Crystal structure of 10-[(3-oxo-3H-benzo[f]chromen-1-yl)meth­yl]-2-tri­fluoro­methyl-9a,10-di­hydro­benz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one

Chandra; Shamantha Kumar; K B Puttaraju; K Shivashankar; M Mahendra

doi:10.1107/S2056989015014425

. 2015 Aug 22;71(Pt 9):o672–o673. doi: 10.1107/S2056989015014425

Crystal structure of 10-[(3-oxo-3H-benzo[f]chromen-1-yl)methyl]-2-trifluoromethyl-9a,10-dihydrobenz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one

Chandra ^a, Shamantha Kumar ^b, K B Puttaraju ^c, K Shivashankar ^c, M Mahendra ^a,^*

PMCID: PMC4555409 PMID: 26396897

Abstract

In the title compound, C₂₅H₁₄F₃N₃O₃, the dihedral angle between the planes of the benz[4,5]imidazo[1,2-a]pyrimidine unit (r.m.s. deviation = 0.035 Å) and the benzochromene ring system (r.m.s. deviation = 0.106 Å) is 72.82 (5)°. In the crystal, molecules are linked by C—H⋯O interactions, generating [010] C(9) chains. A weak aromatic π–π stacking interaction [centroid–centroid separation = 3.5376 (15) Å] is also observed.

Keywords: crystal structure, fused-ring system, chromene, benzimidazole, pyrimidinone, benzopyrimidine, π–π stacking interactions

Related literature

For background to benzopyrimidine derivatives, see: Bodke et al. (2003 ▸); Moneam et al. (2004 ▸). For the synthesis of the title compound, see: Puttaraju et al. (2013 ▸). For a related structure, see: Chandra et al. (2013 ▸). graphic file with name e-71-0o672-scheme1.jpg

Experimental

Crystal data

C₂₅H₁₄F₃N₃O₃
M _r = 461.39
Monoclinic,
a = 9.7665 (5) Å
b = 7.7950 (4) Å
c = 27.0602 (16) Å
β = 95.186 (5)°
V = 2051.66 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
9209 measured reflections
5020 independent reflections
2637 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.176
S = 1.00
5020 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014425/hb7467sup1.cif

e-71-0o672-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014425/hb7467Isup2.hkl

e-71-0o672-Isup2.hkl^{(245.9KB, hkl)}

Click here for additional data file.^{(8.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015014425/hb7467Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015014425/hb7467fig1.tif

Perspective diagram of the molecule with 50% probability displacement ellipsoids.

Click here for additional data file.^{(1.4MB, tif)}

b . DOI: 10.1107/S2056989015014425/hb7467fig2.tif

Packing diagram of the molecule viewed down the b axis.

CCDC reference: 1416062

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C21H21O11ⁱ	0.93	2.33	3.241(3)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

MM would like to thank UGC, New Delhi, Government of India, for awarding a project under the head F. No. 41–920/2012(SR) (dated 25-07-2012).

supplementary crystallographic information

S1. Comment

The heterocycles containing benzopyrimidine moiety has a variety of biological activities such as analgesic, anti-inflammatory and antimicrobial activities (Moneam et al., 2004 and Bodke et al., 2003). As part of our studies of these systems (Puttaraju et al., 2013), the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), the three fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar; the maximum deviation from the mean plane being -0.084 (2) Å for atom O11. The dihedral angle between the three fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine with the benzochromene moiety is 72.82 (5)°. Benzochromene moiety and fused rings of the benz[4,5]imidazo[1,2-a]pyrimidine derivatives bridged by the carbon atom (C19) and this inter atomic bond conformation is characterized by torsion angles of 116.5 (2)° (C2–N3–C19–C20) and 160.66 (18)° (N3–C19–C20–C26), respectively. The bond lengths and angles are generally within normal ranges and are comparable to a related structure (Chandra et al., 2013). The packing diagram of the molecule exhibits chain when viewed down the b axis as shown in Fig. 2.

S2. Experimental

The compound was synthesized by microwave irradiation method (Puttaraju et al., 2013). The synthesized compound (yield = 93%, m.p = 228–230 °C) was recrystallized from 1:3 ethyl acetate and chloroform solution to get yellow block shaped crystals.