N-(Diethyl-carbamothio-yl)-4-nitro-benzamide.

In the title compound, C(12)H(15)N(3)O(3)S, the 4-nitro and carbonyl groups are nearly coplanar with the benzene ring [C-C-N-O = -175.72 (14) and C-C-C-O = 172.75 (14)°]. The diethyl-carbamothioyl group is twisted significantly from the plane of the benzene ring [C-N-C-N = -89.79 (15)°] with the S atom pointing away from each of these groups [C-N-C-S = 91.12 (14)°]. In the crystal, an inter-molecular N-H⋯O hydrogen bond, which forms an infinite polymeric chain along the c axis, and weak C-H⋯O and C-H⋯S hydrogen bonds are observed.

Related literature

For background to the use of thio­ureas in coordination chemistry, see: Burrows et al. (1999 ▶); Henderson et al. (2002 ▶), Schuster et al. (1990 ▶); Che et al. (1999 ▶); For their biological and catalytic activity, see: Saeed et al. (2009 ▶, 2010a ▶,b ▶); Maddani et al. (2010 ▶); Jung et al. (2008 ▶); For related literature, see: Zhang et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H15N3O3S

M = 281.33

Monoclinic,

a = 6.884 (5) Å

b = 19.237 (5) Å

c = 10.146 (5) Å

β = 92.983 (5)°

V = 1341.8 (12) Å3

Z = 4

Cu Kα radiation

μ = 2.23 mm−1

T = 295 K

0.52 × 0.41 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini Cu diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.769, T max = 1.000

5616 measured reflections

2790 independent reflections

2507 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.05

2790 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED; data n class="Disease">reduction: CrysAlis RED; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036366/vm2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036366/vm2042Isup2.hkl

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

C12H15N3O3S	F(000) = 592
Mr = 281.33	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Melting point: 434 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 6.884 (5) Å	Cell parameters from 4133 reflections
b = 19.237 (5) Å	θ = 4.6–77.2°
c = 10.146 (5) Å	µ = 2.23 mm−1
β = 92.983 (5)°	T = 295 K
V = 1341.8 (12) Å3	Block, pale yellow
Z = 4	0.52 × 0.41 × 0.35 mm

