Ethyl 2-[3-(4-nitro-benzo-yl)thio-ureido]benzoate.

In the title compound, C(17)H(15)N(3)O(5)S, the nitro and thio-ureido groups are twisted by 7.2 (7) and 21.4 (2)°, respectively, from the nitro-benzene ring plane whereas the thio-ureido and the ethyl ester group make dihedral angles of 43.0 (1) and 18.0 (2)°, respectively, with the benzene rings to which they are attached. Intra-molecular N-H⋯O hydrogen-bonding inter-actions are observed. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into chains running along the a axis.

Related literature

For general background to the chemistry of thio­urea derivatives, see: Ugur et al. (2006 ▶). For related compounds with anti­tubercular properties, see: Huebner et al. (1953 ▶) and for other biological activities of thio­urea compounds, see: Glasser & Doughty (1964 ▶). For related structures, see: Saeed et al. (2008a ▶,b ▶). For the cytotoxicity of anti­cancer drugs to normal cells in cancer therapy, see: Saeed et al. (2010 ▶). For the herbicidal activity of thio­urea derivatives, see: Zheng et al. (2004 ▶).

Experimental

Crystal data

C17H15N3O5S

M = 373.38

Orthorhombic,

a = 9.0698 (13) Å

b = 15.778 (2) Å

c = 24.889 (4) Å

V = 3561.7 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.36 × 0.25 × 0.03 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.927, T max = 0.994

23121 measured reflections

4362 independent reflections

2877 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.171

S = 1.07

4362 reflections

244 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT and CrystalStructure (Rigaku/MSC and Rigaku, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011116/si2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011116/si2248Isup2.hkl

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

C17H15N3O5S	Dx = 1.393 Mg m−3
Mr = 373.38	Melting point: 438 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 23121 reflections
a = 9.0698 (13) Å	θ = 1.6–28.3°
b = 15.778 (2) Å	µ = 0.22 mm−1
c = 24.889 (4) Å	T = 295 K
V = 3561.7 (9) Å3	Plate, yellow
Z = 8	0.36 × 0.25 × 0.03 mm
F(000) = 1552

Bruker SMART 1000 CCD diffractometer	4362 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scan	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
Tmin = 0.927, Tmax = 0.994	k = −21→21
23121 measured reflections	l = −33→32

