Monoclinic modification of bis­(μ2-pyridine-2,6-dicarboxyl­ato)-κ4O2,N,O6:O6;κ4O2:O2,N,O6-bis­[aqua­dibutyl­tin(IV)]

Ng, S.W.

doi:10.1107/S1600536811002935

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m277

doi:10.1107/S1600536811002935

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Monoclinic modification of bis(μ₂-pyridine-2,6-dicarboxylato)-κ⁴O²,N,O⁶:O⁶;κ⁴O²:O²,N,O⁶-bis[aquadibutyltin(IV)]

Seik Weng Ng ^a ^*

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

(Received 17 January 2011; accepted 21 January 2011; online 29 January 2011)

The Sn^IV atom in the centrosymmetric dinuclear title compound, [Sn₂(C₄H₉)₄(C₇H₃NO₄)₂(H₂O)₂], exists in a trans-C₂SnNO₄ pentagonal–bipyramidal geometry. There are two half-molecules in the asymmetric unit that are completed by inversion symmetry. The crystal studied was a non-merohedral twin with a ratio of 47.3 (1)% for the minor twin component. Bond dimensions are similar to those found in the tetragonal polymorph [Huber et al. (1989 ). Acta Cryst. C45, 51–54]. O—H⋯O hydrogen-bonding interactions stabilize the crystal packing.

Related literature

For the tetragonal polymorph, see: Huber et al. (1989).

Experimental

Crystal data

[Sn₂(C₄H₉)₄(C₇H₃NO₄)₂(H₂O)₂]
M_r = 832.07
Monoclinic, P 2/n
a = 16.8882 (8) Å
b = 11.0957 (4) Å
c = 18.0940 (8) Å
β = 90.251 (4)°
V = 3390.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual with Atlas detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.767, T_max = 1.000
25121 measured reflections
12181 independent reflections
9129 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.126
S = 1.05
12181 reflections
400 parameters
H-atom parameters constrained
Δρ_max = 1.58 e Å⁻³
Δρ_min = −1.81 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O4ⁱ	0.84	1.81	2.635 (4)	166
O1w—H1w2⋯O6	0.84	1.98	2.695 (4)	142
O2w—H2w1⋯O8ⁱⁱ	0.84	1.83	2.647 (4)	165
O2w—H2w2⋯O2ⁱⁱⁱ	0.84	1.94	2.719 (4)	153
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+2; (iii) $[-x+{\script{1\over 2}}, y+1, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 10.1107/S1600536811002935/bt5468sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002935/bt5468Isup2.hkl

checkCIF report

Comment top

Bis[aquadibutyl(2,6-pyridinedicarboxylato)tin] (Scheme I), which was synthesized by condensing dibutyltin oxide with 2,6-pyridinedicarboxylic acid in methanol, is reported to belong to the tetragonal P4₂/n space group [a 17.684 (2), c 11.148 (12) Å; V 3486 (5) Å³]. The carboxylate dianion chelates to the tin atom in a tridentate manner; the asymmetric unit is connected to an inversion-related molecule by a long oxygen_carboxyl–tin bond [2.783 (4) Å] (Huber et al., 1989). A different synthetic route but with the same solvent has yielded the title monoclinic polymorph (Fig. 1). The tin atom shows trans-pentagonal bipyramidal coordination with the alkyl groups being in the apical positions [C–Sn–C 166.2 (3) °]. The chelating carboxylate uses one of the two carboxyl oxygen atoms (that which is not involved in chelation) to bind about a center-of-inversion to generate a dinuclear molecule [Sn–O 2.671 (3), 2.689 (3) Å]. The C₂Sn angles are similar to those of the tetragonal modification. The two independent molecules are linked by extensive O···H···O hydrogen bonds to form a three-dimensional nework.

Related literature top

For the tetragonal polymorph, see: Huber et al. (1989).

Experimental top

Di-n-butyltin diisothiocyanate (1 mmol) and 2,6-pyridinedicarboxylic acid (1 mmol) were loaded into a convection tube. The tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of one of the independent molecules of [Sn(H₂O)(C₄H₉)₂(C₇H₃NO₄)]₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the second dinuclear molecule.

bis(µ₂-pyridine-2,6-dicarboxylato)- κ⁴O²,N,O⁶:O⁶; κ⁴O²:O²,N,O⁶-bis[aquadibutyltin(IV)] top

Crystal data top

[Sn₂(C₄H₉)₄(C₇H₃NO₄)₂(H₂O)₂]	F(000) = 1680
M_r = 832.07	D_x = 1.631 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 11217 reflections
a = 16.8882 (8) Å	θ = 2.2–29.4°
b = 11.0957 (4) Å	µ = 1.53 mm⁻¹
c = 18.0940 (8) Å	T = 100 K
β = 90.251 (4)°	Block, colorless
V = 3390.5 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual with Atlas detector diffractometer	12181 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	9129 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.054
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.2°
ω scans	h = −21→20
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
T_min = 0.767, T_max = 1.000	l = −23→23
25121 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0608P)²] where P = (F_o² + 2F_c²)/3
12181 reflections	(Δ/σ)_max = 0.001
400 parameters	Δρ_max = 1.58 e Å⁻³
0 restraints	Δρ_min = −1.81 e Å⁻³

Crystal data top

[Sn₂(C₄H₉)₄(C₇H₃NO₄)₂(H₂O)₂]	V = 3390.5 (3) Å³
M_r = 832.07	Z = 4
Monoclinic, P2/n	Mo Kα radiation
a = 16.8882 (8) Å	µ = 1.53 mm⁻¹
b = 11.0957 (4) Å	T = 100 K
c = 18.0940 (8) Å	0.30 × 0.25 × 0.20 mm
β = 90.251 (4)°

Data collection top

Agilent SuperNova Dual with Atlas detector diffractometer	12181 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	9129 reflections with I > 2σ(I)
T_min = 0.767, T_max = 1.000	R_int = 0.054
25121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	Δρ_max = 1.58 e Å⁻³
12181 reflections	Δρ_min = −1.81 e Å⁻³
400 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.399301 (17)	0.48229 (3)	0.572478 (16)	0.01440 (8)
Sn2	0.432572 (17)	0.98366 (3)	0.898790 (16)	0.01470 (9)
O1	0.29816 (18)	0.4421 (3)	0.64381 (16)	0.0175 (7)
O2	0.21061 (17)	0.3039 (3)	0.67936 (17)	0.0187 (7)
O3	0.50412 (17)	0.3733 (3)	0.50538 (16)	0.0173 (7)
O4	0.5499 (2)	0.1918 (3)	0.47472 (18)	0.0279 (8)
O5	0.36299 (18)	0.9449 (3)	0.79949 (16)	0.0188 (7)
O6	0.32794 (19)	0.8071 (3)	0.71597 (17)	0.0229 (7)
O7	0.48802 (16)	0.8760 (3)	1.00654 (15)	0.0159 (6)
O8	0.50111 (19)	0.6946 (3)	1.06117 (18)	0.0240 (7)
O1w	0.34736 (18)	0.6700 (3)	0.59441 (17)	0.0210 (7)
H1w1	0.3778	0.7228	0.5773	0.032*
H1w2	0.3424	0.6803	0.6402	0.032*
O2w	0.42201 (18)	1.1692 (3)	0.84214 (17)	0.0193 (7)
H2w1	0.4476	1.2206	0.8666	0.029*
H2w2	0.3742	1.1897	0.8400	0.029*
N1	0.3915 (2)	0.2801 (3)	0.58810 (19)	0.0158 (8)
N2	0.4107 (2)	0.7816 (3)	0.8935 (2)	0.0159 (8)
C1	0.3352 (3)	0.4873 (4)	0.4731 (3)	0.0230 (10)
H1A	0.3172	0.5711	0.4649	0.028*
H1B	0.3718	0.4668	0.4324	0.028*
C2	0.2646 (3)	0.4061 (4)	0.4674 (2)	0.0227 (10)
H2A	0.2306	0.4202	0.5110	0.027*
H2B	0.2832	0.3216	0.4698	0.027*
C3	0.2144 (3)	0.4204 (4)	0.3988 (3)	0.0249 (11)
H3A	0.2475	0.4034	0.3549	0.030*
H3B	0.1965	0.5051	0.3953	0.030*
C4	0.1424 (3)	0.3386 (5)	0.3968 (3)	0.0373 (13)
H4A	0.1129	0.3520	0.3508	0.056*
H4B	0.1083	0.3566	0.4391	0.056*
H4C	0.1595	0.2543	0.3994	0.056*
C5	0.4806 (3)	0.5117 (4)	0.6600 (3)	0.0207 (10)
H5A	0.5211	0.5697	0.6428	0.025*
H5B	0.4518	0.5504	0.7012	0.025*
C6	0.5233 (3)	0.4003 (4)	0.6903 (2)	0.0212 (10)
H6A	0.5540	0.3626	0.6499	0.025*
H6B	0.4833	0.3411	0.7069	0.025*
C7	0.5797 (3)	0.4278 (5)	0.7551 (3)	0.0279 (11)
H7A	0.6187	0.4893	0.7395	0.033*
H7B	0.5489	0.4615	0.7968	0.033*
C8	0.6233 (3)	0.3152 (5)	0.7809 (3)	0.0384 (14)
H8A	0.6583	0.3358	0.8224	0.058*
H8B	0.6549	0.2830	0.7402	0.058*
H8C	0.5849	0.2545	0.7968	0.058*
C9	0.2753 (3)	0.3336 (4)	0.6549 (2)	0.0173 (9)
C10	0.3346 (3)	0.2387 (4)	0.6322 (2)	0.0150 (9)
C11	0.3312 (3)	0.1182 (4)	0.6541 (2)	0.0167 (9)
H11	0.2906	0.0905	0.6861	0.020*
C12	0.3885 (3)	0.0404 (4)	0.6278 (2)	0.0201 (10)
H12	0.3883	−0.0419	0.6423	0.024*
C13	0.4459 (3)	0.0826 (4)	0.5804 (2)	0.0192 (10)
H13	0.4850	0.0297	0.5613	0.023*
C14	0.4457 (3)	0.2041 (4)	0.5609 (2)	0.0154 (9)
C15	0.5051 (3)	0.2612 (4)	0.5090 (2)	0.0189 (10)
C16	0.5466 (3)	0.9732 (4)	0.8504 (2)	0.0183 (9)
H16A	0.5673	1.0559	0.8436	0.022*
H16B	0.5826	0.9307	0.8849	0.022*
C17	0.5478 (3)	0.9083 (4)	0.7758 (2)	0.0233 (10)
H17A	0.5240	0.8274	0.7819	0.028*
H17B	0.5145	0.9537	0.7403	0.028*
C18	0.6303 (3)	0.8940 (5)	0.7435 (3)	0.0299 (12)
H18A	0.6651	0.8547	0.7805	0.036*
H18B	0.6525	0.9747	0.7328	0.036*
C19	0.6300 (4)	0.8194 (5)	0.6728 (3)	0.0496 (18)
H19A	0.6842	0.8120	0.6542	0.074*
H19B	0.5968	0.8592	0.6355	0.074*
H19C	0.6087	0.7390	0.6831	0.074*
C20	0.3346 (3)	1.0267 (4)	0.9664 (3)	0.0200 (10)
H20A	0.3525	1.0849	1.0044	0.024*
H20B	0.2945	1.0680	0.9354	0.024*
C21	0.2945 (3)	0.9221 (4)	1.0054 (3)	0.0207 (10)
H21A	0.3344	0.8776	1.0348	0.025*
H21B	0.2726	0.8662	0.9679	0.025*
C22	0.2278 (3)	0.9627 (5)	1.0564 (3)	0.0277 (11)
H22A	0.2483	1.0250	1.0907	0.033*
H22B	0.1850	0.9996	1.0264	0.033*
C23	0.1939 (3)	0.8590 (5)	1.1008 (3)	0.0349 (13)
H23A	0.1504	0.8884	1.1316	0.052*
H23B	0.2355	0.8248	1.1325	0.052*
H23C	0.1741	0.7967	1.0671	0.052*
C24	0.4781 (3)	0.7627 (4)	1.0112 (3)	0.0187 (9)
C25	0.4334 (2)	0.7055 (4)	0.9464 (2)	0.0167 (9)
C26	0.4195 (3)	0.5834 (4)	0.9416 (3)	0.0232 (10)
H26	0.4369	0.5303	0.9796	0.028*
C27	0.3793 (3)	0.5397 (4)	0.8800 (3)	0.0248 (11)
H27	0.3684	0.4560	0.8755	0.030*
C28	0.3552 (3)	0.6188 (4)	0.8250 (3)	0.0206 (10)
H28	0.3281	0.5906	0.7823	0.025*
C29	0.3718 (3)	0.7404 (4)	0.8340 (2)	0.0183 (9)
C30	0.3515 (3)	0.8379 (4)	0.7786 (3)	0.0194 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01628 (16)	0.00938 (14)	0.01755 (16)	−0.00094 (11)	0.00007 (12)	0.00030 (11)
Sn2	0.01571 (16)	0.01010 (15)	0.01830 (17)	0.00106 (11)	−0.00022 (12)	0.00099 (11)
O1	0.0229 (17)	0.0106 (14)	0.0191 (16)	0.0012 (12)	0.0024 (13)	0.0019 (12)
O2	0.0172 (16)	0.0179 (16)	0.0208 (17)	−0.0013 (13)	−0.0003 (13)	0.0046 (13)
O3	0.0208 (16)	0.0107 (15)	0.0205 (16)	−0.0007 (12)	−0.0010 (13)	−0.0006 (12)
O4	0.039 (2)	0.0124 (16)	0.032 (2)	−0.0010 (14)	0.0171 (17)	−0.0029 (14)
O5	0.0219 (17)	0.0168 (15)	0.0175 (16)	−0.0018 (13)	−0.0019 (13)	0.0019 (13)
O6	0.0253 (19)	0.0262 (18)	0.0172 (17)	−0.0086 (14)	−0.0010 (14)	−0.0001 (14)
O7	0.0160 (16)	0.0123 (15)	0.0195 (16)	−0.0022 (12)	−0.0021 (13)	−0.0018 (12)
O8	0.0295 (19)	0.0124 (15)	0.0299 (19)	−0.0023 (13)	−0.0089 (15)	0.0049 (13)
O1w	0.0275 (18)	0.0133 (15)	0.0224 (17)	−0.0016 (13)	0.0083 (14)	0.0008 (13)
O2w	0.0202 (17)	0.0111 (14)	0.0267 (18)	0.0017 (12)	−0.0045 (14)	0.0018 (13)
N1	0.019 (2)	0.0130 (17)	0.0154 (19)	−0.0037 (14)	−0.0050 (15)	0.0033 (15)
N2	0.0150 (19)	0.0149 (18)	0.0177 (19)	0.0002 (14)	0.0038 (15)	0.0020 (15)
C1	0.023 (3)	0.020 (2)	0.026 (3)	−0.0022 (19)	−0.002 (2)	0.0073 (19)
C2	0.032 (3)	0.023 (2)	0.014 (2)	−0.003 (2)	0.001 (2)	−0.0015 (18)
C3	0.025 (3)	0.020 (2)	0.029 (3)	−0.003 (2)	−0.008 (2)	−0.001 (2)
C4	0.039 (3)	0.048 (3)	0.025 (3)	−0.012 (3)	−0.007 (2)	−0.005 (2)
C5	0.021 (2)	0.024 (2)	0.018 (2)	−0.0018 (19)	0.0028 (18)	−0.0009 (18)
C6	0.023 (3)	0.020 (2)	0.020 (2)	−0.0039 (19)	−0.0019 (19)	0.0002 (18)
C7	0.030 (3)	0.028 (3)	0.025 (3)	0.003 (2)	−0.009 (2)	−0.010 (2)
C8	0.048 (4)	0.036 (3)	0.032 (3)	0.007 (3)	−0.011 (3)	−0.009 (2)
C9	0.020 (2)	0.016 (2)	0.015 (2)	−0.0026 (18)	−0.0008 (18)	−0.0010 (17)
C10	0.018 (2)	0.014 (2)	0.013 (2)	−0.0029 (17)	−0.0051 (17)	−0.0015 (16)
C11	0.022 (2)	0.017 (2)	0.011 (2)	−0.0041 (17)	−0.0005 (18)	−0.0001 (17)
C12	0.035 (3)	0.008 (2)	0.017 (2)	0.0010 (18)	−0.0030 (19)	0.0022 (17)
C13	0.030 (3)	0.013 (2)	0.014 (2)	0.0043 (19)	−0.0029 (19)	0.0027 (17)
C14	0.025 (2)	0.012 (2)	0.010 (2)	−0.0004 (17)	−0.0020 (18)	−0.0026 (16)
C15	0.027 (3)	0.017 (2)	0.012 (2)	−0.0039 (18)	0.0005 (19)	−0.0010 (17)
C16	0.015 (2)	0.022 (2)	0.018 (2)	0.0042 (18)	0.0051 (18)	0.0000 (18)
C17	0.025 (3)	0.027 (2)	0.018 (2)	−0.007 (2)	0.005 (2)	−0.0028 (19)
C18	0.024 (3)	0.027 (3)	0.038 (3)	−0.005 (2)	0.012 (2)	−0.003 (2)
C19	0.047 (4)	0.042 (3)	0.060 (4)	−0.012 (3)	0.034 (3)	−0.022 (3)
C20	0.019 (2)	0.019 (2)	0.022 (2)	−0.0018 (18)	0.0036 (19)	0.0000 (18)
C21	0.023 (2)	0.015 (2)	0.025 (3)	−0.0070 (18)	0.003 (2)	−0.0005 (18)
C22	0.024 (3)	0.038 (3)	0.021 (2)	0.003 (2)	0.003 (2)	−0.004 (2)
C23	0.026 (3)	0.044 (3)	0.035 (3)	−0.001 (2)	0.009 (2)	−0.006 (3)
C24	0.013 (2)	0.016 (2)	0.026 (3)	0.0012 (17)	0.0009 (18)	0.0023 (18)
C25	0.013 (2)	0.015 (2)	0.022 (2)	0.0008 (17)	0.0007 (18)	0.0039 (18)
C26	0.016 (2)	0.016 (2)	0.037 (3)	−0.0010 (18)	−0.005 (2)	0.003 (2)
C27	0.018 (2)	0.018 (2)	0.038 (3)	−0.0097 (19)	−0.002 (2)	−0.007 (2)
C28	0.014 (2)	0.024 (2)	0.024 (2)	−0.0018 (18)	0.0025 (18)	−0.0076 (19)
C29	0.013 (2)	0.022 (2)	0.021 (2)	−0.0035 (17)	0.0022 (18)	0.0017 (18)
C30	0.013 (2)	0.022 (2)	0.023 (2)	−0.0013 (18)	0.0043 (18)	0.0024 (19)

Geometric parameters (Å, º) top

Sn1—C1	2.095 (5)	C7—C8	1.523 (7)
Sn1—C5	2.116 (5)	C7—H7A	0.9900
Sn1—O1	2.191 (3)	C7—H7B	0.9900
Sn1—N1	2.265 (3)	C8—H8A	0.9800
Sn1—O1w	2.296 (3)	C8—H8B	0.9800
Sn1—O3	2.468 (3)	C8—H8C	0.9800
Sn1—O3ⁱ	2.689 (3)	C9—C10	1.511 (6)
Sn2—C20	2.116 (4)	C10—C11	1.395 (6)
Sn2—C16	2.122 (4)	C11—C12	1.383 (6)
Sn2—O5	2.185 (3)	C11—H11	0.9500
Sn2—N2	2.274 (4)	C12—C13	1.380 (6)
Sn2—O2w	2.307 (3)	C12—H12	0.9500
Sn2—O7	2.467 (3)	C13—C14	1.393 (6)
Sn2—O7ⁱⁱ	2.671 (3)	C13—H13	0.9500
O1—C9	1.281 (5)	C14—C15	1.516 (6)
O2—C9	1.226 (5)	C16—C17	1.529 (6)
O3—C15	1.246 (5)	C16—H16A	0.9900
O4—C15	1.246 (5)	C16—H16B	0.9900
O5—C30	1.261 (5)	C17—C18	1.522 (6)
O6—C30	1.247 (5)	C17—H17A	0.9900
O7—C24	1.272 (5)	C17—H17B	0.9900
O8—C24	1.239 (5)	C18—C19	1.524 (7)
O1w—H1w1	0.8400	C18—H18A	0.9900
O1w—H1w2	0.8400	C18—H18B	0.9900
O2w—H2w1	0.8400	C19—H19A	0.9800
O2w—H2w2	0.8400	C19—H19B	0.9800
N1—C10	1.333 (5)	C19—H19C	0.9800
N1—C14	1.340 (5)	C20—C21	1.519 (6)
N2—C25	1.331 (5)	C20—H20A	0.9900
N2—C29	1.339 (5)	C20—H20B	0.9900
C1—C2	1.498 (6)	C21—C22	1.526 (6)
C1—H1A	0.9900	C21—H21A	0.9900
C1—H1B	0.9900	C21—H21B	0.9900
C2—C3	1.509 (6)	C22—C23	1.518 (7)
C2—H2A	0.9900	C22—H22A	0.9900
C2—H2B	0.9900	C22—H22B	0.9900
C3—C4	1.518 (7)	C23—H23A	0.9800
C3—H3A	0.9900	C23—H23B	0.9800
C3—H3B	0.9900	C23—H23C	0.9800
C4—H4A	0.9800	C24—C25	1.530 (6)
C4—H4B	0.9800	C25—C26	1.378 (6)
C4—H4C	0.9800	C26—C27	1.391 (6)
C5—C6	1.532 (6)	C26—H26	0.9500
C5—H5A	0.9900	C27—C28	1.386 (7)
C5—H5B	0.9900	C27—H27	0.9500
C6—C7	1.538 (6)	C28—C29	1.387 (6)
C6—H6A	0.9900	C28—H28	0.9500
C6—H6B	0.9900	C29—C30	1.514 (6)

C1—Sn1—C5	165.64 (17)	C6—C7—H7B	109.3
C1—Sn1—O1	96.31 (15)	H7A—C7—H7B	108.0
C5—Sn1—O1	95.48 (15)	C7—C8—H8A	109.5
C1—Sn1—N1	95.91 (15)	C7—C8—H8B	109.5
C5—Sn1—N1	95.61 (15)	H8A—C8—H8B	109.5
O1—Sn1—N1	71.27 (12)	C7—C8—H8C	109.5
C1—Sn1—O1w	85.88 (15)	H8A—C8—H8C	109.5
C5—Sn1—O1w	88.72 (15)	H8B—C8—H8C	109.5
O1—Sn1—O1w	77.48 (11)	O2—C9—O1	125.4 (4)
N1—Sn1—O1w	148.72 (12)	O2—C9—C10	120.2 (4)
C1—Sn1—O3	87.68 (15)	O1—C9—C10	114.4 (4)
C5—Sn1—O3	88.82 (14)	N1—C10—C11	122.0 (4)
O1—Sn1—O3	138.84 (10)	N1—C10—C9	113.7 (4)
N1—Sn1—O3	67.57 (11)	C11—C10—C9	124.2 (4)
O1w—Sn1—O3	143.64 (11)	C12—C11—C10	118.1 (4)
C1—Sn1—O3ⁱ	81.19 (14)	C12—C11—H11	121.0
C5—Sn1—O3ⁱ	84.66 (14)	C10—C11—H11	121.0
O1—Sn1—O3ⁱ	154.94 (10)	C13—C12—C11	119.8 (4)
N1—Sn1—O3ⁱ	133.74 (11)	C13—C12—H12	120.1
O1w—Sn1—O3ⁱ	77.47 (10)	C11—C12—H12	120.1
O3—Sn1—O3ⁱ	66.18 (11)	C12—C13—C14	119.0 (4)
C20—Sn2—C16	164.57 (17)	C12—C13—H13	120.5
C20—Sn2—O5	95.78 (15)	C14—C13—H13	120.5
C16—Sn2—O5	97.78 (14)	N1—C14—C13	121.1 (4)
C20—Sn2—N2	96.85 (15)	N1—C14—C15	114.9 (4)
C16—Sn2—N2	94.39 (15)	C13—C14—C15	124.0 (4)
O5—Sn2—N2	71.61 (12)	O4—C15—O3	126.8 (4)
C20—Sn2—O2w	89.79 (15)	O4—C15—C14	117.0 (4)
C16—Sn2—O2w	86.22 (14)	O3—C15—C14	116.1 (4)
O5—Sn2—O2w	76.71 (11)	C17—C16—Sn2	113.9 (3)
N2—Sn2—O2w	148.11 (12)	C17—C16—H16A	108.8
C20—Sn2—O7	86.99 (14)	Sn2—C16—H16A	108.8
C16—Sn2—O7	87.57 (14)	C17—C16—H16B	108.8
O5—Sn2—O7	139.04 (10)	Sn2—C16—H16B	108.8
N2—Sn2—O7	67.49 (11)	H16A—C16—H16B	107.7
O2w—Sn2—O7	144.24 (10)	C18—C17—C16	113.9 (4)
C20—Sn2—O7ⁱⁱ	83.65 (14)	C18—C17—H17A	108.8
C16—Sn2—O7ⁱⁱ	80.95 (13)	C16—C17—H17A	108.8
O5—Sn2—O7ⁱⁱ	155.31 (10)	C18—C17—H17B	108.8
N2—Sn2—O7ⁱⁱ	133.04 (11)	C16—C17—H17B	108.8
O2w—Sn2—O7ⁱⁱ	78.60 (10)	H17A—C17—H17B	107.7
O7—Sn2—O7ⁱⁱ	65.65 (11)	C17—C18—C19	112.3 (4)
C9—O1—Sn1	121.3 (3)	C17—C18—H18A	109.1
C15—O3—Sn1	118.3 (3)	C19—C18—H18A	109.1
C30—O5—Sn2	120.9 (3)	C17—C18—H18B	109.1
C24—O7—Sn2	118.8 (3)	C19—C18—H18B	109.1
Sn1—O1w—H1w1	109.5	H18A—C18—H18B	107.9
Sn1—O1w—H1w2	109.5	C18—C19—H19A	109.5
H1w1—O1w—H1w2	109.5	C18—C19—H19B	109.5
Sn2—O2w—H2w1	109.5	H19A—C19—H19B	109.5
Sn2—O2w—H2w2	109.5	C18—C19—H19C	109.5
H2w1—O2w—H2w2	109.5	H19A—C19—H19C	109.5
C10—N1—C14	119.9 (4)	H19B—C19—H19C	109.5
C10—N1—Sn1	117.3 (3)	C21—C20—Sn2	116.6 (3)
C14—N1—Sn1	122.5 (3)	C21—C20—H20A	108.1
C25—N2—C29	119.9 (4)	Sn2—C20—H20A	108.1
C25—N2—Sn2	123.3 (3)	C21—C20—H20B	108.1
C29—N2—Sn2	116.7 (3)	Sn2—C20—H20B	108.1
C2—C1—Sn1	116.8 (3)	H20A—C20—H20B	107.3
C2—C1—H1A	108.1	C20—C21—C22	112.8 (4)
Sn1—C1—H1A	108.1	C20—C21—H21A	109.0
C2—C1—H1B	108.1	C22—C21—H21A	109.0
Sn1—C1—H1B	108.1	C20—C21—H21B	109.0
H1A—C1—H1B	107.3	C22—C21—H21B	109.0
C1—C2—C3	116.0 (4)	H21A—C21—H21B	107.8
C1—C2—H2A	108.3	C23—C22—C21	112.2 (4)
C3—C2—H2A	108.3	C23—C22—H22A	109.2
C1—C2—H2B	108.3	C21—C22—H22A	109.2
C3—C2—H2B	108.3	C23—C22—H22B	109.2
H2A—C2—H2B	107.4	C21—C22—H22B	109.2
C2—C3—C4	113.8 (4)	H22A—C22—H22B	107.9
C2—C3—H3A	108.8	C22—C23—H23A	109.5
C4—C3—H3A	108.8	C22—C23—H23B	109.5
C2—C3—H3B	108.8	H23A—C23—H23B	109.5
C4—C3—H3B	108.8	C22—C23—H23C	109.5
H3A—C3—H3B	107.7	H23A—C23—H23C	109.5
C3—C4—H4A	109.5	H23B—C23—H23C	109.5
C3—C4—H4B	109.5	O8—C24—O7	127.6 (4)
H4A—C4—H4B	109.5	O8—C24—C25	117.3 (4)
C3—C4—H4C	109.5	O7—C24—C25	115.1 (4)
H4A—C4—H4C	109.5	N2—C25—C26	122.1 (4)
H4B—C4—H4C	109.5	N2—C25—C24	115.3 (4)
C6—C5—Sn1	116.5 (3)	C26—C25—C24	122.6 (4)
C6—C5—H5A	108.2	C25—C26—C27	118.4 (4)
Sn1—C5—H5A	108.2	C25—C26—H26	120.8
C6—C5—H5B	108.2	C27—C26—H26	120.8
Sn1—C5—H5B	108.2	C28—C27—C26	119.7 (4)
H5A—C5—H5B	107.3	C28—C27—H27	120.2
C5—C6—C7	113.7 (4)	C26—C27—H27	120.2
C5—C6—H6A	108.8	C27—C28—C29	118.3 (4)
C7—C6—H6A	108.8	C27—C28—H28	120.9
C5—C6—H6B	108.8	C29—C28—H28	120.9
C7—C6—H6B	108.8	N2—C29—C28	121.7 (4)
H6A—C6—H6B	107.7	N2—C29—C30	113.4 (4)
C8—C7—C6	111.6 (4)	C28—C29—C30	124.9 (4)
C8—C7—H7A	109.3	O6—C30—O5	125.3 (4)
C6—C7—H7A	109.3	O6—C30—C29	118.5 (4)
C8—C7—H7B	109.3	O5—C30—C29	116.1 (4)

C1—Sn1—O1—C9	86.4 (3)	C14—N1—C10—C11	2.9 (6)
C5—Sn1—O1—C9	−101.8 (3)	Sn1—N1—C10—C11	−170.7 (3)
N1—Sn1—O1—C9	−7.7 (3)	C14—N1—C10—C9	−176.7 (4)
O1w—Sn1—O1—C9	170.7 (3)	Sn1—N1—C10—C9	9.8 (5)
O3—Sn1—O1—C9	−7.3 (4)	O2—C9—C10—N1	162.0 (4)
O3ⁱ—Sn1—O1—C9	169.1 (3)	O1—C9—C10—N1	−15.9 (5)
C1—Sn1—O3—C15	−96.4 (3)	O2—C9—C10—C11	−17.6 (7)
C5—Sn1—O3—C15	97.6 (3)	O1—C9—C10—C11	164.5 (4)
O1—Sn1—O3—C15	0.6 (4)	N1—C10—C11—C12	−0.9 (6)
N1—Sn1—O3—C15	1.0 (3)	C9—C10—C11—C12	178.6 (4)
O1w—Sn1—O3—C15	−176.2 (3)	C10—C11—C12—C13	−1.0 (6)
O3ⁱ—Sn1—O3—C15	−177.8 (4)	C11—C12—C13—C14	1.1 (7)
C20—Sn2—O5—C30	−104.5 (3)	C10—N1—C14—C13	−2.8 (6)
C16—Sn2—O5—C30	82.8 (3)	Sn1—N1—C14—C13	170.4 (3)
N2—Sn2—O5—C30	−9.2 (3)	C10—N1—C14—C15	177.6 (4)
O2w—Sn2—O5—C30	167.1 (3)	Sn1—N1—C14—C15	−9.1 (5)
O7—Sn2—O5—C30	−12.4 (4)	C12—C13—C14—N1	0.9 (7)
O7ⁱⁱ—Sn2—O5—C30	168.1 (3)	C12—C13—C14—C15	−179.6 (4)
C20—Sn2—O7—C24	97.0 (3)	Sn1—O3—C15—O4	174.6 (4)
C16—Sn2—O7—C24	−97.4 (3)	Sn1—O3—C15—C14	−5.7 (5)
O5—Sn2—O7—C24	1.6 (4)	N1—C14—C15—O4	−170.7 (4)
N2—Sn2—O7—C24	−1.7 (3)	C13—C14—C15—O4	9.8 (7)
O2w—Sn2—O7—C24	−177.6 (3)	N1—C14—C15—O3	9.5 (6)
O7ⁱⁱ—Sn2—O7—C24	−178.6 (4)	C13—C14—C15—O3	−170.0 (4)
C1—Sn1—N1—C10	−96.8 (3)	C20—Sn2—C16—C17	−168.9 (5)
C5—Sn1—N1—C10	91.8 (3)	O5—Sn2—C16—C17	−17.5 (3)
O1—Sn1—N1—C10	−2.1 (3)	N2—Sn2—C16—C17	54.5 (3)
O1w—Sn1—N1—C10	−5.0 (4)	O2w—Sn2—C16—C17	−93.6 (3)
O3—Sn1—N1—C10	178.2 (3)	O7—Sn2—C16—C17	121.7 (3)
O3ⁱ—Sn1—N1—C10	179.7 (2)	O7ⁱⁱ—Sn2—C16—C17	−172.6 (3)
C1—Sn1—N1—C14	89.8 (3)	Sn2—C16—C17—C18	−176.4 (3)
C5—Sn1—N1—C14	−81.6 (3)	C16—C17—C18—C19	175.0 (4)
O1—Sn1—N1—C14	−175.5 (3)	C16—Sn2—C20—C21	−121.9 (6)
O1w—Sn1—N1—C14	−178.4 (3)	O5—Sn2—C20—C21	86.6 (3)
O3—Sn1—N1—C14	4.8 (3)	N2—Sn2—C20—C21	14.5 (3)
O3ⁱ—Sn1—N1—C14	6.3 (4)	O2w—Sn2—C20—C21	163.2 (3)
C20—Sn2—N2—C25	−82.1 (4)	O7—Sn2—C20—C21	−52.4 (3)
C16—Sn2—N2—C25	87.3 (3)	O7ⁱⁱ—Sn2—C20—C21	−118.2 (3)
O5—Sn2—N2—C25	−176.0 (4)	Sn2—C20—C21—C22	176.5 (3)
O2w—Sn2—N2—C25	177.2 (3)	C20—C21—C22—C23	−174.1 (4)
O7—Sn2—N2—C25	1.7 (3)	Sn2—O7—C24—O8	−179.4 (4)
O7ⁱⁱ—Sn2—N2—C25	5.6 (4)	Sn2—O7—C24—C25	1.5 (5)
C20—Sn2—N2—C29	96.9 (3)	C29—N2—C25—C26	1.2 (7)
C16—Sn2—N2—C29	−93.7 (3)	Sn2—N2—C25—C26	−179.9 (3)
O5—Sn2—N2—C29	3.1 (3)	C29—N2—C25—C24	179.3 (4)
O2w—Sn2—N2—C29	−3.8 (4)	Sn2—N2—C25—C24	−1.7 (5)
O7—Sn2—N2—C29	−179.2 (3)	O8—C24—C25—N2	−179.2 (4)
O7ⁱⁱ—Sn2—N2—C29	−175.4 (3)	O7—C24—C25—N2	0.0 (6)
C5—Sn1—C1—C2	−176.9 (6)	O8—C24—C25—C26	−1.0 (7)
O1—Sn1—C1—C2	−31.8 (4)	O7—C24—C25—C26	178.2 (4)
N1—Sn1—C1—C2	39.9 (4)	N2—C25—C26—C27	−1.0 (7)
O1w—Sn1—C1—C2	−108.7 (4)	C24—C25—C26—C27	−179.0 (4)
O3—Sn1—C1—C2	107.1 (4)	C25—C26—C27—C28	0.7 (7)
O3ⁱ—Sn1—C1—C2	173.4 (4)	C26—C27—C28—C29	−0.5 (7)
Sn1—C1—C2—C3	173.8 (3)	C25—N2—C29—C28	−1.0 (6)
C1—C2—C3—C4	−178.3 (4)	Sn2—N2—C29—C28	180.0 (3)
C1—Sn1—C5—C6	−128.1 (7)	C25—N2—C29—C30	−179.0 (4)
O1—Sn1—C5—C6	86.7 (3)	Sn2—N2—C29—C30	2.0 (5)
N1—Sn1—C5—C6	15.1 (3)	C27—C28—C29—N2	0.6 (7)
O1w—Sn1—C5—C6	164.0 (3)	C27—C28—C29—C30	178.4 (4)
O3—Sn1—C5—C6	−52.3 (3)	Sn2—O5—C30—O6	−163.8 (3)
O3ⁱ—Sn1—C5—C6	−118.4 (3)	Sn2—O5—C30—C29	13.3 (5)
Sn1—C5—C6—C7	−178.4 (3)	N2—C29—C30—O6	167.6 (4)
C5—C6—C7—C8	−177.4 (4)	C28—C29—C30—O6	−10.3 (7)
Sn1—O1—C9—O2	−162.7 (3)	N2—C29—C30—O5	−9.7 (6)
Sn1—O1—C9—C10	15.1 (5)	C28—C29—C30—O5	172.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4ⁱ	0.84	1.81	2.635 (4)	166
O1w—H1w2···O6	0.84	1.98	2.695 (4)	142
O2w—H2w1···O8ⁱⁱ	0.84	1.83	2.647 (4)	165
O2w—H2w2···O2ⁱⁱⁱ	0.84	1.94	2.719 (4)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x+1/2, y+1, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Sn₂(C₄H₉)₄(C₇H₃NO₄)₂(H₂O)₂]
M_r	832.07
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	100
a, b, c (Å)	16.8882 (8), 11.0957 (4), 18.0940 (8)
β (°)	90.251 (4)
V (Å³)	3390.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual with Atlas detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.767, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	25121, 12181, 9129
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.126, 1.05
No. of reflections	12181
No. of parameters	400
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.58, −1.81

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4ⁱ	0.84	1.81	2.635 (4)	166
O1w—H1w2···O6	0.84	1.98	2.695 (4)	142
O2w—H2w1···O8ⁱⁱ	0.84	1.83	2.647 (4)	165
O2w—H2w2···O2ⁱⁱⁱ	0.84	1.94	2.719 (4)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x+1/2, y+1, −z+3/2.

Acknowledgements

I thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Huber, F., Preut, H., Hoffmann, E. & Gielen, M. (1989). Acta Cryst. C45, 51–54. CSD CrossRef CAS Web of Science IUCr Journals 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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