2-Methyl-3-(2-methyl­phen­yl)-7-nitro­quinazolin-4(3H)-one

El-Azab, A.S.; Abdel-Aziz, A.A.-M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812007350

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o863

doi:10.1107/S1600536812007350

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2-Methyl-3-(2-methylphenyl)-7-nitroquinazolin-4(3H)-one

Adel S. El-Azab,^a,^b ‡ Alaa A.-M. Abdel-Aziz,^a,^c Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 February 2012; accepted 18 February 2012; online 29 February 2012)

In the title methaqualone analogue, C₁₆H₁₃N₃O₃, the 2-tolyl group is almost orthogonal [dihedral angle = 85.20 (5)°] to the fused ring system (r.m.s. deviation of fitted non-H atoms = 0.029 Å). In the crystal, twofold symmetry generates two-molecule aggregates linked by C—H⋯O and π–π interactions [ring centroid–centroid distance = 3.4967 (6) Å].

Related literature

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2010 , 2012 ). For the anti-convulsant activity of the title methaqualone analogue, see: El-Azab et al. (2011 ). For a related structure, see: Stephenson et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₃N₃O₃
M_r = 295.29
Monoclinic, C 2/c
a = 14.4614 (5) Å
b = 16.5383 (4) Å
c = 12.9968 (4) Å
β = 119.072 (4)°
V = 2716.78 (14) Å³
Z = 8
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.967, T_max = 0.998
5450 measured reflections
2783 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 1.02
2783 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.95	2.54	3.4530 (15)	161
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007350/hb6642sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007350/hb6642Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007350/hb6642Isup3.cml

checkCIF report

Comment top

The title methaqualone analogue, 2-methyl-7-nitro-3-o-tolylquinazolin-4(3H)-one (I), has been investigated previously for its anti-convulsant activity (El-Azab et al., 2012) as quinazoline-4(3H)-one derivatives are known for their various biological activities (El-Azab et al., 2011, 2010). Herein, the crystal and molecular structure of (I) is described. A related structure with a similar conformation has been reported recently (Stephenson et al., 2011).

The ten atoms comprising the fused ring system in (I), Fig. 1, are almost co-planar with the r.m.s. deviation for the non-hydrogen atoms being 0.029 Å. The 2-tolyl group is approximately orthogonal to this plane, forming a dihedral angle of 85.20 (5) °. The nitro group is almost co-planar with the ring to which it is connected as seen in the value of the O2—N3—C3—C2 torsion angle of 179.07 (10)°.

The main feature of the crystal packing is the formation of two molecule aggregates sustained by C—H···O, Table 1, and π–π interactions, Fig. 2. The π–π interactions occur between (C1–C6) rings, i.e. the C₆ group within the fused ring system, with a ring centroid-to-centroid distance of 3.4967 (6) Å [symmetry operation: 1 - x, y, 1/2 - z]. There are no specific intermolecular interactions between the two-molecule aggregates [generated by 2-fold symmetry]. They assemble into layers in the bc plane, Fig. 3, and these stack along the a axis, Fig. 4.

Related literature top

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2012, 2010). For the anti-convulsant activity of the title methaqualone analogue, see: El-Azab et al. (2011). For a related structure, see: Stephenson et al. (2011).

Experimental top

4-Nitroanthranilic acid (1.82 g, 10 mmol) was refluxed with acetic anhydride (20 ml) for 3 h. The reaction mixture was cooled, filtered, washed with petroleum ether, and dried to yield 2-methyl-7-nitro-4H-3,1-benzoxazin-4-one as an a solid compound. This was refluxed with o-toludine (1.18 g, 11 mmol) in pyridine (30 ml) for 8 h. The reaction mixture was cooled, the solvent was removed under reduced pressure and the residue was triturated with water and filtered. The solid obtained was dried, chromatographed with CHCl₃ and recrystallized from its EtOH solution as colourless cubes.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the two-molecular aggregate in (I) sustained by C—H···O and π–π interactions shown as orange and purple dashed lines, respectively.
	Fig. 3. A view of the assembly of two-molecule aggregates in the bc plane in (I). The C—H···O and π–π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 4. A view in projection down the a axis of the unit-cell contents of (I). The C—H···O and π–π interactions are shown as orange and purple dashed lines, respectively.

2-Methyl-3-(2-methylphenyl)-7-nitroquinazolin-4(3H)-one top

Crystal data top

C₁₆H₁₃N₃O₃	F(000) = 1232
M_r = 295.29	D_x = 1.444 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 3546 reflections
a = 14.4614 (5) Å	θ = 3.9–76.4°
b = 16.5383 (4) Å	µ = 0.85 mm⁻¹
c = 12.9968 (4) Å	T = 100 K
β = 119.072 (4)°	Cube, colourless
V = 2716.78 (14) Å³	0.25 × 0.25 × 0.25 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2783 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2570 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.013
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.4°
ω scan	h = −18→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −20→18
T_min = 0.967, T_max = 0.998	l = −10→16
5450 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0566P)² + 1.6285P] where P = (F_o² + 2F_c²)/3
2783 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₃N₃O₃	V = 2716.78 (14) Å³
M_r = 295.29	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 14.4614 (5) Å	µ = 0.85 mm⁻¹
b = 16.5383 (4) Å	T = 100 K
c = 12.9968 (4) Å	0.25 × 0.25 × 0.25 mm
β = 119.072 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2783 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2570 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.998	R_int = 0.013
5450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
2783 reflections	Δρ_min = −0.24 e Å⁻³
201 parameters

Special details top

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	0.59490 (6)	0.19268 (5)	0.43782 (7)	0.0250 (2)
O2	0.65765 (7)	0.61062 (5)	0.45232 (9)	0.0338 (2)
O3	0.48735 (7)	0.62439 (5)	0.36278 (8)	0.0330 (2)
N1	0.41702 (7)	0.21605 (6)	0.35394 (8)	0.0201 (2)
N2	0.34237 (7)	0.34733 (6)	0.30533 (8)	0.0217 (2)
N3	0.56777 (8)	0.58294 (6)	0.40625 (9)	0.0247 (2)
C1	0.44368 (9)	0.37812 (7)	0.35225 (9)	0.0196 (2)
C2	0.45504 (9)	0.46277 (7)	0.35369 (9)	0.0208 (2)
H2	0.3949	0.4972	0.3210	0.025*
C3	0.55556 (9)	0.49398 (7)	0.40369 (10)	0.0214 (2)
C4	0.64664 (9)	0.44647 (7)	0.45173 (10)	0.0225 (2)
H4	0.7148	0.4707	0.4859	0.027*
C5	0.63564 (9)	0.36354 (7)	0.44855 (9)	0.0215 (2)
H5	0.6964	0.3298	0.4795	0.026*
C6	0.53454 (9)	0.32924 (7)	0.39953 (9)	0.0195 (2)
C7	0.52197 (8)	0.24124 (7)	0.39980 (9)	0.0200 (2)
C8	0.33210 (8)	0.26981 (7)	0.30874 (9)	0.0211 (2)
C9	0.22363 (9)	0.23499 (7)	0.26233 (11)	0.0273 (3)
