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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-[4-(2-Meth­­oxy­phen­yl)piperazin-1-yl]-N-(pyridin-2-yl)acetamide

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: ipcom10@163.com

(Received 2 December 2010; accepted 17 December 2010; online 24 December 2010)

In the title compound, C18H22N4O2, the piperizine ring adopts a chair conformation and the dihedral angle between the pyridine and benzene rings is 67.6 (9)°. The conformations of the attachment of the anisole and N-ethyl­pyridin-2-amine groups to the piperazine ring are (+)anti­periplanar. Intra­molecular C—H⋯O and N—H⋯N inter­actions occur. In the crystal, inter­molecular C—H⋯N hydrogen bonds are present. There are two crystallographically independent but identical mol­ecules per asymmetric unit.

Related literature

For the use of the title compound in the synthesis of receptor imaging agents, see: Lebars et al. (1998[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.]); Zhuang et al. (1994[Zhuang, Z. P., Kung, M. P. & Kung, H. F. (1994). J. Med. Chem. 37, 1406-1407.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N4O2

  • Mr = 326.40

  • Triclinic, [P \overline 1]

  • a = 11.595 (4) Å

  • b = 12.382 (4) Å

  • c = 14.073 (4) Å

  • α = 106.228 (4)°

  • β = 91.767 (3)°

  • γ = 114.627 (2)°

  • V = 1738.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 143 K

  • 0.21 × 0.17 × 0.09 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 16957 measured reflections

  • 7823 independent reflections

  • 4689 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.134

  • S = 1.00

  • 7823 reflections

  • 443 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.74 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H03⋯N2 0.85 (2) 2.20 (3) 2.692 (3) 117.0 (19)
N7—H07⋯N6 0.86 (2) 2.26 (3) 2.734 (3) 115.3 (19)
C2—H2⋯N8 0.95 2.44 3.354 (3) 161
C14—H14⋯O2 0.95 2.33 2.923 (3) 120
C20—H20⋯N4 0.95 2.59 3.527 (3) 168

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(pyridin-2-yl)acetamide, (I), is an important intermediate product in the synthesis of 131I-MPPI (Zhuang et al., 1994) and 18 F-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 18 F-MPPF = 4-(2'-methoxyphenyl)-1-[2'-(N-2''-pyridinyl) -p-18 F-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 67.6 (9)°. The conformations of the attachment of the anisole and N-ethylpyridin-2-amine groups to the piperazine ring are best described by the torsion angles of 171.99 (18)° and -174.56 (18)° for C6—N1—C7—C8 and C11—N2—C9—C10, respectively; i.e. they adopt +antiperiplanar conformations. The molecules show intra- and intermolecular hydrogen-bonding interactions of types N—H···N, C—H···N 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); colourless block-shaped crystals were obtained after several days.

Refinement top

The amino H atoms were located in a difference Fourier map and refined with N—H distance restrained to 0.85 Å. 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) =1.2 or 1.5 (methyl) Ueq of the parent atoms.

Structure description top

2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(pyridin-2-yl)acetamide, (I), is an important intermediate product in the synthesis of 131I-MPPI (Zhuang et al., 1994) and 18 F-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 18 F-MPPF = 4-(2'-methoxyphenyl)-1-[2'-(N-2''-pyridinyl) -p-18 F-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 67.6 (9)°. The conformations of the attachment of the anisole and N-ethylpyridin-2-amine groups to the piperazine ring are best described by the torsion angles of 171.99 (18)° and -174.56 (18)° for C6—N1—C7—C8 and C11—N2—C9—C10, respectively; i.e. they adopt +antiperiplanar conformations. The molecules show intra- and intermolecular hydrogen-bonding interactions of types N—H···N, C—H···N and C—H···O (Table 1).

