2-(4-Meth-oxy-phen-yl)-1-pentyl-4,5-di-phenyl-1H-imidazole.

The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-meth-oxy substituent on the benzene ring. The two phenyl and meth-oxy-benzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the meth-oxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the meth-oxy C atom. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R2(2)(22) loops. These dimers are stacked along the a-axis direction.

Related literature

For the non-linear optical and chemiluminescence properties of lophine and its derivatives, see: Santos et al. (2001 ▶); Radziszewski (1877 ▶); Maeda & Hayashi (1969 ▶, 1970 ▶). For the bioactivity of imidazoles, see: Antolini et al. (1999 ▶); Eyers et al. (1998 ▶); Laszlo et al. (1999 ▶); Newman et al. (2000 ▶); Veisi et al. (2012 ▶); Wang et al. (2002 ▶). For related structures, see, for example: Yanover & Kaftory (2009a ▶,b ▶); Kison & Opatz (2009 ▶); Zhao et al. (2012 ▶). For representative bond lengths, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C27H28N2O

M = 396.51

Triclinic,

a = 9.7214 (19) Å

b = 10.739 (1) Å

c = 11.7367 (10) Å

α = 114.069 (4)°

β = 99.021 (6)°

γ = 95.425 (6)°

V = 1087.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 93 K

0.47 × 0.18 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.619, T max = 0.746

15574 measured reflections

4968 independent reflections

3542 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.06

4968 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: APEX2 and SAINT (Bruker, 2011 ▶); data reduction: SAINT (Bruker, 2011 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049100/bt6874sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049100/bt6874Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049100/bt6874Isup3.cml

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

C27H28N2O	Z = 2
Mr = 396.51	F(000) = 424
Triclinic, P1	Dx = 1.211 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7214 (19) Å	Cell parameters from 3238 reflections
b = 10.739 (1) Å	θ = 2.6–26.1°
c = 11.7367 (10) Å	µ = 0.07 mm−1
α = 114.069 (4)°	T = 93 K
β = 99.021 (6)°	Rectangular plate, colourless
γ = 95.425 (6)°	0.47 × 0.18 × 0.08 mm
V = 1087.7 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4968 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 27.6°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −12→12
Tmin = 0.619, Tmax = 0.746	k = −13→14
15574 measured 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0663P)2 + 0.0245P] where P = (Fo2 + 2Fc2)/3
4968 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.25 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	0.65447 (14)	1.04609 (14)	0.93573 (12)	0.0209 (3)
C2	0.63626 (14)	0.90460 (14)	0.87092 (12)	0.0208 (3)
N2	0.73101 (12)	0.86376 (11)	0.94408 (10)	0.0214 (3)
C3	0.80178 (14)	0.98139 (14)	1.04912 (13)	0.0206 (3)
N1	0.75725 (12)	1.09265 (12)	1.04654 (10)	0.0218 (3)
C4	0.58701 (15)	1.14575 (14)	0.89992 (12)	0.0213 (3)
C5	0.65877 (16)	1.28159 (15)	0.94687 (13)	0.0252 (3)
H5	0.7490	1.3086	1.0031	0.030*
C6	0.60042 (16)	1.37763 (15)	0.91278 (14)	0.0276 (3)
H6	0.6507	1.4696	0.9454	0.033*
C7	0.46848 (16)	1.33933 (16)	0.83088 (14)	0.0290 (4)
H7	0.4288	1.4045	0.8064	0.035*
C8	0.39535 (17)	1.20596 (16)	0.78529 (14)	0.0283 (4)
H8	0.3045	1.1798	0.7302	0.034*
C9	0.45371 (15)	1.11015 (15)	0.81940 (13)	0.0244 (3)
H9	0.4022	1.0188	0.7875	0.029*
C10	0.54830 (15)	0.80462 (14)	0.74497 (13)	0.0210 (3)
C11	0.42624 (16)	0.71869 (15)	0.73438 (14)	0.0279 (4)
H11	0.3970	0.7226	0.8091	0.033*
C12	0.34667 (17)	0.62676 (16)	0.61431 (15)	0.0334 (4)
H12	0.2637	0.5677	0.6077	0.040*
C13	0.38700 (17)	0.62053 (16)	0.50497 (14)	0.0310 (4)
H13	0.3321	0.5577	0.4233	0.037*
C14	0.50733 (17)	0.70598 (16)	0.51489 (14)	0.0329 (4)
H14	0.5353	0.7026	0.4398	0.040*
C15	0.58783 (16)	0.79690 (15)	0.63386 (13)	0.0280 (4)
H15	0.6713	0.8548	0.6396	0.034*
C16	0.90797 (15)	0.98543 (14)	1.15551 (13)	0.0216 (3)
C17	1.00822 (15)	0.89913 (15)	1.14112 (13)	0.0240 (3)
H17	1.0102	0.8329	1.0579	0.029*
C18	1.10545 (15)	0.90705 (15)	1.24484 (13)	0.0249 (3)
H18	1.1723	0.8462	1.2326	0.030*
C19	1.10445 (15)	1.00433 (15)	1.36650 (13)	0.0243 (3)
O119	1.19783 (10)	1.02238 (11)	1.47489 (9)	0.0288 (3)
C119	1.28969 (17)	0.92355 (17)	1.46185 (15)	0.0351 (4)
H11A	1.2332	0.8303	1.4256	0.053*
H11B	1.3471	0.9442	1.5459	0.053*
H11C	1.3518	0.9283	1.4050	0.053*
C20	1.00777 (15)	1.09470 (15)	1.38280 (13)	0.0255 (3)
H20	1.0087	1.1633	1.4658	0.031*
C21	0.91080 (15)	1.08526 (15)	1.27931 (13)	0.0242 (3)
H21	0.8450	1.1471	1.2918	0.029*
C22	0.75400 (15)	0.72148 (14)	0.90983 (13)	0.0228 (3)
H22A	0.6625	0.6574	0.8669	0.027*
H22B	0.7908	0.7114	0.9886	0.027*
C23	0.85838 (15)	0.68150 (14)	0.82145 (13)	0.0241 (3)
H23A	0.8103	0.6648	0.7344	0.029*
H23B	0.9379	0.7599	0.8518	0.029*
C24	0.91712 (16)	0.55285 (15)	0.81503 (14)	0.0260 (3)
H24A	0.9624	0.5680	0.9024	0.031*
H24B	0.8381	0.4734	0.7814	0.031*
C25	1.02476 (16)	0.51780 (16)	0.73060 (14)	0.0311 (4)
H25A	0.9762	0.4906	0.6411	0.037*
H25B	1.0966	0.6017	0.7571	0.037*
C26	1.09912 (18)	0.40151 (16)	0.73654 (16)	0.0359 (4)
H26A	1.1529	0.4301	0.8237	0.054*
H26B	1.1637	0.3809	0.6775	0.054*
H26C	1.0286	0.3185	0.7122	0.054*

	U11	U22	U33	U12	U13	U23
C1	0.0207 (7)	0.0229 (7)	0.0170 (7)	0.0013 (6)	0.0033 (6)	0.0072 (6)
C2	0.0205 (7)	0.0251 (7)	0.0170 (7)	0.0031 (6)	0.0037 (5)	0.0097 (6)
N2	0.0241 (6)	0.0216 (6)	0.0168 (6)	0.0025 (5)	0.0030 (5)	0.0075 (5)
C3	0.0221 (7)	0.0216 (7)	0.0172 (7)	0.0025 (6)	0.0059 (6)	0.0071 (6)
N1	0.0229 (6)	0.0238 (6)	0.0180 (6)	0.0035 (5)	0.0047 (5)	0.0081 (5)
C4	0.0243 (7)	0.0244 (7)	0.0154 (7)	0.0067 (6)	0.0074 (6)	0.0070 (6)
C5	0.0268 (8)	0.0255 (8)	0.0196 (7)	0.0052 (6)	0.0032 (6)	0.0066 (6)
C6	0.0352 (9)	0.0212 (7)	0.0255 (8)	0.0044 (6)	0.0090 (7)	0.0083 (6)
C7	0.0373 (9)	0.0294 (8)	0.0235 (8)	0.0136 (7)	0.0083 (7)	0.0124 (7)
C8	0.0292 (8)	0.0331 (8)	0.0209 (7)	0.0088 (7)	0.0034 (6)	0.0098 (7)
C9	0.0259 (8)	0.0235 (8)	0.0211 (7)	0.0045 (6)	0.0054 (6)	0.0067 (6)
C10	0.0229 (7)	0.0201 (7)	0.0182 (7)	0.0053 (6)	0.0031 (6)	0.0067 (6)
C11	0.0296 (8)	0.0271 (8)	0.0222 (7)	0.0021 (6)	0.0084 (6)	0.0056 (6)
C12	0.0265 (8)	0.0299 (8)	0.0327 (9)	−0.0018 (7)	0.0048 (7)	0.0047 (7)
C13	0.0321 (9)	0.0293 (8)	0.0208 (7)	0.0055 (7)	−0.0042 (6)	0.0038 (6)
C14	0.0405 (9)	0.0363 (9)	0.0184 (7)	0.0037 (7)	0.0042 (7)	0.0096 (7)
C15	0.0292 (8)	0.0305 (8)	0.0223 (7)	−0.0008 (6)	0.0031 (6)	0.0116 (7)
C16	0.0223 (7)	0.0227 (7)	0.0187 (7)	0.0009 (6)	0.0033 (6)	0.0089 (6)
C17	0.0254 (8)	0.0257 (8)	0.0177 (7)	0.0023 (6)	0.0049 (6)	0.0065 (6)
C18	0.0225 (8)	0.0286 (8)	0.0238 (7)	0.0046 (6)	0.0053 (6)	0.0114 (6)
C19	0.0217 (7)	0.0316 (8)	0.0189 (7)	−0.0009 (6)	0.0008 (6)	0.0128 (6)
O119	0.0271 (6)	0.0383 (6)	0.0204 (5)	0.0066 (5)	0.0007 (4)	0.0135 (5)
C119	0.0310 (9)	0.0456 (10)	0.0290 (8)	0.0105 (8)	−0.0007 (7)	0.0180 (8)
C20	0.0277 (8)	0.0267 (8)	0.0185 (7)	0.0024 (6)	0.0055 (6)	0.0064 (6)
C21	0.0243 (8)	0.0255 (7)	0.0210 (7)	0.0040 (6)	0.0048 (6)	0.0084 (6)
C22	0.0249 (7)	0.0206 (7)	0.0214 (7)	0.0022 (6)	0.0013 (6)	0.0092 (6)
C23	0.0268 (8)	0.0234 (7)	0.0188 (7)	0.0033 (6)	0.0026 (6)	0.0068 (6)
C24	0.0276 (8)	0.0263 (8)	0.0227 (7)	0.0054 (6)	0.0037 (6)	0.0095 (6)
C25	0.0320 (9)	0.0300 (8)	0.0292 (8)	0.0073 (7)	0.0080 (7)	0.0097 (7)
C26	0.0339 (9)	0.0317 (9)	0.0369 (9)	0.0088 (7)	0.0076 (7)	0.0091 (7)

C1—C2	1.3721 (19)	C16—C17	1.390 (2)
C1—N1	1.3811 (17)	C16—C21	1.4045 (19)
C1—C4	1.4716 (19)	C17—C18	1.3864 (19)
C2—N2	1.3833 (17)	C17—H17	0.9500
C2—C10	1.4848 (18)	C18—C19	1.386 (2)
N2—C3	1.3742 (17)	C18—H18	0.9500
N2—C22	1.4622 (17)	C19—O119	1.3724 (16)
C3—N1	1.3188 (17)	C19—C20	1.393 (2)
C3—C16	1.4730 (19)	O119—C119	1.4272 (18)
C4—C9	1.3950 (19)	C119—H11A	0.9800
C4—C5	1.396 (2)	C119—H11B	0.9800
C5—C6	1.386 (2)	C119—H11C	0.9800
C5—H5	0.9500	C20—C21	1.3772 (19)
C6—C7	1.389 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.381 (2)	C22—C23	1.529 (2)
C7—H7	0.9500	C22—H22A	0.9900
C8—C9	1.384 (2)	C22—H22B	0.9900
C8—H8	0.9500	C23—C24	1.5225 (19)
C9—H9	0.9500	C23—H23A	0.9900
C10—C15	1.389 (2)	C23—H23B	0.9900
C10—C11	1.389 (2)	C24—C25	1.521 (2)
C11—C12	1.392 (2)	C24—H24A	0.9900
C11—H11	0.9500	C24—H24B	0.9900
C12—C13	1.378 (2)	C25—C26	1.521 (2)
C12—H12	0.9500	C25—H25A	0.9900
C13—C14	1.375 (2)	C25—H25B	0.9900
C13—H13	0.9500	C26—H26A	0.9800
C14—C15	1.384 (2)	C26—H26B	0.9800
C14—H14	0.9500	C26—H26C	0.9800
C15—H15	0.9500
C2—C1—N1	110.31 (12)	C18—C17—C16	121.84 (13)
C2—C1—C4	129.52 (12)	C18—C17—H17	119.1
N1—C1—C4	120.10 (12)	C16—C17—H17	119.1
C1—C2—N2	105.42 (11)	C19—C18—C17	119.52 (14)
C1—C2—C10	132.42 (13)	C19—C18—H18	120.2
N2—C2—C10	121.98 (12)	C17—C18—H18	120.2
C3—N2—C2	107.27 (11)	O119—C19—C18	124.04 (13)
C3—N2—C22	127.52 (12)	O119—C19—C20	116.28 (12)
C2—N2—C22	125.14 (11)	C18—C19—C20	119.63 (13)
N1—C3—N2	111.01 (12)	C19—O119—C119	117.07 (11)
N1—C3—C16	123.28 (12)	O119—C119—H11A	109.5
N2—C3—C16	125.62 (12)	O119—C119—H11B	109.5
C3—N1—C1	105.98 (11)	H11A—C119—H11B	109.5
C9—C4—C5	118.02 (13)	O119—C119—H11C	109.5
C9—C4—C1	122.72 (13)	H11A—C119—H11C	109.5
C5—C4—C1	119.25 (13)	H11B—C119—H11C	109.5
C6—C5—C4	121.02 (13)	C21—C20—C19	120.41 (13)
C6—C5—H5	119.5	C21—C20—H20	119.8
C4—C5—H5	119.5	C19—C20—H20	119.8
C5—C6—C7	119.98 (14)	C20—C21—C16	120.87 (14)
C5—C6—H6	120.0	C20—C21—H21	119.6
C7—C6—H6	120.0	C16—C21—H21	119.6
C8—C7—C6	119.63 (14)	N2—C22—C23	112.03 (12)
C8—C7—H7	120.2	N2—C22—H22A	109.2
C6—C7—H7	120.2	C23—C22—H22A	109.2
C7—C8—C9	120.34 (14)	N2—C22—H22B	109.2
C7—C8—H8	119.8	C23—C22—H22B	109.2
C9—C8—H8	119.8	H22A—C22—H22B	107.9
C8—C9—C4	121.00 (14)	C24—C23—C22	113.10 (12)
C8—C9—H9	119.5	C24—C23—H23A	109.0
C4—C9—H9	119.5	C22—C23—H23A	109.0
C15—C10—C11	118.59 (13)	C24—C23—H23B	109.0
C15—C10—C2	119.43 (13)	C22—C23—H23B	109.0
C11—C10—C2	121.97 (13)	H23A—C23—H23B	107.8
C10—C11—C12	120.06 (14)	C25—C24—C23	112.34 (12)
C10—C11—H11	120.0	C25—C24—H24A	109.1
C12—C11—H11	120.0	C23—C24—H24A	109.1
C13—C12—C11	120.69 (15)	C25—C24—H24B	109.1
C13—C12—H12	119.7	C23—C24—H24B	109.1
C11—C12—H12	119.7	H24A—C24—H24B	107.9
C14—C13—C12	119.50 (14)	C26—C25—C24	113.26 (14)
C14—C13—H13	120.2	C26—C25—H25A	108.9
C12—C13—H13	120.2	C24—C25—H25A	108.9
C13—C14—C15	120.24 (15)	C26—C25—H25B	108.9
C13—C14—H14	119.9	C24—C25—H25B	108.9
C15—C14—H14	119.9	H25A—C25—H25B	107.7
C14—C15—C10	120.91 (15)	C25—C26—H26A	109.5
C14—C15—H15	119.5	C25—C26—H26B	109.5
C10—C15—H15	119.5	H26A—C26—H26B	109.5
C17—C16—C21	117.68 (13)	C25—C26—H26C	109.5
C17—C16—C3	124.27 (12)	H26A—C26—H26C	109.5
C21—C16—C3	118.03 (13)	H26B—C26—H26C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O119i	0.95	2.61	3.4393 (19)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O119i	0.95	2.61	3.4393 (19)	146

Symmetry code: (i) .