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All three title compounds, C4H7N2+·C4H5O4-, (I), C4H7N2+·C5H7O4-, (II), and C4H7N2+·C6H9O4-·H2O, (III), can be regarded as 1:1 organic salts. The dicarboxylic acids join through short acid bridges into infinite chains. Compound (I) crystallizes in the noncentrosymmetric Cmc21 space group and the asymmetric unit consists of a hydrogen succinate anion located on a mirror plane and a 2-methyl­imidazolium cation disordered across the same mirror. The other two compounds crystallize in the triclinic P\overline{1} space group. The carboxylic acid H atom in (II) is disordered over both ends of the anion and sits on inversion centres between adjacent anions, forming symmetric short O...H...O bridges. Two independent anions in (III) sit across inversion centres, again with the carboxylic acid H atom disordered in short O...H...O bridges. The mol­ecules in all three compounds are linked into two-dimensional networks by combinations of imidazolium-carboxylate N+-H...O and carboxylate-carboxylate O-H...O hydrogen bonds. The two-dimensional networks are further linked into three-dimensional networks by C-H...O hydrogen bonds in (I) and by Owater-H...O hydrogen bonds in (III). According to the [Delta]pKa rule, such 1:1 types of organic salts can be expected unambiguously. However, a 2:1 type of organic salt may be more easily obtained in (II) and (III) than in (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109012530/sk3296sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109012530/sk3296Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109012530/sk3296IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109012530/sk3296IIIsup4.hkl
Contains datablock III

CCDC references: 735125; 735126; 735127

Comment top

In a continuation of our studies of organic salts formed by organic acids and imidazole derivatives (Meng, Xiao et al., 2008; Meng, Lin & Li 2008; Zhou et al., 2009), we now report our findings on the three title compounds, (I)–(III), formed by aliphatic diacids and 2-methylimidazole (2-MeIm).

All three title compounds were obtained as 1:1 organic salts with one H atom transferred from a carboxyl group to an imidazole N atom. This can be corroborated by the distinct variations in the two carboxyl C—O bond lengths [C8—O3 = 1.231 (3) and C8—O4 = 1.278 (2) Å in (I); C5—O1 = 1.276 (2), C5—O2 = 1.218 (2), C9—O3 = 1.273 (2) and C9—O4 = 1.219 (2) Å in (II); C5—O1 = 1.244 (2), C50—O2 = 1.264 (2), C8—O4 = 1.232 (2) and C8—O3 = 1.294 (2) Å in (III)], and by the C—N—C bond angles in the 2-HMeIm cation [108.9 (3) and 109.7 (3)° in (I); 109.79 (17) and 109.72 (17)° in (II); 109.70 (16) and 109.24 (17)° in (III)]. These angles are 108.5 and 109.0° in an analogous compound in the Cambridge Structural Database (Allen, 2002), refcode HILSOL (Qu, 2007). Besides the above-mentioned variations, some differences are also observed in the crystal structures of the three compounds.

Compound (I) crystallizes in the noncentrosymmetric space group Cmc21 and its asymmetric unit consists of a succinate monoanion and a 2-HMeIm cation. During the initial structure determination of (I), two sets of peaks were identified forming intertwined five-membered rings, related by a crystallographic mirror plane (Fig. 1). In the packing of (I), molecules are linked by six intermolecular hydrogen bonds (Table 1) into a three-dimensional network which can be easily analysed in terms of three substructures. Firstly, the succinate anion forms a one-dimensional anionic chain through the O1—H1A···O4(x, 1 + y, z) hydrogen bond running parallel to the [010] direction. Secondly, the 2-HMeIm cation joins these adjacent [010] chains together via an R66(28) hydrogen-bond motif (Bernstein et al., 1995), generating a two-dimensional network parallel to the (100) plane (Fig. 2). Finally, these neighbouring (100) networks are linked by C2—H6···O2(x - 1/2, y - 1/2, z) and C3—H7···O3(-x + 1/2, -y + 1/2, z - 1/2) hydrogen bonds into a three-dimensional network.

The asymmetric unit of (II) contains one 2-HMeIm cation and one hydrogen glutarate anion (Fig. 3). The single carboxylic acid H atom is statistically distributed over the two ends of the carboxylate in short O···H···O bridges over centres of inversion. They link the glutarate anions into a one-dimensional chain parallel to the [211] direction. The 2-HMeIm cations then connect adjacent chains via N1—H1A···O2 and N2—H2A···O4(2 - x, 1 - y, 1 - z) hydrogen bonds, resulting in a two-dimensional network parallel to the (120) plane (Fig. 4). In contrast with (I), all methyl groups on one side of the [211] chain in (II) adopt a head-to-head arrangement, i.e. methyl pointing to methyl (Fig. 4). In the two-dimensional network, R44(24) and R44(32) hydrogen-bonding motifs are shaped by a combination of O1···H1B···O1(2 - x, 1 - y, -z) and O3···H1C···O3(-x, 2 - y, 1 - z) hydrogen bonds. No hydrogen-bond interactions are present between adjacent two-dimensional networks, as reported by PLATON (Spek, 2009).

Similar to (II), compound (III) crystallizes in the P1 space group, but its asymmetric unit is composed of two independent adipate half-molecules and one water molecule (Fig. 5). The two half-molecules are linked into a one-dimensional chain parallel to the [101] direction via the O2—H2B···O3 hydrogen bond. The 2-HMeIm cation links neighbouring chains together, forming a two-dimensional network parallel to the (111) plane. If atom H2B is regarded as a discrete atom, two types of R44(34) hydrogen-bonding motifs are formed (Fig. 6), one narrow and the other wide. It is worth mentioning that the methyl groups on both sides of the [101] chain in (III) adopt an inclined side-by-side arrangement, which is very different from those in (I) and (II). Unlike the anhydrous compounds, (I) and (II), one water solvent molecule is incorporated into the crystal lattice of (III) and plays a pivotal role in forming the three-dimensional network. These water molecules assemble into a one-dimensional water chain via two Owater···Owater hydrogen bonds [2.715 (4) Å, symmetry code (1 - x, 2 - y, -z), and 2.770 (4) Å, symmetry code (2 - x, 2 - y, -z)] parallel to the [100] direction (Fig. 7). The water chain is hydrogen-bonded to the two-dimensional (111) network via O5···O1 [2.843 (2) Å], resulting in a three-dimensional network in (III).

In summary, compounds (I) to (III) are all 1:1 organic salts in which two- or three-dimensional networks are formed. One remaining question is whether a 1:2 salt of an aliphatic diacid with 2-MeIm can be formed. According to the ΔpKa rule [ΔpKa = pKa(base H+) - pKa(acid)], an organic salt is formed when ΔpKa is greater than 3 and a cocrystal is obtained when ΔpKa is less than 0 (Childs & Hardcastle, 2007; Childs et al., 2007). For a system with 0 < ΔpKa < 3, the outcome will be easily affected by the crystallization conditions, such as solvent polarity, temperature, concentration, rate of cooling, etc. In order to identify whether a 1:2 salt of an aliphatic diacid with 2-MeIm exists theoretically, the pKa and ΔpKa values of these diacids and bases in an aqueous medium at 300 K have been calculated using the program SOLARIS (Advanced Chemistry Development, 2005). It can be seen from Table 4 that 1:1 organic salts can be easily formed when they are mixed in aqueous solution. In addition, 2:1 salts may be more likely to be formed in (II) and (III) than in (I). Further work on this is in progress.

Experimental top

1:2 Molar quantities of succinic acid (0.2 mmol, 23.6 mg) and 2-methylimidazole (0.4 mmol, 32.8 mg) for (I), glutaric acid (0.2 mmol, 26.4 mg) and 2-methylimidazole (0.4 mmol, 32.8 mg) for (II), and adipic acid (0.2 mmol, 29.2 mg) and 2-methylimidazole (0.4 mmol, 32.8 mg) for (III) were dissolved in water (15 ml). The mixtures were stirred for 10 min at ambient temperature and then filtered. The resulting colourless solutions were kept in air for several days. Crystals of (I), (II) and (III) were grown by slow evaporation.

Refinement top

For all three compounds, H atoms bonded to C atoms were positioned geometrically, with C—H = 0.93 (aromatic), 0.96 (methyl) or 0.97 Å (methylene), and refined in riding mode, with Uiso(H) = 1.2Ueq(aromatic and methylene C) or 1.5Ueq(methyl C). In (I), H atoms bonded to N and O atoms were found in a difference map and the N—H and O—H distances were refined with constraints [Restraints?] of N—H = 0.86 (2) Å and O—H = 0.82 (2) Å, and with Uiso(H) = 1.2Ueq(N) and 1.5Ueq(O). The cation is disordered over a mirror plane. Friedel pairs were averaged. H atoms bonded to N atoms in (II) were also found in a difference map and refined with the restraint N—H = 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N). The acid H atom is statistically disordered over two locations, both of which lie on inversion centres, and was refined with Uiso(H1B) = 1.5Ueq(O1) and Uiso(H1C) = 1.5Ueq(O3). In (III), H atoms bonded to N atoms were similarly found in a difference map and refined with the restraint N—H = 0.86 (2) Å and with Uiso(H) = 1.2Ueq(N). Atom H2B was found 1.22 Å away from atom O2 and placed on a general position. The O2—H2B distance was refined freely and the final outcome gave an indication of hydrogen-bridging in the adipate monoanion. Two water H atoms were also found in a difference map, one of which was disordered over two sites with occupancies of 0.5; these H atoms were refined with restraints of O—H = 0.82 (2) Å and H···H = 1.35 (2) Å, and with Uiso(H) = 1.5Ueq(O).

Computing details top

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines. Both components of the disordered 2-HMeIm are shown.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the two-dimensional network built from R66(28) hydrogen-bonded rings. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted. [Symmetry codes: (i) 2 - x, -y, 1 - z; (ii) 1 + x, y, -1 + z.]
[Figure 3] Fig. 3. The molecular structure of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
[Figure 4] Fig. 4. Part of the crystal structure of (II), showing the formation of the two-dimensional network built from R44(24) and R44(32) hydrogen-bonded rings. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted. [Symmetry codes: (i) -x, y, 1/2 - z; (ii) 1/2 - x, 3/2 - y, 1 - z; (iii) x, 1 - y, 1/2 + z.]
[Figure 5] Fig. 5. The molecular structure of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
[Figure 6] Fig. 6. Part of the crystal structure of (III), showing the formation of the (111) two-dimensional network built from two different sized edge-fused R44(34) hydrogen-bonded rings. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the motif have been omitted. [Symmetry code: (i) x - 1, y + 1, z.]
[Figure 7] Fig. 7. Part of the crystal structure of (III), showing the formation of the three-dimensional network (left) built from N1···O1, N2···O4(x - 1, 1 + 1 [y?], z) and O2···O3 hydrogen bonds, and the one-dimensional water chain (right). Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms bonded to C atoms and the disordered water H atoms have been omitted. [Symmetry codes: (ii) -x + 2, -y + 2, -z; (iii) -x + 1, -y + 2, -z.]
(I) 2-Methylimidazolium hydrogen succinate top
Crystal data top
C4H7N2+·C4H5O4F(000) = 424
Mr = 200.20Dx = 1.374 Mg m3
Orthorhombic, Cmc21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2Cell parameters from 2108 reflections
a = 6.8017 (10) Åθ = 2.3–26.6°
b = 8.1580 (11) ŵ = 0.11 mm1
c = 17.438 (2) ÅT = 296 K
V = 967.6 (2) Å3Block, colourless
Z = 40.25 × 0.12 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
654 independent reflections
Radiation source: fine focus sealed Siemens Mo tube573 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
0.3° wide ω exposures scansθmax = 28.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 98
Tmin = 0.963, Tmax = 0.991k = 1010
5389 measured reflectionsl = 2220
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0665P)2 + 0.0213P]
where P = (Fo2 + 2Fc2)/3
654 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.21 e Å3
4 restraintsΔρmin = 0.14 e Å3
Crystal data top
C4H7N2+·C4H5O4V = 967.6 (2) Å3
Mr = 200.20Z = 4
Orthorhombic, Cmc21Mo Kα radiation
a = 6.8017 (10) ŵ = 0.11 mm1
b = 8.1580 (11) ÅT = 296 K
c = 17.438 (2) Å0.25 × 0.12 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
654 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
573 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.991Rint = 0.024
5389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0344 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.21 e Å3
654 reflectionsΔρmin = 0.14 e Å3
112 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.

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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
C10.5457 (4)0.0023 (4)0.7332 (2)0.0344 (11)0.50
C20.2982 (7)0.1668 (6)0.7569 (3)0.0504 (11)0.50
H60.20880.23230.78320.061*0.50
C30.3004 (7)0.1383 (5)0.6818 (3)0.0497 (10)0.50
H70.21330.17990.64550.060*0.50
C40.7232 (7)0.1032 (4)0.74288 (13)0.0603 (12)0.50
H4A0.82960.03850.76270.090*0.50
H4B0.76010.14840.69410.090*0.50
H4C0.69420.19050.77800.090*0.50
C50.5000 (8)0.67258 (16)0.96057 (13)0.0312 (6)
C60.5000 (8)0.51001 (15)1.00107 (11)0.0329 (6)
H6A0.38480.50341.03370.040*0.50
H6B0.61520.50341.03370.040*0.50
C70.5000 (8)0.36551 (16)0.94673 (10)0.0319 (6)
H7A0.61510.37290.91410.038*0.50
H7B0.38490.37290.91410.038*0.50
C80.5000 (8)0.19911 (18)0.98588 (10)0.0269 (5)
N10.4561 (6)0.0359 (4)0.66822 (18)0.0413 (15)0.50
H10.470 (8)0.013 (5)0.6247 (16)0.050*0.50
N20.4518 (5)0.0818 (4)0.78840 (19)0.0409 (12)0.50
H20.475 (9)0.079 (4)0.8376 (13)0.049*0.50
O10.50000.7967 (2)1.00811 (13)0.0503 (6)
H1A0.50000.878 (4)0.982 (2)0.075*
O20.50000.6891 (3)0.89195 (12)0.0536 (6)
O30.50000.1882 (2)1.05627 (11)0.0442 (5)
O40.50000.0755 (2)0.94090 (11)0.0418 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.040 (3)0.0301 (13)0.0331 (18)0.0017 (11)0.0004 (12)0.0013 (14)
C20.057 (3)0.053 (2)0.041 (2)0.0156 (19)0.0008 (17)0.0063 (18)
C30.064 (3)0.051 (2)0.034 (2)0.0155 (19)0.0054 (17)0.0010 (18)
C40.072 (3)0.059 (3)0.050 (3)0.022 (2)0.007 (2)0.003 (2)
C50.0402 (14)0.0210 (11)0.0325 (14)0.0000.0000.0019 (9)
C60.0494 (13)0.0201 (10)0.0294 (13)0.0000.0000.0024 (9)
C70.0510 (14)0.0192 (10)0.0255 (13)0.0000.0000.0052 (9)
C80.0375 (13)0.0190 (10)0.0244 (12)0.0000.0000.0019 (8)
N10.062 (4)0.0367 (15)0.0255 (15)0.0043 (14)0.0004 (13)0.0054 (12)
N20.062 (4)0.0386 (15)0.0220 (14)0.0007 (13)0.0013 (12)0.0026 (12)
O10.0936 (16)0.0201 (8)0.0371 (13)0.0000.0000.0010 (8)
O20.1059 (17)0.0274 (10)0.0276 (12)0.0000.0000.0027 (8)
O30.0789 (15)0.0266 (9)0.0273 (11)0.0000.0000.0044 (8)
O40.0776 (12)0.0182 (7)0.0296 (10)0.0000.0000.0008 (8)
Geometric parameters (Å, º) top
C1—N2i1.160 (5)C6—C71.513 (2)
C1—N1i1.166 (5)C6—H6A0.9700
C1—N11.316 (5)C6—H6B0.9700
C1—N21.324 (5)C7—C81.520 (2)
C1—C41.492 (5)C7—H7A0.9700
C2—C31.331 (6)C7—H7B0.9700
C2—N21.369 (5)C8—O31.231 (3)
C2—N2i1.917 (5)C8—O41.278 (2)
C2—H60.9300N1—N1i0.598 (8)
C3—N11.370 (6)N1—C1i1.166 (5)
C3—N1i1.871 (6)N1—C3i1.871 (6)
C3—H70.9300N1—H10.86 (2)
C4—H4A0.9600N2—N2i0.655 (6)
C4—H4B0.9600N2—C1i1.160 (5)
C4—H4C0.9600N2—C2i1.917 (5)
C5—O21.204 (3)N2—H20.87 (2)
C5—O11.309 (3)O1—H1A0.81 (2)
C5—C61.503 (2)
N2i—C1—N1i132.4 (4)H6A—C6—H6B107.8
N2i—C1—N1127.2 (4)C6—C7—C8114.51 (14)
N1i—C1—N2125.9 (4)C6—C7—H7A108.6
N1—C1—N2107.5 (3)C8—C7—H7A108.6
N2i—C1—C4102.5 (3)C6—C7—H7B108.6
N1i—C1—C4104.7 (3)C8—C7—H7B108.6
N1—C1—C4126.3 (3)H7A—C7—H7B107.6
N2—C1—C4126.2 (3)O3—C8—O4123.73 (16)
C3—C2—N2107.3 (4)O3—C8—C7120.83 (13)
C3—C2—N2i102.1 (3)O4—C8—C7115.43 (12)
C3—C2—H6126.3N1i—N1—C3140.6 (3)
N2—C2—H6126.3C1—N1—C3109.7 (3)
N2i—C2—H6130.3C3—N1—C3i113.0 (4)
C2—C3—N1106.6 (4)C1i—N1—H1138 (3)
C2—C3—N1i102.3 (3)C1—N1—H1127 (3)
C2—C3—H7126.7C3—N1—H1121 (3)
N1—C3—H7126.7C3i—N1—H1103 (3)
N1i—C3—H7129.9N2i—N2—C2139.8 (3)
O2—C5—O1122.89 (17)C1—N2—C2108.9 (3)
O2—C5—C6124.44 (13)C2—N2—C2i112.3 (4)
O1—C5—C6112.66 (12)C1i—N2—H2143 (3)
C5—C6—C7113.17 (16)C1—N2—H2128 (3)
C5—C6—H6A108.9C2—N2—H2123 (4)
C7—C6—H6A108.9C2i—N2—H297 (4)
C5—C6—H6B108.9C5—O1—H1A106 (3)
C7—C6—H6B108.9
N2—C2—C3—N10.0 (5)C2—C3—N1—C10.2 (5)
N2i—C2—C3—N112.0 (5)N1i—C3—N1—C170.1 (4)
N2—C2—C3—N1i11.2 (5)C2—C3—N1—C3i69.9 (5)
N2i—C2—C3—N1i0.8 (4)N1i—C3—N1—C3i0.001 (2)
O2—C5—C6—C70.0 (3)N1i—C1—N2—N2i114.4 (4)
O1—C5—C6—C7180.0 (3)N1—C1—N2—N2i136.7 (3)
C5—C6—C7—C8180.0C4—C1—N2—N2i42.1 (3)
C6—C7—C8—O30.0 (3)N2i—C1—N2—C1i180.001 (3)
C6—C7—C8—O4180.0 (3)N1i—C1—N2—C1i65.6 (4)
N2i—C1—N1—N1i112.1 (4)N1—C1—N2—C1i43.3 (3)
N2—C1—N1—N1i137.3 (3)C4—C1—N2—C1i137.9 (3)
C4—C1—N1—N1i41.5 (3)N2i—C1—N2—C2137.1 (3)
N2i—C1—N1—C1i67.9 (4)N1i—C1—N2—C222.7 (6)
N1i—C1—N1—C1i179.999 (4)N1—C1—N2—C20.4 (4)
N2—C1—N1—C1i42.7 (3)C4—C1—N2—C2179.2 (4)
C4—C1—N1—C1i138.5 (3)N2i—C1—N2—C2i31.2 (2)
N2i—C1—N1—C325.6 (6)N1i—C1—N2—C2i83.2 (4)
N1i—C1—N1—C3137.7 (3)N1—C1—N2—C2i105.5 (3)
N2—C1—N1—C30.4 (4)C4—C1—N2—C2i73.3 (4)
C4—C1—N1—C3179.2 (4)C3—C2—N2—N2i67.2 (5)
N2i—C1—N1—C3i81.2 (4)C3—C2—N2—C1i18.9 (5)
N1i—C1—N1—C3i30.9 (2)N2i—C2—N2—C1i86.1 (3)
N2—C1—N1—C3i106.5 (3)C3—C2—N2—C10.2 (5)
C4—C1—N1—C3i72.4 (4)N2i—C2—N2—C167.5 (3)
C2—C3—N1—N1i69.9 (5)C3—C2—N2—C2i67.2 (5)
C2—C3—N1—C1i18.8 (4)N2i—C2—N2—C2i0.003 (4)
N1i—C3—N1—C1i88.7 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3ii0.86 (2)1.87 (2)2.691 (4)158 (4)
N2—H2···O40.87 (2)1.81 (2)2.680 (4)175 (6)
O1—H1A···O4iii0.81 (2)1.76 (2)2.558 (3)169 (5)
C2—H6···O2iv0.932.403.113 (5)134
C3—H7···O3v0.932.383.311 (5)175
C4—H4C···O2vi0.962.583.455 (5)152
Symmetry codes: (ii) x+1, y, z1/2; (iii) x, y+1, z; (iv) x1/2, y1/2, z; (v) x+1/2, y+1/2, z1/2; (vi) x, y1, z.
(II) 2-methylimidazolium hydrogen glutarate] top
Crystal data top
C4H7N2+·C5H7O4Z = 2
Mr = 214.22F(000) = 228
Triclinic, P1Dx = 1.283 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4433 (10) ÅCell parameters from 2213 reflections
b = 8.3842 (16) Åθ = 2.5–27.2°
c = 12.598 (2) ŵ = 0.10 mm1
α = 77.910 (3)°T = 295 K
β = 82.342 (3)°Plate, colourless
γ = 82.971 (3)°0.40 × 0.15 × 0.04 mm
V = 554.51 (18) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2151 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1720 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
0.3° wide ω exposures scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 66
Tmin = 0.951, Tmax = 0.996k = 1010
5770 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0847P)2 + 0.1211P]
where P = (Fo2 + 2Fc2)/3
2151 reflections(Δ/σ)max < 0.001
144 parametersΔρmax = 0.30 e Å3
2 restraintsΔρmin = 0.20 e Å3
Crystal data top
C4H7N2+·C5H7O4γ = 82.971 (3)°
Mr = 214.22V = 554.51 (18) Å3
Triclinic, P1Z = 2
a = 5.4433 (10) ÅMo Kα radiation
b = 8.3842 (16) ŵ = 0.10 mm1
c = 12.598 (2) ÅT = 295 K
α = 77.910 (3)°0.40 × 0.15 × 0.04 mm
β = 82.342 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2151 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
1720 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.996Rint = 0.022
5770 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0522 restraints
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.30 e Å3
2151 reflectionsΔρmin = 0.20 e Å3
144 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.

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 > 2sigma(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
xyzUiso*/Ueq
C11.3853 (4)0.3476 (2)0.31741 (16)0.0485 (5)
C21.5761 (4)0.3084 (3)0.15818 (17)0.0533 (5)
H21.61060.31350.08330.064*
C31.7171 (4)0.2286 (3)0.23501 (17)0.0539 (5)
H31.86940.16740.22390.065*
C41.2019 (4)0.4052 (3)0.4020 (2)0.0693 (7)
H4A1.15110.31280.45600.104*
H4B1.05940.46330.36890.104*
H4C1.27610.47690.43600.104*
C50.8425 (3)0.6691 (2)0.09582 (15)0.0458 (5)
C60.6260 (4)0.7925 (3)0.12038 (16)0.0541 (5)
H6A0.66540.90080.08200.065*
H6B0.48050.76780.09230.065*
C70.5627 (3)0.7953 (2)0.24066 (14)0.0453 (5)
H7A0.69500.84010.26610.054*
H7B0.55190.68410.28130.054*
C80.3183 (3)0.8970 (2)0.26297 (14)0.0445 (5)
H8A0.33191.00860.22340.053*
H8B0.18830.85400.23480.053*
C90.2418 (3)0.9001 (2)0.38207 (15)0.0434 (4)
N11.3706 (3)0.3814 (2)0.21091 (14)0.0520 (5)
H1A1.254 (4)0.450 (2)0.1791 (18)0.062*
N21.5957 (3)0.2536 (2)0.33310 (14)0.0521 (5)
H2A1.641 (4)0.218 (3)0.3976 (14)0.062*
O10.8437 (3)0.61753 (19)0.00735 (11)0.0612 (5)
H1B1.00000.50000.00000.092*
O21.0001 (3)0.6231 (2)0.15861 (15)0.0774 (6)
O30.0638 (3)1.0070 (2)0.40194 (11)0.0676 (5)
H1C0.00001.00000.50000.101*
O40.3432 (3)0.8026 (2)0.45303 (12)0.0759 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0462 (10)0.0512 (11)0.0479 (11)0.0012 (9)0.0067 (8)0.0114 (9)
C20.0522 (11)0.0641 (13)0.0431 (11)0.0048 (10)0.0076 (9)0.0142 (9)
C30.0460 (11)0.0615 (12)0.0519 (12)0.0092 (9)0.0064 (9)0.0136 (10)
C40.0612 (14)0.0805 (16)0.0641 (14)0.0048 (12)0.0043 (11)0.0234 (12)
C50.0430 (10)0.0518 (11)0.0413 (10)0.0118 (8)0.0044 (8)0.0155 (8)
C60.0547 (11)0.0634 (12)0.0405 (10)0.0250 (10)0.0069 (8)0.0182 (9)
C70.0435 (10)0.0524 (11)0.0387 (10)0.0112 (8)0.0060 (8)0.0144 (8)
C80.0413 (9)0.0539 (11)0.0374 (10)0.0100 (8)0.0059 (7)0.0145 (8)
C90.0418 (9)0.0502 (10)0.0376 (10)0.0067 (8)0.0047 (7)0.0135 (8)
N10.0482 (9)0.0571 (10)0.0495 (10)0.0106 (8)0.0154 (7)0.0106 (8)
N20.0523 (10)0.0617 (11)0.0398 (9)0.0056 (8)0.0126 (7)0.0063 (8)
O10.0630 (9)0.0801 (10)0.0388 (7)0.0296 (8)0.0106 (6)0.0260 (7)
O20.0673 (10)0.0933 (12)0.0841 (12)0.0448 (9)0.0411 (9)0.0554 (10)
O30.0694 (10)0.0807 (11)0.0419 (8)0.0377 (8)0.0005 (7)0.0172 (7)
O40.0836 (11)0.0936 (12)0.0380 (8)0.0439 (10)0.0083 (8)0.0143 (8)
Geometric parameters (Å, º) top
C1—N21.322 (3)C6—H6A0.9700
C1—N11.323 (3)C6—H6B0.9700
C1—C41.476 (3)C7—C81.516 (2)
C2—C31.332 (3)C7—H7A0.9700
C2—N11.368 (3)C7—H7B0.9700
C2—H20.9300C8—C91.508 (2)
C3—N21.366 (3)C8—H8A0.9700
C3—H30.9300C8—H8B0.9700
C4—H4A0.9600C9—O41.219 (2)
C4—H4B0.9600C9—O31.273 (2)
C4—H4C0.9600N1—H1A0.879 (16)
C5—O21.218 (2)N2—H2A0.863 (15)
C5—O11.276 (2)O1—H1B1.2300
C5—C61.514 (2)O3—H1C1.2300
C6—C71.513 (2)
N2—C1—N1106.83 (17)C6—C7—H7A109.2
N2—C1—C4126.8 (2)C8—C7—H7A109.2
N1—C1—C4126.36 (19)C6—C7—H7B109.2
C3—C2—N1106.63 (18)C8—C7—H7B109.2
C3—C2—H2126.7H7A—C7—H7B107.9
N1—C2—H2126.7C9—C8—C7114.24 (15)
C2—C3—N2107.02 (18)C9—C8—H8A108.7
C2—C3—H3126.5C7—C8—H8A108.7
N2—C3—H3126.5C9—C8—H8B108.7
C1—C4—H4A109.5C7—C8—H8B108.7
C1—C4—H4B109.5H8A—C8—H8B107.6
H4A—C4—H4B109.5O4—C9—O3123.56 (17)
C1—C4—H4C109.5O4—C9—C8120.82 (16)
H4A—C4—H4C109.5O3—C9—C8115.60 (16)
H4B—C4—H4C109.5C1—N1—C2109.79 (17)
O2—C5—O1123.74 (16)C1—N1—O2110.98 (13)
O2—C5—C6120.79 (16)C2—N1—O2137.56 (14)
O1—C5—C6115.46 (16)C1—N1—H1A124.3 (15)
C7—C6—C5113.96 (16)C2—N1—H1A125.5 (15)
C7—C6—H6A108.8C1—N2—C3109.72 (17)
C5—C6—H6A108.8C1—N2—H2A121.6 (15)
C7—C6—H6B108.8C3—N2—H2A128.6 (15)
C5—C6—H6B108.8C5—O1—H1B112
H6A—C6—H6B107.7C5—O2—N1142.40 (13)
C6—C7—C8111.89 (15)C9—O3—H1C113
N1—C2—C3—N20.2 (2)C4—C1—N1—O211.3 (3)
O2—C5—C6—C724.7 (3)C3—C2—N1—C10.1 (2)
O1—C5—C6—C7154.35 (19)C3—C2—N1—O2163.37 (17)
C5—C6—C7—C8169.60 (17)N1—C1—N2—C30.5 (2)
C6—C7—C8—C9178.28 (17)C4—C1—N2—C3179.1 (2)
C7—C8—C9—O414.0 (3)C2—C3—N2—C10.4 (2)
C7—C8—C9—O3167.67 (18)O1—C5—O2—N116.5 (4)
N2—C1—N1—C20.4 (2)C6—C5—O2—N1162.5 (2)
C4—C1—N1—C2179.2 (2)C1—N1—O2—C5145.3 (3)
N2—C1—N1—O2168.37 (13)C2—N1—O2—C551.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.86 (2)1.87 (2)2.695 (2)161 (2)
O1—H1B···O1ii1.231.232.462 (3)180
O3—H1C···O3iii1.231.232.458 (3)180
N1—H1A···O20.88 (2)1.88 (2)2.720 (2)159 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z; (iii) x, y+2, z+1.
(III) 2-methylimidazolium hydrogen adipate monohydrate top
Crystal data top
C4H7N2+·C6H9O4·H2OZ = 2
Mr = 246.26F(000) = 264
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.9383 (4) ÅCell parameters from 2128 reflections
b = 8.0682 (6) Åθ = 2.5–28.3°
c = 16.6840 (13) ŵ = 0.10 mm1
α = 96.880 (1)°T = 297 K
β = 92.794 (1)°Block, colourless
γ = 106.611 (1)°0.20 × 0.20 × 0.10 mm
V = 630.00 (8) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2421 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1905 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
0.3° wide ω exposures scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 66
Tmin = 0.970, Tmax = 0.990k = 99
6477 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0972P)2 + 0.0502P]
where P = (Fo2 + 2Fc2)/3
2421 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.25 e Å3
7 restraintsΔρmin = 0.21 e Å3
Crystal data top
C4H7N2+·C6H9O4·H2Oγ = 106.611 (1)°
Mr = 246.26V = 630.00 (8) Å3
Triclinic, P1Z = 2
a = 4.9383 (4) ÅMo Kα radiation
b = 8.0682 (6) ŵ = 0.10 mm1
c = 16.6840 (13) ÅT = 297 K
α = 96.880 (1)°0.20 × 0.20 × 0.10 mm
β = 92.794 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2421 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
1905 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.990Rint = 0.019
6477 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0507 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.25 e Å3
2421 reflectionsΔρmin = 0.21 e Å3
173 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.

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 > 2sigma(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
xyzUiso*/UeqOcc. (<1)
C10.2664 (4)0.9849 (2)0.26207 (12)0.0407 (5)
C20.2364 (4)0.8946 (2)0.38189 (13)0.0486 (5)
H20.19300.88430.43500.058*
C30.3761 (5)0.8038 (3)0.33743 (14)0.0530 (5)
H30.44820.71740.35370.064*
C40.2385 (5)1.0795 (3)0.19338 (13)0.0579 (6)
H4A0.05831.02430.16300.087*
H4B0.38801.07750.15890.087*
H4C0.25101.19830.21340.087*
C50.7289 (4)0.5974 (2)0.16367 (10)0.0371 (4)
C60.8623 (5)0.4902 (3)0.10637 (11)0.0445 (5)
H6A1.03370.48150.13420.053*
H6B0.73270.37300.09390.053*
C70.9369 (4)0.5593 (2)0.02766 (11)0.0400 (5)
H7A1.07230.67480.03930.048*
H7B0.76740.57030.00040.048*
C80.8109 (3)0.3255 (2)0.36414 (11)0.0341 (4)
C90.6488 (4)0.4454 (2)0.39884 (10)0.0333 (4)
H9A0.47610.42400.36390.040*
H9B0.76160.56480.39700.040*
C100.5691 (4)0.4305 (2)0.48431 (10)0.0326 (4)
H10A0.73780.44240.51950.039*
H10B0.43860.31560.48590.039*
N10.3944 (4)0.8610 (2)0.26335 (11)0.0463 (4)
H10.472 (4)0.821 (3)0.2210 (11)0.056*
N20.1689 (3)1.0066 (2)0.33376 (10)0.0428 (4)
H2A0.076 (4)1.086 (2)0.3508 (12)0.051*
O10.6446 (3)0.71668 (17)0.14081 (8)0.0495 (4)
O20.7027 (3)0.5613 (2)0.23510 (8)0.0565 (4)
H2B0.795 (5)0.453 (3)0.2611 (15)0.085*
O30.8821 (3)0.33834 (18)0.29100 (8)0.0516 (4)
O40.8761 (3)0.22082 (16)0.40353 (8)0.0445 (4)
O50.7220 (4)0.9398 (4)0.01894 (16)0.0995 (8)
H5D0.699 (9)0.876 (5)0.053 (2)0.149*
H5E0.610 (13)0.998 (8)0.018 (4)0.149*0.50
H5F0.870 (9)0.964 (11)0.001 (4)0.149*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0427 (10)0.0395 (9)0.0424 (11)0.0173 (8)0.0078 (8)0.0005 (8)
C20.0633 (13)0.0473 (11)0.0439 (12)0.0252 (9)0.0188 (10)0.0125 (9)
C30.0687 (13)0.0504 (11)0.0548 (13)0.0349 (10)0.0185 (10)0.0176 (9)
C40.0728 (15)0.0595 (13)0.0463 (13)0.0262 (11)0.0057 (11)0.0098 (10)
C50.0465 (10)0.0427 (9)0.0289 (10)0.0207 (8)0.0135 (8)0.0088 (7)
C60.0622 (12)0.0503 (10)0.0345 (11)0.0328 (9)0.0206 (9)0.0126 (8)
C70.0528 (11)0.0465 (10)0.0310 (10)0.0271 (8)0.0170 (8)0.0090 (8)
C80.0360 (9)0.0373 (9)0.0331 (10)0.0177 (7)0.0066 (7)0.0024 (7)
C90.0412 (9)0.0376 (9)0.0294 (10)0.0229 (7)0.0104 (7)0.0061 (7)
C100.0401 (9)0.0373 (9)0.0276 (9)0.0218 (7)0.0082 (7)0.0052 (7)
N10.0551 (10)0.0455 (9)0.0475 (11)0.0279 (7)0.0186 (8)0.0046 (7)
N20.0485 (9)0.0402 (8)0.0461 (10)0.0239 (7)0.0132 (7)0.0006 (7)
O10.0721 (9)0.0555 (8)0.0392 (8)0.0406 (7)0.0257 (7)0.0162 (6)
O20.0887 (11)0.0718 (10)0.0346 (8)0.0548 (8)0.0298 (7)0.0207 (7)
O30.0747 (10)0.0631 (9)0.0363 (8)0.0454 (7)0.0260 (7)0.0115 (6)
O40.0567 (8)0.0489 (7)0.0420 (8)0.0354 (6)0.0121 (6)0.0098 (6)
O50.0818 (14)0.1386 (19)0.1154 (19)0.0578 (14)0.0331 (12)0.0908 (15)
Geometric parameters (Å, º) top
C1—N21.322 (2)C7—H7A0.9700
C1—N11.329 (2)C7—H7B0.9700
C1—C41.472 (3)C8—O41.232 (2)
C2—C31.331 (3)C8—O31.294 (2)
C2—N21.376 (3)C8—C91.505 (2)
C2—H20.9300C9—C101.507 (2)
C3—N11.368 (3)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—H4A0.9600C10—C10ii1.526 (3)
C4—H4B0.9600C10—H10A0.9700
C4—H4C0.9600C10—H10B0.9700
C5—O11.244 (2)N1—H10.890 (15)
C5—O21.264 (2)N2—H2A0.915 (15)
C5—C61.511 (2)O2—H2B1.21 (3)
C6—C71.509 (3)O3—H2B1.26 (3)
C6—H6A0.9700O5—H5D0.80 (4)
C6—H6B0.9700O5—H5E0.82 (2)
C7—C7i1.530 (3)O5—H5F0.785 (19)
N2—C1—N1107.10 (18)C7i—C7—H7B109.1
N2—C1—C4126.71 (18)H7A—C7—H7B107.9
N1—C1—C4126.18 (18)O4—C8—O3121.13 (15)
C3—C2—N2106.48 (18)O4—C8—C9121.84 (16)
C3—C2—H2126.8O3—C8—C9117.03 (14)
N2—C2—H2126.8C8—C9—C10116.58 (14)
C2—C3—N1107.48 (19)C8—C9—H9A108.1
C2—C3—H3126.3C10—C9—H9A108.1
N1—C3—H3126.3C8—C9—H9B108.1
C1—C4—H4A109.5C10—C9—H9B108.2
C1—C4—H4B109.5H9A—C9—H9B107.3
H4A—C4—H4B109.5C9—C10—C10ii111.84 (17)
C1—C4—H4C109.5C9—C10—H10A109.2
H4A—C4—H4C109.5C10ii—C10—H10A109.2
H4B—C4—H4C109.5C9—C10—H10B109.3
O1—C5—O2120.97 (16)C10ii—C10—H10B109.2
O1—C5—C6120.80 (15)H10A—C10—H10B107.9
O2—C5—C6118.23 (16)C1—N1—C3109.24 (17)
C7—C6—C5115.71 (15)C1—N1—H1123.6 (14)
C7—C6—H6A108.4C3—N1—H1127.1 (14)
C5—C6—H6A108.4C1—N2—C2109.70 (16)
C7—C6—H6B108.4C1—N2—H2A126.5 (13)
C5—C6—H6B108.4C2—N2—H2A123.8 (13)
H6A—C6—H6B107.4C5—O2—H2B123.0 (13)
C6—C7—C7i112.34 (18)C8—O3—H2B111.4 (12)
C6—C7—H7A109.1H5D—O5—H5E114 (3)
C7i—C7—H7A109.1H5D—O5—H5F118 (4)
C6—C7—H7B109.1H5E—O5—H5F125 (6)
N2—C2—C3—N10.3 (2)N2—C1—N1—C30.1 (2)
O1—C5—C6—C711.5 (3)C4—C1—N1—C3179.76 (19)
O2—C5—C6—C7169.22 (17)C2—C3—N1—C10.3 (2)
C5—C6—C7—C7i178.4 (2)N1—C1—N2—C20.1 (2)
O4—C8—C9—C100.2 (2)C4—C1—N2—C2179.98 (18)
O3—C8—C9—C10179.49 (14)C3—C2—N2—C10.3 (2)
C8—C9—C10—C10ii174.59 (17)
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.89 (2)1.87 (2)2.751 (2)172 (2)
N2—H2A···O4iii0.91 (2)1.85 (2)2.7464 (19)168 (2)
O2—H2B···O31.22 (2)1.25 (2)2.4747 (19)177 (2)
O5—H5D···O10.80 (4)2.04 (4)2.843 (2)178 (4)
O5—H5F···O5iv0.79 (2)2.01 (3)2.770 (4)162 (7)
O5—H5E···O5v0.83 (2)1.93 (3)2.715 (4)157 (7)
Symmetry codes: (iii) x1, y+1, z; (iv) x+2, y+2, z; (v) x+1, y+2, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC4H7N2+·C4H5O4C4H7N2+·C5H7O4C4H7N2+·C6H9O4·H2O
Mr200.20214.22246.26
Crystal system, space groupOrthorhombic, Cmc21Triclinic, P1Triclinic, P1
Temperature (K)296295297
a, b, c (Å)6.8017 (10), 8.1580 (11), 17.438 (2)5.4433 (10), 8.3842 (16), 12.598 (2)4.9383 (4), 8.0682 (6), 16.6840 (13)
α, β, γ (°)90, 90, 9077.910 (3), 82.342 (3), 82.971 (3)96.880 (1), 92.794 (1), 106.611 (1)
V3)967.6 (2)554.51 (18)630.00 (8)
Z422
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.110.100.10
Crystal size (mm)0.25 × 0.12 × 0.080.40 × 0.15 × 0.040.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Multi-scan
(SADABS; Sheldrick, 1997)
Multi-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.963, 0.9910.951, 0.9960.970, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
5389, 654, 573 5770, 2151, 1720 6477, 2421, 1905
Rint0.0240.0220.019
(sin θ/λ)max1)0.6660.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.092, 1.10 0.052, 0.158, 1.09 0.050, 0.159, 1.10
No. of reflections65421512421
No. of parameters112144173
No. of restraints427
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.140.30, 0.200.25, 0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.86 (2)1.87 (2)2.691 (4)158 (4)
N2—H2···O40.87 (2)1.81 (2)2.680 (4)175 (6)
O1—H1A···O4ii0.81 (2)1.76 (2)2.558 (3)169 (5)
C2—H6···O2iii0.932.403.113 (5)133.8
C3—H7···O3iv0.932.383.311 (5)174.5
C4—H4C···O2v0.962.583.455 (5)151.5
Symmetry codes: (i) x+1, y, z1/2; (ii) x, y+1, z; (iii) x1/2, y1/2, z; (iv) x+1/2, y+1/2, z1/2; (v) x, y1, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O4i0.863 (15)1.865 (17)2.695 (2)161 (2)
O1—H1B···O1ii1.231.232.462 (3)180
O3—H1C···O3iii1.231.232.458 (3)180
N1—H1A···O20.879 (16)1.881 (17)2.720 (2)159 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z; (iii) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.889 (15)1.867 (16)2.751 (2)172 (2)
N2—H2A···O4i0.913 (15)1.846 (16)2.7464 (19)168.4 (19)
O2—H2B···O31.22 (2)1.25 (2)2.4747 (19)177 (2)
O5—H5D···O10.80 (4)2.04 (4)2.843 (2)178 (4)
O5—H5F···O5ii0.785 (19)2.01 (3)2.770 (4)162 (7)
O5—H5E···O5iii0.825 (19)1.93 (3)2.715 (4)157 (7)
Symmetry codes: (i) x1, y+1, z; (ii) x+2, y+2, z; (iii) x+1, y+2, z.
ΔpKa [= pKa (BaseH+ - Acid)] for the three title compounds in water top
CompoundMolecular componentΔpKa1ΔpKa2
(I)2-MeIm and Succ3.912.63
(II)2-MeIm and Glut3.822.88
(III)2-MeIm and Adip3.763.02
2-MeIm = 2-methyl-imidazole, pKa = 8.15 for its conjugated cation. Succ = succinic acid, pKa1 = 4.24, pKa2 = 5.52. Glut = glutaric acid, pKa1 = 4.33, pKa2 = 5.27. Adip = adipic acid, pKa1 = 4.39, pKa2 = 5.13. All the pKa values were calculated using SOLARIS (Advanced Chemistry Development, 2005).
 

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