N-{2-[4-(2-Meth-oxy-phen-yl)piperazin-1-yl]eth-yl}pyridin-2-amine monohydrate.

In the title compound, C(18)H(24)N(4)O·H(2)O, 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-ethyl-pyridin-2-amine groups to the piperazine ring are +anti-periplanar. An intra-molecular C-H⋯O inter-action occurs. In the crystal, the water mol-ecule links the mol-ecules into chains through O-H⋯N hydrogen bonds. Weak N-H⋯O, C-H⋯N and C-H⋯O inter-actions 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 = 330.43

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.091

S = 1.00

2261 reflections

230 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022816/pv2288sup1.cif

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

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

C18H24N4O·H2O	F(000) = 712
Mr = 330.43	Dx = 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

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

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(Fo2) + (0.0505P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
2261 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) .