organic compounds
H-benzo[f]chromen-1-yl)methyl]-2-trifluoromethyl-9a,10-dihydrobenz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one
of 10-[(3-oxo-3aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Physics, SJB Institute of Technology, Kengeri, Bangalore 560 060, India, and cDepartment of Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, India
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in
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.
CCDC reference: 1416062
1. 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).
2. Experimental
2.1. Crystal data
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2.2. Data collection
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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.
Supporting information
CCDC reference: 1416062
https://doi.org/10.1107/S2056989015014425/hb7467sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014425/hb7467Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014425/hb7467Isup3.cml
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.
H atoms were placed at idealized positions and allowed to ride on their parent atoms with C–H distances in the range of 0.93 to 0.97 Å; Uiso(H) = 1.2–1.5Ueq(carrier atom) for all H atoms.
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.
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).
Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. Perspective diagram of the molecule with 50% probability displacement ellipsoids. | |
Fig. 2. Packing diagram of the molecule viewed down the b axis. |
C25H14F3N3O3 | F(000) = 944 |
Mr = 461.39 | Dx = 1.494 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5020 reflections |
a = 9.7665 (5) Å | θ = 2.7–28.3° |
b = 7.7950 (4) Å | µ = 0.12 mm−1 |
c = 27.0602 (16) Å | T = 293 K |
β = 95.186 (5)° | Bolck, yellow |
V = 2051.66 (19) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | Rint = 0.033 |
ω and φ scans | θmax = 28.3°, θmin = 2.7° |
9209 measured reflections | h = −11→12 |
5020 independent reflections | k = −5→10 |
2637 reflections with I > 2σ(I) | l = −27→36 |
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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
5020 reflections | Δρmax = 0.21 e Å−3 |
308 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0030 (8) |
C25H14F3N3O3 | V = 2051.66 (19) Å3 |
Mr = 461.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.7665 (5) Å | µ = 0.12 mm−1 |
b = 7.7950 (4) Å | T = 293 K |
c = 27.0602 (16) Å | 0.30 × 0.25 × 0.20 mm |
β = 95.186 (5)° |
Bruker APEXII CCD area-detector diffractometer | 2637 reflections with I > 2σ(I) |
9209 measured reflections | Rint = 0.033 |
5020 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
5020 reflections | Δρmin = −0.19 e Å−3 |
308 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
F16 | −0.06281 (18) | 0.8341 (3) | 0.10659 (8) | 0.1073 (9) | |
F17 | −0.01199 (16) | 0.6009 (3) | 0.07308 (6) | 0.0921 (8) | |
F18 | −0.14200 (15) | 0.5991 (3) | 0.13215 (7) | 0.1024 (9) | |
O11 | 0.20544 (19) | 0.5442 (3) | 0.27911 (6) | 0.0737 (8) | |
O23 | 0.4824 (2) | 1.3933 (2) | 0.15054 (8) | 0.0862 (9) | |
O24 | 0.62445 (19) | 1.3111 (2) | 0.09616 (7) | 0.0628 (7) | |
N1 | 0.31775 (19) | 0.6564 (2) | 0.21634 (7) | 0.0455 (6) | |
N3 | 0.44740 (17) | 0.7624 (2) | 0.16034 (6) | 0.0409 (6) | |
N14 | 0.21121 (18) | 0.7121 (2) | 0.13481 (7) | 0.0463 (6) | |
C2 | 0.3181 (2) | 0.7104 (3) | 0.16781 (8) | 0.0410 (7) | |
C4 | 0.5313 (2) | 0.7441 (3) | 0.20479 (8) | 0.0447 (7) | |
C5 | 0.4513 (2) | 0.6770 (3) | 0.24038 (9) | 0.0478 (8) | |
C6 | 0.5044 (3) | 0.6466 (3) | 0.28881 (9) | 0.0618 (9) | |
C7 | 0.6405 (3) | 0.6880 (4) | 0.29999 (10) | 0.0739 (11) | |
C8 | 0.7211 (3) | 0.7556 (4) | 0.26516 (11) | 0.0725 (11) | |
C9 | 0.6678 (2) | 0.7831 (3) | 0.21638 (10) | 0.0592 (9) | |
C10 | 0.1990 (3) | 0.5950 (3) | 0.23595 (9) | 0.0545 (8) | |
C12 | 0.0819 (3) | 0.6013 (3) | 0.20043 (9) | 0.0587 (9) | |
C13 | 0.0939 (2) | 0.6575 (3) | 0.15344 (9) | 0.0515 (8) | |
C15 | −0.0306 (3) | 0.6693 (4) | 0.11661 (10) | 0.0623 (10) | |
C19 | 0.4956 (2) | 0.7898 (3) | 0.11163 (8) | 0.0424 (7) | |
C20 | 0.5353 (2) | 0.9744 (3) | 0.10211 (8) | 0.0402 (7) | |
C21 | 0.4909 (2) | 1.0969 (3) | 0.13174 (9) | 0.0511 (8) | |
C22 | 0.5260 (3) | 1.2748 (3) | 0.12793 (10) | 0.0608 (10) | |
C25 | 0.6706 (3) | 1.1898 (3) | 0.06486 (9) | 0.0538 (8) | |
C26 | 0.6241 (2) | 1.0222 (3) | 0.06349 (8) | 0.0418 (7) | |
C27 | 0.6713 (2) | 0.9122 (3) | 0.02498 (8) | 0.0461 (7) | |
C28 | 0.7704 (2) | 0.9786 (4) | −0.00588 (9) | 0.0598 (9) | |
C29 | 0.8182 (3) | 1.1485 (4) | 0.00084 (11) | 0.0763 (11) | |
C30 | 0.7689 (3) | 1.2528 (4) | 0.03478 (11) | 0.0730 (11) | |
C31 | 0.8178 (3) | 0.8749 (5) | −0.04365 (11) | 0.0803 (13) | |
C32 | 0.7698 (3) | 0.7147 (5) | −0.05239 (11) | 0.0787 (13) | |
C33 | 0.6709 (3) | 0.6507 (4) | −0.02363 (10) | 0.0682 (10) | |
C34 | 0.6220 (3) | 0.7459 (3) | 0.01357 (9) | 0.0536 (8) | |
H6 | 0.45110 | 0.60090 | 0.31240 | 0.0740* | |
H7 | 0.67990 | 0.66990 | 0.33210 | 0.0890* | |
H8 | 0.81240 | 0.78320 | 0.27460 | 0.0870* | |
H9 | 0.72200 | 0.82580 | 0.19270 | 0.0710* | |
H12 | −0.00350 | 0.56670 | 0.20950 | 0.0700* | |
H19A | 0.42380 | 0.75540 | 0.08650 | 0.0510* | |
H19B | 0.57470 | 0.71680 | 0.10830 | 0.0510* | |
H21 | 0.43440 | 1.06460 | 0.15600 | 0.0610* | |
H29 | 0.88510 | 1.18930 | −0.01850 | 0.0920* | |
H30 | 0.79970 | 1.36540 | 0.03820 | 0.0880* | |
H31 | 0.88380 | 0.91840 | −0.06300 | 0.0960* | |
H32 | 0.80250 | 0.64810 | −0.07730 | 0.0950* | |
H33 | 0.63690 | 0.54050 | −0.02970 | 0.0820* | |
H34 | 0.55460 | 0.69940 | 0.03170 | 0.0640* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F16 | 0.0900 (14) | 0.0943 (15) | 0.1297 (18) | 0.0138 (11) | −0.0336 (12) | 0.0102 (13) |
F17 | 0.0675 (10) | 0.1379 (17) | 0.0697 (11) | −0.0180 (11) | −0.0005 (8) | −0.0251 (11) |
F18 | 0.0503 (10) | 0.1613 (19) | 0.0968 (14) | −0.0305 (11) | 0.0128 (9) | 0.0081 (13) |
O11 | 0.0810 (13) | 0.0911 (15) | 0.0517 (11) | −0.0130 (11) | 0.0211 (9) | 0.0169 (11) |
O23 | 0.1251 (18) | 0.0480 (11) | 0.0847 (15) | 0.0111 (11) | 0.0045 (13) | −0.0181 (11) |
O24 | 0.0774 (13) | 0.0432 (9) | 0.0664 (12) | −0.0115 (9) | −0.0012 (10) | 0.0027 (9) |
N1 | 0.0509 (11) | 0.0471 (11) | 0.0396 (10) | −0.0036 (9) | 0.0106 (8) | 0.0015 (9) |
N3 | 0.0404 (10) | 0.0434 (10) | 0.0397 (10) | −0.0047 (9) | 0.0083 (7) | −0.0002 (9) |
N14 | 0.0429 (10) | 0.0540 (12) | 0.0426 (10) | −0.0056 (10) | 0.0078 (8) | 0.0004 (10) |
C2 | 0.0463 (13) | 0.0375 (12) | 0.0402 (12) | −0.0020 (10) | 0.0101 (9) | −0.0008 (10) |
C4 | 0.0462 (13) | 0.0448 (13) | 0.0435 (12) | 0.0003 (11) | 0.0068 (10) | −0.0018 (11) |
C5 | 0.0510 (14) | 0.0490 (14) | 0.0434 (12) | 0.0005 (12) | 0.0048 (10) | −0.0012 (12) |
C6 | 0.0688 (17) | 0.0678 (18) | 0.0484 (14) | 0.0022 (14) | 0.0038 (12) | 0.0029 (14) |
C7 | 0.076 (2) | 0.090 (2) | 0.0520 (16) | 0.0069 (17) | −0.0137 (14) | 0.0015 (16) |
C8 | 0.0582 (17) | 0.086 (2) | 0.0704 (19) | 0.0014 (16) | −0.0095 (14) | −0.0032 (17) |
C9 | 0.0480 (14) | 0.0681 (17) | 0.0612 (16) | −0.0014 (13) | 0.0038 (12) | −0.0014 (15) |
C10 | 0.0614 (15) | 0.0549 (15) | 0.0502 (14) | −0.0069 (13) | 0.0210 (12) | 0.0048 (13) |
C12 | 0.0488 (14) | 0.0646 (17) | 0.0651 (17) | −0.0092 (13) | 0.0189 (12) | 0.0038 (14) |
C13 | 0.0443 (13) | 0.0544 (15) | 0.0574 (15) | −0.0057 (12) | 0.0136 (11) | 0.0026 (13) |
C15 | 0.0518 (16) | 0.076 (2) | 0.0597 (17) | −0.0108 (15) | 0.0080 (12) | −0.0019 (16) |
C19 | 0.0450 (12) | 0.0405 (12) | 0.0434 (12) | −0.0041 (10) | 0.0128 (9) | −0.0030 (10) |
