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

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ISSN: 2056-9890

Ethyl 2-di­ethyl­amino-4-oxo-3,5-di­phenyl-4,5-di­hydro-3H-pyrrolo­[3,2-d]pyrimidine-7-carboxyl­ate

aInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, People's Republic of China, bThe Library of Hubei University of Medicine, Shiyan 442000, People's Republic of China, and cDepartment of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000, People's Republic of China
*Correspondence e-mail: , huyangg111@yahoo.com.cn

(Received 12 November 2011; accepted 8 December 2011; online 14 December 2011)

In the title compound, C25H26N4O3, the two fused pyrrolo­[3,2-d]pyrimidine rings form a dihedral angle of 3.7 (2)°. The two substituent phenyl rings are twisted with respect to the pyrrole and pyrimidine rings, making dihedral angles of 57.2 (2) and 69.0 (2)°, respectively. The ethyl and eth­oxy groups are disordered over two positions; the site occupancies are 0.53 (1) and 0.47 (1) for ethyl, and 0.63 (1) and 0.37 (1) for eth­oxy. The crystal packing features C—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Hu et al. (2006[Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.], 2007[Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735.], 2010[Hu, Y. G., Wang, Y., Du, S. M., Chen, X. B. & Ding, M. W. (2010). Bioorg. Med. Chem. Lett. 20, 6188-6190.]). For related structures, see: He et al. (2007a[He, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884.],b[He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185.]); Ma et al. (2009[Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629.]); Zeng & Yan (2008[Zeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680.]).

[Scheme 1]

Experimental

Crystal data
  • C25H26N4O3

  • Mr = 430.50

  • Monoclinic, C c

  • a = 19.481 (2) Å

  • b = 12.0745 (13) Å

  • c = 10.4393 (11) Å

  • β = 115.006 (2)°

  • V = 2225.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART 4K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.991

  • 7050 measured reflections

  • 2192 independent reflections

  • 1846 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.104

  • S = 1.00

  • 2192 reflections

  • 332 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.15 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
C6—H6⋯O1i 0.93 2.50 3.320 (5) 147
C19—H19B⋯O1ii 0.96 2.59 3.545 (8) 175
C25—H25⋯O2iii 0.93 2.60 3.295 (5) 132
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

As a part of our ongoing work in the preparation of derivatives of heterocyclic compounds (Hu et al., 2006, 2007, 2010; He et al., 2007a,b; Ma et al. 2009; Zeng et al., 2008), we have synthesized and structurally characterized the title compound (Fig. 1). In the molecule, the two fused rings of pyrrolo[3,2-d]pyrimidine form a dihedral angle of 3.7 (2)°. The attached two phenyl rings are twisted with respect to the heterocyclic pyrrolo[3,2-d]pyrimidine system, making dihedral angles of 56.8 (2)° and 69.3 (2)°, respectively. The ethyl group (C13—C14) is disordered over two sites with occupancies that refined to 0.53 (1) and 0.47 (1); the ethoxy group (C18—C19) is also disordered over two sites with occupancies 0.63 (1) and 0.37 (1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. There are no π-π interactions.

Related literature top

For the synthesis, see: Hu et al. (2006, 2007, 2010). For related structures, see: He et al. (2007a,b); Ma et al. (2009); Zeng & Yan (2008).

Experimental top

The title compound was obtained in good yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixture of ethanol and dichloromethane (1:1 v/v) at room temperature.

Refinement top

All H atoms were located in difference maps and treated as riding atoms with C—H = 0.93 Å, Uiso=1.2Ueq (C) for Csp2, C—H = 0.97 Å, Uiso = 1.2Ueq (C) for CH2, C—H = 0.96 Å, Uiso = 1.5Ueq (C) for CH3. N—H = 0.86 Å, Uiso = 1.2Ueq (N) for NH.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme with displacement ellipsoids drawn at the 30% probability level.
Ethyl 2-diethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-3H- pyrrolo[3,2-d]pyrimidine-7-carboxylate top
Crystal data top
C25H26N4O3F(000) = 912
Mr = 430.50Dx = 1.285 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2386 reflections
a = 19.481 (2) Åθ = 2.3–23.4°
b = 12.0745 (13) ŵ = 0.09 mm1
c = 10.4393 (11) ÅT = 298 K
β = 115.006 (2)°Block, colourless
V = 2225.4 (4) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2192 independent reflections
Radiation source: fine-focus sealed tube1846 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ϕ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2424
Tmin = 0.973, Tmax = 0.991k = 1414
7050 measured reflectionsl = 1012
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.063P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2192 reflectionsΔρmax = 0.15 e Å3
332 parametersΔρmin = 0.19 e Å3
12 restraintsAbsolute structure: no
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H26N4O3V = 2225.4 (4) Å3
Mr = 430.50Z = 4
Monoclinic, CcMo Kα radiation
a = 19.481 (2) ŵ = 0.09 mm1
b = 12.0745 (13) ÅT = 298 K
c = 10.4393 (11) Å0.20 × 0.10 × 0.10 mm
β = 115.006 (2)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2192 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1846 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.991Rint = 0.050
7050 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04612 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.00Δρmax = 0.15 e Å3
2192 reflectionsΔρmin = 0.19 e Å3
332 parametersAbsolute structure: no
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*/UeqOcc. (<1)
C10.35411 (19)0.5896 (2)0.3254 (4)0.0403 (7)
C20.3739 (3)0.6278 (3)0.4599 (4)0.0603 (10)
H20.35540.59350.51880.072*
C30.4218 (3)0.7183 (4)0.5069 (5)0.0839 (15)
H30.43570.74520.59800.101*
C40.4489 (3)0.7682 (3)0.4199 (7)0.0839 (15)
H40.48020.83000.45130.101*
C50.4306 (2)0.7280 (3)0.2885 (6)0.0697 (13)
H50.45000.76150.23060.084*
C60.3834 (2)0.6381 (3)0.2401 (4)0.0489 (8)
H60.37130.61020.15010.059*
C70.33929 (19)0.3910 (3)0.3331 (3)0.0401 (8)
C80.23552 (19)0.5019 (3)0.1557 (4)0.0481 (8)
C90.29509 (19)0.3005 (2)0.2527 (3)0.0398 (7)
C100.22868 (18)0.3156 (3)0.1325 (3)0.0415 (7)
C110.1974 (3)0.6797 (3)0.2194 (6)0.0808 (14)
H11A0.22290.64640.31220.097*
H11B0.14380.68300.19720.097*
C120.2268 (3)0.7972 (3)0.2256 (6)0.0738 (12)
H12A0.27890.79490.24070.111*
H12B0.22250.83650.30190.111*
H12C0.19740.83430.13810.111*
C130.1572 (6)0.6089 (8)0.0445 (10)0.063 (3)0.53
