2,3-Diamino­pyridinium 6-carb­oxy­pyridine-2-carboxyl­ate

Foroughian, M.; Foroumadi, A.; Notash, B.; Bruno, G.; Amiri Rudbari, H.; Aghabozorg, H.

doi:10.1107/S1600536811047647

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3325

https://doi.org/10.1107/S1600536811047647

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2,3-Diaminopyridinium 6-carboxypyridine-2-carboxylate

Mahsa Foroughian,^a Alireza Foroumadi,^b ^* Behrouz Notash,^c Giuseppe Bruno,^d Hadi Amiri Rudbari ^d and Hossein Aghabozorg ^a

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDrug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran, ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran, and ^dDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina, 98166 Messina, Italy
^*Correspondence e-mail: aforoumadi@yahoo.com

(Received 4 November 2011; accepted 10 November 2011; online 16 November 2011)

The asymmetric unit of the title proton-transfer compound, C₅H₈N₃⁺·C₇H₄NO₄⁻, consists of one mono-deprotonated pyridine-2,6-dicarboxylic acid as anion and one protonated 2,3-diaminopyridine as cation. The crystal packing shows extensive O—H⋯O, N—H⋯O and N—H⋯N hydrogen bonds. Thre are also several π–π interactions between the anions and also between the cations [centriod–centroid distances = 3.6634 (7), 3.7269 (7), 3.6705 (7) and 3.4164 (7) Å].

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008b ). For related structures, see: Aghabozorg et al. (2008a , 2011a ,b ); Sharif et al. (2010 ).

Experimental

Crystal data

C₅H₈N₃⁺·C₇H₄NO₄⁻
M_r = 276.26
Triclinic, $[P \overline 1]$
a = 6.9138 (1) Å
b = 8.3364 (2) Å
c = 11.2358 (2) Å
α = 81.448 (1)°
β = 73.831 (1)°
γ = 82.486 (1)°
V = 612.33 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.706, T_max = 0.746
34839 measured reflections
2654 independent reflections
2348 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.107
S = 1.07
2654 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H⋯O1ⁱ	0.86	1.94	2.7872 (12)	167
N2—H2B⋯O3ⁱⁱ	0.87 (2)	2.329 (19)	3.1108 (14)	150.0 (15)
N3—H3A⋯O2ⁱ	0.86	2.03	2.8674 (14)	163
N3—H3B⋯O2	0.86	2.17	2.9427 (14)	149
O4—H1⋯O1ⁱⁱⁱ	0.89 (2)	1.75 (2)	2.5673 (12)	151.9 (18)
N2—H2A⋯O2	0.868 (19)	2.32 (2)	3.1290 (15)	156.0 (16)
N2—H2A⋯N1	0.868 (19)	2.491 (18)	3.0999 (14)	127.8 (15)
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047647/bt5705sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047647/bt5705Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047647/bt5705Isup3.cml

checkCIF report

Comment top

Pyridinedicarboxylic acids are present in many natural products, such as vitamins, coenzymes, and alkaloids. Pyridine-2,6-dicarboxylic acid has been used to synthesize several proton transfer compounds in which pyridine-2,6-dicarboxylic acid acts as a monoacidic fragment (Aghabozorg et al. 2008b).In this regards, several organic bases were used such as propane-1,2-diamine (Aghabozorg et al. 2008a), N¹,N¹-dimethylpropane-1,2-diamine (Aghabozorg et al. 2011a), 2-amino-4-methylpyridinie (Sharif et al. 2010) and 2-amino-4-methylpyridine (Aghabozorg et al., 2011b).

The structure of the title compounds contains one deprotonated pyridine-2,6-dicarboxylic acid as anion and one protonated 2,3-diaminopyridine as cation (Fig.1). The cations and anions are linked by several O—H···O, N—H···O and N—H···N hydrogen bonds with D···A distances ranging from 2.5673 (12) Å to 3.1290 (15) Å (Table.1 & Fig. 2). Furthermore, there are several π-π interactions which formed between (py-2,6-dcH)^- anions and also between (dapyH)⁺ cations with centriod-to-centroid distances = 3.6634 (7), 3.7269 (7), 3.6705 (7), 3.4164 (7) Å (Fig. 3). These hydrogen bonds and π-π interactions play important role in the stabilization of crystal packing.

Related literature top

For background to proton-transfer compounds, see: Aghabozorg et al. (2008b). For related structures, see: Aghabozorg et al. (2008a, 2011a,b); Sharif et al. (2010).

Experimental top

The solution of pyridine-2,6-dicarboxylic acid (0.334 g, 2 mmol) in 7 ml water was added to solution of 2,3-diaminopyridine (0.218 g, 2 mmol) in 4 ml water in 1:1 molar ratios. The reaction mixture was stirred for 3hrs at room temprature. The colorless crystals of the title compound appeared after slow evaporation of solvent at room temperature.

Structure description top

For background to proton-transfer compounds, see: Aghabozorg et al. (2008b). For related structures, see: Aghabozorg et al. (2008a, 2011a,b); Sharif et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. The packing diagram of the title compound showing hydrogen bonding interactions as blue dashed lines.
	Fig. 3. The packing diagram of the title compound showing π-π interactions between (py-2,6-dcH)^- anions and between (dapyH)⁺ cations.

2,3-Diaminopyridinium 6-carboxypyridine-2-carboxylate top

Crystal data top

C₅H₈N₃⁺·C₇H₄NO₄⁻	Z = 2
M_r = 276.26	F(000) = 288
Triclinic, P1	D_x = 1.498 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9138 (1) Å	Cell parameters from 9842 reflections
b = 8.3364 (2) Å	θ = 2.9–30.0°
c = 11.2358 (2) Å	µ = 0.12 mm⁻¹
α = 81.448 (1)°	T = 296 K
β = 73.831 (1)°	Irregular, colorless
γ = 82.486 (1)°	0.24 × 0.20 × 0.12 mm
V = 612.33 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	2654 independent reflections
Radiation source: fine-focus sealed tube	2348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
T_min = 0.706, T_max = 0.746	k = −10→10
34839 measured reflections	l = −14→14

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.060P)² + 0.1194P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2654 reflections	Δρ_max = 0.30 e Å⁻³
194 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00070 (17)

Crystal data top

C₅H₈N₃⁺·C₇H₄NO₄⁻	γ = 82.486 (1)°
M_r = 276.26	V = 612.33 (2) Å³
Triclinic, P1	Z = 2
a = 6.9138 (1) Å	Mo Kα radiation
b = 8.3364 (2) Å	µ = 0.12 mm⁻¹
c = 11.2358 (2) Å	T = 296 K
α = 81.448 (1)°	0.24 × 0.20 × 0.12 mm
β = 73.831 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2654 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2348 reflections with I > 2σ(I)
T_min = 0.706, T_max = 0.746	R_int = 0.025
34839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.30 e Å⁻³
2654 reflections	Δρ_min = −0.17 e Å⁻³
194 parameters

Special details top

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
O3	0.64901 (16)	0.46889 (11)	0.60916 (9)	0.0508 (3)
O2	0.91253 (17)	−0.01029 (10)	0.21751 (8)	0.0479 (3)
O1	0.91229 (15)	−0.25266 (10)	0.32864 (8)	0.0419 (2)
O4	0.83898 (16)	0.45238 (11)	0.41533 (8)	0.0480 (3)
C8	0.72493 (16)	0.42375 (14)	0.08478 (10)	0.0310 (2)
N4	0.85753 (15)	0.42597 (12)	−0.13478 (9)	0.0352 (2)
H	0.9115	0.3742	−0.1986	0.042*
N1	0.79718 (13)	0.13922 (10)	0.42873 (8)	0.0271 (2)
C9	0.81096 (17)	0.33895 (14)	−0.02186 (10)	0.0314 (2)
C10	0.8247 (2)	0.59072 (16)	−0.15453 (11)	0.0400 (3)
H10	0.8605	0.6451	−0.2349	0.048*
N3	0.84405 (18)	0.17690 (13)	−0.01308 (10)	0.0451 (3)
H3A	0.8947	0.1294	−0.0793	0.054*
H3B	0.8148	0.1199	0.0588	0.054*
C11	0.7393 (2)	0.67446 (15)	−0.05574 (12)	0.0417 (3)
H11	0.7130	0.7872	−0.0675	0.050*
C12	0.69064 (19)	0.58993 (15)	0.06456 (11)	0.0379 (3)
H12	0.6336	0.6481	0.1324	0.045*
C7	0.73268 (17)	0.39063 (13)	0.52423 (10)	0.0319 (3)
C6	0.72505 (16)	0.20977 (13)	0.53341 (10)	0.0276 (2)
C2	0.79375 (15)	−0.02216 (12)	0.43816 (9)	0.0262 (2)
C1	0.87808 (17)	−0.10003 (13)	0.31804 (10)	0.0299 (2)
C3	0.71865 (17)	−0.11635 (13)	0.55079 (10)	0.0307 (2)
H3	0.7201	−0.2286	0.5541	0.037*
C4	0.64189 (18)	−0.04065 (14)	0.65777 (11)	0.0350 (3)
H4	0.5889	−0.1007	0.7340	0.042*
C5	0.64532 (18)	0.12568 (14)	0.64934 (10)	0.0332 (3)
H5	0.5953	0.1802	0.7197	0.040*
N2	0.67215 (18)	0.33369 (15)	0.20004 (10)	0.0402 (3)
H2A	0.755 (3)	0.253 (2)	0.2184 (16)	0.057 (5)*
H2B	0.625 (3)	0.397 (2)	0.2583 (17)	0.057 (5)*
H1	0.840 (3)	0.560 (2)	0.4101 (17)	0.067 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0713 (7)	0.0303 (5)	0.0412 (5)	−0.0035 (4)	0.0066 (4)	−0.0163 (4)
O2	0.0818 (7)	0.0281 (4)	0.0250 (4)	0.0055 (4)	−0.0045 (4)	−0.0033 (3)
O1	0.0636 (6)	0.0200 (4)	0.0345 (5)	−0.0030 (4)	0.0009 (4)	−0.0068 (3)
O4	0.0736 (7)	0.0227 (4)	0.0374 (5)	−0.0120 (4)	0.0082 (4)	−0.0080 (3)
C8	0.0314 (5)	0.0338 (6)	0.0267 (5)	−0.0006 (4)	−0.0060 (4)	−0.0059 (4)
N4	0.0408 (5)	0.0369 (5)	0.0247 (5)	0.0027 (4)	−0.0051 (4)	−0.0064 (4)
N1	0.0332 (5)	0.0206 (4)	0.0257 (4)	−0.0017 (3)	−0.0049 (3)	−0.0040 (3)
C9	0.0327 (5)	0.0319 (6)	0.0285 (5)	0.0003 (4)	−0.0071 (4)	−0.0054 (4)
C10	0.0457 (7)	0.0385 (6)	0.0311 (6)	0.0024 (5)	−0.0092 (5)	0.0028 (5)
N3	0.0653 (7)	0.0318 (5)	0.0317 (5)	0.0031 (5)	−0.0038 (5)	−0.0069 (4)
C11	0.0500 (7)	0.0299 (6)	0.0420 (7)	0.0053 (5)	−0.0121 (5)	−0.0025 (5)
C12	0.0430 (6)	0.0356 (6)	0.0331 (6)	0.0044 (5)	−0.0069 (5)	−0.0110 (5)
C7	0.0378 (6)	0.0252 (5)	0.0312 (5)	−0.0023 (4)	−0.0046 (4)	−0.0076 (4)
C6	0.0303 (5)	0.0233 (5)	0.0283 (5)	−0.0015 (4)	−0.0050 (4)	−0.0058 (4)
C2	0.0303 (5)	0.0211 (5)	0.0267 (5)	−0.0005 (4)	−0.0072 (4)	−0.0035 (4)
C1	0.0384 (6)	0.0220 (5)	0.0280 (5)	−0.0016 (4)	−0.0064 (4)	−0.0046 (4)
C3	0.0384 (6)	0.0209 (5)	0.0309 (5)	−0.0033 (4)	−0.0073 (4)	−0.0008 (4)
C4	0.0421 (6)	0.0314 (6)	0.0269 (5)	−0.0057 (5)	−0.0030 (4)	0.0011 (4)
C5	0.0395 (6)	0.0313 (6)	0.0257 (5)	−0.0022 (4)	−0.0017 (4)	−0.0077 (4)
N2	0.0489 (6)	0.0394 (6)	0.0263 (5)	0.0006 (5)	−0.0022 (4)	−0.0043 (4)

Geometric parameters (Å, º) top

O3—C7	1.2041 (14)	N3—H3A	0.8600
O2—C1	1.2401 (14)	N3—H3B	0.8600
O1—C1	1.2574 (13)	C11—C12	1.4008 (18)
O4—C7	1.3088 (14)	C11—H11	0.9300
O4—H1	0.89 (2)	C12—H12	0.9300
C8—C12	1.3702 (17)	C7—C6	1.5028 (15)
C8—N2	1.3760 (15)	C6—C5	1.3862 (15)
C8—C9	1.4262 (15)	C2—C3	1.3903 (14)
N4—C9	1.3414 (14)	C2—C1	1.5185 (14)
N4—C10	1.3575 (16)	C3—C4	1.3811 (16)
N4—H	0.8600	C3—H3	0.9300
N1—C6	1.3343 (14)	C4—C5	1.3786 (16)
N1—C2	1.3365 (13)	C4—H4	0.9300
C9—N3	1.3338 (15)	C5—H5	0.9300
C10—C11	1.3512 (18)	N2—H2A	0.868 (19)
C10—H10	0.9300	N2—H2B	0.87 (2)

C7—O4—H1	112.4 (12)	O3—C7—C6	122.78 (10)
C12—C8—N2	124.24 (10)	O4—C7—C6	112.99 (9)
C12—C8—C9	117.42 (10)	N1—C6—C5	123.76 (10)
N2—C8—C9	118.25 (10)	N1—C6—C7	117.67 (9)
C9—N4—C10	124.00 (10)	C5—C6—C7	118.57 (10)
C9—N4—H	118.0	N1—C2—C3	122.83 (9)
C10—N4—H	118.0	N1—C2—C1	116.38 (9)
C6—N1—C2	117.28 (9)	C3—C2—C1	120.79 (9)
N3—C9—N4	119.21 (10)	O2—C1—O1	124.63 (10)
N3—C9—C8	122.31 (10)	O2—C1—C2	118.57 (9)
N4—C9—C8	118.47 (10)	O1—C1—C2	116.78 (9)
C11—C10—N4	119.02 (11)	C4—C3—C2	118.99 (10)
C11—C10—H10	120.5	C4—C3—H3	120.5
N4—C10—H10	120.5	C2—C3—H3	120.5
C9—N3—H3A	120.0	C5—C4—C3	118.73 (10)
C9—N3—H3B	120.0	C5—C4—H4	120.6
H3A—N3—H3B	120.0	C3—C4—H4	120.6
C10—C11—C12	119.37 (11)	C4—C5—C6	118.40 (10)
C10—C11—H11	120.3	C4—C5—H5	120.8
C12—C11—H11	120.3	C6—C5—H5	120.8
C8—C12—C11	121.69 (11)	C8—N2—H2A	118.7 (12)
C8—C12—H12	119.2	C8—N2—H2B	110.6 (12)
C11—C12—H12	119.2	H2A—N2—H2B	113.8 (16)
O3—C7—O4	124.23 (10)

C10—N4—C9—N3	178.04 (12)	O3—C7—C6—C5	−10.12 (18)
C10—N4—C9—C8	−1.15 (17)	O4—C7—C6—C5	169.81 (11)
C12—C8—C9—N3	−177.65 (11)	C6—N1—C2—C3	0.21 (16)
N2—C8—C9—N3	−0.97 (17)	C6—N1—C2—C1	−179.54 (9)
C12—C8—C9—N4	1.52 (16)	N1—C2—C1—O2	−11.91 (15)
N2—C8—C9—N4	178.20 (10)	C3—C2—C1—O2	168.34 (11)
C9—N4—C10—C11	−0.31 (19)	N1—C2—C1—O1	166.52 (10)
N4—C10—C11—C12	1.3 (2)	C3—C2—C1—O1	−13.22 (16)
N2—C8—C12—C11	−176.99 (12)	N1—C2—C3—C4	0.76 (17)
C9—C8—C12—C11	−0.54 (18)	C1—C2—C3—C4	−179.51 (10)
C10—C11—C12—C8	−0.9 (2)	C2—C3—C4—C5	−0.98 (17)
C2—N1—C6—C5	−0.96 (16)	C3—C4—C5—C6	0.29 (18)
C2—N1—C6—C7	178.62 (9)	N1—C6—C5—C4	0.71 (18)
O3—C7—C6—N1	170.28 (12)	C7—C6—C5—C4	−178.86 (10)
O4—C7—C6—N1	−9.79 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H···O1ⁱ	0.86	1.94	2.7872 (12)	167
N2—H2B···O3ⁱⁱ	0.87 (2)	2.329 (19)	3.1108 (14)	150.0 (15)
N3—H3A···O2ⁱ	0.86	2.03	2.8674 (14)	163
N3—H3B···O2	0.86	2.17	2.9427 (14)	149
O4—H1···O1ⁱⁱⁱ	0.89 (2)	1.75 (2)	2.5673 (12)	151.9 (18)
N2—H2A···O2	0.868 (19)	2.32 (2)	3.1290 (15)	156.0 (16)
N2—H2A···N1	0.868 (19)	2.491 (18)	3.0999 (14)	127.8 (15)

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

Experimental details

Crystal data
Chemical formula	C₅H₈N₃⁺·C₇H₄NO₄⁻
M_r	276.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9138 (1), 8.3364 (2), 11.2358 (2)
α, β, γ (°)	81.448 (1), 73.831 (1), 82.486 (1)
V (Å³)	612.33 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.706, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	34839, 2654, 2348
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.107, 1.07
No. of reflections	2654
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H···O1ⁱ	0.86	1.94	2.7872 (12)	166.9
N2—H2B···O3ⁱⁱ	0.87 (2)	2.329 (19)	3.1108 (14)	150.0 (15)
N3—H3A···O2ⁱ	0.8600	2.0300	2.8674 (14)	163.00
N3—H3B···O2	0.8600	2.1700	2.9427 (14)	149.00
O4—H1···O1ⁱⁱⁱ	0.89 (2)	1.75 (2)	2.5673 (12)	151.9 (18)
N2—H2A···O2	0.868 (19)	2.32 (2)	3.1290 (15)	156.0 (16)
N2—H2A···N1	0.868 (19)	2.491 (18)	3.0999 (14)	127.8 (15)

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

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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