N-(2-Nitro-phenyl-carbamothio-yl)acetamide.

In the title compound, C(9)H(9)N(3)O(3)S, the benzene ring and the N-carbamothio-ylacetamide unit are oriented at a dihedral angle of 54.82 (4)°. The dihedral angle between the ring and its attached nitro group is 28.54 (12)°. An intra-molecular, bifurcated N-H⋯(O,O) hydrogen bond generates two S(6) rings. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops. Weak C-H⋯O inter-actions link the dimers.

Related literature

For related structures, see: Shahwar et al. (2012 ▶,c ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H9N3O3S

M = 239.25

Monoclinic,

a = 4.1992 (1) Å

b = 11.6081 (3) Å

c = 22.1035 (6) Å

β = 94.815 (1)°

V = 1073.63 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.965

10065 measured reflections

2711 independent reflections

1969 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.01

2711 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.22 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016947/hb6744sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016947/hb6744Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016947/hb6744Isup3.cml

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

C9H9N3O3S	F(000) = 496
Mr = 239.25	Dx = 1.480 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1969 reflections
a = 4.1992 (1) Å	θ = 1.9–28.4°
b = 11.6081 (3) Å	µ = 0.30 mm−1
c = 22.1035 (6) Å	T = 296 K
β = 94.815 (1)°	Needle, colourless
V = 1073.63 (5) Å3	0.35 × 0.15 × 0.13 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2711 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 1.9°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.945, Tmax = 0.965	l = −29→29
10065 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3324P] where P = (Fo2 + 2Fc2)/3
2711 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	1.09141 (12)	0.18209 (4)	0.01646 (2)	0.0470 (2)
O1	1.0422 (5)	0.23102 (15)	0.24000 (7)	0.0772 (7)
O2	1.4312 (4)	0.3495 (2)	0.25974 (8)	0.1053 (8)
O3	0.5502 (4)	0.04876 (12)	0.17207 (6)	0.0676 (5)
N1	1.1962 (4)	0.31649 (18)	0.22843 (7)	0.0608 (6)
N2	0.8449 (4)	0.22014 (12)	0.12253 (6)	0.0441 (5)
N3	0.7962 (3)	0.03702 (12)	0.08415 (6)	0.0405 (4)
C1	0.9181 (4)	0.33887 (14)	0.12522 (7)	0.0402 (5)
C2	1.0856 (4)	0.38734 (16)	0.17587 (8)	0.0465 (6)
C3	1.1536 (5)	0.50364 (19)	0.17923 (11)	0.0654 (8)
C4	1.0529 (6)	0.57302 (19)	0.13141 (12)	0.0763 (9)
C5	0.8855 (6)	0.52747 (18)	0.08093 (11)	0.0678 (8)
C6	0.8168 (5)	0.41127 (16)	0.07781 (9)	0.0537 (7)
C7	0.9000 (4)	0.14835 (14)	0.07749 (7)	0.0369 (5)
C8	0.6239 (4)	−0.00808 (16)	0.12923 (8)	0.0449 (6)
C9	0.5378 (5)	−0.13221 (17)	0.12095 (8)	0.0522 (6)
H2	0.75624	0.19142	0.15281	0.0529*
H3	1.26623	0.53434	0.21351	0.0785*
H3A	0.84485	−0.01078	0.05666	0.0485*
H4	1.09789	0.65145	0.13307	0.0915*
H5	0.81794	0.57530	0.04862	0.0814*
H6	0.70161	0.38146	0.04358	0.0645*
H9A	0.72667	−0.17858	0.12780	0.0784*
H9B	0.44403	−0.14442	0.08033	0.0784*
H9C	0.38729	−0.15343	0.14937	0.0784*

	U11	U22	U33	U12	U13	U23
S1	0.0619 (3)	0.0391 (2)	0.0416 (3)	−0.0060 (2)	0.0135 (2)	−0.0040 (2)
O1	0.1231 (15)	0.0614 (10)	0.0455 (9)	0.0175 (10)	−0.0028 (9)	0.0020 (7)
O2	0.0672 (11)	0.177 (2)	0.0673 (11)	0.0072 (12)	−0.0204 (9)	−0.0075 (12)
O3	0.0970 (11)	0.0569 (9)	0.0533 (8)	−0.0117 (8)	0.0325 (8)	−0.0063 (7)
N1	0.0646 (11)	0.0792 (13)	0.0381 (9)	0.0208 (10)	0.0014 (8)	−0.0132 (9)
N2	0.0628 (9)	0.0352 (7)	0.0350 (8)	0.0011 (7)	0.0087 (7)	−0.0019 (6)
N3	0.0512 (8)	0.0335 (7)	0.0371 (7)	0.0002 (6)	0.0064 (6)	−0.0022 (6)
C1	0.0491 (10)	0.0345 (9)	0.0375 (9)	0.0039 (7)	0.0063 (7)	−0.0051 (7)
C2	0.0500 (10)	0.0498 (10)	0.0401 (9)	0.0066 (8)	0.0066 (8)	−0.0085 (8)
C3	0.0704 (14)	0.0558 (13)	0.0700 (14)	−0.0081 (11)	0.0060 (11)	−0.0250 (11)
C4	0.0957 (18)	0.0385 (11)	0.0970 (19)	−0.0106 (11)	0.0224 (15)	−0.0133 (12)
C5	0.0949 (17)	0.0420 (11)	0.0676 (14)	0.0081 (11)	0.0134 (13)	0.0081 (10)
C6	0.0704 (13)	0.0411 (10)	0.0488 (11)	0.0069 (9)	−0.0004 (9)	−0.0004 (8)
C7	0.0411 (9)	0.0341 (8)	0.0345 (8)	0.0033 (7)	−0.0026 (7)	−0.0017 (6)
C8	0.0503 (10)	0.0454 (10)	0.0390 (9)	−0.0017 (8)	0.0033 (8)	0.0036 (8)
C9	0.0594 (12)	0.0500 (11)	0.0470 (10)	−0.0126 (9)	0.0031 (9)	0.0041 (8)

