Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Page o2519
doi:10.1107/S1600536810035464

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

P. Gayathri,a A. Thiruvalluvar,a* N. Srinivasan,b J. Jayabharathib and R. J. Butcherc

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 26 August 2010; accepted 2 September 2010; online 8 September 2010)

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[Nagalakshmi, G. (2008). Eur. J. Chem. 5, 447-452.]). For contact allergy to imidazoles used as anti­mycotic agents, see: Dooms-Goossens et al. (1995[Dooms-Goossens, A., Matura, M., Drieghe, J. & Degreeef, H. (1995). Contact Dermatitis, 33, 73-77.]). For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a[Gayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791.],b[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703.],c[Gayathri, P., Thiruvalluvar, A., Saravanan, K., Jayabharathi, J. & Butcher, R. J. (2010c). Acta Cryst. E66, o2219.]).

[Scheme 1]

Experimental

Crystal data

  • C27H19FN2

  • Mr = 390.44

  • Triclinic, [P \overline 1]

  • 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[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.973, Tmax = 1.000

  • 15513 measured reflections

  • 8350 independent reflections

  • 3489 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

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

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

checkCIF report


Comment top

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.

Related literature top

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).

Experimental top

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 top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top
[Figure 1] 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.
2-(4-Fluorophenyl)-1,4,5-triphenyl-1H-imidazole top
Crystal data top
C27H19FN2Z = 2
Mr = 390.44F(000) = 408
Triclinic, P1Dx = 1.252 Mg m−3
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 mm−1
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 top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		8350 independent reflections
Radiation source: Enhance (Mo) X-ray Source3489 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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 = 0.86 w = 1/[σ2(Fo2) + (0.0586P)2]
where P = (Fo2 + 2Fc2)/3
8350 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C27H19FN2γ = 67.348 (5)°
Mr = 390.44V = 1035.95 (11) Å3
Triclinic, P1Z = 2
a = 10.1794 (5) ÅMo Kα radiation
b = 10.5239 (6) ŵ = 0.08 mm−1
c = 10.6175 (6) ÅT = 295 K
α = 80.750 (5)°0.51 × 0.44 × 0.15 mm
β = 85.776 (4)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		8350 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		3489 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 1.000Rint = 0.030
15513 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 0.86Δρmax = 0.22 e Å−3
8350 reflectionsΔρmin = −0.19 e Å−3
271 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 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) top
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) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC27H19FN2
Mr390.44
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)10.1794 (5), 10.5239 (6), 10.6175 (6)
α, β, γ (°)80.750 (5), 85.776 (4), 67.348 (5)
V (Å3)1035.95 (11)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.51 × 0.44 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.973, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		15513, 8350, 3489
Rint0.030
(sin θ/λ)max (Å−1)0.806
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.128, 0.86
No. of reflections8350
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

 

Acknowledgements

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.

References

First citationDooms-Goossens, A., Matura, M., Drieghe, J. & Degreeef, H. (1995). Contact Dermatitis, 33, 73–77.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGayathri, P., Thiruvalluvar, A., Saravanan, K., Jayabharathi, J. & Butcher, R. J. (2010c). Acta Cryst. E66, o2219.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNagalakshmi, G. (2008). Eur. J. Chem. 5, 447–452.  CAS Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Page o2519
doi:10.1107/S1600536810035464
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS