Aqua­chloro­triphenyl­tin(IV) pyridine disolvate

In the structure of the title mononuclear Sn complex, [Sn(C₆H₅)₃Cl(H₂O)]·2C₅H₅N, the Sn^IV atom is coordinated in a slightly distorted trigonal–bipyramidal geometry by three phenyl C atoms, one water mol­ecule and one Cl⁻ anion. Two pyridine mol­ecules are O—H...N hydrogen bonded to the coordinated water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.019
• wR factor = 0.049
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   C16     ..       5.32 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   C22     ..       5.24 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.38
           From the CIF: _reflns_number_total               5668
           Count of symmetry unique reflns         3538
           Completeness (_total/calc)            160.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2130
           Fraction of Friedel pairs measured     0.602
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

In recent years, there have been many reports on the syntheses and structure determinations of various organotin(IV) compounds (e.g. Lockhart et al., 1987; Teoh et al., 1997; Basu et al., 2005). These compounds have special applications, such as as PVC stabilizers, agricultural biocides, additives for antifouling paints, and catalysts for the production of polyurethanes and silicones, and are potential antitumor agents (Thoonen et al., 2004). Furthermore, several structures of Ph₃SnCl(H₂O) cocrystallized with other molecules have been determined, for example 3-[2-(1,10-phenanthrolyl)]-5,6-diphenyl-1,2,4-triazine (Ladd et al., 1984), 3,4,7,8-tetramethyl-1,10-phenanthroline (Ng & Kumar Das, 1996), [N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine]nickel(II) (Clarke et al., 1994), di-2-pyridylketone 2-aminobenzoylhydrazone (Lanelli et al., 1995), o-phenanthroline (Ng & Kumar Das, 1996), 2,2':6',2''-terpyridyl (Prasad et al., 1982), 18-crown-6 (Amini et al., 2003), 8-methoxyquinoline (Khoo et al., 2000) and di-2-pyridyl-2-thenoylhydrazone (Carcelli et al., 1995). In these structures, there is hydrogen bonding between the coordinated water molecule of Ph₃SnCl(H₂O) and the cocrystallized molecule in the structure. In this paper, we report a structure in which two pyridine molecules are hydrogen bonded to Ph₃SnCl(H₂O).

In the molecular structure of the title compound, (I), the Sn atom is five-coordinated in a slightly distorted trigonal-bipyramidal geometry by three C atoms of three phenyl groups in the equatorial plane, and by one Cl⁻ anion and one water molecule in the axial positions (Fig. 1). The slight distortion from the ideal trigonal-bipyramidal geometry is reflected in the O1—Sn1—Cl1 angle of 175.34 (8)°, and the three C—Sn—C angles of 116.54 (9), 119.84 (7) and 122.39 (7)°. The two pyridine molecules are connected to the coordinated water molecule through O—H···O hydrogen bonds (Fig. 1 and Table 2).

S2. Experimental

A mixture of Ph₃SnCl (0.385 g, 0.1 mmol) and pyridine (0.198 g, 0.2 mmol) in 95% ethanol (13 ml) was stirred for 0.5 h. The mixture was then transferred and sealed into an 18 ml Teflon-lined autoclave, which was heated at 393 K for 89 h. After the mixture was cooled to room temperature, colorless blocks of the title complex were filtered off, washed with ether and dried at ambient temperature in air (yield 56% based on Sn). Analysis calculated for the title compound: C 59.88, H 4.85, N 4.99%; found: C 59.65, H 4.93, N 5.02%.

S3. Refinement

All H atoms bonded to C atoms were positioned geometrically and refined as riding atoms with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). The H atoms of the coordinated water molecule were located in a difference Fourier map and then refined isotropically.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. View of the structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate hydrogen bonds.

Aquachlorotriphenyltin(IV) pyridine disolvate

Crystal data

[Sn(C6H5)3Cl(H2O)]·2C5H5N	Dx = 1.389 Mg m^−3
Mr = 561.66	Melting point: not measured K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2n	Cell parameters from 8982 reflections
a = 15.492 (5) Å	θ = 2.2–28.2°
b = 15.925 (5) Å	µ = 1.07 mm^−1
c = 10.885 (5) Å	T = 293 K
V = 2685.4 (17) Å^3	Needle, colorless
Z = 4	0.43 × 0.13 × 0.11 mm
F(000) = 1136

Data collection

Bruker APEX CCD area-detector diffractometer	5668 independent reflections
Radiation source: fine-focus sealed tube	5086 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→20
Tmin = 0.623, Tmax = 0.882	k = −20→20
15753 measured reflections	l = −10→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.0281P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.049	(Δ/σ)max = 0.002
S = 1.04	Δρmax = 0.30 e Å^−3
5668 reflections	Δρmin = −0.22 e Å^−3
307 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0062 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2299 Friedels
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.005 (16)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.51354 (18)	0.82066 (19)	0.6124 (3)	0.0883 (9)
H1	0.4845	0.8540	0.6690	0.106*
C2	0.5405 (2)	0.85287 (16)	0.5045 (3)	0.0850 (8)
H2	0.5304	0.9089	0.4853	0.102*
C3	0.5825 (2)	0.80206 (19)	0.4246 (3)	0.0785 (8)
H3	0.6017	0.8227	0.3495	0.094*
C4	0.59618 (16)	0.72082 (16)	0.4556 (2)	0.0691 (6)
H4	0.6246	0.6865	0.3995	0.083*
C5	0.52989 (14)	0.73769 (15)	0.6370 (3)	0.0776 (6)
H5	0.5107	0.7155	0.7112	0.093*
C6	0.46244 (16)	0.43538 (16)	0.4866 (2)	0.0700 (6)
H6	0.4664	0.4874	0.4482	0.084*
C7	0.40878 (17)	0.3772 (2)	0.4368 (2)	0.0813 (8)
H7	0.3759	0.3896	0.3677	0.098*
C8	0.40433 (19)	0.3001 (2)	0.4905 (3)	0.0876 (9)
H8	0.3694	0.2584	0.4574	0.105*
C9	0.45174 (18)	0.28495 (17)	0.5935 (2)	0.0793 (8)
H9	0.4491	0.2331	0.6327	0.095*
C10	0.50346 (12)	0.34791 (12)	0.6381 (3)	0.0643 (5)
H10	0.5359	0.3373	0.7083	0.077*
C11	0.77724 (13)	0.68223 (14)	0.7079 (2)	0.0551 (5)
H11	0.7440	0.6884	0.6373	0.066*
C12	0.79864 (17)	0.75269 (15)	0.7782 (3)	0.0721 (7)
