4-Methyl-2-oxo-2H-chromen-7-yl 4-fluoro­benzene­sulfonate

Sinha, S.; Osman, H.; Wahab, H.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536812004394

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o641-o642

doi:10.1107/S1600536812004394

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4-Methyl-2-oxo-2H-chromen-7-yl 4-fluorobenzenesulfonate

Suman Sinha,^a Hasnah Osman,^b Habibah A. Wahab,^a ‡ Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*§

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

(Received 26 January 2012; accepted 2 February 2012; online 10 February 2012)

In the asymmetric unit of the title compound, C₁₆H₁₁FO₅S, the 2H-chromene ring is essentially planar, with a maximum deviation of 0.040 (2) Å. The dihedral angle between the 2H-chromene ring and the 4-fluorophenyl ring is 2.17 (8)°. One of the sulfonamide O atoms is approximately coplanar with the benzene ring [C—C—S—O torsion angle = 166.00 (14)°], whereas the other O atom lies well below the plane [C—C—S—O = −61.35 (17)°]. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds, forming two-dimensional networks parallel to the ac plane.

Related literature

For details and applications of coumarines, see: Gu et al. (2007 ); Wrobel et al. (2002 ); Kostova (2005 ). For related structures, see: Sinha et al. (2011a ,b ); Al-Najjar et al. (2012 ). For the synthetic procedure, see: Sinha et al. (2011a,b); Fusegi et al. (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₁FO₅S
M_r = 334.31
Monoclinic, P 2₁ /c
a = 17.2983 (4) Å
b = 5.3397 (1) Å
c = 17.1669 (4) Å
β = 118.195 (1)°
V = 1397.52 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.36 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.911, T_max = 0.959
26795 measured reflections
4303 independent reflections
3494 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.156
S = 1.04
4303 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3ⁱ	0.95	2.48	3.314 (2)	147
C4—H4A⋯O5ⁱⁱ	0.95	2.57	3.214 (3)	126
C8—H8A⋯O4ⁱⁱ	0.95	2.37	3.288 (3)	162
C11—H11A⋯O5ⁱⁱⁱ	0.95	2.45	3.349 (3)	158
C15—H15A⋯O3^iv	0.95	2.59	3.502 (3)	160
C16—H16A⋯O5ⁱⁱⁱ	0.98	2.60	3.522 (3)	157
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1; (iii) $[-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y-1, z.

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, a. DOI: 10.1107/S1600536812004394/rz2704sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004394/rz2704Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004394/rz2704Isup3.cml

checkCIF report

Comment top

This work is to further explore the structural features of sulphur- containing small molecule derivatives which are being recently published from our laboratory (Sinha et al., 2011a,b; Al-Najjar et al., 2012). Recently, the O–SO₂ group have attracted attention in organic chemistry (Gu et al., 2007) and medicinal chemistry (Wrobel et al., 2002). Coumarines are also proven to be cytotoxic agents (Kostova, 2005). In this paper, we report the crystal structure of the title compound, which belongs to this class of compounds.

The asymmetric unit of the title compound is shown in Fig. 1. The 2H-chromene (O2/C7–C15) ring is essentially planar, with a maximum deviation of 0.040 (2) Å for atom C12. The dihedral angle between the 2H-chromene (O2/C7–C15) ring and fluoro-substituted phenyl (C1–C6) ring is 2.17 (8)°. The S atom adopts a distorted tetrahedral geometry. The sulfonamide O4 atom is approximately co-planar with the benzene ring [the O4-S1-C1-C6 torsion angle is 166.00 (14)°] whereas the O3 atom lies well below the plane [O3-S1-C1-C6 = -61.35 (17)°].

In the crystal, (Fig. 2), the molecules are connected via weak intermolecular C—H···O hydrogen bonds (Table 1) to form two-dimensional networks parallel to the ac plane.

Related literature top

For details and applications of coumarines, see: Gu et al. (2007); Wrobel et al. (2002); Kostova (2005). For related structures, see: Sinha et al. (2011a,b); Al-Najjar et al. (2012). For the synthetic procedure, see: Sinha et al. (2011a,b); Fusegi et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Detailed synthetic procedure has been described in Sinha et al. (2011a,b) and Fusegi et al. (2009).

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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

4-Methyl-2-oxo-2H-chromen-7-yl 4-fluorobenzenesulfonate top

Crystal data top

C₁₆H₁₁FO₅S	F(000) = 688
M_r = 334.31	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9952 reflections
a = 17.2983 (4) Å	θ = 2.4–30.6°
b = 5.3397 (1) Å	µ = 0.27 mm⁻¹
c = 17.1669 (4) Å	T = 100 K
β = 118.195 (1)°	Block, colourless
V = 1397.52 (5) Å³	0.36 × 0.19 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	3494 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 30.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
T_min = 0.911, T_max = 0.959	k = −7→7
26795 measured reflections	l = −24→24

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0914P)² + 0.9651P] where P = (F_o² + 2F_c²)/3
4303 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 1.14 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

C₁₆H₁₁FO₅S	V = 1397.52 (5) Å³
M_r = 334.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.2983 (4) Å	µ = 0.27 mm⁻¹
b = 5.3397 (1) Å	T = 100 K
c = 17.1669 (4) Å	0.36 × 0.19 × 0.16 mm
β = 118.195 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4303 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3494 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.959	R_int = 0.047
26795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.04	Δρ_max = 1.14 e Å⁻³
4303 reflections	Δρ_min = −0.72 e Å⁻³
209 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.05985 (3)	0.71221 (8)	0.40375 (3)	0.01356 (13)
F1	0.39345 (8)	0.2691 (3)	0.47175 (9)	0.0276 (3)
O1	0.00823 (8)	0.4700 (3)	0.40935 (9)	0.0161 (3)
O2	−0.26376 (8)	0.8084 (3)	0.36579 (9)	0.0161 (3)
O3	0.01710 (9)	0.8017 (3)	0.31455 (9)	0.0187 (3)
O4	0.07250 (9)	0.8822 (3)	0.47276 (9)	0.0207 (3)
O5	−0.38605 (9)	0.9692 (3)	0.35461 (9)	0.0222 (3)
C1	0.15987 (12)	0.3544 (4)	0.38064 (12)	0.0163 (4)
H1A	0.1064	0.2816	0.3380	0.020*
C2	0.23997 (13)	0.2524 (4)	0.39694 (13)	0.0182 (4)
H2A	0.2424	0.1061	0.3667	0.022*
C3	0.31602 (12)	0.3684 (4)	0.45807 (13)	0.0187 (4)
C4	0.31704 (12)	0.5773 (4)	0.50573 (13)	0.0188 (4)
H4A	0.3708	0.6504	0.5476	0.023*
C5	0.23669 (12)	0.6784 (4)	0.49075 (12)	0.0163 (4)
H5A	0.2346	0.8214	0.5227	0.020*
C6	0.15971 (11)	0.5657 (3)	0.42815 (12)	0.0140 (3)
C7	−0.08408 (11)	0.4728 (3)	0.36472 (12)	0.0139 (3)
C8	−0.12939 (11)	0.6500 (4)	0.38628 (12)	0.0147 (3)
H8A	−0.0998	0.7771	0.4288	0.018*
C9	−0.22037 (11)	0.6323 (3)	0.34251 (12)	0.0139 (3)
C10	−0.35402 (12)	0.8098 (4)	0.32803 (13)	0.0169 (4)
C11	−0.40187 (12)	0.6269 (4)	0.25971 (12)	0.0177 (4)
H11A	−0.4642	0.6291	0.2315	0.021*
C12	−0.36115 (12)	0.4529 (4)	0.23449 (12)	0.0156 (3)
C13	−0.26579 (12)	0.4483 (4)	0.27933 (12)	0.0146 (3)
C14	−0.21569 (12)	0.2714 (4)	0.26141 (12)	0.0160 (4)
H14A	−0.2447	0.1423	0.2196	0.019*
C15	−0.12520 (12)	0.2829 (4)	0.30367 (12)	0.0157 (3)
H15A	−0.0918	0.1634	0.2912	0.019*
C16	−0.41273 (13)	0.2751 (4)	0.16052 (14)	0.0209 (4)
H16A	−0.4755	0.2979	0.1408	0.031*
H16B	−0.3959	0.1027	0.1811	0.031*
H16C	−0.4006	0.3084	0.1112	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0139 (2)	0.0141 (2)	0.0135 (2)	0.00107 (14)	0.00718 (18)	0.00011 (15)
F1	0.0170 (6)	0.0382 (8)	0.0280 (7)	0.0093 (5)	0.0110 (5)	0.0014 (6)
O1	0.0137 (6)	0.0158 (6)	0.0191 (7)	0.0007 (5)	0.0079 (5)	0.0029 (5)
O2	0.0129 (6)	0.0189 (7)	0.0170 (6)	0.0011 (5)	0.0075 (5)	−0.0029 (5)
O3	0.0185 (7)	0.0217 (7)	0.0162 (7)	0.0037 (5)	0.0085 (6)	0.0058 (5)
O4	0.0216 (7)	0.0206 (7)	0.0213 (7)	0.0000 (5)	0.0111 (6)	−0.0068 (6)
O5	0.0172 (6)	0.0259 (8)	0.0236 (7)	0.0024 (5)	0.0098 (6)	−0.0048 (6)
C1	0.0182 (9)	0.0188 (9)	0.0127 (8)	0.0001 (7)	0.0079 (7)	−0.0002 (7)
C2	0.0211 (9)	0.0192 (9)	0.0170 (9)	0.0033 (7)	0.0112 (8)	0.0010 (7)
C3	0.0140 (8)	0.0264 (10)	0.0171 (9)	0.0053 (7)	0.0085 (7)	0.0041 (8)
C4	0.0139 (8)	0.0240 (10)	0.0172 (9)	−0.0004 (7)	0.0063 (7)	0.0011 (7)
C5	0.0167 (8)	0.0182 (9)	0.0141 (8)	−0.0005 (6)	0.0074 (7)	0.0002 (7)
C6	0.0134 (8)	0.0170 (8)	0.0119 (8)	0.0012 (6)	0.0063 (7)	0.0005 (6)
C7	0.0135 (8)	0.0158 (8)	0.0126 (8)	0.0012 (6)	0.0064 (7)	0.0032 (6)
C8	0.0154 (8)	0.0165 (8)	0.0131 (8)	−0.0004 (6)	0.0073 (7)	−0.0007 (7)
C9	0.0147 (8)	0.0152 (8)	0.0134 (8)	0.0006 (6)	0.0080 (7)	0.0006 (6)
C10	0.0142 (8)	0.0213 (9)	0.0161 (9)	0.0014 (6)	0.0079 (7)	0.0011 (7)
C11	0.0130 (8)	0.0225 (9)	0.0162 (9)	−0.0020 (7)	0.0059 (7)	−0.0015 (7)
C12	0.0163 (8)	0.0192 (9)	0.0118 (8)	−0.0023 (6)	0.0069 (7)	−0.0003 (7)
C13	0.0168 (8)	0.0161 (8)	0.0123 (8)	−0.0004 (6)	0.0079 (7)	0.0005 (6)
C14	0.0196 (9)	0.0157 (8)	0.0134 (8)	−0.0007 (6)	0.0084 (7)	−0.0014 (6)
C15	0.0201 (9)	0.0152 (8)	0.0141 (8)	0.0011 (6)	0.0101 (7)	−0.0004 (6)
C16	0.0186 (9)	0.0232 (10)	0.0189 (9)	−0.0044 (7)	0.0071 (8)	−0.0046 (7)

Geometric parameters (Å, º) top

S1—O4	1.4249 (14)	C5—H5A	0.9500
S1—O3	1.4318 (14)	C7—C8	1.386 (2)
S1—O1	1.6003 (14)	C7—C15	1.389 (3)
S1—C6	1.7572 (18)	C8—C9	1.390 (2)
F1—C3	1.354 (2)	C8—H8A	0.9500
O1—C7	1.407 (2)	C9—C13	1.398 (3)
O2—C9	1.375 (2)	C10—C11	1.448 (3)
O2—C10	1.379 (2)	C11—C12	1.355 (3)
O5—C10	1.216 (2)	C11—H11A	0.9500
C1—C2	1.389 (3)	C12—C13	1.454 (2)
C1—C6	1.393 (3)	C12—C16	1.496 (3)
C1—H1A	0.9500	C13—C14	1.411 (2)
C2—C3	1.382 (3)	C14—C15	1.381 (3)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.379 (3)	C15—H15A	0.9500
C4—C5	1.397 (3)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.392 (3)	C16—H16C	0.9800

O4—S1—O3	118.38 (9)	C7—C8—H8A	121.7
O4—S1—O1	109.63 (8)	C9—C8—H8A	121.7
O3—S1—O1	108.24 (8)	O2—C9—C8	115.48 (16)
O4—S1—C6	109.75 (9)	O2—C9—C13	121.48 (15)
O3—S1—C6	110.88 (8)	C8—C9—C13	123.03 (16)
O1—S1—C6	98.01 (8)	O5—C10—O2	116.29 (17)
C7—O1—S1	118.71 (11)	O5—C10—C11	126.04 (17)
C9—O2—C10	121.29 (15)	O2—C10—C11	117.66 (16)
C2—C1—C6	118.51 (18)	C12—C11—C10	122.46 (17)
C2—C1—H1A	120.7	C12—C11—H11A	118.8
C6—C1—H1A	120.7	C10—C11—H11A	118.8
C3—C2—C1	118.60 (18)	C11—C12—C13	118.27 (17)
C3—C2—H2A	120.7	C11—C12—C16	120.97 (17)
C1—C2—H2A	120.7	C13—C12—C16	120.73 (16)
F1—C3—C4	118.67 (18)	C9—C13—C14	117.50 (16)
F1—C3—C2	117.72 (18)	C9—C13—C12	118.70 (16)
C4—C3—C2	123.61 (17)	C14—C13—C12	123.79 (17)
C3—C4—C5	118.10 (18)	C15—C14—C13	121.10 (17)
C3—C4—H4A	121.0	C15—C14—H14A	119.4
C5—C4—H4A	120.9	C13—C14—H14A	119.4
C6—C5—C4	118.71 (18)	C14—C15—C7	118.56 (16)
C6—C5—H5A	120.6	C14—C15—H15A	120.7
C4—C5—H5A	120.6	C7—C15—H15A	120.7
C5—C6—C1	122.44 (16)	C12—C16—H16A	109.5
C5—C6—S1	117.74 (14)	C12—C16—H16B	109.5
C1—C6—S1	119.65 (14)	H16A—C16—H16B	109.5
C8—C7—C15	123.20 (16)	C12—C16—H16C	109.5
C8—C7—O1	120.08 (16)	H16A—C16—H16C	109.5
C15—C7—O1	116.60 (15)	H16B—C16—H16C	109.5
C7—C8—C9	116.60 (17)

