Structural characterization of two tetra­chlorido­zincate salts of 4-carb­oxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate

Martens, S.J.; Geiger, D.K.

doi:10.1107/S2056989017000317

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Volume 73| Part 2| February 2017| Pages 162-167

https://doi.org/10.1107/S2056989017000317

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Structural characterization of two tetrachloridozincate salts of 4-carboxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate

Sean J. Martens ^a and David K Geiger ^a ^*

^aDepartment of Chemistry, SUNY–College at Geneseo, Geneseo, New York 14454, USA
^*Correspondence e-mail: geiger@geneseo.edu

Edited by T. J. Prior, University of Hull, England (Received 20 December 2016; accepted 7 January 2017; online 13 January 2017)

Imidazole-containing compounds exhibit a myriad of pharmacological activities. Two tetrachloridozincate salts of 4-carboxy-1H-imidazol-3-ium, ImHCO₂H⁺, are reported. Bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate monohydrate, (C₄H₅N₂O₂)₂[ZnCl₄]·H₂O, (I), crystallizes as a monohydrate salt, while bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate bis(1H-imidazol-3-ium-4-carboxylato) monohydrate, (C₄H₅N₂O₂)₂[ZnCl₄]·2C₄H₄N₂O₂·H₂O, (II), is a co-crystal salt with six residues: two ImHCO₂H⁺ cations, two formula units of the zwitterionic 1H-imidazol-3-ium-4-carboxylate, ImHCO₂, one tetrachloridozincate anion and one water molecule disordered over two sites in a 0.60 (4):0.40 (4) ratio. The geometric parameters of the ImHCO₂H⁺ and the ImHCO₂ moieties are the same within the standard uncertainties of the measurements. Both compounds exhibit extensive hydrogen bonding, including involvement of the tetrachloridozincate anion, resulting in interconnected chains of anions joined by water molecules.

Keywords: crystal structure; co-crystal; hydrate; tetrachloridozincate; imidazolium.

CCDC references: 1526096; 1526095

1. Chemical context

Imidazole-containing compounds find use in numerous pharmaceuticals including fungicides, antiviral agents, antiarrhythmics, antihistamines, and anthelmintics (Varala et al., 2007 ; Horton et al., 2003 ; López-Rodríguez et al., 1999 ). Recent studies have shown that imidazole and benzimidazole derivatives exhibit pharmacological activity in histamine signaling (Tichenor et al., 2015 ; Marson, 2011 ), and act as tau aggregation inhibitors for Alzheimer's disease (Bulic et al., 2013 ), and in the central nervous system (Robichaud et al., 2011 ; Sheffler et al., 2011 ). Further, derivatized imidazole-5-carboxylic acids have been shown to be angiotensin-converting enzyme (ACE) inhibitors (Jallapally et al., 2015 ; Li et al., 1998 ; Yanagisawa et al., 1996 ).

As a result of the myriad binding modes available to imidazole ligands that bear carboxylic acid substituents, they have found use in the preparation of several metal organic frameworks, MOFs (Starosta & Leciejewicz, 2006 ; Yin et al., 2009 , 2012 ; Sun & Yang, 2007 ; Sun et al., 2006 ). The synthesis and characterization of novel MOFs is an area of active research because of their potential use in such diverse areas as gas storage, catalysis, chemical sensors and molecular separation (Dey et al., 2014 ; Kreno et al., 2012 ; Farha & Hupp, 2010 ). Neutral carboxyimidazoles exist in their zwitterionic form and none of the reported compounds have the carboxyimidazole ligand in the fully protonated form. However, there are examples of MOFs with anionic repeating units and imidazolium cations (Shao & Yu, 2014 ; Wang et al., 2013 ).

Although the structures of the zwitterionic 1H-imidazol-3-ium-4-carboxylate, (III), (Cao et al., 2012 ) and the corresponding 2-isopropyl (Du et al., 2011 ) and 2-methyl (Guo, 2009 ) derivatives have been reported, to our knowledge, fully protonated imidazolecarboxylic acid species have not been structurally characterized. Compounds (I) and (II) possess the carboxyimidazole in its fully protonated form and so contribute to the knowledge base of this class of compounds.

2. Structural commentary

Fig. 1 shows the atom-labeling scheme employed for (I). The asymmetric unit consists of two 4-carboxy-1H-imidazol-3-ium cations (ImHCO₂H⁺), one tetrachloridozincate anion, and one water molecule. Thus, compound (I) is classified as a salt solvate (Grothe et al., 2016 ) with four residues.

Figure 1
The molecular structure of (I)

, showing the atom-labeling scheme. Non-hydrogen anisotropic displacement parameters are drawn at the 50% probability level.

Compound (II) is an example of a rare co-crystal salt solvate with six residues (Grothe et al., 2016). The asymmetric unit consists of two ImHCO₂H⁺ cations, one tetrachloridozincate anion, two 1H-imidazol-3-ium-4-carboxylate zwitterions (ImHCO₂), and one water molecule. The atom-labeling scheme employed is shown in Fig. 2.

Figure 2
The molecular structure of (II)

, showing the atom-labeling scheme. Non-hydrogen anisotropic displacement parameters are drawn at the 50% probability level.

The geometric parameters determined for the tetrachloridozincate anions in (I) and (II) are found in Tables 1 and 2, respectively. The average Zn—Cl bond length is 2.273 (3) and 2.272 (15) Å, respectively, for (I) and (II), which are within the range 2.2409 (3)–2.3085 (7) Å found in other examples of tetrachloridozincate salts (Govindan et al., 2014a ,b ; Leesakul et al., 2012 ; Goh et al., 2012 ; Kefi et al., 2011 ). The same example structures exhibit Cl—Zn—Cl angles in the range 102.256 (10) to 112.72 (3)°. The average angles found in (I) and (II) are 109 (2)° and 109 (3)°, respectively, and the individual values exhibit comparable ranges (Tables 1 and 2).

Table 1
Selected geometric parameters (Å, °) for (I)

Zn1—Cl2	2.2690 (7)	O1—C1	1.313 (2)
Zn1—Cl3	2.2704 (6)	O2—C1	1.200 (2)
Zn1—Cl4	2.2737 (6)	O3—C5	1.305 (2)
Zn1—Cl1	2.2794 (6)	O4—C5	1.201 (3)

Cl2—Zn1—Cl3	107.93 (2)	Cl3—Zn1—Cl1	112.84 (2)
Cl2—Zn1—Cl4	111.11 (2)	Cl4—Zn1—Cl1	107.92 (2)
Cl3—Zn1—Cl4	109.21 (3)	O2—C1—O1	124.9 (2)
Cl2—Zn1—Cl1	107.85 (2)	O4—C5—O3	125.4 (2)

O2—C1—C2—N1	4.6 (3)	O4—C5—C6—N3	−1.8 (3)

Table 2
Selected geometric parameters (Å, °) for (II)

Zn1—Cl3	2.2577 (12)	O3—C8	1.220 (5)
Zn1—Cl4	2.2589 (11)	O4—C8	1.277 (5)
Zn1—Cl1	2.2758 (12)	O5—C12	1.274 (5)
Zn1—Cl2	2.2948 (12)	O6—C12	1.222 (5)
O1—C4	1.271 (4)	O7—C16	1.224 (5)
O2—C4	1.229 (4)	O8—C16	1.267 (5)

