3-[1-(3-Hydroxy-benz-yl)-1H-benz-imid-azol-2-yl]phenol.

In the title mol-ecule, C(20)H(16)N(2)O(2), the benzimidazole mean plane forms dihedral angles of 56.55 (3) and 81.65 (4)° with the two benzene rings. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into layers parallel to the (101) plane. The crystal packing also exhibits weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Demirayak et al. (2002 ▶); Minoura et al. (2004 ▶); Pawar et al. (2004 ▶); Tomei et al. (2003 ▶). For related structures, see: Eltayeb et al. (2007a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H16N2O2

M = 316.35

Monoclinic,

a = 10.5128 (2) Å

b = 12.1096 (2) Å

c = 12.5235 (2) Å

β = 96.948 (1)°

V = 1582.61 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.55 × 0.34 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.954, T max = 0.987

34106 measured reflections

7426 independent reflections

6004 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.05

7426 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809018698/cv2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018698/cv2563Isup2.hkl

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

C20H16N2O2	F(000) = 664
Mr = 316.35	Dx = 1.328 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8327 reflections
a = 10.5128 (2) Å	θ = 2.4–37.2°
b = 12.1096 (2) Å	µ = 0.09 mm−1
c = 12.5235 (2) Å	T = 100 K
β = 96.948 (1)°	Plate, colourless
V = 1582.61 (5) Å3	0.55 × 0.34 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7426 independent reflections
Radiation source: fine-focus sealed tube	6004 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 36.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→17
Tmin = 0.954, Tmax = 0.987	k = −20→20
34106 measured reflections	l = −19→20

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) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0723P)2 + 0.2344P] where P = (Fo2 + 2Fc2)/3
7426 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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

