2-[4,5-Diphenyl-2-(pyridin-2-yl)-1H-imidazol-1-yl]-3-phenyl-propan-1-ol.

In the title compound, C(29)H(25)N(3)O, the central imidazole ring forms dihedral angles of 64.7 (3), 33.5 (3) and 81.2 (2)° with the pyridyl and two phenyl substituents, respectively. An intra-molecular C-H⋯N hydrogen bond is observed. In the crystal, O-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the a axis.

Related literature

For the synthesis and properties of chiral ionic liquids, see: Ding & Armstrong (2005 ▶); Bwambok et al. (2008 ▶); Mao et al. (2010 ▶). For a related structure, see: Xiao et al. (2012 ▶).

Experimental

Crystal data

C29H25N3O

M = 431.52

Orthorhombic,

a = 9.2695 (4) Å

b = 15.8818 (6) Å

c = 16.0498 (6) Å

V = 2362.79 (16) Å3

Z = 4

Cu Kα radiation

μ = 0.58 mm−1

T = 291 K

0.38 × 0.28 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.809, T max = 0.868

9413 measured reflections

4442 independent reflections

3981 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.04

4442 reflections

311 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 1871 Friedel pairs

Flack parameter: 0.2 (4)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018703/rz2739sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018703/rz2739Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018703/rz2739Isup3.cml

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

C29H25N3O	F(000) = 912
Mr = 431.52	Dx = 1.213 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3448 reflections
a = 9.2695 (4) Å	θ = 3.9–70.3°
b = 15.8818 (6) Å	µ = 0.58 mm−1
c = 16.0498 (6) Å	T = 291 K
V = 2362.79 (16) Å3	Prismatic, colourless
Z = 4	0.38 × 0.28 × 0.25 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4442 independent reflections
Radiation source: fine-focus sealed tube	3981 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 70.4°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −11→6
Tmin = 0.809, Tmax = 0.868	k = −19→19
9413 measured reflections	l = −19→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.1152P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.12 e Å−3
4442 reflections	Δρmin = −0.13 e Å−3
311 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0043 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1871 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.2 (4)

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
O1	0.74800 (17)	0.67325 (12)	0.63461 (10)	0.0746 (4)
H1	0.788 (3)	0.6736 (19)	0.5871 (18)	0.094 (9)*
N1	0.38909 (18)	0.81423 (9)	0.51834 (9)	0.0550 (4)
N2	0.45320 (16)	0.73451 (8)	0.62480 (8)	0.0463 (3)
N3	0.3134 (2)	0.60522 (11)	0.49389 (10)	0.0667 (5)
C1	0.3385 (3)	1.00699 (12)	0.64156 (14)	0.0632 (5)
H1A	0.3170	0.9829	0.6929	0.076*
C2	0.3175 (3)	1.09285 (14)	0.63001 (17)	0.0765 (7)
H2	0.2801	1.1254	0.6731	0.092*
C3	0.3515 (4)	1.12968 (14)	0.55573 (18)	0.0897 (9)
H3	0.3390	1.1873	0.5484	0.108*
C4	0.4043 (4)	1.08104 (15)	0.49205 (18)	0.0922 (8)
H4	0.4270	1.1059	0.4413	0.111*
C5	0.4241 (3)	0.99523 (14)	0.50254 (15)	0.0744 (6)
H5	0.4599	0.9629	0.4588	0.089*
C6	0.3908 (2)	0.95713 (11)	0.57826 (12)	0.0559 (5)
C7	0.4089 (2)	0.86522 (10)	0.58664 (11)	0.0507 (4)
C8	0.44924 (19)	0.81699 (10)	0.65331 (10)	0.0462 (4)
C9	0.5020 (2)	0.84066 (10)	0.73772 (10)	0.0499 (4)
C10	0.6491 (3)	0.84668 (14)	0.75092 (14)	0.0680 (5)
H10	0.7133	0.8351	0.7079	0.082*
C11	0.7002 (4)	0.87002 (17)	0.82853 (18)	0.0939 (9)
H11	0.7990	0.8748	0.8372	0.113*
C12	0.6071 (5)	0.88607 (16)	0.89254 (16)	0.1047 (13)
H12	0.6425	0.9013	0.9446	0.126*
C13	0.4622 (4)	0.87974 (17)	0.87992 (14)	0.0975 (10)
H13	0.3989	0.8909	0.9235	0.117*
C14	0.4087 (3)	0.85679 (14)	0.80277 (13)	0.0712 (6)
H14	0.3096	0.8522	0.7947	0.085*
C15	0.4153 (2)	0.73696 (11)	0.54294 (10)	0.0496 (4)
C16	0.4123 (2)	0.66518 (10)	0.48335 (10)	0.0503 (4)
C17	0.5080 (3)	0.66655 (14)	0.41749 (13)	0.0661 (5)
H17	0.5735	0.7105	0.4115	0.079*
C18	0.5044 (3)	0.60158 (16)	0.36082 (15)	0.0778 (6)
H18	0.5682	0.6007	0.3161	0.093*
C19	0.4059 (3)	0.53848 (14)	0.37106 (15)	0.0769 (6)
H19	0.4017	0.4934	0.3342	0.092*
C20	0.3140 (3)	0.54377 (14)	0.43719 (14)	0.0771 (7)
H20	0.2462	0.5011	0.4433	0.093*
C21	0.1277 (2)	0.65894 (16)	0.71789 (14)	0.0702 (5)
H21	0.1068	0.6486	0.6621	0.084*
C22	0.0228 (3)	0.69407 (19)	0.7686 (2)	0.0900 (8)
H22	−0.0677	0.7066	0.7469	0.108*
C23	0.0523 (3)	0.71040 (17)	0.85053 (19)	0.0858 (8)
H23	−0.0175	0.7347	0.8845	0.103*
C24	0.1850 (3)	0.69072 (16)	0.88228 (15)	0.0768 (6)
H24	0.2050	0.7012	0.9381	0.092*
C25	0.2892 (2)	0.65539 (14)	0.83191 (13)	0.0620 (5)
H25	0.3791	0.6423	0.8543	0.074*
C26	0.2624 (2)	0.63902 (11)	0.74854 (11)	0.0518 (4)
C27	0.3778 (2)	0.60045 (11)	0.69460 (11)	0.0550 (4)
H27A	0.3347	0.5818	0.6427	0.066*
H27B	0.4167	0.5513	0.7226	0.066*
C28	0.5014 (2)	0.66113 (10)	0.67490 (10)	0.0475 (4)
H28	0.5348	0.6836	0.7284	0.057*
C29	0.6303 (2)	0.61828 (12)	0.63495 (11)	0.0552 (4)
H29A	0.607 (2)	0.5961 (13)	0.5795 (12)	0.054 (5)*
H29B	0.656 (2)	0.5676 (14)	0.6711 (13)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0663 (9)	0.0981 (12)	0.0593 (8)	−0.0147 (9)	0.0172 (7)	−0.0167 (8)
N1	0.0679 (9)	0.0455 (7)	0.0516 (8)	−0.0010 (7)	−0.0131 (7)	0.0021 (6)
N2	0.0545 (8)	0.0394 (6)	0.0449 (7)	−0.0044 (6)	0.0003 (6)	0.0021 (5)
N3	0.0840 (12)	0.0588 (9)	0.0571 (9)	−0.0182 (9)	−0.0078 (8)	−0.0028 (8)
C1	0.0696 (13)	0.0496 (9)	0.0703 (12)	−0.0003 (9)	−0.0161 (11)	−0.0032 (9)
C2	0.0835 (15)	0.0513 (11)	0.0947 (17)	0.0112 (11)	−0.0284 (14)	−0.0126 (11)
C3	0.115 (2)	0.0438 (9)	0.110 (2)	0.0078 (12)	−0.0412 (17)	0.0066 (12)
C4	0.131 (2)	0.0600 (13)	0.0858 (16)	−0.0023 (15)	−0.0165 (18)	0.0223 (12)
C5	0.1002 (18)	0.0520 (10)	0.0711 (12)	0.0030 (11)	−0.0102 (13)	0.0109 (9)
C6	0.0619 (12)	0.0431 (8)	0.0626 (10)	−0.0013 (8)	−0.0200 (9)	0.0003 (8)
C7	0.0562 (10)	0.0428 (8)	0.0530 (9)	−0.0027 (8)	−0.0081 (8)	−0.0006 (7)
C8	0.0498 (9)	0.0419 (7)	0.0470 (8)	−0.0029 (7)	0.0014 (7)	0.0001 (6)
C9	0.0668 (10)	0.0383 (7)	0.0446 (8)	−0.0040 (7)	−0.0009 (8)	0.0027 (6)
C10	0.0750 (13)	0.0635 (11)	0.0654 (11)	−0.0066 (10)	−0.0133 (11)	−0.0033 (10)
C11	0.118 (2)	0.0734 (14)	0.0907 (18)	−0.0084 (15)	−0.0504 (17)	−0.0026 (14)
C12	0.199 (4)	0.0574 (12)	0.0574 (13)	−0.0037 (19)	−0.0422 (19)	−0.0018 (10)
C13	0.172 (3)	0.0718 (15)	0.0484 (11)	0.0041 (18)	0.0144 (16)	−0.0023 (10)
C14	0.0922 (16)	0.0635 (11)	0.0578 (11)	−0.0013 (11)	0.0134 (11)	0.0014 (9)
C15	0.0545 (10)	0.0452 (8)	0.0492 (8)	−0.0024 (8)	−0.0041 (8)	0.0019 (7)
C16	0.0595 (10)	0.0438 (8)	0.0478 (8)	0.0027 (8)	−0.0096 (8)	0.0010 (7)
C17	0.0654 (12)	0.0655 (11)	0.0675 (11)	−0.0032 (10)	0.0017 (10)	−0.0087 (9)
C18	0.0777 (14)	0.0837 (15)	0.0721 (13)	0.0122 (13)	0.0085 (12)	−0.0193 (12)
C19	0.1013 (18)	0.0572 (11)	0.0721 (13)	0.0065 (12)	−0.0160 (14)	−0.0179 (10)
C20	0.1032 (19)	0.0589 (11)	0.0693 (13)	−0.0229 (13)	−0.0153 (13)	−0.0068 (10)
C21	0.0683 (13)	0.0761 (13)	0.0663 (12)	−0.0071 (11)	−0.0070 (10)	0.0059 (10)
C22	0.0617 (14)	0.0954 (18)	0.113 (2)	0.0056 (13)	0.0016 (14)	0.0151 (16)
C23	0.0765 (16)	0.0768 (15)	0.1042 (19)	0.0024 (12)	0.0317 (15)	0.0014 (14)
C24	0.0943 (17)	0.0745 (13)	0.0616 (12)	−0.0117 (13)	0.0199 (12)	−0.0041 (10)
C25	0.0652 (12)	0.0650 (11)	0.0557 (10)	−0.0059 (9)	0.0038 (9)	0.0049 (9)
C26	0.0590 (10)	0.0444 (8)	0.0521 (9)	−0.0102 (8)	0.0057 (8)	0.0076 (7)
C27	0.0706 (12)	0.0403 (8)	0.0542 (9)	−0.0067 (8)	0.0078 (9)	0.0018 (7)
C28	0.0596 (10)	0.0407 (7)	0.0423 (7)	0.0000 (7)	0.0018 (7)	0.0049 (6)
C29	0.0674 (11)	0.0531 (9)	0.0452 (8)	0.0070 (9)	0.0046 (8)	0.0036 (8)

O1—H1	0.85 (3)	C13—H13	0.9300
O1—C29	1.397 (3)	C13—C14	1.383 (4)
N1—C7	1.375 (2)	C14—H14	0.9300
N1—C15	1.312 (2)	C15—C16	1.488 (2)
N2—C8	1.388 (2)	C16—C17	1.380 (3)
N2—C15	1.360 (2)	C17—H17	0.9300
N2—C28	1.485 (2)	C17—C18	1.376 (3)
N3—C16	1.333 (3)	C18—H18	0.9300
N3—C20	1.334 (3)	C18—C19	1.366 (4)
C1—H1A	0.9300	C19—H19	0.9300
C1—C2	1.390 (3)	C19—C20	1.364 (4)
C1—C6	1.376 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—H21	0.9300
C2—C3	1.365 (4)	C21—C22	1.385 (4)
C3—H3	0.9300	C21—C26	1.379 (3)
C3—C4	1.371 (4)	C22—H22	0.9300
C4—H4	0.9300	C22—C23	1.368 (4)
C4—C5	1.385 (3)	C23—H23	0.9300
C5—H5	0.9300	C23—C24	1.368 (4)
C5—C6	1.392 (3)	C24—H24	0.9300
C6—C7	1.476 (2)	C24—C25	1.379 (3)
C7—C8	1.368 (2)	C25—H25	0.9300
C8—C9	1.488 (2)	C25—C26	1.386 (3)
C9—C10	1.384 (3)	C26—C27	1.507 (3)
C9—C14	1.380 (3)	C27—H27A	0.9700
C10—H10	0.9300	C27—H27B	0.9700
C10—C11	1.383 (3)	C27—C28	1.530 (2)
C11—H11	0.9300	C28—H28	0.9800
C11—C12	1.366 (5)	C28—C29	1.517 (3)
C12—H12	0.9300	C29—H29A	0.98 (2)
C12—C13	1.361 (5)	C29—H29B	1.02 (2)
C29—O1—H1	110 (2)	N3—C16—C15	118.61 (17)
C15—N1—C7	106.63 (14)	N3—C16—C17	123.39 (18)
C8—N2—C28	124.76 (14)	C17—C16—C15	117.91 (17)
C15—N2—C8	106.54 (14)	C16—C17—H17	120.7
C15—N2—C28	128.55 (14)	C18—C17—C16	118.6 (2)
C16—N3—C20	115.7 (2)	C18—C17—H17	120.7
C2—C1—H1A	119.5	C17—C18—H18	120.4
C6—C1—H1A	119.5	C19—C18—C17	119.1 (2)
C6—C1—C2	121.0 (2)	C19—C18—H18	120.4
C1—C2—H2	119.9	C18—C19—H19	121.1
C3—C2—C1	120.3 (2)	C20—C19—C18	117.8 (2)
C3—C2—H2	119.9	C20—C19—H19	121.1
C2—C3—H3	120.3	N3—C20—C19	125.3 (2)
C2—C3—C4	119.5 (2)	N3—C20—H20	117.3
C4—C3—H3	120.3	C19—C20—H20	117.3
C3—C4—H4	119.6	C22—C21—H21	119.4
C3—C4—C5	120.7 (3)	C26—C21—H21	119.4
C5—C4—H4	119.6	C26—C21—C22	121.2 (2)
C4—C5—H5	119.9	C21—C22—H22	120.0
C4—C5—C6	120.3 (2)	C23—C22—C21	120.1 (3)
C6—C5—H5	119.9	C23—C22—H22	120.0
C1—C6—C5	118.20 (19)	C22—C23—H23	120.2
C1—C6—C7	122.82 (19)	C24—C23—C22	119.6 (3)
C5—C6—C7	118.96 (19)	C24—C23—H23	120.2
N1—C7—C6	119.65 (16)	C23—C24—H24	119.8
C8—C7—N1	109.29 (15)	C23—C24—C25	120.3 (2)
C8—C7—C6	131.02 (16)	C25—C24—H24	119.8
N2—C8—C9	121.99 (15)	C24—C25—H25	119.4
C7—C8—N2	106.12 (14)	C24—C25—C26	121.1 (2)
C7—C8—C9	131.32 (15)	C26—C25—H25	119.4
C10—C9—C8	118.72 (18)	C21—C26—C25	117.7 (2)
C14—C9—C8	122.0 (2)	C21—C26—C27	122.11 (18)
C14—C9—C10	119.3 (2)	C25—C26—C27	120.24 (19)
C9—C10—H10	120.2	C26—C27—H27A	108.9
C11—C10—C9	119.6 (3)	C26—C27—H27B	108.9
C11—C10—H10	120.2	C26—C27—C28	113.23 (14)
C10—C11—H11	119.6	H27A—C27—H27B	107.7
C12—C11—C10	120.7 (3)	C28—C27—H27A	108.9
C12—C11—H11	119.6	C28—C27—H27B	108.9
