1-(3,5-Dimethyl-phenyl)-2-(4-fluoro-phenyl)-4,5-dimethyl-1H-imidazole.

In the title compound, C(19)H(19)FN(2), the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å] and makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to nitro-gen and carbon, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C-H⋯π inter-action is found in the crystal structure.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C19H19FN2

M = 294.36

Triclinic,

a = 8.4226 (10) Å

b = 9.5572 (10) Å

c = 11.0351 (11) Å

α = 105.423 (9)°

β = 105.677 (9)°

γ = 95.781 (9)°

V = 810.07 (17) Å3

Z = 2

Cu Kα radiation

μ = 0.63 mm−1

T = 170 K

0.25 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.858, T max = 0.911

5121 measured reflections

3054 independent reflections

2771 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.07

3054 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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/S1600536811012098/hg5018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012098/hg5018Isup2.hkl

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

C19H19FN2	Z = 2
Mr = 294.36	F(000) = 312
Triclinic, P1	Dx = 1.207 Mg m−3
Hall symbol: -P 1	Melting point: 377 K
a = 8.4226 (10) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.5572 (10) Å	Cell parameters from 3721 reflections
c = 11.0351 (11) Å	θ = 5.6–71.2°
α = 105.423 (9)°	µ = 0.63 mm−1
β = 105.677 (9)°	T = 170 K
γ = 95.781 (9)°	Block, colourless
V = 810.07 (17) Å3	0.25 × 0.20 × 0.15 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3054 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2771 reflections with I > 2σ(I)
graphite	Rint = 0.011
Detector resolution: 16.1500 pixels mm-1	θmax = 71.3°, θmin = 5.6°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.858, Tmax = 0.911	l = −13→10
5121 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0944P)2 + 0.144P] where P = (Fo2 + 2Fc2)/3
3054 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 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	0.29950 (19)	0.53513 (14)	0.86850 (14)	0.0964 (5)
N1	0.19985 (15)	−0.06005 (14)	0.37504 (12)	0.0449 (4)
N3	0.32289 (16)	−0.11576 (15)	0.55605 (13)	0.0520 (4)
C2	0.27033 (18)	−0.00885 (17)	0.50979 (14)	0.0453 (4)
C4	0.2859 (2)	−0.23874 (19)	0.44868 (16)	0.0532 (5)
C5	0.20944 (19)	−0.20827 (17)	0.33550 (15)	0.0488 (5)
C11	0.14226 (18)	0.02522 (16)	0.28741 (14)	0.0435 (4)
C12	−0.02859 (18)	0.01651 (18)	0.23336 (15)	0.0480 (5)
C13	−0.08585 (19)	0.10368 (18)	0.15377 (15)	0.0494 (5)
C14	0.0323 (2)	0.19566 (17)	0.12941 (14)	0.0515 (5)
C15	0.2035 (2)	0.20141 (16)	0.17950 (15)	0.0487 (5)
C16	0.25852 (18)	0.11506 (16)	0.26059 (14)	0.0464 (4)
C17	−0.2713 (2)	0.0990 (2)	0.0987 (2)	0.0692 (7)
C18	0.3276 (3)	0.2979 (2)	0.1464 (2)	0.0698 (7)
C21	0.28022 (18)	0.14031 (17)	0.59540 (15)	0.0472 (5)
C22	0.1660 (2)	0.2313 (2)	0.56533 (17)	0.0566 (5)
C23	0.1740 (3)	0.3655 (2)	0.6562 (2)	0.0654 (6)
C24	0.2952 (3)	0.4060 (2)	0.77740 (19)	0.0660 (6)
C25	0.4109 (2)	0.3201 (2)	0.81121 (19)	0.0655 (6)
C26	0.4030 (2)	0.1881 (2)	0.71957 (16)	0.0558 (5)
C41	0.3314 (3)	−0.3824 (2)	0.4636 (2)	0.0787 (8)
C51	0.1442 (2)	−0.3012 (2)	0.19482 (17)	0.0623 (6)
H12	−0.10645	−0.04873	0.25055	0.0575*
H14	−0.00553	0.25686	0.07653	0.0618*
H16	0.37514	0.11800	0.29712	0.0556*
H17A	−0.29302	0.13147	0.01961	0.1037*
H17B	−0.30948	0.16460	0.16526	0.1037*
H17C	−0.33197	−0.00229	0.07526	0.1037*
H18A	0.34608	0.24283	0.06431	0.1046*
H18B	0.43413	0.32742	0.21839	0.1046*
H18C	0.28339	0.38610	0.13490	0.1046*
H22	0.08176	0.20091	0.48163	0.0679*
H23	0.09729	0.42825	0.63510	0.0784*
H25	0.49398	0.35114	0.89552	0.0785*
H26	0.48261	0.12777	0.74092	0.0670*
H41A	0.45009	−0.38100	0.47068	0.1181*
H41B	0.26202	−0.46386	0.38633	0.1181*
H41C	0.31177	−0.39629	0.54360	0.1181*
H51A	0.14887	−0.40467	0.18925	0.0934*
H51B	0.21302	−0.26845	0.14515	0.0934*
H51C	0.02775	−0.29169	0.15728	0.0934*

	U11	U22	U33	U12	U13	U23
F4	0.1034 (10)	0.0696 (8)	0.0947 (9)	0.0084 (7)	0.0297 (8)	−0.0060 (7)
N1	0.0417 (6)	0.0541 (7)	0.0451 (7)	0.0131 (5)	0.0125 (5)	0.0248 (5)
N3	0.0508 (7)	0.0622 (8)	0.0497 (7)	0.0169 (6)	0.0121 (6)	0.0291 (6)
C2	0.0399 (7)	0.0568 (9)	0.0451 (7)	0.0108 (6)	0.0128 (6)	0.0250 (6)
C4	0.0533 (9)	0.0573 (9)	0.0561 (9)	0.0180 (7)	0.0150 (7)	0.0279 (7)
C5	0.0466 (8)	0.0547 (9)	0.0516 (8)	0.0152 (6)	0.0156 (6)	0.0243 (7)
C11	0.0430 (7)	0.0527 (8)	0.0410 (7)	0.0148 (6)	0.0131 (6)	0.0222 (6)
C12	0.0418 (8)	0.0586 (9)	0.0494 (8)	0.0121 (6)	0.0143 (6)	0.0250 (7)
C13	0.0469 (8)	0.0581 (9)	0.0445 (8)	0.0182 (7)	0.0102 (6)	0.0187 (7)
C14	0.0634 (10)	0.0533 (9)	0.0448 (8)	0.0218 (7)	0.0150 (7)	0.0243 (7)
C15	0.0567 (9)	0.0479 (8)	0.0496 (8)	0.0139 (6)	0.0223 (7)	0.0206 (6)
C16	0.0418 (7)	0.0533 (8)	0.0490 (8)	0.0134 (6)	0.0155 (6)	0.0207 (6)
C17	0.0519 (10)	0.0793 (12)	0.0756 (12)	0.0238 (9)	0.0056 (8)	0.0327 (10)
C18	0.0764 (12)	0.0665 (11)	0.0864 (13)	0.0152 (9)	0.0385 (11)	0.0419 (10)
C21	0.0437 (7)	0.0569 (9)	0.0481 (8)	0.0075 (6)	0.0178 (6)	0.0248 (7)
C22	0.0565 (9)	0.0630 (10)	0.0535 (9)	0.0151 (7)	0.0163 (7)	0.0224 (8)
C23	0.0670 (11)	0.0609 (10)	0.0762 (12)	0.0192 (8)	0.0287 (9)	0.0248 (9)
C24	0.0680 (11)	0.0561 (10)	0.0684 (11)	−0.0007 (8)	0.0275 (9)	0.0082 (8)
C25	0.0548 (10)	0.0716 (11)	0.0589 (10)	−0.0022 (8)	0.0124 (8)	0.0123 (8)
C26	0.0460 (8)	0.0654 (10)	0.0559 (9)	0.0054 (7)	0.0132 (7)	0.0227 (8)
C41	0.1018 (16)	0.0660 (12)	0.0736 (12)	0.0332 (11)	0.0157 (11)	0.0351 (10)
C51	0.0685 (11)	0.0640 (10)	0.0532 (9)	0.0186 (8)	0.0135 (8)	0.0192 (8)

F4—C24	1.359 (2)	C24—C25	1.375 (3)
N1—C2	1.3713 (19)	C25—C26	1.374 (3)
N1—C5	1.385 (2)	C12—H12	0.9500
N1—C11	1.442 (2)	C14—H14	0.9500
N3—C2	1.322 (2)	C16—H16	0.9500
N3—C4	1.367 (2)	C17—H17A	0.9800
C2—C21	1.466 (2)	C17—H17B	0.9800
C4—C5	1.362 (2)	C17—H17C	0.9800
C4—C41	1.500 (3)	C18—H18A	0.9800
C5—C51	1.486 (2)	C18—H18B	0.9800
C11—C12	1.385 (2)	C18—H18C	0.9800
C11—C16	1.381 (2)	C22—H22	0.9500
C12—C13	1.393 (2)	C23—H23	0.9500
C13—C14	1.389 (2)	C25—H25	0.9500
C13—C17	1.507 (2)	C26—H26	0.9500
C14—C15	1.387 (2)	C41—H41A	0.9800
C15—C16	1.394 (2)	C41—H41B	0.9800
C15—C18	1.506 (3)	C41—H41C	0.9800
C21—C22	1.393 (2)	C51—H51A	0.9800
C21—C26	1.401 (2)	C51—H51B	0.9800
C22—C23	1.385 (3)	C51—H51C	0.9800
C23—C24	1.374 (3)
C2—N1—C5	107.12 (13)	C13—C14—H14	119.00
C2—N1—C11	127.30 (14)	C15—C14—H14	119.00
C5—N1—C11	125.28 (12)	C11—C16—H16	120.00
C2—N3—C4	106.09 (13)	C15—C16—H16	120.00
N1—C2—N3	110.65 (14)	C13—C17—H17A	109.00
N1—C2—C21	126.33 (14)	C13—C17—H17B	109.00
N3—C2—C21	122.95 (13)	C13—C17—H17C	109.00
N3—C4—C5	110.80 (16)	H17A—C17—H17B	110.00
N3—C4—C41	121.02 (15)	H17A—C17—H17C	109.00
C5—C4—C41	128.18 (16)	H17B—C17—H17C	110.00
N1—C5—C4	105.35 (14)	C15—C18—H18A	109.00
N1—C5—C51	122.36 (14)	C15—C18—H18B	109.00
C4—C5—C51	132.29 (16)	C15—C18—H18C	109.00
N1—C11—C12	119.20 (14)	H18A—C18—H18B	109.00
N1—C11—C16	119.31 (14)	H18A—C18—H18C	109.00
C12—C11—C16	121.49 (15)	H18B—C18—H18C	110.00
C11—C12—C13	119.80 (15)	C21—C22—H22	120.00
C12—C13—C14	118.19 (15)	C23—C22—H22	120.00
C12—C13—C17	120.13 (16)	C22—C23—H23	121.00
C14—C13—C17	121.67 (16)	C24—C23—H23	121.00
C13—C14—C15	122.39 (15)	C24—C25—H25	121.00
C14—C15—C16	118.59 (15)	C26—C25—H25	121.00
C14—C15—C18	120.88 (16)	C21—C26—H26	119.00
C16—C15—C18	120.54 (16)	C25—C26—H26	119.00
C11—C16—C15	119.50 (15)	C4—C41—H41A	109.00
C2—C21—C22	123.84 (14)	C4—C41—H41B	109.00
C2—C21—C26	117.57 (15)	C4—C41—H41C	109.00
C22—C21—C26	118.34 (16)	H41A—C41—H41B	109.00
C21—C22—C23	120.67 (17)	H41A—C41—H41C	109.00
C22—C23—C24	118.6 (2)	H41B—C41—H41C	109.00
F4—C24—C23	118.8 (2)	C5—C51—H51A	109.00
F4—C24—C25	118.53 (18)	C5—C51—H51B	109.00
C23—C24—C25	122.71 (19)	C5—C51—H51C	109.00
C24—C25—C26	118.09 (17)	H51A—C51—H51B	109.00
C21—C26—C25	121.54 (17)	H51A—C51—H51C	109.00
C11—C12—H12	120.00	H51B—C51—H51C	109.00
C13—C12—H12	120.00
C5—N1—C2—N3	0.02 (19)	C41—C4—C5—C51	1.4 (3)
C5—N1—C2—C21	−176.74 (15)	N1—C11—C12—C13	176.87 (14)
C11—N1—C2—N3	−173.88 (14)	C16—C11—C12—C13	−2.3 (2)
C11—N1—C2—C21	9.4 (3)	N1—C11—C16—C15	−177.86 (14)
C2—N1—C5—C4	−0.20 (18)	C12—C11—C16—C15	1.3 (2)
C2—N1—C5—C51	179.77 (15)	C11—C12—C13—C14	1.1 (2)
C11—N1—C5—C4	173.87 (15)	C11—C12—C13—C17	−177.75 (15)
C11—N1—C5—C51	−6.2 (2)	C12—C13—C14—C15	1.1 (2)
C2—N1—C11—C12	−105.84 (19)	C17—C13—C14—C15	179.93 (15)
C2—N1—C11—C16	73.4 (2)	C13—C14—C15—C16	−2.1 (2)
C5—N1—C11—C12	81.3 (2)	C13—C14—C15—C18	177.47 (16)
C5—N1—C11—C16	−99.51 (18)	C14—C15—C16—C11	0.9 (2)
C4—N3—C2—N1	0.16 (18)	C18—C15—C16—C11	−178.71 (15)
C4—N3—C2—C21	177.05 (15)	C2—C21—C22—C23	174.03 (18)
C2—N3—C4—C5	−0.3 (2)	C26—C21—C22—C23	0.0 (3)
C2—N3—C4—C41	178.74 (17)	C2—C21—C26—C25	−173.55 (16)
N1—C2—C21—C22	27.5 (3)	C22—C21—C26—C25	0.9 (3)
N1—C2—C21—C26	−158.45 (16)	C21—C22—C23—C24	−1.0 (3)
N3—C2—C21—C22	−148.95 (17)	C22—C23—C24—F4	−177.64 (19)
N3—C2—C21—C26	25.2 (2)	C22—C23—C24—C25	1.3 (3)
N3—C4—C5—N1	0.30 (19)	F4—C24—C25—C26	178.47 (18)
N3—C4—C5—C51	−179.66 (17)	C23—C24—C25—C26	−0.5 (3)
C41—C4—C5—N1	−178.63 (19)	C24—C25—C26—C21	−0.7 (3)

Cg3 is the centroid of the C21–C26 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg3i	0.95	2.86	3.7969 (19)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg3i	0.95	2.86	3.7969 (19)	169

Symmetry code: (i) .