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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Sep 8;66(Pt 10):o2519. doi: 10.1107/S1600536810035464

2-(4-Fluoro­phen­yl)-1,4,5-triphenyl-1H-imidazole

P Gayathri a, A Thiruvalluvar a,*, N Srinivasan b, J Jayabharathi b, R J Butcher c
PMCID: PMC2983138  PMID: 21587513

Abstract

In the title mol­ecule, C27H19FN2, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 62.80 (6), 36.98 (6), 33.16 (6) and 46.24 (6)°, respectively, with the substituent rings in the 1-, 2-, 4- and 5-positions. No classical hydrogen bonds are observed in the crystal structure.

Related literature

For the synthesis and pharmacological evaluation of substituted 1H-imidazoles, see: (Nagalakshmi, 2008 ▶). For contact allergy to imidazoles used as anti­mycotic agents, see: Dooms-Goossens et al. (1995 ▶). For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a ▶,b ▶,c ▶).graphic file with name e-66-o2519-scheme1.jpg

Experimental

Crystal data

  • C27H19FN2

  • M r = 390.44

  • Triclinic, Inline graphic

  • a = 10.1794 (5) Å

  • b = 10.5239 (6) Å

  • c = 10.6175 (6) Å

  • α = 80.750 (5)°

  • β = 85.776 (4)°

  • γ = 67.348 (5)°

  • V = 1035.95 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.51 × 0.44 × 0.15 mm

Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.973, T max = 1.000

  • 15513 measured reflections

  • 8350 independent reflections

  • 3489 reflections with I > 2σ(I)

  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049

  • wR(F 2) = 0.128

  • S = 0.86

  • 8350 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035464/tk2707sup1.cif

e-66-o2519-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035464/tk2707Isup2.hkl

e-66-o2519-Isup2.hkl (400.2KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

JJ is thankful to the Department of Science and Technology [No. SR/S1/IC-07/2007] and the University Grants Commission (F. No. 36–21/2008 (SR)) for providing funds for this research. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

Nagalakshmi (2008) has reported synthesis and pharmacological evaluation of 2-(4-Halo substituted phenyl)-4,5-diphenyl-1H-imidazoles, and Dooms-Goossens et al. (1995) have reported contact allergy to imidazoles used as antimycotic agents. As part of our research (Gayathri et al., (2010a,b,c)), we have synthesized the title compound (I) and report its crystal structure here.

In (I), Fig. 1, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å for N1]. The imidazole ring makes dihedral angles of 62.80 (6), 36.98 (6), 33.16 (6) and 46.24 (6) ° with the phenyl (C11—C16) attached to N1, fluorophenyl (C21—C26) attached to C2, and two phenyl rings (C41—C46) & (C51—C56) attached to C4 and C5, respectively. The phenyl ring at N1 makes dihedral angles of 54.26 (6), 85.21 (7) and 65.02 (6) ° with the fluorophenyl at C2, and phenyl rings attached to C4 and C5, respectively. The fluorophenyl ring makes dihedral angles of 63.01 (6) and 78.99 (6) ° with the phenyl rings at C4 and C5, respectively. Finally, the dihedral angle between the phenyl rings at C4 and C5 is 51.10 (6) °. In the crystal structure no classical hydrogen bonds are observed.

Experimental

To benzil (3.15 g, 15 mmol) in ethanol (10 ml), aniline (1.5 g, 15 mmol), ammonium acetate (7 g, 15 mmol) and p-fluorobenzaldehyde (1.7 g, 15 mmol) were added over about 1 h while maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid that separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 3.51 g (60%).

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(parent atom).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.

Crystal data

C27H19FN2 Z = 2
Mr = 390.44 F(000) = 408
Triclinic, P1 Dx = 1.252 Mg m−3
Hall symbol: -P 1 Melting point: 509 K
a = 10.1794 (5) Å Mo Kα radiation, λ = 0.71073 Å
b = 10.5239 (6) Å Cell parameters from 3942 reflections
c = 10.6175 (6) Å θ = 5.1–34.9°
α = 80.750 (5)° µ = 0.08 mm−1
β = 85.776 (4)° T = 295 K
γ = 67.348 (5)° Plate, colourless
V = 1035.95 (11) Å3 0.51 × 0.44 × 0.15 mm
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Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer 8350 independent reflections
Radiation source: Enhance (Mo) X-ray Source 3489 reflections with I > 2σ(I)
graphite Rint = 0.030
Detector resolution: 10.5081 pixels mm-1 θmax = 35.0°, θmin = 5.1°
ω scans h = −15→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) k = −16→14
Tmin = 0.973, Tmax = 1.000 l = −17→16
15513 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128 H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
8350 reflections (Δ/σ)max = 0.001
271 parameters Δρmax = 0.22 e Å−3
0 restraints Δρmin = −0.19 e Å−3
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Special details

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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
F4 0.80372 (8) 0.08837 (10) −0.40649 (7) 0.0903 (3)
N1 0.26200 (8) 0.23531 (9) −0.01235 (8) 0.0437 (3)
N3 0.42488 (8) 0.27540 (10) 0.08546 (8) 0.0497 (3)
C2 0.39877 (10) 0.23282 (11) −0.01679 (10) 0.0459 (3)
C4 0.30225 (10) 0.30605 (11) 0.15929 (9) 0.0455 (3)
C5 0.19960 (10) 0.28135 (11) 0.10135 (9) 0.0429 (3)
C11 0.20194 (9) 0.18684 (11) −0.10385 (9) 0.0439 (3)
C12 0.16843 (11) 0.07116 (13) −0.06763 (11) 0.0556 (4)
C13 0.11969 (13) 0.01955 (16) −0.15797 (15) 0.0743 (5)
C14 0.10664 (14) 0.08323 (18) −0.28296 (15) 0.0794 (6)
C15 0.14007 (13) 0.19852 (16) −0.31824 (12) 0.0715 (5)
C16 0.18572 (11) 0.25319 (13) −0.22810 (11) 0.0560 (4)
C21 0.50330 (10) 0.19099 (12) −0.12073 (10) 0.0477 (3)
C22 0.51945 (10) 0.08114 (12) −0.18562 (11) 0.0528 (4)
C23 0.62124 (11) 0.04652 (13) −0.28141 (11) 0.0590 (4)
C24 0.70603 (12) 0.12091 (15) −0.30998 (11) 0.0625 (4)
C25 0.69616 (13) 0.22763 (16) −0.24730 (12) 0.0694 (5)
C26 0.59330 (12) 0.26275 (14) −0.15231 (11) 0.0607 (4)
C41 0.30110 (11) 0.35537 (12) 0.28205 (10) 0.0468 (3)
C42 0.42822 (12) 0.30638 (14) 0.34878 (11) 0.0602 (4)
C43 0.43495 (14) 0.35356 (16) 0.46073 (12) 0.0713 (5)
C44 0.31579 (15) 0.44905 (16) 0.50961 (12) 0.0688 (5)
C45 0.19033 (14) 0.49726 (14) 0.44586 (12) 0.0654 (5)
C46 0.18239 (12) 0.45176 (12) 0.33263 (11) 0.0554 (4)
C51 0.05103 (10) 0.30008 (11) 0.13802 (10) 0.0438 (3)
C52 0.01739 (12) 0.25395 (13) 0.26117 (11) 0.0549 (4)
C53 −0.12281 (14) 0.27662 (14) 0.29629 (13) 0.0693 (5)
C54 −0.23054 (13) 0.34450 (15) 0.20932 (15) 0.0724 (5)
C55 −0.19831 (11) 0.38917 (14) 0.08727 (13) 0.0638 (4)
C56 −0.05946 (10) 0.36777 (12) 0.05109 (11) 0.0510 (4)
H12 0.17852 0.02828 0.01676 0.0667*
H13 0.09574 −0.05792 −0.13455 0.0892*
H14 0.07489 0.04771 −0.34393 0.0952*
H15 0.13200 0.24004 −0.40303 0.0857*
H16 0.20515 0.33333 −0.25085 0.0672*
H22 0.46150 0.03061 −0.16453 0.0633*
H23 0.63160 −0.02634 −0.32557 0.0708*
H25 0.75675 0.27545 −0.26776 0.0832*
H26 0.58432 0.33573 −0.10885 0.0728*
H42 0.50945 0.24100 0.31717 0.0722*
H43 0.52075 0.32058 0.50362 0.0856*
H44 0.32052 0.48059 0.58545 0.0825*
H45 0.10930 0.56144 0.47900 0.0785*
H46 0.09631 0.48633 0.29000 0.0664*
H52 0.08926 0.20754 0.32054 0.0659*
H53 −0.14438 0.24575 0.37930 0.0831*
H54 −0.32448 0.35981 0.23351 0.0868*
H55 −0.27068 0.43437 0.02817 0.0766*
H56 −0.03911 0.39881 −0.03226 0.0612*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
F4 0.0761 (5) 0.1160 (7) 0.0732 (5) −0.0356 (5) 0.0285 (4) −0.0132 (5)
N1 0.0411 (4) 0.0500 (5) 0.0453 (5) −0.0228 (4) 0.0001 (3) −0.0076 (4)
N3 0.0443 (4) 0.0584 (6) 0.0520 (5) −0.0254 (4) −0.0013 (4) −0.0083 (4)
C2 0.0411 (5) 0.0509 (7) 0.0499 (6) −0.0229 (5) 0.0000 (4) −0.0051 (5)
C4 0.0445 (5) 0.0491 (6) 0.0468 (6) −0.0223 (5) −0.0025 (4) −0.0051 (5)
C5 0.0426 (5) 0.0447 (6) 0.0442 (5) −0.0206 (4) 0.0001 (4) −0.0046 (5)
C11 0.0387 (5) 0.0495 (6) 0.0472 (6) −0.0196 (5) 0.0009 (4) −0.0107 (5)
C12 0.0570 (6) 0.0552 (7) 0.0621 (7) −0.0296 (6) 0.0038 (5) −0.0103 (6)
C13 0.0762 (8) 0.0745 (9) 0.0928 (11) −0.0446 (7) 0.0064 (7) −0.0319 (8)
C14 0.0734 (8) 0.0955 (12) 0.0841 (10) −0.0365 (8) −0.0108 (7) −0.0387 (9)
C15 0.0701 (8) 0.0869 (10) 0.0561 (8) −0.0245 (8) −0.0131 (6) −0.0144 (7)
C16 0.0571 (6) 0.0572 (7) 0.0551 (7) −0.0235 (6) −0.0057 (5) −0.0050 (5)
C21 0.0404 (5) 0.0545 (7) 0.0494 (6) −0.0210 (5) −0.0011 (4) −0.0027 (5)
C22 0.0437 (5) 0.0523 (7) 0.0614 (7) −0.0188 (5) 0.0039 (5) −0.0062 (5)
C23 0.0524 (6) 0.0580 (8) 0.0604 (7) −0.0144 (6) 0.0025 (5) −0.0091 (6)
C24 0.0487 (6) 0.0770 (9) 0.0532 (7) −0.0191 (6) 0.0092 (5) −0.0017 (6)
C25 0.0587 (7) 0.0863 (10) 0.0723 (8) −0.0427 (7) 0.0096 (6) −0.0028 (7)
C26 0.0563 (6) 0.0712 (8) 0.0653 (7) −0.0360 (6) 0.0062 (5) −0.0127 (6)
C41 0.0512 (6) 0.0504 (6) 0.0466 (6) −0.0287 (5) −0.0033 (4) −0.0032 (5)
C42 0.0540 (6) 0.0720 (9) 0.0595 (7) −0.0282 (6) −0.0073 (5) −0.0093 (6)
C43 0.0750 (8) 0.0885 (10) 0.0608 (8) −0.0413 (8) −0.0212 (6) −0.0043 (7)
C44 0.0920 (9) 0.0822 (10) 0.0509 (7) −0.0515 (8) −0.0007 (7) −0.0146 (7)
C45 0.0749 (8) 0.0694 (9) 0.0625 (7) −0.0356 (7) 0.0050 (6) −0.0209 (6)
C46 0.0563 (6) 0.0572 (7) 0.0580 (7) −0.0255 (6) −0.0053 (5) −0.0112 (6)
C51 0.0442 (5) 0.0435 (6) 0.0509 (6) −0.0231 (5) 0.0041 (4) −0.0125 (5)
C52 0.0611 (6) 0.0548 (7) 0.0552 (7) −0.0291 (6) 0.0088 (5) −0.0117 (5)
C53 0.0808 (9) 0.0690 (9) 0.0711 (8) −0.0434 (7) 0.0320 (7) −0.0235 (7)
C54 0.0520 (7) 0.0751 (9) 0.1043 (11) −0.0360 (7) 0.0224 (7) −0.0331 (8)
C55 0.0454 (6) 0.0611 (8) 0.0917 (9) −0.0240 (6) −0.0002 (6) −0.0207 (7)
C56 0.0470 (6) 0.0503 (7) 0.0620 (7) −0.0247 (5) −0.0009 (5) −0.0095 (5)
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Geometric parameters (Å, °)

F4—C24 1.3626 (15) C45—C46 1.3822 (18)
N1—C2 1.3798 (14) C51—C52 1.3859 (16)
N1—C5 1.3905 (13) C51—C56 1.3960 (16)
N1—C11 1.4370 (13) C52—C53 1.386 (2)
N3—C2 1.3194 (14) C53—C54 1.378 (2)
N3—C4 1.3798 (14) C54—C55 1.367 (2)
C2—C21 1.4718 (15) C55—C56 1.3779 (17)
C4—C5 1.3759 (15) C12—H12 0.9300
C4—C41 1.4761 (15) C13—H13 0.9300
C5—C51 1.4785 (16) C14—H14 0.9300
C11—C12 1.3771 (16) C15—H15 0.9300
C11—C16 1.3793 (15) C16—H16 0.9300
C12—C13 1.381 (2) C22—H22 0.9300
C13—C14 1.378 (2) C23—H23 0.9300
C14—C15 1.372 (2) C25—H25 0.9300
C15—C16 1.3825 (19) C26—H26 0.9300
C21—C22 1.3897 (16) C42—H42 0.9300
C21—C26 1.3887 (18) C43—H43 0.9300
C22—C23 1.3834 (17) C44—H44 0.9300
C23—C24 1.3621 (19) C45—H45 0.9300
C24—C25 1.363 (2) C46—H46 0.9300
C25—C26 1.3843 (19) C52—H52 0.9300
C41—C42 1.3950 (18) C53—H53 0.9300
C41—C46 1.3831 (17) C54—H54 0.9300
C42—C43 1.3755 (18) C55—H55 0.9300
C43—C44 1.374 (2) C56—H56 0.9300
C44—C45 1.365 (2)
F4···H14i 2.7400 C42···H54i 2.9300
F4···H53ii 2.7400 C44···H16vi 2.9800
N1···H22 2.9400 C45···H25vii 3.0000
N1···H56 2.8800 C46···H52 3.0900
N3···H26 2.6800 C51···H12 3.1000
N3···H42 2.5900 C51···H46 2.9100
N3···H55iii 2.9400 C52···H46 2.9200
C2···C22iv 3.4772 (16) C53···H44viii 2.9800
C4···C23iv 3.5258 (17) C53···H13ix 3.0100
C5···C56iii 3.5569 (16) C54···H13ix 3.0100
C5···C23iv 3.5260 (16) C54···H44viii 2.9400
C11···C56 3.1419 (16) C56···H56iii 2.9700
C11···C22 3.0928 (15) H12···C5 3.0300
C12···C51 3.3300 (16) H12···C51 3.1000
C12···C56 3.4599 (17) H13···C53ix 3.0100
C16···C21 3.2942 (17) H13···C54ix 3.0100
C16···C22 3.2012 (17) H14···F4x 2.7400
C21···C16 3.2942 (17) H16···C2 3.0700
C22···C11 3.0928 (15) H16···C44v 2.9800
C22···C2iv 3.4772 (16) H22···N1 2.9400
C22···C16 3.2012 (17) H22···C11 2.6200
C23···C4iv 3.5258 (17) H22···C12 2.9700
C23···C5iv 3.5260 (16) H22···C16 2.9200
C41···C52 3.4747 (18) H22···C2iv 3.0100
C46···C51 3.4230 (16) H23···C4iv 3.0400
C46···C52 3.3345 (18) H25···C45vii 3.0000
C51···C46 3.4230 (16) H26···N3 2.6800
C51···C12 3.3300 (16) H42···N3 2.5900
C52···C46 3.3345 (18) H42···H54i 2.5000
C52···C41 3.4747 (18) H43···C24vi 2.8400
C56···C11 3.1419 (16) H44···C53viii 2.9800
C56···C56iii 3.4379 (16) H44···C54viii 2.9400
C56···C5iii 3.5569 (16) H46···C5 3.0200
C56···C12 3.4599 (17) H46···C51 2.9100
C2···H22iv 3.0100 H46···C52 2.9200
C2···H16 3.0700 H52···C4 3.0500
C4···H55iii 3.0300 H52···C41 3.0800
C4···H23iv 3.0400 H52···C46 3.0900
C4···H52 3.0500 H53···F4xi 2.7400
C5···H46 3.0200 H54···C42x 2.9300
C5···H12 3.0300 H54···H42x 2.5000
C11···H56 2.7600 H55···N3iii 2.9400
C11···H22 2.6200 H55···C4iii 3.0300
C12···H22 2.9700 H56···N1 2.8800
C16···H22 2.9200 H56···C11 2.7600
C16···H56 3.0900 H56···C16 3.0900
C24···H43v 2.8400 H56···C56iii 2.9700
C41···H52 3.0800
C2—N1—C5 107.30 (9) C52—C53—C54 120.60 (13)
C2—N1—C11 125.41 (9) C53—C54—C55 119.52 (13)
C5—N1—C11 127.07 (9) C54—C55—C56 120.53 (12)
C2—N3—C4 106.26 (9) C51—C56—C55 120.81 (11)
N1—C2—N3 110.82 (9) C11—C12—H12 120.00
N1—C2—C21 125.85 (9) C13—C12—H12 120.00
N3—C2—C21 123.32 (10) C12—C13—H13 120.00
N3—C4—C5 110.51 (9) C14—C13—H13 120.00
N3—C4—C41 118.29 (10) C13—C14—H14 120.00
C5—C4—C41 131.20 (10) C15—C14—H14 120.00
N1—C5—C4 105.11 (9) C14—C15—H15 120.00
N1—C5—C51 122.73 (9) C16—C15—H15 120.00
C4—C5—C51 132.12 (9) C11—C16—H16 121.00
N1—C11—C12 119.53 (9) C15—C16—H16 121.00
N1—C11—C16 119.13 (10) C21—C22—H22 120.00
C12—C11—C16 121.26 (10) C23—C22—H22 120.00
C11—C12—C13 119.27 (11) C22—C23—H23 121.00
C12—C13—C14 119.78 (14) C24—C23—H23 121.00
C13—C14—C15 120.59 (14) C24—C25—H25 121.00
C14—C15—C16 120.18 (12) C26—C25—H25 121.00
C11—C16—C15 118.87 (12) C21—C26—H26 119.00
C2—C21—C22 123.50 (10) C25—C26—H26 119.00
C2—C21—C26 117.88 (10) C41—C42—H42 120.00
C22—C21—C26 118.59 (10) C43—C42—H42 120.00
C21—C22—C23 120.38 (11) C42—C43—H43 120.00
C22—C23—C24 118.91 (12) C44—C43—H43 120.00
F4—C24—C23 118.56 (12) C43—C44—H44 120.00
F4—C24—C25 118.58 (12) C45—C44—H44 120.00
C23—C24—C25 122.85 (12) C44—C45—H45 120.00
C24—C25—C26 118.04 (13) C46—C45—H45 120.00
C21—C26—C25 121.21 (12) C41—C46—H46 120.00
C4—C41—C42 118.31 (11) C45—C46—H46 120.00
C4—C41—C46 123.79 (11) C51—C52—H52 120.00
C42—C41—C46 117.86 (11) C53—C52—H52 120.00
C41—C42—C43 120.84 (13) C52—C53—H53 120.00
C42—C43—C44 120.44 (14) C54—C53—H53 120.00
C43—C44—C45 119.41 (13) C53—C54—H54 120.00
C44—C45—C46 120.75 (13) C55—C54—H54 120.00
C41—C46—C45 120.70 (12) C54—C55—H55 120.00
C5—C51—C52 120.62 (10) C56—C55—H55 120.00
C5—C51—C56 121.15 (9) C51—C56—H56 120.00
C52—C51—C56 118.21 (11) C55—C56—H56 120.00
C51—C52—C53 120.33 (12)
C5—N1—C2—N3 −0.64 (12) C16—C11—C12—C13 0.98 (18)
C5—N1—C2—C21 −179.79 (10) N1—C11—C16—C15 174.19 (11)
C11—N1—C2—N3 −175.57 (9) C12—C11—C16—C15 −2.50 (18)
C11—N1—C2—C21 5.28 (17) C11—C12—C13—C14 0.7 (2)
C2—N1—C5—C4 0.72 (11) C12—C13—C14—C15 −0.8 (2)
C2—N1—C5—C51 178.72 (10) C13—C14—C15—C16 −0.8 (2)
C11—N1—C5—C4 175.54 (10) C14—C15—C16—C11 2.4 (2)
C11—N1—C5—C51 −6.46 (16) C2—C21—C22—C23 −179.20 (11)
C2—N1—C11—C12 112.68 (12) C26—C21—C22—C23 −1.36 (17)
C2—N1—C11—C16 −64.07 (15) C2—C21—C26—C25 178.74 (12)
C5—N1—C11—C12 −61.25 (15) C22—C21—C26—C25 0.78 (18)
C5—N1—C11—C16 122.00 (12) C21—C22—C23—C24 0.66 (18)
C4—N3—C2—N1 0.28 (12) C22—C23—C24—F4 −178.45 (11)
C4—N3—C2—C21 179.46 (10) C22—C23—C24—C25 0.7 (2)
C2—N3—C4—C5 0.20 (12) F4—C24—C25—C26 177.87 (12)
C2—N3—C4—C41 179.33 (10) C23—C24—C25—C26 −1.3 (2)
N1—C2—C21—C22 −38.85 (17) C24—C25—C26—C21 0.5 (2)
N1—C2—C21—C26 143.30 (11) C4—C41—C42—C43 177.03 (12)
N3—C2—C21—C22 142.10 (12) C46—C41—C42—C43 −0.48 (19)
N3—C2—C21—C26 −35.75 (16) C4—C41—C46—C45 −177.52 (12)
N3—C4—C5—N1 −0.57 (12) C42—C41—C46—C45 −0.15 (18)
N3—C4—C5—C51 −178.31 (11) C41—C42—C43—C44 0.7 (2)
C41—C4—C5—N1 −179.56 (11) C42—C43—C44—C45 −0.2 (2)
C41—C4—C5—C51 2.7 (2) C43—C44—C45—C46 −0.4 (2)
N3—C4—C41—C42 −31.76 (15) C44—C45—C46—C41 0.6 (2)
N3—C4—C41—C46 145.60 (12) C5—C51—C52—C53 177.49 (11)
C5—C4—C41—C42 147.16 (13) C56—C51—C52—C53 −0.79 (18)
C5—C4—C41—C46 −35.48 (19) C5—C51—C56—C55 −177.69 (11)
N1—C5—C51—C52 135.85 (11) C52—C51—C56—C55 0.59 (17)
N1—C5—C51—C56 −45.92 (16) C51—C52—C53—C54 0.4 (2)
C4—C5—C51—C52 −46.76 (18) C52—C53—C54—C55 0.3 (2)
C4—C5—C51—C56 131.48 (13) C53—C54—C55—C56 −0.5 (2)
N1—C11—C12—C13 −175.70 (11) C54—C55—C56—C51 0.1 (2)
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Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) x, y, z−1; (vi) x, y, z+1; (vii) −x+1, −y+1, −z; (viii) −x, −y+1, −z+1; (ix) −x, −y, −z; (x) x−1, y, z; (xi) x−1, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2707).

References

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  3. Gayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791. [DOI] [PMC free article] [PubMed]
  4. Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703. [DOI] [PMC free article] [PubMed]
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  6. Nagalakshmi, G. (2008). Eur. J. Chem.5, 447–452.
  7. Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035464/tk2707sup1.cif

e-66-o2519-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035464/tk2707Isup2.hkl

e-66-o2519-Isup2.hkl (400.2KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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