N-Benzyl-carbamothioyl-2-chloro-benzamide.

In the title compound, C(15)H(13)ClN(2)OS, the dihedral angles between the sulfourea group and the benzene ring and the chloro-benzene ring are 35.8 (6) and 81.6 (6)° respectively. An intra-molecular N-H⋯O inter-action occurs. In the crystal, a combination of inter-molecular π-π stacking inter-actions [centroid-centroid distance = 4.0616 (16) Å] and N-H⋯S hydrogen bonds stabilizes the structure.

Related literature

For general background to the chemistry and biological activity of thio­urea derivatives and their use, see: Jain & Rao (2003 ▶); Zeng et al. (2003 ▶); Xu et al. (2004 ▶); Zheng et al. (2004 ▶); D’hooghe et al. (2005 ▶); Saeed et al. (2008 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C15H13ClN2OS

M = 304.78

Triclinic,

a = 7.347 (2) Å

b = 9.658 (3) Å

c = 11.003 (3) Å

α = 110.150 (5)°

β = 90.767 (3)°

γ = 104.058 (3)°

V = 707.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 153 K

0.40 × 0.30 × 0.30 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.852, T max = 0.886

5691 measured reflections

2481 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.01

2481 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023822/pk2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023822/pk2248Isup2.hkl

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

C15H13ClN2OS	Z = 2
Mr = 304.78	F(000) = 316
Triclinic, P1	Dx = 1.432 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.347 (2) Å	Cell parameters from 2259 reflections
b = 9.658 (3) Å	θ = 3.2–27.5°
c = 11.003 (3) Å	µ = 0.41 mm−1
α = 110.150 (5)°	T = 153 K
β = 90.767 (3)°	Block, colorless
γ = 104.058 (3)°	0.40 × 0.30 × 0.30 mm
V = 707.0 (4) Å3

Rigaku AFC10/Saturn724+ diffractometer	2481 independent reflections
Radiation source: Rotating Anode	2194 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 28.6 pixels mm-1	θmax = 25.3°, θmin = 3.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.852, Tmax = 0.886	l = −13→13
5691 measured 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.265P] where P = (Fo2 + 2Fc2)/3
2481 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.18 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
Cl1	0.69955 (6)	0.10088 (5)	0.08296 (4)	0.03365 (14)
S1	0.81096 (6)	0.64421 (5)	0.00524 (4)	0.02590 (13)
O1	0.71779 (16)	0.46704 (14)	0.34073 (11)	0.0283 (3)
N1	0.84005 (19)	0.48399 (15)	0.15434 (13)	0.0203 (3)
N2	0.62797 (19)	0.63073 (16)	0.20842 (13)	0.0219 (3)
C1	0.9133 (2)	0.18430 (18)	0.18156 (14)	0.0202 (3)
C2	1.0373 (2)	0.09656 (19)	0.18009 (15)	0.0243 (4)
H2	1.0062	−0.0087	0.1267	0.029*
C3	1.2074 (2)	0.1651 (2)	0.25780 (16)	0.0264 (4)
H3	1.2953	0.1069	0.2562	0.032*
C4	1.2512 (2)	0.3177 (2)	0.33806 (16)	0.0261 (4)
H4	1.3678	0.3632	0.3919	0.031*
C5	1.1247 (2)	0.40367 (18)	0.33975 (15)	0.0226 (3)
H5	1.1539	0.5079	0.3956	0.027*
C6	0.9550 (2)	0.33762 (17)	0.25978 (14)	0.0181 (3)
C7	0.8239 (2)	0.43410 (17)	0.25728 (15)	0.0192 (3)
C8	0.7526 (2)	0.58559 (17)	0.12955 (14)	0.0193 (3)
C9	0.5298 (2)	0.74124 (19)	0.19805 (16)	0.0254 (4)
H9A	0.4528	0.6995	0.1126	0.030*
H9B	0.6234	0.8366	0.2031	0.030*
C10	0.4041 (2)	0.77650 (17)	0.30540 (15)	0.0201 (3)
C11	0.4601 (2)	0.79494 (18)	0.43245 (15)	0.0227 (3)
H11	0.5805	0.7838	0.4530	0.027*
C12	0.3419 (2)	0.82945 (18)	0.52955 (16)	0.0253 (4)
H12	0.3805	0.8400	0.6158	0.030*
C13	0.1679 (2)	0.84838 (18)	0.50053 (17)	0.0279 (4)
H13	0.0868	0.8722	0.5668	0.033*
C14	0.1120 (2)	0.83262 (19)	0.37480 (17)	0.0285 (4)
H14	−0.0065	0.8474	0.3552	0.034*
C15	0.2287 (2)	0.79521 (19)	0.27727 (16)	0.0248 (4)
H15	0.1884	0.7823	0.1907	0.030*
H1N	0.924 (3)	0.459 (2)	0.1044 (18)	0.030 (5)*
H2N	0.605 (3)	0.593 (2)	0.2644 (19)	0.032 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0275 (2)	0.0300 (2)	0.0343 (3)	0.00316 (18)	−0.00924 (18)	0.00382 (19)
S1	0.0321 (2)	0.0347 (3)	0.0234 (2)	0.01932 (19)	0.01270 (17)	0.01826 (19)
O1	0.0315 (7)	0.0388 (7)	0.0274 (6)	0.0197 (6)	0.0153 (5)	0.0201 (6)
N1	0.0235 (7)	0.0238 (7)	0.0197 (7)	0.0131 (6)	0.0087 (6)	0.0103 (6)
N2	0.0253 (7)	0.0261 (7)	0.0240 (7)	0.0137 (6)	0.0106 (6)	0.0158 (6)
C1	0.0195 (8)	0.0234 (8)	0.0171 (8)	0.0041 (6)	0.0018 (6)	0.0077 (7)
C2	0.0319 (9)	0.0219 (8)	0.0223 (8)	0.0115 (7)	0.0074 (7)	0.0086 (7)
C3	0.0250 (9)	0.0334 (9)	0.0304 (9)	0.0158 (7)	0.0087 (7)	0.0176 (8)
C4	0.0183 (8)	0.0344 (9)	0.0298 (9)	0.0058 (7)	0.0004 (7)	0.0175 (8)
C5	0.0233 (8)	0.0213 (8)	0.0228 (8)	0.0030 (7)	0.0018 (6)	0.0095 (7)
C6	0.0194 (8)	0.0211 (8)	0.0171 (8)	0.0062 (6)	0.0062 (6)	0.0103 (7)
C7	0.0193 (8)	0.0198 (8)	0.0187 (8)	0.0041 (6)	0.0027 (6)	0.0080 (7)
C8	0.0200 (8)	0.0195 (8)	0.0189 (8)	0.0065 (6)	0.0025 (6)	0.0066 (7)
C9	0.0302 (9)	0.0292 (9)	0.0269 (9)	0.0174 (7)	0.0105 (7)	0.0157 (8)
C10	0.0223 (8)	0.0159 (7)	0.0248 (8)	0.0066 (6)	0.0066 (6)	0.0095 (7)
C11	0.0216 (8)	0.0228 (8)	0.0262 (9)	0.0071 (7)	0.0036 (6)	0.0108 (7)
C12	0.0308 (9)	0.0222 (8)	0.0226 (8)	0.0061 (7)	0.0059 (7)	0.0082 (7)
C13	0.0293 (9)	0.0228 (9)	0.0325 (10)	0.0089 (7)	0.0150 (7)	0.0094 (8)
C14	0.0207 (9)	0.0278 (9)	0.0393 (10)	0.0115 (7)	0.0066 (7)	0.0114 (8)
C15	0.0259 (9)	0.0256 (8)	0.0259 (9)	0.0109 (7)	0.0029 (7)	0.0101 (7)

Cl1—C1	1.7409 (16)	C5—C6	1.390 (2)
S1—C8	1.6752 (16)	C5—H5	0.9500
O1—C7	1.2207 (19)	C6—C7	1.500 (2)
N1—C7	1.371 (2)	C9—C10	1.506 (2)
N1—C8	1.3913 (19)	C9—H9A	0.9900
N1—H1N	0.85 (2)	C9—H9B	0.9900
N2—C8	1.318 (2)	C10—C15	1.389 (2)
N2—C9	1.459 (2)	C10—C11	1.390 (2)
N2—H2N	0.82 (2)	C11—C12	1.388 (2)
C1—C2	1.383 (2)	C11—H11	0.9500
C1—C6	1.386 (2)	C12—C13	1.383 (2)
C2—C3	1.382 (2)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.384 (3)
C3—C4	1.386 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.387 (2)
C4—C5	1.385 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
C7—N1—C8	127.85 (13)	N2—C8—N1	116.48 (14)
C7—N1—H1N	116.5 (13)	N2—C8—S1	124.11 (12)
C8—N1—H1N	115.2 (13)	N1—C8—S1	119.41 (11)
C8—N2—C9	122.95 (14)	N2—C9—C10	110.88 (13)
C8—N2—H2N	117.3 (13)	N2—C9—H9A	109.5
C9—N2—H2N	119.8 (13)	C10—C9—H9A	109.5
C2—C1—C6	121.61 (15)	N2—C9—H9B	109.5
C2—C1—Cl1	119.44 (13)	C10—C9—H9B	109.5
C6—C1—Cl1	118.95 (12)	H9A—C9—H9B	108.1
C3—C2—C1	118.67 (15)	C15—C10—C11	118.98 (14)
C3—C2—H2	120.7	C15—C10—C9	118.94 (14)
C1—C2—H2	120.7	C11—C10—C9	122.06 (14)
C2—C3—C4	120.76 (15)	C12—C11—C10	120.64 (15)
C2—C3—H3	119.6	C12—C11—H11	119.7
C4—C3—H3	119.6	C10—C11—H11	119.7
C5—C4—C3	119.94 (15)	C13—C12—C11	119.88 (16)
C5—C4—H4	120.0	C13—C12—H12	120.1
C3—C4—H4	120.0	C11—C12—H12	120.1
C4—C5—C6	120.07 (15)	C12—C13—C14	119.91 (15)
C4—C5—H5	120.0	C12—C13—H13	120.0
C6—C5—H5	120.0	C14—C13—H13	120.0
C1—C6—C5	118.92 (14)	C13—C14—C15	120.18 (15)
C1—C6—C7	121.51 (14)	C13—C14—H14	119.9
C5—C6—C7	119.54 (14)	C15—C14—H14	119.9
O1—C7—N1	124.11 (14)	C14—C15—C10	120.39 (15)
O1—C7—C6	122.83 (13)	C14—C15—H15	119.8
N1—C7—C6	113.03 (13)	C10—C15—H15	119.8
C6—C1—C2—C3	−0.7 (2)	C5—C6—C7—N1	98.18 (17)
Cl1—C1—C2—C3	179.23 (12)	C9—N2—C8—N1	177.65 (14)
C1—C2—C3—C4	1.6 (2)	C9—N2—C8—S1	−1.7 (2)
C2—C3—C4—C5	−0.8 (2)	C7—N1—C8—N2	−5.7 (2)
C3—C4—C5—C6	−0.8 (2)	C7—N1—C8—S1	173.68 (13)
C2—C1—C6—C5	−0.9 (2)	C8—N2—C9—C10	−177.02 (15)
Cl1—C1—C6—C5	179.18 (11)	N2—C9—C10—C15	−141.11 (15)
C2—C1—C6—C7	177.52 (14)	N2—C9—C10—C11	40.6 (2)
Cl1—C1—C6—C7	−2.4 (2)	C15—C10—C11—C12	0.9 (2)
C4—C5—C6—C1	1.6 (2)	C9—C10—C11—C12	179.12 (15)
C4—C5—C6—C7	−176.77 (14)	C10—C11—C12—C13	−1.1 (2)
C8—N1—C7—O1	4.5 (3)	C11—C12—C13—C14	0.1 (2)
C8—N1—C7—C6	−173.81 (14)	C12—C13—C14—C15	1.1 (3)
C1—C6—C7—O1	101.52 (19)	C13—C14—C15—C10	−1.4 (3)
C5—C6—C7—O1	−80.1 (2)	C11—C10—C15—C14	0.4 (2)
C1—C6—C7—N1	−80.19 (18)	C9—C10—C15—C14	−177.92 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.86 (2)	2.53 (2)	3.3698 (18)	166.2 (18)
N2—H2N···O1	0.82 (2)	2.01 (2)	2.669 (2)	137 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1i	0.86 (2)	2.53 (2)	3.3698 (18)	166.2 (18)
N2—H2N⋯O1	0.82 (2)	2.01 (2)	2.669 (2)	137 (2)

Symmetry code: (i) .