Crystal structure of N-(4-chloro-phen-yl)benzo-thio-amide.

The title compound, C13H10ClNS, exhibits a trans conformation with regard to the axis of the C-N bond. The benzene and phenyl rings are inclined to one another by 85.06 (8)°. In the crystal, mol-ecules are linked by N-H⋯S=C hydrogen bonds, forming chains along [001].

Related literature

For hydrogen bonding of amides, see: Taylor et al. (1984 ▸); Leiserowitz & Schmidt (1969 ▸). For the preparation and for the use of thio­amides as inter­mediates in chemical transformations, see: Li et al. (2012 ▸, 2015 ▸). For related structures, see: Omondi et al. (2012 ▸); Nagasawa et al. (2014 ▸).

Experimental

Crystal data

C13H10ClNS

M = 247.73

Monoclinic,

a = 11.943 (2) Å

b = 12.689 (3) Å

c = 7.9764 (16) Å

β = 109.30 (3)°

V = 1140.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 113 K

0.22 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▸) T min = 0.901, T max = 0.944

7517 measured reflections

2010 independent reflections

1701 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.05

2010 reflections

150 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 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: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015008075/su5123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008075/su5123Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008075/su5123Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008075/su5123fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015008075/su5123fig2.tif

A view along the b axis of the crystal packing of the title compound. The N—H⋯S hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1061304

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H10ClNS	F(000) = 512
Mr = 247.73	Dx = 1.442 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3499 reflections
a = 11.943 (2) Å	θ = 1.8–27.9°
b = 12.689 (3) Å	µ = 0.49 mm−1
c = 7.9764 (16) Å	T = 113 K
β = 109.30 (3)°	Block, yellow
V = 1140.9 (4) Å3	0.22 × 0.20 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2010 independent reflections
Radiation source: rotating anode	1701 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.030
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −11→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
Tmin = 0.901, Tmax = 0.944	l = −9→9
7517 measured reflections

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1743P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2010 reflections	Δρmax = 0.22 e Å−3
150 parameters	Δρmin = −0.18 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (4)

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	0.94504 (4)	0.58973 (3)	1.20150 (5)	0.01919 (16)
Cl1	1.47747 (4)	0.84240 (4)	1.54329 (6)	0.02760 (17)
N1	1.02619 (11)	0.71403 (10)	0.99722 (17)	0.0160 (3)
C1	1.13474 (13)	0.74209 (12)	1.1311 (2)	0.0159 (3)
C2	1.21244 (14)	0.66609 (13)	1.2321 (2)	0.0201 (4)
H2	1.1936	0.5949	1.2147	0.024*
C3	1.31777 (14)	0.69722 (13)	1.3583 (2)	0.0218 (4)
H3	1.3698	0.6470	1.4264	0.026*
C4	1.34551 (14)	0.80302 (13)	1.3828 (2)	0.0186 (4)
C5	1.26984 (15)	0.87901 (13)	1.2816 (2)	0.0219 (4)
H5	1.2895	0.9501	1.2982	0.026*
C6	1.16448 (15)	0.84782 (13)	1.1550 (2)	0.0194 (4)
H6	1.1134	0.8982	1.0857	0.023*
C7	0.94159 (14)	0.64895 (12)	1.0128 (2)	0.0159 (4)
C8	0.83987 (14)	0.63239 (12)	0.8467 (2)	0.0161 (4)
C9	0.85648 (15)	0.62942 (12)	0.6821 (2)	0.0182 (4)
H9	0.9320	0.6389	0.6751	0.022*
C10	0.76076 (16)	0.61237 (13)	0.5280 (2)	0.0226 (4)
H10	0.7725	0.6106	0.4184	0.027*
C11	0.64826 (16)	0.59810 (13)	0.5376 (2)	0.0249 (4)
H11	0.5842	0.5868	0.4347	0.030*
C12	0.63130 (15)	0.60079 (13)	0.7015 (2)	0.0251 (4)
H12	0.5557	0.5910	0.7082	0.030*
C13	0.72593 (14)	0.61784 (12)	0.8545 (2)	0.0201 (4)
H13	0.7137	0.6197	0.9637	0.024*
H1	1.0058 (16)	0.7552 (13)	0.9013 (17)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0205 (2)	0.0192 (2)	0.0179 (3)	−0.00251 (17)	0.00650 (18)	0.00248 (16)
Cl1	0.0174 (2)	0.0353 (3)	0.0268 (3)	−0.00442 (18)	0.00281 (18)	−0.00048 (18)
N1	0.0177 (7)	0.0151 (7)	0.0155 (7)	−0.0010 (6)	0.0057 (6)	0.0010 (6)
C1	0.0158 (8)	0.0181 (8)	0.0164 (8)	−0.0003 (7)	0.0090 (7)	−0.0010 (6)
C2	0.0187 (9)	0.0154 (8)	0.0280 (9)	0.0004 (7)	0.0102 (7)	0.0010 (7)
C3	0.0170 (8)	0.0215 (9)	0.0279 (10)	0.0042 (7)	0.0089 (7)	0.0066 (7)
C4	0.0138 (8)	0.0245 (9)	0.0186 (8)	−0.0014 (7)	0.0070 (7)	−0.0008 (7)
C5	0.0231 (9)	0.0177 (8)	0.0249 (9)	−0.0026 (7)	0.0081 (8)	−0.0024 (7)
C6	0.0192 (9)	0.0175 (8)	0.0211 (9)	0.0029 (7)	0.0063 (7)	0.0016 (6)
C7	0.0173 (8)	0.0118 (7)	0.0210 (9)	0.0028 (6)	0.0096 (7)	−0.0021 (6)
C8	0.0186 (8)	0.0098 (7)	0.0201 (8)	0.0007 (6)	0.0065 (7)	−0.0005 (6)
C9	0.0202 (9)	0.0133 (8)	0.0223 (9)	−0.0018 (7)	0.0085 (7)	0.0000 (7)
C10	0.0300 (10)	0.0194 (8)	0.0186 (9)	−0.0017 (8)	0.0081 (8)	−0.0018 (7)
C11	0.0234 (9)	0.0257 (9)	0.0202 (9)	−0.0010 (8)	0.0001 (7)	−0.0017 (7)
C12	0.0171 (9)	0.0280 (9)	0.0285 (10)	0.0010 (8)	0.0052 (7)	0.0009 (8)
C13	0.0192 (9)	0.0210 (9)	0.0212 (9)	0.0019 (7)	0.0080 (7)	0.0011 (7)