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

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme with displacement ellipsoids drawn at the 50% probability level.
2-[4-(2-Methoxyphenyl)piperazin-1-yl]-N-(pyridin-2-yl)acetamide top
Crystal data top
C18H22N4O2Z = 4
Mr = 326.40F(000) = 696
Triclinic, P1Dx = 1.247 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.595 (4) ÅCell parameters from 3991 reflections
b = 12.382 (4) Åθ = 3.0–27.5°
c = 14.073 (4) ŵ = 0.08 mm1
α = 106.228 (4)°T = 143 K
β = 91.767 (3)°Prism, colourless
γ = 114.627 (2)°0.21 × 0.17 × 0.09 mm
V = 1738.2 (9) Å3
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4689 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.041
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm-1h = 1515
φ and ω scansk = 1612
16957 measured reflectionsl = 1818
7823 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: difmap and geom
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.168P]
where P = (Fo2 + 2Fc2)/3
7823 reflections(Δ/σ)max = 0.001
443 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C18H22N4O2γ = 114.627 (2)°
Mr = 326.40V = 1738.2 (9) Å3
Triclinic, P1Z = 4
a = 11.595 (4) ÅMo Kα radiation
b = 12.382 (4) ŵ = 0.08 mm1
c = 14.073 (4) ÅT = 143 K
α = 106.228 (4)°0.21 × 0.17 × 0.09 mm
β = 91.767 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4689 reflections with I > 2σ(I)
16957 measured reflectionsRint = 0.041
7823 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.74 e Å3
7823 reflectionsΔρmin = 0.19 e Å3
443 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
xyzUiso*/Ueq
O10.16031 (14)0.19320 (13)0.60110 (10)0.0318 (4)
O20.26509 (14)0.03711 (15)0.17233 (10)0.0389 (4)
N10.04151 (16)0.31688 (15)0.51774 (11)0.0248 (4)
N20.15938 (16)0.22961 (16)0.35729 (11)0.0264 (4)
N30.35747 (16)0.17050 (17)0.33185 (12)0.0260 (4)
N40.54677 (16)0.24391 (16)0.43628 (12)0.0290 (4)
C10.0797 (2)0.31511 (19)0.65726 (14)0.0263 (4)
C20.0993 (2)0.3747 (2)0.75015 (14)0.0304 (5)
H20.17190.33120.77740.037*
C30.0128 (2)0.4982 (2)0.80355 (16)0.0371 (5)
H30.02630.53860.86730.044*
C40.0919 (2)0.5616 (2)0.76425 (16)0.0388 (6)
H40.15070.64590.80050.047*
C50.1115 (2)0.5019 (2)0.67106 (15)0.0330 (5)
H50.18460.54610.64460.040*
C60.02656 (19)0.37892 (19)0.61564 (13)0.0254 (4)
C70.0808 (2)0.2177 (2)0.51565 (14)0.0291 (5)