H13A0.18040.56210.09070.075*0.53
H13B0.10850.57670.06130.075*0.53
C140.1442 (5)0.7208 (7)0.1108 (8)0.071 (2)0.53
H14A0.11940.76710.06860.107*0.53
H14B0.11300.71430.21030.107*0.53
H14C0.19200.75320.09620.107*0.53
C13'0.1387 (5)0.6277 (11)0.0102 (11)0.060 (4)0.47
H13C0.11440.69600.00320.072*0.47
H13D0.10330.56680.02820.072*0.47
C14'0.1678 (6)0.6352 (11)0.1238 (9)0.080 (3)0.47
H14D0.21010.68510.09360.120*0.47
H14E0.12830.66220.20980.120*0.47
H14F0.18350.56320.13980.120*0.47
C150.19836 (18)0.2084 (3)0.0816 (4)0.0438 (8)
C160.2478 (2)0.1342 (3)0.1758 (4)0.0460 (8)
H160.24180.05770.16960.055*
C170.1284 (2)0.1791 (3)0.0417 (4)0.0497 (8)
C180.0502 (6)0.0198 (12)0.1557 (11)0.066 (4)0.63
H18A0.00790.06940.17440.079*0.63
H18B0.04030.04990.12030.079*0.63
C190.0625 (5)0.0017 (8)0.2874 (9)0.069 (2)0.63
H19A0.07050.07180.32240.103*0.63
H19B0.01870.03360.35810.103*0.63
H19C0.10610.04450.26560.103*0.63
C18'0.0571 (10)0.0377 (18)0.1873 (18)0.066 (7)0.37
H18C0.04650.09710.25560.079*0.37
H18D0.01220.02580.17080.079*0.37
C19'0.0759 (11)0.0666 (16)0.245 (2)0.097 (5)0.37
H19D0.11680.05230.27080.146*0.37
H19E0.03220.09060.32660.146*0.37
H19F0.09060.12340.17390.146*0.37
C200.3654 (2)0.1325 (2)0.3965 (3)0.0411 (7)
C210.3453 (2)0.0630 (3)0.4797 (4)0.0541 (9)
H210.29460.05400.46160.065*
C220.4006 (3)0.0071 (3)0.5897 (5)0.0684 (12)
H220.38720.04020.64570.082*
C230.4755 (3)0.0207 (3)0.6173 (4)0.0635 (11)
H230.51290.01670.69240.076*
C240.4952 (2)0.0900 (3)0.5332 (4)0.0558 (9)
H240.54590.09840.55080.067*
C250.4401 (2)0.1468 (3)0.4232 (4)0.0477 (8)
H250.45350.19450.36760.057*
N10.30567 (16)0.4938 (2)0.2734 (3)0.0427 (6)
N20.19752 (16)0.4179 (2)0.0831 (3)0.0499 (7)
N30.20773 (19)0.6083 (2)0.1163 (4)0.0717 (11)
N40.30646 (16)0.18742 (19)0.2789 (3)0.0411 (6)
O10.39918 (14)0.38737 (18)0.4370 (3)0.0535 (6)
O20.08390 (15)0.2436 (2)0.1197 (3)0.0663 (8)
O30.12107 (15)0.0691 (2)0.0540 (3)0.0713 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0400 (17)0.0294 (14)0.0459 (19)0.0009 (13)0.0126 (15)0.0004 (13)
C20.086 (3)0.0422 (18)0.049 (2)0.0030 (18)0.024 (2)0.0038 (17)
C30.107 (4)0.051 (2)0.060 (3)0.002 (3)0.002 (3)0.019 (2)
C40.062 (3)0.046 (2)0.117 (4)0.018 (2)0.012 (3)0.015 (3)
C50.054 (2)0.0420 (19)0.116 (4)0.0014 (18)0.039 (3)0.015 (2)
C60.050 (2)0.0412 (17)0.059 (2)0.0023 (15)0.0267 (18)0.0026 (15)
C70.0405 (19)0.0384 (16)0.0391 (19)0.0017 (13)0.0146 (17)0.0007 (13)
C80.041 (2)0.0399 (18)0.054 (2)0.0010 (15)0.0115 (18)0.0056 (15)
C90.0412 (18)0.0346 (15)0.0420 (18)0.0043 (14)0.0159 (15)0.0034 (13)
C100.0368 (18)0.0405 (16)0.0429 (18)0.0054 (14)0.0126 (15)0.0032 (14)
C110.060 (3)0.048 (2)0.141 (5)0.0094 (19)0.048 (3)0.006 (3)
C120.071 (3)0.047 (2)0.096 (3)0.009 (2)0.028 (2)0.005 (2)
C130.034 (5)0.049 (6)0.082 (9)0.013 (4)0.001 (5)0.011 (5)
C140.071 (6)0.067 (5)0.067 (5)0.005 (4)0.020 (5)0.002 (4)
C13'0.027 (6)0.044 (5)0.094 (8)0.010 (4)0.012 (5)0.005 (5)
C14'0.076 (7)0.095 (9)0.057 (7)0.012 (6)0.017 (6)0.010 (6)
C150.0385 (19)0.0446 (18)0.0441 (19)0.0059 (14)0.0136 (15)0.0065 (15)
C160.0461 (19)0.0362 (16)0.053 (2)0.0108 (15)0.0184 (16)0.0120 (15)
C170.037 (2)0.055 (2)0.054 (2)0.0072 (17)0.0166 (17)0.0114 (18)
C180.050 (5)0.067 (6)0.071 (6)0.028 (4)0.018 (5)0.018 (5)
C190.050 (4)0.074 (5)0.062 (5)0.006 (4)0.004 (4)0.008 (4)
C18'0.050 (9)0.067 (11)0.071 (12)0.028 (8)0.018 (9)0.018 (9)
C19'0.091 (12)0.102 (13)0.085 (12)0.015 (11)0.024 (10)0.028 (10)
C200.0461 (19)0.0305 (15)0.0409 (18)0.0023 (14)0.0129 (15)0.0044 (13)
C210.055 (2)0.0455 (18)0.063 (2)0.0034 (17)0.0259 (19)0.0050 (18)
C220.081 (3)0.053 (2)0.069 (3)0.001 (2)0.029 (2)0.017 (2)
C230.066 (3)0.047 (2)0.057 (2)0.0078 (18)0.007 (2)0.0025 (18)
C240.044 (2)0.051 (2)0.061 (2)0.0010 (16)0.0110 (18)0.0144 (18)
C250.047 (2)0.0423 (17)0.049 (2)0.0041 (15)0.0159 (17)0.0048 (15)
N10.0402 (15)0.0330 (13)0.0479 (16)0.0051 (12)0.0118 (13)0.0016 (12)
N20.0387 (16)0.0438 (16)0.0527 (17)0.0048 (12)0.0054 (14)0.0019 (13)
N30.049 (2)0.0425 (17)0.089 (3)0.0028 (14)0.0042 (19)0.0060 (17)
N40.0415 (15)0.0316 (12)0.0454 (15)0.0047 (12)0.0139 (13)0.0031 (12)
O10.0523 (15)0.0408 (12)0.0467 (14)0.0044 (11)0.0007 (13)0.0021 (10)
O20.0453 (15)0.0629 (16)0.0679 (18)0.0027 (13)0.0018 (14)0.0078 (13)
O30.0526 (17)0.0558 (15)0.0760 (19)0.0153 (13)0.0016 (14)0.0192 (15)
Geometric parameters (Å, º) top
C1—C21.370 (5)C13'—H13C0.9700
C1—C61.375 (5)C13'—H13D0.9700
C1—N11.446 (4)C14'—H14D0.9600
C2—C31.386 (6)C14'—H14E0.9600
C2—H20.9300C14'—H14F0.9600
C3—C41.369 (8)C15—C161.378 (5)
C3—H30.9300C15—C171.469 (5)
C4—C51.353 (7)C16—N41.355 (4)
C4—H40.9300C16—H160.9300
C5—C61.374 (5)C17—O21.194 (5)
C5—H50.9300C17—O31.336 (4)
C6—H60.9300C18—O31.466 (8)
C7—O11.212 (4)C18—C191.509 (10)
C7—N11.419 (4)C18—H18A0.9700
C7—C91.424 (4)C18—H18B0.9700
C8—N21.295 (4)C19—H19A0.9600
C8—N31.387 (4)C19—H19B0.9600
C8—N11.402 (4)C19—H19C0.9600
C9—C101.382 (5)C18'—O31.472 (11)
C9—N41.392 (4)C18'—C19'1.505 (11)
C10—N21.377 (4)C18'—H18C0.9700
C10—C151.429 (5)C18'—H18D0.9700
C11—N31.458 (6)C19'—H19D0.9600
C11—C121.521 (6)C19'—H19E0.9600
C11—H11A0.9700C19'—H19F0.9600
C11—H11B0.9700C20—C251.373 (5)
C12—H12A0.9600C20—C211.378 (5)
C12—H12B0.9600C20—N41.440 (4)
C12—H12C0.9600C21—C221.374 (6)
C13—C141.490 (9)C21—H210.9300
C13—N31.546 (9)C22—C231.373 (6)
C13—H13A0.9700C22—H220.9300
C13—H13B0.9700C23—C241.378 (6)
C14—H14A0.9600C23—H230.9300
C14—H14B0.9600C24—C251.378 (5)
C14—H14C0.9600C24—H240.9300
C13'—N31.451 (9)C25—H250.9300
C13'—C14'1.518 (10)
C2—C1—C6120.5 (3)C16—C15—C17125.4 (3)
C2—C1—N1120.7 (3)C10—C15—C17129.0 (3)
C6—C1—N1118.7 (3)N4—C16—C15111.0 (3)
C1—C2—C3118.9 (4)N4—C16—H16124.5
C1—C2—H2120.5C15—C16—H16124.5
C3—C2—H2120.5O2—C17—O3124.5 (3)
C4—C3—C2120.3 (4)O2—C17—C15125.3 (3)
C4—C3—H3119.9O3—C17—C15110.2 (3)
