2-(4-Fluoro-phen-yl)-1-(4-meth-oxy-phen-yl)-4,5-dimethyl-1H-imidazole.

In the title compound, C(18)H(17)FN(2)O, the imidazole ring makes dihedral angles of 76.46 (7) and 40.68 (7)° with the meth-oxy-phenyl and fluoro-phenyl rings, respectively. The dihedral angle between the two benzene rings is 71.25 (6)°.

Related literature

For the optical properties of heterocyclic imidazole derivatives, see: Santos et al. (2001 ▶); Huang et al. (2004 ▶). For their role in the preparation of functionalized materials, see: Kamidate et al. (1989 ▶). For their fluorescence and chemiluminescence properties, see: Ucucu et al. (2001 ▶). For their use in the construction of fluorescent chemisensors, see: Jayabharathi et al. (2009 ▶, 2010 ▶); Zhou & Fahrni (2004 ▶).

Experimental

Crystal data

C18H17FN2O

M = 296.34

Monoclinic,

a = 8.5132 (1) Å

b = 9.5128 (2) Å

c = 19.2610 (3) Å

β = 96.798 (2)°

V = 1548.87 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 295 K

0.40 × 0.32 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.835, T max = 1.000

6517 measured reflections

3235 independent reflections

2744 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.130

S = 1.08

3235 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (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/S1600536810024104/wn2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024104/wn2396Isup2.hkl

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

C18H17FN2O	F(000) = 624
Mr = 296.34	Dx = 1.271 Mg m−3
Monoclinic, P21/c	Melting point: 385 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 8.5132 (1) Å	Cell parameters from 4271 reflections
b = 9.5128 (2) Å	θ = 4.6–77.3°
c = 19.2610 (3) Å	µ = 0.72 mm−1
β = 96.798 (2)°	T = 295 K
V = 1548.87 (4) Å3	Prism, colourless
Z = 4	0.40 × 0.32 × 0.22 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3235 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2744 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.5081 pixels mm-1	θmax = 77.5°, θmin = 4.6°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→9
Tmin = 0.835, Tmax = 1.000	l = −23→24
6517 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.076P)2 + 0.1231P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3235 reflections	Δρmax = 0.16 e Å−3
200 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0214 (14)

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	0.28268 (12)	−0.00876 (12)	0.68530 (5)	0.0874 (4)
O17	0.19515 (13)	−0.00279 (11)	0.26852 (6)	0.0708 (4)
N1	0.26219 (12)	0.46448 (11)	0.44385 (5)	0.0517 (3)
N3	0.22859 (14)	0.59440 (12)	0.53660 (6)	0.0604 (4)
C2	0.24814 (14)	0.46597 (14)	0.51401 (6)	0.0530 (4)
C4	0.22762 (16)	0.68002 (15)	0.47855 (7)	0.0623 (4)
C5	0.24779 (16)	0.60275 (14)	0.42099 (7)	0.0581 (4)
C11	0.25104 (14)	0.34332 (12)	0.39879 (6)	0.0480 (3)
C12	0.38038 (14)	0.29589 (14)	0.36872 (6)	0.0531 (4)
C13	0.36702 (15)	0.18029 (14)	0.32457 (6)	0.0540 (4)
C14	0.22295 (15)	0.11173 (13)	0.31098 (6)	0.0529 (4)
C15	0.09313 (16)	0.16030 (15)	0.34140 (7)	0.0609 (4)
C16	0.10672 (14)	0.27585 (14)	0.38472 (7)	0.0561 (4)
C17	0.3214 (2)	−0.05517 (17)	0.23377 (8)	0.0719 (5)
C21	0.25773 (14)	0.33905 (14)	0.55796 (6)	0.0531 (4)
C22	0.36774 (16)	0.23360 (16)	0.55099 (7)	0.0617 (4)
C23	0.37767 (17)	0.11663 (17)	0.59375 (7)	0.0664 (5)
C24	0.27481 (16)	0.10690 (16)	0.64337 (7)	0.0629 (4)
C25	0.16576 (18)	0.20821 (18)	0.65268 (7)	0.0684 (5)
C26	0.15801 (13)	0.32536 (12)	0.60982 (6)	0.0620 (4)
C41	0.20446 (13)	0.83510 (12)	0.48384 (6)	0.0871 (7)
C51	0.2531 (2)	0.64214 (17)	0.34669 (8)	0.0771 (6)
H12	0.47707	0.34170	0.37811	0.0636*
H13	0.45430	0.14889	0.30417	0.0647*
H15	−0.00361	0.11441	0.33243	0.0731*
H16	0.01913	0.30851	0.40450	0.0674*
H17A	0.40446	−0.08890	0.26772	0.1079*
H17B	0.28354	−0.13078	0.20326	0.1079*
H17C	0.36133	0.01881	0.20685	0.1079*
H22	0.43594	0.24196	0.51689	0.0740*
H23	0.45182	0.04651	0.58909	0.0797*
H25	0.09829	0.19875	0.68700	0.0820*
H26	0.08516	0.39590	0.61576	0.0744*
H41A	0.09876	0.85400	0.49396	0.1306*
H41B	0.27883	0.87228	0.52062	0.1306*
H41C	0.22090	0.87872	0.44034	0.1306*
H51A	0.22550	0.73950	0.34023	0.1157*
H51B	0.35792	0.62701	0.33449	0.1157*
H51C	0.17938	0.58537	0.31733	0.1157*

	U11	U22	U33	U12	U13	U23
F4	0.0794 (6)	0.0928 (7)	0.0893 (6)	−0.0048 (5)	0.0075 (5)	0.0315 (5)
O17	0.0808 (7)	0.0606 (6)	0.0735 (6)	−0.0040 (5)	0.0191 (5)	−0.0211 (5)
N1	0.0556 (5)	0.0500 (5)	0.0508 (5)	−0.0028 (4)	0.0114 (4)	−0.0055 (4)
N3	0.0624 (6)	0.0605 (7)	0.0591 (6)	−0.0047 (5)	0.0109 (5)	−0.0151 (5)
C2	0.0516 (6)	0.0578 (7)	0.0502 (6)	−0.0020 (5)	0.0080 (5)	−0.0098 (5)
C4	0.0626 (8)	0.0534 (7)	0.0723 (8)	−0.0063 (5)	0.0143 (6)	−0.0103 (6)
C5	0.0611 (7)	0.0511 (7)	0.0641 (7)	−0.0044 (5)	0.0152 (5)	−0.0028 (5)
C11	0.0525 (6)	0.0479 (6)	0.0448 (5)	0.0004 (5)	0.0103 (4)	−0.0021 (4)
C12	0.0486 (6)	0.0571 (7)	0.0546 (6)	−0.0029 (5)	0.0109 (5)	−0.0009 (5)
C13	0.0558 (7)	0.0566 (7)	0.0518 (6)	0.0074 (5)	0.0161 (5)	0.0000 (5)
C14	0.0644 (7)	0.0479 (6)	0.0475 (6)	0.0019 (5)	0.0114 (5)	−0.0021 (5)
C15	0.0546 (7)	0.0617 (8)	0.0681 (8)	−0.0097 (5)	0.0144 (6)	−0.0120 (6)
C16	0.0505 (6)	0.0593 (7)	0.0614 (7)	−0.0011 (5)	0.0183 (5)	−0.0083 (6)
C17	0.0900 (10)	0.0660 (8)	0.0607 (8)	0.0139 (7)	0.0130 (7)	−0.0143 (7)
C21	0.0521 (6)	0.0609 (7)	0.0457 (6)	−0.0053 (5)	0.0029 (4)	−0.0085 (5)
C22	0.0580 (7)	0.0754 (9)	0.0526 (7)	0.0050 (6)	0.0104 (5)	0.0022 (6)
C23	0.0619 (7)	0.0734 (9)	0.0630 (8)	0.0089 (7)	0.0035 (6)	0.0035 (7)
C24	0.0598 (7)	0.0707 (8)	0.0560 (7)	−0.0085 (6)	−0.0019 (5)	0.0060 (6)
C25	0.0640 (8)	0.0852 (10)	0.0574 (7)	−0.0100 (7)	0.0136 (6)	0.0001 (7)
C26	0.0602 (7)	0.0692 (8)	0.0579 (7)	−0.0010 (6)	0.0125 (5)	−0.0090 (6)
C41	0.1054 (13)	0.0557 (9)	0.1035 (13)	−0.0034 (8)	0.0256 (10)	−0.0168 (8)
C51	0.1017 (12)	0.0617 (9)	0.0721 (9)	0.0013 (8)	0.0276 (8)	0.0082 (7)

F4—C24	1.3618 (18)	C23—C24	1.374 (2)
O17—C14	1.3660 (16)	C24—C25	1.365 (2)
O17—C17	1.422 (2)	C25—C26	1.384 (2)
N1—C2	1.3707 (15)	C12—H12	0.9300
N1—C5	1.3879 (17)	C13—H13	0.9300
N1—C11	1.4392 (15)	C15—H15	0.9300
N3—C2	1.3141 (17)	C16—H16	0.9300
N3—C4	1.3825 (18)	C17—H17A	0.9600
C2—C21	1.4713 (18)	C17—H17B	0.9600
C4—C5	1.3579 (19)	C17—H17C	0.9600
C4—C41	1.4934 (18)	C22—H22	0.9300
C5—C51	1.485 (2)	C23—H23	0.9300
C11—C12	1.3793 (17)	C25—H25	0.9300
C11—C16	1.3842 (17)	C26—H26	0.9300
C12—C13	1.3865 (18)	C41—H41A	0.9600
C13—C14	1.3864 (18)	C41—H41B	0.9600
C14—C15	1.3898 (19)	C41—H41C	0.9600
C15—C16	1.3766 (19)	C51—H51A	0.9600
C21—C22	1.3897 (19)	C51—H51B	0.9600
C21—C26	1.3915 (16)	C51—H51C	0.9600
C22—C23	1.381 (2)
F4···H13i	2.5900	C26···H17Cvii	2.8100
F4···H15ii	2.5600	C41···H51A	2.9400
F4···H17Ai	2.8600	C51···H41C	2.9200
O17···H51Aiii	2.8100	C51···H26v	3.0700
N1···H22	2.8600	H12···C17ix	3.0700
N3···H26	2.8000	H12···N3iv	2.8900
N3···H12iv	2.8900	H13···C17	2.5500
N3···H16v	2.6700	H13···H17A	2.3900
C4···C26v	3.5149 (18)	H13···H17C	2.3100
C5···C26v	3.5027 (18)	H13···F4i	2.5900
C11···C22	3.1592 (18)	H15···F4ii	2.5600
C12···C51	3.478 (2)	H16···C2	3.0900
C12···C22	3.5745 (18)	H16···N3v	2.6700
C14···C25vi	3.4808 (19)	H17A···C13	2.8200
C16···C21	3.4832 (18)	H17A···H13	2.3900
C17···C26vi	3.410 (2)	H17A···F4i	2.8600
C21···C16	3.4832 (18)	H17A···C23i	3.0800
C22···C11	3.1592 (18)	H17A···C24i	3.0500
C22···C12	3.5745 (18)	H17C···C13	2.7300
C25···C14vii	3.4808 (19)	H17C···H13	2.3100
C26···C17vii	3.410 (2)	H17C···C26vi	2.8100
C26···C4v	3.5149 (18)	H22···N1	2.8600
C26···C5v	3.5027 (18)	H22···C11	2.7800
C51···C12	3.478 (2)	H22···C12	2.8800
C2···H16	3.0900	H22···C4iv	2.9500
C4···H22iv	2.9500	H23···H41Biii	2.4900
C5···H26v	2.8400	H23···C13i	3.0300
C11···H22	2.7800	H25···C14vii	3.0800
C11···H51C	2.8100	H26···N3	2.8000
C12···H22	2.8800	H26···C5v	2.8400
C13···H17A	2.8200	H26···C51v	3.0700
C13···H23i	3.0300	H41B···C23x	2.8000
C13···H17C	2.7300	H41B···H23x	2.4900
C14···H25vi	3.0800	H41C···C51	2.9200
C17···H12viii	3.0700	H41C···H51A	2.3400
C17···H13	2.5500	H51A···O17x	2.8100
C17···H51Aiii	3.0100	H51A···C17x	3.0100
C23···H17Ai	3.0800	H51A···C41	2.9400
C23···H41Biii	2.8000	H51A···H41C	2.3400
C24···H17Ai	3.0500	H51C···C11	2.8100
C14—O17—C17	118.31 (12)	C11—C12—H12	120.00
C2—N1—C5	106.75 (10)	C13—C12—H12	120.00
C2—N1—C11	126.56 (10)	C12—C13—H13	120.00
C5—N1—C11	124.79 (10)	C14—C13—H13	120.00
C2—N3—C4	105.59 (11)	C14—C15—H15	120.00