H9A	0.1715	0.2788	0.2356	0.041*
H9B	0.2199	0.2044	0.3248	0.041*
H9C	0.2084	0.1989	0.1962	0.041*
C10	0.39793 (8)	0.13076 (7)	0.36267 (10)	0.0207 (2)
C11	0.37329 (9)	0.08065 (7)	0.26703 (10)	0.0236 (2)
H11	0.3732	0.1011	0.1987	0.028*
C12	0.34882 (9)	0.00019 (7)	0.27286 (11)	0.0252 (3)
H12	0.3291	−0.0345	0.2071	0.030*
C13	0.35326 (9)	−0.02949 (7)	0.37522 (11)	0.0242 (3)
H13	0.3371	−0.0846	0.3798	0.029*
C14	0.38125 (9)	0.02132 (7)	0.47070 (10)	0.0232 (2)
H14	0.3863	−0.0001	0.5411	0.028*
C15	0.40209 (8)	0.10313 (7)	0.46597 (10)	0.0214 (2)
C16	0.42659 (10)	0.15867 (8)	0.56764 (10)	0.0270 (3)
H16A	0.4905	0.1899	0.5866	0.040*
H16B	0.4381	0.1266	0.6363	0.040*
H16C	0.3671	0.1957	0.5463	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0190 (4)	0.0239 (4)	0.0292 (4)	0.0027 (3)	0.0094 (3)	0.0001 (3)
O2	0.0311 (5)	0.0281 (5)	0.0405 (5)	−0.0096 (4)	0.0161 (4)	−0.0045 (4)
O3	0.0324 (5)	0.0247 (4)	0.0405 (5)	0.0026 (4)	0.0166 (4)	0.0039 (4)
N1	0.0172 (5)	0.0203 (5)	0.0208 (5)	−0.0004 (3)	0.0077 (4)	0.0000 (3)
N2	0.0180 (4)	0.0233 (5)	0.0217 (5)	0.0007 (4)	0.0080 (4)	0.0022 (4)
N3	0.0284 (5)	0.0241 (5)	0.0238 (5)	−0.0033 (4)	0.0143 (4)	−0.0008 (4)
C1	0.0190 (5)	0.0242 (5)	0.0158 (5)	0.0000 (4)	0.0087 (4)	0.0003 (4)
C2	0.0213 (5)	0.0237 (6)	0.0182 (5)	0.0017 (4)	0.0101 (4)	0.0015 (4)
C3	0.0265 (6)	0.0218 (5)	0.0183 (5)	−0.0021 (4)	0.0126 (4)	−0.0007 (4)
C4	0.0195 (5)	0.0275 (6)	0.0194 (5)	−0.0046 (4)	0.0088 (4)	−0.0023 (4)
C5	0.0185 (5)	0.0262 (6)	0.0187 (5)	0.0003 (4)	0.0082 (4)	−0.0005 (4)
C6	0.0194 (5)	0.0230 (5)	0.0160 (5)	−0.0002 (4)	0.0087 (4)	−0.0005 (4)
C7	0.0170 (5)	0.0245 (6)	0.0173 (5)	0.0003 (4)	0.0075 (4)	−0.0010 (4)
C8	0.0171 (5)	0.0251 (5)	0.0188 (5)	0.0004 (4)	0.0069 (4)	0.0014 (4)
C9	0.0175 (5)	0.0265 (6)	0.0326 (6)	−0.0001 (4)	0.0080 (5)	0.0038 (5)
C10	0.0161 (5)	0.0208 (5)	0.0226 (5)	−0.0002 (4)	0.0073 (4)	0.0006 (4)
C11	0.0216 (5)	0.0262 (6)	0.0217 (5)	−0.0001 (4)	0.0094 (4)	0.0001 (4)
C12	0.0223 (6)	0.0252 (6)	0.0260 (6)	−0.0021 (4)	0.0101 (5)	−0.0049 (4)
C13	0.0182 (5)	0.0221 (5)	0.0291 (6)	−0.0014 (4)	0.0090 (5)	0.0007 (4)
C14	0.0164 (5)	0.0269 (6)	0.0240 (6)	−0.0010 (4)	0.0081 (4)	0.0030 (4)
C15	0.0145 (5)	0.0252 (6)	0.0219 (5)	−0.0002 (4)	0.0068 (4)	−0.0010 (4)
C16	0.0270 (6)	0.0301 (6)	0.0227 (6)	−0.0035 (5)	0.0112 (5)	−0.0025 (5)

Geometric parameters (Å, º) top

O1—C7	1.2227 (14)	C8—C9	1.4955 (15)
O2—N3	1.2253 (13)	C9—H9A	0.9800
O3—N3	1.2261 (14)	C9—H9B	0.9800
N1—C8	1.3938 (14)	C9—H9C	0.9800
N1—C7	1.3976 (14)	C10—C11	1.3887 (16)
N1—C10	1.4522 (14)	C10—C15	1.3915 (16)
N2—C8	1.2939 (15)	C11—C12	1.3885 (16)
N2—C1	1.3818 (14)	C11—H11	0.9500
N3—C3	1.4803 (14)	C12—C13	1.3899 (17)
C1—C6	1.4046 (15)	C12—H12	0.9500
C1—C2	1.4086 (15)	C13—C14	1.3863 (17)
C2—C3	1.3724 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3939 (16)
C3—C4	1.3939 (16)	C14—H14	0.9500
C4—C5	1.3790 (16)	C15—C16	1.5035 (15)
C4—H4	0.9500	C16—H16A	0.9800
C5—C6	1.4000 (15)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.4670 (15)

C8—N1—C7	122.78 (9)	C8—C9—H9A	109.5
C8—N1—C10	119.37 (9)	C8—C9—H9B	109.5
C7—N1—C10	117.68 (9)	H9A—C9—H9B	109.5
C8—N2—C1	117.70 (9)	C8—C9—H9C	109.5
O2—N3—O3	124.04 (10)	H9A—C9—H9C	109.5
O2—N3—C3	117.96 (10)	H9B—C9—H9C	109.5
O3—N3—C3	117.99 (10)	C11—C10—C15	122.65 (11)
N2—C1—C6	123.15 (10)	C11—C10—N1	119.05 (10)
N2—C1—C2	117.64 (10)	C15—C10—N1	118.27 (10)
C6—C1—C2	119.20 (10)	C12—C11—C10	118.98 (11)
C3—C2—C1	118.02 (10)	C12—C11—H11	120.5
C3—C2—H2	121.0	C10—C11—H11	120.5
C1—C2—H2	121.0	C11—C12—C13	119.74 (11)
C2—C3—C4	123.58 (10)	C11—C12—H12	120.1
C2—C3—N3	118.14 (10)	C13—C12—H12	120.1
C4—C3—N3	118.28 (10)	C14—C13—C12	120.02 (11)
C5—C4—C3	118.49 (10)	C14—C13—H13	120.0
C5—C4—H4	120.8	C12—C13—H13	120.0
C3—C4—H4	120.8	C13—C14—C15	121.61 (11)
C4—C5—C6	119.76 (10)	C13—C14—H14	119.2
C4—C5—H5	120.1	C15—C14—H14	119.2
C6—C5—H5	120.1	C10—C15—C14	116.90 (10)
C5—C6—C1	120.93 (10)	C10—C15—C16	121.90 (10)
C5—C6—C7	120.27 (10)	C14—C15—C16	121.19 (10)
C1—C6—C7	118.77 (10)	C15—C16—H16A	109.5
O1—C7—N1	121.42 (10)	C15—C16—H16B	109.5
O1—C7—C6	124.68 (10)	H16A—C16—H16B	109.5
N1—C7—C6	113.88 (9)	C15—C16—H16C	109.5
N2—C8—N1	123.66 (10)	H16A—C16—H16C	109.5
N2—C8—C9	118.89 (10)	H16B—C16—H16C	109.5
N1—C8—C9	117.45 (10)

C8—N2—C1—C6	2.02 (16)	C1—C6—C7—O1	179.56 (10)
C8—N2—C1—C2	−176.98 (10)	C5—C6—C7—N1	176.62 (9)
N2—C1—C2—C3	177.87 (10)	C1—C6—C7—N1	−1.68 (14)
C6—C1—C2—C3	−1.17 (15)	C1—N2—C8—N1	−1.83 (16)
C1—C2—C3—C4	0.77 (17)	C1—N2—C8—C9	177.94 (10)
C1—C2—C3—N3	−179.48 (9)	C7—N1—C8—N2	−0.21 (17)
O2—N3—C3—C2	179.07 (10)	C10—N1—C8—N2	174.96 (10)
O3—N3—C3—C2	−0.50 (15)	C7—N1—C8—C9	−179.98 (10)
O2—N3—C3—C4	−1.17 (15)	C10—N1—C8—C9	−4.82 (15)
O3—N3—C3—C4	179.26 (10)	C8—N1—C10—C11	88.12 (13)
C2—C3—C4—C5	0.36 (17)	C7—N1—C10—C11	−96.47 (12)
N3—C3—C4—C5	−179.39 (9)	C8—N1—C10—C15	−90.00 (12)
C3—C4—C5—C6	−1.07 (16)	C7—N1—C10—C15	85.41 (13)
C4—C5—C6—C1	0.66 (16)	C15—C10—C11—C12	1.87 (17)
C4—C5—C6—C7	−177.60 (10)	N1—C10—C11—C12	−176.16 (10)
N2—C1—C6—C5	−178.50 (10)	C10—C11—C12—C13	−2.42 (17)
C2—C1—C6—C5	0.48 (16)	C11—C12—C13—C14	0.49 (17)
N2—C1—C6—C7	−0.22 (15)	C12—C13—C14—C15	2.14 (17)
C2—C1—C6—C7	178.77 (9)	C11—C10—C15—C14	0.65 (16)
C8—N1—C7—O1	−179.25 (10)	N1—C10—C15—C14	178.70 (9)
C10—N1—C7—O1	5.51 (15)	C11—C10—C15—C16	−178.64 (10)
C8—N1—C7—C6	1.94 (14)	N1—C10—C15—C16	−0.59 (16)
C10—N1—C7—C6	−173.30 (9)	C13—C14—C15—C10	−2.66 (16)
C5—C6—C7—O1	−2.15 (17)	C13—C14—C15—C16	176.63 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.95	2.54	3.4530 (15)	161

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃O₃
M_r	295.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	14.4614 (5), 16.5383 (4), 12.9968 (4)
β (°)	119.072 (4)
V (Å³)	2716.78 (14)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.967, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	5450, 2783, 2570
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.099, 1.02
No. of reflections	2783
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.24

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.95	2.54	3.4530 (15)	161

Symmetry code: (i) −x+1, y, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: adelazaba@yahoo.com.

Acknowledgements

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM·C/HIR/MOHE/SC/12).

References

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