S1—C7	1.6705 (16)	C6—H6	0.9300
Cl1—C4	1.7430 (17)	C7—C8	1.487 (2)
N1—C7	1.342 (2)	C8—C9	1.391 (2)
N1—C1	1.426 (2)	C8—C13	1.395 (2)
N1—H1	0.891 (9)	C9—C10	1.392 (2)
C1—C6	1.385 (2)	C9—H9	0.9300
C1—C2	1.395 (2)	C10—C11	1.383 (2)
C2—C3	1.384 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.388 (3)
C3—C4	1.381 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.379 (2)
C4—C5	1.384 (2)	C12—H12	0.9300
C5—C6	1.385 (2)	C13—H13	0.9300
C5—H5	0.9300
C7—N1—C1	127.60 (13)	N1—C7—C8	115.00 (13)
C7—N1—H1	116.1 (12)	N1—C7—S1	124.40 (13)
C1—N1—H1	114.8 (12)	C8—C7—S1	120.59 (12)
C6—C1—C2	119.92 (15)	C9—C8—C13	118.95 (15)
C6—C1—N1	118.25 (14)	C9—C8—C7	121.01 (15)
C2—C1—N1	121.77 (14)	C13—C8—C7	120.03 (15)
C3—C2—C1	119.60 (15)	C8—C9—C10	120.42 (16)
C3—C2—H2	120.2	C8—C9—H9	119.8
C1—C2—H2	120.2	C10—C9—H9	119.8
C4—C3—C2	119.90 (15)	C11—C10—C9	120.03 (16)
C4—C3—H3	120.0	C11—C10—H10	120.0
C2—C3—H3	120.0	C9—C10—H10	120.0
C3—C4—C5	120.96 (15)	C10—C11—C12	119.76 (16)
C3—C4—Cl1	119.94 (13)	C10—C11—H11	120.1
C5—C4—Cl1	119.09 (13)	C12—C11—H11	120.1
C4—C5—C6	119.13 (15)	C13—C12—C11	120.34 (16)
C4—C5—H5	120.4	C13—C12—H12	119.8
C6—C5—H5	120.4	C11—C12—H12	119.8
C1—C6—C5	120.46 (15)	C12—C13—C8	120.50 (16)
C1—C6—H6	119.8	C12—C13—H13	119.7
C5—C6—H6	119.8	C8—C13—H13	119.7
C7—N1—C1—C6	−131.37 (16)	C1—N1—C7—S1	2.6 (2)
C7—N1—C1—C2	51.1 (2)	N1—C7—C8—C9	35.2 (2)
C6—C1—C2—C3	1.3 (2)	S1—C7—C8—C9	−145.34 (13)
N1—C1—C2—C3	178.80 (14)	N1—C7—C8—C13	−145.86 (15)
C1—C2—C3—C4	−0.3 (2)	S1—C7—C8—C13	33.62 (19)
C2—C3—C4—C5	−0.7 (2)	C13—C8—C9—C10	0.1 (2)
C2—C3—C4—Cl1	179.35 (12)	C7—C8—C9—C10	179.08 (14)
C3—C4—C5—C6	0.5 (2)	C8—C9—C10—C11	−0.1 (2)
Cl1—C4—C5—C6	−179.46 (12)	C9—C10—C11—C12	0.0 (2)
C2—C1—C6—C5	−1.5 (2)	C10—C11—C12—C13	0.2 (3)
N1—C1—C6—C5	−179.01 (14)	C11—C12—C13—C8	−0.1 (2)
C4—C5—C6—C1	0.5 (2)	C9—C8—C13—C12	0.0 (2)
C1—N1—C7—C8	−177.96 (13)	C7—C8—C13—C12	−178.98 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.89 (1)	2.49 (1)	3.346 (15)	163 (1)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1S1i	0.89(1)	2.49(1)	3.346(15)	163(1)

Symmetry code: (i) .