2-(3,4-Di-meth-oxy-phen-yl)-1-pentyl-4,5-diphenyl-1H-imidazole.

The central imidazole ring in the title compound, C28H30N2O2, makes dihedral angles of 28.42 (13), 71.22 (15) and 29.50 (14)°, respectively, with the phenyl rings in the 4- and 5-positions and the 3,4-di-meth-oxy-phenyl group. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, weak π-π stacking inter-actions [centroid-centroid distance = 3.760 (2) Å] and C-H⋯π contacts, forming a three-dimensional network.

Related literature

For medicinal and industrial applications of imidazole-containing compounds see: Oyeka & Gugnani (1992 ▶); Schrekker et al. (2013 ▶); Mital (2009 ▶); Juchau (1989 ▶); Rondu et al. (1997 ▶); Bousquet & Feldman (1999 ▶); Ueno et al. (1995 ▶); Jung & Huang (2000 ▶); Isobe et al. (2001 ▶). For similar structures, see: Akkurt et al. (2013 ▶); Mohamed et al. (2013 ▶).

Experimental

Crystal data

C28H30N2O2

M = 426.54

Triclinic,

a = 8.900 (2) Å

b = 11.915 (3) Å

c = 12.009 (3) Å

α = 106.757 (6)°

β = 96.007 (5)°

γ = 108.170 (6)°

V = 1131.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.24 × 0.21 × 0.11 mm

Data collection

Bruker APEX2000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.668, T max = 0.981

8350 measured reflections

3953 independent reflections

2219 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.127

S = 0.87

3953 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031759/sj5371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031759/sj5371Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031759/sj5371Isup3.cml

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

C28H30N2O2	Z = 2
Mr = 426.54	F(000) = 456
Triclinic, P1	Dx = 1.252 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.900 (2) Å	Cell parameters from 856 reflections
b = 11.915 (3) Å	θ = 2.5–20.8°
c = 12.009 (3) Å	µ = 0.08 mm−1
α = 106.757 (6)°	T = 150 K
β = 96.007 (5)°	Block, colourless
γ = 108.170 (6)°	0.24 × 0.21 × 0.11 mm
V = 1131.8 (5) Å3

Bruker APEX2000 CCD area-detector diffractometer	3953 independent reflections
Radiation source: fine-focus sealed tube	2219 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −10→10
Tmin = 0.668, Tmax = 0.981	k = −13→14
8350 measured reflections	l = −14→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3
3953 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 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
O1	1.0678 (2)	1.23924 (16)	1.28583 (16)	0.0391 (7)
O2	1.0748 (2)	1.05208 (17)	1.34508 (16)	0.0404 (7)
N1	0.5735 (2)	0.70894 (19)	0.89430 (18)	0.0259 (8)
N2	0.7629 (2)	0.66063 (19)	0.98101 (18)	0.0278 (8)
C1	0.7160 (3)	0.7530 (2)	0.9748 (2)	0.0262 (9)
C2	0.6472 (3)	0.5534 (2)	0.9023 (2)	0.0257 (9)
C3	0.5296 (3)	0.5811 (2)	0.8472 (2)	0.0272 (9)
C4	0.8031 (3)	0.8829 (2)	1.0501 (2)	0.0268 (9)
C5	0.8063 (3)	0.9857 (2)	1.0185 (2)	0.0305 (9)
C6	0.8932 (3)	1.1059 (2)	1.0950 (2)	0.0316 (10)
C7	0.9794 (3)	1.1250 (2)	1.2033 (2)	0.0287 (9)
C8	0.9822 (3)	1.0229 (2)	1.2361 (2)	0.0291 (9)
C9	0.8945 (3)	0.9045 (2)	1.1609 (2)	0.0282 (9)
C10	0.4779 (3)	0.7773 (2)	0.8591 (2)	0.0302 (9)
C11	0.5026 (3)	0.7972 (3)	0.7431 (2)	0.0338 (10)
C12	0.3887 (4)	0.8550 (3)	0.7021 (2)	0.0409 (11)
C13	0.4153 (4)	0.8893 (3)	0.5935 (3)	0.0567 (12)
C14	0.3796 (5)	0.7783 (3)	0.4835 (3)	0.0731 (16)
C15	0.6611 (3)	0.4312 (2)	0.8838 (2)	0.0269 (9)
C16	0.8124 (3)	0.4217 (2)	0.9029 (2)	0.0306 (9)
C17	0.8291 (3)	0.3083 (3)	0.8889 (2)	0.0348 (10)
C18	0.6946 (4)	0.2014 (3)	0.8543 (2)	0.0355 (10)
C19	0.5440 (3)	0.2083 (3)	0.8336 (2)	0.0360 (10)
C20	0.5276 (3)	0.3225 (2)	0.8490 (2)	0.0316 (10)
C21	0.3856 (3)	0.5008 (2)	0.7528 (2)	0.0285 (9)
C22	0.4042 (3)	0.4467 (3)	0.6400 (2)	0.0371 (10)
C23	0.2726 (4)	0.3681 (3)	0.5509 (3)	0.0432 (11)
C24	0.1200 (4)	0.3430 (3)	0.5736 (3)	0.0392 (11)
C25	0.0999 (3)	0.3960 (3)	0.6849 (2)	0.0370 (10)
C26	0.2314 (3)	0.4741 (2)	0.7744 (2)	0.0330 (10)
C27	1.0564 (3)	1.3462 (2)	1.2624 (2)	0.0410 (11)
C28	1.0836 (4)	0.9506 (3)	1.3800 (2)	0.0448 (11)
H5	0.74750	0.97340	0.94260	0.0370*
H6	0.89280	1.17570	1.07190	0.0380*
H9	0.89540	0.83510	1.18430	0.0340*
H10A	0.50770	0.86000	0.92220	0.0360*
H10B	0.36180	0.73020	0.85150	0.0360*
H11A	0.48440	0.71550	0.68170	0.0410*
H11B	0.61570	0.85280	0.75310	0.0410*
H12A	0.27640	0.79520	0.68590	0.0490*
H12B	0.39940	0.93160	0.76790	0.0490*
H13A	0.52930	0.94520	0.60760	0.0680*
H13B	0.34560	0.93680	0.58040	0.0680*
H14A	0.45340	0.73410	0.49350	0.1100*
H14B	0.39440	0.80680	0.41520	0.1100*
H14C	0.26760	0.72140	0.46970	0.1100*
H16	0.90650	0.49540	0.92620	0.0370*
H17	0.93380	0.30400	0.90320	0.0420*
H18	0.70560	0.12260	0.84460	0.0430*
H19	0.45050	0.13390	0.80840	0.0430*
H20	0.42250	0.32630	0.83550	0.0380*
H22	0.50970	0.46410	0.62370	0.0450*
H23	0.28690	0.33090	0.47340	0.0520*
H24	0.02840	0.28870	0.51160	0.0470*
H25	−0.00590	0.37880	0.70060	0.0440*
H26	0.21640	0.51020	0.85200	0.0400*
H27A	1.09610	1.35060	1.19010	0.0610*
H27B	1.12200	1.42190	1.32970	0.0610*
H27C	0.94320	1.34030	1.25110	0.0610*
H28A	0.97510	0.89910	1.38300	0.0670*
H28B	1.15480	0.98290	1.45900	0.0670*
H28C	1.12690	0.89930	1.32240	0.0670*

	U11	U22	U33	U12	U13	U23
O1	0.0477 (13)	0.0262 (12)	0.0363 (12)	0.0116 (10)	−0.0006 (10)	0.0057 (10)
O2	0.0492 (13)	0.0345 (12)	0.0327 (12)	0.0150 (10)	−0.0060 (10)	0.0095 (10)
N1	0.0273 (13)	0.0266 (13)	0.0258 (13)	0.0145 (11)	0.0038 (10)	0.0073 (10)
N2	0.0298 (13)	0.0273 (13)	0.0285 (13)	0.0127 (11)	0.0052 (11)	0.0102 (11)
C1	0.0301 (16)	0.0270 (16)	0.0233 (15)	0.0122 (13)	0.0046 (13)	0.0094 (13)
C2	0.0266 (15)	0.0259 (15)	0.0257 (15)	0.0119 (13)	0.0053 (12)	0.0079 (13)
C3	0.0313 (16)	0.0249 (16)	0.0255 (15)	0.0129 (13)	0.0068 (13)	0.0054 (13)
C4	0.0268 (15)	0.0273 (16)	0.0264 (16)	0.0130 (13)	0.0065 (12)	0.0056 (13)
C5	0.0304 (16)	0.0346 (17)	0.0267 (16)	0.0136 (14)	0.0020 (13)	0.0100 (14)
C6	0.0310 (16)	0.0291 (17)	0.0357 (17)	0.0119 (14)	0.0064 (14)	0.0114 (14)
C7	0.0278 (16)	0.0226 (16)	0.0303 (16)	0.0092 (13)	0.0040 (13)	0.0017 (13)
C8	0.0308 (16)	0.0304 (17)	0.0243 (15)	0.0138 (14)	0.0023 (13)	0.0047 (13)
C9	0.0304 (16)	0.0282 (16)	0.0295 (16)	0.0140 (13)	0.0081 (13)	0.0105 (13)
C10	0.0317 (16)	0.0296 (16)	0.0332 (16)	0.0178 (13)	0.0050 (13)	0.0096 (13)
C11	0.0352 (17)	0.0371 (17)	0.0342 (17)	0.0185 (14)	0.0072 (14)	0.0137 (14)
C12	0.053 (2)	0.0359 (18)	0.0388 (18)	0.0242 (16)	0.0055 (15)	0.0127 (15)
C13	0.072 (2)	0.062 (2)	0.049 (2)	0.032 (2)	0.0108 (19)	0.0298 (19)
C14	0.097 (3)	0.094 (3)	0.046 (2)	0.054 (3)	0.018 (2)	0.027 (2)
C15	0.0303 (16)	0.0279 (16)	0.0258 (15)	0.0145 (13)	0.0057 (13)	0.0096 (13)
C16	0.0292 (16)	0.0297 (16)	0.0320 (16)	0.0125 (13)	0.0016 (13)	0.0088 (13)
C17	0.0357 (18)	0.0369 (18)	0.0384 (18)	0.0208 (15)	0.0080 (14)	0.0141 (15)
C18	0.0472 (19)	0.0318 (17)	0.0375 (18)	0.0230 (16)	0.0131 (15)	0.0154 (14)
C19	0.0410 (19)	0.0280 (17)	0.0423 (18)	0.0120 (14)	0.0129 (15)	0.0159 (14)
C20	0.0297 (16)	0.0314 (17)	0.0378 (17)	0.0139 (14)	0.0096 (14)	0.0137 (14)
C21	0.0329 (16)	0.0265 (16)	0.0291 (16)	0.0163 (13)	0.0038 (13)	0.0086 (13)
C22	0.0347 (17)	0.0388 (18)	0.0362 (18)	0.0152 (15)	0.0061 (15)	0.0086 (15)
C23	0.043 (2)	0.049 (2)	0.0300 (18)	0.0180 (17)	0.0035 (15)	0.0021 (15)
C24	0.0372 (19)	0.0351 (18)	0.0375 (19)	0.0095 (15)	−0.0021 (15)	0.0083 (15)
C25	0.0298 (17)	0.0424 (19)	0.0365 (18)	0.0100 (15)	0.0039 (14)	0.0143 (15)
C26	0.0339 (17)	0.0326 (17)	0.0321 (16)	0.0131 (14)	0.0059 (14)	0.0094 (14)
C27	0.050 (2)	0.0277 (17)	0.0433 (19)	0.0128 (15)	0.0063 (16)	0.0117 (15)
C28	0.060 (2)	0.046 (2)	0.0379 (18)	0.0316 (18)	0.0031 (16)	0.0171 (16)

O1—C7	1.358 (3)	C24—C25	1.361 (4)
O1—C27	1.413 (3)	C25—C26	1.368 (4)
O2—C8	1.359 (3)	C5—H5	0.9500
O2—C28	1.410 (4)	C6—H6	0.9500
N1—C1	1.362 (3)	C9—H9	0.9500
N1—C3	1.371 (3)	C10—H10A	0.9900
N1—C10	1.457 (3)	C10—H10B	0.9900
N2—C1	1.311 (3)	C11—H11A	0.9900
N2—C2	1.366 (3)	C11—H11B	0.9900
C1—C4	1.453 (3)	C12—H12A	0.9900
C2—C3	1.356 (4)	C12—H12B	0.9900
C2—C15	1.455 (4)	C13—H13A	0.9900
C3—C21	1.466 (4)	C13—H13B	0.9900
C4—C5	1.376 (3)	C14—H14A	0.9800
C4—C9	1.394 (3)	C14—H14B	0.9800
C5—C6	1.377 (3)	C14—H14C	0.9800
C6—C7	1.358 (3)	C16—H16	0.9500
C7—C8	1.389 (3)	C17—H17	0.9500
C8—C9	1.359 (3)	C18—H18	0.9500
C10—C11	1.506 (3)	C19—H19	0.9500
C11—C12	1.507 (5)	C20—H20	0.9500
C12—C13	1.495 (4)	C22—H22	0.9500
C13—C14	1.496 (5)	C23—H23	0.9500
C15—C16	1.387 (4)	C24—H24	0.9500
C15—C20	1.374 (4)	C25—H25	0.9500
C16—C17	1.370 (4)	C26—H26	0.9500
C17—C18	1.367 (5)	C27—H27A	0.9800
C18—C19	1.370 (5)	C27—H27B	0.9800
C19—C20	1.375 (4)	C27—H27C	0.9800
C21—C22	1.374 (3)	C28—H28A	0.9800
C21—C26	1.379 (4)	C28—H28B	0.9800
C22—C23	1.367 (4)	C28—H28C	0.9800
C23—C24	1.371 (5)
C7—O1—C27	117.52 (19)	C11—C10—H10B	109.00
C8—O2—C28	116.8 (2)	H10A—C10—H10B	108.00
C1—N1—C3	107.2 (2)	C10—C11—H11A	109.00
C1—N1—C10	129.6 (2)	C10—C11—H11B	109.00
C3—N1—C10	123.3 (2)	C12—C11—H11A	109.00
C1—N2—C2	106.1 (2)	C12—C11—H11B	109.00
N1—C1—N2	110.8 (2)	H11A—C11—H11B	108.00
N1—C1—C4	126.0 (2)	C11—C12—H12A	108.00
N2—C1—C4	123.1 (2)	C11—C12—H12B	108.00
N2—C2—C3	110.3 (2)	C13—C12—H12A	109.00
N2—C2—C15	121.4 (2)	C13—C12—H12B	109.00
C3—C2—C15	128.3 (2)	H12A—C12—H12B	108.00
N1—C3—C2	105.7 (2)	C12—C13—H13A	109.00
N1—C3—C21	123.1 (2)	C12—C13—H13B	109.00
C2—C3—C21	131.1 (2)	C14—C13—H13A	109.00
C1—C4—C5	124.9 (2)	C14—C13—H13B	109.00
C1—C4—C9	117.4 (2)	H13A—C13—H13B	108.00
C5—C4—C9	117.7 (2)	C13—C14—H14A	109.00
C4—C5—C6	121.1 (2)	C13—C14—H14B	109.00
C5—C6—C7	120.2 (2)	C13—C14—H14C	110.00
O1—C7—C6	125.0 (2)	H14A—C14—H14B	109.00
O1—C7—C8	115.1 (2)	H14A—C14—H14C	109.00
C6—C7—C8	119.9 (2)	H14B—C14—H14C	109.00
O2—C8—C7	115.3 (2)	C15—C16—H16	119.00
O2—C8—C9	125.1 (2)	C17—C16—H16	119.00
C7—C8—C9	119.7 (2)	C16—C17—H17	120.00
C4—C9—C8	121.3 (2)	C18—C17—H17	120.00
N1—C10—C11	112.6 (2)	C17—C18—H18	120.00
C10—C11—C12	111.4 (2)	C19—C18—H18	120.00
C11—C12—C13	115.0 (3)	C18—C19—H19	120.00
C12—C13—C14	113.5 (3)	C20—C19—H19	120.00
C2—C15—C16	120.2 (2)	C15—C20—H20	120.00
C2—C15—C20	122.1 (2)	C19—C20—H20	120.00
C16—C15—C20	117.8 (2)	C21—C22—H22	120.00
C15—C16—C17	121.5 (2)	C23—C22—H22	120.00
C16—C17—C18	119.8 (3)	C22—C23—H23	120.00
C17—C18—C19	119.8 (3)	C24—C23—H23	120.00
C18—C19—C20	120.3 (3)	C23—C24—H24	120.00
C15—C20—C19	120.9 (3)	C25—C24—H24	120.00
C3—C21—C22	119.3 (2)	C24—C25—H25	120.00
C3—C21—C26	122.0 (2)	C26—C25—H25	120.00
C22—C21—C26	118.6 (2)	C21—C26—H26	120.00
C21—C22—C23	120.7 (3)	C25—C26—H26	120.00
C22—C23—C24	120.0 (3)	O1—C27—H27A	109.00
C23—C24—C25	119.9 (3)	O1—C27—H27B	109.00
C24—C25—C26	120.3 (3)	O1—C27—H27C	110.00
C21—C26—C25	120.5 (2)	H27A—C27—H27B	109.00
C4—C5—H5	119.00	H27A—C27—H27C	109.00
C6—C5—H5	120.00	H27B—C27—H27C	109.00
C5—C6—H6	120.00	O2—C28—H28A	109.00
C7—C6—H6	120.00	O2—C28—H28B	109.00
C4—C9—H9	119.00	O2—C28—H28C	109.00
C8—C9—H9	119.00	H28A—C28—H28B	109.00
N1—C10—H10A	109.00	H28A—C28—H28C	109.00
N1—C10—H10B	109.00	H28B—C28—H28C	110.00
C11—C10—H10A	109.00
C27—O1—C7—C6	6.7 (4)	C2—C3—C21—C26	109.2 (3)
C27—O1—C7—C8	−173.8 (2)	C1—C4—C5—C6	−179.5 (3)
C28—O2—C8—C7	−178.5 (3)	C9—C4—C5—C6	−1.8 (4)
C28—O2—C8—C9	2.2 (4)	C1—C4—C9—C8	178.7 (3)
C3—N1—C1—N2	−0.3 (3)	C5—C4—C9—C8	0.9 (4)
C3—N1—C1—C4	−177.0 (2)	C4—C5—C6—C7	0.8 (4)
C10—N1—C1—N2	179.9 (2)	C5—C6—C7—O1	−179.3 (3)
C10—N1—C1—C4	3.2 (4)	C5—C6—C7—C8	1.2 (4)
C1—N1—C3—C2	0.5 (3)	O1—C7—C8—O2	−1.0 (3)
C1—N1—C3—C21	−177.1 (2)	O1—C7—C8—C9	178.4 (2)
C10—N1—C3—C2	−179.6 (2)	C6—C7—C8—O2	178.6 (2)
C10—N1—C3—C21	2.8 (4)	C6—C7—C8—C9	−2.0 (4)
C1—N1—C10—C11	100.4 (3)	O2—C8—C9—C4	−179.7 (3)
C3—N1—C10—C11	−79.4 (3)	C7—C8—C9—C4	1.0 (4)
C2—N2—C1—N1	−0.1 (3)	N1—C10—C11—C12	173.6 (2)
C2—N2—C1—C4	176.7 (2)	C10—C11—C12—C13	174.5 (3)
C1—N2—C2—C3	0.5 (3)	C11—C12—C13—C14	66.4 (4)
C1—N2—C2—C15	178.9 (2)	C2—C15—C16—C17	178.5 (2)
N1—C1—C4—C5	−33.0 (4)	C20—C15—C16—C17	−0.7 (3)
N1—C1—C4—C9	149.3 (3)	C2—C15—C20—C19	−179.2 (2)
N2—C1—C4—C5	150.7 (3)	C16—C15—C20—C19	−0.1 (3)
N2—C1—C4—C9	−27.0 (4)	C15—C16—C17—C18	0.6 (4)
N2—C2—C3—N1	−0.6 (3)	C16—C17—C18—C19	0.1 (4)
N2—C2—C3—C21	176.7 (2)	C17—C18—C19—C20	−0.9 (4)
C15—C2—C3—N1	−178.9 (2)	C18—C19—C20—C15	0.8 (4)
C15—C2—C3—C21	−1.5 (5)	C3—C21—C22—C23	177.9 (3)
N2—C2—C15—C16	−27.4 (3)	C26—C21—C22—C23	0.1 (5)
N2—C2—C15—C20	151.7 (2)	C3—C21—C26—C25	−178.2 (3)
C3—C2—C15—C16	150.8 (3)	C22—C21—C26—C25	−0.5 (4)
C3—C2—C15—C20	−30.2 (4)	C21—C22—C23—C24	0.3 (5)
N1—C3—C21—C22	108.4 (3)	C22—C23—C24—C25	−0.3 (5)
N1—C3—C21—C26	−73.9 (3)	C23—C24—C25—C26	−0.1 (5)
C2—C3—C21—C22	−68.5 (4)	C24—C25—C26—C21	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1i	0.95	2.53	3.168 (4)	125
C27—H27A···N2ii	0.98	2.51	3.474 (3)	168
C27—H27A···Cg1ii	0.98	2.77	3.608 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O1i	0.95	2.53	3.168 (4)	125
C27—H27A⋯N2ii	0.98	2.51	3.474 (3)	168
C27—H27A⋯Cg1ii	0.98	2.77	3.608 (3)	144

Symmetry codes: (i) ; (ii) .