Crystal structure of bis­(2-methyl-1H-imidazol-3-ium) di­hydroxidobis(oxalato-κ2O1,O2)stannate(IV) monohydrate

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

doi:10.1107/S2056989016002061

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 3| March 2016| Pages 355-357

doi:10.1107/S2056989016002061

Open

access

Crystal structure of bis(2-methyl-1H-imidazol-3-ium) dihydroxidobis(oxalato-κ²O¹,O²)stannate(IV) monohydrate

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

^aLaboratoire 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

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 January 2016; accepted 2 February 2016; online 17 February 2016)

In the structure of the hydrated title salt, (C₄H₇N₂)₂[Sn(C₂O₄)₂(OH)₂]·H₂O, the asymmetric unit 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 Sn^IV 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 oxidation state +IV. A similar oxidation of Sn^II to Sn^IV has been reported recently (Diop et al., 2015).

2. Structural commentary

The Sn^IV 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.

Figure 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.

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).

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O3^iv	0.88	1.97	2.793 (4)	156
N1—H1⋯O4^iv	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⋯O8^v	0.88	1.94	2.787 (4)	161
C5—H5A⋯O4	0.98	2.55	3.460 (4)	155
C7—H7⋯O2^vi	0.95	2.39	3.327 (4)	169
C8—H8⋯O4ⁱⁱ	0.95	2.58	3.444 (4)	152
C12—H12⋯O5^vii	0.95	2.33	3.232 (4)	159
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) -x, -y+2, -z; (v) -x+1, -y, -z+1; (vi) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) -x+1, -y+1, -z+1.

Figure 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.

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 refinement 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 U_iso(H) = xU_eq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	(C₄H₇N₂)₂[Sn(C₂O₄)₂(H₂O)₂]·H₂O
M_r	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 )
T_min, T_max	0.509, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	42907, 4235, 4110
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	1.87, −0.81
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1451548

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989016002061/wm5268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016002061/wm5268Isup2.hkl

checkCIF report

Chemical context top

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 oxidation state +IV. A similar oxidation of Sn^II to Sn^IV has been reported recently (Diop et al., 2015).

Structural commentary top

The Sn^IV 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.

Supramolecular features top

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).

Synthesis and crystallization top

Refinement top

Crystal data, data collection and structure refinement 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 U_iso(H) = xU_eq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.

Structure description top

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 oxidation state +IV. A similar oxidation of Sn^II to Sn^IV has been reported recently (Diop et al., 2015).

The Sn^IV 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.

Synthesis and crystallization top

Refinement details top

Crystal data, data collection and structure refinement 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 U_iso(H) = xU_eq(C, N) with x = 1.5 for methyl and x = 1.2 for other H atoms.

Computing details top

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

Figures top

	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.

Bis(2-methyl-1H-imidazol-3-ium) dihydroxidobis(oxalato-κ²O¹,O²)stannate(IV) monohydrate top

Crystal data top

(C₄H₇N₂)₂[Sn(C₂O₄)₂(H₂O)₂]·H₂O	F(000) = 1024
M_r = 512.99	D_x = 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

Data collection top

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	R_int = 0.058
Detector resolution: 10.24 pixels mm^-1	θ_max = 60.9°, θ_min = 2.0°
ω and φ scans	h = −26→26
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −8→9
T_min = 0.509, T_max = 0.752	l = −17→17
42907 measured reflections

Refinement top

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(F_o²) + (0.0612P)² + 2.7674P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4235 reflections	Δρ_max = 1.87 e Å⁻³
265 parameters	Δρ_min = −0.81 e Å⁻³
4 restraints

Crystal data top

(C₄H₇N₂)₂[Sn(C₂O₄)₂(H₂O)₂]·H₂O	V = 1840.2 (2) Å³
M_r = 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)°

Data collection top

Bruker Venture Metaljet diffractometer	4235 independent reflections
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	4110 reflections with I > 2σ(I)
T_min = 0.509, T_max = 0.752	R_int = 0.058
42907 measured reflections

Refinement top

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	Δρ_max = 1.87 e Å⁻³
4235 reflections	Δρ_min = −0.81 e Å⁻³
265 parameters

Special details top

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

Geometry. All 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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.88	1.97	2.793 (4)	156
N1—H1···O4^iv	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···O8^v	0.88	1.94	2.787 (4)	161
C5—H5A···O4	0.98	2.55	3.460 (4)	155
C7—H7···O2^vi	0.95	2.39	3.327 (4)	169
C8—H8···O4ⁱⁱ	0.95	2.58	3.444 (4)	152
C12—H12···O5^vii	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.

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.88	1.97	2.793 (4)	156.1
N1—H1···O4^iv	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···O8^v	0.88	1.94	2.787 (4)	160.5
C5—H5A···O4	0.98	2.55	3.460 (4)	154.5
C7—H7···O2^vi	0.95	2.39	3.327 (4)	168.9
C8—H8···O4ⁱⁱ	0.95	2.58	3.444 (4)	151.9
C12—H12···O5^vii	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
M_r	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)
T_min, T_max	0.509, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	42907, 4235, 4110
R_int	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
Δρ_max, Δρ_min (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.

References

Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Davies, A. G., Gielen, M., Pannell, K. H. & Tiekink, E. R. T. (2008). In Tin Chemistry, Fundamentals, Frontiers and Applications. Chichester, UK: John Wiley & Sons Ltd. Google Scholar
Diop, M. B., Diop, L., Plasseraud, L. & Maris, T. (2015). Acta Cryst. E71, 520–522. CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gueye, N., Diop, L. & Stoeckli-Evans, H. (2014). Acta Cryst. E70, m49–m50. CSD CrossRef IUCr Journals Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Meneghetti, M. R. & Meneghetti, S. M. P. (2015). Catal. Sci. Technol. 5, 765–771. Web of Science CrossRef CAS Google Scholar
Sarr, M., Diasse-Sarr, A., Diop, L., Plasseraud, L. & Cattey, H. (2015). Acta Cryst. E71, 151–153. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sirajuddin, M., Ali, S., McKee, V., Zaib, S. & Iqbal, J. (2014). RSC Adv. 4, 57505–57521. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 72| Part 3| March 2016| Pages 355-357

doi:10.1107/S2056989016002061

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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