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

Abstract

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.

Full text

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N-(4-Bromobenzoyl)-N,N0 0 0-dicyclohexyl-
urea
Ya-Wen Wang and Yu Peng*
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and
Chemical Engineering, Lanzhou University, Lanzhou 730000, People’s Republic of
China
Correspondence e-mail: pengyu@lzu.edu.cn
Received 14 November 2007; accepted 30 November 2007
Key indicators: single-crystal X-ray study; T = 113 K; mean ?(C–C) = 0.003 A ˚;
R factor = 0.036; wR factor = 0.078; data-to-parameter ratio = 19.6.
In the title compound, C20H27BrN2O2, molecules are linked
into one-dimensional chains through (amide)N—H???O
C(amide) intermolecular hydrogen bonds.
Related literature
For related literature, see: Bohne et al. (2005); Bondy et al.
(2004); Bruker (2000); S´lebioda (1995). For literature on
related crystal structures, see: Ball et al. (1990); Che ´rioux et al.
(2002); Gallagher et al. (1999); Govindasamy & Subramanian
(1997); Toniolo et al. (1990); Wu et al. (2006).
Experimental
Crystal data
C20H27BrN2O2
Mr= 407.35
Monoclinic, P21=n
a = 13.501 (2) A˚
b = 9.5621 (10) A˚
c = 16.306 (2) A˚
? = 114.443 (6)?
V = 1916.3 (4) A˚3
Z = 4
Mo K? radiation
? = 2.16 mm?1
T = 113 (2) K
0.38 ? 0.16 ? 0.14 mm
Data collection
Rigaku Saturn CCD diffractometerAbsorption correction: multi-scan
(REQABS; Jacobson, 1998)
Tmin= 0.484, Tmax= 0.739
17461 measured reflections
4526 independent reflections
3651 reflections with I > 2?(I)
Rint= 0.044
Refinement
R[F2> 2?(F2)] = 0.036
wR(F2) = 0.078
S = 1.06
4526 reflections
231 parameters
1 restraint
H atoms treated by a mixture of
independent and constrained
refinement
??max= 0.45 e A˚?3
??min= ?0.44 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N2—H2A???O2i
Symmetry code: (i) ?x þ3
D—HH???AD???AD—H???A
0.898 (10)2.072 (11) 2.961 (2)170 (2)
2;y þ1
2;?z þ3
2.
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,
ORTEP-3 (Farrugia, 1997); software used to prepare material for
publication: CrystalStructure (Rigaku, 1999).
1997);moleculargraphics:
The authors acknowledge financial support from the
Research Fund for New Faculty at the State Key Laboratory
of Applied Organic Chemistry.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: PK2071).
References
Ball, R. G., Brown, R. S. & Bennet, A. J. (1990). Acta Cryst. C46, 2491–2493.
Bohne, C., Ihmels, H., Waidelich, M. & Yihwa, C. (2005). J. Am. Chem. Soc.
127, 17158–17159.
Bondy, C. R., Gale, P. A. & Loeb, S. J. (2004). J. Am. Chem. Soc. 126, 5030–
5031.
Bruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison,
Wisconsin, USA.
Che ´rioux, F., Therrien, B., Stoeckli-Evans, H. & Su ¨ss-Fink, G. (2002). Acta
Cryst. E58, o27–o29.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565
Gallagher, J. F., Kenny, P. T. M. & Sheehy, M. J. (1999). Acta Cryst. C55, 1607–
1610.
Govindasamy, L. & Subramanian, E. (1997). Acta Cryst. C53, 927–928.
Jacobson, R. A. (1998). REQABS. Version 1.1. MSC, The Woodlands, Texas,
USA.
Jacobson, R. A. (1999). CrystalClear. Rigaku Corporation, The Woodlands,
Texas, USA.
Rigaku (1999). CrystalStructure. Version 3.7.0. Rigaku Corporation, Tokyo,
Japan.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go ¨ttingen, Germany.
S´lebioda, M. (1995). Tetrahedron, 51, 7829–7834.
Toniolo, C., Valle, G., Crisma, M., Moretto, V., Izdebski, J., Pelka, J. &
Schneider, C. H. (1990). Helv. Chim. Acta, 73, 626–634.
Wu, L., Liu, H.-M., Zhao, W.-T. & Zhang, W.-Q. (2006). Acta Cryst. C62, o435–
o437.
organic compounds
o160
Wang and Peng doi:10.1107/S1600536807064756
Acta Cryst. (2008). E64, o160
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
sup-1
Acta Cryst. (2008). E64, o160 [ doi:10.1107/S1600536807064756 ]
N-(4-Bromobenzoyl)-N,N'-dicyclohexylurea
Y.-W. Wang and Y. Peng
Comment
The first conscious total synthesis of a natural product was that of urea in 1828 by Wohler, which marks the beginnings
of organic synthesis. Since then, many urea derivatives have been prepared and have demonstrated a wide range of uses,
including fluorescence probes (Bohne et al., 2005) and anion receptors (Bondy et al., 2004).
The title compound, an N-acylurea derivative, can be conveniently prepared from dicyclohexylcarbodiimide (DCC) and
p-bromobenzoic acid according to reported methods (Ślebioda, 1995). The molecular structure is shown in Fig.1. Each
cyclohexyl group adopts the chair conformation, as is required for energy minimization. The two carbonyl groups are twisted
substantially at the central atom, N1, with a dihedral angle of 66.43 (10)° between the O1/C7/N1 and O2/C14/N2 planes,
which increases the distance between atoms O1 and N2. As a result, no intramolecular N2–H2A···O1 hydrogen bond is
formed. However, molecules are linked into chains through (amide) N–H···O=C (amide) intermolecular hydrogen bonds,
reinforced by C–H···O=C interactions. Surprisingly, this supramolecular arrangement is not observed in a closely related
X-ray structure (Gallagher et al., 1999).
Experimental
p-bromobenzoic acid (201 mg, 1 mmol) was dissolved in CHCl3 (5 ml) and DCC (206 mg, 1 mmol) and N,N-dimethyl-
pyridin-4-amine (122 mg, 1 mmol) were added to the solution. The resulting mixture was stirred for 1 h at 298 K. After
evaporation of the solvent, a colorless solid was isolated. Single crystals suitable for X-ray structure determination were
obtained by slow evaporation of a EtOAc solution over a period of several days.
Refinement
The H atom bonded to N2 was found in a difference map and refined freely to obtain an unbiased geometry for the hydrogen
bonding scheme. The H atoms bonded to C were placed geometrically (C—H values were set to 1.00, 0.99 and 0.95 A° for
atoms CH2 and CH, respectively) and refined with a riding model, with Uiso(H) = 1.2 times Ueq(C).
Figures
Fig. 1. An ellipsoid plot of the title compound, showing the atom-labelling scheme. Displace-
ment ellipsoids are drawn at the 50% probability level.

