3-Cyclo-hexyl-1-(3,5-dinitro-benzo-yl)thio-urea.

The structure of the title thio-urea derivative, C(14)H(16)N(4)O(5)S, features an almost planar central C(2)N(2)OS fragment (r.m.s. deviation = 0.005 Å), an arrangement stabilized by an intra-molecular N-H⋯O hydrogen bond. The terminal rings are twisted out of this plane, the dihedral angle formed with the benzene ring being 33.22 (10)°. The cyclo-hexyl ring is disordered, with two orientations (50:50) being resolved. The mean plane passing through the atoms of each disordered component forms dihedral angles of 65.7 (2) and 82.4 (3)° with the central plane. Centrosymmetric dimers mediated by an eight-membered {⋯HNC=S}(2) synthon occur in the crystal.

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

C14H16N4O5S

M = 352.37

Monoclinic,

a = 12.3404 (7) Å

b = 9.0506 (5) Å

c = 14.6534 (6) Å

β = 90.385 (5)°

V = 1636.57 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.20 × 0.15 × 0.10 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.955, T max = 0.977

7954 measured reflections

3649 independent reflections

1948 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.211

S = 1.01

3649 reflections

271 parameters

25 restraints

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 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/S1600536811013377/hb5839sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013377/hb5839Isup2.hkl

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

C14H16N4O5S	F(000) = 736
Mr = 352.37	Dx = 1.430 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2522 reflections
a = 12.3404 (7) Å	θ = 2.6–29.2°
b = 9.0506 (5) Å	µ = 0.23 mm−1
c = 14.6534 (6) Å	T = 295 K
β = 90.385 (5)°	Prism, colorless
V = 1636.57 (15) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector	3649 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1948 reflections with I > 2σ(I)
Mirror	Rint = 0.024
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −11→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→9
Tmin = 0.955, Tmax = 0.977	l = −19→18
7954 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0901P)2 + 0.5204P] where P = (Fo2 + 2Fc2)/3
3649 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.22 e Å−3
25 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.41365 (9)	0.64167 (12)	0.59283 (6)	0.0914 (4)
O1	0.2058 (2)	0.5972 (4)	0.33847 (18)	0.1069 (9)
O2	0.1940 (3)	0.2554 (4)	0.0798 (2)	0.1410 (13)
O3	0.3315 (3)	0.2306 (4)	−0.0052 (3)	0.1351 (13)
O4	0.6723 (3)	0.4548 (4)	0.0872 (2)	0.1237 (11)
O5	0.6733 (2)	0.6067 (4)	0.2004 (2)	0.1140 (10)
N1	0.2226 (2)	0.6699 (3)	0.5124 (2)	0.0864 (9)
H1	0.1881	0.6629	0.4598	0.104*	0.50
H1'	0.1777	0.6614	0.4657	0.104*	0.50
N2	0.3606 (2)	0.5812 (3)	0.42290 (16)	0.0689 (7)
H2	0.4294	0.5564	0.4197	0.083*
N3	0.2883 (4)	0.2769 (4)	0.0621 (3)	0.0964 (10)
N4	0.6288 (3)	0.5175 (4)	0.1510 (2)	0.0907 (9)
C1	0.1543 (7)	0.7215 (9)	0.5861 (6)	0.074 (3)	0.50
H1A	0.1990	0.7735	0.6313	0.088*	0.50
C2	0.0991 (8)	0.5900 (9)	0.6317 (6)	0.084 (3)	0.50
H2A	0.1529	0.5203	0.6537	0.101*	0.50
H2B	0.0520	0.5398	0.5885	0.101*	0.50
C3	0.0323 (6)	0.6513 (8)	0.7122 (4)	0.094 (2)	0.50
H3A	−0.0055	0.5709	0.7420	0.113*	0.50
H3B	0.0807	0.6964	0.7567	0.113*	0.50
C4	−0.0488 (6)	0.7647 (9)	0.6791 (5)	0.106 (3)	0.50
H4A	−0.1009	0.7171	0.6389	0.127*	0.50
H4B	−0.0879	0.8040	0.7309	0.127*	0.50
C5	0.0049 (6)	0.8899 (8)	0.6289 (5)	0.098 (3)	0.50
H5A	0.0532	0.9427	0.6700	0.117*	0.50
H5B	−0.0496	0.9586	0.6069	0.117*	0.50
C6	0.0701 (8)	0.8278 (11)	0.5471 (5)	0.091 (3)	0.50
H6A	0.0222	0.7764	0.5051	0.109*	0.50
H6B	0.1054	0.9075	0.5146	0.109*	0.50
C1'	0.1883 (7)	0.7287 (12)	0.6020 (6)	0.121 (6)	0.50
H1B	0.2530	0.7692	0.6321	0.145*	0.50
C2'	0.1393 (7)	0.6133 (12)	0.6672 (7)	0.101 (4)	0.50
H2C	0.1891	0.5312	0.6747	0.121*	0.50
H2D	0.1277	0.6576	0.7267	0.121*	0.50
C3'	0.0326 (8)	0.5580 (10)	0.6290 (9)	0.149 (6)	0.50
H3C	0.0025	0.4846	0.6699	0.179*	0.50
H3D	0.0448	0.5112	0.5704	0.179*	0.50
C4'	−0.0484 (6)	0.6857 (12)	0.6172 (9)	0.146 (5)	0.50
H4C	−0.0635	0.7300	0.6760	0.175*	0.50
H4D	−0.1159	0.6487	0.5917	0.175*	0.50
C5'	0.0006 (8)	0.8018 (12)	0.5529 (10)	0.150 (5)	0.50
H5C	0.0107	0.7586	0.4930	0.180*	0.50
H5D	−0.0492	0.8842	0.5467	0.180*	0.50
C6'	0.1077 (7)	0.8568 (10)	0.5890 (8)	0.106 (3)	0.50
H6C	0.0968	0.9063	0.6469	0.127*	0.50
H6D	0.1376	0.9281	0.5466	0.127*	0.50
C7	0.3244 (3)	0.6318 (3)	0.5079 (2)	0.0695 (8)
C8	0.3013 (3)	0.5664 (4)	0.3450 (2)	0.0755 (9)
C9	0.3604 (3)	0.5071 (4)	0.2637 (2)	0.0701 (8)
C10	0.3015 (3)	0.4227 (4)	0.2026 (2)	0.0757 (9)
H10	0.2288	0.4025	0.2131	0.091*
C11	0.3514 (3)	0.3689 (3)	0.1262 (2)	0.0753 (9)
C12	0.4585 (3)	0.3965 (3)	0.1073 (2)	0.0751 (9)
H12	0.4916	0.3582	0.0556	0.090*
C13	0.5142 (3)	0.4833 (3)	0.1684 (2)	0.0700 (8)
C14	0.4681 (3)	0.5400 (3)	0.2462 (2)	0.0691 (8)
H14	0.5082	0.5988	0.2860	0.083*

	U11	U22	U33	U12	U13	U23
S1	0.0966 (7)	0.1080 (8)	0.0695 (5)	0.0228 (6)	0.0037 (5)	−0.0177 (5)
O1	0.0737 (17)	0.145 (3)	0.1016 (18)	0.0229 (17)	−0.0108 (14)	−0.0007 (17)
O2	0.127 (3)	0.161 (3)	0.135 (3)	−0.052 (3)	−0.019 (2)	−0.027 (2)
O3	0.144 (3)	0.126 (3)	0.136 (3)	−0.003 (2)	−0.014 (2)	−0.066 (2)
O4	0.117 (2)	0.121 (2)	0.134 (2)	−0.0209 (19)	0.045 (2)	−0.043 (2)
O5	0.108 (2)	0.131 (2)	0.1037 (19)	−0.0431 (19)	0.0195 (17)	−0.0334 (18)
N1	0.0751 (18)	0.095 (2)	0.0897 (19)	0.0212 (16)	0.0215 (15)	0.0104 (16)
N2	0.0680 (15)	0.0767 (16)	0.0620 (14)	0.0098 (13)	0.0057 (12)	0.0030 (12)
N3	0.111 (3)	0.080 (2)	0.098 (2)	−0.012 (2)	−0.019 (2)	−0.0087 (18)
N4	0.102 (2)	0.086 (2)	0.0843 (19)	−0.0157 (19)	0.0192 (18)	−0.0099 (17)
C1	0.058 (5)	0.071 (6)	0.093 (5)	0.015 (4)	0.026 (4)	0.001 (4)
C2	0.097 (8)	0.077 (5)	0.078 (6)	0.007 (6)	0.011 (6)	−0.005 (5)
C3	0.115 (6)	0.100 (5)	0.069 (4)	−0.024 (5)	0.029 (4)	−0.017 (4)
C4	0.085 (5)	0.131 (8)	0.103 (6)	−0.007 (5)	0.020 (5)	−0.071 (6)
C5	0.085 (5)	0.095 (6)	0.114 (6)	0.018 (4)	0.022 (5)	−0.037 (5)
C6	0.070 (6)	0.099 (7)	0.103 (7)	0.023 (6)	−0.007 (5)	−0.006 (5)
C1'	0.088 (8)	0.119 (11)	0.157 (11)	0.041 (7)	0.051 (7)	0.032 (8)
C2'	0.087 (7)	0.128 (8)	0.087 (7)	−0.004 (6)	0.009 (5)	0.007 (6)
C3'	0.106 (8)	0.160 (12)	0.180 (12)	−0.038 (8)	−0.043 (8)	0.069 (10)
C4'	0.071 (5)	0.162 (10)	0.203 (13)	−0.001 (7)	−0.014 (7)	0.077 (10)
C5'	0.099 (8)	0.124 (9)	0.227 (15)	−0.010 (8)	−0.057 (9)	0.049 (10)
C6'	0.090 (7)	0.092 (7)	0.136 (9)	0.007 (5)	−0.004 (6)	0.000 (6)
C7	0.076 (2)	0.0639 (18)	0.0689 (18)	0.0095 (16)	0.0127 (16)	0.0061 (14)
C8	0.077 (2)	0.076 (2)	0.073 (2)	0.0066 (18)	−0.0027 (17)	0.0090 (16)
C9	0.083 (2)	0.0665 (18)	0.0607 (16)	0.0028 (17)	−0.0076 (15)	0.0113 (15)
C10	0.078 (2)	0.0711 (19)	0.077 (2)	−0.0019 (17)	−0.0112 (17)	0.0110 (17)
C11	0.096 (3)	0.0574 (18)	0.0726 (19)	−0.0027 (18)	−0.0183 (18)	0.0045 (15)
C12	0.102 (3)	0.0593 (18)	0.0641 (18)	0.0011 (18)	−0.0014 (18)	0.0019 (15)
C13	0.083 (2)	0.0607 (17)	0.0665 (18)	−0.0054 (16)	−0.0008 (16)	0.0053 (15)
C14	0.084 (2)	0.0631 (18)	0.0598 (16)	−0.0052 (16)	−0.0035 (16)	0.0051 (14)

S1—C7	1.659 (4)	C5—H5B	0.9700
O1—C8	1.215 (4)	C6—H6A	0.9700
O2—N3	1.210 (5)	C6—H6B	0.9700
O3—N3	1.200 (4)	C1'—C6'	1.539 (8)
O4—N4	1.221 (4)	C1'—C2'	1.542 (8)
O5—N4	1.213 (4)	C1'—H1B	0.9800
N1—C7	1.305 (4)	C2'—C3'	1.512 (8)
N1—C1	1.452 (6)	C2'—H2C	0.9700
N1—C1'	1.481 (8)	C2'—H2D	0.9700
N1—H1	0.8800	C3'—C4'	1.537 (9)
N1—H1'	0.8800	C3'—H3C	0.9700
N2—C8	1.358 (4)	C3'—H3D	0.9700
N2—C7	1.402 (4)	C4'—C5'	1.537 (8)
N2—H2	0.8800	C4'—H4C	0.9700
N3—C11	1.474 (5)	C4'—H4D	0.9700
N4—C13	1.471 (5)	C5'—C6'	1.505 (8)
C1—C6	1.524 (8)	C5'—H5C	0.9700
C1—C2	1.527 (8)	C5'—H5D	0.9700
C1—H1A	0.9800	C6'—H6C	0.9700
C2—C3	1.547 (7)	C6'—H6D	0.9700
C2—H2A	0.9700	C8—C9	1.501 (5)
C2—H2B	0.9700	C9—C10	1.380 (5)
C3—C4	1.511 (8)	C9—C14	1.388 (4)
C3—H3A	0.9700	C10—C11	1.370 (5)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.507 (7)	C11—C12	1.375 (5)
C4—H4A	0.9700	C12—C13	1.372 (5)
C4—H4B	0.9700	C12—H12	0.9300
C5—C6	1.552 (8)	C13—C14	1.376 (4)
C5—H5A	0.9700	C14—H14	0.9300
C7—N1—C1	133.3 (5)	C2'—C1'—H1B	107.3
C7—N1—C1'	114.9 (5)	C3'—C2'—C1'	109.8 (7)
C7—N1—H1	113.3	C3'—C2'—H2C	109.7
C1—N1—H1	113.3	C1'—C2'—H2C	109.7
C7—N1—H1'	122.6	C3'—C2'—H2D	109.7
C1'—N1—H1'	122.6	C1'—C2'—H2D	109.7
C8—N2—C7	127.2 (3)	H2C—C2'—H2D	108.2
C8—N2—H2	116.4	C2'—C3'—C4'	110.9 (7)
C7—N2—H2	116.4	C2'—C3'—H3C	109.5
O3—N3—O2	123.5 (4)	C4'—C3'—H3C	109.5
O3—N3—C11	119.1 (4)	C2'—C3'—H3D	109.5
O2—N3—C11	117.4 (4)	C4'—C3'—H3D	109.5
O5—N4—O4	124.5 (3)	H3C—C3'—H3D	108.1
O5—N4—C13	117.9 (3)	C3'—C4'—C5'	109.0 (7)
O4—N4—C13	117.6 (3)	C3'—C4'—H4C	109.9
N1—C1—C6	108.7 (6)	C5'—C4'—H4C	109.9
N1—C1—C2	109.8 (6)	C3'—C4'—H4D	109.9
C6—C1—C2	110.6 (7)	C5'—C4'—H4D	109.9
N1—C1—H1A	109.3	H4C—C4'—H4D	108.3
C6—C1—H1A	109.3	C6'—C5'—C4'	111.1 (7)
C2—C1—H1A	109.3	C6'—C5'—H5C	109.4
C1—C2—C3	107.2 (5)	C4'—C5'—H5C	109.4
C1—C2—H2A	110.3	C6'—C5'—H5D	109.4
C3—C2—H2A	110.3	C4'—C5'—H5D	109.4
C1—C2—H2B	110.3	H5C—C5'—H5D	108.0
C3—C2—H2B	110.3	C5'—C6'—C1'	111.1 (7)
H2A—C2—H2B	108.5	C5'—C6'—H6C	109.4
C4—C3—C2	110.7 (5)	C1'—C6'—H6C	109.4
C4—C3—H3A	109.5	C5'—C6'—H6D	109.4
C2—C3—H3A	109.5	C1'—C6'—H6D	109.4
C4—C3—H3B	109.5	H6C—C6'—H6D	108.0
C2—C3—H3B	109.5	N1—C7—N2	116.4 (3)
H3A—C3—H3B	108.1	N1—C7—S1	125.6 (3)
C5—C4—C3	112.0 (6)	N2—C7—S1	118.0 (2)
C5—C4—H4A	109.2	O1—C8—N2	124.1 (3)
C3—C4—H4A	109.2	O1—C8—C9	119.7 (3)
C5—C4—H4B	109.2	N2—C8—C9	116.2 (3)
C3—C4—H4B	109.2	C10—C9—C14	120.0 (3)
H4A—C4—H4B	107.9	C10—C9—C8	117.2 (3)
C4—C5—C6	109.7 (6)	C14—C9—C8	122.8 (3)
C4—C5—H5A	109.7	C11—C10—C9	119.2 (3)
C6—C5—H5A	109.7	C11—C10—H10	120.4
C4—C5—H5B	109.7	C9—C10—H10	120.4
C6—C5—H5B	109.7	C10—C11—C12	122.6 (3)
H5A—C5—H5B	108.2	C10—C11—N3	118.8 (4)
C1—C6—C5	107.1 (5)	C12—C11—N3	118.6 (3)
C1—C6—H6A	110.3	C13—C12—C11	116.7 (3)
C5—C6—H6A	110.3	C13—C12—H12	121.6
C1—C6—H6B	110.3	C11—C12—H12	121.6
C5—C6—H6B	110.3	C12—C13—C14	123.1 (3)
H6A—C6—H6B	108.5	C12—C13—N4	119.0 (3)
N1—C1'—C6'	110.4 (8)	C14—C13—N4	117.9 (3)
N1—C1'—C2'	115.0 (8)	C13—C14—C9	118.3 (3)
C6'—C1'—C2'	109.4 (6)	C13—C14—H14	120.8
N1—C1'—H1B	107.3	C9—C14—H14	120.8
C6'—C1'—H1B	107.3
C7—N1—C1—C6	147.6 (6)	C8—N2—C7—N1	−0.6 (5)
C1'—N1—C1—C6	134 (2)	C8—N2—C7—S1	−179.3 (3)
C7—N1—C1—C2	−91.4 (9)	C7—N2—C8—O1	0.6 (6)
C1'—N1—C1—C2	−105 (2)	C7—N2—C8—C9	−179.1 (3)
N1—C1—C2—C3	177.3 (7)	O1—C8—C9—C10	−31.7 (5)
C6—C1—C2—C3	−62.8 (10)	N2—C8—C9—C10	148.0 (3)
C1—C2—C3—C4	57.7 (10)	O1—C8—C9—C14	145.0 (4)
C2—C3—C4—C5	−56.9 (9)	N2—C8—C9—C14	−35.3 (4)
C3—C4—C5—C6	57.5 (9)	C14—C9—C10—C11	1.7 (5)
N1—C1—C6—C5	−175.5 (8)	C8—C9—C10—C11	178.6 (3)
C2—C1—C6—C5	63.9 (10)	C9—C10—C11—C12	−0.5 (5)
C4—C5—C6—C1	−59.6 (10)	C9—C10—C11—N3	179.1 (3)
C7—N1—C1'—C6'	141.7 (5)	O3—N3—C11—C10	179.4 (4)
C1—N1—C1'—C6'	−49.4 (18)	O2—N3—C11—C10	1.2 (5)
C7—N1—C1'—C2'	−94.0 (7)	O3—N3—C11—C12	−1.1 (5)
C1—N1—C1'—C2'	74.9 (19)	O2—N3—C11—C12	−179.3 (4)
N1—C1'—C2'—C3'	−66.7 (10)	C10—C11—C12—C13	−0.8 (5)
C6'—C1'—C2'—C3'	58.1 (11)	N3—C11—C12—C13	179.6 (3)
C1'—C2'—C3'—C4'	−59.8 (12)	C11—C12—C13—C14	0.9 (5)
C2'—C3'—C4'—C5'	58.6 (13)	C11—C12—C13—N4	−179.4 (3)
C3'—C4'—C5'—C6'	−57.3 (14)	O5—N4—C13—C12	172.3 (3)
C4'—C5'—C6'—C1'	57.8 (13)	O4—N4—C13—C12	−7.0 (5)
N1—C1'—C6'—C5'	69.9 (10)	O5—N4—C13—C14	−8.0 (5)
C2'—C1'—C6'—C5'	−57.5 (11)	O4—N4—C13—C14	172.6 (3)
C1—N1—C7—N2	177.5 (5)	C12—C13—C14—C9	0.3 (5)
C1'—N1—C7—N2	−177.5 (5)	N4—C13—C14—C9	−179.4 (3)
C1—N1—C7—S1	−3.8 (7)	C10—C9—C14—C13	−1.6 (5)
C1'—N1—C7—S1	1.1 (6)	C8—C9—C14—C13	−178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.89	2.639 (4)	142
N1—H1'···O1	0.88	1.99	2.639 (4)	130
N2—H2···S1i	0.88	2.65	3.449 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.88	1.89	2.639 (4)	142
N1—H1′⋯O1	0.88	1.99	2.639 (4)	130
N2—H2⋯S1i	0.88	2.65	3.449 (3)	152

Symmetry code: (i) .