Tricyclo­hex­yl(3,5-dibromo-2-hy­droxy­benzoato-κO)tin(IV)

Liu, X.-C.; Jiang, W.-T.; Shan, P.-C.; Ding, W.-C.

doi:10.1107/S1600536811020496

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m883

doi:10.1107/S1600536811020496

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Tricyclohexyl(3,5-dibromo-2-hydroxybenzoato-κO)tin(IV)

Xi-Cheng Liu,^a ^* Wen-Tao Jiang,^a Peng-Cheng Shan ^a and Wen-Chao Ding ^a

^aDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: chemlxc@163.com

(Received 14 April 2011; accepted 28 May 2011; online 11 June 2011)

In the title compound, [Sn(C₆H₁₁)₃(C₇H₃Br₂O₃)], the Sn atom is four-coordinate and possesses a distorted Sn(C₃O) tetrahedral geometry, with Sn—C bond lengths in the range 2.132 (6)–2.144 (6) Å and with Sn—O = 2.086 (4) Å. The uncoordinated carboxylate O atom forms a weak contact with the Sn atom, with an Sn⋯O separation of 2.962 (2) Å.

Related literature

For background information on organotin carboxylate compounds, see: Davies et al. (2008 ); Tian et al. (2005 ). For related structures, see: Baul et al. (2001 ); Rauf et al. (2008 ); Smith et al. (1986 ); Song et al. (2002 ); Wang et al. (2007 ); Willem et al. (1998 ).

Experimental

Crystal data

[Sn(C₆H₁₁)₃(C₇H₃Br₂O₃)]
M_r = 663.05
Monoclinic, P 2₁ /c
a = 9.4912 (13) Å
b = 17.640 (2) Å
c = 18.0655 (18) Å
β = 117.200 (5)°
V = 2690.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.94 mm⁻¹
T = 295 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.506, T_max = 0.694
19711 measured reflections
5000 independent reflections
3416 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.03
5000 reflections
280 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020496/bh2352sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020496/bh2352Isup2.hkl

checkCIF report

Comment top

Organotin carboxylates form an important class of compounds that have been receiving increasing attention, not only because of their structural interest but also owing to their varied applications (Davies et al., 2008; Tian et al., 2005). Several structures of triorganotin 2-hydroxybenzoates, such as (2-hydroxybenzoato)triphenyltin (Rauf et al., 2008), (2-hydroxybenzoato)trimethyltin (Smith et al., 1986), [5-(2-phenyl-1-diazenyl)-2-hydroxybenzoato]triphenyltin (Baul et al., 2001) and (5-bromo-2-hydroxybenzoato)triphenyltin (Wang et al., 2007), have been reported. As a continuation of these studies, the structure of the title compound is here described.

The coordination geometry of the Sn atom is that of a distorted tetrahedron (Fig. 1). The Sn···O1 separation of 2.962 (2) Å indicates there is a weak interaction between these atoms, which distorts the tetrahedral geometry by opening up the C1—Sn1—C7 angle to 116.2 (2)° and reducing the O2—Sn1—C13 angle to 94.9 (2)°. The monodentate mode of coordination of the benzoate group is reflected in the disparate O1—C19 and O2—C19 bond lengths of 1.227 (7) and 1.294 (7) Å, respectively. Bond dimensions around Sn atom are similar to those found in the structures of tricyclohexyltin benzoates such as tricyclohexyl(4-hydroxylbenzoato)tin (Song et al., 2002) and tricyclohexyl[2-(2-(2-hydroxy-5-methylphenyl)-1-diazenyl)benzoato]tin (Willem et al., 1998). An intramolecular O—H···O hydrogen bond is found between the carboxyl O1 atom and the phenolic hydroxy group (Fig. 1, Table 1).

Related literature top

For background information on organotin carboxylate compounds, see: Davies et al. (2008); Tian et al. (2005). For related structures, see: Baul et al. (2001); Rauf et al. (2008); Smith et al. (1986); Song et al. (2002); Wang et al. (2007); Willem et al. (1998).

Experimental top

Tricyclohexyltin hydroxide (1.05 g, 1 mmol) and 2-hydroxy-3,5-dibromobenzoic acid (0.77 g, 2 mmol) in toluene (50 ml) were refluxed for 5 h with azeotropic removal of water via a Dean–Stark trap. The resulting clear solution was evaporated under reduced pressure. The white solid obtained was purified by recrystallization from ethanol, and crystals of the title compound were obtained from a chloroform–hexane (1:1, v/v) solution by slow evaporation at room temperature (yield 74%, m.p. 392–393 K). Analysis, found: C 45.28, H 5.47%; calculated for C₂₅H₃₆Br₂O₃Sn: C 45.18, H 5.33%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Tricyclohexyl(3,5-dibromo-2-hydroxybenzoato-κO)tin(IV) top

Crystal data top

[Sn(C₆H₁₁)₃(C₇H₃Br₂O₃)]	F(000) = 1320
M_r = 663.05	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 392 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4912 (13) Å	Cell parameters from 3561 reflections
b = 17.640 (2) Å	θ = 2.4–21.4°
c = 18.0655 (18) Å	µ = 3.94 mm⁻¹
β = 117.200 (5)°	T = 295 K
V = 2690.1 (5) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	5000 independent reflections
Radiation source: fine-focus sealed tube	3416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω and ϕ scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
T_min = 0.506, T_max = 0.694	k = −21→21
19711 measured reflections	l = −21→21

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0654P)² + 2.5252P] where P = (F_o² + 2F_c²)/3
5000 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 1.18 e Å⁻³
20 restraints	Δρ_min = −0.93 e Å⁻³
0 constraints

Crystal data top

[Sn(C₆H₁₁)₃(C₇H₃Br₂O₃)]	V = 2690.1 (5) Å³
M_r = 663.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4912 (13) Å	µ = 3.94 mm⁻¹
b = 17.640 (2) Å	T = 295 K
c = 18.0655 (18) Å	0.20 × 0.20 × 0.10 mm
β = 117.200 (5)°

Data collection top

Bruker SMART APEX area-detector diffractometer	5000 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3416 reflections with I > 2σ(I)
T_min = 0.506, T_max = 0.694	R_int = 0.050
19711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	20 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	Δρ_max = 1.18 e Å⁻³
5000 reflections	Δρ_min = −0.93 e Å⁻³
280 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	−0.02284 (5)	−0.03487 (2)	0.17370 (2)	0.05127 (16)
Br1	−0.05150 (12)	−0.16443 (5)	0.55475 (5)	0.0916 (3)
Br2	−0.41868 (12)	0.10396 (7)	0.46748 (6)	0.1157 (4)
O1	−0.2363 (6)	0.0418 (3)	0.2289 (3)	0.0745 (13)
O2	−0.0590 (5)	−0.0504 (2)	0.2783 (2)	0.0581 (11)
O3	−0.3647 (6)	0.0922 (3)	0.3169 (3)	0.0827 (15)
H3	−0.3468	0.0897	0.2767	0.124*
C1	−0.2443 (7)	−0.0635 (4)	0.0695 (3)	0.0531 (14)
H1	−0.3199	−0.0234	0.0640	0.064*
C2	−0.3114 (9)	−0.1376 (4)	0.0826 (5)	0.088 (2)
H2A	−0.3320	−0.1330	0.1303	0.105*
H2B	−0.2345	−0.1779	0.0940	0.105*
C3	−0.4648 (11)	−0.1577 (5)	0.0055 (6)	0.111 (3)
H3A	−0.4961	−0.2086	0.0118	0.134*
H3B	−0.5476	−0.1234	0.0018	0.134*
C4	−0.4523 (11)	−0.1535 (6)	−0.0729 (6)	0.112 (3)
H4A	−0.5565	−0.1614	−0.1192	0.135*
H4B	−0.3843	−0.1943	−0.0737	0.135*
C5	−0.3877 (9)	−0.0797 (6)	−0.0853 (5)	0.095 (3)
H5A	−0.3737	−0.0818	−0.1352	0.113*
H5B	−0.4608	−0.0388	−0.0915	0.113*
C6	−0.2316 (9)	−0.0658 (5)	−0.0107 (4)	0.086 (2)
H6A	−0.1887	−0.0180	−0.0177	0.103*
H6B	−0.1582	−0.1055	−0.0071	0.103*
C7	0.0607 (8)	0.0785 (3)	0.1761 (4)	0.0616 (17)
H7	0.1360	0.0750	0.1531	0.074*
C8	−0.0656 (9)	0.1329 (4)	0.1204 (5)	0.081 (2)
H8A	−0.1512	0.1334	0.1357	0.097*
H8B	−0.1083	0.1157	0.0632	0.097*
C9	−0.0006 (12)	0.2130 (5)	0.1271 (6)	0.105 (3)
H9A	0.0668	0.2146	0.0998	0.126*
H9B	−0.0883	0.2475	0.0978	0.126*
C10	0.0909 (11)	0.2395 (4)	0.2135 (6)	0.100 (3)
H10A	0.0200	0.2456	0.2383	0.120*
H10B	0.1362	0.2888	0.2133	0.120*
C11	0.2194 (11)	0.1868 (4)	0.2650 (6)	0.099 (3)
H11A	0.2720	0.2051	0.3219	0.118*
H11B	0.2971	0.1848	0.2441	0.118*
C12	0.1548 (9)	0.1075 (4)	0.2636 (4)	0.079 (2)
H12A	0.2422	0.0732	0.2942	0.095*
H12B	0.0877	0.1084	0.2911	0.095*
C13	0.1573 (8)	−0.1191 (4)	0.2083 (4)	0.0667 (18)
H13	0.1141	−0.1665	0.2178	0.080*
C14	0.3015 (12)	−0.0985 (6)	0.2890 (6)	0.128 (4)
H14A	0.3449	−0.0511	0.2811	0.154*
H14B	0.2685	−0.0904	0.3319	0.154*
C15	0.4288 (14)	−0.1575 (7)	0.3182 (7)	0.156 (5)
H15A	0.5200	−0.1398	0.3678	0.188*
H15B	0.3905	−0.2037	0.3320	0.188*
C16	0.4755 (12)	−0.1732 (8)	0.2513 (8)	0.162 (5)
H16A	0.5512	−0.2146	0.2689	0.194*
H16B	0.5280	−0.1287	0.2439	0.194*
C17	0.3380 (14)	−0.1934 (7)	0.1690 (8)	0.157 (5)
H17A	0.2955	−0.2421	0.1739	0.189*
H17B	0.3752	−0.1983	0.1273	0.189*
C18	0.2065 (12)	−0.1340 (6)	0.1403 (6)	0.125 (4)
H18A	0.2435	−0.0873	0.1268	0.150*
H18B	0.1158	−0.1517	0.0904	0.150*
C19	−0.1639 (8)	−0.0060 (4)	0.2822 (4)	0.0560 (15)
C20	−0.1898 (7)	−0.0157 (3)	0.3567 (3)	0.0498 (14)
C21	−0.1200 (7)	−0.0745 (4)	0.4126 (4)	0.0539 (15)
H21	−0.0564	−0.1092	0.4031	0.065*
C22	−0.1430 (8)	−0.0821 (4)	0.4808 (4)	0.0580 (16)
C23	−0.2333 (8)	−0.0288 (4)	0.4974 (4)	0.0690 (19)
H23	−0.2459	−0.0329	0.5454	0.083*
C24	−0.3028 (8)	0.0290 (4)	0.4433 (4)	0.0684 (19)
C25	−0.2866 (8)	0.0358 (4)	0.3710 (4)	0.0625 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0568 (3)	0.0573 (3)	0.0429 (2)	−0.0012 (2)	0.0256 (2)	0.00025 (19)
Br1	0.1340 (8)	0.0825 (5)	0.0670 (5)	−0.0002 (5)	0.0536 (5)	0.0160 (4)
Br2	0.1133 (8)	0.1531 (9)	0.0973 (7)	0.0402 (7)	0.0625 (6)	−0.0059 (6)
O1	0.079 (3)	0.093 (4)	0.052 (3)	0.026 (3)	0.031 (2)	0.024 (2)
O2	0.068 (3)	0.068 (3)	0.045 (2)	0.006 (2)	0.031 (2)	0.0053 (19)
O3	0.081 (3)	0.101 (4)	0.064 (3)	0.037 (3)	0.031 (3)	0.013 (3)
C1	0.051 (4)	0.062 (4)	0.042 (3)	0.004 (3)	0.018 (3)	0.001 (3)
C2	0.073 (5)	0.082 (5)	0.081 (5)	−0.016 (4)	0.012 (4)	0.015 (4)
C3	0.094 (6)	0.108 (6)	0.107 (6)	−0.035 (5)	0.024 (5)	0.012 (5)
C4	0.085 (6)	0.129 (8)	0.081 (6)	0.011 (6)	0.002 (5)	−0.046 (6)
C5	0.066 (5)	0.155 (9)	0.051 (4)	−0.007 (5)	0.017 (4)	−0.025 (5)
C6	0.072 (5)	0.135 (7)	0.050 (4)	0.000 (5)	0.029 (4)	−0.008 (4)
C7	0.075 (5)	0.060 (4)	0.064 (4)	−0.011 (3)	0.044 (4)	−0.005 (3)
C8	0.085 (5)	0.075 (5)	0.070 (5)	0.008 (4)	0.024 (4)	0.018 (4)
C9	0.118 (6)	0.085 (5)	0.100 (6)	−0.004 (5)	0.040 (5)	0.031 (4)
C10	0.129 (8)	0.063 (5)	0.108 (7)	0.008 (5)	0.055 (6)	0.004 (5)
C11	0.110 (7)	0.068 (5)	0.097 (6)	−0.016 (5)	0.029 (5)	−0.012 (5)
C12	0.090 (5)	0.058 (4)	0.067 (5)	−0.005 (4)	0.017 (4)	−0.006 (3)
C13	0.064 (4)	0.065 (4)	0.080 (5)	0.010 (3)	0.040 (4)	0.006 (4)
C14	0.113 (7)	0.138 (8)	0.080 (6)	0.068 (7)	−0.003 (5)	−0.012 (6)
C15	0.123 (9)	0.152 (11)	0.138 (10)	0.069 (8)	0.011 (8)	0.000 (8)
C16	0.079 (7)	0.166 (12)	0.223 (15)	0.022 (7)	0.054 (9)	−0.046 (10)
C17	0.151 (7)	0.163 (7)	0.171 (7)	0.039 (6)	0.085 (6)	−0.036 (6)
C18	0.118 (8)	0.169 (10)	0.093 (7)	0.061 (7)	0.051 (6)	−0.007 (6)
C19	0.056 (4)	0.068 (4)	0.044 (4)	−0.002 (3)	0.023 (3)	−0.002 (3)
C20	0.048 (3)	0.061 (4)	0.040 (3)	−0.005 (3)	0.020 (3)	−0.007 (3)
C21	0.050 (4)	0.062 (4)	0.049 (3)	−0.012 (3)	0.023 (3)	−0.004 (3)
C22	0.063 (4)	0.069 (4)	0.042 (3)	−0.012 (3)	0.025 (3)	−0.001 (3)
C23	0.065 (4)	0.099 (6)	0.047 (4)	−0.014 (4)	0.029 (3)	−0.002 (4)
C24	0.062 (4)	0.096 (5)	0.054 (4)	0.007 (4)	0.032 (3)	−0.006 (4)
C25	0.054 (4)	0.081 (5)	0.050 (4)	0.003 (4)	0.022 (3)	−0.003 (3)

Geometric parameters (Å, º) top

Sn1—O2	2.086 (4)	C9—H9B	0.9700
Sn1—C13	2.132 (6)	C10—C11	1.477 (11)
Sn1—C7	2.144 (6)	C10—H10A	0.9700
Sn1—C1	2.144 (6)	C10—H10B	0.9700
Br1—C22	1.894 (6)	C11—C12	1.523 (10)
Br2—C24	1.894 (7)	C11—H11A	0.9700
O1—C19	1.227 (7)	C11—H11B	0.9700
O2—C19	1.294 (7)	C12—H12A	0.9700
O3—C25	1.353 (8)	C12—H12B	0.9700
O3—H3	0.8200	C13—C14	1.519 (11)
C1—C6	1.508 (9)	C13—C18	1.524 (10)
C1—C2	1.520 (9)	C13—H13	0.9800
C1—H1	0.9800	C14—C15	1.496 (12)
C2—C3	1.527 (11)	C14—H14A	0.9700
C2—H2A	0.9700	C14—H14B	0.9700
C2—H2B	0.9700	C15—C16	1.492 (9)
C3—C4	1.476 (13)	C15—H15A	0.9700
C3—H3A	0.9700	C15—H15B	0.9700
C3—H3B	0.9700	C16—C17	1.506 (9)
C4—C5	1.499 (13)	C16—H16A	0.9700
C4—H4A	0.9700	C16—H16B	0.9700
C4—H4B	0.9700	C17—C18	1.527 (13)
C5—C6	1.498 (10)	C17—H17A	0.9700
C5—H5A	0.9700	C17—H17B	0.9700
C5—H5B	0.9700	C18—H18A	0.9700
C6—H6A	0.9700	C18—H18B	0.9700
C6—H6B	0.9700	C19—C20	1.484 (8)
C7—C12	1.505 (9)	C20—C21	1.387 (8)
C7—C8	1.506 (9)	C20—C25	1.398 (8)
C7—H7	0.9800	C21—C22	1.353 (8)
C8—C9	1.525 (10)	C21—H21	0.9300
C8—H8A	0.9700	C22—C23	1.394 (9)
C8—H8B	0.9700	C23—C24	1.357 (9)
C9—C10	1.473 (12)	C23—H23	0.9300
C9—H9A	0.9700	C24—C25	1.389 (9)

O2—Sn1—C13	94.9 (2)	C10—C11—H11A	109.4
O2—Sn1—C7	108.4 (2)	C12—C11—H11A	109.4
C13—Sn1—C7	113.9 (3)	C10—C11—H11B	109.4
O2—Sn1—C1	105.2 (2)	C12—C11—H11B	109.4
C13—Sn1—C1	115.2 (3)	H11A—C11—H11B	108.0
C7—Sn1—C1	116.2 (2)	C7—C12—C11	111.8 (6)
C19—O2—Sn1	114.8 (4)	C7—C12—H12A	109.3
C25—O3—H3	109.5	C11—C12—H12A	109.3
C6—C1—C2	110.5 (6)	C7—C12—H12B	109.3
C6—C1—Sn1	111.9 (4)	C11—C12—H12B	109.3
C2—C1—Sn1	112.2 (4)	H12A—C12—H12B	107.9
C6—C1—H1	107.3	C14—C13—C18	109.9 (7)
C2—C1—H1	107.3	C14—C13—Sn1	111.4 (5)
Sn1—C1—H1	107.3	C18—C13—Sn1	112.6 (5)
C1—C2—C3	110.4 (6)	C14—C13—H13	107.6
C1—C2—H2A	109.6	C18—C13—H13	107.6
C3—C2—H2A	109.6	Sn1—C13—H13	107.6
C1—C2—H2B	109.6	C15—C14—C13	113.6 (8)
C3—C2—H2B	109.6	C15—C14—H14A	108.8
H2A—C2—H2B	108.1	C13—C14—H14A	108.8
C4—C3—C2	113.8 (8)	C15—C14—H14B	108.8
C4—C3—H3A	108.8	C13—C14—H14B	108.8
C2—C3—H3A	108.8	H14A—C14—H14B	107.7
C4—C3—H3B	108.8	C16—C15—C14	109.5 (9)
C2—C3—H3B	108.8	C16—C15—H15A	109.8
H3A—C3—H3B	107.7	C14—C15—H15A	109.8
C3—C4—C5	113.8 (7)	C16—C15—H15B	109.8
C3—C4—H4A	108.8	C14—C15—H15B	109.8
C5—C4—H4A	108.8	H15A—C15—H15B	108.2
C3—C4—H4B	108.8	C15—C16—C17	113.5 (9)
C5—C4—H4B	108.8	C15—C16—H16A	108.9
H4A—C4—H4B	107.7	C17—C16—H16A	108.9
C6—C5—C4	108.2 (8)	C15—C16—H16B	108.9
C6—C5—H5A	110.1	C17—C16—H16B	108.9
C4—C5—H5A	110.1	H16A—C16—H16B	107.7
C6—C5—H5B	110.1	C16—C17—C18	112.2 (9)
C4—C5—H5B	110.1	C16—C17—H17A	109.2
H5A—C5—H5B	108.4	C18—C17—H17A	109.2
C5—C6—C1	112.8 (6)	C16—C17—H17B	109.2
C5—C6—H6A	109.0	C18—C17—H17B	109.2
C1—C6—H6A	109.0	H17A—C17—H17B	107.9
C5—C6—H6B	109.0	C13—C18—C17	110.4 (8)
C1—C6—H6B	109.0	C13—C18—H18A	109.6
H6A—C6—H6B	107.8	C17—C18—H18A	109.6
C12—C7—C8	113.2 (6)	C13—C18—H18B	109.6
C12—C7—Sn1	112.0 (4)	C17—C18—H18B	109.6
C8—C7—Sn1	114.0 (5)	H18A—C18—H18B	108.1
C12—C7—H7	105.6	O1—C19—O2	122.8 (6)
C8—C7—H7	105.6	O1—C19—C20	121.7 (6)
Sn1—C7—H7	105.6	O2—C19—C20	115.5 (6)
C7—C8—C9	111.6 (7)	C21—C20—C25	119.1 (6)
C7—C8—H8A	109.3	C21—C20—C19	121.7 (6)
C9—C8—H8A	109.3	C25—C20—C19	119.2 (6)
C7—C8—H8B	109.3	C22—C21—C20	121.1 (6)
C9—C8—H8B	109.3	C22—C21—H21	119.5
H8A—C8—H8B	108.0	C20—C21—H21	119.5
C10—C9—C8	113.6 (7)	C21—C22—C23	120.0 (6)
C10—C9—H9A	108.9	C21—C22—Br1	120.4 (5)
C8—C9—H9A	108.9	C23—C22—Br1	119.6 (5)
C10—C9—H9B	108.9	C24—C23—C22	119.8 (6)
C8—C9—H9B	108.9	C24—C23—H23	120.1
H9A—C9—H9B	107.7	C22—C23—H23	120.1
C9—C10—C11	112.6 (7)	C23—C24—C25	121.1 (6)
C9—C10—H10A	109.1	C23—C24—Br2	120.1 (5)
C11—C10—H10A	109.1	C25—C24—Br2	118.8 (5)
C9—C10—H10B	109.1	O3—C25—C24	118.9 (6)
C11—C10—H10B	109.1	O3—C25—C20	122.3 (6)
H10A—C10—H10B	107.8	C24—C25—C20	118.8 (6)
C10—C11—C12	111.0 (7)

C13—Sn1—O2—C19	178.6 (5)	O2—Sn1—C13—C18	172.8 (6)
C7—Sn1—O2—C19	61.4 (5)	C7—Sn1—C13—C18	−74.6 (7)
C1—Sn1—O2—C19	−63.6 (5)	C1—Sn1—C13—C18	63.5 (7)
O2—Sn1—C1—C6	−172.0 (5)	C18—C13—C14—C15	−57.2 (12)
C13—Sn1—C1—C6	−69.0 (6)	Sn1—C13—C14—C15	177.3 (8)
C7—Sn1—C1—C6	68.0 (6)	C13—C14—C15—C16	55.9 (14)
O2—Sn1—C1—C2	−47.2 (5)	C14—C15—C16—C17	−53.6 (15)
C13—Sn1—C1—C2	55.9 (6)	C15—C16—C17—C18	53.7 (16)
C7—Sn1—C1—C2	−167.2 (5)	C14—C13—C18—C17	53.9 (11)
C6—C1—C2—C3	−51.7 (9)	Sn1—C13—C18—C17	178.8 (7)
Sn1—C1—C2—C3	−177.3 (6)	C16—C17—C18—C13	−53.0 (14)
C1—C2—C3—C4	49.6 (11)	Sn1—O2—C19—O1	−0.3 (8)
C2—C3—C4—C5	−52.3 (11)	Sn1—O2—C19—C20	−179.4 (4)
C3—C4—C5—C6	54.8 (10)	O1—C19—C20—C21	173.5 (6)
C4—C5—C6—C1	−58.5 (10)	O2—C19—C20—C21	−7.4 (8)
C2—C1—C6—C5	58.7 (9)	O1—C19—C20—C25	−6.7 (9)
Sn1—C1—C6—C5	−175.5 (6)	O2—C19—C20—C25	172.4 (6)
O2—Sn1—C7—C12	30.2 (6)	C25—C20—C21—C22	−0.6 (9)
C13—Sn1—C7—C12	−74.0 (6)	C19—C20—C21—C22	179.1 (6)
C1—Sn1—C7—C12	148.5 (5)	C20—C21—C22—C23	−2.4 (9)
O2—Sn1—C7—C8	−99.9 (5)	C20—C21—C22—Br1	178.2 (4)
C13—Sn1—C7—C8	155.9 (5)	C21—C22—C23—C24	2.5 (10)
C1—Sn1—C7—C8	18.3 (6)	Br1—C22—C23—C24	−178.1 (5)
C12—C7—C8—C9	48.3 (9)	C22—C23—C24—C25	0.5 (10)
Sn1—C7—C8—C9	177.9 (6)	C22—C23—C24—Br2	−177.4 (5)
C7—C8—C9—C10	−49.3 (11)	C23—C24—C25—O3	176.7 (6)
C8—C9—C10—C11	53.8 (11)	Br2—C24—C25—O3	−5.3 (9)
C9—C10—C11—C12	−55.8 (11)	C23—C24—C25—C20	−3.5 (10)
C8—C7—C12—C11	−51.7 (9)	Br2—C24—C25—C20	174.5 (5)
Sn1—C7—C12—C11	177.7 (6)	C21—C20—C25—O3	−176.7 (6)
C10—C11—C12—C7	54.6 (10)	C19—C20—C25—O3	3.6 (9)
O2—Sn1—C13—C14	−63.2 (7)	C21—C20—C25—C24	3.5 (9)
C7—Sn1—C13—C14	49.5 (7)	C19—C20—C25—C24	−176.3 (6)
C1—Sn1—C13—C14	−172.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.84	2.564 (7)	147

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₁₁)₃(C₇H₃Br₂O₃)]
M_r	663.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	9.4912 (13), 17.640 (2), 18.0655 (18)
β (°)	117.200 (5)
V (Å³)	2690.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.94
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.506, 0.694
No. of measured, independent and observed [I > 2σ(I)] reflections	19711, 5000, 3416
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.136, 1.03
No. of reflections	5000
No. of parameters	280
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.93

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 2002).

Acknowledgements

This work was supported by the Shandong Provincial Natural Science Foundation, China (grant No. ZR2010BL012).

References

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