The title compound, bis[(5-amino-1H-1,2,4-triazol-3-yl-κN 4)acetato-κO]diaqua)nickel(II) dihydrate, is the first transition metal complex of 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid (ATAA).
Keywords: Crystal structure; triazole; 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid; chelating ligand; nickel coordination compound; crystal structure
Abstract
The title compound, [Ni(C4H5N4O2)2(H2O)2]·2H2O, represents the first transition metal complex of the novel chelating triazole ligand, 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid (ATAA), to be structurally characterized. In the molecule of the title complex, the nickel(II) cation is located on an inversion centre and is coordinated by two water molecules in axial positions and two O and two N atoms from two trans-oriented chelating anions of the deprotonated ATAA ligand, forming a slightly distorted octahedron. The trans angles of the octahedron are all 180° due to the inversion symmetry of the molecule. The cis-angles are in the range 87.25 (8)–92.75 (8)°. The six-membered chelate ring adopts a slightly twisted boat conformation with puckering parameters Q = 0.542 (2) Å, Θ = 88.5 (2) and ϕ = 15.4 (3)°. The molecular conformation is stabilized by intramolecular N—H⋯O hydrogen bonds between the amino group and the chelating carboxylate O atom of two trans-oriented ligands. In the crystal, the complex molecules and lattice water molecules are linked into a three-dimensional framework by an extensive network of N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds.
Chemical context
C-amino-1,2,4-triazoles are employed as polydentate ligands for the synthesis of coordination compounds with various metals that demonstrate useful spectroscopic, magnetic, biological and catalytic properties (Aromí et al., 2011 ▶; Liu et al., 2011 ▶; Gao et al., 2013 ▶; Hernández-Gil et al., 2014 ▶). Generally, aminotriazoles coordinate metals by either pyridine-type endocyclic nitrogen atoms or by the amino group (Aromí et al., 2011 ▶; Liu et al., 2011 ▶). Furthermore, aminotriazoles containing substituents with favorably oriented atoms bearing unshared electron pairs (N, S, O etc.) can act as chelating polydentate ligands (Biagini-Cingi et al., 1994 ▶; Prins et al., 1996 ▶; Ferrer et al., 2004 ▶, 2012 ▶). 5-Amino-1H-1,2,4-triazole-3-carboxylic acid (ATCA, Fig. 1 ▶) was found to be a promising chelating ligand for which complexes with various metal cations have been reported recently (Chen et al., 2011 ▶; Sun et al., 2011 ▶; Wang et al., 2011 ▶; Hernández-Gil et al., 2012 ▶; Tseng et al., 2014 ▶). In these complexes, metal cations are chelated by the anions of ATCA owing to the formation of coordination bonds with nitrogen atoms of the triazole ring and the oxygen atom of the deprotonated carboxylic group.
Figure 1.
Structural formulas of 5-amino-1H-1,2,4-triazole-3-carboxylic acid (ATCA) and 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid (ATAA).
In a continuation of our work on the synthesis and reactivity of aminotriazole carboxylic acids (Chernyshev et al., 2006 ▶, 2009 ▶, 2010 ▶), we have focused our attention on another chelating ligand, namely 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid (ATAA, Fig. 1 ▶), which can be considered as a homologue of ATCA. To the best of our knowledge, ATAA or its derivatives have not been studied previously for the synthesis of coordination compounds. Herein, we report the synthesis and crystal structure of an NiII complex of ATAA, the title compound [Ni(C4H5N4O2)2(H2O)2]·2H2O (1).
Structural commentary
In the molecule of the title complex (1), the NiII cation is six-coordinated by two bidentate chelating ligands, anions of ATAA, and by two water molecules, forming a slightly distorted octahedron (Fig. 2 ▶). The trans-angles of the octahedron are all 180° due to the inversion symmetry of the complete molecule. The cis-angles are in the range 87.25 (8)–92.75 (8)°. The third water molecule is not involved in coordination. The anions of ATAA coordinate the NiII cation through the nitrogen atom N1 of the triazole ring and the oxygen atom O53 of the carboxylate group (Fig. 2 ▶), similarly to the complexes of ATCA with various metal cations (Chen et al., 2011 ▶; Sun et al., 2011 ▶; Wang et al., 2011 ▶; Hernández-Gil et al., 2012 ▶). The six-membered chelate ring adopts a slightly twisted boat conformation with puckering parameters of Q = 0.542 (2) Å, Θ = 88.5 (2), ϕ = 15.4 (3)°. The Ni—N1 bond length is 2.051 (2) Å, and the Ni—O1 and Ni—O53 bond lengths are 2.083 (2) and 2.059 (2) Å, respectively, within the normal ranges for other reported NiII complexes (Lenstra et al., 1989 ▶; Virovets et al., 2000 ▶; Bushuev et al., 2002 ▶; Drozdzewski et al., 2003 ▶; Fan et al., 2010 ▶; Zheng et al., 2011 ▶; Jin et al., 2011 ▶). The aminotriazole fragment N1/C2/N3/N4/C5/N21 is planar (maximum deviation = 0.021 (3) Å for C2), its bond lengths and angles being analogous to complexes of C-amino-1,2,4-triazoles with transition metals (Ferrer et al., 2004 ▶; Siddiqui et al., 2011 ▶; Tabatabaee et al., 2011 ▶). The bonds C2—N3 [1.330 (4) Å] and C5—N4 [1.304 (3) Å] are shorter than the bonds C2—N1 [1.342 (3) Å] and C5—N1 [1.365 (3) Å]. The molecular conformation is stabilized by intramolecular N21—H21B⋯O53 hydrogen bonds (Fig. 2 ▶, Table 1 ▶).
Figure 2.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Intramolecular N—H⋯O hydrogen bonds are shown as dashed lines. Equivalent atoms are generated by symmetry code −x, −y, −z.
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| N21H21AO2i | 0.83(2) | 2.04(2) | 2.876(3) | 176(3) |
| N21H21BO53ii | 0.83(2) | 2.19(2) | 2.941(3) | 151(3) |
| N3H3O54iii | 0.83(3) | 2.10(3) | 2.885(3) | 156(3) |
| O1H1AO2iv | 0.82(2) | 1.92(2) | 2.739(3) | 176(3) |
| O1H1BO54v | 0.82(2) | 1.96(2) | 2.780(3) | 173(4) |
| O2H2AN4vi | 0.83(2) | 2.09(2) | 2.903(3) | 164(3) |
| O2H2BO53vii | 0.83(2) | 1.98(2) | 2.811(3) | 176(3) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
; (vi) 
; (vii) 
.
Supramolecular features
In the crystal, molecules of the complex and lattice water molecules are linked into a three–dimensional framework by extensive N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds (Table 1 ▶, Fig. 3 ▶).
Figure 3.
The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.
Database survey
More than twenty structures of chelate complexes of 3-substituted 5-amino-1,2,4-triazoles, in which N, O or S atoms of the substituent in the position 3 of the triazole ring play the role of a donor atom, were found in the Cambridge Structural Database (Version 5.35, November 2013 with 2 updates; Thomas et al., 2010 ▶). The database reveals a total of seven structures of coordination compounds of 5-amino-1H-1,2,4-triazole-3-carboxylic acid (ATCA) with various metals (Chen et al., 2011 ▶; Sun et al., 2011 ▶; Wang et al., 2011 ▶; Hernández-Gil et al., 2012 ▶; Tseng et al., 2014 ▶; Siddiqui et al., 2011 ▶), six of which are chelate complexes. Coordination compounds of metals with the ATAA ligands or its derivatives were not found in the literature.
Synthesis and crystallization
All attempts to prepare crystals of complex (1) suitable for X-ray investigation by mixing solutions of ATAA or its sodium salt with solutions of NiII salts were unsuccessful and only microcrystalline precipitates of the sparingly soluble complex were obtained. Crystals of acceptable quality were prepared by slow hydrolysis of ethyl 2-(5-amino-1H-1,2,4-triazol-3-yl)acetate (2) in an aqueous solution of nickel nitrate (Fig. 4 ▶). A solution of 0.65 g (3.8 mmol) of compound (2) in water (10 ml) was added to a solution of 0.55 g, (1.9 mmol) of Ni(NO3)2·6H2O in water (5 ml). After standing at room temperature for two weeks, the formed crystals were collected by filtration yielding the target compound (1).
Figure 4.
Reaction scheme showing the synthesis of the title compound (1).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▶. C-bound H atoms were placed in calculated positions with C—H = 0.97 Å for the CH2 group and refined as riding, with U iso(H) = 1.2U eq(C). The N,O-bound H atoms that are involved in hydrogen bonds were found from difference Fourier maps. Their distances to the parent atoms were refined to be equal, with a common U iso(H) value for pairs of related H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | |
| M r | 412.99 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 295 |
| a, b, c () | 7.6270(17), 7.2603(16), 13.580(3) |
| () | 91.91(2) |
| V (3) | 751.6(3) |
| Z | 2 |
| Radiation type | Ag K, = 0.56085 |
| (mm1) | 0.72 |
| Crystal size (mm) | 0.20 0.20 0.20 |
| Data collection | |
| Diffractometer | EnrafNonius CAD-4 |
| Absorption correction | scan (North et al., 1968 ▶) |
| T min, T max | 0.945, 0.958 |
| No. of measured, independent and observed [I > 2(I)] reflections | 1706, 1640, 1215 |
| R int | 0.021 |
| (sin /)max (1) | 0.638 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.035, 0.077, 1.02 |
| No. of reflections | 1640 |
| No. of parameters | 140 |
| No. of restraints | 3 |
| max, min (e 3) | 0.34, 0.31 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814021436/wm5066sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021436/wm5066Isup2.hkl
CCDC reference: 1026535
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported financially by the Ministry of Education and Science of the Russian Federation (project No. 2945 of State Order No. 2014/143).
supplementary crystallographic information
Crystal data
| F(000) = 428 | |
| Mr = 412.99 | Dx = 1.825 Mg m−3 |
| Monoclinic, P21/n | Ag Kα radiation, λ = 0.56085 Å |
| Hall symbol: -P 2yn | Cell parameters from 25 reflections |
| a = 7.6270 (17) Å | θ = 10.8–12.9° |
| b = 7.2603 (16) Å | µ = 0.72 mm−1 |
| c = 13.580 (3) Å | T = 295 K |
| β = 91.91 (2)° | Prism, light green |
| V = 751.6 (3) Å3 | 0.20 × 0.20 × 0.20 mm |
| Z = 2 |
Data collection
| Enraf–Nonius CAD-4 diffractometer | 1215 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.021 |
| Graphite monochromator | θmax = 21.0°, θmin = 2.4° |
| non–profiled ω–scans | h = −9→9 |
| Absorption correction: ψ scan (North et al., 1968) | k = 0→9 |
| Tmin = 0.945, Tmax = 0.958 | l = 0→17 |
| 1706 measured reflections | 1 standard reflections every 60 min |
| 1640 independent reflections | intensity decay: 1% |
Refinement
| Refinement on F2 | 3 restraints |
| Least-squares matrix: full | Primary atom site location: structure-invariant direct methods |
| R[F2 > 2σ(F2)] = 0.035 | Secondary atom site location: difference Fourier map |
| wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0282P)2 + 0.467P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 1640 reflections | Δρmax = 0.34 e Å−3 |
| 140 parameters | Δρmin = −0.31 e Å−3 |
Special details
| Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
| Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(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)
| x | y | z | Uiso*/Ueq | ||
| Ni | 0.0000 | 0.0000 | 0.0000 | 0.01840 (14) | |
| N1 | −0.0590 (3) | 0.0113 (4) | −0.14834 (14) | 0.0215 (5) | |
| C2 | 0.0459 (3) | 0.0087 (5) | −0.22579 (18) | 0.0237 (5) | |
| N21 | 0.2095 (3) | −0.0555 (4) | −0.22436 (19) | 0.0380 (8) | |
| H21A | 0.278 (3) | −0.036 (5) | −0.2696 (17) | 0.040 (7)* | |
| H21B | 0.248 (4) | −0.090 (5) | −0.1692 (15) | 0.040 (7)* | |
| N3 | −0.0433 (3) | 0.0713 (4) | −0.30469 (18) | 0.0307 (6) | |
| H3 | −0.010 (4) | 0.083 (4) | −0.362 (2) | 0.029 (9)* | |
| N4 | −0.2124 (3) | 0.1187 (4) | −0.28023 (17) | 0.0289 (6) | |
| C5 | −0.2135 (4) | 0.0798 (4) | −0.18651 (19) | 0.0218 (6) | |
| C51 | −0.3727 (3) | 0.1003 (4) | −0.12754 (19) | 0.0242 (6) | |
| H51A | −0.4200 | −0.0215 | −0.1160 | 0.029* | |
| H51B | −0.4597 | 0.1678 | −0.1668 | 0.029* | |
| C52 | −0.3496 (3) | 0.1962 (4) | −0.02933 (19) | 0.0206 (6) | |
| O53 | −0.2044 (2) | 0.1806 (3) | 0.01848 (14) | 0.0248 (5) | |
| O54 | −0.4765 (3) | 0.2802 (3) | 0.00309 (17) | 0.0335 (5) | |
| O1 | −0.1634 (3) | −0.2263 (3) | 0.01911 (18) | 0.0327 (5) | |
| H1A | −0.129 (4) | −0.313 (3) | 0.053 (2) | 0.048 (8)* | |
| H1B | −0.271 (2) | −0.238 (5) | 0.017 (3) | 0.048 (8)* | |
| O2 | 0.4528 (3) | 0.0268 (3) | 0.62437 (15) | 0.0320 (5) | |
| H2A | 0.556 (3) | 0.054 (5) | 0.641 (2) | 0.039 (7)* | |
| H2B | 0.404 (4) | 0.110 (4) | 0.591 (2) | 0.039 (7)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni | 0.0162 (2) | 0.0239 (3) | 0.0150 (2) | 0.0020 (2) | −0.00011 (16) | 0.0011 (3) |
| N1 | 0.0180 (10) | 0.0313 (13) | 0.0150 (9) | 0.0003 (12) | −0.0003 (8) | 0.0021 (12) |
| C2 | 0.0253 (13) | 0.0265 (14) | 0.0193 (12) | −0.0005 (14) | 0.0020 (10) | 0.0020 (15) |
| N21 | 0.0282 (14) | 0.063 (2) | 0.0236 (13) | 0.0098 (13) | 0.0102 (10) | 0.0131 (13) |
| N3 | 0.0322 (14) | 0.0449 (16) | 0.0152 (12) | 0.0033 (12) | 0.0051 (10) | 0.0053 (11) |
| N4 | 0.0275 (13) | 0.0400 (16) | 0.0190 (12) | 0.0058 (12) | −0.0017 (9) | 0.0048 (11) |
| C5 | 0.0225 (13) | 0.0246 (14) | 0.0181 (13) | −0.0026 (12) | −0.0009 (11) | 0.0006 (11) |
| C51 | 0.0161 (13) | 0.0340 (17) | 0.0224 (14) | 0.0006 (12) | −0.0015 (11) | 0.0017 (13) |
| C52 | 0.0202 (13) | 0.0221 (14) | 0.0196 (13) | 0.0002 (11) | 0.0032 (10) | 0.0040 (11) |
| O53 | 0.0208 (10) | 0.0322 (11) | 0.0210 (10) | 0.0049 (9) | −0.0042 (8) | −0.0041 (9) |
| O54 | 0.0238 (11) | 0.0486 (13) | 0.0282 (10) | 0.0106 (10) | 0.0032 (9) | −0.0058 (12) |
| O1 | 0.0202 (10) | 0.0327 (13) | 0.0448 (14) | −0.0046 (10) | −0.0041 (10) | 0.0108 (11) |
| O2 | 0.0309 (11) | 0.0371 (14) | 0.0280 (11) | −0.0022 (11) | 0.0007 (9) | 0.0026 (11) |
Geometric parameters (Å, º)
| Ni—N1 | 2.051 (2) | N3—H3 | 0.83 (3) |
| Ni—N1i | 2.051 (2) | N4—C5 | 1.304 (3) |
| Ni—O53 | 2.0590 (19) | C5—C51 | 1.484 (4) |
| Ni—O53i | 2.0590 (19) | C51—C52 | 1.509 (4) |
| Ni—O1 | 2.083 (2) | C51—H51A | 0.9700 |
| Ni—O1i | 2.084 (2) | C51—H51B | 0.9700 |
| N1—C2 | 1.342 (3) | C52—O54 | 1.238 (3) |
| N1—C5 | 1.365 (3) | C52—O53 | 1.270 (3) |
| C2—N3 | 1.330 (4) | O1—H1A | 0.822 (19) |
| C2—N21 | 1.332 (4) | O1—H1B | 0.822 (19) |
| N21—H21A | 0.834 (19) | O2—H2A | 0.83 (2) |
| N21—H21B | 0.834 (19) | O2—H2B | 0.83 (2) |
| N3—N4 | 1.386 (3) | ||
| N1—Ni—N1i | 180.0 | H21A—N21—H21B | 120 (3) |
| N1—Ni—O53 | 87.25 (8) | C2—N3—N4 | 110.3 (2) |
| N1i—Ni—O53 | 92.75 (8) | C2—N3—H3 | 129 (2) |
| N1—Ni—O53i | 92.75 (8) | N4—N3—H3 | 121 (2) |
| N1i—Ni—O53i | 87.25 (8) | C5—N4—N3 | 102.5 (2) |
| O53—Ni—O53i | 180.00 (13) | N4—C5—N1 | 114.6 (2) |
| N1—Ni—O1 | 92.36 (9) | N4—C5—C51 | 122.5 (2) |
| N1i—Ni—O1 | 87.63 (9) | N1—C5—C51 | 122.9 (2) |
| O53—Ni—O1 | 91.63 (9) | C5—C51—C52 | 116.7 (2) |
| O53i—Ni—O1 | 88.37 (9) | C5—C51—H51A | 108.1 |
| N1—Ni—O1i | 87.63 (9) | C52—C51—H51A | 108.1 |
| N1i—Ni—O1i | 92.37 (9) | C5—C51—H51B | 108.1 |
| O53—Ni—O1i | 88.37 (9) | C52—C51—H51B | 108.1 |
| O53i—Ni—O1i | 91.63 (9) | H51A—C51—H51B | 107.3 |
| O1—Ni—O1i | 180.0 | O54—C52—O53 | 122.8 (3) |
| C2—N1—C5 | 103.7 (2) | O54—C52—C51 | 118.2 (2) |
| C2—N1—Ni | 130.69 (17) | O53—C52—C51 | 119.0 (2) |
| C5—N1—Ni | 123.09 (17) | C52—O53—Ni | 130.20 (18) |
| N3—C2—N21 | 125.8 (2) | Ni—O1—H1A | 120 (2) |
| N3—C2—N1 | 108.9 (2) | Ni—O1—H1B | 132 (3) |
| N21—C2—N1 | 125.2 (2) | H1A—O1—H1B | 104 (3) |
| C2—N21—H21A | 123 (2) | H2A—O2—H2B | 112 (3) |
| C2—N21—H21B | 115 (2) | ||
| C5—N1—C2—N3 | −0.3 (3) | Ni—N1—C5—N4 | 163.8 (2) |
| Ni—N1—C2—N3 | −162.2 (2) | C2—N1—C5—C51 | 177.4 (3) |
| C5—N1—C2—N21 | −177.1 (3) | Ni—N1—C5—C51 | −18.9 (4) |
| Ni—N1—C2—N21 | 21.0 (5) | N4—C5—C51—C52 | −133.3 (3) |
| N21—C2—N3—N4 | 177.1 (3) | N1—C5—C51—C52 | 49.6 (4) |
| N1—C2—N3—N4 | 0.4 (4) | C5—C51—C52—O54 | 151.7 (3) |
| C2—N3—N4—C5 | −0.2 (3) | C5—C51—C52—O53 | −31.5 (4) |
| N3—N4—C5—N1 | 0.0 (3) | O54—C52—O53—Ni | 162.5 (2) |
| N3—N4—C5—C51 | −177.2 (3) | C51—C52—O53—Ni | −14.2 (4) |
| C2—N1—C5—N4 | 0.2 (4) |
Symmetry code: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N21—H21A···O2ii | 0.83 (2) | 2.04 (2) | 2.876 (3) | 176 (3) |
| N21—H21B···O53i | 0.83 (2) | 2.19 (2) | 2.941 (3) | 151 (3) |
| N3—H3···O54iii | 0.83 (3) | 2.10 (3) | 2.885 (3) | 156 (3) |
| O1—H1A···O2iv | 0.82 (2) | 1.92 (2) | 2.739 (3) | 176 (3) |
| O1—H1B···O54v | 0.82 (2) | 1.96 (2) | 2.780 (3) | 173 (4) |
| O2—H2A···N4vi | 0.83 (2) | 2.09 (2) | 2.903 (3) | 164 (3) |
| O2—H2B···O53vii | 0.83 (2) | 1.98 (2) | 2.811 (3) | 176 (3) |
Symmetry codes: (i) −x, −y, −z; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, z−1/2; (iv) x−1/2, −y−1/2, z−1/2; (v) −x−1, −y, −z; (vi) x+1, y, z+1; (vii) x+1/2, −y+1/2, z+1/2.
References
- Aromí, G., Barrios, L. A., Roubeau, O. & Gamez, P. (2011). Coord. Chem. Rev. 255, 485–546.
- Biagini-Cingi, M., Manotti-Lanfredi, A. M., Ugozzoli, F. & Haasnoot, J. G. (1994). Inorg. Chim. Acta, 227, 181–184.
- Bushuev, M. B., Virovets, A. V., Garcia, Y., Gieck, C., Sheludyakova, L. A., Ikorskii, V. N., Tremel, W., Gütlich, P. & Lavrenova, L. G. (2002). Polyhedron, 21, 797–804.
- Chen, Y.-C., Xu, J.-J., Wang, K.-B. & Wang, Y. (2011). Chin. J. Struct. Chem. 30, 799–804.
- Chernyshev, V. M., Chernysheva, A. V. & Starikova, Z. A. (2010). Heterocycles, 81, 2291–2311.
- Chernyshev, V. M., Chernysheva, A. V. & Taranushich, V. A. (2006). Russ. J. Appl. Chem. 79, 783–786.
- Chernyshev, V. M., Chernysheva, A. V. & Taranushich, V. A. (2009). Russ. J. Appl. Chem. 82, 276–281.
- Drożdżewski, P., Pawlak, B. & Głowiak, T. (2003). Transition Met. Chem. 28, 727–731.
- Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.
- Fan, R.-Z., Li, S.-J., Song, W.-D., Miao, D.-L. & Hu, S.-W. (2010). Acta Cryst. E66, m897–m898. [DOI] [PMC free article] [PubMed]
- Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
- Ferrer, S., Ballesteros, R., Sambartolomé, A., González, M., Alzuet, G., Borrás, J. & Liu, M. (2004). J. Inorg. Biochem. 98, 1436–1446. [DOI] [PubMed]
- Ferrer, S., Lloret, F., Pardo, E., Clemente-Juan, J. M., Liu-González, M. & García-Granda, S. (2012). Inorg. Chem. 51, 985–1001. [DOI] [PubMed]
- Gao, J.-Y., Xiong, X.-H., Chen, C.-J., Xie, W.-P., Ran, X.-R. & Yue, S.-T. (2013). Z. Anorg. Allg. Chem. 639, 582–586.
- Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
- Hernández-Gil, J., Ferrer, S., Castiñeiras, A., Liu-González, M., Lloret, F., Ribes, Á., Coga, L., Bernecker, A. & Mareque-Rivas, J. C. (2014). Inorg. Chem. 53, 578–593. [DOI] [PubMed]
- Hernández-Gil, J., Ferrer, S., Castiñeiras, A. & Lloret, F. (2012). Inorg. Chem. 51, 9809–9819. [DOI] [PubMed]
- Jin, G.-H., Li, X., Hu, C. & Hu, L. (2011). Acta Cryst. E67, m988. [DOI] [PMC free article] [PubMed]
- Lenstra, A. T. H., Slot, H. J. B., Beurskens, P. T., Haasnoot, J. G. & Reedijk, J. (1989). Rec. Trav. Chim. Pays-Bas, 108, 133–138.
- Liu, K., Shi, W. & Cheng, P. (2011). Dalton Trans. 40, 8475–8490. [DOI] [PubMed]
- North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
- Prins, R., Biagini-Cingi, M., Drillon, M., de Graaff, R. A. G., Haasnoot, J., Manotti-Lanfredi, A.-M., Rabu, P., Reedijk, J. & Ugozzoli, F. (1996). Inorg. Chim. Acta, 248, 35–44.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Siddiqui, K. A., Mehrotra, G. K., Narvi, S. S. & Butcher, R. J. (2011). Inorg. Chem. Commun. 14, 814–817.
- Sun, Y.-G., Xiong, G., Guo, M.-Y., Ding, F., Wang, L., Gao, E.-J., Zhu, M.-C. & Verpoort, F. (2011). Z. Anorg. Allg. Chem. 637, 293–300.
- Tabatabaee, M., Kukovec, B.-M. & Kazeroonizadeh, M. (2011). Polyhedron, 30, 1114–1119.
- Thomas, I. R., Bruno, I. J., Cole, J. C., Macrae, C. F., Pidcock, E. & Wood, P. A. (2010). J. Appl. Cryst. 43, 362–366. [DOI] [PMC free article] [PubMed]
- Tseng, T.-W., Luo, T.-T. & Lu, K.-H. (2014). CrystEngComm, 16, 5516–5519.
- Virovets, A. V., Bushuev, M. B. & Lavrenova, L. G. (2000). J. Struct. Chem. 41, 717–720.
- Wang, J., Li, W.-Z., Wang, J.-G. & Xiao, H.-P. (2011). Z. Kristallogr. New Cryst. Struct. 226, 163–164.
- Zheng, S., Cai, S., Fan, J. & Zhang, W. (2011). Acta Cryst. E67, m865. [DOI] [PMC free article] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814021436/wm5066sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021436/wm5066Isup2.hkl
CCDC reference: 1026535
Additional supporting information: crystallographic information; 3D view; checkCIF report