2-Amino-5-chloro­pyridinium hydrogen succinate

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

doi:10.1107/S1600536810002990

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o464-o465

https://doi.org/10.1107/S1600536810002990

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2-Amino-5-chloropyridinium hydrogen succinate

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 19 January 2010; accepted 25 January 2010; online 30 January 2010)

In the title salt, C₅H₆ClN₂⁺·C₄H₅O₄⁻, the pyridine N atom is protonated. The pyridinium and amino groups associate via a pair of N—H⋯O hydrogen bonds to the carboxylate O atoms of the singly deprotonated succinate anion. The hydrogen succinate anions self-assemble via O—H⋯O hydrogen bonds into chains along the b axis. The crystal structure is further stabilized by additional N—H⋯O hydrogen bonds involving the second amino H atoms, as well as C—H⋯O contacts, forming a three-dimensional network.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ); Katritzky et al. (1996 ). For related structures, see: Pourayoubi et al. (2007 ); Akriche & Rzaigui (2005 ); Zaouali Zgolli et al. (2009 ). For the structure of succinic acid, see: Gopalan et al. (2000 ); Leviel et al. (1981 ). For applications of succinic acid, see: Sauer et al. (2008 ); Song & Lee (2006 ); Zeikus et al. (1999 )·For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ); Jeffrey (1997 ); Scheiner (1997 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₅H₆ClN₂⁺·C₄H₅O₄⁻
M_r = 246.65
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.2263 (1) Å
b = 13.5997 (3) Å
c = 14.9019 (3) Å
V = 1059.17 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 100 K
0.41 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.866, T_max = 0.965
11594 measured reflections
3934 independent reflections
3581 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.082
S = 1.02
3934 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1604 Friedel pairs
Flack parameter: 0.05 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2ⁱ	0.821 (19)	1.819 (19)	2.5891 (15)	156 (2)
N1—H1N1⋯O2ⁱⁱ	0.86 (2)	1.85 (2)	2.7023 (15)	172.4 (19)
N2—H1N2⋯O1ⁱⁱ	0.84 (2)	1.95 (2)	2.7814 (15)	177 (2)
N2—H2N2⋯O1	0.826 (19)	2.004 (19)	2.8002 (16)	162 (2)
C5—H5⋯O4ⁱⁱⁱ	0.964 (17)	2.391 (17)	3.2216 (18)	144.0 (13)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002990/tk2616sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002990/tk2616Isup2.hkl

checkCIF report

Comment top

Pyridine and its derivatives play an important role in heterocyclic chemistry (Pozharski et al., 1997; Katritzky et al., 1996). They are often involved in hydrogen-bonding interactions (Jeffrey & Saenger, 1991; Jeffrey, 1997; Scheiner, 1997). The dicarboxylic acid, succinic acid, is a precursor for many chemicals of industrial importance (Zeikus et al., 1999; Song & Lee, 2006). Succinic acid derivatives are mostly used in chemicals, food and pharmaceuticals (Sauer et al., 2008). The crystal structure of succinic acid has been reported (Gopalan et al., 2000; Leviel et al., 1981). The crystal structures of 2-amino-5-chloropyridine (Pourayoubi et al., 2007), 2-amino-5-chloropyridinium nitrate (Zaouali Zgolli et al., 2009) and bis (2-amino-5-chloropyridinium) dihydrogen diphosphate (Akriche & Rzaigui, 2005) have been reported in literature. In this paper, we present the X-ray single-crystal structure of 2-amino-5-chloropyridinium hydrogen succinate, (I).

The asymmetric unit of (I), Fig. 1, contains a 2-amino-5-chloropyridinium cation and a hydrogen succinate anion, indicating that proton transfer has occurred during the co-crystallisation experiment. In the 2-amino-5-chloropyridinium cation, a wider than normal angle (123.22 (12)°) is subtended at the protonated N1 atom.

In the crystal packing (Fig. 2), the protonated N1 atom and the 2-amino group is hydrogen-bonded to the carboxylate oxygen atoms (O1 and O2) via a pair of N–H···O hydrogen bonds forming a R₂²(8) ring motif (Bernstein et al. 1995). The hydrogen succinate anions self-assemble via O—H···O hydrogen bonds. The second amino-H atom forms a hydrogen bond with the carboxylate-O1 atom. Furthermore, the crystal structure is stabilized by C—H···O contacts, Table 1, forming a 3D-network.

