Crystal structure of N-carbamo-thioyl-2-methyl-benzamide.

There are two mol-ecules in the asymmetric unit of the title compound, C9H10N2OS. In one, the dihedral angle between the aromatic ring and the carbamo-thioyl group is 52.31 (7)° and in the other it is 36.16 (6)°. Each mol-ecule features an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring and the O and S atoms have an anti disposition. In the crystal, mol-ecules are linked by N-H⋯S and N-H⋯O hydrogen bonds, generating separate [130] and [1-30] infinite chains. Weak C-H⋯O and C-H⋯S inter-actions are also observed.

Related literature

For related structures, see: Saeed & Flörke (2007 ▸); Shoukat et al. (2007 ▸); Hassan et al. (2008a ▸,b ▸,c ▸); Ameram et al. (2015 ▸).

Experimental

Crystal data

C9H10N2OS

M = 194.25

Monoclinic,

a = 22.7886 (12) Å

b = 7.1133 (3) Å

c = 25.5388 (13) Å

β = 113.664 (3)°

V = 3791.8 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.46 × 0.33 × 0.10 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.814, T max = 0.872

70711 measured reflections

5697 independent reflections

4862 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.10

5697 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009585/hb7426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009585/hb7426Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009585/hb7426Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009585/hb7426fig1.tif

A view of the mol­ecular structure of the title compound, showing the atom labellling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015009585/hb7426fig2.tif

A view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1401733

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

C9H10N2OS	F(000) = 1632
Mr = 194.25	Dx = 1.361 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.7886 (12) Å	Cell parameters from 9948 reflections
b = 7.1133 (3) Å	θ = 3.0–29.9°
c = 25.5388 (13) Å	µ = 0.30 mm−1
β = 113.664 (3)°	T = 100 K
V = 3791.8 (3) Å3	Plate, colourless
Z = 16	0.46 × 0.33 × 0.10 mm

Bruker APEX DUO CCD diffractometer	5697 independent reflections
Radiation source: fine-focus sealed tube	4862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 30.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −32→32
Tmin = 0.814, Tmax = 0.872	k = −10→10
70711 measured reflections	l = −36→36

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0488P)2 + 4.2106P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
5697 reflections	Δρmax = 0.45 e Å−3
261 parameters	Δρmin = −0.22 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.

	x	y	z	Uiso*/Ueq
S1A	0.20453 (2)	0.37036 (5)	0.04623 (2)	0.02123 (9)
O1A	0.05447 (5)	0.09550 (16)	−0.11126 (5)	0.0285 (3)
N1A	0.15344 (6)	0.12795 (17)	−0.03834 (5)	0.0195 (2)
N2A	0.08336 (6)	0.3410 (2)	−0.02644 (7)	0.0264 (3)
C1A	0.12721 (8)	−0.1174 (2)	−0.16760 (7)	0.0255 (3)
C2A	0.14877 (8)	−0.2742 (2)	−0.18702 (7)	0.0290 (3)
H2AA	0.1428	−0.2801	−0.2260	0.035*
C3A	0.17880 (7)	−0.4224 (2)	−0.15103 (7)	0.0257 (3)
H3AA	0.1925	−0.5289	−0.1656	0.031*
C4A	0.18880 (7)	−0.4154 (2)	−0.09401 (7)	0.0239 (3)
H4AA	0.2096	−0.5165	−0.0692	0.029*
C5A	0.16820 (7)	−0.2595 (2)	−0.07329 (6)	0.0215 (3)
H5AA	0.1756	−0.2531	−0.0340	0.026*
C6A	0.13688 (7)	−0.11301 (19)	−0.10979 (6)	0.0190 (3)
C7A	0.11026 (7)	0.0452 (2)	−0.08773 (6)	0.0202 (3)
C8A	0.14215 (7)	0.27880 (19)	−0.00939 (6)	0.0186 (3)
C9A	0.09650 (12)	0.0421 (3)	−0.20800 (9)	0.0462 (5)
H9AA	0.1169	0.1608	−0.1906	0.069*
H9AB	0.0507	0.0472	−0.2159	0.069*
H9AC	0.1019	0.0222	−0.2438	0.069*
S1B	0.45007 (2)	0.73146 (5)	−0.00298 (2)	0.02408 (10)
O1B	0.31413 (5)	0.45230 (16)	−0.16642 (5)	0.0258 (2)
N1B	0.40643 (6)	0.47799 (17)	−0.08568 (5)	0.0187 (2)
N2B	0.33660 (6)	0.71847 (19)	−0.08869 (6)	0.0227 (3)
C1B	0.35431 (7)	0.0654 (2)	−0.17791 (6)	0.0199 (3)
C2B	0.38290 (8)	−0.0911 (2)	−0.19102 (6)	0.0240 (3)
H2BA	0.3574	−0.1983	−0.2076	0.029*
C3B	0.44736 (8)	−0.0943 (2)	−0.18057 (7)	0.0278 (3)
H3BA	0.4653	−0.2025	−0.1903	0.033*
C4B	0.48592 (7)	0.0595 (2)	−0.15600 (7)	0.0276 (3)
H4BA	0.5300	0.0586	−0.1496	0.033*
C5B	0.45933 (7)	0.2151 (2)	−0.14083 (6)	0.0231 (3)
H5BA	0.4856	0.3203	−0.1234	0.028*
C6B	0.39425 (7)	0.2184 (2)	−0.15102 (6)	0.0184 (3)
C7B	0.36692 (7)	0.3907 (2)	−0.13618 (6)	0.0190 (3)
C8B	0.39349 (6)	0.64135 (19)	−0.06277 (6)	0.0177 (3)
C9B	0.28310 (7)	0.0629 (2)	−0.19377 (7)	0.0244 (3)
H9BA	0.2741	0.1143	−0.1622	0.037*
H9BB	0.2674	−0.0667	−0.2014	0.037*
H9BC	0.2615	0.1396	−0.2281	0.037*
H1B	0.4428 (11)	0.433 (3)	−0.0664 (9)	0.038 (6)*
H3A	0.0543 (11)	0.291 (3)	−0.0542 (10)	0.039 (6)*
H1A	0.1904 (10)	0.102 (3)	−0.0300 (8)	0.028 (5)*
H3B	0.3275 (10)	0.827 (3)	−0.0763 (9)	0.037 (6)*
H2B	0.3111 (11)	0.667 (3)	−0.1184 (10)	0.039 (6)*
H2A	0.0765 (10)	0.437 (3)	−0.0096 (9)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
S1A	0.02084 (16)	0.02238 (18)	0.01948 (17)	0.00473 (13)	0.00704 (13)	−0.00419 (13)
O1A	0.0193 (5)	0.0211 (5)	0.0368 (6)	0.0039 (4)	0.0025 (4)	−0.0060 (5)
N1A	0.0165 (5)	0.0181 (6)	0.0231 (6)	0.0031 (4)	0.0070 (5)	−0.0040 (5)
N2A	0.0192 (6)	0.0210 (6)	0.0374 (8)	0.0021 (5)	0.0098 (6)	−0.0096 (6)
C1A	0.0309 (8)	0.0211 (7)	0.0227 (7)	−0.0002 (6)	0.0089 (6)	0.0015 (6)
C2A	0.0364 (8)	0.0294 (8)	0.0220 (7)	0.0000 (7)	0.0127 (6)	−0.0030 (6)
C3A	0.0257 (7)	0.0225 (7)	0.0313 (8)	−0.0003 (6)	0.0140 (6)	−0.0073 (6)
C4A	0.0245 (7)	0.0184 (7)	0.0281 (8)	0.0049 (5)	0.0100 (6)	0.0013 (6)
C5A	0.0232 (7)	0.0197 (7)	0.0211 (7)	0.0037 (5)	0.0085 (5)	0.0004 (5)
C6A	0.0187 (6)	0.0152 (6)	0.0213 (7)	−0.0007 (5)	0.0062 (5)	−0.0021 (5)
C7A	0.0203 (6)	0.0143 (6)	0.0242 (7)	−0.0003 (5)	0.0070 (5)	−0.0004 (5)
C8A	0.0198 (6)	0.0153 (6)	0.0225 (7)	0.0004 (5)	0.0104 (5)	−0.0004 (5)
C9A	0.0681 (14)	0.0369 (10)	0.0309 (9)	0.0167 (10)	0.0169 (9)	0.0128 (8)
S1B	0.01921 (17)	0.02226 (18)	0.02552 (19)	0.00457 (13)	0.00349 (14)	−0.00916 (14)
O1B	0.0238 (5)	0.0242 (5)	0.0222 (5)	0.0056 (4)	0.0017 (4)	−0.0022 (4)
N1B	0.0178 (5)	0.0167 (5)	0.0182 (6)	0.0029 (4)	0.0035 (4)	−0.0036 (4)
N2B	0.0201 (6)	0.0209 (6)	0.0231 (6)	0.0052 (5)	0.0044 (5)	−0.0038 (5)
C1B	0.0230 (6)	0.0196 (7)	0.0142 (6)	−0.0007 (5)	0.0045 (5)	−0.0002 (5)
C2B	0.0297 (7)	0.0183 (7)	0.0200 (7)	−0.0002 (6)	0.0059 (6)	−0.0032 (5)
C3B	0.0304 (8)	0.0240 (7)	0.0248 (7)	0.0073 (6)	0.0068 (6)	−0.0060 (6)
C4B	0.0220 (7)	0.0303 (8)	0.0277 (8)	0.0038 (6)	0.0069 (6)	−0.0079 (6)
C5B	0.0223 (7)	0.0227 (7)	0.0216 (7)	−0.0004 (5)	0.0059 (5)	−0.0056 (6)
C6B	0.0215 (6)	0.0174 (6)	0.0147 (6)	0.0015 (5)	0.0056 (5)	−0.0012 (5)
C7B	0.0207 (6)	0.0171 (6)	0.0179 (6)	−0.0005 (5)	0.0063 (5)	−0.0020 (5)
C8B	0.0188 (6)	0.0155 (6)	0.0195 (6)	0.0015 (5)	0.0083 (5)	−0.0003 (5)
C9B	0.0227 (7)	0.0265 (8)	0.0216 (7)	−0.0043 (6)	0.0063 (6)	−0.0044 (6)

S1A—C8A	1.6858 (15)	S1B—C8B	1.6806 (14)
O1A—C7A	1.2215 (17)	O1B—C7B	1.2207 (17)
N1A—C7A	1.3818 (19)	N1B—C8B	1.3850 (18)
N1A—C8A	1.3845 (18)	N1B—C7B	1.3883 (18)
N1A—H1A	0.80 (2)	N1B—H1B	0.84 (2)
N2A—C8A	1.3083 (18)	N2B—C8B	1.3156 (18)
N2A—H3A	0.83 (2)	N2B—H3B	0.89 (2)
N2A—H2A	0.86 (2)	N2B—H2B	0.83 (2)
C1A—C2A	1.388 (2)	C1B—C2B	1.397 (2)
C1A—C6A	1.403 (2)	C1B—C6B	1.408 (2)
C1A—C9A	1.504 (2)	C1B—C9B	1.507 (2)
C2A—C3A	1.385 (2)	C2B—C3B	1.384 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.381 (2)	C3B—C4B	1.386 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.389 (2)	C4B—C5B	1.390 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.389 (2)	C5B—C6B	1.399 (2)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.492 (2)	C6B—C7B	1.4909 (19)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C7A—N1A—C8A	126.92 (12)	C8B—N1B—C7B	126.81 (12)
C7A—N1A—H1A	115.6 (14)	C8B—N1B—H1B	113.6 (15)
C8A—N1A—H1A	115.7 (14)	C7B—N1B—H1B	119.6 (15)
C8A—N2A—H3A	119.9 (16)	C8B—N2B—H3B	120.3 (14)
C8A—N2A—H2A	118.2 (14)	C8B—N2B—H2B	117.4 (16)
H3A—N2A—H2A	122 (2)	H3B—N2B—H2B	122 (2)
C2A—C1A—C6A	117.74 (14)	C2B—C1B—C6B	117.41 (13)
C2A—C1A—C9A	119.66 (15)	C2B—C1B—C9B	118.81 (13)
C6A—C1A—C9A	122.58 (15)	C6B—C1B—C9B	123.77 (13)
C3A—C2A—C1A	121.71 (15)	C3B—C2B—C1B	121.89 (14)
C3A—C2A—H2AA	119.1	C3B—C2B—H2BA	119.1
C1A—C2A—H2AA	119.1	C1B—C2B—H2BA	119.1
C4A—C3A—C2A	120.05 (14)	C2B—C3B—C4B	120.35 (14)
C4A—C3A—H3AA	120.0	C2B—C3B—H3BA	119.8
C2A—C3A—H3AA	120.0	C4B—C3B—H3BA	119.8
C3A—C4A—C5A	119.48 (14)	C3B—C4B—C5B	119.14 (14)
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.4
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.4
C4A—C5A—C6A	120.29 (14)	C4B—C5B—C6B	120.64 (14)
C4A—C5A—H5AA	119.9	C4B—C5B—H5BA	119.7
C6A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.7
C5A—C6A—C1A	120.71 (13)	C5B—C6B—C1B	120.48 (13)
C5A—C6A—C7A	119.33 (13)	C5B—C6B—C7B	119.09 (13)
C1A—C6A—C7A	119.88 (13)	C1B—C6B—C7B	120.34 (13)
O1A—C7A—N1A	122.93 (13)	O1B—C7B—N1B	122.28 (13)
O1A—C7A—C6A	122.40 (13)	O1B—C7B—C6B	122.72 (13)
N1A—C7A—C6A	114.67 (12)	N1B—C7B—C6B	115.00 (12)
N2A—C8A—N1A	117.98 (13)	N2B—C8B—N1B	118.11 (13)
N2A—C8A—S1A	123.67 (12)	N2B—C8B—S1B	122.68 (11)
N1A—C8A—S1A	118.34 (10)	N1B—C8B—S1B	119.21 (10)
C1A—C9A—H9AA	109.5	C1B—C9B—H9BA	109.5
C1A—C9A—H9AB	109.5	C1B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C1A—C9A—H9AC	109.5	C1B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C6A—C1A—C2A—C3A	0.1 (2)	C6B—C1B—C2B—C3B	−2.8 (2)
C9A—C1A—C2A—C3A	178.34 (18)	C9B—C1B—C2B—C3B	176.38 (14)
C1A—C2A—C3A—C4A	−0.9 (3)	C1B—C2B—C3B—C4B	0.5 (2)
C2A—C3A—C4A—C5A	0.4 (2)	C2B—C3B—C4B—C5B	1.4 (3)
C3A—C4A—C5A—C6A	1.0 (2)	C3B—C4B—C5B—C6B	−1.0 (2)
C4A—C5A—C6A—C1A	−1.9 (2)	C4B—C5B—C6B—C1B	−1.3 (2)
C4A—C5A—C6A—C7A	174.80 (13)	C4B—C5B—C6B—C7B	−177.71 (14)
C2A—C1A—C6A—C5A	1.3 (2)	C2B—C1B—C6B—C5B	3.2 (2)
C9A—C1A—C6A—C5A	−176.90 (17)	C9B—C1B—C6B—C5B	−175.98 (14)
C2A—C1A—C6A—C7A	−175.35 (14)	C2B—C1B—C6B—C7B	179.53 (13)
C9A—C1A—C6A—C7A	6.5 (2)	C9B—C1B—C6B—C7B	0.4 (2)
C8A—N1A—C7A—O1A	−2.2 (2)	C8B—N1B—C7B—O1B	−0.6 (2)
C8A—N1A—C7A—C6A	178.65 (13)	C8B—N1B—C7B—C6B	178.45 (13)
C5A—C6A—C7A—O1A	−126.72 (16)	C5B—C6B—C7B—O1B	139.95 (15)
C1A—C6A—C7A—O1A	50.0 (2)	C1B—C6B—C7B—O1B	−36.5 (2)
C5A—C6A—C7A—N1A	52.41 (18)	C5B—C6B—C7B—N1B	−39.13 (19)
C1A—C6A—C7A—N1A	−130.91 (15)	C1B—C6B—C7B—N1B	144.47 (13)
C7A—N1A—C8A—N2A	7.1 (2)	C7B—N1B—C8B—N2B	4.7 (2)
C7A—N1A—C8A—S1A	−173.59 (12)	C7B—N1B—C8B—S1B	−176.08 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S1Ai	0.80 (2)	2.60 (2)	3.3227 (16)	151.2 (18)
N1B—H1B···S1Bii	0.84 (2)	2.65 (2)	3.4780 (14)	172 (2)
N2A—H2A···S1Biii	0.85 (2)	2.49 (2)	3.2945 (15)	157.8 (19)
N2B—H2B···O1B	0.83 (2)	1.98 (2)	2.6404 (18)	136 (2)
N2A—H3A···O1A	0.83 (2)	2.02 (2)	2.6515 (19)	133 (2)
N2B—H3B···S1Aiii	0.89 (2)	2.49 (2)	3.3800 (14)	177 (2)
C5B—H5BA···O1Aiv	0.95	2.45	3.3584 (19)	160
C9B—H9BA···S1Ai	0.98	2.80	3.6946 (17)	152

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1AH1AS1A i	0.80(2)	2.60(2)	3.3227(16)	151.2(18)
N1BH1BS1B ii	0.84(2)	2.65(2)	3.4780(14)	172(2)
N2AH2AS1B iii	0.85(2)	2.49(2)	3.2945(15)	157.8(19)
N2BH2BO1B	0.83(2)	1.98(2)	2.6404(18)	136(2)
N2AH3AO1A	0.83(2)	2.02(2)	2.6515(19)	133(2)
N2BH3BS1A iii	0.89(2)	2.49(2)	3.3800(14)	177(2)
C5BH5BAO1A iv	0.95	2.45	3.3584(19)	160
C9BH9BAS1A i	0.98	2.80	3.6946(17)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .