1,3-Dicyclo­hexyl-3-[(pyridin-2-yl)carbon­yl]urea monohydrate from synchrotron radiation

Pinheiro, A.C.; Souza, M.V.N. de; Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.

doi:10.1107/S1600536811037512

Volume 67
Part 10
Pages o2676-o2677
October 2011

Received 14 September 2011
Accepted 14 September 2011
Online 17 September 2011

Key indicators
Single-crystal Synchrotron study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.126
Data-to-parameter ratio = 16.0
Details

1,3-Dicyclohexyl-3-[(pyridin-2-yl)carbonyl]urea monohydrate from synchrotron radiation

Alessandra C. Pinheiro,^a Marcus V. N. de Souza,^a James L. Wardell,^b ⁺ Solange M. S. V. Wardell ^c and Edward R. T. Tiekink ^d ^*

^aInstituto de Tecnologia em Farmacos, Fundação Oswaldo Cruz (FIOCRUZ), FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil,^bCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil,^cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The title urea derivative crystallizes as a monohydrate, C₁₉H₂₇N₃O₂·H₂O. The central C₃N grouping is almost planar (r.m.s. deviation = 0.0092 Å), and the amide and pyridine groups are substantially twisted out this plane [dihedral angles = 62.80 (12) and 34.98 (10)°, respectively]. Supramolecular double chains propagating along the b-axis direction feature in the crystal packing whereby linear chains sustained by N-HO hydrogen bonds formed between the amide groups are linked by helical chains of water molecules (linked by O-HO hydrogen bonds). The H atom that participates in these water chains is disordered over two positions of equal occupancy. The double chains are connected into a two-dimensional array by C-HO contacts and the layers stack along the a axis.

Related literature

For the preparation of N-(arenecarbonyl)-N,N'-dicyclohexylurea derivatives, see: Kaiser et al. (2008); Neves Filho et al. (2007); Schotman (1991). For the crystal structures of related N-(arenecarbonyl)-N,N'-dicyclohexylurea derivatives, see: Chérioux et al. (2002); Cai et al. (2009); Dhinaa et al. (2010); Orea Flores et al. (2006); Gallagher et al. (1999); Wang & Zhou (2008); Wu et al. (2006).

Experimental

Crystal data

C₁₉H₂₇N₃O₂·H₂O
M_r = 347.46
Monoclinic, P 2₁ /c
a = 18.639 (19) Å
b = 5.035 (5) Å
c = 21.59 (2) Å
= 111.395 (9)°
V = 1887 (3) Å³
Z = 4
Synchrotron radiation
= 0.6905 Å
= 0.05 mm^-1
T = 120 K
0.25 × 0.08 × 0.02 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.743, T_max = 1.000
13440 measured reflections
3810 independent reflections
3200 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.126
S = 1.06
3810 reflections
238 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1nO1ⁱ	0.88 (1)	2.07 (1)	2.908 (3)	160 (2)
O1w-H1wO2	0.84 (2)	1.98 (2)	2.820 (3)	174 (2)
O1w-H2wO1wⁱⁱ	0.84 (3)	1.97 (3)	2.773 (4)	162 (4)
O1w-H3wO1wⁱⁱⁱ	0.84 (3)	1.98 (3)	2.799 (4)	167 (4)
C17-H17O1w^iv	0.95	2.59	3.517 (4)	164
C18-H18O2^v	0.95	2.47	3.367 (4)	157
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6408 ).

Acknowledgements

We thank Professor W. Clegg and the synchrotron component, based at Daresbury, of the EPSRC National Crystallographic Service, University of Southampton, for the data collection. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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organic compounds