catena-Poly[[[bis­(1H-imidazole-κN3)zinc(II)]-μ2-imidazol-1-ido-κ2N:N′] nitrate]

Govindhan, E.; Ganeshraja, A.S.; Bhavana, B.; Anbalagan, K.; SubbiahPandi, A.

doi:10.1107/S1600536814015232

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages m298-m299

doi:10.1107/S1600536814015232

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catena-Poly[[[bis(1H-imidazole-κN³)zinc(II)]-μ₂-imidazol-1-ido-κ²N:N′] nitrate]

Elumalai Govindhan,^a A. S. Ganeshraja,^b B. Bhavana,^b Krishnamoorthy Anbalagan ^b and Arunachalam SubbiahPandi ^c,^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, ^bDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_sp59@yahoo.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 April 2014; accepted 28 June 2014; online 11 July 2014)

The title compound, {[Zn(C₃H₃N₂)(C₃H₄N₂)₂]NO₃}_n, is a one-dimensional coordination polymer along [01-1] with the Zn^II atom coordinating to four imidazole/imidazolide rings. The Zn^II atom has a regular tetrahedral geometry with the planes of the two monodentate imidazole rings inclined to one another by 87.94 (17)°, while the planes of the bridging imidazolide rings are inclined to one another by 39.06 (17)°. In the crystal, the chains are linked via bifurcated N—H⋯(O,O) hydrogen bonds, forming sheets parallel to (001). These two-dimensional networks are linked via C—H⋯O hydrogen bonds and a C—H⋯π interaction, forming a three-dimensional structure.

Keywords: crystal structure.

CCDC reference: 1011008

Related literature

For imidazole systems in biological systems, see: Brooks & Davidson, (1960 ). For the crystal structure of a similar compound, see: Fu et al. (2007 ). For the synthesis of the title compound, see: Anbalagan & Lydia (2011 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[Zn(C₃H₃N₂)(C₃H₄N₂)₂]NO₃
M_r = 330.62
Monoclinic, P 2₁ /c
a = 12.1812 (10) Å
b = 10.0713 (7) Å
c = 11.3628 (10) Å
β = 91.011 (8)°
V = 1393.78 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.78 mm⁻¹
T = 293 K
0.45 × 0.35 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.478, T_max = 0.536
7564 measured reflections
3132 independent reflections
2419 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.083
S = 1.03
3132 reflections
188 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N6	1.9871 (18)
Zn1—N1	1.990 (2)
Zn1—N3	1.994 (2)
Zn1—N5	1.9954 (19)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.92 (3)	1.92 (3)	2.809 (3)	162 (3)
N4—H4N⋯O1ⁱⁱ	0.87 (2)	1.99 (3)	2.826 (3)	161 (3)
N4—H4N⋯O3ⁱⁱ	0.87 (2)	2.52 (3)	3.074 (3)	122 (2)
C2—H2⋯O3ⁱⁱⁱ	0.93	2.37	3.289 (4)	172
C4—H4⋯O3	0.93	2.55	3.283 (4)	135
C7—H7⋯Cg1^iv	0.93	2.88	3.587 (4)	133
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009).

Supporting information

CCDC reference: 1011008

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015232/su2723sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015232/su2723Isup2.hkl

checkCIF report

Comment top

Imidazoles are of considerable interest as ligands in many biological systems as they provide potential binding sites for metal ions (Brooks & Davidson, 1960). Against this background and to ascertain the molecular structure and conformation of the title compound, the crystal structure determination has been carried out.

The molecular structure of the title compound is shown in Fig. 1. Atom Zn1 has a regular tetrahedral geometry and the bond lengths (Allen et al., 1987) and angles are normal. It is a one-dimensional zigzag polymer with atom Zn1 coordinating to four imidazole units. This structure is similar to that observed for the compound catena-(bis(µ2-Imidazole)-tetrakis(1H-imidazole)-di-Zn^II 4,4'-bis(2-sulfonatostyryl)biphenyl) [Fu et al., 2007]. Two of the imidazole units are related by a two-fold screw axis and bridge the zinc atoms. The Zn-N bond distances vary from 1.9871 (18) to 1.9954 (19) Å, while the N-Zn-N bond angles vary from 105.86 (2) to 112.65 (8) °. The two monodentate coordinated imidazole rings [N1/N2/C1-C3 and N3/N4/C4-C6] are inclined to one another by 87.94 (17) °, while the bridging imidazole rings [N5/N6ⁱ/C9/C7ⁱ/C8ⁱ and N5ⁱⁱ/N6/C7ⁱⁱ/C8ⁱⁱ/C9] are inclined to one another by 39.06 (17) ° [symmetry codes: (i) -x+1, y+1/2, -z+1/2; (ii) -x+1, y-1/2, -z+1/2].

In the crystal, the chains are linked via bifurcated N—H···O/O hydrogen bonds forming sheets parallel to (001); (Table 1 and Fig. 2). These two-dimensional networks are linked via C-H···O hydrogen bonds and a C-H···π interaction forming a three-dimensional structure.

Related literature top

For imidazoles in biological systems, see: Brooks & Davidson, (1960). For the crystal structure of a similar compound, see: Fu et al. (2007). For the synthesis of the title compound, see: Anbalagan & Lydia (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized following a published procedure (Anbalagan & Lydia, 2011). To an ethanol solution (30 ml) of imidazole (1.0 g, 4.2 mmol) was added an ethanol solution of Zn(NO₃)₂.6H₂O (0.32 g, 1.1 mmol) and the mixture was stirred for 30 min at room temperature. The solvent was removed under vacuum. The white powder obtained was washed several times with water and ether. The final product was dissolved in 5–10 ml of ethanol and allowed to crystallize in a desiccator containing P₂O₅ for 4 days. Colourless crystals were obtained [yield > 90%], which were filtered, washed with cold ethanol and dried under vacuum.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atomic labelling [Symmetry codes: (a) -x+1, y+1/2, -z+1/2; (b) -x+1, y-1/2, -z+1/2]. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b-axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed bonds (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).

catena-Poly[[[bis(1H-imidazole-κN³)zinc(II)]-µ₂-imidazol-1-ido-κ²N:N'] nitrate] top

Crystal data top

[Zn(C₃H₃N₂)(C₃H₄N₂)₂]NO₃	F(000) = 672
M_r = 330.62	D_x = 1.576 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1812 (10) Å	Cell parameters from 1994 reflections
b = 10.0713 (7) Å	θ = 3.9–25.0°
c = 11.3628 (10) Å	µ = 1.78 mm⁻¹
β = 91.011 (8)°	T = 293 K
V = 1393.78 (19) Å³	Block, pink
Z = 4	0.45 × 0.35 × 0.35 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3132 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 29.1°, θ_min = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −16→16
T_min = 0.478, T_max = 0.536	k = −13→13
7564 measured reflections	l = −13→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0384P)² + 0.2989P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3132 reflections	Δρ_max = 0.26 e Å⁻³
188 parameters	Δρ_min = −0.30 e Å⁻³
2 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0081 (9)

Crystal data top

[Zn(C₃H₃N₂)(C₃H₄N₂)₂]NO₃	V = 1393.78 (19) Å³
M_r = 330.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1812 (10) Å	µ = 1.78 mm⁻¹
b = 10.0713 (7) Å	T = 293 K
c = 11.3628 (10) Å	0.45 × 0.35 × 0.35 mm
β = 91.011 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3132 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2419 reflections with I > 2σ(I)
T_min = 0.478, T_max = 0.536	R_int = 0.025
7564 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.26 e Å⁻³
3132 reflections	Δρ_min = −0.30 e Å⁻³
188 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.36252 (2)	0.46682 (2)	0.22841 (2)	0.03923 (12)
N1	0.25332 (15)	0.47069 (19)	0.35663 (18)	0.0432 (5)
N2	0.13625 (19)	0.4040 (3)	0.4868 (2)	0.0660 (7)
H2N	0.087 (2)	0.347 (3)	0.521 (3)	0.079*
N3	0.28898 (17)	0.5089 (2)	0.07477 (18)	0.0453 (5)
N4	0.1623 (2)	0.5621 (2)	−0.0543 (2)	0.0629 (6)
H4N	0.0994 (18)	0.591 (3)	−0.081 (3)	0.075*
N5	0.42417 (16)	0.28445 (18)	0.21108 (18)	0.0445 (5)
N6	0.47785 (15)	0.59804 (18)	0.27271 (17)	0.0417 (4)
C1	0.1922 (2)	0.3708 (3)	0.3939 (2)	0.0542 (7)
H1	0.1894	0.2875	0.3585	0.065*
C2	0.1596 (2)	0.5311 (4)	0.5132 (3)	0.0699 (9)
H2	0.1314	0.5802	0.5750	0.084*
C3	0.2327 (2)	0.5742 (3)	0.4320 (3)	0.0591 (7)
H3	0.2632	0.6587	0.4282	0.071*
C4	0.1872 (2)	0.5504 (3)	0.0592 (3)	0.0547 (7)
H4	0.1392	0.5689	0.1198	0.066*
C5	0.2504 (3)	0.5270 (3)	−0.1158 (3)	0.0730 (9)
H5	0.2564	0.5264	−0.1973	0.088*
C6	0.3286 (3)	0.4929 (3)	−0.0364 (3)	0.0642 (8)
H6	0.3986	0.4632	−0.0542	0.077*
C7	0.3839 (3)	0.1932 (3)	0.1340 (3)	0.0754 (10)
H7	0.3248	0.2063	0.0824	0.090*
C8	0.50637 (19)	0.2215 (2)	0.2642 (2)	0.0445 (6)
H8	0.5497	0.2606	0.3227	0.053*
C9	0.5567 (3)	0.5799 (3)	0.3560 (3)	0.0733 (10)
H9	0.5684	0.5026	0.3993	0.088*
O1	−0.02383 (16)	0.7857 (2)	0.38003 (18)	0.0670 (5)
O2	−0.0378 (2)	0.6253 (3)	0.2556 (2)	0.0974 (8)
O3	0.0817 (2)	0.7775 (2)	0.23084 (19)	0.0834 (7)
N7	0.00643 (19)	0.7290 (2)	0.2867 (2)	0.0568 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04116 (18)	0.03470 (16)	0.04196 (18)	0.00129 (11)	0.00404 (12)	−0.00016 (11)
N1	0.0413 (11)	0.0480 (11)	0.0405 (11)	0.0025 (9)	0.0064 (9)	0.0014 (9)
N2	0.0451 (13)	0.097 (2)	0.0562 (16)	−0.0008 (13)	0.0111 (12)	0.0142 (15)
N3	0.0462 (11)	0.0477 (11)	0.0420 (12)	0.0069 (9)	0.0037 (9)	0.0008 (9)
N4	0.0626 (16)	0.0636 (15)	0.0620 (16)	0.0042 (12)	−0.0114 (14)	0.0139 (12)
N5	0.0454 (11)	0.0360 (10)	0.0520 (12)	0.0020 (8)	−0.0039 (10)	−0.0049 (9)
N6	0.0455 (11)	0.0358 (9)	0.0436 (11)	−0.0035 (8)	0.0004 (9)	0.0027 (9)
C1	0.0436 (14)	0.0641 (16)	0.0549 (16)	−0.0020 (12)	0.0030 (13)	0.0091 (13)
C2	0.0556 (17)	0.108 (3)	0.0462 (17)	0.0285 (17)	0.0086 (14)	−0.0098 (17)
C3	0.0615 (17)	0.0609 (16)	0.0552 (17)	0.0117 (13)	0.0055 (14)	−0.0091 (14)
C4	0.0530 (16)	0.0567 (16)	0.0544 (17)	0.0098 (12)	0.0033 (13)	0.0038 (13)
C5	0.096 (3)	0.082 (2)	0.0402 (16)	0.0060 (19)	−0.0029 (17)	0.0034 (15)
C6	0.0610 (17)	0.081 (2)	0.0515 (17)	0.0143 (14)	0.0134 (15)	−0.0019 (14)
C7	0.085 (2)	0.0483 (15)	0.091 (2)	0.0114 (14)	−0.0504 (19)	−0.0149 (16)
C8	0.0456 (13)	0.0385 (12)	0.0492 (14)	0.0000 (10)	−0.0062 (11)	−0.0063 (11)
C9	0.097 (2)	0.0430 (14)	0.078 (2)	−0.0117 (15)	−0.0373 (19)	0.0206 (15)
O1	0.0679 (12)	0.0734 (13)	0.0602 (12)	−0.0107 (10)	0.0150 (10)	−0.0139 (11)
O2	0.117 (2)	0.0852 (17)	0.0903 (18)	−0.0450 (15)	0.0065 (15)	−0.0264 (14)
O3	0.1114 (17)	0.0825 (15)	0.0574 (13)	−0.0286 (14)	0.0313 (13)	0.0009 (12)
N7	0.0637 (14)	0.0596 (14)	0.0469 (12)	−0.0080 (12)	−0.0052 (12)	0.0048 (11)

Geometric parameters (Å, º) top

Zn1—N6	1.9871 (18)	C1—H1	0.9300
Zn1—N1	1.990 (2)	C2—C3	1.364 (4)
Zn1—N3	1.994 (2)	C2—H2	0.9300
Zn1—N5	1.9954 (19)	C3—H3	0.9300
N1—C1	1.325 (3)	C4—H4	0.9300
N1—C3	1.375 (3)	C5—C6	1.345 (4)
N2—C1	1.310 (4)	C5—H5	0.9300
N2—C2	1.344 (4)	C6—H6	0.9300
N2—H2N	0.915 (18)	C7—C9ⁱⁱ	1.355 (4)
N3—C4	1.317 (3)	C7—H7	0.9300
N3—C6	1.369 (3)	C8—N6ⁱⁱ	1.327 (3)
N4—C4	1.325 (4)	C8—H8	0.9300
N4—C5	1.339 (4)	C9—C7ⁱ	1.355 (4)
N4—H4N	0.872 (17)	C9—H9	0.9300
N5—C8	1.322 (3)	O1—N7	1.265 (3)
N5—C7	1.355 (3)	O2—N7	1.224 (3)
N6—C8ⁱ	1.327 (3)	O3—N7	1.226 (3)
N6—C9	1.349 (3)

N6—Zn1—N1	106.27 (8)	N2—C2—C3	106.9 (3)
N6—Zn1—N3	112.65 (8)	N2—C2—H2	126.6
N1—Zn1—N3	109.94 (8)	C3—C2—H2	126.6
N6—Zn1—N5	111.81 (8)	C2—C3—N1	108.0 (3)
N1—Zn1—N5	110.35 (8)	C2—C3—H3	126.0
N3—Zn1—N5	105.86 (8)	N1—C3—H3	126.0
C1—N1—C3	105.5 (2)	N3—C4—N4	111.0 (3)
C1—N1—Zn1	127.24 (18)	N3—C4—H4	124.5
C3—N1—Zn1	127.06 (19)	N4—C4—H4	124.5
C1—N2—C2	108.1 (3)	N4—C5—C6	106.3 (3)
C1—N2—H2N	122 (2)	N4—C5—H5	126.8
C2—N2—H2N	130 (2)	C6—C5—H5	126.8
C4—N3—C6	105.0 (2)	C5—C6—N3	109.4 (3)
C4—N3—Zn1	126.31 (19)	C5—C6—H6	125.3
C6—N3—Zn1	128.51 (18)	N3—C6—H6	125.3
C4—N4—C5	108.2 (3)	N5—C7—C9ⁱⁱ	109.3 (2)
C4—N4—H4N	124 (2)	N5—C7—H7	125.3
C5—N4—H4N	128 (2)	C9ⁱⁱ—C7—H7	125.3
C8—N5—C7	103.4 (2)	N5—C8—N6ⁱⁱ	114.7 (2)
C8—N5—Zn1	132.85 (15)	N5—C8—H8	122.6
C7—N5—Zn1	123.74 (16)	N6ⁱⁱ—C8—H8	122.6
C8ⁱ—N6—C9	104.1 (2)	N6—C9—C7ⁱ	108.5 (2)
C8ⁱ—N6—Zn1	130.45 (16)	N6—C9—H9	125.8
C9—N6—Zn1	125.38 (17)	C7ⁱ—C9—H9	125.8
N2—C1—N1	111.5 (3)	O2—N7—O3	121.4 (3)
N2—C1—H1	124.2	O2—N7—O1	119.6 (2)
N1—C1—H1	124.2	O3—N7—O1	119.1 (2)

C2—N2—C1—N1	0.4 (3)	C4—N4—C5—C6	0.5 (4)
C3—N1—C1—N2	−0.6 (3)	N4—C5—C6—N3	−0.9 (4)
Zn1—N1—C1—N2	174.19 (16)	C4—N3—C6—C5	0.9 (3)
C1—N2—C2—C3	−0.1 (3)	Zn1—N3—C6—C5	176.7 (2)
N2—C2—C3—N1	−0.3 (3)	C8—N5—C7—C9ⁱⁱ	0.0 (4)
C1—N1—C3—C2	0.5 (3)	Zn1—N5—C7—C9ⁱⁱ	−179.8 (2)
Zn1—N1—C3—C2	−174.26 (18)	C7—N5—C8—N6ⁱⁱ	0.2 (3)
C6—N3—C4—N4	−0.6 (3)	Zn1—N5—C8—N6ⁱⁱ	179.99 (17)
Zn1—N3—C4—N4	−176.58 (18)	C8ⁱ—N6—C9—C7ⁱ	0.3 (4)
C5—N4—C4—N3	0.1 (3)	Zn1—N6—C9—C7ⁱ	−176.6 (2)

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱⁱⁱ	0.92 (3)	1.92 (3)	2.809 (3)	162 (3)
N4—H4N···O1^iv	0.87 (2)	1.99 (3)	2.826 (3)	161 (3)
N4—H4N···O3^iv	0.87 (2)	2.52 (3)	3.074 (3)	122 (2)
C2—H2···O3^v	0.93	2.37	3.289 (4)	172
C4—H4···O3	0.93	2.55	3.283 (4)	135
C7—H7···Cg1^vi	0.93	2.88	3.587 (4)	133

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

Selected bond lengths (Å) top

Zn1—N6	1.9871 (18)	Zn1—N3	1.994 (2)
Zn1—N1	1.990 (2)	Zn1—N5	1.9954 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C1–C3 imidazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.92 (3)	1.92 (3)	2.809 (3)	162 (3)
N4—H4N···O1ⁱⁱ	0.87 (2)	1.99 (3)	2.826 (3)	161 (3)
N4—H4N···O3ⁱⁱ	0.87 (2)	2.52 (3)	3.074 (3)	122 (2)
C2—H2···O3ⁱⁱⁱ	0.93	2.37	3.289 (4)	172
C4—H4···O3	0.93	2.55	3.283 (4)	135
C7—H7···Cg1^iv	0.93	2.88	3.587 (4)	133

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

Acknowledgements

EG and KA thank the CSIR, New Delhi (Lr: No. 01 (2570)/12/EMR-II/3.4.2012) for financial support through a major research project. The authors are grateful to the Department of Chemistry, Pondicherry University, for access to the single-crystal XRD facilities.

References

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Volume 70| Part 8| August 2014| Pages m298-m299

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