2-(4-Fluoro-phen-yl)-1,4,5-triphenyl-1H-imidazole.

In the title mol-ecule, C(27)H(19)FN(2), 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 ▶).

Experimental

Crystal data

C27H19FN2

M = 390.44

Triclinic,

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 ▶).

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

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

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

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

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.

	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*

	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)

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)