3-Amino­benzoic acid–4-nitro­benzoic acid (1/1)

Quah, C.K.; Jebas, S.R.; Fun, H.-K.

doi:10.1107/S1600536808037112

organic compounds

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Volume 64| Part 12| December 2008| Page o2333

doi:10.1107/S1600536808037112

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3-Aminobenzoic acid–4-nitrobenzoic acid (1/1)

Ching Kheng Quah,^a Samuel Robinson Jebas ^a ‡§ and Hoong-Kun Fun ^a ^*

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

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

In the title 1:1 adduct, C₇H₅NO₄·C₇H₇NO₂, the nitro group of the 4-nitro benzoic acid is twisted from the attached ring by 4.40 (8)°. In the crystal, the molecules are linked into ribbon-like structures along [150] and [1 $[\overline{5}]$ 0] via O—H⋯O, N—H⋯O, N—H⋯N and C—H⋯O intermolecular hydrogen bonds.

Related literature

For the applications of 3-aminobenzoic acid, see; Windholz (1976 ). For related structures, see: Bowers et al. (2005 ); Tonogaki et al. (1993 ); Voogd et al. (1980 ).

Experimental

Crystal data

C₇H₅NO₄·C₇H₇NO₂
M_r = 304.26
Monoclinic, C 2/c
a = 25.3707 (8) Å
b = 4.9875 (2) Å
c = 21.7276 (7) Å
β = 109.230 (2)°
V = 2595.93 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100.0 (1) K
0.24 × 0.09 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.971, T_max = 0.993
15472 measured reflections
3759 independent reflections
2197 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.179
S = 1.01
3759 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O5ⁱ	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6⋯O3ⁱⁱ	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1⋯O2ⁱⁱⁱ	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2⋯O2^iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A⋯O5^v	0.95	2.58	3.288 (3)	131
C4—H4A⋯O6^iv	0.95	2.55	3.339 (3)	141
C10—H10A⋯O1ⁱⁱⁱ	0.95	2.57	3.460 (3)	156
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ ; (iii) x, y-1, z; (iv) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (v) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037112/ci2714sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037112/ci2714Isup2.hkl

checkCIF report

Comment top

3-Aminobenzoic acid is used as an intermediate for dyes, pesticides and in other organic synthesis (Windholz, 1976). The crystal structures of 3-aminobenzoic acid (Voogd et al., 1980) and 4-aminobenzoic acid-4-nitrobenzoic acid have been reported (Bowers et al., 2005). As a part of our investigation of the interactions between acids, we report herein the crystal structure of the title compound.

The asymmetric unit (Fig. 1) contains one 3-aminobenzoic acid molecule and one 4-nitrobenzoic acid molecule. The bond lengths and angles of 3-aminobenzoic acid and 4-nitrobenzoic acid are found to have normal values (Voogd et al., 1980; Tonogaki et al., 1993). Both the molecules are almost planar with the maximum deviation from planarity being 0.026 (2) Å for atom O5 of 3-aminobenzoic acid molecule, and 0.078 (2) Å for atom O1 of nitrobenzoic acid molecule. In the 4-nitrobenzoic acid molecule, the nitro group is twisted slightly from the attached ring; the dihedral angle between C1—C6 and O1—O2/C3/N1 planes is 4.40 (8)°.

The crystal packing is consolidated by O—H···O, N—H···O, N—H···N and C—H···O intermolecular hydrogen bonds (Table 1). These hydrogen bonds link the molecules into ribbon like structures along [1 5 0] and [1 5 0] (Fig.2).

Related literature top

For the applications of 3-aminobenzoic acid, see; Windholz (1976). For related structures, see: Bowers et al. (2005); Tonogaki et al. (1993); Voogd et al. (1980).

Experimental top

3-Aminobenzoic acid and 4-nitrobenzoic acid were mixed in methanol (20 ml) in a 1:1 molar ratio. The clear colourless solution obtained was allowed to evaporate slowly. Colourless crystals were obtained after 2 d.

