1,3-Dicyclo-hexyl-1-isonicotinoylurea monohydrate.

The title organic compound, C(19)H(27)N(3)O(2)·H(2)O, was synthesized from methyl-ene dicyclo-hexyl-amine, 4-pyridine-carboxylic acid and N,N'-dicyclo-hexyl-carbodiimide. The water molecule is involved in inter-molecular hydrogen bonds, linking symmetry-related urea mol-ecules into a two-dimensional supra-molecular ladder-like structure.

Related literature

For related literature, see: Iyer et al. (1971 ▶); Jew et al. (2003 ▶); Li et al. (2006 ▶); Mu & Qin (2003 ▶); Wachter et al. (1998 ▶).

Experimental

Crystal data

C19H27N3O2·H2O

M = 347.45

Triclinic,

a = 6.6694 (13) Å

b = 11.106 (2) Å

c = 13.248 (3) Å

α = 98.55 (3)°

β = 94.11 (3)°

γ = 97.49 (3)°

V = 958.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.40 × 0.33 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.977

9385 measured reflections

4284 independent reflections

2948 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.04

4284 reflections

342 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019430/cs2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019430/cs2080Isup2.hkl

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

C19H27N3O2·H2O	Z = 2
Mr = 347.45	F000 = 376
Triclinic, P1	Dx = 1.205 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.6694 (13) Å	Cell parameters from 3059 reflections
b = 11.106 (2) Å	θ = 3.1–27.5º
c = 13.248 (3) Å	µ = 0.08 mm−1
α = 98.55 (3)º	T = 298 (2) K
β = 94.11 (3)º	Block, colorless
γ = 97.49 (3)º	0.40 × 0.33 × 0.28 mm
V = 958.0 (3) Å3

Bruker SMART CCD APEXII diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 8.40 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 3.1º
ω scans	h = −8→7
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.968, Tmax = 0.977	l = −17→17
9385 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.054P)2 + 0.1047P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4284 reflections	Δρmax = 0.14 e Å−3
342 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	0.25983 (16)	0.03443 (9)	0.01466 (8)	0.0451 (3)
O2	0.57498 (15)	0.02624 (10)	0.32408 (8)	0.0437 (3)
O3	0.11137 (18)	−0.00473 (13)	−0.19210 (11)	0.0546 (3)
N1	0.2456 (3)	−0.40235 (13)	0.05844 (13)	0.0635 (4)
N2	0.23694 (19)	−0.04403 (11)	0.29989 (9)	0.0357 (3)
N3	0.38649 (17)	0.06272 (10)	0.18085 (8)	0.0325 (3)
C1	0.6570 (4)	0.39594 (16)	0.21113 (19)	0.0636 (5)
C2	0.3121 (3)	0.39686 (17)	0.2711 (2)	0.0667 (6)
C3	0.0813 (4)	−0.32783 (19)	0.47794 (19)	0.0731 (6)
C4	−0.0296 (4)	−0.2166 (2)	0.48890 (18)	0.0690 (6)
C5	0.0909 (3)	−0.34257 (17)	0.03668 (17)	0.0650 (5)
C6	0.5319 (3)	0.45402 (16)	0.29056 (16)	0.0602 (5)
C7	0.2898 (3)	0.25718 (15)	0.26796 (16)	0.0536 (5)
C8	0.6370 (3)	0.25617 (14)	0.20801 (17)	0.0513 (4)
C9	0.3026 (3)	−0.29165 (18)	0.46441 (15)	0.0593 (5)
C10	0.4223 (3)	−0.33354 (15)	0.09157 (14)	0.0524 (4)
C11	0.1057 (3)	−0.21635 (15)	0.04690 (14)	0.0498 (4)
C12	−0.0014 (3)	−0.1451 (2)	0.40009 (15)	0.0539 (4)
C13	0.3287 (3)	−0.22376 (17)	0.37377 (14)	0.0505 (4)
C14	0.4515 (3)	−0.20672 (14)	0.10728 (12)	0.0414 (4)
C15	0.2219 (2)	−0.11014 (14)	0.38727 (11)	0.0371 (3)
C16	0.4161 (2)	0.19968 (12)	0.18824 (12)	0.0376 (3)
C17	0.4089 (2)	0.01254 (12)	0.27488 (10)	0.0326 (3)
C18	0.2898 (2)	−0.14614 (12)	0.08435 (10)	0.0351 (3)
C19	0.3093 (2)	−0.00917 (12)	0.09085 (10)	0.0324 (3)
H1	0.289 (2)	−0.0558 (14)	0.4476 (12)	0.039 (4)*
H2	0.365 (2)	0.2150 (14)	0.1216 (13)	0.045 (4)*
H3	0.579 (3)	−0.1618 (15)	0.1334 (12)	0.047 (4)*
H4	−0.010 (3)	−0.1756 (17)	0.0266 (14)	0.064 (5)*
H5	0.260 (3)	−0.2770 (17)	0.3092 (15)	0.063 (5)*
H6	0.153 (4)	−0.014 (2)	−0.128 (2)	0.093 (8)*
H7	−0.061 (3)	−0.1957 (18)	0.3374 (16)	0.064 (6)*
H8	0.341 (3)	0.2358 (16)	0.3374 (15)	0.060 (5)*
H9	0.542 (3)	0.5415 (19)	0.2889 (15)	0.074 (6)*
H10	0.118 (3)	−0.0381 (17)	0.2633 (15)	0.063 (5)*
H11	0.686 (3)	0.2370 (19)	0.2787 (17)	0.078 (6)*
H12	0.212 (4)	−0.019 (2)	−0.2310 (18)	0.084 (7)*
H13	0.538 (3)	−0.3773 (17)	0.1074 (14)	0.063 (5)*
H14	0.599 (3)	0.4149 (19)	0.1418 (19)	0.084 (7)*
H15	0.373 (3)	−0.2369 (19)	0.5286 (17)	0.075 (6)*
H16	0.706 (3)	0.2202 (18)	0.1530 (16)	0.072 (6)*
H17	0.473 (3)	−0.1978 (17)	0.3659 (14)	0.065 (6)*
H18	0.587 (3)	0.4396 (17)	0.3617 (16)	0.067 (6)*
H19	0.015 (3)	−0.387 (2)	0.4148 (18)	0.086 (7)*
H20	−0.041 (3)	−0.3951 (19)	0.0133 (16)	0.078 (6)*
H21	0.258 (3)	0.4170 (19)	0.2025 (18)	0.079 (7)*
H22	0.150 (3)	0.2190 (17)	0.2552 (14)	0.066 (6)*
H23	0.067 (3)	−0.369 (2)	0.5385 (18)	0.087 (7)*
H24	0.018 (4)	−0.160 (2)	0.554 (2)	0.094 (8)*
H25	0.379 (3)	−0.3669 (19)	0.4574 (15)	0.072 (6)*
H26	0.235 (3)	0.431 (2)	0.3277 (19)	0.093 (7)*
H27	−0.064 (3)	−0.0673 (19)	0.4108 (15)	0.071 (6)*
H28	−0.174 (4)	−0.239 (2)	0.4927 (19)	0.099 (8)*
H29	0.800 (4)	0.430 (2)	0.2219 (18)	0.091 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0575 (7)	0.0422 (6)	0.0340 (6)	0.0022 (5)	−0.0074 (5)	0.0113 (5)
O2	0.0385 (6)	0.0526 (6)	0.0395 (6)	0.0011 (5)	−0.0045 (5)	0.0143 (5)
O3	0.0408 (6)	0.0825 (9)	0.0413 (7)	0.0172 (6)	−0.0019 (5)	0.0078 (6)
N1	0.0736 (11)	0.0339 (7)	0.0786 (11)	−0.0003 (8)	0.0038 (9)	0.0040 (7)
N2	0.0354 (7)	0.0420 (7)	0.0322 (6)	0.0058 (5)	0.0029 (5)	0.0134 (5)
N3	0.0406 (7)	0.0281 (6)	0.0287 (6)	0.0027 (5)	0.0015 (5)	0.0066 (4)
C1	0.0734 (14)	0.0375 (9)	0.0786 (15)	−0.0047 (9)	0.0201 (11)	0.0097 (9)
C2	0.0732 (14)	0.0413 (10)	0.0859 (16)	0.0170 (10)	0.0152 (12)	−0.0004 (10)
C3	0.1100 (19)	0.0512 (11)	0.0591 (13)	−0.0050 (12)	0.0115 (12)	0.0254 (10)
C4	0.0696 (14)	0.0793 (15)	0.0660 (14)	0.0037 (12)	0.0264 (11)	0.0335 (12)
C5	0.0594 (12)	0.0423 (10)	0.0837 (14)	−0.0081 (9)	−0.0013 (10)	−0.0042 (9)
C6	0.0873 (15)	0.0319 (9)	0.0589 (12)	0.0045 (9)	0.0076 (10)	0.0019 (8)
C7	0.0506 (11)	0.0397 (9)	0.0706 (13)	0.0082 (8)	0.0159 (9)	0.0022 (8)
C8	0.0533 (10)	0.0342 (8)	0.0661 (12)	−0.0008 (7)	0.0210 (9)	0.0059 (8)
C9	0.0894 (15)	0.0476 (10)	0.0478 (11)	0.0204 (10)	0.0105 (10)	0.0192 (8)
C10	0.0619 (11)	0.0392 (9)	0.0578 (11)	0.0116 (9)	0.0042 (9)	0.0102 (8)
C11	0.0461 (9)	0.0397 (9)	0.0580 (11)	−0.0006 (8)	−0.0036 (8)	−0.0007 (7)
C12	0.0492 (10)	0.0645 (12)	0.0537 (11)	0.0056 (9)	0.0152 (9)	0.0253 (9)
C13	0.0656 (12)	0.0488 (9)	0.0435 (10)	0.0182 (9)	0.0106 (9)	0.0172 (8)
C14	0.0468 (9)	0.0357 (8)	0.0411 (8)	0.0023 (7)	0.0018 (7)	0.0082 (6)
C15	0.0449 (8)	0.0391 (8)	0.0289 (7)	0.0050 (7)	0.0041 (6)	0.0108 (6)
C16	0.0530 (9)	0.0272 (7)	0.0323 (8)	0.0048 (6)	0.0011 (6)	0.0064 (6)
C17	0.0387 (8)	0.0289 (7)	0.0302 (7)	0.0056 (6)	0.0026 (6)	0.0049 (5)
C18	0.0427 (8)	0.0320 (7)	0.0291 (7)	0.0006 (6)	0.0047 (6)	0.0039 (5)
C19	0.0321 (7)	0.0336 (7)	0.0309 (7)	0.0013 (6)	0.0026 (6)	0.0067 (6)

O1—C19	1.2253 (16)	C5—H20	0.99 (2)
O2—C17	1.2239 (17)	C6—H9	0.97 (2)
O3—H6	0.89 (3)	C6—H18	1.03 (2)
O3—H12	0.89 (2)	C7—C16	1.516 (2)
N1—C10	1.325 (2)	C7—H8	1.030 (19)
N1—C5	1.335 (3)	C7—H22	0.96 (2)
N2—C17	1.3222 (19)	C8—C16	1.513 (2)
N2—C15	1.4628 (18)	C8—H11	1.03 (2)
N2—H10	0.91 (2)	C8—H16	0.95 (2)
N3—C19	1.3587 (18)	C9—C13	1.518 (2)
N3—C17	1.4443 (17)	C9—H15	1.01 (2)
N3—C16	1.4957 (17)	C9—H25	1.03 (2)
C1—C6	1.511 (3)	C10—C14	1.379 (2)
C1—C8	1.535 (2)	C10—H13	0.988 (19)
C1—H14	1.03 (2)	C11—C18	1.382 (2)
C1—H29	0.97 (2)	C11—H4	0.98 (2)
C2—C6	1.508 (3)	C12—C15	1.518 (2)
C2—C7	1.533 (2)	C12—H7	0.96 (2)
C2—H21	1.02 (2)	C12—H27	1.00 (2)
C2—H26	0.99 (2)	C13—C15	1.522 (2)
C3—C9	1.509 (3)	C13—H5	1.008 (19)
C3—C4	1.515 (3)	C13—H17	0.98 (2)
C3—H19	1.02 (2)	C14—C18	1.382 (2)
C3—H23	0.99 (2)	C14—H3	0.943 (17)
C4—C12	1.523 (3)	C15—H1	0.969 (16)
C4—H24	0.99 (3)	C16—H2	0.970 (17)
C4—H28	0.97 (3)	C18—C19	1.4988 (19)
C5—C11	1.378 (2)
H6—O3—H12	107 (2)	C1—C8—H16	109.9 (12)
C10—N1—C5	116.45 (15)	H11—C8—H16	114.0 (16)
C17—N2—C15	124.07 (13)	C3—C9—C13	111.55 (18)
C17—N2—H10	118.8 (12)	C3—C9—H15	110.0 (12)
C15—N2—H10	117.0 (12)	C13—C9—H15	108.9 (12)
C19—N3—C17	121.70 (11)	C3—C9—H25	111.3 (11)
C19—N3—C16	119.75 (11)	C13—C9—H25	110.8 (11)
C17—N3—C16	117.70 (11)	H15—C9—H25	104.0 (16)
C6—C1—C8	111.14 (16)	N1—C10—C14	124.03 (17)
C6—C1—H14	105.6 (12)	N1—C10—H13	116.8 (11)
C8—C1—H14	109.7 (12)	C14—C10—H13	119.1 (11)
C6—C1—H29	113.1 (14)	C5—C11—C18	118.67 (17)
C8—C1—H29	108.9 (14)	C5—C11—H4	121.7 (11)
H14—C1—H29	108.3 (19)	C18—C11—H4	119.6 (11)
C6—C2—C7	111.16 (17)	C15—C12—C4	111.31 (16)
C6—C2—H21	107.2 (12)	C15—C12—H7	106.9 (12)
C7—C2—H21	110.3 (12)	C4—C12—H7	109.6 (12)
C6—C2—H26	109.6 (13)	C15—C12—H27	107.6 (11)
C7—C2—H26	107.3 (13)	C4—C12—H27	111.5 (11)
H21—C2—H26	111.3 (18)	H7—C12—H27	109.9 (16)
C9—C3—C4	111.04 (17)	C9—C13—C15	110.16 (14)
C9—C3—H19	109.2 (13)	C9—C13—H5	109.9 (11)
C4—C3—H19	107.8 (12)	C15—C13—H5	105.7 (10)
C9—C3—H23	110.5 (13)	C9—C13—H17	111.8 (11)
C4—C3—H23	109.8 (13)	C15—C13—H17	108.5 (11)
H19—C3—H23	108.4 (18)	H5—C13—H17	110.5 (16)
C3—C4—C12	111.67 (18)	C10—C14—C18	118.81 (16)
C3—C4—H24	111.1 (14)	C10—C14—H3	120.8 (10)
C12—C4—H24	108.5 (14)	C18—C14—H3	120.3 (10)
C3—C4—H28	112.3 (14)	N2—C15—C12	108.20 (13)
C12—C4—H28	108.1 (15)	N2—C15—C13	112.09 (12)
H24—C4—H28	105 (2)	C12—C15—C13	110.68 (15)
N1—C5—C11	123.98 (18)	N2—C15—H1	108.0 (9)
N1—C5—H20	115.5 (11)	C12—C15—H1	110.7 (9)
C11—C5—H20	120.5 (12)	C13—C15—H1	107.1 (9)
C2—C6—C1	110.99 (17)	N3—C16—C8	112.88 (13)
C2—C6—H9	109.3 (12)	N3—C16—C7	110.71 (13)
C1—C6—H9	109.7 (12)	C8—C16—C7	111.38 (14)
C2—C6—H18	108.5 (11)	N3—C16—H2	105.2 (9)
C1—C6—H18	108.6 (11)	C8—C16—H2	108.1 (9)
H9—C6—H18	109.8 (16)	C7—C16—H2	108.2 (9)
C16—C7—C2	110.43 (16)	O2—C17—N2	126.20 (13)
C16—C7—H8	107.0 (10)	O2—C17—N3	120.23 (13)
C2—C7—H8	111.0 (10)	N2—C17—N3	113.55 (12)
C16—C7—H22	110.3 (11)	C11—C18—C14	118.01 (14)
C2—C7—H22	112.4 (11)	C11—C18—C19	118.81 (14)
H8—C7—H22	105.5 (15)	C14—C18—C19	123.02 (13)
C16—C8—C1	110.19 (16)	O1—C19—N3	122.14 (13)
C16—C8—H11	105.7 (12)	O1—C19—C18	119.26 (12)
C1—C8—H11	109.8 (12)	N3—C19—C18	118.59 (12)
C16—C8—H16	107.1 (12)
C9—C3—C4—C12	54.2 (3)	C1—C8—C16—N3	178.11 (14)
C10—N1—C5—C11	−0.1 (3)	C1—C8—C16—C7	−56.6 (2)
C7—C2—C6—C1	56.2 (3)	C2—C7—C16—N3	−177.01 (16)
C8—C1—C6—C2	−56.5 (3)	C2—C7—C16—C8	56.5 (2)
C6—C2—C7—C16	−56.0 (3)	C15—N2—C17—O2	−6.0 (2)
C6—C1—C8—C16	56.4 (2)	C15—N2—C17—N3	175.33 (11)
C4—C3—C9—C13	−56.0 (2)	C19—N3—C17—O2	123.81 (15)
C5—N1—C10—C14	2.1 (3)	C16—N3—C17—O2	−66.79 (17)
N1—C5—C11—C18	−1.7 (3)	C19—N3—C17—N2	−57.40 (17)
C3—C4—C12—C15	−54.4 (3)	C16—N3—C17—N2	111.99 (14)
C3—C9—C13—C15	57.5 (2)	C5—C11—C18—C14	1.6 (2)
N1—C10—C14—C18	−2.2 (3)	C5—C11—C18—C19	177.11 (16)
C17—N2—C15—C12	171.48 (14)	C10—C14—C18—C11	0.2 (2)
C17—N2—C15—C13	−66.20 (19)	C10—C14—C18—C19	−175.11 (14)
C4—C12—C15—N2	179.01 (16)	C17—N3—C19—O1	168.24 (12)
C4—C12—C15—C13	55.8 (2)	C16—N3—C19—O1	−0.9 (2)
C9—C13—C15—N2	−178.00 (15)	C17—N3—C19—C18	−13.44 (19)
C9—C13—C15—C12	−57.1 (2)	C16—N3—C19—C18	177.38 (12)
C19—N3—C16—C8	−115.27 (16)	C11—C18—C19—O1	−52.43 (19)
C17—N3—C16—C8	75.12 (17)	C14—C18—C19—O1	122.84 (16)
C19—N3—C16—C7	119.10 (16)	C11—C18—C19—N3	129.19 (15)
C17—N3—C16—C7	−50.51 (18)	C14—C18—C19—N3	−55.53 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O1	0.89 (3)	1.95 (3)	2.7959 (18)	158 (2)
N2—H10···O3i	0.91 (2)	1.89 (2)	2.7949 (19)	170 (2)
O3—H12···O2ii	0.89 (2)	1.95 (3)	2.8319 (19)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H6⋯O1	0.89 (3)	1.95 (3)	2.7959 (18)	158 (2)
N2—H10⋯O3i	0.91 (2)	1.89 (2)	2.7949 (19)	170 (2)
O3—H12⋯O2ii	0.89 (2)	1.95 (3)	2.8319 (19)	171 (2)

Symmetry codes: (i) ; (ii) .