O4—S1—O1—C7	88.16 (14)	C10—O2—C9—C8	−179.26 (16)
O3—S1—O1—C7	−42.30 (14)	C10—O2—C9—C13	0.4 (3)
C6—S1—O1—C7	−157.48 (13)	C7—C8—C9—O2	179.28 (15)
C6—C1—C2—C3	−1.5 (3)	C7—C8—C9—C13	−0.3 (3)
C1—C2—C3—F1	−178.69 (17)	C9—O2—C10—O5	178.24 (17)
C1—C2—C3—C4	1.7 (3)	C9—O2—C10—C11	−3.0 (2)
F1—C3—C4—C5	179.75 (17)	O5—C10—C11—C12	−179.18 (19)
C2—C3—C4—C5	−0.6 (3)	O2—C10—C11—C12	2.2 (3)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	1.2 (3)
C4—C5—C6—C1	0.7 (3)	C10—C11—C12—C16	−176.90 (18)
C4—C5—C6—S1	−174.62 (14)	O2—C9—C13—C14	−178.34 (16)
C2—C1—C6—C5	0.4 (3)	C8—C9—C13—C14	1.3 (3)
C2—C1—C6—S1	175.59 (14)	O2—C9—C13—C12	3.1 (3)
O4—S1—C6—C5	−18.55 (17)	C8—C9—C13—C12	−177.28 (17)
O3—S1—C6—C5	114.09 (15)	C11—C12—C13—C9	−3.8 (3)
O1—S1—C6—C5	−132.82 (15)	C16—C12—C13—C9	174.28 (17)
O4—S1—C6—C1	166.00 (14)	C11—C12—C13—C14	177.74 (18)
O3—S1—C6—C1	−61.35 (17)	C16—C12—C13—C14	−4.2 (3)
O1—S1—C6—C1	51.73 (16)	C9—C13—C14—C15	−1.1 (3)
S1—O1—C7—C8	−60.4 (2)	C12—C13—C14—C15	177.33 (17)
S1—O1—C7—C15	123.36 (15)	C13—C14—C15—C7	0.1 (3)
C15—C7—C8—C9	−0.8 (3)	C8—C7—C15—C14	0.9 (3)
O1—C7—C8—C9	−176.72 (15)	O1—C7—C15—C14	176.96 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱ	0.95	2.48	3.314 (2)	147
C4—H4A···O5ⁱⁱ	0.95	2.57	3.214 (3)	126
C8—H8A···O4ⁱⁱ	0.95	2.37	3.288 (3)	162
C11—H11A···O5ⁱⁱⁱ	0.95	2.45	3.349 (3)	158
C15—H15A···O3^iv	0.95	2.59	3.502 (3)	160
C16—H16A···O5ⁱⁱⁱ	0.98	2.60	3.522 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁FO₅S
M_r	334.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.2983 (4), 5.3397 (1), 17.1669 (4)
β (°)	118.195 (1)
V (Å³)	1397.52 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.36 × 0.19 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.911, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	26795, 4303, 3494
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.717

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.156, 1.04
No. of reflections	4303
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.72

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
C1—H1A···O3ⁱ	0.9500	2.4800	3.314 (2)	147.00
C4—H4A···O5ⁱⁱ	0.9500	2.5700	3.214 (3)	126.00
C8—H8A···O4ⁱⁱ	0.9500	2.3700	3.288 (3)	162.00
C11—H11A···O5ⁱⁱⁱ	0.9500	2.4500	3.349 (3)	158.00
C15—H15A···O3^iv	0.9500	2.5900	3.502 (3)	160.00
C16—H16A···O5ⁱⁱⁱ	0.9800	2.6000	3.522 (3)	157.00

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

Footnotes

‡Additional correspondence author, email: habibahw@usm.my

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SS, HO and HAW gratefully acknowledge the Malaysian Ministry of Science, Technology and Innovation for the synthesis work funded by grant Nos. 09-05-lfn-meb-004 and 304/PFARMASI/650545/I121. MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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