4-(4-Fluoro-phen-yl)-1-methoxy-methyl-2-phenyl-1H-imidazole.

In the crystal structure of the title compound, C(17)H(15)FN(2)O, the mol-ecules form a three-dimensional network stabilized by π-π inter-actions between two imidazole rings related by a centre of symmetry. The distance between the centroids is 3.5488 (8) Å. The imidazole ring makes dihedral angles of 14.30 (7) and 33.39 (7)° with the 4-fluoro-phenyl ring and the phenyl ring, respectively.

Related literature

For the preparation of diaryl­imidazoles, see: Li et al. (2002 ▶). For synthesis of and with related diarylimidazoles, see: Liverton et al. (1999 ▶); Kawasaki et al. (1996 ▶).

Experimental

Crystal data

C17H15FN2O

M = 282.31

Monoclinic,

a = 10.524 (1) Å

b = 11.248 (1) Å

c = 11.981 (1) Å

β = 92.206 (3)°

V = 1417.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

37183 measured reflections

3319 independent reflections

2745 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.07

3319 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042366/bt5098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042366/bt5098Isup2.hkl

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

C17H15FN2O	F(000) = 592
Mr = 282.31	Dx = 1.323 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 9878 reflections
a = 10.524 (1) Å	θ = 2.4–27.6°
b = 11.2480 (11) Å	µ = 0.09 mm−1
c = 11.9810 (12) Å	T = 173 K
β = 92.206 (3)°	Needle, colourless
V = 1417.2 (2) Å3	0.40 × 0.30 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2745 reflections with I > 2σ(I)
Radiation source: sealed Tube	Rint = 0.043
graphite	θmax = 27.7°, θmin = 2.5°
CCD scan	h = −13→13
37183 measured reflections	k = −14→14
3319 independent reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.5423P] where P = (Fo2 + 2Fc2)/3
3319 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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 > σ(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
C1	0.37469 (12)	0.48140 (11)	0.36743 (10)	0.0272 (3)
N2	0.47445 (10)	0.45452 (9)	0.30842 (8)	0.0284 (2)
C3	0.55709 (12)	0.54982 (10)	0.32055 (10)	0.0268 (3)
C4	0.50522 (12)	0.63404 (11)	0.38760 (10)	0.0289 (3)
H4	0.5423	0.7079	0.4093	0.035*
N5	0.38931 (10)	0.59103 (9)	0.41746 (8)	0.0281 (2)
C6	0.26578 (12)	0.40118 (11)	0.38101 (10)	0.0282 (3)
C7	0.14177 (12)	0.44168 (12)	0.39029 (11)	0.0348 (3)
H7	0.1246	0.5246	0.3893	0.042*
C8	0.04297 (14)	0.36122 (14)	0.40103 (13)	0.0414 (3)
H8	−0.0413	0.3896	0.4082	0.050*
C9	0.06605 (14)	0.23974 (14)	0.40139 (12)	0.0424 (3)
H9	−0.0019	0.1852	0.4097	0.051*
C10	0.18894 (14)	0.19848 (13)	0.38951 (12)	0.0390 (3)
H10	0.2051	0.1154	0.3879	0.047*
C11	0.28813 (13)	0.27826 (11)	0.37999 (11)	0.0323 (3)
H11	0.3723	0.2494	0.3727	0.039*
C12	0.68112 (12)	0.55033 (10)	0.26877 (10)	0.0270 (3)
C13	0.70870 (13)	0.46715 (11)	0.18610 (11)	0.0318 (3)
H13	0.6454	0.4118	0.1618	0.038*
C14	0.82693 (13)	0.46451 (11)	0.13935 (11)	0.0342 (3)
H14	0.8453	0.4076	0.0837	0.041*
C15	0.91715 (13)	0.54576 (12)	0.17496 (11)	0.0334 (3)
C16	0.89444 (13)	0.62991 (12)	0.25570 (12)	0.0370 (3)
H16	0.9582	0.6856	0.2784	0.044*
C17	0.77620 (13)	0.63091 (12)	0.30265 (11)	0.0340 (3)
H17	0.7593	0.6875	0.3590	0.041*
F18	1.03312 (8)	0.54292 (8)	0.12881 (8)	0.0482 (2)
C19	0.30688 (12)	0.64839 (12)	0.49708 (10)	0.0312 (3)
H19A	0.2692	0.5866	0.5445	0.037*
H19B	0.3591	0.7012	0.5464	0.037*
O20	0.20865 (9)	0.71516 (8)	0.44560 (8)	0.0363 (2)
C21	0.25020 (16)	0.82639 (13)	0.40291 (12)	0.0446 (4)
H21A	0.2889	0.8737	0.4639	0.067*
H21B	0.1772	0.8694	0.3694	0.067*
H21C	0.3130	0.8125	0.3460	0.067*