H7A0.02250.16010.54840.035*
H7B0.16930.25570.55330.035*
C80.0760 (2)0.14470 (19)0.40775 (14)0.0297 (5)
H8A0.10470.07960.40700.036*
H8B0.01360.10230.37130.036*
C90.1161 (2)0.3261 (2)0.35931 (14)0.0310 (5)
H9A0.02600.28580.32430.037*
H9B0.17050.38270.32400.037*
C100.1254 (2)0.4008 (2)0.46679 (14)0.0304 (5)
H10A0.21550.44130.50180.036*
H10B0.09870.46750.46840.036*
C110.1642 (2)0.1621 (2)0.25557 (13)0.0297 (5)
H11A0.18080.21840.21440.036*
H11B0.07880.08980.22630.036*
C120.26561 (19)0.11417 (19)0.24878 (14)0.0270 (5)
C130.47825 (19)0.17094 (19)0.34499 (14)0.0244 (4)
C140.5227 (2)0.1054 (2)0.27087 (15)0.0326 (5)
H140.46970.05200.20780.039*
C150.6471 (2)0.1202 (2)0.29197 (16)0.0367 (5)
H150.68160.07830.24250.044*
C160.7206 (2)0.1964 (2)0.38561 (16)0.0346 (5)
H160.80620.20840.40150.042*
C170.6659 (2)0.2542 (2)0.45484 (16)0.0336 (5)
H170.71530.30450.51970.040*
C180.2720 (2)0.1297 (2)0.64012 (17)0.0411 (6)
H18A0.24600.12350.70450.062*
H18B0.32360.04530.59260.062*
H18C0.32340.17670.65000.062*
H030.345 (2)0.224 (2)0.3780 (15)0.036 (7)*
O30.31024 (14)0.19997 (13)0.69524 (10)0.0328 (4)
O40.20714 (14)0.09195 (14)1.08091 (10)0.0364 (4)
N50.27157 (15)0.34038 (15)0.86559 (11)0.0247 (4)
N60.07490 (15)0.27036 (16)0.98664 (11)0.0258 (4)
N70.17632 (17)0.22583 (16)0.99004 (12)0.0261 (4)
N80.31000 (17)0.26615 (17)0.89803 (12)0.0318 (4)
C190.37328 (19)0.3275 (2)0.71544 (14)0.0278 (5)
C200.4550 (2)0.3846 (2)0.65566 (15)0.0341 (5)
H200.46890.33480.59650.041*
C210.5165 (2)0.5145 (2)0.68257 (17)0.0442 (6)
H210.57200.55340.64140.053*
C220.4978 (2)0.5871 (2)0.76827 (18)0.0459 (6)
H220.54110.67600.78690.055*
C230.4155 (2)0.5301 (2)0.82765 (16)0.0362 (5)
H230.40250.58120.88650.043*
C240.35148 (19)0.4006 (2)0.80341 (14)0.0266 (5)
C250.13434 (19)0.26517 (19)0.82010 (14)0.0276 (5)
H25A0.12610.20880.75200.033*
H25B0.09600.32150.81390.033*
C260.0632 (2)0.1882 (2)0.88466 (14)0.0301 (5)
H26A0.02880.13820.85390.036*
H26B0.09910.12930.88830.036*
C270.21204 (19)0.3438 (2)1.03070 (14)0.0302 (5)
H27A0.24960.28651.03530.036*
H27B0.22150.39941.09940.036*
C280.2834 (2)0.4222 (2)0.96688 (14)0.0311 (5)
H28A0.24710.48080.96340.037*
H28B0.37530.47230.99770.037*
C290.0039 (2)0.1977 (2)1.04953 (14)0.0296 (5)
H29A0.04440.24601.12060.036*
H29B0.01330.11891.03260.036*
C300.1381 (2)0.16446 (19)1.04003 (14)0.0264 (5)
C310.30054 (19)0.21492 (19)0.96784 (13)0.0250 (4)
