Dichloridoocta­kis(2-chloro­benz­yl)di-μ2-hydroxido-di-μ3-oxido-tetra­tin(IV)

Zhang, Q.-J.; Yin, H.-D.; Wen, L.-Y.; Wang, D.-Q.

doi:10.1107/S1600536809045176

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1494

https://doi.org/10.1107/S1600536809045176

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Dichloridooctakis(2-chlorobenzyl)di-μ₂-hydroxido-di-μ₃-oxido-tetratin(IV)

Qi-Jun Zhang,^a Han-Dong Yin,^a ^* Li-Yuan Wen ^a and Da-Qi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 21 October 2009; accepted 28 October 2009; online 31 October 2009)

The title tetranuclear Sn^IV compound, [Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂], has site symmetry $[\overline{1}]$ . Two O²⁻ and two OH⁻ anions bridge four Sn^IV cations to form the tetranuclear compound. The two independent Sn^IV cations assume SnO₃C₂ and SnO₂C₂Cl distorted trigonal-bipyramidal coordination geometries. Intramolecular O—H⋯Cl hydrogen bonding is present in the structure. One Cl atom of a chlorobenzyl ligand is disordered over two sites with an occupancy ratio of 0.693 (2):0.307 (2).

Related literature

For a related structure, see: Li et al. (2006 ). For the corresponding bond distances in an organotin compound, see: Lo & Ng (2009 ).

Experimental

Crystal data

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]
M_r = 1616.22
Triclinic, $[P \overline 1]$
a = 10.986 (2) Å
b = 11.227 (2) Å
c = 13.573 (3) Å
α = 74.656 (2)°
β = 67.942 (2)°
γ = 75.753 (2)°
V = 1475.9 (6) Å³
Z = 1
Mo Kα radiation
μ = 2.17 mm⁻¹
T = 298 K
0.44 × 0.37 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.449, T_max = 0.535
7669 measured reflections
5112 independent reflections
3865 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.074
S = 1.04
5112 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 1.27 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O1	2.148 (3)
Sn1—O2	2.050 (3)
Sn1—O2ⁱ	2.146 (3)
Sn1—C1	2.126 (5)
Sn1—C8	2.146 (5)
Sn2—O1	2.276 (3)
Sn2—O2	2.025 (3)
Sn2—C15	2.147 (5)
Sn2—C22	2.149 (5)
Sn2—Cl1	2.4376 (13)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl2	0.86	2.80	3.386 (4)	127

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809045176/xu2652sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809045176/xu2652Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was obtained as an adventitious product of the partial hydrolysis of di(2-chlorobenzyl)dichloridotin(IV) during the attempted preparation of adducts of this tin precursor complex with 5-chlorosalicylaldehyde benzoyldrazone in benzene and ethanol. It crystallizes from dichloromethane and ethanol. From Fig. 1, it can be seen that complex (I) contains two independent penta-coordinated Sn atoms. It is a centrosymmetric complex, where one half of the molecule comprises the crystallographic asymmetric unit and the other half is generated by an inversion centre. Each of the two independent Sn atoms is five-coordinate, adopting approximate trigonal bipyramidal coordination (Table 1). These are similar to those in the related organotin compound (Li et al., 2006). The molecular conformation is stabilized by O1—H1···Cl2 hydrogen bond (Table 2). The Sn—C distances lie in the rather narrow range 2.126 (5)–2.149 (5) Å, which are closed to the corresponding distances reported in the organotin compound (Lo & Ng, 2009).

Related literature top

For a related structure, see: Li et al. (2006). For the corresponding bond distances in an organotin compound, see: Lo & Ng (2009).

Experimental top

Di(2-chlorobenzyl)dichloridotin(IV) (2 mmol) and 5-chlorosalicylaldehyde benzoyldrazone(2 mmol) was added to a solution of sodium methoxide (3 mmol) in benzene (15 ml) and ethanol (15 ml, 95%). The mixture was then heated under reflux with stirring for 5 h and the solvent was removed by evaporation in vacuo. The crude adduct was recrystallized from dichloromethane/ethanol and colourless crystals suitable for X-ray diffraction were obtained.

Structure description top

For a related structure, see: Li et al. (2006). For the corresponding bond distances in an organotin compound, see: Lo & Ng (2009).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the compound showing 50% probability displacement ellipsoids [symmetry code: (A) = 1-x, 1-y, 1-z].

Dichloridooctakis(2-chlorobenzyl)di-µ₂-hydroxido-di-µ₃-oxido-tetratin(IV) top

Crystal data top

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]	Z = 1
M_r = 1616.22	F(000) = 788
Triclinic, P1	D_x = 1.818 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.986 (2) Å	Cell parameters from 4036 reflections
b = 11.227 (2) Å	θ = 2.6–27.4°
c = 13.573 (3) Å	µ = 2.17 mm⁻¹
α = 74.656 (2)°	T = 298 K
β = 67.942 (2)°	Block, colourless
γ = 75.753 (2)°	0.44 × 0.37 × 0.33 mm
V = 1475.9 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5112 independent reflections
Radiation source: fine-focus sealed tube	3865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.449, T_max = 0.535	k = −13→13
7669 measured reflections	l = −16→10

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0262P)² + 2.2448P] where P = (F_o² + 2F_c²)/3
5112 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 1.27 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]	γ = 75.753 (2)°
M_r = 1616.22	V = 1475.9 (6) Å³
Triclinic, P1	Z = 1
a = 10.986 (2) Å	Mo Kα radiation
b = 11.227 (2) Å	µ = 2.17 mm⁻¹
c = 13.573 (3) Å	T = 298 K
α = 74.656 (2)°	0.44 × 0.37 × 0.33 mm
β = 67.942 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5112 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3865 reflections with I > 2σ(I)
T_min = 0.449, T_max = 0.535	R_int = 0.015
7669 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	Δρ_max = 1.27 e Å⁻³
5112 reflections	Δρ_min = −0.57 e Å⁻³
338 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.59257 (3)	0.37338 (3)	0.44839 (2)	0.03438 (10)
Sn2	0.49384 (3)	0.58881 (3)	0.25330 (2)	0.03713 (10)
Cl1	0.35586 (14)	0.79133 (11)	0.28147 (11)	0.0516 (3)
Cl2	0.6318 (2)	0.0780 (2)	0.34868 (19)	0.0704 (6)	0.693 (2)
Cl2'	0.2326 (5)	0.3325 (5)	0.5648 (4)	0.0704 (6)	0.307 (2)
Cl3	0.96390 (18)	0.40745 (16)	0.17259 (15)	0.0897 (6)
Cl4	0.09931 (19)	0.5877 (2)	0.36984 (14)	0.0927 (6)
Cl5	0.6057 (2)	0.72167 (16)	−0.03870 (14)	0.0908 (6)
O1	0.6121 (3)	0.3933 (3)	0.2815 (2)	0.0444 (8)
H1	0.6408	0.3297	0.2503	0.053*
O2	0.4776 (3)	0.5414 (3)	0.4119 (2)	0.0365 (7)
C1	0.4860 (7)	0.2203 (6)	0.5202 (5)	0.077 (2)
H1A	0.5486	0.1446	0.5314	0.092*
H1B	0.4238	0.2336	0.5908	0.092*
C2	0.4103 (7)	0.2003 (5)	0.4555 (5)	0.0597 (16)
C3	0.4702 (6)	0.1302 (5)	0.3739 (5)	0.0646 (17)
H3A	0.5605	0.0982	0.3588	0.077*	0.307 (2)
C4	0.4013 (7)	0.1078 (6)	0.3160 (5)	0.0697 (18)
H4	0.4440	0.0592	0.2629	0.084*
C5	0.2691 (8)	0.1581 (7)	0.3376 (6)	0.078 (2)
H5	0.2210	0.1431	0.2998	0.093*
C6	0.2087 (7)	0.2301 (6)	0.4146 (6)	0.0775 (19)
H6	0.1197	0.2663	0.4277	0.093*
C7	0.2776 (8)	0.2497 (6)	0.4731 (5)	0.0724 (18)
H7A	0.2335	0.2980	0.5263	0.087*	0.693 (2)
C8	0.8018 (5)	0.3527 (5)	0.4200 (4)	0.0541 (14)
H8A	0.8337	0.4296	0.3766	0.065*
H8B	0.8166	0.3377	0.4887	0.065*
C9	0.8788 (5)	0.2460 (5)	0.3625 (4)	0.0469 (12)
C10	0.9489 (5)	0.2595 (5)	0.2531 (4)	0.0510 (13)
C11	1.0141 (5)	0.1589 (6)	0.2019 (5)	0.0630 (16)
H11	1.0598	0.1719	0.1278	0.076*
C12	1.0104 (6)	0.0399 (6)	0.2620 (6)	0.080 (2)
H12	1.0524	−0.0287	0.2285	0.096*
C13	0.9448 (7)	0.0222 (6)	0.3713 (7)	0.086 (2)
H13	0.9450	−0.0587	0.4121	0.103*
C14	0.8791 (6)	0.1218 (6)	0.4213 (5)	0.0666 (16)
H14	0.8337	0.1074	0.4955	0.080*
C15	0.3720 (6)	0.5022 (5)	0.2102 (4)	0.0541 (14)
H15A	0.4308	0.4523	0.1568	0.065*
H15B	0.3287	0.4446	0.2740	0.065*
C16	0.2673 (6)	0.5833 (5)	0.1664 (4)	0.0488 (13)
C17	0.1427 (6)	0.6287 (5)	0.2294 (5)	0.0596 (15)
C18	0.0470 (7)	0.7033 (6)	0.1868 (6)	0.0728 (18)
H18	−0.0357	0.7343	0.2323	0.087*
C19	0.0748 (7)	0.7312 (6)	0.0775 (6)	0.080 (2)
H19	0.0110	0.7812	0.0480	0.096*
C20	0.1997 (8)	0.6846 (6)	0.0096 (5)	0.0760 (19)
H20	0.2185	0.7022	−0.0650	0.091*
C21	0.2924 (6)	0.6141 (5)	0.0526 (5)	0.0632 (16)
H21	0.3754	0.5846	0.0065	0.076*
C22	0.6829 (5)	0.6492 (5)	0.1629 (4)	0.0546 (14)
H22A	0.7318	0.6346	0.2126	0.066*
H22B	0.7322	0.5957	0.1103	0.066*
C23	0.6833 (5)	0.7819 (4)	0.1041 (4)	0.0445 (12)
C24	0.6538 (5)	0.8249 (5)	0.0094 (4)	0.0491 (13)
