1,3-Dicyclo-hexyl-1-(4-nitro-benzo-yl)urea.

In the title compound, C(20)H(27)N(3)O(4), both cyclo-hexane rings adopt chair conformations. The benzene ring and the amide group are oriented at a dihedral angle of 62.1 (2)°. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010], which contain R(2) (2)(12) ring motifs.

Related literature

For the biological activity of benzoyl­urea and N-aroylurea derivatives, see: Song et al. (2008 ▶, 2009 ▶); Amornraksa et al. (2009 ▶). For related N-benzoyl-N,N′-dicyclo­hexyl­urea structures, see: Orea Flores et al. (2006 ▶); Wang & Peng (2008 ▶).

Experimental

Crystal data

C20H27N3O4

M = 373.45

Monoclinic,

a = 25.294 (2) Å

b = 9.5757 (7) Å

c = 16.6943 (14) Å

β = 105.140 (2)°

V = 3903.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 1999 ▶) T min = 0.836, T max = 0.982

22623 measured reflections

5012 independent reflections

3152 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.138

S = 1.02

5012 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016107/hb5432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016107/hb5432Isup2.hkl

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

C20H27N3O4	F(000) = 1600
Mr = 373.45	Dx = 1.271 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4827 reflections
a = 25.294 (2) Å	θ = 2.5–23.4°
b = 9.5757 (7) Å	µ = 0.09 mm−1
c = 16.6943 (14) Å	T = 292 K
β = 105.140 (2)°	Block, pale-yellow
V = 3903.1 (5) Å3	0.25 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	5012 independent reflections
Radiation source: fine-focus sealed tube	3152 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scan	θmax = 28.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −34→34
Tmin = 0.836, Tmax = 0.982	k = −12→12
22623 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0549P)2 + 1.482P] where P = (Fo2 + 2Fc2)/3
5012 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.14 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
C1	0.18614 (6)	0.20858 (14)	0.12793 (9)	0.0419 (3)
H1	0.1969	0.1116	0.1220	0.050*
C2	0.12619 (7)	0.2094 (2)	0.12851 (11)	0.0651 (5)
H2A	0.1151	0.3039	0.1374	0.078*
H2B	0.1212	0.1517	0.1738	0.078*
C3	0.09045 (7)	0.1538 (3)	0.04623 (12)	0.0795 (6)
H3A	0.0991	0.0563	0.0402	0.095*
H3B	0.0522	0.1596	0.0466	0.095*
C4	0.09915 (8)	0.2346 (2)	−0.02572 (12)	0.0786 (6)
H4A	0.0870	0.3301	−0.0228	0.094*
H4B	0.0775	0.1938	−0.0770	0.094*
C5	0.15886 (8)	0.2338 (2)	−0.02557 (11)	0.0713 (5)
H5A	0.1638	0.2902	−0.0713	0.086*
H5B	0.1700	0.1391	−0.0337	0.086*
C6	0.19480 (8)	0.29061 (19)	0.05559 (10)	0.0603 (4)
H6A	0.2330	0.2850	0.0549	0.072*
H6B	0.1860	0.3880	0.0615	0.072*
C7	0.25502 (6)	0.18506 (14)	0.26110 (9)	0.0405 (3)
C8	0.34370 (6)	0.27308 (16)	0.35126 (10)	0.0511 (4)
H8	0.3545	0.3551	0.3869	0.061*
C9	0.36104 (7)	0.2997 (2)	0.27233 (12)	0.0665 (5)
H9A	0.3436	0.3841	0.2460	0.080*
H9B	0.3492	0.2226	0.2341	0.080*
C10	0.42312 (8)	0.3153 (3)	0.29111 (15)	0.0843 (6)
H10A	0.4335	0.3269	0.2396	0.101*
H10B	0.4345	0.3982	0.3246	0.101*
C11	0.45178 (8)	0.1898 (3)	0.33654 (17)	0.0955 (8)
H11A	0.4911	0.2037	0.3493	0.115*
H11B	0.4427	0.1081	0.3013	0.115*
C12	0.43525 (8)	0.1653 (3)	0.41589 (16)	0.1003 (8)
