organic compounds
N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridin-2-amine monohydrate
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
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
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Data collection
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 2004); cell 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
10.1107/S1600536810022816/pv2288sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810022816/pv2288Isup2.hkl
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.
An
could not be determined dfue to lack of sufficient dispersion effects. Therefore, Friedel pairs (1894) were merged. Positional parameters of all the H atoms bonded to C atoms were calculated geometrically and were allowed to ride on the C atoms to which they were bonded, with C—H distances of 0.95Å (CH), 0.98Å (CH3) or 0.99Å (CH2), and with Uiso(H) = 1.2Ueq of the parent atoms. The H-atoms bonded to N and O atoms were taken from a difference map and were allowed to refine freely.Data collection: RAPID-AUTO (Rigaku, 2004); cell
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).Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level. |
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 monochromator | 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 |
C18H24N4O·H2O | V = 1831.2 (7) Å3 |
Mr = 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 |
Rigaku R-AXIS Spider diffractometer | 1985 reflections with I > 2σ(I) |
14086 measured reflections | Rint = 0.049 |
2261 independent reflections |
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 | Δρmax = 0.18 e Å−3 |
2261 reflections | Δρmin = −0.15 e Å−3 |
230 parameters |
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 |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.18, −0.15 |
Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lebars, D., Lemaire, C., Ginovart, N., Plenevaux, A., Aerts, J., Brihaye, C., Hassoun, W., Leviel, V., Mekhsian, P., Weissmann, D., Pujol, J. F., Luxen, A., & Comar, D. (1998). Nucl. Med. Biol. 25, 343–350. Web of Science CAS PubMed Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhuang, Z. P., Kung, M. P. & Kung, H. F. (1994). J. Med. Chem. 37, 1406–1407. CrossRef CAS PubMed Web of Science Google Scholar
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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-HT1A) 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).