Triclinic modification of di-n-butyl­bis(2-hydroxy­benzoato-κ2O1,O1′)tin(IV)

Reisi, R.; Misran, M.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808023799

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1187

doi:10.1107/S1600536808023799

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Triclinic modification of di-n-butylbis(2-hydroxybenzoato-κ²O¹,O^1′)tin(IV)

Reza Reisi,^a Misni Misran,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

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

(Received 22 July 2008; accepted 28 July 2008; online 20 August 2008)

The Sn atom in the title compound, [Sn(C₄H₉)₂(C₇H₅O₃)₂], is chelated by the carboxylate groups of 2-hydroxybenzoate liagnds, and exists in a six-coordinate skew-trapezoidal bipyramidal coordination geometry [C—Sn—C = 140.1 (3)°].

Related literature

For the monoclinic modification, see: Narula et al. (1992 ). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991 , 1994 ). For a discussion of skew-trapezoidal bipyramidal diorganotin bis(chelates), see: Ng et al. (1987 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₇H₅O₃)₂]
M_r = 507.13
Triclinic, $[P \overline 1]$
a = 9.1652 (2) Å
b = 11.2111 (2) Å
c = 12.2620 (2) Å
α = 94.759 (1)°
β = 106.872 (1)°
γ = 108.586 (1)°
V = 1121.24 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 100 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.758, T_max = 0.844
11666 measured reflections
5068 independent reflections
4633 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.189
S = 1.18
5068 reflections
262 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 2.57 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2	0.84	1.96	2.599 (9)	132
O6—H6o⋯O5	0.84	2.00	2.626 (8)	131

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023799/tk2286sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023799/tk2286Isup2.hkl

checkCIF report

Comment top

Diorganotin dicarboxylates generally exist as monomeric molecules in which the carboxylate groups chelate in an anisobidentate manner (Tiekink, 1991; 1994). The R₂Sn unit is bent, and the geometry at tin is described as being skew-trapezoidal bipyramidal (Ng et al., 1987). The title compound has been reported in a monoclinic form (Narula et al., 1992). This structure has one n-butyl group in a W conformation and the other in a U conformation. In the present triclinic modification (Scheme I, Fig. 1), both groups adopt a W conformation. Intramolecular O-H···O hydrogen bonds are noted (Table 1).

Related literature top

For the monoclinic modification, see: Narula et al. (1992). For a review of the structural chemistry of organotin carboxylates, see: Tiekink (1991, 1994). For a discussion of skew-trapezoidal bipyramidal diorganotin bis(chelates), see: Ng et al. (1987).

Experimental top

Dibutyltin oxide (2 g, 8 mmol) and salicylic acid (2.2 g, 16 mmol) were heated in toluene (100 ml) in a Dean-Stark water apparatus. Slow evaporation of the filtered solution yielded colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of the triclinic form of [Sn(C₄H₉)₂(C₇H₅O₃] at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

di-n-butylbis(2-hydroxybenzoato-κ²O¹,O^1')tin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₇H₅O₃)₂]	Z = 2
M_r = 507.13	F(000) = 516
Triclinic, P1	D_x = 1.502 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1652 (2) Å	Cell parameters from 6302 reflections
b = 11.2111 (2) Å	θ = 2.5–27.7°
c = 12.2620 (2) Å	µ = 1.17 mm⁻¹
α = 94.759 (1)°	T = 100 K
β = 106.872 (1)°	Block, colorless
γ = 108.586 (1)°	0.25 × 0.20 × 0.15 mm
V = 1121.24 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	5068 independent reflections
Radiation source: fine-focus sealed tube	4633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
T_min = 0.758, T_max = 0.844	k = −14→14
11666 measured reflections	l = −15→15

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0604P)² + 8.6498P] where P = (F_o² + 2F_c²)/3
5068 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 2.57 e Å⁻³
2 restraints	Δρ_min = −1.40 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₇H₅O₃)₂]	γ = 108.586 (1)°
M_r = 507.13	V = 1121.24 (4) Å³
Triclinic, P1	Z = 2
a = 9.1652 (2) Å	Mo Kα radiation
b = 11.2111 (2) Å	µ = 1.17 mm⁻¹
c = 12.2620 (2) Å	T = 100 K
α = 94.759 (1)°	0.25 × 0.20 × 0.15 mm
β = 106.872 (1)°

Data collection top

Bruker SMART APEX diffractometer	5068 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4633 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.844	R_int = 0.034
11666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	2 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.18	Δρ_max = 2.57 e Å⁻³
5068 reflections	Δρ_min = −1.40 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.50157 (6)	0.34322 (5)	0.64132 (4)	0.03511 (17)
O1	0.6039 (7)	0.5445 (5)	0.6922 (5)	0.0424 (11)
O2	0.4303 (7)	0.4748 (5)	0.7850 (5)	0.0495 (13)
O3	0.4148 (9)	0.6313 (7)	0.9462 (6)	0.0687 (19)
H3O	0.3802	0.5549	0.9111	0.103*
O4	0.6470 (6)	0.3786 (5)	0.5355 (4)	0.0391 (11)
O5	0.5384 (8)	0.1687 (6)	0.5037 (5)	0.0535 (14)
O6	0.5995 (9)	0.0298 (5)	0.3515 (6)	0.0634 (18)
H6O	0.5475	0.0276	0.3980	0.095*
C1	0.2603 (9)	0.2912 (8)	0.5242 (7)	0.0452 (17)
H1A	0.2522	0.3652	0.4873	0.054*
H1B	0.2412	0.2201	0.4620	0.054*
C2	0.1264 (10)	0.2505 (8)	0.5755 (8)	0.0512 (19)
H2A	0.1354	0.3253	0.6296	0.061*
H2B	0.0198	0.2243	0.5123	0.061*
C3	0.1281 (12)	0.1422 (9)	0.6398 (9)	0.059 (2)
H3A	0.2243	0.1738	0.7118	0.071*
H3B	0.1410	0.0738	0.5911	0.071*
C4	−0.0260 (15)	0.0841 (11)	0.6719 (11)	0.077 (3)
H4A	−0.0159	0.0150	0.7140	0.116*
H4B	−0.1217	0.0496	0.6009	0.116*
H4C	−0.0389	0.1507	0.7212	0.116*
C5	0.6353 (10)	0.2839 (7)	0.7842 (7)	0.0429 (16)
H5A	0.6076	0.3066	0.8534	0.051*
H5B	0.6034	0.1895	0.7669	0.051*
C6	0.8165 (10)	0.3455 (7)	0.8106 (7)	0.0423 (16)
H6A	0.8473	0.4399	0.8259	0.051*
H6B	0.8436	0.3215	0.7415	0.051*
C7	0.9178 (12)	0.3068 (9)	0.9151 (8)	0.059 (2)
H7A	0.8917	0.3318	0.9845	0.070*
H7B	0.8861	0.2124	0.9003	0.070*
C8	1.0967 (13)	0.3666 (13)	0.9401 (10)	0.079 (3)
H8A	1.1547	0.3411	1.0093	0.118*
H8B	1.1288	0.4602	0.9538	0.118*
H8C	1.1245	0.3381	0.8736	0.118*
C9	0.5369 (9)	0.5664 (7)	0.7668 (6)	0.0391 (15)
C10	0.5867 (10)	0.6976 (7)	0.8301 (6)	0.0391 (15)
C11	0.5246 (11)	0.7235 (8)	0.9170 (7)	0.0466 (18)
C12	0.5768 (15)	0.8474 (9)	0.9784 (8)	0.066 (3)
H12	0.5344	0.8648	1.0375	0.079*
C13	0.6896 (18)	0.9447 (9)	0.9535 (11)	0.085 (4)
H13	0.7237	1.0298	0.9949	0.102*
C14	0.7559 (19)	0.9206 (9)	0.8676 (11)	0.091 (5)
H14	0.8361	0.9884	0.8522	0.109*
C15	0.7029 (12)	0.7971 (8)	0.8060 (8)	0.053 (2)
H15	0.7457	0.7799	0.7471	0.064*
C16	0.6292 (8)	0.2670 (7)	0.4830 (6)	0.0350 (14)
C17	0.7181 (8)	0.2616 (7)	0.4013 (6)	0.0344 (14)
C18	0.6975 (10)	0.1431 (7)	0.3404 (7)	0.0420 (16)
C19	0.7814 (12)	0.1408 (9)	0.2613 (7)	0.052 (2)
H19	0.7649	0.0615	0.2163	0.063*
C20	0.8863 (13)	0.2521 (10)	0.2488 (8)	0.061 (2)
H20	0.9441	0.2489	0.1964	0.074*
C21	0.9105 (12)	0.3695 (9)	0.3108 (8)	0.056 (2)
H21	0.9849	0.4463	0.3020	0.067*
C22	0.8242 (9)	0.3729 (7)	0.3858 (7)	0.0419 (16)
H22	0.8380	0.4532	0.4276	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0326 (3)	0.0370 (3)	0.0356 (3)	0.00980 (19)	0.01499 (19)	0.00458 (18)
O1	0.048 (3)	0.040 (3)	0.042 (3)	0.015 (2)	0.020 (2)	0.006 (2)
O2	0.049 (3)	0.045 (3)	0.052 (3)	0.010 (2)	0.021 (3)	0.006 (2)
O3	0.078 (5)	0.059 (4)	0.071 (4)	0.009 (3)	0.048 (4)	0.003 (3)
O4	0.044 (3)	0.038 (3)	0.041 (3)	0.014 (2)	0.022 (2)	0.006 (2)
O5	0.058 (4)	0.046 (3)	0.060 (4)	0.010 (3)	0.035 (3)	0.010 (3)
O6	0.076 (4)	0.036 (3)	0.076 (4)	0.006 (3)	0.041 (4)	−0.002 (3)
C1	0.041 (4)	0.054 (4)	0.039 (4)	0.014 (3)	0.013 (3)	0.011 (3)
C2	0.040 (4)	0.051 (5)	0.065 (5)	0.017 (4)	0.020 (4)	0.019 (4)
C3	0.055 (5)	0.055 (5)	0.077 (6)	0.019 (4)	0.034 (5)	0.022 (5)
C4	0.080 (7)	0.070 (7)	0.098 (8)	0.019 (6)	0.062 (7)	0.014 (6)
C5	0.050 (4)	0.040 (4)	0.039 (4)	0.012 (3)	0.019 (3)	0.010 (3)
C6	0.048 (4)	0.039 (4)	0.041 (4)	0.013 (3)	0.017 (3)	0.010 (3)
C7	0.063 (6)	0.057 (5)	0.054 (5)	0.024 (4)	0.011 (4)	0.016 (4)
C8	0.056 (6)	0.104 (9)	0.074 (7)	0.037 (6)	0.008 (5)	0.020 (6)
C9	0.042 (4)	0.046 (4)	0.034 (3)	0.021 (3)	0.014 (3)	0.008 (3)
C10	0.049 (4)	0.036 (3)	0.032 (3)	0.017 (3)	0.011 (3)	0.009 (3)
C11	0.057 (5)	0.044 (4)	0.044 (4)	0.017 (4)	0.024 (4)	0.008 (3)
C12	0.099 (8)	0.055 (5)	0.054 (5)	0.027 (5)	0.043 (5)	0.003 (4)
C13	0.136 (11)	0.037 (5)	0.086 (8)	0.010 (6)	0.068 (8)	−0.001 (5)
C14	0.145 (12)	0.038 (5)	0.100 (9)	0.007 (6)	0.089 (9)	0.002 (5)
C15	0.073 (6)	0.044 (4)	0.051 (5)	0.017 (4)	0.038 (4)	0.009 (4)
C16	0.033 (3)	0.040 (4)	0.033 (3)	0.013 (3)	0.012 (3)	0.007 (3)
C17	0.036 (3)	0.041 (4)	0.031 (3)	0.017 (3)	0.013 (3)	0.008 (3)
C18	0.043 (4)	0.039 (4)	0.046 (4)	0.013 (3)	0.020 (3)	0.008 (3)
C19	0.068 (6)	0.055 (5)	0.041 (4)	0.026 (4)	0.025 (4)	0.003 (3)
C20	0.074 (6)	0.082 (7)	0.048 (5)	0.039 (5)	0.036 (5)	0.018 (4)
C21	0.064 (6)	0.059 (5)	0.060 (5)	0.023 (4)	0.038 (5)	0.028 (4)
C22	0.044 (4)	0.043 (4)	0.048 (4)	0.020 (3)	0.022 (3)	0.016 (3)

Geometric parameters (Å, º) top

Sn1—C1	2.118 (8)	C6—H6A	0.9900
Sn1—C5	2.117 (8)	C6—H6B	0.9900
Sn1—O1	2.106 (5)	C7—C8	1.485 (15)
Sn1—O2	2.561 (6)	C7—H7A	0.9900
Sn1—O4	2.090 (5)	C7—H7B	0.9900
Sn1—O5	2.645 (6)	C8—H8A	0.9800
O1—C9	1.288 (9)	C8—H8B	0.9800
O2—C9	1.259 (9)	C8—H8C	0.9800
O3—C11	1.348 (10)	C9—C10	1.467 (10)
O3—H3O	0.8400	C10—C11	1.396 (11)
O4—C16	1.296 (8)	C10—C15	1.395 (11)
O5—C16	1.247 (9)	C11—C12	1.386 (12)
O6—C18	1.346 (9)	C12—C13	1.368 (15)
O6—H6O	0.8400	C12—H12	0.9500
C1—C2	1.501 (11)	C13—C14	1.408 (15)
C1—H1A	0.9900	C13—H13	0.9500
C1—H1B	0.9900	C14—C15	1.382 (12)
C2—C3	1.503 (12)	C14—H14	0.9500
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—C17	1.472 (9)
C3—C4	1.534 (13)	C17—C22	1.383 (10)
C3—H3A	0.9900	C17—C18	1.397 (10)
C3—H3B	0.9900	C18—C19	1.405 (11)
C4—H4A	0.9800	C19—C20	1.362 (14)
C4—H4B	0.9800	C19—H19	0.9500
C4—H4C	0.9800	C20—C21	1.382 (14)
C5—C6	1.503 (11)	C20—H20	0.9500
C5—H5A	0.9900	C21—C22	1.382 (11)
C5—H5B	0.9900	C21—H21	0.9500
C6—C7	1.533 (11)	C22—H22	0.9500

O4—Sn1—O1	82.3 (2)	H6A—C6—H6B	107.7
O4—Sn1—C5	104.7 (3)	C8—C7—C6	113.3 (8)
O1—Sn1—C5	102.1 (3)	C8—C7—H7A	108.9
O4—Sn1—C1	104.1 (3)	C6—C7—H7A	108.9
O1—Sn1—C1	108.7 (3)	C8—C7—H7B	108.9
C1—Sn1—C5	140.1 (3)	C6—C7—H7B	108.9
O4—Sn1—O2	137.44 (19)	H7A—C7—H7B	107.7
O1—Sn1—O2	55.25 (19)	C7—C8—H8A	109.5
C5—Sn1—O2	88.1 (3)	C7—C8—H8B	109.5
C1—Sn1—O2	89.0 (3)	H8A—C8—H8B	109.5
O4—Sn1—O5	53.64 (18)	C7—C8—H8C	109.5
O1—Sn1—O5	135.77 (19)	H8A—C8—H8C	109.5
C5—Sn1—O5	87.8 (3)	H8B—C8—H8C	109.5
C1—Sn1—O5	87.5 (3)	O2—C9—O1	119.5 (7)
O2—Sn1—O5	168.92 (18)	O2—C9—C10	120.8 (7)
C9—O1—Sn1	102.7 (5)	O1—C9—C10	119.6 (7)
C9—O2—Sn1	82.4 (4)	C11—C10—C15	119.7 (7)
C11—O3—H3O	120.0	C11—C10—C9	121.1 (7)
C16—O4—Sn1	106.0 (4)	C15—C10—C9	119.2 (7)
C16—O5—Sn1	81.3 (4)	O3—C11—C12	117.1 (8)
C18—O6—H6O	120.0	O3—C11—C10	122.6 (7)
C2—C1—Sn1	116.0 (5)	C12—C11—C10	120.3 (8)
C2—C1—H1A	108.3	C13—C12—C11	119.7 (9)
Sn1—C1—H1A	108.3	C13—C12—H12	120.1
C2—C1—H1B	108.3	C11—C12—H12	120.1
Sn1—C1—H1B	108.3	C12—C13—C14	121.0 (9)
H1A—C1—H1B	107.4	C12—C13—H13	119.5
C3—C2—C1	114.3 (7)	C14—C13—H13	119.5
C3—C2—H2A	108.7	C15—C14—C13	119.2 (9)
C1—C2—H2A	108.7	C15—C14—H14	120.4
C3—C2—H2B	108.7	C13—C14—H14	120.4
C1—C2—H2B	108.7	C14—C15—C10	120.2 (8)
H2A—C2—H2B	107.6	C14—C15—H15	119.9
C2—C3—C4	114.0 (9)	C10—C15—H15	119.9
C2—C3—H3A	108.8	O5—C16—O4	119.1 (6)
C4—C3—H3A	108.8	O5—C16—C17	122.5 (7)
C2—C3—H3B	108.8	O4—C16—C17	118.4 (6)
C4—C3—H3B	108.8	C22—C17—C18	119.7 (7)
H3A—C3—H3B	107.7	C22—C17—C16	120.5 (6)
C3—C4—H4A	109.5	C18—C17—C16	119.9 (6)
C3—C4—H4B	109.5	O6—C18—C19	117.5 (7)
H4A—C4—H4B	109.5	O6—C18—C17	123.8 (7)
C3—C4—H4C	109.5	C19—C18—C17	118.7 (7)
H4A—C4—H4C	109.5	C20—C19—C18	120.2 (8)
H4B—C4—H4C	109.5	C20—C19—H19	119.9
C6—C5—Sn1	111.8 (5)	C18—C19—H19	119.9
C6—C5—H5A	109.2	C19—C20—C21	121.5 (8)
Sn1—C5—H5A	109.2	C19—C20—H20	119.2
C6—C5—H5B	109.2	C21—C20—H20	119.2
Sn1—C5—H5B	109.2	C22—C21—C20	118.6 (8)
H5A—C5—H5B	107.9	C22—C21—H21	120.7
C5—C6—C7	113.4 (7)	C20—C21—H21	120.7
C5—C6—H6A	108.9	C17—C22—C21	121.3 (8)
C7—C6—H6A	108.9	C17—C22—H22	119.4
C5—C6—H6B	108.9	C21—C22—H22	119.4
C7—C6—H6B	108.9

O4—Sn1—O1—C9	179.6 (5)	Sn1—O1—C9—O2	−4.1 (8)
C5—Sn1—O1—C9	−76.9 (5)	Sn1—O1—C9—C10	175.5 (5)
C1—Sn1—O1—C9	77.3 (5)	O2—C9—C10—C11	3.9 (11)
O2—Sn1—O1—C9	2.1 (4)	O1—C9—C10—C11	−175.7 (7)
O5—Sn1—O1—C9	−176.4 (4)	O2—C9—C10—C15	−178.8 (8)
O4—Sn1—O2—C9	−5.8 (6)	O1—C9—C10—C15	1.7 (11)
O1—Sn1—O2—C9	−2.1 (4)	C15—C10—C11—O3	−178.5 (9)
C5—Sn1—O2—C9	104.0 (5)	C9—C10—C11—O3	−1.2 (13)
C1—Sn1—O2—C9	−115.8 (5)	C15—C10—C11—C12	0.7 (13)
O5—Sn1—O2—C9	172.4 (9)	C9—C10—C11—C12	178.0 (8)
O1—Sn1—O4—C16	176.7 (5)	O3—C11—C12—C13	179.2 (11)
C5—Sn1—O4—C16	76.2 (5)	C10—C11—C12—C13	0.0 (17)
C1—Sn1—O4—C16	−75.8 (5)	C11—C12—C13—C14	−1 (2)
O2—Sn1—O4—C16	179.8 (4)	C12—C13—C14—C15	1 (2)
O5—Sn1—O4—C16	0.2 (4)	C13—C14—C15—C10	−1 (2)
O4—Sn1—O5—C16	−0.2 (4)	C11—C10—C15—C14	−0.2 (15)
O1—Sn1—O5—C16	−5.1 (6)	C9—C10—C15—C14	−177.6 (10)
C5—Sn1—O5—C16	−110.3 (5)	Sn1—O5—C16—O4	0.3 (6)
C1—Sn1—O5—C16	109.4 (5)	Sn1—O5—C16—C17	−179.9 (7)
O2—Sn1—O5—C16	−178.7 (9)	Sn1—O4—C16—O5	−0.4 (8)
O4—Sn1—C1—C2	175.7 (6)	Sn1—O4—C16—C17	179.8 (5)
O1—Sn1—C1—C2	−97.9 (6)	O5—C16—C17—C22	−176.5 (7)
C5—Sn1—C1—C2	40.6 (9)	O4—C16—C17—C22	3.2 (10)
O2—Sn1—C1—C2	−45.3 (6)	O5—C16—C17—C18	2.4 (11)
O5—Sn1—C1—C2	124.2 (6)	O4—C16—C17—C18	−177.9 (7)
Sn1—C1—C2—C3	−55.4 (10)	C22—C17—C18—O6	178.7 (8)
C1—C2—C3—C4	−169.0 (9)	C16—C17—C18—O6	−0.2 (12)
O4—Sn1—C5—C6	30.8 (6)	C22—C17—C18—C19	−2.3 (11)
O1—Sn1—C5—C6	−54.3 (6)	C16—C17—C18—C19	178.8 (7)
C1—Sn1—C5—C6	165.7 (5)	O6—C18—C19—C20	−177.9 (9)
O2—Sn1—C5—C6	−108.1 (5)	C17—C18—C19—C20	3.0 (13)
O5—Sn1—C5—C6	82.2 (5)	C18—C19—C20—C21	−1.5 (15)
Sn1—C5—C6—C7	178.9 (6)	C19—C20—C21—C22	−0.7 (15)
C5—C6—C7—C8	179.3 (9)	C18—C17—C22—C21	0.1 (12)
Sn1—O2—C9—O1	3.3 (6)	C16—C17—C22—C21	179.0 (7)
Sn1—O2—C9—C10	−176.3 (7)	C20—C21—C22—C17	1.4 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.84	1.96	2.599 (9)	132
O6—H6o···O5	0.84	2.00	2.626 (8)	131

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₇H₅O₃)₂]
M_r	507.13
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.1652 (2), 11.2111 (2), 12.2620 (2)
α, β, γ (°)	94.759 (1), 106.872 (1), 108.586 (1)
V (Å³)	1121.24 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.758, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	11666, 5068, 4633
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.189, 1.18
No. of reflections	5068
No. of parameters	262
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.57, −1.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.84	1.96	2.599 (9)	132
O6—H6o···O5	0.84	2.00	2.626 (8)	131

Acknowledgements

We thank the University of Malaya for funding this study (SF022/2007 A, FS339/2008 A) and also for the purchase of the diffractometer.

References

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