Literature DB >> 24098223

2-Tri-fluoro-methyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one.

K B Puttaraju, K Shivashankar, E A Jithesh Babu, M Mahendra.   

Abstract

In the mol-ecule of the title compound, C11H6F3N3O, the three fused rings of the benzo[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar, the maximum deviation from the mean plane being 0.096 (2) Å. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains running along the b-axis direction.

Entities:  

Year:  2013        PMID： 24098223      PMCID： PMC3790404          DOI： 10.1107/S160053681302401X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the bioactivity of benzo[4,5] imidazo[1,2-a]-pyrimidine derivatives, see: Abdel-Hafez (2007 ▶); Nunes et al. (2005 ▶); Duval et al. (2005 ▶); Palacios et al. (2007 ▶); Teimouria & Bazhrang (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H6F3N3O M = 253.19 Monoclinic, a = 20.940 (3) Å b = 13.760 (3) Å c = 7.2852 (11) Å β = 96.369 (4)° V = 2086.2 (6) Å3 Z = 8 Mo Kα radiation μ = 0.14 mm−1 T = 273 K 0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer 9665 measured reflections 1846 independent reflections 1603 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.143 S = 1.06 1846 reflections 164 parameters H-atom parameters constrained Δρmax = 0.42 e Å−3 Δρmin = −0.37 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302401X/ff2117sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302401X/ff2117Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S160053681302401X/ff2117Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C11H6F3N3OF(000) = 1024
Mr = 253.19Dx = 1.612 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1846 reflections
a = 20.940 (3) Åθ = 1.8–25.0°
b = 13.760 (3) ŵ = 0.14 mm−1
c = 7.2852 (11) ÅT = 273 K
β = 96.369 (4)°Block, yellow
V = 2086.2 (6) Å30.30 × 0.25 × 0.20 mm
Z = 8
Bruker APEXII CCD area-detector diffractometerRint = 0.022
ω and φ scansθmax = 25.0°, θmin = 1.8°
9665 measured reflectionsh = −24→24
1846 independent reflectionsk = −16→16
1603 reflections with I > 2σ(I)l = −8→8
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.143w = 1/[σ2(Fo2) + (0.0749P)2 + 1.7218P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1846 reflectionsΔρmax = 0.42 e Å−3
164 parametersΔρmin = −0.37 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0057 (9)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
F160.47675 (10)0.39833 (15)0.5311 (4)0.1414 (12)
F170.42292 (10)0.28999 (15)0.6463 (3)0.1136 (9)
F180.45363 (9)0.26760 (18)0.3881 (3)0.1191 (9)
O150.29126 (9)0.60626 (10)0.2890 (3)0.0714 (6)
N10.21914 (9)0.30385 (11)0.1890 (2)0.0536 (6)
N80.25963 (8)0.44972 (11)0.2391 (2)0.0447 (5)