Related literature top

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For related structures, see: Pourayoubi et al. (2007); Akriche & Rzaigui (2005); Zaouali Zgolli et al. (2009). For the structure of succinic acid, see: Gopalan et al. (2000); Leviel et al. (1981). For applications of succinic acid, see: Sauer et al. (2008); Song & Lee (2006); Zeikus et al. (1999).For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A hot methanolic solution (10 ml) of 2-amino-5-chloropyridine (32 mg, Aldrich) and a hot aqueous solution (10 ml) of succinic acid (29 mg, Merck) were mixed and warmed over a water bath for 10 minutes. The resulting solution was allowed to cool slowly at room temperature. Single crystals of (I) appeared from the mother liquor after a few days.

Structure description top

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For related structures, see: Pourayoubi et al. (2007); Akriche & Rzaigui (2005); Zaouali Zgolli et al. (2009). For the structure of succinic acid, see: Gopalan et al. (2000); Leviel et al. (1981). For applications of succinic acid, see: Sauer et al. (2008); Song & Lee (2006); Zeikus et al. (1999).For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 asymmetric unit of (I) showing atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), showing intermolecular interactions as dashed lines.

2-Amino-5-chloropyridinium hydrogen succinate top

Crystal data top

C₅H₆ClN₂⁺·C₄H₅O₄⁻	F(000) = 512
M_r = 246.65	D_x = 1.547 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3633 reflections
a = 5.2263 (1) Å	θ = 2.7–33.2°
b = 13.5997 (3) Å	µ = 0.36 mm⁻¹
c = 14.9019 (3) Å	T = 100 K
V = 1059.17 (4) Å³	Blcok, yellow
Z = 4	0.41 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3934 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 33.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→6
T_min = 0.866, T_max = 0.965	k = −17→20
11594 measured reflections	l = −21→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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0404P)² + 0.0588P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3934 reflections	Δρ_max = 0.33 e Å⁻³
189 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1604 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (5)

Crystal data top

C₅H₆ClN₂⁺·C₄H₅O₄⁻	V = 1059.17 (4) Å³
M_r = 246.65	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.2263 (1) Å	µ = 0.36 mm⁻¹
b = 13.5997 (3) Å	T = 100 K
c = 14.9019 (3) Å	0.41 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3934 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3581 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.965	R_int = 0.033
11594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	Δρ_max = 0.33 e Å⁻³
S = 1.02	Δρ_min = −0.27 e Å⁻³
3934 reflections	Absolute structure: Flack (1983), 1604 Friedel pairs
189 parameters	Absolute structure parameter: 0.05 (5)
0 restraints

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 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
Cl1	−0.16471 (6)	0.66417 (3)	0.01385 (3)	0.02344 (8)
N1	0.3976 (2)	0.47974 (9)	−0.04334 (8)	0.0152 (2)
N2	0.5510 (2)	0.33552 (9)	0.01762 (9)	0.0194 (2)
C1	0.3838 (2)	0.40861 (10)	0.02044 (9)	0.0152 (2)
C2	0.1897 (3)	0.41668 (10)	0.08661 (9)	0.0170 (2)
C3	0.0245 (3)	0.49419 (11)	0.08409 (10)	0.0183 (3)
C4	0.0469 (2)	0.56603 (10)	0.01630 (10)	0.0180 (2)
C5	0.2340 (3)	0.55775 (10)	−0.04688 (10)	0.0168 (2)
O1	0.42571 (19)	0.16607 (8)	0.11491 (6)	0.0208 (2)
O2	0.24386 (19)	0.03548 (7)	0.17729 (7)	0.0184 (2)
O3	0.8289 (2)	0.36179 (8)	0.25630 (8)	0.0232 (2)
O4	0.4478 (2)	0.29887 (8)	0.29328 (8)	0.0277 (3)
C6	0.4118 (2)	0.10302 (9)	0.17571 (9)	0.0142 (2)
C7	0.6061 (3)	0.10441 (10)	0.25145 (10)	0.0179 (3)
C8	0.7907 (2)	0.19017 (10)	0.24860 (10)	0.0181 (3)
C9	0.6663 (3)	0.28792 (10)	0.26836 (8)	0.0158 (2)
H2	0.180 (3)	0.3686 (13)	0.1322 (11)	0.020 (4)*
H3	−0.110 (3)	0.4991 (12)	0.1279 (11)	0.020 (4)*
H5	0.262 (3)	0.6021 (12)	−0.0964 (12)	0.016 (4)*
H7A	0.713 (4)	0.0395 (14)	0.2466 (13)	0.029 (5)*
H7B	0.504 (4)	0.1041 (13)	0.3078 (13)	0.033 (5)*
H8A	0.925 (4)	0.1818 (13)	0.2917 (12)	0.026 (5)*
H8B	0.883 (4)	0.1978 (13)	0.1893 (12)	0.023 (5)*
H1O3	0.764 (4)	0.4144 (14)	0.2709 (13)	0.026 (5)*
H1N1	0.517 (4)	0.4729 (13)	−0.0823 (13)	0.026 (5)*
H1N2	0.667 (4)	0.3364 (14)	−0.0209 (13)	0.029 (5)*
H2N2	0.538 (4)	0.2904 (14)	0.0544 (13)	0.027 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01978 (14)	0.01782 (15)	0.03271 (18)	0.00423 (12)	0.00071 (13)	−0.00177 (14)
N1	0.0162 (5)	0.0134 (5)	0.0162 (5)	−0.0010 (4)	0.0012 (4)	0.0015 (4)
N2	0.0200 (5)	0.0154 (5)	0.0227 (6)	0.0009 (5)	0.0046 (5)	0.0071 (5)
C1	0.0156 (5)	0.0133 (5)	0.0168 (6)	−0.0035 (4)	−0.0024 (4)	0.0009 (5)
C2	0.0188 (6)	0.0168 (6)	0.0154 (6)	−0.0038 (5)	0.0007 (5)	0.0013 (5)
C3	0.0177 (6)	0.0193 (6)	0.0180 (6)	−0.0033 (5)	0.0013 (5)	−0.0030 (5)
C4	0.0176 (5)	0.0154 (6)	0.0209 (6)	0.0001 (5)	−0.0026 (5)	−0.0021 (5)
C5	0.0175 (5)	0.0124 (6)	0.0205 (7)	−0.0014 (5)	−0.0030 (5)	0.0008 (5)
O1	0.0257 (5)	0.0174 (5)	0.0194 (5)	−0.0048 (4)	−0.0037 (4)	0.0068 (4)
O2	0.0197 (4)	0.0132 (4)	0.0222 (5)	−0.0027 (4)	−0.0035 (4)	0.0039 (4)
O3	0.0242 (5)	0.0129 (5)	0.0326 (6)	−0.0011 (4)	0.0082 (5)	−0.0048 (4)
O4	0.0192 (5)	0.0251 (6)	0.0387 (6)	−0.0001 (4)	0.0062 (4)	−0.0112 (5)
C6	0.0153 (5)	0.0118 (5)	0.0154 (6)	0.0024 (4)	0.0000 (4)	−0.0013 (5)
C7	0.0226 (6)	0.0140 (6)	0.0169 (6)	−0.0011 (5)	−0.0027 (5)	0.0027 (5)
C8	0.0169 (6)	0.0156 (6)	0.0218 (7)	0.0014 (5)	−0.0023 (5)	−0.0016 (5)
C9	0.0184 (5)	0.0153 (6)	0.0138 (6)	0.0011 (5)	−0.0014 (5)	−0.0017 (5)

Geometric parameters (Å, º) top

Cl1—C4	1.7336 (13)	C5—H5	0.965 (17)
N1—C1	1.3580 (17)	O1—C6	1.2496 (16)
N1—C5	1.3636 (18)	O2—C6	1.2708 (16)
N1—H1N1	0.86 (2)	O3—C9	1.3281 (17)
N2—C1	1.3242 (17)	O3—H1O3	0.822 (19)
N2—H1N2	0.83 (2)	O4—C9	1.2100 (17)
N2—H2N2	0.83 (2)	C6—C7	1.5183 (19)
C1—C2	1.4189 (18)	C7—C8	1.5141 (19)
C2—C3	1.363 (2)	C7—H7A	1.047 (19)
C2—H2	0.944 (18)	C7—H7B	0.99 (2)
C3—C4	1.410 (2)	C8—C9	1.5090 (19)
C3—H3	0.961 (17)	C8—H8A	0.959 (19)
C4—C5	1.362 (2)	C8—H8B	1.010 (18)

