4-Amino-3-ammonio­pyridinium dinitrate

Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810005556

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o639-o640

doi:10.1107/S1600536810005556

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4-Amino-3-ammoniopyridinium dinitrate

Madhukar Hemamalini ^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 4 February 2010; accepted 10 February 2010; online 17 February 2010)

In the crystal structure of the title compound, C₅H₉N₃²⁺·2NO₃⁻, the cations and anions are connected by intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by π⋯π interactions between pyridinium rings [centroid–centroid distance = 3.775 (4) Å].

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ); Katritzky et al. (1996 ); Abu Zuhri & Cox (1989 ). For related structures, see: Fun & Balasubramani (2009 ); Rubin-Preminger & Englert (2007 ); Qin & Wang (2009 ). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ); Jeffrey (1997 ); Scheiner (1997 ). For reference bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₅H₉N₃²⁺·2NO₃⁻
M_r = 235.17
Monoclinic, P 2₁ /c
a = 12.3008 (5) Å
b = 10.5086 (5) Å
c = 7.1411 (3) Å
β = 97.546 (1)°
V = 915.09 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.65 × 0.37 × 0.28 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.906, T_max = 0.958
18234 measured reflections
4796 independent reflections
4129 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.06
4796 reflections
181 parameters
All H-atom parameters refined
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.874 (13)	2.001 (13)	2.7750 (7)	147.0 (12)
N2—H1N2⋯O5	0.935 (14)	2.105 (15)	2.9070 (8)	143.1 (12)
N2—H1N2⋯O2ⁱⁱ	0.935 (14)	2.211 (14)	2.7767 (7)	118.1 (11)
N2—H2N2⋯O3ⁱⁱⁱ	0.881 (14)	2.193 (14)	3.0006 (7)	152.3 (12)
N2—H2N2⋯O3^iv	0.881 (14)	2.482 (14)	2.9231 (7)	111.6 (11)
N3—H1N3⋯O4	0.844 (16)	2.054 (16)	2.8653 (8)	161.0 (14)
N3—H2N3⋯O6^v	0.827 (12)	2.130 (12)	2.9442 (7)	168.0 (12)
N2—H3N2⋯O5^iv	0.871 (12)	1.963 (12)	2.8227 (8)	169.0 (12)
N2—H3N2⋯O6^iv	0.871 (12)	2.494 (12)	3.1217 (7)	129.5 (10)
C2—H2⋯O3ⁱⁱⁱ	0.910 (11)	2.439 (11)	3.0489 (8)	124.6 (9)
C2—H2⋯O1^vi	0.910 (11)	2.552 (11)	3.1834 (8)	127.0 (9)
C2—H2⋯O3^iv	0.910 (11)	2.570 (11)	3.1277 (8)	120.2 (9)
C3—H3⋯O6ⁱ	0.979 (12)	2.253 (12)	3.1170 (8)	146.6 (10)
C4—H4⋯O4^v	0.926 (12)	2.559 (12)	3.4274 (8)	156.3 (10)
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x, -y+1, -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/S1600536810005556/rz2419sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005556/rz2419Isup2.hkl

checkCIF report

Comment top

Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996). In particular, diaminopyridines play an important role in the preparation of aromatic azo dyes, the subject of many polarographic investigations (Abu Zuhri & Cox, 1989). Pyridine and its substituted derivatives are often involved in hydrogen-bond interactions (Jeffrey & Saenger, 1991; Jeffrey, 1997; Scheiner, 1997). The crystal structures of 3,4-diaminopyridine (Rubin-Preminger & Englert, 2007), 3,4-diaminopyridinium hydrogen succinate (Fun & Balasubramani, 2009) and 4-amino-3-ammoniopyridinium dichloride (Qin & Wang, 2009) have been reported in the literature. In order to study some interesting hydrogen bonding interactions, the synthesis and structure of the title salt is presented here.

The asymmetric unit of the title compound (Fig. 1) consists of a diprotonated 3,4-diaminopyridine cation and two nitrate anions. In the 3,4-diaminopyridinium cation, protonation at atom N1 has lead to a slight increase in the C2—N1—C3 angle to 121.45 (5)° compared to those of an unprotonated structure (Rubin-Preminger & Englert, 2007). The 3-amino N atom (N2) is also protonated. This type of protonation has also been observed in the crystal structure of 4-amino-3-ammoniopyridinium dichloride (Qin & Wang, 2009). The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal structure (Fig. 2), the anions and cations are connected by intermolecular strong N—H···O and weak C—H···O hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by π···π interactions between the pyridinium rings (N1/C1–C5) [centroid-to-centroid (x, 3/2-y, -1/2+z and x, 3/2-y, 1/2+z) distance = 3.775 (4)Å].