N100.32492 (9)0.31321 (12)0.3422 (3)0.0542 (6)
C20.17285 (10)0.36901 (14)0.1150 (3)0.0487 (6)
C30.11203 (12)0.35408 (18)0.0256 (3)0.0600 (8)
C40.07724 (12)0.43589 (19)−0.0316 (3)0.0642 (8)
C50.10216 (12)0.52902 (18)−0.0013 (3)0.0630 (8)
C60.16278 (11)0.54443 (15)0.0884 (3)0.0543 (7)
C70.19775 (10)0.46220 (13)0.1455 (3)0.0456 (6)
C90.27155 (10)0.35158 (13)0.2628 (3)0.0469 (6)
C110.36977 (11)0.37977 (15)0.4020 (3)0.0539 (7)
C120.43075 (12)0.33566 (19)0.4922 (4)0.0703 (9)
C130.36306 (11)0.47831 (15)0.3890 (3)0.0559 (7)
C140.30517 (11)0.51983 (13)0.3069 (3)0.0508 (7)
H10.214800.241700.187800.0640*
H30.095300.291900.004900.0720*
H40.036000.42860−0.092100.0770*
H50.077200.58230−0.042600.0760*
H60.179400.606600.109300.0650*
H130.396900.518400.434600.0670*
U11U22U33U12U13U23
F160.0922 (14)0.0935 (14)0.221 (3)−0.0293 (11)−0.0608 (16)0.0449 (15)
F170.1047 (14)0.1321 (17)0.1016 (13)0.0193 (12)0.0007 (10)0.0543 (12)
F180.0868 (12)0.1397 (18)0.1283 (16)0.0457 (12)0.0013 (11)−0.0196 (14)
O150.0854 (12)0.0276 (7)0.1030 (13)−0.0046 (7)0.0190 (10)−0.0015 (7)
N10.0663 (11)0.0265 (8)0.0674 (11)−0.0028 (7)0.0048 (9)−0.0015 (7)
N80.0584 (10)0.0277 (8)0.0497 (9)−0.0007 (7)0.0139 (7)−0.0005 (6)
N100.0630 (11)0.0337 (9)0.0653 (11)0.0000 (8)0.0046 (9)0.0000 (7)
C20.0595 (12)0.0390 (10)0.0489 (11)0.0001 (8)0.0118 (9)0.0002 (8)
C30.0668 (14)0.0560 (13)0.0573 (12)−0.0062 (11)0.0079 (11)−0.0034 (10)
C40.0621 (14)0.0758 (16)0.0549 (13)0.0070 (12)0.0071 (10)0.0027 (11)
C50.0699 (15)0.0645 (15)0.0564 (13)0.0181 (11)0.0154 (11)0.0111 (10)
C60.0710 (14)0.0396 (10)0.0554 (12)0.0065 (9)0.0208 (10)0.0047 (9)
C70.0576 (12)0.0371 (10)0.0446 (10)0.0020 (8)0.0162 (9)0.0010 (8)
C90.0609 (12)0.0282 (9)0.0527 (11)−0.0008 (8)0.0106 (9)−0.0004 (8)
C110.0632 (13)0.0455 (11)0.0536 (12)−0.0033 (9)0.0089 (10)0.0026 (9)
C120.0673 (15)0.0603 (14)0.0817 (17)−0.0031 (12)0.0017 (13)0.0072 (13)
C130.0650 (13)0.0440 (11)0.0592 (12)−0.0128 (10)0.0093 (10)−0.0030 (9)
C140.0674 (13)0.0311 (10)0.0565 (11)−0.0066 (9)0.0189 (10)−0.0023 (8)
F16—C121.301 (3)C2—C71.393 (3)
F17—C121.313 (4)C3—C41.380 (4)
F18—C121.328 (4)C4—C51.392 (4)
O15—C141.228 (2)C5—C61.378 (3)
N1—C21.385 (3)C6—C71.386 (3)
N1—C91.339 (3)C11—C131.365 (3)
N8—C71.406 (3)C11—C121.498 (3)
N8—C91.381 (2)C13—C141.412 (3)
N8—C141.407 (3)C3—H30.9300
N10—C91.311 (3)C4—H40.9300
N10—C111.349 (3)C5—H50.9300
N1—H10.8600C6—H60.9300
C2—C31.380 (3)C13—H130.9300
F16···F16i3.013 (3)C5···C4vi3.551 (3)
F17···N102.866 (3)C5···C7vii3.433 (3)
F17···C3ii3.251 (3)C6···C4vi3.471 (3)
F18···F18iii2.947 (3)C6···O153.037 (3)
F18···N102.751 (3)C6···N8vii3.426 (3)
F16···H13i2.8700C6···C5vi3.523 (3)
F16···H132.4000C6···C7vii3.388 (3)
