2-Meth­oxy-6-(6-methyl-1H-benzimid­azol-2-yl)phenol

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

doi:10.1107/S1600536809022478

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1613-o1614

doi:10.1107/S1600536809022478

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2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Ching Kheng Quah,^b § Hoong-Kun Fun ^b ^*¶ and Rohana Adnan ^a

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 8 June 2009; accepted 12 June 2009; online 17 June 2009)

In the title molecule, C₁₅H₁₄N₂O₂, the substituted benzene ring forms a dihedral angle of 4.15 (1)° with the benzimidazole ring system. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the solid state, molecules are linked into chains along the [001] via intermolecular bifurcated N—H⋯(O,O) hydrogen bonds, which generate R₁²(5) ring motifs. The crystal packing is also consolidated by C—H⋯π interactions, and π–π stacking interactions between the imidazole and substituted benzene rings [centroid–centroid distance = 3.5746 (13) Å]. The methyl group attached to the benzimidazole ring system is disordered over two positions with occupancies of 0.587 (6) and 0.413 (6), suggesting 180° rotational disorder for the benzimidazole group.

Related literature

For the biological activity of benzimidazole derivatives, see: Minoura et al. (2004 ); Pawar et al. (2004 ); Tomei et al. (2003 ); Rao et al. (2003 ); Demirayak et al. (2002 ). For related structures, see: Eltayeb et al. (2007a ,b ,c ); Yeap et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M_r = 254.28
Tetragonal, P 4₂ /n
a = 14.4118 (2) Å
c = 12.0995 (2) Å
V = 2513.07 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.27 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.969, T_max = 0.978
28200 measured reflections
2215 independent reflections
1725 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.156
S = 1.08
2215 reflections
193 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.92 (4)	2.03 (3)	2.919 (3)	164 (2)
N1—H1N⋯O2ⁱ	0.92 (4)	2.58 (3)	3.168 (3)	123 (2)
O1—H1O⋯N2	0.97 (3)	1.61 (3)	2.572 (3)	167 (3)
C14—H14B⋯Cg1ⁱⁱ	0.96	2.95	3.840 (3)	154
Symmetry codes: (i) $[y+{\script{1\over 2}}, -x+1, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z. Cg1 is the centroid of the C8–C13 benzene ring.

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/S1600536809022478/ci2825sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022478/ci2825Isup2.hkl

checkCIF report

Comment top

The synthesis of benzimidazoles has received much attention owing to the varied biological activity such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), antiHIV (Rao et al., 2003), and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. Previously we reported crystal structures of 4-allyl-2-[1-(5-allyl-2-hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6- methoxyphenol (Eltayeb et al., 2007a), 2-(2-methoxynaphthalen-1-yl)-1- [(2-methoxynaphthalen-1-yl)methyl]-1H-benzimidazole (Eltayeb et al., 2007b) and 2-(benzimidazol-2-yl)-6-methoxyphenol (Eltayeb et al., 2007c). Owing to the biological importance of the attached benzimidazole ring system, we report here the single-crystal X-ray diffraction study of 2-methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol.

The bond lengths (Allen et al., 1987) and angles in the title molecule (Fig. 1) are normal and are comparable to those observed in a closely related structure (Yeap et al., 2009). The dihedral angle between the C8-C13 and N1/N2/C1-C7 rings is 4.15 (1)°. The molecular structure is stabilized by an intramolecular O1—H1O···N2 hydrogen bond which generates an S(6) ring motif (Bernstein et al., 1995).

In the solid state, the molecules are linked via intermolecular N1—H1N···O1 and N1—H1N···O2 bifurcated donor bonds into chains along the [001] (Fig. 2). These hydrogen bonds form an R₁²(5) ring motif. The crystal packing is consolidated by C—H···π (Table 1) interactions involving the C8-C13 benzene ring, and π–π stacking interactions between the C8—C13 (centroid Cg1) ring at (3/2-x, 1/2-y, z) and the N1/C1/C6/N2/C7 (centroid Cg2) ring at (x, y, z), with a Cg1···Cg2 distance of 3.5746 (13) Å.

Related literature top

For the biological activity of benzimidazoles derivatives, see: Minoura et al. (2004); Pawar et al. (2004); Tomei et al. (2003); Rao et al. (2003); Demirayak et al. (2002). For related structures, see: Eltayeb et al. (2007a,b,c); Yeap et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of 4-methyl-1,2-phenylenediamine (0.244 g, 2 mmol) in ethanol (30 ml) was added 3-methoxysalicylaldehyde (0.604 g, 4 mmol). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. The red powder obtained was dissolved in dichloromethane. Crystals suitable for XRD were formed after several days of slow evaporation of solvent at room temperature.

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, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular interactions are shown as dashed lines. Both disorder components are shown.
	Fig. 2. The crystal packing of the title compound, viewed along the [110]. Hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol top

Crystal data top

C₁₅H₁₄N₂O₂	D_x = 1.344 Mg m⁻³
M_r = 254.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₂/n	Cell parameters from 9054 reflections
Hall symbol: -P 4bc	θ = 2.2–29.6°
a = 14.4118 (2) Å	µ = 0.09 mm⁻¹
c = 12.0995 (2) Å	T = 100 K
V = 2513.07 (6) Å³	Block, yellow
Z = 8	0.35 × 0.27 × 0.24 mm
F(000) = 1072

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2215 independent reflections
Radiation source: fine-focus sealed tube	1725 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→16
T_min = 0.969, T_max = 0.978	k = −17→17
28200 measured reflections	l = −14→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0696P)² + 1.1514P] where P = (F_o² + 2F_c²)/3
2215 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.29 e Å⁻³
6 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂	Z = 8
M_r = 254.28	Mo Kα radiation
Tetragonal, P4₂/n	µ = 0.09 mm⁻¹
a = 14.4118 (2) Å	T = 100 K
c = 12.0995 (2) Å	0.35 × 0.27 × 0.24 mm
V = 2513.07 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2215 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1725 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.978	R_int = 0.033
28200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	6 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.29 e Å⁻³
2215 reflections	Δρ_min = −0.17 e Å⁻³
193 parameters

Special details top

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 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 > 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.63382 (12)	0.20396 (13)	−0.12954 (12)	0.0575 (5)
H1O	0.632 (2)	0.268 (2)	−0.104 (3)	0.094 (10)*
O2	0.63393 (12)	0.02461 (12)	−0.12218 (13)	0.0641 (5)
N1	0.62805 (13)	0.37806 (15)	0.14723 (17)	0.0556 (5)
H1N	0.6438 (18)	0.3647 (18)	0.219 (3)	0.077 (8)*
N2	0.62434 (13)	0.36357 (13)	−0.03521 (15)	0.0506 (5)
C1	0.62626 (15)	0.46707 (17)	0.1047 (2)	0.0579 (6)
C2	0.62707 (18)	0.5541 (2)	0.1545 (3)	0.0726 (8)
H2	0.6299	0.5608	0.2309	0.087*
C3	0.62340 (18)	0.63115 (19)	0.0839 (3)	0.0753 (8)
H3	0.6235	0.6906	0.1139	0.090*	0.413 (6)
C4	0.6197 (2)	0.6204 (2)	−0.0292 (3)	0.0787 (9)
H4	0.6168	0.6729	−0.0738	0.094*	0.587 (6)
C5	0.62015 (19)	0.53499 (19)	−0.0773 (3)	0.0730 (8)
H5	0.6182	0.5289	−0.1538	0.088*
C6	0.62354 (15)	0.45686 (17)	−0.0092 (2)	0.0540 (6)
C7	0.62715 (14)	0.31865 (16)	0.06068 (17)	0.0469 (6)
C8	0.62766 (14)	0.21826 (16)	0.06973 (17)	0.0456 (5)
C9	0.63060 (14)	0.16508 (16)	−0.02796 (16)	0.0456 (5)
C10	0.63048 (15)	0.06902 (17)	−0.02064 (18)	0.0511 (6)
C11	0.62696 (16)	0.02486 (17)	0.0801 (2)	0.0559 (6)
H11	0.6263	−0.0396	0.0838	0.067*
C12	0.62437 (16)	0.07732 (17)	0.17613 (19)	0.0572 (6)
H12	0.6227	0.0478	0.2444	0.069*
C13	0.62424 (15)	0.17223 (16)	0.17120 (18)	0.0513 (6)
H13	0.6218	0.2065	0.2363	0.062*
C14	0.6320 (2)	−0.07360 (18)	−0.1201 (2)	0.0739 (8)
H14A	0.6353	−0.0970	−0.1942	0.111*
H14B	0.5754	−0.0942	−0.0862	0.111*
H14C	0.6840	−0.0962	−0.0784	0.111*
C15	0.6189 (3)	0.7303 (3)	0.1250 (4)	0.0672 (15)	0.587 (6)
H15A	0.6664	0.7664	0.0896	0.101*	0.587 (6)
H15B	0.6282	0.7314	0.2035	0.101*	0.587 (6)
H15C	0.5592	0.7561	0.1078	0.101*	0.587 (6)
C15A	0.6243 (6)	0.7101 (5)	−0.0739 (9)	0.106 (3)	0.413 (6)
H15D	0.5763	0.7175	−0.1282	0.160*	0.413 (6)
H15E	0.6837	0.7191	−0.1080	0.160*	0.413 (6)
H15F	0.6159	0.7549	−0.0161	0.160*	0.413 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0754 (11)	0.0642 (11)	0.0329 (9)	0.0026 (8)	0.0016 (7)	0.0016 (7)
O2	0.0800 (12)	0.0649 (11)	0.0474 (10)	0.0083 (9)	−0.0050 (8)	−0.0113 (8)
N1	0.0574 (12)	0.0687 (14)	0.0407 (11)	0.0040 (10)	−0.0037 (9)	−0.0075 (10)
N2	0.0537 (12)	0.0567 (12)	0.0415 (11)	0.0009 (9)	0.0024 (8)	0.0063 (9)
C1	0.0444 (13)	0.0568 (15)	0.0725 (17)	0.0022 (10)	0.0038 (11)	−0.0055 (12)
C2	0.0608 (16)	0.079 (2)	0.0781 (18)	0.0009 (13)	0.0067 (14)	−0.0209 (16)
C3	0.0564 (15)	0.0563 (16)	0.113 (2)	−0.0023 (12)	0.0144 (15)	−0.0108 (15)
C4	0.0736 (19)	0.071 (2)	0.092 (2)	−0.0012 (14)	0.0211 (16)	0.0047 (16)
C5	0.0750 (18)	0.0601 (17)	0.0837 (19)	0.0024 (13)	0.0163 (15)	0.0105 (15)
C6	0.0490 (13)	0.0562 (15)	0.0568 (15)	−0.0009 (10)	0.0053 (11)	0.0012 (11)
C7	0.0393 (12)	0.0602 (14)	0.0413 (13)	−0.0005 (10)	−0.0004 (9)	−0.0022 (10)
C8	0.0388 (11)	0.0593 (14)	0.0387 (12)	0.0020 (9)	−0.0018 (9)	0.0024 (10)
C9	0.0405 (12)	0.0641 (15)	0.0323 (11)	0.0027 (10)	0.0007 (9)	0.0040 (10)
C10	0.0476 (13)	0.0619 (15)	0.0438 (13)	0.0049 (10)	−0.0056 (10)	−0.0051 (10)
C11	0.0579 (14)	0.0548 (14)	0.0549 (15)	0.0010 (11)	−0.0065 (11)	0.0047 (11)
C12	0.0632 (15)	0.0655 (16)	0.0429 (13)	0.0008 (12)	−0.0042 (11)	0.0075 (11)
C13	0.0563 (14)	0.0637 (15)	0.0338 (12)	0.0018 (11)	−0.0030 (10)	0.0008 (10)
C14	0.085 (2)	0.0676 (18)	0.0689 (18)	0.0108 (14)	−0.0186 (15)	−0.0187 (14)
C15	0.066 (3)	0.061 (3)	0.074 (3)	0.001 (2)	0.005 (2)	−0.009 (2)
C15A	0.102 (6)	0.056 (5)	0.162 (9)	0.003 (4)	0.001 (6)	0.031 (5)

Geometric parameters (Å, º) top

O1—C9	1.352 (2)	C5—H5	0.93
O1—H1O	0.97 (3)	C7—C8	1.451 (3)
O2—C10	1.386 (3)	C8—C13	1.396 (3)
O2—C14	1.416 (3)	C8—C9	1.409 (3)
N1—C7	1.353 (3)	C9—C10	1.387 (3)
N1—C1	1.382 (3)	C10—C11	1.376 (3)
N1—H1N	0.92 (3)	C11—C12	1.387 (3)
N2—C7	1.329 (3)	C11—H11	0.93
N2—C6	1.381 (3)	C12—C13	1.369 (3)
C1—C6	1.387 (4)	C12—H12	0.93
C1—C2	1.392 (4)	C13—H13	0.93
C2—C3	1.402 (4)	C14—H14A	0.96
C2—H2	0.93	C14—H14B	0.96
C3—C4	1.378 (5)	C14—H14C	0.96
C3—C15	1.515 (5)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.362 (4)	C15—H15C	0.96
C4—C15A	1.403 (8)	C15A—H15D	0.96
C4—H4	0.93	C15A—H15E	0.96
C5—C6	1.396 (4)	C15A—H15F	0.96

C9—O1—H1O	95.9 (19)	C13—C8—C7	122.7 (2)
C10—O2—C14	116.42 (19)	C9—C8—C7	118.62 (19)
C7—N1—C1	107.4 (2)	O1—C9—C10	118.15 (19)
C7—N1—H1N	127.0 (17)	O1—C9—C8	122.6 (2)
C1—N1—H1N	123.5 (16)	C10—C9—C8	119.28 (19)
C7—N2—C6	106.02 (19)	C11—C10—O2	125.0 (2)
N1—C1—C6	105.8 (2)	C11—C10—C9	121.2 (2)
N1—C1—C2	132.5 (3)	O2—C10—C9	113.8 (2)
C6—C1—C2	121.8 (3)	C10—C11—C12	119.4 (2)
C1—C2—C3	116.7 (3)	C10—C11—H11	120.3
C1—C2—H2	121.6	C12—C11—H11	120.3
C3—C2—H2	121.6	C13—C12—C11	120.5 (2)
C4—C3—C2	121.2 (3)	C13—C12—H12	119.7
C4—C3—C15	115.5 (3)	C11—C12—H12	119.7
C2—C3—C15	123.3 (3)	C12—C13—C8	120.8 (2)
C4—C3—H3	119.4	C12—C13—H13	119.6
C2—C3—H3	119.4	C8—C13—H13	119.6
C5—C4—C3	121.7 (3)	O2—C14—H14A	109.5
C5—C4—C15A	131.9 (5)	O2—C14—H14B	109.5
C3—C4—C15A	106.1 (5)	H14A—C14—H14B	109.5
C5—C4—H4	119.1	O2—C14—H14C	109.5
C3—C4—H4	119.1	H14A—C14—H14C	109.5
C4—C5—C6	118.5 (3)	H14B—C14—H14C	109.5
C4—C5—H5	120.8	C3—C15—H15A	109.5
C6—C5—H5	120.8	C3—C15—H15B	109.5
N2—C6—C1	109.2 (2)	C3—C15—H15C	109.5
N2—C6—C5	130.7 (2)	C4—C15A—H15D	109.5
C1—C6—C5	120.1 (2)	C4—C15A—H15E	109.5
N2—C7—N1	111.6 (2)	H15D—C15A—H15E	109.5
N2—C7—C8	123.48 (19)	C4—C15A—H15F	109.5
N1—C7—C8	124.9 (2)	H15D—C15A—H15F	109.5
C13—C8—C9	118.7 (2)	H15E—C15A—H15F	109.5

C7—N1—C1—C6	0.5 (2)	C1—N1—C7—N2	−0.4 (2)
C7—N1—C1—C2	−179.3 (2)	C1—N1—C7—C8	−179.45 (19)
N1—C1—C2—C3	−179.2 (2)	N2—C7—C8—C13	−175.5 (2)
C6—C1—C2—C3	1.1 (4)	N1—C7—C8—C13	3.5 (3)
C1—C2—C3—C4	−0.4 (4)	N2—C7—C8—C9	3.7 (3)
C1—C2—C3—C15	176.8 (3)	N1—C7—C8—C9	−177.3 (2)
C2—C3—C4—C5	−0.5 (4)	C13—C8—C9—O1	179.87 (19)
C15—C3—C4—C5	−177.9 (3)	C7—C8—C9—O1	0.6 (3)
C2—C3—C4—C15A	−175.4 (4)	C13—C8—C9—C10	−0.3 (3)
C15—C3—C4—C15A	7.2 (5)	C7—C8—C9—C10	−179.56 (19)
C3—C4—C5—C6	0.6 (4)	C14—O2—C10—C11	1.1 (3)
C15A—C4—C5—C6	174.0 (5)	C14—O2—C10—C9	−178.7 (2)
C7—N2—C6—C1	0.2 (2)	O1—C9—C10—C11	−179.8 (2)
C7—N2—C6—C5	−179.4 (2)	C8—C9—C10—C11	0.4 (3)
N1—C1—C6—N2	−0.4 (3)	O1—C9—C10—O2	0.1 (3)
C2—C1—C6—N2	179.4 (2)	C8—C9—C10—O2	−179.74 (18)
N1—C1—C6—C5	179.3 (2)	O2—C10—C11—C12	179.6 (2)
C2—C1—C6—C5	−0.9 (4)	C9—C10—C11—C12	−0.6 (3)
C4—C5—C6—N2	179.7 (2)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C1	0.1 (4)	C11—C12—C13—C8	−0.7 (3)
C6—N2—C7—N1	0.1 (2)	C9—C8—C13—C12	0.4 (3)
C6—N2—C7—C8	179.20 (19)	C7—C8—C13—C12	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.92 (4)	2.03 (3)	2.919 (3)	164 (2)
N1—H1N···O2ⁱ	0.92 (4)	2.58 (3)	3.168 (3)	123 (2)
O1—H1O···N2	0.97 (3)	1.61 (3)	2.572 (3)	167 (3)
C14—H14B···Cg1ⁱⁱ	0.96	2.95	3.840 (3)	154

Symmetry codes: (i) y+1/2, −x+1, z+1/2; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Tetragonal, P4₂/n
Temperature (K)	100
a, c (Å)	14.4118 (2), 12.0995 (2)
V (Å³)	2513.07 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.27 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.969, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	28200, 2215, 1725
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.156, 1.08
No. of reflections	2215
No. of parameters	193
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17

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
N1—H1N···O1ⁱ	0.92 (4)	2.03 (3)	2.919 (3)	164 (2)
N1—H1N···O2ⁱ	0.92 (4)	2.58 (3)	3.168 (3)	123 (2)
O1—H1O···N2	0.97 (3)	1.61 (3)	2.572 (3)	167 (3)
C14—H14B···Cg1ⁱⁱ	0.96	2.95	3.840 (3)	154

Symmetry codes: (i) y+1/2, −x+1, z+1/2; (ii) −x+1, −y, −z.

Footnotes

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

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia (USM) for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). HKF and CKQ thank USM for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). CKQ thanks USM for a research fellowship. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE.

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