2-[2-(4-Meth-oxy-phen-yl)-4,5-diphenyl-1H-imidazol-1-yl]ethanol.

In the title compound, C24H22N2O2, the central imidazole ring makes dihedral angles of 49.45 (8), 88.94 (9) and 19.43 (8)° with the benzene ring and the two phenyl rings, respectively. The dihedral angle between the phenyl rings is 77.86 (9)°, and they form dihedral angles of 49.06 (9) and 67.31 (8)° with the benzene ring. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming chains along the b axis. These chains are connected by C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). In addition, C-H⋯π inter-actions are also observed. The terminal C and O atoms of the ethanol group are disordered over two sets of sites with an occupancy ratio of 0.801 (5):0.199 (5).

Related literature

For imidazole derivatives as anti­cancer agents, see, for example: Krezel (1998 ▶); Andreani et al. (2000 ▶). For related structures, see: Akkurt et al. (2012 ▶); Mohamed et al. (2012 ▶). For further biological applications of imidazoles, see: Maier et al. (1989a ▶,b ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H22N2O2

M = 370.44

Monoclinic,

a = 14.3570 (4) Å

b = 13.2820 (4) Å

c = 10.7380 (3) Å

β = 108.212 (1)°

V = 1945.05 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.976

18622 measured reflections

3822 independent reflections

3046 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.04

3822 reflections

269 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004285/su2561sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004285/su2561Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004285/su2561Isup3.cml

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

C24H22N2O2	F(000) = 784
Mr = 370.44	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6445 reflections
a = 14.3570 (4) Å	θ = 2.5–28.1°
b = 13.2820 (4) Å	µ = 0.08 mm−1
c = 10.7380 (3) Å	T = 296 K
β = 108.212 (1)°	Prism, colourless
V = 1945.05 (10) Å3	0.30 × 0.30 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	3046 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.976, Tmax = 0.976	k = −16→16
18622 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.4175P] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max < 0.001
269 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.18 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
O1A	0.4684 (2)	0.37249 (19)	0.2105 (2)	0.0601 (7)	0.801 (5)
O2	0.85914 (8)	0.08118 (11)	0.17179 (13)	0.0735 (5)
N1	0.39627 (8)	0.18785 (8)	0.09335 (11)	0.0404 (3)
N2	0.43176 (8)	0.05860 (9)	0.22977 (11)	0.0417 (4)
C1	0.31198 (10)	0.16540 (10)	0.12402 (13)	0.0392 (4)
C2	0.33467 (10)	0.08474 (10)	0.20781 (13)	0.0386 (4)
C3	0.46645 (10)	0.12152 (10)	0.16028 (14)	0.0400 (4)
C4	0.56824 (10)	0.11574 (11)	0.15705 (14)	0.0426 (4)
C5	0.64400 (12)	0.10619 (14)	0.27435 (16)	0.0554 (6)
C6	0.73926 (12)	0.09378 (15)	0.27566 (17)	0.0621 (6)
C7	0.76170 (11)	0.09152 (12)	0.16002 (17)	0.0523 (5)
C8	0.68762 (12)	0.09900 (12)	0.04244 (16)	0.0518 (5)
C9	0.59175 (11)	0.11052 (12)	0.04197 (15)	0.0496 (5)
C10	0.88821 (14)	0.09847 (18)	0.0591 (2)	0.0797 (8)
C11	0.40902 (12)	0.27268 (11)	0.01273 (15)	0.0507 (5)
C12A	0.40758 (15)	0.37524 (14)	0.0781 (2)	0.0462 (7)	0.801 (5)
C13	0.21836 (10)	0.22019 (11)	0.06779 (14)	0.0428 (5)
C14	0.19561 (13)	0.30302 (13)	0.13025 (18)	0.0605 (6)
C15	0.10593 (15)	0.34991 (17)	0.0819 (2)	0.0764 (8)
C16	0.03897 (14)	0.31534 (19)	−0.0294 (2)	0.0799 (8)
C17	0.06034 (14)	0.23439 (19)	−0.0938 (2)	0.0808 (8)
C18	0.15028 (12)	0.18658 (14)	−0.04567 (17)	0.0616 (6)
C19	0.27150 (10)	0.02319 (10)	0.26213 (13)	0.0413 (4)
C20	0.18141 (12)	0.05525 (13)	0.26891 (17)	0.0543 (6)
C21	0.12225 (13)	−0.00802 (14)	0.31328 (18)	0.0628 (6)
C22	0.15231 (14)	−0.10348 (14)	0.35442 (18)	0.0632 (7)
C23	0.24208 (15)	−0.13547 (14)	0.3522 (2)	0.0707 (7)
C24	0.30092 (13)	−0.07337 (12)	0.30620 (18)	0.0593 (6)
O1B	0.4482 (10)	0.3797 (10)	0.1690 (11)	0.0601 (7)	0.199 (5)
C12B	0.4757 (6)	0.3448 (6)	0.0623 (8)	0.053 (3)	0.199 (5)
H6	0.78890	0.08690	0.35510	0.0750*
H8	0.70200	0.09630	−0.03620	0.0620*
H9	0.54190	0.11480	−0.03780	0.0600*
H10A	0.86270	0.04600	−0.00370	0.1200*
H10B	0.95850	0.09890	0.08350	0.1200*
H1OA	0.49500	0.42730	0.23080	0.0900*	0.801 (5)
H5	0.63000	0.10820	0.35320	0.0670*
H11B	0.47090	0.26510	−0.00480	0.0610*	0.801 (5)
H12A	0.43070	0.42700	0.03120	0.0550*	0.801 (5)
H12B	0.34100	0.39170	0.07450	0.0550*	0.801 (5)
H14	0.24140	0.32750	0.20600	0.0730*
H15	0.09120	0.40520	0.12540	0.0920*
H16	−0.02160	0.34690	−0.06170	0.0960*
H17	0.01440	0.21120	−0.17030	0.0970*
H18	0.16470	0.13160	−0.09010	0.0740*
H20	0.16040	0.12040	0.24320	0.0650*
H21	0.06140	0.01450	0.31520	0.0750*
H22	0.11210	−0.14610	0.38360	0.0760*
H23	0.26370	−0.19970	0.38190	0.0850*
H24	0.36160	−0.09670	0.30470	0.0710*
H10C	0.86310	0.16230	0.02120	0.1200*
H11A	0.35710	0.27100	−0.07060	0.0610*	0.801 (5)
H1OB	0.47760	0.43200	0.19690	0.0900*	0.199 (5)
H11C	0.42580	0.24450	−0.06080	0.0610*	0.199 (5)
H11D	0.34540	0.30450	−0.02310	0.0610*	0.199 (5)
H12C	0.47170	0.39800	−0.00110	0.0640*	0.199 (5)
H12D	0.54170	0.31760	0.09060	0.0640*	0.199 (5)

	U11	U22	U33	U12	U13	U23
O1A	0.0760 (15)	0.0472 (8)	0.0422 (14)	−0.0150 (9)	−0.0031 (11)	0.0009 (10)
O2	0.0444 (6)	0.1058 (11)	0.0707 (8)	0.0008 (6)	0.0188 (6)	−0.0010 (7)
N1	0.0451 (6)	0.0354 (6)	0.0391 (6)	−0.0005 (5)	0.0107 (5)	0.0024 (5)
N2	0.0440 (7)	0.0361 (6)	0.0427 (7)	0.0011 (5)	0.0102 (5)	0.0016 (5)
C1	0.0428 (7)	0.0357 (7)	0.0378 (7)	−0.0013 (6)	0.0108 (6)	−0.0019 (6)
C2	0.0425 (7)	0.0345 (7)	0.0369 (7)	−0.0003 (6)	0.0099 (6)	−0.0029 (6)
C3	0.0437 (8)	0.0353 (7)	0.0384 (7)	−0.0007 (6)	0.0091 (6)	−0.0010 (6)
C4	0.0434 (8)	0.0378 (7)	0.0445 (8)	−0.0017 (6)	0.0106 (6)	−0.0002 (6)
C5	0.0494 (9)	0.0732 (11)	0.0426 (9)	−0.0019 (8)	0.0128 (7)	0.0073 (8)
C6	0.0453 (9)	0.0859 (13)	0.0487 (10)	−0.0025 (8)	0.0054 (7)	0.0085 (9)
C7	0.0424 (8)	0.0537 (9)	0.0595 (10)	−0.0027 (7)	0.0141 (7)	−0.0029 (7)
C8	0.0532 (9)	0.0559 (9)	0.0478 (9)	−0.0034 (7)	0.0179 (7)	−0.0124 (7)
C9	0.0471 (8)	0.0538 (9)	0.0434 (8)	−0.0008 (7)	0.0077 (7)	−0.0101 (7)
C10	0.0578 (11)	0.1018 (16)	0.0886 (15)	−0.0032 (10)	0.0361 (11)	−0.0036 (12)
C11	0.0593 (9)	0.0455 (9)	0.0474 (9)	0.0017 (7)	0.0170 (7)	0.0112 (7)
C12A	0.0448 (12)	0.0388 (10)	0.0489 (13)	−0.0008 (8)	0.0059 (10)	0.0084 (8)
C13	0.0429 (8)	0.0424 (8)	0.0421 (8)	−0.0005 (6)	0.0118 (6)	0.0086 (6)
C14	0.0619 (10)	0.0560 (10)	0.0594 (10)	0.0146 (8)	0.0130 (8)	0.0008 (8)
C15	0.0730 (13)	0.0769 (13)	0.0854 (15)	0.0310 (11)	0.0337 (12)	0.0189 (11)
C16	0.0457 (10)	0.1047 (17)	0.0919 (16)	0.0193 (11)	0.0254 (11)	0.0434 (14)
C17	0.0498 (11)	0.1072 (17)	0.0695 (13)	−0.0099 (11)	−0.0044 (9)	0.0164 (12)
C18	0.0567 (10)	0.0660 (11)	0.0535 (10)	−0.0065 (8)	0.0049 (8)	0.0003 (8)
C19	0.0475 (8)	0.0397 (8)	0.0350 (7)	−0.0050 (6)	0.0105 (6)	−0.0034 (6)
C20	0.0587 (10)	0.0475 (9)	0.0615 (10)	0.0017 (7)	0.0259 (8)	0.0015 (8)
C21	0.0595 (10)	0.0703 (12)	0.0669 (11)	−0.0057 (9)	0.0317 (9)	−0.0016 (9)
C22	0.0722 (12)	0.0628 (11)	0.0594 (11)	−0.0201 (9)	0.0277 (9)	0.0015 (9)
C23	0.0804 (13)	0.0481 (10)	0.0867 (14)	−0.0044 (9)	0.0308 (11)	0.0179 (9)
C24	0.0584 (10)	0.0467 (9)	0.0751 (12)	0.0015 (8)	0.0244 (9)	0.0127 (8)
O1B	0.0760 (15)	0.0472 (8)	0.0422 (14)	−0.0150 (9)	−0.0031 (11)	0.0009 (10)
C12B	0.051 (5)	0.053 (5)	0.058 (5)	−0.005 (4)	0.021 (4)	−0.007 (4)

O1A—C12A	1.417 (3)	C19—C24	1.386 (2)
O1B—C12B	1.402 (15)	C20—C21	1.381 (3)
O2—C10	1.417 (2)	C21—C22	1.367 (3)
O2—C7	1.372 (2)	C22—C23	1.364 (3)
O1A—H1OA	0.8200	C23—C24	1.378 (3)
O1B—H1OB	0.8200	C5—H5	0.9300
N1—C11	1.4668 (19)	C6—H6	0.9300
N1—C1	1.3824 (19)	C8—H8	0.9300
N1—C3	1.3621 (18)	C9—H9	0.9300
N2—C2	1.3834 (19)	C10—H10A	0.9600
N2—C3	1.3174 (18)	C10—H10C	0.9600
C1—C2	1.3712 (19)	C10—H10B	0.9600
C1—C13	1.481 (2)	C11—H11A	0.9700
C2—C19	1.470 (2)	C11—H11C	0.9700
C3—C4	1.475 (2)	C11—H11D	0.9700
C4—C9	1.381 (2)	C11—H11B	0.9700
C4—C5	1.389 (2)	C12A—H12A	0.9700
C5—C6	1.373 (3)	C12A—H12B	0.9700
C6—C7	1.377 (2)	C12B—H12C	0.9700
C7—C8	1.377 (2)	C12B—H12D	0.9700
C8—C9	1.383 (2)	C14—H14	0.9300
C11—C12B	1.341 (9)	C15—H15	0.9300
C11—C12A	1.536 (2)	C16—H16	0.9300
C13—C14	1.380 (2)	C17—H17	0.9300
C13—C18	1.377 (2)	C18—H18	0.9300
C14—C15	1.377 (3)	C20—H20	0.9300
C15—C16	1.358 (3)	C21—H21	0.9300
C16—C17	1.364 (3)	C22—H22	0.9300
C17—C18	1.386 (3)	C23—H23	0.9300
C19—C20	1.385 (2)	C24—H24	0.9300
C7—O2—C10	117.99 (15)	C9—C8—H8	120.00
C12A—O1A—H1OA	109.00	C7—C8—H8	120.00
C12B—O1B—H1OB	110.00	C4—C9—H9	119.00
C1—N1—C11	125.90 (12)	C8—C9—H9	119.00
C3—N1—C11	126.88 (13)	O2—C10—H10B	109.00
C1—N1—C3	107.04 (11)	O2—C10—H10C	109.00
C2—N2—C3	106.46 (12)	O2—C10—H10A	109.00
N1—C1—C2	106.18 (12)	H10A—C10—H10C	109.00
C2—C1—C13	130.59 (14)	H10B—C10—H10C	109.00
N1—C1—C13	123.19 (12)	H10A—C10—H10B	110.00
N2—C2—C1	109.15 (13)	N1—C11—H11A	109.00
C1—C2—C19	130.18 (14)	N1—C11—H11C	107.00
N2—C2—C19	120.43 (12)	N1—C11—H11D	107.00
N1—C3—N2	111.16 (13)	N1—C11—H11B	109.00
N1—C3—C4	126.61 (13)	C12A—C11—H11B	109.00
N2—C3—C4	122.22 (13)	H11A—C11—H11B	108.00
C3—C4—C9	123.02 (13)	C12B—C11—H11C	106.00
C5—C4—C9	117.76 (15)	C12B—C11—H11D	108.00
C3—C4—C5	118.97 (14)	H11C—C11—H11D	107.00
C4—C5—C6	121.02 (15)	C12A—C11—H11A	109.00
C5—C6—C7	120.42 (16)	O1A—C12A—H12B	110.00
O2—C7—C8	124.40 (16)	C11—C12A—H12A	110.00
O2—C7—C6	116.00 (15)	O1A—C12A—H12A	110.00
C6—C7—C8	119.60 (16)	H12A—C12A—H12B	108.00
C7—C8—C9	119.60 (15)	C11—C12A—H12B	110.00
C4—C9—C8	121.57 (15)	C11—C12B—H12D	111.00
N1—C11—C12B	121.3 (4)	O1B—C12B—H12C	111.00
N1—C11—C12A	112.93 (13)	H12C—C12B—H12D	109.00
O1A—C12A—C11	110.10 (17)	O1B—C12B—H12D	111.00
O1B—C12B—C11	102.2 (8)	C11—C12B—H12C	111.00
C1—C13—C14	121.08 (14)	C13—C14—H14	120.00
C14—C13—C18	118.58 (15)	C15—C14—H14	120.00
C1—C13—C18	120.29 (14)	C16—C15—H15	120.00
C13—C14—C15	120.84 (17)	C14—C15—H15	120.00
C14—C15—C16	120.0 (2)	C15—C16—H16	120.00
C15—C16—C17	120.2 (2)	C17—C16—H16	120.00
C16—C17—C18	120.20 (19)	C16—C17—H17	120.00
C13—C18—C17	120.17 (17)	C18—C17—H17	120.00
C2—C19—C20	123.49 (13)	C17—C18—H18	120.00
C2—C19—C24	119.33 (14)	C13—C18—H18	120.00
C20—C19—C24	117.15 (15)	C19—C20—H20	119.00
C19—C20—C21	121.07 (16)	C21—C20—H20	119.00
C20—C21—C22	120.64 (18)	C20—C21—H21	120.00
C21—C22—C23	119.18 (18)	C22—C21—H21	120.00
C22—C23—C24	120.54 (18)	C23—C22—H22	120.00
C19—C24—C23	121.37 (17)	C21—C22—H22	120.00
C6—C5—H5	119.00	C22—C23—H23	120.00
C4—C5—H5	119.00	C24—C23—H23	120.00
C5—C6—H6	120.00	C23—C24—H24	119.00
C7—C6—H6	120.00	C19—C24—H24	119.00
C10—O2—C7—C6	−167.65 (17)	N2—C3—C4—C5	−47.3 (2)
C10—O2—C7—C8	12.7 (3)	N2—C3—C4—C9	126.90 (16)
C3—N1—C1—C2	−0.76 (14)	C3—C4—C5—C6	175.61 (16)
C3—N1—C1—C13	−178.72 (13)	C9—C4—C5—C6	1.1 (3)
C11—N1—C1—C2	−176.05 (12)	C3—C4—C9—C8	−176.00 (14)
C11—N1—C1—C13	6.0 (2)	C5—C4—C9—C8	−1.8 (2)
C1—N1—C3—N2	0.55 (15)	C4—C5—C6—C7	0.6 (3)
C1—N1—C3—C4	179.26 (13)	C5—C6—C7—O2	178.52 (17)
C11—N1—C3—N2	175.78 (12)	C5—C6—C7—C8	−1.8 (3)
C11—N1—C3—C4	−5.5 (2)	O2—C7—C8—C9	−179.18 (15)
C1—N1—C11—C12A	67.64 (19)	C6—C7—C8—C9	1.2 (2)
C3—N1—C11—C12A	−106.74 (18)	C7—C8—C9—C4	0.6 (2)
C3—N2—C2—C1	−0.39 (15)	N1—C11—C12A—O1A	46.6 (2)
C3—N2—C2—C19	174.53 (12)	C1—C13—C14—C15	−175.92 (17)
C2—N2—C3—N1	−0.10 (16)	C18—C13—C14—C15	1.4 (3)
C2—N2—C3—C4	−178.89 (13)	C1—C13—C18—C17	176.12 (17)
N1—C1—C2—N2	0.71 (15)	C14—C13—C18—C17	−1.2 (3)
N1—C1—C2—C19	−173.56 (13)	C13—C14—C15—C16	−0.7 (3)
C13—C1—C2—N2	178.46 (13)	C14—C15—C16—C17	−0.2 (3)
C13—C1—C2—C19	4.2 (2)	C15—C16—C17—C18	0.4 (3)
N1—C1—C13—C14	−91.53 (18)	C16—C17—C18—C13	0.4 (3)
N1—C1—C13—C18	91.21 (18)	C2—C19—C20—C21	175.87 (15)
C2—C1—C13—C14	91.1 (2)	C24—C19—C20—C21	−2.3 (2)
C2—C1—C13—C18	−86.2 (2)	C2—C19—C24—C23	−176.95 (16)
N2—C2—C19—C20	165.59 (14)	C20—C19—C24—C23	1.3 (2)
N2—C2—C19—C24	−16.3 (2)	C19—C20—C21—C22	1.4 (3)
C1—C2—C19—C20	−20.7 (2)	C20—C21—C22—C23	0.5 (3)
C1—C2—C19—C24	157.46 (15)	C21—C22—C23—C24	−1.5 (3)
N1—C3—C4—C5	134.15 (16)	C22—C23—C24—C19	0.6 (3)
N1—C3—C4—C9	−51.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N2i	0.82	2.01	2.829 (3)	175
C9—H9···O1Aii	0.93	2.58	3.452 (3)	156
C24—H24···O1Aiii	0.93	2.53	3.448 (4)	170
C23—H23···Cg1iii	0.93	2.90	3.736 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N2i	0.82	2.01	2.829 (3)	175
C9—H9⋯O1A ii	0.93	2.58	3.452 (3)	156
C24—H24⋯O1A iii	0.93	2.53	3.448 (4)	170
C23—H23⋯Cg1iii	0.93	2.90	3.736 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) .