N′-[(3-Methyl-2-thien­yl)carbon­yl]isonicotinohydrazide

Naveenkumar, H.S.; Sadikun, A.; Ibrahim, P.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536809033030

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2235-o2236

doi:10.1107/S1600536809033030

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N′-[(3-Methyl-2-thienyl)carbonyl]isonicotinohydrazide

H. S. Naveenkumar,^a Amirin Sadikun,^a ‡ Pazilah Ibrahim,^a Jia Hao Goh ^b and Hoong-Kun Fun ^b ^*§

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

(Received 17 August 2009; accepted 19 August 2009; online 26 August 2009)

In the title compound, C₁₂H₁₁N₃O₂S, the pyridine ring is inclined to the thiophene ring, forming a dihedral angle of 34.96 (7)°. The mean plane through the hydrazide unit forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thiophene rings. The two O atoms are twisted away from each other, as indicated by the C—N—N—C torsion angle of −81.27 (15)°. In the crystal structure, molecules are linked into an extended three-dimensional network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure also features a short S⋯O [3.2686 (10) Å] interaction and a weak intermolecular C—H⋯π interaction.

Related literature

For general background to and application of isoniazid derivatives, see: Janin (2007 ); Maccari et al. (2005 ); Slayden et al. (2000 ). For the preparation of the title compound, see: Besra et al. (1993 ). For bond-length data, see: Allen et al. (1987 ). For a closely related structure, see: Naveenkumar et al. (2009 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₂S
M_r = 261.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9206 (1) Å
b = 10.7552 (2) Å
c = 12.4934 (2) Å
V = 1198.65 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.58 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.861, T_max = 0.961
17333 measured reflections
4355 independent reflections
4078 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.05
4355 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 1856 Friedel pairs
Flack parameter: −0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1ⁱ	0.86	2.14	2.9068 (17)	149
N3—H1N3⋯O2ⁱⁱ	0.86	1.99	2.8034 (15)	158
C4—H4A⋯O1ⁱⁱⁱ	0.93	2.58	3.2047 (17)	125
C10—H10A⋯O2^iv	0.93	2.51	3.3928 (19)	159
C11—H11A⋯Cg1^v	0.93	2.80	3.3760 (17)	121
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is centroid of the C1/C2/N1/C3–C5 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809033030/is2451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033030/is2451Isup2.hkl

checkCIF report

Comment top

In the search of new compounds, isoniazid derivatives have been found to possess potential tuberculostatic activity (Janin, 2007; Maccari et al., 2005; Slayden et al., 2000). As a part of a current work on synthesis of such derivatives, in this paper we present the crystal structure of the title compound, (I) which was synthesized in our lab.

In (I), the pyridine ring (C1/C2/N1/C3-C5) is inclined to the thiophene ring (C8-C11/S1), forming a dihedral angle of 34.96 (7)° (Fig. 1). The mean plane through the hydrazide unit (C7/N2/N3/O2) forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thiophene rings. The O1 and O2 atoms are twisted away from each other as indicated by torsion angle C6–N2–N3–C7 [-81.27 (15)°]. The bond lengths (Allen et al., 1987) and angles are comparable to a closely related structure (Naveenkumar et al., 2009).

In the crystal structure (Fig. 2), the molecules are linked into an extended three-dimensional network by intermolecular C4—H4A···O1, C10—H10A···O2, N2—H1N2···N1 and N3—H1N3···O2 hydrogen bonds (Table 1). The crystal structure is further stabilized by short S1···O2 interactions of 3.2686 (10) Å [symmetry code: 1/2+x, 3/2-y, -z] and by weak intermolecular C11—H11A···Cg1 interactions (Table 1; Cg1 is the centroid of the pyridine ring).

Related literature top

For general background to and application of isoniazid derivatives, see: Janin (2007); Maccari et al. (2005); Slayden et al. (2000). For the preparation of the title compound, see: Besra et al. (1993). For bond-length data, see: Allen et al. (1987). For a closely related structure, see: Naveenkumar et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is centroid of the C1/C2/N1/C3–C5 ring.

Experimental top

Compound (I) was prepared following the procedure by literature (Besra et al., 1993). Dry dichloromethane (30 ml) and 4-dimethylaminopyridine (4-DMAP) (1.2 eq) was added to 3-methylthiophene-2-carbonyl chloride followed by isoniazid (1.1 eq). The reaction mixture was kept in an ice bath for 1 h and then left stirring under nitrogen atmosphere overnight at room temperature. Dichloromethane (20 ml) was added to the reaction mixture, which was then washed with water, and the organic layer dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to afford the crude product which was purified by column chromatography and recrystallized from ethanol to afford colorless single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top

	Fig. 1. The molecular structure of the (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Three dimensional extended network, viewed along the b axis. Intermolecular interactions are shown as dashed lines.

N'-[(3-Methyl-2-thienyl)carbonyl]isonicotinohydrazide top

Crystal data top

C₁₂H₁₁N₃O₂S	F(000) = 544
M_r = 261.30	D_x = 1.448 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9634 reflections
a = 8.9206 (1) Å	θ = 2.5–32.7°
b = 10.7552 (2) Å	µ = 0.27 mm⁻¹
c = 12.4934 (2) Å	T = 100 K
V = 1198.65 (3) Å³	Block, colourless
Z = 4	0.58 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4355 independent reflections
Radiation source: fine-focus sealed tube	4078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.861, T_max = 0.961	k = −14→16
17333 measured reflections	l = −17→18

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0542P)² + 0.3319P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4355 reflections	Δρ_max = 0.79 e Å⁻³
165 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1856 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (6)

Crystal data top

C₁₂H₁₁N₃O₂S	V = 1198.65 (3) Å³
M_r = 261.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9206 (1) Å	µ = 0.27 mm⁻¹
b = 10.7552 (2) Å	T = 100 K
c = 12.4934 (2) Å	0.58 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4355 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4078 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.961	R_int = 0.025
17333 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.79 e Å⁻³
S = 1.05	Δρ_min = −0.43 e Å⁻³
4355 reflections	Absolute structure: Flack (1983), 1856 Friedel pairs
165 parameters	Absolute structure parameter: −0.04 (6)
0 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.26735 (4)	0.98879 (3)	0.04525 (3)	0.01858 (8)
O1	0.29108 (13)	0.48575 (10)	0.02488 (8)	0.0221 (2)
O2	0.01066 (11)	0.69442 (9)	0.07046 (8)	0.01664 (19)
N1	0.03034 (14)	0.21406 (11)	−0.25010 (10)	0.0159 (2)
N2	0.18343 (13)	0.62066 (10)	−0.09379 (9)	0.0137 (2)
H1N2	0.1404	0.6288	−0.1550	0.016*
N3	0.21647 (13)	0.72506 (10)	−0.03274 (9)	0.01367 (19)
H1N3	0.2954	0.7684	−0.0458	0.016*
C1	0.11893 (17)	0.29049 (12)	−0.08076 (11)	0.0165 (2)
H1A	0.1343	0.2764	−0.0081	0.020*
C2	0.05396 (17)	0.19936 (13)	−0.14457 (11)	0.0174 (2)
H2A	0.0255	0.1248	−0.1128	0.021*
C3	0.07732 (15)	0.32069 (12)	−0.29452 (11)	0.0153 (2)
H3A	0.0653	0.3306	−0.3680	0.018*
C4	0.14288 (15)	0.41719 (12)	−0.23723 (11)	0.0143 (2)
H4A	0.1741	0.4894	−0.2716	0.017*
C5	0.16079 (15)	0.40323 (12)	−0.12698 (10)	0.0136 (2)
C6	0.21924 (14)	0.50531 (11)	−0.05670 (10)	0.0138 (2)
C7	0.12212 (14)	0.75769 (11)	0.04814 (11)	0.0125 (2)
C8	0.15680 (15)	0.87488 (12)	0.10399 (11)	0.0142 (2)
C9	0.10620 (16)	0.91137 (14)	0.20356 (11)	0.0177 (2)
C10	0.15852 (18)	1.03210 (14)	0.23047 (13)	0.0209 (3)
H10A	0.1356	1.0716	0.2947	0.025*
C11	0.24567 (18)	1.08445 (13)	0.15288 (12)	0.0214 (3)
H11A	0.2883	1.1631	0.1581	0.026*
C12	0.0117 (2)	0.83596 (16)	0.27738 (13)	0.0259 (3)
H12A	0.0530	0.7538	0.2835	0.039*
H12B	−0.0884	0.8309	0.2496	0.039*
H12C	0.0097	0.8745	0.3466	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02092 (15)	0.01399 (13)	0.02083 (16)	−0.00198 (11)	0.00366 (12)	−0.00283 (12)
O1	0.0302 (5)	0.0186 (4)	0.0176 (5)	0.0033 (4)	−0.0104 (4)	−0.0021 (4)
O2	0.0134 (4)	0.0166 (4)	0.0200 (5)	−0.0026 (3)	0.0000 (3)	0.0000 (4)
N1	0.0187 (5)	0.0131 (5)	0.0160 (5)	−0.0004 (4)	−0.0017 (4)	−0.0018 (4)
N2	0.0177 (5)	0.0113 (4)	0.0120 (5)	−0.0003 (4)	−0.0028 (4)	−0.0031 (4)
N3	0.0150 (5)	0.0122 (4)	0.0138 (5)	−0.0024 (4)	0.0005 (4)	−0.0046 (4)
C1	0.0229 (6)	0.0140 (6)	0.0125 (5)	0.0003 (5)	−0.0015 (5)	0.0011 (4)
C2	0.0226 (6)	0.0123 (5)	0.0173 (6)	−0.0006 (5)	−0.0006 (5)	0.0004 (5)
C3	0.0182 (6)	0.0163 (6)	0.0114 (5)	−0.0001 (4)	0.0005 (4)	−0.0028 (4)
C4	0.0172 (6)	0.0127 (5)	0.0131 (5)	−0.0014 (4)	−0.0001 (4)	−0.0011 (4)
C5	0.0158 (5)	0.0123 (5)	0.0128 (5)	0.0014 (4)	−0.0015 (4)	−0.0018 (4)
C6	0.0159 (5)	0.0133 (5)	0.0122 (5)	0.0008 (4)	−0.0012 (4)	−0.0018 (4)
C7	0.0129 (5)	0.0123 (5)	0.0124 (5)	0.0012 (4)	−0.0020 (4)	0.0002 (4)
C8	0.0139 (5)	0.0128 (5)	0.0160 (6)	0.0008 (4)	−0.0015 (4)	−0.0016 (4)
C9	0.0180 (6)	0.0188 (6)	0.0165 (6)	0.0005 (5)	−0.0001 (5)	−0.0021 (5)
C10	0.0230 (6)	0.0194 (6)	0.0205 (6)	0.0026 (5)	−0.0022 (5)	−0.0084 (5)
C11	0.0246 (7)	0.0152 (5)	0.0245 (7)	−0.0008 (5)	−0.0006 (5)	−0.0079 (5)
C12	0.0299 (8)	0.0246 (7)	0.0234 (7)	−0.0028 (6)	0.0019 (6)	−0.0040 (6)

Geometric parameters (Å, º) top

S1—C11	1.7041 (14)	C3—C4	1.3898 (18)
S1—C8	1.7355 (14)	C3—H3A	0.9300
O1—C6	1.2222 (15)	C4—C5	1.3948 (19)
O2—C7	1.2367 (15)	C4—H4A	0.9300
N1—C3	1.3412 (18)	C5—C6	1.4994 (18)
N1—C2	1.3445 (18)	C7—C8	1.4736 (17)
N2—C6	1.3623 (16)	C8—C9	1.3803 (19)
N2—N3	1.3890 (14)	C9—C10	1.420 (2)
N2—H1N2	0.8600	C9—C12	1.489 (2)
N3—C7	1.3611 (17)	C10—C11	1.364 (2)
N3—H1N3	0.8600	C10—H10A	0.9300
C1—C2	1.3899 (19)	C11—H11A	0.9300
C1—C5	1.3940 (18)	C12—H12A	0.9600
C1—H1A	0.9300	C12—H12B	0.9600
C2—H2A	0.9300	C12—H12C	0.9600

C11—S1—C8	91.61 (7)	O1—C6—C5	123.00 (12)
C3—N1—C2	117.21 (12)	N2—C6—C5	112.71 (11)
C6—N2—N3	119.98 (11)	O2—C7—N3	121.52 (11)
C6—N2—H1N2	120.0	O2—C7—C8	122.19 (12)
N3—N2—H1N2	120.0	N3—C7—C8	116.25 (11)
C7—N3—N2	119.00 (11)	C9—C8—C7	126.96 (13)
C7—N3—H1N3	120.5	C9—C8—S1	111.48 (10)
N2—N3—H1N3	120.5	C7—C8—S1	121.53 (10)
C2—C1—C5	119.18 (12)	C8—C9—C10	111.46 (13)
C2—C1—H1A	120.4	C8—C9—C12	126.03 (14)
C5—C1—H1A	120.4	C10—C9—C12	122.50 (13)
N1—C2—C1	123.01 (13)	C11—C10—C9	113.35 (13)
N1—C2—H2A	118.5	C11—C10—H10A	123.3
C1—C2—H2A	118.5	C9—C10—H10A	123.3
N1—C3—C4	123.85 (12)	C10—C11—S1	112.10 (11)
N1—C3—H3A	118.1	C10—C11—H11A	124.0
C4—C3—H3A	118.1	S1—C11—H11A	124.0
C3—C4—C5	118.45 (12)	C9—C12—H12A	109.5
C3—C4—H4A	120.8	C9—C12—H12B	109.5
C5—C4—H4A	120.8	H12A—C12—H12B	109.5
C1—C5—C4	118.16 (12)	C9—C12—H12C	109.5
C1—C5—C6	119.18 (11)	H12A—C12—H12C	109.5
C4—C5—C6	122.64 (12)	H12B—C12—H12C	109.5
O1—C6—N2	124.29 (12)

C6—N2—N3—C7	−81.27 (15)	N2—N3—C7—C8	−175.15 (11)
C3—N1—C2—C1	2.3 (2)	O2—C7—C8—C9	21.3 (2)
C5—C1—C2—N1	0.6 (2)	N3—C7—C8—C9	−161.26 (13)
C2—N1—C3—C4	−2.5 (2)	O2—C7—C8—S1	−156.60 (11)
N1—C3—C4—C5	−0.2 (2)	N3—C7—C8—S1	20.83 (16)
C2—C1—C5—C4	−3.4 (2)	C11—S1—C8—C9	−0.12 (11)
C2—C1—C5—C6	175.06 (12)	C11—S1—C8—C7	178.09 (12)
C3—C4—C5—C1	3.2 (2)	C7—C8—C9—C10	−178.07 (13)
C3—C4—C5—C6	−175.20 (12)	S1—C8—C9—C10	0.02 (15)
N3—N2—C6—O1	−6.2 (2)	C7—C8—C9—C12	3.3 (2)
N3—N2—C6—C5	173.77 (11)	S1—C8—C9—C12	−178.58 (13)
C1—C5—C6—O1	32.1 (2)	C8—C9—C10—C11	0.12 (19)
C4—C5—C6—O1	−149.49 (14)	C12—C9—C10—C11	178.78 (14)
C1—C5—C6—N2	−147.86 (13)	C9—C10—C11—S1	−0.21 (17)
C4—C5—C6—N2	30.54 (18)	C8—S1—C11—C10	0.19 (12)
N2—N3—C7—O2	2.30 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1ⁱ	0.86	2.14	2.9068 (17)	149
N3—H1N3···O2ⁱⁱ	0.86	1.99	2.8034 (15)	158
C4—H4A···O1ⁱⁱⁱ	0.93	2.58	3.2047 (17)	125
C10—H10A···O2^iv	0.93	2.51	3.3928 (19)	159
C11—H11A···Cg1^v	0.93	2.80	3.3760 (17)	121

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₂S
M_r	261.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.9206 (1), 10.7552 (2), 12.4934 (2)
V (Å³)	1198.65 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.58 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.861, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	17333, 4355, 4078
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.05
No. of reflections	4355
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.43
Absolute structure	Flack (1983), 1856 Friedel pairs
Absolute structure parameter	−0.04 (6)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N2—H1N2···N1ⁱ	0.86	2.14	2.9068 (17)	149
N3—H1N3···O2ⁱⁱ	0.86	1.99	2.8034 (15)	158
C4—H4A···O1ⁱⁱⁱ	0.93	2.58	3.2047 (17)	125
C10—H10A···O2^iv	0.93	2.51	3.3928 (19)	159
C11—H11A···Cg1^v	0.93	2.80	3.3760 (17)	121

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

Footnotes

‡Additional correspondence author, e-mail: amirin@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815005). HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). HSNK and JHG thank USM for the award of a USM Fellowship.

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