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

Eltayeb, N.E.; Teoh, S.G.; Adnan, R.; Fun, H.-K.; Chantrapromma, S.

doi:10.1107/S1600536809049770

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3227-o3228

doi:10.1107/S1600536809049770

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

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Rohana Adnan,^a Hoong-Kun Fun ^b ^*§ and Suchada Chantrapromma ^c ¶

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 16 November 2009; accepted 20 November 2009; online 28 November 2009)

The title compound, 0.75C₁₅H₁₄N₂O·0.25C₁₅H₁₄N₂O, 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-benzimidazol-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 molecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal packing, molecules 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 intermolecular C—H⋯π interactions. A π–π interaction 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_r = 238.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.131
S = 1.07
3703 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 and Cg3 are the centroids of the C1–C6 and C8–C13 rings, respectively.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049770/sj2688sup1.cif

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

checkCIF report

Comment top

Benzimidazoles are regarded as a promising class of bioactive heterocyclic compounds that exhibit a variety of bioactivities displaying antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Guven et al., 2007; Pawar et al., 2005), antiviral (Tomei et al., 2003); anti-inflammatory (Thakurdesai et al., 2007) and anticancer (Demirayak et al., 2002) properties. As part of our research on screening benzimidazoles for their biological activities, we have previously reported the synthesis and crystal structures of some benzimidazoles (Eltayeb et al., 2007; 2009a,b). In continuation of this research the title compound (I) was synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound (Fig. 1) consists of [2-methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol] as a major component and [2-methyl-6-(5-methyl-1H-benzimidazol-2-yl)phenol] as a minor component. The refined site-occupancy ratio of the major and the minor components is 0.746 (4)/0.254 (4). The conformation of both components are identical except the benzimidazole methyl group is positionally disordered over two positions on atoms C10 and C11 (Fig. 1). The molecule is essentially planar with the dihedral angle between the benzimidazole and benzene ring being 3.49 (4)°. The benzimidazole ring system (N1/N2/C7–C13) is planar with an rms deviation of 0.008 (1)Å. The imidazole ring (N1/N2/C7–C8/C13) makes the dihedral angles of 1.28 (6) and 3.01 (6)° with the C8–C13 and C1–C6 benzene rings, respectively. An intramolecular O—H···N hydrogen bond (Fig. 1) generates an S(6) ring motif (Bernstein et al., 1995) and helps to maintain the planarity of the molecule. Bond lengths in (I) are in normal ranges (Allen et al., 1987) and comparable with those in related structures (Eltayeb et al., 2007; 2009a, b; Xiao et al., 2009).

The crystal packing of the major component was shown in Fig. 2, the molecules being linked in an antiparallel manner through an N—H···O hydrogen bond into chains along the [2 0 1] direction. These chains are stacked approximately along the a axis (Table 1). C—H···π (Table 1) and π–π interactions were also present with the distance Cg₁···Cg₂ = 3.6241 (6) Å (symmetry code -1+x, y, z); Cg₁, Cg₂ and Cg₃ are the centroids of the N1/N2/C7–C8/C13, C1–C6 and C8–C13 rings, respectively.

Related literature top

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). Cg2 and Cg3 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Experimental top

3-Methylsalicylaldehyde (0.5 g, 4 mmol) was added to a solution of 4-methyl-1,2-phenylenediamine (0.244 g, 2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow needle-shaped single crystals of the title compound suitable for x-ray structure determination were obtained by slow evaporation of the filtrate at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. Open bonds show the minor disorder component
	Fig. 2. The crystal packing of the major component of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines and only the major disorder component is shown.

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

Crystal data top

0.75C₁₅H₁₄N₂O·0.25C₁₅H₁₄N₂O	F(000) = 504
M_r = 238.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0668P)² + 0.4392P] where P = (F_o² + 2F_c²)/3
3703 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

0.75C₁₅H₁₄N₂O·0.25C₁₅H₁₄N₂O	V = 1164.80 (5) Å³
M_r = 238.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9231 (1) Å	µ = 0.09 mm⁻¹
b = 19.8900 (6) Å	T = 100 K
c = 12.3199 (3) Å	0.59 × 0.17 × 0.10 mm
β = 105.085 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3703 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3165 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.992	R_int = 0.030
34431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.61 e Å⁻³
3703 reflections	Δρ_min = −0.20 e Å⁻³
184 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	0.75C₁₅H₁₄N₂O·0.25C₁₅H₁₄N₂O
M_r	238.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	4.9231 (1), 19.8900 (6), 12.3199 (3)
β (°)	105.085 (1)
V (Å³)	1164.80 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.59 × 0.17 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.951, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	34431, 3703, 3165
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 1.07
No. of reflections	3703
No. of parameters	184
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2.

Footnotes

‡On study leave from: Department of Chemistry, International University of Africa, Khartoum, Sudan. E-mail: nasertaha90@hotmail.com.

§Thomson Reuters ResearcherID: A-3561-2009.

¶Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank the Malaysian Government, Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the FRGS, RU research grants (PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120) and the University Golden Goose grant No. 1001/PFIZIK/811012. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE.

References

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Volume 65| Part 12| December 2009| Pages o3227-o3228

doi:10.1107/S1600536809049770

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

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