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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022173/bx2008sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022173/bx2008Isup2.hkl
Contains datablock I

CCDC reference: 613615

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

Computing details top

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
C20H28N2O2F(000) = 712
Mr = 328.44Dx = 1.153 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 75 reflections
a = 9.7060 (14) Åθ = 4.6–12.0°
b = 12.0125 (12) ŵ = 0.07 mm1
c = 16.2342 (13) ÅT = 296 K
V = 1892.8 (4) Å3Needle, colourless
Z = 40.60 × 0.28 × 0.14 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.020
Radiation source: fine-focus sealed tube, FN4θmax = 25.0°, θmin = 2.1°
Graphite monochromatorh = 114
2θ/ω scansk = 114
3205 measured reflectionsl = 191
1922 independent reflections3 standard reflections every 97 reflections
1411 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: see text
R[F2 > 2σ(F2)] = 0.037H 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 reflectionsΔρmax = 0.12 e Å3
222 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
N10.0440 (2)0.67467 (15)0.57540 (11)0.0499 (5)
C20.0286 (2)0.72856 (19)0.50901 (15)0.0473 (6)
N30.0494 (2)0.79584 (19)0.46457 (12)0.0532 (5)
H30.135 (3)0.800 (2)0.4748 (16)0.063 (8)*
C40.1063 (2)0.7350 (2)0.63678 (15)0.0472 (6)
O50.18775 (17)0.69383 (15)0.68546 (10)0.0604 (5)
C60.0622 (3)0.8540 (2)0.64531 (14)0.0502 (6)
C70.1573 (3)0.9393 (2)0.64149 (16)0.0655 (8)
H7A0.24960.92340.63170.079*
C80.1155 (4)1.0483 (3)0.65226 (19)0.0796 (9)
H8A0.17931.10570.64700.095*
C90.0177 (4)1.0724 (3)0.67040 (18)0.0825 (10)
H9A0.04411.14580.67910.099*
C100.1130 (3)0.9892 (3)0.67587 (19)0.0782 (9)
H10A0.20391.00620.68890.094*
C110.0746 (3)0.8789 (2)0.66201 (17)0.0652 (8)
H11A0.14010.82250.66390.078*
C120.0577 (3)0.5513 (2)0.57283 (15)0.0546 (7)
H12A0.13010.53100.61210.066*
C130.0723 (3)0.4941 (2)0.60069 (19)0.0736 (8)
H13A0.09570.51870.65580.088*
H13B0.14750.51420.56430.088*
C140.0534 (4)0.3670 (2)0.6003 (2)0.0900 (10)
H14A0.13980.33150.61480.108*
H14B0.01470.34640.64130.108*
C150.0075 (4)0.3267 (2)0.5169 (2)0.0970 (11)
H15A0.08010.34030.47710.116*
H15B0.00860.24710.51920.116*
C160.1218 (4)0.3841 (3)0.4891 (2)0.0902 (10)
H16A0.19710.36390.52540.108*
H16B0.14510.35930.43390.108*
C170.1042 (3)0.5114 (2)0.48922 (18)0.0723 (8)
H17A0.03660.53260.44810.087*
H17B0.19100.54650.47510.087*
O180.14985 (16)0.70806 (15)0.49562 (11)0.0620 (5)
C190.0035 (3)0.8651 (2)0.39744 (15)0.0526 (7)
H19A0.10020.84520.38820.063*
C200.0029 (3)0.9881 (2)0.41910 (16)0.0668 (7)
H20A0.05261.00210.46770.080*
H20B0.09731.00860.43160.080*
C210.0499 (4)1.0593 (3)0.34779 (18)0.0853 (10)
H21A0.03901.13740.36150.102*
H21B0.14731.04500.33960.102*
C220.0273 (4)1.0343 (3)0.26879 (18)0.0849 (10)
H22A0.12281.05690.27480.102*
H22B0.01251.07710.22410.102*
C230.0214 (3)0.9126 (3)0.24792 (16)0.0775 (9)
H23A0.07300.89170.23600.093*
H23B0.07610.89860.19900.093*
C240.0757 (3)0.8417 (2)0.31875 (15)0.0640 (8)
H24A0.17260.85760.32740.077*
H24B0.06690.76350.30470.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0541 (12)0.0466 (11)0.0491 (11)0.0026 (10)0.0054 (11)0.0047 (10)
C20.0468 (14)0.0455 (13)0.0496 (13)0.0004 (12)0.0033 (13)0.0003 (12)
N30.0417 (12)0.0630 (13)0.0550 (12)0.0031 (12)0.0066 (11)0.0130 (11)
C40.0445 (13)0.0537 (14)0.0435 (12)0.0005 (13)0.0015 (12)0.0055 (12)
O50.0604 (11)0.0688 (11)0.0521 (9)0.0062 (11)0.0095 (9)0.0082 (10)
C60.0526 (15)0.0556 (15)0.0424 (12)0.0035 (14)0.0018 (13)0.0019 (11)
C70.0633 (17)0.0679 (18)0.0653 (16)0.0050 (16)0.0054 (16)0.0085 (16)
C80.099 (3)0.0598 (19)0.080 (2)0.0124 (19)0.001 (2)0.0153 (17)
C90.121 (3)0.0605 (18)0.0658 (18)0.016 (2)0.001 (2)0.0087 (15)
C100.079 (2)0.084 (2)0.0716 (18)0.030 (2)0.0092 (17)0.0102 (17)
C110.0612 (17)0.0700 (18)0.0643 (17)0.0071 (17)0.0062 (14)0.0029 (15)
C120.0596 (16)0.0489 (15)0.0555 (14)0.0079 (14)0.0069 (14)0.0035 (12)
C130.088 (2)0.0572 (17)0.0754 (17)0.0073 (18)0.0140 (17)0.0037 (14)
C140.122 (3)0.0536 (18)0.095 (2)0.015 (2)0.007 (2)0.0086 (16)
C150.141 (3)0.0542 (17)0.096 (2)0.001 (2)0.023 (3)0.0040 (17)
C160.122 (3)0.0683 (19)0.080 (2)0.023 (2)0.003 (2)0.0141 (17)
C170.084 (2)0.0622 (16)0.0708 (17)0.0091 (16)0.0149 (17)0.0011 (15)
O180.0451 (9)0.0712 (11)0.0696 (11)0.0070 (9)0.0087 (9)0.0151 (10)
C190.0474 (14)0.0588 (16)0.0516 (13)0.0028 (13)0.0077 (12)0.0131 (12)
C200.0709 (17)0.0669 (17)0.0626 (15)0.0117 (16)0.0072 (15)0.0051 (13)
C210.100 (2)0.0659 (17)0.090 (2)0.019 (2)0.015 (2)0.0207 (17)
C220.098 (2)0.083 (2)0.0735 (18)0.008 (2)0.0112 (19)0.0302 (17)
C230.091 (2)0.092 (2)0.0496 (14)0.0004 (19)0.0029 (16)0.0120 (15)
C240.0787 (19)0.0601 (16)0.0531 (14)0.0014 (16)0.0055 (15)0.0023 (13)
Geometric parameters (Å, º) top
N1—C21.441 (3)C14—H14A0.9700
N1—C41.372 (3)C14—H14B0.9700
N1—C121.489 (3)C15—C161.501 (5)
C2—O181.222 (3)C15—H15A0.9700
C2—N31.321 (3)C15—H15B0.9700
N3—C191.464 (3)C16—C171.539 (4)
N3—H30.85 (3)C16—H16A0.9700
C4—O51.223 (3)C16—H16B0.9700
C4—C61.498 (3)C17—H17A0.9700
C6—C71.381 (3)C17—H17B0.9700
C6—C111.388 (4)C19—C241.517 (4)
C7—C81.381 (4)C19—C201.520 (4)
C7—H7A0.9300C19—H19A0.9800
C8—C91.357 (5)C20—C211.528 (4)
C8—H8A0.9300C20—H20A0.9700
C9—C101.364 (4)C20—H20B0.9700
C9—H9A0.9300C21—C221.515 (4)
C10—C111.395 (4)C21—H21A0.9700
C10—H10A0.9300C21—H21B0.9700
C11—H11A0.9300C22—C231.503 (4)
C12—C131.506 (4)C22—H22A0.9700
C12—C171.508 (4)C22—H22B0.9700
C12—H12A0.9800C23—C241.525 (4)
C13—C141.537 (4)C23—H23A0.9700
C13—H13A0.9700C23—H23B0.9700
C13—H13B0.9700C24—H24A0.9700
C14—C151.506 (5)C24—H24B0.9700
C4—N1—C2121.40 (19)C16—C15—H15B109.3
C2—N1—C12118.02 (19)C14—C15—H15B109.3
C4—N1—C12120.5 (2)H15A—C15—H15B107.9
O18—C2—N1120.9 (2)C15—C16—C17111.2 (3)
O18—C2—N3125.3 (2)C15—C16—H16A109.4
N3—C2—N1113.77 (19)C17—C16—H16A109.4
C2—N3—C19123.6 (2)C15—C16—H16B109.4
C2—N3—H3119.3 (19)C17—C16—H16B109.4
C19—N3—H3117.1 (19)H16A—C16—H16B108.0
O5—C4—N1122.7 (2)C12—C17—C16110.5 (3)
O5—C4—C6120.7 (2)C12—C17—H17A109.6
N1—C4—C6116.4 (2)C16—C17—H17A109.6
C7—C6—C11119.2 (3)C12—C17—H17B109.6
C7—C6—C4120.9 (2)C16—C17—H17B109.6
C11—C6—C4119.8 (2)H17A—C17—H17B108.1
C6—C7—C8120.1 (3)N3—C19—C24110.1 (2)
C6—C7—H7A119.9N3—C19—C20111.5 (2)
C8—C7—H7A119.9C24—C19—C20110.8 (2)
C9—C8—C7120.6 (3)N3—C19—H19A108.1
C9—C8—H8A119.7C24—C19—H19A108.1
C7—C8—H8A119.7C20—C19—H19A108.1
C8—C9—C10120.3 (3)C19—C20—C21110.8 (2)
C8—C9—H9A119.9C19—C20—H20A109.5
C10—C9—H9A119.9C21—C20—H20A109.5
C9—C10—C11120.2 (3)C19—C20—H20B109.5
C9—C10—H10A119.9C21—C20—H20B109.5
C11—C10—H10A119.9H20A—C20—H20B108.1
C6—C11—C10119.5 (3)C22—C21—C20111.4 (2)
C6—C11—H11A120.2C22—C21—H21A109.3
C10—C11—H11A120.2C20—C21—H21A109.3
N1—C12—C13111.8 (2)C22—C21—H21B109.3
N1—C12—C17111.6 (2)C20—C21—H21B109.3
C13—C12—C17112.1 (2)H21A—C21—H21B108.0
N1—C12—H12A107.0C23—C22—C21111.4 (2)
C13—C12—H12A107.0C23—C22—H22A109.4
C17—C12—H12A107.0C21—C22—H22A109.4
C12—C13—C14110.6 (3)C23—C22—H22B109.4
C12—C13—H13A109.5C21—C22—H22B109.4
C14—C13—H13A109.5H22A—C22—H22B108.0
C12—C13—H13B109.5C22—C23—C24111.1 (2)
C14—C13—H13B109.5C22—C23—H23A109.4
H13A—C13—H13B108.1C24—C23—H23A109.4
C15—C14—C13111.0 (3)C22—C23—H23B109.4
C15—C14—H14A109.4C24—C23—H23B109.4
C13—C14—H14A109.4H23A—C23—H23B108.0
C15—C14—H14B109.4C19—C24—C23110.9 (2)
C13—C14—H14B109.4C19—C24—H24A109.5
H14A—C14—H14B108.0C23—C24—H24A109.5
C16—C15—C14111.8 (3)C19—C24—H24B109.5
C16—C15—H15A109.3C23—C24—H24B109.5
C14—C15—H15A109.3H24A—C24—H24B108.0
C4—N1—C2—O18122.4 (3)C4—N1—C12—C13104.7 (3)
C12—N1—C2—O1861.6 (3)C2—N1—C12—C1379.2 (3)
C4—N1—C2—N360.1 (3)C4—N1—C12—C17128.9 (2)
C12—N1—C2—N3115.9 (2)C2—N1—C12—C1747.3 (3)
O18—C2—N3—C196.8 (4)N1—C12—C13—C14178.0 (3)
N1—C2—N3—C19175.8 (2)C17—C12—C13—C1455.9 (3)
C2—N1—C4—O5167.0 (2)C12—C13—C14—C1555.3 (4)
C12—N1—C4—O59.0 (3)C13—C14—C15—C1655.8 (4)
C2—N1—C4—C617.0 (3)C14—C15—C16—C1755.7 (4)
C12—N1—C4—C6167.0 (2)N1—C12—C17—C16178.2 (3)
O5—C4—C6—C760.3 (3)C13—C12—C17—C1655.5 (3)
N1—C4—C6—C7123.6 (3)C15—C16—C17—C1254.9 (4)
O5—C4—C6—C11115.9 (3)C2—N3—C19—C24124.8 (2)
N1—C4—C6—C1160.2 (3)C2—N3—C19—C20111.9 (3)
C11—C6—C7—C81.5 (4)N3—C19—C20—C21178.8 (2)
C4—C6—C7—C8177.8 (3)C24—C19—C20—C2155.9 (3)
C6—C7—C8—C93.0 (5)C19—C20—C21—C2255.1 (4)
C7—C8—C9—C101.9 (5)C20—C21—C22—C2355.3 (4)
C8—C9—C10—C110.7 (5)C21—C22—C23—C2455.8 (4)
C7—C6—C11—C101.0 (4)N3—C19—C24—C23179.7 (2)
C4—C6—C11—C10175.3 (3)C20—C19—C24—C2356.6 (3)
C9—C10—C11—C62.1 (5)C22—C23—C24—C1956.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O18i0.85 (3)2.14 (3)2.990 (3)174 (3)
C19—H19A···O5ii0.982.433.361 (3)159
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+1/2, y+3/2, z+1.
 

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