S1—C7	1.6737 (17)	C2—C3	1.381 (3)
O1—N1	1.223 (3)	C3—C4	1.367 (3)
O2—N1	1.219 (2)	C4—C5	1.374 (4)
O3—C8	1.215 (2)	C5—C6	1.380 (3)
N1—C2	1.467 (2)	C8—C9	1.493 (3)
N2—C1	1.412 (2)	C3—H3	0.9300
N2—C7	1.333 (2)	C4—H4	0.9300
N3—C7	1.376 (2)	C5—H5	0.9300
N3—C8	1.383 (2)	C6—H6	0.9300
N2—H2	0.8600	C9—H9A	0.9600
N3—H3A	0.8600	C9—H9B	0.9600
C1—C6	1.382 (3)	C9—H9C	0.9600
C1—C2	1.390 (2)
O1—N1—O2	123.61 (19)	S1—C7—N3	118.95 (12)
O1—N1—C2	118.86 (16)	N2—C7—N3	115.52 (14)
O2—N1—C2	117.45 (19)	O3—C8—C9	123.00 (17)
C1—N2—C7	126.20 (14)	N3—C8—C9	114.40 (15)
C7—N3—C8	128.50 (14)	O3—C8—N3	122.61 (17)
C1—N2—H2	117.00	C2—C3—H3	120.00
C7—N2—H2	117.00	C4—C3—H3	120.00
C7—N3—H3A	116.00	C3—C4—H4	120.00
C8—N3—H3A	116.00	C5—C4—H4	120.00
N2—C1—C2	121.50 (15)	C4—C5—H5	120.00
N2—C1—C6	120.62 (15)	C6—C5—H5	120.00
C2—C1—C6	117.85 (16)	C1—C6—H6	120.00
C1—C2—C3	121.84 (18)	C5—C6—H6	120.00
N1—C2—C1	121.07 (16)	C8—C9—H9A	109.00
N1—C2—C3	117.09 (17)	C8—C9—H9B	109.00
C2—C3—C4	119.0 (2)	C8—C9—H9C	109.00
C3—C4—C5	120.3 (2)	H9A—C9—H9B	109.00
C4—C5—C6	120.5 (2)	H9A—C9—H9C	109.00
C1—C6—C5	120.45 (19)	H9B—C9—H9C	109.00
S1—C7—N2	125.50 (13)
O1—N1—C2—C3	149.7 (2)	C6—C1—C2—N1	178.95 (17)
O1—N1—C2—C1	−30.0 (3)	C6—C1—C2—C3	−0.7 (3)
O2—N1—C2—C1	153.06 (19)	N2—C1—C6—C5	179.21 (19)
O2—N1—C2—C3	−27.3 (3)	C2—C1—C6—C5	0.9 (3)
C7—N2—C1—C2	−129.53 (19)	N2—C1—C2—N1	0.7 (3)
C7—N2—C1—C6	52.2 (3)	N2—C1—C2—C3	−178.95 (17)
C1—N2—C7—S1	4.5 (3)	N1—C2—C3—C4	−179.54 (19)
C1—N2—C7—N3	−177.62 (15)	C1—C2—C3—C4	0.1 (3)
C8—N3—C7—N2	4.8 (2)	C2—C3—C4—C5	0.3 (3)
C7—N3—C8—O3	−2.9 (3)	C3—C4—C5—C6	0.0 (4)
C7—N3—C8—C9	177.33 (16)	C4—C5—C6—C1	−0.6 (3)
C8—N3—C7—S1	−177.15 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.23	2.661 (2)	111
N2—H2···O3	0.86	1.93	2.630 (2)	137
N3—H3A···S1i	0.86	2.59	3.4371 (14)	168
C9—H9C···O2ii	0.96	2.51	3.428 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.23	2.661 (2)	111
N2—H2⋯O3	0.86	1.93	2.630 (2)	137
N3—H3A⋯S1i	0.86	2.59	3.4371 (14)	168
C9—H9C⋯O2ii	0.96	2.51	3.428 (3)	161

Symmetry codes: (i) ; (ii) .