2,3-Dibromo-3-(4-bromo­phen­yl)-1-[3-(4-meth­oxy­phen­yl)sydnon-4-yl]propan-1-one

Fun, H.-K.; Hemamalini, M.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811010002

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o951

doi:10.1107/S1600536811010002

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2,3-Dibromo-3-(4-bromophenyl)-1-[3-(4-methoxyphenyl)sydnon-4-yl]propan-1-one

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 March 2011; accepted 17 March 2011; online 23 March 2011)

In the title compound {systematic name: 4-[2,3-dibromo-3-(4-bromophenyl)propanoyl]-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ylium-5-olate}, C₁₈H₁₃Br₃N₂O₄, the central oxadiazole ring, which is essentially planar with a maximum deviation of 0.016 (3) Å, makes dihedral angles of 29.98 (16) and 52.04 (16)°, respectively, with the terminal bromo-substituted and methoxy-substituted benzene rings. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif.

Related literature

For applications of sydnones, see: Rai et al. (2008 ); Jyothi et al. (2008 ). For details of chalcones, see: Rai et al. (2007 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₃Br₃N₂O₄
M_r = 561.03
Monoclinic, P 2₁ /n
a = 7.8024 (1) Å
b = 24.0261 (3) Å
c = 10.8211 (1) Å
β = 108.848 (1)°
V = 1919.76 (4) Å³
Z = 4
Mo Kα radiation
μ = 6.33 mm⁻¹
T = 296 K
0.39 × 0.27 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.191, T_max = 0.496
20615 measured reflections
5841 independent reflections
3490 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.00
5841 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.98	2.35	3.032 (4)	126

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/S1600536811010002/is2691sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010002/is2691Isup2.hkl

checkCIF report

Comment top

Sydnones constitute a well-defined class of mesoionic compounds that contain the 1,2,3-oxadiazole ring system. The study of sydnones still remains a field of interest because of their electronic structure and also because of the varied types of biological activities (Rai et al., 2008). Recently, sydnone derivatives were found to exhibit promising antimicrobial properties (Jyothi et al., 2008). Chalcones were obtained by the base-catalyzed condensation of 4-acetyl-3-aryl sydnones with aromatic aldehydes in alcoholic medium employing sodium hydroxide as catalyst at 0–5 °C. Bromination of chalcones with bromine in glacial acetic acid afforded dibromo chalcones (Rai et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. The oxadiazole (N1/N2/O3/C10/C11) ring is essentially planar, with a maximum deviation of 0.016 (3) Å for atom C11. The central oxadiazole ring makes dihedral angles of 29.98 (16)° and 52.04 (16)°, with the terminal bromo-substituted phenyl (C1–C6) and the methoxy-substituted phenyl( C12–C17) rings, respectively.

In the crystal, (Fig. 2), there is an intramolecular C8—H8A···O2 (Table 1) hydrogen bond, which generates an S(6) ring motif (Bernstein et al., 1995).

Related literature top

For applications of sydnones, see: Rai et al. (2008); Jyothi et al. (2008). For details of chalcones, see: Rai et al. (2007). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

1-(3¹-Phenylsydnon-4¹-yl)-3-(p-bromophenyl)- propen-1-one (0.01 mol) was dissolved in glacial acetic acid (25–30 ml) by gentle warming. A solution of bromine in glacial acetic acid (30% w/v) was added to it with constant stirring till the yellow colour of the bromine persisted. The reaction mixture was stirred at room temperature for 1–2 hours. The solid which separated was filtered, washed with methanol and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.

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 50% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound (I).

4-[2,3-dibromo-3-(4-bromophenyl)propanoyl]-3-(4-methoxyphenyl)- 1,2,3-oxadiazol-3-ylium-5-olate top

Crystal data top

C₁₈H₁₃Br₃N₂O₄	F(000) = 1088
M_r = 561.03	D_x = 1.941 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6367 reflections
a = 7.8024 (1) Å	θ = 2.6–28.3°
b = 24.0261 (3) Å	µ = 6.33 mm⁻¹
c = 10.8211 (1) Å	T = 296 K
β = 108.848 (1)°	Plate, colourless
V = 1919.76 (4) Å³	0.39 × 0.27 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5841 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 30.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.191, T_max = 0.496	k = −34→23
20615 measured reflections	l = −14→15

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) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0481P)² + 0.1633P] where P = (F_o² + 2F_c²)/3
5841 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₈H₁₃Br₃N₂O₄	V = 1919.76 (4) Å³
M_r = 561.03	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8024 (1) Å	µ = 6.33 mm⁻¹
b = 24.0261 (3) Å	T = 296 K
c = 10.8211 (1) Å	0.39 × 0.27 × 0.13 mm
β = 108.848 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5841 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3490 reflections with I > 2σ(I)
T_min = 0.191, T_max = 0.496	R_int = 0.034
20615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	Δρ_max = 0.63 e Å⁻³
5841 reflections	Δρ_min = −0.74 e Å⁻³
245 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
Br1	1.14574 (6)	−0.038999 (13)	0.37333 (4)	0.06333 (13)
Br2	0.95173 (5)	0.252012 (13)	0.22636 (3)	0.05191 (11)
Br3	0.87928 (7)	0.183591 (15)	0.60488 (4)	0.07974 (16)
O1	0.9670 (3)	0.31433 (8)	0.5109 (2)	0.0525 (6)
O2	0.4433 (3)	0.22666 (9)	0.3829 (2)	0.0557 (6)
O3	0.3565 (3)	0.31283 (9)	0.4242 (2)	0.0513 (5)
O4	1.0534 (3)	0.52989 (8)	0.7386 (2)	0.0541 (6)
N1	0.4365 (3)	0.36133 (10)	0.4786 (2)	0.0462 (6)
N2	0.6087 (3)	0.35365 (9)	0.5050 (2)	0.0347 (5)
C1	0.9177 (4)	0.11794 (11)	0.2936 (3)	0.0427 (7)
H1A	0.8111	0.1332	0.2379	0.051*
C2	0.9488 (4)	0.06109 (12)	0.2902 (3)	0.0468 (7)
H2A	0.8635	0.0382	0.2329	0.056*
C3	1.1067 (4)	0.03920 (11)	0.3725 (3)	0.0420 (7)
C4	1.2369 (4)	0.07204 (13)	0.4552 (3)	0.0479 (8)
H4A	1.3447	0.0565	0.5084	0.057*
C5	1.2064 (4)	0.12855 (12)	0.4587 (3)	0.0420 (7)
H5A	1.2945	0.1512	0.5145	0.050*
C6	1.0445 (4)	0.15199 (11)	0.3793 (3)	0.0362 (6)
C7	1.0097 (4)	0.21271 (11)	0.3953 (3)	0.0337 (6)
H7A	1.1185	0.2293	0.4570	0.040*
C8	0.8505 (4)	0.22382 (11)	0.4423 (3)	0.0395 (6)
H8A	0.7381	0.2121	0.3755	0.047*
C9	0.8350 (4)	0.28446 (11)	0.4789 (3)	0.0374 (6)
C10	0.6552 (4)	0.30218 (11)	0.4736 (3)	0.0354 (6)
C11	0.4882 (4)	0.27294 (12)	0.4223 (3)	0.0429 (7)
C12	0.7239 (4)	0.40007 (11)	0.5653 (3)	0.0342 (6)
C13	0.8625 (4)	0.39242 (11)	0.6808 (3)	0.0389 (7)
H13A	0.8838	0.3576	0.7206	0.047*
C14	0.9684 (4)	0.43718 (12)	0.7358 (3)	0.0423 (7)
H14A	1.0633	0.4328	0.8135	0.051*
C15	0.9355 (4)	0.48902 (11)	0.6766 (3)	0.0406 (7)
C16	0.7926 (4)	0.49630 (12)	0.5621 (3)	0.0447 (7)
H16A	0.7685	0.5312	0.5233	0.054*
C17	0.6866 (4)	0.45139 (12)	0.5062 (3)	0.0433 (7)
H17A	0.5905	0.4557	0.4291	0.052*
C18	1.0212 (5)	0.58493 (13)	0.6871 (4)	0.0671 (10)
H18A	1.1193	0.6087	0.7345	0.101*
H18B	0.9100	0.5987	0.6954	0.101*
H18C	1.0126	0.5844	0.5966	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0987 (3)	0.02994 (17)	0.0680 (2)	0.00875 (16)	0.0361 (2)	0.00131 (14)
Br2	0.0698 (2)	0.04374 (19)	0.04443 (19)	0.00350 (15)	0.02161 (16)	0.00642 (13)
Br3	0.1518 (4)	0.0394 (2)	0.0769 (3)	0.0121 (2)	0.0770 (3)	0.01108 (17)
O1	0.0444 (12)	0.0336 (11)	0.0857 (16)	−0.0076 (9)	0.0296 (11)	−0.0153 (11)
O2	0.0558 (13)	0.0399 (12)	0.0737 (15)	−0.0161 (11)	0.0243 (11)	−0.0118 (11)
O3	0.0404 (12)	0.0495 (13)	0.0626 (14)	−0.0055 (10)	0.0149 (10)	−0.0070 (11)
O4	0.0582 (14)	0.0369 (12)	0.0598 (14)	−0.0091 (10)	0.0087 (11)	−0.0069 (10)
N1	0.0429 (15)	0.0402 (14)	0.0546 (15)	−0.0011 (11)	0.0145 (12)	−0.0050 (12)
N2	0.0362 (13)	0.0325 (12)	0.0370 (12)	0.0008 (10)	0.0140 (10)	−0.0008 (9)
C1	0.0403 (16)	0.0350 (15)	0.0506 (17)	0.0012 (12)	0.0116 (14)	−0.0072 (13)
C2	0.0555 (19)	0.0331 (15)	0.0527 (18)	−0.0051 (14)	0.0187 (15)	−0.0107 (14)
C3	0.0583 (19)	0.0270 (14)	0.0501 (17)	0.0016 (13)	0.0308 (15)	0.0008 (12)
C4	0.0545 (19)	0.0405 (17)	0.0468 (18)	0.0080 (15)	0.0138 (15)	0.0036 (14)
C5	0.0470 (17)	0.0357 (15)	0.0404 (16)	−0.0007 (13)	0.0102 (14)	−0.0026 (12)
C6	0.0432 (16)	0.0293 (14)	0.0398 (15)	−0.0002 (12)	0.0186 (13)	−0.0050 (11)
C7	0.0377 (15)	0.0291 (13)	0.0360 (14)	−0.0008 (11)	0.0142 (12)	−0.0021 (11)
C8	0.0493 (17)	0.0288 (14)	0.0441 (16)	−0.0053 (12)	0.0202 (13)	−0.0030 (12)
C9	0.0457 (16)	0.0268 (13)	0.0453 (16)	−0.0017 (12)	0.0225 (13)	−0.0012 (12)
C10	0.0413 (16)	0.0286 (14)	0.0397 (15)	−0.0034 (11)	0.0177 (12)	−0.0007 (11)
C11	0.0458 (17)	0.0410 (17)	0.0443 (17)	−0.0078 (14)	0.0178 (14)	0.0008 (13)
C12	0.0389 (15)	0.0261 (13)	0.0404 (15)	0.0007 (11)	0.0166 (12)	−0.0047 (11)
C13	0.0467 (17)	0.0294 (14)	0.0410 (16)	0.0092 (12)	0.0147 (13)	0.0059 (12)
C14	0.0428 (17)	0.0390 (16)	0.0407 (16)	0.0061 (13)	0.0074 (13)	−0.0013 (13)
C15	0.0457 (17)	0.0314 (15)	0.0461 (17)	0.0012 (12)	0.0168 (14)	−0.0043 (12)
C16	0.0534 (18)	0.0292 (15)	0.0476 (17)	0.0017 (13)	0.0110 (15)	0.0037 (13)
C17	0.0453 (17)	0.0361 (16)	0.0430 (16)	0.0056 (13)	0.0067 (13)	0.0032 (12)
C18	0.082 (3)	0.0320 (18)	0.084 (3)	−0.0109 (17)	0.022 (2)	−0.0017 (17)

Geometric parameters (Å, º) top

Br1—C3	1.903 (3)	C5—H5A	0.9300
Br2—C7	1.976 (3)	C6—C7	1.504 (4)
Br3—C8	1.956 (3)	C7—C8	1.510 (4)
O1—C9	1.211 (3)	C7—H7A	0.9800
O2—C11	1.202 (3)	C8—C9	1.525 (4)
O3—N1	1.362 (3)	C8—H8A	0.9800
O3—C11	1.411 (4)	C9—C10	1.449 (4)
O4—C15	1.364 (3)	C10—C11	1.425 (4)
O4—C18	1.426 (4)	C12—C13	1.376 (4)
N1—N2	1.293 (3)	C12—C17	1.376 (4)
N2—C10	1.363 (3)	C13—C14	1.369 (4)
N2—C12	1.449 (3)	C13—H13A	0.9300
C1—C6	1.384 (4)	C14—C15	1.386 (4)
C1—C2	1.390 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.385 (4)
C2—C3	1.371 (4)	C16—C17	1.375 (4)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.367 (4)	C17—H17A	0.9300
C4—C5	1.381 (4)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.396 (4)	C18—H18C	0.9600

N1—O3—C11	110.7 (2)	Br3—C8—H8A	109.8
C15—O4—C18	118.0 (2)	O1—C9—C10	124.1 (2)
N2—N1—O3	105.8 (2)	O1—C9—C8	120.6 (3)
N1—N2—C10	114.6 (2)	C10—C9—C8	115.3 (2)
N1—N2—C12	116.0 (2)	N2—C10—C11	105.1 (2)
C10—N2—C12	129.4 (2)	N2—C10—C9	126.1 (2)
C6—C1—C2	120.3 (3)	C11—C10—C9	128.5 (3)
C6—C1—H1A	119.8	O2—C11—O3	120.2 (3)
C2—C1—H1A	119.8	O2—C11—C10	136.0 (3)
C3—C2—C1	119.2 (3)	O3—C11—C10	103.8 (2)
C3—C2—H2A	120.4	C13—C12—C17	121.9 (3)
C1—C2—H2A	120.4	C13—C12—N2	119.8 (2)
C4—C3—C2	121.7 (3)	C17—C12—N2	118.2 (2)
C4—C3—Br1	118.9 (2)	C14—C13—C12	118.5 (3)
C2—C3—Br1	119.4 (2)	C14—C13—H13A	120.8
C3—C4—C5	119.2 (3)	C12—C13—H13A	120.8
C3—C4—H4A	120.4	C13—C14—C15	120.6 (3)
C5—C4—H4A	120.4	C13—C14—H14A	119.7
C4—C5—C6	120.6 (3)	C15—C14—H14A	119.7
C4—C5—H5A	119.7	O4—C15—C16	124.7 (3)
C6—C5—H5A	119.7	O4—C15—C14	115.1 (3)
C1—C6—C5	118.9 (3)	C16—C15—C14	120.2 (3)
C1—C6—C7	122.2 (2)	C17—C16—C15	119.4 (3)
C5—C6—C7	118.8 (2)	C17—C16—H16A	120.3
C6—C7—C8	114.1 (2)	C15—C16—H16A	120.3
C6—C7—Br2	110.67 (18)	C16—C17—C12	119.5 (3)
C8—C7—Br2	105.06 (18)	C16—C17—H17A	120.3
C6—C7—H7A	108.9	C12—C17—H17A	120.3
C8—C7—H7A	108.9	O4—C18—H18A	109.5
Br2—C7—H7A	108.9	O4—C18—H18B	109.5
C7—C8—C9	113.5 (2)	H18A—C18—H18B	109.5
C7—C8—Br3	110.34 (19)	O4—C18—H18C	109.5
C9—C8—Br3	103.54 (18)	H18A—C18—H18C	109.5
C7—C8—H8A	109.8	H18B—C18—H18C	109.5
C9—C8—H8A	109.8

C11—O3—N1—N2	2.3 (3)	C12—N2—C10—C9	−8.6 (4)
O3—N1—N2—C10	−0.6 (3)	O1—C9—C10—N2	−1.1 (5)
O3—N1—N2—C12	−179.6 (2)	C8—C9—C10—N2	178.2 (2)
C6—C1—C2—C3	−0.2 (5)	O1—C9—C10—C11	171.4 (3)
C1—C2—C3—C4	−1.9 (5)	C8—C9—C10—C11	−9.3 (4)
C1—C2—C3—Br1	177.5 (2)	N1—O3—C11—O2	176.8 (3)
C2—C3—C4—C5	1.9 (5)	N1—O3—C11—C10	−3.0 (3)
Br1—C3—C4—C5	−177.5 (2)	N2—C10—C11—O2	−177.3 (3)
C3—C4—C5—C6	0.2 (5)	C9—C10—C11—O2	9.0 (6)
C2—C1—C6—C5	2.3 (5)	N2—C10—C11—O3	2.5 (3)
C2—C1—C6—C7	−174.2 (3)	C9—C10—C11—O3	−171.2 (3)
C4—C5—C6—C1	−2.3 (5)	N1—N2—C12—C13	125.9 (3)
C4—C5—C6—C7	174.3 (3)	C10—N2—C12—C13	−52.8 (4)
C1—C6—C7—C8	60.9 (4)	N1—N2—C12—C17	−52.1 (3)
C5—C6—C7—C8	−115.6 (3)	C10—N2—C12—C17	129.2 (3)
C1—C6—C7—Br2	−57.4 (3)	C17—C12—C13—C14	−1.7 (4)
C5—C6—C7—Br2	126.1 (2)	N2—C12—C13—C14	−179.6 (3)
C6—C7—C8—C9	170.7 (2)	C12—C13—C14—C15	0.4 (4)
Br2—C7—C8—C9	−67.9 (2)	C18—O4—C15—C16	4.2 (5)
C6—C7—C8—Br3	55.0 (3)	C18—O4—C15—C14	−176.5 (3)
Br2—C7—C8—Br3	176.43 (11)	C13—C14—C15—O4	−178.2 (3)
C7—C8—C9—O1	−24.4 (4)	C13—C14—C15—C16	1.2 (5)
Br3—C8—C9—O1	95.3 (3)	O4—C15—C16—C17	177.7 (3)
C7—C8—C9—C10	156.2 (2)	C14—C15—C16—C17	−1.6 (5)
Br3—C8—C9—C10	−84.1 (2)	C15—C16—C17—C12	0.3 (5)
N1—N2—C10—C11	−1.3 (3)	C13—C12—C17—C16	1.4 (5)
C12—N2—C10—C11	177.5 (2)	N2—C12—C17—C16	179.3 (3)
N1—N2—C10—C9	172.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.98	2.35	3.032 (4)	126

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Br₃N₂O₄
M_r	561.03
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.8024 (1), 24.0261 (3), 10.8211 (1)
β (°)	108.848 (1)
V (Å³)	1919.76 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.33
Crystal size (mm)	0.39 × 0.27 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.191, 0.496
No. of measured, independent and observed [I > 2σ(I)] reflections	20615, 5841, 3490
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.00
No. of reflections	5841
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.74

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
C8—H8A···O2	0.98	2.35	3.032 (4)	126

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH 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.

References

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