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

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

doi:10.1107/S1600536808038695

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2424

doi:10.1107/S1600536808038695

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(E)-N′-(5-Chloro-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 6 November 2008; accepted 19 November 2008; online 22 November 2008)

The title compound, C₁₄H₁₃ClN₂O₃S, features an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring motif. Intermolecular N—H⋯O hydrogen bonds and C—H⋯O close contacts link neighbouring molecules forming R₂²(13) ring motifs. In the crystal structure, molecules are further linked by C—H⋯Cl interactions, forming one-dimensional extended chains along the c axis. The dihedral angle between the two benzene rings is 86.06 (3)°. The crystal structure is further stabilized by weak intermolecular π–π interactions [interplanar stacking distance = 3.357 (7) Å].

Related literature

For related structures and applications, see, for example: Kayser et al. (2004 ); Tierney et al. (2006 ); Tabatabaee et al. (2007 ); Ali et al. (2007 ); Mehrabi et al. (2008 ); Kia et al. (2008 ). For the values of bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃ClN₂O₃S
M_r = 324.78
Monoclinic, P 2₁ /c
a = 15.7454 (3) Å
b = 9.8338 (2) Å
c = 9.8455 (2) Å
β = 105.941 (1)°
V = 1465.83 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100.0 (1) K
0.45 × 0.38 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.836, T_max = 0.883
16498 measured reflections
5274 independent reflections
4761 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.093
S = 1.10
5274 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.75 (2)	2.00 (2)	2.6690 (13)	149 (2)
N2—H1N2⋯O2ⁱ	0.881 (16)	1.961 (17)	2.8375 (12)	172.8 (17)
C7—H7A⋯O1ⁱ	0.93	2.59	3.3679 (14)	142
C10—H10A⋯Cl1ⁱⁱ	0.93	2.82	3.7256 (12)	164
C12—H12A⋯O3ⁱⁱⁱ	0.93	2.48	3.3549 (14)	157
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808038695/pk2133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038695/pk2133Isup2.hkl

checkCIF report

Comment top

Sulfonamides were the first class of antimicrobial agents to be discovered. Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid (Kayser et al., 2004). These agents are generally used in combination with other drugs (usually sulfonamides) to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). With regard to all of the above important features, we report the crystal structure of the title compound.

The title compund (Fig. I), is a novel sulfonamide derivative. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with those in related structures (Kia et al., 2008; Mehrabi et al., 2008; Ali et al. 2007). An intramolecular O—H···N hydrogen bond generates S(6) ring motif, and the molecule adopts a 'vault' shape. Intermolecular N—H···O and C—H···O interactions link neighbouring molecules by R₂²(13) ring motifs. The two benzene rings make a dihedral angle of 86.06 (3)°. In the crystal structure, molecules are linked together by intermolecular C—H···Cl, N—H···O and C—H···O interactions, forming one-dimensional extended chains along the c axis. The crystal structure is further stabilized by weak intermolecular π-π interactions [interplanar distance = 3.357 (7) Å].

Related literature top

For related structures and applications, see, for example: Kayser et al. (2004); Tierney et al. (2006);Tabatabaee et al. (2007); Ali et al. (2007); Mehrabi et al. (2008); Kia et al. (2008). For the values of bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The synthetic method has been described earlier (Kia et al., 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

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 the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing viewed down the b-axis, showing one-dimensional extended chains along the c-axis. Intermolecular interactions are shown as dashed lines.

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

Crystal data top

C₁₄H₁₃ClN₂O₃S	F(000) = 672
M_r = 324.78	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9969 reflections
a = 15.7454 (3) Å	θ = 2.7–36.2°
b = 9.8338 (2) Å	µ = 0.41 mm⁻¹
c = 9.8455 (2) Å	T = 100 K
β = 105.941 (1)°	Block, colourless
V = 1465.83 (5) Å³	0.45 × 0.38 × 0.31 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5274 independent reflections
Radiation source: fine-focus sealed tube	4761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→23
T_min = 0.836, T_max = 0.883	k = −11→14
16498 measured reflections	l = −14→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0458P)² + 0.5147P] where P = (F_o² + 2F_c²)/3
5274 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₄H₁₃ClN₂O₃S	V = 1465.83 (5) Å³
M_r = 324.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.7454 (3) Å	µ = 0.41 mm⁻¹
b = 9.8338 (2) Å	T = 100 K
c = 9.8455 (2) Å	0.45 × 0.38 × 0.31 mm
β = 105.941 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5274 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4761 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.883	R_int = 0.020
16498 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.44 e Å⁻³
5274 reflections	Δρ_min = −0.38 e Å⁻³
199 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cryosystems 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
Cl1	0.694874 (18)	0.12795 (3)	0.64129 (3)	0.03146 (8)
S1	0.146818 (15)	0.24140 (2)	0.10615 (2)	0.01365 (6)
O1	0.41411 (6)	0.06452 (10)	0.11049 (9)	0.02515 (17)
O2	0.17263 (6)	0.28771 (8)	−0.01531 (8)	0.02080 (15)
O3	0.07539 (5)	0.30583 (8)	0.14463 (8)	0.01865 (14)
N1	0.31124 (5)	0.20818 (9)	0.23227 (9)	0.01581 (15)
N2	0.23293 (5)	0.26798 (9)	0.24403 (9)	0.01551 (15)
C1	0.47774 (7)	0.08266 (11)	0.23401 (11)	0.02019 (19)
C2	0.56194 (8)	0.03165 (13)	0.24406 (13)	0.0267 (2)
H2A	0.5731	−0.0121	0.1670	0.032*
C3	0.62907 (8)	0.04587 (13)	0.36843 (14)	0.0277 (2)
H3A	0.6850	0.0113	0.3751	0.033*
C4	0.61217 (7)	0.11203 (12)	0.48286 (13)	0.0234 (2)
C5	0.52935 (7)	0.16436 (11)	0.47481 (12)	0.02130 (19)
H5A	0.5191	0.2088	0.5522	0.026*
C6	0.46098 (6)	0.15033 (10)	0.34992 (11)	0.01791 (18)
C7	0.37483 (7)	0.20586 (11)	0.34673 (11)	0.01807 (18)
H7A	0.3655	0.2405	0.4294	0.022*
C8	0.13003 (6)	0.06529 (10)	0.09358 (10)	0.01422 (16)
C9	0.16949 (7)	−0.01247 (11)	0.00975 (11)	0.01837 (18)
H9A	0.2011	0.0290	−0.0460	0.022*
C10	0.16103 (7)	−0.15310 (11)	0.01051 (11)	0.01982 (19)
H10A	0.1873	−0.2056	−0.0453	0.024*
C11	0.11378 (6)	−0.21695 (10)	0.09355 (10)	0.01714 (17)
C12	0.07307 (7)	−0.13615 (11)	0.17433 (11)	0.01804 (18)
H12A	0.0400	−0.1773	0.2280	0.022*
C13	0.08123 (6)	0.00428 (10)	0.17580 (10)	0.01632 (17)
H13A	0.0545	0.0571	0.2308	0.020*
C14	0.10817 (8)	−0.36948 (11)	0.09768 (13)	0.0235 (2)
H14A	0.1204	−0.4070	0.0150	0.035*
H14B	0.0499	−0.3958	0.1001	0.035*
H14C	0.1506	−0.4030	0.1805	0.035*
H1N2	0.2190 (11)	0.2514 (16)	0.3232 (17)	0.028 (4)*
H1O1	0.3722 (14)	0.093 (2)	0.120 (2)	0.050 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01936 (12)	0.03239 (16)	0.03641 (16)	−0.00588 (10)	−0.00283 (10)	0.01246 (12)
S1	0.01639 (11)	0.01291 (11)	0.01269 (10)	0.00087 (7)	0.00572 (8)	0.00034 (7)
O1	0.0244 (4)	0.0326 (5)	0.0194 (4)	0.0074 (3)	0.0076 (3)	0.0000 (3)
O2	0.0311 (4)	0.0184 (3)	0.0158 (3)	0.0000 (3)	0.0114 (3)	0.0026 (3)
O3	0.0183 (3)	0.0169 (3)	0.0220 (3)	0.0041 (3)	0.0076 (3)	−0.0002 (3)
N1	0.0157 (3)	0.0144 (4)	0.0188 (4)	0.0000 (3)	0.0072 (3)	−0.0004 (3)
N2	0.0154 (3)	0.0173 (4)	0.0151 (3)	−0.0003 (3)	0.0064 (3)	−0.0029 (3)
C1	0.0208 (4)	0.0195 (5)	0.0215 (4)	0.0030 (4)	0.0079 (4)	0.0043 (4)
C2	0.0249 (5)	0.0272 (6)	0.0307 (5)	0.0076 (4)	0.0123 (4)	0.0047 (4)
C3	0.0197 (4)	0.0264 (6)	0.0384 (6)	0.0053 (4)	0.0101 (4)	0.0096 (5)
C4	0.0170 (4)	0.0210 (5)	0.0300 (5)	−0.0019 (4)	0.0026 (4)	0.0084 (4)
C5	0.0191 (4)	0.0194 (5)	0.0244 (5)	−0.0022 (4)	0.0042 (4)	0.0019 (4)
C6	0.0170 (4)	0.0156 (4)	0.0214 (4)	−0.0002 (3)	0.0059 (3)	0.0021 (3)
C7	0.0181 (4)	0.0169 (4)	0.0195 (4)	−0.0008 (3)	0.0057 (3)	−0.0020 (3)
C8	0.0148 (4)	0.0136 (4)	0.0140 (4)	0.0000 (3)	0.0036 (3)	−0.0005 (3)
C9	0.0231 (4)	0.0164 (4)	0.0182 (4)	−0.0009 (3)	0.0099 (3)	−0.0018 (3)
C10	0.0238 (4)	0.0165 (4)	0.0207 (4)	0.0007 (4)	0.0087 (4)	−0.0033 (3)
C11	0.0168 (4)	0.0145 (4)	0.0179 (4)	−0.0004 (3)	0.0009 (3)	0.0000 (3)
C12	0.0169 (4)	0.0177 (4)	0.0201 (4)	−0.0017 (3)	0.0060 (3)	0.0019 (3)
C13	0.0158 (4)	0.0168 (4)	0.0176 (4)	0.0002 (3)	0.0067 (3)	−0.0004 (3)
C14	0.0267 (5)	0.0151 (4)	0.0265 (5)	−0.0005 (4)	0.0037 (4)	0.0006 (4)

Geometric parameters (Å, º) top

Cl1—C4	1.7429 (12)	C5—H5A	0.9300
S1—O3	1.4296 (7)	C6—C7	1.4545 (14)
S1—O2	1.4386 (7)	C7—H7A	0.9300
S1—N2	1.6548 (9)	C8—C9	1.3905 (13)
S1—C8	1.7512 (10)	C8—C13	1.3954 (13)
O1—C1	1.3585 (14)	C9—C10	1.3895 (15)
O1—H1O1	0.75 (2)	C9—H9A	0.9300
N1—C7	1.2858 (13)	C10—C11	1.3965 (15)
N1—N2	1.3994 (11)	C10—H10A	0.9300
N2—H1N2	0.881 (17)	C11—C12	1.3982 (15)
C1—C2	1.3954 (15)	C11—C14	1.5037 (15)
C1—C6	1.4071 (15)	C12—C13	1.3866 (14)
C2—C3	1.3875 (18)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.3886 (18)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.3838 (15)	C14—H14C	0.9600
C5—C6	1.4010 (14)

O3—S1—O2	120.16 (5)	C1—C6—C7	122.79 (9)
O3—S1—N2	103.86 (4)	N1—C7—C6	121.51 (9)
O2—S1—N2	106.09 (5)	N1—C7—H7A	119.2
O3—S1—C8	110.03 (5)	C6—C7—H7A	119.2
O2—S1—C8	109.02 (5)	C9—C8—C13	120.99 (9)
N2—S1—C8	106.73 (4)	C9—C8—S1	120.16 (7)
C1—O1—H1O1	107.2 (16)	C13—C8—S1	118.73 (7)
C7—N1—N2	115.26 (8)	C10—C9—C8	119.01 (9)
N1—N2—S1	114.07 (6)	C10—C9—H9A	120.5
N1—N2—H1N2	115.8 (11)	C8—C9—H9A	120.5
S1—N2—H1N2	110.5 (11)	C9—C10—C11	121.19 (9)
O1—C1—C2	117.97 (10)	C9—C10—H10A	119.4
O1—C1—C6	122.12 (9)	C11—C10—H10A	119.4
C2—C1—C6	119.91 (10)	C10—C11—C12	118.60 (9)
C3—C2—C1	120.33 (11)	C10—C11—C14	120.60 (10)
C3—C2—H2A	119.8	C12—C11—C14	120.79 (10)
C1—C2—H2A	119.8	C13—C12—C11	121.08 (9)
C2—C3—C4	119.61 (10)	C13—C12—H12A	119.5
C2—C3—H3A	120.2	C11—C12—H12A	119.5
C4—C3—H3A	120.2	C12—C13—C8	119.10 (9)
C5—C4—C3	121.01 (11)	C12—C13—H13A	120.4
C5—C4—Cl1	118.60 (10)	C8—C13—H13A	120.4
C3—C4—Cl1	120.38 (9)	C11—C14—H14A	109.5
C4—C5—C6	119.90 (11)	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	119.23 (9)	H14A—C14—H14C	109.5
C5—C6—C7	117.98 (9)	H14B—C14—H14C	109.5

C7—N1—N2—S1	−167.94 (8)	C5—C6—C7—N1	173.45 (10)
O3—S1—N2—N1	177.60 (7)	C1—C6—C7—N1	−7.19 (16)
O2—S1—N2—N1	−54.83 (8)	O3—S1—C8—C9	155.84 (8)
C8—S1—N2—N1	61.33 (8)	O2—S1—C8—C9	22.10 (10)
O1—C1—C2—C3	−179.18 (11)	N2—S1—C8—C9	−92.09 (8)
C6—C1—C2—C3	0.77 (17)	O3—S1—C8—C13	−28.14 (9)
C1—C2—C3—C4	−0.41 (18)	O2—S1—C8—C13	−161.88 (8)
C2—C3—C4—C5	−0.12 (18)	N2—S1—C8—C13	83.93 (8)
C2—C3—C4—Cl1	178.67 (9)	C13—C8—C9—C10	−1.10 (15)
C3—C4—C5—C6	0.28 (17)	S1—C8—C9—C10	174.83 (8)
Cl1—C4—C5—C6	−178.53 (8)	C8—C9—C10—C11	0.05 (16)
C4—C5—C6—C1	0.08 (16)	C9—C10—C11—C12	1.41 (16)
C4—C5—C6—C7	179.47 (10)	C9—C10—C11—C14	−177.60 (10)
O1—C1—C6—C5	179.34 (10)	C10—C11—C12—C13	−1.86 (15)
C2—C1—C6—C5	−0.60 (16)	C14—C11—C12—C13	177.14 (10)
O1—C1—C6—C7	−0.01 (16)	C11—C12—C13—C8	0.84 (15)
C2—C1—C6—C7	−179.95 (10)	C9—C8—C13—C12	0.66 (15)
N2—N1—C7—C6	−178.29 (9)	S1—C8—C13—C12	−175.32 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.75 (2)	2.00 (2)	2.6690 (13)	149 (2)
N2—H1N2···O2ⁱ	0.881 (16)	1.961 (17)	2.8375 (12)	172.8 (17)
C7—H7A···O1ⁱ	0.93	2.59	3.3679 (14)	142
C10—H10A···Cl1ⁱⁱ	0.93	2.82	3.7256 (12)	164
C12—H12A···O3ⁱⁱⁱ	0.93	2.48	3.3549 (14)	157

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃ClN₂O₃S
M_r	324.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.7454 (3), 9.8338 (2), 9.8455 (2)
β (°)	105.941 (1)
V (Å³)	1465.83 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.45 × 0.38 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.836, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	16498, 5274, 4761
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.093, 1.10
No. of reflections	5274
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)	0.44, −0.38

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
O1—H1O1···N1	0.75 (2)	2.00 (2)	2.6690 (13)	149 (2)
N2—H1N2···O2ⁱ	0.881 (16)	1.961 (17)	2.8375 (12)	172.8 (17)
C7—H7A···O1ⁱ	0.9300	2.5900	3.3679 (14)	142.00
C10—H10A···Cl1ⁱⁱ	0.9300	2.8200	3.7256 (12)	164.00
C12—H12A···O3ⁱⁱⁱ	0.9300	2.4800	3.3549 (14)	157.00

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

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti sains Malaysia for the 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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