3-(1H-Imidazol-1-yl)-1-phenyl-propan-1-ol.

In the title compound, C(12)H(14)N(2)O, the imidazole ring forms a dihedral angle of 66.73 (5)° with the phenyl ring. In the crystal, mol-ecules are linked via O-H⋯N and C-H⋯O hydrogen bonds into sheets lying parallel to (100). The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For general background to and the pharmacological activities of the title compound, see: Latge (1999 ▶); Steenbergn & Casadevall (2000 ▶); Pacetti & Gelone (2003 ▶); Spellberg et al. (2006 ▶). For the preparation of the title compound, see: Aboul-Enein et al. (2011 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H14N2O

M = 202.25

Monoclinic,

a = 9.0352 (5) Å

b = 11.8521 (7) Å

c = 10.3462 (6) Å

β = 109.688 (1)°

V = 1043.17 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.34 × 0.26 × 0.19 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.972, T max = 0.985

14426 measured reflections

3777 independent reflections

3245 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.05

3777 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004254/hb6620sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004254/hb6620Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004254/hb6620Isup3.cml

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

C12H14N2O	F(000) = 432
Mr = 202.25	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6547 reflections
a = 9.0352 (5) Å	θ = 3.0–32.6°
b = 11.8521 (7) Å	µ = 0.08 mm−1
c = 10.3462 (6) Å	T = 100 K
β = 109.688 (1)°	Block, colourless
V = 1043.17 (10) Å3	0.34 × 0.26 × 0.19 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 32.6°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
Tmin = 0.972, Tmax = 0.985	k = −17→17
14426 measured reflections	l = −14→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.3608P] where P = (Fo2 + 2Fc2)/3
3777 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.48286 (8)	0.08562 (6)	0.36457 (8)	0.02067 (16)
N1	0.25481 (8)	0.31589 (7)	0.35682 (8)	0.01420 (15)
N2	0.32358 (10)	0.45590 (7)	0.24613 (9)	0.02066 (17)
C1	0.31643 (10)	−0.13411 (8)	0.29554 (9)	0.01560 (16)
H1B	0.3689	−0.1285	0.3918	0.019*
C2	0.27877 (11)	−0.23971 (8)	0.23471 (10)	0.01808 (18)
H2B	0.3073	−0.3059	0.2892	0.022*
C3	0.19909 (12)	−0.24865 (8)	0.09354 (10)	0.01975 (18)
H3A	0.1735	−0.3208	0.0519	0.024*
C4	0.15757 (11)	−0.15146 (9)	0.01470 (9)	0.01935 (18)
H4A	0.1013	−0.1570	−0.0809	0.023*
C5	0.19809 (11)	−0.04577 (8)	0.07534 (9)	0.01624 (17)
H5A	0.1713	0.0203	0.0203	0.019*
C6	0.27760 (10)	−0.03610 (8)	0.21592 (9)	0.01380 (16)
C7	0.32242 (10)	0.07925 (8)	0.28116 (9)	0.01549 (16)
H7A	0.3017	0.1370	0.2066	0.019*
C8	0.22380 (10)	0.10796 (8)	0.37099 (9)	0.01587 (16)
H8A	0.1118	0.1116	0.3124	0.019*
H8B	0.2350	0.0464	0.4383	0.019*
C9	0.26905 (11)	0.21929 (8)	0.44836 (9)	0.01656 (17)
H9A	0.2007	0.2317	0.5044	0.020*
H9B	0.3789	0.2142	0.5117	0.020*
C10	0.37482 (11)	0.37408 (8)	0.33713 (10)	0.01860 (18)
H10A	0.4828	0.3579	0.3833	0.022*
C11	0.16177 (11)	0.44949 (8)	0.20509 (10)	0.01811 (18)
H11A	0.0914	0.4980	0.1397	0.022*
C12	0.11734 (10)	0.36343 (8)	0.27205 (9)	0.01602 (17)
H12A	0.0131	0.3411	0.2621	0.019*
H1O1	0.543 (2)	0.0448 (17)	0.3186 (19)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0152 (3)	0.0220 (4)	0.0251 (3)	−0.0023 (2)	0.0071 (3)	−0.0072 (3)
N1	0.0142 (3)	0.0116 (3)	0.0184 (3)	0.0000 (2)	0.0076 (3)	−0.0010 (2)
N2	0.0182 (3)	0.0179 (4)	0.0290 (4)	0.0007 (3)	0.0120 (3)	0.0036 (3)
C1	0.0146 (3)	0.0167 (4)	0.0159 (3)	0.0024 (3)	0.0057 (3)	0.0012 (3)
C2	0.0204 (4)	0.0137 (4)	0.0232 (4)	0.0028 (3)	0.0114 (3)	0.0018 (3)
C3	0.0227 (4)	0.0154 (4)	0.0244 (4)	−0.0015 (3)	0.0121 (3)	−0.0055 (3)
C4	0.0207 (4)	0.0212 (4)	0.0160 (4)	−0.0009 (3)	0.0060 (3)	−0.0035 (3)
C5	0.0174 (4)	0.0158 (4)	0.0159 (4)	0.0010 (3)	0.0062 (3)	0.0007 (3)
C6	0.0125 (3)	0.0141 (4)	0.0160 (3)	−0.0003 (3)	0.0063 (3)	−0.0015 (3)
C7	0.0155 (3)	0.0142 (4)	0.0180 (4)	−0.0009 (3)	0.0072 (3)	−0.0011 (3)
C8	0.0176 (4)	0.0127 (4)	0.0205 (4)	−0.0004 (3)	0.0106 (3)	−0.0001 (3)
C9	0.0207 (4)	0.0135 (4)	0.0176 (4)	0.0012 (3)	0.0091 (3)	0.0003 (3)
C10	0.0141 (4)	0.0174 (4)	0.0262 (4)	−0.0003 (3)	0.0092 (3)	0.0014 (3)
C11	0.0176 (4)	0.0168 (4)	0.0219 (4)	0.0032 (3)	0.0092 (3)	0.0020 (3)
C12	0.0136 (3)	0.0160 (4)	0.0195 (4)	0.0003 (3)	0.0069 (3)	−0.0012 (3)

O1—C7	1.4173 (11)	C4—H4A	0.9500
O1—H1O1	0.97 (2)	C5—C6	1.3931 (12)
N1—C10	1.3571 (11)	C5—H5A	0.9500
N1—C12	1.3767 (11)	C6—C7	1.5180 (12)
N1—C9	1.4636 (12)	C7—C8	1.5269 (12)
N2—C10	1.3218 (13)	C7—H7A	1.0000
N2—C11	1.3802 (12)	C8—C9	1.5260 (13)
C1—C2	1.3907 (13)	C8—H8A	0.9900
C1—C6	1.3986 (12)	C8—H8B	0.9900
C1—H1B	0.9500	C9—H9A	0.9900
C2—C3	1.3979 (14)	C9—H9B	0.9900
C2—H2B	0.9500	C10—H10A	0.9500
C3—C4	1.3881 (14)	C11—C12	1.3671 (13)
C3—H3A	0.9500	C11—H11A	0.9500
C4—C5	1.3936 (13)	C12—H12A	0.9500
C7—O1—H1O1	107.8 (11)	C6—C7—C8	110.39 (7)
C10—N1—C12	106.94 (8)	O1—C7—H7A	108.7
C10—N1—C9	126.45 (8)	C6—C7—H7A	108.7
C12—N1—C9	126.60 (7)	C8—C7—H7A	108.7
C10—N2—C11	105.03 (8)	C9—C8—C7	113.82 (7)
C2—C1—C6	120.42 (8)	C9—C8—H8A	108.8
C2—C1—H1B	119.8	C7—C8—H8A	108.8
C6—C1—H1B	119.8	C9—C8—H8B	108.8
C1—C2—C3	120.16 (9)	C7—C8—H8B	108.8
C1—C2—H2B	119.9	H8A—C8—H8B	107.7
C3—C2—H2B	119.9	N1—C9—C8	112.79 (7)
C4—C3—C2	119.55 (9)	N1—C9—H9A	109.0
C4—C3—H3A	120.2	C8—C9—H9A	109.0
C2—C3—H3A	120.2	N1—C9—H9B	109.0
C3—C4—C5	120.22 (8)	C8—C9—H9B	109.0
C3—C4—H4A	119.9	H9A—C9—H9B	107.8
C5—C4—H4A	119.9	N2—C10—N1	111.96 (8)
C6—C5—C4	120.59 (8)	N2—C10—H10A	124.0
C6—C5—H5A	119.7	N1—C10—H10A	124.0
C4—C5—H5A	119.7	C12—C11—N2	110.28 (8)
C5—C6—C1	119.04 (8)	C12—C11—H11A	124.9
C5—C6—C7	120.32 (8)	N2—C11—H11A	124.9
C1—C6—C7	120.64 (8)	C11—C12—N1	105.80 (8)
O1—C7—C6	112.55 (7)	C11—C12—H12A	127.1
O1—C7—C8	107.72 (7)	N1—C12—H12A	127.1
C6—C1—C2—C3	−1.16 (13)	O1—C7—C8—C9	52.81 (10)
C1—C2—C3—C4	−0.15 (14)	C6—C7—C8—C9	176.07 (7)
C2—C3—C4—C5	1.41 (14)	C10—N1—C9—C8	−107.01 (10)
C3—C4—C5—C6	−1.37 (14)	C12—N1—C9—C8	71.41 (11)
C4—C5—C6—C1	0.06 (13)	C7—C8—C9—N1	59.04 (10)
C4—C5—C6—C7	179.56 (8)	C11—N2—C10—N1	−0.15 (11)
C2—C1—C6—C5	1.20 (12)	C12—N1—C10—N2	0.31 (11)
C2—C1—C6—C7	−178.30 (8)	C9—N1—C10—N2	178.99 (8)
C5—C6—C7—O1	−129.62 (8)	C10—N2—C11—C12	−0.07 (11)
C1—C6—C7—O1	49.88 (10)	N2—C11—C12—N1	0.25 (11)
C5—C6—C7—C8	109.98 (9)	C10—N1—C12—C11	−0.33 (10)
C1—C6—C7—C8	−70.52 (10)	C9—N1—C12—C11	−179.01 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N2i	0.964 (19)	1.89 (2)	2.8432 (12)	171.7 (17)
C1—H1B···O1ii	0.95	2.48	3.4188 (12)	172
C10—H10A···Cg1iii	0.95	2.68	3.4778 (12)	142
C12—H12A···Cg1iv	0.95	2.69	3.5373 (11)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N2i	0.964 (19)	1.89 (2)	2.8432 (12)	171.7 (17)
C1—H1B⋯O1ii	0.95	2.48	3.4188 (12)	172
C10—H10A⋯Cg1iii	0.95	2.68	3.4778 (12)	142
C12—H12A⋯Cg1iv	0.95	2.69	3.5373 (11)	149

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