Ethyl 2-[3-(3,5-Dinitrobenzo-yl)thio-ureido]benzoate.

In the title compound, C(17)H(14)N(4)O(7)S, the dihedral angle between the two benzene rings is 9.04 (15)°. The centroid-centroid distance of 3.9825 (19) Å between nearly parallel benzene rings of adjacent mol-ecules suggests the existence of π-π stacking. Inter-molecular and intra-mol-ecular N-H⋯O hydrogen bonding is present in the structure. The eth-oxy group is disordered over two sets of sites with an occupancy ratio of 0.580 (15):0.420 (15). The crystal studied was an inversion twin.

Related literature

For background to the chemistry of thiourea derivatives and their bioloical activity, and a related structure, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C17H14N4O7S

M = 418.38

Monoclinic,

a = 11.7264 (19) Å

b = 16.617 (3) Å

c = 9.9630 (16) Å

β = 101.522 (2)°

V = 1902.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.27 × 0.16 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.943, T max = 0.983

4944 measured reflections

3011 independent reflections

2727 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.10

3011 reflections

301 parameters

42 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1340 Friedel pairs

Flack parameter: 0.39 (8)

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012918/xu5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012918/xu5177Isup2.hkl

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

C17H14N4O7S	F(000) = 864
Mr = 418.38	Dx = 1.461 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6458 reflections
a = 11.7264 (19) Å	θ = 2.1–25.0°
b = 16.617 (3) Å	µ = 0.22 mm−1
c = 9.9630 (16) Å	T = 299 K
β = 101.522 (2)°	Block, yellow
V = 1902.3 (5) Å3	0.27 × 0.16 × 0.08 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3011 independent reflections
Radiation source: fine-focus sealed tube	2727 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω and φ scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→13
Tmin = 0.943, Tmax = 0.983	k = −19→15
4944 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.3273P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3011 reflections	Δρmax = 0.22 e Å−3
301 parameters	Δρmin = −0.24 e Å−3
42 restraints	Absolute structure: Flack (1983), 1340 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.39 (8)

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	Occ. (<1)
S1	0.94150 (8)	0.19793 (4)	0.68183 (8)	0.0759 (3)
O2	0.8103 (2)	0.05570 (13)	1.0967 (3)	0.0866 (7)
O3	0.99391 (19)	−0.01499 (10)	0.97679 (18)	0.0663 (5)
O4	1.0187 (3)	−0.31100 (14)	0.9255 (4)	0.1022 (8)
O5	1.1263 (3)	−0.35915 (14)	0.7937 (3)	0.1095 (10)
O6	1.2496 (4)	−0.1832 (2)	0.4646 (3)	0.1355 (14)
O7	1.2710 (4)	−0.0571 (3)	0.5114 (4)	0.1459 (15)
N1	0.9176 (2)	0.13747 (12)	0.9269 (2)	0.0543 (5)
H1	0.911 (2)	0.0912 (17)	0.974 (3)	0.064 (8)*
H2	0.997 (2)	0.0472 (15)	0.704 (3)	0.045 (7)*
N2	0.9902 (2)	0.05353 (12)	0.7789 (2)	0.0555 (5)
N3	1.0798 (3)	−0.30348 (14)	0.8423 (3)	0.0773 (8)
N4	1.2402 (3)	−0.1244 (3)	0.5338 (3)	0.0976 (10)
C1	0.7736 (3)	0.11786 (17)	1.1281 (3)	0.0647 (7)
C2	0.8103 (2)	0.19844 (15)	1.0865 (3)	0.0563 (6)
C3	0.7770 (3)	0.26756 (18)	1.1485 (3)	0.0713 (8)
H3	0.7296	0.2626	1.2125	0.086*
C4	0.8124 (4)	0.3418 (2)	1.1176 (4)	0.0842 (10)
H4	0.7885	0.3870	1.1596	0.101*
C5	0.8830 (3)	0.35007 (17)	1.0248 (3)	0.0782 (9)
H5	0.9080	0.4010	1.0051	0.094*
C6	0.9179 (3)	0.28322 (16)	0.9596 (3)	0.0657 (7)
H6	0.9662	0.2896	0.8968	0.079*
C7	0.8809 (2)	0.20717 (14)	0.9882 (2)	0.0531 (6)
C8	0.9476 (2)	0.13033 (14)	0.8043 (3)	0.0525 (6)
C9	1.0156 (2)	−0.01157 (13)	0.8622 (2)	0.0518 (6)
C10	1.0713 (2)	−0.08065 (14)	0.8043 (3)	0.0539 (6)
C11	1.0528 (2)	−0.15737 (14)	0.8509 (3)	0.0555 (6)
H11	1.0103	−0.1650	0.9193	0.067*
C12	1.0991 (2)	−0.22190 (15)	0.7933 (3)	0.0595 (7)
C13	1.1609 (3)	−0.21360 (18)	0.6905 (3)	0.0695 (8)
H13	1.1890	−0.2582	0.6508	0.083*
C14	1.1797 (3)	−0.1366 (2)	0.6489 (3)	0.0677 (8)
C15	1.1379 (3)	−0.07002 (16)	0.7053 (3)	0.0618 (7)
H15	1.1542	−0.0186	0.6775	0.074*
O1	0.7136 (10)	0.1247 (5)	1.2262 (9)	0.083 (2)	0.580 (15)
C16	0.6730 (10)	0.0532 (7)	1.2838 (13)	0.113 (4)	0.580 (15)
H16A	0.6931	0.0548	1.3830	0.135*	0.580 (15)
H16B	0.7077	0.0056	1.2523	0.135*	0.580 (15)
C17	0.5404 (10)	0.0522 (6)	1.2345 (19)	0.161 (6)	0.580 (15)
H17A	0.5070	0.0125	1.2851	0.193*	0.580 (15)
H17B	0.5219	0.0392	1.1387	0.193*	0.580 (15)
H17C	0.5093	0.1042	1.2489	0.193*	0.580 (15)
O1'	0.6758 (12)	0.1178 (7)	1.1805 (14)	0.085 (3)	0.420 (15)
C16'	0.6436 (15)	0.0411 (7)	1.2287 (14)	0.084 (4)	0.420 (15)
H16C	0.7119	0.0073	1.2549	0.101*	0.420 (15)
H16D	0.5889	0.0139	1.1571	0.101*	0.420 (15)
C17'	0.5883 (19)	0.0568 (8)	1.3511 (18)	0.134 (6)	0.420 (15)
H17D	0.5738	0.0065	1.3920	0.161*	0.420 (15)
H17E	0.5162	0.0850	1.3219	0.161*	0.420 (15)
H17F	0.6399	0.0888	1.4169	0.161*	0.420 (15)

	U11	U22	U33	U12	U13	U23
S1	0.1117 (6)	0.0590 (4)	0.0655 (4)	0.0263 (4)	0.0381 (4)	0.0158 (3)
O2	0.1105 (17)	0.0589 (12)	0.1056 (17)	0.0112 (11)	0.0580 (14)	0.0120 (11)
O3	0.1054 (16)	0.0478 (10)	0.0498 (10)	0.0112 (9)	0.0252 (10)	−0.0004 (7)
O4	0.131 (2)	0.0570 (13)	0.122 (2)	−0.0046 (13)	0.031 (2)	0.0083 (13)
O5	0.118 (2)	0.0524 (12)	0.153 (3)	0.0257 (13)	0.0147 (19)	−0.0192 (14)
O6	0.172 (3)	0.163 (3)	0.0823 (18)	0.073 (3)	0.052 (2)	−0.0065 (18)
O7	0.179 (4)	0.131 (3)	0.163 (3)	0.028 (3)	0.119 (3)	0.026 (2)
N1	0.0734 (15)	0.0413 (10)	0.0509 (12)	0.0056 (9)	0.0185 (10)	−0.0003 (8)
N2	0.0776 (15)	0.0480 (11)	0.0434 (12)	0.0094 (10)	0.0178 (11)	−0.0029 (9)
N3	0.0820 (18)	0.0479 (13)	0.092 (2)	0.0105 (12)	−0.0056 (16)	−0.0079 (13)
N4	0.099 (2)	0.123 (3)	0.0795 (19)	0.049 (2)	0.0396 (17)	0.0068 (19)
C1	0.076 (2)	0.0658 (17)	0.0559 (15)	0.0108 (14)	0.0209 (14)	0.0059 (12)
C2	0.0635 (17)	0.0569 (14)	0.0459 (13)	0.0114 (11)	0.0046 (12)	−0.0053 (10)
C3	0.081 (2)	0.0679 (18)	0.0663 (18)	0.0144 (14)	0.0178 (16)	−0.0096 (14)
C4	0.103 (3)	0.0639 (19)	0.086 (2)	0.0187 (17)	0.0186 (19)	−0.0250 (16)
C5	0.103 (2)	0.0453 (14)	0.084 (2)	0.0031 (14)	0.0121 (18)	−0.0134 (13)
C6	0.080 (2)	0.0526 (14)	0.0644 (17)	−0.0012 (12)	0.0144 (15)	−0.0065 (12)
C7	0.0631 (16)	0.0459 (12)	0.0478 (13)	0.0070 (10)	0.0049 (12)	−0.0029 (10)
C8	0.0577 (15)	0.0476 (13)	0.0520 (13)	0.0034 (10)	0.0100 (11)	−0.0010 (10)
C9	0.0643 (17)	0.0453 (13)	0.0462 (14)	0.0029 (10)	0.0119 (12)	−0.0023 (10)
C10	0.0649 (17)	0.0507 (13)	0.0445 (12)	0.0062 (11)	0.0069 (12)	−0.0030 (10)
C11	0.0637 (17)	0.0486 (13)	0.0516 (13)	0.0047 (11)	0.0056 (12)	−0.0062 (10)
C12	0.0622 (17)	0.0462 (13)	0.0641 (17)	0.0098 (11)	−0.0015 (14)	−0.0033 (11)
C13	0.0718 (19)	0.0740 (18)	0.0574 (16)	0.0290 (14)	0.0001 (14)	−0.0162 (14)
C14	0.0655 (18)	0.082 (2)	0.0568 (16)	0.0240 (14)	0.0151 (14)	0.0023 (14)
C15	0.0686 (18)	0.0592 (14)	0.0581 (15)	0.0113 (13)	0.0138 (13)	0.0029 (12)
O1	0.103 (6)	0.083 (3)	0.075 (4)	0.006 (3)	0.043 (4)	0.008 (3)
C16	0.130 (8)	0.116 (7)	0.104 (7)	−0.012 (5)	0.053 (6)	0.018 (5)
C17	0.191 (12)	0.086 (5)	0.212 (14)	−0.002 (6)	0.056 (10)	0.002 (7)
O1'	0.087 (6)	0.081 (4)	0.093 (7)	0.005 (4)	0.035 (5)	−0.008 (4)
C16'	0.090 (7)	0.070 (5)	0.108 (8)	−0.013 (4)	0.055 (6)	0.007 (5)
C17'	0.209 (14)	0.092 (7)	0.135 (10)	0.039 (8)	0.116 (10)	0.024 (7)

S1—C8	1.649 (2)	C6—C7	1.385 (4)
O2—C1	1.185 (3)	C6—H6	0.9300
O3—C9	1.219 (3)	C9—C10	1.493 (3)
O4—N3	1.205 (4)	C10—C15	1.386 (4)
O5—N3	1.222 (4)	C10—C11	1.388 (3)
O6—N4	1.213 (4)	C11—C12	1.377 (4)
O7—N4	1.210 (5)	C11—H11	0.9300
N1—C8	1.342 (3)	C12—C13	1.375 (4)
N1—C7	1.416 (3)	C13—C14	1.376 (5)
N1—H1	0.91 (3)	C13—H13	0.9300
N2—C9	1.360 (3)	C14—C15	1.375 (4)
N2—C8	1.412 (3)	C15—H15	0.9300
N2—H2	0.77 (3)	O1—C16	1.442 (8)
N3—C12	1.474 (4)	C16—C17	1.535 (9)
N4—C14	1.478 (4)	C16—H16A	0.9700
C1—O1	1.318 (10)	C16—H16B	0.9700
C1—O1'	1.351 (14)	C17—H17A	0.9600
C1—C2	1.490 (4)	C17—H17B	0.9600
C2—C3	1.396 (4)	C17—H17C	0.9600
C2—C7	1.410 (4)	O1'—C16'	1.440 (9)
C3—C4	1.356 (5)	C16'—C17'	1.514 (9)
C3—H3	0.9300	C16'—H16C	0.9700
C4—C5	1.365 (5)	C16'—H16D	0.9700
C4—H4	0.9300	C17'—H17D	0.9600
C5—C6	1.389 (4)	C17'—H17E	0.9600
C5—H5	0.9300	C17'—H17F	0.9600
C8—N1—C7	128.5 (2)	N2—C9—C10	115.8 (2)
C8—N1—H1	117.1 (18)	C15—C10—C11	120.2 (2)
C7—N1—H1	114.0 (18)	C15—C10—C9	122.0 (2)
C9—N2—C8	130.7 (2)	C11—C10—C9	117.9 (2)
C9—N2—H2	115.4 (18)	C12—C11—C10	118.4 (3)
C8—N2—H2	113.8 (19)	C12—C11—H11	120.8
O4—N3—O5	124.6 (3)	C10—C11—H11	120.8
O4—N3—C12	118.4 (2)	C13—C12—C11	122.8 (3)
O5—N3—C12	117.1 (3)	C13—C12—N3	118.5 (2)
O7—N4—O6	125.1 (4)	C11—C12—N3	118.6 (3)
O7—N4—C14	118.6 (3)	C12—C13—C14	117.2 (2)
O6—N4—C14	116.2 (4)	C12—C13—H13	121.4
O2—C1—O1	123.2 (5)	C14—C13—H13	121.4
O2—C1—O1'	118.9 (6)	C15—C14—C13	122.3 (3)
O2—C1—C2	124.7 (3)	C15—C14—N4	118.1 (3)
O1—C1—C2	110.8 (4)	C13—C14—N4	119.5 (3)
O1'—C1—C2	115.0 (5)	C14—C15—C10	119.0 (3)
C3—C2—C7	118.5 (2)	C14—C15—H15	120.5
C3—C2—C1	119.6 (3)	C10—C15—H15	120.5
C7—C2—C1	121.9 (2)	C1—O1—C16	119.4 (9)
C4—C3—C2	121.5 (3)	O1—C16—C17	106.0 (9)
C4—C3—H3	119.2	O1—C16—H16A	110.5
C2—C3—H3	119.2	C17—C16—H16A	110.5
C3—C4—C5	120.0 (3)	O1—C16—H16B	110.5
C3—C4—H4	120.0	C17—C16—H16B	110.5
C5—C4—H4	120.0	H16A—C16—H16B	108.7
C4—C5—C6	120.7 (3)	C1—O1'—C16'	115.3 (10)
C4—C5—H5	119.6	O1'—C16'—C17'	107.4 (10)
C6—C5—H5	119.6	O1'—C16'—H16C	110.2
C7—C6—C5	120.0 (3)	C17'—C16'—H16C	110.2
C7—C6—H6	120.0	O1'—C16'—H16D	110.2
C5—C6—H6	120.0	C17'—C16'—H16D	110.2
C6—C7—C2	119.3 (2)	H16C—C16'—H16D	108.5
C6—C7—N1	121.5 (2)	C16'—C17'—H17D	109.5
C2—C7—N1	119.1 (2)	C16'—C17'—H17E	109.5
N1—C8—N2	114.2 (2)	H17D—C17'—H17E	109.5
N1—C8—S1	129.22 (19)	C16'—C17'—H17F	109.5
N2—C8—S1	116.62 (19)	H17D—C17'—H17F	109.5
O3—C9—N2	123.2 (2)	H17E—C17'—H17F	109.5
O3—C9—C10	121.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1—H1···O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2—H2···O3i	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1—H1⋯O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2—H2⋯O3i	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)

Symmetry code: (i) .