(Z)-2-(4-Chloro­benzyl­idene)benzo[d]thia­zolo[3,2-a]imidazol-3(2H)-one

Fun, H.-K.; Chantrapromma, S.; Abdel-Aziz, H.A.

doi:10.1107/S1600536812015516

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1393-o1394

doi:10.1107/S1600536812015516

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(Z)-2-(4-Chlorobenzylidene)benzo[d]thiazolo[3,2-a]imidazol-3(2H)-one

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma ^b § and Hatem A. Abdel-Aziz ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 8 April 2012; accepted 10 April 2012; online 18 April 2012)

The molecule of the title compound, C₁₆H₉ClN₂OS, is approximately planar, the dihedral angle between the thiazolo[3,2-a]benzimidazole ring system and the 4-chlorophenyl ring being 2.10 (5)°. An intramolecular C—H⋯S interaction generates an S(6) ring motif. In the crystal, molecules are stacked into columns along the b axis by π–π interactions with centroid–centroid distances of 3.6495 (7)–3.9546 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to and the biological activity of thiazolo[3,2-a]benzimidazoles, see: Abdel-Aziz, El-Zahabi & Dawood (2010 ); Abdel-Aziz, Hamdy et al. (2007 , 2008 ); Abdel-Aziz, Saleh & El-Zahabi (2010 ); Al-Rashood & Abdel-Aziz (2010 ); Chimirri et al. (1988 ); Farag et al. (2011 ); Hamdy et al. (2007 ); Mavrova et al. (2005 ). For the stability of the temperature controller, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₉ClN₂OS
M_r = 312.77
Triclinic, $[P \overline 1]$
a = 7.0182 (4) Å
b = 7.3443 (4) Å
c = 13.7142 (8) Å
α = 91.742 (1)°
β = 100.836 (1)°
γ = 112.878 (1)°
V = 635.47 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 100 K
0.37 × 0.18 × 0.06 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.848, T_max = 0.973
14145 measured reflections
3660 independent reflections
3233 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.05
3660 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯S1	0.93	2.50	3.2161 (13)	133

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536812015516/is5117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015516/is5117Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015516/is5117Isup3.cml

checkCIF report

Comment top

There are considerable interest in the chemistry of thiazolo[3,2-a]benzimidazoles and their unique pharmaceutical and medicinal applications have been reported. These activities including antibacterial, antifungal, anti-inflammatory, antiulcer, antiviral, anthelmintic and anticancer properties (Al-Rashood et al., 2010; Chimirri et al., 1988). The parasitological study in vitro has also shown that the analogs of the title compound exhibited higher activity than albendazole against T. spiralis (Mavrova et al., 2005). These considerable biological activities as well as in continuation of our interests in the chemistry and biological activities of these compounds (Abdel-Aziz, Hamdy et al., 2007, 2008; Abdel-Aziz, Saleh & El-Zahabi, 2010; Farag et al., 2011; Hamdy et al., 2007) have lead us to synthesize and present the X-ray structural analysis of the title compound (I).

In the molecular structure of (I), C₁₄H₁₁ClN₄O₄, the thiazolo[3,2-a]benzimidazole ring system is planar with an r.m.s. deviation 0.019 (12) Å for the thirteen non H-atoms (C1–C9/N1/N2/O1/S1) and the 4-chlorobenzilidene unit is also planar with an r.m.s deviation 0.002 (12) Å for the eight non H-atoms (C10–C16/Cl1). The dihedral between the mean plane through the thiazolo[3,2-a]benzimidazole ring system and 4-chlorophenyl ring is 2.10 (5)°. An intramolecular C—H···S weak interaction (Fig. 1 and Table 1) generates an S(6) ring motif (Bernstein et al., 1995) which help to stabilize the planarity of the molecule. The bond distances agree with the literature values (Allen et al., 1987).

In the crystal packing (Fig. 2), the molecules are stacked into column along the b axis by π–π interactions with the distances of Cg1···Cg1ⁱ = 3.8297 (7) Å, Cg2···Cg4ⁱⁱ = 3.9545 (8) Å, Cg3···Cg4ⁱ = 3.7691 (8) Å and Cg3···Cg4ⁱⁱ = 3.6495 (7) Å [symmetry codes: (i) 1-x, 1-y, -z; (ii) 1-x, -y, -z]. Cg1, Cg2, Cg3 and Cg4 are the centroids of S1/C1/N2/C8/C9, C1/C2/C7/N1/N2, C2–C7 and C11–C16 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 and the biological activity of thiazolo[3,2-a]benzimidazoles, see: Abdel-Aziz, El-Zahabi & Dawood (2010); Abdel-Aziz, Hamdy et al. (2007, 2008); Abdel-Aziz, Saleh & El-Zahabi (2010); Al-Rashood & Abdel-Aziz (2010); Chimirri et al. (1988); Farag et al. (2011); Hamdy et al. (2007); Mavrova et al. (2005). For the stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental top

The one-pot synthesis of the title compound was carried out by a cyclocondensation of 2-mercaptobenzimidazole, chloroacetic acid, 4-chloro benzaldehyde, acetic anhydride and glacial acetic acid in the presence of sodium acetate to afford the title compound (Mavrova et al., 2005; Abdel-Aziz, El-Zahabi & Dawood, 2010). Yellow needle-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol by slow evaporation of the solvent at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Intramolecular C—H···S weak interaction was shown as dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis.

(Z)-2-(4-Chlorobenzylidene)benzo[d]thiazolo[3,2- a]imidazol-3(2H)-one top

Crystal data top

C₁₆H₉ClN₂OS	Z = 2
M_r = 312.77	F(000) = 320
Triclinic, P1	D_x = 1.635 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0182 (4) Å	Cell parameters from 3660 reflections
b = 7.3443 (4) Å	θ = 1.5–30.0°
c = 13.7142 (8) Å	µ = 0.46 mm⁻¹
α = 91.742 (1)°	T = 100 K
β = 100.836 (1)°	Needle, yellow
γ = 112.878 (1)°	0.37 × 0.18 × 0.06 mm
V = 635.47 (6) Å³

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3660 independent reflections
Radiation source: sealed tube	3233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.848, T_max = 0.973	k = −10→10
14145 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0366P)² + 0.3855P] where P = (F_o² + 2F_c²)/3
3660 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₉ClN₂OS	γ = 112.878 (1)°
M_r = 312.77	V = 635.47 (6) Å³
Triclinic, P1	Z = 2
a = 7.0182 (4) Å	Mo Kα radiation
b = 7.3443 (4) Å	µ = 0.46 mm⁻¹
c = 13.7142 (8) Å	T = 100 K
α = 91.742 (1)°	0.37 × 0.18 × 0.06 mm
β = 100.836 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3660 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3233 reflections with I > 2σ(I)
T_min = 0.848, T_max = 0.973	R_int = 0.026
14145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
3660 reflections	Δρ_min = −0.27 e Å⁻³
190 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
S1	0.34693 (4)	0.25459 (4)	0.03735 (2)	0.01299 (8)
Cl1	−0.35675 (5)	−0.18707 (5)	−0.43869 (2)	0.02057 (9)
O1	0.88271 (14)	0.27130 (14)	−0.01062 (7)	0.01625 (18)
N1	0.58054 (16)	0.43157 (15)	0.22785 (8)	0.0138 (2)
N2	0.75134 (15)	0.36857 (15)	0.11464 (7)	0.01179 (19)
C1	0.56374 (18)	0.36129 (17)	0.13730 (9)	0.0123 (2)
C2	0.79803 (18)	0.49233 (17)	0.27094 (9)	0.0125 (2)
C3	0.90598 (19)	0.57701 (18)	0.36781 (9)	0.0147 (2)
H3A	0.8365	0.6030	0.4144	0.018*
C4	1.1227 (2)	0.62158 (18)	0.39238 (9)	0.0156 (2)
H4A	1.1988	0.6788	0.4566	0.019*
C5	1.22857 (19)	0.58244 (18)	0.32293 (9)	0.0149 (2)
H5A	1.3731	0.6138	0.3422	0.018*
C6	1.12230 (18)	0.49741 (18)	0.22550 (9)	0.0135 (2)
H6A	1.1918	0.4713	0.1789	0.016*
C7	0.90738 (18)	0.45404 (17)	0.20197 (9)	0.0117 (2)
C8	0.73740 (18)	0.28632 (17)	0.01951 (9)	0.0121 (2)
C9	0.51258 (18)	0.21858 (17)	−0.03702 (9)	0.0120 (2)
C10	0.45896 (18)	0.14096 (17)	−0.13349 (9)	0.0129 (2)
H10A	0.5708	0.1362	−0.1591	0.015*
C11	0.25559 (18)	0.06330 (17)	−0.20435 (9)	0.0125 (2)
C12	0.25076 (19)	−0.00568 (18)	−0.30184 (9)	0.0140 (2)
H12A	0.3757	0.0004	−0.3181	0.017*
C13	0.0643 (2)	−0.08267 (18)	−0.37443 (9)	0.0154 (2)
H13A	0.0636	−0.1272	−0.4388	0.018*
C14	−0.12171 (19)	−0.09177 (18)	−0.34886 (9)	0.0144 (2)
C15	−0.12333 (19)	−0.02595 (18)	−0.25342 (9)	0.0149 (2)
H15A	−0.2493	−0.0337	−0.2377	0.018*
C16	0.06430 (19)	0.05172 (18)	−0.18134 (9)	0.0141 (2)
H16A	0.0635	0.0965	−0.1173	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01026 (13)	0.01520 (14)	0.01318 (14)	0.00536 (10)	0.00154 (10)	−0.00024 (10)
Cl1	0.01474 (14)	0.02600 (17)	0.01591 (15)	0.00557 (12)	−0.00226 (11)	−0.00026 (11)
O1	0.0137 (4)	0.0197 (4)	0.0166 (4)	0.0080 (3)	0.0038 (3)	−0.0002 (3)
N1	0.0123 (4)	0.0143 (5)	0.0146 (5)	0.0056 (4)	0.0021 (4)	0.0006 (4)
N2	0.0103 (4)	0.0130 (4)	0.0123 (4)	0.0052 (3)	0.0018 (3)	0.0012 (4)
C1	0.0108 (5)	0.0127 (5)	0.0145 (5)	0.0056 (4)	0.0029 (4)	0.0021 (4)
C2	0.0126 (5)	0.0113 (5)	0.0140 (5)	0.0056 (4)	0.0024 (4)	0.0015 (4)
C3	0.0163 (5)	0.0142 (5)	0.0136 (5)	0.0065 (4)	0.0029 (4)	0.0007 (4)
C4	0.0176 (5)	0.0135 (5)	0.0134 (5)	0.0057 (4)	−0.0007 (4)	0.0004 (4)
C5	0.0129 (5)	0.0139 (5)	0.0163 (6)	0.0050 (4)	0.0001 (4)	0.0021 (4)
C6	0.0124 (5)	0.0131 (5)	0.0153 (5)	0.0056 (4)	0.0028 (4)	0.0021 (4)
C7	0.0131 (5)	0.0108 (5)	0.0108 (5)	0.0050 (4)	0.0013 (4)	0.0013 (4)
C8	0.0125 (5)	0.0104 (5)	0.0126 (5)	0.0044 (4)	0.0016 (4)	0.0013 (4)
C9	0.0096 (5)	0.0112 (5)	0.0155 (5)	0.0047 (4)	0.0023 (4)	0.0023 (4)
C10	0.0125 (5)	0.0121 (5)	0.0149 (5)	0.0059 (4)	0.0029 (4)	0.0024 (4)
C11	0.0130 (5)	0.0106 (5)	0.0135 (5)	0.0047 (4)	0.0017 (4)	0.0017 (4)
C12	0.0141 (5)	0.0141 (5)	0.0143 (5)	0.0062 (4)	0.0030 (4)	0.0013 (4)
C13	0.0176 (5)	0.0152 (5)	0.0125 (5)	0.0064 (4)	0.0020 (4)	0.0008 (4)
C14	0.0136 (5)	0.0125 (5)	0.0142 (5)	0.0042 (4)	−0.0009 (4)	0.0016 (4)
C15	0.0129 (5)	0.0158 (5)	0.0161 (6)	0.0059 (4)	0.0033 (4)	0.0027 (4)
C16	0.0148 (5)	0.0144 (5)	0.0131 (5)	0.0061 (4)	0.0028 (4)	0.0010 (4)

Geometric parameters (Å, º) top

S1—C1	1.7411 (12)	C6—C7	1.3849 (16)
S1—C9	1.7692 (12)	C6—H6A	0.9300
Cl1—C14	1.7363 (12)	C8—C9	1.4981 (16)
O1—C8	1.2108 (14)	C9—C10	1.3480 (16)
N1—C1	1.2967 (15)	C10—C11	1.4556 (16)
N1—C2	1.4119 (15)	C10—H10A	0.9300
N2—C1	1.3903 (14)	C11—C12	1.4049 (16)
N2—C8	1.3909 (15)	C11—C16	1.4076 (16)
N2—C7	1.3980 (15)	C12—C13	1.3871 (17)
C2—C3	1.3895 (16)	C12—H12A	0.9300
C2—C7	1.4097 (16)	C13—C14	1.3917 (17)
C3—C4	1.3955 (17)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.3850 (17)
C4—C5	1.3990 (17)	C15—C16	1.3888 (17)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.3942 (17)	C16—H16A	0.9300
C5—H5A	0.9300

C1—S1—C9	90.12 (5)	O1—C8—C9	126.82 (11)
C1—N1—C2	103.32 (10)	N2—C8—C9	107.93 (10)
C1—N2—C8	116.71 (10)	C10—C9—C8	119.68 (10)
C1—N2—C7	105.85 (9)	C10—C9—S1	128.06 (9)
C8—N2—C7	137.35 (10)	C8—C9—S1	112.26 (8)
N1—C1—N2	115.19 (10)	C9—C10—C11	130.90 (11)
N1—C1—S1	131.92 (9)	C9—C10—H10A	114.5
N2—C1—S1	112.88 (9)	C11—C10—H10A	114.5
C3—C2—C7	120.04 (11)	C12—C11—C16	118.15 (11)
C3—C2—N1	128.60 (11)	C12—C11—C10	117.52 (10)
C7—C2—N1	111.36 (10)	C16—C11—C10	124.33 (11)
C2—C3—C4	117.38 (11)	C13—C12—C11	121.66 (11)
C2—C3—H3A	121.3	C13—C12—H12A	119.2
C4—C3—H3A	121.3	C11—C12—H12A	119.2
C3—C4—C5	121.78 (11)	C12—C13—C14	118.53 (11)
C3—C4—H4A	119.1	C12—C13—H13A	120.7
C5—C4—H4A	119.1	C14—C13—H13A	120.7
C6—C5—C4	121.47 (11)	C15—C14—C13	121.46 (11)
C6—C5—H5A	119.3	C15—C14—Cl1	119.27 (9)
C4—C5—H5A	119.3	C13—C14—Cl1	119.26 (9)
C7—C6—C5	116.23 (11)	C14—C15—C16	119.61 (11)
C7—C6—H6A	121.9	C14—C15—H15A	120.2
C5—C6—H6A	121.9	C16—C15—H15A	120.2
C6—C7—N2	132.61 (11)	C15—C16—C11	120.58 (11)
C6—C7—C2	123.10 (11)	C15—C16—H16A	119.7
N2—C7—C2	104.28 (10)	C11—C16—H16A	119.7
O1—C8—N2	125.24 (11)

C2—N1—C1—N2	0.05 (14)	C1—N2—C8—O1	−176.11 (12)
C2—N1—C1—S1	179.02 (10)	C7—N2—C8—O1	−0.2 (2)
C8—N2—C1—N1	177.22 (10)	C1—N2—C8—C9	3.12 (14)
C7—N2—C1—N1	0.13 (14)	C7—N2—C8—C9	178.99 (13)
C8—N2—C1—S1	−1.95 (13)	O1—C8—C9—C10	−3.77 (19)
C7—N2—C1—S1	−179.04 (8)	N2—C8—C9—C10	177.02 (11)
C9—S1—C1—N1	−178.97 (13)	O1—C8—C9—S1	176.23 (11)
C9—S1—C1—N2	0.01 (9)	N2—C8—C9—S1	−2.99 (12)
C1—N1—C2—C3	−179.20 (12)	C1—S1—C9—C10	−178.28 (12)
C1—N1—C2—C7	−0.20 (13)	C1—S1—C9—C8	1.72 (9)
C7—C2—C3—C4	0.23 (18)	C8—C9—C10—C11	179.37 (11)
N1—C2—C3—C4	179.15 (12)	S1—C9—C10—C11	−0.6 (2)
C2—C3—C4—C5	−0.26 (18)	C9—C10—C11—C12	178.99 (12)
C3—C4—C5—C6	0.22 (19)	C9—C10—C11—C16	−1.5 (2)
C4—C5—C6—C7	−0.14 (18)	C16—C11—C12—C13	0.28 (18)
C5—C6—C7—N2	−179.28 (12)	C10—C11—C12—C13	179.85 (11)
C5—C6—C7—C2	0.12 (18)	C11—C12—C13—C14	−0.30 (19)
C1—N2—C7—C6	179.25 (13)	C12—C13—C14—C15	0.04 (19)
C8—N2—C7—C6	3.1 (2)	C12—C13—C14—Cl1	179.84 (9)
C1—N2—C7—C2	−0.24 (12)	C13—C14—C15—C16	0.24 (19)
C8—N2—C7—C2	−176.40 (13)	Cl1—C14—C15—C16	−179.57 (9)
C3—C2—C7—C6	−0.17 (18)	C14—C15—C16—C11	−0.26 (19)
N1—C2—C7—C6	−179.26 (11)	C12—C11—C16—C15	0.01 (18)
C3—C2—C7—N2	179.38 (11)	C10—C11—C16—C15	−179.53 (11)
N1—C2—C7—N2	0.28 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···S1	0.93	2.50	3.2161 (13)	133

Experimental details

Crystal data
Chemical formula	C₁₆H₉ClN₂OS
M_r	312.77
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.0182 (4), 7.3443 (4), 13.7142 (8)
α, β, γ (°)	91.742 (1), 100.836 (1), 112.878 (1)
V (Å³)	635.47 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.37 × 0.18 × 0.06

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.848, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	14145, 3660, 3233
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.05
No. of reflections	3660
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C16—H16A···S1	0.93	2.50	3.2161 (13)	133

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

HAAA thanks the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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