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

The title mol-ecule, C(16)H(15)ClN(2)OS, 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 and inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers. The dihedral angle between the aromatic rings is 50.18 (5)°.

Related literature

For related compounds, see: Khawar Rauf et al. (2006a ▶,b ▶,c ▶,d ▶). For reference bond-length data, see: Allen (2002 ▶).

Experimental

Crystal data

C16H15ClN2OS

M = 318.81

Triclinic,

a = 8.1315 (9) Å

b = 9.3906 (12) Å

c = 10.5310 (12) Å

α = 93.296 (8)°

β = 92.623 (8)°

γ = 102.579 (9)°

V = 782.14 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 173 (2) K

0.46 × 0.42 × 0.41 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.846, T max = 0.861

8257 measured reflections

3066 independent reflections

2846 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.04

3066 reflections

201 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.33 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000063/bv2114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000063/bv2114Isup2.hkl

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

C16H15ClN2OS	Z = 2
Mr = 318.81	F(000) = 332
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1315 (9) Å	Cell parameters from 7706 reflections
b = 9.3906 (12) Å	θ = 3.7–26.1°
c = 10.5310 (12) Å	µ = 0.38 mm−1
α = 93.296 (8)°	T = 173 K
β = 92.623 (8)°	Block, colourless
γ = 102.579 (9)°	0.46 × 0.42 × 0.41 mm
V = 782.14 (16) Å3

Stoe IPDS II two-circle diffractometer	3066 independent reflections
Radiation source: fine-focus sealed tube	2846 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 26.1°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −10→10
Tmin = 0.846, Tmax = 0.861	k = −10→11
8257 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.041P)2 + 0.3782P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3066 reflections	Δρmax = 0.27 e Å−3
201 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.097 (5)

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
S1	0.23509 (5)	0.60717 (4)	0.59551 (4)	0.02881 (14)
Cl1	−0.24623 (5)	−0.05881 (5)	0.30214 (4)	0.03438 (14)
O1	−0.01441 (13)	0.25159 (11)	0.84778 (9)	0.0258 (2)
N1	0.03004 (15)	0.36655 (13)	0.66166 (11)	0.0201 (3)
H1	−0.014 (2)	0.3701 (19)	0.5889 (18)	0.025 (4)*
N2	0.24161 (15)	0.47809 (13)	0.81460 (11)	0.0215 (3)
H2	0.192 (2)	0.412 (2)	0.8612 (19)	0.034 (5)*
C1	−0.04406 (17)	0.25179 (15)	0.73206 (13)	0.0192 (3)
C2	0.16893 (17)	0.48027 (14)	0.69839 (13)	0.0190 (3)
C11	−0.16148 (16)	0.12650 (14)	0.65810 (13)	0.0190 (3)
C12	−0.15027 (17)	0.09819 (15)	0.52694 (13)	0.0203 (3)
H12	−0.0703	0.1612	0.4809	0.024*
C13	−0.25894 (18)	−0.02426 (15)	0.46557 (14)	0.0232 (3)
C14	−0.37636 (19)	−0.11864 (16)	0.53128 (16)	0.0280 (3)
H14	−0.4495	−0.2015	0.4877	0.034*
C15	−0.38527 (18)	−0.09009 (16)	0.66142 (16)	0.0280 (3)
H15	−0.4650	−0.1538	0.7071	0.034*
C16	−0.27787 (18)	0.03152 (16)	0.72518 (14)	0.0238 (3)
H16	−0.2837	0.0499	0.8143	0.029*
C21	0.39206 (17)	0.58278 (15)	0.86417 (13)	0.0194 (3)
C22	0.55031 (18)	0.56849 (15)	0.82648 (13)	0.0213 (3)
C23	0.69413 (18)	0.67134 (16)	0.88045 (14)	0.0240 (3)
C24	0.67324 (19)	0.78059 (16)	0.96980 (14)	0.0255 (3)
H24	0.7701	0.8486	1.0066	0.031*
C25	0.5146 (2)	0.79247 (17)	1.00630 (14)	0.0280 (3)
H25	0.5034	0.8679	1.0671	0.034*
C26	0.37181 (18)	0.69272 (16)	0.95296 (14)	0.0243 (3)
H26	0.2624	0.6996	0.9768	0.029*
C27	0.5701 (2)	0.44874 (18)	0.73006 (16)	0.0325 (4)
H27A	0.4650	0.3736	0.7199	0.049*
H27B	0.6625	0.4049	0.7598	0.049*
H27C	0.5956	0.4901	0.6480	0.049*
C28	0.8687 (2)	0.6643 (2)	0.84115 (18)	0.0412 (4)
H28A	0.9513	0.7479	0.8823	0.062*
H28B	0.8720	0.6671	0.7484	0.062*
H28C	0.8961	0.5732	0.8672	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0257 (2)	0.0279 (2)	0.0257 (2)	−0.00979 (15)	−0.00909 (14)	0.01144 (15)
Cl1	0.0333 (2)	0.0398 (2)	0.0276 (2)	0.00868 (17)	−0.00649 (16)	−0.01303 (16)
O1	0.0274 (5)	0.0271 (5)	0.0184 (5)	−0.0040 (4)	−0.0013 (4)	0.0031 (4)
N1	0.0201 (6)	0.0193 (6)	0.0172 (6)	−0.0028 (4)	−0.0054 (5)	0.0021 (4)
N2	0.0202 (6)	0.0212 (6)	0.0188 (6)	−0.0040 (5)	−0.0040 (5)	0.0030 (5)
C1	0.0175 (6)	0.0190 (6)	0.0199 (7)	0.0015 (5)	0.0001 (5)	0.0016 (5)
C2	0.0171 (6)	0.0180 (6)	0.0201 (7)	0.0008 (5)	−0.0019 (5)	0.0007 (5)
C11	0.0159 (6)	0.0166 (6)	0.0234 (7)	0.0020 (5)	−0.0026 (5)	0.0019 (5)
C12	0.0179 (6)	0.0182 (6)	0.0238 (7)	0.0026 (5)	−0.0021 (5)	0.0008 (5)
C13	0.0227 (7)	0.0216 (7)	0.0253 (7)	0.0078 (5)	−0.0061 (6)	−0.0046 (6)
C14	0.0222 (7)	0.0184 (7)	0.0395 (9)	−0.0007 (5)	−0.0090 (6)	−0.0025 (6)
C15	0.0215 (7)	0.0211 (7)	0.0384 (9)	−0.0023 (6)	−0.0023 (6)	0.0078 (6)
C16	0.0215 (7)	0.0226 (7)	0.0255 (7)	0.0009 (5)	−0.0006 (6)	0.0046 (6)
C21	0.0206 (7)	0.0189 (6)	0.0163 (6)	0.0002 (5)	−0.0050 (5)	0.0023 (5)
C22	0.0236 (7)	0.0211 (7)	0.0184 (7)	0.0041 (5)	−0.0029 (5)	0.0011 (5)
C23	0.0204 (7)	0.0285 (7)	0.0220 (7)	0.0032 (6)	−0.0033 (5)	0.0038 (6)
C24	0.0235 (7)	0.0249 (7)	0.0240 (7)	−0.0014 (6)	−0.0084 (6)	0.0014 (6)
C25	0.0321 (8)	0.0252 (7)	0.0245 (7)	0.0056 (6)	−0.0055 (6)	−0.0073 (6)
C26	0.0206 (7)	0.0286 (7)	0.0229 (7)	0.0053 (6)	−0.0018 (5)	−0.0021 (6)
C27	0.0316 (8)	0.0343 (8)	0.0311 (8)	0.0092 (7)	0.0010 (6)	−0.0083 (7)
C28	0.0225 (8)	0.0568 (11)	0.0410 (10)	0.0047 (7)	−0.0002 (7)	−0.0057 (8)

S1—C2	1.6751 (14)	C16—H16	0.9500
Cl1—C13	1.7450 (15)	C21—C26	1.394 (2)
O1—C1	1.2315 (17)	C21—C22	1.395 (2)
N1—C1	1.3871 (18)	C22—C23	1.417 (2)
N1—C2	1.3974 (17)	C22—C27	1.511 (2)
N1—H1	0.836 (19)	C23—C24	1.395 (2)
N2—C2	1.3377 (18)	C23—C28	1.511 (2)
N2—C21	1.4472 (17)	C24—C25	1.388 (2)
N2—H2	0.86 (2)	C24—H24	0.9500
C1—C11	1.4966 (18)	C25—C26	1.395 (2)
C11—C16	1.3986 (19)	C25—H25	0.9500
C11—C12	1.402 (2)	C26—H26	0.9500
C12—C13	1.3930 (19)	C27—H27A	0.9800
C12—H12	0.9500	C27—H27B	0.9800
C13—C14	1.392 (2)	C27—H27C	0.9800
C14—C15	1.390 (2)	C28—H28A	0.9800
C14—H14	0.9500	C28—H28B	0.9800
C15—C16	1.393 (2)	C28—H28C	0.9800
C15—H15	0.9500
C1—N1—C2	127.82 (12)	C26—C21—C22	122.41 (13)
C1—N1—H1	117.0 (12)	C26—C21—N2	117.43 (13)
C2—N1—H1	115.2 (12)	C22—C21—N2	120.12 (12)
C2—N2—C21	123.54 (12)	C21—C22—C23	117.98 (13)
C2—N2—H2	116.1 (13)	C21—C22—C27	121.75 (13)
C21—N2—H2	120.3 (13)	C23—C22—C27	120.27 (13)
O1—C1—N1	122.49 (12)	C24—C23—C22	119.38 (13)
O1—C1—C11	121.81 (12)	C24—C23—C28	120.03 (14)
N1—C1—C11	115.70 (12)	C22—C23—C28	120.59 (14)
N2—C2—N1	116.65 (12)	C25—C24—C23	121.69 (13)
N2—C2—S1	124.50 (10)	C25—C24—H24	119.2
N1—C2—S1	118.84 (10)	C23—C24—H24	119.2
C16—C11—C12	120.14 (12)	C24—C25—C26	119.50 (14)
C16—C11—C1	117.91 (12)	C24—C25—H25	120.2
C12—C11—C1	121.84 (12)	C26—C25—H25	120.2
C13—C12—C11	118.60 (13)	C21—C26—C25	119.04 (13)
C13—C12—H12	120.7	C21—C26—H26	120.5
C11—C12—H12	120.7	C25—C26—H26	120.5
C14—C13—C12	121.68 (14)	C22—C27—H27A	109.5
C14—C13—Cl1	119.67 (11)	C22—C27—H27B	109.5
C12—C13—Cl1	118.64 (12)	H27A—C27—H27B	109.5
C15—C14—C13	119.17 (13)	C22—C27—H27C	109.5
C15—C14—H14	120.4	H27A—C27—H27C	109.5
C13—C14—H14	120.4	H27B—C27—H27C	109.5
C14—C15—C16	120.31 (14)	C23—C28—H28A	109.5
C14—C15—H15	119.8	C23—C28—H28B	109.5
C16—C15—H15	119.8	H28A—C28—H28B	109.5
C15—C16—C11	120.08 (14)	C23—C28—H28C	109.5
C15—C16—H16	120.0	H28A—C28—H28C	109.5
C11—C16—H16	120.0	H28B—C28—H28C	109.5
C2—N1—C1—O1	14.4 (2)	C12—C11—C16—C15	−1.2 (2)
C2—N1—C1—C11	−164.92 (13)	C1—C11—C16—C15	−177.41 (13)
C21—N2—C2—N1	176.32 (12)	C2—N2—C21—C26	103.83 (16)
C21—N2—C2—S1	−2.7 (2)	C2—N2—C21—C22	−78.45 (18)
C1—N1—C2—N2	1.0 (2)	C26—C21—C22—C23	−0.6 (2)
C1—N1—C2—S1	−179.91 (11)	N2—C21—C22—C23	−178.24 (12)
O1—C1—C11—C16	20.3 (2)	C26—C21—C22—C27	−179.96 (14)
N1—C1—C11—C16	−160.43 (12)	N2—C21—C22—C27	2.4 (2)
O1—C1—C11—C12	−155.86 (13)	C21—C22—C23—C24	1.0 (2)
N1—C1—C11—C12	23.43 (19)	C27—C22—C23—C24	−179.67 (14)
C16—C11—C12—C13	1.1 (2)	C21—C22—C23—C28	−178.42 (14)
C1—C11—C12—C13	177.14 (12)	C27—C22—C23—C28	0.9 (2)
C11—C12—C13—C14	−0.5 (2)	C22—C23—C24—C25	−0.8 (2)
C11—C12—C13—Cl1	179.51 (10)	C28—C23—C24—C25	178.63 (15)
C12—C13—C14—C15	−0.1 (2)	C23—C24—C25—C26	0.2 (2)
Cl1—C13—C14—C15	179.96 (11)	C22—C21—C26—C25	0.0 (2)
C13—C14—C15—C16	0.0 (2)	N2—C21—C26—C25	177.71 (13)
C14—C15—C16—C11	0.7 (2)	C24—C25—C26—C21	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1···S1i	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1⋯S1i	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)

Symmetry code: (i) .