1,3-Dicyclo­hexyl-1-isonicotinoylurea monohydrate

Wang, C.-K.; Zhou, F.-Y.

doi:10.1107/S1600536808019430

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1451

doi:10.1107/S1600536808019430

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1,3-Dicyclohexyl-1-isonicotinoylurea monohydrate

Cun-Kuan Wang ^a ^* and Feng-Yan Zhou ^b

^aFaculty of Yang-Ming, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China, and ^bDepartment of Chemistry, Zaozhuang University, Zaozhuang, Shandong 277100, People's Republic of China
^*Correspondence e-mail: wcklx@nbu.edu.cn

(Received 19 May 2008; accepted 26 June 2008; online 9 July 2008)

The title organic compound, C₁₉H₂₇N₃O₂·H₂O, was synthesized from methylene dicyclohexylamine, 4-pyridinecarboxylic acid and N,N′-dicyclohexylcarbodiimide. The water molecule is involved in intermolecular hydrogen bonds, linking symmetry-related urea molecules into a two-dimensional supramolecular 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_r = 347.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.119
S = 1.04
4284 reflections
342 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x, -y, -z; (ii) -x+1, -y, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

Pyridine derivatives are important intermediates widely used in the synthesis of drugs (Wachter et al., 1998; Jew et al., 2003) and pesticides (Li et al., 2006; Mu & Qin, 2003). The title organic compound, 1,3-dicyclohexyl-1-isonicotinoyl-urea, is an intermediate for the synthesis of an anti-tuberculosis drug (Iyer et al., 1971). We report here its synthesis and the crystal structure of its hydrate.

The title compound was synthesized from methylene dicyclohexylamine, 4-pyridinecarboxylic acid and N,N'-dicyclohexylcarbodiimide. Asymmetric unit of the crystal structure consists of the organic molecule and one H₂O molecule, C₁₉H₂₇N₃O₂.H₂O. As shown in Fig. 1 and Table 1, the cyclohexyl groups display chair-type conformation. Interestingly, there are some strong intermolecular hydrogen bonds between the organic molecules and the crystal water. Thus each water effectively links two molecules as O–H···O donor to their O=C groups and accepts one N–H···O hydrogen bridge from a third molecule into a novel two-dimensional supramolecular ladder-like structure through both O—H···O and N—H···O hydrogen bonds (Fig.2 and Table 2).

Related literature top

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

Experimental top

Methylene dicyclohexylamine (0.21 g, 1 mmol), 4-pyridinecarboxylic acid (0.12 g, 1 mmol) and N,N'-dicyclohexylcarbodiimide (0.25 g, 1.2 mmol) were added to a 50 ml round bottom flask, then added dichloromethane (25 ml). The mixture was stirred for 12 h at 298 K, after that the reaction mixture was washed with water (10 ml × 3). The organic layer was dried with anhydrous Na₂SO₄ and evaporated in vacuo to give a residue. The crude product was purified by column chromatography (SiO₂–EtOAc and hexane, 1:10) to afford the title compound as a colorless solid (yield 69%). ¹H NMR (400 MHz, CDCl₃): d 8.57 (d, J = 5.6 Hz, 2 H), 7.37 (d, J = 5.6 Hz, 2 H), 4.16–4.11 (m, 1 H), 3.27–3.22 (m, 1 H), 1.81–1.64 (m, 8 H), 1.60–1.57 (m, 2 H), 1.51–1.22 (m, 4 H), 1.17–1.08 (m, 2 H), 1.00–0.94 (m, 2 H), 0.85–0.76 (m, 2 H).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title complex with the atom-numbering scheme. Atomic displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. View of the two-dimensional hydrogen-bonded supramolecular structure.

1,3-Dicyclohexyl-1-isonicotinoylurea monohydrate top

Crystal data top

C₁₉H₂₇N₃O₂·H₂O	Z = 2
M_r = 347.45	F(000) = 376
Triclinic, P1	D_x = 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 = 3.1–27.5°
c = 13.248 (3) Å	µ = 0.08 mm⁻¹
α = 98.55 (3)°	T = 298 K
β = 94.11 (3)°	Block, colorless
γ = 97.49 (3)°	0.40 × 0.33 × 0.28 mm
V = 958.0 (3) Å³

Data collection top

Bruker SMART CCD APEXII diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.40 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.968, T_max = 0.977	l = −17→17
9385 measured reflections

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.054P)² + 0.1047P] where P = (F_o² + 2F_c²)/3
4284 reflections	(Δ/σ)_max < 0.001
342 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₂₇N₃O₂·H₂O	γ = 97.49 (3)°
M_r = 347.45	V = 958.0 (3) Å³
Triclinic, P1	Z = 2
a = 6.6694 (13) Å	Mo Kα radiation
b = 11.106 (2) Å	µ = 0.08 mm⁻¹
c = 13.248 (3) Å	T = 298 K
α = 98.55 (3)°	0.40 × 0.33 × 0.28 mm
β = 94.11 (3)°

Data collection top

Bruker SMART CCD APEXII diffractometer	4284 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2948 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.977	R_int = 0.029
9385 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.14 e Å⁻³
4284 reflections	Δρ_min = −0.19 e Å⁻³
342 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₇N₃O₂·H₂O
M_r	347.45
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.6694 (13), 11.106 (2), 13.248 (3)
α, β, γ (°)	98.55 (3), 94.11 (3), 97.49 (3)
V (Å³)	958.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.33 × 0.28

Data collection
Diffractometer	Bruker SMART CCD APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	9385, 4284, 2948
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.119, 1.05
No. of reflections	4284
No. of parameters	342
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

O1—C19	1.2253 (16)	N3—C19	1.3587 (18)
O2—C17	1.2239 (17)	N3—C17	1.4443 (17)
N2—C17	1.3222 (19)	N3—C16	1.4957 (17)
N2—C15	1.4628 (18)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z; (ii) −x+1, −y, −z.

Acknowledgements

The authors are grateful to the K. C. Wong Magna Fund of Ningbo University.

References

Bruker (2003). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Iyer, K. S. N., Iyer, B. H. & Sirsi, M. (1971). J. Indian Chem. Soc. 48, 182–184. CAS Google Scholar
Jew, S., Park, B., Lim, D., Kim, M. G., Chung, I. K., Kim, J. H., Hong, C. I., Kim, J.-K., Park, H.-J., Lee, J.-H. & Park, H. (2003). Bioorg. Med. Chem. Lett. 13, 609–612. CrossRef PubMed CAS Google Scholar
Li, G., Qian, X., Cui, J., Huang, Q., Zhang, R. & Guan, H. (2006). J. Agric. Food Chem. 54, 125–129. Web of Science CrossRef PubMed CAS Google Scholar
Mu, C. & Qin, Z. (2003). Modern Agrochem. 2, 1–6. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wachter, G. A., Davis, M. C., Martin, A. R. & Franzblau, S. G. (1998). J. Med. Chem. 41, 2436–2438. CrossRef CAS PubMed Google Scholar