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0709P)2 + 2.2491P] where P = (Fo2 + 2Fc2)/3
4362 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.63 e Å−3
6 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.51557 (9)	0.11637 (5)	0.20685 (4)	0.0587 (3)
O1	0.3603 (6)	0.5330 (3)	0.44429 (14)	0.1331 (16)
O2	0.1862 (4)	0.6034 (2)	0.40527 (18)	0.1245 (13)
O3	0.1165 (2)	0.29106 (13)	0.21392 (8)	0.0476 (5)
O4	0.0879 (3)	0.24551 (13)	0.09489 (9)	0.0641 (6)
O5	0.0925 (3)	0.19226 (14)	0.01211 (9)	0.0662 (7)
N1	0.2655 (5)	0.5415 (2)	0.41024 (19)	0.0936 (13)
N2	0.3396 (2)	0.23826 (15)	0.23814 (10)	0.0428 (5)
N3	0.2463 (3)	0.15722 (15)	0.16898 (9)	0.0414 (5)
C1	0.2484 (4)	0.4741 (2)	0.36882 (15)	0.0648 (9)
C2	0.1512 (4)	0.4866 (2)	0.32689 (17)	0.0690 (10)
H2	0.0937	0.5353	0.3250	0.083*
C3	0.1416 (4)	0.4242 (2)	0.28770 (13)	0.0552 (8)
H3	0.0758	0.4306	0.2593	0.066*
C4	0.2296 (3)	0.35235 (17)	0.29062 (11)	0.0423 (6)
C5	0.3214 (3)	0.3409 (2)	0.33479 (12)	0.0516 (7)
H5	0.3764	0.2914	0.3379	0.062*
C6	0.3312 (4)	0.4026 (2)	0.37399 (13)	0.0630 (9)
H6	0.3932	0.3955	0.4034	0.076*
C7	0.2219 (3)	0.29142 (16)	0.24481 (10)	0.0388 (6)
C8	0.3576 (3)	0.17016 (17)	0.20286 (10)	0.0411 (6)
C9	0.2299 (3)	0.08868 (17)	0.13261 (11)	0.0423 (6)
C10	0.2679 (4)	0.00680 (19)	0.14754 (13)	0.0575 (8)
H10	0.3060	−0.0030	0.1817	0.069*
C11	0.2504 (4)	−0.0600 (2)	0.11286 (15)	0.0661 (9)
H11	0.2767	−0.1144	0.1236	0.079*
C12	0.1938 (4)	−0.0466 (2)	0.06204 (15)	0.0659 (9)
H12	0.1837	−0.0916	0.0382	0.079*
C13	0.1526 (4)	0.03375 (19)	0.04696 (13)	0.0552 (8)
H13	0.1138	0.0424	0.0128	0.066*
C14	0.1677 (3)	0.10259 (17)	0.08161 (11)	0.0435 (6)
C15	0.1132 (3)	0.18718 (18)	0.06483 (12)	0.0472 (7)
C16	0.0290 (5)	0.2705 (2)	−0.00865 (15)	0.0782 (11)
H16A	0.0907	0.3184	0.0010	0.094*
H16B	−0.0684	0.2794	0.0064	0.094*
C17	0.0198 (5)	0.2627 (3)	−0.06722 (17)	0.0872 (13)
H17A	−0.0220	0.3135	−0.0820	0.105*
H17B	−0.0414	0.2152	−0.0763	0.105*
H17C	0.1168	0.2543	−0.0817	0.105*
H2N	0.409 (4)	0.2503 (19)	0.2566 (13)	0.047 (9)*
H3N	0.177 (3)	0.200 (2)	0.1694 (12)	0.050 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0427 (4)	0.0648 (5)	0.0686 (5)	0.0143 (3)	−0.0073 (4)	−0.0180 (4)
O1	0.208 (5)	0.116 (3)	0.075 (2)	−0.037 (3)	−0.004 (3)	−0.037 (2)
O2	0.099 (2)	0.104 (2)	0.171 (3)	−0.0053 (18)	0.0240 (19)	−0.073 (2)
O3	0.0353 (10)	0.0564 (12)	0.0511 (11)	0.0026 (8)	−0.0027 (8)	0.0000 (9)
O4	0.0893 (17)	0.0445 (12)	0.0584 (13)	0.0126 (11)	−0.0185 (12)	−0.0062 (10)
O5	0.0994 (19)	0.0516 (13)	0.0476 (12)	0.0076 (12)	−0.0137 (12)	0.0037 (10)
N1	0.094 (3)	0.073 (2)	0.114 (3)	−0.026 (2)	0.042 (2)	−0.039 (2)
N2	0.0302 (11)	0.0540 (14)	0.0442 (13)	0.0015 (10)	−0.0021 (10)	−0.0106 (10)
N3	0.0400 (12)	0.0416 (12)	0.0425 (12)	0.0015 (10)	−0.0035 (10)	−0.0026 (10)
C1	0.065 (2)	0.062 (2)	0.067 (2)	−0.0163 (17)	0.0258 (18)	−0.0232 (17)
C2	0.066 (2)	0.0466 (18)	0.094 (3)	0.0033 (15)	0.027 (2)	−0.0093 (18)
C3	0.0485 (17)	0.0510 (17)	0.0661 (19)	0.0060 (13)	0.0097 (15)	0.0010 (15)
C4	0.0356 (13)	0.0448 (14)	0.0466 (14)	−0.0019 (11)	0.0115 (11)	−0.0026 (12)
C5	0.0468 (16)	0.0601 (18)	0.0479 (16)	0.0042 (13)	0.0045 (13)	−0.0090 (14)
C6	0.058 (2)	0.083 (2)	0.0482 (17)	−0.0072 (18)	0.0094 (15)	−0.0178 (16)
C7	0.0310 (12)	0.0442 (14)	0.0410 (13)	−0.0020 (10)	0.0057 (11)	0.0024 (11)
C8	0.0379 (13)	0.0476 (15)	0.0378 (13)	−0.0009 (11)	0.0031 (11)	−0.0008 (11)
C9	0.0416 (14)	0.0404 (14)	0.0448 (14)	−0.0014 (11)	0.0001 (12)	−0.0015 (11)
C10	0.068 (2)	0.0458 (16)	0.0589 (19)	0.0016 (15)	−0.0138 (16)	0.0046 (14)
C11	0.079 (2)	0.0407 (17)	0.079 (2)	0.0046 (16)	−0.0134 (19)	0.0007 (15)
C12	0.086 (3)	0.0419 (17)	0.070 (2)	0.0032 (16)	−0.0107 (19)	−0.0121 (15)
C13	0.067 (2)	0.0484 (17)	0.0496 (16)	0.0006 (14)	−0.0096 (15)	−0.0070 (13)
C14	0.0460 (15)	0.0416 (14)	0.0429 (14)	−0.0026 (11)	−0.0026 (12)	−0.0010 (11)
C15	0.0489 (16)	0.0447 (16)	0.0481 (16)	−0.0025 (12)	−0.0088 (13)	0.0004 (12)
C16	0.107 (3)	0.059 (2)	0.069 (2)	0.012 (2)	−0.021 (2)	0.0121 (18)
C17	0.103 (3)	0.083 (3)	0.076 (3)	−0.005 (2)	−0.026 (2)	0.021 (2)

S1—C8	1.668 (3)	C4—C7	1.493 (4)
O1—N1	1.215 (6)	C5—C6	1.381 (4)
O2—N1	1.219 (5)	C5—H5	0.9300
O3—C7	1.227 (3)	C6—H6	0.9300
O4—C15	1.208 (3)	C9—C10	1.388 (4)
O5—C15	1.328 (3)	C9—C14	1.406 (4)
O5—C16	1.457 (4)	C10—C11	1.371 (4)
N1—C1	1.489 (5)	C10—H10	0.9300
N2—C7	1.368 (3)	C11—C12	1.381 (5)
N2—C8	1.397 (3)	C11—H11	0.9300
N2—H2N	0.80 (3)	C12—C13	1.373 (5)
N3—C8	1.331 (3)	C12—H12	0.9300
N3—C9	1.418 (3)	C13—C14	1.394 (4)
N3—H3N	0.91 (3)	C13—H13	0.9300
C1—C6	1.361 (5)	C14—C15	1.483 (4)
C1—C2	1.380 (6)	C16—C17	1.465 (6)
C2—C3	1.388 (5)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.388 (4)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.391 (4)	C17—H17C	0.9600
C15—O5—C16	117.2 (3)	C10—C9—C14	119.1 (3)
O1—N1—O2	125.2 (4)	C10—C9—N3	120.9 (3)
O1—N1—C1	118.6 (4)	C14—C9—N3	119.9 (2)
O2—N1—C1	116.1 (5)	C11—C10—C9	121.2 (3)
C7—N2—C8	129.7 (2)	C11—C10—H10	119.4
C7—N2—H2N	113 (2)	C9—C10—H10	119.4
C8—N2—H2N	117 (2)	C10—C11—C12	120.1 (3)
C8—N3—C9	126.9 (2)	C10—C11—H11	119.9
C8—N3—H3N	113.5 (19)	C12—C11—H11	119.9
C9—N3—H3N	119.5 (19)	C13—C12—C11	119.5 (3)
C6—C1—C2	122.8 (3)	C13—C12—H12	120.2
C6—C1—N1	117.9 (4)	C11—C12—H12	120.2
C2—C1—N1	119.2 (4)	C12—C13—C14	121.6 (3)
C1—C2—C3	118.0 (3)	C12—C13—H13	119.2
C1—C2—H2	121.0	C14—C13—H13	119.2
C3—C2—H2	121.0	C13—C14—C9	118.4 (3)
C2—C3—C4	120.4 (3)	C13—C14—C15	119.6 (3)
C2—C3—H3	119.8	C9—C14—C15	121.9 (2)
C4—C3—H3	119.8	O4—C15—O5	122.6 (3)
C3—C4—C5	119.4 (3)	O4—C15—C14	125.1 (3)
C3—C4—C7	117.3 (3)	O5—C15—C14	112.3 (2)
C5—C4—C7	123.2 (2)	O5—C16—C17	107.7 (3)
C6—C5—C4	120.4 (3)	O5—C16—H16A	110.2
C6—C5—H5	119.8	C17—C16—H16A	110.2
C4—C5—H5	119.8	O5—C16—H16B	110.2
C1—C6—C5	118.8 (3)	C17—C16—H16B	110.2
C1—C6—H6	120.6	H16A—C16—H16B	108.5
C5—C6—H6	120.6	C16—C17—H17A	109.5
O3—C7—N2	122.0 (2)	C16—C17—H17B	109.5
O3—C7—C4	121.2 (2)	H17A—C17—H17B	109.5
N2—C7—C4	116.8 (2)	C16—C17—H17C	109.5
N3—C8—N2	115.3 (2)	H17A—C17—H17C	109.5
N3—C8—S1	127.7 (2)	H17B—C17—H17C	109.5
N2—C8—S1	117.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3i	0.80 (4)	2.12 (4)	2.903 (3)	165 (3)
N3—H3N···O3	0.91 (3)	1.91 (3)	2.664 (3)	139 (3)
N3—H3N···O4	0.91 (3)	2.15 (3)	2.721 (3)	120 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3i	0.80 (4)	2.12 (4)	2.903 (3)	165 (3)
N3—H3N⋯O3	0.91 (3)	1.91 (3)	2.664 (3)	139 (3)
N3—H3N⋯O4	0.91 (3)	2.15 (3)	2.721 (3)	120 (2)

Symmetry code: (i) .