Aquadi-n-but­yl(5-methyl­pyrazine-2-carboxyl­ato)tin(IV) methanol solvate

Gao, Z.

doi:10.1107/S1600536808016140

metal-organic compounds

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Volume 64| Part 7| July 2008| Page m864

doi:10.1107/S1600536808016140

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Aquadi-n-butyl(5-methylpyrazine-2-carboxylato)tin(IV) methanol solvate

Zhongjun Gao ^a ^*

^aDeapartment of Chemistry, Jining University, Shandong 273155, People's Republic of China
^*Correspondence e-mail: zhongjungao@yahoo.cn

(Received 23 April 2008; accepted 28 May 2008; online 7 June 2008)

In the monomeric title compound, [Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₃OH, the Sn atom is seven-coordinate, displaying a distorted pentagonal bipyramidal SnC₂N₂O₃ geometry with the two C atoms in the axial sites. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the complex and solvent molecules into infinite chains.

Related literature

For general background, see: Gielen et al. (1988 ). For a related structure, see: Ma et al. (2004 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₄O
M_r = 557.21
Monoclinic, C 2/c
a = 20.609 (5) Å
b = 17.119 (4) Å
c = 14.558 (3) Å
β = 98.178 (3)°
V = 5084 (2) Å³
Z = 8
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 298 (2) K
0.58 × 0.56 × 0.49 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.582, T_max = 0.628
12959 measured reflections
4462 independent reflections
2981 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.122
S = 1.12
4462 reflections
289 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C17	2.103 (5)
Sn1—C13	2.107 (6)
Sn1—O1	2.161 (4)
Sn1—O3	2.167 (4)
Sn1—N1	2.481 (4)
Sn1—N3	2.635 (5)
Sn1—O5	2.770 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O6	0.85	1.92	2.755 (6)	169
O5—H2⋯O1ⁱ	0.85	2.19	3.039 (5)	172
O6—H6⋯O4ⁱ	0.82	1.93	2.703 (6)	156
Symmetry code: (i) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016140/hb2726sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016140/hb2726Isup2.hkl

checkCIF report

Comment top

Self-assembled organotin derivatives of carboxylic acid ligands have been extensively studied due to their biological activities (Gielen et al., 1988). 2-Methylpyrazine-5-carboxylic acid is a good bridging ligand that can sometimes be used to generate unexpected and interesting coordination polymers, and small changes in experimental conditions can lead to very different architectures.

The title compound, (I), consists of two butyl, two N,O-bidentate 2-methylpyrazine-5-carboxylate groups and a water molecule bonded to the Sn atom and has a monomeric structure. The Sn atom is seven-coordinate with a distorted pentagonal bipyramidal SnC₂N₂O₃ geometry (Table 1, Fig. 1). Around the central Sn atom, atoms C13 and C17 of the two butyl groups occupy the axial position, while O and N atoms lie in equatorial positions. The sum of the angles between the tin atom and the equatorial atoms is 360.4°. The axial bond angle C17—Sn1—C13 [161.6 (3)°] deviates from linearity by over 18°, which shows that these atoms have significant deviations from ideal pentagonal bipyramidal geometry. Otherwise, the bond lenghts and angles in (I) are similar to those in related structures (Ma et al., 2004).

In the crystal, strong intermolecular O—H···O hydrogen bonds (Table 2) between O atoms of the carboxyl groups, methanol and coordinate water molecules result in the formation of one-dimensional polymeric chains (Fig. 2).

Related literature top

For general background, see: Gielen et al. (1988). For a related structure, see: Ma et al. (2004).

Experimental top

A mixture of dibutyltin dichloride (1.0 mmol, 0.304 g), 2-methylpyrazine-5-carboxylic acid (2.0 mmol, 0.276 g) and sodium ethoxide (0.136 g, 2.0 mmol) in ethanol (with 5% water) (80 ml) was heated under reflux for 8 h at 303 K. The resulting clear solution was evaporated under vacuum and the product recrystallized from a mixture of methanol to yield colourless, blocks of (I). Yield 0.452 g, 78%, m.p. 438 K, analysis, calculated for C₂₁H₃₄N₄O₆Sn: C 45.26, H, 6.15; N 10.05%; found: C 45.39, H 6.29, N, 10.12%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. The hydrogen bond is indicated by a double-dashed line.
	Fig. 2. Packing diagram of the crystal structure of (I), showing the one-dimensional chains that form along the c axis. H atoms are omitted for clarity and dashed lines link the donor and acceptor O atoms of the hydrogen bonds.

Aquadi-n-butyl(5-methylpyrazine-2-carboxylato)tin(IV) methanol solvate top

Crystal data top

[Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₄O	F(000) = 2288
M_r = 557.21	D_x = 1.456 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4606 reflections
a = 20.609 (5) Å	θ = 2.4–25.3°
b = 17.119 (4) Å	µ = 1.05 mm⁻¹
c = 14.558 (3) Å	T = 298 K
β = 98.178 (3)°	Block, colourless
V = 5084 (2) Å³	0.58 × 0.56 × 0.49 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	4462 independent reflections
Radiation source: fine-focus sealed tube	2981 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −15→24
T_min = 0.582, T_max = 0.628	k = −20→20
12959 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0455P)² + 11.2132P] where P = (F_o² + 2F_c²)/3
4462 reflections	(Δ/σ)_max = 0.002
289 parameters	Δρ_max = 0.58 e Å⁻³
12 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₄O	V = 5084 (2) Å³
M_r = 557.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.609 (5) Å	µ = 1.05 mm⁻¹
b = 17.119 (4) Å	T = 298 K
c = 14.558 (3) Å	0.58 × 0.56 × 0.49 mm
β = 98.178 (3)°

Data collection top

Bruker SMART CCD diffractometer	4462 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2981 reflections with I > 2σ(I)
T_min = 0.582, T_max = 0.628	R_int = 0.039
12959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	12 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0455P)² + 11.2132P] where P = (F_o² + 2F_c²)/3
4462 reflections	Δρ_max = 0.58 e Å⁻³
289 parameters	Δρ_min = −0.67 e Å⁻³

Special details top

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.

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 > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.256428 (17)	1.005653 (19)	0.41391 (2)	0.05022 (15)
N1	0.3679 (2)	0.9489 (2)	0.4509 (3)	0.0496 (10)
N2	0.4975 (2)	0.9001 (3)	0.4682 (4)	0.0746 (15)
N3	0.1453 (2)	1.0475 (3)	0.4696 (3)	0.0597 (12)
N4	0.0240 (3)	1.1105 (4)	0.4929 (4)	0.0858 (17)
O1	0.30863 (18)	1.0137 (2)	0.2956 (2)	0.0579 (9)
O2	0.4017 (2)	1.0160 (3)	0.2351 (3)	0.0784 (12)
O3	0.18771 (19)	1.0558 (2)	0.3031 (3)	0.0673 (11)
O4	0.09289 (19)	1.1052 (3)	0.2392 (3)	0.0757 (12)
O5	0.26009 (19)	0.9499 (2)	0.5931 (3)	0.0736 (11)
H1	0.2327	0.9135	0.5983	0.088*
H2	0.2730	0.9647	0.6484	0.088*
C1	0.3704 (3)	1.0012 (3)	0.2976 (4)	0.0529 (13)
C2	0.4039 (3)	0.9618 (3)	0.3833 (4)	0.0513 (13)
C3	0.4686 (3)	0.9380 (4)	0.3940 (4)	0.0679 (16)
H3	0.4932	0.9491	0.3467	0.082*
C4	0.4612 (3)	0.8866 (3)	0.5350 (4)	0.0620 (15)
C5	0.3965 (3)	0.9124 (3)	0.5273 (4)	0.0591 (14)
H5	0.3727	0.9042	0.5762	0.071*
C6	0.4918 (3)	0.8426 (4)	0.6191 (4)	0.090 (2)
H6A	0.5364	0.8300	0.6129	0.135*
H6B	0.4677	0.7953	0.6250	0.135*
H6C	0.4910	0.8743	0.6733	0.135*
C7	0.1295 (3)	1.0804 (3)	0.3063 (4)	0.0586 (14)
C8	0.1057 (3)	1.0790 (3)	0.3989 (4)	0.0532 (13)
C9	0.0454 (3)	1.1085 (4)	0.4106 (5)	0.0747 (18)
H9	0.0183	1.1279	0.3591	0.090*
C10	0.0627 (3)	1.0788 (4)	0.5628 (5)	0.0722 (17)
C11	0.1233 (3)	1.0474 (4)	0.5517 (4)	0.0729 (17)
H11	0.1492	1.0256	0.6027	0.087*
C12	0.0393 (4)	1.0786 (5)	0.6554 (5)	0.103 (3)
H12A	−0.0033	1.1022	0.6499	0.155*
H12B	0.0694	1.1076	0.6989	0.155*
H12C	0.0368	1.0258	0.6767	0.155*
C13	0.2915 (4)	1.1117 (4)	0.4756 (5)	0.091 (2)
H13A	0.3165	1.1364	0.4319	0.110*
H13B	0.2532	1.1442	0.4778	0.110*
C14	0.3295 (5)	1.1185 (4)	0.5624 (6)	0.128 (3)
H14A	0.3671	1.0843	0.5633	0.153*
H14B	0.3038	1.0990	0.6084	0.153*
C15	0.3547 (4)	1.1996 (4)	0.5931 (7)	0.111 (3)
H15A	0.3814	1.2197	0.5488	0.133*
H15B	0.3178	1.2346	0.5938	0.133*
C16	0.3937 (5)	1.1977 (5)	0.6860 (7)	0.139 (4)
H16A	0.4091	1.2494	0.7029	0.208*
H16B	0.4305	1.1634	0.6854	0.208*
H16C	0.3670	1.1792	0.7303	0.208*
C17	0.2167 (3)	0.8926 (3)	0.3962 (4)	0.0697 (17)
H17A	0.2404	0.8590	0.4431	0.084*
H17B	0.1716	0.8946	0.4079	0.084*
C18	0.2177 (4)	0.8561 (4)	0.3060 (5)	0.107 (3)
H18A	0.2627	0.8497	0.2950	0.129*
H18B	0.1955	0.8895	0.2577	0.129*
C19	0.1832 (6)	0.7749 (5)	0.3022 (7)	0.148 (4)
H19A	0.2050	0.7431	0.3525	0.178*
H19B	0.1384	0.7826	0.3133	0.178*
C20	0.1821 (7)	0.7340 (7)	0.2212 (9)	0.217 (7)
H20A	0.1597	0.6853	0.2258	0.326*
H20B	0.2262	0.7240	0.2103	0.326*
H20C	0.1596	0.7640	0.1707	0.326*
C21	0.1267 (4)	0.7823 (4)	0.5608 (5)	0.104 (3)
H21A	0.1147	0.7483	0.6081	0.156*
H21B	0.1551	0.7550	0.5249	0.156*
H21C	0.0879	0.7986	0.5210	0.156*
O6	0.1586 (3)	0.8466 (3)	0.6014 (4)	0.123 (2)
H6	0.1340	0.8703	0.6312	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0454 (2)	0.0530 (2)	0.0517 (2)	0.00077 (18)	0.00511 (16)	−0.00375 (17)
N1	0.048 (2)	0.050 (2)	0.051 (3)	0.001 (2)	0.006 (2)	−0.002 (2)
N2	0.057 (3)	0.092 (4)	0.074 (3)	0.017 (3)	0.004 (3)	0.000 (3)
N3	0.055 (3)	0.062 (3)	0.062 (3)	0.010 (2)	0.010 (2)	0.000 (2)
N4	0.066 (3)	0.111 (5)	0.084 (4)	0.014 (3)	0.024 (3)	0.010 (3)
O1	0.046 (2)	0.077 (2)	0.050 (2)	0.0019 (19)	0.0050 (17)	0.0063 (18)
O2	0.065 (3)	0.114 (3)	0.059 (3)	0.007 (2)	0.018 (2)	0.018 (2)
O3	0.056 (2)	0.088 (3)	0.058 (2)	0.019 (2)	0.0097 (19)	0.005 (2)
O4	0.057 (2)	0.110 (3)	0.058 (3)	0.018 (2)	0.002 (2)	0.011 (2)
O5	0.072 (3)	0.078 (3)	0.069 (3)	−0.014 (2)	0.003 (2)	0.000 (2)
C1	0.053 (3)	0.058 (3)	0.047 (3)	0.001 (3)	0.007 (3)	−0.003 (3)
C2	0.049 (3)	0.056 (3)	0.049 (3)	0.004 (3)	0.006 (3)	−0.007 (2)
C3	0.061 (4)	0.083 (4)	0.061 (4)	0.012 (3)	0.012 (3)	−0.006 (3)
C4	0.061 (4)	0.058 (3)	0.063 (4)	0.009 (3)	−0.005 (3)	−0.001 (3)
C5	0.058 (4)	0.064 (3)	0.054 (3)	−0.002 (3)	0.002 (3)	−0.007 (3)
C6	0.087 (5)	0.103 (5)	0.077 (5)	0.022 (4)	0.000 (4)	0.009 (4)
C7	0.051 (3)	0.063 (3)	0.060 (4)	0.000 (3)	0.001 (3)	−0.004 (3)
C8	0.048 (3)	0.054 (3)	0.058 (3)	0.002 (3)	0.007 (3)	−0.004 (3)
C9	0.052 (4)	0.096 (5)	0.075 (4)	0.011 (3)	0.006 (3)	0.009 (4)
C10	0.072 (4)	0.076 (4)	0.073 (4)	0.006 (4)	0.024 (4)	0.002 (3)
C11	0.074 (4)	0.082 (4)	0.062 (4)	0.016 (4)	0.010 (3)	0.001 (3)
C12	0.101 (6)	0.129 (7)	0.090 (5)	0.021 (5)	0.048 (5)	0.011 (5)
C13	0.122 (6)	0.059 (4)	0.084 (5)	0.006 (4)	−0.020 (5)	−0.013 (3)
C14	0.136 (8)	0.087 (6)	0.148 (8)	−0.019 (5)	−0.023 (7)	−0.027 (5)
C15	0.102 (6)	0.070 (5)	0.157 (8)	−0.022 (4)	0.007 (6)	−0.034 (5)
C16	0.165 (10)	0.097 (6)	0.153 (9)	−0.007 (6)	0.016 (8)	−0.028 (6)
C17	0.071 (4)	0.053 (3)	0.083 (4)	−0.013 (3)	0.005 (3)	−0.003 (3)
C18	0.131 (7)	0.083 (5)	0.108 (6)	−0.028 (5)	0.021 (5)	−0.037 (4)
C19	0.191 (11)	0.111 (7)	0.142 (9)	−0.040 (7)	0.023 (8)	−0.055 (6)
C20	0.265 (17)	0.138 (10)	0.244 (16)	−0.054 (11)	0.022 (13)	−0.074 (11)
C21	0.115 (6)	0.093 (5)	0.107 (6)	−0.020 (5)	0.028 (5)	−0.019 (5)
O6	0.118 (4)	0.129 (4)	0.134 (4)	−0.045 (4)	0.065 (3)	−0.047 (3)

Geometric parameters (Å, º) top

Sn1—C17	2.103 (5)	C10—C12	1.494 (9)
Sn1—C13	2.107 (6)	C11—H11	0.9300
Sn1—O1	2.161 (4)	C12—H12A	0.9600
Sn1—O3	2.167 (4)	C12—H12B	0.9600
Sn1—N1	2.481 (4)	C12—H12C	0.9600
Sn1—N3	2.635 (5)	C13—C14	1.392 (9)
Sn1—O5	2.770 (4)	C13—H13A	0.9700
N1—C2	1.331 (6)	C13—H13B	0.9700
N1—C5	1.337 (6)	C14—C15	1.526 (8)
N2—C3	1.326 (7)	C14—H14A	0.9700
N2—C4	1.330 (8)	C14—H14B	0.9700
N3—C8	1.333 (6)	C15—C16	1.473 (10)
N3—C11	1.337 (7)	C15—H15A	0.9700
N4—C10	1.317 (8)	C15—H15B	0.9700
N4—C9	1.334 (8)	C16—H16A	0.9600
O1—C1	1.288 (6)	C16—H16B	0.9600
O2—C1	1.215 (7)	C16—H16C	0.9600
O3—C7	1.278 (6)	C17—C18	1.456 (8)
O4—C7	1.223 (6)	C17—H17A	0.9700
O5—H2	0.8500	C17—H17B	0.9700
O5—H1	0.8500	C18—C19	1.558 (9)
C1—C2	1.498 (7)	C18—H18A	0.9700
C2—C3	1.383 (7)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.369 (11)
C4—C5	1.395 (8)	C19—H19A	0.9700
C4—C6	1.498 (8)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6A	0.9600	C20—H20B	0.9600
C6—H6B	0.9600	C20—H20C	0.9600
C6—H6C	0.9600	C21—O6	1.372 (8)
C7—C8	1.498 (8)	C21—H21A	0.9600
C8—C9	1.376 (8)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.390 (8)	O6—H6	0.8200

C17—Sn1—C13	161.7 (3)	N4—C10—C12	117.4 (6)
C17—Sn1—O1	100.9 (2)	C11—C10—C12	121.0 (6)
C13—Sn1—O1	96.1 (2)	N3—C11—C10	121.9 (6)
C17—Sn1—O3	94.1 (2)	N3—C11—H11	119.0
C13—Sn1—O3	97.1 (2)	C10—C11—H11	119.0
O1—Sn1—O3	74.24 (14)	C10—C12—H12A	109.5
C17—Sn1—N1	89.9 (2)	C10—C12—H12B	109.5
C13—Sn1—N1	89.6 (2)	H12A—C12—H12B	109.5
O1—Sn1—N1	69.34 (14)	C10—C12—H12C	109.5
O3—Sn1—N1	143.46 (14)	H12A—C12—H12C	109.5
C17—Sn1—N3	87.0 (2)	H12B—C12—H12C	109.5
C13—Sn1—N3	84.0 (2)	C14—C13—Sn1	125.0 (5)
O1—Sn1—N3	141.33 (14)	C14—C13—H13A	106.1
O3—Sn1—N3	67.44 (15)	Sn1—C13—H13A	106.1
N1—Sn1—N3	149.10 (14)	C14—C13—H13B	106.1
C17—Sn1—O5	75.89 (18)	Sn1—C13—H13B	106.1
C13—Sn1—O5	86.2 (2)	H13A—C13—H13B	106.3
O1—Sn1—O5	145.38 (13)	C13—C14—C15	117.7 (7)
O3—Sn1—O5	139.93 (13)	C13—C14—H14A	107.9
N1—Sn1—O5	76.15 (13)	C15—C14—H14A	107.9
N3—Sn1—O5	73.29 (13)	C13—C14—H14B	107.9
C2—N1—C5	117.8 (5)	C15—C14—H14B	107.9
C2—N1—Sn1	111.8 (3)	H14A—C14—H14B	107.2
C5—N1—Sn1	130.4 (4)	C16—C15—C14	111.6 (7)
C3—N2—C4	116.5 (5)	C16—C15—H15A	109.3
C8—N3—C11	116.3 (5)	C14—C15—H15A	109.3
C8—N3—Sn1	109.6 (3)	C16—C15—H15B	109.3
C11—N3—Sn1	134.0 (4)	C14—C15—H15B	109.3
C10—N4—C9	116.3 (6)	H15A—C15—H15B	108.0
C1—O1—Sn1	125.1 (3)	C15—C16—H16A	109.5
C7—O3—Sn1	128.4 (4)	C15—C16—H16B	109.5
H2—O5—Sn1	138.8	H16A—C16—H16B	109.5
Sn1—O5—H1	113.9	C15—C16—H16C	109.5
Sn1—O5—H2	138.8	H16A—C16—H16C	109.5
H1—O5—H2	105.0	H16B—C16—H16C	109.5
O2—C1—O1	125.3 (5)	C18—C17—Sn1	116.8 (4)
O2—C1—C2	119.2 (5)	C18—C17—H17A	108.1
O1—C1—C2	115.5 (5)	Sn1—C17—H17A	108.1
N1—C2—C3	119.9 (5)	C18—C17—H17B	108.1
N1—C2—C1	116.8 (5)	Sn1—C17—H17B	108.1
C3—C2—C1	123.3 (5)	H17A—C17—H17B	107.3
N2—C3—C2	123.4 (6)	C17—C18—C19	110.5 (6)
N2—C3—H3	118.3	C17—C18—H18A	109.6
C2—C3—H3	118.3	C19—C18—H18A	109.6
N2—C4—C5	121.1 (5)	C17—C18—H18B	109.6
N2—C4—C6	118.0 (5)	C19—C18—H18B	109.6
C5—C4—C6	120.9 (6)	H18A—C18—H18B	108.1
N1—C5—C4	121.2 (6)	C20—C19—C18	116.0 (9)
N1—C5—H5	119.4	C20—C19—H19A	108.3
C4—C5—H5	119.4	C18—C19—H19A	108.3
C4—C6—H6A	109.5	C20—C19—H19B	108.3
C4—C6—H6B	109.5	C18—C19—H19B	108.3
H6A—C6—H6B	109.5	H19A—C19—H19B	107.4
C4—C6—H6C	109.5	C19—C20—H20A	109.5
H6A—C6—H6C	109.5	C19—C20—H20B	109.5
H6B—C6—H6C	109.5	H20A—C20—H20B	109.5
O4—C7—O3	124.2 (6)	C19—C20—H20C	109.5
O4—C7—C8	118.7 (5)	H20A—C20—H20C	109.5
O3—C7—C8	117.2 (5)	H20B—C20—H20C	109.5
N3—C8—C9	121.1 (5)	O6—C21—H21A	109.5
N3—C8—C7	117.3 (5)	O6—C21—H21B	109.5
C9—C8—C7	121.6 (5)	H21A—C21—H21B	109.5
N4—C9—C8	122.8 (6)	O6—C21—H21C	109.5
N4—C9—H9	118.6	H21A—C21—H21C	109.5
C8—C9—H9	118.6	H21B—C21—H21C	109.5
N4—C10—C11	121.6 (6)	C21—O6—H6	109.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O6	0.85	1.92	2.755 (6)	169
O5—H2···O1ⁱ	0.85	2.19	3.039 (5)	172
O6—H6···O4ⁱ	0.82	1.93	2.703 (6)	156

Symmetry code: (i) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₆H₅N₂O₂)₂(H₂O)]·CH₄O
M_r	557.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	20.609 (5), 17.119 (4), 14.558 (3)
β (°)	98.178 (3)
V (Å³)	5084 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.58 × 0.56 × 0.49

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.582, 0.628
No. of measured, independent and observed [I > 2σ(I)] reflections	12959, 4462, 2981
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.122, 1.12
No. of reflections	4462
No. of parameters	289
No. of restraints	12
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0455P)² + 11.2132P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.67

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C17	2.103 (5)	Sn1—N1	2.481 (4)
Sn1—C13	2.107 (6)	Sn1—N3	2.635 (5)
Sn1—O1	2.161 (4)	Sn1—O5	2.770 (4)
Sn1—O3	2.167 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O6	0.85	1.92	2.755 (6)	169
O5—H2···O1ⁱ	0.85	2.19	3.039 (5)	172
O6—H6···O4ⁱ	0.82	1.93	2.703 (6)	156

Symmetry code: (i) x, −y+2, z+1/2.

Acknowledgements

The authors acknowledge the financial support of the Science Foundation of Shandong.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gielen, M., Vanbellinghen, C., Gelan, J. & Willem, R. (1988). Bull. Soc. Chim. Belg. 97, 873–876. CAS Google Scholar
Ma, C., Han, Y., Zhang, R. & Wang, D. (2004). J. Chem. Soc. Dalton Trans. pp. 1832–1840. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar