1-(3,5-Dinitro-benzo-yl)-3,3-dipropyl-thio-urea.

The title thio-urea derivative, C(14)H(18)N(4)O(5)S, features two substantial twists between its component fragments: the dihedral angle between the SN(2)C (thio-urea) and ONC(2) (amide) residues is 48.89 (7)° and that between the benzene ring and the amide residue is 30.27 (7)°. In the crystal, mol-ecules are linked by bifurcated N-H⋯(O,S) hydrogen bonds, generating [001] supra-molecular chains.

Related literature

For the biological activity of thio­urea derivatives, see: Venkatachalam et al., (2004 ▶); Saeed et al. (2011 ▶). For related thio­urea structures, see: Gunasekaran et al. (2010 ▶); Saeed et al. (2010 ▶); Dzulkifli et al. (2011 ▶).

Experimental

Crystal data

C14H18N4O5S

M = 354.38

Monoclinic,

a = 7.9406 (4) Å

b = 21.2839 (10) Å

c = 9.5967 (4) Å

β = 94.379 (4)°

V = 1617.17 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.933, T max = 0.977

8055 measured reflections

3614 independent reflections

2878 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.154

S = 1.02

3614 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.04 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013638/hb5845sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013638/hb5845Isup2.hkl

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

C14H18N4O5S	F(000) = 744
Mr = 354.38	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3443 reflections
a = 7.9406 (4) Å	θ = 2.3–29.3°
b = 21.2839 (10) Å	µ = 0.23 mm−1
c = 9.5967 (4) Å	T = 295 K
β = 94.379 (4)°	Prism, light yellow
V = 1617.17 (13) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3614 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2878 reflections with I > 2σ(I)
Mirror	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −27→26
Tmin = 0.933, Tmax = 0.977	l = −12→10
8055 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0697P)2 + 1.1729P] where P = (Fo2 + 2Fc2)/3
3614 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 1.04 e Å−3
1 restraint	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.37257 (8)	0.21276 (3)	0.24866 (6)	0.0405 (2)
O1	0.7561 (2)	0.24758 (9)	0.29218 (19)	0.0505 (5)
O2	0.5844 (3)	0.44242 (11)	0.7375 (2)	0.0621 (6)
O3	0.8149 (3)	0.49393 (11)	0.7748 (3)	0.0761 (7)
O4	1.2906 (3)	0.44304 (11)	0.5156 (3)	0.0711 (7)
O5	1.3052 (3)	0.35161 (11)	0.4221 (2)	0.0623 (6)
N1	0.4129 (2)	0.15013 (9)	0.4887 (2)	0.0334 (4)
N2	0.5882 (3)	0.23606 (9)	0.4730 (2)	0.0343 (4)
H2	0.581 (3)	0.2455 (12)	0.5607 (13)	0.044 (7)*
N3	0.7311 (3)	0.45149 (10)	0.7190 (2)	0.0451 (5)
N4	1.2306 (3)	0.39224 (11)	0.4807 (2)	0.0440 (5)
C1	0.2706 (3)	0.10939 (12)	0.4387 (3)	0.0433 (6)
H1A	0.2787	0.0701	0.4899	0.052*
H1B	0.2802	0.0999	0.3408	0.052*
C2	0.0973 (4)	0.1384 (2)	0.4550 (4)	0.0746 (10)
H2A	0.0819	0.1733	0.3903	0.089*
H2B	0.0117	0.1073	0.4280	0.089*
C3	0.0687 (5)	0.1608 (2)	0.5930 (5)	0.0882 (13)
H3A	−0.0414	0.1795	0.5919	0.132*
H3B	0.1528	0.1915	0.6217	0.132*
H3C	0.0757	0.1262	0.6574	0.132*
C4	0.5096 (3)	0.12842 (12)	0.6168 (2)	0.0396 (6)
H4A	0.4329	0.1098	0.6791	0.047*
H4B	0.5640	0.1641	0.6642	0.047*
C5	0.6417 (4)	0.08077 (13)	0.5847 (3)	0.0510 (7)
H5A	0.7223	0.1002	0.5270	0.061*
H5B	0.5880	0.0464	0.5318	0.061*
C6	0.7351 (4)	0.05486 (15)	0.7163 (4)	0.0659 (9)
H6A	0.8211	0.0262	0.6912	0.099*
H6B	0.6569	0.0332	0.7708	0.099*
H6C	0.7862	0.0888	0.7701	0.099*
C7	0.4603 (3)	0.19711 (10)	0.4084 (2)	0.0313 (5)
C8	0.7150 (3)	0.26338 (11)	0.4063 (2)	0.0339 (5)
C9	0.8066 (3)	0.31654 (10)	0.4830 (2)	0.0320 (5)
C10	0.7262 (3)	0.35735 (11)	0.5703 (2)	0.0337 (5)
H10	0.6152	0.3502	0.5908	0.040*
C11	0.8147 (3)	0.40847 (11)	0.6256 (2)	0.0350 (5)
C12	0.9793 (3)	0.42129 (11)	0.5982 (2)	0.0367 (5)
H12	1.0361	0.4564	0.6352	0.044*
C13	1.0552 (3)	0.37937 (11)	0.5132 (2)	0.0353 (5)
C14	0.9729 (3)	0.32754 (11)	0.4549 (2)	0.0338 (5)
H14	1.0280	0.3004	0.3976	0.041*

	U11	U22	U33	U12	U13	U23
S1	0.0449 (4)	0.0445 (4)	0.0315 (3)	−0.0042 (3)	−0.0021 (2)	0.0030 (2)
O1	0.0508 (11)	0.0646 (12)	0.0378 (10)	−0.0172 (9)	0.0146 (8)	−0.0188 (9)
O2	0.0525 (12)	0.0665 (14)	0.0695 (14)	0.0005 (10)	0.0182 (10)	−0.0207 (11)
O3	0.0734 (15)	0.0652 (14)	0.0909 (17)	−0.0130 (12)	0.0146 (13)	−0.0475 (13)
O4	0.0519 (12)	0.0681 (15)	0.0941 (18)	−0.0262 (11)	0.0118 (12)	−0.0156 (13)
O5	0.0438 (11)	0.0814 (15)	0.0636 (13)	−0.0046 (10)	0.0156 (10)	−0.0176 (12)
N1	0.0346 (10)	0.0325 (10)	0.0331 (10)	−0.0015 (8)	0.0025 (8)	−0.0001 (8)
N2	0.0410 (11)	0.0364 (10)	0.0259 (9)	−0.0079 (8)	0.0048 (8)	−0.0052 (8)
N3	0.0514 (14)	0.0432 (12)	0.0409 (12)	0.0023 (10)	0.0037 (10)	−0.0077 (10)
N4	0.0355 (11)	0.0570 (14)	0.0393 (11)	−0.0067 (10)	0.0005 (9)	0.0007 (10)
C1	0.0423 (14)	0.0389 (13)	0.0486 (14)	−0.0094 (11)	0.0036 (11)	−0.0017 (11)
C2	0.0510 (18)	0.097 (3)	0.076 (2)	−0.0187 (18)	0.0090 (16)	−0.015 (2)
C3	0.059 (2)	0.102 (3)	0.107 (3)	−0.015 (2)	0.022 (2)	−0.040 (3)
C4	0.0476 (14)	0.0394 (13)	0.0317 (12)	−0.0022 (11)	0.0031 (10)	0.0047 (10)
C5	0.0528 (16)	0.0482 (15)	0.0500 (16)	0.0068 (13)	−0.0093 (13)	−0.0058 (12)
C6	0.072 (2)	0.0484 (17)	0.072 (2)	0.0038 (15)	−0.0257 (17)	0.0032 (15)
C7	0.0323 (11)	0.0305 (11)	0.0315 (11)	0.0008 (9)	0.0055 (9)	−0.0042 (9)
C8	0.0363 (12)	0.0348 (12)	0.0308 (11)	−0.0036 (9)	0.0035 (9)	−0.0035 (9)
C9	0.0362 (12)	0.0337 (11)	0.0259 (10)	−0.0029 (9)	0.0015 (9)	0.0012 (9)
C10	0.0353 (12)	0.0372 (12)	0.0285 (11)	−0.0025 (10)	0.0019 (9)	0.0023 (9)
C11	0.0398 (13)	0.0344 (12)	0.0304 (11)	0.0023 (10)	0.0006 (9)	−0.0022 (9)
C12	0.0424 (13)	0.0351 (12)	0.0318 (11)	−0.0063 (10)	−0.0024 (10)	−0.0029 (9)
C13	0.0341 (12)	0.0416 (13)	0.0299 (11)	−0.0042 (10)	0.0002 (9)	0.0037 (9)
C14	0.0364 (12)	0.0363 (12)	0.0290 (11)	0.0003 (10)	0.0040 (9)	−0.0005 (9)

S1—C7	1.668 (2)	C3—H3B	0.9600
O1—C8	1.214 (3)	C3—H3C	0.9600
O2—N3	1.207 (3)	C4—C5	1.508 (4)
O3—N3	1.221 (3)	C4—H4A	0.9700
O4—N4	1.218 (3)	C4—H4B	0.9700
O5—N4	1.211 (3)	C5—C6	1.519 (4)
N1—C7	1.334 (3)	C5—H5A	0.9700
N1—C4	1.473 (3)	C5—H5B	0.9700
N1—C1	1.475 (3)	C6—H6A	0.9600
N2—C8	1.364 (3)	C6—H6B	0.9600
N2—C7	1.417 (3)	C6—H6C	0.9600
N2—H2	0.871 (10)	C8—C9	1.507 (3)
N3—C11	1.474 (3)	C9—C14	1.388 (3)
N4—C13	1.476 (3)	C9—C10	1.394 (3)
C1—C2	1.527 (4)	C10—C11	1.379 (3)
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700	C11—C12	1.380 (3)
C2—C3	1.441 (5)	C12—C13	1.378 (3)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.379 (3)
C3—H3A	0.9600	C14—H14	0.9300
C7—N1—C4	124.44 (19)	C4—C5—C6	112.2 (2)
C7—N1—C1	119.7 (2)	C4—C5—H5A	109.2
C4—N1—C1	115.12 (19)	C6—C5—H5A	109.2
C8—N2—C7	125.03 (19)	C4—C5—H5B	109.2
C8—N2—H2	117.3 (18)	C6—C5—H5B	109.2
C7—N2—H2	117.5 (18)	H5A—C5—H5B	107.9
O2—N3—O3	123.6 (2)	C5—C6—H6A	109.5
O2—N3—C11	118.3 (2)	C5—C6—H6B	109.5
O3—N3—C11	118.1 (2)	H6A—C6—H6B	109.5
O5—N4—O4	124.5 (2)	C5—C6—H6C	109.5
O5—N4—C13	117.9 (2)	H6A—C6—H6C	109.5
O4—N4—C13	117.5 (2)	H6B—C6—H6C	109.5
N1—C1—C2	113.7 (2)	N1—C7—N2	114.2 (2)
N1—C1—H1A	108.8	N1—C7—S1	124.35 (18)
C2—C1—H1A	108.8	N2—C7—S1	121.38 (17)
N1—C1—H1B	108.8	O1—C8—N2	124.3 (2)
C2—C1—H1B	108.8	O1—C8—C9	119.7 (2)
H1A—C1—H1B	107.7	N2—C8—C9	115.93 (19)
C3—C2—C1	115.8 (3)	C14—C9—C10	119.9 (2)
C3—C2—H2A	108.3	C14—C9—C8	117.6 (2)
C1—C2—H2A	108.3	C10—C9—C8	122.3 (2)
C3—C2—H2B	108.3	C11—C10—C9	118.6 (2)
C1—C2—H2B	108.3	C11—C10—H10	120.7
H2A—C2—H2B	107.4	C9—C10—H10	120.7
C2—C3—H3A	109.5	C10—C11—C12	123.0 (2)
C2—C3—H3B	109.5	C10—C11—N3	118.9 (2)
H3A—C3—H3B	109.5	C12—C11—N3	118.1 (2)
C2—C3—H3C	109.5	C13—C12—C11	116.6 (2)
H3A—C3—H3C	109.5	C13—C12—H12	121.7
H3B—C3—H3C	109.5	C11—C12—H12	121.7
N1—C4—C5	111.5 (2)	C12—C13—C14	122.9 (2)
N1—C4—H4A	109.3	C12—C13—N4	117.9 (2)
C5—C4—H4A	109.3	C14—C13—N4	119.2 (2)
N1—C4—H4B	109.3	C13—C14—C9	119.0 (2)
C5—C4—H4B	109.3	C13—C14—H14	120.5
H4A—C4—H4B	108.0	C9—C14—H14	120.5
C7—N1—C1—C2	−79.3 (3)	C8—C9—C10—C11	−173.6 (2)
C4—N1—C1—C2	110.2 (3)	C9—C10—C11—C12	0.2 (3)
N1—C1—C2—C3	−52.9 (4)	C9—C10—C11—N3	−179.4 (2)
C7—N1—C4—C5	−86.1 (3)	O2—N3—C11—C10	−4.2 (3)
C1—N1—C4—C5	83.9 (3)	O3—N3—C11—C10	174.9 (2)
N1—C4—C5—C6	−176.4 (2)	O2—N3—C11—C12	176.2 (2)
C4—N1—C7—N2	−15.8 (3)	O3—N3—C11—C12	−4.8 (4)
C1—N1—C7—N2	174.7 (2)	C10—C11—C12—C13	−1.2 (3)
C4—N1—C7—S1	167.53 (18)	N3—C11—C12—C13	178.5 (2)
C1—N1—C7—S1	−2.0 (3)	C11—C12—C13—C14	1.2 (3)
C8—N2—C7—N1	144.3 (2)	C11—C12—C13—N4	179.3 (2)
C8—N2—C7—S1	−38.9 (3)	O5—N4—C13—C12	170.3 (2)
C7—N2—C8—O1	−16.5 (4)	O4—N4—C13—C12	−9.3 (3)
C7—N2—C8—C9	163.4 (2)	O5—N4—C13—C14	−11.5 (3)
O1—C8—C9—C14	−27.4 (3)	O4—N4—C13—C14	168.9 (2)
N2—C8—C9—C14	152.7 (2)	C12—C13—C14—C9	−0.3 (3)
O1—C8—C9—C10	147.1 (2)	N4—C13—C14—C9	−178.4 (2)
N2—C8—C9—C10	−32.8 (3)	C10—C9—C14—C13	−0.7 (3)
C14—C9—C10—C11	0.7 (3)	C8—C9—C14—C13	173.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.87 (1)	2.53 (2)	3.264 (3)	142 (2)
N2—H2···S1i	0.87 (1)	2.69 (2)	3.436 (2)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.87 (1)	2.53 (2)	3.264 (3)	142 (2)
N2—H2⋯S1i	0.87 (1)	2.69 (2)	3.436 (2)	144 (2)

Symmetry code: (i) .