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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o672-o673
https://doi.org/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

CROSSMARK_Color_square_no_text.svg
Chandra,a Shamantha Kumar.,b K. B. Puttaraju,c K. Shivashankarc and M. Mahendraa*

aDepartment 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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 July 2015; accepted 30 July 2015; online 22 August 2015)

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.

CCDC reference: 1416062

Similar articles

1. Related literature

For background to benzo­pyrimidine derivatives, see: Bodke et al. (2003[Bodke, Y. & Sangapure, S. S. (2003). J. Indian Chem. Soc. 80, 187-189.]); Moneam et al. (2004[Moneam, M., Geies, A., El-Naggar, G. & Mousa, S. (2004). Jnl Chin. Chem. Soc. 51, 1357-1366.]). For the synthesis of the title compound, see: Puttaraju et al. (2013[Puttaraju, K. B., Shivashankar, K., Chandra, Mahendra, M., Rasal, V. P., Vivek, P. N. V. Rai, K. & Chanu, M. B. (2013). Eur. J. Med. Chem. 69, 316-322.]). For a related structure, see: Chandra et al. (2013[Chandra, Puttaraju, K. B., Shivashankar, K., Jithesh Babu, E. A. & Mahendra, M. (2013). Acta Cryst. E69, o1536.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C25H14F3N3O3

  • Mr = 461.39

  • Monoclinic, P 21 /n

  • 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

2.2. Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • 9209 measured reflections

  • 5020 independent reflections

  • 2637 reflections with I > 2σ(I)

  • Rint = 0.033

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.176

  • S = 1.00

  • 5020 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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+{\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

CCDC reference: 1416062

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015014425/hb7467sup1.cif

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

checkCIF report


Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

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 b axis.
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 top
Crystal data top
C25H14F3N3O3F(000) = 944
Mr = 461.39Dx = 1.494 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5020 reflections
a = 9.7665 (5) Åθ = 2.7–28.3°
b = 7.7950 (4) ŵ = 0.12 mm−1
c = 27.0602 (16) ÅT = 293 K
β = 95.186 (5)°Bolck, yellow
V = 2051.66 (19) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		Rint = 0.033
ω and φ scansθmax = 28.3°, θmin = 2.7°
9209 measured reflectionsh = −11→12
5020 independent reflectionsk = −5→10
2637 reflections with I > 2σ(I)l = −27→36
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)] = 0.057H-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 reflectionsΔρmax = 0.21 e Å−3
308 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (8)
Crystal data top
C25H14F3N3O3V = 2051.66 (19) Å3
Mr = 461.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7665 (5) ŵ = 0.12 mm−1
b = 7.7950 (4) ÅT = 293 K
c = 27.0602 (16) Å0.30 × 0.25 × 0.20 mm
β = 95.186 (5)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2637 reflections with I > 2σ(I)
9209 measured reflectionsRint = 0.033
5020 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.176H-atom parameters constrained
S = 1.00Δρmax = 0.21 e Å−3
5020 reflectionsΔρmin = −0.19 e Å−3
308 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
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)
O110.20544 (19)0.5442 (3)0.27911 (6)0.0737 (8)
O230.4824 (2)1.3933 (2)0.15054 (8)0.0862 (9)
O240.62445 (19)1.3111 (2)0.09616 (7)0.0628 (7)
N10.31775 (19)0.6564 (2)0.21634 (7)0.0455 (6)
N30.44740 (17)0.7624 (2)0.16034 (6)0.0409 (6)
N140.21121 (18)0.7121 (2)0.13481 (7)0.0463 (6)
C20.3181 (2)0.7104 (3)0.16781 (8)0.0410 (7)
C40.5313 (2)0.7441 (3)0.20479 (8)0.0447 (7)
C50.4513 (2)0.6770 (3)0.24038 (9)0.0478 (8)
C60.5044 (3)0.6466 (3)0.28881 (9)0.0618 (9)
C70.6405 (3)0.6880 (4)0.29999 (10)0.0739 (11)
C80.7211 (3)0.7556 (4)0.26516 (11)0.0725 (11)
C90.6678 (2)0.7831 (3)0.21638 (10)0.0592 (9)
C100.1990 (3)0.5950 (3)0.23595 (9)0.0545 (8)
C120.0819 (3)0.6013 (3)0.20043 (9)0.0587 (9)
C130.0939 (2)0.6575 (3)0.15344 (9)0.0515 (8)
C15−0.0306 (3)0.6693 (4)0.11661 (10)0.0623 (10)
C190.4956 (2)0.7898 (3)0.11163 (8)0.0424 (7)
C200.5353 (2)0.9744 (3)0.10211 (8)0.0402 (7)
C210.4909 (2)1.0969 (3)0.13174 (9)0.0511 (8)
C220.5260 (3)1.2748 (3)0.12793 (10)0.0608 (10)
C250.6706 (3)1.1898 (3)0.06486 (9)0.0538 (8)
C260.6241 (2)1.0222 (3)0.06349 (8)0.0418 (7)
C270.6713 (2)0.9122 (3)0.02498 (8)0.0461 (7)
C280.7704 (2)0.9786 (4)−0.00588 (9)0.0598 (9)
C290.8182 (3)1.1485 (4)0.00084 (11)0.0763 (11)
C300.7689 (3)1.2528 (4)0.03478 (11)0.0730 (11)
C310.8178 (3)0.8749 (5)−0.04365 (11)0.0803 (13)
C320.7698 (3)0.7147 (5)−0.05239 (11)0.0787 (13)
C330.6709 (3)0.6507 (4)−0.02363 (10)0.0682 (10)
C340.6220 (3)0.7459 (3)0.01357 (9)0.0536 (8)
H60.451100.600900.312400.0740*
H70.679900.669900.332100.0890*
H80.812400.783200.274600.0870*
H90.722000.825800.192700.0710*
H12−0.003500.566700.209500.0700*
H19A0.423800.755400.086500.0510*
H19B0.574700.716800.108300.0510*
H210.434401.064600.156000.0610*
H290.885101.18930−0.018500.0920*
H300.799701.365400.038200.0880*
H310.883800.91840−0.063000.0960*
H320.802500.64810−0.077300.0950*
H330.636900.54050−0.029700.0820*
H340.554600.699400.031700.0640*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F160.0900 (14)0.0943 (15)0.1297 (18)0.0138 (11)−0.0336 (12)0.0102 (13)
F170.0675 (10)0.1379 (17)0.0697 (11)−0.0180 (11)−0.0005 (8)−0.0251 (11)
F180.0503 (10)0.1613 (19)0.0968 (14)−0.0305 (11)0.0128 (9)0.0081 (13)
O110.0810 (13)0.0911 (15)0.0517 (11)−0.0130 (11)0.0211 (9)0.0169 (11)
O230.1251 (18)0.0480 (11)0.0847 (15)0.0111 (11)0.0045 (13)−0.0181 (11)
O240.0774 (13)0.0432 (9)0.0664 (12)−0.0115 (9)−0.0012 (10)0.0027 (9)
N10.0509 (11)0.0471 (11)0.0396 (10)−0.0036 (9)0.0106 (8)0.0015 (9)
N30.0404 (10)0.0434 (10)0.0397 (10)−0.0047 (9)0.0083 (7)−0.0002 (9)
N140.0429 (10)0.0540 (12)0.0426 (10)−0.0056 (10)0.0078 (8)0.0004 (10)
C20.0463 (13)0.0375 (12)0.0402 (12)−0.0020 (10)0.0101 (9)−0.0008 (10)
C40.0462 (13)0.0448 (13)0.0435 (12)0.0003 (11)0.0068 (10)−0.0018 (11)
C50.0510 (14)0.0490 (14)0.0434 (12)0.0005 (12)0.0048 (10)−0.0012 (12)
C60.0688 (17)0.0678 (18)0.0484 (14)0.0022 (14)0.0038 (12)0.0029 (14)
C70.076 (2)0.090 (2)0.0520 (16)0.0069 (17)−0.0137 (14)0.0015 (16)
C80.0582 (17)0.086 (2)0.0704 (19)0.0014 (16)−0.0095 (14)−0.0032 (17)
C90.0480 (14)0.0681 (17)0.0612 (16)−0.0014 (13)0.0038 (12)−0.0014 (15)
C100.0614 (15)0.0549 (15)0.0502 (14)−0.0069 (13)0.0210 (12)0.0048 (13)
C120.0488 (14)0.0646 (17)0.0651 (17)−0.0092 (13)0.0189 (12)0.0038 (14)
C130.0443 (13)0.0544 (15)0.0574 (15)−0.0057 (12)0.0136 (11)0.0026 (13)
C150.0518 (16)0.076 (2)0.0597 (17)−0.0108 (15)0.0080 (12)−0.0019 (16)
C190.0450 (12)0.0405 (12)0.0434 (12)−0.0041 (10)0.0128 (9)−0.0030 (10)
C200.0414 (12)0.0378 (11)0.0409 (11)−0.0025 (10)0.0016 (9)0.0000 (10)
C210.0587 (15)0.0443 (13)0.0506 (14)0.0006 (12)0.0070 (11)−0.0034 (12)
C220.0789 (19)0.0460 (15)0.0558 (16)0.0076 (14)−0.0039 (14)−0.0056 (13)
C250.0565 (15)0.0501 (14)0.0531 (14)−0.0076 (12)−0.0043 (11)0.0045 (13)
C260.0403 (11)0.0460 (13)0.0384 (11)−0.0023 (10)0.0006 (9)0.0052 (10)
C270.0388 (11)0.0601 (15)0.0391 (11)0.0036 (11)0.0018 (9)0.0043 (12)
C280.0456 (14)0.085 (2)0.0498 (14)−0.0011 (14)0.0095 (11)0.0087 (15)
C290.0701 (19)0.097 (2)0.0637 (19)−0.0268 (18)0.0162 (15)0.0151 (18)
C300.0746 (19)0.0704 (19)0.0729 (19)−0.0324 (16)0.0013 (15)0.0196 (17)
C310.0624 (18)0.122 (3)0.0605 (18)0.006 (2)0.0279 (14)0.005 (2)
C320.077 (2)0.108 (3)0.0533 (17)0.024 (2)0.0178 (15)−0.0043 (19)
C330.081 (2)0.0726 (19)0.0519 (15)0.0111 (15)0.0106 (14)−0.0084 (15)
C340.0634 (15)0.0552 (15)0.0435 (13)−0.0026 (13)0.0115 (11)−0.0066 (12)
Geometric parameters (Å, º) top
F16—C151.344 (4)C21—C221.434 (3)
F17—C151.320 (3)C25—C261.383 (3)
F18—C151.320 (3)C25—C301.402 (4)
O11—C101.229 (3)C26—C271.456 (3)
O23—C221.207 (3)C27—C281.431 (3)
O24—C221.376 (3)C27—C341.407 (3)
O24—C251.372 (3)C28—C291.411 (4)
N1—C21.379 (3)C28—C311.414 (4)
N1—C51.413 (3)C29—C301.348 (4)
N1—C101.403 (3)C31—C321.347 (5)
N3—C21.359 (3)C32—C331.387 (4)
N3—C41.400 (3)C33—C341.371 (4)
N3—C191.455 (3)C6—H60.9300
N14—C21.311 (3)C7—H70.9300
N14—C131.361 (3)C8—H80.9300
C4—C51.396 (3)C9—H90.9300
C4—C91.376 (3)C12—H120.9300
C5—C61.386 (3)C19—H19A0.9700
C6—C71.375 (4)C19—H19B0.9700
C7—C81.386 (4)C21—H210.9300
C8—C91.391 (4)C29—H290.9300
C10—C121.427 (4)C30—H300.9300
C12—C131.360 (3)C31—H310.9300
C13—C151.504 (4)C32—H320.9300
C19—C201.518 (3)C33—H330.9300
C20—C211.344 (3)C34—H340.9300
C20—C261.465 (3)
F16···N142.878 (3)C32···C22iii3.386 (4)
F16···C27i3.310 (3)C32···C21iii3.502 (4)
F17···N142.763 (2)C33···C22iii3.320 (4)
F17···H30ii2.7100C33···O24iii3.352 (3)
F17···H29iii2.5900C33···C30viii3.572 (4)
F17···H32iv2.8100C34···C193.045 (3)
F18···H9i2.8200C34···C25iii3.439 (4)
F18···H122.4000C34···C26iii3.534 (3)
O11···C63.015 (3)C2···H213.0100
O11···C2v2.991 (3)C4···H212.9400
O11···N1v3.035 (3)C9···H19B3.0300
O11···N3v3.191 (3)C10···H63.0700
O11···C21v3.241 (3)C19···H92.9800
O11···C4v3.345 (3)C19···H342.3900
O11···C5v3.266 (3)C20···H342.8900
O23···N3vi2.912 (2)C22···H7vii3.0900
O23···C2vi3.006 (3)C22···H8vii2.9500
O23···N1vi3.237 (3)C25···H7vii3.0300
O23···C5vi3.321 (3)C27···H19B2.9500
O23···C19vi3.271 (3)C30···H33vi3.0500
O23···C4vi3.120 (3)C33···H30viii2.9900
O24···C33iii3.352 (3)C34···H19B2.6600
O11···H62.5200C34···H19A2.8900
O11···H21v2.3300H6···O112.5200
O23···H8vii2.8500H6···C103.0700
O24···H7vii2.8200H7···O24xi2.8200
N1···O23viii3.237 (3)H7···C22xi3.0900
N1···O11ix3.035 (3)H7···C25xi3.0300
N3···O23viii2.912 (2)H8···O23xi2.8500
N3···O11ix3.191 (3)H8···C22xi2.9500
N14···F172.763 (2)H9···F18x2.8200
N14···F162.878 (3)H9···C192.9800
N3···H212.3600H12···F182.4000
N14···H19A2.5700H19A···N142.5700
C2···O23viii3.006 (3)H19A···C342.8900
C2···O11ix2.991 (3)H19A···H342.0900
C4···C213.389 (3)H19B···C93.0300
C4···O23viii3.120 (3)H19B···C272.9500
C4···O11ix3.345 (3)H19B···C342.6600
C5···O11ix3.266 (3)H19B···H342.0700
C5···O23viii3.321 (3)H21···N32.3600
C6···O113.015 (3)H21···C23.0100
C9···C203.569 (3)H21···C42.9400
C19···C343.045 (3)H21···O11ix2.3300
C19···O23viii3.271 (3)H29···H312.4300
C20···C93.569 (3)H29···F17iii2.5900
C21···O11ix3.241 (3)H30···F17xii2.7100
C21···C43.389 (3)H30···C33vi2.9900
C21···C32iii3.502 (4)H31···H292.4300
C22···C33iii3.320 (4)H32···F17iv2.8100
C22···C32iii3.386 (4)H33···C30viii3.0500
C25···C34iii3.439 (4)H34···C192.3900
C26···C34iii3.534 (3)H34···C202.8900
C27···F16x3.310 (3)H34···H19A2.0900
C30···C33vi3.572 (4)H34···H19B2.0700
C22—O24—C25122.07 (19)C20—C26—C25115.8 (2)
C2—N1—C5108.78 (18)C20—C26—C27127.4 (2)
C2—N1—C10122.53 (19)C25—C26—C27116.8 (2)
C5—N1—C10128.7 (2)C26—C27—C28118.6 (2)
C2—N3—C4108.75 (17)C26—C27—C34125.1 (2)
C2—N3—C19124.04 (17)C28—C27—C34116.2 (2)
C4—N3—C19125.53 (16)C27—C28—C29119.9 (2)
C2—N14—C13112.93 (19)C27—C28—C31119.9 (3)
N1—C2—N3108.36 (17)C29—C28—C31120.3 (2)
N1—C2—N14125.54 (19)C28—C29—C30121.3 (3)
N3—C2—N14126.1 (2)C25—C30—C29119.3 (3)
N3—C4—C5108.08 (17)C28—C31—C32121.7 (3)
N3—C4—C9130.8 (2)C31—C32—C33118.9 (3)
C5—C4—C9121.1 (2)C32—C33—C34121.6 (3)
N1—C5—C4106.02 (19)C27—C34—C33121.7 (2)
N1—C5—C6131.8 (2)C5—C6—H6122.00
C4—C5—C6122.1 (2)C7—C6—H6122.00
C5—C6—C7116.1 (2)C6—C7—H7119.00
C6—C7—C8122.5 (3)C8—C7—H7119.00
C7—C8—C9121.1 (3)C7—C8—H8119.00
C4—C9—C8117.0 (2)C9—C8—H8119.00
O11—C10—N1119.8 (2)C4—C9—H9122.00
O11—C10—C12128.3 (3)C8—C9—H9121.00
N1—C10—C12111.9 (2)C10—C12—H12120.00
C10—C12—C13120.6 (2)C13—C12—H12120.00
N14—C13—C12126.4 (2)N3—C19—H19A109.00
N14—C13—C15113.1 (2)N3—C19—H19B109.00
C12—C13—C15120.4 (2)C20—C19—H19A109.00
F16—C15—F17104.7 (2)C20—C19—H19B109.00
F16—C15—F18106.0 (2)H19A—C19—H19B108.00
F16—C15—C13110.7 (2)C20—C21—H21118.00
F17—C15—F18107.5 (2)C22—C21—H21118.00
F17—C15—C13113.5 (2)C28—C29—H29119.00
F18—C15—C13113.8 (2)C30—C29—H29119.00
N3—C19—C20113.66 (18)C25—C30—H30120.00
C19—C20—C21118.11 (19)C29—C30—H30120.00
C19—C20—C26122.60 (19)C28—C31—H31119.00
C21—C20—C26119.3 (2)C32—C31—H31119.00
C20—C21—C22123.5 (2)C31—C32—H32121.00
O23—C22—O24117.3 (2)C33—C32—H32121.00
O23—C22—C21127.3 (3)C32—C33—H33119.00
O24—C22—C21115.4 (2)C34—C33—H33119.00
O24—C25—C26122.8 (2)C27—C34—H34119.00
O24—C25—C30113.4 (2)C33—C34—H34119.00
C26—C25—C30123.8 (2)
C22—O24—C25—C30178.8 (2)C10—C12—C13—C15−178.0 (2)
C25—O24—C22—O23−173.1 (2)C10—C12—C13—N140.0 (4)
C25—O24—C22—C219.3 (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—F1749.4 (3)
C10—N1—C2—N3179.82 (18)N14—C13—C15—F18172.8 (2)
C10—N1—C2—N140.3 (3)C12—C13—C15—F16110.3 (3)
C5—N1—C2—N30.7 (2)C12—C13—C15—F17−132.3 (3)
C2—N1—C10—O11178.1 (2)N3—C19—C20—C26160.66 (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—C22177.3 (2)
C2—N1—C5—C4−0.2 (2)C21—C20—C26—C27−173.5 (2)
C2—N1—C5—C6178.2 (2)C19—C20—C26—C25−169.1 (2)
C10—N1—C5—C4−179.3 (2)C19—C20—C26—C279.1 (3)
C10—N1—C5—C6−0.9 (4)C26—C20—C21—C22−0.2 (3)
C5—N1—C10—C12177.1 (2)C21—C20—C26—C258.3 (3)
C19—N3—C2—N14−15.4 (3)C20—C21—C22—O23174.1 (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—C50.7 (2)O24—C25—C26—C27173.9 (2)
C2—N3—C19—C20116.5 (2)C30—C25—C26—C20172.2 (2)
C4—N3—C19—C20−80.0 (2)C30—C25—C26—C27−6.2 (4)
C19—N3—C2—N1165.06 (18)O24—C25—C30—C29−177.2 (3)
C19—N3—C4—C916.2 (4)C26—C25—C30—C292.9 (4)
C4—N3—C2—N1−0.8 (2)C20—C26—C27—C28−173.0 (2)
C4—N3—C2—N14178.7 (2)C20—C26—C27—C3410.4 (4)
C13—N14—C2—N3−178.0 (2)C25—C26—C27—C285.2 (3)
C2—N14—C13—C12−1.6 (3)C25—C26—C27—C34−171.4 (2)
C2—N14—C13—C15176.5 (2)C26—C27—C28—C29−1.2 (3)
C13—N14—C2—N11.5 (3)C26—C27—C28—C31−179.8 (2)
N3—C4—C9—C8177.6 (2)C34—C27—C28—C29175.7 (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—C33179.4 (2)
N3—C4—C5—C6−178.9 (2)C28—C27—C34—C332.7 (4)
C9—C4—C5—N1178.7 (2)C27—C28—C29—C30−2.3 (4)
C9—C4—C5—C60.1 (4)C31—C28—C29—C30176.3 (3)
C4—C5—C6—C70.6 (4)C27—C28—C31—C321.5 (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—C251.6 (4)
C6—C7—C8—C9−0.8 (5)C28—C31—C32—C330.3 (5)
C7—C8—C9—C41.5 (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—C131.7 (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.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O11ix0.932.333.241 (3)168
Symmetry code: (ix) −x+1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O11i0.932.333.241 (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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 First citationPuttaraju, K. B., Shivashankar, K., Chandra, Mahendra, M., Rasal, V. P., Vivek, P. N. V. Rai, K. & Chanu, M. B. (2013). Eur. J. Med. Chem. 69, 316–322.  CSD CrossRef CAS PubMed Google Scholar
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ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o672-o673
https://doi.org/10.1107/S2056989015014425
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