Cl3—Zn1—Cl4	111.21 (4)	Cl1—Zn1—Cl2	108.62 (5)
Cl3—Zn1—Cl1	112.42 (5)	O2—C4—O1	126.3 (4)
Cl4—Zn1—Cl1	109.31 (5)	O3—C8—O4	125.6 (4)
Cl3—Zn1—Cl2	104.23 (5)	O6—C12—O5	126.3 (4)
Cl4—Zn1—Cl2	110.95 (4)	O7—C16—O8	126.3 (4)

N2—C1—C4—O2	5.7 (6)	N5—C9—C12—O6	3.2 (6)
N3—C5—C8—O3	−2.3 (6)	N7—C13—C16—O7	6.3 (6)

There are no noteworthy differences in the C—C and C—N bond lengths between the ImHCO₂H⁺ cations and ImHCO₂ zwitterions found in (I) and (II). The N—C′ bond length, where C′ is the carbon atom bonded to both nitrogen atoms in a given ring (formally, the 2 position in the ring), is consistently shorter than the N—C′′ bond length, where C′′ represents the carbon in the formal 4 or 5 position in the ring, for all of the ImHCO₂H⁺ and ImHCO₂ residues. This observation is consistent with other reported imidazoles and imidazolium salts (e.g., Mohamed et al., 2014 ; Trifa et al., 2013 ; Chérif et al., 2013 ; Yu, 2012 ; Zhu, 2012 ).

The carboxy and carboxylate groups are tilted slightly from the imidazole plane in all cases. The N—C—C—O torsion angles are reported in Tables 1 and 2. In both (I) and (II), the carboxy and carboxylate groups are unsymmetrical. For the carboxy groups, the C—OH bond is longer than the C=O bond. These observations are consistent with the geometric parameters found in similar imidazolecarboxylic acids (Cao et al., 2012; Du et al., 2011; Guo, 2009). The observed O—C—O bond angles of the fully protonated form in (I) and (II) and the zwitterionic form in (II) are the same within the standard uncertainties of the refinement.

3. Supramolecular features

An extensive hydrogen-bonding network in (I) involving the tetrachloridozincate anion and the water of hydration results in chains parallel to [2 $[\overline{2}]$ 0], as seen in Fig. 3 and Table 3. Additional Cl⋯H—O—H⋯Cl interactions along [100] join the chains (Fig. 4). N—H⋯O(water), N—H⋯Cl, and O—H⋯O hydrogen bonds incorporate the ImHCO₂H⁺ cations into the three-dimensional extended structure. Using graph-set analysis to describe the hydrogen bonding (Etter et al., 1990 ), an R₄⁴(20) ring is observed with four oxygen acceptors, two oxygen donors and two nitrogen donors. One oxygen donor, two oxygen acceptor rings, R₁²(4), involving a carboxy group are also present.

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1SA⋯Cl2	0.83 (2)	2.42 (2)	3.192 (3)	155 (4)
O1S—H1SB⋯Cl4ⁱ	0.81 (2)	2.94 (4)	3.392 (2)	118 (3)
O1S—H1SB⋯Cl1ⁱⁱ	0.81 (2)	3.05 (4)	3.540 (3)	122 (4)
O1—H1A⋯Cl4ⁱⁱⁱ	0.83 (2)	2.25 (2)	3.0723 (19)	171 (3)
O3—H3A⋯O1S^iv	0.83 (2)	1.77 (2)	2.576 (3)	163 (3)
N1—H1N⋯Cl1	0.84 (2)	2.37 (2)	3.2105 (17)	178 (2)
N2—H2N⋯Cl1ⁱ	0.86 (2)	2.85 (2)	3.3787 (19)	122 (2)
N2—H2N⋯O2ⁱ	0.86 (2)	1.99 (2)	2.745 (2)	146 (2)
N3—H3N⋯Cl3^v	0.83 (2)	2.37 (2)	3.1941 (18)	177 (2)
N4—H4N⋯Cl3^vi	0.86 (2)	2.83 (2)	3.3586 (19)	121 (2)
N4—H4N⋯O4ⁱ	0.86 (2)	2.00 (2)	2.753 (2)	146 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y-1, z; (iii) -x, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) x, y, z+1; (vi) x+1, y, z+1.

Figure 3
Partial packing diagram of (I)

, showing the water–tetrachloridozincate chains. Only the tetrachloridozincate anion and the water of hydration are shown.

Figure 4
Packing diagram of (I)

, showing the hydrogen-bonding scheme. Only H atoms involved in the interactions are shown.

Figs. 5 and 6 show two views of the crystal packing observed in (II). Hydrogen-bonding parameters are found in Table 4. As seen in Fig. 5, there are several hydrogen-bonding ring motifs that are common to (I) and (II). An R₄⁴(20) ring is observed with four oxygen acceptors, two oxygen donors and two nitrogen donors, and there is a one oxygen donor, two oxygen acceptor ring, R₁²(4), involving a carboxy group. R₂²(7) rings involving two nitrogen donors and two oxygen acceptors are also observed. There are two rings containing chlorine acceptor atoms: an R₄⁴(15) system with one oxygen donor, three nitrogen donors, one oxygen acceptor and three chlorine acceptors; and an R₁²(4) ring with a single oxygen donor and two chlorine acceptors. Similarly to (I), chains of hydrogen-bonded tetrachloridozincate anions and water molecules of hydration are found parallel to [2 $[\overline{2}]$ 0].

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O5ⁱ	0.87 (2)	1.63 (2)	2.476 (4)	163 (5)
O4—H4A⋯O6ⁱ	0.87 (2)	2.52 (4)	3.205 (4)	136 (4)
O8—H8A⋯O1ⁱⁱ	0.85 (2)	1.65 (2)	2.484 (4)	166 (5)
O8—H8A⋯O2ⁱⁱ	0.85 (2)	2.63 (4)	3.162 (4)	122 (4)
O1S—H1A⋯Cl2	0.85 (2)	2.52 (5)	3.330 (9)	159 (10)
O1S—H1B⋯Cl1ⁱⁱⁱ	0.84 (2)	2.97 (9)	3.546 (15)	128 (10)
O1S—H1B⋯Cl4ⁱⁱⁱ	0.84 (2)	2.93 (7)	3.499 (11)	127 (8)
O2S—H2A⋯Cl2	0.85 (2)	2.61 (12)	3.382 (17)	150.20
O2S—H2B⋯Cl1ⁱⁱⁱ	0.85 (2)	2.36 (10)	3.13 (2)	150 (17)
N1—H1N⋯O2^iv	0.88 (2)	1.86 (2)	2.712 (4)	160 (4)
N2—H2N⋯Cl2	0.87 (2)	2.44 (2)	3.297 (3)	167 (4)
N3—H3N⋯O1S	0.87 (2)	2.01 (2)	2.860 (10)	168 (4)
N3—H3N⋯O2S	0.87 (2)	1.89 (2)	2.739 (12)	165 (4)
N4—H4N⋯O3^iv	0.85 (2)	1.92 (3)	2.677 (5)	148 (4)
N5—H5N⋯Cl4	0.86 (2)	2.39 (2)	3.247 (3)	173 (4)
N6—H6N⋯O6^iv	0.87 (2)	1.85 (3)	2.661 (4)	156 (4)
N7—H7N⋯Cl1	0.89 (2)	2.32 (2)	3.205 (3)	175 (4)
N8—H8N⋯O7^iv	0.87 (2)	1.78 (2)	2.628 (4)	164 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) x+1, y-1, z; (iv) x+1, y, z.

Figure 5
A view of the hydrogen bonding in (II)

, showing the ring motifs. Only H atoms involved in the interactions are shown. Only the major contributor to the disorder model of the water molecule is shown.

Figure 6
A second view of the hydrogen bonding in (II)

. Only H atoms involved in the hydrogen bonds are shown. Only the major contributor to the disorder model of the water molecule is shown.

In (I), a weak π–π interaction between ImHCO₂H⁺ cations related by a crystallographically imposed center of symmetry is observed with a centroid-to-centroid distance of 3.5781 (15) Å and an interplanar distance of 3.4406 (9) Å, corresponding to 0.983 Å slippage (Spek, 2009 ). Two independent weak π–π interactions between ImHCO₂H⁺ cations and ImHCO₂ zwitterions are observed in (II). The principal one involves the rings containing N1 and N7 with a centroid-to-centroid distance of 3.5871 (3) Å, an interplanar distance of 3.3591 (18) Å and a dihedral angle of 2.6 (2)° between rings (Spek, 2009). The weaker π–π interaction involves the rings containing N3 and N5 and has a centroid-to-centroid distance of 3.740 (3) Å, an interplanar distance of 3.3140 (17) Å and a dihedral angle of 1.2 (2) Å between planes.

Fig. 7 shows representations of the observed π stacking in which members of interacting pairs of molecules are projected into the same plane. A π–π interaction is also observed in the solid-state structure of the ImHCO₂ zwitterion, labeled (III) (Cao et al., 2012). In (III), the centroid–centroid distance is longer [3.674 (4) Å] than that observed between the fully protonated form in (I) and the principal interaction between the zwitterion and the protonated form in (II). In all of the pairs except in (I), the members of the pairs are arranged in a head-to-head configuration.

Figure 7
Projections of π-stacked molecules. The molecules are related by the symmetry transformations (I)

−x + 1, −y + 1, −z + 1; (IIa) x, y, z; (IIb) x + 1, y − 1,z; (III) x, y, z + 1.

4. Database survey

The structure of 1-H-imidazol-3-ium-4-carboxylate has been reported (Cao et al., 2012) and the structures of the 2-methyl and 2-isopropyl derivatives of the zwitterion 5-carboxy-1H-3-ium-4-carboxylate monohydrate have been reported (Guo, 2009; Du et al., 2011). Several polymeric compounds with bridging 1H-imidazole-4-carboxylato ligands have been reported, including one with Ca^II (Starosta & Leciejewicz, 2006) and two with Cd^II (Yin et al., 2009, 2012). The structures of monomeric compounds with 1H-imidazole-4-carboxylato-κ²N,O ligands and Mg^II (Gryz et al., 2007 ), Mn^II (Xiong et al., 2013 ), Co^II (Chen, 2012 ; Artetxe et al., 2013 ), Ni^II (Zheng et al., 2011 ), Cu^II (Reinoso et al., 2015 ), and Zn^II (Gryz et al., 2007; He, 2006 ; Shuai et al., 2011 ) have been determined. Tetranuclear Mn^II complexes with 1H-imidazole-4-carboxylato-κ²N,O and the structurally similar 4-imidazoleacetate ligand have also been characterized (Boskovic et al., 2000 ). The structures of numerous imidazolium salts are known (e.g., Mohamed et al.,, 2014; Trifa et al., 2013; Chérif et al., 2013; Yu, 2012; Zhu, 2012; Ishida & Kashino, 2001 ; Gili et al., 2000 ; Pavan Kumar & Kumara Swamy, 2005 ; Hashizume et al., 2001 ; Moreno-Fuquen et al., 2009a ,b , 2011 ; Zhang et al., 2011 ; Sun et al., 2002 ; Fukunaga & Ishida, 2003 ). There are many examples of reported structures of tetrachloridozincate salts (e.g., Govindan et al., 2014a,b; Leesakul et al., 2012; Goh et al., 2012; Kefi et al., 2011).

5. Synthesis and crystallization

Compounds (I) and (II) were obtained during the attempted syntheses of Zn^II coordination polymers. (I) was obtained by dissolving 113 mg (0.829 mmol) ZnCl₂ and 194 mg (1.73 mmol) 1H-imidazole-4-carboxylic acid in ethanol. Six drops of 6 M HCl were added and the mixture was heated to reflux with stirring. The warm solution was filtered and the filtrate was allowed to cool. After a few days, crystalline clumps of the product were obtained. ¹H NMR (400 MHz, dmso-d₆, p.p.m.): 7.97 (s, 2H), 8.51 (s, 2H). ¹³C NMR (100 MHz, dmso-d₆, p.p.m.): 126.1, 127.4, 137.7, 161.3. A crystal cut from a larger mass of crystals was used for X-ray analysis.

Compound (II) was prepared similarly to (I) except that methanol was the solvent and no HCl was added to the reaction mixture. Single crystals for X-ray analysis were obtained by slow evaporation of a methanol solution.¹H NMR (400 MHz, dmso-d₆, p.p.m.): 8.15 (s, 4H), 8.95 (s, 4H). ¹³C NMR (100 MHz, dmso-d₆, p.p.m.): 125.4, 126.1, 137.6, 160.3.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. For (I), data completeness was 97.9% and for (II) it was 95.2%. For both (I) and (II), all hydrogen atoms were located in difference Fourier maps. The hydrogen atoms bonded to carbon were refined using a riding model with a C—H distance of 0.95 Å and hydrogen-atom isotropic displacement parameters were set using the approximation U_iso(H) = 1.2U_eq(C). The O—H and N—H distances were restrained to 0.84 and 0.88 Å, respectively. The isotropic displacement parameters of the hydrogen atoms bonded to nitrogen were set using the approximation U_iso(H) = 1.2U_eq(N). In (I), isotropic displacement parameters of the hydrogen atoms bonded to oxygen were refined freely, but for (II) they were set using the approximation U_iso(H) = 1.5U_eq(O). For (II), the water molecule is disordered over two positions. In addition to the aforementioned distance restraint, an H—O—H angle restraint of 105° was employed. The occupancies refined to 0.60 (4):0.40 (4).

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	(C₄H₅N₂O₂)₂[ZnCl₄]·H₂O	(C₄H₄N₂O₂)₂[ZnCl₄]·2C₄H₅N₂O₂H₂O
M_r	451.39	675.57
Crystal system, space group	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$
Temperature (K)	200	200
a, b, c (Å)	6.9094 (10), 7.5828 (12), 16.468 (3)	6.9369 (19), 6.9624 (15), 28.483 (8)
α, β, γ (°)	79.455 (4), 84.489 (4), 83.833 (4)	89.524 (9), 85.622 (9), 71.202 (8)
V (Å³)	840.7 (2)	1298.3 (6)
Z	2	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	2.12	1.42
Crystal size (mm)	0.60 × 0.50 × 0.20	0.50 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART X2S benchtop	Bruker SMART X2S benchtop
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.41, 0.68	0.50, 0.76
No. of measured, independent and observed [I > 2σ(I)] reflections	10429, 3375, 2995	10560, 4855, 3619
R_int	0.032	0.042
(sin θ/λ)_max (Å⁻¹)	0.625	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.064, 1.03	0.050, 0.135, 1.03
No. of reflections	3375	4855
No. of parameters	227	395
No. of restraints	8	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.28	0.63, −0.71
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1526096; 1526095

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989017000317/pj2040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017000317/pj2040Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989017000317/pj2040IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989017000317/pj2040Isup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989017000317/pj2040IIsup5.mol

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) Bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate monohydrate top

Crystal data top

(C₄H₅N₂O₂)₂[ZnCl₄]·H₂O	Z = 2
M_r = 451.39	F(000) = 452
Triclinic, P1	D_x = 1.783 Mg m⁻³
a = 6.9094 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5828 (12) Å	Cell parameters from 6894 reflections
c = 16.468 (3) Å	θ = 2.5–27.5°
α = 79.455 (4)°	µ = 2.12 mm⁻¹
β = 84.489 (4)°	T = 200 K
γ = 83.833 (4)°	Plate, clear colourless
V = 840.7 (2) Å³	0.60 × 0.50 × 0.20 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	3375 independent reflections
Radiation source: sealed microfocus tube	2995 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.032
Detector resolution: 8.3330 pixels mm^-1	θ_max = 26.4°, θ_min = 2.5°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
T_min = 0.41, T_max = 0.68	l = −20→19
10429 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)] = 0.024	Hydrogen site location: mixed
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0292P)² + 0.2531P] where P = (F_o² + 2F_c²)/3
3375 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.53 e Å⁻³
8 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Zn1	0.24426 (3)	0.35245 (3)	0.23892 (2)	0.03225 (8)
Cl1	0.07702 (7)	0.58951 (7)	0.29003 (3)	0.04037 (13)
Cl2	0.56514 (8)	0.40109 (8)	0.22143 (4)	0.04596 (14)
Cl3	0.14855 (8)	0.32216 (8)	0.11448 (3)	0.04391 (14)
Cl4	0.19391 (9)	0.09768 (8)	0.33224 (3)	0.04754 (14)
O1S	0.7881 (4)	0.0065 (3)	0.25272 (16)	0.0744 (6)
H1SA	0.755 (6)	0.114 (3)	0.256 (2)	0.113 (16)*
H1SB	0.902 (3)	−0.023 (6)	0.241 (3)	0.112 (17)*
O1	0.2088 (3)	0.8341 (3)	0.57654 (11)	0.0583 (5)
H1A	0.096 (3)	0.846 (4)	0.5976 (19)	0.080 (11)*
O2	0.0547 (2)	0.7334 (2)	0.48378 (10)	0.0499 (4)
O3	0.4700 (2)	0.1089 (2)	0.82247 (10)	0.0488 (4)
H3A	0.371 (3)	0.082 (4)	0.8047 (18)	0.068 (9)*
O4	0.2491 (2)	0.1786 (3)	0.92209 (10)	0.0509 (4)
N1	0.4180 (2)	0.6761 (2)	0.39214 (10)	0.0328 (4)
H1N	0.328 (3)	0.656 (3)	0.3653 (13)	0.039*
N2	0.7041 (3)	0.6977 (3)	0.42572 (12)	0.0398 (4)
H2N	0.830 (2)	0.694 (3)	0.4249 (15)	0.048*
N3	0.5549 (2)	0.2595 (2)	1.00903 (11)	0.0354 (4)
H3N	0.448 (3)	0.280 (3)	1.0351 (14)	0.042*
N4	0.8615 (3)	0.2308 (3)	0.97687 (12)	0.0414 (4)
H4N	0.985 (2)	0.234 (3)	0.9774 (16)	0.05*
C1	0.2014 (3)	0.7670 (3)	0.50896 (12)	0.0340 (4)
C2	0.3956 (3)	0.7354 (3)	0.46709 (12)	0.0304 (4)
C3	0.6053 (3)	0.6554 (3)	0.36821 (13)	0.0374 (5)
H3	0.6597	0.6168	0.3185	0.045*
C4	0.5780 (3)	0.7487 (3)	0.48777 (13)	0.0365 (4)
H4	0.6113	0.7864	0.5362	0.044*
C5	0.4145 (3)	0.1639 (3)	0.89239 (12)	0.0352 (4)
C6	0.5806 (3)	0.2008 (3)	0.93398 (12)	0.0320 (4)
C7	0.7275 (3)	0.2773 (3)	1.03332 (14)	0.0404 (5)
H7	0.7507	0.3166	1.0828	0.048*
C8	0.7758 (3)	0.1833 (3)	0.91435 (13)	0.0395 (5)
H8	0.8402	0.1452	0.8661	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03082 (14)	0.03910 (14)	0.02828 (13)	−0.00235 (10)	−0.00091 (9)	−0.01089 (10)
Cl1	0.0302 (3)	0.0506 (3)	0.0444 (3)	0.0027 (2)	−0.0016 (2)	−0.0234 (2)
Cl2	0.0303 (3)	0.0544 (3)	0.0579 (3)	−0.0051 (2)	−0.0010 (2)	−0.0226 (3)
Cl3	0.0329 (3)	0.0699 (4)	0.0337 (3)	−0.0025 (2)	−0.0048 (2)	−0.0219 (2)
Cl4	0.0491 (3)	0.0446 (3)	0.0421 (3)	0.0028 (2)	0.0056 (2)	0.0016 (2)
O1S	0.0736 (16)	0.0632 (14)	0.0966 (17)	0.0020 (12)	−0.0382 (14)	−0.0293 (12)
O1	0.0376 (10)	0.0984 (14)	0.0484 (10)	−0.0049 (9)	−0.0019 (8)	−0.0392 (10)
O2	0.0282 (8)	0.0812 (12)	0.0462 (9)	−0.0099 (8)	−0.0035 (7)	−0.0234 (8)
O3	0.0444 (10)	0.0668 (11)	0.0403 (9)	−0.0072 (8)	−0.0005 (7)	−0.0231 (8)
O4	0.0276 (8)	0.0815 (12)	0.0447 (9)	−0.0031 (8)	−0.0002 (7)	−0.0164 (8)
N1	0.0264 (9)	0.0406 (9)	0.0332 (9)	−0.0024 (7)	−0.0075 (7)	−0.0089 (7)
N2	0.0227 (9)	0.0491 (10)	0.0480 (10)	−0.0037 (8)	−0.0042 (8)	−0.0081 (8)
N3	0.0266 (9)	0.0453 (10)	0.0340 (9)	−0.0015 (8)	0.0024 (7)	−0.0098 (8)
N4	0.0235 (9)	0.0515 (11)	0.0478 (11)	−0.0049 (8)	−0.0014 (8)	−0.0046 (9)
C1	0.0316 (11)	0.0408 (11)	0.0299 (10)	−0.0025 (9)	−0.0045 (8)	−0.0064 (8)
C2	0.0286 (10)	0.0335 (10)	0.0297 (9)	−0.0016 (8)	−0.0055 (8)	−0.0060 (8)
C3	0.0308 (11)	0.0429 (11)	0.0383 (11)	−0.0020 (9)	−0.0016 (9)	−0.0080 (9)
C4	0.0323 (11)	0.0411 (11)	0.0381 (11)	−0.0051 (9)	−0.0085 (9)	−0.0082 (9)
C5	0.0343 (12)	0.0373 (11)	0.0324 (10)	−0.0011 (9)	−0.0016 (8)	−0.0034 (8)
C6	0.0295 (11)	0.0351 (10)	0.0298 (9)	−0.0017 (8)	0.0008 (8)	−0.0043 (8)
C7	0.0330 (12)	0.0484 (12)	0.0410 (11)	−0.0048 (9)	−0.0045 (9)	−0.0094 (10)
C8	0.0310 (11)	0.0479 (12)	0.0369 (11)	−0.0013 (9)	0.0063 (9)	−0.0062 (9)

Geometric parameters (Å, º) top

Zn1—Cl2	2.2690 (7)	N2—C4	1.362 (3)
Zn1—Cl3	2.2704 (6)	N2—H2N	0.864 (16)
Zn1—Cl4	2.2737 (6)	N3—C7	1.321 (3)
Zn1—Cl1	2.2794 (6)	N3—C6	1.378 (2)
O1S—H1SA	0.829 (19)	N3—H3N	0.830 (16)
O1S—H1SB	0.806 (18)	N4—C7	1.316 (3)
O1—C1	1.313 (2)	N4—C8	1.356 (3)
O1—H1A	0.828 (18)	N4—H4N	0.858 (16)
O2—C1	1.200 (2)	C1—C2	1.465 (3)
O3—C5	1.305 (2)	C2—C4	1.355 (3)
O3—H3A	0.827 (17)	C3—H3	0.95
O4—C5	1.201 (3)	C4—H4	0.95
N1—C3	1.317 (3)	C5—C6	1.468 (3)
N1—C2	1.379 (2)	C6—C8	1.354 (3)
N1—H1N	0.838 (16)	C7—H7	0.95
N2—C3	1.323 (3)	C8—H8	0.95

Cl2—Zn1—Cl3	107.93 (2)	O1—C1—C2	112.04 (17)
Cl2—Zn1—Cl4	111.11 (2)	C4—C2—N1	106.33 (17)
Cl3—Zn1—Cl4	109.21 (3)	C4—C2—C1	132.70 (18)
Cl2—Zn1—Cl1	107.85 (2)	N1—C2—C1	120.95 (17)
Cl3—Zn1—Cl1	112.84 (2)	N1—C3—N2	107.86 (18)
Cl4—Zn1—Cl1	107.92 (2)	N1—C3—H3	126.1
H1SA—O1S—H1SB	119 (4)	N2—C3—H3	126.1
C1—O1—H1A	107 (2)	C2—C4—N2	106.69 (18)
C5—O3—H3A	107 (2)	C2—C4—H4	126.7
C3—N1—C2	109.33 (16)	N2—C4—H4	126.7
C3—N1—H1N	124.5 (16)	O4—C5—O3	125.4 (2)
C2—N1—H1N	126.2 (16)	O4—C5—C6	122.53 (18)
C3—N2—C4	109.79 (17)	O3—C5—C6	112.00 (18)
C3—N2—H2N	125.9 (17)	C8—C6—N3	106.23 (18)
C4—N2—H2N	124.3 (17)	C8—C6—C5	132.12 (18)
C7—N3—C6	109.06 (17)	N3—C6—C5	121.61 (17)
C7—N3—H3N	125.3 (17)	N4—C7—N3	107.89 (19)
C6—N3—H3N	125.6 (17)	N4—C7—H7	126.1
C7—N4—C8	110.01 (18)	N3—C7—H7	126.1
C7—N4—H4N	126.0 (17)	C6—C8—N4	106.81 (18)
C8—N4—H4N	123.9 (17)	C6—C8—H8	126.6
O2—C1—O1	124.9 (2)	N4—C8—H8	126.6
O2—C1—C2	123.11 (18)

C3—N1—C2—C4	−0.3 (2)	C7—N3—C6—C8	0.2 (2)
C3—N1—C2—C1	−178.98 (18)	C7—N3—C6—C5	178.29 (19)
O2—C1—C2—C4	−173.6 (2)	O4—C5—C6—C8	175.7 (2)
O1—C1—C2—C4	6.0 (3)	O3—C5—C6—C8	−2.2 (3)
O2—C1—C2—N1	4.6 (3)	O4—C5—C6—N3	−1.8 (3)
O1—C1—C2—N1	−175.81 (19)	O3—C5—C6—N3	−179.68 (18)
C2—N1—C3—N2	0.6 (2)	C8—N4—C7—N3	0.5 (3)
C4—N2—C3—N1	−0.6 (2)	C6—N3—C7—N4	−0.5 (3)
N1—C2—C4—N2	−0.1 (2)	N3—C6—C8—N4	0.1 (2)
C1—C2—C4—N2	178.4 (2)	C5—C6—C8—N4	−177.7 (2)
C3—N2—C4—C2	0.4 (2)	C7—N4—C8—C6	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1SA···Cl2	0.83 (2)	2.42 (2)	3.192 (3)	155 (4)
O1S—H1SB···Cl4ⁱ	0.81 (2)	2.94 (4)	3.392 (2)	118 (3)
O1S—H1SB···Cl1ⁱⁱ	0.81 (2)	3.05 (4)	3.540 (3)	122 (4)
O1—H1A···Cl4ⁱⁱⁱ	0.83 (2)	2.25 (2)	3.0723 (19)	171 (3)
O3—H3A···O1S^iv	0.83 (2)	1.77 (2)	2.576 (3)	163 (3)
N1—H1N···Cl1	0.84 (2)	2.37 (2)	3.2105 (17)	178 (2)
N2—H2N···Cl1ⁱ	0.86 (2)	2.85 (2)	3.3787 (19)	122 (2)
N2—H2N···O2ⁱ	0.86 (2)	1.99 (2)	2.745 (2)	146 (2)
N3—H3N···Cl3^v	0.83 (2)	2.37 (2)	3.1941 (18)	177 (2)
N4—H4N···Cl3^vi	0.86 (2)	2.83 (2)	3.3586 (19)	121 (2)
N4—H4N···O4ⁱ	0.86 (2)	2.00 (2)	2.753 (2)	146 (2)

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

(II) bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate bis(1H-imidazol-3-ium-4-carboxylato) monohydrate top

Crystal data top

(C₄H₄N₂O₂)₂[ZnCl₄]·2C₄H₅N₂O₂H₂O	Z = 2
M_r = 675.57	F(000) = 684
Triclinic, P1	D_x = 1.728 Mg m⁻³
a = 6.9369 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.9624 (15) Å	Cell parameters from 3388 reflections
c = 28.483 (8) Å	θ = 3.1–23.6°
α = 89.524 (9)°	µ = 1.42 mm⁻¹
β = 85.622 (9)°	T = 200 K
γ = 71.202 (8)°	Block, clear colourless
V = 1298.3 (6) Å³	0.50 × 0.25 × 0.20 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	4855 independent reflections
Radiation source: sealed microfocus tube	3619 reflections with I > 2σ(I)
Detector resolution: 8.3330 pixels mm^-1	R_int = 0.042
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −8→8
T_min = 0.50, T_max = 0.76	k = −8→7
10560 measured reflections	l = −35→21

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)] = 0.050	Hydrogen site location: mixed
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0739P)² + 0.0203P] where P = (F_o² + 2F_c²)/3
4855 reflections	(Δ/σ)_max < 0.001
395 parameters	Δρ_max = 0.63 e Å⁻³
16 restraints	Δρ_min = −0.71 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)
Zn1	−0.05225 (7)	0.61778 (7)	0.24502 (2)	0.03731 (17)
Cl1	−0.26017 (17)	0.82285 (19)	0.19411 (4)	0.0531 (3)
Cl2	0.05785 (16)	0.29226 (16)	0.21504 (3)	0.0436 (3)
Cl3	0.23787 (18)	0.6937 (2)	0.25097 (4)	0.0560 (3)
Cl4	−0.22620 (16)	0.63506 (17)	0.31606 (3)	0.0408 (3)
O1	0.3219 (4)	0.2856 (5)	0.02796 (9)	0.0471 (8)
O2	0.1247 (4)	0.3358 (5)	0.09533 (10)	0.0517 (8)
O3	0.3667 (5)	0.1705 (6)	0.39393 (12)	0.0661 (10)
O4	0.4907 (5)	0.2123 (5)	0.46135 (10)	0.0559 (9)
H4A	0.379 (5)	0.223 (8)	0.4788 (16)	0.084*
O5	−0.1453 (5)	0.7598 (5)	0.50318 (10)	0.0537 (8)
O6	−0.2533 (5)	0.6845 (6)	0.43625 (10)	0.0615 (9)
O7	−0.2136 (5)	0.8281 (6)	0.07375 (11)	0.0685 (10)
O8	−0.0196 (5)	0.7583 (5)	0.00627 (10)	0.0508 (8)
H8A	−0.114 (6)	0.723 (8)	−0.0045 (16)	0.076*
O1S	0.414 (2)	0.099 (2)	0.2899 (6)	0.070 (4)	0.60 (4)
H1A	0.334 (16)	0.176 (12)	0.272 (3)	0.105*	0.60 (4)
H1B	0.459 (16)	−0.021 (6)	0.279 (3)	0.105*	0.60 (4)
O2S	0.495 (5)	0.150 (4)	0.2703 (12)	0.093 (10)	0.40 (4)
H2A	0.381 (15)	0.15 (3)	0.262 (8)	0.14*	0.40 (4)
H2B	0.59 (2)	0.08 (3)	0.251 (5)	0.14*	0.40 (4)
N1	0.7400 (5)	0.3481 (6)	0.12509 (13)	0.0451 (9)
H1N	0.870 (3)	0.342 (7)	0.1225 (15)	0.054*
N2	0.4407 (5)	0.3466 (6)	0.14633 (11)	0.0392 (8)
H2N	0.328 (4)	0.352 (6)	0.1626 (12)	0.047*
N3	0.7314 (6)	0.1382 (5)	0.34378 (11)	0.0405 (8)
H3N	0.644 (5)	0.134 (6)	0.3241 (12)	0.049*
N4	1.0110 (6)	0.1551 (6)	0.36673 (14)	0.0460 (9)
H4N	1.133 (4)	0.158 (7)	0.3638 (15)	0.055*
N5	0.1092 (5)	0.6640 (5)	0.38684 (11)	0.0370 (8)
H5N	0.024 (5)	0.646 (6)	0.3686 (12)	0.044*
N6	0.3850 (5)	0.6882 (6)	0.41028 (12)	0.0437 (9)
H6N	0.511 (4)	0.687 (7)	0.4100 (15)	0.052*
N7	0.1081 (5)	0.8476 (5)	0.12179 (11)	0.0370 (8)
H7N	0.006 (5)	0.834 (6)	0.1409 (12)	0.044*
N8	0.4083 (5)	0.8406 (5)	0.09664 (12)	0.0392 (8)
H8N	0.533 (4)	0.846 (6)	0.0945 (14)	0.047*
C1	0.4601 (6)	0.3304 (6)	0.09817 (12)	0.0317 (9)
C2	0.6497 (6)	0.3318 (6)	0.08465 (14)	0.0403 (10)
H2	0.7095	0.3232	0.0533	0.048*
C3	0.6112 (6)	0.3560 (7)	0.16165 (15)	0.0463 (11)
H3	0.6366	0.3667	0.1937	0.056*
C4	0.2872 (6)	0.3160 (6)	0.07221 (13)	0.0352 (9)
C5	0.7016 (6)	0.1709 (6)	0.39137 (13)	0.0349 (9)
C6	0.8780 (6)	0.1832 (6)	0.40570 (13)	0.0385 (9)
H6	0.9044	0.207	0.437	0.046*
C7	0.9189 (7)	0.1297 (6)	0.32923 (14)	0.0443 (10)
H7	0.9775	0.1092	0.2977	0.053*
C8	0.5038 (7)	0.1835 (6)	0.41683 (14)	0.0412 (10)
C9	0.0765 (6)	0.6982 (6)	0.43471 (12)	0.0332 (9)
C10	0.2521 (6)	0.7147 (6)	0.44949 (13)	0.0411 (10)
H10	0.2774	0.7396	0.4808	0.049*
C11	0.2965 (6)	0.6581 (7)	0.37284 (14)	0.0415 (10)
H11	0.357	0.6361	0.3415	0.05*
C12	−0.1239 (6)	0.7129 (6)	0.45951 (13)	0.0387 (9)
C13	0.1228 (6)	0.8218 (6)	0.07366 (12)	0.0327 (9)
C14	0.3108 (6)	0.8187 (6)	0.05808 (13)	0.0359 (9)
H14	0.3661	0.804	0.0262	0.043*
C15	0.2828 (6)	0.8583 (6)	0.13502 (13)	0.0395 (10)
H15	0.313	0.8756	0.1664	0.047*
C16	−0.0527 (6)	0.8025 (6)	0.04986 (13)	0.0371 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0263 (3)	0.0572 (3)	0.0303 (2)	−0.0159 (2)	−0.00276 (18)	0.0010 (2)
Cl1	0.0298 (6)	0.0833 (8)	0.0449 (6)	−0.0162 (6)	−0.0066 (4)	0.0210 (5)
Cl2	0.0350 (6)	0.0569 (7)	0.0396 (5)	−0.0163 (5)	0.0002 (4)	−0.0053 (4)
Cl3	0.0384 (7)	0.0955 (9)	0.0465 (6)	−0.0383 (7)	−0.0061 (5)	0.0008 (6)
Cl4	0.0300 (6)	0.0627 (7)	0.0325 (5)	−0.0195 (5)	0.0005 (4)	−0.0008 (4)
O1	0.0278 (17)	0.083 (2)	0.0384 (15)	−0.0286 (17)	−0.0010 (12)	−0.0070 (14)
O2	0.0223 (16)	0.092 (2)	0.0451 (16)	−0.0247 (17)	0.0012 (12)	−0.0051 (15)
O3	0.034 (2)	0.106 (3)	0.067 (2)	−0.032 (2)	−0.0113 (16)	−0.0099 (19)
O4	0.0332 (19)	0.089 (2)	0.0449 (18)	−0.0209 (19)	0.0054 (13)	−0.0038 (16)
O5	0.0321 (18)	0.090 (2)	0.0411 (16)	−0.0239 (18)	0.0005 (13)	−0.0055 (15)
O6	0.0292 (18)	0.112 (3)	0.0530 (18)	−0.035 (2)	−0.0055 (14)	−0.0124 (18)
O7	0.0241 (18)	0.138 (3)	0.0505 (18)	−0.036 (2)	0.0012 (14)	−0.0083 (19)
O8	0.0326 (18)	0.086 (2)	0.0427 (16)	−0.0312 (18)	−0.0062 (13)	−0.0057 (15)
O1S	0.042 (6)	0.110 (6)	0.048 (6)	−0.008 (5)	−0.014 (5)	−0.020 (4)
O2S	0.060 (14)	0.130 (12)	0.068 (13)	0.008 (11)	−0.035 (11)	−0.019 (11)
N1	0.0172 (19)	0.063 (2)	0.060 (2)	−0.0188 (19)	−0.0057 (16)	−0.0067 (18)
N2	0.0176 (18)	0.060 (2)	0.0417 (18)	−0.0154 (18)	−0.0014 (14)	−0.0019 (16)
N3	0.032 (2)	0.052 (2)	0.0397 (18)	−0.0163 (18)	−0.0075 (15)	0.0016 (16)
N4	0.023 (2)	0.050 (2)	0.069 (2)	−0.0163 (18)	−0.0057 (17)	0.0118 (18)
N5	0.0210 (18)	0.052 (2)	0.0406 (18)	−0.0135 (17)	−0.0100 (14)	−0.0015 (15)
N6	0.0174 (18)	0.060 (2)	0.058 (2)	−0.0166 (18)	−0.0085 (16)	0.0067 (17)
N7	0.0236 (19)	0.056 (2)	0.0353 (17)	−0.0183 (17)	−0.0008 (13)	0.0015 (15)
N8	0.0171 (18)	0.050 (2)	0.056 (2)	−0.0168 (17)	−0.0054 (15)	0.0018 (16)
C1	0.020 (2)	0.040 (2)	0.0378 (19)	−0.0145 (18)	−0.0013 (15)	−0.0030 (16)
C2	0.020 (2)	0.055 (3)	0.044 (2)	−0.011 (2)	0.0009 (16)	−0.0067 (19)
C3	0.028 (2)	0.068 (3)	0.047 (2)	−0.020 (2)	−0.0079 (19)	−0.002 (2)
C4	0.023 (2)	0.045 (2)	0.041 (2)	−0.0149 (19)	−0.0041 (16)	0.0011 (17)
C5	0.031 (2)	0.036 (2)	0.040 (2)	−0.0118 (19)	−0.0084 (17)	0.0009 (17)
C6	0.036 (2)	0.043 (2)	0.040 (2)	−0.015 (2)	−0.0093 (18)	−0.0013 (17)
C7	0.039 (3)	0.050 (3)	0.044 (2)	−0.015 (2)	0.0016 (19)	0.0033 (19)
C8	0.027 (2)	0.049 (3)	0.050 (2)	−0.015 (2)	−0.0047 (18)	−0.0028 (19)
C9	0.020 (2)	0.044 (2)	0.0370 (19)	−0.0120 (19)	−0.0081 (15)	0.0046 (17)
C10	0.031 (2)	0.056 (3)	0.038 (2)	−0.014 (2)	−0.0110 (17)	−0.0017 (18)
C11	0.026 (2)	0.058 (3)	0.042 (2)	−0.015 (2)	−0.0014 (17)	0.0025 (19)
C12	0.025 (2)	0.052 (3)	0.041 (2)	−0.014 (2)	−0.0040 (17)	−0.0012 (18)
C13	0.022 (2)	0.044 (2)	0.0352 (19)	−0.0141 (19)	−0.0042 (15)	0.0015 (16)
C14	0.023 (2)	0.047 (2)	0.038 (2)	−0.013 (2)	−0.0007 (16)	−0.0019 (17)
C15	0.032 (2)	0.052 (3)	0.039 (2)	−0.017 (2)	−0.0118 (17)	0.0020 (18)
C16	0.020 (2)	0.055 (3)	0.039 (2)	−0.015 (2)	−0.0053 (16)	0.0019 (18)

Geometric parameters (Å, º) top

Zn1—Cl3	2.2577 (12)	N4—H4N	0.849 (19)
Zn1—Cl4	2.2589 (11)	N5—C11	1.317 (5)
Zn1—Cl1	2.2758 (12)	N5—C9	1.375 (5)
Zn1—Cl2	2.2948 (12)	N5—H5N	0.858 (19)
O1—C4	1.271 (4)	N6—C11	1.321 (5)
O2—C4	1.229 (4)	N6—C10	1.367 (5)
O3—C8	1.220 (5)	N6—H6N	0.868 (19)
O4—C8	1.277 (5)	N7—C15	1.321 (5)
O4—H4A	0.87 (2)	N7—C13	1.376 (4)
O5—C12	1.274 (5)	N7—H7N	0.889 (19)
O6—C12	1.222 (5)	N8—C15	1.325 (5)
O7—C16	1.224 (5)	N8—C14	1.367 (5)
O8—C16	1.267 (5)	N8—H8N	0.872 (19)
O8—H8A	0.851 (19)	C1—C2	1.345 (5)
O1S—H1A	0.85 (2)	C1—C4	1.487 (5)
O1S—H1B	0.84 (2)	C2—H2	0.95
O2S—H2A	0.85 (2)	C3—H3	0.95
O2S—H2B	0.85 (2)	C5—C6	1.347 (5)
N1—C3	1.309 (5)	C5—C8	1.479 (5)
N1—C2	1.375 (5)	C6—H6	0.95
N1—H1N	0.884 (19)	C7—H7	0.95
N2—C3	1.312 (5)	C9—C10	1.357 (5)
N2—C1	1.370 (5)	C9—C12	1.484 (5)
N2—H2N	0.871 (19)	C10—H10	0.95
N3—C7	1.318 (5)	C11—H11	0.95
N3—C5	1.365 (5)	C13—C14	1.339 (5)
N3—H3N	0.866 (19)	C13—C16	1.481 (5)
N4—C7	1.327 (6)	C14—H14	0.95
N4—C6	1.361 (5)	C15—H15	0.95

Cl3—Zn1—Cl4	111.21 (4)	N1—C3—H3	126.0
Cl3—Zn1—Cl1	112.42 (5)	N2—C3—H3	126.0
Cl4—Zn1—Cl1	109.31 (5)	O2—C4—O1	126.3 (4)
Cl3—Zn1—Cl2	104.23 (5)	O2—C4—C1	117.2 (3)
Cl4—Zn1—Cl2	110.95 (4)	O1—C4—C1	116.5 (3)
Cl1—Zn1—Cl2	108.62 (5)	C6—C5—N3	106.6 (3)
C8—O4—H4A	122 (4)	C6—C5—C8	132.8 (4)
C16—O8—H8A	113 (3)	N3—C5—C8	120.6 (3)
H1A—O1S—H1B	111 (5)	C5—C6—N4	106.8 (3)
H2A—O2S—H2B	113 (6)	C5—C6—H6	126.6
C3—N1—C2	109.4 (3)	N4—C6—H6	126.6
C3—N1—H1N	132 (3)	N3—C7—N4	107.5 (4)
C2—N1—H1N	118 (3)	N3—C7—H7	126.3
C3—N2—C1	109.7 (3)	N4—C7—H7	126.3
C3—N2—H2N	128 (3)	O3—C8—O4	125.6 (4)
C1—N2—H2N	122 (3)	O3—C8—C5	118.2 (4)
C7—N3—C5	109.6 (3)	O4—C8—C5	116.2 (4)
C7—N3—H3N	121 (3)	C10—C9—N5	106.6 (3)
C5—N3—H3N	129 (3)	C10—C9—C12	133.0 (3)
C7—N4—C6	109.4 (4)	N5—C9—C12	120.4 (3)
C7—N4—H4N	120 (3)	C9—C10—N6	106.2 (3)
C6—N4—H4N	130 (3)	C9—C10—H10	126.9
C11—N5—C9	109.5 (3)	N6—C10—H10	126.9
C11—N5—H5N	124 (3)	N5—C11—N6	107.7 (3)
C9—N5—H5N	126 (3)	N5—C11—H11	126.1
C11—N6—C10	110.0 (3)	N6—C11—H11	126.1
C11—N6—H6N	125 (3)	O6—C12—O5	126.3 (4)
C10—N6—H6N	125 (3)	O6—C12—C9	117.6 (3)
C15—N7—C13	109.3 (3)	O5—C12—C9	116.1 (3)
C15—N7—H7N	126 (3)	C14—C13—N7	106.7 (3)
C13—N7—H7N	124 (3)	C14—C13—C16	133.2 (3)
C15—N8—C14	109.4 (3)	N7—C13—C16	120.1 (3)
C15—N8—H8N	128 (3)	C13—C14—N8	107.0 (3)
C14—N8—H8N	122 (3)	C13—C14—H14	126.5
C2—C1—N2	106.3 (3)	N8—C14—H14	126.5
C2—C1—C4	133.6 (3)	N7—C15—N8	107.6 (3)
N2—C1—C4	120.2 (3)	N7—C15—H15	126.2
C1—C2—N1	106.6 (3)	N8—C15—H15	126.2
C1—C2—H2	126.7	O7—C16—O8	126.3 (4)
N1—C2—H2	126.7	O7—C16—C13	117.8 (3)
N1—C3—N2	108.0 (4)	O8—C16—C13	115.9 (3)

C3—N2—C1—C2	−0.4 (5)	C11—N5—C9—C10	0.5 (5)
C3—N2—C1—C4	179.6 (4)	C11—N5—C9—C12	179.7 (4)
N2—C1—C2—N1	0.2 (5)	N5—C9—C10—N6	−0.5 (5)
C4—C1—C2—N1	−179.9 (4)	C12—C9—C10—N6	−179.6 (4)
C3—N1—C2—C1	0.1 (5)	C11—N6—C10—C9	0.4 (5)
C2—N1—C3—N2	−0.4 (5)	C9—N5—C11—N6	−0.2 (5)
C1—N2—C3—N1	0.5 (5)	C10—N6—C11—N5	−0.1 (5)
C2—C1—C4—O2	−174.2 (5)	C10—C9—C12—O6	−177.8 (5)
N2—C1—C4—O2	5.7 (6)	N5—C9—C12—O6	3.2 (6)
C2—C1—C4—O1	5.4 (7)	C10—C9—C12—O5	4.0 (7)
N2—C1—C4—O1	−174.7 (4)	N5—C9—C12—O5	−175.0 (4)
C7—N3—C5—C6	0.3 (5)	C15—N7—C13—C14	−0.4 (5)
C7—N3—C5—C8	−179.0 (4)	C15—N7—C13—C16	179.2 (4)
N3—C5—C6—N4	−0.8 (5)	N7—C13—C14—N8	0.5 (5)
C8—C5—C6—N4	178.4 (4)	C16—C13—C14—N8	−179.0 (4)
C7—N4—C6—C5	1.1 (5)	C15—N8—C14—C13	−0.4 (5)
C5—N3—C7—N4	0.4 (5)	C13—N7—C15—N8	0.1 (5)
C6—N4—C7—N3	−0.9 (5)	C14—N8—C15—N7	0.2 (5)
C6—C5—C8—O3	178.6 (5)	C14—C13—C16—O7	−174.2 (5)
N3—C5—C8—O3	−2.3 (6)	N7—C13—C16—O7	6.3 (6)
C6—C5—C8—O4	0.2 (7)	C14—C13—C16—O8	6.5 (7)
N3—C5—C8—O4	179.3 (4)	N7—C13—C16—O8	−173.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O5ⁱ	0.87 (2)	1.63 (2)	2.476 (4)	163 (5)
O4—H4A···O6ⁱ	0.87 (2)	2.52 (4)	3.205 (4)	136 (4)
O8—H8A···O1ⁱⁱ	0.85 (2)	1.65 (2)	2.484 (4)	166 (5)
O8—H8A···O2ⁱⁱ	0.85 (2)	2.63 (4)	3.162 (4)	122 (4)
O1S—H1A···Cl2	0.85 (2)	2.52 (5)	3.330 (9)	159 (10)
O1S—H1B···Cl1ⁱⁱⁱ	0.84 (2)	2.97 (9)	3.546 (15)	128 (10)
O1S—H1B···Cl4ⁱⁱⁱ	0.84 (2)	2.93 (7)	3.499 (11)	127 (8)
O2S—H2A···Cl2	0.85 (2)	2.61 (12)	3.382 (17)	150.20
O2S—H2B···Cl1ⁱⁱⁱ	0.85 (2)	2.36 (10)	3.13 (2)	150 (17)
N1—H1N···O2^iv	0.88 (2)	1.86 (2)	2.712 (4)	160 (4)
N2—H2N···Cl2	0.87 (2)	2.44 (2)	3.297 (3)	167 (4)
N3—H3N···O1S	0.87 (2)	2.01 (2)	2.860 (10)	168 (4)
N3—H3N···O2S	0.87 (2)	1.89 (2)	2.739 (12)	165 (4)
N4—H4N···O3^iv	0.85 (2)	1.92 (3)	2.677 (5)	148 (4)
N5—H5N···Cl4	0.86 (2)	2.39 (2)	3.247 (3)	173 (4)
N6—H6N···O6^iv	0.87 (2)	1.85 (3)	2.661 (4)	156 (4)
N7—H7N···Cl1	0.89 (2)	2.32 (2)	3.205 (3)	175 (4)
N8—H8N···O7^iv	0.87 (2)	1.78 (2)	2.628 (4)	164 (4)
C2—H2···O8^v	0.95	2.55	3.414 (5)	152
C3—H3···Cl2^iv	0.95	2.91	3.454 (4)	118
C6—H6···O5^vi	0.95	2.54	3.400 (5)	151
C7—H7···Cl2^iv	0.95	2.77	3.599 (4)	146
C10—H10···O4^vi	0.95	2.49	3.345 (5)	151
C11—H11···Cl3	0.95	2.75	3.523 (4)	139
C11—H11···Cl4^iv	0.95	2.92	3.528 (4)	123
C14—H14···O1^v	0.95	2.47	3.303 (5)	147
C15—H15···Cl3	0.95	2.8	3.511 (4)	132

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

Acknowledgements

This work was supported by a Congressionally directed grant from the US Department of Education for the X-ray diffractometer and a grant from the Geneseo Foundation.

Funding information

Funding for this research was provided by: U.S. Department of Education (award No. P116Z100020); Geneseo Foundation

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Volume 73| Part 2| February 2017| Pages 162-167

https://doi.org/10.1107/S2056989017000317

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

Structural characterization of two tetra­chlorido­zincate salts of 4-carb­­oxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Structural characterization of two tetrachloridozincate salts of 4-carboxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate

3. Supramolecular features