The title compound, C
20H
28N
2O
2, 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.
Supporting information
CCDC reference: 613615
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.60 × 0.28 × 0.14 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: see text |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0443P)2 + 0.0188P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0077 (11) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O18i | 0.85 (3) | 2.14 (3) | 2.990 (3) | 174 (3) |
C19—H19A···O5ii | 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. |