organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-{2-[4-(2-Meth­­oxy­phen­yl)piperazin-1-yl]eth­yl}-4-nitro-N-(2-pyrid­yl)benzamide

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 10 September 2010; accepted 23 September 2010; online 30 September 2010)

In the title compound, C25H27N5O4, the piperizine ring adopts a chair conformation. The dihedral angles between the pyridine ring and the two benzene rings are 65.5 (4) and 70.7 (4)°, while the dihedral angle between the two benzene rings is 17.3 (3)°. An intra­molecular C—H⋯O hydrogen bond occurs.

Related literature

For the use of the title compound as a labeling precursor of the serotonin (5-HT1 A) receptor imaging agent,18F-MPPF, see: Le Bars et al. (1998[Le Bars, D., Lemaire, C., Ginovart, N., Plenevaux, A., Aerts, J., Brihaye, C. & 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
  • C25H27N5O4

  • Mr = 461.52

  • Monoclinic, P 21 /n

  • a = 11.480 (2) Å

  • b = 15.512 (3) Å

  • c = 13.235 (2) Å

  • β = 108.505 (3)°

  • V = 2234.9 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 103 K

  • 0.50 × 0.50 × 0.33 mm

Data collection
  • Rigaku SPIDER diffractometer

  • 17307 measured reflections

  • 5066 independent reflections

  • 4318 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.098

  • S = 1.00

  • 5066 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10A⋯O1 0.99 2.35 2.9536 (18) 119

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL.

Supporting information


Comment top

N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}-4-nitro-N-(2-pyridyl)benzamide, (I), is a labeling precursor of 18F-MPPF, serotonin (5-HT1A) receptor imaging agents (18F-MPPF = 4-(2-methoxyphenyl)-1-[2-(N-2-pyridinyl)-p-18F-fluorobenzamido]ethylpiperazine). We report here the crystal structure of (I). Two phenyl rings and pyridine rings are planar with a maximum deviation of 0.004 (2)Å for atom C1, 0.010 (9)Å for atom C20 and 0.012 (7)Å for atom N4. The dihedral angles between the pyridine ring and the other two phenyl rings are 65.5 (4) and 70.7 (4)°, respectively, while the dihedral angle between the two phenyl rings is 17.3 (3)°. The piperazine ring adopts a chair conformation. Intramolecular C—H···O hydrogen bond could be found in the crystal structure of the title compound.

Related literature top

For the use of the title compound as a labeling precursor of the serotonin (5-HT1 A) receptor imaging agent,18F-MPPF, see: Le Bars 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 ethyl acetate and petroleum ether (1:1); colorless block-shaped crystals were obtained after several days.

Refinement top

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 are attached with C—H distances of 0.95Å (CH), 0.98Å (CH3) or 0.99Å (CH2), and with Uiso(H) = 1.2Ueq (or 1.5 for CH3) of the parent atoms.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}-4-nitro- N-(2-pyridyl)benzamide top
Crystal data top
C25H27N5O4F(000) = 976
Mr = 461.52Dx = 1.372 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6374 reflections
a = 11.480 (2) Åθ = 3.1–27.5°
b = 15.512 (3) ŵ = 0.10 mm1
c = 13.235 (2) ÅT = 103 K
β = 108.505 (3)°Block, yellow
V = 2234.9 (7) Å30.50 × 0.50 × 0.33 mm
Z = 4
Data collection top
Rigaku SPIDER
diffractometer
4318 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1414
17307 measured reflectionsk = 2019
5066 independent reflectionsl = 1317
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.850P]
where P = (Fo2 + 2Fc2)/3
5066 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C25H27N5O4V = 2234.9 (7) Å3
Mr = 461.52Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.480 (2) ŵ = 0.10 mm1
b = 15.512 (3) ÅT = 103 K
c = 13.235 (2) Å0.50 × 0.50 × 0.33 mm
β = 108.505 (3)°
Data collection top
Rigaku SPIDER
diffractometer
4318 reflections with I > 2σ(I)
17307 measured reflectionsRint = 0.028
5066 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.00Δρmax = 0.31 e Å3
5066 reflectionsΔρmin = 0.17 e Å3
308 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
O10.63130 (9)0.66210 (6)0.68937 (8)0.0225 (2)
O20.27919 (9)0.13878 (6)0.52481 (7)0.0206 (2)
O30.25952 (9)0.31358 (6)0.59155 (8)0.0251 (2)
O40.35176 (10)0.30235 (6)0.47275 (9)0.0291 (2)
N10.53263 (10)0.53783 (7)0.77943 (8)0.0151 (2)
N20.44755 (10)0.36714 (6)0.70911 (8)0.0158 (2)
N30.39572 (10)0.12774 (6)0.69878 (8)0.0149 (2)
N40.57867 (10)0.05037 (7)0.73066 (9)0.0171 (2)
N50.30875 (10)0.27110 (7)0.53821 (9)0.0192 (2)
C10.57913 (11)0.68987 (8)0.76307 (10)0.0171 (3)
C20.57713 (12)0.77550 (8)0.79298 (11)0.0211 (3)
H20.61130.81870.76000.025*
C30.52534 (13)0.79824 (9)0.87100 (11)0.0227 (3)
H30.52440.85690.89130.027*
C40.47553 (13)0.73621 (9)0.91885 (11)0.0220 (3)
H40.44050.75180.97240.026*
C50.47655 (12)0.64994 (9)0.88842 (10)0.0187 (3)
H50.44170.60730.92170.022*
C60.52736 (11)0.62517 (8)0.81082 (10)0.0158 (3)
C70.51121 (12)0.47400 (8)0.85260 (10)0.0175 (3)
H7A0.42620.47960.85490.021*
H7B0.56830.48440.92530.021*
C80.53066 (13)0.38377 (8)0.81686 (10)0.0194 (3)
H8A0.61680.37730.81790.023*
H8B0.51550.34110.86690.023*
C90.47539 (12)0.42937 (8)0.63708 (10)0.0177 (3)
H9A0.42230.41830.56310.021*
H9B0.56200.42290.63960.021*
C100.45397 (12)0.52014 (8)0.66945 (10)0.0176 (3)
H10A0.47260.56200.62020.021*
H10B0.36660.52710.66450.021*
C110.45819 (12)0.27806 (8)0.67654 (10)0.0170 (3)
H11A0.54450.25870.70630.020*
H11B0.43420.27480.59790.020*
C120.37576 (12)0.21947 (8)0.71606 (10)0.0163 (3)
H12A0.39160.22970.79310.020*
H12B0.28880.23420.67850.020*
C130.49869 (11)0.08612 (8)0.77229 (10)0.0144 (2)
C140.51295 (12)0.08617 (8)0.88043 (10)0.0187 (3)
H140.45440.11340.90690.022*
C150.61517 (13)0.04521 (9)0.94863 (11)0.0222 (3)
H150.62850.04461.02320.027*
C160.69744 (13)0.00529 (9)0.90684 (11)0.0212 (3)
H160.76700.02450.95170.025*
C170.67581 (12)0.00988 (9)0.79809 (11)0.0206 (3)
H170.73280.01710.76950.025*
C180.33804 (11)0.09378 (8)0.59942 (10)0.0150 (2)
C190.33808 (11)0.00235 (8)0.58734 (10)0.0145 (3)
C200.31415 (12)0.05593 (8)0.66290 (10)0.0163 (3)
H200.30630.03190.72650.020*
C210.30169 (12)0.14415 (8)0.64579 (10)0.0178 (3)
H210.28270.18090.69580.021*
C220.31762 (11)0.17711 (8)0.55421 (10)0.0163 (3)
C230.34266 (12)0.12582 (8)0.47817 (10)0.0177 (3)
H230.35410.15040.41630.021*
C240.35056 (12)0.03751 (8)0.49471 (10)0.0173 (3)
H240.36460.00070.44240.021*
C250.68011 (14)0.72601 (9)0.63702 (12)0.0257 (3)
H25A0.61400.76460.59690.039*
H25B0.71690.69810.58800.039*
H25C0.74300.75930.69010.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0285 (5)0.0173 (5)0.0263 (5)0.0025 (4)0.0150 (4)0.0013 (4)
O20.0239 (5)0.0177 (5)0.0172 (5)0.0010 (4)0.0020 (4)0.0021 (4)
O30.0281 (5)0.0165 (5)0.0313 (6)0.0037 (4)0.0104 (4)0.0022 (4)
O40.0346 (6)0.0198 (5)0.0385 (6)0.0003 (4)0.0194 (5)0.0083 (4)
N10.0191 (5)0.0111 (5)0.0137 (5)0.0013 (4)0.0031 (4)0.0002 (4)
N20.0216 (6)0.0110 (5)0.0136 (5)0.0013 (4)0.0036 (4)0.0009 (4)
N30.0176 (5)0.0110 (5)0.0154 (5)0.0004 (4)0.0041 (4)0.0016 (4)
N40.0165 (5)0.0167 (5)0.0176 (5)0.0006 (4)0.0048 (4)0.0002 (4)
N50.0176 (5)0.0145 (5)0.0244 (6)0.0003 (4)0.0050 (5)0.0013 (4)
C10.0161 (6)0.0169 (6)0.0164 (6)0.0007 (5)0.0022 (5)0.0003 (5)
C20.0236 (7)0.0148 (6)0.0218 (7)0.0027 (5)0.0027 (5)0.0017 (5)
C30.0271 (7)0.0148 (6)0.0223 (7)0.0007 (5)0.0022 (6)0.0034 (5)
C40.0250 (7)0.0208 (7)0.0184 (7)0.0013 (5)0.0043 (5)0.0037 (5)
C50.0201 (6)0.0173 (6)0.0174 (6)0.0013 (5)0.0042 (5)0.0000 (5)
C60.0152 (6)0.0131 (6)0.0159 (6)0.0005 (5)0.0003 (5)0.0001 (4)
C70.0226 (6)0.0139 (6)0.0150 (6)0.0024 (5)0.0045 (5)0.0001 (5)
C80.0258 (7)0.0139 (6)0.0153 (6)0.0011 (5)0.0018 (5)0.0011 (5)
C90.0234 (7)0.0146 (6)0.0143 (6)0.0011 (5)0.0047 (5)0.0001 (5)
C100.0206 (6)0.0141 (6)0.0154 (6)0.0002 (5)0.0018 (5)0.0011 (5)
C110.0211 (6)0.0130 (6)0.0163 (6)0.0004 (5)0.0049 (5)0.0013 (5)
C120.0194 (6)0.0117 (6)0.0175 (6)0.0016 (5)0.0051 (5)0.0020 (5)
C130.0160 (6)0.0100 (5)0.0162 (6)0.0028 (5)0.0036 (5)0.0010 (4)
C140.0225 (6)0.0175 (6)0.0169 (6)0.0005 (5)0.0072 (5)0.0004 (5)
C150.0285 (7)0.0212 (7)0.0145 (6)0.0022 (6)0.0036 (5)0.0008 (5)
C160.0201 (6)0.0164 (6)0.0226 (7)0.0002 (5)0.0006 (5)0.0031 (5)
C170.0176 (6)0.0184 (6)0.0244 (7)0.0010 (5)0.0044 (5)0.0020 (5)
C180.0149 (6)0.0150 (6)0.0157 (6)0.0009 (5)0.0055 (5)0.0002 (5)
C190.0119 (6)0.0140 (6)0.0160 (6)0.0007 (5)0.0019 (5)0.0012 (5)
C200.0175 (6)0.0175 (6)0.0141 (6)0.0017 (5)0.0052 (5)0.0021 (5)
C210.0178 (6)0.0171 (6)0.0183 (6)0.0029 (5)0.0054 (5)0.0020 (5)
C220.0142 (6)0.0126 (6)0.0208 (6)0.0012 (5)0.0035 (5)0.0019 (5)
