N-{2-[4-(2-Meth­oxy­phen­yl)piperazin-1-yl]eth­yl}pyridin-2-amine monohydrate

Jiang, Q.-F.; Lu, C.-X.

doi:10.1107/S1600536810022816

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1727

doi:10.1107/S1600536810022816

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N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridin-2-amine monohydrate

Quan-Fu Jiang ^a and Chun-Xiong Lu ^a ^*

^aKey Laboratory of Nuclear Medicine, Ministry of Health, Jiangsu Key Laboratory of Molecular Nuclear Medicine, Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: luchunxiong@yahoo.com.cn

(Received 27 May 2010; accepted 14 June 2010; online 23 June 2010)

In the title compound, C₁₈H₂₄N₄O·H₂O, the piperizine ring adopts a chair conformation and the dihedral angle between the phenyl and pyridine rings is 39.9 (3)°. The comformations of the attachment of the anisole and N-ethylpyridin-2-amine groups to the piperazine ring are +antiperiplanar. An intramolecular C—H⋯O interaction occurs. In the crystal, the water molecule links the molecules into chains through O—H⋯N hydrogen bonds. Weak N—H⋯O, C—H⋯N and C—H⋯O interactions further stabilize the crystal structure.

Related literature

For the use of the title compound in the synthesis of receptor imaging agents, see: Lebars et al. (1998 ); Zhuang et al. (1994 ).

Experimental

Crystal data

C₁₈H₂₄N₄O·H₂O
M_r = 330.43
Orthorhombic, P n a 2₁
a = 13.451 (3) Å
b = 19.847 (4) Å
c = 6.8596 (15) Å
V = 1831.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.40 × 0.23 × 0.09 mm

Data collection

Rigaku R-AXIS Spider diffractometer
14086 measured reflections
2261 independent reflections
1985 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.091
S = 1.00
2261 reflections
230 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H0A⋯N1ⁱ	0.87 (3)	2.01 (3)	2.877 (3)	179 (4)
O2—H0B⋯N3	0.83 (3)	2.01 (3)	2.831 (2)	174 (3)
N2—H2N⋯O2ⁱ	0.83 (3)	2.05 (3)	2.864 (3)	168 (3)
C3—H3⋯N4ⁱⁱ	0.95	2.56	3.471 (3)	161
C10—H10A⋯O1	0.99	2.36	2.957 (3)	118
C15—H15⋯O2ⁱⁱⁱ	0.95	2.58	3.379 (3)	142
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 I, global. DOI: 10.1107/S1600536810022816/pv2288sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022816/pv2288Isup2.hkl

checkCIF report

Comment top

N-(2-(4-(2-Methoxyphenyl)piperazin-1-yl)ethyl)pyridin-2-amine, (I), is an important intermediate product in the synthesis of ¹³¹I-MPPI (Zhuang et al., 1994) and ¹⁸F-MPPF (Lebars et al., 1998), serotonin(5-HT_1A) receptor imaging agents (¹³¹I-MPPI = 4-(2'-methoxypheny)-1-[2'-(N-2''-pyridinyl)- p-¹³¹I-iodobenzamido]ethyl-piperazine and ¹⁸F-MPPF = 4-(2'-methoxyphenyl)-1-[2'-(N-2''-pyridinyl) -p-¹⁸F-fluorobenzamido]ethylpiperazine). We report here the crystal structure of (I).hydrate (Fig. 1). The molecule of (I) consists of an anisole and an N-ethylpyridin-2-amine arms connected to a piperazine ring. The piperazine ring adopts a chair conformation. The dihedral angle between the phenyl and pyridine rings is 39.9 (3)°. The comformation of the attachment of the anisole and N-ethylpyridin-2-amine groups to the piperazine ring are best described by the torsion angles of 168.35 (19)° and 179.45 (17)° for C12—N4—C10—C11 and C7—N3—C8—C9, respectively; i.e. they adopt +antiperiplanar conformations. The molecules are linked through hydrogen-bonding interactions of types O—H···O, N—H···O and C—H···O (Table 1).

Related literature top

For the use of the title compound in the synthesis of receptor imaging agents, see: Lebars et al. (1998); Zhuang et al. (1994).

Experimental top

The title compound was synthesized according to the method reported in the literature (Zhuang et al., 1994) and crystallized from a mixed solvent composed of acetone and water (1:1); colorless block-shaped crystals were obtained after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); 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. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level.

N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridin-2-amine monohydrate top

Crystal data top

C₁₈H₂₄N₄O·H₂O	F(000) = 712
M_r = 330.43	D_x = 1.199 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4880 reflections
a = 13.451 (3) Å	θ = 3.0–27.5°
b = 19.847 (4) Å	µ = 0.08 mm⁻¹
c = 6.8596 (15) Å	T = 153 K
V = 1831.2 (7) Å³	Prism, colorless
Z = 4	0.40 × 0.23 × 0.09 mm

Data collection top

Rigaku R-AXIS Spider diffractometer	1985 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.049
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −17→17
14086 measured reflections	k = −25→22
2261 independent reflections	l = −8→8

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0505P)² + 0.160P] where P = (F_o² + 2F_c²)/3
2261 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₄N₄O·H₂O	V = 1831.2 (7) Å³
M_r = 330.43	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.451 (3) Å	µ = 0.08 mm⁻¹
b = 19.847 (4) Å	T = 153 K
c = 6.8596 (15) Å	0.40 × 0.23 × 0.09 mm

Data collection top

Rigaku R-AXIS Spider diffractometer	1985 reflections with I > 2σ(I)
14086 measured reflections	R_int = 0.049
2261 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.18 e Å⁻³
2261 reflections	Δρ_min = −0.15 e Å⁻³
230 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.43965 (12)	0.13354 (8)	0.6019 (3)	0.0352 (4)
O2	0.35365 (13)	0.46544 (8)	0.6564 (3)	0.0296 (4)
N1	0.75758 (14)	0.58179 (9)	0.4876 (3)	0.0254 (4)
N2	0.69260 (15)	0.52222 (10)	0.7505 (3)	0.0258 (4)
N3	0.52175 (13)	0.38007 (8)	0.6319 (3)	0.0218 (4)
N4	0.44650 (13)	0.25939 (8)	0.4558 (3)	0.0222 (4)
C1	0.82362 (19)	0.62843 (12)	0.4242 (4)	0.0341 (6)
H1	0.8274	0.6364	0.2879	0.041*
C2	0.88518 (19)	0.66487 (13)	0.5425 (4)	0.0357 (6)
H2	0.9308	0.6966	0.4900	0.043*
C3	0.87886 (17)	0.65392 (12)	0.7421 (4)	0.0316 (6)
H3	0.9195	0.6789	0.8293	0.038*
C4	0.81411 (17)	0.60715 (11)	0.8117 (3)	0.0267 (5)
H4	0.8095	0.5990	0.9479	0.032*
C5	0.75372 (15)	0.57077 (10)	0.6798 (3)	0.0212 (5)
C6	0.62161 (16)	0.48524 (10)	0.6333 (3)	0.0257 (5)
H6A	0.6490	0.4776	0.5012	0.031*
H6B	0.5593	0.5115	0.6204	0.031*
C7	0.60037 (17)	0.41825 (11)	0.7313 (3)	0.0251 (5)
H7A	0.6620	0.3910	0.7333	0.030*
H7B	0.5802	0.4265	0.8681	0.030*
C8	0.55437 (16)	0.35756 (11)	0.4378 (3)	0.0228 (5)
H8A	0.6145	0.3291	0.4509	0.027*
H8B	0.5718	0.3972	0.3572	0.027*
C9	0.47335 (16)	0.31789 (10)	0.3383 (3)	0.0243 (5)
H9A	0.4142	0.3469	0.3195	0.029*
H9B	0.4966	0.3029	0.2084	0.029*
C10	0.41288 (17)	0.28054 (11)	0.6490 (3)	0.0283 (5)
H10A	0.3967	0.2404	0.7288	0.034*
H10B	0.3520	0.3083	0.6367	0.034*
C11	0.49388 (19)	0.32103 (11)	0.7477 (3)	0.0286 (5)
H11A	0.4704	0.3359	0.8776	0.034*
H11B	0.5530	0.2921	0.7671	0.034*
C12	0.38607 (15)	0.21023 (10)	0.3614 (3)	0.0243 (5)
C13	0.33403 (17)	0.22331 (11)	0.1915 (4)	0.0300 (5)
H13	0.3335	0.2678	0.1403	0.036*
C14	0.28283 (19)	0.17297 (13)	0.0947 (4)	0.0394 (6)
H14	0.2476	0.1831	−0.0218	0.047*
C15	0.28287 (19)	0.10831 (13)	0.1670 (4)	0.0388 (6)
H15	0.2484	0.0736	0.0997	0.047*
C16	0.33326 (18)	0.09392 (12)	0.3380 (4)	0.0338 (6)
H16	0.3322	0.0494	0.3889	0.041*
C17	0.38516 (16)	0.14392 (11)	0.4357 (4)	0.0274 (5)
C18	0.4404 (2)	0.06745 (13)	0.6815 (5)	0.0505 (8)
H18A	0.3720	0.0530	0.7072	0.061*
H18B	0.4782	0.0674	0.8036	0.061*
H18C	0.4715	0.0364	0.5886	0.061*
H0A	0.320 (2)	0.4515 (15)	0.757 (5)	0.051 (9)*
H2N	0.686 (2)	0.5217 (13)	0.871 (4)	0.033 (7)*
H0B	0.400 (2)	0.4384 (17)	0.647 (6)	0.063 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0412 (9)	0.0224 (8)	0.0420 (10)	−0.0083 (7)	−0.0081 (9)	0.0084 (8)
O2	0.0339 (9)	0.0310 (9)	0.0239 (9)	0.0051 (8)	0.0037 (8)	0.0022 (7)
N1	0.0265 (10)	0.0241 (10)	0.0257 (10)	−0.0036 (8)	−0.0005 (8)	−0.0006 (8)
N2	0.0314 (10)	0.0257 (9)	0.0203 (10)	−0.0092 (8)	−0.0007 (9)	−0.0035 (8)
N3	0.0277 (9)	0.0194 (8)	0.0183 (9)	−0.0054 (7)	0.0004 (8)	0.0000 (7)
N4	0.0256 (9)	0.0182 (8)	0.0228 (9)	−0.0045 (7)	−0.0002 (8)	−0.0013 (8)
C1	0.0380 (14)	0.0343 (13)	0.0300 (13)	−0.0063 (11)	0.0025 (11)	0.0049 (11)
C2	0.0341 (13)	0.0321 (13)	0.0410 (15)	−0.0149 (11)	0.0015 (12)	0.0029 (11)
C3	0.0253 (11)	0.0277 (12)	0.0418 (14)	−0.0039 (10)	−0.0071 (11)	−0.0046 (11)
C4	0.0261 (11)	0.0277 (11)	0.0263 (12)	−0.0004 (10)	−0.0034 (10)	−0.0037 (10)
C5	0.0206 (10)	0.0175 (10)	0.0256 (11)	0.0019 (8)	0.0008 (9)	−0.0023 (9)
C6	0.0300 (11)	0.0206 (10)	0.0264 (12)	−0.0066 (9)	−0.0063 (10)	0.0021 (9)
C7	0.0306 (11)	0.0240 (11)	0.0208 (11)	−0.0045 (9)	−0.0066 (10)	−0.0002 (9)
C8	0.0256 (10)	0.0197 (10)	0.0231 (11)	−0.0043 (9)	0.0033 (10)	0.0005 (9)
C9	0.0289 (11)	0.0198 (10)	0.0242 (11)	−0.0032 (9)	−0.0005 (10)	−0.0014 (9)
C10	0.0350 (12)	0.0241 (11)	0.0258 (12)	−0.0061 (9)	0.0079 (11)	−0.0004 (10)
C11	0.0409 (13)	0.0247 (11)	0.0204 (11)	−0.0102 (10)	−0.0004 (11)	0.0019 (10)
C12	0.0203 (10)	0.0233 (10)	0.0292 (12)	−0.0034 (9)	0.0019 (10)	−0.0044 (10)
C13	0.0307 (12)	0.0273 (12)	0.0320 (13)	−0.0040 (10)	−0.0009 (11)	−0.0030 (10)
C14	0.0384 (13)	0.0416 (14)	0.0381 (14)	−0.0114 (11)	−0.0092 (13)	−0.0024 (13)
C15	0.0379 (13)	0.0358 (13)	0.0427 (14)	−0.0144 (11)	−0.0008 (13)	−0.0110 (12)
C16	0.0330 (13)	0.0237 (11)	0.0448 (15)	−0.0093 (10)	0.0057 (12)	−0.0036 (11)
C17	0.0243 (11)	0.0245 (11)	0.0335 (13)	−0.0024 (9)	0.0026 (10)	−0.0029 (10)
C18	0.0586 (18)	0.0296 (13)	0.063 (2)	−0.0095 (12)	−0.0168 (17)	0.0175 (14)

Geometric parameters (Å, º) top

O1—C17	1.371 (3)	C7—H7A	0.9900
O1—C18	1.421 (3)	C7—H7B	0.9900
O2—H0A	0.88 (3)	C8—C9	1.508 (3)
O2—H0B	0.83 (3)	C8—H8A	0.9900
N1—C5	1.338 (3)	C8—H8B	0.9900
N1—C1	1.354 (3)	C9—H9A	0.9900
N2—C5	1.356 (3)	C9—H9B	0.9900
N2—C6	1.448 (3)	C10—C11	1.514 (3)
N2—H2N	0.83 (3)	C10—H10A	0.9900
N3—C11	1.464 (3)	C10—H10B	0.9900
N3—C7	1.469 (3)	C11—H11A	0.9900
N3—C8	1.472 (3)	C11—H11B	0.9900
N4—C12	1.426 (3)	C12—C13	1.384 (3)
N4—C9	1.459 (3)	C12—C17	1.411 (3)
N4—C10	1.462 (3)	C13—C14	1.383 (3)
C1—C2	1.366 (4)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.376 (4)
C2—C3	1.389 (4)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.385 (4)
C3—C4	1.360 (3)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.386 (3)
C4—C5	1.414 (3)	C16—H16	0.9500
C4—H4	0.9500	C18—H18A	0.9800
C6—C7	1.517 (3)	C18—H18B	0.9800
C6—H6A	0.9900	C18—H18C	0.9800
C6—H6B	0.9900

C17—O1—C18	117.5 (2)	H8A—C8—H8B	108.1
H0A—O2—H0B	105 (3)	N4—C9—C8	110.15 (18)
C5—N1—C1	117.0 (2)	N4—C9—H9A	109.6
C5—N2—C6	124.1 (2)	C8—C9—H9A	109.6
C5—N2—H2N	115.1 (19)	N4—C9—H9B	109.6
C6—N2—H2N	118.7 (19)	C8—C9—H9B	109.6
C11—N3—C7	110.20 (17)	H9A—C9—H9B	108.1
C11—N3—C8	108.93 (16)	N4—C10—C11	109.59 (18)
C7—N3—C8	111.22 (17)	N4—C10—H10A	109.8
C12—N4—C9	115.76 (18)	C11—C10—H10A	109.8
C12—N4—C10	115.61 (17)	N4—C10—H10B	109.8
C9—N4—C10	110.42 (16)	C11—C10—H10B	109.8
N1—C1—C2	124.7 (2)	H10A—C10—H10B	108.2
N1—C1—H1	117.7	N3—C11—C10	111.48 (19)
C2—C1—H1	117.7	N3—C11—H11A	109.3
C1—C2—C3	117.7 (2)	C10—C11—H11A	109.3
C1—C2—H2	121.1	N3—C11—H11B	109.3
C3—C2—H2	121.1	C10—C11—H11B	109.3
C4—C3—C2	119.5 (2)	H11A—C11—H11B	108.0
C4—C3—H3	120.3	C13—C12—C17	118.3 (2)
C2—C3—H3	120.3	C13—C12—N4	122.9 (2)
C3—C4—C5	119.5 (2)	C17—C12—N4	118.6 (2)
C3—C4—H4	120.3	C14—C13—C12	121.4 (2)
C5—C4—H4	120.3	C14—C13—H13	119.3
N1—C5—N2	119.5 (2)	C12—C13—H13	119.3
N1—C5—C4	121.7 (2)	C15—C14—C13	120.0 (2)
N2—C5—C4	118.8 (2)	C15—C14—H14	120.0
N2—C6—C7	108.79 (18)	C13—C14—H14	120.0
N2—C6—H6A	109.9	C14—C15—C16	119.9 (2)
C7—C6—H6A	109.9	C14—C15—H15	120.1
N2—C6—H6B	109.9	C16—C15—H15	120.1
C7—C6—H6B	109.9	C15—C16—C17	120.6 (2)
H6A—C6—H6B	108.3	C15—C16—H16	119.7
N3—C7—C6	112.45 (17)	C17—C16—H16	119.7
N3—C7—H7A	109.1	O1—C17—C16	124.3 (2)
C6—C7—H7A	109.1	O1—C17—C12	115.84 (19)
N3—C7—H7B	109.1	C16—C17—C12	119.8 (2)
C6—C7—H7B	109.1	O1—C18—H18A	109.5
H7A—C7—H7B	107.8	O1—C18—H18B	109.5
N3—C8—C9	110.64 (18)	H18A—C18—H18B	109.5
N3—C8—H8A	109.5	O1—C18—H18C	109.5
C9—C8—H8A	109.5	H18A—C18—H18C	109.5
N3—C8—H8B	109.5	H18B—C18—H18C	109.5
C9—C8—H8B	109.5

C5—N1—C1—C2	−0.5 (4)	C7—N3—C11—C10	−179.99 (19)
N1—C1—C2—C3	−0.8 (4)	C8—N3—C11—C10	−57.7 (2)
C1—C2—C3—C4	1.3 (4)	N4—C10—C11—N3	58.0 (2)
C2—C3—C4—C5	−0.5 (4)	C9—N4—C12—C13	−16.5 (3)
C1—N1—C5—N2	−176.7 (2)	C10—N4—C12—C13	114.8 (2)
C1—N1—C5—C4	1.4 (3)	C9—N4—C12—C17	158.5 (2)
C6—N2—C5—N1	−7.0 (3)	C10—N4—C12—C17	−70.1 (3)
C6—N2—C5—C4	174.9 (2)	C17—C12—C13—C14	−0.6 (3)
C3—C4—C5—N1	−0.9 (3)	N4—C12—C13—C14	174.5 (2)
C3—C4—C5—N2	177.2 (2)	C12—C13—C14—C15	0.1 (4)
C5—N2—C6—C7	155.8 (2)	C13—C14—C15—C16	0.8 (4)
C11—N3—C7—C6	−171.59 (19)	C14—C15—C16—C17	−1.1 (4)
C8—N3—C7—C6	67.5 (2)	C18—O1—C17—C16	−1.8 (3)
N2—C6—C7—N3	174.53 (18)	C18—O1—C17—C12	179.8 (2)
C11—N3—C8—C9	57.8 (2)	C15—C16—C17—O1	−177.7 (2)
C7—N3—C8—C9	179.45 (17)	C15—C16—C17—C12	0.6 (4)
C12—N4—C9—C8	−167.51 (17)	C13—C12—C17—O1	178.7 (2)
C10—N4—C9—C8	58.7 (2)	N4—C12—C17—O1	3.4 (3)
N3—C8—C9—N4	−58.9 (2)	C13—C12—C17—C16	0.3 (3)
C12—N4—C10—C11	168.35 (19)	N4—C12—C17—C16	−175.0 (2)
C9—N4—C10—C11	−57.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H0A···N1ⁱ	0.87 (3)	2.01 (3)	2.877 (3)	179 (4)
O2—H0B···N3	0.83 (3)	2.01 (3)	2.831 (2)	174 (3)
N2—H2N···O2ⁱ	0.83 (3)	2.05 (3)	2.864 (3)	168 (3)
C3—H3···N4ⁱⁱ	0.95	2.56	3.471 (3)	161
C10—H10A···O1	0.99	2.36	2.957 (3)	118
C15—H15···O2ⁱⁱⁱ	0.95	2.58	3.379 (3)	142

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+3/2, y+1/2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄N₄O·H₂O
M_r	330.43
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	153
a, b, c (Å)	13.451 (3), 19.847 (4), 6.8596 (15)
V (Å³)	1831.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.23 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS Spider diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14086, 2261, 1985
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.091, 1.00
No. of reflections	2261
No. of parameters	230
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H0A···N1ⁱ	0.87 (3)	2.01 (3)	2.877 (3)	179 (4)
O2—H0B···N3	0.83 (3)	2.01 (3)	2.831 (2)	174 (3)
N2—H2N···O2ⁱ	0.83 (3)	2.05 (3)	2.864 (3)	168 (3)
C3—H3···N4ⁱⁱ	0.9500	2.5600	3.471 (3)	161.00
C10—H10A···O1	0.9900	2.3600	2.957 (3)	118.00
C15—H15···O2ⁱⁱⁱ	0.9500	2.5800	3.379 (3)	142.00

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+3/2, y+1/2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangsu Province (BK2008112) and the Science Foundation of the Health Department of Jiangsu Province (H200624).

References

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