H12A	0.4471	0.2434	0.4532	0.120*
H12B	0.4531	0.0817	0.4428	0.120*
C13	0.37307 (7)	0.1487 (2)	0.39846 (13)	0.0748 (6)
H13A	0.3617	0.0644	0.3663	0.090*
H13B	0.3631	0.1393	0.4505	0.090*
C14	0.25633 (7)	0.32416 (15)	0.38509 (9)	0.0478 (4)
C15	0.19665 (6)	0.29435 (15)	0.37139 (9)	0.0462 (3)
C16	0.16036 (8)	0.40464 (17)	0.36337 (13)	0.0689 (5)
H16	0.1732	0.4956	0.3632	0.083*
C17	0.10558 (9)	0.3818 (2)	0.35558 (14)	0.0784 (6)
H17	0.0811	0.4560	0.3489	0.094*
C18	0.08794 (7)	0.2471 (2)	0.35787 (11)	0.0611 (4)
C19	0.12263 (7)	0.13583 (19)	0.36631 (11)	0.0599 (4)
H19	0.1095	0.0453	0.3674	0.072*
C20	0.17750 (7)	0.15920 (16)	0.37322 (10)	0.0521 (4)
H20	0.2016	0.0842	0.3791	0.063*
N1	0.22096 (5)	0.26334 (11)	0.20560 (7)	0.0426 (3)
H1A	0.2192	0.3510	0.2157	0.051*
N2	0.28337 (5)	0.25964 (12)	0.33451 (7)	0.0450 (3)
N3	0.02944 (8)	0.2204 (3)	0.35113 (12)	0.0897 (6)
O1	0.26427 (4)	0.06149 (10)	0.25260 (6)	0.0535 (3)
O2	0.27950 (5)	0.40101 (12)	0.44180 (7)	0.0660 (3)
O3	0.01453 (7)	0.1016 (3)	0.35244 (15)	0.1366 (8)
O4	−0.00053 (8)	0.3209 (3)	0.34562 (14)	0.1356 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0420 (8)	0.0411 (7)	0.0381 (8)	0.0019 (6)	0.0026 (6)	−0.0032 (6)
C2	0.0507 (10)	0.0968 (13)	0.0464 (10)	−0.0144 (9)	0.0101 (8)	−0.0049 (9)
C3	0.0459 (10)	0.1293 (18)	0.0568 (12)	−0.0117 (11)	0.0016 (8)	−0.0154 (12)
C4	0.0766 (14)	0.0941 (14)	0.0491 (11)	0.0318 (11)	−0.0122 (9)	−0.0059 (10)
C5	0.0924 (15)	0.0818 (12)	0.0369 (9)	−0.0024 (10)	0.0122 (9)	0.0032 (8)
C6	0.0683 (11)	0.0700 (10)	0.0455 (9)	−0.0077 (9)	0.0199 (8)	−0.0026 (8)
C7	0.0382 (7)	0.0415 (7)	0.0391 (8)	−0.0064 (6)	0.0052 (6)	−0.0011 (6)
C8	0.0437 (8)	0.0566 (8)	0.0464 (9)	−0.0144 (7)	0.0000 (7)	−0.0014 (7)
C9	0.0496 (10)	0.0845 (12)	0.0617 (11)	−0.0081 (9)	0.0079 (8)	0.0146 (9)
C10	0.0558 (12)	0.1142 (17)	0.0825 (15)	−0.0205 (11)	0.0175 (10)	0.0039 (13)
C11	0.0434 (11)	0.1230 (19)	0.109 (2)	−0.0024 (12)	−0.0003 (11)	−0.0069 (16)
C12	0.0559 (12)	0.1229 (19)	0.1000 (19)	−0.0031 (12)	−0.0191 (12)	0.0269 (15)
C13	0.0529 (11)	0.0874 (13)	0.0695 (13)	−0.0088 (9)	−0.0099 (9)	0.0259 (10)
C14	0.0610 (10)	0.0460 (7)	0.0338 (8)	−0.0122 (7)	0.0075 (7)	0.0021 (6)
C15	0.0602 (10)	0.0465 (8)	0.0329 (7)	−0.0064 (7)	0.0142 (7)	−0.0015 (6)
C16	0.0856 (14)	0.0472 (9)	0.0866 (14)	0.0010 (8)	0.0453 (11)	0.0004 (9)
C17	0.0818 (14)	0.0768 (13)	0.0902 (15)	0.0217 (10)	0.0466 (12)	0.0135 (11)
C18	0.0551 (10)	0.0856 (12)	0.0461 (10)	−0.0019 (9)	0.0198 (8)	0.0029 (8)
C19	0.0637 (11)	0.0619 (10)	0.0558 (10)	−0.0155 (8)	0.0188 (8)	−0.0026 (8)
C20	0.0582 (10)	0.0475 (8)	0.0505 (9)	−0.0055 (7)	0.0140 (7)	0.0030 (7)
N1	0.0465 (7)	0.0358 (6)	0.0405 (7)	0.0001 (5)	0.0020 (5)	−0.0033 (5)
N2	0.0433 (7)	0.0482 (7)	0.0384 (7)	−0.0094 (5)	0.0019 (5)	−0.0027 (5)
N3	0.0614 (12)	0.1421 (19)	0.0727 (12)	−0.0012 (13)	0.0299 (9)	0.0005 (12)
O1	0.0563 (7)	0.0400 (5)	0.0544 (7)	0.0028 (4)	−0.0028 (5)	−0.0017 (5)
O2	0.0836 (9)	0.0709 (7)	0.0413 (6)	−0.0298 (6)	0.0121 (6)	−0.0137 (5)
O3	0.0837 (12)	0.1591 (19)	0.183 (2)	−0.0499 (13)	0.0636 (13)	−0.0461 (16)
O4	0.0759 (11)	0.192 (2)	0.1528 (19)	0.0377 (13)	0.0546 (12)	0.0442 (16)

C1—N1	1.4613 (17)	C10—C11	1.503 (3)
C1—C6	1.504 (2)	C10—H10A	0.97
C1—C2	1.519 (2)	C10—H10B	0.97
C1—H1	0.98	C11—C12	1.508 (4)
C2—C3	1.530 (2)	C11—H11A	0.97
C2—H2A	0.97	C11—H11B	0.97
C2—H2B	0.97	C12—C13	1.531 (3)
C3—C4	1.493 (3)	C12—H12A	0.97
C3—H3A	0.97	C12—H12B	0.97
C3—H3B	0.97	C13—H13A	0.97
C4—C5	1.510 (3)	C13—H13B	0.97
C4—H4A	0.97	C14—O2	1.2213 (17)
C4—H4B	0.97	C14—N2	1.365 (2)
C5—C6	1.521 (2)	C14—C15	1.494 (2)
C5—H5A	0.97	C15—C16	1.383 (2)
C5—H5B	0.97	C15—C20	1.385 (2)
C6—H6A	0.97	C16—C17	1.375 (3)
C6—H6B	0.97	C16—H16	0.93
C7—O1	1.2217 (16)	C17—C18	1.369 (3)
C7—N1	1.3213 (18)	C17—H17	0.93
C7—N2	1.4377 (17)	C18—C19	1.364 (3)
C8—N2	1.4834 (19)	C18—N3	1.477 (3)
C8—C13	1.512 (2)	C19—C20	1.381 (2)
C8—C9	1.515 (2)	C19—H19	0.93
C8—H8	0.98	C20—H20	0.93
C9—C10	1.526 (2)	N1—H1A	0.86
C9—H9A	0.97	N3—O3	1.200 (3)
C9—H9B	0.97	N3—O4	1.213 (3)
N1—C1—C6	110.17 (12)	C9—C10—H10A	109.4
N1—C1—C2	111.33 (12)	C11—C10—H10B	109.4
C6—C1—C2	110.94 (13)	C9—C10—H10B	109.4
N1—C1—H1	108.1	H10A—C10—H10B	108.0
C6—C1—H1	108.1	C10—C11—C12	111.1 (2)
C2—C1—H1	108.1	C10—C11—H11A	109.4
C1—C2—C3	110.45 (15)	C12—C11—H11A	109.4
C1—C2—H2A	109.6	C10—C11—H11B	109.4
C3—C2—H2A	109.6	C12—C11—H11B	109.4
C1—C2—H2B	109.6	H11A—C11—H11B	108.0
C3—C2—H2B	109.6	C11—C12—C13	110.85 (17)
H2A—C2—H2B	108.1	C11—C12—H12A	109.5
C4—C3—C2	111.43 (17)	C13—C12—H12A	109.5
C4—C3—H3A	109.3	C11—C12—H12B	109.5
C2—C3—H3A	109.3	C13—C12—H12B	109.5
C4—C3—H3B	109.3	H12A—C12—H12B	108.1
C2—C3—H3B	109.3	C8—C13—C12	110.96 (16)
H3A—C3—H3B	108.0	C8—C13—H13A	109.4
C3—C4—C5	110.71 (15)	C12—C13—H13A	109.4
C3—C4—H4A	109.5	C8—C13—H13B	109.4
C5—C4—H4A	109.5	C12—C13—H13B	109.4
C3—C4—H4B	109.5	H13A—C13—H13B	108.0
C5—C4—H4B	109.5	O2—C14—N2	122.40 (15)
H4A—C4—H4B	108.1	O2—C14—C15	119.65 (15)
C4—C5—C6	111.38 (16)	N2—C14—C15	117.92 (12)
C4—C5—H5A	109.4	C16—C15—C20	119.26 (16)
C6—C5—H5A	109.4	C16—C15—C14	119.19 (14)
C4—C5—H5B	109.4	C20—C15—C14	121.35 (14)
C6—C5—H5B	109.4	C17—C16—C15	120.97 (16)
H5A—C5—H5B	108.0	C17—C16—H16	119.5
C1—C6—C5	110.49 (14)	C15—C16—H16	119.5
C1—C6—H6A	109.6	C18—C17—C16	118.38 (17)
C5—C6—H6A	109.6	C18—C17—H17	120.8
C1—C6—H6B	109.6	C16—C17—H17	120.8
C5—C6—H6B	109.6	C19—C18—C17	122.23 (17)
H6A—C6—H6B	108.1	C19—C18—N3	118.54 (18)
O1—C7—N1	125.28 (13)	C17—C18—N3	119.23 (19)
O1—C7—N2	120.81 (12)	C18—C19—C20	119.19 (16)
N1—C7—N2	113.87 (12)	C18—C19—H19	120.4
N2—C8—C13	111.79 (13)	C20—C19—H19	120.4
N2—C8—C9	111.58 (12)	C19—C20—C15	119.96 (16)
C13—C8—C9	111.80 (16)	C19—C20—H20	120.0
N2—C8—H8	107.1	C15—C20—H20	120.0
C13—C8—H8	107.1	C7—N1—C1	123.38 (11)
C9—C8—H8	107.1	C7—N1—H1A	118.3
C8—C9—C10	110.73 (15)	C1—N1—H1A	118.3
C8—C9—H9A	109.5	C14—N2—C7	122.22 (12)
C10—C9—H9A	109.5	C14—N2—C8	120.06 (12)
C8—C9—H9B	109.5	C7—N2—C8	117.59 (12)
C10—C9—H9B	109.5	O3—N3—O4	124.0 (2)
H9A—C9—H9B	108.1	O3—N3—C18	118.4 (2)
C11—C10—C9	111.10 (17)	O4—N3—C18	117.5 (2)
C11—C10—H10A	109.4
N1—C1—C2—C3	179.16 (15)	C17—C18—C19—C20	0.3 (3)
C6—C1—C2—C3	56.1 (2)	N3—C18—C19—C20	−179.59 (16)
C1—C2—C3—C4	−56.0 (2)	C18—C19—C20—C15	−0.1 (3)
C2—C3—C4—C5	56.1 (2)	C16—C15—C20—C19	0.6 (2)
C3—C4—C5—C6	−56.5 (2)	C14—C15—C20—C19	175.33 (14)
N1—C1—C6—C5	179.75 (13)	O1—C7—N1—C1	4.9 (2)
C2—C1—C6—C5	−56.51 (19)	N2—C7—N1—C1	−177.33 (12)
C4—C5—C6—C1	56.7 (2)	C6—C1—N1—C7	−126.35 (15)
N2—C8—C9—C10	179.16 (15)	C2—C1—N1—C7	110.13 (16)
C13—C8—C9—C10	−54.8 (2)	O2—C14—N2—C7	−171.22 (13)
C8—C9—C10—C11	55.8 (2)	C15—C14—N2—C7	10.96 (19)
C9—C10—C11—C12	−57.2 (3)	O2—C14—N2—C8	4.6 (2)
C10—C11—C12—C13	56.8 (3)	C15—C14—N2—C8	−173.21 (12)
N2—C8—C13—C12	−179.41 (17)	O1—C7—N2—C14	−121.45 (16)
C9—C8—C13—C12	54.7 (2)	N1—C7—N2—C14	60.66 (18)
C11—C12—C13—C8	−55.3 (3)	O1—C7—N2—C8	62.63 (18)
O2—C14—C15—C16	53.2 (2)	N1—C7—N2—C8	−115.27 (14)
N2—C14—C15—C16	−128.91 (16)	C13—C8—N2—C14	97.56 (18)
O2—C14—C15—C20	−121.55 (17)	C9—C8—N2—C14	−136.42 (15)
N2—C14—C15—C20	56.33 (19)	C13—C8—N2—C7	−86.42 (17)
C20—C15—C16—C17	−1.3 (3)	C9—C8—N2—C7	39.60 (18)
C14—C15—C16—C17	−176.15 (17)	C19—C18—N3—O3	−0.8 (3)
C15—C16—C17—C18	1.5 (3)	C17—C18—N3—O3	179.3 (2)
C16—C17—C18—C19	−1.0 (3)	C19—C18—N3—O4	178.3 (2)
C16—C17—C18—N3	178.90 (17)	C17—C18—N3—O4	−1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.10	2.9396 (15)	166
C1—H1···O2ii	0.98	2.43	3.3636 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.10	2.9396 (15)	166
C1—H1⋯O2ii	0.98	2.43	3.3636 (18)	160

Symmetry codes: (i) ; (ii) .