C1—N1—C5	123.22 (12)	N1—C5—H5	115.0 (10)
C1—N1—H1N1	115.7 (12)	C9—O3—H1O3	110.9 (14)
C5—N1—H1N1	121.0 (12)	O1—C6—O2	123.33 (12)
C1—N2—H1N2	119.3 (14)	O1—C6—C7	119.44 (11)
C1—N2—H2N2	118.7 (13)	O2—C6—C7	117.21 (11)
H1N2—N2—H2N2	122.0 (19)	C8—C7—C6	114.51 (11)
N2—C1—N1	118.52 (12)	C8—C7—H7A	107.9 (10)
N2—C1—C2	123.49 (12)	C6—C7—H7A	107.2 (10)
N1—C1—C2	117.99 (12)	C8—C7—H7B	111.6 (11)
C3—C2—C1	119.57 (13)	C6—C7—H7B	105.6 (12)
C3—C2—H2	121.4 (11)	H7A—C7—H7B	109.9 (15)
C1—C2—H2	119.0 (11)	C9—C8—C7	113.48 (11)
C2—C3—C4	120.21 (13)	C9—C8—H8A	106.9 (11)
C2—C3—H3	119.8 (10)	C7—C8—H8A	110.9 (11)
C4—C3—H3	119.9 (10)	C9—C8—H8B	106.5 (10)
C5—C4—C3	119.81 (12)	C7—C8—H8B	114.0 (10)
C5—C4—Cl1	120.47 (11)	H8A—C8—H8B	104.4 (14)
C3—C4—Cl1	119.71 (11)	O4—C9—O3	123.52 (13)
C4—C5—N1	119.20 (13)	O4—C9—C8	125.11 (13)
C4—C5—H5	125.8 (10)	O3—C9—C8	111.36 (12)

C5—N1—C1—N2	179.59 (12)	Cl1—C4—C5—N1	−179.96 (10)
C5—N1—C1—C2	−0.30 (18)	C1—N1—C5—C4	0.21 (19)
N2—C1—C2—C3	−179.60 (13)	O1—C6—C7—C8	4.56 (19)
N1—C1—C2—C3	0.29 (18)	O2—C6—C7—C8	−176.50 (12)
C1—C2—C3—C4	−0.2 (2)	C6—C7—C8—C9	69.12 (16)
C2—C3—C4—C5	0.1 (2)	C7—C8—C9—O4	7.3 (2)
C2—C3—C4—Cl1	179.95 (11)	C7—C8—C9—O3	−173.70 (12)
C3—C4—C5—N1	−0.10 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2ⁱ	0.821 (19)	1.819 (19)	2.5891 (15)	156 (2)
N1—H1N1···O2ⁱⁱ	0.86 (2)	1.85 (2)	2.7023 (15)	172.4 (19)
N2—H1N2···O1ⁱⁱ	0.84 (2)	1.95 (2)	2.7814 (15)	177 (2)
N2—H2N2···O1	0.826 (19)	2.004 (19)	2.8002 (16)	162 (2)
C5—H5···O4ⁱⁱⁱ	0.964 (17)	2.391 (17)	3.2216 (18)	144.0 (13)

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

Experimental details

Crystal data
Chemical formula	C₅H₆ClN₂⁺·C₄H₅O₄⁻
M_r	246.65
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.2263 (1), 13.5997 (3), 14.9019 (3)
V (Å³)	1059.17 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.41 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.866, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	11594, 3934, 3581
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.771

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.082, 1.02
No. of reflections	3934
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27
Absolute structure	Flack (1983), 1604 Friedel pairs
Absolute structure parameter	0.05 (5)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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
O3—H1O3···O2ⁱ	0.821 (19)	1.819 (19)	2.5891 (15)	156 (2)
N1—H1N1···O2ⁱⁱ	0.86 (2)	1.85 (2)	2.7023 (15)	172.4 (19)
N2—H1N2···O1ⁱⁱ	0.84 (2)	1.95 (2)	2.7814 (15)	177 (2)
N2—H2N2···O1	0.826 (19)	2.004 (19)	2.8002 (16)	162 (2)
C5—H5···O4ⁱⁱⁱ	0.964 (17)	2.391 (17)	3.2216 (18)	144.0 (13)

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

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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