	U11	U22	U33	U12	U13	U23
C1	0.0285 (6)	0.0255 (6)	0.0277 (6)	0.0024 (5)	0.0004 (4)	0.0019 (4)
N2	0.0283 (5)	0.0269 (5)	0.0302 (5)	0.0001 (4)	0.0024 (4)	0.0008 (4)
C3	0.0284 (6)	0.0253 (6)	0.0265 (6)	0.0001 (5)	−0.0001 (4)	0.0030 (4)
C4	0.0293 (6)	0.0260 (6)	0.0315 (6)	−0.0014 (5)	0.0017 (5)	0.0010 (5)
N5	0.0294 (5)	0.0259 (5)	0.0291 (5)	0.0012 (4)	0.0026 (4)	−0.0001 (4)
C6	0.0287 (6)	0.0290 (6)	0.0269 (6)	−0.0012 (5)	0.0016 (4)	−0.0001 (5)
C7	0.0311 (7)	0.0337 (7)	0.0394 (7)	0.0012 (5)	0.0013 (5)	−0.0020 (5)
C8	0.0294 (7)	0.0493 (9)	0.0458 (8)	−0.0034 (6)	0.0047 (6)	−0.0048 (6)
C9	0.0398 (8)	0.0453 (8)	0.0424 (8)	−0.0156 (6)	0.0044 (6)	−0.0012 (6)
C10	0.0477 (8)	0.0295 (7)	0.0395 (7)	−0.0060 (6)	0.0000 (6)	0.0004 (5)
C11	0.0328 (7)	0.0294 (6)	0.0346 (6)	0.0004 (5)	0.0008 (5)	−0.0005 (5)
C12	0.0291 (6)	0.0245 (6)	0.0275 (6)	0.0009 (5)	0.0019 (4)	0.0047 (4)
C13	0.0350 (7)	0.0277 (6)	0.0327 (6)	−0.0038 (5)	0.0029 (5)	−0.0005 (5)
C14	0.0398 (7)	0.0288 (6)	0.0345 (6)	0.0000 (5)	0.0095 (5)	−0.0013 (5)
C15	0.0302 (7)	0.0327 (7)	0.0380 (7)	0.0012 (5)	0.0092 (5)	0.0053 (5)
C16	0.0340 (7)	0.0326 (7)	0.0447 (8)	−0.0070 (5)	0.0056 (6)	−0.0033 (6)
C17	0.0351 (7)	0.0295 (6)	0.0377 (7)	−0.0020 (5)	0.0058 (5)	−0.0043 (5)
F18	0.0380 (5)	0.0473 (5)	0.0609 (6)	−0.0051 (4)	0.0216 (4)	−0.0058 (4)
C19	0.0341 (7)	0.0293 (6)	0.0305 (6)	0.0043 (5)	0.0060 (5)	0.0008 (5)
O20	0.0355 (5)	0.0292 (5)	0.0444 (5)	0.0070 (4)	0.0049 (4)	0.0032 (4)
C21	0.0661 (10)	0.0279 (7)	0.0394 (7)	0.0026 (7)	−0.0033 (7)	0.0026 (6)

C1—N2	1.3231 (15)	C11—H11	0.9500
C1—N5	1.3772 (16)	C12—C17	1.3987 (18)
C1—C6	1.4727 (17)	C12—C13	1.4010 (17)
N2—C3	1.3844 (15)	C13—C14	1.3844 (18)
C3—C4	1.3691 (17)	C13—H13	0.9500
C3—C12	1.4666 (17)	C14—C15	1.3738 (19)
C4—N5	1.3725 (16)	C14—H14	0.9500
C4—H4	0.9500	C15—F18	1.3595 (15)
N5—C19	1.4637 (15)	C15—C16	1.3808 (19)
C6—C7	1.3907 (18)	C16—C17	1.3853 (18)
C6—C11	1.4026 (18)	C16—H16	0.9500
C7—C8	1.3882 (19)	C17—H17	0.9500
C7—H7	0.9500	C19—O20	1.4014 (15)
C8—C9	1.388 (2)	C19—H19A	0.9900
C8—H8	0.9500	C19—H19B	0.9900
C9—C10	1.387 (2)	O20—C21	1.4266 (17)
C9—H9	0.9500	C21—H21A	0.9800
C10—C11	1.3846 (19)	C21—H21B	0.9800
C10—H10	0.9500	C21—H21C	0.9800
N2—C1—N5	111.07 (11)	C17—C12—C13	118.20 (12)
N2—C1—C6	123.78 (11)	C17—C12—C3	121.21 (11)
N5—C1—C6	125.09 (11)	C13—C12—C3	120.56 (11)
C1—N2—C3	105.97 (10)	C14—C13—C12	120.95 (12)
C4—C3—N2	109.53 (11)	C14—C13—H13	119.5
C4—C3—C12	128.82 (11)	C12—C13—H13	119.5
N2—C3—C12	121.62 (11)	C15—C14—C13	118.77 (12)
C3—C4—N5	106.71 (11)	C15—C14—H14	120.6
C3—C4—H4	126.6	C13—C14—H14	120.6
N5—C4—H4	126.6	F18—C15—C14	118.59 (12)
C4—N5—C1	106.72 (10)	F18—C15—C16	118.90 (12)
C4—N5—C19	124.72 (11)	C14—C15—C16	122.51 (12)
C1—N5—C19	128.27 (11)	C15—C16—C17	118.19 (12)
C7—C6—C11	118.81 (12)	C15—C16—H16	120.9
C7—C6—C1	123.02 (12)	C17—C16—H16	120.9
C11—C6—C1	118.13 (11)	C16—C17—C12	121.38 (12)
C8—C7—C6	120.16 (13)	C16—C17—H17	119.3
C8—C7—H7	119.9	C12—C17—H17	119.3
C6—C7—H7	119.9	O20—C19—N5	113.27 (10)
C9—C8—C7	120.70 (14)	O20—C19—H19A	108.9
C9—C8—H8	119.7	N5—C19—H19A	108.9
C7—C8—H8	119.7	O20—C19—H19B	108.9
C10—C9—C8	119.54 (13)	N5—C19—H19B	108.9
C10—C9—H9	120.2	H19A—C19—H19B	107.7
C8—C9—H9	120.2	C19—O20—C21	113.37 (11)
C11—C10—C9	120.04 (13)	O20—C21—H21A	109.5
C11—C10—H10	120.0	O20—C21—H21B	109.5
C9—C10—H10	120.0	H21A—C21—H21B	109.5
C10—C11—C6	120.72 (13)	O20—C21—H21C	109.5
C10—C11—H11	119.6	H21A—C21—H21C	109.5
C6—C11—H11	119.6	H21B—C21—H21C	109.5
N5—C1—N2—C3	0.12 (13)	C9—C10—C11—C6	−0.7 (2)
C6—C1—N2—C3	−177.34 (11)	C7—C6—C11—C10	−0.84 (19)
C1—N2—C3—C4	−0.04 (13)	C1—C6—C11—C10	−178.34 (12)
C1—N2—C3—C12	178.28 (10)	C4—C3—C12—C17	13.98 (19)
N2—C3—C4—N5	−0.04 (13)	N2—C3—C12—C17	−163.99 (11)
C12—C3—C4—N5	−178.21 (11)	C4—C3—C12—C13	−168.03 (12)
C3—C4—N5—C1	0.11 (13)	N2—C3—C12—C13	14.00 (17)
C3—C4—N5—C19	174.26 (11)	C17—C12—C13—C14	0.16 (19)
N2—C1—N5—C4	−0.15 (13)	C3—C12—C13—C14	−177.89 (11)
C6—C1—N5—C4	177.27 (11)	C12—C13—C14—C15	−0.4 (2)
N2—C1—N5—C19	−174.02 (11)	C13—C14—C15—F18	−179.97 (12)
C6—C1—N5—C19	3.40 (19)	C13—C14—C15—C16	0.1 (2)
N2—C1—C6—C7	−146.46 (13)	F18—C15—C16—C17	−179.40 (12)
N5—C1—C6—C7	36.44 (18)	C14—C15—C16—C17	0.6 (2)
N2—C1—C6—C11	30.93 (17)	C15—C16—C17—C12	−0.8 (2)
N5—C1—C6—C11	−146.17 (12)	C13—C12—C17—C16	0.49 (19)
C11—C6—C7—C8	1.54 (19)	C3—C12—C17—C16	178.53 (12)
C1—C6—C7—C8	178.91 (12)	C4—N5—C19—O20	99.09 (14)
C6—C7—C8—C9	−0.7 (2)	C1—N5—C19—O20	−88.05 (15)
C7—C8—C9—C10	−0.8 (2)	N5—C19—O20—C21	−76.19 (14)
C8—C9—C10—C11	1.5 (2)