N-Benzoyl-N,N′-dicyclo­hexyl­urea

The title compound, C₂₀H₂₈N₂O₂, and N,N′-dicyclo­hexyl-N-(2-pyrazino­yl)urea are isostructural. Mol­ecules are linked into chains through (amide)N—H...O=C(amide) inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.092
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               1922
           Count of symmetry unique reflns         1923
           Completeness (_total/calc)             99.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

N-Benzoyl-N,N'-dicyclohexylurea

Crystal data

C20H28N2O2	F(000) = 712
Mr = 328.44	Dx = 1.153 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 75 reflections
a = 9.7060 (14) Å	θ = 4.6–12.0°
b = 12.0125 (12) Å	µ = 0.07 mm^−1
c = 16.2342 (13) Å	T = 296 K
V = 1892.8 (4) Å^3	Needle, colourless
Z = 4	0.60 × 0.28 × 0.14 mm

Data collection

Bruker P4 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube, FN4	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = −11→4
2θ/ω scans	k = −1→14
3205 measured reflections	l = −19→1
1922 independent reflections	3 standard reflections every 97 reflections
1411 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: see text
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.0188P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1922 reflections	Δρmax = 0.12 e Å^−3
222 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (11)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.0440 (2)	0.67467 (15)	0.57540 (11)	0.0499 (5)
C2	0.0286 (2)	0.72856 (19)	0.50901 (15)	0.0473 (6)
N3	−0.0494 (2)	0.79584 (19)	0.46457 (12)	0.0532 (5)
H3	−0.135 (3)	0.800 (2)	0.4748 (16)	0.063 (8)*
C4	−0.1063 (2)	0.7350 (2)	0.63678 (15)	0.0472 (6)
O5	−0.18775 (17)	0.69383 (15)	0.68546 (10)	0.0604 (5)
C6	−0.0622 (3)	0.8540 (2)	0.64531 (14)	0.0502 (6)
C7	−0.1573 (3)	0.9393 (2)	0.64149 (16)	0.0655 (8)
H7A	−0.2496	0.9234	0.6317	0.079*
C8	−0.1155 (4)	1.0483 (3)	0.65226 (19)	0.0796 (9)
H8A	−0.1793	1.1057	0.6470	0.095*
C9	0.0177 (4)	1.0724 (3)	0.67040 (18)	0.0825 (10)
H9A	0.0441	1.1458	0.6791	0.099*
C10	0.1130 (3)	0.9892 (3)	0.67587 (19)	0.0782 (9)
H10A	0.2039	1.0062	0.6889	0.094*
C11	0.0746 (3)	0.8789 (2)	0.66201 (17)	0.0652 (8)
H11A	0.1401	0.8225	0.6639	0.078*
C12	−0.0577 (3)	0.5513 (2)	0.57283 (15)	0.0546 (7)
H12A	−0.1301	0.5310	0.6121	0.066*
C13	0.0723 (3)	0.4941 (2)	0.60069 (19)	0.0736 (8)
H13A	0.0957	0.5187	0.6558	0.088*
H13B	0.1475	0.5142	0.5643	0.088*
C14	0.0534 (4)	0.3670 (2)	0.6003 (2)	0.0900 (10)
H14A	0.1398	0.3315	0.6148	0.108*
H14B	−0.0147	0.3464	0.6413	0.108*
C15	0.0075 (4)	0.3267 (2)	0.5169 (2)	0.0970 (11)
H15A	0.0801	0.3403	0.4771	0.116*
H15B	−0.0086	0.2471	0.5192	0.116*
C16	−0.1218 (4)	0.3841 (3)	0.4891 (2)	0.0902 (10)
H16A	−0.1971	0.3639	0.5254	0.108*