C320.4019 (2)0.15893 (19)1.01496 (15)0.0300 (5)
H320.39070.12481.06520.036*
C330.5194 (2)0.1543 (2)0.98670 (16)0.0346 (5)
H330.59070.11631.01740.042*
C340.5328 (2)0.2049 (2)0.91386 (16)0.0362 (5)
H340.61300.20190.89290.043*
C350.4262 (2)0.2599 (2)0.87240 (16)0.0369 (5)
H350.43500.29560.82270.044*
C360.3320 (2)0.1232 (2)0.60821 (16)0.0408 (6)
H36A0.30840.14080.54870.061*
H36B0.27930.03460.60070.061*
H36C0.42310.14140.61540.061*
H070.118 (2)0.271 (2)0.9629 (15)0.032 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0284 (8)0.0330 (8)0.0296 (7)0.0089 (7)0.0087 (6)0.0107 (6)
O20.0337 (9)0.0433 (10)0.0289 (8)0.0161 (8)0.0021 (6)0.0025 (7)
N10.0269 (9)0.0278 (9)0.0236 (8)0.0136 (8)0.0063 (7)0.0114 (7)
N20.0258 (9)0.0322 (10)0.0233 (8)0.0134 (8)0.0046 (7)0.0109 (7)
N30.0252 (10)0.0298 (10)0.0227 (9)0.0137 (8)0.0045 (7)0.0054 (8)
N40.0278 (10)0.0306 (10)0.0279 (9)0.0126 (8)0.0011 (7)0.0095 (7)
C10.0273 (11)0.0306 (11)0.0258 (10)0.0162 (9)0.0028 (8)0.0110 (9)
C20.0292 (12)0.0393 (13)0.0298 (11)0.0185 (10)0.0089 (9)0.0154 (10)
C30.0426 (14)0.0390 (14)0.0304 (11)0.0226 (12)0.0086 (10)0.0049 (10)
C40.0404 (14)0.0320 (13)0.0383 (12)0.0153 (11)0.0069 (10)0.0043 (10)
C50.0297 (12)0.0317 (12)0.0349 (11)0.0107 (10)0.0081 (9)0.0112 (10)
C60.0261 (11)0.0331 (12)0.0231 (10)0.0164 (10)0.0049 (8)0.0124 (9)
C70.0319 (12)0.0320 (12)0.0301 (11)0.0170 (10)0.0083 (9)0.0150 (9)
C80.0297 (12)0.0288 (12)0.0326 (11)0.0142 (10)0.0073 (9)0.0106 (9)
C90.0313 (12)0.0395 (13)0.0329 (11)0.0193 (11)0.0105 (9)0.0209 (10)
C100.0325 (12)0.0290 (12)0.0327 (11)0.0143 (10)0.0105 (9)0.0129 (9)
C110.0234 (11)0.0397 (13)0.0245 (10)0.0133 (10)0.0015 (8)0.0099 (9)
C120.0247 (11)0.0288 (11)0.0235 (10)0.0075 (9)0.0052 (8)0.0093 (9)
C130.0235 (11)0.0261 (11)0.0254 (10)0.0093 (9)0.0068 (8)0.0131 (8)
C140.0313 (12)0.0410 (13)0.0283 (11)0.0180 (11)0.0073 (9)0.0117 (10)
C150.0353 (13)0.0464 (15)0.0371 (12)0.0232 (12)0.0140 (10)0.0171 (11)
C160.0243 (12)0.0376 (13)0.0461 (13)0.0123 (10)0.0074 (9)0.0214 (11)
C170.0289 (12)0.0350 (12)0.0346 (11)0.0116 (10)0.0006 (9)0.0127 (10)
C180.0376 (14)0.0358 (14)0.0423 (13)0.0059 (11)0.0162 (10)0.0166 (11)
O30.0421 (10)0.0291 (8)0.0297 (8)0.0180 (7)0.0115 (6)0.0088 (6)
O40.0331 (9)0.0422 (9)0.0377 (8)0.0140 (8)0.0107 (7)0.0224 (7)
N50.0219 (9)0.0281 (9)0.0215 (8)0.0093 (8)0.0031 (6)0.0070 (7)
N60.0203 (9)0.0317 (10)0.0236 (8)0.0092 (8)0.0041 (6)0.0096 (7)
N70.0221 (9)0.0293 (10)0.0272 (9)0.0091 (8)0.0068 (7)0.0129 (8)
N80.0339 (11)0.0384 (11)0.0279 (9)0.0182 (9)0.0064 (7)0.0142 (8)
C190.0257 (11)0.0303 (12)0.0288 (10)0.0139 (10)0.0020 (8)0.0095 (9)
C200.0315 (13)0.0424 (14)0.0299 (11)0.0162 (11)0.0085 (9)0.0137 (10)
C210.0377 (15)0.0455 (15)0.0464 (14)0.0100 (12)0.0181 (11)0.0225 (12)
C220.0468 (16)0.0318 (13)0.0498 (14)0.0065 (12)0.0155 (12)0.0160 (11)
C230.0349 (13)0.0293 (12)0.0390 (12)0.0093 (10)0.0092 (10)0.0105 (10)
C240.0210 (11)0.0314 (12)0.0272 (10)0.0107 (9)0.0042 (8)0.0105 (9)
C250.0241 (11)0.0309 (12)0.0243 (10)0.0096 (9)0.0012 (8)0.0082 (9)
C260.0259 (11)0.0326 (12)0.0266 (10)0.0091 (10)0.0025 (8)0.0082 (9)
C270.0231 (11)0.0389 (13)0.0250 (10)0.0128 (10)0.0013 (8)0.0070 (9)
C280.0237 (11)0.0328 (12)0.0284 (10)0.0081 (10)0.0036 (8)0.0049 (9)
C290.0286 (12)0.0370 (13)0.0270 (10)0.0166 (10)0.0047 (8)0.0125 (9)
C300.0297 (12)0.0265 (11)0.0215 (9)0.0112 (10)0.0046 (8)0.0075 (8)
C310.0238 (11)0.0255 (11)0.0235 (9)0.0112 (9)0.0025 (8)0.0043 (8)
C320.0270 (12)0.0296 (12)0.0321 (11)0.0109 (10)0.0077 (9)0.0105 (9)
C330.0270 (12)0.0298 (12)0.0415 (12)0.0103 (10)0.0088 (9)0.0065 (10)
C340.0287 (13)0.0388 (14)0.0390 (12)0.0178 (11)0.0009 (9)0.0053 (10)
C350.0367 (14)0.0467 (15)0.0329 (11)0.0246 (12)0.0040 (9)0.0117 (10)
C360.0558 (17)0.0380 (14)0.0356 (12)0.0285 (13)0.0134 (11)0.0094 (11)
Geometric parameters (Å, º) top
O1—C11.374 (2)O3—C191.372 (2)
O1—C181.426 (2)O3—C361.427 (2)
O2—C121.220 (2)O4—C301.223 (2)
N1—C61.433 (2)N5—C241.421 (2)
N1—C101.469 (2)N5—C281.464 (2)
N1—C71.470 (3)N5—C251.476 (2)
N2—C111.458 (2)N6—C291.464 (2)
N2—C81.469 (2)N6—C271.469 (2)
N2—C91.470 (3)N6—C261.473 (2)
N3—C121.355 (2)N7—C301.352 (3)
N3—C131.404 (3)N7—C311.406 (3)
N3—H030.85 (2)N7—H070.86 (2)
N4—C131.337 (2)N8—C311.334 (3)
N4—C171.343 (3)N8—C351.348 (3)
C1—C21.387 (3)C19—C201.389 (3)
C1—C61.406 (3)C19—C241.414 (3)
C2—C31.394 (3)C20—C211.388 (3)
C2—H20.9500C20—H200.9500
C3—C41.374 (3)C21—C221.372 (3)
C3—H30.9500C21—H210.9500
C4—C51.391 (3)C22—C231.387 (3)
C4—H40.9500C22—H220.9500
C5—C61.391 (3)C23—C241.388 (3)
C5—H50.9500C23—H230.9500
C7—C81.521 (3)C25—C261.513 (3)
C7—H7A0.9900C25—H25A0.9900
C7—H7B0.9900C25—H25B0.9900
C8—H8A0.9900C26—H26A0.9900
C8—H8B0.9900C26—H26B0.9900
C9—C101.510 (3)C27—C281.515 (3)
C9—H9A0.9900C27—H27A0.9900
C9—H9B0.9900C27—H27B0.9900
C10—H10A0.9900C28—H28A0.9900
C10—H10B0.9900C28—H28B0.9900
C11—C121.517 (3)C29—C301.513 (3)
C11—H11A0.9900C29—H29A0.9900
C11—H11B0.9900C29—H29B0.9900
C13—C141.386 (3)C31—C321.388 (3)
C14—C151.387 (3)C32—C331.381 (3)
C14—H140.9500C32—H320.9500
C15—C161.386 (3)C33—C341.378 (3)
C15—H150.9500C33—H330.9500
C16—C171.375 (3)C34—C351.377 (3)
C16—H160.9500C34—H340.9500
C17—H170.9500C35—H350.9500
C18—H18A0.9800C36—H36A0.9800
C18—H18B0.9800C36—H36B0.9800
C18—H18C0.9800C36—H36C0.9800
C1—O1—C18116.84 (15)C19—O3—C36117.38 (16)
C6—N1—C10114.88 (16)C24—N5—C28115.19 (16)
C6—N1—C7113.42 (15)C24—N5—C25114.62 (15)
C10—N1—C7110.02 (15)C28—N5—C25109.58 (14)
C11—N2—C8111.99 (16)C29—N6—C27110.89 (15)
C11—N2—C9112.14 (16)C29—N6—C26111.33 (16)
C8—N2—C9109.09 (15)C27—N6—C26108.63 (15)
C12—N3—C13129.39 (18)C30—N7—C31128.76 (18)
C12—N3—H03113.4 (15)C30—N7—H07114.5 (15)
C13—N3—H03116.0 (15)C31—N7—H07116.3 (15)
C13—N4—C17116.92 (17)C31—N8—C35116.63 (18)
O1—C1—C2123.16 (18)O3—C19—C20123.64 (18)
O1—C1—C6116.37 (16)O3—C19—C24115.77 (17)
C2—C1—C6120.46 (19)C20—C19—C24120.6 (2)
C1—C2—C3120.11 (19)C21—C20—C19119.8 (2)
C1—C2—H2119.9C21—C20—H20120.1
C3—C2—H2119.9C19—C20—H20120.1
C4—C3—C2120.17 (19)C22—C21—C20120.5 (2)
C4—C3—H3119.9C22—C21—H21119.8
C2—C3—H3119.9C20—C21—H21119.8
C3—C4—C5119.7 (2)C21—C22—C23119.7 (2)
C3—C4—H4120.2C21—C22—H22120.1
C5—C4—H4120.2C23—C22—H22120.1
C4—C5—C6121.55 (19)C22—C23—C24121.8 (2)
C4—C5—H5119.2C22—C23—H23119.1
C6—C5—H5119.2C24—C23—H23119.1
C5—C6—C1118.02 (17)C23—C24—C19117.59 (18)
C5—C6—N1122.69 (17)C23—C24—N5122.76 (18)
C1—C6—N1119.26 (18)C19—C24—N5119.57 (19)
N1—C7—C8110.03 (16)N5—C25—C26109.92 (16)
N1—C7—H7A109.7N5—C25—H25A109.7
C8—C7—H7A109.7C26—C25—H25A109.7
N1—C7—H7B109.7N5—C25—H25B109.7
C8—C7—H7B109.7C26—C25—H25B109.7
H7A—C7—H7B108.2H25A—C25—H25B108.2
N2—C8—C7110.27 (16)N6—C26—C25110.55 (17)
N2—C8—H8A109.6N6—C26—H26A109.5
C7—C8—H8A109.6C25—C26—H26A109.5
N2—C8—H8B109.6N6—C26—H26B109.5
C7—C8—H8B109.6C25—C26—H26B109.5
H8A—C8—H8B108.1H26A—C26—H26B108.1
N2—C9—C10109.63 (16)N6—C27—C28110.30 (16)
N2—C9—H9A109.7N6—C27—H27A109.6
C10—C9—H9A109.7C28—C27—H27A109.6
N2—C9—H9B109.7N6—C27—H27B109.6
C10—C9—H9B109.7C28—C27—H27B109.6
H9A—C9—H9B108.2H27A—C27—H27B108.1
N1—C10—C9109.40 (16)N5—C28—C27109.87 (17)
N1—C10—H10A109.8N5—C28—H28A109.7