N1—C2—N3	111.43 (11)	C16—C15—H15	120.00
N1—C2—C21	123.60 (11)	C11—C16—H16	120.00
N3—C2—C21	124.96 (11)	C15—C16—H16	120.00
N3—C4—C5	110.62 (12)	O17—C17—H17A	109.00
N3—C4—C41	121.00 (11)	O17—C17—H17B	109.00
C5—C4—C41	128.38 (12)	O17—C17—H17C	109.00
N1—C5—C4	105.60 (11)	H17A—C17—H17B	109.00
N1—C5—C51	122.22 (12)	H17A—C17—H17C	109.00
C4—C5—C51	132.17 (13)	H17B—C17—H17C	109.00
N1—C11—C12	121.08 (11)	C21—C22—H22	119.00
N1—C11—C16	118.89 (11)	C23—C22—H22	119.00
C12—C11—C16	120.02 (11)	C22—C23—H23	121.00
C11—C12—C13	120.36 (11)	C24—C23—H23	121.00
C12—C13—C14	119.70 (11)	C24—C25—H25	121.00
O17—C14—C13	125.09 (12)	C26—C25—H25	121.00
O17—C14—C15	115.31 (12)	C21—C26—H26	120.00
C13—C14—C15	119.60 (12)	C25—C26—H26	120.00
C14—C15—C16	120.47 (12)	C4—C41—H41A	109.00
C11—C16—C15	119.86 (12)	C4—C41—H41B	109.00
C2—C21—C22	121.93 (11)	C4—C41—H41C	109.00
C2—C21—C26	119.53 (11)	H41A—C41—H41B	109.00
C22—C21—C26	118.50 (12)	H41A—C41—H41C	109.00
C21—C22—C23	121.22 (13)	H41B—C41—H41C	109.00
C22—C23—C24	118.05 (14)	C5—C51—H51A	109.00
F4—C24—C23	118.45 (13)	C5—C51—H51B	109.00
F4—C24—C25	118.63 (12)	C5—C51—H51C	109.00
C23—C24—C25	122.92 (14)	H51A—C51—H51B	109.00
C24—C25—C26	118.39 (13)	H51A—C51—H51C	109.00
C21—C26—C25	120.90 (12)	H51B—C51—H51C	109.00
C17—O17—C14—C13	−1.62 (19)	N3—C4—C5—C51	178.88 (15)
C17—O17—C14—C15	177.89 (12)	C41—C4—C5—N1	−179.32 (12)
C5—N1—C2—N3	−0.96 (14)	C41—C4—C5—C51	−0.3 (3)
C5—N1—C2—C21	−179.65 (11)	N1—C11—C12—C13	−179.00 (11)
C11—N1—C2—N3	−165.76 (11)	C16—C11—C12—C13	−0.29 (18)
C11—N1—C2—C21	15.55 (19)	N1—C11—C16—C15	179.58 (11)
C2—N1—C5—C4	0.64 (14)	C12—C11—C16—C15	0.84 (19)
C2—N1—C5—C51	−178.50 (13)	C11—C12—C13—C14	−0.36 (18)
C11—N1—C5—C4	165.78 (11)	C12—C13—C14—O17	179.95 (13)
C11—N1—C5—C51	−13.4 (2)	C12—C13—C14—C15	0.46 (18)
C2—N1—C11—C12	−113.75 (14)	O17—C14—C15—C16	−179.44 (12)
C2—N1—C11—C16	67.52 (16)	C13—C14—C15—C16	0.10 (19)
C5—N1—C11—C12	84.05 (16)	C14—C15—C16—C11	−0.8 (2)
C5—N1—C11—C16	−94.68 (15)	C2—C21—C22—C23	178.47 (12)
C4—N3—C2—N1	0.86 (14)	C26—C21—C22—C23	0.7 (2)
C4—N3—C2—C21	179.52 (12)	C2—C21—C26—C25	−179.05 (12)
C2—N3—C4—C5	−0.43 (16)	C22—C21—C26—C25	−1.26 (18)
C2—N3—C4—C41	178.82 (12)	C21—C22—C23—C24	0.3 (2)
N1—C2—C21—C22	40.96 (18)	C22—C23—C24—F4	179.35 (13)
N1—C2—C21—C26	−141.33 (12)	C22—C23—C24—C25	−1.0 (2)
N3—C2—C21—C22	−137.56 (14)	F4—C24—C25—C26	−179.85 (12)
N3—C2—C21—C26	40.16 (18)	C23—C24—C25—C26	0.5 (2)
N3—C4—C5—N1	−0.14 (15)	C24—C25—C26—C21	0.7 (2)