Ethyl 4-(4-nitro-phen-yl)-2-(trifluoro-meth-yl)pyrimido[1,2-a]benzimidazole-3-carboxyl-ate.

In the title compound, C(20)H(13)F(3)N(4)O(4), 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. Mol-ecules are linked by C-H⋯N and C-H⋯O hydrogen bonds and by π-π inter-actions with inter-planar 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 = 430.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 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

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H13F3N4O4	F000 = 880
Mr = 430.34	Dx = 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 = 2.3–27.9º
b = 26.6904 (14) Å	µ = 0.13 mm−1
c = 9.0559 (5) Å	T = 113 (2) K
β = 111.027 (2)º	Block, orange
V = 1896.82 (18) Å3	0.32 × 0.30 × 0.26 mm
Z = 4

Rigaku Saturn diffractometer	4492 independent reflections
Radiation source: rotating anode	3911 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.039
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.5º
ω scans	h = −11→11
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2002)	k = −34→35
Tmin = 0.961, Tmax = 0.968	l = −11→11
18499 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.3435P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.35 e Å−3
4492 reflections	Δρmin = −0.22 e Å−3
282 parameters	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)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .