(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)-p-toluene­sulfonohydrazide

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536808037069

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2341

doi:10.1107/S1600536808037069

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(E)-N′-(5-Bromo-2-hydroxybenzylidene)-p-toluenesulfonohydrazide

Reza Kia,^a Hoong-Kun Fun ^a ^* and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 3 November 2008; accepted 10 November 2008; online 13 November 2008)

The title compound, C₁₄H₁₃BrN₂O₃S, features an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the two benzene rings is 86.47 (6)°. Intermolecular N—H⋯O and C—H⋯O interactions link neighbouring molecules via R₂²(13) ring motifs, forming one-dimensional extended chains along the c axis.

Related literature

For background to sulfonamides, see: Kayser et al. (2004 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures and applications see: Tabatabaee et al. (2007 ); Mehrabi et al. (2008 ); Ali et al. (2007 ); Tierney et al. (2006 ); Krygowski et al. (1998 ).

Experimental

Crystal data

C₁₄H₁₃BrN₂O₃S
M_r = 369.23
Monoclinic, P 2₁ /c
a = 15.8890 (3) Å
b = 9.8502 (2) Å
c = 9.8702 (2) Å
β = 105.475 (1)°
V = 1488.78 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 100.0 (1) K
0.45 × 0.34 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.308, T_max = 0.407
41486 measured reflections
7057 independent reflections
5961 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.06
7057 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.28 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.851 (19)	2.002 (19)	2.8476 (13)	172.4 (19)
O1—H1O1⋯N1	0.84 (3)	1.94 (3)	2.6740 (14)	146 (3)
C7—H7A⋯O1ⁱ	0.93	2.60	3.3793 (15)	142
C10—H10A⋯Br1ⁱⁱ	0.93	2.91	3.8082 (12)	164
C12—H12A⋯O3ⁱⁱⁱ	0.93	2.49	3.3691 (15)	158
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037069/tk2325sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037069/tk2325Isup2.hkl

checkCIF report

Comment top

Sulfonamides were the first class of antimicrobial agents to be discovered. They inhibit dihydropteroate synthetase in the bacterial folic acid pathway. Although their clinical role has diminished, they are still useful in certain situations, because of their efficacy and low cost (Krygowski et al., 1998). Sulfonamides (e.g. sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid. These agents are generally used in combination with other drugs to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). With regard to all of the above, we report herein the crystal structure of the title compound, (I).

Bond lengths and angles in (I), Fig. 1, are comparable with those in related structures (Mehrabi et al., 2008; Ali et al. 2007). An intramolecular O—H···N hydrogen bond is noted which generates a S(6) ring motif. The two benzene rings make the dihedral angle of 86.47 (6)°. Intermolecular N—H···O and C—H···O interactions link neighbouring molecules via R₂²(13) ring motifs to form 1-D extended chains along the c-axis, Fig. 2 and Table 1. The crystal structure is further stabilized by intermolecular N—H···O, C—H···Br, C—H···O and π···π [Cg1···Cg1 = 3.9548 (8) Å; symmetry code: 2 - x, 1 - y, 2 - z] interactions.

Related literature top

For background on sulfonamides, see: Kayser et al. (2004). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures and applications see: Tabatabaee et al. (2007); Mehrabi et al. (2008); Ali et al. (2007); Tierney et al. (2006); Krygowski et al. (1998).

Experimental top

p-Tosylhydrazine (2 mmol) was added to a refluxing ethanolic solution (50 ml) of 5-bromosalicylaldehyde (2 mmol). The mixture was stirred for 2 h. After cooling, the colorless crystalline solid was isolated by filtration, washed with cold ethanol, and recrystallized from an ethanol solution of (I).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% displacement ellipsoids and the atomic numbering. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of (I) viewed down the b-axis, showing 1-D extended chains along the c-axis through N—H···O hydrogen bonding. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-p-toluenesulfonohydrazide top

