catena-Poly­[[tri-n-butyl­tin]-μ-N-(1-naphthyl)­maleamato]

The crystal structure of catena-poly­[[tri-n-butyl­tin]-μ-3-(1-naph­thyl­amino­carbonyl)­acrylato-κ²O¹:O³], [Sn(C₄H₉)₃(C₁₄H₁₀NO₃)]_n, is composed of polymeric chains wherein the metal center exhibits a distorted trigonal-bipyramidal geometry, with three n-butyl groups defining the trigonal plane [mean Sn—C 2.133 (7) Å] and the axial positions being occupied by the carboxyl­ate O atoms of two different N-(1-naphthyl)­maleamate ligands with inequivalent Sn—O distances [2.167 (4) and 2.457 (4) Å]. The N-(1-naphthyl)­maleamate fragment forms an essentially planar seven-membered ring involving an intramolecular N—H...O hydrogen bond.

S1. Comment

There have been several reports dealing with the impact of organotin chemistry in the biosphere (Gielen, 1994; Ng et al., 1991). The exploration of the structure–activity relationships of such systems has led to numerous reports in recent years (Gielen et al., 1994; Selvaratnam et al., 1994; McManus et al., 1994). Furthermore, the structural chemistry of organotin compounds with a coordination number higher than four is being extensively studied because of their biological activity, enhanced reactivity and stereochemical non-rigidity (Mehring et al., 1998). Our contributions in this field have been related to the synthesis and structural characterization of organotin derivatives of donor ligands containing chalcogens, with special reference to their biological applications (Badshah et al., 1994; Danish et al., 1995; Ali et al., 1993; Choudhary et al., 2001; Bhatti et al., 2000). In a continuation of our studies on the structural chemistry of organotin carboxylates (Parvez, Ali, Mazhar, Bhatti & Khokhar, 1999; Parvez, Ali, Mazhar, Bhatti & Choudhary. 1999; Parvez et al., 2000), we have prepared catena-poly[[tri-n-butyltin]-µ-N-(1-naphthyl)maleamato], (I), the crystal structure of which is reported in this paper.

The structure of (I) (Fig. 1) is composed of polymeric chains wherein O atoms of both ends of the N-(1-naphthyl)maleamate ligand coordinate the Sn atoms of the trigonal-planar tri-n-butyltin moiety. The Sn—C distances are identical within 3σ limits [mean Sn—C 2.133 (7) Å]. On the other hand, the Sn—O1 and Sn—O3 distances are significantly different from each other, with values of 2.167 (4) and 2.457 (4) Å, respectively, indicating that the former is a covalent bond and the latter is a coordinate bond. The Sn atom has a distorted trigonal-bipyramidal geometry, with the Sn atom 0.153 (2) Å out of the equatorial plane formed by the three C atoms bonded to it, towards the more strongly bonded O1 atom. The O1—Sn1—O3 angle is almost linear [177.97 (17)°], the C—Sn—C angles deviate somewhat from the ideal value of 120° [range 114.5 (3)–128.5 (3)°] and the O—Sn—C angles lie in the range 82.1 (2)–97.8 (2)°. These bond distances and angles are in agreement with the corresponding values found for similar Sn complexes contained in the Cambridge Structural Database (Allen & Kennard, 1993).

The molecular dimensions in the N-(1-naphthyl)maleamate ligand are normal. The ligand forms an essentially planar seven-membered ring involving an intramolecular N—H···O hydrogen bond [H1···O2 and N1···O1 1.82 and 2.669 (7) Å, respectively, and N—H···O 162°]. In terms of graph-set representation (Bernstein et al., 1994), this ring exhibits a S(7) hydrogen-bond pattern.

S2. Experimental

N-(1-Naphthyl)maleamic acid was prepared by adding 1-naphthylamine (8.59 g, 0.06 mole) to a solution containing an equimolar quantity of maleic anhydride (5.88 g, 0.06 mol) in glacial acetic acid (100 ml). The reaction mixture was stirred for 1 h, which afforded a yellow solid. The yellow product was washed with water, dried and recrystallized from ethanol–water (m.p. 421–422 K). The silver salt of N-(1-naphthyl)maleamic acid was prepared by dissolving the acid (4.82 g, 0.02 mol) in ethanol (200 ml) and adding to it a solution of an equimolar quantity of sodium bicarbonate (1.68 g, 0.02 mol). A solution of silver nitrate (3.397 g, 0.02 mol) was added dropwise to the above mixture. The precipitates thus formed were filtered off under suction, washed with water and dried over anhydrous calcium chloride in the dark. The silver salt (1.735 g, 0.005 mol) was suspended in dry chloroform (50 ml) in a 250 ml two-neck round-bottomed flask equipped with a magnetic stirrer bar and a condenser. Tributyltin chloride (1.22 ml, 0.005 mol) was added slowly with constant stirring. The reaction mixture was refluxed for 8 h under an inert atmosphere. Silver chloride which formed during the reaction was removed by filtration and the solvent was evaporated under reduced pressure. Purified (I) was obtained by crystallization of the product from chloroform–n-hexane (1:1) at room temperature by slow evaporation.

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with displacement ellipsoids plotted at the 50% probability level. [Symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z.]

(I)

Crystal data

C26H37NO3Sn	Z = 2
Mr = 530.26	F(000) = 548
Triclinic, P1	Dx = 1.377 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5705 (7) Å	Cell parameters from 8025 reflections
b = 11.7377 (9) Å	θ = 1.0–25.0°
c = 12.4726 (11) Å	µ = 1.02 mm^−1
α = 97.011 (3)°	T = 170 K
β = 107.571 (4)°	Block, yellow
γ = 102.297 (6)°	0.15 × 0.10 × 0.08 mm
V = 1278.71 (18) Å^3

Data collection

Nonius KappaCCD diffractometer	4329 independent reflections
Radiation source: fine-focus sealed tube	3640 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and ϕ scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (SORTAV: Blessing, 1997)	h = −11→11
Tmin = 0.861, Tmax = 0.922	k = −13→13
8025 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 3.9999P] where P = (Fo^2 + 2Fc^2)/3
4329 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 1.80 e Å^−3
0 restraints	Δρmin = −1.43 e Å^−3

Special details

Refinement. The H atoms were located from difference Fourier syntheses and were included in the refinements at idealized positions with isotropic displacement parameters 1.5 (methyl) and 1.2 (non-methyl) times the equivalent displacement parameters of the atoms to which they were bonded. The final difference map was free of any chemically significant features with some electron density in the vicinity of the Sn atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.22096 (5)	0.23271 (4)	0.55844 (4)	0.0376 (2)
O1	−0.0238 (5)	0.1951 (4)	0.4825 (5)	0.0463 (12)
O2	−0.0329 (5)	0.3347 (5)	0.6164 (5)	0.0498 (13)
O3	−0.5023 (5)	0.2679 (4)	0.6421 (4)	0.0420 (11)
N1	−0.2518 (6)	0.3604 (5)	0.7011 (5)	0.0387 (13)
H1	−0.1686	0.3661	0.6833	0.046*
C1	0.2107 (8)	0.0846 (6)	0.4366 (6)	0.0429 (17)
H1A	0.3064	0.0604	0.4634	0.051*
H1B	0.1264	0.0171	0.4332	0.051*
C2	0.1872 (8)	0.1093 (7)	0.3157 (7)	0.0486 (18)
H2A	0.0917	0.1337	0.2891	0.058*
H2B	0.2716	0.1769	0.3193	0.058*
C3	0.1797 (9)	0.0041 (8)	0.2278 (8)	0.062 (2)
H3A	0.1044	−0.0665	0.2311	0.075*
H3B	0.1433	0.0220	0.1501	0.075*
C4	0.3301 (9)	−0.0257 (8)	0.2456 (8)	0.056 (2)
H4A	0.3169	−0.0944	0.1868	0.084*
H4B	0.3664	−0.0447	0.3218	0.084*
H4C	0.4045	0.0428	0.2396	0.084*
C5	0.2702 (8)	0.4026 (6)	0.5116 (7)	0.0443 (17)
H5A	0.3051	0.3926	0.4449	0.053*
H5B	0.1739	0.4261	0.4857	0.053*
C6	0.3875 (9)	0.5052 (7)	0.6027 (7)	0.0498 (19)
H6A	0.4801	0.4789	0.6362	0.060*
H6B	0.4156	0.5717	0.5649	0.060*
C7	0.3374 (11)	0.5513 (8)	0.6985 (8)	0.063 (2)
H7A	0.3140	0.4864	0.7393	0.076*
H7B	0.2428	0.5754	0.6656	0.076*
C8	0.4563 (12)	0.6566 (8)	0.7840 (8)	0.074 (3)
H8A	0.4167	0.6846	0.8432	0.111*
H8B	0.4806	0.7210	0.7440	0.111*
H8C	0.5484	0.6322	0.8199	0.111*
C9	0.2300 (8)	0.1950 (7)	0.7226 (7)	0.0462 (18)
H9A	0.3045	0.2616	0.7829	0.055*
H9B	0.1292	0.1885	0.7311	0.055*
C10	0.2756 (9)	0.0788 (7)	0.7390 (7)	0.0523 (19)
H10A	0.2034	0.0142	0.6755	0.063*
H10B	0.3774	0.0875	0.7319	0.063*
C11	0.2802 (12)	0.0409 (9)	0.8495 (9)	0.075 (3)
H11A	0.1773	0.0285	0.8553	0.091*
H11B	0.3054	−0.0367	0.8476	0.091*
C12	0.3876 (17)	0.1233 (11)	0.9519 (10)	0.102 (4)
H12A	0.3820	0.0913	1.0199	0.153*
H12B	0.3626	0.2002	0.9560	0.153*
H12C	0.4906	0.1342	0.9489	0.153*
C13	−0.0952 (7)	0.2523 (6)	0.5332 (7)	0.0416 (16)
C14	−0.2644 (7)	0.2095 (6)	0.4770 (6)	0.0417 (16)
H14	−0.2976	0.1644	0.4011	0.050*
C15	−0.3749 (7)	0.2241 (6)	0.5157 (6)	0.0403 (16)
H15	−0.4731	0.1864	0.4614	0.048*
C16	−0.3797 (7)	0.2864 (6)	0.6255 (6)	0.0362 (15)
C17	−0.2369 (8)	0.4304 (6)	0.8064 (6)	0.0397 (16)
C18	−0.3221 (9)	0.3905 (7)	0.8721 (7)	0.0490 (18)
H18	−0.3943	0.3149	0.8459	0.059*
C19	−0.3030 (10)	0.4605 (8)	0.9775 (7)	0.058 (2)
H19	−0.3652	0.4329	1.0207	0.069*
C20	−0.1983 (11)	0.5661 (8)	1.0186 (7)	0.059 (2)
H20	−0.1847	0.6104	1.0917	0.070*
C21	−0.1082 (9)	0.6121 (7)	0.9542 (7)	0.0482 (18)
C22	−0.0005 (10)	0.7234 (8)	0.9929 (8)	0.061 (2)
H22	0.0131	0.7698	1.0650	0.073*
C23	0.0842 (11)	0.7662 (8)	0.9303 (8)	0.063 (2)
H23	0.1562	0.8418	0.9586	0.076*
C24	0.0662 (10)	0.6995 (7)	0.8240 (7)	0.053 (2)
H24	0.1254	0.7300	0.7799	0.064*
C25	−0.0363 (8)	0.5905 (7)	0.7835 (7)	0.0453 (17)
H25	−0.0471	0.5459	0.7112	0.054*
C26	−0.1263 (8)	0.5430 (6)	0.8461 (6)	0.0407 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0266 (3)	0.0457 (3)	0.0427 (3)	0.01165 (19)	0.0152 (2)	0.0041 (2)
O1	0.030 (2)	0.055 (3)	0.053 (3)	0.013 (2)	0.016 (2)	−0.001 (2)
O2	0.026 (2)	0.058 (3)	0.059 (3)	0.009 (2)	0.014 (2)	−0.010 (3)
O3	0.023 (2)	0.057 (3)	0.047 (3)	0.013 (2)	0.014 (2)	0.006 (2)
N1	0.029 (3)	0.047 (3)	0.044 (3)	0.013 (2)	0.018 (3)	0.007 (3)
C1	0.032 (4)	0.046 (4)	0.047 (4)	0.009 (3)	0.015 (3)	−0.002 (3)
C2	0.036 (4)	0.066 (5)	0.046 (4)	0.027 (3)	0.012 (3)	0.001 (4)
C3	0.043 (4)	0.077 (6)	0.055 (5)	0.021 (4)	0.007 (4)	−0.012 (4)
C4	0.047 (4)	0.065 (5)	0.058 (5)	0.022 (4)	0.023 (4)	−0.005 (4)
C5	0.038 (4)	0.049 (4)	0.051 (5)	0.016 (3)	0.018 (3)	0.015 (3)
C6	0.048 (4)	0.042 (4)	0.062 (5)	0.012 (3)	0.020 (4)	0.016 (4)
C7	0.070 (6)	0.053 (5)	0.062 (6)	0.003 (4)	0.029 (5)	0.007 (4)
C8	0.093 (7)	0.055 (5)	0.062 (6)	0.003 (5)	0.023 (5)	0.005 (4)
C9	0.032 (4)	0.064 (5)	0.050 (5)	0.015 (3)	0.022 (3)	0.010 (4)
C10	0.046 (4)	0.057 (5)	0.060 (5)	0.021 (4)	0.020 (4)	0.017 (4)
C11	0.073 (6)	0.076 (6)	0.076 (7)	0.024 (5)	0.018 (5)	0.023 (5)
C12	0.131 (11)	0.094 (9)	0.074 (8)	0.025 (8)	0.023 (8)	0.030 (7)
C13	0.025 (3)	0.050 (4)	0.048 (4)	0.011 (3)	0.013 (3)	0.003 (3)
C14	0.028 (3)	0.052 (4)	0.040 (4)	0.009 (3)	0.009 (3)	−0.001 (3)
C15	0.021 (3)	0.050 (4)	0.046 (4)	0.011 (3)	0.007 (3)	0.002 (3)
C16	0.025 (3)	0.043 (4)	0.042 (4)	0.014 (3)	0.010 (3)	0.009 (3)
C17	0.035 (4)	0.051 (4)	0.040 (4)	0.021 (3)	0.014 (3)	0.011 (3)
C18	0.045 (4)	0.060 (5)	0.047 (5)	0.015 (4)	0.022 (4)	0.012 (4)
C19	0.056 (5)	0.078 (6)	0.050 (5)	0.024 (4)	0.027 (4)	0.017 (4)
C20	0.071 (6)	0.075 (6)	0.040 (5)	0.034 (5)	0.025 (4)	0.009 (4)
C21	0.051 (4)	0.051 (4)	0.040 (4)	0.020 (4)	0.009 (4)	0.002 (3)
C22	0.068 (6)	0.057 (5)	0.045 (5)	0.018 (4)	0.003 (4)	0.001 (4)
C23	0.065 (6)	0.053 (5)	0.055 (5)	0.005 (4)	0.008 (4)	0.004 (4)
C24	0.056 (5)	0.053 (5)	0.044 (5)	0.011 (4)	0.008 (4)	0.011 (4)
C25	0.043 (4)	0.048 (4)	0.039 (4)	0.011 (3)	0.007 (3)	0.005 (3)
C26	0.035 (4)	0.047 (4)	0.041 (4)	0.019 (3)	0.008 (3)	0.009 (3)

Geometric parameters (Å, º)

Sn1—C1	2.129 (7)	C9—C10	1.537 (11)
Sn1—C9	2.127 (8)	C9—H9A	0.9900
Sn1—C5	2.142 (7)	C9—H9B	0.9900
Sn1—O1	2.167 (5)	C10—C11	1.490 (13)
Sn1—O3^i	2.457 (4)	C10—H10A	0.9900
O1—C13	1.293 (8)	C10—H10B	0.9900
O2—C13	1.226 (9)	C11—C12	1.451 (15)
O3—C16	1.231 (8)	C11—H11A	0.9900
O3—Sn1^ii	2.457 (4)	C11—H11B	0.9900
N1—C16	1.339 (9)	C12—H12A	0.9800
N1—C17	1.412 (9)	C12—H12B	0.9800
N1—H1	0.8800	C12—H12C	0.9800
C1—C2	1.529 (11)	C13—C14	1.499 (9)
C1—H1A	0.9900	C14—C15	1.321 (10)
C1—H1B	0.9900	C14—H14	0.9500
C2—C3	1.521 (11)	C15—C16	1.491 (10)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C17—C18	1.375 (10)
C3—C4	1.511 (11)	C17—C26	1.429 (10)
C3—H3A	0.9900	C18—C19	1.402 (12)
C3—H3B	0.9900	C18—H18	0.9500
C4—H4A	0.9800	C19—C20	1.345 (13)
C4—H4B	0.9800	C19—H19	0.9500
C4—H4C	0.9800	C20—C21	1.416 (12)
C5—C6	1.524 (11)	C20—H20	0.9500
C5—H5A	0.9900	C21—C22	1.405 (12)
C5—H5B	0.9900	C21—C26	1.428 (10)
C6—C7	1.499 (12)	C22—C23	1.350 (13)
C6—H6A	0.9900	C22—H22	0.9500
C6—H6B	0.9900	C23—C24	1.397 (12)
C7—C8	1.519 (12)	C23—H23	0.9500
C7—H7A	0.9900	C24—C25	1.364 (11)
C7—H7B	0.9900	C24—H24	0.9500
C8—H8A	0.9800	C25—C26	1.403 (10)
C8—H8B	0.9800	C25—H25	0.9500
C8—H8C	0.9800
C1—Sn1—C9	114.5 (3)	Sn1—C9—H9A	109.3
C1—Sn1—C5	115.5 (3)	C10—C9—H9B	109.3
C9—Sn1—C5	128.5 (3)	Sn1—C9—H9B	109.3
C1—Sn1—O1	87.8 (2)	H9A—C9—H9B	108.0
C9—Sn1—O1	97.8 (2)	C11—C10—C9	116.4 (8)
C5—Sn1—O1	95.8 (2)	C11—C10—H10A	108.2
C1—Sn1—O3^i	90.3 (2)	C9—C10—H10A	108.2
C9—Sn1—O3^i	82.1 (2)	C11—C10—H10B	108.2
C5—Sn1—O3^i	85.8 (2)	C9—C10—H10B	108.2
O1—Sn1—O3^i	177.97 (17)	H10A—C10—H10B	107.3
C13—O1—Sn1	118.6 (4)	C12—C11—C10	115.3 (9)
C16—O3—Sn1^ii	147.0 (5)	C12—C11—H11A	108.4
C16—N1—C17	126.6 (6)	C10—C11—H11A	108.4
C16—N1—H1	116.7	C12—C11—H11B	108.4
C17—N1—H1	116.7	C10—C11—H11B	108.4
C2—C1—Sn1	113.9 (5)	H11A—C11—H11B	107.5
C2—C1—H1A	108.8	C11—C12—H12A	109.5
Sn1—C1—H1A	108.8	C11—C12—H12B	109.5
C2—C1—H1B	108.8	H12A—C12—H12B	109.5
Sn1—C1—H1B	108.8	C11—C12—H12C	109.5
H1A—C1—H1B	107.7	H12A—C12—H12C	109.5
C3—C2—C1	114.4 (7)	H12B—C12—H12C	109.5
C3—C2—H2A	108.7	O2—C13—O1	124.3 (6)
C1—C2—H2A	108.7	O2—C13—C14	123.0 (6)
C3—C2—H2B	108.7	O1—C13—C14	112.7 (6)
C1—C2—H2B	108.7	C15—C14—C13	130.7 (7)
H2A—C2—H2B	107.6	C15—C14—H14	114.6
C4—C3—C2	113.7 (7)	C13—C14—H14	114.6
C4—C3—H3A	108.8	C14—C15—C16	134.2 (6)
C2—C3—H3A	108.8	C14—C15—H15	112.9
C4—C3—H3B	108.8	C16—C15—H15	112.9
C2—C3—H3B	108.8	O3—C16—N1	123.0 (6)
H3A—C3—H3B	107.7	O3—C16—C15	118.1 (6)
C3—C4—H4A	109.5	N1—C16—C15	119.0 (6)
C3—C4—H4B	109.5	C18—C17—N1	121.5 (7)
H4A—C4—H4B	109.5	C18—C17—C26	120.1 (7)
C3—C4—H4C	109.5	N1—C17—C26	118.4 (6)
H4A—C4—H4C	109.5	C17—C18—C19	120.4 (8)
H4B—C4—H4C	109.5	C17—C18—H18	119.8
C6—C5—Sn1	117.7 (5)	C19—C18—H18	119.8
C6—C5—H5A	107.9	C20—C19—C18	121.2 (8)
Sn1—C5—H5A	107.9	C20—C19—H19	119.4
C6—C5—H5B	107.9	C18—C19—H19	119.4
Sn1—C5—H5B	107.9	C19—C20—C21	120.8 (8)
H5A—C5—H5B	107.2	C19—C20—H20	119.6
C7—C6—C5	115.2 (7)	C21—C20—H20	119.6
C7—C6—H6A	108.5	C22—C21—C20	122.5 (8)
C5—C6—H6A	108.5	C22—C21—C26	118.4 (8)
C7—C6—H6B	108.5	C20—C21—C26	119.1 (7)
C5—C6—H6B	108.5	C23—C22—C21	121.8 (8)
H6A—C6—H6B	107.5	C23—C22—H22	119.1
C6—C7—C8	112.8 (8)	C21—C22—H22	119.1
C6—C7—H7A	109.0	C22—C23—C24	120.1 (8)
C8—C7—H7A	109.0	C22—C23—H23	120.0
C6—C7—H7B	109.0	C24—C23—H23	120.0
C8—C7—H7B	109.0	C25—C24—C23	120.1 (8)
H7A—C7—H7B	107.8	C25—C24—H24	119.9
C7—C8—H8A	109.5	C23—C24—H24	119.9
C7—C8—H8B	109.5	C24—C25—C26	121.4 (7)
H8A—C8—H8B	109.5	C24—C25—H25	119.3
C7—C8—H8C	109.5	C26—C25—H25	119.3
H8A—C8—H8C	109.5	C25—C26—C21	118.2 (7)
H8B—C8—H8C	109.5	C25—C26—C17	123.5 (7)
C10—C9—Sn1	111.6 (5)	C21—C26—C17	118.3 (7)
C10—C9—H9A	109.3
C1—Sn1—O1—C13	171.1 (6)	C17—N1—C16—O3	−2.4 (11)
C9—Sn1—O1—C13	56.7 (6)	C17—N1—C16—C15	177.0 (6)
C5—Sn1—O1—C13	−73.5 (6)	C14—C15—C16—O3	−168.7 (8)
C9—Sn1—C1—C2	173.8 (5)	C14—C15—C16—N1	11.9 (12)
C5—Sn1—C1—C2	−19.2 (6)	C16—N1—C17—C18	34.8 (11)
O1—Sn1—C1—C2	76.2 (5)	C16—N1—C17—C26	−147.5 (7)
O3^i—Sn1—C1—C2	−104.7 (5)	N1—C17—C18—C19	178.7 (7)
Sn1—C1—C2—C3	−180.0 (5)	C26—C17—C18—C19	1.0 (11)
C1—C2—C3—C4	−70.2 (10)	C17—C18—C19—C20	−2.1 (13)
C1—Sn1—C5—C6	−134.8 (5)	C18—C19—C20—C21	2.6 (13)
C9—Sn1—C5—C6	30.0 (7)	C19—C20—C21—C22	178.3 (8)
O1—Sn1—C5—C6	134.8 (5)	C19—C20—C21—C26	−2.0 (12)
O3^i—Sn1—C5—C6	−46.5 (5)	C20—C21—C22—C23	−179.8 (8)
Sn1—C5—C6—C7	−71.0 (8)	C26—C21—C22—C23	0.5 (13)
C5—C6—C7—C8	−177.7 (7)	C21—C22—C23—C24	0.0 (14)
C1—Sn1—C9—C10	17.1 (6)	C22—C23—C24—C25	−0.4 (14)
C5—Sn1—C9—C10	−147.8 (5)	C23—C24—C25—C26	0.4 (12)
O1—Sn1—C9—C10	108.3 (5)	C24—C25—C26—C21	0.2 (11)
O3^i—Sn1—C9—C10	−69.6 (5)	C24—C25—C26—C17	178.9 (7)
Sn1—C9—C10—C11	−177.8 (6)	C22—C21—C26—C25	−0.6 (10)
C9—C10—C11—C12	−61.2 (13)	C20—C21—C26—C25	179.7 (7)
Sn1—O1—C13—O2	6.8 (10)	C22—C21—C26—C17	−179.4 (7)
Sn1—O1—C13—C14	−174.8 (5)	C20—C21—C26—C17	0.9 (10)
O2—C13—C14—C15	−19.2 (13)	C18—C17—C26—C25	−179.2 (7)
O1—C13—C14—C15	162.4 (8)	N1—C17—C26—C25	3.1 (10)
C13—C14—C15—C16	0.4 (15)	C18—C17—C26—C21	−0.4 (10)
Sn1^ii—O3—C16—N1	142.2 (7)	N1—C17—C26—C21	−178.2 (6)
Sn1^ii—O3—C16—C15	−37.2 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88	1.82	2.669 (7)	162