2-(4-Fluoro-phen-yl)-1-(3-meth-oxy-phen-yl)-4,5-dimethyl-1H-imidazole.

In the title compound, C18H17FN2O, the imidazole ring makes dihedral angles of 68.81 (6) and 25.20 (8)° with the meth-oxy-phenyl and fluoro-phenyl rings, respectively. The dihedral angle between the meth-oxy-phenyl and fluoro-phenyl ring is 71.89 (6)°. In the crystal, mol-ecules are linked into inversion dimers with an R 2 (2)(8) graph-set motif by pairs of weak C-H⋯F inter-actions.

Related literature

For related structures, see: Rizwana Begum et al. (2013 ▶); Srinivasan et al. (2013 ▶); Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H17FN2O

M = 296.34

Triclinic,

a = 8.1196 (5) Å

b = 9.6014 (6) Å

c = 10.6116 (6) Å

α = 106.818 (3)°

β = 92.059 (3)°

γ = 96.114 (3)°

V = 785.45 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.974, T max = 0.979

15949 measured reflections

3597 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 1.03

3597 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813032492/hg5365sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032492/hg5365Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032492/hg5365Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H17FN2O	Z = 2
Mr = 296.34	F(000) = 312
Triclinic, P1	Dx = 1.253 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1196 (5) Å	Cell parameters from 3597 reflections
b = 9.6014 (6) Å	θ = 2.5–30.3°
c = 10.6116 (6) Å	µ = 0.09 mm−1
α = 106.818 (3)°	T = 293 K
β = 92.059 (3)°	Block, colourless
γ = 96.114 (3)°	0.30 × 0.30 × 0.25 mm
V = 785.45 (8) Å3

Bruker Kappa APEXII CCD diffractometer	3597 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.974, Tmax = 0.979	k = −12→12
15949 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.1414P] where P = (Fo2 + 2Fc2)/3
3597 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 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	0.2524 (2)	0.71718 (19)	0.06251 (16)	0.0606 (4)
C2	0.2395 (3)	0.8699 (2)	0.0606 (2)	0.0941 (7)
H2A	0.2741	0.9366	0.1462	0.141*
H2B	0.1265	0.8791	0.0378	0.141*
H2C	0.3096	0.8927	−0.0035	0.141*
C3	0.2938 (2)	0.66931 (18)	0.16587 (15)	0.0574 (4)
C4	0.3379 (3)	0.7478 (2)	0.30717 (17)	0.0771 (5)
H4A	0.3221	0.8491	0.3241	0.116*
H4B	0.4521	0.7407	0.3284	0.116*
H4C	0.2683	0.7046	0.3605	0.116*
C5	0.29393 (19)	0.41950 (17)	0.19342 (14)	0.0504 (4)
C6	0.1516 (2)	0.33657 (19)	0.20825 (17)	0.0597 (4)
H6	0.0503	0.3431	0.1679	0.072*
C7	0.1631 (2)	0.2430 (2)	0.2848 (2)	0.0709 (5)
H7	0.0683	0.1851	0.2952	0.085*
C8	0.3106 (3)	0.2339 (2)	0.34526 (19)	0.0705 (5)
H8	0.3157	0.1707	0.3968	0.085*
C9	0.4529 (2)	0.3186 (2)	0.33012 (15)	0.0609 (4)
C10	0.4455 (2)	0.41192 (18)	0.25281 (14)	0.0551 (4)
H10	0.5408	0.4684	0.2410	0.066*
C11	0.7407 (3)	0.3921 (3)	0.3874 (2)	0.0872 (6)
H11A	0.7659	0.3754	0.2969	0.131*
H11B	0.8308	0.3691	0.4358	0.131*
H11C	0.7252	0.4931	0.4250	0.131*
C12	0.23901 (18)	0.48287 (17)	−0.01663 (14)	0.0504 (4)
C13	0.22060 (19)	0.33656 (18)	−0.11246 (14)	0.0526 (4)
C14	0.1224 (2)	0.3145 (2)	−0.22791 (17)	0.0648 (5)
H14	0.0651	0.3896	−0.2386	0.078*
C15	0.1082 (3)	0.1840 (2)	−0.32662 (19)	0.0757 (5)
H15	0.0429	0.1705	−0.4041	0.091*
C16	0.1914 (3)	0.0748 (2)	−0.30879 (19)	0.0712 (5)
C17	0.2885 (3)	0.0901 (2)	−0.1976 (2)	0.0758 (5)
H17	0.3439	0.0135	−0.1880	0.091*
C18	0.3031 (2)	0.2221 (2)	−0.09918 (17)	0.0662 (5)
H18	0.3696	0.2344	−0.0226	0.079*
N1	0.21906 (17)	0.60175 (15)	−0.05036 (12)	0.0574 (4)
N2	0.28515 (16)	0.51797 (14)	0.11500 (12)	0.0509 (3)
O1	0.59387 (18)	0.30194 (18)	0.39395 (14)	0.0866 (4)
F2	0.17789 (18)	−0.05430 (14)	−0.40697 (13)	0.1043 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0682 (11)	0.0603 (10)	0.0551 (9)	0.0035 (8)	0.0008 (7)	0.0217 (8)
C2	0.138 (2)	0.0661 (12)	0.0821 (14)	0.0073 (12)	−0.0133 (13)	0.0318 (11)
C3	0.0622 (10)	0.0604 (10)	0.0495 (8)	0.0004 (7)	0.0018 (7)	0.0189 (7)
C4	0.1045 (15)	0.0707 (12)	0.0521 (10)	0.0007 (10)	−0.0037 (9)	0.0166 (9)
C5	0.0560 (9)	0.0580 (9)	0.0406 (7)	0.0081 (7)	0.0066 (6)	0.0193 (7)
C6	0.0564 (9)	0.0641 (10)	0.0604 (9)	0.0043 (7)	0.0071 (7)	0.0220 (8)
C7	0.0715 (12)	0.0672 (11)	0.0807 (12)	−0.0006 (9)	0.0158 (9)	0.0342 (10)
C8	0.0898 (14)	0.0664 (11)	0.0691 (11)	0.0158 (10)	0.0175 (10)	0.0377 (9)
C9	0.0691 (11)	0.0733 (11)	0.0482 (8)	0.0194 (9)	0.0073 (7)	0.0260 (8)
C10	0.0549 (9)	0.0699 (10)	0.0460 (8)	0.0071 (7)	0.0062 (6)	0.0255 (7)
C11	0.0686 (13)	0.1295 (19)	0.0757 (13)	0.0226 (12)	−0.0032 (10)	0.0468 (13)
C12	0.0480 (8)	0.0630 (9)	0.0450 (8)	0.0069 (7)	0.0037 (6)	0.0230 (7)
C13	0.0505 (8)	0.0642 (10)	0.0463 (8)	0.0052 (7)	0.0073 (6)	0.0215 (7)
C14	0.0676 (11)	0.0681 (11)	0.0582 (10)	0.0073 (8)	−0.0056 (8)	0.0196 (8)
C15	0.0791 (13)	0.0805 (13)	0.0592 (11)	0.0014 (10)	−0.0100 (9)	0.0122 (10)
C16	0.0795 (13)	0.0648 (11)	0.0614 (11)	0.0019 (9)	0.0099 (9)	0.0081 (9)
C17	0.0929 (14)	0.0700 (12)	0.0691 (12)	0.0250 (10)	0.0141 (10)	0.0212 (10)
C18	0.0733 (11)	0.0773 (12)	0.0516 (9)	0.0212 (9)	0.0039 (8)	0.0205 (9)
N1	0.0623 (8)	0.0642 (8)	0.0497 (7)	0.0067 (6)	0.0007 (6)	0.0241 (7)
N2	0.0523 (7)	0.0595 (8)	0.0446 (6)	0.0049 (6)	0.0026 (5)	0.0222 (6)
O1	0.0781 (9)	0.1210 (12)	0.0843 (9)	0.0234 (8)	−0.0001 (7)	0.0640 (9)
F2	0.1274 (11)	0.0784 (8)	0.0861 (9)	0.0117 (7)	0.0010 (7)	−0.0073 (7)

C1—C3	1.351 (2)	C9—C10	1.383 (2)
C1—N1	1.371 (2)	C10—H10	0.9300
C1—C2	1.488 (3)	C11—O1	1.413 (3)
C2—H2A	0.9600	C11—H11A	0.9600
C2—H2B	0.9600	C11—H11B	0.9600
C2—H2C	0.9600	C11—H11C	0.9600
C3—N2	1.389 (2)	C12—N1	1.3149 (19)
C3—C4	1.481 (2)	C12—N2	1.3667 (18)
C4—H4A	0.9600	C12—C13	1.465 (2)
C4—H4B	0.9600	C13—C18	1.384 (2)
C4—H4C	0.9600	C13—C14	1.388 (2)
C5—C6	1.372 (2)	C14—C15	1.372 (3)
C5—C10	1.381 (2)	C14—H14	0.9300
C5—N2	1.4342 (18)	C15—C16	1.360 (3)
C6—C7	1.382 (2)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.357 (3)
C7—C8	1.361 (3)	C16—F2	1.360 (2)
C7—H7	0.9300	C17—C18	1.380 (3)
C8—C9	1.382 (3)	C17—H17	0.9300
C8—H8	0.9300	C18—H18	0.9300
C9—O1	1.357 (2)
C3—C1—N1	110.58 (15)	C5—C10—H10	120.7
C3—C1—C2	128.58 (17)	C9—C10—H10	120.7
N1—C1—C2	120.83 (15)	O1—C11—H11A	109.5
C1—C2—H2A	109.5	O1—C11—H11B	109.5
C1—C2—H2B	109.5	H11A—C11—H11B	109.5
H2A—C2—H2B	109.5	O1—C11—H11C	109.5
C1—C2—H2C	109.5	H11A—C11—H11C	109.5
H2A—C2—H2C	109.5	H11B—C11—H11C	109.5
H2B—C2—H2C	109.5	N1—C12—N2	110.49 (14)
C1—C3—N2	105.43 (14)	N1—C12—C13	122.62 (13)
C1—C3—C4	131.90 (17)	N2—C12—C13	126.82 (13)
N2—C3—C4	122.66 (14)	C18—C13—C14	117.93 (16)
C3—C4—H4A	109.5	C18—C13—C12	124.26 (14)
C3—C4—H4B	109.5	C14—C13—C12	117.67 (14)
H4A—C4—H4B	109.5	C15—C14—C13	121.29 (17)
C3—C4—H4C	109.5	C15—C14—H14	119.4
H4A—C4—H4C	109.5	C13—C14—H14	119.4
H4B—C4—H4C	109.5	C16—C15—C14	118.56 (17)
C6—C5—C10	121.91 (14)	C16—C15—H15	120.7
C6—C5—N2	119.19 (14)	C14—C15—H15	120.7
C10—C5—N2	118.89 (14)	C17—C16—C15	122.62 (18)
C5—C6—C7	118.12 (16)	C17—C16—F2	118.87 (18)
C5—C6—H6	120.9	C15—C16—F2	118.51 (18)
C7—C6—H6	120.9	C16—C17—C18	118.46 (18)
C8—C7—C6	121.27 (17)	C16—C17—H17	120.8
C8—C7—H7	119.4	C18—C17—H17	120.8
C6—C7—H7	119.4	C17—C18—C13	121.13 (17)
C7—C8—C9	120.05 (16)	C17—C18—H18	119.4
C7—C8—H8	120.0	C13—C18—H18	119.4
C9—C8—H8	120.0	C12—N1—C1	106.37 (13)
O1—C9—C8	115.78 (15)	C12—N2—C3	107.12 (12)
O1—C9—C10	124.26 (16)	C12—N2—C5	127.45 (13)
C8—C9—C10	119.96 (16)	C3—N2—C5	124.53 (12)
C5—C10—C9	118.68 (15)	C9—O1—C11	117.83 (14)
N1—C1—C3—N2	−0.23 (19)	C15—C16—C17—C18	−0.1 (3)
C2—C1—C3—N2	179.2 (2)	F2—C16—C17—C18	179.23 (17)
N1—C1—C3—C4	−179.06 (18)	C16—C17—C18—C13	0.3 (3)
C2—C1—C3—C4	0.4 (4)	C14—C13—C18—C17	0.1 (3)
C10—C5—C6—C7	−0.3 (2)	C12—C13—C18—C17	−175.54 (16)
N2—C5—C6—C7	−179.69 (15)	N2—C12—N1—C1	−0.27 (17)
C5—C6—C7—C8	0.7 (3)	C13—C12—N1—C1	−177.54 (14)
C6—C7—C8—C9	−0.4 (3)	C3—C1—N1—C12	0.32 (19)
C7—C8—C9—O1	−179.92 (17)	C2—C1—N1—C12	−179.21 (18)
C7—C8—C9—C10	−0.4 (3)	N1—C12—N2—C3	0.13 (17)
C6—C5—C10—C9	−0.5 (2)	C13—C12—N2—C3	177.25 (14)
N2—C5—C10—C9	178.94 (14)	N1—C12—N2—C5	169.55 (14)
O1—C9—C10—C5	−179.70 (15)	C13—C12—N2—C5	−13.3 (2)
C8—C9—C10—C5	0.8 (2)	C1—C3—N2—C12	0.07 (17)
N1—C12—C13—C18	151.38 (16)	C4—C3—N2—C12	179.02 (16)
N2—C12—C13—C18	−25.4 (2)	C1—C3—N2—C5	−169.74 (15)
N1—C12—C13—C14	−24.2 (2)	C4—C3—N2—C5	9.2 (2)
N2—C12—C13—C14	158.97 (15)	C6—C5—N2—C12	−62.4 (2)
C18—C13—C14—C15	−0.5 (3)	C10—C5—N2—C12	118.14 (17)
C12—C13—C14—C15	175.38 (16)	C6—C5—N2—C3	105.29 (18)
C13—C14—C15—C16	0.7 (3)	C10—C5—N2—C3	−74.2 (2)
C14—C15—C16—C17	−0.3 (3)	C8—C9—O1—C11	−176.56 (17)
C14—C15—C16—F2	−179.68 (17)	C10—C9—O1—C11	3.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···F2i	0.93	2.55	3.437 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯F2i	0.93	2.55	3.437 (2)	160

Symmetry code: (i) .