H16B	−0.1451	0.3593	0.4339	0.108*
C17	−0.1042 (3)	0.5114 (2)	0.48922 (18)	0.0723 (8)
H17A	−0.0366	0.5326	0.4481	0.087*
H17B	−0.1910	0.5465	0.4751	0.087*
O18	0.14985 (16)	0.70806 (15)	0.49562 (11)	0.0620 (5)
C19	0.0035 (3)	0.8651 (2)	0.39744 (15)	0.0526 (7)
H19A	0.1002	0.8452	0.3882	0.063*
C20	−0.0029 (3)	0.9881 (2)	0.41910 (16)	0.0668 (7)
H20A	0.0526	1.0021	0.4677	0.080*
H20B	−0.0973	1.0086	0.4316	0.080*
C21	0.0499 (4)	1.0593 (3)	0.34779 (18)	0.0853 (10)
H21A	0.0390	1.1374	0.3615	0.102*
H21B	0.1473	1.0450	0.3396	0.102*
C22	−0.0273 (4)	1.0343 (3)	0.26879 (18)	0.0849 (10)
H22A	−0.1228	1.0569	0.2748	0.102*
H22B	0.0125	1.0771	0.2241	0.102*
C23	−0.0214 (3)	0.9126 (3)	0.24792 (16)	0.0775 (9)
H23A	0.0730	0.8917	0.2360	0.093*
H23B	−0.0761	0.8986	0.1990	0.093*
C24	−0.0757 (3)	0.8417 (2)	0.31875 (15)	0.0640 (8)
H24A	−0.1726	0.8576	0.3274	0.077*
H24B	−0.0669	0.7635	0.3047	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0541 (12)	0.0466 (11)	0.0491 (11)	−0.0026 (10)	0.0054 (11)	0.0047 (10)
C2	0.0468 (14)	0.0455 (13)	0.0496 (13)	−0.0004 (12)	0.0033 (13)	−0.0003 (12)
N3	0.0417 (12)	0.0630 (13)	0.0550 (12)	0.0031 (12)	0.0066 (11)	0.0130 (11)
C4	0.0445 (13)	0.0537 (14)	0.0435 (12)	−0.0005 (13)	−0.0015 (12)	0.0055 (12)
O5	0.0604 (11)	0.0688 (11)	0.0521 (9)	−0.0062 (11)	0.0095 (9)	0.0082 (10)
C6	0.0526 (15)	0.0556 (15)	0.0424 (12)	−0.0035 (14)	0.0018 (13)	−0.0019 (11)
C7	0.0633 (17)	0.0679 (18)	0.0653 (16)	0.0050 (16)	0.0054 (16)	−0.0085 (16)
C8	0.099 (3)	0.0598 (19)	0.080 (2)	0.0124 (19)	−0.001 (2)	−0.0153 (17)
C9	0.121 (3)	0.0605 (18)	0.0658 (18)	−0.016 (2)	0.001 (2)	−0.0087 (15)
C10	0.079 (2)	0.084 (2)	0.0716 (18)	−0.030 (2)	−0.0092 (17)	−0.0102 (17)
C11	0.0612 (17)	0.0700 (18)	0.0643 (17)	−0.0071 (17)	−0.0062 (14)	−0.0029 (15)
C12	0.0596 (16)	0.0489 (15)	0.0555 (14)	−0.0079 (14)	0.0069 (14)	0.0035 (12)
C13	0.088 (2)	0.0572 (17)	0.0754 (17)	0.0073 (18)	−0.0140 (17)	0.0037 (14)
C14	0.122 (3)	0.0536 (18)	0.095 (2)	0.015 (2)	−0.007 (2)	0.0086 (16)
C15	0.141 (3)	0.0542 (17)	0.096 (2)	0.001 (2)	0.023 (3)	−0.0040 (17)
C16	0.122 (3)	0.0683 (19)	0.080 (2)	−0.023 (2)	0.003 (2)	−0.0141 (17)
C17	0.084 (2)	0.0622 (16)	0.0708 (17)	−0.0091 (16)	−0.0149 (17)	0.0011 (15)
O18	0.0451 (9)	0.0712 (11)	0.0696 (11)	0.0070 (9)	0.0087 (9)	0.0151 (10)
C19	0.0474 (14)	0.0588 (16)	0.0516 (13)	0.0028 (13)	0.0077 (12)	0.0131 (12)
C20	0.0709 (17)	0.0669 (17)	0.0626 (15)	−0.0117 (16)	−0.0072 (15)	0.0051 (13)
C21	0.100 (2)	0.0659 (17)	0.090 (2)	−0.019 (2)	−0.015 (2)	0.0207 (17)
C22	0.098 (2)	0.083 (2)	0.0735 (18)	−0.008 (2)	−0.0112 (19)	0.0302 (17)
C23	0.091 (2)	0.092 (2)	0.0496 (14)	−0.0004 (19)	0.0029 (16)	0.0120 (15)
C24	0.0787 (19)	0.0601 (16)	0.0531 (14)	0.0014 (16)	0.0055 (15)	−0.0023 (13)

Geometric parameters (Å, º)

N1—C2	1.441 (3)	C14—H14A	0.9700
N1—C4	1.372 (3)	C14—H14B	0.9700
N1—C12	1.489 (3)	C15—C16	1.501 (5)
C2—O18	1.222 (3)	C15—H15A	0.9700
C2—N3	1.321 (3)	C15—H15B	0.9700
N3—C19	1.464 (3)	C16—C17	1.539 (4)
N3—H3	0.85 (3)	C16—H16A	0.9700
C4—O5	1.223 (3)	C16—H16B	0.9700
C4—C6	1.498 (3)	C17—H17A	0.9700
C6—C7	1.381 (3)	C17—H17B	0.9700
C6—C11	1.388 (4)	C19—C24	1.517 (4)
C7—C8	1.381 (4)	C19—C20	1.520 (4)
C7—H7A	0.9300	C19—H19A	0.9800
C8—C9	1.357 (5)	C20—C21	1.528 (4)
C8—H8A	0.9300	C20—H20A	0.9700
C9—C10	1.364 (4)	C20—H20B	0.9700
C9—H9A	0.9300	C21—C22	1.515 (4)
C10—C11	1.395 (4)	C21—H21A	0.9700
C10—H10A	0.9300	C21—H21B	0.9700
C11—H11A	0.9300	C22—C23	1.503 (4)
C12—C13	1.506 (4)	C22—H22A	0.9700
C12—C17	1.508 (4)	C22—H22B	0.9700
C12—H12A	0.9800	C23—C24	1.525 (4)
C13—C14	1.537 (4)	C23—H23A	0.9700
C13—H13A	0.9700	C23—H23B	0.9700
C13—H13B	0.9700	C24—H24A	0.9700
C14—C15	1.506 (5)	C24—H24B	0.9700
C4—N1—C2	121.40 (19)	C16—C15—H15B	109.3
C2—N1—C12	118.02 (19)	C14—C15—H15B	109.3
C4—N1—C12	120.5 (2)	H15A—C15—H15B	107.9
O18—C2—N1	120.9 (2)	C15—C16—C17	111.2 (3)
O18—C2—N3	125.3 (2)	C15—C16—H16A	109.4
N3—C2—N1	113.77 (19)	C17—C16—H16A	109.4
C2—N3—C19	123.6 (2)	C15—C16—H16B	109.4
C2—N3—H3	119.3 (19)	C17—C16—H16B	109.4
C19—N3—H3	117.1 (19)	H16A—C16—H16B	108.0
O5—C4—N1	122.7 (2)	C12—C17—C16	110.5 (3)
O5—C4—C6	120.7 (2)	C12—C17—H17A	109.6
N1—C4—C6	116.4 (2)	C16—C17—H17A	109.6
C7—C6—C11	119.2 (3)	C12—C17—H17B	109.6
C7—C6—C4	120.9 (2)	C16—C17—H17B	109.6
C11—C6—C4	119.8 (2)	H17A—C17—H17B	108.1
C6—C7—C8	120.1 (3)	N3—C19—C24	110.1 (2)
C6—C7—H7A	119.9	N3—C19—C20	111.5 (2)
C8—C7—H7A	119.9	C24—C19—C20	110.8 (2)
C9—C8—C7	120.6 (3)	N3—C19—H19A	108.1
C9—C8—H8A	119.7	C24—C19—H19A	108.1
C7—C8—H8A	119.7	C20—C19—H19A	108.1
C8—C9—C10	120.3 (3)	C19—C20—C21	110.8 (2)
C8—C9—H9A	119.9	C19—C20—H20A	109.5
C10—C9—H9A	119.9	C21—C20—H20A	109.5
C9—C10—C11	120.2 (3)	C19—C20—H20B	109.5
C9—C10—H10A	119.9	C21—C20—H20B	109.5
C11—C10—H10A	119.9	H20A—C20—H20B	108.1
C6—C11—C10	119.5 (3)	C22—C21—C20	111.4 (2)
C6—C11—H11A	120.2	C22—C21—H21A	109.3
C10—C11—H11A	120.2	C20—C21—H21A	109.3
N1—C12—C13	111.8 (2)	C22—C21—H21B	109.3
N1—C12—C17	111.6 (2)	C20—C21—H21B	109.3
C13—C12—C17	112.1 (2)	H21A—C21—H21B	108.0
N1—C12—H12A	107.0	C23—C22—C21	111.4 (2)
C13—C12—H12A	107.0	C23—C22—H22A	109.4
C17—C12—H12A	107.0	C21—C22—H22A	109.4
C12—C13—C14	110.6 (3)	C23—C22—H22B	109.4
C12—C13—H13A	109.5	C21—C22—H22B	109.4
C14—C13—H13A	109.5	H22A—C22—H22B	108.0
C12—C13—H13B	109.5	C22—C23—C24	111.1 (2)
C14—C13—H13B	109.5	C22—C23—H23A	109.4
H13A—C13—H13B	108.1	C24—C23—H23A	109.4
C15—C14—C13	111.0 (3)	C22—C23—H23B	109.4
C15—C14—H14A	109.4	C24—C23—H23B	109.4
C13—C14—H14A	109.4	H23A—C23—H23B	108.0
C15—C14—H14B	109.4	C19—C24—C23	110.9 (2)
C13—C14—H14B	109.4	C19—C24—H24A	109.5
H14A—C14—H14B	108.0	C23—C24—H24A	109.5
C16—C15—C14	111.8 (3)	C19—C24—H24B	109.5
C16—C15—H15A	109.3	C23—C24—H24B	109.5
C14—C15—H15A	109.3	H24A—C24—H24B	108.0
C4—N1—C2—O18	122.4 (3)	C4—N1—C12—C13	−104.7 (3)
C12—N1—C2—O18	−61.6 (3)	C2—N1—C12—C13	79.2 (3)
C4—N1—C2—N3	−60.1 (3)	C4—N1—C12—C17	128.9 (2)
C12—N1—C2—N3	115.9 (2)	C2—N1—C12—C17	−47.3 (3)
O18—C2—N3—C19	−6.8 (4)	N1—C12—C13—C14	178.0 (3)
N1—C2—N3—C19	175.8 (2)	C17—C12—C13—C14	−55.9 (3)
C2—N1—C4—O5	167.0 (2)	C12—C13—C14—C15	55.3 (4)
C12—N1—C4—O5	−9.0 (3)	C13—C14—C15—C16	−55.8 (4)
C2—N1—C4—C6	−17.0 (3)	C14—C15—C16—C17	55.7 (4)
C12—N1—C4—C6	167.0 (2)	N1—C12—C17—C16	−178.2 (3)
O5—C4—C6—C7	−60.3 (3)	C13—C12—C17—C16	55.5 (3)
N1—C4—C6—C7	123.6 (3)	C15—C16—C17—C12	−54.9 (4)
O5—C4—C6—C11	115.9 (3)	C2—N3—C19—C24	124.8 (2)
N1—C4—C6—C11	−60.2 (3)	C2—N3—C19—C20	−111.9 (3)
C11—C6—C7—C8	1.5 (4)	N3—C19—C20—C21	−178.8 (2)
C4—C6—C7—C8	177.8 (3)	C24—C19—C20—C21	−55.9 (3)
C6—C7—C8—C9	−3.0 (5)	C19—C20—C21—C22	55.1 (4)
C7—C8—C9—C10	1.9 (5)	C20—C21—C22—C23	−55.3 (4)
C8—C9—C10—C11	0.7 (5)	C21—C22—C23—C24	55.8 (4)
C7—C6—C11—C10	1.0 (4)	N3—C19—C24—C23	−179.7 (2)
C4—C6—C11—C10	−175.3 (3)	C20—C19—C24—C23	56.6 (3)
C9—C10—C11—C6	−2.1 (5)	C22—C23—C24—C19	−56.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O18^i	0.85 (3)	2.14 (3)	2.990 (3)	174 (3)
C19—H19A···O5^ii	0.98	2.43	3.361 (3)	159

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, −z+1.