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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Ethyl 4-(4-nitro­phen­yl)-2-(tri­fluoro­meth­yl)pyrimido[1,2-a]benzimidazole-3-carboxyl­ate

aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China, and bSchool of Chemistry and Chemical Engineering and Key Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
*Correspondence e-mail: actaeli@gmail.com

(Received 11 November 2008; accepted 24 November 2008; online 29 November 2008)

In the title compound, C20H13F3N4O4, the fused pyrimido[1,2-a]benzimidazole ring system is nearly planar, with a maximum deviation from the mean plane of 0.126 (1) Å. Mol­ecules are linked by C—H⋯N and C—H⋯O hydrogen bonds and by ππ inter­actions with inter­planar distances of 3.2661 (6) and 3.2775 (6) Å.

Related literature

For the bioactivity of benzo[4,5] imidazo[1,2-a]-pyrimidine derivatives, see: Abdel-Hafez (2007[Abdel-Hafez, A. A. M. (2007). Arch. Pharm. Res. 30, 678-684.]); Cheung et al. (2002[Cheung, M., Harris, P. A., Hasegawa, M., Ida, S., Kano, K., Nishigaki, N., Sato, H., Veal, J. M., Washio, Y. & West, R. I. (2002). WO Patent No. 2 002 044 156.]); Nunes, Zhu, Amouzegh et al. (2005[Nunes, J. J., Zhu, X. T., Amouzegh, P., Ghiron, C., Johnston, D. N. & Power, E. C. (2005). WO Patent No. 2 005 009 443.]); Nunes, Zhu, Ermann et al. (2005[Nunes, J. J., Zhu, X. T., Ermann, M., Ghiron, C., Johnston, D. N. & Saluste, C. G. P. (2005). WO Patent No. 2 005 021 551.][Nunes, J. J., Zhu, X. T., Amouzegh, P., Ghiron, C., Johnston, D. N. & Power, E. C. (2005). WO Patent No. 2 005 009 443.]). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003[Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2 003 176 284.]); Ulrich (2004[Ulrich, H. (2004). US Patent No. 2 004 033 897.]).

[Scheme 1]

Experimental

Crystal data
  • C20H13F3N4O4

  • Mr = 430.34

  • Monoclinic, P 21 /c

  • a = 8.4075 (5) Å

  • b = 26.6904 (14) Å

  • c = 9.0559 (5) Å

  • β = 111.027 (2)°

  • V = 1896.82 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 113 (2) K

  • 0.32 × 0.30 × 0.26 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.961, Tmax = 0.968

  • 18499 measured reflections

  • 4492 independent reflections

  • 3911 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.116

  • S = 1.11

  • 4492 reflections

  • 282 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯N3i 0.95 2.41 3.2987 (18) 156
C16—H16⋯O3ii 0.95 2.55 3.2096 (18) 127
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXTL.

Supporting information


Comment top

Among the derivatives of the dihydropyrimidine, the derivatives of pyrimido[1,2-a]benzimidazole have been reported to have a variety of biological activities, such as antineoplastic activity (Abdel-Hafez, 2007), protein kinase inhibitor (Nunes, Zhu, Amouzegh et al., 2005), T cell activation (Nunes, Zhu, Ermann et al., 2005), TIE-2 and/or VEGFR2 inhibitory activities (Cheung et al, 2002). Besides, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay much attention to the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. To further study the relationship between the structure and bioactivity, we synthesised series of derivatives of benzo[4,5] pyrimido[1,2-a]benzimidazole. Here we report the crystal structure of the title compound, (I).

In the title molecule (Fig.1), the fused ring are near planar, for the dihedral angle between the phenyl ring/imidazole ring/pyrimidine ring are 3.68 (9) and 3.65 (8)°, respectively. The conformation of the attachment of the phenyl ring to the fused ring is described by the torsion angle of N2-C2-C11-C16 of 123.17 (14)°.

The crystal packing is stabilized by C—H···N and C—H···O intermolecular hydrogen bond (Table 1, Fig. 2). In addition, there are the intermolecular ππ stacking interacions between the two neighbouring parallel imidazole rings(symmetry code: 1-x,1-y,1-z; centroid-to-centroid distance: 3.3386 (9)Å, plane-plane distance: 3.2661 (6)Å, displacement distance: 0.692Å) and phenyl rings (C5-C10, symmetry code: -x,1-y,1-z; centroid-to-centroid distance: 3.9822 (9)Å, plane-plane distance: 3.2775 (6)Å, displacement distance: 2.262Å) in the title compound.

Related literature top

For the bioactivity of benzo[4,5] imidazo[1,2-a]-pyrimidine derivatives, see: Abdel-Hafez (2007); Cheung et al. (2002); Nunes, Zhu, Amouzegh et al. (2005); Nunes, Zhu, Ermann et al. (2005).For the bioactivity of organofluorine compounds, see: Hermann et al. (2003); Ulrich (2004).

Experimental top

The title compound was synthesized by the reaction of 4-nitrobenzaldehyde (1 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate (1 mmol) and 1H-benzo[d]imidazol-2-amine (1 mmol) in 3-butyl-1-methyl-1H- imidazol-3-ium chloride (1.5 mL) at 363 K for a certain time (monitered by TLC). After cooling, the reaction mixture was washed with water and recrystallized from ethanol, to obtain single crystals suitable for X-ray diffraction.

Refinement top

H atoms were placed in calculated positions (C-H = 0.95–0.99 Å) and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); 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, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.
Ethyl 4-(4-nitrophenyl)-2-(trifluoromethyl)pyrimido[1,2-a]benzimidazole- 3-carboxylate top
Crystal data top
C20H13F3N4O4F(000) = 880
Mr = 430.34Dx = 1.507 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4213 reflections
a = 8.4075 (5) Åθ = 2.3–27.9°
b = 26.6904 (14) ŵ = 0.13 mm1
c = 9.0559 (5) ÅT = 113 K
β = 111.027 (2)°Block, orange
V = 1896.82 (18) Å30.32 × 0.30 × 0.26 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer
4492 independent reflections
Radiation source: rotating anode3911 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.039
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.5°
ω scansh = 1111
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2002)
k = 3435
Tmin = 0.961, Tmax = 0.968l = 1111
18499 measured reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.3435P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
4492 reflectionsΔρmax = 0.35 e Å3
282 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0129 (15)
Crystal data top
C20H13F3N4O4V = 1896.82 (18) Å3
Mr = 430.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4075 (5) ŵ = 0.13 mm1
b = 26.6904 (14) ÅT = 113 K
c = 9.0559 (5) Å0.32 × 0.30 × 0.26 mm
β = 111.027 (2)°
Data collection top
Rigaku Saturn
diffractometer
4492 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2002)
3911 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.968Rint = 0.039
18499 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.11Δρmax = 0.35 e Å3
4492 reflectionsΔρmin = 0.22 e Å3
282 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F10.84705 (13)0.60521 (4)0.95949 (11)0.0426 (3)
F20.69893 (13)0.67273 (4)0.89880 (11)0.0385 (3)
F30.89019 (12)0.65773 (4)0.79846 (11)0.0409 (3)
O10.62940 (15)0.71967 (4)0.55129 (14)0.0356 (3)
O20.75651 (13)0.66746 (4)0.43224 (12)0.0274 (2)
O30.21549 (16)0.71512 (4)0.24329 (13)0.0346 (3)
O40.26759 (14)0.64080 (4)0.30905 (12)0.0308 (3)
N10.57725 (14)0.56861 (4)0.74106 (13)0.0219 (3)
N20.37814 (14)0.56650 (4)0.47093 (13)0.0189 (2)
N30.37200 (15)0.50437 (4)0.64198 (13)0.0229 (3)
N40.26160 (15)0.67171 (4)0.21060 (14)0.0223 (3)
C10.44825 (17)0.54571 (5)0.62568 (15)0.0202 (3)
C20.45006 (17)0.60793 (5)0.43043 (15)0.0191 (3)
C30.57796 (17)0.63165 (5)0.54926 (16)0.0209 (3)
C40.63487 (17)0.61029 (5)0.70372 (15)0.0215 (3)
C50.24130 (17)0.53536 (5)0.38824 (16)0.0204 (3)
C60.24395 (18)0.49711 (5)0.49625 (17)0.0220 (3)
C70.12231 (19)0.45881 (5)0.45180 (18)0.0266 (3)
H70.12440.43220.52220.032*
C80.00046 (19)0.46102 (6)0.30259 (18)0.0293 (3)
H80.08370.43530.26940.035*
C90.0057 (2)0.50043 (6)0.19808 (18)0.0293 (3)
H90.09460.50110.09730.035*
C100.11445 (18)0.53821 (6)0.23755 (16)0.0255 (3)
H100.11120.56470.16640.031*
C110.39418 (17)0.62415 (5)0.26248 (15)0.0200 (3)
C120.41635 (18)0.59172 (5)0.15022 (16)0.0223 (3)
H120.46050.55900.18040.027*
C130.37390 (18)0.60735 (5)0.00523 (16)0.0218 (3)
H130.38830.58570.08280.026*
C140.30986 (17)0.65537 (5)0.04460 (15)0.0204 (3)
C150.28857 (18)0.68848 (5)0.06432 (16)0.0235 (3)
H150.24570.72130.03370.028*
C160.33160 (18)0.67247 (5)0.21975 (16)0.0226 (3)
H160.31840.69450.29700.027*
C170.65622 (18)0.67848 (5)0.51235 (16)0.0246 (3)
C180.8334 (2)0.71015 (6)0.3818 (2)0.0351 (4)
H18A0.89540.73170.47350.042*
H18B0.74450.73050.30320.042*
C190.9537 (2)0.68897 (7)0.3101 (2)0.0422 (4)
H19A1.04690.67160.39180.063*
H19B1.00030.71620.26520.063*
H19C0.89280.66530.22630.063*
C200.76917 (19)0.63640 (6)0.84092 (17)0.0284 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0462 (6)0.0400 (6)0.0245 (5)0.0004 (5)0.0079 (4)0.0038 (4)
F20.0469 (6)0.0361 (5)0.0305 (5)0.0008 (4)0.0115 (4)0.0114 (4)
F30.0288 (5)0.0560 (6)0.0329 (5)0.0142 (4)0.0050 (4)0.0033 (4)
O10.0452 (7)0.0252 (6)0.0389 (6)0.0043 (5)0.0181 (5)0.0062 (5)
O20.0309 (6)0.0254 (5)0.0283 (5)0.0041 (4)0.0135 (5)0.0027 (4)
O30.0516 (7)0.0228 (5)0.0276 (6)0.0064 (5)0.0121 (5)0.0081 (4)
O40.0405 (6)0.0326 (6)0.0199 (5)0.0078 (5)0.0116 (5)0.0013 (4)
N10.0222 (6)0.0260 (6)0.0176 (5)0.0036 (5)0.0073 (5)0.0012 (5)
N20.0210 (6)0.0200 (5)0.0162 (5)0.0018 (4)0.0073 (4)0.0010 (4)
N30.0240 (6)0.0228 (6)0.0238 (6)0.0041 (5)0.0109 (5)0.0038 (5)
N40.0244 (6)0.0225 (6)0.0202 (6)0.0011 (5)0.0082 (5)0.0039 (5)
C10.0220 (6)0.0225 (6)0.0183 (6)0.0055 (5)0.0097 (5)0.0035 (5)
C20.0215 (6)0.0188 (6)0.0190 (6)0.0026 (5)0.0097 (5)0.0006 (5)
C30.0227 (7)0.0219 (7)0.0182 (6)0.0010 (5)0.0074 (5)0.0002 (5)
C40.0216 (6)0.0247 (7)0.0180 (6)0.0037 (5)0.0069 (5)0.0001 (5)
C50.0203 (6)0.0208 (6)0.0217 (7)0.0003 (5)0.0096 (5)0.0024 (5)
C60.0231 (7)0.0210 (7)0.0248 (7)0.0034 (5)0.0122 (6)0.0003 (5)
C70.0299 (7)0.0210 (7)0.0352 (8)0.0005 (6)0.0193 (6)0.0006 (6)
C80.0281 (7)0.0271 (7)0.0365 (8)0.0064 (6)0.0163 (7)0.0085 (6)
C90.0279 (8)0.0344 (8)0.0254 (7)0.0046 (6)0.0093 (6)0.0053 (6)
C100.0262 (7)0.0285 (7)0.0216 (7)0.0021 (6)0.0084 (6)0.0012 (6)
C110.0199 (6)0.0219 (6)0.0176 (6)0.0010 (5)0.0062 (5)0.0003 (5)
C120.0269 (7)0.0196 (6)0.0209 (7)0.0032 (5)0.0090 (6)0.0019 (5)
C130.0261 (7)0.0212 (7)0.0198 (6)0.0021 (5)0.0102 (5)0.0010 (5)
C140.0205 (6)0.0232 (7)0.0166 (6)0.0010 (5)0.0057 (5)0.0028 (5)
C150.0273 (7)0.0194 (6)0.0227 (7)0.0028 (5)0.0079 (6)0.0022 (5)
C160.0261 (7)0.0215 (7)0.0198 (7)0.0019 (5)0.0077 (6)0.0008 (5)
C170.0248 (7)0.0276 (7)0.0191 (6)0.0024 (6)0.0051 (6)0.0003 (5)
C180.0380 (9)0.0335 (8)0.0348 (9)0.0097 (7)0.0142 (7)0.0076 (7)
C190.0411 (10)0.0533 (11)0.0367 (9)0.0086 (8)0.0195 (8)0.0058 (8)
C200.0301 (8)0.0311 (8)0.0205 (7)0.0003 (6)0.0047 (6)0.0005 (6)
Geometric parameters (Å, º) top
F1—C201.3304 (17)C7—C81.376 (2)
F2—C201.3365 (17)C7—H70.9500
F3—C201.3372 (18)C8—C91.405 (2)
O1—C171.2004 (18)C8—H80.9500
O2—C171.3277 (17)C9—C101.381 (2)
O2—C181.4617 (17)C9—H90.9500
O3—N41.2239 (15)C10—H100.9500
O4—N41.2289 (15)C11—C161.3941 (19)
N1—C41.3056 (18)C11—C121.3978 (18)
N1—C11.3522 (18)C12—C131.3865 (18)
N2—C21.3719 (17)C12—H120.9500
N2—C51.3989 (17)C13—C141.3864 (19)
N2—C11.4235 (16)C13—H130.9500
N3—C11.3108 (18)C14—C151.3830 (19)
N3—C61.3851 (19)C15—C161.3890 (19)
N4—C141.4755 (16)C15—H150.9500
C2—C31.3729 (19)C16—H160.9500
C2—C111.4861 (18)C18—C191.495 (2)
C3—C41.4248 (18)C18—H18A0.9900
C3—C171.5049 (19)C18—H18B0.9900
C4—C201.516 (2)C19—H19A0.9800
C5—C101.4004 (19)C19—H19B0.9800
C5—C61.4084 (19)C19—H19C0.9800
C6—C71.399 (2)
C17—O2—C18115.89 (12)C16—C11—C12120.43 (12)
C4—N1—C1117.02 (12)C16—C11—C2120.19 (12)
C2—N2—C5133.83 (11)C12—C11—C2119.22 (12)
C2—N2—C1120.72 (11)C13—C12—C11119.95 (13)
C5—N2—C1105.42 (11)C13—C12—H12120.0
C1—N3—C6104.76 (11)C11—C12—H12120.0
O3—N4—O4123.49 (12)C14—C13—C12118.30 (12)
O3—N4—C14118.27 (11)C14—C13—H13120.9
O4—N4—C14118.23 (11)C12—C13—H13120.9
N3—C1—N1125.63 (12)C15—C14—C13123.03 (12)
N3—C1—N2113.11 (12)C15—C14—N4118.63 (12)
N1—C1—N2121.23 (12)C13—C14—N4118.34 (12)
N2—C2—C3117.29 (12)C14—C15—C16118.21 (13)
N2—C2—C11120.05 (12)C14—C15—H15120.9
C3—C2—C11122.61 (12)C16—C15—H15120.9
C2—C3—C4118.54 (13)C15—C16—C11120.07 (13)
C2—C3—C17119.40 (12)C15—C16—H16120.0
C4—C3—C17122.05 (12)C11—C16—H16120.0
N1—C4—C3124.75 (13)O1—C17—O2125.91 (14)
N1—C4—C20114.58 (12)O1—C17—C3123.53 (13)
C3—C4—C20120.66 (13)O2—C17—C3110.57 (12)
N2—C5—C10132.99 (13)O2—C18—C19106.55 (13)
N2—C5—C6104.70 (12)O2—C18—H18A110.4
C10—C5—C6122.20 (13)C19—C18—H18A110.4
N3—C6—C7127.89 (13)O2—C18—H18B110.4
N3—C6—C5111.94 (12)C19—C18—H18B110.4
C7—C6—C5120.13 (13)H18A—C18—H18B108.6
C8—C7—C6117.67 (13)C18—C19—H19A109.5
C8—C7—H7121.2C18—C19—H19B109.5
C6—C7—H7121.2H19A—C19—H19B109.5
C7—C8—C9121.65 (14)C18—C19—H19C109.5
C7—C8—H8119.2H19A—C19—H19C109.5
C9—C8—H8119.2H19B—C19—H19C109.5
C10—C9—C8121.95 (14)F1—C20—F2107.24 (12)
C10—C9—H9119.0F1—C20—F3107.08 (12)
C8—C9—H9119.0F2—C20—F3107.02 (12)
C9—C10—C5116.31 (13)F1—C20—C4112.34 (12)
C9—C10—H10121.8F2—C20—C4110.55 (12)
C5—C10—H10121.8F3—C20—C4112.33 (12)
C6—N3—C1—N1176.80 (12)C7—C8—C9—C101.9 (2)
C6—N3—C1—N21.36 (15)C8—C9—C10—C50.5 (2)
C4—N1—C1—N3178.44 (13)N2—C5—C10—C9177.67 (14)
C4—N1—C1—N20.42 (18)C6—C5—C10—C92.0 (2)
C2—N2—C1—N3175.64 (11)N2—C2—C11—C16123.17 (14)
C5—N2—C1—N32.61 (15)C3—C2—C11—C1659.60 (18)
C2—N2—C1—N16.11 (18)N2—C2—C11—C1261.32 (17)
C5—N2—C1—N1175.64 (11)C3—C2—C11—C12115.92 (15)
C5—N2—C2—C3174.80 (13)C16—C11—C12—C130.8 (2)
C1—N2—C2—C37.54 (18)C2—C11—C12—C13176.33 (12)
C5—N2—C2—C117.8 (2)C11—C12—C13—C140.0 (2)
C1—N2—C2—C11169.83 (11)C12—C13—C14—C150.9 (2)
N2—C2—C3—C43.79 (18)C12—C13—C14—N4178.87 (12)
C11—C2—C3—C4173.52 (12)O3—N4—C14—C154.90 (19)
N2—C2—C3—C17177.54 (11)O4—N4—C14—C15174.11 (13)
C11—C2—C3—C175.16 (19)O3—N4—C14—C13175.37 (13)
C1—N1—C4—C33.5 (2)O4—N4—C14—C135.63 (18)
C1—N1—C4—C20175.22 (12)C13—C14—C15—C160.8 (2)
C2—C3—C4—N11.9 (2)N4—C14—C15—C16178.91 (12)
C17—C3—C4—N1176.76 (13)C14—C15—C16—C110.1 (2)
C2—C3—C4—C20176.79 (12)C12—C11—C16—C150.9 (2)
C17—C3—C4—C204.6 (2)C2—C11—C16—C15176.33 (13)
C2—N2—C5—C108.5 (2)C18—O2—C17—O13.0 (2)
C1—N2—C5—C10173.60 (14)C18—O2—C17—C3176.91 (12)
C2—N2—C5—C6175.31 (13)C2—C3—C17—O1106.37 (17)
C1—N2—C5—C62.60 (13)C4—C3—C17—O175.00 (19)
C1—N3—C6—C7178.26 (13)C2—C3—C17—O273.58 (16)
C1—N3—C6—C50.43 (15)C4—C3—C17—O2105.05 (14)
N2—C5—C6—N31.99 (14)C17—O2—C18—C19174.18 (13)
C10—C5—C6—N3174.73 (12)N1—C4—C20—F122.08 (18)
N2—C5—C6—C7179.99 (12)C3—C4—C20—F1159.12 (13)
C10—C5—C6—C73.3 (2)N1—C4—C20—F297.67 (14)
N3—C6—C7—C8175.79 (13)C3—C4—C20—F281.13 (16)
C5—C6—C7—C81.88 (19)N1—C4—C20—F3142.87 (13)
C6—C7—C8—C90.6 (2)C3—C4—C20—F338.33 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N3i0.952.413.2987 (18)156
C16—H16···O3ii0.952.553.2096 (18)127
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H13F3N4O4
Mr430.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)8.4075 (5), 26.6904 (14), 9.0559 (5)
β (°) 111.027 (2)
V3)1896.82 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.32 × 0.30 × 0.26
Data collection
DiffractometerRigaku Saturn
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2002)
Tmin, Tmax0.961, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections
18499, 4492, 3911
Rint0.039
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.116, 1.11
No. of reflections4492
No. of parameters282
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.22

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N3i0.952.413.2987 (18)156
C16—H16···O3ii0.952.553.2096 (18)127
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z+1/2.
 

Acknowledgements

The authors thank the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Eduation Department, China (grant No. 2007150036) for financial support.

References

First citationAbdel-Hafez, A. A. M. (2007). Arch. Pharm. Res. 30, 678–684.  Web of Science CrossRef PubMed CAS Google Scholar
First citationCheung, M., Harris, P. A., Hasegawa, M., Ida, S., Kano, K., Nishigaki, N., Sato, H., Veal, J. M., Washio, Y. & West, R. I. (2002). WO Patent No. 2 002 044 156.  Google Scholar
First citationHermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2 003 176 284.  Google Scholar
First citationNunes, J. J., Zhu, X. T., Amouzegh, P., Ghiron, C., Johnston, D. N. & Power, E. C. (2005). WO Patent No. 2 005 009 443.  Google Scholar
First citationNunes, J. J., Zhu, X. T., Ermann, M., Ghiron, C., Johnston, D. N. & Saluste, C. G. P. (2005). WO Patent No. 2 005 021 551.  Google Scholar
First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUlrich, H. (2004). US Patent No. 2 004 033 897.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds