Crystal structures of the two salts 2-methyl-1H-imidazol-3-ium nitrate–2-methyl-1H-imidazole (1/1) and 2-methyl-1H-imidazol-3-ium nitrate

Diop, M.B.; Diop, L.; Maris, T.

doi:10.1107/S2056989016003789

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ISSN: 2056-9890

Volume 72| Part 4| April 2016| Pages 482-485

https://doi.org/10.1107/S2056989016003789

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Crystal structures of the two salts 2-methyl-1H-imidazol-3-ium nitrate–2-methyl-1H-imidazole (1/1) and 2-methyl-1H-imidazol-3-ium nitrate

Mouhamadou Birame Diop,^a ^* Libasse Diop ^a and Thierry Maris ^b

^aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDépartement de Chimie, Université de Montréal, 2900 Boulevard Édouard-Montpetit, Montréal, Québec, H3C 3J7, Canada
^*Correspondence e-mail: mouhamadoubdiop@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 19 February 2016; accepted 6 March 2016; online 11 March 2016)

The title salts, C₄H₇N₂⁺·NO₃⁻·C₄H₆N₂, (I), and C₄H₇N₂⁺·NO₃⁻, (II), were obtained from solutions containing 2-methylimidazole and nitric acid in different concentrations. In the crystal structure of salt (I), one of the –NH H atoms of the imidazole ring shows half-occupancy, hence only every second molecule is in its cationic form. The nitrate anion in this structure lies on a twofold rotation axis. The neutral 2-methylimidazole molecule and the 2-methyl-1H-imidazol-3-ium cation interact through N—H⋯N hydrogen bonds to form [(C₄H₆N₂)⋯(C₄H₇N₂)⁺] pairs. These pairs are linked with two nitrate anions on both sides through bifurcated N—H⋯(O,O) hydrogen bonds into chains running parallel to [001]. In the crystal structure of salt (II), the C₄H₇N₂⁺ cation and the NO₃⁻ anion are both located on a mirror plane, leading to a statistical disorder of the methyl H atoms. The cations and anions again interact through bifurcated N—H⋯(O,O) hydrogen bonds, giving rise to the formation of chains consisting of alternating anions and cations parallel to [100].

Keywords: crystal structure; 2-methyl-1H-imidazol-3-ium cations; bifurcated hydrogen bonds; chain structure.

CCDC references: 1458009; 1458008

1. Chemical context

While targeting the synthesis of new Sn^IV complexes, crystals of the salt C₄H₇N₂⁺·NO₃⁻, (II), were obtained serendipitously by mixing trimethyltin acetate with 2-methylimidazole in the presence of nitric acid. In the dynamic of seeking new ammonium salts soluble in organic solvents that can be used for further metallorganic syntheses, we have initiated the targeted preparation of this salt. However, by variation of the ratio between nitric acid and 2-methylimidazole we also obtained crystals of compound (I), C₄H₆N₂·C₄H₇N₂⁺·NO₃⁻, and report the two structures in this communication.

2. Structural commentary

The asymmetric unit of salt (I) consists of a 2-methylimidazole moiety in a general position and part of a nitrate anion. The anion is completed by application of twofold rotation symmetry. The hydrogen atom H1 attached to N1 of the imidazole ring has a statistical occupancy of 0.5, thus leading to a 1:1 mixture of a 2-methyl-1H-imidazol-3-ium cation and a neutral 2-methylimidazole molecule in the crystal applying symmetry operation (i) 1 − x, y, $[{1\over 2}]$ − z (Fig. 1). In the nitrate anion, the N—O bond lengths [1.2433 (11)–1.2774 (19) Å], are in a typical range (see, for example, Diop et al., 2013 ) and indicate some π delocalization over the two oxygen atoms O1 and O1ⁱ. The longer N—O distance is observed for atom O2 involved in the stronger of the two observed N—H⋯O hydrogen bonds (Table 1). The imidazole ring is planar with a maximum deviation of 0.005 (1) Å. The asymmetric unit of salt (II) consists of an ordered 2-methyl-1H-imidazol-3-ium cation and a nitrate anion (Fig. 2), both lying on a mirror plane.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.845 (19)	2.594 (19)	3.1837 (14)	127.9 (15)
N2—H2⋯O2	0.845 (19)	2.06 (2)	2.9031 (10)	172.5 (18)
N1—H1⋯N1ⁱⁱ	0.83 (3)	1.86 (3)	2.678 (2)	173 (4)
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular components of salt (I)

, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius and hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) 1 − x, y, $[{1\over 2}]$ − z, (ii): 1 − x, y, $[{3\over 2}]$ − z.]

Figure 2
The molecular components of salt (II)

, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius and hydrogen bonds are shown as dashed lines.

In the two structures, the O—N—O angles have normal values close to 120° and their sum (360°) reflect a perfect trigonal–planar geometry for each of the nitrate anions. For the 2-methyl-1H-imidazol-3-ium cations and for the neutral 2-methylimidazole molecule, the N—C distances involving C2, the C atom that carries the methyl group, are equal within 0.01 Å, and their values are consistent with double-bond character, as previously observed (Diop et al., 2015 ).

3. Supramolecular features

In the crystal structure of salt (I), the neutral 2-methylimidazole molecule is connected to the 2-methyl-1H-imidazol-3-ium cation through N—H⋯N hydrogen bonds, forming a [(C₄H₆N₂)⋯(C₄H₇N₂)⁺] pair (Fig. 1). Such pairs are then linked to two nitrate anions through bifurcated N—H⋯(O,O) hydrogen bonds (Table 1), leading to chains extending along [001] (Fig. 3).

Figure 3
Partial view of the packing in the crystal structure of (I)

, showing a chain of hydrogen-bonded molecules. Only one of the statistically disordered H-atom positions between the imidazole rings is shown.

In the crystal structure of (II), the 2-methyl-1H-imidazol-3-ium cations and the nitrate anions are alternately linked by bifurcated N—H⋯(O,O) hydrogen bonds (Table 2), leading to the formation of hydrogen-bonded chains parallel to [100] (Fig. 4).

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.82 (4)	2.12 (4)	2.894 (2)	157 (4)
N1—H1⋯O3ⁱ	0.82 (4)	2.41 (4)	3.125 (3)	147 (4)
N2—H2⋯O1	0.94 (3)	1.83 (3)	2.760 (2)	167 (3)
N2—H2⋯O2	0.94 (3)	2.50 (3)	3.231 (2)	135 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Figure 4
Partial view of the packing in the crystal structure of (II)

, showing a chain made up of hydrogen-bonded nitrate anions and 2-methyl-1H-imidazol-3-ium cations.

In the two structures, the stability between the chains is dominated by electrostatic interactions.

4. Database survey

A search of the Cambridge Structural Database (Version 5.37 with one update, Groom & Allen, 2014 ) for structures containing imidazole or imidazolium rings with nitrate anions returned 21 hits. Molecular chains with bifurcated hydrogen bonds between imidazol-3-ium cations and nitrate anions as found in (II) have been reported for 2-(1-naphthyldiazenyl)-1H-imidazol-3-ium nitrate (Pramanik et al., 2010 ), 2-azidoimidazolium nitrate (Tang et al., 2012 ) and 2-phenylimidazolium nitrate hemihydrate (Zhang et al., 2007 ). Molecular chains similar to those observed in (I) with pairs of imidazole and imidazolium rings linked through bifurcated hydrogen bonds to nitrate anions are also found in the structure of 2-(1H-imidazol-2-yl)-1H-imidazol-3-ium nitrate (Jin et al., 2011 ).

5. Synthesis and crystallization

All chemicals were purchased from Aldrich (Germany) and were used as received. Single crystals suitable for X-ray studies of (II) were first obtained by serendipity when a mixture of 2-methylimidazole and concentrated nitric acid was added to trimethyltin acetate in methanol. Colourless single crystals of (I) were obtained after slow evaporation at room temperature of an aqueous solution consisting of 2-methylimidazole and concentrated nitric acid in a 2:1 ratio. Compound (II) can also be prepared in a similar way by changing the ratio between 2-methylimidazole and nitric acid to 1:1.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For (I), all H atoms were clearly discernible from difference Fourier maps and were freely refined. Half-occupancy of H1 is required for structural reasons and was indicated by the values of the residual density peaks found in the difference Fourier map (0.83 vs 0.47 e Å⁻³ for an occupancy factor of 1 and 0.5, respectively). For (II), the H atoms bound to C were placed in calculated positions and then refined using a riding model with C—H = 0.95 Å (aromatic) and 0.98 Å (methyl) and U_iso(H) = 1.2 and 1.5U_eq(C), respectively. As a result of the mirror symmetry of the 2-methyl-1H-imidazol-3-ium cation, the methyl H atoms are statistically disordered over two positions. H atoms bound to N atoms were located from a difference Fourier map and were freely refined.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₄H₆N₂⁺·NO₃⁻·C₄H₇N₂	C₄H₇N²⁺·NO₃⁻
M_r	227.23	145.13
Crystal system, space group	Monoclinic, C2/c	Orthorhombic, Pnma
Temperature (K)	100	110
a, b, c (Å)	10.1879 (4), 10.0912 (4), 11.9055 (5)	14.1402 (11), 6.2297 (5), 7.4571 (6)
α, β, γ (°)	90, 115.188 (2), 90	90, 90, 90
V (Å³)	1107.60 (8)	656.89 (9)
Z	4	4
Radiation type	Ga Kα, λ = 1.34139 Å	Ga Kα, λ = 1.34139 Å
μ (mm⁻¹)	0.58	0.70
Crystal size (mm)	0.25 × 0.19 × 0.19	0.09 × 0.04 × 0.03

Data collection
Diffractometer	Bruker Venture Metaljet	Bruker Venture Metaljet
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.682, 0.752	0.471, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	8771, 1286, 1210	13253, 817, 761
R_int	0.033	0.060
(sin θ/λ)_max (Å⁻¹)	0.650	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.04	0.049, 0.146, 1.04
No. of reflections	1286	817
No. of parameters	102	68
H-atom treatment	All H-atom parameters refined	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20	0.22, −0.28
Computer programs: APEX2 and, SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), Mercury (Macrae et al., 2008 ), and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1458009; 1458008

Crystal structure: contains datablocks global, II, I. DOI: https://doi.org/10.1107/S2056989016003789/wm5276sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016003789/wm5276Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016003789/wm5276IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016003789/wm5276Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016003789/wm5276IIsup5.cml

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

(I) 2-Methyl-1H-imidazol-3-ium nitrate–2-methyl-1H-imidazole (1/1) top

Crystal data top

C₄H₆N₂⁺·NO₃⁻·C₄H₇N₂	F(000) = 480
M_r = 227.23	D_x = 1.363 Mg m⁻³
Monoclinic, C2/c	Ga Kα radiation, λ = 1.34139 Å
a = 10.1879 (4) Å	Cell parameters from 6125 reflections
b = 10.0912 (4) Å	θ = 5.7–60.7°
c = 11.9055 (5) Å	µ = 0.58 mm⁻¹
β = 115.188 (2)°	T = 100 K
V = 1107.60 (8) Å³	Block, clear light colourless
Z = 4	0.25 × 0.19 × 0.19 mm

Data collection top

Bruker Venture Metaljet diffractometer	1286 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	1210 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	R_int = 0.033
Detector resolution: 10.24 pixels mm^-1	θ_max = 60.7°, θ_min = 5.7°
ω and φ scans	h = −12→13
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
T_min = 0.682, T_max = 0.752	l = −15→13
8771 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	All H-atom parameters refined
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.053P)² + 0.953P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1286 reflections	Δρ_max = 0.25 e Å⁻³
102 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

Special details top

Experimental. X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.

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	Occ. (<1)
N1	0.56964 (11)	0.62468 (10)	0.37404 (10)	0.0219 (3)
H1	0.533 (4)	0.626 (3)	0.297 (3)	0.034 (9)*	0.5
N2	0.59828 (11)	0.65353 (10)	0.56421 (9)	0.0198 (2)
C1	0.37127 (14)	0.74799 (14)	0.39888 (12)	0.0265 (3)
H1A	0.386 (2)	0.837 (2)	0.3796 (19)	0.053 (6)*
H1B	0.303 (2)	0.713 (2)	0.3230 (19)	0.049 (5)*
H1C	0.333 (2)	0.741 (2)	0.454 (2)	0.058 (6)*
C2	0.51030 (12)	0.67449 (11)	0.44456 (10)	0.0189 (3)
H2	0.578 (2)	0.6791 (19)	0.6223 (17)	0.036 (4)*
C3	0.70215 (14)	0.57154 (12)	0.45264 (12)	0.0251 (3)
H3	0.766 (2)	0.5300 (18)	0.4208 (15)	0.037 (4)*
C4	0.72067 (13)	0.58907 (12)	0.57091 (12)	0.0238 (3)
H4	0.802 (2)	0.5656 (17)	0.6485 (16)	0.034 (4)*
O1	0.45994 (10)	0.92001 (9)	0.82112 (8)	0.0274 (2)
O2	0.5000	0.73329 (12)	0.7500	0.0229 (3)
N3	0.5000	0.85988 (14)	0.7500	0.0194 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0253 (5)	0.0217 (5)	0.0215 (5)	0.0005 (4)	0.0127 (4)	0.0000 (4)
N2	0.0216 (5)	0.0213 (5)	0.0177 (5)	0.0016 (4)	0.0094 (4)	0.0007 (4)
C1	0.0218 (6)	0.0317 (7)	0.0260 (6)	0.0055 (5)	0.0100 (5)	0.0035 (5)
C2	0.0198 (5)	0.0183 (5)	0.0196 (5)	−0.0012 (4)	0.0094 (4)	0.0005 (4)
C3	0.0253 (6)	0.0228 (6)	0.0315 (6)	0.0045 (5)	0.0164 (5)	0.0010 (5)
C4	0.0216 (6)	0.0215 (6)	0.0269 (6)	0.0036 (4)	0.0089 (5)	0.0029 (4)
O1	0.0335 (5)	0.0278 (5)	0.0261 (5)	0.0028 (4)	0.0176 (4)	−0.0026 (3)
O2	0.0258 (6)	0.0211 (6)	0.0238 (6)	0.000	0.0123 (5)	0.000
N3	0.0164 (6)	0.0234 (7)	0.0170 (6)	0.000	0.0056 (5)	0.000

Geometric parameters (Å, º) top

N1—H1	0.83 (3)	C1—H1C	0.90 (2)
N1—C2	1.3247 (15)	C1—C2	1.4821 (16)
N1—C3	1.3822 (17)	C3—H3	0.974 (19)
N2—C2	1.3381 (15)	C3—C4	1.3504 (18)
N2—H2	0.845 (19)	C4—H4	0.971 (18)
N2—C4	1.3783 (16)	O1—N3	1.2433 (11)
C1—H1A	0.95 (2)	O2—N3	1.2774 (19)
C1—H1B	0.94 (2)	N3—O1ⁱ	1.2433 (11)

C2—N1—H1	125 (3)	N1—C2—N2	109.58 (10)
C2—N1—C3	107.21 (10)	N1—C2—C1	125.45 (11)
C3—N1—H1	128 (3)	N2—C2—C1	124.91 (11)
C2—N2—H2	122.4 (13)	N1—C3—H3	121.6 (10)
C2—N2—C4	108.41 (10)	C4—C3—N1	108.53 (11)
C4—N2—H2	129.1 (13)	C4—C3—H3	129.9 (10)
H1A—C1—H1B	104.5 (17)	N2—C4—H4	123.6 (10)
H1A—C1—H1C	114.3 (18)	C3—C4—N2	106.26 (11)
H1B—C1—H1C	107.4 (19)	C3—C4—H4	130.1 (10)
C2—C1—H1A	109.7 (13)	O1—N3—O1ⁱ	121.58 (14)
C2—C1—H1B	111.1 (12)	O1ⁱ—N3—O2	119.21 (7)
C2—C1—H1C	109.7 (14)	O1—N3—O2	119.21 (7)

N1—C3—C4—N2	−0.02 (14)	C3—N1—C2—C1	176.33 (12)
C2—N1—C3—C4	0.57 (14)	C4—N2—C2—N1	0.92 (13)
C2—N2—C4—C3	−0.53 (14)	C4—N2—C2—C1	−176.35 (11)
C3—N1—C2—N2	−0.91 (13)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.845 (19)	2.594 (19)	3.1837 (14)	127.9 (15)
N2—H2···O2	0.845 (19)	2.06 (2)	2.9031 (10)	172.5 (18)
N1—H1···N1ⁱⁱ	0.83 (3)	1.86 (3)	2.678 (2)	173 (4)

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

(II) 2-Methyl-1H-imidazol-3-ium nitrate top

Crystal data top

C₄H₇N²⁺·NO₃⁻	D_x = 1.467 Mg m⁻³
M_r = 145.13	Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, Pnma	Cell parameters from 9976 reflections
a = 14.1402 (11) Å	θ = 5.2–60.7°
b = 6.2297 (5) Å	µ = 0.70 mm⁻¹
c = 7.4571 (6) Å	T = 110 K
V = 656.89 (9) Å³	Block, clear light colorless
Z = 4	0.09 × 0.04 × 0.03 mm
F(000) = 304

Data collection top

Bruker Venture Metaljet diffractometer	817 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	761 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	R_int = 0.060
Detector resolution: 10.24 pixels mm^-1	θ_max = 60.8°, θ_min = 8.1°
ω and φ scans	h = −16→18
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −8→8
T_min = 0.471, T_max = 0.752	l = −9→9
13253 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0855P)² + 0.2528P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
817 reflections	Δρ_max = 0.22 e Å⁻³
68 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.75103 (14)	0.2500	0.7473 (3)	0.0489 (5)
H1	0.791 (3)	0.2500	0.828 (5)	0.104 (14)*
N2	0.62239 (12)	0.2500	0.5968 (2)	0.0383 (5)
H2	0.558 (2)	0.2500	0.566 (4)	0.065 (9)*
C1	0.6012 (2)	0.2500	0.9290 (3)	0.0581 (7)
H1A	0.6415	0.2943	1.0295	0.087*	0.5
H1B	0.5768	0.1053	0.9515	0.087*	0.5
H1C	0.5483	0.3504	0.9170	0.087*	0.5
C2	0.65719 (16)	0.2500	0.7623 (3)	0.0409 (5)
C3	0.77534 (16)	0.2500	0.5686 (3)	0.0493 (6)
H3	0.8376	0.2500	0.5208	0.059*
C4	0.69503 (16)	0.2500	0.4755 (3)	0.0448 (6)
H4	0.6892	0.2500	0.3486	0.054*
O1	0.42825 (10)	0.2500	0.55858 (18)	0.0449 (5)
O2	0.46812 (12)	0.2500	0.2772 (2)	0.0498 (5)
O3	0.32003 (10)	0.2500	0.3546 (2)	0.0482 (5)
N3	0.40563 (11)	0.2500	0.3932 (2)	0.0384 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0421 (10)	0.0503 (11)	0.0542 (11)	0.000	−0.0184 (8)	0.000
N2	0.0319 (8)	0.0507 (10)	0.0324 (8)	0.000	−0.0023 (6)	0.000
C1	0.0775 (18)	0.0625 (15)	0.0342 (11)	0.000	0.0076 (10)	0.000
C2	0.0430 (11)	0.0460 (11)	0.0337 (10)	0.000	−0.0045 (8)	0.000
C3	0.0357 (11)	0.0509 (13)	0.0612 (14)	0.000	0.0057 (9)	0.000
C4	0.0448 (12)	0.0522 (12)	0.0374 (10)	0.000	0.0064 (8)	0.000
O1	0.0360 (8)	0.0681 (10)	0.0308 (7)	0.000	−0.0011 (5)	0.000
O2	0.0449 (9)	0.0686 (11)	0.0359 (8)	0.000	0.0092 (6)	0.000
O3	0.0348 (7)	0.0592 (10)	0.0507 (9)	0.000	−0.0103 (6)	0.000
N3	0.0344 (8)	0.0485 (10)	0.0323 (8)	0.000	−0.0005 (6)	0.000

Geometric parameters (Å, º) top

N1—H1	0.82 (4)	C1—H1C	0.9800
N1—C2	1.332 (3)	C1—C2	1.474 (3)
N1—C3	1.376 (3)	C3—H3	0.9500
N2—H2	0.94 (3)	C3—C4	1.331 (3)
N2—C2	1.329 (2)	C4—H4	0.9500
N2—C4	1.369 (3)	O1—N3	1.274 (2)
C1—H1A	0.9800	O2—N3	1.237 (2)
C1—H1B	0.9800	O3—N3	1.244 (2)

C2—N1—H1	128 (3)	N1—C2—C1	127.3 (2)
C2—N1—C3	109.29 (19)	N2—C2—N1	106.91 (18)
C3—N1—H1	122 (3)	N2—C2—C1	125.8 (2)
C2—N2—H2	126.1 (18)	N1—C3—H3	126.5
C2—N2—C4	109.63 (18)	C4—C3—N1	106.98 (19)
C4—N2—H2	124.3 (18)	C4—C3—H3	126.5
H1A—C1—H1B	109.5	N2—C4—H4	126.4
H1A—C1—H1C	109.5	C3—C4—N2	107.19 (19)
H1B—C1—H1C	109.5	C3—C4—H4	126.4
C2—C1—H1A	109.5	O2—N3—O1	119.85 (17)
C2—C1—H1B	109.5	O2—N3—O3	122.22 (18)
C2—C1—H1C	109.5	O3—N3—O1	117.93 (16)

N1—C3—C4—N2	0.000 (1)	C3—N1—C2—C1	180.000 (1)
C2—N1—C3—C4	0.000 (1)	C4—N2—C2—N1	0.000 (1)
C2—N2—C4—C3	0.000 (1)	C4—N2—C2—C1	180.000 (1)
C3—N1—C2—N2	0.000 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.82 (4)	2.12 (4)	2.894 (2)	157 (4)
N1—H1···O3ⁱ	0.82 (4)	2.41 (4)	3.125 (3)	147 (4)
N2—H2···O1	0.94 (3)	1.83 (3)	2.760 (2)	167 (3)
N2—H2···O2	0.94 (3)	2.50 (3)	3.231 (2)	135 (2)

Symmetry code: (i) x+1/2, y, −z+3/2.

Acknowledgements

The authors acknowledge the Cheikh Anta Diop University of Dakar (Sénégal), the Canada Foundation for Innovation and Université de Montréal for financial support.

References

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Volume 72| Part 4| April 2016| Pages 482-485

https://doi.org/10.1107/S2056989016003789

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of the two salts 2-methyl-1H-imidazol-3-ium nitrate–2-methyl-1H-imidazole (1/1) and 2-methyl-1H-imidazol-3-ium nitrate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

3. Supramolecular features