Oxford Diffraction Xcalibur Ruby Gemini Cu diffractometer	2790 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2507 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.5081 pixels mm-1	θmax = 77.4°, θmin = 4.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −17→24
Tmin = 0.769, Tmax = 1.000	l = −12→12
5616 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.078P)2 + 0.1589P] where P = (Fo2 + 2Fc2)/3
2790 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.29 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	0.38042 (6)	0.89794 (2)	0.52976 (4)	0.05321 (16)
O1	0.2051 (3)	0.42290 (7)	0.69201 (14)	0.0818 (5)
O2	0.1805 (2)	0.40370 (6)	0.48459 (14)	0.0627 (3)
O3	0.4507 (2)	0.73790 (6)	0.35424 (9)	0.0547 (3)
N1	0.21185 (19)	0.44183 (6)	0.57929 (14)	0.0461 (3)
N2	0.48161 (17)	0.76526 (6)	0.56885 (10)	0.0364 (3)
H2B	0.465 (3)	0.7568 (10)	0.650 (2)	0.054 (5)*
N3	0.73455 (16)	0.84093 (5)	0.53139 (10)	0.0350 (2)
C1	0.36465 (18)	0.65019 (7)	0.50551 (12)	0.0337 (3)
C2	0.3617 (2)	0.62603 (7)	0.63527 (12)	0.0387 (3)
H2A	0.3946	0.6558	0.7051	0.046*
C3	0.3098 (2)	0.55777 (7)	0.66026 (13)	0.0404 (3)
H3A	0.3079	0.5412	0.7463	0.048*
C4	0.26114 (19)	0.51499 (7)	0.55432 (13)	0.0366 (3)
C5	0.2607 (2)	0.53744 (7)	0.42543 (13)	0.0417 (3)
H5A	0.2265	0.5075	0.3561	0.050*
C6	0.3125 (2)	0.60570 (7)	0.40138 (13)	0.0398 (3)
H6A	0.3124	0.6219	0.3150	0.048*
C7	0.43282 (19)	0.72156 (7)	0.46945 (12)	0.0358 (3)
C8	0.54477 (19)	0.83458 (6)	0.54204 (11)	0.0343 (3)
C9	0.8723 (2)	0.78196 (7)	0.54253 (14)	0.0419 (3)
H9A	0.9859	0.7928	0.4937	0.050*
H9B	0.8111	0.7411	0.5029	0.050*
C10	0.9359 (3)	0.76598 (10)	0.68374 (18)	0.0599 (4)
H10A	1.0291	0.7288	0.6858	0.090*
H10B	0.8251	0.7523	0.7312	0.090*
H10C	0.9941	0.8066	0.7241	0.090*
C11	0.8218 (2)	0.90929 (7)	0.50932 (14)	0.0424 (3)
H11A	0.9462	0.9121	0.5585	0.051*
H11B	0.7380	0.9451	0.5423	0.051*
C12	0.8516 (3)	0.92242 (10)	0.36548 (17)	0.0626 (5)
H12A	0.9112	0.9671	0.3555	0.094*
H12B	0.7282	0.9215	0.3169	0.094*
H12C	0.9343	0.8870	0.3324	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0504 (2)	0.0454 (2)	0.0645 (3)	0.01207 (15)	0.00856 (18)	0.01556 (17)
O1	0.1340 (14)	0.0535 (7)	0.0571 (8)	−0.0315 (8)	−0.0022 (8)	0.0155 (6)
O2	0.0811 (9)	0.0375 (6)	0.0697 (8)	−0.0083 (5)	0.0065 (6)	−0.0115 (5)
O3	0.0924 (9)	0.0461 (6)	0.0260 (5)	−0.0114 (5)	0.0046 (5)	0.0040 (4)
N1	0.0475 (6)	0.0360 (6)	0.0549 (7)	−0.0035 (5)	0.0026 (5)	0.0004 (5)
N2	0.0496 (6)	0.0339 (5)	0.0258 (5)	−0.0056 (4)	0.0048 (4)	0.0039 (4)
N3	0.0428 (6)	0.0290 (5)	0.0333 (5)	−0.0008 (4)	0.0032 (4)	0.0024 (4)
C1	0.0386 (6)	0.0338 (6)	0.0288 (6)	0.0001 (5)	0.0030 (4)	−0.0007 (5)
C2	0.0521 (7)	0.0360 (6)	0.0282 (6)	−0.0042 (5)	0.0035 (5)	−0.0018 (5)
C3	0.0515 (7)	0.0386 (7)	0.0313 (6)	−0.0024 (5)	0.0050 (5)	0.0034 (5)
C4	0.0364 (6)	0.0324 (6)	0.0413 (6)	−0.0001 (5)	0.0043 (5)	−0.0002 (5)
C5	0.0494 (7)	0.0400 (7)	0.0354 (6)	−0.0023 (6)	0.0004 (5)	−0.0084 (5)
C6	0.0510 (7)	0.0406 (7)	0.0277 (6)	−0.0011 (5)	0.0007 (5)	−0.0010 (5)
C7	0.0442 (6)	0.0351 (6)	0.0282 (6)	0.0001 (5)	0.0033 (5)	0.0035 (5)
C8	0.0460 (7)	0.0311 (6)	0.0259 (5)	−0.0003 (5)	0.0034 (5)	0.0032 (4)
C9	0.0457 (7)	0.0342 (6)	0.0463 (7)	0.0043 (5)	0.0085 (6)	0.0004 (5)
C10	0.0665 (10)	0.0546 (9)	0.0576 (10)	0.0181 (8)	−0.0072 (8)	0.0076 (8)
C11	0.0503 (8)	0.0336 (6)	0.0433 (7)	−0.0077 (5)	0.0013 (6)	0.0024 (5)
C12	0.0816 (12)	0.0578 (10)	0.0486 (9)	−0.0237 (9)	0.0034 (8)	0.0158 (7)

S1—C8	1.6632 (14)	C3—H3A	0.9300
O1—N1	1.203 (2)	C4—C5	1.377 (2)
O2—N1	1.2191 (19)	C5—C6	1.386 (2)
O3—C7	1.2228 (17)	C5—H5A	0.9300
N1—C4	1.4727 (17)	C6—H6A	0.9300
N2—C7	1.3423 (17)	C9—C10	1.508 (2)
N2—C8	1.4331 (16)	C9—H9A	0.9700
N2—H2B	0.85 (2)	C9—H9B	0.9700
N3—C8	1.322 (2)	C10—H10A	0.9600
N3—C11	1.4678 (17)	C10—H10B	0.9600
N3—C9	1.4792 (17)	C10—H10C	0.9600
C1—C6	1.3921 (18)	C11—C12	1.506 (2)
C1—C2	1.3973 (18)	C11—H11A	0.9700
C1—C7	1.5022 (18)	C11—H11B	0.9700
C2—C3	1.3877 (19)	C12—H12A	0.9600
C2—H2A	0.9300	C12—H12B	0.9600
C3—C4	1.3810 (19)	C12—H12C	0.9600
O1—N1—O2	123.58 (14)	N2—C7—C1	117.30 (11)
O1—N1—C4	118.24 (13)	N3—C8—N2	114.35 (11)
O2—N1—C4	118.18 (13)	N3—C8—S1	126.68 (10)
C7—N2—C8	120.45 (10)	N2—C8—S1	118.96 (10)
C7—N2—H2B	124.5 (14)	N3—C9—C10	112.48 (12)
C8—N2—H2B	114.6 (14)	N3—C9—H9A	109.1
C8—N3—C11	120.62 (11)	C10—C9—H9A	109.1
C8—N3—C9	123.73 (11)	N3—C9—H9B	109.1
C11—N3—C9	115.64 (12)	C10—C9—H9B	109.1
C6—C1—C2	119.65 (13)	H9A—C9—H9B	107.8
C6—C1—C7	116.65 (12)	C9—C10—H10A	109.5
C2—C1—C7	123.60 (11)	C9—C10—H10B	109.5
C3—C2—C1	120.22 (12)	H10A—C10—H10B	109.5
C3—C2—H2A	119.9	C9—C10—H10C	109.5
C1—C2—H2A	119.9	H10A—C10—H10C	109.5
C4—C3—C2	118.43 (12)	H10B—C10—H10C	109.5
C4—C3—H3A	120.8	N3—C11—C12	112.06 (12)
C2—C3—H3A	120.8	N3—C11—H11A	109.2
C5—C4—C3	122.73 (13)	C12—C11—H11A	109.2
C5—C4—N1	118.29 (12)	N3—C11—H11B	109.2
C3—C4—N1	118.97 (12)	C12—C11—H11B	109.2
C4—C5—C6	118.46 (12)	H11A—C11—H11B	107.9
C4—C5—H5A	120.8	C11—C12—H12A	109.5
C6—C5—H5A	120.8	C11—C12—H12B	109.5
C5—C6—C1	120.50 (12)	H12A—C12—H12B	109.5
C5—C6—H6A	119.8	C11—C12—H12C	109.5
C1—C6—H6A	119.8	H12A—C12—H12C	109.5
O3—C7—N2	121.57 (13)	H12B—C12—H12C	109.5
O3—C7—C1	121.07 (12)
C6—C1—C2—C3	0.9 (2)	C8—N2—C7—C1	−178.94 (11)
C7—C1—C2—C3	−175.39 (13)	C6—C1—C7—O3	−3.7 (2)
C1—C2—C3—C4	−0.2 (2)	C2—C1—C7—O3	172.75 (14)
C2—C3—C4—C5	−0.5 (2)	C6—C1—C7—N2	179.30 (12)
C2—C3—C4—N1	178.08 (12)	C2—C1—C7—N2	−4.3 (2)
O1—N1—C4—C5	−177.27 (16)	C11—N3—C8—N2	−177.53 (11)
O2—N1—C4—C5	2.9 (2)	C9—N3—C8—N2	1.45 (17)
O1—N1—C4—C3	4.1 (2)	C11—N3—C8—S1	1.47 (17)
O2—N1—C4—C3	−175.72 (14)	C9—N3—C8—S1	−179.55 (10)
C3—C4—C5—C6	0.4 (2)	C7—N2—C8—N3	−89.79 (15)
N1—C4—C5—C6	−178.16 (13)	C7—N2—C8—S1	91.12 (14)
C4—C5—C6—C1	0.4 (2)	C8—N3—C9—C10	−84.81 (17)
C2—C1—C6—C5	−1.0 (2)	C11—N3—C9—C10	94.21 (15)
C7—C1—C6—C5	175.56 (13)	C8—N3—C11—C12	−96.35 (16)
C8—N2—C7—O3	4.1 (2)	C9—N3—C11—C12	84.59 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3i	0.85 (2)	2.08 (2)	2.915 (2)	165.4 (19)
C2—H2A···O3i	0.93	2.56	3.4671 (19)	165
C6—H6A···S1ii	0.93	2.98	3.824 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3i	0.85 (2)	2.08 (2)	2.915 (2)	165.4 (19)
C2—H2A⋯O3i	0.93	2.56	3.4671 (19)	165
C6—H6A⋯S1ii	0.93	2.98	3.824 (2)	152

Symmetry codes: (i) ; (ii) .