F17···H3ii2.8400C7···C5vi3.433 (3)
O15···C63.037 (3)C7···C6vi3.388 (3)
O15···N1iv2.734 (2)C7···C14vii3.527 (3)
O15···H62.5500C13···C14vi3.400 (3)
O15···H1iv1.8800C14···N8vi3.415 (3)
N1···N82.194 (2)C14···C13vii3.400 (3)
N1···O15v2.734 (2)C14···C7vi3.527 (3)
N8···N12.194 (2)C5···H4viii3.1000
N8···C6vi3.426 (3)C14···H63.1000
N8···C14vii3.415 (3)C14···H1iv3.0800
N10···F172.866 (3)H1···O15v1.8800
N10···F182.751 (3)H1···C14v3.0800
N10···H6v2.8700H3···F17ii2.8400
C2···C5vi3.591 (3)H4···C5viii3.1000
C3···F17ii3.251 (3)H6···O152.5500
C4···C5vii3.551 (3)H6···C143.1000
C4···C6vii3.471 (3)H6···N10iv2.8700
C5···C6vii3.523 (3)H13···F162.4000
C5···C2vii3.591 (3)H13···F16i2.8700
C2—N1—C9110.23 (16)N10—C11—C12113.30 (19)
C7—N8—C9108.92 (16)F16—C12—C11113.7 (2)
C7—N8—C14129.70 (16)F16—C12—F17106.9 (3)
C9—N8—C14121.38 (17)F16—C12—F18106.7 (2)
C9—N10—C11113.45 (17)F18—C12—C11112.3 (2)
C2—N1—H1125.00F17—C12—F18103.8 (2)
C9—N1—H1125.00F17—C12—C11112.8 (2)
N1—C2—C3131.05 (19)C11—C13—C14120.6 (2)
N1—C2—C7107.49 (18)N8—C14—C13112.83 (16)
C3—C2—C7121.5 (2)O15—C14—N8118.9 (2)
C2—C3—C4116.7 (2)O15—C14—C13128.3 (2)
C3—C4—C5121.8 (2)C2—C3—H3122.00
C4—C5—C6121.8 (2)C4—C3—H3122.00
C5—C6—C7116.4 (2)C3—C4—H4119.00
N8—C7—C2105.87 (16)C5—C4—H4119.00
N8—C7—C6132.28 (18)C4—C5—H5119.00
C2—C7—C6121.9 (2)C6—C5—H5119.00
N1—C9—N8107.50 (17)C5—C6—H6122.00
N8—C9—N10125.63 (18)C7—C6—H6122.00
N1—C9—N10126.87 (17)C11—C13—H13120.00
N10—C11—C13126.1 (2)C14—C13—H13120.00
C12—C11—C13120.6 (2)
C9—N1—C2—C3179.8 (2)C7—C2—C3—C4−0.1 (3)
C9—N1—C2—C7−0.4 (2)N1—C2—C7—N80.0 (2)
C2—N1—C9—N80.6 (2)N1—C2—C7—C6−179.6 (2)
C2—N1—C9—N10−178.9 (2)C3—C2—C7—N8179.80 (19)
C9—N8—C7—C20.4 (2)C3—C2—C7—C60.2 (3)
C9—N8—C7—C6179.9 (2)C2—C3—C4—C50.2 (3)
C14—N8—C7—C2−178.33 (19)C3—C4—C5—C6−0.4 (4)
C14—N8—C7—C61.2 (4)C4—C5—C6—C70.5 (3)
C7—N8—C9—N1−0.6 (2)C5—C6—C7—N8−179.9 (2)
C7—N8—C9—N10178.9 (2)C5—C6—C7—C2−0.4 (3)
C14—N8—C9—N1178.23 (17)N10—C11—C12—F16172.5 (2)
C14—N8—C9—N10−2.2 (3)N10—C11—C12—F17−65.5 (3)
C7—N8—C14—O151.5 (3)N10—C11—C12—F1851.3 (3)
C7—N8—C14—C13−178.26 (19)C13—C11—C12—F16−8.5 (4)
C9—N8—C14—O15−177.0 (2)C13—C11—C12—F17113.5 (3)
C9—N8—C14—C133.2 (3)C13—C11—C12—F18−129.7 (2)
C11—N10—C9—N1179.3 (2)N10—C11—C13—C14−0.1 (4)
C11—N10—C9—N8−0.1 (3)C12—C11—C13—C14−178.9 (2)
C9—N10—C11—C12−179.9 (2)C11—C13—C14—O15178.1 (2)
C9—N10—C11—C131.3 (3)C11—C13—C14—N8−2.1 (3)
N1—C2—C3—C4179.7 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O15v0.861.882.734 (2)174
C6—H6···O150.932.553.037 (3)113
C13—H13···F160.932.402.721 (3)100
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O15i 0.861.882.734 (2)174

Symmetry code: (i) .

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