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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2519.
Published online 2010 September 8. doi:  10.1107/S1600536810035464
PMCID: PMC2983138

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

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 [triangle]). For contact allergy to imidazoles used as anti­mycotic agents, see: Dooms-Goossens et al. (1995 [triangle]). For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a [triangle],b [triangle],c [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2519-scheme1.jpg

Experimental

Crystal data

  • C27H19FN2
  • M r = 390.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2519-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Supplementary Material

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

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

C27H19FN2Z = 2
Mr = 390.44F(000) = 408
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Melting point: 509 K
a = 10.1794 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5239 (6) ÅCell parameters from 3942 reflections
c = 10.6175 (6) Åθ = 5.1–34.9°
α = 80.750 (5)°µ = 0.08 mm1
β = 85.776 (4)°T = 295 K
γ = 67.348 (5)°Plate, colourless
V = 1035.95 (11) Å30.51 × 0.44 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer8350 independent reflections
Radiation source: Enhance (Mo) X-ray Source3489 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.5081 pixels mm-1θmax = 35.0°, θmin = 5.1°
ω scansh = −15→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −16→14
Tmin = 0.973, Tmax = 1.000l = −17→16
15513 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3
8350 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.19 e Å3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
F40.80372 (8)0.08837 (10)−0.40649 (7)0.0903 (3)
N10.26200 (8)0.23531 (9)−0.01235 (8)0.0437 (3)
N30.42488 (8)0.27540 (10)0.08546 (8)0.0497 (3)
C20.39877 (10)0.23282 (11)−0.01679 (10)0.0459 (3)
C40.30225 (10)0.30605 (11)0.15929 (9)0.0455 (3)
C50.19960 (10)0.28135 (11)0.10135 (9)0.0429 (3)
C110.20194 (9)0.18684 (11)−0.10385 (9)0.0439 (3)
C120.16843 (11)0.07116 (13)−0.06763 (11)0.0556 (4)
C130.11969 (13)0.01955 (16)−0.15797 (15)0.0743 (5)
C140.10664 (14)0.08323 (18)−0.28296 (15)0.0794 (6)
C150.14007 (13)0.19852 (16)−0.31824 (12)0.0715 (5)
C160.18572 (11)0.25319 (13)−0.22810 (11)0.0560 (4)
C210.50330 (10)0.19099 (12)−0.12073 (10)0.0477 (3)
C220.51945 (10)0.08114 (12)−0.18562 (11)0.0528 (4)
C230.62124 (11)0.04652 (13)−0.28141 (11)0.0590 (4)
C240.70603 (12)0.12091 (15)−0.30998 (11)0.0625 (4)
C250.69616 (13)0.22763 (16)−0.24730 (12)0.0694 (5)
C260.59330 (12)0.26275 (14)−0.15231 (11)0.0607 (4)
C410.30110 (11)0.35537 (12)0.28205 (10)0.0468 (3)
C420.42822 (12)0.30638 (14)0.34878 (11)0.0602 (4)
C430.43495 (14)0.35356 (16)0.46073 (12)0.0713 (5)
C440.31579 (15)0.44905 (16)0.50961 (12)0.0688 (5)
C450.19033 (14)0.49726 (14)0.44586 (12)0.0654 (5)
C460.18239 (12)0.45176 (12)0.33263 (11)0.0554 (4)
C510.05103 (10)0.30008 (11)0.13802 (10)0.0438 (3)
C520.01739 (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)
H120.178520.028280.016760.0667*
H130.09574−0.05792−0.134550.0892*
H140.074890.04771−0.343930.0952*
H150.132000.24004−0.403030.0857*
H160.205150.33333−0.250850.0672*
H220.461500.03061−0.164530.0633*
H230.63160−0.02634−0.325570.0708*
H250.756750.27545−0.267760.0832*
H260.584320.33573−0.108850.0728*
H420.509450.241000.317170.0722*
H430.520750.320580.503620.0856*
H440.320520.480590.585450.0825*
H450.109300.561440.479000.0785*
H460.096310.486330.290000.0664*
H520.089260.207540.320540.0659*
H53−0.144380.245750.379300.0831*
H54−0.324480.359810.233510.0868*
H55−0.270680.434370.028170.0766*
H56−0.039110.39881−0.032260.0612*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F40.0761 (5)0.1160 (7)0.0732 (5)−0.0356 (5)0.0285 (4)−0.0132 (5)
N10.0411 (4)0.0500 (5)0.0453 (5)−0.0228 (4)0.0001 (3)−0.0076 (4)
N30.0443 (4)0.0584 (6)0.0520 (5)−0.0254 (4)−0.0013 (4)−0.0083 (4)
C20.0411 (5)0.0509 (7)0.0499 (6)−0.0229 (5)0.0000 (4)−0.0051 (5)
C40.0445 (5)0.0491 (6)0.0468 (6)−0.0223 (5)−0.0025 (4)−0.0051 (5)
C50.0426 (5)0.0447 (6)0.0442 (5)−0.0206 (4)0.0001 (4)−0.0046 (5)
C110.0387 (5)0.0495 (6)0.0472 (6)−0.0196 (5)0.0009 (4)−0.0107 (5)
C120.0570 (6)0.0552 (7)0.0621 (7)−0.0296 (6)0.0038 (5)−0.0103 (6)
C130.0762 (8)0.0745 (9)0.0928 (11)−0.0446 (7)0.0064 (7)−0.0319 (8)
C140.0734 (8)0.0955 (12)0.0841 (10)−0.0365 (8)−0.0108 (7)−0.0387 (9)
C150.0701 (8)0.0869 (10)0.0561 (8)−0.0245 (8)−0.0131 (6)−0.0144 (7)
C160.0571 (6)0.0572 (7)0.0551 (7)−0.0235 (6)−0.0057 (5)−0.0050 (5)
C210.0404 (5)0.0545 (7)0.0494 (6)−0.0210 (5)−0.0011 (4)−0.0027 (5)
C220.0437 (5)0.0523 (7)0.0614 (7)−0.0188 (5)0.0039 (5)−0.0062 (5)
C230.0524 (6)0.0580 (8)0.0604 (7)−0.0144 (6)0.0025 (5)−0.0091 (6)
C240.0487 (6)0.0770 (9)0.0532 (7)−0.0191 (6)0.0092 (5)−0.0017 (6)
C250.0587 (7)0.0863 (10)0.0723 (8)−0.0427 (7)0.0096 (6)−0.0028 (7)
C260.0563 (6)0.0712 (8)0.0653 (7)−0.0360 (6)0.0062 (5)−0.0127 (6)
C410.0512 (6)0.0504 (6)0.0466 (6)−0.0287 (5)−0.0033 (4)−0.0032 (5)
C420.0540 (6)0.0720 (9)0.0595 (7)−0.0282 (6)−0.0073 (5)−0.0093 (6)
C430.0750 (8)0.0885 (10)0.0608 (8)−0.0413 (8)−0.0212 (6)−0.0043 (7)
C440.0920 (9)0.0822 (10)0.0509 (7)−0.0515 (8)−0.0007 (7)−0.0146 (7)
C450.0749 (8)0.0694 (9)0.0625 (7)−0.0356 (7)0.0050 (6)−0.0209 (6)
C460.0563 (6)0.0572 (7)0.0580 (7)−0.0255 (6)−0.0053 (5)−0.0112 (6)
C510.0442 (5)0.0435 (6)0.0509 (6)−0.0231 (5)0.0041 (4)−0.0125 (5)
C520.0611 (6)0.0548 (7)0.0552 (7)−0.0291 (6)0.0088 (5)−0.0117 (5)
C530.0808 (9)0.0690 (9)0.0711 (8)−0.0434 (7)0.0320 (7)−0.0235 (7)
C540.0520 (7)0.0751 (9)0.1043 (11)−0.0360 (7)0.0224 (7)−0.0331 (8)
C550.0454 (6)0.0611 (8)0.0917 (9)−0.0240 (6)−0.0002 (6)−0.0207 (7)
C560.0470 (6)0.0503 (7)0.0620 (7)−0.0247 (5)−0.0009 (5)−0.0095 (5)

Geometric parameters (Å, °)

F4—C241.3626 (15)C45—C461.3822 (18)
N1—C21.3798 (14)C51—C521.3859 (16)
N1—C51.3905 (13)C51—C561.3960 (16)
N1—C111.4370 (13)C52—C531.386 (2)
N3—C21.3194 (14)C53—C541.378 (2)
N3—C41.3798 (14)C54—C551.367 (2)
C2—C211.4718 (15)C55—C561.3779 (17)
C4—C51.3759 (15)C12—H120.9300
C4—C411.4761 (15)C13—H130.9300
C5—C511.4785 (16)C14—H140.9300
C11—C121.3771 (16)C15—H150.9300
C11—C161.3793 (15)C16—H160.9300
C12—C131.381 (2)C22—H220.9300
C13—C141.378 (2)C23—H230.9300
C14—C151.372 (2)C25—H250.9300
C15—C161.3825 (19)C26—H260.9300
C21—C221.3897 (16)C42—H420.9300
C21—C261.3887 (18)C43—H430.9300
C22—C231.3834 (17)C44—H440.9300
C23—C241.3621 (19)C45—H450.9300
C24—C251.363 (2)C46—H460.9300
C25—C261.3843 (19)C52—H520.9300
C41—C421.3950 (18)C53—H530.9300
C41—C461.3831 (17)C54—H540.9300
C42—C431.3755 (18)C55—H550.9300
C43—C441.374 (2)C56—H560.9300
C44—C451.365 (2)
F4···H14i2.7400C42···H54i2.9300
F4···H53ii2.7400C44···H16vi2.9800
N1···H222.9400C45···H25vii3.0000
N1···H562.8800C46···H523.0900
N3···H262.6800C51···H123.1000
N3···H422.5900C51···H462.9100
N3···H55iii2.9400C52···H462.9200
C2···C22iv3.4772 (16)C53···H44viii2.9800
C4···C23iv3.5258 (17)C53···H13ix3.0100
C5···C56iii3.5569 (16)C54···H13ix3.0100
C5···C23iv3.5260 (16)C54···H44viii2.9400
C11···C563.1419 (16)C56···H56iii2.9700
C11···C223.0928 (15)H12···C53.0300
C12···C513.3300 (16)H12···C513.1000
C12···C563.4599 (17)H13···C53ix3.0100
C16···C213.2942 (17)H13···C54ix3.0100
C16···C223.2012 (17)H14···F4x2.7400
C21···C163.2942 (17)H16···C23.0700
C22···C113.0928 (15)H16···C44v2.9800
C22···C2iv3.4772 (16)H22···N12.9400
C22···C163.2012 (17)H22···C112.6200
C23···C4iv3.5258 (17)H22···C122.9700
C23···C5iv3.5260 (16)H22···C162.9200
C41···C523.4747 (18)H22···C2iv3.0100
C46···C513.4230 (16)H23···C4iv3.0400
C46···C523.3345 (18)H25···C45vii3.0000
C51···C463.4230 (16)H26···N32.6800
C51···C123.3300 (16)H42···N32.5900
C52···C463.3345 (18)H42···H54i2.5000
C52···C413.4747 (18)H43···C24vi2.8400
C56···C113.1419 (16)H44···C53viii2.9800
C56···C56iii3.4379 (16)H44···C54viii2.9400
C56···C5iii3.5569 (16)H46···C53.0200
C56···C123.4599 (17)H46···C512.9100
C2···H22iv3.0100H46···C522.9200
C2···H163.0700H52···C43.0500
C4···H55iii3.0300H52···C413.0800
C4···H23iv3.0400H52···C463.0900
C4···H523.0500H53···F4xi2.7400
C5···H463.0200H54···C42x2.9300
C5···H123.0300H54···H42x2.5000
C11···H562.7600H55···N3iii2.9400
C11···H222.6200H55···C4iii3.0300
C12···H222.9700H56···N12.8800
C16···H222.9200H56···C112.7600
C16···H563.0900H56···C163.0900
C24···H43v2.8400H56···C56iii2.9700
C41···H523.0800
C2—N1—C5107.30 (9)C52—C53—C54120.60 (13)
C2—N1—C11125.41 (9)C53—C54—C55119.52 (13)
C5—N1—C11127.07 (9)C54—C55—C56120.53 (12)
C2—N3—C4106.26 (9)C51—C56—C55120.81 (11)
N1—C2—N3110.82 (9)C11—C12—H12120.00
N1—C2—C21125.85 (9)C13—C12—H12120.00
N3—C2—C21123.32 (10)C12—C13—H13120.00
N3—C4—C5110.51 (9)C14—C13—H13120.00
N3—C4—C41118.29 (10)C13—C14—H14120.00
C5—C4—C41131.20 (10)C15—C14—H14120.00
N1—C5—C4105.11 (9)C14—C15—H15120.00
N1—C5—C51122.73 (9)C16—C15—H15120.00
C4—C5—C51132.12 (9)C11—C16—H16121.00
N1—C11—C12119.53 (9)C15—C16—H16121.00
N1—C11—C16119.13 (10)C21—C22—H22120.00
C12—C11—C16121.26 (10)C23—C22—H22120.00
C11—C12—C13119.27 (11)C22—C23—H23121.00
C12—C13—C14119.78 (14)C24—C23—H23121.00
C13—C14—C15120.59 (14)C24—C25—H25121.00
C14—C15—C16120.18 (12)C26—C25—H25121.00
C11—C16—C15118.87 (12)C21—C26—H26119.00
C2—C21—C22123.50 (10)C25—C26—H26119.00
C2—C21—C26117.88 (10)C41—C42—H42120.00
C22—C21—C26118.59 (10)C43—C42—H42120.00
C21—C22—C23120.38 (11)C42—C43—H43120.00
C22—C23—C24118.91 (12)C44—C43—H43120.00
F4—C24—C23118.56 (12)C43—C44—H44120.00
F4—C24—C25118.58 (12)C45—C44—H44120.00
C23—C24—C25122.85 (12)C44—C45—H45120.00
C24—C25—C26118.04 (13)C46—C45—H45120.00
C21—C26—C25121.21 (12)C41—C46—H46120.00
C4—C41—C42118.31 (11)C45—C46—H46120.00
C4—C41—C46123.79 (11)C51—C52—H52120.00
C42—C41—C46117.86 (11)C53—C52—H52120.00
C41—C42—C43120.84 (13)C52—C53—H53120.00
C42—C43—C44120.44 (14)C54—C53—H53120.00
C43—C44—C45119.41 (13)C53—C54—H54120.00
C44—C45—C46120.75 (13)C55—C54—H54120.00
C41—C46—C45120.70 (12)C54—C55—H55120.00
C5—C51—C52120.62 (10)C56—C55—H55120.00
C5—C51—C56121.15 (9)C51—C56—H56120.00
C52—C51—C56118.21 (11)C55—C56—H56120.00
C51—C52—C53120.33 (12)
C5—N1—C2—N3−0.64 (12)C16—C11—C12—C130.98 (18)
C5—N1—C2—C21−179.79 (10)N1—C11—C16—C15174.19 (11)
C11—N1—C2—N3−175.57 (9)C12—C11—C16—C15−2.50 (18)
C11—N1—C2—C215.28 (17)C11—C12—C13—C140.7 (2)
C2—N1—C5—C40.72 (11)C12—C13—C14—C15−0.8 (2)
C2—N1—C5—C51178.72 (10)C13—C14—C15—C16−0.8 (2)
C11—N1—C5—C4175.54 (10)C14—C15—C16—C112.4 (2)
C11—N1—C5—C51−6.46 (16)C2—C21—C22—C23−179.20 (11)
C2—N1—C11—C12112.68 (12)C26—C21—C22—C23−1.36 (17)
C2—N1—C11—C16−64.07 (15)C2—C21—C26—C25178.74 (12)
C5—N1—C11—C12−61.25 (15)C22—C21—C26—C250.78 (18)
C5—N1—C11—C16122.00 (12)C21—C22—C23—C240.66 (18)
C4—N3—C2—N10.28 (12)C22—C23—C24—F4−178.45 (11)
C4—N3—C2—C21179.46 (10)C22—C23—C24—C250.7 (2)
C2—N3—C4—C50.20 (12)F4—C24—C25—C26177.87 (12)
C2—N3—C4—C41179.33 (10)C23—C24—C25—C26−1.3 (2)
N1—C2—C21—C22−38.85 (17)C24—C25—C26—C210.5 (2)
N1—C2—C21—C26143.30 (11)C4—C41—C42—C43177.03 (12)
N3—C2—C21—C22142.10 (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—C440.7 (2)
C41—C4—C5—N1−179.56 (11)C42—C43—C44—C45−0.2 (2)
C41—C4—C5—C512.7 (2)C43—C44—C45—C46−0.4 (2)
N3—C4—C41—C42−31.76 (15)C44—C45—C46—C410.6 (2)
N3—C4—C41—C46145.60 (12)C5—C51—C52—C53177.49 (11)
C5—C4—C41—C42147.16 (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—C52135.85 (11)C52—C51—C56—C550.59 (17)
N1—C5—C51—C56−45.92 (16)C51—C52—C53—C540.4 (2)
C4—C5—C51—C52−46.76 (18)C52—C53—C54—C550.3 (2)
C4—C5—C51—C56131.48 (13)C53—C54—C55—C56−0.5 (2)
N1—C11—C12—C13−175.70 (11)C54—C55—C56—C510.1 (2)

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).

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