Related literature top

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996); Abu Zuhri & Cox (1989). For related structures, see: Fun & Balasubramani (2009); Rubin-Preminger & Englert (2007); Qin & Wang (2009). For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For reference bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a hot methanol solution (20 ml) of 3,4-diaminopyridine (27 mg, Aldrich) was added a few drops of nitric acid. The solution was warmed over a water bath for a few minutes. The resulting solution was allowed to cool slowly to room temperature. Crystals of the title compound appeared from the mother liquor after a few days.

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 and PLATON (Spek, 2009).

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, showing hydrogen-bonded (dashed lines) networks.

4-amino-3-ammoniopyridinium dinitrate top

Crystal data top

C₅H₉N₃²⁺·2NO³⁻	F(000) = 488
M_r = 235.17	D_x = 1.707 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9066 reflections
a = 12.3008 (5) Å	θ = 3.3–37.5°
b = 10.5086 (5) Å	µ = 0.16 mm⁻¹
c = 7.1411 (3) Å	T = 100 K
β = 97.546 (1)°	Block, colourless
V = 915.09 (7) Å³	0.65 × 0.37 × 0.28 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4796 independent reflections
Radiation source: fine-focus sealed tube	4129 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 37.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→20
T_min = 0.906, T_max = 0.958	k = −17→17
18234 measured reflections	l = −10→12

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0545P)² + 0.1242P] where P = (F_o² + 2F_c²)/3
4796 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₅H₉N₃²⁺·2NO³⁻	V = 915.09 (7) Å³
M_r = 235.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3008 (5) Å	µ = 0.16 mm⁻¹
b = 10.5086 (5) Å	T = 100 K
c = 7.1411 (3) Å	0.65 × 0.37 × 0.28 mm
β = 97.546 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4796 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4129 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.958	R_int = 0.024
18234 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	All H-atom parameters refined
S = 1.06	Δρ_max = 0.66 e Å⁻³
4796 reflections	Δρ_min = −0.26 e Å⁻³
181 parameters

Special details top

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

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
N1	0.18671 (4)	0.78615 (5)	0.42895 (7)	0.01262 (9)
N2	0.17802 (4)	0.43778 (5)	0.39491 (7)	0.01067 (8)
N3	0.39285 (4)	0.50229 (5)	0.29631 (9)	0.01537 (10)
C1	0.21985 (4)	0.56747 (5)	0.39298 (8)	0.00969 (9)
C2	0.15309 (5)	0.66472 (5)	0.43549 (8)	0.01097 (9)
C3	0.28652 (5)	0.81587 (6)	0.38180 (9)	0.01366 (10)
C4	0.35654 (5)	0.72296 (6)	0.33967 (9)	0.01302 (10)
C5	0.32559 (5)	0.59285 (5)	0.34337 (8)	0.01084 (9)
N4	0.07181 (4)	0.08353 (5)	0.36523 (7)	0.01101 (8)
O1	0.03294 (4)	0.19166 (5)	0.37605 (8)	0.01831 (10)
O2	0.12811 (4)	0.03373 (5)	0.50656 (7)	0.01704 (9)
O3	0.05534 (4)	0.02013 (5)	0.21333 (7)	0.01419 (8)
N5	0.34927 (4)	0.17325 (5)	0.27032 (7)	0.01208 (9)
O4	0.41357 (4)	0.23657 (5)	0.38374 (8)	0.01818 (9)
O5	0.25728 (4)	0.21885 (5)	0.20404 (8)	0.01714 (9)
O6	0.37509 (4)	0.06465 (4)	0.21848 (7)	0.01541 (9)
H2	0.0849 (9)	0.6508 (11)	0.4677 (16)	0.015 (2)*
H3	0.3044 (10)	0.9065 (11)	0.3781 (17)	0.019 (3)*
H4	0.4245 (10)	0.7452 (11)	0.3072 (17)	0.018 (2)*
H1N1	0.1431 (11)	0.8483 (12)	0.4515 (19)	0.024 (3)*
H1N2	0.1923 (12)	0.3916 (14)	0.289 (2)	0.036 (3)*
H2N2	0.1064 (11)	0.4422 (13)	0.393 (2)	0.030 (3)*
H1N3	0.3832 (12)	0.4256 (15)	0.325 (2)	0.036 (4)*
H2N3	0.4547 (10)	0.5255 (11)	0.2771 (18)	0.022 (3)*
H3N2	0.2027 (10)	0.3986 (12)	0.4994 (17)	0.022 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0158 (2)	0.00975 (18)	0.01202 (19)	0.00126 (15)	0.00078 (15)	−0.00025 (14)
N2	0.01164 (19)	0.00934 (17)	0.01122 (19)	−0.00130 (14)	0.00219 (15)	−0.00007 (14)
N3	0.0131 (2)	0.0132 (2)	0.0209 (2)	0.00103 (16)	0.00640 (18)	0.00051 (17)
C1	0.01061 (19)	0.00874 (19)	0.00967 (19)	−0.00068 (14)	0.00112 (15)	0.00042 (15)
C2	0.0119 (2)	0.0106 (2)	0.0102 (2)	0.00047 (15)	0.00092 (16)	0.00022 (15)
C3	0.0177 (2)	0.0110 (2)	0.0120 (2)	−0.00248 (17)	0.00083 (18)	0.00069 (17)
C4	0.0137 (2)	0.0124 (2)	0.0130 (2)	−0.00291 (17)	0.00193 (17)	0.00085 (16)
C5	0.0109 (2)	0.0114 (2)	0.0102 (2)	−0.00046 (15)	0.00145 (16)	0.00062 (16)
N4	0.01104 (18)	0.01129 (18)	0.01079 (18)	0.00072 (14)	0.00182 (14)	−0.00057 (14)
O1	0.0205 (2)	0.01273 (19)	0.0212 (2)	0.00626 (15)	0.00077 (17)	−0.00324 (15)
O2	0.0227 (2)	0.0157 (2)	0.01131 (18)	0.00386 (16)	−0.00316 (16)	0.00055 (14)
O3	0.01560 (19)	0.01632 (19)	0.01055 (17)	0.00110 (14)	0.00129 (14)	−0.00395 (14)
N5	0.01301 (19)	0.01063 (18)	0.0129 (2)	−0.00098 (14)	0.00270 (15)	−0.00080 (14)
O4	0.0181 (2)	0.0161 (2)	0.0189 (2)	−0.00316 (15)	−0.00271 (16)	−0.00424 (16)
O5	0.01401 (19)	0.0165 (2)	0.0200 (2)	0.00356 (15)	−0.00103 (15)	−0.00464 (16)
O6	0.0170 (2)	0.00960 (17)	0.0202 (2)	0.00105 (13)	0.00446 (16)	−0.00208 (14)

Geometric parameters (Å, º) top

N1—C2	1.3442 (7)	C2—H2	0.910 (11)
N1—C3	1.3516 (8)	C3—C4	1.3615 (9)
N1—H1N1	0.873 (13)	C3—H3	0.978 (12)
N2—C1	1.4575 (7)	C4—C5	1.4205 (8)
N2—H1N2	0.934 (15)	C4—H4	0.926 (12)
N2—H2N2	0.881 (14)	N4—O1	1.2392 (7)
N2—H3N2	0.871 (13)	N4—O2	1.2603 (7)
N3—C5	1.3327 (8)	N4—O3	1.2664 (7)
N3—H1N3	0.844 (16)	N5—O4	1.2474 (7)
N3—H2N3	0.827 (13)	N5—O6	1.2534 (7)
C1—C2	1.3698 (8)	N5—O5	1.2623 (7)
C1—C5	1.4176 (8)

C2—N1—C3	121.45 (5)	C1—C2—H2	122.4 (7)
C2—N1—H1N1	120.3 (9)	N1—C3—C4	120.74 (5)
C3—N1—H1N1	118.3 (9)	N1—C3—H3	116.5 (7)
C1—N2—H1N2	111.9 (9)	C4—C3—H3	122.7 (7)
C1—N2—H2N2	107.7 (9)	C3—C4—C5	120.48 (5)
H1N2—N2—H2N2	108.1 (13)	C3—C4—H4	119.5 (7)
C1—N2—H3N2	111.5 (8)	C5—C4—H4	120.1 (7)
H1N2—N2—H3N2	111.5 (12)	N3—C5—C1	123.30 (5)
H2N2—N2—H3N2	105.8 (12)	N3—C5—C4	120.39 (5)
C5—N3—H1N3	120.6 (10)	C1—C5—C4	116.28 (5)
C5—N3—H2N3	116.5 (8)	O1—N4—O2	120.45 (5)
H1N3—N3—H2N3	118.9 (13)	O1—N4—O3	121.07 (5)
C2—C1—C5	120.77 (5)	O2—N4—O3	118.47 (5)
C2—C1—N2	118.22 (5)	O4—N5—O6	120.92 (5)
C5—C1—N2	120.99 (5)	O4—N5—O5	120.11 (5)
N1—C2—C1	120.29 (5)	O6—N5—O5	118.97 (5)
N1—C2—H2	117.3 (7)

C3—N1—C2—C1	−0.36 (9)	N2—C1—C5—N3	−0.09 (9)
C5—C1—C2—N1	0.63 (9)	C2—C1—C5—C4	−0.38 (8)
N2—C1—C2—N1	−177.64 (5)	N2—C1—C5—C4	177.85 (5)
C2—N1—C3—C4	−0.16 (9)	C3—C4—C5—N3	177.88 (6)
N1—C3—C4—C5	0.40 (9)	C3—C4—C5—C1	−0.13 (9)
C2—C1—C5—N3	−178.32 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.874 (13)	2.001 (13)	2.7750 (7)	147.0 (12)
N2—H1N2···O5	0.935 (14)	2.105 (15)	2.9070 (8)	143.1 (12)
N2—H1N2···O2ⁱⁱ	0.935 (14)	2.211 (14)	2.7767 (7)	118.1 (11)
N2—H2N2···O3ⁱⁱⁱ	0.881 (14)	2.193 (14)	3.0006 (7)	152.3 (12)
N2—H2N2···O3^iv	0.881 (14)	2.482 (14)	2.9231 (7)	111.6 (11)
N3—H1N3···O4	0.844 (16)	2.054 (16)	2.8653 (8)	161.0 (14)
N3—H2N3···O6^v	0.827 (12)	2.130 (12)	2.9442 (7)	168.0 (12)
N2—H3N2···O5^iv	0.871 (12)	1.963 (12)	2.8227 (8)	169.0 (12)
N2—H3N2···O6^iv	0.871 (12)	2.494 (12)	3.1217 (7)	129.5 (10)
C2—H2···O3ⁱⁱⁱ	0.910 (11)	2.439 (11)	3.0489 (8)	124.6 (9)
C2—H2···O1^vi	0.910 (11)	2.552 (11)	3.1834 (8)	127.0 (9)
C2—H2···O3^iv	0.910 (11)	2.570 (11)	3.1277 (8)	120.2 (9)
C3—H3···O6ⁱ	0.979 (12)	2.253 (12)	3.1170 (8)	146.6 (10)
C4—H4···O4^v	0.926 (12)	2.559 (12)	3.4274 (8)	156.3 (10)

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

Experimental details

Crystal data
Chemical formula	C₅H₉N₃²⁺·2NO³⁻
M_r	235.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.3008 (5), 10.5086 (5), 7.1411 (3)
β (°)	97.546 (1)
V (Å³)	915.09 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.65 × 0.37 × 0.28

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.906, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	18234, 4796, 4129
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.06
No. of reflections	4796
No. of parameters	181
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXTL 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	0.874 (13)	2.001 (13)	2.7750 (7)	147.0 (12)
N2—H1N2···O5	0.935 (14)	2.105 (15)	2.9070 (8)	143.1 (12)
N2—H1N2···O2ⁱⁱ	0.935 (14)	2.211 (14)	2.7767 (7)	118.1 (11)
N2—H2N2···O3ⁱⁱⁱ	0.881 (14)	2.193 (14)	3.0006 (7)	152.3 (12)
N2—H2N2···O3^iv	0.881 (14)	2.482 (14)	2.9231 (7)	111.6 (11)
N3—H1N3···O4	0.844 (16)	2.054 (16)	2.8653 (8)	161.0 (14)
N3—H2N3···O6^v	0.827 (12)	2.130 (12)	2.9442 (7)	168.0 (12)
N2—H3N2···O5^iv	0.871 (12)	1.963 (12)	2.8227 (8)	169.0 (12)
N2—H3N2···O6^iv	0.871 (12)	2.494 (12)	3.1217 (7)	129.5 (10)
C2—H2···O3ⁱⁱⁱ	0.910 (11)	2.439 (11)	3.0489 (8)	124.6 (9)
C2—H2···O1^vi	0.910 (11)	2.552 (11)	3.1834 (8)	127.0 (9)
C2—H2···O3^iv	0.910 (11)	2.570 (11)	3.1277 (8)	120.2 (9)
C3—H3···O6ⁱ	0.979 (12)	2.253 (12)	3.1170 (8)	146.6 (10)
C4—H4···O4^v	0.926 (12)	2.559 (12)	3.4274 (8)	156.3 (10)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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