Poly[1H-imidazol-3-ium [di-μ-nitrato-sodium]]

Trifa, C.; Bouhali, A.; Bouacida, S.; Boudaren, C.; Bataille, T.

doi:10.1107/S1600536813011951

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages m303-m304

doi:10.1107/S1600536813011951

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Poly[1H-imidazol-3-ium [di-μ-nitrato-sodium]]

Chahrazed Trifa,^a Amira Bouhali,^a Sofiane Bouacida,^a,^b ^* Chaouki Boudaren ^a and Thierry Bataille ^c

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine, 25000, Algeria, ^bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, 04000 Oum El Bouaghi, Algeria, and ^cSciences Chimiques de Rennes, UMR 6226 CNRS - Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes Cedex, France
^*Correspondence e-mail: Bouacida_Sofiane@yahoo.fr

(Received 25 April 2013; accepted 1 May 2013; online 11 May 2013)

In the title compound {(C₃H₅N₂)[Na(NO₃)₂]}_n, the Na^I ion is coordinated by eight O atoms from three bidentate nitrate anions and two O atoms from two monodentate nitrate anions, displaying a bicapped trigonal–prismatic geometry. The imidazolium cation is essentially planar (r.m.s. deviation for all non-H atoms = 0.0018 Å). In the crystal, the Na^I ions are connected by bridging nitrate ligands, forming layers parallel to (010). The imidazolium cations are sandwiched between these layers. Weak C—H⋯O hydrogen bonds link the layers into a three-dimensional network. In addtion, π–π interactions between the imidazolium rings [centroid–centroid distance = 3.588 (3) Å] are observed.

Related literature

For applications of imidazole and its derivatives, see: Huang et al. (2008 , 2011 ). For the preparation and characterization of some metal complexes of imidazolium, see: Gao et al. (2009 ); Zhang et al. (2011 ); Zhu (2012 ); Han et al. (2007 ); Wenyan et al. (2011 ).

Experimental

Crystal data

(C₃H₅N₂)[Na(NO₃)₂]
M_r = 216.1
Monoclinic, P 2₁ /c
a = 3.5875 (3) Å
b = 24.8548 (17) Å
c = 8.819 (6) Å
β = 95.546 (4)°
V = 782.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 150 K
0.52 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.884, T_max = 0.972
9892 measured reflections
1778 independent reflections
1541 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.10
1778 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected bond lengths (Å)

Na1—O12	2.4321 (16)
Na1—O21	2.4639 (14)
Na1—O13ⁱ	2.5106 (13)
Na1—O23	2.5338 (13)
Na1—O13ⁱⁱ	2.5730 (14)
Na1—O11ⁱⁱ	2.5910 (19)
Na1—O11	2.6239 (17)
Na1—O21ⁱⁱⁱ	2.6776 (14)
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O23^iv	0.95	2.50	3.438 (3)	168
C4—H4⋯O11^v	0.95	2.41	3.355 (3)	173
Symmetry codes: (iv) -x+1, -y, -z+2; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813011951/lh5609sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011951/lh5609Isup2.hkl

checkCIF report

Comment top

Knowledge of the detailed coordination behavior of imidazoles and their limitation in the possible use in complexes with specific catalytic activity is of great current importance. Imidazole, namely 1,3-diazacyclopenta-2,4-diene and its derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal–organic frameworks (Huang et al. 2011; Huang et al. 2008). Recently, several complexes based on the imidazolium cation were reported (Gao et al. 2009; Zhang et al. 2011; Zhu 2012; Han et al. 2007; Wenyan et al. 2011). This paper describes the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (I) (Fig. 1) contains one Na^I ion, one protonated imidazole molecule and two coordinated nitrate anions. The Na centre is coordinated by eight O atoms from three bidentate nitrate anions and two O atoms from two monodentate nitrate anions, displaying a bicapped trigonal-prismatic geometry (Fig. 2). The Na—O bond distances range from 2.4321 (16) to 2.6239 (17) Å. The C—N distances lie in the range 1.328 (2)- 1.376 (2) A°. The imidazolium cation is essentially planar giving an r.m.s. deviation for all non-H atoms of 0.0018 A°, with a maximum deviation from the mean plane of -0.0028 (1)Å for the C4 atom. The crystal packing can be described by alterning two-dimensional polymecric layers and double layers of imidazolium ions. A two-dimensional layer structure is thus constructed parallel to (010) (Fig. 3). Weak hydrogen bonds are formed between imidazolium cation and the nitrate O atoms of adjacent layers (Fig. 3) further connect the two-dimensional layers into a three-dimensional network. In addition, π···π contacts between the imidazolium rings, [centroid-centroid distance = 3.588 (3) Å with ca 1.382 Å slippage] are also observed.

Related literature top

For applications of imidazole and its derivatives, see: Huang et al. (2008, 2011). For the preparation and characterization of some metal complexes of imidazolium, see: Gao et al. (2009); Zhang et al. (2011); Zhu (2012); Han et al. (2007); Wenyan et al. (2011).

Experimental top

All chemicals used (reagent grade) were commercially available. The compound was obtained by using hydrothermal method in Teflon-lined autoclave. The mixture of barium nitrate, imidazole, sodium hydroxide and deionized water in the molar ratio 1:1:3:264 was stirred for half an hour, and transferred in a Teflon-lined autoclave, then treated at 423 K for 4 d. After the mixture was slowly cooled to room temperature, colorless needles suitable for X-ray diffraction analysis were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Figures top

	Fig. 1. The asymetric unit of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The coordination of the unieque Na^I ion.
	Fig. 3. A partial packing diagram of (I), showing alterning layers with hydrogen bond shown as dashed lines.

Poly[1H-imidazol-3-ium [di-µ-nitrato-sodium]] top

Crystal data top

(C₃H₅N₂)[Na(NO₃)₂]	F(000) = 440
M_r = 216.1	D_x = 1.834 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7048 reflections
a = 3.5875 (3) Å	θ = 2.9–27.5°
b = 24.8548 (17) Å	µ = 0.22 mm⁻¹
c = 8.819 (6) Å	T = 150 K
β = 95.546 (4)°	Stick, colourless
V = 782.7 (5) Å³	0.52 × 0.15 × 0.13 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1778 independent reflections
Radiation source: Enraf Nonius FR590	1541 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 4.0°
CCD rotation images, thin slices scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −32→32
T_min = 0.884, T_max = 0.972	l = −11→11
9892 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0303P)² + 0.6068P] where P = (F_o² + 2F_c²)/3
1778 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

(C₃H₅N₂)[Na(NO₃)₂]	V = 782.7 (5) Å³
M_r = 216.1	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.5875 (3) Å	µ = 0.22 mm⁻¹
b = 24.8548 (17) Å	T = 150 K
c = 8.819 (6) Å	0.52 × 0.15 × 0.13 mm
β = 95.546 (4)°

Data collection top

Nonius KappaCCD diffractometer	1778 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	1541 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.972	R_int = 0.029
9892 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.10	Δρ_max = 0.19 e Å⁻³
1778 reflections	Δρ_min = −0.29 e Å⁻³
127 parameters

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
Na1	0.51191 (18)	0.19828 (2)	1.30182 (7)	0.02160 (17)
O21	0.9994 (3)	0.13952 (4)	1.42898 (13)	0.0229 (3)
N22	0.8825 (4)	0.09735 (5)	1.35908 (15)	0.0179 (3)
O23	0.6569 (3)	0.10118 (5)	1.24273 (13)	0.0236 (3)
O22	0.9921 (3)	0.05206 (4)	1.40834 (13)	0.0243 (3)
O12	0.0537 (3)	0.18850 (4)	1.08164 (13)	0.0221 (3)
N1	0.1514 (4)	0.22797 (5)	1.00369 (15)	0.0172 (3)
O11	0.3871 (3)	0.26060 (4)	1.06212 (13)	0.0228 (3)
O13	0.0153 (3)	0.23312 (5)	0.86783 (13)	0.0234 (3)
C4	0.5075 (5)	0.12044 (6)	0.74003 (19)	0.0223 (3)
H4	0.4512	0.1537	0.6896	0.027*
N3	0.6807 (4)	0.11445 (5)	0.87906 (16)	0.0208 (3)
H3	0.7619	0.1408	0.9403	0.025*
C2	0.7128 (5)	0.06034 (6)	0.91212 (19)	0.0212 (3)
H2	0.8252	0.0449	1.0039	0.025*
C1	0.5545 (4)	0.03354 (6)	0.78945 (18)	0.0207 (3)
H1	0.5348	−0.0044	0.778	0.025*
N5	0.4268 (4)	0.07172 (5)	0.68401 (15)	0.0203 (3)
H5	0.3101	0.065	0.5936	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0229 (3)	0.0196 (3)	0.0211 (3)	0.0029 (2)	−0.0037 (3)	−0.0020 (2)
O21	0.0284 (6)	0.0159 (5)	0.0235 (6)	−0.0015 (5)	−0.0022 (5)	−0.0039 (4)
N22	0.0200 (6)	0.0169 (6)	0.0169 (7)	−0.0007 (5)	0.0019 (5)	−0.0006 (5)
O23	0.0273 (6)	0.0246 (6)	0.0178 (6)	−0.0012 (5)	−0.0046 (5)	0.0006 (4)
O22	0.0313 (7)	0.0153 (5)	0.0251 (6)	0.0018 (5)	−0.0033 (5)	0.0009 (4)
O12	0.0297 (6)	0.0169 (5)	0.0188 (6)	−0.0040 (4)	−0.0019 (5)	0.0045 (4)
N1	0.0194 (6)	0.0157 (6)	0.0165 (7)	0.0024 (5)	0.0020 (5)	−0.0005 (5)
O11	0.0225 (6)	0.0192 (5)	0.0263 (6)	−0.0052 (4)	0.0001 (5)	−0.0025 (5)
O13	0.0309 (6)	0.0239 (6)	0.0144 (6)	0.0022 (5)	−0.0024 (5)	0.0022 (4)
C4	0.0246 (8)	0.0206 (7)	0.0219 (8)	0.0004 (6)	0.0035 (6)	0.0015 (6)
N3	0.0221 (7)	0.0190 (6)	0.0214 (7)	−0.0022 (5)	0.0023 (5)	−0.0045 (5)
C2	0.0222 (8)	0.0205 (8)	0.0210 (8)	0.0012 (6)	0.0022 (6)	0.0010 (6)
C1	0.0207 (8)	0.0195 (7)	0.0219 (8)	−0.0003 (6)	0.0025 (6)	−0.0012 (6)
N5	0.0202 (7)	0.0242 (7)	0.0161 (7)	−0.0009 (5)	0.0003 (5)	−0.0025 (5)

Geometric parameters (Å, º) top

Na1—O12	2.4321 (16)	O12—Na1ⁱⁱⁱ	2.8874 (17)
Na1—O21	2.4639 (14)	N1—O11	1.2467 (17)
Na1—O13ⁱ	2.5106 (13)	N1—O13	1.2560 (19)
Na1—O23	2.5338 (13)	N1—Na1^v	2.9406 (16)
Na1—O13ⁱⁱ	2.5730 (14)	O11—Na1^v	2.5910 (19)
Na1—O11ⁱⁱ	2.5910 (19)	O13—Na1^vi	2.5106 (13)
Na1—O11	2.6239 (17)	O13—Na1^v	2.5730 (14)
Na1—O21ⁱⁱⁱ	2.6776 (14)	C4—N3	1.328 (2)
Na1—O12^iv	2.8874 (17)	C4—N5	1.329 (2)
Na1—N1	2.911 (2)	C4—H4	0.95
Na1—N1ⁱⁱ	2.9406 (16)	N3—C2	1.379 (2)
Na1—Na1ⁱⁱⁱ	3.5875 (3)	N3—H3	0.88
O21—N22	1.2668 (17)	C2—C1	1.348 (2)
O21—Na1^iv	2.6776 (14)	C2—H2	0.95
N22—O23	1.2475 (19)	C1—N5	1.376 (2)
N22—O22	1.2558 (17)	C1—H1	0.95
O12—N1	1.2666 (17)	N5—H5	0.88

O12—Na1—O21	134.38 (5)	N1—Na1—N1ⁱⁱ	101.88 (5)
O12—Na1—O13ⁱ	131.96 (5)	O12—Na1—Na1ⁱⁱⁱ	53.22 (4)
O21—Na1—O13ⁱ	80.44 (4)	O21—Na1—Na1ⁱⁱⁱ	131.75 (3)
O12—Na1—O23	82.93 (4)	O13ⁱ—Na1—Na1ⁱⁱⁱ	134.17 (3)
O21—Na1—O23	51.55 (4)	O23—Na1—Na1ⁱⁱⁱ	103.01 (3)
O13ⁱ—Na1—O23	122.49 (5)	O13ⁱⁱ—Na1—Na1ⁱⁱⁱ	44.41 (3)
O12—Na1—O13ⁱⁱ	79.49 (5)	O11ⁱⁱ—Na1—Na1ⁱⁱⁱ	75.02 (3)
O21—Na1—O13ⁱⁱ	140.03 (5)	O11—Na1—Na1ⁱⁱⁱ	84.68 (3)
O13ⁱ—Na1—O13ⁱⁱ	89.76 (4)	O21ⁱⁱⁱ—Na1—Na1ⁱⁱⁱ	43.36 (3)
O23—Na1—O13ⁱⁱ	146.94 (5)	O12^iv—Na1—Na1ⁱⁱⁱ	137.57 (3)
O12—Na1—O11ⁱⁱ	125.84 (5)	N1—Na1—Na1ⁱⁱⁱ	69.08 (3)
O21—Na1—O11ⁱⁱ	90.37 (5)	N1ⁱⁱ—Na1—Na1ⁱⁱⁱ	60.11 (3)
O13ⁱ—Na1—O11ⁱⁱ	73.07 (4)	N22—O21—Na1	94.69 (9)
O23—Na1—O11ⁱⁱ	127.91 (4)	N22—O21—Na1^iv	117.13 (10)
O13ⁱⁱ—Na1—O11ⁱⁱ	49.87 (4)	Na1—O21—Na1^iv	88.39 (4)
O12—Na1—O11	50.67 (4)	O23—N22—O22	120.63 (13)
O21—Na1—O11	140.80 (5)	O23—N22—O21	119.68 (13)
O13ⁱ—Na1—O11	81.31 (4)	O22—N22—O21	119.69 (13)
O23—Na1—O11	114.77 (5)	N22—O23—Na1	91.91 (9)
O13ⁱⁱ—Na1—O11	73.93 (5)	N1—O12—Na1	98.90 (9)
O11ⁱⁱ—Na1—O11	116.76 (4)	N1—O12—Na1ⁱⁱⁱ	122.64 (9)
O12—Na1—O21ⁱⁱⁱ	80.87 (5)	Na1—O12—Na1ⁱⁱⁱ	84.35 (5)
O21—Na1—O21ⁱⁱⁱ	88.39 (4)	O11—N1—O13	120.90 (13)
O13ⁱ—Na1—O21ⁱⁱⁱ	141.34 (5)	O11—N1—O12	119.46 (13)
O23—Na1—O21ⁱⁱⁱ	74.30 (4)	O13—N1—O12	119.62 (13)
O13ⁱⁱ—Na1—O21ⁱⁱⁱ	75.42 (4)	O11—N1—Na1	64.35 (8)
O11ⁱⁱ—Na1—O21ⁱⁱⁱ	70.10 (4)	O13—N1—Na1	170.21 (10)
O11—Na1—O21ⁱⁱⁱ	126.07 (4)	O12—N1—Na1	55.64 (7)
O12—Na1—O12^iv	84.35 (5)	O11—N1—Na1^v	61.59 (8)
O21—Na1—O12^iv	76.22 (5)	O13—N1—Na1^v	60.79 (8)
O13ⁱ—Na1—O12^iv	72.38 (4)	O12—N1—Na1^v	166.49 (10)
O23—Na1—O12^iv	67.45 (4)	Na1—N1—Na1^v	121.45 (5)
O13ⁱⁱ—Na1—O12^iv	137.21 (4)	N1—O11—Na1^v	93.37 (9)
O11ⁱⁱ—Na1—O12^iv	144.51 (4)	N1—O11—Na1	90.29 (9)
O11—Na1—O12^iv	65.26 (5)	Na1^v—O11—Na1	156.34 (6)
O21ⁱⁱⁱ—Na1—O12^iv	140.33 (4)	N1—O13—Na1^vi	119.68 (9)
O12—Na1—N1	25.46 (4)	N1—O13—Na1^v	93.99 (9)
O21—Na1—N1	142.68 (4)	Na1^vi—O13—Na1^v	89.76 (4)
O13ⁱ—Na1—N1	106.51 (4)	N3—C4—N5	107.85 (14)
O23—Na1—N1	97.92 (4)	N3—C4—H4	126.1
O13ⁱⁱ—Na1—N1	77.26 (5)	N5—C4—H4	126.1
O11ⁱⁱ—Na1—N1	126.91 (5)	C4—N3—C2	109.07 (14)
O11—Na1—N1	25.36 (4)	C4—N3—H3	125.5
O21ⁱⁱⁱ—Na1—N1	104.68 (5)	C2—N3—H3	125.5
O12^iv—Na1—N1	71.53 (5)	C1—C2—N3	106.99 (15)
O12—Na1—N1ⁱⁱ	104.05 (5)	C1—C2—H2	126.5
O21—Na1—N1ⁱⁱ	115.36 (5)	N3—C2—H2	126.5
O13ⁱ—Na1—N1ⁱⁱ	77.58 (4)	C2—C1—N5	106.76 (14)
O23—Na1—N1ⁱⁱ	146.03 (5)	C2—C1—H1	126.6
O13ⁱⁱ—Na1—N1ⁱⁱ	25.22 (4)	N5—C1—H1	126.6
O11ⁱⁱ—Na1—N1ⁱⁱ	25.04 (4)	C4—N5—C1	109.33 (14)
O11—Na1—N1ⁱⁱ	93.96 (5)	C4—N5—H5	125.3
O21ⁱⁱⁱ—Na1—N1ⁱⁱ	74.13 (4)	C1—N5—H5	125.3
O12^iv—Na1—N1ⁱⁱ	145.46 (4)

O12—Na1—O21—N22	−12.65 (12)	O21—Na1—N1—O11	−102.52 (10)
O13ⁱ—Na1—O21—N22	−154.26 (9)	O13ⁱ—Na1—N1—O11	−6.60 (9)
O23—Na1—O21—N22	−8.23 (8)	O23—Na1—N1—O11	−133.96 (9)
O13ⁱⁱ—Na1—O21—N22	127.71 (9)	O13ⁱⁱ—Na1—N1—O11	79.31 (8)
O11ⁱⁱ—Na1—O21—N22	132.99 (9)	O11ⁱⁱ—Na1—N1—O11	74.35 (7)
O11—Na1—O21—N22	−90.93 (11)	O21ⁱⁱⁱ—Na1—N1—O11	150.27 (8)
O21ⁱⁱⁱ—Na1—O21—N22	62.90 (10)	O12^iv—Na1—N1—O11	−71.01 (8)
O12^iv—Na1—O21—N22	−80.21 (9)	N1ⁱⁱ—Na1—N1—O11	73.79 (10)
N1—Na1—O21—N22	−49.51 (12)	Na1ⁱⁱⁱ—Na1—N1—O11	125.07 (8)
N1ⁱⁱ—Na1—O21—N22	134.48 (8)	O21—Na1—N1—O12	85.90 (11)
Na1ⁱⁱⁱ—Na1—O21—N22	62.90 (10)	O13ⁱ—Na1—N1—O12	−178.18 (9)
O12—Na1—O21—Na1^iv	104.45 (7)	O23—Na1—N1—O12	54.46 (9)
O13ⁱ—Na1—O21—Na1^iv	−37.16 (4)	O13ⁱⁱ—Na1—N1—O12	−92.27 (9)
O23—Na1—O21—Na1^iv	108.86 (6)	O11ⁱⁱ—Na1—N1—O12	−97.23 (10)
O13ⁱⁱ—Na1—O21—Na1^iv	−115.19 (7)	O11—Na1—N1—O12	−171.58 (14)
O11ⁱⁱ—Na1—O21—Na1^iv	−109.92 (4)	O21ⁱⁱⁱ—Na1—N1—O12	−21.31 (9)
O11—Na1—O21—Na1^iv	26.17 (8)	O12^iv—Na1—N1—O12	117.41 (10)
O21ⁱⁱⁱ—Na1—O21—Na1^iv	180	N1ⁱⁱ—Na1—N1—O12	−97.78 (8)
O12^iv—Na1—O21—Na1^iv	36.89 (4)	Na1ⁱⁱⁱ—Na1—N1—O12	−46.51 (8)
N1—Na1—O21—Na1^iv	67.58 (8)	O12—Na1—N1—Na1^v	−164.26 (12)
N1ⁱⁱ—Na1—O21—Na1^iv	−108.43 (5)	O21—Na1—N1—Na1^v	−78.36 (8)
Na1ⁱⁱⁱ—Na1—O21—Na1^iv	180	O13ⁱ—Na1—N1—Na1^v	17.56 (7)
Na1—O21—N22—O23	15.20 (14)	O23—Na1—N1—Na1^v	−109.81 (5)
Na1^iv—O21—N22—O23	−75.40 (16)	O13ⁱⁱ—Na1—N1—Na1^v	103.46 (6)
Na1—O21—N22—O22	−164.17 (12)	O11ⁱⁱ—Na1—N1—Na1^v	98.51 (7)
Na1^iv—O21—N22—O22	105.23 (14)	O11—Na1—N1—Na1^v	24.16 (7)
O22—N22—O23—Na1	164.63 (12)	O21ⁱⁱⁱ—Na1—N1—Na1^v	174.43 (5)
O21—N22—O23—Na1	−14.73 (14)	O12^iv—Na1—N1—Na1^v	−46.85 (5)
O12—Na1—O23—N22	−174.84 (9)	N1ⁱⁱ—Na1—N1—Na1^v	97.95 (7)
O21—Na1—O23—N22	8.34 (8)	Na1ⁱⁱⁱ—Na1—N1—Na1^v	149.23 (5)
O13ⁱ—Na1—O23—N22	49.13 (10)	O13—N1—O11—Na1^v	−14.00 (14)
O13ⁱⁱ—Na1—O23—N22	−116.69 (11)	O12—N1—O11—Na1^v	164.60 (12)
O11ⁱⁱ—Na1—O23—N22	−44.21 (11)	Na1—N1—O11—Na1^v	156.62 (6)
O11—Na1—O23—N22	144.67 (9)	O13—N1—O11—Na1	−170.61 (12)
O21ⁱⁱⁱ—Na1—O23—N22	−92.38 (10)	O12—N1—O11—Na1	7.98 (13)
O12^iv—Na1—O23—N22	98.36 (10)	Na1^v—N1—O11—Na1	−156.62 (6)
N1—Na1—O23—N22	164.52 (9)	O12—Na1—O11—N1	−4.67 (8)
N1ⁱⁱ—Na1—O23—N22	−70.14 (13)	O21—Na1—O11—N1	110.55 (10)
Na1ⁱⁱⁱ—Na1—O23—N22	−125.23 (8)	O13ⁱ—Na1—O11—N1	173.60 (9)
O21—Na1—O12—N1	−122.22 (9)	O23—Na1—O11—N1	51.74 (9)
O13ⁱ—Na1—O12—N1	2.35 (12)	O13ⁱⁱ—Na1—O11—N1	−94.12 (9)
O23—Na1—O12—N1	−125.70 (9)	O11ⁱⁱ—Na1—O11—N1	−120.42 (7)
O13ⁱⁱ—Na1—O12—N1	82.42 (9)	O21ⁱⁱⁱ—Na1—O11—N1	−36.40 (10)
O11ⁱⁱ—Na1—O12—N1	101.91 (10)	O12^iv—Na1—O11—N1	99.07 (9)
O11—Na1—O12—N1	4.65 (8)	N1ⁱⁱ—Na1—O11—N1	−109.62 (10)
O21ⁱⁱⁱ—Na1—O12—N1	159.15 (9)	Na1ⁱⁱⁱ—Na1—O11—N1	−50.16 (8)
O12^iv—Na1—O12—N1	−57.79 (9)	O12—Na1—O11—Na1^v	−103.77 (14)
N1ⁱⁱ—Na1—O12—N1	88.16 (7)	O21—Na1—O11—Na1^v	11.44 (17)
Na1ⁱⁱⁱ—Na1—O12—N1	122.21 (9)	O13ⁱ—Na1—O11—Na1^v	74.50 (12)
O21—Na1—O12—Na1ⁱⁱⁱ	115.57 (6)	O23—Na1—O11—Na1^v	−47.37 (14)
O13ⁱ—Na1—O12—Na1ⁱⁱⁱ	−119.86 (5)	O13ⁱⁱ—Na1—O11—Na1^v	166.77 (13)
O23—Na1—O12—Na1ⁱⁱⁱ	112.09 (4)	O11ⁱⁱ—Na1—O11—Na1^v	140.47 (11)
O13ⁱⁱ—Na1—O12—Na1ⁱⁱⁱ	−39.79 (4)	O21ⁱⁱⁱ—Na1—O11—Na1^v	−135.51 (12)
O11ⁱⁱ—Na1—O12—Na1ⁱⁱⁱ	−20.30 (6)	O12^iv—Na1—O11—Na1^v	−0.03 (12)
O11—Na1—O12—Na1ⁱⁱⁱ	−117.56 (5)	N1—Na1—O11—Na1^v	−99.10 (15)
O21ⁱⁱⁱ—Na1—O12—Na1ⁱⁱⁱ	36.93 (4)	N1ⁱⁱ—Na1—O11—Na1^v	151.28 (12)
O12^iv—Na1—O12—Na1ⁱⁱⁱ	180	Na1ⁱⁱⁱ—Na1—O11—Na1^v	−149.26 (12)
N1—Na1—O12—Na1ⁱⁱⁱ	−122.21 (9)	O11—N1—O13—Na1^vi	−77.90 (15)
N1ⁱⁱ—Na1—O12—Na1ⁱⁱⁱ	−34.05 (4)	O12—N1—O13—Na1^vi	103.51 (13)
Na1—O12—N1—O11	−8.72 (14)	Na1^v—N1—O13—Na1^vi	−92.00 (8)
Na1ⁱⁱⁱ—O12—N1—O11	80.25 (15)	O11—N1—O13—Na1^v	14.11 (14)
Na1—O12—N1—O13	169.89 (11)	O12—N1—O13—Na1^v	−164.48 (12)
Na1ⁱⁱⁱ—O12—N1—O13	−101.14 (14)	N5—C4—N3—C2	0.31 (19)
Na1ⁱⁱⁱ—O12—N1—Na1	88.97 (9)	C4—N3—C2—C1	0.00 (19)
Na1—O12—N1—Na1^v	82.0 (4)	N3—C2—C1—N5	−0.30 (18)
Na1ⁱⁱⁱ—O12—N1—Na1^v	170.9 (4)	N3—C4—N5—C1	−0.50 (19)
O12—Na1—N1—O11	171.58 (14)	C2—C1—N5—C4	0.50 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O23^vii	0.95	2.50	3.438 (3)	168
C4—H4···O11^v	0.95	2.41	3.355 (3)	173

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

Experimental details

Crystal data
Chemical formula	(C₃H₅N₂)[Na(NO₃)₂]
M_r	216.1
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	3.5875 (3), 24.8548 (17), 8.819 (6)
β (°)	95.546 (4)
V (Å³)	782.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.52 × 0.15 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.884, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	9892, 1778, 1541
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.10
No. of reflections	1778
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.29

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Selected bond lengths (Å) top

Na1—O12	2.4321 (16)	Na1—O13ⁱⁱ	2.5730 (14)
Na1—O21	2.4639 (14)	Na1—O11ⁱⁱ	2.5910 (19)
Na1—O13ⁱ	2.5106 (13)	Na1—O11	2.6239 (17)
Na1—O23	2.5338 (13)	Na1—O21ⁱⁱⁱ	2.6776 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O23^iv	0.95	2.50	3.438 (3)	168.00
C4—H4···O11^v	0.95	2.41	3.355 (3)	173.00

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

Acknowledgements

The authors thank MESRS and ATRST (Algérie) for financial support. They also thank Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for his technical assistance with the data collection.

References

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