C11—C12—H12	120.1	N2—C28—C27	112.40 (15)
C13—C12—C11	119.8 (2)	N2—C28—H28	106.5
C13—C12—H12	120.1	N2—C28—C29	111.11 (13)
C12—C13—H13	119.8	C27—C28—H28	106.5
C12—C13—C14	120.4 (3)	C29—C28—C27	113.22 (15)
C14—C13—H13	119.8	C29—C28—H28	106.5
C9—C14—C13	120.1 (3)	O1—C29—C28	109.65 (16)
C9—C14—H14	119.9	O1—C29—H29A	113.2 (12)
C13—C14—H14	119.9	O1—C29—H29B	108.3 (13)
N1—C15—N2	111.42 (15)	C28—C29—H29A	111.7 (12)
N1—C15—C16	121.31 (15)	C28—C29—H29B	107.3 (12)
N2—C15—C16	127.12 (15)	H29A—C29—H29B	106.5 (16)
N1—C7—C8—N2	−0.3 (2)	C10—C9—C14—C13	0.8 (3)
N1—C7—C8—C9	170.93 (19)	C10—C11—C12—C13	−0.5 (4)
N1—C15—C16—N3	−116.1 (2)	C11—C12—C13—C14	0.3 (4)
N1—C15—C16—C17	60.7 (3)	C12—C13—C14—C9	−0.5 (4)
N2—C8—C9—C10	77.2 (2)	C14—C9—C10—C11	−1.0 (3)
N2—C8—C9—C14	−102.9 (2)	C15—N1—C7—C6	178.44 (19)
N2—C15—C16—N3	68.7 (3)	C15—N1—C7—C8	0.6 (2)
N2—C15—C16—C17	−114.5 (2)	C15—N2—C8—C7	0.0 (2)
N2—C28—C29—O1	64.47 (19)	C15—N2—C8—C9	−172.28 (17)
N3—C16—C17—C18	−1.9 (3)	C15—N2—C28—C27	−72.9 (2)
C1—C2—C3—C4	1.1 (4)	C15—N2—C28—C29	55.2 (2)
C1—C6—C7—N1	147.0 (2)	C15—C16—C17—C18	−178.6 (2)
C1—C6—C7—C8	−35.7 (3)	C16—N3—C20—C19	−0.2 (4)
C2—C1—C6—C5	0.9 (3)	C16—C17—C18—C19	0.6 (4)
C2—C1—C6—C7	−177.3 (2)	C17—C18—C19—C20	0.8 (4)
C2—C3—C4—C5	−0.4 (5)	C18—C19—C20—N3	−1.0 (4)
C3—C4—C5—C6	−0.1 (5)	C20—N3—C16—C15	178.34 (19)
C4—C5—C6—C1	−0.2 (4)	C20—N3—C16—C17	1.7 (3)
C4—C5—C6—C7	178.2 (2)	C21—C22—C23—C24	−0.9 (4)
C5—C6—C7—N1	−31.3 (3)	C21—C26—C27—C28	108.7 (2)
C5—C6—C7—C8	146.0 (2)	C22—C21—C26—C25	0.0 (3)
C6—C1—C2—C3	−1.4 (4)	C22—C21—C26—C27	179.8 (2)
C6—C7—C8—N2	−177.9 (2)	C22—C23—C24—C25	0.6 (4)
C6—C7—C8—C9	−6.6 (4)	C23—C24—C25—C26	0.0 (4)
C7—N1—C15—N2	−0.6 (2)	C24—C25—C26—C21	−0.3 (3)
C7—N1—C15—C16	−176.46 (17)	C24—C25—C26—C27	179.95 (18)
C7—C8—C9—C10	−92.9 (3)	C25—C26—C27—C28	−71.5 (2)
C7—C8—C9—C14	87.0 (3)	C26—C21—C22—C23	0.6 (4)
C8—N2—C15—N1	0.4 (2)	C26—C27—C28—N2	−64.04 (19)
C8—N2—C15—C16	175.96 (18)	C26—C27—C28—C29	169.04 (15)
C8—N2—C28—C27	112.38 (18)	C27—C28—C29—O1	−167.93 (15)
C8—N2—C28—C29	−119.57 (18)	C28—N2—C8—C7	175.71 (16)
C8—C9—C10—C11	178.9 (2)	C28—N2—C8—C9	3.4 (3)
C8—C9—C14—C13	−179.1 (2)	C28—N2—C15—N1	−175.13 (17)
C9—C10—C11—C12	0.9 (4)	C28—N2—C15—C16	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···N3	0.97	2.42	3.277 (2)	146
C22—H22···O1i	0.93	2.54	3.350 (3)	146
O1—H1···N1ii	0.85 (3)	1.94 (3)	2.789 (2)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27A⋯N3	0.97	2.42	3.277 (2)	146
C22—H22⋯O1i	0.93	2.54	3.350 (3)	146
O1—H1⋯N1ii	0.85 (3)	1.94 (3)	2.789 (2)	174 (3)

Symmetry codes: (i) ; (ii) .