Bis(4-fluoro­anilinium) sulfate

Fun, H.-K.; Arshad, S.; Dinesha; Laxmeshwar, S.; Nagaraja, G.K.

doi:10.1107/S1600536811033137

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2408

doi:10.1107/S1600536811033137

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Bis(4-fluoroanilinium) sulfate

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a Dinesha,^b Sandeep Laxmeshwar ^b and G. K. Nagaraja ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 August 2011; accepted 16 August 2011; online 27 August 2011)

In the crystal of the title molecular salt, 2C₆H₇FN⁺·SO₄²⁻, the cations and anions are linked by N—H⋯O and C—H⋯O hydrogen bonds into sheets parallel to the ab plane. The crystal studied was found to be a racemic twin with a 0.50 (10):0.50 (10) domain ratio.

Related literature

For related literature on phase transition dielectric materials, see: Fu et al. (2007 , 2008 , 2009 ); Fu & Xiong (2008 ). For hydrogen bonding studies, see: Zimmerman & Corbin (2000 ); Brunsveld et al. (2001 ); Desiraju (2002 ); Steiner (2002 ); Desiraju & Steiner (1999 ); Boutobba et al. (2010 ). For reference bond-length data, see: Allen et al. (1987 ). For a related crystal structure, see: Boutobba et al. (2010)

Experimental

Crystal data

2C₆H₇FN⁺·SO₄²⁻
M_r = 320.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2907 (5) Å
b = 7.4155 (6) Å
c = 30.168 (3) Å
V = 1407.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.58 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.859, T_max = 0.982
31062 measured reflections
4292 independent reflections
3503 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 0.98
4292 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1794 Friedel pairs
Flack parameter: 0.50 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3N1⋯O3	0.97	2.09	2.887 (3)	138
N2—H2N2⋯O3	0.85	1.90	2.741 (3)	168
N1—H1N1⋯O1ⁱ	0.86	1.92	2.761 (2)	162
N1—H2N1⋯O3ⁱⁱ	0.82	2.25	2.967 (2)	146
N1—H2N1⋯O4ⁱⁱ	0.82	2.55	3.151 (3)	131
N1—H3N1⋯O2ⁱⁱⁱ	0.97	2.24	2.925 (2)	126
N2—H1N2⋯O4^iv	0.94	1.78	2.7121 (18)	170
N2—H3N2⋯O2^v	0.99	1.72	2.702 (2)	170
C11—H11A⋯O4ⁱⁱⁱ	0.93	2.53	3.374 (3)	151
Symmetry codes: (i) x, y+1, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (v) x+1, y, z.

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/S1600536811033137/wn2446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033137/wn2446Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033137/wn2446Isup3.cml

checkCIF report

Comment top

Amine salts have attracted much attention as phase transition dielectric materials for their application in memory storage (Fu et al. 2007; Fu & Xiong 2008; Fu et al. 2008; Fu et al. 2009). Hydrogen bonding is one of the most versatile non-covalent forces in supramolecular chemistry and crystal engineering (Zimmerman & Corbin, 2000; Brunsveld et al., 2001; Desiraju, 2002). Therefore, in the past decades assessment of discrete hydrogen bonding patterns has received great attention (Steiner, 2002; Desiraju & Steiner, 1999; Boutobba et al., 2010) because of their widespread occurrence in biological systems.

The asymmetric unit of the title compound (Fig 1), contains two crystallographically independent 4-fluoroanilinium cations and a sulfate anion. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those in a closely related crystal structure (Boutobba et al., 2010).

The cations and anions are linked via intermolecular N1—H3N1···O3 and N2—H2N2···O3 hydrogen bonds (Table 1). In the crystal packing (Fig. 2), the intermolecular N1—H1N1···O1, N1—H2N1···O3, N1—H2N1···O4, N1—H3N1···O2, N2—H1N2···O4, N2—H3N2···O2 and C11—H11A···O4 hydrogen bonds (Table 1) link the molecules into sheets parallel to the ab plane.

Related literature top

For related literature on phase transition dielectric materials, see: Fu et al. (2007, 2008, 2009); Fu & Xiong (2008). For hydrogen bonding studies, see: Zimmerman & Corbin (2000); Brunsveld et al. (2001); Desiraju (2002); Steiner (2002); Desiraju & Steiner (1999); Boutobba et al. (2010). For reference bond-length data, see: Allen et al. (1987). For a related crystal structure, see: Boutobba et al. (2010)

Experimental top

To a solution of 4-fluoroaniline (10 mmol) in absolute ethanol was added sulfuric acid (5 drops) and the mixture refluxed for 4 h. After cooling the mixture to room temperature, a white solid appeared. This crude product was recrystallized from dimethylformamide to afford the desired product. M.p: 151–153°C.

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 with 30% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound. Dashed lines represent hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

Bis(4-fluoroanilinium) sulfate top

Crystal data top

2C₆H₇FN⁺·SO₄²⁻	F(000) = 664
M_r = 320.31	D_x = 1.512 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5694 reflections
a = 6.2907 (5) Å	θ = 2.7–27.5°
b = 7.4155 (6) Å	µ = 0.27 mm⁻¹
c = 30.168 (3) Å	T = 296 K
V = 1407.3 (2) Å³	Needle, colourless
Z = 4	0.58 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4292 independent reflections
Radiation source: fine-focus sealed tube	3503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 30.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.859, T_max = 0.982	k = −10→10
31062 measured reflections	l = −43→43

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0492P)² + 0.377P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
4292 reflections	Δρ_max = 0.18 e Å⁻³
191 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1794 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.50 (10)

Crystal data top

2C₆H₇FN⁺·SO₄²⁻	V = 1407.3 (2) Å³
M_r = 320.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.2907 (5) Å	µ = 0.27 mm⁻¹
b = 7.4155 (6) Å	T = 296 K
c = 30.168 (3) Å	0.58 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4292 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3503 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.982	R_int = 0.044
31062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.103	Δρ_max = 0.18 e Å⁻³
S = 0.98	Δρ_min = −0.39 e Å⁻³
4292 reflections	Absolute structure: Flack (1983), 1794 Friedel pairs
191 parameters	Absolute structure parameter: 0.50 (10)
0 restraints

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
S1	−0.00432 (8)	0.47390 (4)	0.013801 (11)	0.02691 (9)
F1	0.5089 (5)	0.3730 (3)	0.25139 (4)	0.1033 (6)
F2	−0.0181 (4)	0.8372 (3)	0.22704 (4)	0.1096 (7)
O1	−0.0040 (3)	0.29560 (14)	0.03416 (4)	0.0452 (3)
O2	−0.2002 (2)	0.5713 (2)	0.02606 (5)	0.0372 (3)
O3	0.1801 (2)	0.5795 (2)	0.02941 (5)	0.0381 (4)
O4	0.0060 (3)	0.45980 (17)	−0.03476 (4)	0.0470 (3)
N1	−0.0142 (3)	0.92624 (16)	0.04544 (4)	0.0309 (3)
H1N1	0.0125	1.0369	0.0384	0.046*
H2N1	−0.1252	0.8982	0.0330	0.046*
H3N1	0.0935	0.8514	0.0315	0.046*
N2	0.4960 (3)	0.37944 (17)	0.06828 (4)	0.0332 (3)
H1N2	0.5163	0.2639	0.0563	0.050*
H2N2	0.3856	0.4288	0.0573	0.050*
H3N2	0.6038	0.4605	0.0553	0.050*
C1	0.3283 (3)	0.4459 (4)	0.13955 (7)	0.0492 (5)
H1A	0.2115	0.4926	0.1245	0.059*
C2	0.3318 (4)	0.4435 (4)	0.18574 (7)	0.0639 (7)
H2A	0.2179	0.4881	0.2020	0.077*
C3	0.5047 (5)	0.3749 (3)	0.20625 (6)	0.0634 (6)
C4	0.6765 (5)	0.3079 (4)	0.18406 (8)	0.0646 (7)
H4A	0.7923	0.2611	0.1994	0.077*
C5	0.6742 (4)	0.3113 (3)	0.13811 (7)	0.0487 (5)
H5A	0.7901	0.2686	0.1221	0.058*
C6	0.4990 (4)	0.37857 (19)	0.11639 (5)	0.0326 (3)
C7	−0.1933 (3)	0.8307 (3)	0.11348 (6)	0.0434 (5)
H7A	−0.3113	0.7982	0.0967	0.052*
C8	−0.1934 (4)	0.8076 (4)	0.15908 (7)	0.0583 (6)
H8A	−0.3101	0.7575	0.1734	0.070*
C9	−0.0178 (5)	0.8602 (4)	0.18240 (6)	0.0636 (7)
C10	0.1576 (4)	0.9328 (4)	0.16300 (8)	0.0671 (7)
H10A	0.2739	0.9677	0.1800	0.081*
C11	0.1593 (4)	0.9536 (3)	0.11737 (7)	0.0496 (5)
H11A	0.2778	1.0015	0.1032	0.059*
C12	−0.0157 (3)	0.9027 (2)	0.09331 (5)	0.0317 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02748 (16)	0.02319 (15)	0.03006 (16)	−0.0005 (2)	0.0004 (2)	0.00064 (11)
F1	0.1150 (14)	0.1674 (18)	0.0274 (6)	−0.006 (2)	−0.0039 (9)	0.0034 (8)
F2	0.1171 (15)	0.1814 (19)	0.0301 (6)	0.013 (2)	0.0030 (10)	0.0157 (9)
O1	0.0549 (8)	0.0257 (5)	0.0550 (7)	0.0033 (10)	0.0022 (10)	0.0096 (5)
O2	0.0269 (6)	0.0333 (9)	0.0515 (8)	0.0032 (6)	0.0029 (6)	−0.0008 (7)
O3	0.0295 (6)	0.0324 (9)	0.0524 (8)	−0.0017 (6)	−0.0039 (6)	−0.0042 (7)
O4	0.0639 (8)	0.0467 (7)	0.0303 (6)	0.0010 (14)	0.0026 (8)	−0.0026 (5)
N1	0.0369 (7)	0.0261 (5)	0.0298 (6)	0.0007 (9)	0.0015 (7)	0.0008 (4)
N2	0.0321 (6)	0.0393 (6)	0.0283 (6)	−0.0015 (10)	0.0003 (9)	0.0001 (4)
C1	0.0423 (10)	0.0681 (15)	0.0373 (10)	0.0054 (11)	0.0034 (8)	−0.0018 (10)
C2	0.0595 (14)	0.095 (2)	0.0372 (11)	0.0064 (16)	0.0121 (10)	−0.0068 (13)
C3	0.0767 (16)	0.0857 (16)	0.0279 (8)	−0.008 (2)	−0.0039 (15)	0.0008 (8)
C4	0.0707 (17)	0.0807 (19)	0.0424 (12)	0.0137 (15)	−0.0198 (11)	0.0016 (12)
C5	0.0482 (12)	0.0584 (14)	0.0394 (10)	0.0137 (11)	−0.0061 (9)	−0.0058 (10)
C6	0.0364 (8)	0.0336 (7)	0.0279 (6)	−0.0029 (12)	−0.0022 (10)	−0.0012 (5)
C7	0.0436 (11)	0.0487 (12)	0.0380 (10)	−0.0036 (10)	0.0068 (8)	−0.0001 (9)
C8	0.0661 (16)	0.0679 (16)	0.0409 (11)	−0.0040 (14)	0.0180 (11)	0.0081 (11)
C9	0.0770 (18)	0.0866 (16)	0.0272 (8)	0.010 (2)	0.0032 (13)	0.0061 (9)
C10	0.0642 (15)	0.097 (2)	0.0400 (11)	−0.0012 (16)	−0.0178 (11)	−0.0017 (14)
C11	0.0458 (11)	0.0629 (14)	0.0399 (10)	−0.0086 (11)	−0.0051 (9)	0.0039 (10)
C12	0.0372 (9)	0.0281 (6)	0.0298 (7)	0.0017 (10)	0.0002 (9)	0.0012 (5)

Geometric parameters (Å, º) top

S1—O1	1.4579 (11)	C2—C3	1.350 (4)
S1—O4	1.4700 (11)	C2—H2A	0.9300
S1—O2	1.4755 (14)	C3—C4	1.365 (4)
S1—O3	1.4767 (14)	C4—C5	1.387 (3)
F1—C3	1.362 (2)	C4—H4A	0.9300
F2—C9	1.357 (2)	C5—C6	1.376 (3)
N1—C12	1.4548 (19)	C5—H5A	0.9300
N1—H1N1	0.8644	C7—C12	1.379 (3)
N1—H2N1	0.8198	C7—C8	1.386 (3)
N1—H3N1	0.9724	C7—H7A	0.9300
N2—C6	1.4513 (17)	C8—C9	1.366 (4)
N2—H1N2	0.9393	C8—H8A	0.9300
N2—H2N2	0.8524	C9—C10	1.360 (4)
N2—H3N2	0.9875	C10—C11	1.385 (3)
C1—C6	1.376 (3)	C10—H10A	0.9300
C1—C2	1.394 (3)	C11—C12	1.371 (3)
C1—H1A	0.9300	C11—H11A	0.9300

O1—S1—O4	110.81 (7)	C3—C4—C5	118.4 (2)
O1—S1—O2	109.84 (10)	C3—C4—H4A	120.8
O4—S1—O2	108.76 (10)	C5—C4—H4A	120.8
O1—S1—O3	110.21 (10)	C6—C5—C4	119.4 (2)
O4—S1—O3	108.71 (10)	C6—C5—H5A	120.3
O2—S1—O3	108.45 (7)	C4—C5—H5A	120.3
C12—N1—H1N1	111.1	C1—C6—C5	121.03 (16)
C12—N1—H2N1	114.8	C1—C6—N2	119.73 (19)
H1N1—N1—H2N1	107.0	C5—C6—N2	119.24 (19)
C12—N1—H3N1	111.5	C12—C7—C8	119.1 (2)
H1N1—N1—H3N1	107.5	C12—C7—H7A	120.5
H2N1—N1—H3N1	104.5	C8—C7—H7A	120.5
C6—N2—H1N2	112.3	C9—C8—C7	118.4 (2)
C6—N2—H2N2	113.7	C9—C8—H8A	120.8
H1N2—N2—H2N2	110.6	C7—C8—H8A	120.8
C6—N2—H3N2	113.0	F2—C9—C10	118.5 (3)
H1N2—N2—H3N2	108.0	F2—C9—C8	118.3 (3)
H2N2—N2—H3N2	98.3	C10—C9—C8	123.19 (19)
C6—C1—C2	119.4 (2)	C9—C10—C11	118.5 (2)
C6—C1—H1A	120.3	C9—C10—H10A	120.7
C2—C1—H1A	120.3	C11—C10—H10A	120.7
C3—C2—C1	118.4 (2)	C12—C11—C10	119.3 (2)
C3—C2—H2A	120.8	C12—C11—H11A	120.4
C1—C2—H2A	120.8	C10—C11—H11A	120.4
C2—C3—F1	118.5 (3)	C11—C12—C7	121.54 (17)
C2—C3—C4	123.4 (2)	C11—C12—N1	119.15 (19)
F1—C3—C4	118.1 (3)	C7—C12—N1	119.31 (18)

C6—C1—C2—C3	0.2 (4)	C12—C7—C8—C9	1.1 (4)
C1—C2—C3—F1	179.8 (2)	C7—C8—C9—F2	−179.9 (2)
C1—C2—C3—C4	0.1 (5)	C7—C8—C9—C10	−0.5 (4)
C2—C3—C4—C5	0.4 (5)	F2—C9—C10—C11	179.0 (3)
F1—C3—C4—C5	−179.3 (2)	C8—C9—C10—C11	−0.4 (5)
C3—C4—C5—C6	−1.1 (4)	C9—C10—C11—C12	0.8 (4)
C2—C1—C6—C5	−0.9 (4)	C10—C11—C12—C7	−0.2 (4)
C2—C1—C6—N2	179.6 (2)	C10—C11—C12—N1	179.4 (2)
C4—C5—C6—C1	1.4 (4)	C8—C7—C12—C11	−0.8 (3)
C4—C5—C6—N2	−179.1 (2)	C8—C7—C12—N1	179.62 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3N1···O3	0.97	2.09	2.887 (3)	138
N2—H2N2···O3	0.85	1.90	2.741 (3)	168
N1—H1N1···O1ⁱ	0.86	1.92	2.761 (2)	162
N1—H2N1···O3ⁱⁱ	0.82	2.25	2.967 (2)	146
N1—H2N1···O4ⁱⁱ	0.82	2.55	3.151 (3)	131
N1—H3N1···O2ⁱⁱⁱ	0.97	2.24	2.925 (2)	126
N2—H1N2···O4^iv	0.94	1.78	2.7121 (18)	170
N2—H3N2···O2^v	0.99	1.72	2.702 (2)	170
C11—H11A···O4ⁱⁱⁱ	0.93	2.53	3.374 (3)	151

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

Experimental details

Crystal data
Chemical formula	2C₆H₇FN⁺·SO₄²⁻
M_r	320.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.2907 (5), 7.4155 (6), 30.168 (3)
V (Å³)	1407.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.58 × 0.12 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.859, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	31062, 4292, 3503
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 0.98
No. of reflections	4292
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.39
Absolute structure	Flack (1983), 1794 Friedel pairs
Absolute structure parameter	0.50 (10)

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—H3N1···O3	0.97	2.09	2.887 (3)	138
N2—H2N2···O3	0.85	1.90	2.741 (3)	168
N1—H1N1···O1ⁱ	0.86	1.92	2.761 (2)	162
N1—H2N1···O3ⁱⁱ	0.82	2.25	2.967 (2)	145.9
N1—H2N1···O4ⁱⁱ	0.82	2.55	3.151 (3)	131.4
N1—H3N1···O2ⁱⁱⁱ	0.97	2.24	2.925 (2)	126.4
N2—H1N2···O4^iv	0.94	1.78	2.7121 (18)	170
N2—H3N2···O2^v	0.99	1.72	2.702 (2)	170
C11—H11A···O4ⁱⁱⁱ	0.93	2.53	3.374 (3)	150.8

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the award of a research scholarship.

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