C2—C3—H3119.9O3—C18—C19104.8 (8)
C5—C4—C3120.3 (4)O3—C18—H18A110.8
C5—C4—H4119.9C19—C18—H18A110.8
C3—C4—H4119.9O3—C18—H18B110.8
C4—C5—C6120.4 (4)C19—C18—H18B110.8
C4—C5—H5119.8H18A—C18—H18B108.9
C6—C5—H5119.8O3—C18'—C19'110.0 (13)
C5—C6—C1119.6 (4)O3—C18'—H18C109.7
C5—C6—H6120.2C19'—C18'—H18C109.7
C1—C6—H6120.2O3—C18'—H18D109.7
O1—C7—N1121.0 (3)C19'—C18'—H18D109.7
O1—C7—C9127.8 (3)H18C—C18'—H18D108.2
N1—C7—C9111.1 (3)C18'—C19'—H19D109.5
N2—C8—N3119.8 (3)C18'—C19'—H19E109.5
N2—C8—N1124.2 (3)H19D—C19'—H19E109.5
N3—C8—N1116.0 (3)C18'—C19'—H19F109.5
C10—C9—N4108.5 (3)H19D—C19'—H19F109.5
C10—C9—C7122.3 (3)H19E—C19'—H19F109.5
N4—C9—C7129.1 (3)C25—C20—C21120.5 (3)
N2—C10—C9123.6 (3)C25—C20—N4120.7 (3)
N2—C10—C15128.8 (3)C21—C20—N4118.8 (3)
C9—C10—C15107.4 (3)C22—C21—C20119.7 (4)
N3—C11—C12114.6 (4)C22—C21—H21120.2
N3—C11—H11A108.6C20—C21—H21120.2
C12—C11—H11A108.6C23—C22—C21120.3 (4)
N3—C11—H11B108.6C23—C22—H22119.8
C12—C11—H11B108.6C21—C22—H22119.8
H11A—C11—H11B107.6C22—C23—C24119.7 (4)
C11—C12—H12A109.5C22—C23—H23120.1
C11—C12—H12B109.5C24—C23—H23120.1
H12A—C12—H12B109.5C25—C24—C23120.3 (4)
C11—C12—H12C109.5C25—C24—H24119.9
H12A—C12—H12C109.5C23—C24—H24119.9
H12B—C12—H12C109.5C20—C25—C24119.5 (3)
C14—C13—N3114.5 (7)C20—C25—H25120.2
C14—C13—H13A108.6C24—C25—H25120.2
N3—C13—H13A108.6C8—N1—C7122.9 (2)
C14—C13—H13B108.6C8—N1—C1120.9 (3)
N3—C13—H13B108.6C7—N1—C1115.3 (3)
H13A—C13—H13B107.6C8—N2—C10115.6 (3)
N3—C13'—C14'102.3 (7)C8—N3—C13'121.0 (6)
N3—C13'—H13C111.3C8—N3—C11119.2 (4)
C14'—C13'—H13C111.3C13'—N3—C11102.3 (6)
N3—C13'—H13D111.3C8—N3—C13108.4 (4)
C14'—C13'—H13D111.3C13'—N3—C1324.6 (4)
H13C—C13'—H13D109.2C11—N3—C13125.1 (5)
C13'—C14'—H14D109.5C16—N4—C9107.4 (3)
C13'—C14'—H14E109.5C16—N4—C20124.0 (2)
H14D—C14'—H14E109.5C9—N4—C20128.5 (3)
C13'—C14'—H14F109.5C17—O3—C18120.2 (7)
H14D—C14'—H14F109.5C17—O3—C18'111.1 (9)
H14E—C14'—H14F109.5C18—O3—C18'18.0 (13)
C16—C15—C10105.6 (3)
C6—C1—C2—C32.1 (6)C2—C1—N1—C8119.2 (4)
N1—C1—C2—C3178.5 (4)C6—C1—N1—C864.3 (4)
C1—C2—C3—C40.1 (7)C2—C1—N1—C771.1 (4)
C2—C3—C4—C51.5 (8)C6—C1—N1—C7105.4 (3)
C3—C4—C5—C61.2 (7)N3—C8—N2—C10178.4 (3)
C4—C5—C6—C10.7 (6)N1—C8—N2—C102.9 (5)
C2—C1—C6—C52.4 (5)C9—C10—N2—C81.3 (5)
N1—C1—C6—C5178.9 (3)C15—C10—N2—C8175.7 (3)
O1—C7—C9—C10177.6 (3)N2—C8—N3—C13'3.7 (8)
N1—C7—C9—C100.3 (4)N1—C8—N3—C13'175.1 (6)
O1—C7—C9—N45.3 (6)N2—C8—N3—C11124.5 (4)
N1—C7—C9—N4176.9 (3)N1—C8—N3—C1156.7 (5)
N4—C9—C10—N2174.7 (3)N2—C8—N3—C1327.1 (7)
C7—C9—C10—N23.0 (5)N1—C8—N3—C13151.7 (6)
N4—C9—C10—C150.7 (3)C14'—C13'—N3—C886.6 (10)
C7—C9—C10—C15178.3 (3)C14'—C13'—N3—C11138.0 (8)
N2—C10—C15—C16174.1 (3)C14'—C13'—N3—C1321.7 (15)
C9—C10—C15—C160.9 (4)C12—C11—N3—C8134.4 (4)
N2—C10—C15—C174.2 (6)C12—C11—N3—C13'89.2 (7)
C9—C10—C15—C17179.2 (3)C12—C11—N3—C1379.0 (8)
C10—C15—C16—N40.9 (4)C14—C13—N3—C8160.6 (8)
C17—C15—C16—N4179.3 (3)C14—C13—N3—C13'74.4 (19)
C16—C15—C17—O2176.5 (4)C14—C13—N3—C1149.9 (12)
C10—C15—C17—O21.4 (6)C15—C16—N4—C90.5 (4)
C16—C15—C17—O33.0 (5)C15—C16—N4—C20176.8 (3)
C10—C15—C17—O3179.0 (3)C10—C9—N4—C160.1 (4)
C25—C20—C21—C220.5 (5)C7—C9—N4—C16177.6 (3)
N4—C20—C21—C22177.9 (3)C10—C9—N4—C20175.9 (3)
C20—C21—C22—C230.4 (6)C7—C9—N4—C201.5 (6)
C21—C22—C23—C240.7 (6)C25—C20—N4—C16124.3 (3)
C22—C23—C24—C251.0 (6)C21—C20—N4—C1654.1 (5)
C21—C20—C25—C240.8 (5)C25—C20—N4—C960.2 (5)
N4—C20—C25—C24177.5 (3)C21—C20—N4—C9121.4 (4)
C23—C24—C25—C201.1 (5)O2—C17—O3—C189.1 (8)
N2—C8—N1—C75.8 (5)C15—C17—O3—C18170.5 (6)
N3—C8—N1—C7175.4 (3)O2—C17—O3—C18'8.2 (12)
N2—C8—N1—C1163.1 (3)C15—C17—O3—C18'172.2 (11)
N3—C8—N1—C115.6 (5)C19—C18—O3—C1793.6 (10)
O1—C7—N1—C8178.2 (3)C19—C18—O3—C18'30 (3)
C9—C7—N1—C83.8 (4)C19'—C18'—O3—C17144.4 (15)
O1—C7—N1—C112.3 (4)C19'—C18'—O3—C1892 (4)
C9—C7—N1—C1165.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.503.320 (5)147
C19—H19B···O1ii0.962.593.545 (8)175
C25—H25···O2iii0.932.603.295 (5)132
Symmetry codes: (i) x, y+1, z1/2; (ii) x1/2, y1/2, z1; (iii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC25H26N4O3
Mr430.50
Crystal system, space groupMonoclinic, Cc
Temperature (K)298
a, b, c (Å)19.481 (2), 12.0745 (13), 10.4393 (11)
β (°) 115.006 (2)
V3)2225.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.973, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
7050, 2192, 1846
Rint0.050
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.104, 1.00
No. of reflections2192
No. of parameters332
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.19
Absolute structureNo

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.503.320 (5)146.7
C19—H19B···O1ii0.962.593.545 (8)174.7
C25—H25···O2iii0.932.603.295 (5)132.2
Symmetry codes: (i) x, y+1, z1/2; (ii) x1/2, y1/2, z1; (iii) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

We gratefully acknowledge financial support of this work by the Science Research Project of Hubei University of Medicine (Nos. 2008CXG01 and 2009QDJ15).

References

First citationBruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHe, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884.  Web of Science CSD CrossRef IUCr Journals
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First citationHu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735.  Web of Science CSD CrossRef IUCr Journals
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First citationHu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459.  Web of Science CSD CrossRef IUCr Journals
First citationMa, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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First citationZeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680.  Web of Science CSD CrossRef IUCr Journals

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