Tricyclo­hexyl(4-nitro­phenoxy­acetato)tin(IV)

Tian, L.-J.; Yu, H.-X.; Sun, Y.-X.; Yu, F.-Y.

doi:10.1107/S1600536805039541

Tricyclohexyl(4-nitrophenoxyacetato)tin(IV)

L.-J. Tian, H.-X. Yu, Y.-X. Sun and F.-Y. Yu

The coordination geometry about the Sn atom in the title compound, [Sn(C₆H₁₁)₃(C₈H₆NO₅)], is best described as highly distorted tetrahedral. There is an intermolecular interaction, 2.769 (2) Å, between the Sn atom and the carbonyl O atom of the carboxylate group of an adjacent molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039541/bh6052sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039541/bh6052Isup2.hkl Contains datablock I

CCDC reference: 296714

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.032
wR factor = 0.076
Data-to-parameter ratio = 18.1

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Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19

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   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

Tricyclohexyltin carboxylates, (C₆H₁₁)₃Sn(O₂CR), generally have a tetrahedral structure and do not auto-associate into chain structures via carboxylate bridging, due to the effects of the three bulky organic groups at Sn (Chandrasekhar et al., 2002; Tiekink, 1991, 1994). 4-Nitrophenoxyacetic acid, whose crystal structure has been reported previously (Kumar & Rao, 1980), is a pesticide intermediate used in the synthesis of fungicides and plant-growth regulators (Xue & Zou, 1999). We present here the crystal structure analysis of its tricyclohexyltin ester, (I).

In (I), the Sn atom is best described as having a highly distorted tetrahedral geometry, with the range of angles subtended at Sn being 89.83 (9)–124.93 (11)° (Fig. 1, Table 1). An Sn1···O2ⁱ intermolecular contact of 2.769 (2) Å [symmetry code: (i) −x + 2, y + 1/2, −z + 1/2] is not considered to be a significant bonding interaction (Willem et al., 1998). If the Sn1···O2ⁱ interaction were considered as a significant bonding interaction, then (I) would be described as a five-coordinate complex with the Sn atom having a trans-R₃SnO₂ trigonal–bipyramidal geometry. In that case, atoms C9, C15 and C21 would define the trigonal plane and a one-dimensional polymer would be formed through the apical positions occupied by O1 and O2 (Fig. 2). However, in this description, the Sn atom would lie 0.238 (2) Å out of the trigonal plane.

Atom O2ⁱ exerts a steric influence on atom Sn1 from the opposite of atom O1, and thus contributes to the distortion of the tetrahedral geometry around the Sn atom, by opening up the C—Sn1—C angles and contracting the O1—Sn1—C angles. The Sn1···O2 separation of 3.523 (3) Å, and the Sn1—O1 distance of 2.1317 (19) Å, are longer than those found in previously reported tricyclohexyltin carboxylates, such as tricyclohexyltin indole-3-acetate (Molloy et al., 1986), trifluoroacetate (Calogero et al., 1980), N-phthaloylglycinate (Ng & Kumar Das, 1997a), (N,N-diethylthiocarbamoylthio)acetate (Ng & Kumar Das, 1997b), 2-[2-(2-hydroxy-5-methylphenyl)-1-diazenyl]benzoate (Willem et al., 1998), 2-(4-chlorophenyl)-3-methylbutyrate (Song et al., 2003) and 4-biphenylacetate (Tian et al., 2005). However, the three Sn—C distances in (I) are similar to those of the carboxylate structures mentioned above (Table 1).

Experimental top

Tricyclohexyltin hydroxide (0.577 g, 1.5 mmol) and 4-nitrophenoxyacetic acid (0.30 g, 1.5 mmol) in toluene (60 ml) were refluxed for 4 h with azeotropic removal of water via a Dean–Stark trap. The resulting clear solution was rotary evaporated under vacuum. The pale-yellow solid obtained, (I), was recrystallized from ethanol and crystals of (I) were obtained from hexane–chloroform (1:1) by slow evaporation at 298 K (yield 70.3%; m.p. 358–359 K). Analysis, found: C 55.22, H 6.69, N 2.37%; calculated for C₂₆H₃₉NO₅Sn: C 55.34, H 6.97, N 2.48%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of (I), viewed along the a axis.

Tricyclohexyl(4-nitrophenoxyacetato)tin(IV) top

Crystal data top

[Sn(C₆H₁₁)₃(C₈H₆NO₅)]	F(000) = 1168
M_r = 564.27	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 358–359 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8892 (15) Å	Cell parameters from 5699 reflections
b = 11.7837 (16) Å	θ = 2.5–27.6°
c = 20.768 (3) Å	µ = 1.01 mm⁻¹
β = 101.456 (2)°	T = 295 K
V = 2611.8 (6) Å³	Prism, pale-yellow
Z = 4	0.22 × 0.09 × 0.09 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	5390 independent reflections
Radiation source: fine-focus sealed tube	4395 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→13
T_min = 0.808, T_max = 0.914	k = −14→14
20503 measured reflections	l = −26→25

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.037P)² + 0.0495P] where P = (F_o² + 2F_c²)/3
5390 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Sn(C₆H₁₁)₃(C₈H₆NO₅)]	V = 2611.8 (6) Å³
M_r = 564.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8892 (15) Å	µ = 1.01 mm⁻¹
b = 11.7837 (16) Å	T = 295 K
c = 20.768 (3) Å	0.22 × 0.09 × 0.09 mm
β = 101.456 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	5390 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	4395 reflections with I > 2σ(I)
T_min = 0.808, T_max = 0.914	R_int = 0.040
20503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
5390 reflections	Δρ_min = −0.41 e Å⁻³
298 parameters

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	0.951222 (15)	0.883451 (15)	0.225197 (8)	0.03471 (8)
N1	0.2815 (3)	0.5962 (2)	0.05501 (19)	0.0701 (9)
O1	0.89188 (18)	0.74291 (15)	0.16204 (10)	0.0483 (5)
O2	0.9826 (2)	0.58741 (17)	0.21113 (10)	0.0525 (5)
O3	0.7902 (2)	0.63325 (18)	0.05222 (10)	0.0571 (6)
O4	0.2495 (3)	0.5532 (3)	0.10184 (17)	0.0992 (10)
O5	0.2095 (3)	0.6298 (2)	0.00551 (17)	0.0986 (10)
C1	0.9230 (3)	0.6386 (2)	0.16429 (14)	0.0395 (6)
C2	0.8826 (3)	0.5762 (3)	0.09964 (14)	0.0519 (8)
H2A	0.9559	0.5633	0.0807	0.062*
H2B	0.8498	0.5025	0.1086	0.062*
C3	0.6687 (3)	0.6261 (2)	0.05845 (14)	0.0470 (7)
C4	0.5810 (3)	0.6657 (3)	0.00457 (15)	0.0585 (9)
H4	0.6082	0.6978	−0.0310	0.070*
C5	0.4557 (3)	0.6573 (3)	0.00405 (17)	0.0599 (9)
H5A	0.3976	0.6840	−0.0317	0.072*
C6	0.4160 (3)	0.6097 (2)	0.05625 (17)	0.0538 (8)
C7	0.5007 (3)	0.5729 (3)	0.11058 (16)	0.0556 (8)
H7	0.4724	0.5421	0.1462	0.067*
C8	0.6273 (3)	0.5818 (3)	0.11194 (14)	0.0494 (7)
H8	0.6848	0.5581	0.1488	0.059*
C9	0.8754 (2)	0.8342 (2)	0.30918 (13)	0.0399 (6)
H9	0.8450	0.9035	0.3269	0.048*
C10	0.7627 (3)	0.7557 (3)	0.28923 (17)	0.0599 (9)
H10A	0.7016	0.7917	0.2549	0.072*
H10B	0.7895	0.6857	0.2716	0.072*
C11	0.7021 (3)	0.7286 (3)	0.34714 (19)	0.0730 (11)
H11A	0.6341	0.6752	0.3335	0.088*
H11B	0.6671	0.7974	0.3618	0.088*
C12	0.7966 (3)	0.6782 (3)	0.40366 (17)	0.0656 (10)
H12A	0.7569	0.6674	0.4411	0.079*
H12B	0.8230	0.6045	0.3908	0.079*
C13	0.9098 (3)	0.7532 (3)	0.42346 (15)	0.0608 (9)
H13A	0.9706	0.7155	0.4572	0.073*
H13B	0.8853	0.8234	0.4418	0.073*
C14	0.9697 (3)	0.7799 (3)	0.36470 (14)	0.0457 (7)
H14A	1.0399	0.8310	0.3783	0.055*
H14B	1.0015	0.7104	0.3490	0.055*
C15	1.1474 (3)	0.8819 (2)	0.22108 (15)	0.0435 (7)
H15	1.1735	0.9617	0.2230	0.052*
C16	1.1720 (3)	0.8362 (3)	0.15582 (16)	0.0597 (9)
H16A	1.1471	0.7571	0.1511	0.072*
H16B	1.1219	0.8783	0.1198	0.072*
C17	1.3102 (3)	0.8470 (3)	0.15274 (19)	0.0684 (10)
H17A	1.3240	0.8136	0.1121	0.082*
H17B	1.3323	0.9267	0.1525	0.082*
C18	1.3922 (3)	0.7906 (4)	0.20863 (19)	0.0757 (11)
H18A	1.4791	0.8036	0.2061	0.091*
H18B	1.3771	0.7094	0.2061	0.091*
C19	1.3688 (3)	0.8347 (4)	0.27340 (19)	0.0840 (12)
H19A	1.3943	0.9136	0.2784	0.101*
H19B	1.4193	0.7920	0.3090	0.101*
C20	1.2314 (3)	0.8249 (3)	0.27766 (16)	0.0608 (9)
H20A	1.2089	0.7453	0.2783	0.073*
H20B	1.2189	0.8589	0.3184	0.073*
C21	0.8370 (2)	0.9942 (2)	0.15620 (12)	0.0369 (6)
H21	0.8544	1.0720	0.1722	0.044*
C22	0.6970 (3)	0.9733 (3)	0.15166 (15)	0.0532 (8)
H22A	0.6778	0.8949	0.1394	0.064*
H22B	0.6761	0.9859	0.1944	0.064*
C23	0.6175 (3)	1.0515 (3)	0.10124 (16)	0.0617 (9)
H23A	0.5297	1.0325	0.0975	0.074*
H23B	0.6292	1.1295	0.1162	0.074*
C24	0.6527 (3)	1.0407 (3)	0.03479 (15)	0.0599 (9)
H24A	0.6337	0.9645	0.0181	0.072*
H24B	0.6031	1.0934	0.0044	0.072*
C25	0.7895 (3)	1.0647 (3)	0.03856 (15)	0.0576 (8)
H25A	0.8069	1.1433	0.0511	0.069*
H25B	0.8100	1.0535	−0.0044	0.069*
C26	0.8703 (3)	0.9875 (2)	0.08817 (13)	0.0471 (7)
H26A	0.9576	1.0082	0.0916	0.056*
H26B	0.8602	0.9098	0.0725	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02916 (11)	0.03885 (12)	0.03603 (12)	0.00299 (8)	0.00626 (8)	0.00653 (8)
N1	0.063 (2)	0.0443 (17)	0.095 (3)	−0.0010 (14)	−0.0023 (19)	−0.0102 (16)
O1	0.0547 (13)	0.0347 (11)	0.0534 (13)	−0.0010 (9)	0.0057 (10)	−0.0028 (9)
O2	0.0559 (13)	0.0508 (12)	0.0487 (13)	0.0055 (10)	0.0049 (10)	0.0068 (10)
O3	0.0655 (15)	0.0666 (15)	0.0387 (12)	0.0008 (11)	0.0092 (11)	0.0010 (10)
O4	0.0727 (19)	0.096 (2)	0.129 (3)	−0.0126 (17)	0.0192 (19)	0.021 (2)
O5	0.0691 (18)	0.091 (2)	0.118 (3)	0.0074 (15)	−0.0260 (18)	−0.0011 (17)
C1	0.0360 (15)	0.0408 (17)	0.0440 (16)	−0.0038 (12)	0.0132 (13)	0.0000 (13)
C2	0.060 (2)	0.0463 (17)	0.0498 (19)	0.0051 (15)	0.0118 (15)	−0.0067 (15)
C3	0.062 (2)	0.0372 (16)	0.0406 (16)	−0.0015 (14)	0.0071 (15)	−0.0070 (13)
C4	0.079 (3)	0.0522 (19)	0.0411 (18)	0.0051 (18)	0.0046 (17)	0.0088 (15)
C5	0.068 (2)	0.0491 (18)	0.054 (2)	0.0077 (17)	−0.0088 (17)	−0.0004 (16)
C6	0.057 (2)	0.0380 (17)	0.061 (2)	0.0030 (14)	−0.0009 (16)	−0.0098 (15)
C7	0.066 (2)	0.0508 (18)	0.0496 (19)	−0.0001 (16)	0.0095 (16)	0.0028 (15)
C8	0.054 (2)	0.0527 (18)	0.0388 (17)	0.0038 (15)	0.0026 (14)	0.0028 (14)
C9	0.0374 (15)	0.0416 (15)	0.0438 (16)	0.0071 (12)	0.0158 (13)	0.0069 (13)
C10	0.0384 (17)	0.077 (2)	0.064 (2)	−0.0040 (16)	0.0102 (15)	0.0218 (18)
C11	0.0446 (19)	0.091 (3)	0.090 (3)	0.0035 (19)	0.0309 (19)	0.033 (2)
C12	0.063 (2)	0.070 (2)	0.075 (2)	0.0108 (18)	0.0376 (19)	0.0292 (19)
C13	0.070 (2)	0.069 (2)	0.0462 (19)	0.0116 (18)	0.0191 (17)	0.0152 (16)
C14	0.0410 (16)	0.0525 (17)	0.0438 (17)	−0.0021 (13)	0.0090 (13)	0.0037 (13)
C15	0.0324 (15)	0.0426 (16)	0.0574 (18)	−0.0012 (12)	0.0137 (13)	−0.0031 (13)
C16	0.0490 (19)	0.079 (2)	0.055 (2)	0.0127 (17)	0.0189 (16)	0.0057 (18)
C17	0.058 (2)	0.079 (2)	0.077 (3)	0.0061 (19)	0.035 (2)	0.000 (2)
C18	0.0378 (19)	0.099 (3)	0.090 (3)	0.0100 (19)	0.0136 (18)	−0.018 (2)
C19	0.0388 (19)	0.136 (4)	0.074 (3)	0.010 (2)	0.0028 (18)	−0.019 (3)
C20	0.0388 (17)	0.087 (2)	0.055 (2)	0.0065 (17)	0.0059 (15)	0.0005 (18)
C21	0.0365 (14)	0.0319 (13)	0.0380 (15)	0.0003 (11)	−0.0032 (12)	0.0004 (11)
C22	0.0390 (17)	0.062 (2)	0.057 (2)	0.0047 (14)	0.0054 (14)	0.0055 (16)
C23	0.0381 (17)	0.072 (2)	0.069 (2)	0.0141 (16)	−0.0046 (16)	0.0063 (18)
C24	0.054 (2)	0.060 (2)	0.055 (2)	0.0025 (16)	−0.0144 (16)	0.0074 (16)
C25	0.063 (2)	0.059 (2)	0.0434 (18)	−0.0018 (17)	−0.0071 (15)	0.0124 (15)
C26	0.0432 (17)	0.0530 (18)	0.0429 (17)	−0.0008 (14)	0.0036 (13)	0.0109 (14)

Geometric parameters (Å, º) top

Sn1—O1	2.1317 (19)	C13—H13A	0.9700
Sn1—C21	2.144 (2)	C13—H13B	0.9700
Sn1—C9	2.152 (3)	C14—H14A	0.9700
Sn1—C15	2.155 (3)	C14—H14B	0.9700
Sn1—O2ⁱ	2.769 (2)	C15—C20	1.497 (4)
N1—O4	1.208 (4)	C15—C16	1.531 (4)
N1—O5	1.228 (4)	C15—H15	0.9800
N1—C6	1.469 (5)	C16—C17	1.524 (4)
O1—C1	1.274 (3)	C16—H16A	0.9700
O2—C1	1.217 (3)	C16—H16B	0.9700
O3—C3	1.358 (4)	C17—C18	1.475 (5)
O3—C2	1.428 (3)	C17—H17A	0.9700
C1—C2	1.518 (4)	C17—H17B	0.9700
C2—H2A	0.9700	C18—C19	1.510 (5)
C2—H2B	0.9700	C18—H18A	0.9700
C3—C8	1.381 (4)	C18—H18B	0.9700
C3—C4	1.399 (4)	C19—C20	1.521 (4)
C4—C5	1.367 (5)	C19—H19A	0.9700
C4—H4	0.9300	C19—H19B	0.9700
C5—C6	1.365 (5)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C6—C7	1.378 (4)	C21—C22	1.528 (4)
C7—C8	1.378 (4)	C21—C26	1.529 (4)
C7—H7	0.9300	C21—H21	0.9800
C8—H8	0.9300	C22—C23	1.528 (4)
C9—C14	1.524 (4)	C22—H22A	0.9700
C9—C10	1.527 (4)	C22—H22B	0.9700
C9—H9	0.9800	C23—C24	1.509 (4)
C10—C11	1.517 (4)	C23—H23A	0.9700
C10—H10A	0.9700	C23—H23B	0.9700
C10—H10B	0.9700	C24—C25	1.503 (4)
C11—C12	1.520 (4)	C24—H24A	0.9700
C11—H11A	0.9700	C24—H24B	0.9700
C11—H11B	0.9700	C25—C26	1.518 (4)
C12—C13	1.506 (5)	C25—H25A	0.9700
C12—H12A	0.9700	C25—H25B	0.9700
C12—H12B	0.9700	C26—H26A	0.9700
C13—C14	1.527 (4)	C26—H26B	0.9700

O1—Sn1—C21	89.83 (9)	C9—C14—H14B	109.4
O1—Sn1—C9	99.86 (9)	C13—C14—H14B	109.4
C21—Sn1—C9	116.16 (10)	H14A—C14—H14B	108.0
O1—Sn1—C15	98.68 (9)	C20—C15—C16	110.5 (2)
C21—Sn1—C15	115.26 (11)	C20—C15—Sn1	115.4 (2)
C9—Sn1—C15	124.93 (11)	C16—C15—Sn1	112.8 (2)
O1—Sn1—O2ⁱ	170.61 (11)	C20—C15—H15	105.8
C21—Sn1—O2ⁱ	81.49 (9)	C16—C15—H15	105.8
C9—Sn1—O2ⁱ	87.27 (9)	Sn1—C15—H15	105.8
C15—Sn1—O2ⁱ	81.95 (9)	C17—C16—C15	110.8 (3)
O4—N1—O5	124.9 (4)	C17—C16—H16A	109.5
O4—N1—C6	118.5 (3)	C15—C16—H16A	109.5
O5—N1—C6	116.6 (4)	C17—C16—H16B	109.5
C1—O1—Sn1	132.96 (19)	C15—C16—H16B	109.5
C3—O3—C2	118.1 (2)	H16A—C16—H16B	108.1
O2—C1—O1	127.1 (3)	C18—C17—C16	112.2 (3)
O2—C1—C2	118.8 (3)	C18—C17—H17A	109.2
O1—C1—C2	114.0 (3)	C16—C17—H17A	109.2
O3—C2—C1	115.0 (2)	C18—C17—H17B	109.2
O3—C2—H2A	108.5	C16—C17—H17B	109.2
C1—C2—H2A	108.5	H17A—C17—H17B	107.9
O3—C2—H2B	108.5	C17—C18—C19	111.3 (3)
C1—C2—H2B	108.5	C17—C18—H18A	109.4
H2A—C2—H2B	107.5	C19—C18—H18A	109.4
O3—C3—C8	125.4 (3)	C17—C18—H18B	109.4
O3—C3—C4	115.2 (3)	C19—C18—H18B	109.4
C8—C3—C4	119.3 (3)	H18A—C18—H18B	108.0
C5—C4—C3	120.3 (3)	C18—C19—C20	111.5 (3)
C5—C4—H4	119.9	C18—C19—H19A	109.3
C3—C4—H4	119.9	C20—C19—H19A	109.3
C6—C5—C4	119.8 (3)	C18—C19—H19B	109.3
C6—C5—H5A	120.1	C20—C19—H19B	109.3
C4—C5—H5A	120.1	H19A—C19—H19B	108.0
C5—C6—C7	120.9 (3)	C15—C20—C19	112.0 (3)
C5—C6—N1	120.2 (3)	C15—C20—H20A	109.2
C7—C6—N1	118.9 (3)	C19—C20—H20A	109.2
C8—C7—C6	119.8 (3)	C15—C20—H20B	109.2
C8—C7—H7	120.1	C19—C20—H20B	109.2
C6—C7—H7	120.1	H20A—C20—H20B	107.9
C7—C8—C3	119.8 (3)	C22—C21—C26	110.6 (2)
C7—C8—H8	120.1	C22—C21—Sn1	112.46 (18)
C3—C8—H8	120.1	C26—C21—Sn1	111.92 (17)
C14—C9—C10	109.6 (2)	C22—C21—H21	107.2
C14—C9—Sn1	114.66 (18)	C26—C21—H21	107.2
C10—C9—Sn1	111.11 (19)	Sn1—C21—H21	107.2
C14—C9—H9	107.0	C23—C22—C21	111.5 (2)
C10—C9—H9	107.0	C23—C22—H22A	109.3
Sn1—C9—H9	107.0	C21—C22—H22A	109.3
C11—C10—C9	111.4 (3)	C23—C22—H22B	109.3
C11—C10—H10A	109.3	C21—C22—H22B	109.3
C9—C10—H10A	109.3	H22A—C22—H22B	108.0
C11—C10—H10B	109.3	C24—C23—C22	111.3 (3)
C9—C10—H10B	109.3	C24—C23—H23A	109.4
H10A—C10—H10B	108.0	C22—C23—H23A	109.4
C10—C11—C12	111.1 (3)	C24—C23—H23B	109.4
C10—C11—H11A	109.4	C22—C23—H23B	109.4
C12—C11—H11A	109.4	H23A—C23—H23B	108.0
C10—C11—H11B	109.4	C25—C24—C23	111.4 (3)
C12—C11—H11B	109.4	C25—C24—H24A	109.3
H11A—C11—H11B	108.0	C23—C24—H24A	109.3
C13—C12—C11	112.0 (3)	C25—C24—H24B	109.3
C13—C12—H12A	109.2	C23—C24—H24B	109.3
C11—C12—H12A	109.2	H24A—C24—H24B	108.0
C13—C12—H12B	109.2	C24—C25—C26	110.9 (3)
C11—C12—H12B	109.2	C24—C25—H25A	109.5
H12A—C12—H12B	107.9	C26—C25—H25A	109.5
C12—C13—C14	111.1 (3)	C24—C25—H25B	109.5
C12—C13—H13A	109.4	C26—C25—H25B	109.5
C14—C13—H13A	109.4	H25A—C25—H25B	108.0
C12—C13—H13B	109.4	C25—C26—C21	112.6 (2)
C14—C13—H13B	109.4	C25—C26—H26A	109.1
H13A—C13—H13B	108.0	C21—C26—H26A	109.1
C9—C14—C13	111.1 (2)	C25—C26—H26B	109.1
C9—C14—H14A	109.4	C21—C26—H26B	109.1
C13—C14—H14A	109.4	H26A—C26—H26B	107.8

C21—Sn1—O1—C1	175.0 (3)	C10—C11—C12—C13	54.4 (4)
C9—Sn1—O1—C1	−68.5 (3)	C11—C12—C13—C14	−54.6 (4)
C15—Sn1—O1—C1	59.5 (3)	C10—C9—C14—C13	−57.1 (3)
Sn1—O1—C1—O2	13.8 (4)	Sn1—C9—C14—C13	177.1 (2)
Sn1—O1—C1—C2	−164.07 (19)	C12—C13—C14—C9	56.4 (3)
C3—O3—C2—C1	−80.2 (3)	O1—Sn1—C15—C20	−98.5 (2)
O2—C1—C2—O3	166.4 (3)	C21—Sn1—C15—C20	167.5 (2)
O1—C1—C2—O3	−15.6 (4)	C9—Sn1—C15—C20	10.0 (3)
C2—O3—C3—C8	9.8 (4)	O1—Sn1—C15—C16	29.7 (2)
C2—O3—C3—C4	−168.9 (3)	C21—Sn1—C15—C16	−64.2 (2)
O3—C3—C4—C5	176.7 (3)	C9—Sn1—C15—C16	138.2 (2)
C8—C3—C4—C5	−2.1 (5)	C20—C15—C16—C17	−54.5 (4)
C3—C4—C5—C6	−0.3 (5)	Sn1—C15—C16—C17	174.8 (2)
C4—C5—C6—C7	2.0 (5)	C15—C16—C17—C18	55.7 (4)
C4—C5—C6—N1	−177.5 (3)	C16—C17—C18—C19	−55.5 (4)
O4—N1—C6—C5	179.6 (3)	C17—C18—C19—C20	54.6 (5)
O5—N1—C6—C5	−0.2 (4)	C16—C15—C20—C19	54.6 (4)
O4—N1—C6—C7	0.0 (5)	Sn1—C15—C20—C19	−176.0 (2)
O5—N1—C6—C7	−179.8 (3)	C18—C19—C20—C15	−54.8 (5)
C5—C6—C7—C8	−1.4 (5)	O1—Sn1—C21—C22	68.5 (2)
N1—C6—C7—C8	178.2 (3)	C9—Sn1—C21—C22	−32.4 (2)
C6—C7—C8—C3	−0.9 (5)	C15—Sn1—C21—C22	168.00 (19)
O3—C3—C8—C7	−176.0 (3)	O1—Sn1—C21—C26	−56.69 (18)
C4—C3—C8—C7	2.7 (4)	C9—Sn1—C21—C26	−157.60 (18)
O1—Sn1—C9—C14	99.3 (2)	C15—Sn1—C21—C26	42.8 (2)
C21—Sn1—C9—C14	−166.04 (19)	C26—C21—C22—C23	−53.0 (3)
C15—Sn1—C9—C14	−8.7 (3)	Sn1—C21—C22—C23	−178.9 (2)
O1—Sn1—C9—C10	−25.7 (2)	C21—C22—C23—C24	55.2 (4)
C21—Sn1—C9—C10	69.0 (2)	C22—C23—C24—C25	−56.8 (4)
C15—Sn1—C9—C10	−133.62 (19)	C23—C24—C25—C26	56.3 (4)
C14—C9—C10—C11	57.1 (3)	C24—C25—C26—C21	−55.1 (3)
Sn1—C9—C10—C11	−175.2 (2)	C22—C21—C26—C25	53.3 (3)
C9—C10—C11—C12	−55.7 (4)	Sn1—C21—C26—C25	179.5 (2)

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₃(C₈H₆NO₅)]
M_r	564.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.8892 (15), 11.7837 (16), 20.768 (3)
β (°)	101.456 (2)
V (Å³)	2611.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.22 × 0.09 × 0.09

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.808, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	20503, 5390, 4395
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.076, 1.02
No. of reflections	5390
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.41

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Sn1—O1	2.1317 (19)	Sn1—O2ⁱ	2.769 (2)
Sn1—C21	2.144 (2)	O1—C1	1.274 (3)
Sn1—C9	2.152 (3)	O2—C1	1.217 (3)
Sn1—C15	2.155 (3)

O1—Sn1—C21	89.83 (9)	C9—Sn1—C15	124.93 (11)
O1—Sn1—C9	99.86 (9)	O1—Sn1—O2ⁱ	170.61 (11)
C21—Sn1—C9	116.16 (10)	C21—Sn1—O2ⁱ	81.49 (9)
O1—Sn1—C15	98.68 (9)	C9—Sn1—O2ⁱ	87.27 (9)
C21—Sn1—C15	115.26 (11)	C15—Sn1—O2ⁱ	81.95 (9)