C25	0.6586 (6)	0.9448 (5)	−0.0481 (4)	0.0566 (14)
H25	0.6375	0.9697	−0.1116	0.068*
C26	0.6952 (6)	1.0277 (5)	−0.0102 (5)	0.0672 (17)
H26	0.7000	1.1093	−0.0487	0.081*
C27	0.7244 (7)	0.9914 (6)	0.0830 (5)	0.0712 (18)
H27	0.7487	1.0480	0.1085	0.085*
C28	0.7178 (6)	0.8692 (6)	0.1404 (5)	0.0666 (16)
H28	0.7370	0.8454	0.2047	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0413 (2)	0.02862 (17)	0.03475 (19)	−0.00165 (14)	−0.01569 (15)	−0.00788 (13)
Sn2	0.0458 (2)	0.03431 (18)	0.03224 (19)	−0.00562 (15)	−0.01628 (15)	−0.00401 (14)
Cl1	0.0610 (8)	0.0372 (6)	0.0546 (8)	0.0030 (6)	−0.0240 (7)	−0.0085 (6)
Cl2	0.0727 (14)	0.0590 (12)	0.0858 (15)	−0.0032 (10)	−0.0315 (12)	−0.0237 (10)
Cl2'	0.0727 (14)	0.0590 (12)	0.0858 (15)	−0.0032 (10)	−0.0315 (12)	−0.0237 (10)
Cl3	0.0743 (11)	0.0692 (11)	0.0932 (13)	−0.0020 (9)	−0.0141 (10)	0.0080 (9)
Cl4	0.0917 (13)	0.1304 (16)	0.0571 (10)	−0.0280 (12)	−0.0216 (9)	−0.0155 (10)
Cl5	0.1487 (18)	0.0662 (10)	0.0763 (12)	−0.0408 (11)	−0.0494 (12)	−0.0049 (8)
O1	0.054 (2)	0.0381 (18)	0.0397 (19)	−0.0030 (16)	−0.0209 (16)	−0.0015 (14)
O2	0.0440 (19)	0.0304 (16)	0.0341 (17)	0.0006 (14)	−0.0169 (15)	−0.0051 (13)
C1	0.137 (6)	0.064 (4)	0.056 (4)	−0.059 (4)	−0.052 (4)	0.014 (3)
C2	0.097 (5)	0.048 (3)	0.048 (3)	−0.043 (3)	−0.034 (3)	0.011 (3)
C3	0.081 (5)	0.060 (4)	0.067 (4)	−0.028 (3)	−0.041 (4)	0.003 (3)
C4	0.099 (5)	0.068 (4)	0.063 (4)	−0.032 (4)	−0.038 (4)	−0.013 (3)
C5	0.093 (6)	0.082 (5)	0.084 (5)	−0.041 (4)	−0.051 (4)	−0.002 (4)
C6	0.074 (5)	0.074 (4)	0.090 (5)	−0.029 (4)	−0.031 (4)	−0.003 (4)
C7	0.101 (6)	0.065 (4)	0.061 (4)	−0.042 (4)	−0.027 (4)	0.000 (3)
C8	0.047 (3)	0.063 (4)	0.064 (4)	0.000 (3)	−0.022 (3)	−0.033 (3)
C9	0.035 (3)	0.054 (3)	0.055 (3)	−0.001 (2)	−0.019 (2)	−0.016 (3)
C10	0.039 (3)	0.058 (3)	0.058 (4)	−0.003 (3)	−0.020 (3)	−0.013 (3)
C11	0.045 (3)	0.075 (4)	0.068 (4)	0.005 (3)	−0.015 (3)	−0.031 (3)
C12	0.062 (4)	0.068 (4)	0.108 (6)	0.004 (3)	−0.016 (4)	−0.044 (4)
C13	0.069 (5)	0.052 (4)	0.112 (6)	−0.008 (3)	−0.016 (4)	0.003 (4)
C14	0.051 (4)	0.064 (4)	0.069 (4)	0.004 (3)	−0.014 (3)	−0.007 (3)
C15	0.065 (4)	0.048 (3)	0.060 (4)	−0.013 (3)	−0.029 (3)	−0.013 (3)
C16	0.061 (4)	0.045 (3)	0.055 (3)	−0.013 (3)	−0.030 (3)	−0.014 (2)
C17	0.063 (4)	0.067 (4)	0.057 (4)	−0.013 (3)	−0.026 (3)	−0.015 (3)
C18	0.064 (4)	0.079 (4)	0.085 (5)	−0.005 (3)	−0.038 (4)	−0.020 (4)
C19	0.082 (5)	0.077 (5)	0.095 (6)	−0.004 (4)	−0.057 (5)	−0.005 (4)
C20	0.106 (6)	0.083 (5)	0.058 (4)	−0.030 (4)	−0.045 (4)	−0.005 (3)
C21	0.066 (4)	0.063 (4)	0.074 (4)	−0.011 (3)	−0.030 (3)	−0.025 (3)
C22	0.047 (3)	0.046 (3)	0.058 (3)	−0.004 (2)	−0.016 (3)	0.005 (3)
C23	0.033 (3)	0.041 (3)	0.048 (3)	−0.006 (2)	−0.006 (2)	−0.002 (2)
C24	0.049 (3)	0.044 (3)	0.047 (3)	−0.008 (2)	−0.009 (3)	−0.006 (2)
C25	0.064 (4)	0.046 (3)	0.048 (3)	−0.005 (3)	−0.013 (3)	−0.002 (3)
C26	0.072 (4)	0.039 (3)	0.070 (4)	−0.002 (3)	−0.007 (3)	−0.007 (3)
C27	0.089 (5)	0.065 (4)	0.062 (4)	−0.033 (4)	−0.011 (4)	−0.016 (3)
C28	0.065 (4)	0.076 (4)	0.061 (4)	−0.020 (3)	−0.024 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.148 (3)	C9—C14	1.412 (7)
Sn1—O2	2.050 (3)	C10—C11	1.385 (8)
Sn1—O2ⁱ	2.146 (3)	C11—C12	1.370 (8)
Sn1—C1	2.126 (5)	C11—H11	0.9300
Sn1—C8	2.146 (5)	C12—C13	1.368 (9)
Sn2—O1	2.276 (3)	C12—H12	0.9300
Sn2—O2	2.025 (3)	C13—C14	1.367 (9)
Sn2—C15	2.147 (5)	C13—H13	0.9300
Sn2—C22	2.149 (5)	C14—H14	0.9300
Sn2—Cl1	2.4376 (13)	C15—C16	1.489 (7)
Cl2—C3	1.658 (7)	C15—H15A	0.9700
Cl2—H3A	0.7301	C15—H15B	0.9700
Cl2'—C7	1.606 (8)	C16—C17	1.368 (8)
Cl2'—H7A	0.7242	C16—C21	1.424 (7)
Cl3—C10	1.737 (6)	C17—C18	1.381 (8)
Cl4—C17	1.742 (6)	C18—C19	1.361 (9)
Cl5—C24	1.735 (5)	C18—H18	0.9300
O1—H1	0.8590	C19—C20	1.399 (9)
C1—C2	1.503 (7)	C19—H19	0.9300
C1—H1A	0.9700	C20—C21	1.345 (8)
C1—H1B	0.9700	C20—H20	0.9300
C2—C7	1.379 (9)	C21—H21	0.9300
C2—C3	1.391 (8)	C22—C23	1.492 (6)
C3—C4	1.379 (7)	C22—H22A	0.9700
C3—H3A	0.9301	C22—H22B	0.9700
C4—C5	1.371 (9)	C23—C24	1.377 (7)
C4—H4	0.9300	C23—C28	1.388 (7)
C5—C6	1.359 (9)	C24—C25	1.369 (7)
C5—H5	0.9300	C25—C26	1.374 (8)
C6—C7	1.371 (8)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.355 (8)
C7—H7A	0.9300	C26—H26	0.9300
C8—C9	1.502 (7)	C27—C28	1.391 (8)
C8—H8A	0.9700	C27—H27	0.9300
C8—H8B	0.9700	C28—H28	0.9300
C9—C10	1.379 (7)

O2—Sn1—C1	114.2 (2)	C10—C9—C8	124.6 (5)
O2—Sn1—O2ⁱ	73.49 (12)	C14—C9—C8	119.6 (5)
C1—Sn1—O2ⁱ	97.25 (19)	C9—C10—C11	123.1 (5)
O2—Sn1—C8	123.37 (17)	C9—C10—Cl3	120.6 (4)
C1—Sn1—C8	122.4 (3)	C11—C10—Cl3	116.3 (5)
O2ⁱ—Sn1—C8	97.54 (16)	C12—C11—C10	119.1 (6)
O2—Sn1—O1	74.51 (12)	C12—C11—H11	120.5
C1—Sn1—O1	100.54 (17)	C10—C11—H11	120.5
O2ⁱ—Sn1—O1	147.55 (11)	C13—C12—C11	119.8 (6)
C8—Sn1—O1	95.50 (17)	C13—C12—H12	120.1
O2—Sn2—C15	114.44 (17)	C11—C12—H12	120.1
O2—Sn2—C22	108.14 (17)	C14—C13—C12	120.9 (6)
C15—Sn2—C22	131.7 (2)	C14—C13—H13	119.6
O2—Sn2—O1	72.21 (11)	C12—C13—H13	119.6
C15—Sn2—O1	85.91 (16)	C13—C14—C9	121.3 (6)
C22—Sn2—O1	86.30 (16)	C13—C14—H14	119.4
O2—Sn2—Cl1	90.33 (9)	C9—C14—H14	119.4
C15—Sn2—Cl1	102.16 (15)	C16—C15—Sn2	118.8 (3)
C22—Sn2—Cl1	99.22 (15)	C16—C15—H15A	107.6
O1—Sn2—Cl1	162.53 (9)	Sn2—C15—H15A	107.6
C3—Cl2—H3A	3.0	C16—C15—H15B	107.6
C7—Cl2'—H7A	15.7	Sn2—C15—H15B	107.6
Sn1—O1—Sn2	100.13 (13)	H15A—C15—H15B	107.0
Sn1—O1—H1	120.9	C17—C16—C21	115.9 (5)
Sn2—O1—H1	137.0	C17—C16—C15	124.1 (5)
Sn2—O2—Sn1	112.76 (14)	C21—C16—C15	119.9 (5)
Sn2—O2—Sn1ⁱ	139.33 (14)	C16—C17—C18	123.0 (6)
Sn1—O2—Sn1ⁱ	106.51 (12)	C16—C17—Cl4	119.2 (4)
C2—C1—Sn1	114.9 (3)	C18—C17—Cl4	117.8 (5)
C2—C1—H1A	108.5	C19—C18—C17	119.4 (6)
Sn1—C1—H1A	108.5	C19—C18—H18	120.3
C2—C1—H1B	108.5	C17—C18—H18	120.3
Sn1—C1—H1B	108.5	C18—C19—C20	119.8 (6)
H1A—C1—H1B	107.5	C18—C19—H19	120.1
C7—C2—C3	115.8 (5)	C20—C19—H19	120.1
C7—C2—C1	122.3 (6)	C21—C20—C19	119.8 (6)
C3—C2—C1	121.9 (6)	C21—C20—H20	120.1
C4—C3—C2	122.6 (6)	C19—C20—H20	120.1
C4—C3—Cl2	121.9 (6)	C20—C21—C16	122.0 (6)
C2—C3—Cl2	115.4 (5)	C20—C21—H21	119.0
C4—C3—H3A	119.9	C16—C21—H21	119.0
C2—C3—H3A	117.5	C23—C22—Sn2	118.1 (3)
Cl2—C3—H3A	2.4	C23—C22—H22A	107.8
C5—C4—C3	119.1 (6)	Sn2—C22—H22A	107.8
C5—C4—H4	120.5	C23—C22—H22B	107.8
C3—C4—H4	120.5	Sn2—C22—H22B	107.8
C6—C5—C4	119.7 (6)	H22A—C22—H22B	107.1
C6—C5—H5	120.2	C24—C23—C28	115.7 (5)
C4—C5—H5	120.2	C24—C23—C22	122.7 (5)
C5—C6—C7	120.7 (7)	C28—C23—C22	121.5 (5)
C5—C6—H6	119.7	C25—C24—C23	123.7 (5)
C7—C6—H6	119.7	C25—C24—Cl5	118.1 (4)
C6—C7—C2	122.1 (7)	C23—C24—Cl5	118.1 (4)
C6—C7—Cl2'	130.8 (7)	C24—C25—C26	118.6 (5)
C2—C7—Cl2'	107.1 (5)	C24—C25—H25	120.7
C6—C7—H7A	119.0	C26—C25—H25	120.7
C2—C7—H7A	119.0	C27—C26—C25	120.4 (5)
Cl2'—C7—H7A	12.1	C27—C26—H26	119.8
C9—C8—Sn1	111.3 (3)	C25—C26—H26	119.8
C9—C8—H8A	109.4	C26—C27—C28	119.8 (6)
Sn1—C8—H8A	109.4	C26—C27—H27	120.1
C9—C8—H8B	109.4	C28—C27—H27	120.1
Sn1—C8—H8B	109.4	C23—C28—C27	121.7 (6)
H8A—C8—H8B	108.0	C23—C28—H28	119.2
C10—C9—C14	115.9 (5)	C27—C28—H28	119.2

O2—Sn1—O1—Sn2	4.51 (11)	Sn1—C8—C9—C10	100.7 (5)
C1—Sn1—O1—Sn2	116.9 (2)	Sn1—C8—C9—C14	−77.6 (5)
O2ⁱ—Sn1—O1—Sn2	−5.2 (3)	C14—C9—C10—C11	1.2 (8)
C8—Sn1—O1—Sn2	−118.63 (17)	C8—C9—C10—C11	−177.1 (5)
O2—Sn2—O1—Sn1	−4.61 (11)	C14—C9—C10—Cl3	−176.6 (4)
C15—Sn2—O1—Sn1	−121.91 (19)	C8—C9—C10—Cl3	5.0 (7)
C22—Sn2—O1—Sn1	105.78 (19)	C9—C10—C11—C12	−0.5 (9)
Cl1—Sn2—O1—Sn1	−3.5 (4)	Cl3—C10—C11—C12	177.4 (5)
C15—Sn2—O2—Sn1	82.0 (2)	C10—C11—C12—C13	−1.2 (10)
C22—Sn2—O2—Sn1	−74.7 (2)	C11—C12—C13—C14	2.0 (11)
O1—Sn2—O2—Sn1	5.17 (13)	C12—C13—C14—C9	−1.3 (10)
Cl1—Sn2—O2—Sn1	−174.49 (13)	C10—C9—C14—C13	−0.3 (8)
C15—Sn2—O2—Sn1ⁱ	−114.1 (3)	C8—C9—C14—C13	178.1 (6)
C22—Sn2—O2—Sn1ⁱ	89.3 (3)	O2—Sn2—C15—C16	118.1 (4)
O1—Sn2—O2—Sn1ⁱ	169.1 (3)	C22—Sn2—C15—C16	−92.2 (5)
Cl1—Sn2—O2—Sn1ⁱ	−10.5 (2)	O1—Sn2—C15—C16	−173.6 (4)
C1—Sn1—O2—Sn2	−100.2 (2)	Cl1—Sn2—C15—C16	22.1 (5)
O2ⁱ—Sn1—O2—Sn2	169.2 (2)	Sn2—C15—C16—C17	−83.9 (6)
C8—Sn1—O2—Sn2	81.0 (2)	Sn2—C15—C16—C21	98.5 (5)
O1—Sn1—O2—Sn2	−5.41 (13)	C21—C16—C17—C18	−2.0 (8)
C1—Sn1—O2—Sn1ⁱ	90.6 (2)	C15—C16—C17—C18	−179.7 (5)
O2ⁱ—Sn1—O2—Sn1ⁱ	0.000 (1)	C21—C16—C17—Cl4	176.0 (4)
C8—Sn1—O2—Sn1ⁱ	−88.2 (2)	C15—C16—C17—Cl4	−1.6 (7)
O1—Sn1—O2—Sn1ⁱ	−174.57 (16)	C16—C17—C18—C19	1.9 (9)
O2—Sn1—C1—C2	55.6 (6)	Cl4—C17—C18—C19	−176.2 (5)
O2ⁱ—Sn1—C1—C2	130.8 (5)	C17—C18—C19—C20	−0.2 (10)
C8—Sn1—C1—C2	−125.5 (5)	C18—C19—C20—C21	−1.1 (10)
O1—Sn1—C1—C2	−22.0 (6)	C19—C20—C21—C16	0.9 (9)
Sn1—C1—C2—C7	−94.6 (6)	C17—C16—C21—C20	0.6 (8)
Sn1—C1—C2—C3	85.5 (6)	C15—C16—C21—C20	178.4 (5)
C7—C2—C3—C4	−1.9 (8)	O2—Sn2—C22—C23	−116.2 (4)
C1—C2—C3—C4	178.0 (5)	C15—Sn2—C22—C23	92.7 (5)
C7—C2—C3—Cl2	176.7 (4)	O1—Sn2—C22—C23	173.9 (4)
C1—C2—C3—Cl2	−3.4 (7)	Cl1—Sn2—C22—C23	−22.8 (4)
C2—C3—C4—C5	1.3 (9)	Sn2—C22—C23—C24	−74.9 (6)
Cl2—C3—C4—C5	−177.2 (5)	Sn2—C22—C23—C28	107.0 (5)
C3—C4—C5—C6	0.7 (9)	C28—C23—C24—C25	0.8 (8)
C4—C5—C6—C7	−2.0 (10)	C22—C23—C24—C25	−177.4 (5)
C5—C6—C7—C2	1.3 (9)	C28—C23—C24—Cl5	−178.4 (4)
C5—C6—C7—Cl2'	177.9 (6)	C22—C23—C24—Cl5	3.5 (7)
C3—C2—C7—C6	0.6 (8)	C23—C24—C25—C26	0.2 (9)
C1—C2—C7—C6	−179.3 (5)	Cl5—C24—C25—C26	179.3 (4)
C3—C2—C7—Cl2'	−176.7 (4)	C24—C25—C26—C27	−0.8 (9)
C1—C2—C7—Cl2'	3.3 (7)	C25—C26—C27—C28	0.3 (10)
O2—Sn1—C8—C9	−131.3 (3)	C24—C23—C28—C27	−1.3 (8)
C1—Sn1—C8—C9	50.0 (5)	C22—C23—C28—C27	176.9 (5)
O2ⁱ—Sn1—C8—C9	153.6 (4)	C26—C27—C28—C23	0.7 (10)
O1—Sn1—C8—C9	−56.2 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2	0.86	2.80	3.386 (4)	127

Experimental details

Crystal data
Chemical formula	[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]
M_r	1616.22
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.986 (2), 11.227 (2), 13.573 (3)
α, β, γ (°)	74.656 (2), 67.942 (2), 75.753 (2)
V (Å³)	1475.9 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.44 × 0.37 × 0.33

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.449, 0.535
No. of measured, independent and observed [I > 2σ(I)] reflections	7669, 5112, 3865
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.074, 1.04
No. of reflections	5112
No. of parameters	338
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.27, −0.57

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Sn1—O1	2.148 (3)	Sn2—O1	2.276 (3)
Sn1—O2	2.050 (3)	Sn2—O2	2.025 (3)
Sn1—O2ⁱ	2.146 (3)	Sn2—C15	2.147 (5)
Sn1—C1	2.126 (5)	Sn2—C22	2.149 (5)
Sn1—C8	2.146 (5)	Sn2—Cl1	2.4376 (13)

O2—Sn1—O1—Sn2	4.51 (11)	O2ⁱ—Sn1—O2—Sn2	169.2 (2)
O1—Sn2—O2—Sn1	5.17 (13)	O1—Sn1—O2—Sn2	−5.41 (13)
Cl1—Sn2—O2—Sn1	−174.49 (13)	O2ⁱ—Sn1—O2—Sn1ⁱ	0.000 (1)
O1—Sn2—O2—Sn1ⁱ	169.1 (3)	O1—Sn1—O2—Sn1ⁱ	−174.57 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2	0.86	2.80	3.386 (4)	127.4

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province, China (Y2008B48) for financial support.

References

Li, G., Yin, H. & Wang, D. (2006). Acta Cryst. E62, m366–m368. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m593. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar