1-Ethyl-1-methyl-3-(2-nitro-benzo-yl)thio-urea.

In the title compound, C(11)H(13)N(3)O(3)S, the benzene ring is twisted relative to the amidic fragment, forming a dihedral angle of 27.26 (9)°. The thiono and carbonyl groups are trans with respect to the C-N bond. Inter-molecular N-H⋯S and C-H⋯O hydrogen bonds link the mol-ecules in the crystal structure.

Related literature

For the synthesis, see: Al-abbasi et al. (2010 ▶). For related structures and background references, see: Shanmuga Sundara Raj et al. (1999 ▶); Arslan et al. (2003 ▶); Al-abbasi & Kassim (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶) and for bond lengths in other substituted thio­ureas, see: Nasir et al. (2011 ▶); Pérez et al. (2011 ▶).

Experimental

Crystal data

C11H13N3O3S

M = 267.30

Monoclinic,

a = 11.447 (2) Å

b = 7.8664 (15) Å

c = 15.159 (3) Å

β = 107.128 (4)°

V = 1304.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.55 × 0.38 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.874, T max = 0.949

7105 measured reflections

2294 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.06

2294 reflections

169 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024652/jh2299sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024652/jh2299Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024652/jh2299Isup3.cml

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

C11H13N3O3S	F(000) = 560
Mr = 267.30	Dx = 1.361 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4015 reflections
a = 11.447 (2) Å	θ = 2.0–25.0°
b = 7.8664 (15) Å	µ = 0.25 mm−1
c = 15.159 (3) Å	T = 298 K
β = 107.128 (4)°	Block, brown
V = 1304.5 (4) Å3	0.55 × 0.38 × 0.21 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2294 independent reflections
Radiation source: fine-focus sealed tube	1971 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.874, Tmax = 0.949	k = −7→9
7105 measured reflections	l = −15→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.065P)2 + 0.531P] where P = (Fo2 + 2Fc2)/3
2294 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.19 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
S1	0.69163 (5)	0.06431 (8)	0.07382 (4)	0.0575 (2)
O1	0.49702 (13)	0.2128 (2)	0.24893 (10)	0.0608 (4)
O2	0.44396 (18)	−0.1541 (2)	0.17973 (16)	0.0811 (6)
O3	0.2858 (2)	−0.3156 (2)	0.14610 (17)	0.0984 (7)
N1	0.48480 (14)	0.1814 (2)	0.09706 (11)	0.0435 (4)
N2	0.65025 (15)	0.3643 (2)	0.14053 (13)	0.0528 (5)
N3	0.3344 (2)	−0.1771 (2)	0.15678 (14)	0.0612 (5)
C1	0.30487 (17)	0.1334 (2)	0.14682 (13)	0.0401 (4)
C2	0.25371 (19)	−0.0265 (3)	0.14295 (14)	0.0459 (5)
C3	0.1301 (2)	−0.0513 (4)	0.12710 (16)	0.0636 (7)
H3	0.0984	−0.1604	0.1258	0.076*
C4	0.0545 (2)	0.0879 (4)	0.11328 (18)	0.0731 (8)
H4	−0.0291	0.0735	0.1026	0.088*
C5	0.1024 (2)	0.2479 (4)	0.11526 (19)	0.0728 (8)
H5	0.0507	0.3418	0.1050	0.087*
C6	0.2264 (2)	0.2709 (3)	0.13230 (16)	0.0558 (6)
H6	0.2577	0.3803	0.1341	0.067*
C7	0.43942 (17)	0.1743 (2)	0.17127 (14)	0.0433 (5)
C8	0.60936 (17)	0.2138 (3)	0.10694 (13)	0.0441 (5)
C9	0.7795 (2)	0.4114 (3)	0.16004 (17)	0.0607 (6)
H9A	0.8292	0.3093	0.1710	0.073*
H9B	0.8039	0.4801	0.2156	0.073*
C10	0.8020 (3)	0.5099 (4)	0.0808 (2)	0.0793 (8)
H10A	0.7897	0.4366	0.0282	0.119*
H10B	0.8844	0.5518	0.0987	0.119*
H10C	0.7461	0.6038	0.0651	0.119*
C11	0.5729 (2)	0.5026 (3)	0.1556 (2)	0.0737 (8)
H11A	0.4905	0.4853	0.1175	0.111*
H11B	0.6028	0.6090	0.1400	0.111*
H11C	0.5747	0.5042	0.2193	0.111*
H1A	0.4498 (18)	0.123 (3)	0.0494 (11)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0395 (3)	0.0708 (4)	0.0647 (4)	0.0004 (2)	0.0194 (3)	−0.0241 (3)
O1	0.0506 (9)	0.0857 (12)	0.0461 (9)	−0.0004 (8)	0.0142 (7)	−0.0123 (8)
O2	0.0695 (12)	0.0584 (11)	0.1181 (16)	0.0213 (9)	0.0318 (11)	0.0114 (10)
O3	0.134 (2)	0.0423 (10)	0.1218 (18)	−0.0117 (11)	0.0429 (15)	−0.0064 (10)
N1	0.0362 (8)	0.0513 (10)	0.0453 (9)	−0.0046 (7)	0.0156 (7)	−0.0126 (8)
N2	0.0415 (9)	0.0572 (11)	0.0618 (11)	−0.0084 (8)	0.0185 (8)	−0.0138 (9)
N3	0.0866 (15)	0.0377 (10)	0.0639 (12)	0.0017 (10)	0.0295 (11)	0.0017 (8)
C1	0.0402 (10)	0.0417 (10)	0.0428 (10)	0.0035 (8)	0.0190 (8)	−0.0007 (8)
C2	0.0504 (11)	0.0470 (11)	0.0449 (11)	0.0001 (9)	0.0209 (9)	0.0002 (8)
C3	0.0608 (14)	0.0764 (17)	0.0602 (14)	−0.0244 (13)	0.0279 (12)	−0.0070 (12)
C4	0.0389 (12)	0.118 (2)	0.0658 (16)	−0.0025 (14)	0.0213 (11)	−0.0029 (15)
C5	0.0510 (14)	0.090 (2)	0.0805 (18)	0.0280 (14)	0.0242 (12)	0.0086 (14)
C6	0.0536 (12)	0.0485 (12)	0.0698 (14)	0.0113 (10)	0.0252 (11)	0.0041 (10)
C7	0.0405 (10)	0.0429 (11)	0.0497 (11)	0.0049 (8)	0.0181 (9)	−0.0035 (8)
C8	0.0367 (10)	0.0560 (12)	0.0400 (10)	−0.0039 (9)	0.0122 (8)	−0.0071 (8)
C9	0.0448 (12)	0.0725 (15)	0.0638 (14)	−0.0165 (11)	0.0145 (10)	−0.0187 (12)
C10	0.0656 (16)	0.0856 (19)	0.090 (2)	−0.0134 (14)	0.0287 (14)	−0.0004 (16)
C11	0.0675 (16)	0.0533 (14)	0.107 (2)	−0.0033 (12)	0.0356 (15)	−0.0200 (14)

S1—C8	1.674 (2)	C3—H3	0.9300
O1—C7	1.206 (2)	C4—C5	1.370 (4)
O2—N3	1.212 (3)	C4—H4	0.9300
O3—N3	1.212 (3)	C5—C6	1.378 (3)
N1—C7	1.372 (2)	C5—H5	0.9300
N1—C8	1.412 (2)	C6—H6	0.9300
N1—H1A	0.849 (10)	C9—C10	1.514 (4)
N2—C8	1.319 (3)	C9—H9A	0.9700
N2—C11	1.462 (3)	C9—H9B	0.9700
N2—C9	1.469 (3)	C10—H10A	0.9600
N3—C2	1.479 (3)	C10—H10B	0.9600
C1—C2	1.381 (3)	C10—H10C	0.9600
C1—C6	1.382 (3)	C11—H11A	0.9600
C1—C7	1.509 (3)	C11—H11B	0.9600
C2—C3	1.378 (3)	C11—H11C	0.9600
C3—C4	1.372 (4)
C7—N1—C8	122.31 (16)	C1—C6—H6	119.6
C7—N1—H1A	118.6 (15)	O1—C7—N1	124.04 (18)
C8—N1—H1A	113.3 (15)	O1—C7—C1	121.22 (17)
C8—N2—C11	124.45 (18)	N1—C7—C1	114.38 (17)
C8—N2—C9	121.75 (18)	N2—C8—N1	115.81 (17)
C11—N2—C9	113.66 (19)	N2—C8—S1	125.42 (15)
O3—N3—O2	124.6 (2)	N1—C8—S1	118.75 (15)
O3—N3—C2	117.3 (2)	N2—C9—C10	111.5 (2)
O2—N3—C2	118.12 (18)	N2—C9—H9A	109.3
C2—C1—C6	117.29 (18)	C10—C9—H9A	109.3
C2—C1—C7	126.44 (17)	N2—C9—H9B	109.3
C6—C1—C7	116.16 (18)	C10—C9—H9B	109.3
C3—C2—C1	122.5 (2)	H9A—C9—H9B	108.0
C3—C2—N3	118.5 (2)	C9—C10—H10A	109.5
C1—C2—N3	118.97 (18)	C9—C10—H10B	109.5
C4—C3—C2	118.9 (2)	H10A—C10—H10B	109.5
C4—C3—H3	120.6	C9—C10—H10C	109.5
C2—C3—H3	120.6	H10A—C10—H10C	109.5
C5—C4—C3	120.0 (2)	H10B—C10—H10C	109.5
C5—C4—H4	120.0	N2—C11—H11A	109.5
C3—C4—H4	120.0	N2—C11—H11B	109.5
C4—C5—C6	120.5 (2)	H11A—C11—H11B	109.5
C4—C5—H5	119.8	N2—C11—H11C	109.5
C6—C5—H5	119.8	H11A—C11—H11C	109.5
C5—C6—C1	120.9 (2)	H11B—C11—H11C	109.5
C5—C6—H6	119.6
C6—C1—C2—C3	−1.2 (3)	C8—N1—C7—O1	8.5 (3)
C7—C1—C2—C3	174.71 (19)	C8—N1—C7—C1	−178.37 (17)
C6—C1—C2—N3	179.13 (19)	C2—C1—C7—O1	−95.5 (3)
C7—C1—C2—N3	−5.0 (3)	C6—C1—C7—O1	80.5 (3)
O3—N3—C2—C3	5.7 (3)	C2—C1—C7—N1	91.2 (2)
O2—N3—C2—C3	−172.8 (2)	C6—C1—C7—N1	−92.9 (2)
O3—N3—C2—C1	−174.6 (2)	C11—N2—C8—N1	−8.5 (3)
O2—N3—C2—C1	6.9 (3)	C9—N2—C8—N1	176.06 (19)
C1—C2—C3—C4	1.0 (3)	C11—N2—C8—S1	170.1 (2)
N3—C2—C3—C4	−179.3 (2)	C9—N2—C8—S1	−5.4 (3)
C2—C3—C4—C5	0.1 (4)	C7—N1—C8—N2	−63.8 (3)
C3—C4—C5—C6	−0.9 (4)	C7—N1—C8—S1	117.53 (18)
C4—C5—C6—C1	0.6 (4)	C8—N2—C9—C10	96.1 (3)
C2—C1—C6—C5	0.4 (3)	C11—N2—C9—C10	−79.8 (3)
C7—C1—C6—C5	−175.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.85 (2)	2.55 (2)	3.3828 (18)	167.(2)
C6—H6···O3ii	0.93	2.41	3.317 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.85 (2)	2.55 (2)	3.3828 (18)	167 (2)
C6—H6⋯O3ii	0.93	2.41	3.317 (3)	164

Symmetry codes: (i) ; (ii) .