2-Methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol-2-methyl-6-(5-methyl-1H-benzimidazol-2-yl)phenol (3/1).

The title compound, 0.75C(15)H(14)N(2)O·0.25C(15)H(14)N(2)O, is a co-crystal of 2-methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol as the major component and 2-methyl-6-(5-methyl-1H-benz-imidazol-2-yl)phenol as the minor component. The refined site-occupancy ratio is 0.746 (4)/0.254 (4). The conformations of both components are identical except for that of the methyl substituent on the benzene ring of the benzimidazole unit which is positionally disordered over two positions. The mol-ecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4)°. An intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal packing, mol-ecules are linked through N-H⋯O hydrogen bonds into chains along [201]. These chains are stacked approximately along the a-axis direction. The crystal packing is further stabilized by weak N-H⋯O and O⋯H⋯N hydrogen bonds, together with weak inter-molecular C-H⋯π inter-actions. A π-π inter-action with a centroid-centroid distance of 3.6241 (6) Å is also observed between the substituted phenyl ring and that of the benzimidazole system.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to benzimidazoles and their bioactivity, see: Demirayak et al. (2002 ▶); Guven et al. (2007 ▶); Minoura et al. (2004 ▶); Pawar et al. (2005 ▶); Thakurdesai et al. (2007 ▶); Tomei et al. (2003 ▶). For related structures, see: Eltayeb et al. (2007 ▶, 2009a ▶,b ▶); Xiao et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

0.75C15H14N2O·0.25C15H14N2O

M = 238.28

Monoclinic,

a = 4.9231 (1) Å

b = 19.8900 (6) Å

c = 12.3199 (3) Å

β = 105.085 (1)°

V = 1164.80 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.59 × 0.17 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.951, T max = 0.992

34431 measured reflections

3703 independent reflections

3165 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.131

S = 1.07

3703 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.20 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/S1600536809049770/sj2688sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049770/sj2688Isup2.hkl

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

0.75C15H14N2O·0.25C15H14N2O	F(000) = 504
Mr = 238.28	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Melting point: ?' K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.9231 (1) Å	Cell parameters from 3703 reflections
b = 19.8900 (6) Å	θ = 2.0–31.0°
c = 12.3199 (3) Å	µ = 0.09 mm−1
β = 105.085 (1)°	T = 100 K
V = 1164.80 (5) Å3	Needle, yellow
Z = 4	0.59 × 0.17 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	3703 independent reflections
Radiation source: sealed tube	3165 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 31.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.951, Tmax = 0.992	k = −28→28
34431 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.4392P] where P = (Fo2 + 2Fc2)/3
3703 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.20 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	Occ. (<1)
O1	1.19279 (16)	0.73306 (4)	0.38129 (6)	0.01798 (17)
N1	0.75983 (18)	0.80945 (5)	0.29676 (7)	0.01616 (18)
N2	0.51410 (19)	0.79954 (5)	0.11676 (8)	0.01659 (18)
C1	1.1529 (2)	0.70454 (5)	0.27765 (8)	0.01503 (19)
C2	1.3414 (2)	0.65397 (5)	0.26490 (9)	0.0167 (2)
C3	1.3081 (2)	0.62518 (6)	0.15941 (10)	0.0202 (2)
H3A	1.4326	0.5918	0.1501	0.024*
C4	1.0927 (2)	0.64511 (6)	0.06716 (10)	0.0226 (2)
H4A	1.0756	0.6256	−0.0029	0.027*
C5	0.9042 (2)	0.69426 (6)	0.08074 (9)	0.0189 (2)
H5A	0.7591	0.7073	0.0196	0.023*
C6	0.9303 (2)	0.72445 (5)	0.18570 (8)	0.01520 (19)
C7	0.7363 (2)	0.77685 (5)	0.20056 (8)	0.01523 (19)
C8	0.3873 (2)	0.85056 (5)	0.16229 (9)	0.0164 (2)
C9	0.1586 (2)	0.89213 (5)	0.11465 (9)	0.0187 (2)
H9A	0.0587	0.8876	0.0398	0.022*
C10	0.0862 (2)	0.94063 (6)	0.18357 (10)	0.0197 (2)
H10A	−0.0692	0.9702	0.1537	0.024*	0.254 (4)
C11	0.2396 (2)	0.94650 (6)	0.29702 (10)	0.0202 (2)
H11A	0.1853	0.9801	0.3432	0.024*	0.746 (4)
C12	0.4672 (2)	0.90501 (6)	0.34381 (9)	0.0199 (2)
H12A	0.5665	0.9094	0.4188	0.024*
C13	0.5427 (2)	0.85640 (5)	0.27486 (9)	0.0163 (2)
C14	1.5751 (2)	0.63299 (6)	0.36352 (9)	0.0208 (2)
H14A	1.6860	0.5988	0.3405	0.031*
H14B	1.4973	0.6156	0.4216	0.031*
H14C	1.6918	0.6711	0.3916	0.031*
C15	−0.1576 (3)	0.98865 (7)	0.13834 (13)	0.0201 (3)	0.746 (4)
H15A	−0.2119	0.9866	0.0577	0.030*	0.746 (4)
H15B	−0.1006	1.0336	0.1620	0.030*	0.746 (4)
H15C	−0.3142	0.9760	0.1668	0.030*	0.746 (4)
C15A	0.1355 (10)	0.9949 (2)	0.3651 (5)	0.0267 (11)	0.254 (4)
H15D	0.2593	0.9959	0.4395	0.040*	0.254 (4)
H15E	−0.0496	0.9820	0.3689	0.040*	0.254 (4)
H15F	0.1282	1.0387	0.3317	0.040*	0.254 (4)
H1N2	0.445 (4)	0.7809 (10)	0.0451 (16)	0.041 (5)*
H1O1	1.058 (5)	0.7671 (11)	0.3717 (19)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0181 (4)	0.0218 (4)	0.0123 (3)	0.0025 (3)	0.0008 (3)	−0.0007 (3)
N1	0.0156 (4)	0.0180 (4)	0.0141 (4)	0.0009 (3)	0.0025 (3)	0.0006 (3)
N2	0.0152 (4)	0.0189 (4)	0.0138 (4)	0.0011 (3)	0.0005 (3)	0.0000 (3)
C1	0.0143 (4)	0.0174 (4)	0.0126 (4)	−0.0020 (3)	0.0021 (3)	0.0010 (3)
C2	0.0149 (4)	0.0180 (4)	0.0164 (5)	−0.0004 (3)	0.0026 (3)	0.0014 (4)
C3	0.0183 (5)	0.0219 (5)	0.0196 (5)	0.0025 (4)	0.0037 (4)	−0.0019 (4)
C4	0.0211 (5)	0.0272 (5)	0.0181 (5)	0.0024 (4)	0.0030 (4)	−0.0046 (4)
C5	0.0174 (5)	0.0238 (5)	0.0137 (4)	0.0013 (4)	0.0007 (4)	−0.0014 (4)
C6	0.0142 (4)	0.0174 (4)	0.0133 (4)	−0.0003 (3)	0.0024 (3)	0.0001 (3)
C7	0.0136 (4)	0.0175 (4)	0.0136 (4)	−0.0005 (3)	0.0019 (3)	0.0018 (3)
C8	0.0148 (4)	0.0172 (4)	0.0163 (5)	−0.0010 (3)	0.0024 (3)	0.0008 (3)
C9	0.0157 (4)	0.0201 (5)	0.0184 (5)	0.0001 (4)	0.0010 (4)	0.0022 (4)
C10	0.0162 (4)	0.0194 (5)	0.0228 (5)	−0.0002 (4)	0.0037 (4)	0.0032 (4)
C11	0.0197 (5)	0.0195 (5)	0.0216 (5)	0.0008 (4)	0.0060 (4)	−0.0005 (4)
C12	0.0201 (5)	0.0220 (5)	0.0172 (5)	0.0007 (4)	0.0040 (4)	−0.0007 (4)
C13	0.0152 (4)	0.0174 (4)	0.0157 (5)	−0.0002 (3)	0.0027 (3)	0.0020 (3)
C14	0.0177 (5)	0.0234 (5)	0.0192 (5)	0.0033 (4)	0.0012 (4)	0.0023 (4)
C15	0.0167 (6)	0.0179 (7)	0.0243 (7)	0.0024 (5)	0.0027 (5)	0.0019 (5)
C15A	0.023 (2)	0.024 (2)	0.035 (3)	0.0009 (17)	0.0110 (19)	−0.0034 (18)

O1—C1	1.3639 (12)	C9—H9A	0.9300
O1—H1O1	0.93 (2)	C10—C11	1.4100 (16)
N1—C7	1.3291 (13)	C10—C15	1.5217 (18)
N1—C13	1.3919 (13)	C10—H10A	0.9599
N2—C7	1.3706 (13)	C11—C12	1.3902 (15)
N2—C8	1.3842 (14)	C11—C15A	1.454 (5)
N2—H1N2	0.936 (19)	C11—H11A	0.9600
C1—C2	1.4045 (14)	C12—C13	1.3996 (15)
C1—C6	1.4124 (14)	C12—H12A	0.9300
C2—C3	1.3904 (15)	C14—H14A	0.9600
C2—C14	1.4990 (15)	C14—H14B	0.9600
C3—C4	1.3951 (16)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H10A	0.5624
C4—C5	1.3877 (15)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.4009 (14)	C15—H15C	0.9600
C5—H5A	0.9300	C15A—H11A	0.5030
C6—C7	1.4572 (14)	C15A—H15D	0.9600
C8—C9	1.3970 (14)	C15A—H15E	0.9600
C8—C13	1.4035 (14)	C15A—H15F	0.9600
C9—C10	1.3915 (16)
C1—O1—H1O1	105.0 (14)	C9—C10—C15	120.98 (11)
C7—N1—C13	105.67 (8)	C11—C10—C15	118.62 (11)
C7—N2—C8	106.97 (9)	C9—C10—H10A	119.8
C7—N2—H1N2	127.1 (12)	C11—C10—H10A	119.8
C8—N2—H1N2	125.5 (12)	C12—C11—C10	121.86 (10)
O1—C1—C2	117.66 (9)	C12—C11—C15A	121.4 (2)
O1—C1—C6	121.79 (9)	C10—C11—C15A	116.6 (2)
C2—C1—C6	120.55 (9)	C12—C11—H11A	119.1
C3—C2—C1	118.62 (10)	C10—C11—H11A	119.0
C3—C2—C14	121.45 (10)	C11—C12—C13	118.11 (10)
C1—C2—C14	119.92 (9)	C11—C12—H12A	120.9
C2—C3—C4	121.60 (10)	C13—C12—H12A	120.9
C2—C3—H3A	119.2	N1—C13—C12	131.12 (10)
C4—C3—H3A	119.2	N1—C13—C8	109.24 (9)
C5—C4—C3	119.50 (10)	C12—C13—C8	119.63 (10)
C5—C4—H4A	120.2	C2—C14—H14A	109.5
C3—C4—H4A	120.2	C2—C14—H14B	109.5
C4—C5—C6	120.63 (10)	H14A—C14—H14B	109.5
C4—C5—H5A	119.7	C2—C14—H14C	109.5
C6—C5—H5A	119.7	H14A—C14—H14C	109.5
C5—C6—C1	119.07 (9)	H14B—C14—H14C	109.5
C5—C6—C7	121.12 (9)	C10—C15—H15A	109.5
C1—C6—C7	119.80 (9)	H10A—C15—H15A	107.6
N1—C7—N2	112.23 (9)	C10—C15—H15B	109.5
N1—C7—C6	123.58 (9)	H10A—C15—H15B	111.4
N2—C7—C6	124.17 (9)	C10—C15—H15C	109.5
N2—C8—C9	131.51 (10)	H10A—C15—H15C	109.4
N2—C8—C13	105.89 (9)	C11—C15A—H15D	109.5
C9—C8—C13	122.58 (10)	C11—C15A—H15E	109.5
C10—C9—C8	117.42 (10)	H15D—C15A—H15E	109.5
C10—C9—H9A	121.3	C11—C15A—H15F	109.5
C8—C9—H9A	121.3	H15D—C15A—H15F	109.5
C9—C10—C11	120.40 (10)	H15E—C15A—H15F	109.5
O1—C1—C2—C3	−178.69 (9)	C1—C6—C7—N2	−179.91 (9)
C6—C1—C2—C3	1.56 (15)	C7—N2—C8—C9	178.20 (11)
O1—C1—C2—C14	0.27 (14)	C7—N2—C8—C13	−0.17 (11)
C6—C1—C2—C14	−179.49 (9)	N2—C8—C9—C10	−178.36 (11)
C1—C2—C3—C4	−0.34 (17)	C13—C8—C9—C10	−0.22 (16)
C14—C2—C3—C4	−179.28 (10)	C8—C9—C10—C11	−0.31 (16)
C2—C3—C4—C5	−0.80 (18)	C8—C9—C10—C15	179.22 (11)
C3—C4—C5—C6	0.73 (17)	C9—C10—C11—C12	0.42 (17)
C4—C5—C6—C1	0.46 (16)	C15—C10—C11—C12	−179.13 (11)
C4—C5—C6—C7	179.02 (10)	C9—C10—C11—C15A	−175.2 (2)
O1—C1—C6—C5	178.63 (9)	C15—C10—C11—C15A	5.2 (3)
C2—C1—C6—C5	−1.62 (15)	C10—C11—C12—C13	0.03 (17)
O1—C1—C6—C7	0.06 (15)	C15A—C11—C12—C13	175.5 (2)
C2—C1—C6—C7	179.81 (9)	C7—N1—C13—C12	−178.89 (11)
C13—N1—C7—N2	−0.43 (12)	C7—N1—C13—C8	0.31 (11)
C13—N1—C7—C6	177.88 (9)	C11—C12—C13—N1	178.57 (10)
C8—N2—C7—N1	0.39 (12)	C11—C12—C13—C8	−0.56 (16)
C8—N2—C7—C6	−177.91 (9)	N2—C8—C13—N1	−0.08 (11)
C5—C6—C7—N1	−176.56 (10)	C9—C8—C13—N1	−178.63 (9)
C1—C6—C7—N1	1.98 (15)	N2—C8—C13—C12	179.22 (9)
C5—C6—C7—N2	1.55 (16)	C9—C8—C13—C12	0.67 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.936 (19)	2.095 (19)	2.9916 (12)	160.1 (18)
O1—H1O1···N1	0.93 (2)	1.74 (2)	2.6040 (12)	153 (2)
C15—H15C···Cg3ii	0.96	2.66	3.5731 (16)	160
C15A—H15F···Cg2iii	0.96	2.96	3.780 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.936 (19)	2.095 (19)	2.9916 (12)	160.1 (18)
O1—H1O1⋯N1	0.93 (2)	1.74 (2)	2.6040 (12)	153 (2)
C15—H15C⋯Cg3ii	0.96	2.66	3.5731 (16)	160
C15A—H15F⋯Cg2iii	0.96	2.96	3.780 (4)	144

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of the C1–C6 and C8–C13 rings, respectively.