6-Methyl-3-phenyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­quinazolin-4-one

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

doi:10.1107/S1600536812007301

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o862

doi:10.1107/S1600536812007301

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6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-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 16 February 2012; accepted 17 February 2012; online 29 February 2012)

The title compound, C₁₅H₁₂N₂OS, exists as the thione tautomer in the solid state. The phenyl group is almost perpendicular [dihedral angle = 87.96 (5)°] to the fused ring system (r.m.s. deviation = 0.036 Å for 13 ring and exocyclic non-H atoms). In the crystal, centrosymmetric dimers, sustained by pairs of N—H⋯S hydrogen bonds, are connected into layers parallel to (-101) by C—H⋯O and C—H⋯S interactions.

Related literature

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab & El-Tahir (2012 ); El-Azab et al. (2011 , 2010 ). For the antimicrobial activity of the title compound, see: Al-Omar et al. (2004 ). For the structures of related compounds, see: Bowman et al. (2007 ); Hashim et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₂N₂OS
M_r = 268.33
Monoclinic, P 2₁ /n
a = 12.7770 (3) Å
b = 5.1384 (1) Å
c = 19.0973 (4) Å
β = 91.814 (2)°
V = 1253.17 (5) Å³
Z = 4
Cu Kα radiation
μ = 2.23 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.05 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
4636 measured reflections
2576 independent reflections
2348 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.098
S = 1.06
2576 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1n⋯S1ⁱ	0.91 (2)	2.49 (2)	3.3662 (12)	163.6 (17)
C3—H3⋯O1ⁱⁱ	0.95	2.33	3.2522 (17)	163
C11—H11⋯S1ⁱⁱⁱ	0.95	2.86	3.7333 (16)	154
C15—H15⋯O1^iv	0.95	2.32	3.1988 (18)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) x, y+1, z.

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/S1600536812007301/qm2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007301/qm2054Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007301/qm2054Isup3.cml

checkCIF report

Comment top

Quinazoline-4(3H)-one derivatives are known for their various biological activities (El-Azab & El-Tahir, 2012; El-Azab et al. (2011, 2010). The title compound (I) has been investigated previously for its anti-microbial activity (Al-Omar et al., 2004). Herein, its crystal and molecular structure is described.

The key result of the crystal structure determination of (I), Fig. 1, is the confirmation that the compound exists as the thione tautomer in the solid-state. The non-hydrogen atoms comprising the fused ring system, including the exocyclic atoms, are co-planar with a r.m.s. deviation = 0.036 Å. The maximum deviations from the least-squares plane through these atoms are 0.038 (1) Å for the S1 atom and -0.085 (1) Å for N1, consistent with some pyramidal character for the latter atom. The phenyl group is almost perpendicular to the aforementioned plane: the dihedral angle = 87.96 (5)°.

The presence of the thione tautomer confirms the results of previous structure determinations on related compounds (Bowman et al., 2007; Hashim et al., 2010).

The key feature of the crystal packing is the formation of N—H···S hydrogen bonds between centrosymmetrically related molecules, Table 1. The dimeric aggregates thus formed are connected into layers parallel to (1 0 1) by C—H···O interactions, involving the bifurcated carbonyl-O atom, and C—H···S interactions, Fig. 2 and Table 1. Layers stack with no specific intermolecular interactions between them, Fig. 3.

Related literature top

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab & El-Tahir (2012); El-Azab et al. (2011, 2010). For the antimicrobial activity of the title compound, see: Al-Omar et al. (2004). For the structures of related compounds, see: Bowman et al. (2007); Hashim et al. (2010).

Experimental top

A mixture of 2-amino-5-methylbenzoic acid (1.51 g m, 10 mmol) and phenyl isothiocyanate (1.35 g m, 10 mmol) in absolute ethanol (30 ml) containing triethylamine (1.1 mg, 10 mmol) was refluxed for 3 h. The reaction mixture was allowed to cool, the solvent was removed under reduced pressure, and the solid obtained was dried and recrystallized from EtOH. Yield 90%; M.pt: 340–342 K; ¹H NMR (500 MHz, DMSO-d6): δ 12.98 (s, 1H, exchangeable), 7.75 (s, 1H), 7.60 (d, 1H, J=8.0 Hz), 7.48 (t, 2H, J=7.0, 7.5 Hz), 7.41 (d, 1H, J=7.0 Hz), 7.36 (d, 1H, J=8.0 Hz), 7.26 (d, 2H, J=8.0 Hz), 2.37 (s, 3H). ¹³C NMR (DMSO-d6): δ 176.0, 160.2, 139.8, 138.1, 137.1, 134.4, 129.5, 129.3, 128.5, 127.2, 116.5, 116.2, 20.9.

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 the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular layer parallel to (1 0 1) in (I) mediated by N—H···S, C—H···O and C—H···S interactions, shown as blue, orange and brown dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents of (I). The N—H···S, C—H···O and C—H···S interactions are shown as blue, orange and brown dashed lines, respectively.

6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one top

Crystal data top

C₁₅H₁₂N₂OS	F(000) = 560
M_r = 268.33	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 2386 reflections
a = 12.7770 (3) Å	θ = 3.5–76.4°
b = 5.1384 (1) Å	µ = 2.23 mm⁻¹
c = 19.0973 (4) Å	T = 100 K
β = 91.814 (2)°	Prism, colourless
V = 1253.17 (5) Å³	0.35 × 0.15 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2576 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2348 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.1°
ω scan	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→6
T_min = 0.967, T_max = 0.998	l = −14→24
4636 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0613P)² + 0.3083P] where P = (F_o² + 2F_c²)/3
2576 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₂N₂OS	V = 1253.17 (5) Å³
M_r = 268.33	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 12.7770 (3) Å	µ = 2.23 mm⁻¹
b = 5.1384 (1) Å	T = 100 K
c = 19.0973 (4) Å	0.35 × 0.15 × 0.05 mm
β = 91.814 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2576 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2348 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.998	R_int = 0.016
4636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
2576 reflections	Δρ_min = −0.25 e Å⁻³
177 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
S1	0.56616 (3)	0.52832 (7)	0.394981 (16)	0.01717 (12)
O1	0.35822 (8)	−0.1192 (2)	0.25706 (5)	0.0181 (2)
N1	0.45653 (9)	0.1596 (2)	0.32532 (6)	0.0149 (2)
H1n	0.4357 (15)	0.305 (4)	0.4827 (11)	0.029 (5)*
N2	0.42228 (9)	0.2138 (2)	0.44293 (6)	0.0161 (2)
C1	0.37571 (11)	−0.0266 (3)	0.31493 (7)	0.0150 (3)
C2	0.31942 (10)	−0.0982 (3)	0.37768 (7)	0.0156 (3)
C3	0.24261 (10)	−0.2920 (3)	0.37432 (7)	0.0173 (3)
H3	0.2250	−0.3722	0.3307	0.021*
C4	0.19179 (11)	−0.3686 (3)	0.43408 (7)	0.0182 (3)
C5	0.22073 (11)	−0.2484 (3)	0.49797 (7)	0.0195 (3)
H5	0.1871	−0.3001	0.5394	0.023*
C6	0.29690 (11)	−0.0568 (3)	0.50213 (7)	0.0179 (3)
H6	0.3156	0.0210	0.5459	0.021*
C7	0.34592 (11)	0.0206 (3)	0.44129 (7)	0.0156 (3)
C9	0.47714 (10)	0.2888 (3)	0.38744 (7)	0.0149 (3)
C8	0.10873 (12)	−0.5770 (3)	0.42997 (8)	0.0229 (3)
H8A	0.1314	−0.7176	0.3993	0.034*
H8B	0.0432	−0.5024	0.4110	0.034*
H8C	0.0976	−0.6465	0.4769	0.034*
C10	0.52338 (10)	0.2014 (3)	0.26589 (7)	0.0154 (3)
C11	0.60838 (11)	0.0364 (3)	0.25902 (8)	0.0188 (3)
H11	0.6233	−0.0942	0.2931	0.023*
C12	0.67148 (12)	0.0652 (3)	0.20130 (8)	0.0208 (3)
H12	0.7303	−0.0452	0.1959	0.025*
C13	0.64818 (11)	0.2554 (3)	0.15178 (7)	0.0208 (3)
H13	0.6910	0.2746	0.1124	0.025*
C14	0.56249 (12)	0.4182 (3)	0.15946 (7)	0.0217 (3)
H14	0.5471	0.5485	0.1254	0.026*
C15	0.49894 (11)	0.3912 (3)	0.21705 (7)	0.0193 (3)
H15	0.4400	0.5013	0.2225	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0194 (2)	0.01951 (19)	0.01264 (19)	−0.00399 (12)	0.00160 (13)	−0.00051 (12)
O1	0.0211 (5)	0.0210 (5)	0.0122 (5)	−0.0004 (4)	−0.0006 (4)	−0.0024 (4)
N1	0.0169 (5)	0.0178 (6)	0.0102 (5)	−0.0002 (4)	0.0019 (4)	−0.0005 (4)
N2	0.0189 (6)	0.0194 (6)	0.0101 (5)	−0.0025 (5)	0.0016 (4)	−0.0016 (5)
C1	0.0154 (6)	0.0161 (6)	0.0136 (6)	0.0029 (5)	−0.0003 (5)	0.0006 (5)
C2	0.0156 (6)	0.0179 (6)	0.0132 (6)	0.0015 (5)	0.0007 (5)	0.0012 (5)
C3	0.0168 (6)	0.0197 (7)	0.0153 (6)	0.0001 (5)	−0.0004 (5)	−0.0009 (5)
C4	0.0158 (6)	0.0190 (7)	0.0199 (7)	0.0012 (5)	0.0008 (5)	0.0013 (5)
C5	0.0193 (6)	0.0229 (7)	0.0165 (6)	0.0013 (5)	0.0052 (5)	0.0029 (6)
C6	0.0201 (7)	0.0212 (7)	0.0125 (6)	0.0008 (5)	0.0023 (5)	−0.0002 (5)
C7	0.0145 (6)	0.0176 (6)	0.0145 (6)	0.0011 (5)	0.0005 (5)	0.0002 (5)
C9	0.0155 (6)	0.0163 (6)	0.0129 (6)	0.0015 (5)	0.0002 (5)	0.0004 (5)
C8	0.0198 (7)	0.0245 (7)	0.0245 (7)	−0.0038 (6)	0.0032 (6)	0.0017 (6)
C10	0.0176 (6)	0.0183 (6)	0.0103 (6)	−0.0027 (5)	0.0026 (5)	−0.0021 (5)
C11	0.0199 (7)	0.0199 (7)	0.0166 (7)	0.0013 (5)	0.0024 (5)	0.0032 (5)
C12	0.0187 (7)	0.0225 (7)	0.0213 (7)	0.0011 (6)	0.0056 (6)	−0.0005 (6)
C13	0.0230 (7)	0.0249 (7)	0.0148 (6)	−0.0055 (6)	0.0060 (5)	−0.0011 (6)
C14	0.0283 (8)	0.0220 (7)	0.0148 (7)	−0.0007 (6)	0.0024 (6)	0.0051 (6)
C15	0.0226 (7)	0.0192 (7)	0.0161 (6)	0.0025 (6)	0.0024 (5)	−0.0008 (6)

Geometric parameters (Å, º) top

S1—C9	1.6788 (14)	C6—C7	1.3953 (19)
O1—C1	1.2175 (17)	C6—H6	0.9500
N1—C9	1.3776 (17)	C8—H8A	0.9800
N1—C1	1.4171 (18)	C8—H8B	0.9800
N1—C10	1.4578 (16)	C8—H8C	0.9800
N2—C9	1.3454 (17)	C10—C15	1.379 (2)
N2—C7	1.3913 (18)	C10—C11	1.388 (2)
N2—H1n	0.91 (2)	C11—C12	1.3940 (19)
C1—C2	1.4639 (18)	C11—H11	0.9500
C2—C7	1.3918 (19)	C12—C13	1.386 (2)
C2—C3	1.398 (2)	C12—H12	0.9500
C3—C4	1.3877 (19)	C13—C14	1.389 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.3945 (19)
C4—C8	1.508 (2)	C14—H14	0.9500
C5—C6	1.385 (2)	C15—H15	0.9500
C5—H5	0.9500

C9—N1—C1	124.38 (11)	N2—C9—N1	116.73 (12)
C9—N1—C10	119.89 (11)	N2—C9—S1	120.73 (10)
C1—N1—C10	115.66 (11)	N1—C9—S1	122.54 (10)
C9—N2—C7	124.69 (12)	C4—C8—H8A	109.5
C9—N2—H1n	115.0 (13)	C4—C8—H8B	109.5
C7—N2—H1n	120.2 (13)	H8A—C8—H8B	109.5
O1—C1—N1	120.20 (12)	C4—C8—H8C	109.5
O1—C1—C2	124.34 (13)	H8A—C8—H8C	109.5
N1—C1—C2	115.45 (12)	H8B—C8—H8C	109.5
C7—C2—C3	120.25 (12)	C15—C10—C11	121.98 (12)
C7—C2—C1	119.46 (13)	C15—C10—N1	120.36 (12)
C3—C2—C1	120.24 (12)	C11—C10—N1	117.59 (12)
C4—C3—C2	120.66 (13)	C10—C11—C12	118.93 (13)
C4—C3—H3	119.7	C10—C11—H11	120.5
C2—C3—H3	119.7	C12—C11—H11	120.5
C3—C4—C5	118.17 (13)	C13—C12—C11	119.84 (14)
C3—C4—C8	120.35 (13)	C13—C12—H12	120.1
C5—C4—C8	121.48 (13)	C11—C12—H12	120.1
C6—C5—C4	121.79 (13)	C12—C13—C14	120.37 (13)
C6—C5—H5	119.1	C12—C13—H13	119.8
C4—C5—H5	119.1	C14—C13—H13	119.8
C5—C6—C7	119.22 (13)	C13—C14—C15	120.25 (13)
C5—C6—H6	120.4	C13—C14—H14	119.9
C7—C6—H6	120.4	C15—C14—H14	119.9
N2—C7—C2	118.93 (12)	C10—C15—C14	118.62 (13)
N2—C7—C6	121.17 (13)	C10—C15—H15	120.7
C2—C7—C6	119.90 (13)	C14—C15—H15	120.7

C9—N1—C1—O1	175.07 (13)	C5—C6—C7—N2	179.51 (13)
C10—N1—C1—O1	−7.96 (18)	C5—C6—C7—C2	−1.2 (2)
C9—N1—C1—C2	−6.19 (19)	C7—N2—C9—N1	−1.3 (2)
C10—N1—C1—C2	170.77 (11)	C7—N2—C9—S1	178.88 (10)
O1—C1—C2—C7	−179.92 (13)	C1—N1—C9—N2	6.2 (2)
N1—C1—C2—C7	1.40 (19)	C10—N1—C9—N2	−170.65 (12)
O1—C1—C2—C3	2.7 (2)	C1—N1—C9—S1	−173.97 (10)
N1—C1—C2—C3	−176.00 (12)	C10—N1—C9—S1	9.18 (18)
C7—C2—C3—C4	0.0 (2)	C9—N1—C10—C15	−91.74 (16)
C1—C2—C3—C4	177.40 (13)	C1—N1—C10—C15	91.15 (16)
C2—C3—C4—C5	−0.9 (2)	C9—N1—C10—C11	91.23 (16)
C2—C3—C4—C8	179.76 (13)	C1—N1—C10—C11	−85.88 (15)
C3—C4—C5—C6	0.6 (2)	C15—C10—C11—C12	0.6 (2)
C8—C4—C5—C6	−179.97 (13)	N1—C10—C11—C12	177.61 (13)
C4—C5—C6—C7	0.4 (2)	C10—C11—C12—C13	−0.5 (2)
C9—N2—C7—C2	−3.2 (2)	C11—C12—C13—C14	0.2 (2)
C9—N2—C7—C6	176.10 (13)	C12—C13—C14—C15	−0.2 (2)
C3—C2—C7—N2	−179.69 (12)	C11—C10—C15—C14	−0.6 (2)
C1—C2—C7—N2	2.9 (2)	N1—C10—C15—C14	−177.45 (13)
C3—C2—C7—C6	1.0 (2)	C13—C14—C15—C10	0.3 (2)
C1—C2—C7—C6	−176.36 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1n···S1ⁱ	0.91 (2)	2.49 (2)	3.3662 (12)	163.6 (17)
C3—H3···O1ⁱⁱ	0.95	2.33	3.2522 (17)	163
C11—H11···S1ⁱⁱⁱ	0.95	2.86	3.7333 (16)	154
C15—H15···O1^iv	0.95	2.32	3.1988 (18)	154

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂OS
M_r	268.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.7770 (3), 5.1384 (1), 19.0973 (4)
β (°)	91.814 (2)
V (Å³)	1253.17 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.35 × 0.15 × 0.05

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	4636, 2576, 2348
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.098, 1.06
No. of reflections	2576
No. of parameters	177
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

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
N2—H1n···S1ⁱ	0.91 (2)	2.49 (2)	3.3662 (12)	163.6 (17)
C3—H3···O1ⁱⁱ	0.95	2.33	3.2522 (17)	163
C11—H11···S1ⁱⁱⁱ	0.95	2.86	3.7333 (16)	154
C15—H15···O1^iv	0.95	2.32	3.1988 (18)	154

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

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. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Omar, M. A., Abdel-Hamide, S. G., Al-Khamees, H. A. & El-Subbagh, H. I. (2004). Saudi Pharm. J. 12, 63–71. CAS Google Scholar
Bowman, W. R., Elsegood, M. R. J., Stein, T. & Weaver, G. W. (2007). Org. Biomol. Chem. 5, 103–113. Web of Science CSD CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A.-M., Abdel-Aziz, N. I., El-Sayed, M. A.-A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamide, S. G. (2010). Eur. J. Med. Chem. 45, 4188–4198. Web of Science CAS PubMed Google Scholar
El-Azab, A. S. & El-Tahir, K. H. (2012). Bioorg. Med. Chem. Lett. 22, 327–333. Web of Science CAS PubMed Google Scholar
El-Azab, A. S., El-Tahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, 837–925. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hashim, N. M., Osman, H., Rahim, A. A., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o950. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar