N-(4-Bromo-benzo-yl)-N,N'-dicyclo-hexyl-urea.

In the title compound, C(20)H(27)BrN(2)O(2), mol-ecules are linked into one-dimensional chains through (amide)N-H⋯O=C(amide) inter-molecular hydrogen bonds.

Related literature

For related literature, see: Bohne et al. (2005 ▶); Bondy et al. (2004 ▶); Bruker (2000 ▶); Ślebioda (1995 ▶). For literature on related crystal structures, see: Ball et al. (1990 ▶); Chérioux et al. (2002 ▶); Gallagher et al. (1999 ▶); Govindasamy & Subramanian (1997 ▶); Toniolo et al. (1990 ▶); Wu et al. (2006 ▶).

Experimental

Crystal data

C20H27BrN2O2

M = 407.35

Monoclinic,

a = 13.501 (2) Å

b = 9.5621 (10) Å

c = 16.306 (2) Å

β = 114.443 (6)°

V = 1916.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.16 mm−1

T = 113 (2) K

0.38 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (REQABS; Jacobson, 1998 ▶) T min = 0.484, T max = 0.739

17461 measured reflections

4526 independent reflections

3651 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.078

S = 1.06

4526 reflections

231 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Jacobson, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064756/pk2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064756/pk2071Isup2.hkl

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

C20H27BrN2O2	F000 = 848
Mr = 407.35	Dx = 1.412 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4164 reflections
a = 13.501 (2) Å	θ = 1.7–27.9º
b = 9.5621 (10) Å	µ = 2.16 mm−1
c = 16.306 (2) Å	T = 113 (2) K
β = 114.443 (6)º	Prism, colorless
V = 1916.3 (4) Å3	0.38 × 0.16 × 0.14 mm
Z = 4

Rigaku Saturn CCD diffractometer	4526 independent reflections
Radiation source: Rotating anode	3651 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.044
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 1.7º
ω scans	h = −17→17
Absorption correction: multi-scan(REQABS; Jacobson, 1998)	k = −12→12
Tmin = 0.484, Tmax = 0.739	l = −21→20
17461 measured reflections

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0381P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
4526 reflections	Δρmax = 0.45 e Å−3
231 parameters	Δρmin = −0.44 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 > 2σ(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
Br1	0.615319 (17)	0.39160 (2)	1.092233 (14)	0.03591 (9)
N1	0.86443 (11)	0.53780 (15)	0.80694 (9)	0.0172 (3)
N2	0.67615 (11)	0.53992 (16)	0.73657 (10)	0.0180 (3)
O1	0.95485 (9)	0.68643 (13)	0.92419 (8)	0.0226 (3)
O2	0.76754 (10)	0.34042 (13)	0.73292 (8)	0.0234 (3)
C1	0.69576 (14)	0.4583 (2)	1.02792 (12)	0.0233 (4)
C2	0.69278 (15)	0.5987 (2)	1.00682 (13)	0.0267 (4)
H2	0.6508	0.6624	1.0240	0.032*
C3	0.75215 (15)	0.6450 (2)	0.96011 (13)	0.0246 (4)
H3	0.7519	0.7414	0.9460	0.029*
C4	0.81235 (13)	0.55047 (19)	0.93373 (11)	0.0176 (4)
C5	0.81418 (14)	0.40955 (19)	0.95585 (12)	0.0205 (4)
H5	0.8551	0.3450	0.9381	0.025*
C6	0.75616 (14)	0.3634 (2)	1.00396 (12)	0.0223 (4)
H6	0.7581	0.2677	1.0202	0.027*
C7	0.88221 (13)	0.60122 (18)	0.88777 (12)	0.0179 (4)
C8	0.94261 (14)	0.55666 (19)	0.76516 (12)	0.0199 (4)
H8	0.9907	0.6372	0.7963	0.024*
C9	1.01578 (15)	0.4287 (2)	0.77921 (14)	0.0259 (4)
H9A	0.9702	0.3452	0.7531	0.031*
H9B	1.0574	0.4122	0.8445	0.031*
C10	1.09504 (16)	0.4493 (2)	0.73482 (14)	0.0331 (5)
H10A	1.1462	0.5260	0.7656	0.040*
H10B	1.1380	0.3628	0.7415	0.040*
C11	1.03445 (17)	0.4842 (2)	0.63510 (14)	0.0361 (5)
H11A	0.9878	0.4043	0.6032	0.043*
H11B	1.0874	0.5007	0.6086	0.043*
C12	0.96424 (17)	0.6143 (2)	0.62288 (14)	0.0341 (5)
H12A	0.9238	0.6338	0.5578	0.041*
H12B	1.0117	0.6956	0.6507	0.041*
C13	0.88348 (15)	0.5955 (2)	0.66570 (13)	0.0268 (4)
H13A	0.8424	0.6834	0.6599	0.032*
H13B	0.8308	0.5210	0.6335	0.032*
C14	0.76568 (14)	0.4618 (2)	0.75616 (11)	0.0180 (4)
C15	0.56540 (13)	0.48403 (19)	0.69141 (12)	0.0180 (4)
H15	0.5702	0.3853	0.6733	0.022*
C16	0.50196 (16)	0.5682 (2)	0.60708 (13)	0.0313 (5)
H16A	0.5392	0.5639	0.5661	0.038*
H16B	0.4987	0.6673	0.6233	0.038*
C17	0.38642 (16)	0.5099 (2)	0.55931 (15)	0.0399 (6)
H17A	0.3452	0.5668	0.5051	0.048*
H17B	0.3899	0.4128	0.5396	0.048*
C18	0.32755 (16)	0.5114 (2)	0.62076 (18)	0.0509 (7)
H18A	0.3189	0.6091	0.6368	0.061*
H18B	0.2542	0.4702	0.5890	0.061*
C19	0.39104 (16)	0.4288 (2)	0.70547 (16)	0.0403 (6)
H19A	0.3934	0.3293	0.6896	0.048*
H19B	0.3535	0.4344	0.7462	0.048*
C20	0.50804 (16)	0.4842 (2)	0.75473 (14)	0.0296 (5)
H20A	0.5063	0.5805	0.7764	0.036*
H20B	0.5487	0.4245	0.8077	0.036*
H2A	0.6851 (15)	0.6326 (10)	0.7456 (12)	0.023 (5)*

	U11	U22	U33	U12	U13	U23
Br1	0.03720 (13)	0.04748 (17)	0.03229 (13)	−0.01255 (10)	0.02362 (10)	−0.00410 (10)
N1	0.0147 (7)	0.0164 (8)	0.0206 (8)	−0.0024 (6)	0.0075 (6)	−0.0004 (6)
N2	0.0154 (7)	0.0136 (9)	0.0238 (8)	−0.0013 (6)	0.0070 (6)	−0.0024 (7)
O1	0.0190 (6)	0.0223 (7)	0.0233 (7)	−0.0054 (6)	0.0056 (5)	−0.0015 (6)
O2	0.0213 (6)	0.0140 (7)	0.0322 (8)	0.0006 (5)	0.0084 (6)	−0.0032 (6)
C1	0.0217 (9)	0.0320 (12)	0.0174 (9)	−0.0071 (8)	0.0093 (8)	−0.0027 (9)
C2	0.0257 (10)	0.0269 (12)	0.0320 (11)	−0.0048 (8)	0.0165 (9)	−0.0102 (9)
C3	0.0259 (10)	0.0198 (11)	0.0297 (10)	−0.0034 (8)	0.0132 (8)	−0.0030 (9)
C4	0.0141 (8)	0.0212 (10)	0.0151 (8)	−0.0030 (7)	0.0037 (7)	−0.0019 (8)
C5	0.0164 (8)	0.0239 (11)	0.0194 (9)	0.0003 (8)	0.0057 (7)	0.0005 (8)
C6	0.0218 (9)	0.0244 (11)	0.0191 (9)	−0.0012 (8)	0.0067 (8)	0.0040 (8)
C7	0.0145 (8)	0.0166 (10)	0.0198 (9)	0.0026 (7)	0.0045 (7)	0.0037 (8)
C8	0.0171 (9)	0.0203 (10)	0.0252 (10)	−0.0019 (7)	0.0117 (8)	−0.0001 (8)
C9	0.0188 (9)	0.0267 (11)	0.0306 (11)	0.0044 (8)	0.0087 (8)	0.0030 (9)
C10	0.0221 (10)	0.0396 (13)	0.0405 (12)	0.0087 (9)	0.0159 (9)	0.0002 (11)
C11	0.0321 (11)	0.0479 (14)	0.0351 (12)	0.0045 (10)	0.0209 (10)	−0.0050 (11)
C12	0.0348 (11)	0.0463 (14)	0.0290 (11)	0.0046 (10)	0.0210 (10)	0.0048 (10)
C13	0.0245 (10)	0.0332 (12)	0.0264 (10)	0.0058 (9)	0.0144 (8)	0.0065 (9)
C14	0.0176 (9)	0.0184 (10)	0.0179 (9)	−0.0019 (7)	0.0074 (7)	0.0019 (8)
C15	0.0141 (8)	0.0162 (10)	0.0219 (9)	−0.0008 (7)	0.0055 (7)	−0.0019 (8)
C16	0.0314 (11)	0.0229 (11)	0.0270 (11)	−0.0040 (9)	−0.0006 (9)	0.0023 (9)
C17	0.0268 (11)	0.0284 (13)	0.0408 (13)	0.0028 (9)	−0.0096 (10)	0.0015 (10)
C18	0.0150 (10)	0.0391 (14)	0.0841 (19)	0.0034 (10)	0.0060 (12)	−0.0301 (14)
C19	0.0277 (11)	0.0528 (15)	0.0518 (15)	−0.0179 (10)	0.0279 (11)	−0.0276 (12)
C20	0.0262 (10)	0.0367 (13)	0.0304 (11)	−0.0088 (9)	0.0163 (9)	−0.0101 (10)

Br1—C1	1.9048 (18)	C10—H10A	0.9900
N1—C7	1.379 (2)	C10—H10B	0.9900
N1—C14	1.441 (2)	C11—C12	1.526 (3)
N1—C8	1.485 (2)	C11—H11A	0.9900
N2—C14	1.342 (2)	C11—H11B	0.9900
N2—C15	1.467 (2)	C12—C13	1.529 (2)
N2—H2A	0.898 (9)	C12—H12A	0.9900
O1—C7	1.223 (2)	C12—H12B	0.9900
O2—C14	1.225 (2)	C13—H13A	0.9900
C1—C6	1.380 (3)	C13—H13B	0.9900
C1—C2	1.382 (3)	C15—C16	1.516 (2)
C2—C3	1.387 (3)	C15—C20	1.526 (2)
C2—H2	0.9500	C15—H15	1.0000
C3—C4	1.397 (3)	C16—C17	1.531 (3)
C3—H3	0.9500	C16—H16A	0.9900
C4—C5	1.393 (3)	C16—H16B	0.9900
C4—C7	1.507 (2)	C17—C18	1.515 (3)
C5—C6	1.390 (2)	C17—H17A	0.9900
C5—H5	0.9500	C17—H17B	0.9900
C6—H6	0.9500	C18—C19	1.512 (3)
C8—C13	1.528 (2)	C18—H18A	0.9900
C8—C9	1.529 (3)	C18—H18B	0.9900
C8—H8	1.0000	C19—C20	1.540 (3)
C9—C10	1.532 (3)	C19—H19A	0.9900
C9—H9A	0.9900	C19—H19B	0.9900
C9—H9B	0.9900	C20—H20A	0.9900
C10—C11	1.524 (3)	C20—H20B	0.9900
C7—N1—C14	121.65 (14)	C11—C12—C13	111.49 (17)
C7—N1—C8	120.63 (14)	C11—C12—H12A	109.3
C14—N1—C8	117.50 (14)	C13—C12—H12A	109.3
C14—N2—C15	123.18 (15)	C11—C12—H12B	109.3
C14—N2—H2A	117.5 (12)	C13—C12—H12B	109.3
C15—N2—H2A	118.8 (12)	H12A—C12—H12B	108.0
C6—C1—C2	121.85 (17)	C8—C13—C12	110.81 (16)
C6—C1—Br1	118.30 (15)	C8—C13—H13A	109.5
C2—C1—Br1	119.85 (14)	C12—C13—H13A	109.5
C1—C2—C3	118.86 (18)	C8—C13—H13B	109.5
C1—C2—H2	120.6	C12—C13—H13B	109.5
C3—C2—H2	120.6	H13A—C13—H13B	108.1
C2—C3—C4	120.33 (18)	O2—C14—N2	125.83 (16)
C2—C3—H3	119.8	O2—C14—N1	121.54 (16)
C4—C3—H3	119.8	N2—C14—N1	112.60 (16)
C5—C4—C3	119.75 (17)	N2—C15—C16	109.75 (14)
C5—C4—C7	119.52 (16)	N2—C15—C20	110.93 (14)
C3—C4—C7	120.56 (17)	C16—C15—C20	111.03 (16)
C6—C5—C4	119.98 (17)	N2—C15—H15	108.3
C6—C5—H5	120.0	C16—C15—H15	108.3
C4—C5—H5	120.0	C20—C15—H15	108.3
C1—C6—C5	119.22 (18)	C15—C16—C17	110.02 (16)
C1—C6—H6	120.4	C15—C16—H16A	109.7
C5—C6—H6	120.4	C17—C16—H16A	109.7
O1—C7—N1	122.99 (16)	C15—C16—H16B	109.7
O1—C7—C4	120.93 (16)	C17—C16—H16B	109.7
N1—C7—C4	115.88 (15)	H16A—C16—H16B	108.2
N1—C8—C13	110.98 (14)	C18—C17—C16	111.28 (18)
N1—C8—C9	111.83 (15)	C18—C17—H17A	109.4
C13—C8—C9	112.02 (16)	C16—C17—H17A	109.4
N1—C8—H8	107.2	C18—C17—H17B	109.4
C13—C8—H8	107.2	C16—C17—H17B	109.4
C9—C8—H8	107.2	H17A—C17—H17B	108.0
C8—C9—C10	111.13 (16)	C19—C18—C17	110.18 (17)
C8—C9—H9A	109.4	C19—C18—H18A	109.6
C10—C9—H9A	109.4	C17—C18—H18A	109.6
C8—C9—H9B	109.4	C19—C18—H18B	109.6
C10—C9—H9B	109.4	C17—C18—H18B	109.6
H9A—C9—H9B	108.0	H18A—C18—H18B	108.1
C11—C10—C9	111.13 (16)	C18—C19—C20	111.59 (18)
C11—C10—H10A	109.4	C18—C19—H19A	109.3
C9—C10—H10A	109.4	C20—C19—H19A	109.3
C11—C10—H10B	109.4	C18—C19—H19B	109.3
C9—C10—H10B	109.4	C20—C19—H19B	109.3
H10A—C10—H10B	108.0	H19A—C19—H19B	108.0
C10—C11—C12	110.37 (17)	C15—C20—C19	110.18 (16)
C10—C11—H11A	109.6	C15—C20—H20A	109.6
C12—C11—H11A	109.6	C19—C20—H20A	109.6
C10—C11—H11B	109.6	C15—C20—H20B	109.6
C12—C11—H11B	109.6	C19—C20—H20B	109.6
H11A—C11—H11B	108.1	H20A—C20—H20B	108.1
C6—C1—C2—C3	0.1 (3)	C13—C8—C9—C10	54.1 (2)
Br1—C1—C2—C3	179.88 (14)	C8—C9—C10—C11	−55.5 (2)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	57.0 (2)
C2—C3—C4—C5	−1.1 (3)	C10—C11—C12—C13	−57.3 (2)
C2—C3—C4—C7	−176.41 (17)	N1—C8—C13—C12	−179.79 (15)
C3—C4—C5—C6	0.0 (3)	C9—C8—C13—C12	−54.0 (2)
C7—C4—C5—C6	175.39 (15)	C11—C12—C13—C8	55.7 (2)
C2—C1—C6—C5	−1.2 (3)	C15—N2—C14—O2	6.6 (3)
Br1—C1—C6—C5	179.06 (13)	C15—N2—C14—N1	−175.26 (14)
C4—C5—C6—C1	1.1 (3)	C7—N1—C14—O2	−125.42 (18)
C14—N1—C7—O1	−166.44 (16)	C8—N1—C14—O2	60.0 (2)
C8—N1—C7—O1	7.9 (2)	C7—N1—C14—N2	56.4 (2)
C14—N1—C7—C4	18.6 (2)	C8—N1—C14—N2	−118.19 (17)
C8—N1—C7—C4	−167.06 (14)	C14—N2—C15—C16	−124.11 (18)
C5—C4—C7—O1	−117.18 (19)	C14—N2—C15—C20	112.83 (19)
C3—C4—C7—O1	58.1 (2)	N2—C15—C16—C17	179.70 (16)
C5—C4—C7—N1	57.9 (2)	C20—C15—C16—C17	−57.3 (2)
C3—C4—C7—N1	−126.75 (18)	C15—C16—C17—C18	57.9 (2)
C7—N1—C8—C13	−131.60 (17)	C16—C17—C18—C19	−57.3 (2)
C14—N1—C8—C13	43.0 (2)	C17—C18—C19—C20	56.3 (2)
C7—N1—C8—C9	102.52 (19)	N2—C15—C20—C19	178.56 (17)
C14—N1—C8—C9	−82.87 (19)	C16—C15—C20—C19	56.2 (2)
N1—C8—C9—C10	179.38 (15)	C18—C19—C20—C15	−55.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.898 (10)	2.072 (11)	2.961 (2)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.898 (10)	2.072 (11)	2.961 (2)	170 (2)

Symmetry code: (i) .