Crystal data top

C₁₄H₁₃BrN₂O₃S	F(000) = 744
M_r = 369.23	D_x = 1.647 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9995 reflections
a = 15.8890 (3) Å	θ = 2.5–37.4°
b = 9.8502 (2) Å	µ = 2.91 mm⁻¹
c = 9.8702 (2) Å	T = 100 K
β = 105.475 (1)°	Block, colourless
V = 1488.78 (5) Å³	0.45 × 0.34 × 0.31 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7057 independent reflections
Radiation source: fine-focus sealed tube	5961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 36.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→25
T_min = 0.308, T_max = 0.407	k = −16→16
41486 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0378P)² + 0.5647P] where P = (F_o² + 2F_c²)/3
7057 reflections	(Δ/σ)_max = 0.003
199 parameters	Δρ_max = 1.28 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₄H₁₃BrN₂O₃S	V = 1488.78 (5) Å³
M_r = 369.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8890 (3) Å	µ = 2.91 mm⁻¹
b = 9.8502 (2) Å	T = 100 K
c = 9.8702 (2) Å	0.45 × 0.34 × 0.31 mm
β = 105.475 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7057 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5961 reflections with I > 2σ(I)
T_min = 0.308, T_max = 0.407	R_int = 0.035
41486 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 1.28 e Å⁻³
7057 reflections	Δρ_min = −0.59 e Å⁻³
199 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	1.191754 (8)	0.636650 (14)	1.149579 (15)	0.02941 (4)
S1	0.645085 (17)	0.74186 (3)	0.60027 (3)	0.01571 (5)
O1	0.91105 (6)	0.56509 (11)	0.60615 (10)	0.02610 (17)
O2	0.67053 (6)	0.78504 (9)	0.47792 (9)	0.02295 (16)
O3	0.57441 (5)	0.80755 (8)	0.63807 (9)	0.02088 (15)
N1	0.80775 (6)	0.71072 (9)	0.72484 (10)	0.01769 (15)
N2	0.73002 (6)	0.77064 (9)	0.73584 (10)	0.01728 (15)
C1	0.97310 (8)	0.58383 (12)	0.72937 (13)	0.02124 (19)
C2	1.05653 (9)	0.53277 (14)	0.74093 (15)	0.0272 (2)
H2A	1.0683	0.4878	0.6652	0.033*
C3	1.12225 (8)	0.54873 (14)	0.86523 (15)	0.0279 (2)
H3A	1.1778	0.5144	0.8729	0.033*
C4	1.10429 (8)	0.61625 (12)	0.97777 (14)	0.0237 (2)
C5	1.02200 (8)	0.66843 (12)	0.96797 (13)	0.02211 (19)
H5A	1.0110	0.7138	1.0441	0.027*
C6	0.95532 (7)	0.65296 (11)	0.84359 (12)	0.01914 (18)
C7	0.86985 (7)	0.70900 (11)	0.83885 (12)	0.01990 (18)
H7A	0.8600	0.7445	0.9206	0.024*
C8	0.62834 (7)	0.56588 (10)	0.59177 (11)	0.01615 (16)
C9	0.66712 (8)	0.48649 (11)	0.50865 (12)	0.02087 (19)
H9A	0.6983	0.5265	0.4518	0.025*
C10	0.65842 (8)	0.34621 (11)	0.51211 (13)	0.0223 (2)
H10A	0.6841	0.2924	0.4567	0.027*
C11	0.61190 (7)	0.28427 (11)	0.59702 (12)	0.01949 (18)
C12	0.57195 (8)	0.36678 (11)	0.67689 (13)	0.02032 (18)
H12A	0.5393	0.3271	0.7318	0.024*
C13	0.58016 (7)	0.50714 (11)	0.67562 (12)	0.01874 (17)
H13A	0.5539	0.5612	0.7300	0.022*
C14	0.60620 (9)	0.13240 (11)	0.60308 (15)	0.0257 (2)
H14A	0.6230	0.0935	0.5250	0.039*
H14B	0.5473	0.1063	0.5986	0.039*
H14C	0.6446	0.1003	0.6894	0.039*
H1N2	0.7171 (12)	0.7519 (19)	0.812 (2)	0.027 (4)*
H1O1	0.8634 (18)	0.596 (3)	0.615 (3)	0.057 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01916 (6)	0.02972 (7)	0.03454 (8)	−0.00490 (4)	−0.00119 (5)	0.00973 (5)
S1	0.01756 (10)	0.01561 (10)	0.01476 (10)	0.00098 (7)	0.00568 (8)	0.00033 (7)
O1	0.0248 (4)	0.0345 (5)	0.0198 (4)	0.0064 (3)	0.0074 (3)	0.0009 (3)
O2	0.0322 (4)	0.0216 (3)	0.0178 (4)	0.0002 (3)	0.0114 (3)	0.0031 (3)
O3	0.0191 (3)	0.0196 (3)	0.0246 (4)	0.0042 (3)	0.0069 (3)	−0.0005 (3)
N1	0.0164 (4)	0.0173 (3)	0.0206 (4)	0.0000 (3)	0.0071 (3)	0.0001 (3)
N2	0.0165 (4)	0.0191 (4)	0.0171 (4)	−0.0003 (3)	0.0059 (3)	−0.0025 (3)
C1	0.0217 (5)	0.0216 (4)	0.0217 (5)	0.0026 (4)	0.0081 (4)	0.0037 (4)
C2	0.0245 (5)	0.0295 (5)	0.0305 (6)	0.0072 (4)	0.0122 (5)	0.0035 (5)
C3	0.0208 (5)	0.0282 (5)	0.0359 (7)	0.0051 (4)	0.0095 (5)	0.0075 (5)
C4	0.0172 (4)	0.0233 (5)	0.0290 (6)	−0.0010 (4)	0.0035 (4)	0.0069 (4)
C5	0.0189 (5)	0.0213 (4)	0.0251 (5)	−0.0017 (4)	0.0042 (4)	0.0007 (4)
C6	0.0178 (4)	0.0181 (4)	0.0218 (5)	0.0002 (3)	0.0057 (4)	0.0017 (3)
C7	0.0181 (4)	0.0199 (4)	0.0219 (5)	−0.0005 (3)	0.0057 (4)	−0.0023 (4)
C8	0.0168 (4)	0.0161 (4)	0.0154 (4)	−0.0003 (3)	0.0040 (3)	−0.0008 (3)
C9	0.0253 (5)	0.0193 (4)	0.0211 (5)	−0.0006 (4)	0.0114 (4)	−0.0023 (4)
C10	0.0263 (5)	0.0184 (4)	0.0238 (5)	0.0005 (4)	0.0094 (4)	−0.0037 (4)
C11	0.0181 (4)	0.0174 (4)	0.0209 (5)	−0.0002 (3)	0.0015 (4)	0.0004 (3)
C12	0.0187 (4)	0.0201 (4)	0.0228 (5)	−0.0018 (3)	0.0067 (4)	0.0016 (4)
C13	0.0175 (4)	0.0197 (4)	0.0205 (4)	−0.0001 (3)	0.0075 (3)	−0.0002 (3)
C14	0.0291 (6)	0.0171 (4)	0.0286 (6)	−0.0001 (4)	0.0035 (5)	0.0009 (4)

Geometric parameters (Å, º) top

Br1—C4	1.8947 (13)	C5—H5A	0.9300
S1—O3	1.4292 (8)	C6—C7	1.4551 (16)
S1—O2	1.4363 (9)	C7—H7A	0.9300
S1—N2	1.6518 (10)	C8—C9	1.3907 (15)
S1—C8	1.7524 (10)	C8—C13	1.3943 (15)
O1—C1	1.3585 (16)	C9—C10	1.3900 (16)
O1—H1O1	0.84 (3)	C9—H9A	0.9300
N1—C7	1.2837 (15)	C10—C11	1.3971 (17)
N1—N2	1.3989 (13)	C10—H10A	0.9300
N2—H1N2	0.852 (19)	C11—C12	1.3972 (16)
C1—C2	1.3937 (17)	C11—C14	1.5008 (16)
C1—C6	1.4087 (16)	C12—C13	1.3891 (15)
C2—C3	1.392 (2)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (2)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.3840 (17)	C14—H14C	0.9600
C5—C6	1.3995 (17)

O3—S1—O2	120.16 (5)	C1—C6—C7	122.85 (11)
O3—S1—N2	103.88 (5)	N1—C7—C6	121.72 (10)
O2—S1—N2	106.13 (5)	N1—C7—H7A	119.1
O3—S1—C8	109.91 (5)	C6—C7—H7A	119.1
O2—S1—C8	109.02 (5)	C9—C8—C13	121.11 (10)
N2—S1—C8	106.82 (5)	C9—C8—S1	119.93 (8)
C1—O1—H1O1	108.2 (18)	C13—C8—S1	118.85 (8)
C7—N1—N2	115.19 (9)	C10—C9—C8	118.81 (10)
N1—N2—S1	114.34 (7)	C10—C9—H9A	120.6
N1—N2—H1N2	113.8 (13)	C8—C9—H9A	120.6
S1—N2—H1N2	110.0 (13)	C9—C10—C11	121.39 (10)
O1—C1—C2	118.13 (11)	C9—C10—H10A	119.3
O1—C1—C6	121.98 (10)	C11—C10—H10A	119.3
C2—C1—C6	119.89 (12)	C10—C11—C12	118.51 (10)
C3—C2—C1	120.33 (12)	C10—C11—C14	120.42 (11)
C3—C2—H2A	119.8	C12—C11—C14	121.07 (11)
C1—C2—H2A	119.8	C13—C12—C11	121.06 (10)
C4—C3—C2	119.57 (11)	C13—C12—H12A	119.5
C4—C3—H3A	120.2	C11—C12—H12A	119.5
C2—C3—H3A	120.2	C12—C13—C8	119.09 (10)
C5—C4—C3	120.94 (12)	C12—C13—H13A	120.5
C5—C4—Br1	118.48 (10)	C8—C13—H13A	120.5
C3—C4—Br1	120.58 (9)	C11—C14—H14A	109.5
C4—C5—C6	120.05 (12)	C11—C14—H14B	109.5
C4—C5—H5A	120.0	H14A—C14—H14B	109.5
C6—C5—H5A	120.0	C11—C14—H14C	109.5
C5—C6—C1	119.22 (11)	H14A—C14—H14C	109.5
C5—C6—C7	117.93 (10)	H14B—C14—H14C	109.5

C7—N1—N2—S1	−166.98 (8)	C5—C6—C7—N1	173.17 (11)
O3—S1—N2—N1	177.80 (7)	C1—C6—C7—N1	−7.24 (17)
O2—S1—N2—N1	−54.59 (9)	O3—S1—C8—C9	155.48 (9)
C8—S1—N2—N1	61.63 (8)	O2—S1—C8—C9	21.84 (11)
O1—C1—C2—C3	−179.66 (12)	N2—S1—C8—C9	−92.44 (10)
C6—C1—C2—C3	0.54 (19)	O3—S1—C8—C13	−28.24 (10)
C1—C2—C3—C4	−0.2 (2)	O2—S1—C8—C13	−161.87 (9)
C2—C3—C4—C5	−0.25 (19)	N2—S1—C8—C13	83.85 (9)
C2—C3—C4—Br1	178.81 (10)	C13—C8—C9—C10	−1.12 (18)
C3—C4—C5—C6	0.31 (18)	S1—C8—C9—C10	175.08 (9)
Br1—C4—C5—C6	−178.78 (9)	C8—C9—C10—C11	−0.07 (19)
C4—C5—C6—C1	0.06 (17)	C9—C10—C11—C12	1.54 (18)
C4—C5—C6—C7	179.67 (11)	C9—C10—C11—C14	−177.72 (12)
O1—C1—C6—C5	179.73 (11)	C10—C11—C12—C13	−1.87 (18)
C2—C1—C6—C5	−0.48 (17)	C14—C11—C12—C13	177.39 (11)
O1—C1—C6—C7	0.14 (17)	C11—C12—C13—C8	0.73 (18)
C2—C1—C6—C7	179.92 (11)	C9—C8—C13—C12	0.80 (17)
N2—N1—C7—C6	−178.58 (10)	S1—C8—C13—C12	−175.44 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.851 (19)	2.002 (19)	2.8476 (13)	172.4 (19)
O1—H1O1···N1	0.84 (3)	1.94 (3)	2.6740 (14)	146 (3)
C7—H7A···O1ⁱ	0.93	2.60	3.3793 (15)	142
C10—H10A···Br1ⁱⁱ	0.93	2.91	3.8082 (12)	164
C12—H12A···O3ⁱⁱⁱ	0.93	2.49	3.3691 (15)	158

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃BrN₂O₃S
M_r	369.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.8890 (3), 9.8502 (2), 9.8702 (2)
β (°)	105.475 (1)
V (Å³)	1488.78 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.45 × 0.34 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.308, 0.407
No. of measured, independent and observed [I > 2σ(I)] reflections	41486, 7057, 5961
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.827

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.06
No. of reflections	7057
No. of parameters	199
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.28, −0.59

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.851 (19)	2.002 (19)	2.8476 (13)	172.4 (19)
O1—H1O1···N1	0.84 (3)	1.94 (3)	2.6740 (14)	146 (3)
C7—H7A···O1ⁱ	0.93	2.60	3.3793 (15)	142
C10—H10A···Br1ⁱⁱ	0.93	2.91	3.8082 (12)	164
C12—H12A···O3ⁱⁱⁱ	0.93	2.49	3.3691 (15)	158

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support.

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