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supplementary materials
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N-(4-Bromobenzoyl)-N,N'-dicyclohexylurea
Crystal data
C20H27BrN2O2
F000 = 848
Dx = 1.412 Mg m−3
Mo Kα radiation
λ = 0.71070 Å
Cell parameters from 4164 reflections
θ = 1.7–27.9º
µ = 2.16 mm−1
T = 113 (2) K
Prism, colorless
Mr = 407.35
Monoclinic, P21/n
Hall symbol: -P 2yn
a = 13.501 (2) Å
b = 9.5621 (10) Å
c = 16.306 (2) Å
β = 114.443 (6)º
V = 1916.3 (4) Å3
Z = 4
0.38 × 0.16 × 0.14 mm
Data collection
Rigaku Saturn CCD
diffractometer
Radiation source: Rotating anode
Monochromator: confocal
Detector resolution: 7.31 pixels mm-1
T = 113(2) K
ω scans
Absorption correction: multi-scan
(REQABS; Jacobson, 1998)
Tmin = 0.484, Tmax = 0.739
17461 measured reflections
4526 independent reflections
3651 reflections with I > 2σ(I)
Rint = 0.044
θmax = 27.9º
θmin = 1.7º
h = −17→17
k = −12→12
l = −21→20
Refinement
Refinement on F2
Secondary atom site location: difference Fourier map
Least-squares matrix: full
Hydrogen site location: inferred from neighbouring
sites
H atoms treated by a mixture of
independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0381P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.003
Δρmax = 0.45 e Å−3
Δρmin = −0.44 e Å−3
Extinction correction: none
R[F2 > 2σ(F2)] = 0.036
wR(F2) = 0.078
S = 1.06
4526 reflections
231 parameters
1 restraint
Primary atom site location: structure-invariant direct
methods

