3-[1-(3-Hydroxy­benz­yl)-1H-benz­imid­azol-2-yl]phenol

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

doi:10.1107/S1600536809018698

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1374-o1375

doi:10.1107/S1600536809018698

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3-[1-(3-Hydroxybenzyl)-1H-benzimidazol-2-yl]phenol

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Hoong-Kun Fun,^b ^*§ Samuel Robinson Jebas ^b ¶ and Rohana Adnan ^a

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

(Received 13 May 2009; accepted 18 May 2009; online 23 May 2009)

In the title molecule, C₂₀H₁₆N₂O₂, the benzimidazole mean plane forms dihedral angles of 56.55 (3) and 81.65 (4)° with the two benzene rings. In the crystal structure, intermolecular O—H⋯O and O—H⋯N hydrogen bonds link the molecules into layers parallel to the (101) plane. The crystal packing also exhibits weak intermolecular C—H⋯O and C—H⋯π interactions.

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_r = 316.35
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.05
7426 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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⋯O1^iv	0.93	2.59	3.4287 (10)	150
C12—H12A⋯Cg1ⁱⁱ	0.93	2.67	3.4521 (9)	142
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z. Cg1 is the centroid of the ring C1–C6.

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/S1600536809018698/cv2563sup1.cif

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

checkCIF report

Comment top

The synthesis of benzimidazoles has received much attention owing to the varied biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. In continuation of our structural study of benzimidazole derivatives (Eltayeb et al. 2007a,b,c), we describe in this paper the crystal structure of the title compound (I).

In (I) (Fig. 1), the bond lengths and bond angles are normal (Allen et al., 1987). The benzimidazole unit is planar with the maximum deviation from planarity of 0.0403 (9) Å for atom C3. The dihedral angle formed by the benzimidazole unit with the two benzene rings (C8–C13 and C15–C20) are 56.55 (3)° and 81.65 (4)° respectively. The two benzene rings (C8–C13 and C15–C20) are inclined to each other forming a dihedral angle of 72.54 (4)°.

In the crystal, intermolecular O—H···O, O—H···N hydrogen bonds (Table 1) link the molecules into layers parallel to the (101) plane. The crystal packing exhibits also weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For biological activities 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 normal values of geometric parameters in organic compounds, see: Allen et al. (1987). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml) was added 3-hydroxybenzaldehyde (0.488 g, 4 mmol). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. 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 (I), showing 50% probability displacement ellipsoids and the atom numbering scheme.

3-[1-(3-Hydroxybenzyl)-1H-benzimidazol-2-yl]phenol top

Crystal data top

C₂₀H₁₆N₂O₂	F(000) = 664
M_r = 316.35	D_x = 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

Data collection top

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

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)] = 0.048	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(F_o²) + (0.0723P)² + 0.2344P] where P = (F_o² + 2F_c²)/3
7426 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₆N₂O₂	V = 1582.61 (5) Å³
M_r = 316.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5128 (2) Å	µ = 0.09 mm⁻¹
b = 12.1096 (2) Å	T = 100 K
c = 12.5235 (2) Å	0.55 × 0.34 × 0.15 mm
β = 96.948 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7426 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6004 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.987	R_int = 0.040
34106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.51 e Å⁻³
7426 reflections	Δρ_min = −0.29 e Å⁻³
225 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 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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.59	3.4287 (10)	150
C12—H12A···Cg1ⁱⁱ	0.93	2.67	3.4521 (9)	142

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂O₂
M_r	316.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.5128 (2), 12.1096 (2), 12.5235 (2)
β (°)	96.948 (1)
V (Å³)	1582.61 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.34 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.954, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	34106, 7426, 6004
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.827

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.136, 1.05
No. of reflections	7426
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.29

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
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)	136.1
C9—H9A···O1^iv	0.93	2.59	3.4287 (10)	149.9
C12—H12A···Cg1ⁱⁱ	0.93	2.67	3.4521 (9)	142

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z.

Footnotes

‡On study leave from the International University of Africa, Sudan.

§Thomson Reuters ResearcherID: A-3561-2009.

¶Thomson Reuters ResearcherID: A-5473-2009. Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for a Science Fund grant (No. 305/PFIZIK/613312). SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for a Research University Golden Goose grant (No. 1001/PFIZIK/811012).

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