(Z)-3-p-Tolyl-2-(p-tolyl­imino)-1,3-thia­zolidin-4-one

Abdel-Aziz, H.A.; Ghabbour, H.A.; Chia, T.S.; Fun, H.-K.

doi:10.1107/S160053681201149X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1143

doi:10.1107/S160053681201149X

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(Z)-3-p-Tolyl-2-(p-tolylimino)-1,3-thiazolidin-4-one

Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Tze Shyang Chia ^b and Hoong-Kun Fun ^b ^*‡

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 March 2012; accepted 16 March 2012; online 24 March 2012)

In the title compound, C₁₇H₁₆N₂OS, the central thiazolidin-4-one ring forms dihedral angles of 66.49 (9) and 79.45 (6)° with the two methyl-substituted benzene rings. In the crystal, molecules are stacked in columns along the b axis through C—H⋯π interactions. The H atoms of one of the methyl groups are disordered over two orientations with equal site occupancies.

Related literature

For the chemistry of thiazolidin-4-one and its experimental preparation, see: Abdel-Aziz et al. (2010 ). For a related structure, see: Zeller et al. (2011 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆N₂OS
M_r = 296.38
Monoclinic, P 2₁ /c
a = 14.1321 (4) Å
b = 5.8524 (2) Å
c = 19.0076 (6) Å
β = 100.307 (2)°
V = 1546.69 (8) Å³
Z = 4
Cu Kα radiation
μ = 1.85 mm⁻¹
T = 296 K
0.98 × 0.21 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.264, T_max = 0.897
10830 measured reflections
2849 independent reflections
2293 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.07
2849 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/N2/C1–C3 and C4–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg1ⁱ	0.93	3.00	3.788 (2)	144
C9—H9A⋯Cg2ⁱⁱ	0.93	2.87	3.607 (2)	138
Symmetry codes: (i) x, y-1, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S160053681201149X/is5090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201149X/is5090Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201149X/is5090Isup3.cml

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. The mean planes of the two methyl-substituted benzene rings (C4–C9 & C10–C15) make dihedral angles of 66.49 (9) and 79.45 (6)°, respectively, with the mean plane of the central thiazolidin-4-one ring [S1/N2/C1–C3/O1; maximum deviation = 0.0075 (12) Å at atom C3]. In the molecule, the hydrogen atoms which are attached to atom C17 are disordered over two positions, with equal site-occupancies. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Zeller et al., 2011).

In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure is stabilized by C—H···π interactions (Table 1), involving Cg1 and Cg2 which are the centroids of S1/N2/C1–C3 and C4–C9 rings, respectively.

Related literature top

For the chemistry of thiazolidin-4-one and its experimental preparation, see: Abdel-Aziz et al. (2010). For a related structure, see: Zeller et al. (2011). For reference bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the reported method by Abdel-Aziz et al. (2010). Crystals of the title compound were obtained by slow evaporation from an ethanol solution at room temperature.

Structure description top

For the chemistry of thiazolidin-4-one and its experimental preparation, see: Abdel-Aziz et al. (2010). For a related structure, see: Zeller et al. (2011). For reference bond lengths, see: Allen et al. (1987).

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 with atom labels and 30% probability displacement ellipsoids.

(Z)-3-p-Tolyl-2-(p-tolylimino)-1,3-thiazolidin-4-one top

Crystal data top

C₁₇H₁₆N₂OS	F(000) = 624
M_r = 296.38	D_x = 1.273 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1135 reflections
a = 14.1321 (4) Å	θ = 4.7–69.2°
b = 5.8524 (2) Å	µ = 1.85 mm⁻¹
c = 19.0076 (6) Å	T = 296 K
β = 100.307 (2)°	Needle, colourless
V = 1546.69 (8) Å³	0.98 × 0.21 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	2293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 69.8°, θ_min = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→17
T_min = 0.264, T_max = 0.897	k = −5→6
10830 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0633P)² + 0.2896P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2849 reflections	Δρ_max = 0.35 e Å⁻³
194 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (10)

Crystal data top

C₁₇H₁₆N₂OS	V = 1546.69 (8) Å³
M_r = 296.38	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.1321 (4) Å	µ = 1.85 mm⁻¹
b = 5.8524 (2) Å	T = 296 K
c = 19.0076 (6) Å	0.98 × 0.21 × 0.06 mm
β = 100.307 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2849 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2293 reflections with I > 2σ(I)
T_min = 0.264, T_max = 0.897	R_int = 0.041
10830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.07	Δρ_max = 0.35 e Å⁻³
2849 reflections	Δρ_min = −0.35 e Å⁻³
194 parameters

Special details top

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	Occ. (<1)
S1	0.86258 (4)	−0.00010 (12)	0.47164 (3)	0.0765 (3)
N1	0.84789 (10)	−0.0771 (3)	0.32906 (8)	0.0522 (4)
N2	0.73053 (10)	0.1441 (3)	0.36745 (8)	0.0523 (4)
O1	0.63384 (14)	0.3619 (4)	0.42357 (10)	0.1118 (8)
C1	0.7698 (2)	0.1807 (7)	0.49367 (13)	0.1031 (11)
H1A	0.7349	0.1019	0.5260	0.124*
H1B	0.7977	0.3185	0.5171	0.124*
C2	0.70278 (16)	0.2406 (5)	0.42561 (12)	0.0757 (7)
C3	0.81438 (12)	0.0103 (3)	0.37930 (10)	0.0496 (4)
C4	0.93412 (12)	−0.2091 (3)	0.34399 (9)	0.0479 (4)
C5	0.93843 (14)	−0.4167 (3)	0.37968 (12)	0.0584 (5)
H5A	0.8857	−0.4678	0.3983	0.070*
C6	1.02137 (14)	−0.5478 (3)	0.38750 (12)	0.0591 (5)
H6A	1.0236	−0.6864	0.4117	0.071*
C7	1.10064 (13)	−0.4772 (3)	0.36010 (11)	0.0515 (5)
C8	1.09587 (13)	−0.2684 (3)	0.32587 (10)	0.0530 (4)
H8A	1.1492	−0.2155	0.3083	0.064*
C9	1.01362 (13)	−0.1362 (3)	0.31707 (10)	0.0514 (4)
H9A	1.0117	0.0025	0.2929	0.062*
C10	0.67884 (12)	0.1860 (3)	0.29574 (10)	0.0475 (4)
C11	0.61531 (13)	0.0238 (3)	0.26253 (11)	0.0535 (5)
H11A	0.6064	−0.1124	0.2857	0.064*
C12	0.56500 (14)	0.0659 (4)	0.19452 (11)	0.0584 (5)
H12A	0.5222	−0.0434	0.1721	0.070*
C13	0.57711 (13)	0.2673 (4)	0.15916 (10)	0.0561 (5)
C14	0.64077 (14)	0.4275 (4)	0.19421 (11)	0.0592 (5)
H14A	0.6495	0.5644	0.1714	0.071*
C15	0.69157 (13)	0.3888 (3)	0.26226 (11)	0.0563 (5)
H15A	0.7338	0.4986	0.2851	0.068*
C16	0.52221 (18)	0.3121 (5)	0.08465 (13)	0.0838 (8)
H16A	0.4567	0.2639	0.0816	0.126*
H16B	0.5512	0.2284	0.0506	0.126*
H16C	0.5239	0.4725	0.0744	0.126*
C17	1.18878 (15)	−0.6264 (4)	0.36447 (13)	0.0688 (6)
H17A	1.2442	−0.5449	0.3885	0.103*	0.50
H17B	1.1977	−0.6659	0.3171	0.103*	0.50
H17C	1.1804	−0.7631	0.3906	0.103*	0.50
H17D	1.2256	−0.6203	0.4120	0.103*	0.50
H17E	1.2273	−0.5724	0.3311	0.103*	0.50
H17F	1.1694	−0.7811	0.3530	0.103*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0617 (4)	0.1143 (5)	0.0480 (4)	0.0285 (3)	−0.0047 (2)	0.0048 (3)
N1	0.0461 (8)	0.0559 (9)	0.0516 (9)	0.0101 (7)	0.0007 (6)	0.0030 (7)
N2	0.0441 (8)	0.0635 (10)	0.0461 (8)	0.0110 (7)	−0.0010 (6)	−0.0011 (7)
O1	0.0957 (13)	0.165 (2)	0.0691 (11)	0.0751 (14)	−0.0007 (9)	−0.0207 (12)
C1	0.0900 (18)	0.159 (3)	0.0529 (13)	0.0537 (19)	−0.0063 (12)	−0.0151 (16)
C2	0.0616 (12)	0.1040 (18)	0.0575 (12)	0.0279 (13)	−0.0003 (10)	−0.0105 (12)
C3	0.0412 (9)	0.0541 (10)	0.0502 (10)	0.0044 (7)	−0.0009 (8)	0.0044 (8)
C4	0.0464 (9)	0.0470 (9)	0.0472 (9)	0.0061 (7)	0.0003 (7)	−0.0010 (7)
C5	0.0487 (10)	0.0565 (11)	0.0701 (13)	0.0018 (8)	0.0110 (9)	0.0098 (9)
C6	0.0561 (11)	0.0474 (11)	0.0718 (13)	0.0066 (8)	0.0062 (9)	0.0119 (9)
C7	0.0491 (10)	0.0494 (10)	0.0530 (10)	0.0064 (7)	0.0013 (8)	−0.0053 (8)
C8	0.0492 (9)	0.0546 (11)	0.0550 (10)	0.0001 (8)	0.0092 (8)	−0.0027 (8)
C9	0.0559 (10)	0.0455 (10)	0.0516 (10)	0.0038 (8)	0.0061 (8)	0.0039 (7)
C10	0.0377 (8)	0.0539 (10)	0.0477 (9)	0.0077 (7)	−0.0010 (7)	−0.0008 (7)
C11	0.0495 (10)	0.0507 (10)	0.0573 (11)	−0.0010 (7)	0.0017 (8)	0.0047 (8)
C12	0.0487 (10)	0.0642 (12)	0.0575 (11)	−0.0066 (8)	−0.0030 (8)	−0.0023 (9)
C13	0.0456 (9)	0.0677 (12)	0.0524 (11)	0.0038 (8)	0.0017 (8)	0.0036 (9)
C14	0.0572 (11)	0.0557 (11)	0.0625 (12)	0.0008 (9)	0.0053 (9)	0.0117 (9)
C15	0.0492 (10)	0.0516 (11)	0.0639 (12)	−0.0032 (8)	−0.0011 (8)	−0.0037 (9)
C16	0.0790 (15)	0.108 (2)	0.0574 (13)	−0.0013 (14)	−0.0077 (11)	0.0135 (13)
C17	0.0595 (11)	0.0652 (13)	0.0810 (15)	0.0165 (10)	0.0111 (10)	0.0006 (11)

Geometric parameters (Å, º) top

S1—C3	1.7664 (19)	C9—H9A	0.9300
S1—C1	1.792 (3)	C10—C15	1.374 (3)
N1—C3	1.249 (2)	C10—C11	1.379 (3)
N1—C4	1.428 (2)	C11—C12	1.381 (3)
N2—C2	1.360 (3)	C11—H11A	0.9300
N2—C3	1.405 (2)	C12—C13	1.383 (3)
N2—C10	1.448 (2)	C12—H12A	0.9300
O1—C2	1.200 (3)	C13—C14	1.385 (3)
C1—C2	1.502 (3)	C13—C16	1.511 (3)
C1—H1A	0.9700	C14—C15	1.381 (3)
C1—H1B	0.9700	C14—H14A	0.9300
C4—C9	1.383 (3)	C15—H15A	0.9300
C4—C5	1.387 (3)	C16—H16A	0.9600
C5—C6	1.387 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.381 (3)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.380 (3)	C17—H17C	0.9600
C7—C17	1.511 (3)	C17—H17D	0.9600
C8—C9	1.381 (3)	C17—H17E	0.9600
C8—H8A	0.9300	C17—H17F	0.9600

C3—S1—C1	92.50 (10)	C4—C9—H9A	119.9
C3—N1—C4	119.78 (15)	C15—C10—C11	120.72 (17)
C2—N2—C3	117.32 (15)	C15—C10—N2	119.79 (16)
C2—N2—C10	121.64 (15)	C11—C10—N2	119.46 (17)
C3—N2—C10	120.97 (15)	C10—C11—C12	119.31 (18)
C2—C1—S1	108.16 (17)	C10—C11—H11A	120.3
C2—C1—H1A	110.1	C12—C11—H11A	120.3
S1—C1—H1A	110.1	C11—C12—C13	121.27 (18)
C2—C1—H1B	110.1	C11—C12—H12A	119.4
S1—C1—H1B	110.1	C13—C12—H12A	119.4
H1A—C1—H1B	108.4	C12—C13—C14	118.00 (17)
O1—C2—N2	124.7 (2)	C12—C13—C16	121.1 (2)
O1—C2—C1	123.3 (2)	C14—C13—C16	120.9 (2)
N2—C2—C1	111.96 (18)	C15—C14—C13	121.58 (19)
N1—C3—N2	122.02 (16)	C15—C14—H14A	119.2
N1—C3—S1	127.89 (14)	C13—C14—H14A	119.2
N2—C3—S1	110.05 (13)	C10—C15—C14	119.10 (17)
C9—C4—C5	118.94 (17)	C10—C15—H15A	120.4
C9—C4—N1	118.71 (16)	C14—C15—H15A	120.4
C5—C4—N1	122.16 (17)	C13—C16—H16A	109.5
C6—C5—C4	119.96 (19)	C13—C16—H16B	109.5
C6—C5—H5A	120.0	H16A—C16—H16B	109.5
C4—C5—H5A	120.0	C13—C16—H16C	109.5
C7—C6—C5	121.40 (18)	H16A—C16—H16C	109.5
C7—C6—H6A	119.3	H16B—C16—H16C	109.5
C5—C6—H6A	119.3	C7—C17—H17A	109.5
C8—C7—C6	117.93 (17)	C7—C17—H17B	109.5
C8—C7—C17	120.51 (19)	C7—C17—H17C	109.5
C6—C7—C17	121.51 (19)	C7—C17—H17D	109.5
C7—C8—C9	121.47 (18)	C7—C17—H17E	109.5
C7—C8—H8A	119.3	H17D—C17—H17E	109.5
C9—C8—H8A	119.3	C7—C17—H17F	109.5
C8—C9—C4	120.27 (18)	H17D—C17—H17F	109.5
C8—C9—H9A	119.9	H17E—C17—H17F	109.5

C3—S1—C1—C2	0.6 (3)	C5—C6—C7—C17	−176.1 (2)
C3—N2—C2—O1	178.7 (3)	C6—C7—C8—C9	−2.0 (3)
C10—N2—C2—O1	1.7 (4)	C17—C7—C8—C9	175.62 (19)
C3—N2—C2—C1	−0.4 (3)	C7—C8—C9—C4	1.3 (3)
C10—N2—C2—C1	−177.4 (2)	C5—C4—C9—C8	−0.1 (3)
S1—C1—C2—O1	−179.3 (3)	N1—C4—C9—C8	−175.14 (17)
S1—C1—C2—N2	−0.2 (4)	C2—N2—C10—C15	77.3 (3)
C4—N1—C3—N2	179.14 (16)	C3—N2—C10—C15	−99.6 (2)
C4—N1—C3—S1	1.9 (3)	C2—N2—C10—C11	−101.0 (2)
C2—N2—C3—N1	−176.8 (2)	C3—N2—C10—C11	82.1 (2)
C10—N2—C3—N1	0.2 (3)	C15—C10—C11—C12	0.7 (3)
C2—N2—C3—S1	0.9 (2)	N2—C10—C11—C12	179.01 (17)
C10—N2—C3—S1	177.91 (14)	C10—C11—C12—C13	0.0 (3)
C1—S1—C3—N1	176.7 (2)	C11—C12—C13—C14	−0.5 (3)
C1—S1—C3—N2	−0.82 (19)	C11—C12—C13—C16	179.7 (2)
C3—N1—C4—C9	−118.4 (2)	C12—C13—C14—C15	0.4 (3)
C3—N1—C4—C5	66.7 (3)	C16—C13—C14—C15	−179.9 (2)
C9—C4—C5—C6	−0.4 (3)	C11—C10—C15—C14	−0.9 (3)
N1—C4—C5—C6	174.46 (19)	N2—C10—C15—C14	−179.14 (17)
C4—C5—C6—C7	−0.3 (3)	C13—C14—C15—C10	0.3 (3)
C5—C6—C7—C8	1.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/N2/C1–C3 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1ⁱ	0.93	3.00	3.788 (2)	144
C9—H9A···Cg2ⁱⁱ	0.93	2.87	3.607 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂OS
M_r	296.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.1321 (4), 5.8524 (2), 19.0076 (6)
β (°)	100.307 (2)
V (Å³)	1546.69 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.98 × 0.21 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.264, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	10830, 2849, 2293
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.07
No. of reflections	2849
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.35

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/N2/C1–C3 and C4–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1ⁱ	0.93	3.00	3.788 (2)	144
C9—H9A···Cg2ⁱⁱ	0.93	2.87	3.607 (2)	138

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HAAA and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

References

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Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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