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	0.60369 (7)	0.60548 (5)	0.04595 (5)	0.01932 (13)
O2	0.21201 (7)	0.70928 (6)	0.49193 (6)	0.02850 (16)
N1	0.36876 (7)	0.35014 (5)	0.31082 (5)	0.01366 (12)
N2	0.55084 (7)	0.30903 (6)	0.41524 (5)	0.01468 (12)
C1	0.34113 (8)	0.26119 (6)	0.37376 (6)	0.01385 (13)
C2	0.22644 (8)	0.20556 (7)	0.38301 (6)	0.01625 (14)
H2A	0.1502	0.2247	0.3415	0.019*
C3	0.23254 (9)	0.12006 (7)	0.45759 (7)	0.01787 (15)
H3A	0.1581	0.0820	0.4676	0.021*
C4	0.34872 (9)	0.08978 (7)	0.51829 (7)	0.01903 (16)
H4A	0.3497	0.0308	0.5659	0.023*
C5	0.46206 (9)	0.14602 (7)	0.50872 (7)	0.01765 (15)
H5A	0.5388	0.1255	0.5486	0.021*
C6	0.45615 (8)	0.23468 (6)	0.43671 (6)	0.01408 (13)
C7	0.49493 (8)	0.37658 (6)	0.34028 (6)	0.01328 (13)
C8	0.55758 (8)	0.47449 (6)	0.29966 (6)	0.01346 (13)
C9	0.55681 (8)	0.49315 (6)	0.18938 (6)	0.01442 (13)
H9A	0.5214	0.4411	0.1398	0.017*
C10	0.60956 (8)	0.59058 (6)	0.15413 (6)	0.01466 (14)
C11	0.66423 (8)	0.66833 (7)	0.22849 (6)	0.01679 (15)
H11A	0.6988	0.7333	0.2049	0.020*
C12	0.66666 (9)	0.64783 (7)	0.33810 (7)	0.01769 (15)
H12A	0.7041	0.6990	0.3876	0.021*
C13	0.61356 (8)	0.55155 (7)	0.37433 (6)	0.01600 (14)
H13A	0.6153	0.5385	0.4477	0.019*
C14	0.27189 (8)	0.40916 (7)	0.23858 (6)	0.01493 (14)
H14A	0.2199	0.3560	0.1948	0.018*
H14B	0.3144	0.4556	0.1907	0.018*
C15	0.18581 (8)	0.47993 (7)	0.29866 (6)	0.01546 (14)
C16	0.05416 (9)	0.46392 (8)	0.28541 (7)	0.02214 (17)
H16A	0.0182	0.4078	0.2409	0.027*
C17	−0.02425 (10)	0.53232 (10)	0.33909 (9)	0.0298 (2)
H17A	−0.1126	0.5226	0.3289	0.036*
C18	0.02893 (10)	0.61473 (9)	0.40753 (8)	0.0276 (2)
H18A	−0.0235	0.6601	0.4432	0.033*
C19	0.16150 (9)	0.62907 (8)	0.42254 (7)	0.02011 (16)
C20	0.23951 (8)	0.56315 (7)	0.36681 (6)	0.01647 (14)
H20A	0.3276	0.5746	0.3750	0.020*
H1O1	0.6430 (17)	0.6716 (15)	0.0307 (14)	0.053 (5)*
H1O2	0.3026 (18)	0.6952 (15)	0.5216 (14)	0.055 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0266 (3)	0.0181 (3)	0.0133 (2)	−0.0054 (2)	0.0028 (2)	0.00132 (19)
O2	0.0206 (3)	0.0285 (3)	0.0336 (4)	0.0103 (3)	−0.0083 (3)	−0.0167 (3)
N1	0.0134 (3)	0.0145 (3)	0.0127 (3)	0.0004 (2)	0.0002 (2)	0.0011 (2)
N2	0.0139 (3)	0.0155 (3)	0.0144 (3)	0.0006 (2)	0.0007 (2)	0.0009 (2)
C1	0.0148 (3)	0.0135 (3)	0.0131 (3)	−0.0001 (2)	0.0012 (3)	−0.0002 (2)
C2	0.0151 (3)	0.0170 (3)	0.0162 (3)	−0.0022 (3)	0.0003 (3)	−0.0013 (2)
C3	0.0204 (4)	0.0161 (3)	0.0173 (3)	−0.0041 (3)	0.0029 (3)	−0.0011 (2)
C4	0.0242 (4)	0.0149 (3)	0.0181 (3)	−0.0023 (3)	0.0027 (3)	0.0015 (3)
C5	0.0197 (4)	0.0158 (3)	0.0169 (3)	0.0008 (3)	0.0001 (3)	0.0024 (2)
C6	0.0147 (3)	0.0136 (3)	0.0137 (3)	0.0002 (2)	0.0008 (3)	−0.0003 (2)
C7	0.0131 (3)	0.0143 (3)	0.0124 (3)	0.0001 (2)	0.0013 (2)	−0.0007 (2)
C8	0.0122 (3)	0.0142 (3)	0.0140 (3)	0.0001 (2)	0.0018 (2)	−0.0003 (2)
C9	0.0159 (3)	0.0142 (3)	0.0131 (3)	−0.0019 (2)	0.0018 (3)	−0.0008 (2)
C10	0.0154 (3)	0.0151 (3)	0.0138 (3)	−0.0006 (3)	0.0026 (3)	−0.0001 (2)
C11	0.0183 (4)	0.0148 (3)	0.0173 (3)	−0.0026 (3)	0.0023 (3)	−0.0013 (2)
C12	0.0186 (4)	0.0180 (3)	0.0165 (3)	−0.0035 (3)	0.0021 (3)	−0.0036 (2)
C13	0.0161 (4)	0.0180 (3)	0.0138 (3)	−0.0011 (3)	0.0016 (3)	−0.0019 (2)
C14	0.0145 (3)	0.0177 (3)	0.0120 (3)	0.0020 (3)	−0.0010 (3)	0.0002 (2)
C15	0.0148 (3)	0.0176 (3)	0.0136 (3)	0.0022 (3)	0.0000 (3)	0.0002 (2)
C16	0.0145 (4)	0.0283 (4)	0.0229 (4)	0.0005 (3)	−0.0007 (3)	−0.0069 (3)
C17	0.0133 (4)	0.0409 (6)	0.0349 (5)	0.0020 (4)	0.0017 (4)	−0.0144 (4)
C18	0.0162 (4)	0.0369 (5)	0.0292 (5)	0.0071 (4)	0.0002 (3)	−0.0126 (4)
C19	0.0174 (4)	0.0217 (4)	0.0200 (4)	0.0057 (3)	−0.0028 (3)	−0.0053 (3)
C20	0.0137 (3)	0.0178 (3)	0.0172 (3)	0.0026 (3)	−0.0006 (3)	−0.0017 (3)

O1—C10	1.3607 (10)	C9—C10	1.3977 (11)
O1—H1O1	0.931 (19)	C9—H9A	0.9300
O2—C19	1.3671 (11)	C10—C11	1.3980 (11)
O2—H1O2	0.994 (19)	C11—C12	1.3922 (11)
N1—C7	1.3709 (10)	C11—H11A	0.9300
N1—C1	1.3861 (10)	C12—C13	1.3922 (11)
N1—C14	1.4641 (11)	C12—H12A	0.9300
N2—C7	1.3275 (10)	C13—H13A	0.9300
N2—C6	1.3923 (10)	C14—C15	1.5114 (11)
C1—C2	1.3981 (11)	C14—H14A	0.9700
C1—C6	1.3986 (12)	C14—H14B	0.9700
C2—C3	1.3906 (11)	C15—C16	1.3874 (13)
C2—H2A	0.9300	C15—C20	1.3951 (11)
C3—C4	1.4070 (13)	C16—C17	1.3970 (13)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.3901 (12)	C17—C18	1.3882 (14)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.3987 (11)	C18—C19	1.3944 (14)
C5—H5A	0.9300	C18—H18A	0.9300
C7—C8	1.4763 (10)	C19—C20	1.3911 (11)
C8—C9	1.3985 (10)	C20—H20A	0.9300
C8—C13	1.3995 (11)
C10—O1—H1O1	110.5 (11)	C9—C10—C11	120.33 (7)
C19—O2—H1O2	113.3 (10)	C12—C11—C10	119.59 (7)
C7—N1—C1	106.91 (6)	C12—C11—H11A	120.2
C7—N1—C14	129.07 (7)	C10—C11—H11A	120.2
C1—N1—C14	123.56 (7)	C11—C12—C13	120.69 (8)
C7—N2—C6	105.62 (7)	C11—C12—H12A	119.7
N1—C1—C2	131.58 (8)	C13—C12—H12A	119.7
N1—C1—C6	105.82 (7)	C12—C13—C8	119.56 (7)
C2—C1—C6	122.56 (7)	C12—C13—H13A	120.2
C3—C2—C1	116.37 (8)	C8—C13—H13A	120.2
C3—C2—H2A	121.8	N1—C14—C15	112.50 (6)
C1—C2—H2A	121.8	N1—C14—H14A	109.1
C2—C3—C4	121.56 (8)	C15—C14—H14A	109.1
C2—C3—H3A	119.2	N1—C14—H14B	109.1
C4—C3—H3A	119.2	C15—C14—H14B	109.1
C5—C4—C3	121.52 (8)	H14A—C14—H14B	107.8
C5—C4—H4A	119.2	C16—C15—C20	119.87 (7)
C3—C4—H4A	119.2	C16—C15—C14	120.66 (7)
C4—C5—C6	117.39 (8)	C20—C15—C14	119.46 (7)
C4—C5—H5A	121.3	C15—C16—C17	119.85 (9)
C6—C5—H5A	121.3	C15—C16—H16A	120.1
N2—C6—C1	109.41 (7)	C17—C16—H16A	120.1
N2—C6—C5	130.08 (8)	C18—C17—C16	120.42 (9)
C1—C6—C5	120.50 (7)	C18—C17—H17A	119.8
N2—C7—N1	112.19 (7)	C16—C17—H17A	119.8
N2—C7—C8	124.10 (7)	C17—C18—C19	119.60 (8)
N1—C7—C8	123.52 (7)	C17—C18—H18A	120.2
C9—C8—C13	120.26 (7)	C19—C18—H18A	120.2
C9—C8—C7	121.37 (7)	O2—C19—C20	121.29 (8)
C13—C8—C7	118.31 (7)	O2—C19—C18	118.63 (8)
C10—C9—C8	119.55 (7)	C20—C19—C18	120.08 (8)
C10—C9—H9A	120.2	C19—C20—C15	120.13 (8)
C8—C9—H9A	120.2	C19—C20—H20A	119.9
O1—C10—C9	117.03 (7)	C15—C20—H20A	119.9
O1—C10—C11	122.64 (7)
C7—N1—C1—C2	175.17 (8)	N1—C7—C8—C13	121.97 (8)
C14—N1—C1—C2	2.30 (12)	C13—C8—C9—C10	−1.55 (12)
C7—N1—C1—C6	−2.40 (8)	C7—C8—C9—C10	175.65 (7)
C14—N1—C1—C6	−175.27 (6)	C8—C9—C10—O1	−178.61 (7)
N1—C1—C2—C3	−178.27 (8)	C8—C9—C10—C11	0.81 (12)
C6—C1—C2—C3	−1.05 (11)	O1—C10—C11—C12	179.82 (8)
C1—C2—C3—C4	−1.54 (12)	C9—C10—C11—C12	0.44 (13)
C2—C3—C4—C5	1.89 (13)	C10—C11—C12—C13	−0.95 (13)
C3—C4—C5—C6	0.40 (12)	C11—C12—C13—C8	0.22 (13)
C7—N2—C6—C1	−1.16 (8)	C9—C8—C13—C12	1.04 (12)
C7—N2—C6—C5	180.00 (8)	C7—C8—C13—C12	−176.24 (8)
N1—C1—C6—N2	2.23 (8)	C7—N1—C14—C15	−98.85 (9)
C2—C1—C6—N2	−175.61 (7)	C1—N1—C14—C15	72.35 (9)
N1—C1—C6—C5	−178.80 (7)	N1—C14—C15—C16	−121.88 (9)
C2—C1—C6—C5	3.37 (11)	N1—C14—C15—C20	59.08 (10)
C4—C5—C6—N2	175.81 (8)	C20—C15—C16—C17	0.98 (14)
C4—C5—C6—C1	−2.93 (11)	C14—C15—C16—C17	−178.05 (9)
C6—N2—C7—N1	−0.41 (8)	C15—C16—C17—C18	−1.43 (17)
C6—N2—C7—C8	174.77 (7)	C16—C17—C18—C19	0.02 (18)
C1—N1—C7—N2	1.81 (8)	C17—C18—C19—O2	−178.72 (10)
C14—N1—C7—N2	174.16 (7)	C17—C18—C19—C20	1.83 (16)
C1—N1—C7—C8	−173.40 (7)	O2—C19—C20—C15	178.29 (8)
C14—N1—C7—C8	−1.05 (11)	C18—C19—C20—C15	−2.28 (14)
N2—C7—C8—C9	130.08 (8)	C16—C15—C20—C19	0.86 (13)
N1—C7—C8—C9	−55.28 (11)	C14—C15—C20—C19	179.91 (8)
N2—C7—C8—C13	−52.67 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.931 (19)	1.712 (19)	2.6406 (9)	175.4 (17)
O2—H1O2···N2ii	0.994 (19)	1.646 (19)	2.6297 (10)	169.7 (16)
C3—H3A···O1iii	0.93	2.57	3.2987 (10)	136
C9—H9A···O1iv	0.93	2.59	3.4287 (10)	150
C12—H12A···Cg1ii	0.93	2.67	3.4521 (9)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.931 (19)	1.712 (19)	2.6406 (9)	175.4 (17)
O2—H1O2⋯N2ii	0.994 (19)	1.646 (19)	2.6297 (10)	169.7 (16)
C3—H3A⋯O1iii	0.93	2.57	3.2987 (10)	136
C9—H9A⋯O1iv	0.93	2.59	3.4287 (10)	150
C12—H12A⋯Cg1ii	0.93	2.67	3.4521 (9)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the ring C1–C6.