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

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

doi:10.1107/S1600536811049476

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3457

https://doi.org/10.1107/S1600536811049476

Open

access

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

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 18 November 2011; accepted 19 November 2011; online 30 November 2011)

In the title compound, C₁₇H₁₄O₆S, the 2H-chromene ring is essentially planar, with a maximum deviation of 0.016 (1) Å. The dihedral angle between the 2H-chromene and the benzene rings is 54.61 (5)°. The C atom of the methoxy group is close to coplanar with its attached ring [deviation = 0.082 (2) Å]. In the crystal, molecules are connected via C—H⋯O hydrogen bonds, forming sheets lying parallel to the bc plane. Weak C—H⋯π interactions are also observed.

Related literature

For applications and properties of coumarin derivatives, see: Sinha et al. (2011 ); Valente et al. (2010); Radanyi et al. (2008 ); Han et al. (2005 ); Cheng et al. (2004 ). For further synthetic details, see: Fusegi et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₄O₆S
M_r = 346.34
Triclinic, $[P \overline 1]$
a = 7.9801 (3) Å
b = 9.2234 (4) Å
c = 10.9682 (5) Å
α = 99.049 (1)°
β = 90.288 (1)°
γ = 93.945 (1)°
V = 795.26 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.39 × 0.34 × 0.17 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.913, T_max = 0.962
21468 measured reflections
5907 independent reflections
4468 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.131
S = 1.04
5907 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O2/C9–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O3ⁱ	0.93	2.50	3.4156 (16)	169
C15—H15A⋯O5ⁱⁱ	0.93	2.44	3.2923 (17)	153
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.96	3.8423 (17)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x, -y+1, -z+2.

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: https://doi.org/10.1107/S1600536811049476/hb6524sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049476/hb6524Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049476/hb6524Isup3.cml

checkCIF report

Comment top

This is the continuation of our work regarding synthesis of derivatives of sulphur-containing small molecules (Sinha et al., 2011). Coumarin derivatives have been tested successfully against Cdc25 phosphatases (Valente et al., 2010), HSP 90 (Radanyi et al., 2008), MEK1 (Han et al., 2005) as well as TNF-α (Cheng et al., 2004). Apart from these biological activity, this class of molecules is also widely used as fluorescent labels for molecular studies of nucleic acids and proteins.

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 0.016 (1) Å for atom O2. The dihedral angle between the 2H-chromene (O2/C7–C15) ring and benzene (C1–C6) ring is 54.61 (5)°.

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 bc-plane. Furthermore, the crystal structure is stabilized by weak C—H···π interactions involving the Cg1 (O2/C9–C13) ring.

Related literature top

For applications and properties of coumarin derivatives, see: Sinha et al. (2011); Valente et al. (2010); Radanyi et al. (2008); Han et al. (2005); Cheng et al. (2004). For further synthetic details, see: Fusegi et al. (2009).

Experimental top

The synthetic procedure followed is modified from the recent work by Fusegi et al. (2009). A mixture of 4-methylumbelliferone (0.176 g, 1.00 mmol), K₂CO₃ (0.345 g, 2.5 mmol), and 4 Methoxybenzene sulphonyl chloride (0.130 g, 1.1 mmol) in ethyl acetate (10 ml) was refluxed for 5 hrs. After cooling, the solvent was evaporated under reduced pressure. H₂O (30 ml) was added to the residue and the contents was extracted with AcOEt (3 × 100 ml). The combined organic layer was washed with H₂O (3 × 80 ml) and brine (1 × 100 ml) and was dried over MgSO₄. The solvent was evaporated in vacuo and the residue was recrystallized from hexane - AcOEt (7: 1) to give the title compound as colourless blocks.

Structure description top

For applications and properties of coumarin derivatives, see: Sinha et al. (2011); Valente et al. (2010); Radanyi et al. (2008); Han et al. (2005); Cheng et al. (2004). For further synthetic details, see: 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 (I). H atoms not involved in hydrogen bonding are omitted for clarity.

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

Crystal data top

C₁₇H₁₄O₆S	Z = 2
M_r = 346.34	F(000) = 360
Triclinic, P1	D_x = 1.446 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9801 (3) Å	Cell parameters from 7512 reflections
b = 9.2234 (4) Å	θ = 2.6–32.8°
c = 10.9682 (5) Å	µ = 0.23 mm⁻¹
α = 99.049 (1)°	T = 296 K
β = 90.288 (1)°	Block, colourless
γ = 93.945 (1)°	0.39 × 0.34 × 0.17 mm
V = 795.26 (6) Å³

Data collection top

Bruker APEXII DUO CCD diffractometer	5907 independent reflections
Radiation source: fine-focus sealed tube	4468 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 33.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.913, T_max = 0.962	k = −14→12
21468 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0651P)² + 0.114P] where P = (F_o² + 2F_c²)/3
5907 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₇H₁₄O₆S	γ = 93.945 (1)°
M_r = 346.34	V = 795.26 (6) Å³
Triclinic, P1	Z = 2
a = 7.9801 (3) Å	Mo Kα radiation
b = 9.2234 (4) Å	µ = 0.23 mm⁻¹
c = 10.9682 (5) Å	T = 296 K
α = 99.049 (1)°	0.39 × 0.34 × 0.17 mm
β = 90.288 (1)°

Data collection top

Bruker APEXII DUO CCD diffractometer	5907 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4468 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.962	R_int = 0.022
21468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.34 e Å⁻³
5907 reflections	Δρ_min = −0.36 e Å⁻³
219 parameters

Special details top

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	0.33642 (4)	0.69504 (3)	0.53507 (3)	0.04487 (10)
O1	0.44708 (11)	0.69936 (10)	0.65864 (8)	0.04511 (19)
O2	0.33520 (13)	0.28756 (9)	0.86131 (8)	0.0501 (2)
O3	0.45083 (14)	0.76349 (12)	0.45924 (10)	0.0622 (3)
O4	0.26867 (14)	0.54843 (11)	0.49601 (9)	0.0583 (3)
O5	0.2954 (2)	0.08977 (12)	0.94880 (12)	0.0839 (4)
O6	−0.18253 (12)	1.08511 (11)	0.72509 (10)	0.0568 (2)
C1	0.01468 (16)	0.74728 (13)	0.59708 (11)	0.0438 (2)
H1A	−0.0095	0.6464	0.5755	0.053*
C2	−0.11060 (16)	0.83699 (14)	0.64295 (12)	0.0449 (2)
H2A	−0.2193	0.7970	0.6513	0.054*
C3	−0.07179 (15)	0.98751 (13)	0.67639 (11)	0.0419 (2)
C4	0.08909 (16)	1.04825 (13)	0.65845 (13)	0.0469 (3)
H4A	0.1127	1.1494	0.6781	0.056*
C5	0.21342 (16)	0.96007 (14)	0.61205 (12)	0.0453 (3)
H5A	0.3207	1.0008	0.5999	0.054*
C6	0.17587 (15)	0.80817 (13)	0.58340 (10)	0.0405 (2)
C7	0.37903 (14)	0.63892 (12)	0.75909 (10)	0.0386 (2)
C8	0.38320 (15)	0.49001 (12)	0.75940 (10)	0.0396 (2)
H8A	0.4218	0.4280	0.6918	0.048*
C9	0.32790 (14)	0.43633 (12)	0.86381 (10)	0.0382 (2)
C10	0.2809 (2)	0.21991 (15)	0.95863 (13)	0.0563 (3)
C11	0.2140 (2)	0.31206 (16)	1.06288 (13)	0.0568 (3)
H11A	0.1724	0.2679	1.1282	0.068*
C12	0.20871 (17)	0.45853 (14)	1.07064 (11)	0.0458 (3)
C13	0.26811 (14)	0.52666 (12)	0.96685 (10)	0.0383 (2)
C14	0.26642 (17)	0.67727 (13)	0.96096 (11)	0.0452 (3)
H14A	0.2273	0.7400	1.0279	0.054*
C15	0.32143 (17)	0.73451 (13)	0.85815 (12)	0.0456 (3)
H15A	0.3200	0.8346	0.8552	0.055*
C16	0.1440 (2)	0.55079 (18)	1.18327 (12)	0.0630 (4)
H16A	0.1057	0.4884	1.2412	0.095*
H16B	0.0523	0.6035	1.1600	0.095*
H16C	0.2324	0.6196	1.2206	0.095*
C17	−0.34930 (19)	1.03035 (18)	0.74647 (17)	0.0627 (4)
H17A	−0.4167	1.1113	0.7733	0.094*
H17B	−0.3472	0.9685	0.8091	0.094*
H17C	−0.3963	0.9743	0.6714	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.05261 (18)	0.04271 (16)	0.04015 (15)	0.00954 (12)	0.00695 (11)	0.00638 (11)
O1	0.0427 (4)	0.0443 (4)	0.0496 (4)	0.0032 (3)	0.0038 (3)	0.0114 (3)
O2	0.0732 (6)	0.0319 (4)	0.0456 (4)	0.0135 (4)	0.0032 (4)	0.0030 (3)
O3	0.0705 (7)	0.0656 (6)	0.0567 (6)	0.0191 (5)	0.0255 (5)	0.0214 (5)
O4	0.0723 (7)	0.0449 (5)	0.0543 (5)	0.0094 (4)	−0.0045 (5)	−0.0048 (4)
O5	0.1473 (13)	0.0369 (5)	0.0711 (7)	0.0192 (6)	0.0102 (8)	0.0137 (5)
O6	0.0477 (5)	0.0450 (5)	0.0759 (7)	0.0090 (4)	0.0043 (5)	0.0016 (4)
C1	0.0511 (6)	0.0349 (5)	0.0454 (6)	−0.0002 (4)	0.0022 (5)	0.0075 (4)
C2	0.0427 (6)	0.0412 (6)	0.0511 (6)	−0.0009 (4)	0.0028 (5)	0.0102 (5)
C3	0.0430 (6)	0.0389 (5)	0.0441 (5)	0.0059 (4)	−0.0030 (4)	0.0061 (4)
C4	0.0463 (6)	0.0352 (5)	0.0579 (7)	0.0003 (4)	−0.0065 (5)	0.0040 (5)
C5	0.0402 (6)	0.0405 (6)	0.0553 (7)	0.0000 (4)	−0.0021 (5)	0.0089 (5)
C6	0.0437 (6)	0.0388 (5)	0.0397 (5)	0.0051 (4)	0.0012 (4)	0.0078 (4)
C7	0.0389 (5)	0.0359 (5)	0.0413 (5)	0.0057 (4)	−0.0001 (4)	0.0056 (4)
C8	0.0437 (6)	0.0355 (5)	0.0391 (5)	0.0105 (4)	0.0016 (4)	0.0007 (4)
C9	0.0439 (5)	0.0312 (4)	0.0389 (5)	0.0093 (4)	−0.0034 (4)	0.0006 (4)
C10	0.0830 (10)	0.0385 (6)	0.0486 (7)	0.0097 (6)	−0.0028 (6)	0.0090 (5)
C11	0.0819 (10)	0.0480 (7)	0.0427 (6)	0.0087 (6)	0.0026 (6)	0.0121 (5)
C12	0.0549 (7)	0.0465 (6)	0.0354 (5)	0.0081 (5)	−0.0028 (5)	0.0029 (4)
C13	0.0436 (5)	0.0361 (5)	0.0342 (5)	0.0079 (4)	−0.0033 (4)	0.0000 (4)
C14	0.0578 (7)	0.0358 (5)	0.0400 (5)	0.0114 (5)	0.0008 (5)	−0.0039 (4)
C15	0.0572 (7)	0.0309 (5)	0.0480 (6)	0.0087 (5)	0.0001 (5)	0.0011 (4)
C16	0.0873 (11)	0.0628 (9)	0.0383 (6)	0.0128 (8)	0.0089 (6)	0.0021 (6)
C17	0.0479 (7)	0.0606 (9)	0.0819 (10)	0.0127 (6)	0.0117 (7)	0.0141 (7)

Geometric parameters (Å, º) top

S1—O3	1.4203 (10)	C7—C8	1.3766 (15)
S1—O4	1.4210 (10)	C7—C15	1.3887 (16)
S1—O1	1.6076 (10)	C8—C9	1.3801 (16)
S1—C6	1.7401 (12)	C8—H8A	0.9300
O1—C7	1.4061 (14)	C9—C13	1.4011 (14)
O2—C9	1.3734 (13)	C10—C11	1.441 (2)
O2—C10	1.3760 (17)	C11—C12	1.3439 (19)
O5—C10	1.2018 (16)	C11—H11A	0.9300
O6—C3	1.3563 (15)	C12—C13	1.4509 (17)
O6—C17	1.4244 (18)	C12—C16	1.5011 (18)
C1—C6	1.3862 (17)	C13—C14	1.4017 (16)
C1—C2	1.3875 (18)	C14—C15	1.3796 (18)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.3919 (17)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3924 (18)	C16—H16B	0.9600
C4—C5	1.3751 (18)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.3979 (16)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600

O3—S1—O4	120.27 (7)	O2—C9—C8	115.88 (9)
O3—S1—O1	101.84 (6)	O2—C9—C13	121.43 (10)
O4—S1—O1	108.68 (6)	C8—C9—C13	122.69 (10)
O3—S1—C6	111.00 (6)	O5—C10—O2	116.70 (13)
O4—S1—C6	109.96 (6)	O5—C10—C11	126.35 (14)
O1—S1—C6	103.45 (5)	O2—C10—C11	116.95 (11)
C7—O1—S1	120.22 (7)	C12—C11—C10	123.40 (13)
C9—O2—C10	121.61 (10)	C12—C11—H11A	118.3
C3—O6—C17	118.18 (11)	C10—C11—H11A	118.3
C6—C1—C2	119.95 (11)	C11—C12—C13	118.25 (11)
C6—C1—H1A	120.0	C11—C12—C16	121.49 (12)
C2—C1—H1A	120.0	C13—C12—C16	120.26 (12)
C1—C2—C3	119.29 (11)	C9—C13—C14	117.23 (10)
C1—C2—H2A	120.4	C9—C13—C12	118.30 (10)
C3—C2—H2A	120.4	C14—C13—C12	124.45 (10)
O6—C3—C2	124.50 (11)	C15—C14—C13	121.51 (10)
O6—C3—C4	115.21 (11)	C15—C14—H14A	119.2
C2—C3—C4	120.28 (11)	C13—C14—H14A	119.2
C5—C4—C3	120.64 (11)	C14—C15—C7	118.37 (11)
C5—C4—H4A	119.7	C14—C15—H15A	120.8
C3—C4—H4A	119.7	C7—C15—H15A	120.8
C4—C5—C6	118.91 (11)	C12—C16—H16A	109.5
C4—C5—H5A	120.5	C12—C16—H16B	109.5
C6—C5—H5A	120.5	H16A—C16—H16B	109.5
C1—C6—C5	120.83 (11)	C12—C16—H16C	109.5
C1—C6—S1	120.13 (9)	H16A—C16—H16C	109.5
C5—C6—S1	119.00 (9)	H16B—C16—H16C	109.5
C8—C7—C15	122.74 (11)	O6—C17—H17A	109.5
C8—C7—O1	119.03 (10)	O6—C17—H17B	109.5
C15—C7—O1	118.06 (10)	H17A—C17—H17B	109.5
C7—C8—C9	117.46 (10)	O6—C17—H17C	109.5
C7—C8—H8A	121.3	H17A—C17—H17C	109.5
C9—C8—H8A	121.3	H17B—C17—H17C	109.5

O3—S1—O1—C7	−179.12 (8)	O1—C7—C8—C9	174.84 (10)
O4—S1—O1—C7	−51.20 (10)	C10—O2—C9—C8	−178.76 (12)
C6—S1—O1—C7	65.63 (9)	C10—O2—C9—C13	1.40 (19)
C6—C1—C2—C3	−0.89 (19)	C7—C8—C9—O2	−179.45 (10)
C17—O6—C3—C2	1.5 (2)	C7—C8—C9—C13	0.38 (18)
C17—O6—C3—C4	−179.69 (13)	C9—O2—C10—O5	−178.61 (15)
C1—C2—C3—O6	−178.23 (12)	C9—O2—C10—C11	0.7 (2)
C1—C2—C3—C4	3.04 (19)	O5—C10—C11—C12	176.67 (18)
O6—C3—C4—C5	178.64 (12)	O2—C10—C11—C12	−2.6 (2)
C2—C3—C4—C5	−2.5 (2)	C10—C11—C12—C13	2.2 (2)
C3—C4—C5—C6	−0.2 (2)	C10—C11—C12—C16	−177.60 (15)
C2—C1—C6—C5	−1.80 (19)	O2—C9—C13—C14	179.63 (11)
C2—C1—C6—S1	175.99 (9)	C8—C9—C13—C14	−0.20 (18)
C4—C5—C6—C1	2.33 (19)	O2—C9—C13—C12	−1.81 (17)
C4—C5—C6—S1	−175.49 (10)	C8—C9—C13—C12	178.37 (11)
O3—S1—C6—C1	145.04 (11)	C11—C12—C13—C9	0.03 (19)
O4—S1—C6—C1	9.50 (12)	C16—C12—C13—C9	179.81 (12)
O1—S1—C6—C1	−106.43 (10)	C11—C12—C13—C14	178.48 (13)
O3—S1—C6—C5	−37.13 (12)	C16—C12—C13—C14	−1.7 (2)
O4—S1—C6—C5	−172.67 (10)	C9—C13—C14—C15	−0.06 (18)
O1—S1—C6—C5	71.40 (10)	C12—C13—C14—C15	−178.53 (12)
S1—O1—C7—C8	83.63 (12)	C13—C14—C15—C7	0.1 (2)
S1—O1—C7—C15	−100.99 (12)	C8—C7—C15—C14	0.1 (2)
C15—C7—C8—C9	−0.32 (18)	O1—C7—C15—C14	−175.12 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the O2/C9–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3ⁱ	0.93	2.50	3.4156 (16)	169
C15—H15A···O5ⁱⁱ	0.93	2.44	3.2923 (17)	153
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.96	3.8423 (17)	154

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄O₆S
M_r	346.34
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.9801 (3), 9.2234 (4), 10.9682 (5)
α, β, γ (°)	99.049 (1), 90.288 (1), 93.945 (1)
V (Å³)	795.26 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.39 × 0.34 × 0.17

Data collection
Diffractometer	Bruker APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.913, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	21468, 5907, 4468
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.768

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.131, 1.04
No. of reflections	5907
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.36

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the O2/C9–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3ⁱ	0.93	2.50	3.4156 (16)	169
C15—H15A···O5ⁱⁱ	0.93	2.44	3.2923 (17)	153
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.96	3.8423 (17)	154

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

Footnotes

‡Additional correspondence email: habibahw@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HAW gratefully acknowledges the Malaysian Ministry of Science, Technology and Innovation for the synthesis work funded by grants Nos. 09-05-lfn-meb-004 and 304/PFARMASI/650545/I-121. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH thanks also Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, J.-F., Chen, M., Wallace, D., Tith, S., Arrhenius, T., Kashiwagi, H., Ono, Y., Ishikawa, A., Sato, H., Kozono, T., Sato, H. & Nadzan, A. M. (2004). Bioorg. Med. Chem. Lett. 14, 2411–2415. CrossRef PubMed CAS Google Scholar
Fusegi, K., Kumamoto, T., Nakanishi, W. & Ishikawa, T. (2009). Heterocycles, 77, 503–610. Google Scholar
Han, S., Zhou, V., Pan, S., Liu, Y., Hornsby, M., McMullan, D., Klock, H. E., Haugen, J., Lesley, S. A., Gray, N., Caldwell, J. & Gu, X.-J. (2005). Bioorg. Med. Chem. Lett. 15, 5467–5473. Web of Science CrossRef PubMed CAS Google Scholar
Radanyi, C., Le Bras, G., Messaoudi, S., Bouchlier, C., Peryrat, J.-F., Brion, J. -D., Marsaud, V., Renoir, J. -M. & Alami, M. (2008). Bioorg. Med. Chem. Lett. 18, 2495–2498. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sinha, S., Osman, H., Wahab, H. A., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3275. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Valente, S., Bana, E., Viry, E., Bagrel, D. & Gilbert, S. (2010). Bioorg. Med. Chem. Lett. 20, 5827–5830. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3457

https://doi.org/10.1107/S1600536811049476

Open

access