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supplementary materials
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Special details
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, convention-
al 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.615319 (17)
0.86443 (11)
0.67615 (11)
0.95485 (9)
0.76754 (10)
0.69576 (14)
0.69278 (15)
0.6508
0.75215 (15)
0.7519
0.81235 (13)
0.81418 (14)
0.8551
0.75616 (14)
0.7581
0.88221 (13)
0.94261 (14)
0.9907
1.01578 (15)
0.9702
1.0574
1.09504 (16)
1.1462
1.1380
1.03445 (17)
0.9878
1.0874
0.96424 (17)
0.9238
1.0117
0.88348 (15)
0.8424
0.8308
0.76568 (14)
0.56540 (13)
0.5702
0.50196 (16)
y
0.39160 (2)
0.53780 (15)
0.53992 (16)
0.68643 (13)
0.34042 (13)
0.4583 (2)
0.5987 (2)
0.6624
0.6450 (2)
0.7414
0.55047 (19)
0.40955 (19)
0.3450
0.3634 (2)
0.2677
0.60122 (18)
0.55666 (19)
0.6372
0.4287 (2)
0.3452
0.4122
0.4493 (2)
0.5260
0.3628
0.4842 (2)
0.4043
0.5007
0.6143 (2)
0.6338
0.6956
0.5955 (2)
0.6834
0.5210
0.4618 (2)
0.48403 (19)
0.3853
0.5682 (2)
z
1.092233 (14)
0.80694 (9)
0.73657 (10)
0.92419 (8)
0.73292 (8)
1.02792 (12)
1.00682 (13)
1.0240
0.96011 (13)
0.9460
0.93373 (11)
0.95585 (12)
0.9381
1.00396 (12)
1.0202
0.88777 (12)
0.76516 (12)
0.7963
0.77921 (14)
0.7531
0.8445
0.73482 (14)
0.7656
0.7415
0.63510 (14)
0.6032
0.6086
0.62288 (14)
0.5578
0.6507
0.66570 (13)
0.6599
0.6335
0.75616 (11)
0.69141 (12)
0.6733
0.60708 (13)
Uiso*/Ueq
0.03591 (9)
0.0172 (3)
0.0180 (3)
0.0226 (3)
0.0234 (3)
0.0233 (4)
0.0267 (4)
0.032*
0.0246 (4)
0.029*
0.0176 (4)
0.0205 (4)
0.025*
0.0223 (4)
0.027*
0.0179 (4)
0.0199 (4)
0.024*
0.0259 (4)
0.031*
0.031*
0.0331 (5)
0.040*
0.040*
0.0361 (5)
0.043*
0.043*
0.0341 (5)
0.041*
0.041*
0.0268 (4)
0.032*
0.032*
0.0180 (4)
0.0180 (4)
0.022*
0.0313 (5)
Br1
N1
N2
O1
O2
C1
C2
H2
C3
H3
C4
C5
H5
C6
H6
C7
C8
H8
C9
H9A
H9B
C10
H10A
H10B
C11
H11A
H11B
C12
H12A
H12B
C13
H13A
H13B
C14
C15
H15
C16