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2-Tri­fluoro­methyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, India
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

(Received 20 August 2013; accepted 27 August 2013; online 12 September 2013)

In the mol­ecule 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 mol­ecules into chains running along the b-axis direction.

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.]); Nunes 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.]); Duval et al. (2005[Duval, E., Case, A., Stein, R. L. & Cuny, G. D. (2005). Bioorg. Med. Chem. Lett. 15, 1885-1889.]); Palacios et al. (2007[Palacios, F., Alonso, C., Aparicio, D., Rubiales, G. & Santos, J. M. (2007). Tetrahedron, 63, 523-575.]); Teimouria & Bazhrang (2006[Teimouria, M. B. & Bazhrang, R. (2006). Bioorg. Med. Chem. Lett. 16, 3697-3701.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H6F3N3O

  • Mr = 253.19

  • Monoclinic, C 2/c

  • 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)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O15i 0.86 1.88 2.734 (2) 174
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: SHELXL97.

Supporting information


Comment top

Benzo[4,5]imidazo[1,2-a]pyrimidin-4-one is a class of fused tricyclic system having three nitrogen atoms. The derivatives of benzopyrimidine are of great importance because of their remarkable biological properties. Some of them have shown good antineoplastic (Abdel-Hafez, 2007) and protein kinase inhibitor (Nunes, Zhu, Amouzegh et al., 2005) activities. Also, heterocycles containing an imidazolone moiety exhibits various biological activities such as antibacterial and antifungal activities (Palacios et al., 2007 and Duval et al., 2005, Teimouria et al., 2006). In view of its extensive background, the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). 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 for atom O15. The crystal structure is stabilized by an intramolecular C—H···O and intermolecular N—H···O hydrogen bonds. The packing diagram of the molecule exhibits linear chain when viewed down the c axis as shown in Fig. 2.

Related literature top

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 top

An equimolar mixture of 2-aminobenzimadzole (0.5 g, 3.75 mmol) and 4,4,4-Trifluoro-3-oxo-butyric acid ethyl ester (0.69 g, 3.75 mmol) in DMF (10 ml) were added to a microwave tube equipped with a magnetic stir bar. The microwave tube was fitted with a reflux condenser and irradiated in a microwave reactor at a temperature of 130°C for 3 min at a maximum power of 320 W. Then, the reaction mixture was poured on to crushed ice. The solid was filtered and washed with 100 ml of cold water. The crude product was dried and recrystallized from 1:3 ethyl acetate and chloroform to get title compound (Yield = 74%, MP = 223–225°C).

Refinement top

H atoms were placed at idealized positions and allowed to ride on their parent atoms with C–H and N–H distances equal to 0.93 and 0.86 Å, respectively. Uiso(H) = 1.2–1.5Ueq(carrier atom) for all H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective diagram of the molecule with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the molecule viewed down the c axis.
2-Trifluoromethyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one top
Crystal data top
C11H6F3N3OF(000) = 1024
Mr = 253.19Dx = 1.612 Mg m3
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 mm1
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
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.022
ω and ϕ scansθmax = 25.0°, θmin = 1.8°
9665 measured reflectionsh = 2424
1846 independent reflectionsk = 1616
1603 reflections with I > 2σ(I)l = 88
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.143 w = 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 Å3
164 parametersΔρmin = 0.37 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: 0.0057 (9)
Crystal data top
C11H6F3N3OV = 2086.2 (6) Å3
Mr = 253.19Z = 8
Monoclinic, C2/cMo Kα radiation
a = 20.940 (3) ŵ = 0.14 mm1
b = 13.760 (3) ÅT = 273 K
c = 7.2852 (11) Å0.30 × 0.25 × 0.20 mm
β = 96.369 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1603 reflections with I > 2σ(I)
9665 measured reflectionsRint = 0.022
1846 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.06Δρmax = 0.42 e Å3
1846 reflectionsΔρmin = 0.37 e Å3
164 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
H40.036000.428600.092100.0770*
H50.077200.582300.042600.0760*
H60.179400.606600.109300.0650*
H130.396900.518400.434600.0670*
Atomic displacement parameters (Å2) top
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)
Geometric parameters (Å, º) top
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—C40.1 (3)
C9—N1—C2—C70.4 (2)N1—C2—C7—N80.0 (2)
C2—N1—C9—N80.6 (2)N1—C2—C7—C6179.6 (2)
C2—N1—C9—N10178.9 (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—C2178.33 (19)C3—C4—C5—C60.4 (4)
C14—N8—C7—C61.2 (4)C4—C5—C6—C70.5 (3)
C7—N8—C9—N10.6 (2)C5—C6—C7—N8179.9 (2)
C7—N8—C9—N10178.9 (2)C5—C6—C7—C20.4 (3)
C14—N8—C9—N1178.23 (17)N10—C11—C12—F16172.5 (2)
C14—N8—C9—N102.2 (3)N10—C11—C12—F1765.5 (3)
C7—N8—C14—O151.5 (3)N10—C11—C12—F1851.3 (3)
C7—N8—C14—C13178.26 (19)C13—C11—C12—F168.5 (4)
C9—N8—C14—O15177.0 (2)C13—C11—C12—F17113.5 (3)
C9—N8—C14—C133.2 (3)C13—C11—C12—F18129.7 (2)
C11—N10—C9—N1179.3 (2)N10—C11—C13—C140.1 (4)
C11—N10—C9—N80.1 (3)C12—C11—C13—C14178.9 (2)
C9—N10—C11—C12179.9 (2)C11—C13—C14—O15178.1 (2)
C9—N10—C11—C131.3 (3)C11—C13—C14—N82.1 (3)
N1—C2—C3—C4179.7 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y, z+1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x+1/2, y1/2, z+1/2; (vi) x, y+1, z+1/2; (vii) x, y+1, z1/2; (viii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
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
Symmetry code: (v) x+1/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O15i0.86001.88002.734 (2)174.00
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.

References

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First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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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.
First citationPalacios, F., Alonso, C., Aparicio, D., Rubiales, G. & Santos, J. M. (2007). Tetrahedron, 63, 523–575.  Web of Science CrossRef CAS
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First citationTeimouria, M. B. & Bazhrang, R. (2006). Bioorg. Med. Chem. Lett. 16, 3697–3701.  Web of Science PubMed

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