N,N′-(Ethane-1,2-di­yl)dibenzene­sulfonamide

Al-Dajani, M.T.M.; Talaat, J.; Mohamed, N.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811030157

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2214

doi:10.1107/S1600536811030157

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N,N′-(Ethane-1,2-diyl)dibenzenesulfonamide

Mohammad T. M. Al-Dajani,^a Jamal Talaat,^b Nornisah Mohamed,^a Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*‡

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

(Received 21 July 2011; accepted 26 July 2011; online 2 August 2011)

In the title compound, C₁₄H₁₆N₂O₄S₂, the dihedral angle between the terminal phenyl rings is 77.07 (13)°. The geometries around the S atoms are distorted tetrahedral, with O—S—O angles of 120.66 (12) and 119.44 (11)°. In the crystal, molecules are stacked in columns along the a axis via intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For biological activities and applications of sulfonamide derivatives, see: Misra et al. (1982 ); Maren (1976 ); Li et al. (1995 ); Yoshino et al. (1992 ). For related structures, see: Basak et al. (1982 ); Cotton & Stokley (1970 ).

Experimental

Crystal data

C₁₄H₁₆N₂O₄S₂
M_r = 340.41
Monoclinic, P 2₁ /c
a = 5.2115 (4) Å
b = 16.6905 (13) Å
c = 17.8750 (14) Å
β = 93.187 (2)°
V = 1552.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.46 × 0.08 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.852, T_max = 0.975
14604 measured reflections
3545 independent reflections
2628 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.04
3545 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.73 (3)	2.40 (3)	3.053 (3)	149 (3)
N2—H1N2⋯O3ⁱ	0.83 (3)	2.15 (3)	2.924 (3)	157 (2)
C10—H10A⋯O1ⁱⁱ	0.93	2.57	3.294 (3)	135
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+1.

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/S1600536811030157/is2755sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030157/is2755Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030157/is2755Isup3.cml

checkCIF report

Comment top

Sulfonamide is found in a number of synthetic as well as natural compounds. These molecules exhibit antibacterial (Misra et al., 1982), insulin-releasing (Maren, 1976), anti-inflammatory (Li et al., 1995) and antitumor (Yoshino et al., 1992) activities. An X-ray study of the title compound was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure is shown in Fig. 1.

The molecule is bent at the N atoms with C9-S2-N2-C8 and C7-N1-S1-C6 torsion angles of 58.48 (18) and 72.6 (2)°, respectively. The geometries around the sulfonamide S atoms are in a slightly distorted tetrahedral configuration, similar to that observed in other reported structures (Basak et al., 1982). The maximum and minimum values of the angles around S are 121.62 (17) and 105.92 (11)°, respectively. This deviation can be attributed to the non-bonded interactions involving the S–O bonds, resulting in a structure with less steric interference (Cotton & Stokley, 1970) and the varied steric bulk of the substituents. The dihedral angle between the terminal phenyl C1–C6 and C9–C14 rings is 77.07 (13)°.

In the crystal structure, the molecules are connected via intermolecular N1—H1N1···O2, N2—H1N2···O3 and C10—H10A···O1 hydrogen bonds (Table 1) forming one-dimensional supramolecular chains along the a axis (Fig. 2).

Related literature top

For biological activities and applications of sulfonamide derivatives, see: Misra et al. (1982); Maren (1976); Li et al. (1995); Yoshino et al. (1992). For related structures, see: Basak et al. (1982); Cotton & Stokley (1970).

Experimental top

In a round bottom flask, 25ml from toluene was mixed with benzenesulfonyl chloride (0.02 mol, 3.5 g) with stirring. Drops of ethylenediamine (0.01 mol, 0.5 g ) was added and the mixture was refluxed for 30 min. The yellow gum formed was dissolved in hot water and sodium bicarbonate was added. The yellow precipitate formed was dissolved in methanol at 60 °C, yielding colourless crystals.

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 molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound with dashed lines representing hydrogen bonds.

N,N'-(Ethane-1,2-diyl)dibenzenesulfonamide top

Crystal data top

C₁₄H₁₆N₂O₄S₂	F(000) = 712
M_r = 340.41	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3372 reflections
a = 5.2115 (4) Å	θ = 2.4–32.2°
b = 16.6905 (13) Å	µ = 0.36 mm⁻¹
c = 17.8750 (14) Å	T = 296 K
β = 93.187 (2)°	Needle, colourless
V = 1552.4 (2) Å³	0.46 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3545 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.852, T_max = 0.975	k = −21→21
14604 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.062P)² + 0.174P] where P = (F_o² + 2F_c²)/3
3545 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₄H₁₆N₂O₄S₂	V = 1552.4 (2) Å³
M_r = 340.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.2115 (4) Å	µ = 0.36 mm⁻¹
b = 16.6905 (13) Å	T = 296 K
c = 17.8750 (14) Å	0.46 × 0.08 × 0.07 mm
β = 93.187 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3545 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2628 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.975	R_int = 0.047
14604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
3545 reflections	Δρ_min = −0.33 e Å⁻³
207 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	0.29124 (10)	0.88198 (3)	0.48674 (3)	0.03665 (17)
S2	0.52329 (10)	0.99919 (3)	0.80016 (3)	0.03343 (16)
O1	0.2344 (4)	0.92155 (10)	0.41688 (9)	0.0546 (5)
O2	0.5474 (3)	0.88119 (11)	0.51993 (11)	0.0563 (5)
O3	0.7660 (3)	0.98466 (10)	0.76908 (10)	0.0484 (4)
O4	0.4855 (4)	0.97572 (10)	0.87531 (9)	0.0514 (5)
N1	0.1146 (4)	0.92431 (11)	0.54596 (11)	0.0349 (4)
N2	0.3085 (4)	0.95274 (10)	0.74743 (10)	0.0330 (4)
C1	−0.0240 (5)	0.76368 (15)	0.43026 (14)	0.0502 (6)
H1A	−0.1124	0.8043	0.4042	0.060*
C2	−0.1056 (6)	0.68534 (16)	0.42342 (16)	0.0595 (7)
H2A	−0.2505	0.6731	0.3929	0.071*
C3	0.0258 (6)	0.62555 (15)	0.46139 (17)	0.0606 (8)
H3A	−0.0296	0.5728	0.4560	0.073*
C4	0.2370 (7)	0.64248 (16)	0.50704 (16)	0.0643 (8)
H4A	0.3244	0.6015	0.5328	0.077*
C5	0.3216 (5)	0.72138 (15)	0.51494 (14)	0.0518 (6)
H5A	0.4654	0.7334	0.5461	0.062*
C6	0.1905 (4)	0.78130 (13)	0.47623 (11)	0.0353 (5)
C7	0.1430 (4)	0.90629 (12)	0.62583 (12)	0.0368 (5)
H7A	0.2338	0.8559	0.6332	0.044*
H7B	−0.0255	0.9006	0.6457	0.044*
C8	0.2890 (5)	0.97194 (13)	0.66725 (11)	0.0370 (5)
H8A	0.4596	0.9768	0.6486	0.044*
H8B	0.2006	1.0226	0.6593	0.044*
C9	0.4584 (4)	1.10252 (12)	0.79155 (11)	0.0325 (5)
C10	0.5938 (5)	1.14968 (14)	0.74477 (13)	0.0451 (6)
H10A	0.7253	1.1279	0.7181	0.054*
C11	0.5318 (6)	1.23066 (15)	0.73773 (15)	0.0557 (7)
H11A	0.6214	1.2632	0.7059	0.067*
C12	0.3395 (6)	1.26242 (15)	0.77743 (16)	0.0566 (7)
H12A	0.3001	1.3166	0.7730	0.068*
C13	0.2043 (6)	1.21465 (16)	0.82375 (17)	0.0592 (7)
H13A	0.0721	1.2366	0.8500	0.071*
C14	0.2625 (5)	1.13442 (14)	0.83181 (14)	0.0456 (6)
H14A	0.1720	1.1022	0.8637	0.055*
H1N1	−0.017 (5)	0.9291 (15)	0.5307 (14)	0.034 (7)*
H1N2	0.168 (5)	0.9581 (14)	0.7659 (13)	0.036 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0300 (3)	0.0369 (3)	0.0434 (3)	−0.0052 (2)	0.0060 (2)	−0.0049 (2)
S2	0.0273 (3)	0.0334 (3)	0.0391 (3)	0.0054 (2)	−0.0026 (2)	−0.0020 (2)
O1	0.0715 (13)	0.0515 (10)	0.0419 (9)	−0.0085 (9)	0.0125 (9)	0.0041 (7)
O2	0.0266 (9)	0.0588 (11)	0.0835 (12)	−0.0066 (8)	0.0036 (9)	−0.0167 (9)
O3	0.0240 (8)	0.0516 (10)	0.0694 (11)	0.0088 (7)	−0.0001 (8)	−0.0077 (8)
O4	0.0628 (12)	0.0508 (9)	0.0397 (9)	0.0058 (9)	−0.0064 (8)	0.0064 (7)
N1	0.0268 (10)	0.0378 (10)	0.0397 (10)	0.0006 (8)	−0.0024 (9)	−0.0045 (8)
N2	0.0276 (10)	0.0339 (9)	0.0378 (9)	−0.0010 (8)	0.0057 (8)	−0.0022 (7)
C1	0.0468 (15)	0.0431 (13)	0.0595 (15)	−0.0009 (12)	−0.0085 (13)	−0.0065 (11)
C2	0.0548 (17)	0.0508 (15)	0.0714 (18)	−0.0129 (13)	−0.0094 (15)	−0.0140 (13)
C3	0.075 (2)	0.0389 (13)	0.0684 (17)	−0.0122 (14)	0.0061 (16)	−0.0111 (12)
C4	0.086 (2)	0.0411 (13)	0.0645 (17)	0.0081 (15)	−0.0052 (17)	0.0018 (12)
C5	0.0519 (16)	0.0467 (13)	0.0550 (14)	0.0048 (12)	−0.0123 (13)	−0.0053 (11)
C6	0.0315 (12)	0.0365 (11)	0.0383 (11)	0.0003 (9)	0.0052 (10)	−0.0064 (9)
C7	0.0366 (12)	0.0330 (10)	0.0408 (11)	−0.0065 (9)	0.0033 (10)	−0.0018 (9)
C8	0.0388 (12)	0.0333 (10)	0.0385 (11)	−0.0073 (10)	−0.0012 (10)	0.0005 (9)
C9	0.0285 (11)	0.0341 (10)	0.0340 (10)	0.0012 (9)	−0.0059 (9)	−0.0059 (8)
C10	0.0467 (14)	0.0427 (12)	0.0462 (13)	0.0003 (11)	0.0056 (11)	−0.0038 (10)
C11	0.0676 (19)	0.0419 (13)	0.0573 (15)	−0.0067 (13)	0.0012 (14)	0.0049 (11)
C12	0.0651 (19)	0.0312 (12)	0.0719 (17)	0.0059 (12)	−0.0101 (15)	−0.0042 (11)
C13	0.0524 (16)	0.0446 (14)	0.0805 (19)	0.0124 (13)	0.0043 (15)	−0.0164 (13)
C14	0.0392 (13)	0.0401 (12)	0.0581 (14)	0.0039 (10)	0.0093 (12)	−0.0083 (10)

Geometric parameters (Å, º) top

S1—O1	1.4291 (17)	C4—H4A	0.9300
S1—O2	1.4307 (19)	C5—C6	1.376 (3)
S1—N1	1.605 (2)	C5—H5A	0.9300
S1—C6	1.767 (2)	C7—C8	1.505 (3)
S2—O4	1.4233 (17)	C7—H7A	0.9700
S2—O3	1.4300 (17)	C7—H7B	0.9700
S2—N2	1.6202 (19)	C8—H8A	0.9700
S2—C9	1.763 (2)	C8—H8B	0.9700
N1—C7	1.459 (3)	C9—C10	1.372 (3)
N1—H1N1	0.73 (3)	C9—C14	1.387 (3)
N2—C8	1.467 (3)	C10—C11	1.394 (3)
N2—H1N2	0.82 (3)	C10—H10A	0.9300
C1—C2	1.378 (3)	C11—C12	1.367 (4)
C1—C6	1.382 (3)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.372 (4)
C2—C3	1.369 (4)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.379 (3)
C3—C4	1.363 (4)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.393 (4)

O1—S1—O2	120.66 (12)	C5—C6—C1	120.5 (2)
O1—S1—N1	105.92 (11)	C5—C6—S1	120.09 (19)
O2—S1—N1	106.67 (11)	C1—C6—S1	119.43 (18)
O1—S1—C6	107.49 (10)	N1—C7—C8	110.63 (17)
O2—S1—C6	107.46 (11)	N1—C7—H7A	109.5
N1—S1—C6	108.11 (10)	C8—C7—H7A	109.5
O4—S2—O3	119.44 (11)	N1—C7—H7B	109.5
O4—S2—N2	106.86 (11)	C8—C7—H7B	109.5
O3—S2—N2	106.87 (10)	H7A—C7—H7B	108.1
O4—S2—C9	108.40 (10)	N2—C8—C7	109.10 (17)
O3—S2—C9	107.56 (10)	N2—C8—H8A	109.9
N2—S2—C9	107.12 (10)	C7—C8—H8A	109.9
C7—N1—S1	121.62 (17)	N2—C8—H8B	109.9
C7—N1—H1N1	115.6 (19)	C7—C8—H8B	109.9
S1—N1—H1N1	111 (2)	H8A—C8—H8B	108.3
C8—N2—S2	118.16 (14)	C10—C9—C14	120.9 (2)
C8—N2—H1N2	110.7 (16)	C10—C9—S2	120.78 (17)
S2—N2—H1N2	108.3 (16)	C14—C9—S2	118.26 (17)
C2—C1—C6	119.4 (2)	C9—C10—C11	119.1 (2)
C2—C1—H1A	120.3	C9—C10—H10A	120.4
C6—C1—H1A	120.3	C11—C10—H10A	120.4
C3—C2—C1	120.3 (3)	C12—C11—C10	120.2 (2)
C3—C2—H2A	119.9	C12—C11—H11A	119.9
C1—C2—H2A	119.9	C10—C11—H11A	119.9
C4—C3—C2	120.7 (2)	C11—C12—C13	120.3 (2)
C4—C3—H3A	119.6	C11—C12—H12A	119.9
C2—C3—H3A	119.6	C13—C12—H12A	119.9
C3—C4—C5	119.8 (3)	C12—C13—C14	120.7 (2)
C3—C4—H4A	120.1	C12—C13—H13A	119.7
C5—C4—H4A	120.1	C14—C13—H13A	119.7
C6—C5—C4	119.4 (3)	C13—C14—C9	118.8 (2)
C6—C5—H5A	120.3	C13—C14—H14A	120.6
C4—C5—H5A	120.3	C9—C14—H14A	120.6

O1—S1—N1—C7	−172.40 (17)	N1—S1—C6—C1	80.2 (2)
O2—S1—N1—C7	−42.7 (2)	S1—N1—C7—C8	102.1 (2)
C6—S1—N1—C7	72.6 (2)	S2—N2—C8—C7	162.43 (15)
O4—S2—N2—C8	174.49 (16)	N1—C7—C8—N2	178.68 (19)
O3—S2—N2—C8	−56.57 (19)	O4—S2—C9—C10	145.79 (19)
C9—S2—N2—C8	58.48 (18)	O3—S2—C9—C10	15.4 (2)
C6—C1—C2—C3	−0.5 (4)	N2—S2—C9—C10	−99.2 (2)
C1—C2—C3—C4	0.7 (5)	O4—S2—C9—C14	−35.8 (2)
C2—C3—C4—C5	−0.4 (5)	O3—S2—C9—C14	−166.27 (18)
C3—C4—C5—C6	−0.2 (4)	N2—S2—C9—C14	79.1 (2)
C4—C5—C6—C1	0.4 (4)	C14—C9—C10—C11	−0.2 (4)
C4—C5—C6—S1	178.9 (2)	S2—C9—C10—C11	178.08 (19)
C2—C1—C6—C5	−0.1 (4)	C9—C10—C11—C12	0.4 (4)
C2—C1—C6—S1	−178.6 (2)	C10—C11—C12—C13	−0.8 (4)
O1—S1—C6—C5	147.7 (2)	C11—C12—C13—C14	0.9 (4)
O2—S1—C6—C5	16.4 (2)	C12—C13—C14—C9	−0.7 (4)
N1—S1—C6—C5	−98.4 (2)	C10—C9—C14—C13	0.4 (4)
O1—S1—C6—C1	−33.8 (2)	S2—C9—C14—C13	−178.0 (2)
O2—S1—C6—C1	−165.05 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.73 (3)	2.40 (3)	3.053 (3)	149 (3)
N2—H1N2···O3ⁱ	0.83 (3)	2.15 (3)	2.924 (3)	157 (2)
C10—H10A···O1ⁱⁱ	0.93	2.57	3.294 (3)	135

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₂O₄S₂
M_r	340.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.2115 (4), 16.6905 (13), 17.8750 (14)
β (°)	93.187 (2)
V (Å³)	1552.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.46 × 0.08 × 0.07

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.852, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	14604, 3545, 2628
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.04
No. of reflections	3545
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.33

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
N1—H1N1···O2ⁱ	0.73 (3)	2.40 (3)	3.053 (3)	149 (3)
N2—H1N2···O3ⁱ	0.83 (3)	2.15 (3)	2.924 (3)	157 (2)
C10—H10A···O1ⁱⁱ	0.9300	2.5700	3.294 (3)	135.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the Research University Grant No. 1001/PFARMASI/821142. 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 postdoctoral research fellowship.

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