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 asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

3-Aminobenzoic acid–4-nitrobenzoic acid (1/1) top

Crystal data top

C₇H₅NO₄·C₇H₇NO₂	F(000) = 1264
M_r = 304.26	D_x = 1.557 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2404 reflections
a = 25.3707 (8) Å	θ = 3.0–29.9°
b = 4.9875 (2) Å	µ = 0.12 mm⁻¹
c = 21.7276 (7) Å	T = 100 K
β = 109.230 (2)°	Plate, yellow
V = 2595.93 (16) Å³	0.24 × 0.09 × 0.06 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −34→35
T_min = 0.971, T_max = 0.993	k = −7→7
15472 measured reflections	l = −29→30

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.087P)² + 1.6119P] where P = (F_o² + 2F_c²)/3
3759 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₇H₅NO₄·C₇H₇NO₂	V = 2595.93 (16) Å³
M_r = 304.26	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.3707 (8) Å	µ = 0.12 mm⁻¹
b = 4.9875 (2) Å	T = 100 K
c = 21.7276 (7) Å	0.24 × 0.09 × 0.06 mm
β = 109.230 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3759 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2197 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.993	R_int = 0.068
15472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.50 e Å⁻³
3759 reflections	Δρ_min = −0.36 e Å⁻³
215 parameters

Special details top

Experimental. The 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
O1	0.82025 (7)	0.6966 (4)	0.14306 (8)	0.0238 (4)
O2	0.81699 (7)	0.7604 (3)	0.04310 (8)	0.0236 (4)
O3	1.01559 (7)	−0.2306 (3)	0.07932 (8)	0.0175 (4)
O4	1.01017 (7)	−0.3174 (3)	0.17847 (8)	0.0183 (4)
O5	0.57710 (6)	0.7825 (3)	0.18023 (8)	0.0180 (4)
O6	0.58739 (7)	0.8769 (4)	0.08408 (8)	0.0194 (4)
N1	0.83479 (8)	0.6430 (4)	0.09588 (9)	0.0178 (4)
N2	0.73488 (9)	0.2432 (5)	0.06366 (11)	0.0217 (5)
C1	0.93325 (9)	0.0854 (5)	0.16778 (11)	0.0166 (5)
H1A	0.9461	−0.0152	0.2070	0.020*
C2	0.89370 (9)	0.2853 (5)	0.16067 (11)	0.0167 (5)
H2A	0.8792	0.3241	0.1948	0.020*
C3	0.87598 (9)	0.4267 (5)	0.10277 (11)	0.0158 (5)
C4	0.89605 (9)	0.3786 (5)	0.05146 (11)	0.0160 (5)
H4A	0.8831	0.4800	0.0123	0.019*
C5	0.93576 (9)	0.1775 (5)	0.05923 (11)	0.0164 (5)
H5A	0.9503	0.1395	0.0251	0.020*
C6	0.95413 (8)	0.0322 (5)	0.11703 (10)	0.0136 (5)
C7	0.99642 (9)	−0.1847 (4)	0.12311 (11)	0.0145 (5)
C8	0.66801 (9)	0.4869 (5)	0.10050 (11)	0.0172 (5)
H8A	0.6584	0.5966	0.0627	0.021*
C9	0.70819 (9)	0.2837 (5)	0.10949 (11)	0.0179 (5)
C10	0.72180 (10)	0.1297 (5)	0.16603 (12)	0.0199 (5)
H10A	0.7492	−0.0069	0.1728	0.024*
C11	0.69646 (9)	0.1707 (5)	0.21230 (12)	0.0203 (5)
H11A	0.7066	0.0630	0.2505	0.024*
C12	0.65613 (9)	0.3688 (5)	0.20347 (11)	0.0180 (5)
H12A	0.6383	0.3962	0.2351	0.022*
C13	0.64223 (9)	0.5267 (5)	0.14746 (11)	0.0152 (5)
C14	0.59973 (9)	0.7398 (4)	0.13881 (11)	0.0143 (5)
H1O4	1.0354 (14)	−0.442 (8)	0.1783 (15)	0.056 (11)*
H1O6	0.5600 (15)	0.998 (8)	0.0809 (16)	0.063 (11)*
H1N1	0.7575 (14)	0.064 (8)	0.0643 (16)	0.063 (11)*
H2N2	0.7158 (12)	0.302 (6)	0.0233 (14)	0.029 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0264 (9)	0.0247 (10)	0.0238 (10)	0.0060 (7)	0.0131 (8)	−0.0027 (7)
O2	0.0266 (9)	0.0214 (10)	0.0227 (9)	0.0058 (7)	0.0079 (7)	0.0042 (7)
O3	0.0198 (8)	0.0161 (9)	0.0190 (8)	0.0049 (7)	0.0095 (7)	0.0019 (7)
O4	0.0226 (9)	0.0164 (9)	0.0182 (9)	0.0086 (7)	0.0098 (7)	0.0039 (7)
O5	0.0213 (8)	0.0155 (9)	0.0190 (9)	0.0037 (7)	0.0090 (7)	0.0012 (7)
O6	0.0222 (9)	0.0206 (9)	0.0185 (9)	0.0069 (7)	0.0108 (7)	0.0035 (7)
N1	0.0180 (9)	0.0171 (10)	0.0187 (10)	0.0008 (8)	0.0067 (8)	−0.0014 (8)
N2	0.0229 (11)	0.0244 (12)	0.0197 (11)	0.0051 (9)	0.0096 (9)	0.0015 (9)
C1	0.0168 (11)	0.0159 (12)	0.0173 (12)	0.0005 (9)	0.0060 (9)	0.0008 (9)
C2	0.0180 (11)	0.0171 (12)	0.0173 (12)	−0.0008 (9)	0.0091 (9)	−0.0019 (9)
C3	0.0123 (10)	0.0125 (12)	0.0227 (12)	0.0023 (8)	0.0057 (9)	−0.0028 (9)
C4	0.0180 (11)	0.0138 (11)	0.0173 (12)	0.0020 (9)	0.0073 (9)	0.0034 (9)
C5	0.0181 (11)	0.0164 (12)	0.0168 (12)	0.0000 (9)	0.0087 (9)	0.0002 (9)
C6	0.0121 (10)	0.0125 (11)	0.0164 (11)	−0.0018 (8)	0.0051 (8)	−0.0007 (9)
C7	0.0139 (10)	0.0132 (12)	0.0169 (12)	−0.0018 (9)	0.0058 (9)	−0.0010 (9)
C8	0.0174 (11)	0.0155 (12)	0.0195 (12)	−0.0017 (9)	0.0073 (9)	−0.0011 (9)
C9	0.0151 (11)	0.0173 (12)	0.0222 (12)	−0.0025 (9)	0.0075 (9)	−0.0058 (9)
C10	0.0172 (11)	0.0151 (12)	0.0251 (13)	0.0029 (9)	0.0040 (10)	−0.0019 (10)
C11	0.0193 (12)	0.0179 (13)	0.0224 (13)	0.0012 (9)	0.0052 (10)	0.0006 (9)
C12	0.0184 (11)	0.0163 (12)	0.0197 (12)	0.0025 (9)	0.0069 (9)	0.0000 (9)
C13	0.0126 (10)	0.0138 (11)	0.0201 (12)	0.0010 (9)	0.0066 (9)	−0.0014 (9)
C14	0.0140 (10)	0.0137 (11)	0.0155 (11)	0.0000 (9)	0.0053 (8)	−0.0014 (9)

Geometric parameters (Å, º) top

O1—N1	1.228 (2)	C3—C4	1.391 (3)
O2—N1	1.233 (2)	C4—C5	1.392 (3)
O3—C7	1.225 (3)	C4—H4A	0.95
O4—C7	1.315 (3)	C5—C6	1.391 (3)
O4—H1O4	0.89 (4)	C5—H5A	0.95
O5—C14	1.235 (3)	C6—C7	1.498 (3)
O6—C14	1.317 (3)	C8—C13	1.396 (3)
O6—H1O6	0.91 (4)	C8—C9	1.405 (3)
N1—C3	1.475 (3)	C8—H8A	0.95
N2—C9	1.391 (3)	C9—C10	1.392 (3)
N2—H1N1	1.06 (4)	C10—C11	1.375 (3)
N2—H2N2	0.90 (3)	C10—H10A	0.95
C1—C2	1.387 (3)	C11—C12	1.390 (3)
C1—C6	1.397 (3)	C11—H11A	0.95
C1—H1A	0.95	C12—C13	1.394 (3)
C2—C3	1.382 (3)	C12—H12A	0.95
C2—H2A	0.95	C13—C14	1.481 (3)

C7—O4—H1O4	109 (2)	C1—C6—C7	120.9 (2)
C14—O6—H1O6	111 (2)	O3—C7—O4	124.3 (2)
O1—N1—O2	123.7 (2)	O3—C7—C6	121.5 (2)
O1—N1—C3	118.17 (19)	O4—C7—C6	114.23 (19)
O2—N1—C3	118.17 (18)	C13—C8—C9	119.6 (2)
C9—N2—H1N1	120.1 (18)	C13—C8—H8A	120.2
C9—N2—H2N2	114.7 (18)	C9—C8—H8A	120.2
H1N1—N2—H2N2	114 (3)	N2—C9—C10	120.9 (2)
C2—C1—C6	119.8 (2)	N2—C9—C8	120.5 (2)
C2—C1—H1A	120.1	C10—C9—C8	118.6 (2)
C6—C1—H1A	120.1	C11—C10—C9	121.5 (2)
C3—C2—C1	118.3 (2)	C11—C10—H10A	119.2
C3—C2—H2A	120.8	C9—C10—H10A	119.2
C1—C2—H2A	120.8	C10—C11—C12	120.3 (2)
C2—C3—C4	123.1 (2)	C10—C11—H11A	119.8
C2—C3—N1	118.23 (19)	C12—C11—H11A	119.8
C4—C3—N1	118.6 (2)	C11—C12—C13	119.0 (2)
C3—C4—C5	117.9 (2)	C11—C12—H12A	120.5
C3—C4—H4A	121.0	C13—C12—H12A	120.5
C5—C4—H4A	121.0	C12—C13—C8	120.9 (2)
C6—C5—C4	119.9 (2)	C12—C13—C14	118.7 (2)
C6—C5—H5A	120.0	C8—C13—C14	120.4 (2)
C4—C5—H5A	120.0	O5—C14—O6	122.6 (2)
C5—C6—C1	120.8 (2)	O5—C14—C13	121.7 (2)
C5—C6—C7	118.24 (19)	O6—C14—C13	115.72 (19)

C6—C1—C2—C3	0.1 (3)	C5—C6—C7—O4	−178.0 (2)
C1—C2—C3—C4	−0.3 (3)	C1—C6—C7—O4	1.3 (3)
C1—C2—C3—N1	−178.7 (2)	C13—C8—C9—N2	−179.2 (2)
O1—N1—C3—C2	3.6 (3)	C13—C8—C9—C10	−1.0 (3)
O2—N1—C3—C2	−176.6 (2)	N2—C9—C10—C11	178.8 (2)
O1—N1—C3—C4	−175.0 (2)	C8—C9—C10—C11	0.7 (3)
O2—N1—C3—C4	4.9 (3)	C9—C10—C11—C12	0.1 (4)
C2—C3—C4—C5	0.2 (3)	C10—C11—C12—C13	−0.7 (3)
N1—C3—C4—C5	178.7 (2)	C11—C12—C13—C8	0.3 (3)
C3—C4—C5—C6	−0.1 (3)	C11—C12—C13—C14	−179.2 (2)
C4—C5—C6—C1	0.0 (3)	C9—C8—C13—C12	0.5 (3)
C4—C5—C6—C7	179.3 (2)	C9—C8—C13—C14	−179.9 (2)
C2—C1—C6—C5	0.0 (3)	C12—C13—C14—O5	1.0 (3)
C2—C1—C6—C7	−179.3 (2)	C8—C13—C14—O5	−178.6 (2)
C5—C6—C7—O3	1.7 (3)	C12—C13—C14—O6	−178.2 (2)
C1—C6—C7—O3	−179.0 (2)	C8—C13—C14—O6	2.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O5ⁱ	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6···O3ⁱⁱ	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1···O2ⁱⁱⁱ	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2···O2^iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A···O5^v	0.95	2.58	3.288 (3)	131
C4—H4A···O6^iv	0.95	2.55	3.339 (3)	141
C10—H10A···O1ⁱⁱⁱ	0.95	2.57	3.460 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₇H₅NO₄·C₇H₇NO₂
M_r	304.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	25.3707 (8), 4.9875 (2), 21.7276 (7)
β (°)	109.230 (2)
V (Å³)	2595.93 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.24 × 0.09 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.971, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	15472, 3759, 2197
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.179, 1.01
No. of reflections	3759
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.36

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
O4—H1O4···O5ⁱ	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6···O3ⁱⁱ	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1···O2ⁱⁱⁱ	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2···O2^iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A···O5^v	0.95	2.58	3.288 (3)	131
C4—H4A···O6^iv	0.95	2.55	3.339 (3)	141
C10—H10A···O1ⁱⁱⁱ	0.95	2.57	3.460 (3)	156

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641114, India.

§Additional correspondence author, e-mail: robinsunj@yahoo.com.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. CKQ thanks Universiti Sains Malaysia for a student assistanceship.

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