H12	0.7799	0.8057	0.7542	0.087*
C13	0.8473 (2)	0.7435 (2)	0.8825 (3)	0.0827 (11)
H13	0.8617	0.7905	0.9289	0.099*
C14	0.8745 (2)	0.6664 (2)	0.9188 (2)	0.0852 (9)
H14	0.9071	0.6608	0.9901	0.102*
C15	0.85403 (17)	0.59632 (15)	0.8499 (2)	0.0642 (6)
H15	0.8731	0.5438	0.8757	0.077*
C16	0.80552 (13)	0.60262 (12)	0.74313 (17)	0.0445 (4)
C17	0.69499 (16)	0.39679 (14)	0.85288 (19)	0.0580 (5)
H17	0.6919	0.4498	0.8885	0.070*
C18	0.66487 (18)	0.32782 (19)	0.9169 (2)	0.0774 (8)
H18	0.6409	0.3351	0.9945	0.093*
C19	0.6699 (2)	0.2496 (2)	0.8680 (3)	0.0825 (11)
H19	0.6503	0.2035	0.9123	0.099*
C20	0.70402 (17)	0.23894 (15)	0.7529 (3)	0.0772 (8)
H20	0.7068	0.1855	0.7185	0.093*
C21	0.73442 (14)	0.30760 (14)	0.6877 (2)	0.0573 (6)
H21	0.7583	0.2997	0.6102	0.069*
C22	0.72966 (11)	0.38797 (12)	0.73637 (18)	0.0425 (4)
C23	0.76955 (15)	0.49598 (10)	0.4412 (3)	0.0456 (5)
C24	0.8438 (2)	0.49805 (15)	0.3697 (3)	0.0692 (8)
H24	0.8977	0.4978	0.4075	0.083*
C25	0.8386 (3)	0.50045 (16)	0.2425 (3)	0.0848 (11)
H25	0.8890	0.5026	0.1961	0.102*
C26	0.7610 (3)	0.49965 (14)	0.1849 (4)	0.0792 (10)
H26	0.7582	0.5012	0.0996	0.095*
C27	0.6874 (3)	0.49658 (15)	0.2522 (3)	0.0794 (10)
H27	0.6341	0.4951	0.2128	0.095*
C28	0.6912 (2)	0.49569 (13)	0.3795 (3)	0.0621 (7)
H28	0.6401	0.4949	0.4244	0.075*
N1	0.57166 (13)	0.68770 (12)	0.56033 (19)	0.0644 (5)
N2	0.50952 (11)	0.42256 (11)	0.58661 (17)	0.0599 (5)
O1	0.63289 (8)	0.53842 (9)	0.6501 (2)	0.0478 (3)
Sn1	0.776999 (6)	0.493730 (5)	0.63796 (5)	0.03979 (5)
Cl1	0.93047 (3)	0.44400 (3)	0.64344 (8)	0.06432 (13)
H1B	0.5994 (19)	0.5037 (13)	0.646 (5)	0.070 (8)*
H1A	0.6200 (15)	0.5809 (15)	0.619 (3)	0.071 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0821 (17)	0.0832 (17)	0.100 (3)	0.0289 (13)	0.0149 (17)	−0.0179 (18)
C2	0.0815 (18)	0.0560 (14)	0.117 (2)	0.0082 (13)	−0.0076 (17)	0.0160 (15)
C3	0.0849 (19)	0.0792 (18)	0.0715 (17)	−0.0070 (15)	0.0072 (14)	0.0237 (15)
C4	0.0689 (16)	0.0708 (15)	0.0674 (16)	0.0067 (12)	0.0105 (12)	−0.0028 (12)
C5	0.0716 (13)	0.0954 (16)	0.0657 (14)	0.0131 (12)	0.0106 (19)	0.019 (2)
C6	0.0600 (14)	0.0763 (15)	0.0737 (16)	0.0057 (12)	0.0032 (12)	0.0255 (13)
C7	0.0631 (16)	0.126 (2)	0.0551 (15)	−0.0085 (16)	−0.0078 (12)	0.0116 (16)
C8	0.0811 (19)	0.107 (2)	0.0747 (18)	−0.0416 (17)	0.0023 (15)	−0.0173 (17)
C9	0.0820 (17)	0.0642 (14)	0.092 (2)	−0.0183 (13)	0.0126 (14)	0.0155 (12)
C10	0.0534 (10)	0.0744 (13)	0.0652 (12)	−0.0008 (9)	−0.0013 (16)	0.020 (2)
C11	0.0560 (13)	0.0454 (11)	0.0638 (14)	−0.0054 (9)	0.0009 (10)	−0.0016 (10)
C12	0.0772 (17)	0.0462 (12)	0.093 (2)	−0.0100 (11)	0.0196 (15)	−0.0111 (12)
C13	0.101 (2)	0.080 (2)	0.068 (2)	−0.0286 (19)	0.0122 (16)	−0.0331 (17)
C14	0.114 (2)	0.090 (2)	0.0513 (15)	−0.0262 (17)	−0.0139 (14)	−0.0147 (14)
C15	0.0842 (17)	0.0615 (13)	0.0469 (12)	−0.0112 (12)	−0.0106 (11)	0.0039 (10)
C16	0.0449 (10)	0.0453 (10)	0.0433 (11)	−0.0086 (8)	0.0050 (8)	0.0002 (8)
C17	0.0689 (14)	0.0574 (13)	0.0476 (13)	−0.0010 (11)	0.0028 (10)	0.0040 (9)
C18	0.0793 (18)	0.096 (2)	0.0571 (15)	−0.0071 (14)	0.0074 (13)	0.0312 (15)
C19	0.0777 (19)	0.067 (2)	0.102 (3)	−0.0175 (15)	−0.0097 (18)	0.0453 (18)
C20	0.0747 (17)	0.0393 (12)	0.117 (2)	−0.0087 (11)	−0.0142 (17)	0.0076 (13)
C21	0.0597 (13)	0.0438 (11)	0.0685 (14)	−0.0029 (9)	−0.0012 (10)	−0.0043 (9)
C22	0.0402 (11)	0.0404 (10)	0.0469 (11)	−0.0004 (7)	−0.0049 (8)	0.0035 (8)
C23	0.0565 (14)	0.0373 (11)	0.0431 (14)	−0.0018 (7)	0.0031 (9)	−0.0023 (7)
C24	0.0648 (17)	0.087 (2)	0.0559 (17)	−0.0105 (11)	0.0123 (13)	−0.0073 (11)
C25	0.096 (3)	0.100 (3)	0.058 (2)	−0.0137 (14)	0.0288 (19)	−0.0092 (12)
C26	0.117 (3)	0.080 (2)	0.0407 (14)	−0.0020 (14)	0.0075 (17)	−0.0036 (9)
C27	0.092 (3)	0.094 (2)	0.0523 (18)	0.0076 (14)	−0.0194 (17)	−0.0043 (11)
C28	0.0617 (16)	0.0771 (18)	0.0475 (15)	0.0072 (11)	−0.0006 (12)	−0.0027 (9)
N1	0.0623 (11)	0.0561 (10)	0.0750 (13)	0.0096 (9)	0.0040 (10)	0.0142 (9)
N2	0.0497 (10)	0.0562 (10)	0.0737 (13)	−0.0021 (8)	−0.0049 (8)	0.0047 (8)
O1	0.0475 (7)	0.0400 (6)	0.0559 (10)	0.0022 (6)	−0.0022 (8)	0.0001 (9)
Sn1	0.04407 (7)	0.03517 (6)	0.04012 (7)	−0.00214 (4)	0.00003 (10)	0.00169 (12)
Cl1	0.0463 (2)	0.0562 (2)	0.0904 (4)	0.00624 (17)	0.0004 (4)	0.0133 (5)

Geometric parameters (Å, º)

C1—C2	1.347 (4)	C15—C16	1.388 (3)
C1—C5	1.372 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—Sn1	2.124 (2)
C2—C3	1.355 (4)	C17—C18	1.382 (3)
C2—H2	0.9300	C17—C22	1.384 (3)
C3—C4	1.354 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.357 (4)
C4—N1	1.312 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.370 (4)
C5—N1	1.323 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.386 (3)
C6—N2	1.326 (3)	C20—H20	0.9300
C6—C7	1.358 (4)	C21—C22	1.387 (3)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.361 (4)	C22—Sn1	2.127 (2)
C7—H7	0.9300	C23—C28	1.387 (4)
C8—C9	1.362 (4)	C23—C24	1.390 (4)
C8—H8	0.9300	C23—Sn1	2.145 (3)
C9—C10	1.372 (3)	C24—C25	1.387 (5)
C9—H9	0.9300	C24—H24	0.9300
C10—N2	1.318 (3)	C25—C26	1.356 (6)
C10—H10	0.9300	C25—H25	0.9300
C11—C16	1.395 (3)	C26—C27	1.357 (6)
C11—C12	1.398 (3)	C26—H26	0.9300
C11—H11	0.9300	C27—C28	1.387 (5)
C12—C13	1.371 (4)	C27—H27	0.9300
C12—H12	0.9300	C28—H28	0.9300
C13—C14	1.356 (4)	O1—Sn1	2.3469 (14)
C13—H13	0.9300	O1—H1B	0.76 (3)
C14—C15	1.382 (3)	O1—H1A	0.78 (3)
C14—H14	0.9300	Sn1—Cl1	2.5068 (9)
C2—C1—C5	118.7 (3)	C22—C17—H17	119.6
C2—C1—H1	120.7	C19—C18—C17	120.8 (3)
C5—C1—H1	120.7	C19—C18—H18	119.6
C1—C2—C3	118.7 (2)	C17—C18—H18	119.6
C1—C2—H2	120.6	C18—C19—C20	119.7 (3)
C3—C2—H2	120.6	C18—C19—H19	120.2
C4—C3—C2	119.1 (2)	C20—C19—H19	120.2
C4—C3—H3	120.5	C19—C20—C21	120.1 (3)
C2—C3—H3	120.5	C19—C20—H20	119.9
N1—C4—C3	123.7 (3)	C21—C20—H20	119.9
N1—C4—H4	118.1	C20—C21—C22	120.9 (2)
C3—C4—H4	118.1	C20—C21—H21	119.5
N1—C5—C1	123.1 (3)	C22—C21—H21	119.5
N1—C5—H5	118.4	C17—C22—C21	117.67 (19)
C1—C5—H5	118.4	C17—C22—Sn1	120.99 (15)
N2—C6—C7	124.0 (2)	C21—C22—Sn1	121.32 (16)
N2—C6—H6	118.0	C28—C23—C24	117.0 (3)
C7—C6—H6	118.0	C28—C23—Sn1	122.0 (2)
C6—C7—C8	118.3 (2)	C24—C23—Sn1	121.0 (2)
C6—C7—H7	120.8	C25—C24—C23	120.7 (3)
C8—C7—H7	120.8	C25—C24—H24	119.6
C7—C8—C9	119.1 (3)	C23—C24—H24	119.6
C7—C8—H8	120.4	C26—C25—C24	120.8 (3)
C9—C8—H8	120.4	C26—C25—H25	119.6
C8—C9—C10	118.4 (3)	C24—C25—H25	119.6
C8—C9—H9	120.8	C25—C26—C27	119.8 (4)
C10—C9—H9	120.8	C25—C26—H26	120.1
N2—C10—C9	123.4 (3)	C27—C26—H26	120.1
N2—C10—H10	118.3	C26—C27—C28	120.2 (4)
C9—C10—H10	118.3	C26—C27—H27	119.9
C16—C11—C12	120.3 (2)	C28—C27—H27	119.9
C16—C11—H11	119.9	C27—C28—C23	121.4 (3)
C12—C11—H11	119.9	C27—C28—H28	119.3
C13—C12—C11	119.9 (3)	C23—C28—H28	119.3
C13—C12—H12	120.1	C4—N1—C5	116.6 (2)
C11—C12—H12	120.1	C10—N2—C6	116.7 (2)
C14—C13—C12	120.6 (3)	Sn1—O1—H1B	115.2 (18)
C14—C13—H13	119.7	Sn1—O1—H1A	118.7 (18)
C12—C13—H13	119.7	H1B—O1—H1A	116 (3)
C13—C14—C15	120.1 (3)	C16—Sn1—C22	116.54 (9)
C13—C14—H14	119.9	C16—Sn1—C23	122.39 (7)
C15—C14—H14	119.9	C22—Sn1—C23	119.84 (7)
C14—C15—C16	121.3 (2)	C16—Sn1—O1	85.41 (7)
C14—C15—H15	119.3	C22—Sn1—O1	83.32 (7)
C16—C15—H15	119.3	C23—Sn1—O1	90.01 (9)
C15—C16—C11	117.8 (2)	C16—Sn1—Cl1	92.74 (6)
C15—C16—Sn1	120.33 (16)	C22—Sn1—Cl1	93.72 (5)
C11—C16—Sn1	121.88 (16)	C23—Sn1—Cl1	94.59 (7)
C18—C17—C22	120.8 (2)	O1—Sn1—Cl1	175.34 (8)
C18—C17—H17	119.6
C5—C1—C2—C3	0.1 (5)	C24—C23—C28—C27	0.6 (3)
C1—C2—C3—C4	−0.1 (5)	Sn1—C23—C28—C27	−179.56 (16)
C2—C3—C4—N1	−0.7 (5)	C3—C4—N1—C5	1.3 (4)
C2—C1—C5—N1	0.7 (5)	C1—C5—N1—C4	−1.3 (4)
N2—C6—C7—C8	−1.7 (4)	C9—C10—N2—C6	−0.1 (4)
C6—C7—C8—C9	1.7 (4)	C7—C6—N2—C10	0.9 (4)
C7—C8—C9—C10	−1.0 (4)	C15—C16—Sn1—C22	47.86 (19)
C8—C9—C10—N2	0.2 (4)	C11—C16—Sn1—C22	−132.59 (16)
C16—C11—C12—C13	−0.3 (4)	C15—C16—Sn1—C23	−144.87 (17)
C11—C12—C13—C14	−0.4 (5)	C11—C16—Sn1—C23	34.7 (2)
C12—C13—C14—C15	0.5 (5)	C15—C16—Sn1—O1	128.05 (18)
C13—C14—C15—C16	−0.1 (5)	C11—C16—Sn1—O1	−52.40 (17)
C14—C15—C16—C11	−0.6 (4)	C15—C16—Sn1—Cl1	−47.67 (17)
C14—C15—C16—Sn1	179.0 (2)	C11—C16—Sn1—Cl1	131.88 (16)
C12—C11—C16—C15	0.8 (3)	C17—C22—Sn1—C16	18.84 (18)
C12—C11—C16—Sn1	−178.80 (17)	C21—C22—Sn1—C16	−159.47 (16)
C22—C17—C18—C19	1.1 (4)	C17—C22—Sn1—C23	−148.77 (16)
C17—C18—C19—C20	−1.0 (5)	C21—C22—Sn1—C23	32.92 (18)
C18—C19—C20—C21	1.0 (4)	C17—C22—Sn1—O1	−62.62 (17)
C19—C20—C21—C22	−1.0 (4)	C21—C22—Sn1—O1	119.08 (17)
C18—C17—C22—C21	−1.2 (3)	C17—C22—Sn1—Cl1	113.77 (16)
C18—C17—C22—Sn1	−179.52 (19)	C21—C22—Sn1—Cl1	−64.53 (16)
C20—C21—C22—C17	1.1 (3)	C28—C23—Sn1—C16	−103.04 (16)
C20—C21—C22—Sn1	179.48 (17)	C24—C23—Sn1—C16	76.77 (17)
C28—C23—C24—C25	0.5 (3)	C28—C23—Sn1—C22	63.82 (17)
Sn1—C23—C24—C25	−179.27 (17)	C24—C23—Sn1—C22	−116.37 (16)
C23—C24—C25—C26	−0.9 (4)	C28—C23—Sn1—O1	−18.48 (15)
C24—C25—C26—C27	0.1 (4)	C24—C23—Sn1—O1	161.33 (16)
C25—C26—C27—C28	1.1 (4)	C28—C23—Sn1—Cl1	160.78 (14)
C26—C27—C28—C23	−1.5 (3)	C24—C23—Sn1—Cl1	−19.42 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.78 (3)	1.96 (3)	2.740 (2)	170 (3)
O1—H1B···N2	0.76 (3)	2.01 (3)	2.745 (2)	164 (6)