C9—C10—H10A109.8C27—C28—H28A109.7
N1—C10—H10B109.8N5—C28—H28B109.7
C9—C10—H10B109.8C27—C28—H28B109.7
H10A—C10—H10B108.2H28A—C28—H28B108.2
N2—C11—C12114.41 (16)N6—C29—C30115.62 (17)
N2—C11—H11A108.7N6—C29—H29A108.4
C12—C11—H11A108.7C30—C29—H29A108.4
N2—C11—H11B108.7N6—C29—H29B108.4
C12—C11—H11B108.7C30—C29—H29B108.4
H11A—C11—H11B107.6H29A—C29—H29B107.4
O2—C12—N3125.0 (2)O4—C30—N7125.2 (2)
O2—C12—C11121.35 (18)O4—C30—C29119.63 (19)
N3—C12—C11113.57 (17)N7—C30—C29115.06 (17)
N4—C13—C14123.7 (2)N8—C31—C32123.6 (2)
N4—C13—N3112.45 (17)N8—C31—N7112.81 (17)
C14—C13—N3123.79 (18)C32—C31—N7123.57 (19)
C13—C14—C15117.8 (2)C33—C32—C31118.1 (2)
C13—C14—H14121.1C33—C32—H32121.0
C15—C14—H14121.1C31—C32—H32121.0
C16—C15—C14119.6 (2)C34—C33—C32119.7 (2)
C16—C15—H15120.2C34—C33—H33120.1
C14—C15—H15120.2C32—C33—H33120.1
C17—C16—C15117.9 (2)C35—C34—C33117.9 (2)
C17—C16—H16121.0C35—C34—H34121.0
C15—C16—H16121.0C33—C34—H34121.0
N4—C17—C16124.0 (2)N8—C35—C34124.0 (2)
N4—C17—H17118.0N8—C35—H35118.0
C16—C17—H17118.0C34—C35—H35118.0
O1—C18—H18A109.5O3—C36—H36A109.5
O1—C18—H18B109.5O3—C36—H36B109.5
H18A—C18—H18B109.5H36A—C36—H36B109.5
O1—C18—H18C109.5O3—C36—H36C109.5
H18A—C18—H18C109.5H36A—C36—H36C109.5
H18B—C18—H18C109.5H36B—C36—H36C109.5
C18—O1—C1—C23.2 (3)C36—O3—C19—C200.6 (3)
C18—O1—C1—C6176.80 (19)C36—O3—C19—C24178.73 (19)
O1—C1—C2—C3179.3 (2)O3—C19—C20—C21179.0 (2)
C6—C1—C2—C30.7 (3)C24—C19—C20—C210.3 (3)
C1—C2—C3—C40.3 (3)C19—C20—C21—C220.5 (4)
C2—C3—C4—C50.2 (4)C20—C21—C22—C230.9 (4)
C3—C4—C5—C60.6 (4)C21—C22—C23—C240.6 (4)
C4—C5—C6—C11.0 (3)C22—C23—C24—C190.2 (3)
C4—C5—C6—N1177.4 (2)C22—C23—C24—N5176.9 (2)
O1—C1—C6—C5178.98 (18)O3—C19—C24—C23178.73 (19)
C2—C1—C6—C51.0 (3)C20—C19—C24—C230.6 (3)
O1—C1—C6—N12.6 (3)O3—C19—C24—N51.9 (3)
C2—C1—C6—N1177.39 (18)C20—C19—C24—N5177.44 (19)
C10—N1—C6—C518.5 (3)C28—N5—C24—C2313.1 (3)
C7—N1—C6—C5109.2 (2)C25—N5—C24—C23115.4 (2)
C10—N1—C6—C1159.80 (18)C28—N5—C24—C19163.57 (18)
C7—N1—C6—C172.5 (2)C25—N5—C24—C1967.9 (2)
C6—N1—C7—C8171.99 (16)C24—N5—C25—C26170.29 (17)
C10—N1—C7—C857.8 (2)C28—N5—C25—C2658.4 (2)
C11—N2—C8—C7176.23 (16)C29—N6—C26—C25178.58 (17)
C9—N2—C8—C759.0 (2)C27—N6—C26—C2559.0 (2)
N1—C7—C8—N257.8 (2)N5—C25—C26—N659.0 (2)
C11—N2—C9—C10174.60 (16)C29—N6—C27—C28177.92 (16)
C8—N2—C9—C1060.7 (2)C26—N6—C27—C2859.4 (2)
C6—N1—C10—C9171.08 (16)C24—N5—C28—C27170.09 (17)
C7—N1—C10—C959.5 (2)C25—N5—C28—C2758.9 (2)
N2—C9—C10—N161.1 (2)N6—C27—C28—N560.2 (2)
C8—N2—C11—C1286.9 (2)C27—N6—C29—C30154.65 (17)
C9—N2—C11—C12150.02 (18)C26—N6—C29—C3084.3 (2)
C13—N3—C12—O211.1 (3)C31—N7—C30—O44.8 (3)
C13—N3—C12—C11164.95 (19)C31—N7—C30—C29179.19 (18)
N2—C11—C12—O2166.17 (18)N6—C29—C30—O4171.57 (17)
N2—C11—C12—N317.6 (2)N6—C29—C30—N712.2 (2)
C17—N4—C13—C141.1 (3)C35—N8—C31—C321.1 (3)
C17—N4—C13—N3177.56 (17)C35—N8—C31—N7179.91 (18)
C12—N3—C13—N4175.9 (2)C30—N7—C31—N8165.16 (19)
C12—N3—C13—C142.7 (3)C30—N7—C31—C3216.0 (3)
N4—C13—C14—C152.3 (3)N8—C31—C32—C331.1 (3)
N3—C13—C14—C15176.1 (2)N7—C31—C32—C33179.82 (18)
C13—C14—C15—C161.5 (3)C31—C32—C33—C340.2 (3)
C14—C15—C16—C170.5 (3)C32—C33—C34—C350.6 (3)
C13—N4—C17—C161.1 (3)C31—N8—C35—C340.2 (3)
C15—C16—C17—N41.9 (3)C33—C34—C35—N80.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H03···N20.85 (2)2.20 (3)2.692 (3)117.0 (19)
N7—H07···N60.86 (2)2.26 (3)2.734 (3)115.3 (19)
C2—H2···N80.952.443.354 (3)161
C7—H7A···O10.992.423.010 (3)118
C14—H14···O20.952.332.923 (3)120
C20—H20···N40.952.593.527 (3)168
C25—H25A···O30.992.342.950 (3)119
C32—H32···O40.952.342.917 (3)118

Experimental details

Crystal data
Chemical formulaC18H22N4O2
Mr326.40
Crystal system, space groupTriclinic, P1
Temperature (K)143
a, b, c (Å)11.595 (4), 12.382 (4), 14.073 (4)
α, β, γ (°)106.228 (4), 91.767 (3), 114.627 (2)
V3)1738.2 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.21 × 0.17 × 0.09
Data collection
DiffractometerRigaku AFC10/Saturn724+
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16957, 7823, 4689
Rint0.041
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.134, 1.00
No. of reflections7823
No. of parameters443
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.74, 0.19

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H03···N20.85 (2)2.20 (3)2.692 (3)117.0 (19)
N7—H07···N60.86 (2)2.26 (3)2.734 (3)115.3 (19)
C2—H2···N80.952.443.354 (3)161
C14—H14···O20.952.332.923 (3)120
C20—H20···N40.952.593.527 (3)168
 

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

First citationLebars, 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
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhuang, 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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