research communications
H-imidazol-3-ium) dihydroxidobis(oxalato-κ2O1,O2)stannate(IV) monohydrate
of bis(2-methyl-1aLaboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, bICMUB UMR 6302, Université de Bourgogne, Faculté des Sciences, 9 avenue Alain Savary, 21000 Dijon, France, and cDépartement de Chimie, Université de Montréal, 2900 Boulevard Édouard-Montpetit, Montréal, Québec, H3C 3J7, Canada
*Correspondence e-mail: mouhamadoubdiop@gmail.com
In the structure of the hydrated title salt, (C4H7N2)2[Sn(C2O4)2(OH)2]·H2O, the comprises one stannate(IV) dianion, two organic cations and one water molecule of crystallization. The [Sn(C2O4)2(OH)2]2− dianion consists of an SnIV atom chelated by two oxalate anions and coordinated by two OH− ligands in a cis octahedral arrangement. Neighbouring anions are connected through O—H⋯O hydrogen bonds between hydroxide groups and non-coordinating oxalate O atoms into layers expanding parallel to (100). In addition, cations and anions are linked through N—H⋯O hydrogen bonds, and the water molecule bridges two anions with two O—H⋯O hydrogen bonds and is also the acceptor of an N—H⋯O hydrogen bond with one of the cations. Weak C—H⋯O hydrogen bonds are also observed. The intricate hydrogen bonding leads to the formation of a three-dimensional network.
Keywords: crystal structure; organotin(IV) complex; hydrogen bonds.
CCDC reference: 1451548
1. Chemical context
Organotin(IV) compounds are a class of compounds studied for their numerous applications in various fields involving biological activities (Sirajuddin et al., 2014), biocidal properties (Davies et al., 2008) or catalysis applications (Meneghetti & Meneghetti, 2015). Interested in tin(IV) chemistry, our group has so far synthesized and structurally characterized several compounds of this family, see, for example: Sarr et al. (2015); Diop et al. (2015); Gueye et al. (2014). In the course of designing new oxalatostannate(IV) complexes, we report here the result of the reaction between bis(methyl-2-imidazolium) oxalate and SnCl2·2H2O that yielded the title compound (C4H7N2)2[Sn(C2O4)2(OH)2]·H2O with tin in +IV. A similar oxidation of SnII to SnIV has been reported recently (Diop et al., 2015).
2. Structural commentary
The SnIV atom is chelated by two oxalate anions and is coordinated by two OH groups in a cis arrangement, leading to a distorted octahedral environment (Fig. 1). The Sn—O distances involving the oxalate anions [2.103 (2) (O1), 2.077 (2) (O2), 2.074 (2) (O5) and 2.114 (2) Å (O6)] are in the typical range reported for oxalatostannate(IV) anions (Sarr et al., 2015; Gueye et al., 2014). The Sn—O distances involving the OH groups [2.001 (2) (O9) and 1.973 (2) Å (O10)] are shorter by ca 0.1 Å. The distortion from the ideal octahedron is reflected by the trans angle O1—Sn—O10 of 169.11 (9)° involving one of the hydroxyl groups and the oxalate O1 atom. Within the oxalate ligands, the distances [C1—O1 1.296 (4), C2—O2 1.300 (4), C3—O6 1.290 (4), C4—O5 1.299 (4) Å] and [C2—O3 1.215 (4), C1—O4 1.223 (4), O7—C3 1.220 (4), O8—C4 1.212 (4) Å] are compatible with single C—O and double C=O bonds, respectively. Bond lengths and angles within the two bis(2-methyl-1H-imidazol-3-ium) cations are in normal ranges.
3. Supramolecular features
Each stannate dianion [Sn(C2O4)2(OH)2]2− is linked to two neighbouring anions through hydroxyl(OH)⋯O hydrogen bonds involving the non-coordinating oxalate O atoms as acceptor groups. These interactions lead to the formation of layers extending parallel to (100). The cations interact with the anions via N—H⋯O hydrogen bonds (one bifurcated) whereby the non-coordinating oxalate O atoms again are the acceptor groups with the exception of one hydroxyl O atom (O9) as an acceptor (Table 1). The two hydroxyl groups are also acceptor groups of two (water)OH⋯O interactions, giving a total of nine hydrogen-bonding interactions per stannate dianion (Fig. 2). In addition to the dominant classical O—H⋯O and N—H⋯O interactions, weak C—H⋯O hydrogen bonds are also present in the structure (Table 1).
4. Synthesis and crystallization
The title compound was obtained by reacting in methanol in a 2:1 ratio SnCl2·2H2O with bis(methyl-2-imidazolium) oxalate. The latter was previously prepared in aqueous solution by mixing in a 2:1 ratio methyl-2-imidazole with oxalic acid and allowing the water to evaporate at 333 K. Slow solvent evaporation at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.
5. Refinement
Crystal data, data collection and structure . The coordinates of H atoms of the water molecules and hydroxy groups were obtained from a difference map and were refined using SADI and DFIX restraints (Sheldrick, 2015b). All other H atoms were positioned geometrically (C—H = 0.95, 0.98 Å, N—H = 0.88 Å) and refined as riding with Uiso(H) = xUeq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1451548
10.1107/S2056989016002061/wm5268sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016002061/wm5268Isup2.hkl
Organotin(IV) compounds are a class of compounds studied for their numerous applications in various fields involving biological activities (Sirajuddin et al., 2014), biocidal properties (Davies et al., 2008) or catalysis applications (Meneghetti & Meneghetti, 2015). Interested in tin(IV) chemistry, our group has so far synthesized and structurally characterized several compounds of this family, see, for example: Sarr et al. (2015); Diop et al. (2015); Gueye et al. (2014). In the course of designing new oxalatostannate(IV) complexes, we report here the result of the reaction between bis(methyl-2-imidazolium) oxalate and SnCl2·2H2O that yielded the title compound [(C4H7N2)2[Sn(C2O4)2(OH)2]·H2O] with tin in
+IV. A similar oxidation of SnII to SnIV has been reported recently (Diop et al., 2015).The SnIV atom is chelated by two oxalate anions and is coordinated by two OH groups in a cis arrangement, leading to a distorted octahedral environment (Fig. 1). The Sn—O distances involving the oxalate anions [2.103 (2) (O1), 2.077 (2) (O2), 2.074 (2) (O5) and 2.114 (2) Å (O6)] are in the typical range reported for oxalatostannate(IV) anions (Sarr et al., 2015; Gueye et al., 2014). The Sn—O distances involving the OH groups [2.001 (2) (O9) and 1.973 (2) Å (O10)] are shorter by ca 0.1 Å. The distortion from the ideal octahedron is reflected by the trans angle O1—Sn—O10 of 169.11 (9)° involving one of the hydroxyl groups and the oxalate O1 atom. Within the oxalate ligands, the distances [C1—O1 1.296 (4), C2—O2 1.300 (4), C3—O6 1.290 (4), C4—O5 1.299 (4) Å] and [C2—O3 1.215 (4), C1—O4 1.223 (4), O7—C3 1.220 (4), O8—C4 1.212 (4) Å] are compatible with single C—O and double C═O bonds, respectively. Bond lengths and angles within the two bis(2-methyl-1H-imidazol-3-ium) cations are in normal ranges.
Each stannate dianion [Sn(C2O4)2(OH)2]2− is linked to two neighbouring anions through hydroxyl(OH)···O hydrogen bonds involving the non-coordinating oxalate O atoms as acceptor groups. These interactions lead to the formation of layers extending parallel to (100). The cations interact with the anions via N—H···O hydrogen bonds (one bifurcated) whereby the non-coordinating oxalate O atoms again are the acceptor groups with the exception of one hydroxyl O atom (O9) as an acceptor (Table 1). The two hydroxyl groups are also acceptor groups of two (water)OH···O interactions, giving a total of nine hydrogen-bonding interactions per stannate dianion (Fig. 2). In addition to the dominant classical O—H···O and N—H···O interactions, weak C—H···O hydrogen bonds are also present in the structure (Table 1).
The title compound was obtained by reacting in methanol in a 2:1 ratio SnCl2·2H2O with bis(methyl-2-imidazolium) oxalate. The latter was previously prepared in aqueous solution by mixing in a 2:1 ratio methyl-2-imidazole with oxalic acid and allowing the water to evaporate at 333 K. Slow solvent evaporation at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.
Crystal data, data collection and structure
details are summarized in Table 2. The coordinates of H atoms of the water molecules and hydroxy groups were obtained from a difference map and were refined using SADI and DFIX restraints (Sheldrick, 2015b). All other H atoms were positioned geometrically (C—H = 0.95, 0.98 Å, N—H = 0.88 Å) and refined as riding with Uiso(H) = xUeq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.Organotin(IV) compounds are a class of compounds studied for their numerous applications in various fields involving biological activities (Sirajuddin et al., 2014), biocidal properties (Davies et al., 2008) or catalysis applications (Meneghetti & Meneghetti, 2015). Interested in tin(IV) chemistry, our group has so far synthesized and structurally characterized several compounds of this family, see, for example: Sarr et al. (2015); Diop et al. (2015); Gueye et al. (2014). In the course of designing new oxalatostannate(IV) complexes, we report here the result of the reaction between bis(methyl-2-imidazolium) oxalate and SnCl2·2H2O that yielded the title compound [(C4H7N2)2[Sn(C2O4)2(OH)2]·H2O] with tin in
+IV. A similar oxidation of SnII to SnIV has been reported recently (Diop et al., 2015).The SnIV atom is chelated by two oxalate anions and is coordinated by two OH groups in a cis arrangement, leading to a distorted octahedral environment (Fig. 1). The Sn—O distances involving the oxalate anions [2.103 (2) (O1), 2.077 (2) (O2), 2.074 (2) (O5) and 2.114 (2) Å (O6)] are in the typical range reported for oxalatostannate(IV) anions (Sarr et al., 2015; Gueye et al., 2014). The Sn—O distances involving the OH groups [2.001 (2) (O9) and 1.973 (2) Å (O10)] are shorter by ca 0.1 Å. The distortion from the ideal octahedron is reflected by the trans angle O1—Sn—O10 of 169.11 (9)° involving one of the hydroxyl groups and the oxalate O1 atom. Within the oxalate ligands, the distances [C1—O1 1.296 (4), C2—O2 1.300 (4), C3—O6 1.290 (4), C4—O5 1.299 (4) Å] and [C2—O3 1.215 (4), C1—O4 1.223 (4), O7—C3 1.220 (4), O8—C4 1.212 (4) Å] are compatible with single C—O and double C═O bonds, respectively. Bond lengths and angles within the two bis(2-methyl-1H-imidazol-3-ium) cations are in normal ranges.
Each stannate dianion [Sn(C2O4)2(OH)2]2− is linked to two neighbouring anions through hydroxyl(OH)···O hydrogen bonds involving the non-coordinating oxalate O atoms as acceptor groups. These interactions lead to the formation of layers extending parallel to (100). The cations interact with the anions via N—H···O hydrogen bonds (one bifurcated) whereby the non-coordinating oxalate O atoms again are the acceptor groups with the exception of one hydroxyl O atom (O9) as an acceptor (Table 1). The two hydroxyl groups are also acceptor groups of two (water)OH···O interactions, giving a total of nine hydrogen-bonding interactions per stannate dianion (Fig. 2). In addition to the dominant classical O—H···O and N—H···O interactions, weak C—H···O hydrogen bonds are also present in the structure (Table 1).
The title compound was obtained by reacting in methanol in a 2:1 ratio SnCl2·2H2O with bis(methyl-2-imidazolium) oxalate. The latter was previously prepared in aqueous solution by mixing in a 2:1 ratio methyl-2-imidazole with oxalic acid and allowing the water to evaporate at 333 K. Slow solvent evaporation at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.
detailsCrystal data, data collection and structure
details are summarized in Table 2. The coordinates of H atoms of the water molecules and hydroxy groups were obtained from a difference map and were refined using SADI and DFIX restraints (Sheldrick, 2015b). All other H atoms were positioned geometrically (C—H = 0.95, 0.98 Å, N—H = 0.88 Å) and refined as riding with Uiso(H) = xUeq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).Fig. 1. The structure of the molecular components in the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius and hydrogen bonds are shown as dashed lines. | |
Fig. 2. A view of a central stannate dianion (ball-and-stick representation) surrounded by its hydrogen-bonded neighbours (stick representation), viz three cations, two water molecules and four other stannate anions. Hydrogen bonds are displayed as black dotted lines and H atoms not involved in hydrogen bonding have been omitted for clarity. |
(C4H7N2)2[Sn(C2O4)2(H2O)2]·H2O | F(000) = 1024 |
Mr = 512.99 | Dx = 1.852 Mg m−3 |
Monoclinic, P21/c | Ga Kα radiation, λ = 1.34139 Å |
a = 20.1391 (13) Å | Cell parameters from 9589 reflections |
b = 7.0651 (5) Å | θ = 4.2–60.8° |
c = 13.4942 (9) Å | µ = 7.83 mm−1 |
β = 106.582 (2)° | T = 110 K |
V = 1840.2 (2) Å3 | Block, clear light colourless |
Z = 4 | 0.19 × 0.11 × 0.09 mm |
Bruker Venture Metaljet diffractometer | 4235 independent reflections |
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source | 4110 reflections with I > 2σ(I) |
Helios MX Mirror Optics monochromator | Rint = 0.058 |
Detector resolution: 10.24 pixels mm-1 | θmax = 60.9°, θmin = 2.0° |
ω and φ scans | h = −26→26 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −8→9 |
Tmin = 0.509, Tmax = 0.752 | l = −17→17 |
42907 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0612P)2 + 2.7674P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
4235 reflections | Δρmax = 1.87 e Å−3 |
265 parameters | Δρmin = −0.81 e Å−3 |
4 restraints |
(C4H7N2)2[Sn(C2O4)2(H2O)2]·H2O | V = 1840.2 (2) Å3 |
Mr = 512.99 | Z = 4 |
Monoclinic, P21/c | Ga Kα radiation, λ = 1.34139 Å |
a = 20.1391 (13) Å | µ = 7.83 mm−1 |
b = 7.0651 (5) Å | T = 110 K |
c = 13.4942 (9) Å | 0.19 × 0.11 × 0.09 mm |
β = 106.582 (2)° |
Bruker Venture Metaljet diffractometer | 4235 independent reflections |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | 4110 reflections with I > 2σ(I) |
Tmin = 0.509, Tmax = 0.752 | Rint = 0.058 |
42907 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 4 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 1.87 e Å−3 |
4235 reflections | Δρmin = −0.81 e Å−3 |
265 parameters |
Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.24060 (2) | 0.62119 (3) | 0.27535 (2) | 0.02481 (10) | |
O1 | 0.22492 (11) | 0.6762 (3) | 0.11720 (17) | 0.0312 (4) | |
O2 | 0.13386 (12) | 0.5897 (3) | 0.21916 (18) | 0.0293 (5) | |
O3 | 0.04507 (12) | 0.6473 (3) | 0.07971 (18) | 0.0330 (5) | |
O4 | 0.13911 (12) | 0.7325 (3) | −0.02786 (17) | 0.0347 (5) | |
O5 | 0.34706 (12) | 0.6212 (3) | 0.29967 (19) | 0.0278 (5) | |
O6 | 0.25904 (10) | 0.3368 (3) | 0.24215 (18) | 0.0280 (4) | |
O7 | 0.34600 (13) | 0.1302 (3) | 0.2613 (2) | 0.0368 (6) | |
O8 | 0.43752 (11) | 0.4264 (3) | 0.3297 (2) | 0.0347 (5) | |
O9 | 0.24047 (12) | 0.9006 (3) | 0.2994 (2) | 0.0306 (5) | |
H9 | 0.2722 | 0.9540 | 0.2777 | 0.046* | |
O10 | 0.24113 (12) | 0.5339 (3) | 0.41448 (17) | 0.0321 (5) | |
H10 | 0.2163 | 0.6085 | 0.4403 | 0.048* | |
C1 | 0.16053 (15) | 0.6868 (4) | 0.0632 (2) | 0.0274 (6) | |
C2 | 0.10678 (17) | 0.6380 (4) | 0.1231 (2) | 0.0273 (6) | |
C3 | 0.32352 (15) | 0.2896 (4) | 0.2648 (2) | 0.0280 (6) | |
C4 | 0.37567 (15) | 0.4559 (4) | 0.3017 (2) | 0.0275 (6) | |
N1 | 0.01942 (13) | 1.1771 (4) | 0.1086 (2) | 0.0289 (5) | |
H1 | −0.0115 | 1.2288 | 0.0559 | 0.043* | |
N2 | 0.11571 (14) | 1.0703 (4) | 0.2068 (2) | 0.0299 (5) | |
H2 | 0.1597 | 1.0387 | 0.2303 | 0.045* | |
C5 | 0.12035 (18) | 1.2002 (5) | 0.0351 (3) | 0.0343 (7) | |
H5A | 0.1243 | 1.0864 | −0.0043 | 0.051* | |
H5B | 0.1667 | 1.2509 | 0.0683 | 0.051* | |
H5C | 0.0928 | 1.2956 | −0.0116 | 0.051* | |
C6 | 0.08607 (16) | 1.1515 (4) | 0.1151 (2) | 0.0271 (6) | |
C7 | 0.00616 (19) | 1.1103 (4) | 0.1971 (3) | 0.0332 (7) | |
H7 | −0.0372 | 1.1110 | 0.2118 | 0.040* | |
C8 | 0.06634 (17) | 1.0440 (5) | 0.2585 (2) | 0.0334 (6) | |
H8 | 0.0736 | 0.9893 | 0.3250 | 0.040* | |
N3 | 0.40483 (15) | 0.0861 (4) | 0.5690 (2) | 0.0342 (6) | |
H3 | 0.3611 | 0.1160 | 0.5404 | 0.051* | |
N4 | 0.49720 (14) | −0.0750 (4) | 0.6344 (2) | 0.0306 (5) | |
H4 | 0.5252 | −0.1712 | 0.6567 | 0.046* | |
C9 | 0.38714 (19) | −0.2637 (5) | 0.5737 (3) | 0.0390 (7) | |
H9A | 0.4017 | −0.3457 | 0.6346 | 0.059* | |
H9B | 0.3941 | −0.3298 | 0.5136 | 0.059* | |
H9C | 0.3380 | −0.2320 | 0.5604 | 0.059* | |
C10 | 0.42895 (17) | −0.0874 (5) | 0.5925 (2) | 0.0298 (6) | |
C11 | 0.45913 (19) | 0.2124 (5) | 0.5965 (3) | 0.0380 (7) | |
H11 | 0.4562 | 0.3460 | 0.5881 | 0.046* | |
C12 | 0.5171 (2) | 0.1116 (4) | 0.6374 (3) | 0.0347 (7) | |
H12 | 0.5628 | 0.1599 | 0.6633 | 0.042* | |
O11 | 0.26942 (14) | 0.1609 (4) | 0.4740 (2) | 0.0406 (6) | |
H11A | 0.258 (3) | 0.267 (3) | 0.449 (4) | 0.074 (18)* | |
H11B | 0.259 (4) | 0.079 (6) | 0.428 (4) | 0.10 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01935 (13) | 0.02397 (14) | 0.02993 (14) | 0.00241 (6) | 0.00517 (9) | 0.00129 (6) |
O1 | 0.0245 (10) | 0.0368 (11) | 0.0333 (11) | −0.0011 (9) | 0.0097 (8) | 0.0009 (9) |
O2 | 0.0236 (10) | 0.0338 (11) | 0.0311 (11) | 0.0006 (9) | 0.0088 (9) | 0.0052 (9) |
O3 | 0.0233 (11) | 0.0407 (12) | 0.0327 (11) | −0.0004 (9) | 0.0043 (9) | 0.0021 (9) |
O4 | 0.0353 (12) | 0.0380 (12) | 0.0295 (11) | 0.0011 (9) | 0.0073 (9) | 0.0035 (9) |
O5 | 0.0205 (10) | 0.0245 (11) | 0.0389 (12) | 0.0019 (7) | 0.0092 (9) | 0.0008 (8) |
O6 | 0.0216 (10) | 0.0263 (10) | 0.0357 (11) | −0.0001 (8) | 0.0075 (8) | −0.0016 (9) |
O7 | 0.0286 (12) | 0.0265 (12) | 0.0561 (16) | 0.0006 (8) | 0.0136 (11) | −0.0043 (9) |
O8 | 0.0218 (10) | 0.0284 (10) | 0.0524 (14) | 0.0023 (9) | 0.0080 (10) | 0.0003 (10) |
O9 | 0.0266 (12) | 0.0241 (10) | 0.0408 (12) | 0.0015 (8) | 0.0090 (9) | 0.0010 (9) |
O10 | 0.0329 (11) | 0.0344 (12) | 0.0297 (10) | 0.0044 (9) | 0.0100 (9) | 0.0037 (9) |
C1 | 0.0257 (14) | 0.0237 (14) | 0.0321 (14) | 0.0011 (11) | 0.0070 (11) | −0.0011 (11) |
C2 | 0.0263 (15) | 0.0241 (14) | 0.0295 (14) | −0.0003 (10) | 0.0046 (12) | −0.0011 (10) |
C3 | 0.0250 (14) | 0.0259 (14) | 0.0335 (14) | −0.0011 (11) | 0.0089 (11) | −0.0020 (11) |
C4 | 0.0253 (14) | 0.0256 (14) | 0.0311 (14) | 0.0012 (11) | 0.0071 (11) | 0.0005 (11) |
N1 | 0.0238 (12) | 0.0302 (13) | 0.0311 (12) | 0.0037 (10) | 0.0055 (10) | 0.0016 (10) |
N2 | 0.0241 (12) | 0.0287 (12) | 0.0342 (13) | 0.0026 (10) | 0.0039 (10) | −0.0011 (11) |
C5 | 0.0340 (16) | 0.0342 (17) | 0.0375 (16) | −0.0007 (13) | 0.0146 (13) | −0.0016 (13) |
C6 | 0.0242 (14) | 0.0246 (13) | 0.0324 (15) | 0.0008 (11) | 0.0077 (12) | −0.0019 (11) |
C7 | 0.0300 (17) | 0.0335 (17) | 0.0377 (17) | 0.0005 (12) | 0.0122 (14) | −0.0001 (12) |
C8 | 0.0378 (17) | 0.0298 (16) | 0.0319 (15) | −0.0003 (13) | 0.0086 (13) | 0.0019 (12) |
N3 | 0.0305 (14) | 0.0313 (13) | 0.0377 (14) | 0.0056 (11) | 0.0048 (11) | −0.0020 (11) |
N4 | 0.0262 (13) | 0.0274 (12) | 0.0360 (14) | 0.0032 (11) | 0.0052 (11) | −0.0020 (11) |
C9 | 0.0348 (17) | 0.0329 (17) | 0.0463 (18) | −0.0007 (14) | 0.0067 (14) | −0.0071 (14) |
C10 | 0.0266 (15) | 0.0309 (14) | 0.0313 (15) | 0.0035 (12) | 0.0071 (12) | −0.0041 (12) |
C11 | 0.0416 (18) | 0.0270 (15) | 0.0443 (18) | 0.0000 (13) | 0.0106 (15) | −0.0007 (13) |
C12 | 0.0328 (17) | 0.0324 (17) | 0.0384 (17) | −0.0040 (12) | 0.0092 (14) | −0.0029 (12) |
O11 | 0.0375 (13) | 0.0423 (13) | 0.0409 (13) | 0.0100 (11) | 0.0095 (11) | 0.0049 (12) |
Sn1—O1 | 2.103 (2) | N2—C8 | 1.380 (4) |
Sn1—O2 | 2.077 (2) | C5—H5A | 0.9800 |
Sn1—O5 | 2.074 (2) | C5—H5B | 0.9800 |
Sn1—O6 | 2.114 (2) | C5—H5C | 0.9800 |
Sn1—O9 | 2.001 (2) | C5—C6 | 1.478 (4) |
Sn1—O10 | 1.973 (2) | C7—H7 | 0.9500 |
O1—C1 | 1.296 (4) | C7—C8 | 1.342 (5) |
O2—C2 | 1.300 (4) | C8—H8 | 0.9500 |
O3—C2 | 1.215 (4) | N3—H3 | 0.8800 |
O4—C1 | 1.223 (4) | N3—C10 | 1.324 (4) |
O5—C4 | 1.299 (4) | N3—C11 | 1.378 (5) |
O6—C3 | 1.290 (4) | N4—H4 | 0.8800 |
O7—C3 | 1.220 (4) | N4—C10 | 1.332 (4) |
O8—C4 | 1.212 (4) | N4—C12 | 1.375 (4) |
O9—H9 | 0.8616 | C9—H9A | 0.9800 |
O10—H10 | 0.8653 | C9—H9B | 0.9800 |
C1—C2 | 1.563 (4) | C9—H9C | 0.9800 |
C3—C4 | 1.560 (4) | C9—C10 | 1.484 (5) |
N1—H1 | 0.8800 | C11—H11 | 0.9500 |
N1—C6 | 1.332 (4) | C11—C12 | 1.344 (5) |
N1—C7 | 1.379 (4) | C12—H12 | 0.9500 |
N2—H2 | 0.8800 | O11—H11A | 0.831 (15) |
N2—C6 | 1.339 (4) | O11—H11B | 0.827 (16) |
O1—Sn1—O6 | 86.86 (9) | C8—N2—H2 | 125.4 |
O2—Sn1—O1 | 79.01 (9) | H5A—C5—H5B | 109.5 |
O2—Sn1—O6 | 92.69 (8) | H5A—C5—H5C | 109.5 |
O5—Sn1—O1 | 90.55 (9) | H5B—C5—H5C | 109.5 |
O5—Sn1—O2 | 166.65 (9) | C6—C5—H5A | 109.5 |
O5—Sn1—O6 | 78.32 (8) | C6—C5—H5B | 109.5 |
O9—Sn1—O1 | 88.58 (10) | C6—C5—H5C | 109.5 |
O9—Sn1—O2 | 96.65 (9) | N1—C6—N2 | 107.1 (3) |
O9—Sn1—O5 | 91.33 (8) | N1—C6—C5 | 126.3 (3) |
O9—Sn1—O6 | 168.64 (9) | N2—C6—C5 | 126.6 (3) |
O10—Sn1—O1 | 169.11 (9) | N1—C7—H7 | 126.6 |
O10—Sn1—O2 | 92.17 (9) | C8—C7—N1 | 106.8 (3) |
O10—Sn1—O5 | 97.17 (9) | C8—C7—H7 | 126.6 |
O10—Sn1—O6 | 87.19 (9) | N2—C8—H8 | 126.4 |
O10—Sn1—O9 | 98.87 (10) | C7—C8—N2 | 107.2 (3) |
C1—O1—Sn1 | 114.71 (19) | C7—C8—H8 | 126.4 |
C2—O2—Sn1 | 115.6 (2) | C10—N3—H3 | 125.5 |
C4—O5—Sn1 | 115.80 (18) | C10—N3—C11 | 109.1 (3) |
C3—O6—Sn1 | 114.93 (19) | C11—N3—H3 | 125.5 |
Sn1—O9—H9 | 110.0 | C10—N4—H4 | 125.3 |
Sn1—O10—H10 | 110.2 | C10—N4—C12 | 109.4 (3) |
O1—C1—C2 | 115.2 (3) | C12—N4—H4 | 125.3 |
O4—C1—O1 | 126.1 (3) | H9A—C9—H9B | 109.5 |
O4—C1—C2 | 118.7 (3) | H9A—C9—H9C | 109.5 |
O2—C2—C1 | 114.7 (3) | H9B—C9—H9C | 109.5 |
O3—C2—O2 | 125.1 (3) | C10—C9—H9A | 109.5 |
O3—C2—C1 | 120.2 (3) | C10—C9—H9B | 109.5 |
O6—C3—C4 | 114.9 (3) | C10—C9—H9C | 109.5 |
O7—C3—O6 | 126.1 (3) | N3—C10—N4 | 107.7 (3) |
O7—C3—C4 | 119.0 (3) | N3—C10—C9 | 125.8 (3) |
O5—C4—C3 | 114.6 (2) | N4—C10—C9 | 126.5 (3) |
O8—C4—O5 | 124.8 (3) | N3—C11—H11 | 126.4 |
O8—C4—C3 | 120.6 (3) | C12—C11—N3 | 107.3 (3) |
C6—N1—H1 | 125.2 | C12—C11—H11 | 126.4 |
C6—N1—C7 | 109.7 (3) | N4—C12—H12 | 126.7 |
C7—N1—H1 | 125.2 | C11—C12—N4 | 106.6 (3) |
C6—N2—H2 | 125.4 | C11—C12—H12 | 126.7 |
C6—N2—C8 | 109.2 (3) | H11A—O11—H11B | 110 (3) |
Sn1—O1—C1—O4 | 173.7 (3) | O7—C3—C4—O8 | −2.5 (5) |
Sn1—O1—C1—C2 | −5.5 (3) | N1—C7—C8—N2 | −0.2 (4) |
Sn1—O2—C2—O3 | −172.4 (2) | C6—N1—C7—C8 | 0.4 (4) |
Sn1—O2—C2—C1 | 7.4 (3) | C6—N2—C8—C7 | 0.0 (4) |
Sn1—O5—C4—O8 | −168.6 (3) | C7—N1—C6—N2 | −0.4 (4) |
Sn1—O5—C4—C3 | 11.0 (3) | C7—N1—C6—C5 | 178.5 (3) |
Sn1—O6—C3—O7 | 172.8 (3) | C8—N2—C6—N1 | 0.2 (4) |
Sn1—O6—C3—C4 | −6.1 (3) | C8—N2—C6—C5 | −178.7 (3) |
O1—C1—C2—O2 | −1.2 (4) | N3—C11—C12—N4 | −0.1 (4) |
O1—C1—C2—O3 | 178.6 (3) | C10—N3—C11—C12 | 0.0 (4) |
O4—C1—C2—O2 | 179.6 (3) | C10—N4—C12—C11 | 0.2 (4) |
O4—C1—C2—O3 | −0.7 (4) | C11—N3—C10—N4 | 0.1 (4) |
O6—C3—C4—O5 | −3.2 (4) | C11—N3—C10—C9 | −179.0 (3) |
O6—C3—C4—O8 | 176.5 (3) | C12—N4—C10—N3 | −0.2 (4) |
O7—C3—C4—O5 | 177.8 (3) | C12—N4—C10—C9 | 179.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O7i | 0.86 | 2.00 | 2.835 (3) | 163 |
O10—H10···O4ii | 0.87 | 2.06 | 2.909 (3) | 167 |
O11—H11A···O10 | 0.83 (2) | 1.95 (2) | 2.766 (4) | 169 (5) |
O11—H11B···O9iii | 0.83 (2) | 2.10 (2) | 2.914 (4) | 170 (7) |
N1—H1···O3iv | 0.88 | 1.97 | 2.793 (4) | 156 |
N1—H1···O4iv | 0.88 | 2.50 | 3.131 (3) | 129 |
N2—H2···O9 | 0.88 | 1.90 | 2.742 (3) | 160 |
N3—H3···O11 | 0.88 | 1.84 | 2.713 (4) | 175 |
N4—H4···O8v | 0.88 | 1.94 | 2.787 (4) | 161 |
C5—H5A···O4 | 0.98 | 2.55 | 3.460 (4) | 155 |
C7—H7···O2vi | 0.95 | 2.39 | 3.327 (4) | 169 |
C8—H8···O4ii | 0.95 | 2.58 | 3.444 (4) | 152 |
C12—H12···O5vii | 0.95 | 2.33 | 3.232 (4) | 159 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2; (iii) x, y−1, z; (iv) −x, −y+2, −z; (v) −x+1, −y, −z+1; (vi) −x, y+1/2, −z+1/2; (vii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O7i | 0.86 | 2.00 | 2.835 (3) | 163.1 |
O10—H10···O4ii | 0.87 | 2.06 | 2.909 (3) | 166.8 |
O11—H11A···O10 | 0.831 (15) | 1.946 (17) | 2.766 (4) | 169 (5) |
O11—H11B···O9iii | 0.827 (16) | 2.10 (2) | 2.914 (4) | 170 (7) |
N1—H1···O3iv | 0.88 | 1.97 | 2.793 (4) | 156.1 |
N1—H1···O4iv | 0.88 | 2.50 | 3.131 (3) | 128.7 |
N2—H2···O9 | 0.88 | 1.90 | 2.742 (3) | 160.2 |
N3—H3···O11 | 0.88 | 1.84 | 2.713 (4) | 175.3 |
N4—H4···O8v | 0.88 | 1.94 | 2.787 (4) | 160.5 |
C5—H5A···O4 | 0.98 | 2.55 | 3.460 (4) | 154.5 |
C7—H7···O2vi | 0.95 | 2.39 | 3.327 (4) | 168.9 |
C8—H8···O4ii | 0.95 | 2.58 | 3.444 (4) | 151.9 |
C12—H12···O5vii | 0.95 | 2.33 | 3.232 (4) | 158.7 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2; (iii) x, y−1, z; (iv) −x, −y+2, −z; (v) −x+1, −y, −z+1; (vi) −x, y+1/2, −z+1/2; (vii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | (C4H7N2)2[Sn(C2O4)2(H2O)2]·H2O |
Mr | 512.99 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 110 |
a, b, c (Å) | 20.1391 (13), 7.0651 (5), 13.4942 (9) |
β (°) | 106.582 (2) |
V (Å3) | 1840.2 (2) |
Z | 4 |
Radiation type | Ga Kα, λ = 1.34139 Å |
µ (mm−1) | 7.83 |
Crystal size (mm) | 0.19 × 0.11 × 0.09 |
Data collection | |
Diffractometer | Bruker Venture Metaljet |
Absorption correction | Multi-scan (SADABS; Krause et al., 2015) |
Tmin, Tmax | 0.509, 0.752 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42907, 4235, 4110 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.101, 1.07 |
No. of reflections | 4235 |
No. of parameters | 265 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.87, −0.81 |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).
Acknowledgements
The authors acknowledge the Cheikh Anta Diop University of Dakar (Sénégal), the Canada Foundation for Innovation, Université de Bourgogne and Université de Montréal for financial support.
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