1,3-Dicyclo-hexyl-3-[(pyridin-2-yl)carbon-yl]urea monohydrate from synchrotron radiation.

The title urea derivative crystallizes as a monohydrate, C(19)H(27)N(3)O(2)·H(2)O. The central C(3)N grouping is almost planar (r.m.s. deviation = 0.0092 Å), and the amide and pyridine groups are substanti-ally twisted out this plane [dihedral angles = 62.80 (12) and 34.98 (10)°, respectively]. Supra-molecular double chains propagating along the b-axis direction feature in the crystal packing whereby linear chains sustained by N-H⋯O hydrogen bonds formed between the amide groups are linked by helical chains of water mol-ecules (linked by O-H⋯O 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-H⋯O 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 = 347.46

Monoclinic,

a = 18.639 (19) Å

b = 5.035 (5) Å

c = 21.59 (2) Å

β = 111.395 (9)°

V = 1887 (3) Å3

Z = 4

Synchrotron radiation

λ = 0.6905 Å

μ = 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 > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.126

S = 1.06

3810 reflections

238 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037512/hb6408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037512/hb6408Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037512/hb6408Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H27N3O2·H2O	F(000) = 752
Mr = 347.46	Dx = 1.223 Mg m−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.6905 Å
Hall symbol: -P 2ybc	Cell parameters from 908 reflections
a = 18.639 (19) Å	θ = 4.6–25.5°
b = 5.035 (5) Å	µ = 0.05 mm−1
c = 21.59 (2) Å	T = 120 K
β = 111.395 (9)°	Lath, colourless
V = 1887 (3) Å3	0.25 × 0.08 × 0.02 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3810 independent reflections
Radiation source: Daresbury SRS station 9.8	3200 reflections with I > 2σ(I)
silicon 111	Rint = 0.043
fine–slice ω scans	θmax = 25.6°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −22→23
Tmin = 0.743, Tmax = 1.000	k = −6→6
13440 measured reflections	l = −25→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.9558P] where P = (Fo2 + 2Fc2)/3
3810 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.36 e Å−3
7 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.70258 (7)	−0.1731 (2)	0.59067 (6)	0.0303 (3)
O2	0.91282 (6)	0.2990 (2)	0.60869 (5)	0.0301 (3)
N1	0.69415 (7)	0.2624 (3)	0.61576 (7)	0.0243 (3)
H1N	0.7086 (10)	0.425 (2)	0.6115 (9)	0.029*
N2	0.79274 (7)	0.1277 (3)	0.58142 (6)	0.0234 (3)
N3	0.83745 (8)	0.0413 (3)	0.72128 (7)	0.0337 (3)
C1	0.72692 (9)	0.0548 (3)	0.59806 (7)	0.0240 (3)
C2	0.62543 (9)	0.2342 (3)	0.63269 (8)	0.0258 (3)
H2	0.6196	0.0428	0.6423	0.031*
C3	0.55414 (10)	0.3205 (4)	0.57442 (8)	0.0338 (4)
H3A	0.5482	0.2074	0.5354	0.041*
H3B	0.5606	0.5065	0.5625	0.041*
C4	0.48146 (10)	0.2991 (4)	0.59151 (9)	0.0377 (4)
H4A	0.4366	0.3659	0.5537	0.045*
H4B	0.4719	0.1105	0.5988	0.045*
C5	0.49011 (10)	0.4583 (4)	0.65350 (9)	0.0396 (4)
H5A	0.4935	0.6496	0.6443	0.048*
H5B	0.4440	0.4314	0.6653	0.048*
C6	0.56154 (11)	0.3759 (5)	0.71165 (9)	0.0468 (5)
H6A	0.5553	0.1908	0.7243	0.056*
H6B	0.5673	0.4914	0.7503	0.056*
C7	0.63413 (10)	0.3957 (4)	0.69461 (8)	0.0354 (4)
H7A	0.6438	0.5840	0.6870	0.043*
H7B	0.6790	0.3294	0.7325	0.043*
C8	0.78688 (9)	0.0807 (3)	0.51160 (7)	0.0245 (3)
H8	0.8211	0.2131	0.5015	0.029*
C9	0.81573 (9)	−0.1941 (3)	0.50312 (8)	0.0276 (3)
H9A	0.7841	−0.3306	0.5141	0.033*
H9B	0.8697	−0.2155	0.5341	0.033*
C10	0.81124 (10)	−0.2337 (3)	0.43150 (8)	0.0308 (4)
H10A	0.8470	−0.1091	0.4221	0.037*
H10B	0.8274	−0.4169	0.4261	0.037*
C11	0.72974 (10)	−0.1862 (4)	0.38230 (8)	0.0333 (4)
H11A	0.6947	−0.3211	0.3891	0.040*
H11B	0.7287	−0.2052	0.3363	0.040*
C12	0.70189 (10)	0.0901 (4)	0.39131 (8)	0.0331 (4)
H12A	0.6483	0.1150	0.3599	0.040*
H12B	0.7346	0.2253	0.3812	0.040*
C13	0.70517 (9)	0.1285 (3)	0.46261 (8)	0.0285 (3)
H13A	0.6889	0.3113	0.4681	0.034*
H13B	0.6694	0.0028	0.4717	0.034*
C14	0.85976 (9)	0.2239 (3)	0.62575 (7)	0.0241 (3)
C15	0.87147 (9)	0.2303 (3)	0.69852 (7)	0.0250 (3)
C16	0.85324 (11)	0.0380 (4)	0.78661 (9)	0.0406 (4)
H16	0.8300	−0.0960	0.8039	0.049*
C17	0.90154 (11)	0.2181 (4)	0.83078 (8)	0.0396 (4)
H17	0.9112	0.2064	0.8770	0.048*
C18	0.93532 (11)	0.4146 (4)	0.80637 (9)	0.0408 (4)
H18	0.9679	0.5435	0.8352	0.049*
C19	0.92055 (10)	0.4198 (4)	0.73843 (8)	0.0342 (4)
H19	0.9436	0.5503	0.7199	0.041*
O1W	0.97088 (8)	0.2514 (3)	0.50550 (6)	0.0385 (3)
H1W	0.9509 (12)	0.257 (5)	0.5347 (9)	0.058*
H2W	0.998 (2)	0.385 (5)	0.507 (2)	0.058*	0.50
H3W	0.994 (2)	0.107 (5)	0.508 (2)	0.058*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0384 (6)	0.0207 (6)	0.0363 (6)	−0.0051 (5)	0.0192 (5)	−0.0030 (5)
O2	0.0307 (6)	0.0385 (7)	0.0230 (5)	−0.0049 (5)	0.0121 (5)	0.0002 (5)
N1	0.0300 (7)	0.0190 (6)	0.0281 (7)	−0.0023 (5)	0.0155 (6)	−0.0002 (5)
N2	0.0295 (7)	0.0234 (6)	0.0195 (6)	−0.0012 (5)	0.0116 (5)	−0.0010 (5)
N3	0.0417 (8)	0.0361 (8)	0.0248 (7)	−0.0032 (6)	0.0138 (6)	0.0041 (6)
C1	0.0287 (8)	0.0223 (8)	0.0220 (7)	−0.0013 (6)	0.0104 (6)	0.0004 (6)
C2	0.0305 (8)	0.0239 (8)	0.0284 (8)	−0.0001 (6)	0.0172 (7)	0.0030 (6)
C3	0.0312 (9)	0.0483 (10)	0.0232 (8)	−0.0035 (7)	0.0114 (7)	−0.0021 (7)
C4	0.0293 (9)	0.0512 (11)	0.0327 (9)	−0.0017 (8)	0.0115 (7)	0.0044 (8)
C5	0.0344 (9)	0.0495 (11)	0.0410 (10)	0.0074 (8)	0.0208 (8)	0.0028 (8)
C6	0.0408 (10)	0.0770 (15)	0.0279 (9)	0.0091 (10)	0.0190 (8)	0.0026 (9)
C7	0.0320 (9)	0.0524 (11)	0.0225 (8)	0.0037 (8)	0.0106 (7)	−0.0017 (8)
C8	0.0313 (8)	0.0277 (8)	0.0169 (7)	−0.0018 (6)	0.0116 (6)	−0.0017 (6)
C9	0.0322 (8)	0.0265 (8)	0.0229 (8)	0.0026 (6)	0.0087 (6)	−0.0008 (6)
C10	0.0396 (9)	0.0294 (9)	0.0261 (8)	0.0027 (7)	0.0152 (7)	−0.0037 (7)
C11	0.0419 (10)	0.0359 (9)	0.0199 (8)	−0.0003 (7)	0.0085 (7)	−0.0042 (7)
C12	0.0367 (9)	0.0354 (9)	0.0228 (8)	0.0031 (7)	0.0058 (7)	−0.0014 (7)
C13	0.0320 (8)	0.0275 (8)	0.0266 (8)	0.0016 (7)	0.0113 (7)	−0.0013 (6)
C14	0.0307 (8)	0.0217 (7)	0.0210 (7)	0.0015 (6)	0.0107 (6)	0.0015 (6)
C15	0.0292 (8)	0.0277 (8)	0.0195 (7)	0.0029 (6)	0.0105 (6)	0.0009 (6)
C16	0.0501 (11)	0.0479 (11)	0.0275 (9)	−0.0006 (9)	0.0187 (8)	0.0071 (8)
C17	0.0428 (10)	0.0571 (12)	0.0188 (8)	0.0073 (9)	0.0111 (7)	0.0022 (8)
C18	0.0412 (10)	0.0490 (11)	0.0269 (9)	−0.0013 (8)	0.0061 (8)	−0.0112 (8)
C19	0.0417 (10)	0.0357 (10)	0.0274 (8)	−0.0052 (7)	0.0152 (7)	−0.0043 (7)
O1W	0.0490 (8)	0.0421 (7)	0.0340 (7)	−0.0052 (6)	0.0263 (6)	−0.0011 (6)

O1—C1	1.223 (2)	C8—C13	1.523 (2)
O2—C14	1.234 (2)	C8—H8	1.0000
N1—C1	1.335 (2)	C9—C10	1.531 (3)
N1—C2	1.461 (2)	C9—H9A	0.9900
N1—H1N	0.875 (9)	C9—H9B	0.9900
N2—C14	1.356 (2)	C10—C11	1.522 (3)
N2—C1	1.446 (2)	C10—H10A	0.9900
N2—C8	1.490 (2)	C10—H10B	0.9900
N3—C16	1.332 (3)	C11—C12	1.522 (3)
N3—C15	1.333 (2)	C11—H11A	0.9900
C2—C7	1.522 (3)	C11—H11B	0.9900
C2—C3	1.522 (3)	C12—C13	1.530 (3)
C2—H2	1.0000	C12—H12A	0.9900
C3—C4	1.532 (3)	C12—H12B	0.9900
C3—H3A	0.9900	C13—H13A	0.9900
C3—H3B	0.9900	C13—H13B	0.9900
C4—C5	1.517 (3)	C14—C15	1.506 (2)
C4—H4A	0.9900	C15—C19	1.384 (2)
C4—H4B	0.9900	C16—C17	1.384 (3)
C5—C6	1.517 (3)	C16—H16	0.9500
C5—H5A	0.9900	C17—C18	1.377 (3)
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.529 (3)	C18—C19	1.391 (3)
C6—H6A	0.9900	C18—H18	0.9500
C6—H6B	0.9900	C19—H19	0.9500
C7—H7A	0.9900	O1W—H1W	0.842 (10)
C7—H7B	0.9900	O1W—H2W	0.839 (10)
C8—C9	1.520 (3)	O1W—H3W	0.838 (10)
C1—N1—C2	121.98 (13)	C8—C9—C10	110.41 (13)
C1—N1—H1N	120.7 (12)	C8—C9—H9A	109.6
C2—N1—H1N	116.7 (12)	C10—C9—H9A	109.6
C14—N2—C1	124.18 (14)	C8—C9—H9B	109.6
C14—N2—C8	118.65 (13)	C10—C9—H9B	109.6
C1—N2—C8	117.10 (12)	H9A—C9—H9B	108.1
C16—N3—C15	116.63 (16)	C11—C10—C9	110.95 (14)
O1—C1—N1	125.83 (15)	C11—C10—H10A	109.5
O1—C1—N2	120.91 (13)	C9—C10—H10A	109.4
N1—C1—N2	113.01 (14)	C11—C10—H10B	109.4
N1—C2—C7	110.20 (13)	C9—C10—H10B	109.5
N1—C2—C3	110.25 (14)	H10A—C10—H10B	108.0
C7—C2—C3	110.76 (14)	C10—C11—C12	110.77 (14)
N1—C2—H2	108.5	C10—C11—H11A	109.5
C7—C2—H2	108.5	C12—C11—H11A	109.5
C3—C2—H2	108.5	C10—C11—H11B	109.5
C2—C3—C4	111.27 (15)	C12—C11—H11B	109.5
C2—C3—H3A	109.4	H11A—C11—H11B	108.1
C4—C3—H3A	109.4	C11—C12—C13	110.71 (14)
C2—C3—H3B	109.4	C11—C12—H12A	109.5
C4—C3—H3B	109.4	C13—C12—H12A	109.5
H3A—C3—H3B	108.0	C11—C12—H12B	109.5
C5—C4—C3	110.89 (15)	C13—C12—H12B	109.5
C5—C4—H4A	109.5	H12A—C12—H12B	108.1
C3—C4—H4A	109.5	C8—C13—C12	109.96 (14)
C5—C4—H4B	109.5	C8—C13—H13A	109.7
C3—C4—H4B	109.5	C12—C13—H13A	109.7
H4A—C4—H4B	108.1	C8—C13—H13B	109.7
C6—C5—C4	111.37 (16)	C12—C13—H13B	109.7
C6—C5—H5A	109.4	H13A—C13—H13B	108.2
C4—C5—H5A	109.4	O2—C14—N2	122.07 (15)
C6—C5—H5B	109.4	O2—C14—C15	118.57 (14)
C4—C5—H5B	109.4	N2—C14—C15	119.32 (14)
H5A—C5—H5B	108.0	N3—C15—C19	123.94 (15)
C5—C6—C7	111.68 (16)	N3—C15—C14	117.52 (14)
C5—C6—H6A	109.3	C19—C15—C14	118.40 (14)
C7—C6—H6A	109.3	N3—C16—C17	123.96 (18)
C5—C6—H6B	109.3	N3—C16—H16	118.0
C7—C6—H6B	109.3	C17—C16—H16	118.0
H6A—C6—H6B	107.9	C18—C17—C16	118.71 (17)
C2—C7—C6	110.88 (15)	C18—C17—H17	120.6
C2—C7—H7A	109.5	C16—C17—H17	120.6
C6—C7—H7A	109.5	C17—C18—C19	118.37 (17)
C2—C7—H7B	109.5	C17—C18—H18	120.8
C6—C7—H7B	109.5	C19—C18—H18	120.8
H7A—C7—H7B	108.1	C15—C19—C18	118.38 (17)
N2—C8—C9	111.57 (12)	C15—C19—H19	120.8
N2—C8—C13	111.29 (13)	C18—C19—H19	120.8
C9—C8—C13	111.61 (13)	H1W—O1W—H2W	112 (3)
N2—C8—H8	107.4	H1W—O1W—H3W	109 (3)
C9—C8—H8	107.4	H2W—O1W—H3W	114 (4)
C13—C8—H8	107.4
C2—N1—C1—O1	3.9 (2)	C8—C9—C10—C11	−55.90 (18)
C2—N1—C1—N2	178.19 (12)	C9—C10—C11—C12	56.71 (19)
C14—N2—C1—O1	−118.72 (17)	C10—C11—C12—C13	−57.41 (19)
C8—N2—C1—O1	58.28 (19)	N2—C8—C13—C12	177.61 (13)
C14—N2—C1—N1	66.67 (19)	C9—C8—C13—C12	−57.02 (17)
C8—N2—C1—N1	−116.33 (15)	C11—C12—C13—C8	57.10 (19)
C1—N1—C2—C7	136.11 (15)	C1—N2—C14—O2	−175.44 (14)
C1—N1—C2—C3	−101.33 (17)	C8—N2—C14—O2	7.6 (2)
N1—C2—C3—C4	−178.62 (14)	C1—N2—C14—C15	6.9 (2)
C7—C2—C3—C4	−56.4 (2)	C8—N2—C14—C15	−170.02 (13)
C2—C3—C4—C5	56.0 (2)	C16—N3—C15—C19	−0.6 (3)
C3—C4—C5—C6	−55.1 (2)	C16—N3—C15—C14	174.98 (15)
C4—C5—C6—C7	55.2 (2)	O2—C14—C15—N3	−146.42 (16)
N1—C2—C7—C6	178.06 (15)	N2—C14—C15—N3	31.3 (2)
C3—C2—C7—C6	55.8 (2)	O2—C14—C15—C19	29.4 (2)
C5—C6—C7—C2	−55.4 (2)	N2—C14—C15—C19	−152.84 (15)
C14—N2—C8—C9	87.09 (17)	C15—N3—C16—C17	0.5 (3)
C1—N2—C8—C9	−90.08 (17)	N3—C16—C17—C18	0.4 (3)
C14—N2—C8—C13	−147.52 (15)	C16—C17—C18—C19	−1.3 (3)
C1—N2—C8—C13	35.31 (19)	N3—C15—C19—C18	−0.2 (3)
N2—C8—C9—C10	−178.34 (13)	C14—C15—C19—C18	−175.81 (15)
C13—C8—C9—C10	56.45 (17)	C17—C18—C19—C15	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.877 (12)	2.067 (11)	2.908 (3)	160.4 (18)
O1w—H1w···O2	0.84 (2)	1.98 (2)	2.820 (3)	173.7 (19)
O1w—H2w···O1wii	0.84 (3)	1.97 (3)	2.773 (4)	162 (4)
O1w—H3w···O1wiii	0.84 (3)	1.98 (3)	2.799 (4)	167 (4)
C17—H17···O1wiv	0.95	2.59	3.517 (4)	164
C18—H18···O2v	0.95	2.47	3.367 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.88 (1)	2.07 (1)	2.908 (3)	160 (2)
O1w—H1w⋯O2	0.84 (2)	1.98 (2)	2.820 (3)	174 (2)
O1w—H2w⋯O1wii	0.84 (3)	1.97 (3)	2.773 (4)	162 (4)
O1w—H3w⋯O1wiii	0.84 (3)	1.98 (3)	2.799 (4)	167 (4)
C17—H17⋯O1wiv	0.95	2.59	3.517 (4)	164
C18—H18⋯O2v	0.95	2.47	3.367 (4)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .