299 (17)	C11—C12	1.389 (2)
C2—S1	1.6770 (14)	C11—C16	1.508 (2)
N2—C9	1.4385 (17)	C12—C13	1.388 (2)
N2—H2	0.8800	C12—H12	0.9500
C3—C8	1.389 (2)	C13—C14	1.385 (2)
C3—C4	1.3917 (19)	C13—H13	0.9500
C4—C5	1.390 (2)	C14—H14	0.9500
C4—Cl1	1.7367 (15)	C15—H15C	0.9800
C5—C6	1.385 (2)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.393 (2)	C16—H16C	0.9800
C6—H6	0.9500	C16—H16A	0.9800
C7—C8	1.393 (2)	C16—H16B	0.9800
C7—H7	0.9500
O1—C1—N1	123.81 (12)	C14—C9—C10	122.26 (13)
O1—C1—C3	121.86 (12)	C14—C9—N2	117.73 (12)
N1—C1—C3	114.33 (11)	C10—C9—N2	119.95 (12)
C1—N1—C2	128.06 (11)	C9—C10—C11	117.91 (13)
C1—N1—H1	116.0	C9—C10—C15	121.91 (13)
C2—N1—H1	116.0	C11—C10—C15	120.18 (13)
N2—C2—N1	116.79 (11)	C12—C11—C10	119.49 (13)
N2—C2—S1	124.85 (10)	C12—C11—C16	119.89 (13)
N1—C2—S1	118.37 (10)	C10—C11—C16	120.61 (13)
C2—N2—C9	123.85 (11)	C13—C12—C11	121.55 (13)
C2—N2—H2	118.1	C13—C12—H12	119.2
C9—N2—H2	118.1	C11—C12—H12	119.2
C8—C3—C4	119.39 (12)	C14—C13—C12	119.64 (13)
C8—C3—C1	119.55 (12)	C14—C13—H13	120.2
C4—C3—C1	120.99 (12)	C12—C13—H13	120.2
C5—C4—C3	121.20 (13)	C13—C14—C9	119.12 (13)
C5—C4—Cl1	119.12 (11)	C13—C14—H14	120.4
C3—C4—Cl1	119.67 (11)	C9—C14—H14	120.4
C6—C5—C4	118.81 (14)	C10—C15—H15C	109.5
C6—C5—H5	120.6	C10—C15—H15A	109.5
C4—C5—H5	120.6	H15C—C15—H15A	109.5
C5—C6—C7	120.82 (14)	C10—C15—H15B	109.5
C5—C6—H6	119.6	H15C—C15—H15B	109.5
C7—C6—H6	119.6	H15A—C15—H15B	109.5
C6—C7—C8	119.76 (14)	C11—C16—H16C	109.5
C6—C7—H7	120.1	C11—C16—H16A	109.5
C8—C7—H7	120.1	H16C—C16—H16A	109.5
C3—C8—C7	119.99 (14)	C11—C16—H16B	109.5
C3—C8—H8	120.0	H16C—C16—H16B	109.5
C7—C8—H8	120.0	H16A—C16—H16B	109.5
O1—C1—N1—C2	7.9 (2)	C1—C3—C8—C7	−177.24 (12)
C3—C1—N1—C2	−172.60 (12)	C6—C7—C8—C3	1.1 (2)
C1—N1—C2—N2	2.5 (2)	C2—N2—C9—C14	−64.20 (17)
C1—N1—C2—S1	−177.20 (11)	C2—N2—C9—C10	118.53 (15)
N1—C2—N2—C9	171.32 (12)	C14—C9—C10—C11	−0.39 (19)
S1—C2—N2—C9	−8.96 (19)	N2—C9—C10—C11	176.76 (11)
O1—C1—C3—C8	74.09 (18)	C14—C9—C10—C15	179.07 (12)
N1—C1—C3—C8	−105.46 (15)	N2—C9—C10—C15	−3.78 (19)
O1—C1—C3—C4	−102.77 (16)	C9—C10—C11—C12	1.59 (19)
N1—C1—C3—C4	77.68 (16)	C15—C10—C11—C12	−177.88 (12)
C8—C3—C4—C5	−1.0 (2)	C9—C10—C11—C16	−178.78 (12)
C1—C3—C4—C5	175.84 (12)	C15—C10—C11—C16	1.75 (19)
C8—C3—C4—Cl1	179.64 (10)	C10—C11—C12—C13	−1.4 (2)
C1—C3—C4—Cl1	−3.49 (17)	C16—C11—C12—C13	178.98 (13)
C3—C4—C5—C6	1.6 (2)	C11—C12—C13—C14	−0.1 (2)
Cl1—C4—C5—C6	−179.05 (11)	C12—C13—C14—C9	1.29 (19)
C4—C5—C6—C7	−0.9 (2)	C10—C9—C14—C13	−1.1 (2)
C5—C6—C7—C8	−0.5 (2)	N2—C9—C14—C13	−178.27 (11)
C4—C3—C8—C7	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.88	2.46	3.3104 (15)	164
N2—H2···O1	0.88	2.00	2.6866 (17)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.88	2.46	3.3104 (15)	164
N2—H2⋯O1	0.88	2.00	2.6866 (17)	134

Symmetry code: (i) .