C230.0187 (6)0.0183 (6)0.0166 (6)0.0015 (5)0.0064 (5)0.0043 (5)
C240.0193 (6)0.0173 (6)0.0152 (6)0.0022 (5)0.0053 (5)0.0008 (5)
C250.0288 (7)0.0225 (7)0.0285 (8)0.0060 (6)0.0128 (6)0.0041 (6)
Geometric parameters (Å, º) top
O1—C11.3662 (16)C9—C101.5145 (18)
O1—C251.4223 (16)C9—H9A0.9900
O2—C181.2228 (15)C9—H9B0.9900
O3—N51.2268 (15)C10—H10A0.9900
O4—N51.2251 (15)C10—H10B0.9900
N1—C61.4240 (16)C11—C121.5196 (18)
N1—C71.4594 (16)C11—H11A0.9900
N1—C101.4747 (16)C11—H11B0.9900
N2—C91.4616 (16)C12—H12A0.9900
N2—C111.4641 (16)C12—H12B0.9900
N2—C81.4652 (16)C13—C141.3879 (18)
N3—C181.3758 (16)C14—C151.3867 (19)
N3—C131.4250 (15)C14—H140.9500
N3—C121.4705 (15)C15—C161.383 (2)
N4—C131.3323 (16)C15—H150.9500
N4—C171.3426 (17)C16—C171.383 (2)
N5—C221.4722 (16)C16—H160.9500
C1—C21.3882 (18)C17—H170.9500
C1—C61.4137 (18)C18—C191.4997 (17)
C2—C31.391 (2)C19—C241.3901 (18)
C2—H20.9500C19—C201.3931 (18)
C3—C41.372 (2)C20—C211.3870 (18)
C3—H30.9500C20—H200.9500
C4—C51.3987 (19)C21—C221.3801 (19)
C4—H40.9500C21—H210.9500
C5—C61.3866 (19)C22—C231.3828 (18)
C5—H50.9500C23—C241.3856 (18)
C7—C81.5164 (18)C23—H230.9500
C7—H7A0.9900C24—H240.9500
C7—H7B0.9900C25—H25A0.9800
C8—H8A0.9900C25—H25B0.9800
C8—H8B0.9900C25—H25C0.9800
C1—O1—C25117.24 (11)H10A—C10—H10B108.1
C6—N1—C7114.85 (10)N2—C11—C12110.12 (10)
C6—N1—C10113.30 (10)N2—C11—H11A109.6
C7—N1—C10110.45 (10)C12—C11—H11A109.6
C9—N2—C11112.05 (10)N2—C11—H11B109.6
C9—N2—C8107.99 (10)C12—C11—H11B109.6
C11—N2—C8111.31 (10)H11A—C11—H11B108.2
C18—N3—C13121.49 (10)N3—C12—C11112.36 (10)
C18—N3—C12117.89 (10)N3—C12—H12A109.1
C13—N3—C12117.95 (10)C11—C12—H12A109.1
C13—N4—C17117.12 (11)N3—C12—H12B109.1
O4—N5—O3123.85 (11)C11—C12—H12B109.1
O4—N5—C22117.94 (11)H12A—C12—H12B107.9
O3—N5—C22118.20 (11)N4—C13—C14123.74 (12)
O1—C1—C2123.77 (12)N4—C13—N3115.94 (11)
O1—C1—C6115.92 (11)C14—C13—N3120.30 (11)
C2—C1—C6120.30 (12)C15—C14—C13118.00 (12)
C1—C2—C3120.27 (13)C15—C14—H14121.0
C1—C2—H2119.9C13—C14—H14121.0
C3—C2—H2119.9C16—C15—C14119.28 (13)
C4—C3—C2120.24 (13)C16—C15—H15120.4
C4—C3—H3119.9C14—C15—H15120.4
C2—C3—H3119.9C17—C16—C15118.25 (12)
C3—C4—C5119.68 (13)C17—C16—H16120.9
C3—C4—H4120.2C15—C16—H16120.9
C5—C4—H4120.2N4—C17—C16123.57 (13)
C6—C5—C4121.48 (13)N4—C17—H17118.2
C6—C5—H5119.3C16—C17—H17118.2
C4—C5—H5119.3O2—C18—N3121.88 (11)
C5—C6—C1118.02 (12)O2—C18—C19120.02 (11)
C5—C6—N1123.12 (11)N3—C18—C19117.80 (11)
C1—C6—N1118.83 (11)C24—C19—C20119.87 (12)
N1—C7—C8110.29 (11)C24—C19—C18119.19 (11)
N1—C7—H7A109.6C20—C19—C18120.66 (11)
C8—C7—H7A109.6C21—C20—C19120.34 (12)
N1—C7—H7B109.6C21—C20—H20119.8
C8—C7—H7B109.6C19—C20—H20119.8
H7A—C7—H7B108.1C22—C21—C20118.25 (12)
N2—C8—C7110.57 (10)C22—C21—H21120.9
N2—C8—H8A109.5C20—C21—H21120.9
C7—C8—H8A109.5C21—C22—C23122.82 (12)
N2—C8—H8B109.5C21—C22—N5118.09 (11)
C7—C8—H8B109.5C23—C22—N5119.08 (11)
H8A—C8—H8B108.1C22—C23—C24118.18 (12)
N2—C9—C10109.93 (10)C22—C23—H23120.9
N2—C9—H9A109.7C24—C23—H23120.9
C10—C9—H9A109.7C23—C24—C19120.48 (12)
N2—C9—H9B109.7C23—C24—H24119.8
C10—C9—H9B109.7C19—C24—H24119.8
H9A—C9—H9B108.2O1—C25—H25A109.5
N1—C10—C9110.41 (10)O1—C25—H25B109.5
N1—C10—H10A109.6H25A—C25—H25B109.5
C9—C10—H10A109.6O1—C25—H25C109.5
N1—C10—H10B109.6H25A—C25—H25C109.5
C9—C10—H10B109.6H25B—C25—H25C109.5
C25—O1—C1—C23.46 (18)C17—N4—C13—N3179.26 (11)
C25—O1—C1—C6177.71 (11)C18—N3—C13—N438.82 (16)
O1—C1—C2—C3178.09 (12)C12—N3—C13—N4122.24 (12)
C6—C1—C2—C30.69 (19)C18—N3—C13—C14142.72 (12)
C1—C2—C3—C40.2 (2)C12—N3—C13—C1456.22 (16)
C2—C3—C4—C50.3 (2)N4—C13—C14—C151.27 (19)
C3—C4—C5—C60.2 (2)N3—C13—C14—C15179.60 (11)
C4—C5—C6—C10.29 (19)C13—C14—C15—C160.83 (19)
C4—C5—C6—N1178.53 (12)C14—C15—C16—C171.7 (2)
O1—C1—C6—C5178.13 (11)C13—N4—C17—C161.38 (19)
C2—C1—C6—C50.74 (18)C15—C16—C17—N40.6 (2)
O1—C1—C6—N10.19 (16)C13—N3—C18—O2155.72 (12)
C2—C1—C6—N1179.06 (11)C12—N3—C18—O25.36 (18)
C7—N1—C6—C515.52 (17)C13—N3—C18—C1930.55 (17)
C10—N1—C6—C5112.69 (14)C12—N3—C18—C19168.37 (10)
C7—N1—C6—C1162.70 (11)O2—C18—C19—C2443.64 (17)
C10—N1—C6—C169.08 (15)N3—C18—C19—C24142.51 (12)
C6—N1—C7—C8174.73 (10)O2—C18—C19—C20130.21 (13)
C10—N1—C7—C855.64 (13)N3—C18—C19—C2043.64 (17)
C9—N2—C8—C761.10 (14)C24—C19—C20—C210.53 (19)
C11—N2—C8—C7175.50 (11)C18—C19—C20—C21173.28 (11)
N1—C7—C8—N258.92 (14)C19—C20—C21—C222.09 (19)
C11—N2—C9—C10175.83 (10)C20—C21—C22—C231.46 (19)
C8—N2—C9—C1061.23 (13)C20—C21—C22—N5177.83 (11)
C6—N1—C10—C9173.32 (11)O4—N5—C22—C21162.31 (12)
C7—N1—C10—C956.22 (14)O3—N5—C22—C2117.24 (17)
N2—C9—C10—N159.47 (14)O4—N5—C22—C2317.01 (17)
C9—N2—C11—C12153.57 (10)O3—N5—C22—C23163.44 (12)
C8—N2—C11—C1285.39 (13)C21—C22—C23—C240.75 (19)
C18—N3—C12—C1181.95 (14)N5—C22—C23—C24179.97 (11)
C13—N3—C12—C1179.80 (14)C22—C23—C24—C192.35 (19)
N2—C11—C12—N3171.93 (10)C20—C19—C24—C231.74 (19)
C17—N4—C13—C142.34 (18)C18—C19—C24—C23175.64 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10A···O10.992.352.9536 (18)119

Experimental details

Crystal data
Chemical formulaC25H27N5O4
Mr461.52
Crystal system, space groupMonoclinic, P21/n
Temperature (K)103
a, b, c (Å)11.480 (2), 15.512 (3), 13.235 (2)
β (°) 108.505 (3)
V3)2234.9 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.50 × 0.33
Data collection
DiffractometerRigaku SPIDER
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17307, 5066, 4318
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.098, 1.00
No. of reflections5066
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.17

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10A···O10.992.352.9536 (18)119
 

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 citationLe Bars, D., Lemaire, C., Ginovart, N., Plenevaux, A., Aerts, J., Brihaye, C. & Comar, D. (1998). Nucl. Med. Biol. 25, 343–350.  Web of Science CrossRef CAS PubMed Google Scholar
First citationRigaku (2004). RAPID-AUTO. 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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