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

Yang, F.-L.; Li, G.-C.; Yao, C.-S.

doi:10.1107/S160053680803941X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2469

doi:10.1107/S160053680803941X

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

Feng-Ling Yang,^a ^* Gong-Chun Li ^a and Chang-Sheng Yao ^b

^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 π–π 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 ); 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

Crystal data

C₂₀H₁₃F₃N₄O₄
M_r = 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 ) T_min = 0.961, T_max = 0.968
18499 measured reflections
4492 independent reflections
3911 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.11
4492 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803941X/fj2169sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803941X/fj2169Isup2.hkl

checkCIF report

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 π–π 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.

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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	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

C₂₀H₁₃F₃N₄O₄	F(000) = 880
M_r = 430.34	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4213 reflections
a = 8.4075 (5) Å	θ = 2.3–27.9°
b = 26.6904 (14) Å	µ = 0.13 mm⁻¹
c = 9.0559 (5) Å	T = 113 K
β = 111.027 (2)°	Block, orange
V = 1896.82 (18) Å³	0.32 × 0.30 × 0.26 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	4492 independent reflections
Radiation source: rotating anode	3911 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −34→35
T_min = 0.961, T_max = 0.968	l = −11→11
18499 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0565P)² + 0.3435P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
4492 reflections	Δρ_max = 0.35 e Å⁻³
282 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0129 (15)

Crystal data top

C₂₀H₁₃F₃N₄O₄	V = 1896.82 (18) Å³
M_r = 430.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4075 (5) Å	µ = 0.13 mm⁻¹
b = 26.6904 (14) Å	T = 113 K
c = 9.0559 (5) Å	0.32 × 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)
T_min = 0.961, T_max = 0.968	R_int = 0.039
18499 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.11	Δρ_max = 0.35 e Å⁻³
4492 reflections	Δρ_min = −0.22 e Å⁻³
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

	x	y	z	U_iso*/U_eq
F1	0.84705 (13)	0.60521 (4)	0.95949 (11)	0.0426 (3)
F2	0.69893 (13)	0.67273 (4)	0.89880 (11)	0.0385 (3)
F3	0.89019 (12)	0.65773 (4)	0.79846 (11)	0.0409 (3)
O1	0.62940 (15)	0.71967 (4)	0.55129 (14)	0.0356 (3)
O2	0.75651 (13)	0.66746 (4)	0.43224 (12)	0.0274 (2)
O3	0.21549 (16)	0.71512 (4)	−0.24329 (13)	0.0346 (3)
O4	0.26759 (14)	0.64080 (4)	−0.30905 (12)	0.0308 (3)
N1	0.57725 (14)	0.56861 (4)	0.74106 (13)	0.0219 (3)
N2	0.37814 (14)	0.56650 (4)	0.47093 (13)	0.0189 (2)
N3	0.37200 (15)	0.50437 (4)	0.64198 (13)	0.0229 (3)
N4	0.26160 (15)	0.67171 (4)	−0.21060 (14)	0.0223 (3)
C1	0.44825 (17)	0.54571 (5)	0.62568 (15)	0.0202 (3)
C2	0.45006 (17)	0.60793 (5)	0.43043 (15)	0.0191 (3)
C3	0.57796 (17)	0.63165 (5)	0.54926 (16)	0.0209 (3)
C4	0.63487 (17)	0.61029 (5)	0.70372 (15)	0.0215 (3)
C5	0.24130 (17)	0.53536 (5)	0.38824 (16)	0.0204 (3)
C6	0.24395 (18)	0.49711 (5)	0.49625 (17)	0.0220 (3)
C7	0.12231 (19)	0.45881 (5)	0.45180 (18)	0.0266 (3)
H7	0.1244	0.4322	0.5222	0.032*
C8	−0.00046 (19)	0.46102 (6)	0.30259 (18)	0.0293 (3)
H8	−0.0837	0.4353	0.2694	0.035*
C9	−0.0057 (2)	0.50043 (6)	0.19808 (18)	0.0293 (3)
H9	−0.0946	0.5011	0.0973	0.035*
C10	0.11445 (18)	0.53821 (6)	0.23755 (16)	0.0255 (3)
H10	0.1112	0.5647	0.1664	0.031*
C11	0.39418 (17)	0.62415 (5)	0.26248 (15)	0.0200 (3)
C12	0.41635 (18)	0.59172 (5)	0.15022 (16)	0.0223 (3)
H12	0.4605	0.5590	0.1804	0.027*
C13	0.37390 (18)	0.60735 (5)	−0.00523 (16)	0.0218 (3)
H13	0.3883	0.5857	−0.0828	0.026*
C14	0.30986 (17)	0.65537 (5)	−0.04460 (15)	0.0204 (3)
C15	0.28857 (18)	0.68848 (5)	0.06432 (16)	0.0235 (3)
H15	0.2457	0.7213	0.0337	0.028*
C16	0.33160 (18)	0.67247 (5)	0.21975 (16)	0.0226 (3)
H16	0.3184	0.6945	0.2970	0.027*
C17	0.65622 (18)	0.67848 (5)	0.51235 (16)	0.0246 (3)
C18	0.8334 (2)	0.71015 (6)	0.3818 (2)	0.0351 (4)
H18A	0.8954	0.7317	0.4735	0.042*
H18B	0.7445	0.7305	0.3032	0.042*
C19	0.9537 (2)	0.68897 (7)	0.3101 (2)	0.0422 (4)
H19A	1.0469	0.6716	0.3918	0.063*
H19B	1.0003	0.7162	0.2652	0.063*
H19C	0.8928	0.6653	0.2263	0.063*
C20	0.76917 (19)	0.63640 (6)	0.84092 (17)	0.0284 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0462 (6)	0.0400 (6)	0.0245 (5)	0.0004 (5)	−0.0079 (4)	0.0038 (4)
F2	0.0469 (6)	0.0361 (5)	0.0305 (5)	−0.0008 (4)	0.0115 (4)	−0.0114 (4)
F3	0.0288 (5)	0.0560 (6)	0.0329 (5)	−0.0142 (4)	0.0050 (4)	−0.0033 (4)
O1	0.0452 (7)	0.0252 (6)	0.0389 (6)	−0.0043 (5)	0.0181 (5)	−0.0062 (5)
O2	0.0309 (6)	0.0254 (5)	0.0283 (5)	−0.0041 (4)	0.0135 (5)	0.0027 (4)
O3	0.0516 (7)	0.0228 (5)	0.0276 (6)	0.0064 (5)	0.0121 (5)	0.0081 (4)
O4	0.0405 (6)	0.0326 (6)	0.0199 (5)	0.0078 (5)	0.0116 (5)	0.0013 (4)
N1	0.0222 (6)	0.0260 (6)	0.0176 (5)	0.0036 (5)	0.0073 (5)	0.0012 (5)
N2	0.0210 (6)	0.0200 (5)	0.0162 (5)	0.0018 (4)	0.0073 (4)	0.0010 (4)
N3	0.0240 (6)	0.0228 (6)	0.0238 (6)	0.0041 (5)	0.0109 (5)	0.0038 (5)
N4	0.0244 (6)	0.0225 (6)	0.0202 (6)	0.0011 (5)	0.0082 (5)	0.0039 (5)
C1	0.0220 (6)	0.0225 (6)	0.0183 (6)	0.0055 (5)	0.0097 (5)	0.0035 (5)
C2	0.0215 (6)	0.0188 (6)	0.0190 (6)	0.0026 (5)	0.0097 (5)	0.0006 (5)
C3	0.0227 (7)	0.0219 (7)	0.0182 (6)	0.0010 (5)	0.0074 (5)	0.0002 (5)
C4	0.0216 (6)	0.0247 (7)	0.0180 (6)	0.0037 (5)	0.0069 (5)	−0.0001 (5)
C5	0.0203 (6)	0.0208 (6)	0.0217 (7)	0.0003 (5)	0.0096 (5)	−0.0024 (5)
C6	0.0231 (7)	0.0210 (7)	0.0248 (7)	0.0034 (5)	0.0122 (6)	0.0003 (5)
C7	0.0299 (7)	0.0210 (7)	0.0352 (8)	0.0005 (6)	0.0193 (6)	−0.0006 (6)
C8	0.0281 (7)	0.0271 (7)	0.0365 (8)	−0.0064 (6)	0.0163 (7)	−0.0085 (6)
C9	0.0279 (8)	0.0344 (8)	0.0254 (7)	−0.0046 (6)	0.0093 (6)	−0.0053 (6)
C10	0.0262 (7)	0.0285 (7)	0.0216 (7)	−0.0021 (6)	0.0084 (6)	−0.0012 (6)
C11	0.0199 (6)	0.0219 (6)	0.0176 (6)	−0.0010 (5)	0.0062 (5)	0.0003 (5)
C12	0.0269 (7)	0.0196 (6)	0.0209 (7)	0.0032 (5)	0.0090 (6)	0.0019 (5)
C13	0.0261 (7)	0.0212 (7)	0.0198 (6)	0.0021 (5)	0.0102 (5)	0.0010 (5)
C14	0.0205 (6)	0.0232 (7)	0.0166 (6)	−0.0010 (5)	0.0057 (5)	0.0028 (5)
C15	0.0273 (7)	0.0194 (6)	0.0227 (7)	0.0028 (5)	0.0079 (6)	0.0022 (5)
C16	0.0261 (7)	0.0215 (7)	0.0198 (7)	0.0019 (5)	0.0077 (6)	−0.0008 (5)
C17	0.0248 (7)	0.0276 (7)	0.0191 (6)	−0.0024 (6)	0.0051 (6)	−0.0003 (5)
C18	0.0380 (9)	0.0335 (8)	0.0348 (9)	−0.0097 (7)	0.0142 (7)	0.0076 (7)
C19	0.0411 (10)	0.0533 (11)	0.0367 (9)	−0.0086 (8)	0.0195 (8)	0.0058 (8)
C20	0.0301 (8)	0.0311 (8)	0.0205 (7)	−0.0003 (6)	0.0047 (6)	−0.0005 (6)

Geometric parameters (Å, º) top

F1—C20	1.3304 (17)	C7—C8	1.376 (2)
F2—C20	1.3365 (17)	C7—H7	0.9500
F3—C20	1.3372 (18)	C8—C9	1.405 (2)
O1—C17	1.2004 (18)	C8—H8	0.9500
O2—C17	1.3277 (17)	C9—C10	1.381 (2)
O2—C18	1.4617 (17)	C9—H9	0.9500
O3—N4	1.2239 (15)	C10—H10	0.9500
O4—N4	1.2289 (15)	C11—C16	1.3941 (19)
N1—C4	1.3056 (18)	C11—C12	1.3978 (18)
N1—C1	1.3522 (18)	C12—C13	1.3865 (18)
N2—C2	1.3719 (17)	C12—H12	0.9500
N2—C5	1.3989 (17)	C13—C14	1.3864 (19)
N2—C1	1.4235 (16)	C13—H13	0.9500
N3—C1	1.3108 (18)	C14—C15	1.3830 (19)
N3—C6	1.3851 (19)	C15—C16	1.3890 (19)
N4—C14	1.4755 (16)	C15—H15	0.9500
C2—C3	1.3729 (19)	C16—H16	0.9500
C2—C11	1.4861 (18)	C18—C19	1.495 (2)
C3—C4	1.4248 (18)	C18—H18A	0.9900
C3—C17	1.5049 (19)	C18—H18B	0.9900
C4—C20	1.516 (2)	C19—H19A	0.9800
C5—C10	1.4004 (19)	C19—H19B	0.9800
C5—C6	1.4084 (19)	C19—H19C	0.9800
C6—C7	1.399 (2)

C17—O2—C18	115.89 (12)	C16—C11—C12	120.43 (12)
C4—N1—C1	117.02 (12)	C16—C11—C2	120.19 (12)
C2—N2—C5	133.83 (11)	C12—C11—C2	119.22 (12)
C2—N2—C1	120.72 (11)	C13—C12—C11	119.95 (13)
C5—N2—C1	105.42 (11)	C13—C12—H12	120.0
C1—N3—C6	104.76 (11)	C11—C12—H12	120.0
O3—N4—O4	123.49 (12)	C14—C13—C12	118.30 (12)
O3—N4—C14	118.27 (11)	C14—C13—H13	120.9
O4—N4—C14	118.23 (11)	C12—C13—H13	120.9
N3—C1—N1	125.63 (12)	C15—C14—C13	123.03 (12)
N3—C1—N2	113.11 (12)	C15—C14—N4	118.63 (12)
N1—C1—N2	121.23 (12)	C13—C14—N4	118.34 (12)
N2—C2—C3	117.29 (12)	C14—C15—C16	118.21 (13)
N2—C2—C11	120.05 (12)	C14—C15—H15	120.9
C3—C2—C11	122.61 (12)	C16—C15—H15	120.9
C2—C3—C4	118.54 (13)	C15—C16—C11	120.07 (13)
C2—C3—C17	119.40 (12)	C15—C16—H16	120.0
C4—C3—C17	122.05 (12)	C11—C16—H16	120.0
N1—C4—C3	124.75 (13)	O1—C17—O2	125.91 (14)
N1—C4—C20	114.58 (12)	O1—C17—C3	123.53 (13)
C3—C4—C20	120.66 (13)	O2—C17—C3	110.57 (12)
N2—C5—C10	132.99 (13)	O2—C18—C19	106.55 (13)
N2—C5—C6	104.70 (12)	O2—C18—H18A	110.4
C10—C5—C6	122.20 (13)	C19—C18—H18A	110.4
N3—C6—C7	127.89 (13)	O2—C18—H18B	110.4
N3—C6—C5	111.94 (12)	C19—C18—H18B	110.4
C7—C6—C5	120.13 (13)	H18A—C18—H18B	108.6
C8—C7—C6	117.67 (13)	C18—C19—H19A	109.5
C8—C7—H7	121.2	C18—C19—H19B	109.5
C6—C7—H7	121.2	H19A—C19—H19B	109.5
C7—C8—C9	121.65 (14)	C18—C19—H19C	109.5
C7—C8—H8	119.2	H19A—C19—H19C	109.5
C9—C8—H8	119.2	H19B—C19—H19C	109.5
C10—C9—C8	121.95 (14)	F1—C20—F2	107.24 (12)
C10—C9—H9	119.0	F1—C20—F3	107.08 (12)
C8—C9—H9	119.0	F2—C20—F3	107.02 (12)
C9—C10—C5	116.31 (13)	F1—C20—C4	112.34 (12)
C9—C10—H10	121.8	F2—C20—C4	110.55 (12)
C5—C10—H10	121.8	F3—C20—C4	112.33 (12)

C6—N3—C1—N1	176.80 (12)	C7—C8—C9—C10	1.9 (2)
C6—N3—C1—N2	−1.36 (15)	C8—C9—C10—C5	−0.5 (2)
C4—N1—C1—N3	−178.44 (13)	N2—C5—C10—C9	−177.67 (14)
C4—N1—C1—N2	−0.42 (18)	C6—C5—C10—C9	−2.0 (2)
C2—N2—C1—N3	−175.64 (11)	N2—C2—C11—C16	123.17 (14)
C5—N2—C1—N3	2.61 (15)	C3—C2—C11—C16	−59.60 (18)
C2—N2—C1—N1	6.11 (18)	N2—C2—C11—C12	−61.32 (17)
C5—N2—C1—N1	−175.64 (11)	C3—C2—C11—C12	115.92 (15)
C5—N2—C2—C3	174.80 (13)	C16—C11—C12—C13	−0.8 (2)
C1—N2—C2—C3	−7.54 (18)	C2—C11—C12—C13	−176.33 (12)
C5—N2—C2—C11	−7.8 (2)	C11—C12—C13—C14	0.0 (2)
C1—N2—C2—C11	169.83 (11)	C12—C13—C14—C15	0.9 (2)
N2—C2—C3—C4	3.79 (18)	C12—C13—C14—N4	−178.87 (12)
C11—C2—C3—C4	−173.52 (12)	O3—N4—C14—C15	4.90 (19)
N2—C2—C3—C17	−177.54 (11)	O4—N4—C14—C15	−174.11 (13)
C11—C2—C3—C17	5.16 (19)	O3—N4—C14—C13	−175.37 (13)
C1—N1—C4—C3	−3.5 (2)	O4—N4—C14—C13	5.63 (18)
C1—N1—C4—C20	175.22 (12)	C13—C14—C15—C16	−0.8 (2)
C2—C3—C4—N1	1.9 (2)	N4—C14—C15—C16	178.91 (12)
C17—C3—C4—N1	−176.76 (13)	C14—C15—C16—C11	−0.1 (2)
C2—C3—C4—C20	−176.79 (12)	C12—C11—C16—C15	0.9 (2)
C17—C3—C4—C20	4.6 (2)	C2—C11—C16—C15	176.33 (13)
C2—N2—C5—C10	−8.5 (2)	C18—O2—C17—O1	−3.0 (2)
C1—N2—C5—C10	173.60 (14)	C18—O2—C17—C3	176.91 (12)
C2—N2—C5—C6	175.31 (13)	C2—C3—C17—O1	106.37 (17)
C1—N2—C5—C6	−2.60 (13)	C4—C3—C17—O1	−75.00 (19)
C1—N3—C6—C7	−178.26 (13)	C2—C3—C17—O2	−73.58 (16)
C1—N3—C6—C5	−0.43 (15)	C4—C3—C17—O2	105.05 (14)
N2—C5—C6—N3	1.99 (14)	C17—O2—C18—C19	174.18 (13)
C10—C5—C6—N3	−174.73 (12)	N1—C4—C20—F1	22.08 (18)
N2—C5—C6—C7	−179.99 (12)	C3—C4—C20—F1	−159.12 (13)
C10—C5—C6—C7	3.3 (2)	N1—C4—C20—F2	−97.67 (14)
N3—C6—C7—C8	175.79 (13)	C3—C4—C20—F2	81.13 (16)
C5—C6—C7—C8	−1.88 (19)	N1—C4—C20—F3	142.87 (13)
C6—C7—C8—C9	−0.6 (2)	C3—C4—C20—F3	−38.33 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃F₃N₄O₄
M_r	430.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	8.4075 (5), 26.6904 (14), 9.0559 (5)
β (°)	111.027 (2)
V (Å³)	1896.82 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.32 × 0.30 × 0.26

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.961, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	18499, 4492, 3911
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.11
No. of reflections	4492
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+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

Abdel-Hafez, A. A. M. (2007). Arch. Pharm. Res. 30, 678–684. Web of Science CrossRef PubMed CAS Google Scholar
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. Google Scholar
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US Patent No. 2 003 176 284. Google Scholar
Nunes, 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
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. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulrich, H. (2004). US Patent No. 2 004 033 897. Google Scholar

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Volume 64| Part 12| December 2008| Page o2469

doi:10.1107/S160053680803941X

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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