C20 | 0.0414 (12) | 0.0378 (11) | 0.0409 (11) | −0.0025 (10) | 0.0016 (9) | 0.0000 (10) |
C21 | 0.0587 (15) | 0.0443 (13) | 0.0506 (14) | 0.0006 (12) | 0.0070 (11) | −0.0034 (12) |
C22 | 0.0789 (19) | 0.0460 (15) | 0.0558 (16) | 0.0076 (14) | −0.0039 (14) | −0.0056 (13) |
C25 | 0.0565 (15) | 0.0501 (14) | 0.0531 (14) | −0.0076 (12) | −0.0043 (11) | 0.0045 (13) |
C26 | 0.0403 (11) | 0.0460 (13) | 0.0384 (11) | −0.0023 (10) | 0.0006 (9) | 0.0052 (10) |
C27 | 0.0388 (11) | 0.0601 (15) | 0.0391 (11) | 0.0036 (11) | 0.0018 (9) | 0.0043 (12) |
C28 | 0.0456 (14) | 0.085 (2) | 0.0498 (14) | −0.0011 (14) | 0.0095 (11) | 0.0087 (15) |
C29 | 0.0701 (19) | 0.097 (2) | 0.0637 (19) | −0.0268 (18) | 0.0162 (15) | 0.0151 (18) |
C30 | 0.0746 (19) | 0.0704 (19) | 0.0729 (19) | −0.0324 (16) | 0.0013 (15) | 0.0196 (17) |
C31 | 0.0624 (18) | 0.122 (3) | 0.0605 (18) | 0.006 (2) | 0.0279 (14) | 0.005 (2) |
C32 | 0.077 (2) | 0.108 (3) | 0.0533 (17) | 0.024 (2) | 0.0178 (15) | −0.0043 (19) |
C33 | 0.081 (2) | 0.0726 (19) | 0.0519 (15) | 0.0111 (15) | 0.0106 (14) | −0.0084 (15) |
C34 | 0.0634 (15) | 0.0552 (15) | 0.0435 (13) | −0.0026 (13) | 0.0115 (11) | −0.0066 (12) |
F16—C15 | 1.344 (4) | C21—C22 | 1.434 (3) |
F17—C15 | 1.320 (3) | C25—C26 | 1.383 (3) |
F18—C15 | 1.320 (3) | C25—C30 | 1.402 (4) |
O11—C10 | 1.229 (3) | C26—C27 | 1.456 (3) |
O23—C22 | 1.207 (3) | C27—C28 | 1.431 (3) |
O24—C22 | 1.376 (3) | C27—C34 | 1.407 (3) |
O24—C25 | 1.372 (3) | C28—C29 | 1.411 (4) |
N1—C2 | 1.379 (3) | C28—C31 | 1.414 (4) |
N1—C5 | 1.413 (3) | C29—C30 | 1.348 (4) |
N1—C10 | 1.403 (3) | C31—C32 | 1.347 (5) |
N3—C2 | 1.359 (3) | C32—C33 | 1.387 (4) |
N3—C4 | 1.400 (3) | C33—C34 | 1.371 (4) |
N3—C19 | 1.455 (3) | C6—H6 | 0.9300 |
N14—C2 | 1.311 (3) | C7—H7 | 0.9300 |
N14—C13 | 1.361 (3) | C8—H8 | 0.9300 |
C4—C5 | 1.396 (3) | C9—H9 | 0.9300 |
C4—C9 | 1.376 (3) | C12—H12 | 0.9300 |
C5—C6 | 1.386 (3) | C19—H19A | 0.9700 |
C6—C7 | 1.375 (4) | C19—H19B | 0.9700 |
C7—C8 | 1.386 (4) | C21—H21 | 0.9300 |
C8—C9 | 1.391 (4) | C29—H29 | 0.9300 |
C10—C12 | 1.427 (4) | C30—H30 | 0.9300 |
C12—C13 | 1.360 (3) | C31—H31 | 0.9300 |
C13—C15 | 1.504 (4) | C32—H32 | 0.9300 |
C19—C20 | 1.518 (3) | C33—H33 | 0.9300 |
C20—C21 | 1.344 (3) | C34—H34 | 0.9300 |
C20—C26 | 1.465 (3) | ||
F16···N14 | 2.878 (3) | C32···C22iii | 3.386 (4) |
F16···C27i | 3.310 (3) | C32···C21iii | 3.502 (4) |
F17···N14 | 2.763 (2) | C33···C22iii | 3.320 (4) |
F17···H30ii | 2.7100 | C33···O24iii | 3.352 (3) |
F17···H29iii | 2.5900 | C33···C30viii | 3.572 (4) |
F17···H32iv | 2.8100 | C34···C19 | 3.045 (3) |
F18···H9i | 2.8200 | C34···C25iii | 3.439 (4) |
F18···H12 | 2.4000 | C34···C26iii | 3.534 (3) |
O11···C6 | 3.015 (3) | C2···H21 | 3.0100 |
O11···C2v | 2.991 (3) | C4···H21 | 2.9400 |
O11···N1v | 3.035 (3) | C9···H19B | 3.0300 |
O11···N3v | 3.191 (3) | C10···H6 | 3.0700 |
O11···C21v | 3.241 (3) | C19···H9 | 2.9800 |
O11···C4v | 3.345 (3) | C19···H34 | 2.3900 |
O11···C5v | 3.266 (3) | C20···H34 | 2.8900 |
O23···N3vi | 2.912 (2) | C22···H7vii | 3.0900 |
O23···C2vi | 3.006 (3) | C22···H8vii | 2.9500 |
O23···N1vi | 3.237 (3) | C25···H7vii | 3.0300 |
O23···C5vi | 3.321 (3) | C27···H19B | 2.9500 |
O23···C19vi | 3.271 (3) | C30···H33vi | 3.0500 |
O23···C4vi | 3.120 (3) | C33···H30viii | 2.9900 |
O24···C33iii | 3.352 (3) | C34···H19B | 2.6600 |
O11···H6 | 2.5200 | C34···H19A | 2.8900 |
O11···H21v | 2.3300 | H6···O11 | 2.5200 |
O23···H8vii | 2.8500 | H6···C10 | 3.0700 |
O24···H7vii | 2.8200 | H7···O24xi | 2.8200 |
N1···O23viii | 3.237 (3) | H7···C22xi | 3.0900 |
N1···O11ix | 3.035 (3) | H7···C25xi | 3.0300 |
N3···O23viii | 2.912 (2) | H8···O23xi | 2.8500 |
N3···O11ix | 3.191 (3) | H8···C22xi | 2.9500 |
N14···F17 | 2.763 (2) | H9···F18x | 2.8200 |
N14···F16 | 2.878 (3) | H9···C19 | 2.9800 |
N3···H21 | 2.3600 | H12···F18 | 2.4000 |
N14···H19A | 2.5700 | H19A···N14 | 2.5700 |
C2···O23viii | 3.006 (3) | H19A···C34 | 2.8900 |
C2···O11ix | 2.991 (3) | H19A···H34 | 2.0900 |
C4···C21 | 3.389 (3) | H19B···C9 | 3.0300 |
C4···O23viii | 3.120 (3) | H19B···C27 | 2.9500 |
C4···O11ix | 3.345 (3) | H19B···C34 | 2.6600 |
C5···O11ix | 3.266 (3) | H19B···H34 | 2.0700 |
C5···O23viii | 3.321 (3) | H21···N3 | 2.3600 |
C6···O11 | 3.015 (3) | H21···C2 | 3.0100 |
C9···C20 | 3.569 (3) | H21···C4 | 2.9400 |
C19···C34 | 3.045 (3) | H21···O11ix | 2.3300 |
C19···O23viii | 3.271 (3) | H29···H31 | 2.4300 |
C20···C9 | 3.569 (3) | H29···F17iii | 2.5900 |
C21···O11ix | 3.241 (3) | H30···F17xii | 2.7100 |
C21···C4 | 3.389 (3) | H30···C33vi | 2.9900 |
C21···C32iii | 3.502 (4) | H31···H29 | 2.4300 |
C22···C33iii | 3.320 (4) | H32···F17iv | 2.8100 |
C22···C32iii | 3.386 (4) | H33···C30viii | 3.0500 |
C25···C34iii | 3.439 (4) | H34···C19 | 2.3900 |
C26···C34iii | 3.534 (3) | H34···C20 | 2.8900 |
C27···F16x | 3.310 (3) | H34···H19A | 2.0900 |
C30···C33vi | 3.572 (4) | H34···H19B | 2.0700 |
C22—O24—C25 | 122.07 (19) | C20—C26—C25 | 115.8 (2) |
C2—N1—C5 | 108.78 (18) | C20—C26—C27 | 127.4 (2) |
C2—N1—C10 | 122.53 (19) | C25—C26—C27 | 116.8 (2) |
C5—N1—C10 | 128.7 (2) | C26—C27—C28 | 118.6 (2) |
C2—N3—C4 | 108.75 (17) | C26—C27—C34 | 125.1 (2) |
C2—N3—C19 | 124.04 (17) | C28—C27—C34 | 116.2 (2) |
C4—N3—C19 | 125.53 (16) | C27—C28—C29 | 119.9 (2) |
C2—N14—C13 | 112.93 (19) | C27—C28—C31 | 119.9 (3) |
N1—C2—N3 | 108.36 (17) | C29—C28—C31 | 120.3 (2) |
N1—C2—N14 | 125.54 (19) | C28—C29—C30 | 121.3 (3) |
N3—C2—N14 | 126.1 (2) | C25—C30—C29 | 119.3 (3) |
N3—C4—C5 | 108.08 (17) | C28—C31—C32 | 121.7 (3) |
N3—C4—C9 | 130.8 (2) | C31—C32—C33 | 118.9 (3) |
C5—C4—C9 | 121.1 (2) | C32—C33—C34 | 121.6 (3) |
N1—C5—C4 | 106.02 (19) | C27—C34—C33 | 121.7 (2) |
N1—C5—C6 | 131.8 (2) | C5—C6—H6 | 122.00 |
C4—C5—C6 | 122.1 (2) | C7—C6—H6 | 122.00 |
C5—C6—C7 | 116.1 (2) | C6—C7—H7 | 119.00 |
C6—C7—C8 | 122.5 (3) | C8—C7—H7 | 119.00 |
C7—C8—C9 | 121.1 (3) | C7—C8—H8 | 119.00 |
C4—C9—C8 | 117.0 (2) | C9—C8—H8 | 119.00 |
O11—C10—N1 | 119.8 (2) | C4—C9—H9 | 122.00 |
O11—C10—C12 | 128.3 (3) | C8—C9—H9 | 121.00 |
N1—C10—C12 | 111.9 (2) | C10—C12—H12 | 120.00 |
C10—C12—C13 | 120.6 (2) | C13—C12—H12 | 120.00 |
N14—C13—C12 | 126.4 (2) | N3—C19—H19A | 109.00 |
N14—C13—C15 | 113.1 (2) | N3—C19—H19B | 109.00 |
C12—C13—C15 | 120.4 (2) | C20—C19—H19A | 109.00 |
F16—C15—F17 | 104.7 (2) | C20—C19—H19B | 109.00 |
F16—C15—F18 | 106.0 (2) | H19A—C19—H19B | 108.00 |
F16—C15—C13 | 110.7 (2) | C20—C21—H21 | 118.00 |
F17—C15—F18 | 107.5 (2) | C22—C21—H21 | 118.00 |
F17—C15—C13 | 113.5 (2) | C28—C29—H29 | 119.00 |
F18—C15—C13 | 113.8 (2) | C30—C29—H29 | 119.00 |
N3—C19—C20 | 113.66 (18) | C25—C30—H30 | 120.00 |
C19—C20—C21 | 118.11 (19) | C29—C30—H30 | 120.00 |
C19—C20—C26 | 122.60 (19) | C28—C31—H31 | 119.00 |
C21—C20—C26 | 119.3 (2) | C32—C31—H31 | 119.00 |
C20—C21—C22 | 123.5 (2) | C31—C32—H32 | 121.00 |
O23—C22—O24 | 117.3 (2) | C33—C32—H32 | 121.00 |
O23—C22—C21 | 127.3 (3) | C32—C33—H33 | 119.00 |
O24—C22—C21 | 115.4 (2) | C34—C33—H33 | 119.00 |
O24—C25—C26 | 122.8 (2) | C27—C34—H34 | 119.00 |
O24—C25—C30 | 113.4 (2) | C33—C34—H34 | 119.00 |
C26—C25—C30 | 123.8 (2) | ||
C22—O24—C25—C30 | 178.8 (2) | C10—C12—C13—C15 | −178.0 (2) |
C25—O24—C22—O23 | −173.1 (2) | C10—C12—C13—N14 | 0.0 (4) |
C25—O24—C22—C21 | 9.3 (3) | N14—C13—C15—F16 | −68.0 (3) |
C22—O24—C25—C26 | −1.3 (4) | C12—C13—C15—F18 | −9.0 (4) |
C5—N1—C2—N14 | −178.9 (2) | N14—C13—C15—F17 | 49.4 (3) |
C10—N1—C2—N3 | 179.82 (18) | N14—C13—C15—F18 | 172.8 (2) |
C10—N1—C2—N14 | 0.3 (3) | C12—C13—C15—F16 | 110.3 (3) |
C5—N1—C2—N3 | 0.7 (2) | C12—C13—C15—F17 | −132.3 (3) |
C2—N1—C10—O11 | 178.1 (2) | N3—C19—C20—C26 | 160.66 (18) |
C2—N1—C10—C12 | −1.9 (3) | N3—C19—C20—C21 | −16.8 (3) |
C5—N1—C10—O11 | −3.0 (4) | C19—C20—C21—C22 | 177.3 (2) |
C2—N1—C5—C4 | −0.2 (2) | C21—C20—C26—C27 | −173.5 (2) |
C2—N1—C5—C6 | 178.2 (2) | C19—C20—C26—C25 | −169.1 (2) |
C10—N1—C5—C4 | −179.3 (2) | C19—C20—C26—C27 | 9.1 (3) |
C10—N1—C5—C6 | −0.9 (4) | C26—C20—C21—C22 | −0.2 (3) |
C5—N1—C10—C12 | 177.1 (2) | C21—C20—C26—C25 | 8.3 (3) |
C19—N3—C2—N14 | −15.4 (3) | C20—C21—C22—O23 | 174.1 (3) |
C2—N3—C4—C9 | −178.1 (2) | C20—C21—C22—O24 | −8.6 (4) |
C19—N3—C4—C5 | −164.93 (19) | O24—C25—C26—C20 | −7.7 (3) |
C2—N3—C4—C5 | 0.7 (2) | O24—C25—C26—C27 | 173.9 (2) |
C2—N3—C19—C20 | 116.5 (2) | C30—C25—C26—C20 | 172.2 (2) |
C4—N3—C19—C20 | −80.0 (2) | C30—C25—C26—C27 | −6.2 (4) |
C19—N3—C2—N1 | 165.06 (18) | O24—C25—C30—C29 | −177.2 (3) |
C19—N3—C4—C9 | 16.2 (4) | C26—C25—C30—C29 | 2.9 (4) |
C4—N3—C2—N1 | −0.8 (2) | C20—C26—C27—C28 | −173.0 (2) |
C4—N3—C2—N14 | 178.7 (2) | C20—C26—C27—C34 | 10.4 (4) |
C13—N14—C2—N3 | −178.0 (2) | C25—C26—C27—C28 | 5.2 (3) |
C2—N14—C13—C12 | −1.6 (3) | C25—C26—C27—C34 | −171.4 (2) |
C2—N14—C13—C15 | 176.5 (2) | C26—C27—C28—C29 | −1.2 (3) |
C13—N14—C2—N1 | 1.5 (3) | C26—C27—C28—C31 | −179.8 (2) |
N3—C4—C9—C8 | 177.6 (2) | C34—C27—C28—C29 | 175.7 (2) |
C5—C4—C9—C8 | −1.2 (4) | C34—C27—C28—C31 | −2.9 (3) |
N3—C4—C5—N1 | −0.3 (2) | C26—C27—C34—C33 | 179.4 (2) |
N3—C4—C5—C6 | −178.9 (2) | C28—C27—C34—C33 | 2.7 (4) |
C9—C4—C5—N1 | 178.7 (2) | C27—C28—C29—C30 | −2.3 (4) |
C9—C4—C5—C6 | 0.1 (4) | C31—C28—C29—C30 | 176.3 (3) |
C4—C5—C6—C7 | 0.6 (4) | C27—C28—C31—C32 | 1.5 (4) |
N1—C5—C6—C7 | −177.6 (2) | C29—C28—C31—C32 | −177.1 (3) |
C5—C6—C7—C8 | −0.3 (4) | C28—C29—C30—C25 | 1.6 (4) |
C6—C7—C8—C9 | −0.8 (5) | C28—C31—C32—C33 | 0.3 (5) |
C7—C8—C9—C4 | 1.5 (4) | C31—C32—C33—C34 | −0.5 (5) |
O11—C10—C12—C13 | −178.2 (3) | C32—C33—C34—C27 | −1.1 (4) |
N1—C10—C12—C13 | 1.7 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z; (v) −x+1/2, y−1/2, −z+1/2; (vi) x, y+1, z; (vii) −x+3/2, y+1/2, −z+1/2; (viii) x, y−1, z; (ix) −x+1/2, y+1/2, −z+1/2; (x) x+1, y, z; (xi) −x+3/2, y−1/2, −z+1/2; (xii) x+1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O11ix | 0.93 | 2.33 | 3.241 (3) | 168 |
Symmetry code: (ix) −x+1/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O11i | 0.93 | 2.33 | 3.241 (3) | 168 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
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).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.