Monoclinic modification of aquadi-n-butyl­bis­(pyrazine-2-carboxyl­ato-κ2N1,O)tin(IV)

Ng, S.W.

doi:10.1107/S1600536810032733

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1141

https://doi.org/10.1107/S1600536810032733

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Monoclinic modification of aquadi-n-butylbis(pyrazine-2-carboxylato-κ²N¹,O)tin(IV)

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 August 2010; accepted 14 August 2010; online 21 August 2010)

The asymmetric unit of the title organotin(IV) compound, [Sn(C₄H₉)₂(C₅H₃N₂O₂)₂(H₂O)], contains one-and-a-half molecules. The half-molecule is completed by crystallographic twofold symmetry, with its Sn and water O atoms lying on the rotation axis. Both molecules feature seven-coordinate Sn atoms in trans-C₂SnN₂O₃ pentagonal-bipyramidal coordination environments. The carboxylate anions N,O-chelate to the Sn atom. In the crystal, the carboxylate O atoms not involved in coordination serve as acceptors for O—H⋯O hydrogen bonds from adjacent water molecules, generating a three-dimensional network.

Related literature

For the rhombohedral modification, see: Ma et al. (2004 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₅H₃N₂O₂)₂(H₂O)]
M_r = 497.12
Monoclinic, C 2/c
a = 18.8872 (9) Å
b = 24.4940 (11) Å
c = 15.4417 (7) Å
β = 119.955 (1)°
V = 6189.4 (5) Å³
Z = 12
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 100 K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.701, T_max = 0.883
29386 measured reflections
7105 independent reflections
6558 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.056
S = 1.07
7105 reflections
392 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C1	2.129 (2)
Sn1—O1	2.2590 (13)
Sn1—O1W	2.306 (2)
Sn1—N1	2.5333 (15)
Sn2—C10	2.124 (2)
Sn2—C14	2.128 (2)
Sn2—O5	2.2598 (13)
Sn2—O3	2.2593 (13)
Sn2—O2W	2.3056 (13)
Sn2—N3	2.5232 (16)
Sn2—N5	2.5362 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯O4	0.83 (2)	1.79 (2)	2.611 (2)	170 (3)
O2w—H21⋯O2ⁱ	0.84 (2)	1.79 (2)	2.616 (2)	168 (2)
O2w—H22⋯O6ⁱⁱ	0.84 (2)	1.79 (2)	2.615 (2)	170 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032733/hb5604sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032733/hb5604Isup2.hkl

checkCIF report

Comment top

The title compound (I) is reported to crystallize in the rhombohedral R3c space group; the molecule lies on a twofold rotation axis that relates one alkyl group and one carboxylate anion to the other (Ma et al., 2004). The present monoclinic modification features two molecules, one of which lies on a general position and the other on a twofold rotation axis. Bond dimensions between the two molecules (Fig. 1) are not significantly different, however. The molecules feature seven-coordinate tin in trans-C₂SnN₂O₃ pentagonal bipyramidal environments. The carboxylate anions N,O-chelate to the tin atom. The carboxylate oxygen atoms not involved in coordination serve as hydrogen bond acceptor to adjacent water molecules to generate a three-dimensional hydrogen-bonded network.

Related literature top

For the rhombohedral modification, see: Ma et al. (2004).

Experimental top

The reaction was carried out under a nitrogen atmosphere. Pyrazine-2-carboxylic acid (0.124 g,1 mmol) and sodium ethoxide (0.068 g,1 mmol) were dissolved in to benzene (20 ml) in a Schlenk flask. Dibutyltin dichloride (0.153 g, 0.5 mmol) was added to the mixture; the mixture was stirred for 12 h at 318 K. After cooling down to the room temperature, the solution was filtered. The solvent was removed under reduced pressure to give a solid. The solid was recrystallized from ethanol to yield irregular colourless chunks of (I); yield, 72%; m.p. 517–519 K.

Structure description top

For the rhombohedral modification, see: Ma et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) with displacement wllipses shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. One molecule lies on a twofold rotation axis; the symmetry-related atoms are not labeled.

aquadi-n-butylbis(pyrazine-2-carboxylato- κ²N¹,O)tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₅H₃N₂O₂)₂(H₂O)]	F(000) = 3024
M_r = 497.12	D_x = 1.600 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9879 reflections
a = 18.8872 (9) Å	θ = 2.5–28.3°
b = 24.4940 (11) Å	µ = 1.28 mm⁻¹
c = 15.4417 (7) Å	T = 100 K
β = 119.955 (1)°	Irregular, colorless
V = 6189.4 (5) Å³	0.30 × 0.15 × 0.10 mm
Z = 12

Data collection top

Bruker SMART APEX CCD diffractometer	7105 independent reflections
Radiation source: fine-focus sealed tube	6558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.701, T_max = 0.883	k = −31→28
29386 measured reflections	l = −20→20

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.021P)² + 10.9233P] where P = (F_o² + 2F_c²)/3
7105 reflections	(Δ/σ)_max = 0.001
392 parameters	Δρ_max = 0.76 e Å⁻³
3 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₅H₃N₂O₂)₂(H₂O)]	V = 6189.4 (5) Å³
M_r = 497.12	Z = 12
Monoclinic, C2/c	Mo Kα radiation
a = 18.8872 (9) Å	µ = 1.28 mm⁻¹
b = 24.4940 (11) Å	T = 100 K
c = 15.4417 (7) Å	0.30 × 0.15 × 0.10 mm
β = 119.955 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	7105 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6558 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.883	R_int = 0.032
29386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	3 restraints
wR(F²) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.021P)² + 10.9233P] where P = (F_o² + 2F_c²)/3
7105 reflections	Δρ_max = 0.76 e Å⁻³
392 parameters	Δρ_min = −0.50 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.271645 (7)	0.2500	0.01226 (5)
Sn2	0.239913 (7)	0.510838 (5)	0.272022 (9)	0.01172 (4)
O1	0.58322 (8)	0.19810 (5)	0.29728 (10)	0.0161 (3)
O2	0.70784 (9)	0.16107 (6)	0.38196 (11)	0.0211 (3)
O5	0.20976 (8)	0.49615 (6)	0.11271 (10)	0.0152 (3)
O3	0.34167 (8)	0.45819 (6)	0.28122 (10)	0.0153 (3)
O4	0.46371 (9)	0.41771 (6)	0.37040 (10)	0.0201 (3)
O6	0.12665 (9)	0.50371 (6)	−0.05210 (11)	0.0206 (3)
O1W	0.5000	0.36578 (8)	0.2500	0.0174 (4)
O2W	0.19486 (9)	0.55472 (6)	0.36767 (11)	0.0173 (3)
N1	0.64916 (9)	0.29911 (6)	0.33560 (12)	0.0140 (3)
N2	0.81885 (11)	0.31145 (7)	0.42537 (14)	0.0226 (4)
N3	0.34640 (10)	0.49082 (6)	0.45089 (12)	0.0133 (3)
N4	0.47405 (10)	0.45577 (7)	0.63621 (12)	0.0203 (4)
N5	0.10625 (9)	0.55567 (6)	0.14732 (12)	0.0138 (3)
N6	−0.03695 (10)	0.59800 (7)	−0.01365 (13)	0.0207 (4)
C1	0.51096 (12)	0.27551 (8)	0.39390 (15)	0.0160 (4)
H1A	0.5418	0.2429	0.4319	0.019*
H1B	0.5446	0.3078	0.4288	0.019*
C2	0.43280 (12)	0.27860 (9)	0.40007 (15)	0.0196 (4)
H2A	0.3985	0.2463	0.3666	0.024*
H2B	0.4016	0.3115	0.3640	0.024*
C3	0.45043 (13)	0.28089 (9)	0.50854 (16)	0.0228 (4)
H3A	0.4890	0.3112	0.5436	0.027*
H3B	0.3989	0.2891	0.5081	0.027*
C4	0.48623 (15)	0.22850 (10)	0.56649 (18)	0.0304 (5)
H4A	0.4958	0.2327	0.6346	0.046*
H4B	0.5381	0.2206	0.5690	0.046*
H4C	0.4479	0.1984	0.5333	0.046*
C5	0.66054 (11)	0.20028 (8)	0.34647 (14)	0.0149 (4)
C6	0.69917 (11)	0.25600 (8)	0.36406 (14)	0.0145 (4)
C7	0.78340 (12)	0.26246 (8)	0.40881 (15)	0.0187 (4)
H7	0.8170	0.2308	0.4283	0.022*
C8	0.76820 (12)	0.35409 (9)	0.39651 (15)	0.0197 (4)
H8	0.7906	0.3898	0.4066	0.024*
C9	0.68399 (12)	0.34850 (8)	0.35234 (15)	0.0172 (4)
H9	0.6506	0.3802	0.3337	0.021*
C10	0.30749 (11)	0.58260 (8)	0.28432 (14)	0.0155 (4)
H10A	0.3269	0.5984	0.3515	0.019*
H10B	0.3564	0.5717	0.2807	0.019*
C11	0.26372 (12)	0.62761 (8)	0.20726 (16)	0.0188 (4)
H11A	0.2157	0.6401	0.2116	0.023*
H11B	0.2436	0.6125	0.1394	0.023*
C12	0.31919 (13)	0.67654 (9)	0.22259 (17)	0.0233 (4)
H12A	0.2856	0.7067	0.1785	0.028*
H12B	0.3433	0.6893	0.2925	0.028*
C13	0.38749 (14)	0.66419 (10)	0.20121 (19)	0.0304 (5)
H13A	0.4204	0.6971	0.2122	0.046*
H13B	0.3642	0.6523	0.1316	0.046*
H13C	0.4221	0.6351	0.2459	0.046*
C14	0.16848 (11)	0.44272 (8)	0.26816 (14)	0.0150 (4)
H14A	0.1206	0.4567	0.2711	0.018*
H14B	0.1476	0.4244	0.2027	0.018*
C15	0.21022 (12)	0.39971 (8)	0.34983 (15)	0.0185 (4)
H15A	0.2271	0.4166	0.4156	0.022*
H15B	0.2601	0.3866	0.3505	0.022*
C16	0.15458 (12)	0.35109 (8)	0.33474 (16)	0.0213 (4)
H16A	0.1041	0.3642	0.3325	0.026*
H16B	0.1388	0.3335	0.2698	0.026*
C17	0.19607 (14)	0.30907 (9)	0.41807 (18)	0.0273 (5)
H17A	0.1585	0.2787	0.4059	0.041*
H17B	0.2109	0.3262	0.4823	0.041*
H17C	0.2454	0.2954	0.4196	0.041*
C18	0.40452 (11)	0.44366 (8)	0.36248 (14)	0.0141 (4)
C19	0.40703 (11)	0.45937 (7)	0.45834 (14)	0.0134 (4)
C20	0.47023 (12)	0.44212 (8)	0.55007 (14)	0.0169 (4)
H20	0.5122	0.4199	0.5518	0.020*
C21	0.41298 (13)	0.48679 (8)	0.62802 (15)	0.0193 (4)
H21A	0.4130	0.4972	0.6873	0.023*
C22	0.34938 (12)	0.50456 (8)	0.53674 (15)	0.0161 (4)
H22A	0.3074	0.5267	0.5351	0.019*
C23	0.14592 (11)	0.51309 (8)	0.03584 (14)	0.0144 (4)
C24	0.08750 (11)	0.54742 (8)	0.05262 (14)	0.0136 (4)
C25	0.01660 (12)	0.56846 (8)	−0.02682 (15)	0.0175 (4)
H25	0.0056	0.5617	−0.0930	0.021*
C26	−0.01696 (12)	0.60683 (8)	0.08106 (16)	0.0197 (4)
H26	−0.0525	0.6283	0.0941	0.024*
C27	0.05379 (12)	0.58593 (8)	0.16149 (15)	0.0175 (4)
H27	0.0651	0.5932	0.2276	0.021*
H1	0.4900 (17)	0.3856 (10)	0.2865 (18)	0.035 (7)*
H21	0.1969 (15)	0.5884 (7)	0.3783 (18)	0.023 (6)*
H22	0.1695 (16)	0.5391 (11)	0.392 (2)	0.036 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01380 (9)	0.01078 (9)	0.01431 (9)	0.000	0.00861 (7)	0.000
Sn2	0.01378 (6)	0.01148 (7)	0.01148 (7)	0.00100 (5)	0.00750 (5)	0.00075 (4)
O1	0.0156 (6)	0.0120 (6)	0.0214 (7)	−0.0005 (5)	0.0098 (6)	−0.0008 (5)
O2	0.0192 (7)	0.0133 (7)	0.0297 (8)	0.0028 (6)	0.0113 (6)	0.0005 (6)
O5	0.0153 (6)	0.0182 (7)	0.0129 (7)	0.0039 (5)	0.0077 (5)	0.0007 (5)
O3	0.0165 (6)	0.0171 (7)	0.0129 (6)	0.0032 (5)	0.0078 (5)	0.0010 (5)
O4	0.0201 (7)	0.0234 (8)	0.0163 (7)	0.0076 (6)	0.0088 (6)	0.0002 (6)
O6	0.0226 (7)	0.0264 (8)	0.0140 (7)	0.0073 (6)	0.0101 (6)	0.0009 (6)
O1W	0.0261 (10)	0.0114 (9)	0.0230 (11)	0.000	0.0185 (9)	0.000
O2W	0.0259 (7)	0.0129 (7)	0.0204 (7)	0.0005 (6)	0.0171 (6)	0.0002 (6)
N1	0.0156 (7)	0.0131 (8)	0.0142 (8)	−0.0011 (6)	0.0081 (6)	0.0002 (6)
N2	0.0188 (8)	0.0228 (9)	0.0262 (10)	−0.0029 (7)	0.0112 (8)	−0.0019 (7)
N3	0.0150 (7)	0.0137 (8)	0.0121 (8)	−0.0015 (6)	0.0076 (6)	−0.0005 (6)
N4	0.0207 (8)	0.0243 (9)	0.0141 (8)	0.0004 (7)	0.0073 (7)	0.0008 (7)
N5	0.0139 (7)	0.0132 (8)	0.0150 (8)	0.0003 (6)	0.0079 (6)	−0.0002 (6)
N6	0.0176 (8)	0.0201 (9)	0.0221 (9)	0.0046 (7)	0.0082 (7)	0.0015 (7)
C1	0.0172 (9)	0.0173 (10)	0.0150 (9)	0.0005 (7)	0.0092 (8)	0.0008 (7)
C2	0.0185 (9)	0.0259 (11)	0.0176 (10)	0.0037 (8)	0.0115 (8)	0.0034 (8)
C3	0.0261 (11)	0.0272 (11)	0.0207 (10)	0.0049 (9)	0.0160 (9)	0.0015 (9)
C4	0.0325 (12)	0.0380 (14)	0.0298 (12)	0.0097 (10)	0.0225 (11)	0.0102 (10)
C5	0.0170 (9)	0.0151 (9)	0.0159 (9)	−0.0003 (7)	0.0106 (8)	−0.0016 (7)
C6	0.0164 (9)	0.0156 (9)	0.0138 (9)	−0.0005 (7)	0.0092 (7)	−0.0010 (7)
C7	0.0161 (9)	0.0176 (10)	0.0222 (10)	0.0001 (7)	0.0095 (8)	−0.0006 (8)
C8	0.0200 (10)	0.0178 (10)	0.0210 (10)	−0.0056 (8)	0.0099 (8)	−0.0010 (8)
C9	0.0202 (9)	0.0139 (9)	0.0177 (10)	−0.0021 (7)	0.0096 (8)	−0.0001 (7)
C10	0.0156 (9)	0.0152 (9)	0.0153 (9)	−0.0003 (7)	0.0074 (7)	0.0012 (7)
C11	0.0172 (9)	0.0173 (10)	0.0221 (10)	0.0006 (7)	0.0099 (8)	0.0047 (8)
C12	0.0236 (10)	0.0176 (10)	0.0294 (12)	−0.0025 (8)	0.0139 (9)	0.0052 (9)
C13	0.0238 (11)	0.0314 (13)	0.0398 (14)	−0.0001 (9)	0.0188 (10)	0.0135 (11)
C14	0.0138 (8)	0.0148 (9)	0.0154 (9)	−0.0013 (7)	0.0065 (7)	−0.0002 (7)
C15	0.0185 (9)	0.0152 (9)	0.0181 (10)	−0.0031 (7)	0.0065 (8)	0.0010 (8)
C16	0.0192 (9)	0.0175 (10)	0.0235 (11)	−0.0048 (8)	0.0078 (8)	0.0014 (8)
C17	0.0302 (12)	0.0187 (11)	0.0303 (12)	−0.0039 (9)	0.0130 (10)	0.0035 (9)
C18	0.0169 (9)	0.0116 (9)	0.0147 (9)	−0.0007 (7)	0.0086 (8)	−0.0008 (7)
C19	0.0146 (8)	0.0115 (9)	0.0149 (9)	−0.0023 (7)	0.0081 (7)	−0.0004 (7)
C20	0.0170 (9)	0.0171 (10)	0.0152 (9)	0.0016 (7)	0.0071 (8)	0.0006 (7)
C21	0.0225 (10)	0.0228 (10)	0.0135 (9)	−0.0019 (8)	0.0097 (8)	−0.0014 (8)
C22	0.0169 (9)	0.0181 (9)	0.0157 (9)	−0.0017 (7)	0.0099 (8)	−0.0025 (7)
C23	0.0159 (9)	0.0134 (9)	0.0158 (9)	0.0010 (7)	0.0092 (8)	0.0010 (7)
C24	0.0146 (8)	0.0114 (9)	0.0157 (9)	−0.0017 (7)	0.0083 (7)	0.0000 (7)
C25	0.0173 (9)	0.0184 (10)	0.0163 (9)	0.0013 (7)	0.0079 (8)	0.0007 (8)
C26	0.0176 (9)	0.0184 (10)	0.0249 (11)	0.0024 (8)	0.0121 (8)	−0.0017 (8)
C27	0.0179 (9)	0.0178 (10)	0.0193 (10)	0.0010 (8)	0.0112 (8)	−0.0018 (8)

Geometric parameters (Å, º) top

Sn1—C1	2.129 (2)	C4—H4B	0.9800
Sn1—C1ⁱ	2.129 (2)	C4—H4C	0.9800
Sn1—O1ⁱ	2.2590 (13)	C5—C6	1.507 (3)
Sn1—O1	2.2590 (13)	C6—C7	1.391 (3)
Sn1—O1W	2.306 (2)	C7—H7	0.9500
Sn1—N1	2.5333 (15)	C8—C9	1.389 (3)
Sn1—N1ⁱ	2.5333 (15)	C8—H8	0.9500
Sn2—C10	2.124 (2)	C9—H9	0.9500
Sn2—C14	2.128 (2)	C10—C11	1.527 (3)
Sn2—O5	2.2598 (13)	C10—H10A	0.9900
Sn2—O3	2.2593 (13)	C10—H10B	0.9900
Sn2—O2W	2.3056 (13)	C11—C12	1.530 (3)
Sn2—N3	2.5232 (16)	C11—H11A	0.9900
Sn2—N5	2.5362 (16)	C11—H11B	0.9900
O1—C5	1.267 (2)	C12—C13	1.513 (3)
O2—C5	1.238 (2)	C12—H12A	0.9900
O5—C23	1.267 (2)	C12—H12B	0.9900
O3—C18	1.274 (2)	C13—H13A	0.9800
O4—C18	1.238 (2)	C13—H13B	0.9800
O6—C23	1.239 (2)	C13—H13C	0.9800
O1W—H1	0.833 (16)	C14—C15	1.526 (3)
O2W—H21	0.839 (16)	C14—H14A	0.9900
O2W—H22	0.838 (17)	C14—H14B	0.9900
N1—C6	1.336 (2)	C15—C16	1.527 (3)
N1—C9	1.339 (2)	C15—H15A	0.9900
N2—C8	1.334 (3)	C15—H15B	0.9900
N2—C7	1.335 (3)	C16—C17	1.524 (3)
N3—C19	1.337 (2)	C16—H16A	0.9900
N3—C22	1.341 (2)	C16—H16B	0.9900
N4—C21	1.334 (3)	C17—H17A	0.9800
N4—C20	1.338 (3)	C17—H17B	0.9800
N5—C24	1.337 (2)	C17—H17C	0.9800
N5—C27	1.340 (2)	C18—C19	1.507 (3)
N6—C26	1.333 (3)	C19—C20	1.386 (3)
N6—C25	1.339 (3)	C20—H20	0.9500
C1—C2	1.528 (3)	C21—C22	1.389 (3)
C1—H1A	0.9900	C21—H21A	0.9500
C1—H1B	0.9900	C22—H22A	0.9500
C2—C3	1.537 (3)	C23—C24	1.509 (3)
C2—H2A	0.9900	C24—C25	1.387 (3)
C2—H2B	0.9900	C25—H25	0.9500
C3—C4	1.517 (3)	C26—C27	1.390 (3)
C3—H3A	0.9900	C26—H26	0.9500
C3—H3B	0.9900	C27—H27	0.9500
C4—H4A	0.9800

C1—Sn1—C1ⁱ	174.9 (1)	N1—C6—C5	117.21 (16)
C1—Sn1—O1ⁱ	93.56 (6)	C7—C6—C5	121.55 (17)
C1ⁱ—Sn1—O1ⁱ	90.50 (6)	N2—C7—C6	122.49 (19)
C1—Sn1—O1	90.50 (6)	N2—C7—H7	118.8
C1ⁱ—Sn1—O1	93.56 (6)	C6—C7—H7	118.8
O1ⁱ—Sn1—O1	74.22 (7)	N2—C8—C9	122.76 (19)
C1—Sn1—O1W	87.45 (5)	N2—C8—H8	118.6
C1ⁱ—Sn1—O1W	87.45 (5)	C9—C8—H8	118.6
O1ⁱ—Sn1—O1W	142.89 (3)	N1—C9—C8	121.03 (19)
O1—Sn1—O1W	142.89 (3)	N1—C9—H9	119.5
C1—Sn1—N1	86.58 (6)	C8—C9—H9	119.5
C1ⁱ—Sn1—N1	92.07 (6)	C11—C10—Sn2	117.40 (13)
O1ⁱ—Sn1—N1	142.51 (5)	C11—C10—H10A	108.0
O1—Sn1—N1	68.29 (5)	Sn2—C10—H10A	108.0
O1W—Sn1—N1	74.60 (4)	C11—C10—H10B	108.0
C1—Sn1—N1ⁱ	92.07 (6)	Sn2—C10—H10B	108.0
C1ⁱ—Sn1—N1ⁱ	86.58 (6)	H10A—C10—H10B	107.2
O1ⁱ—Sn1—N1ⁱ	68.29 (5)	C10—C11—C12	112.47 (17)
O1—Sn1—N1ⁱ	142.51 (5)	C10—C11—H11A	109.1
O1W—Sn1—N1ⁱ	74.60 (4)	C12—C11—H11A	109.1
N1—Sn1—N1ⁱ	149.20 (7)	C10—C11—H11B	109.1
C10—Sn2—C14	174.6 (1)	C12—C11—H11B	109.1
C10—Sn2—O5	92.44 (6)	H11A—C11—H11B	107.8
C14—Sn2—O5	91.90 (6)	C13—C12—C11	113.71 (19)
C10—Sn2—O3	90.71 (6)	C13—C12—H12A	108.8
C14—Sn2—O3	93.54 (6)	C11—C12—H12A	108.8
O5—Sn2—O3	73.84 (5)	C13—C12—H12B	108.8
C10—Sn2—O2W	87.39 (6)	C11—C12—H12B	108.8
C14—Sn2—O2W	87.24 (6)	H12A—C12—H12B	107.7
O5—Sn2—O2W	143.00 (5)	C12—C13—H13A	109.5
O3—Sn2—O2W	143.16 (5)	C12—C13—H13B	109.5
C10—Sn2—N3	87.01 (6)	H13A—C13—H13B	109.5
C14—Sn2—N3	91.49 (6)	C12—C13—H13C	109.5
O5—Sn2—N3	142.24 (5)	H13A—C13—H13C	109.5
O3—Sn2—N3	68.42 (5)	H13B—C13—H13C	109.5
O2W—Sn2—N3	74.74 (5)	C15—C14—Sn2	117.36 (13)
C10—Sn2—N5	92.04 (6)	C15—C14—H14A	108.0
C14—Sn2—N5	86.64 (6)	Sn2—C14—H14A	108.0
O5—Sn2—N5	68.17 (5)	C15—C14—H14B	108.0
O3—Sn2—N5	141.98 (5)	Sn2—C14—H14B	108.0
O2W—Sn2—N5	74.85 (5)	H14A—C14—H14B	107.2
N3—Sn2—N5	149.59 (5)	C14—C15—C16	112.34 (16)
C5—O1—Sn1	124.61 (12)	C14—C15—H15A	109.1
C23—O5—Sn2	124.90 (12)	C16—C15—H15A	109.1
C18—O3—Sn2	124.50 (12)	C14—C15—H15B	109.1
Sn1—O1W—H1	125.6 (19)	C16—C15—H15B	109.1
Sn2—O2W—H21	126.0 (17)	H15A—C15—H15B	107.9
Sn2—O2W—H22	124 (2)	C17—C16—C15	111.92 (17)
H21—O2W—H22	110 (3)	C17—C16—H16A	109.2
C6—N1—C9	116.87 (16)	C15—C16—H16A	109.2
C6—N1—Sn1	112.39 (12)	C17—C16—H16B	109.2
C9—N1—Sn1	130.68 (13)	C15—C16—H16B	109.2
C8—N2—C7	115.62 (17)	H16A—C16—H16B	107.9
C19—N3—C22	116.63 (16)	C16—C17—H17A	109.5
C19—N3—Sn2	112.74 (12)	C16—C17—H17B	109.5
C22—N3—Sn2	130.56 (13)	H17A—C17—H17B	109.5
C21—N4—C20	115.68 (17)	C16—C17—H17C	109.5
C24—N5—C27	116.65 (17)	H17A—C17—H17C	109.5
C24—N5—Sn2	112.63 (12)	H17B—C17—H17C	109.5
C27—N5—Sn2	130.72 (13)	O4—C18—O3	126.31 (18)
C26—N6—C25	115.64 (17)	O4—C18—C19	116.75 (17)
C2—C1—Sn1	118.29 (13)	O3—C18—C19	116.94 (16)
C2—C1—H1A	107.7	N3—C19—C20	121.82 (17)
Sn1—C1—H1A	107.7	N3—C19—C18	117.20 (16)
C2—C1—H1B	107.7	C20—C19—C18	120.98 (17)
Sn1—C1—H1B	107.7	N4—C20—C19	122.09 (18)
H1A—C1—H1B	107.1	N4—C20—H20	119.0
C1—C2—C3	112.30 (17)	C19—C20—H20	119.0
C1—C2—H2A	109.1	N4—C21—C22	122.94 (18)
C3—C2—H2A	109.1	N4—C21—H21A	118.5
C1—C2—H2B	109.1	C22—C21—H21A	118.5
C3—C2—H2B	109.1	N3—C22—C21	120.84 (18)
H2A—C2—H2B	107.9	N3—C22—H22A	119.6
C4—C3—C2	113.71 (18)	C21—C22—H22A	119.6
C4—C3—H3A	108.8	O6—C23—O5	125.95 (17)
C2—C3—H3A	108.8	O6—C23—C24	116.85 (17)
C4—C3—H3B	108.8	O5—C23—C24	117.20 (17)
C2—C3—H3B	108.8	N5—C24—C25	121.52 (17)
H3A—C3—H3B	107.7	N5—C24—C23	117.05 (16)
C3—C4—H4A	109.5	C25—C24—C23	121.41 (17)
C3—C4—H4B	109.5	N6—C25—C24	122.37 (18)
H4A—C4—H4B	109.5	N6—C25—H25	118.8
C3—C4—H4C	109.5	C24—C25—H25	118.8
H4A—C4—H4C	109.5	N6—C26—C27	122.66 (18)
H4B—C4—H4C	109.5	N6—C26—H26	118.7
O2—C5—O1	126.44 (18)	C27—C26—H26	118.7
O2—C5—C6	116.45 (17)	N5—C27—C26	121.14 (18)
O1—C5—C6	117.11 (17)	N5—C27—H27	119.4
N1—C6—C7	121.23 (18)	C26—C27—H27	119.4

C1—Sn1—O1—C5	−81.98 (15)	C9—N1—C6—C7	−0.1 (3)
C1ⁱ—Sn1—O1—C5	94.95 (15)	Sn1—N1—C6—C7	177.36 (14)
O1ⁱ—Sn1—O1—C5	−175.54 (17)	C9—N1—C6—C5	179.39 (16)
O1W—Sn1—O1—C5	4.46 (17)	Sn1—N1—C6—C5	−3.17 (19)
N1—Sn1—O1—C5	4.14 (14)	O2—C5—C6—N1	−173.10 (17)
N1ⁱ—Sn1—O1—C5	−176.03 (13)	O1—C5—C6—N1	6.7 (2)
C10—Sn2—O5—C23	−92.57 (15)	O2—C5—C6—C7	6.4 (3)
C14—Sn2—O5—C23	84.26 (15)	O1—C5—C6—C7	−173.81 (17)
O3—Sn2—O5—C23	177.40 (16)	C8—N2—C7—C6	0.2 (3)
O2W—Sn2—O5—C23	−3.67 (19)	N1—C6—C7—N2	−0.3 (3)
N3—Sn2—O5—C23	179.15 (13)	C5—C6—C7—N2	−179.77 (18)
N5—Sn2—O5—C23	−1.36 (14)	C7—N2—C8—C9	0.2 (3)
C10—Sn2—O3—C18	83.97 (15)	C6—N1—C9—C8	0.5 (3)
C14—Sn2—O3—C18	−92.74 (15)	Sn1—N1—C9—C8	−176.36 (14)
O5—Sn2—O3—C18	176.31 (15)	N2—C8—C9—N1	−0.6 (3)
O2W—Sn2—O3—C18	−2.62 (19)	O5—Sn2—C10—C11	55.92 (15)
N3—Sn2—O3—C18	−2.54 (14)	O3—Sn2—C10—C11	129.77 (14)
N5—Sn2—O3—C18	178.18 (13)	O2W—Sn2—C10—C11	−87.04 (15)
C1—Sn1—N1—C6	91.88 (13)	N3—Sn2—C10—C11	−161.89 (15)
C1ⁱ—Sn1—N1—C6	−93.04 (13)	N5—Sn2—C10—C11	−12.31 (15)
O1ⁱ—Sn1—N1—C6	0.48 (17)	Sn2—C10—C11—C12	−178.77 (14)
O1—Sn1—N1—C6	−0.03 (12)	C10—C11—C12—C13	68.0 (2)
O1W—Sn1—N1—C6	−179.83 (13)	O5—Sn2—C14—C15	125.86 (14)
N1ⁱ—Sn1—N1—C6	−179.83 (13)	O3—Sn2—C14—C15	51.94 (14)
C1—Sn1—N1—C9	−91.14 (17)	O2W—Sn2—C14—C15	−91.17 (14)
C1ⁱ—Sn1—N1—C9	83.95 (17)	N3—Sn2—C14—C15	−16.53 (15)
O1ⁱ—Sn1—N1—C9	177.47 (14)	N5—Sn2—C14—C15	−166.15 (15)
O1—Sn1—N1—C9	176.96 (18)	Sn2—C14—C15—C16	−175.97 (13)
O1W—Sn1—N1—C9	−2.84 (15)	C14—C15—C16—C17	−178.56 (18)
N1ⁱ—Sn1—N1—C9	−2.84 (15)	Sn2—O3—C18—O4	−175.31 (15)
C10—Sn2—N3—C19	−92.41 (13)	Sn2—O3—C18—C19	4.9 (2)
C14—Sn2—N3—C19	92.76 (13)	C22—N3—C19—C20	−0.5 (3)
O5—Sn2—N3—C19	−2.27 (17)	Sn2—N3—C19—C20	−177.75 (14)
O3—Sn2—N3—C19	−0.46 (12)	C22—N3—C19—C18	−179.94 (16)
O2W—Sn2—N3—C19	179.49 (13)	Sn2—N3—C19—C18	2.8 (2)
N5—Sn2—N3—C19	178.66 (11)	O4—C18—C19—N3	175.18 (17)
C10—Sn2—N3—C22	90.84 (17)	O3—C18—C19—N3	−5.0 (2)
C14—Sn2—N3—C22	−84.00 (17)	O4—C18—C19—C20	−4.3 (3)
O5—Sn2—N3—C22	−179.03 (14)	O3—C18—C19—C20	175.54 (17)
O3—Sn2—N3—C22	−177.22 (17)	C21—N4—C20—C19	0.3 (3)
O2W—Sn2—N3—C22	2.73 (16)	N3—C19—C20—N4	0.2 (3)
N5—Sn2—N3—C22	1.9 (2)	C18—C19—C20—N4	179.64 (18)
C10—Sn2—N5—C24	91.76 (13)	C20—N4—C21—C22	−0.5 (3)
C14—Sn2—N5—C24	−93.45 (13)	C19—N3—C22—C21	0.3 (3)
O5—Sn2—N5—C24	−0.05 (12)	Sn2—N3—C22—C21	176.94 (14)
O3—Sn2—N5—C24	−1.99 (17)	N4—C21—C22—N3	0.3 (3)
O2W—Sn2—N5—C24	178.51 (13)	Sn2—O5—C23—O6	−176.99 (15)
N3—Sn2—N5—C24	179.33 (11)	Sn2—O5—C23—C24	2.4 (2)
C10—Sn2—N5—C27	−87.34 (17)	C27—N5—C24—C25	−1.0 (3)
C14—Sn2—N5—C27	87.45 (17)	Sn2—N5—C24—C25	179.77 (14)
O5—Sn2—N5—C27	−179.16 (18)	C27—N5—C24—C23	−179.62 (16)
O3—Sn2—N5—C27	178.90 (14)	Sn2—N5—C24—C23	1.1 (2)
O2W—Sn2—N5—C27	−0.60 (16)	O6—C23—C24—N5	177.18 (17)
N3—Sn2—N5—C27	0.2 (2)	O5—C23—C24—N5	−2.3 (3)
O1ⁱ—Sn1—C1—C2	−54.71 (15)	O6—C23—C24—C25	−1.4 (3)
O1—Sn1—C1—C2	−128.93 (15)	O5—C23—C24—C25	179.07 (18)
O1W—Sn1—C1—C2	88.14 (15)	C26—N6—C25—C24	1.3 (3)
N1—Sn1—C1—C2	162.85 (15)	N5—C24—C25—N6	−0.1 (3)
N1ⁱ—Sn1—C1—C2	13.66 (15)	C23—C24—C25—N6	178.49 (18)
Sn1—C1—C2—C3	179.73 (14)	C25—N6—C26—C27	−1.4 (3)
C1—C2—C3—C4	−68.0 (2)	C24—N5—C27—C26	0.9 (3)
Sn1—O1—C5—O2	172.50 (15)	Sn2—N5—C27—C26	179.93 (14)
Sn1—O1—C5—C6	−7.3 (2)	N6—C26—C27—N5	0.4 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O4	0.83 (2)	1.79 (2)	2.611 (2)	170 (3)
O2w—H21···O2ⁱⁱ	0.84 (2)	1.79 (2)	2.616 (2)	168 (2)
O2w—H22···O6ⁱⁱⁱ	0.84 (2)	1.79 (2)	2.615 (2)	170 (3)

Symmetry codes: (ii) x−1/2, y+1/2, z; (iii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₅H₃N₂O₂)₂(H₂O)]
M_r	497.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.8872 (9), 24.4940 (11), 15.4417 (7)
β (°)	119.955 (1)
V (Å³)	6189.4 (5)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.701, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	29386, 7105, 6558
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.056, 1.07
No. of reflections	7105
No. of parameters	392
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.021P)² + 10.9233P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.50

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—C1	2.129 (2)	Sn2—O5	2.2598 (13)
Sn1—O1	2.2590 (13)	Sn2—O3	2.2593 (13)
Sn1—O1W	2.306 (2)	Sn2—O2W	2.3056 (13)
Sn1—N1	2.5333 (15)	Sn2—N3	2.5232 (16)
Sn2—C10	2.124 (2)	Sn2—N5	2.5362 (16)
Sn2—C14	2.128 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O4	0.83 (2)	1.79 (2)	2.611 (2)	170 (3)
O2w—H21···O2ⁱ	0.84 (2)	1.79 (2)	2.616 (2)	168 (2)
O2w—H22···O6ⁱⁱ	0.84 (2)	1.79 (2)	2.615 (2)	170 (3)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x, −y+1, z+1/2.

Acknowledgements

I thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ma, C., Han, Y., Zhang, R. & Wang, D. (2004). J. Organomet. Chem. 689, 1675–1683. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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