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

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 inter-actions 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 = 216.1

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.10

1778 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.29 e Å−3

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).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011951/lh5609sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C3H5N2)[Na(NO3)2]	F(000) = 440
Mr = 216.1	Dx = 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

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

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(Fo2) + (0.0303P)2 + 0.6068P] where P = (Fo2 + 2Fc2)/3
1778 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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—Na1v	2.9406 (16)
Na1—O13ii	2.5730 (14)	O11—Na1v	2.5910 (19)
Na1—O11ii	2.5910 (19)	O13—Na1vi	2.5106 (13)
Na1—O11	2.6239 (17)	O13—Na1v	2.5730 (14)
Na1—O21iii	2.6776 (14)	C4—N3	1.328 (2)
Na1—O12iv	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—Na1iv	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)	O12iv—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—Na1iv	117.13 (10)
O13ii—Na1—O11ii	49.87 (4)	Na1—O21—Na1iv	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—O12iv	84.35 (5)	O11—N1—Na1v	61.59 (8)
O21—Na1—O12iv	76.22 (5)	O13—N1—Na1v	60.79 (8)
O13i—Na1—O12iv	72.38 (4)	O12—N1—Na1v	166.49 (10)
O23—Na1—O12iv	67.45 (4)	Na1—N1—Na1v	121.45 (5)
O13ii—Na1—O12iv	137.21 (4)	N1—O11—Na1v	93.37 (9)
O11ii—Na1—O12iv	144.51 (4)	N1—O11—Na1	90.29 (9)
O11—Na1—O12iv	65.26 (5)	Na1v—O11—Na1	156.34 (6)
O21iii—Na1—O12iv	140.33 (4)	N1—O13—Na1vi	119.68 (9)
O12—Na1—N1	25.46 (4)	N1—O13—Na1v	93.99 (9)
O21—Na1—N1	142.68 (4)	Na1vi—O13—Na1v	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
O12iv—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
O12iv—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)	O12iv—Na1—N1—O11	−71.01 (8)
O12iv—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—Na1iv	104.45 (7)	O23—Na1—N1—O12	54.46 (9)
O13i—Na1—O21—Na1iv	−37.16 (4)	O13ii—Na1—N1—O12	−92.27 (9)
O23—Na1—O21—Na1iv	108.86 (6)	O11ii—Na1—N1—O12	−97.23 (10)
O13ii—Na1—O21—Na1iv	−115.19 (7)	O11—Na1—N1—O12	−171.58 (14)
O11ii—Na1—O21—Na1iv	−109.92 (4)	O21iii—Na1—N1—O12	−21.31 (9)
O11—Na1—O21—Na1iv	26.17 (8)	O12iv—Na1—N1—O12	117.41 (10)
O21iii—Na1—O21—Na1iv	180	N1ii—Na1—N1—O12	−97.78 (8)
O12iv—Na1—O21—Na1iv	36.89 (4)	Na1iii—Na1—N1—O12	−46.51 (8)
N1—Na1—O21—Na1iv	67.58 (8)	O12—Na1—N1—Na1v	−164.26 (12)
N1ii—Na1—O21—Na1iv	−108.43 (5)	O21—Na1—N1—Na1v	−78.36 (8)
Na1iii—Na1—O21—Na1iv	180	O13i—Na1—N1—Na1v	17.56 (7)
Na1—O21—N22—O23	15.20 (14)	O23—Na1—N1—Na1v	−109.81 (5)
Na1iv—O21—N22—O23	−75.40 (16)	O13ii—Na1—N1—Na1v	103.46 (6)
Na1—O21—N22—O22	−164.17 (12)	O11ii—Na1—N1—Na1v	98.51 (7)
Na1iv—O21—N22—O22	105.23 (14)	O11—Na1—N1—Na1v	24.16 (7)
O22—N22—O23—Na1	164.63 (12)	O21iii—Na1—N1—Na1v	174.43 (5)
O21—N22—O23—Na1	−14.73 (14)	O12iv—Na1—N1—Na1v	−46.85 (5)
O12—Na1—O23—N22	−174.84 (9)	N1ii—Na1—N1—Na1v	97.95 (7)
O21—Na1—O23—N22	8.34 (8)	Na1iii—Na1—N1—Na1v	149.23 (5)
O13i—Na1—O23—N22	49.13 (10)	O13—N1—O11—Na1v	−14.00 (14)
O13ii—Na1—O23—N22	−116.69 (11)	O12—N1—O11—Na1v	164.60 (12)
O11ii—Na1—O23—N22	−44.21 (11)	Na1—N1—O11—Na1v	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)
O12iv—Na1—O23—N22	98.36 (10)	Na1v—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)	O12iv—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)
O12iv—Na1—O12—N1	−57.79 (9)	O12—Na1—O11—Na1v	−103.77 (14)
N1ii—Na1—O12—N1	88.16 (7)	O21—Na1—O11—Na1v	11.44 (17)
Na1iii—Na1—O12—N1	122.21 (9)	O13i—Na1—O11—Na1v	74.50 (12)
O21—Na1—O12—Na1iii	115.57 (6)	O23—Na1—O11—Na1v	−47.37 (14)
O13i—Na1—O12—Na1iii	−119.86 (5)	O13ii—Na1—O11—Na1v	166.77 (13)
O23—Na1—O12—Na1iii	112.09 (4)	O11ii—Na1—O11—Na1v	140.47 (11)
O13ii—Na1—O12—Na1iii	−39.79 (4)	O21iii—Na1—O11—Na1v	−135.51 (12)
O11ii—Na1—O12—Na1iii	−20.30 (6)	O12iv—Na1—O11—Na1v	−0.03 (12)
O11—Na1—O12—Na1iii	−117.56 (5)	N1—Na1—O11—Na1v	−99.10 (15)
O21iii—Na1—O12—Na1iii	36.93 (4)	N1ii—Na1—O11—Na1v	151.28 (12)
O12iv—Na1—O12—Na1iii	180	Na1iii—Na1—O11—Na1v	−149.26 (12)
N1—Na1—O12—Na1iii	−122.21 (9)	O11—N1—O13—Na1vi	−77.90 (15)
N1ii—Na1—O12—Na1iii	−34.05 (4)	O12—N1—O13—Na1vi	103.51 (13)
Na1—O12—N1—O11	−8.72 (14)	Na1v—N1—O13—Na1vi	−92.00 (8)
Na1iii—O12—N1—O11	80.25 (15)	O11—N1—O13—Na1v	14.11 (14)
Na1—O12—N1—O13	169.89 (11)	O12—N1—O13—Na1v	−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—Na1v	82.0 (4)	N3—C2—C1—N5	−0.30 (18)
Na1iii—O12—N1—Na1v	170.9 (4)	N3—C4—N5—C1	−0.50 (19)
O12—Na1—N1—O11	171.58 (14)	C2—C1—N5—C4	0.50 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O23vii	0.95	2.50	3.438 (3)	168
C4—H4···O11v	0.95	2.41	3.355 (3)	173

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) ; (ii) ; (iii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O23iv	0.95	2.50	3.438 (3)	168
C4—H4⋯O11v	0.95	2.41	3.355 (3)	173

Symmetry codes: (iv) ; (v) .