metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Davies, A. G., Gielen, M., Pannell, K. H. & Tiekink, E. R. T. (2008). Tin Chemistry: Fundamentals, Frontiers, and Applications. Chichester: John Wiley & Sons.]); Tian et al. (2005[Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646-1652.]). For related structures, see: Baul et al. (2001[Baul, T. S. B., Dhar, S., Pyke, S. M., Tiekink, E. R. T., Rivarola, E., Butcher, R. & Smith, F. E. (2001). J. Organomet. Chem. 633, 7-17.]); Rauf et al. (2008[Rauf, M. K., Saeed, M. A., Din, I.-u., Bolte, M., Badshah, A. & Mirza, B. (2008). J. Organomet. Chem. 693, 3043-3048.]); Smith et al. (1986[Smith, P. J., Day, R. O., Chandrasekhar, V., Holmes, J. M. & Holmes, R. R. (1986). Inorg. Chem. 25, 2495-2499.]); Song et al. (2002[Song, X., Cahill, C. & Eng, G. (2002). Main Group Met. Chem. 25, 703-708.]); Wang et al. (2007[Wang, H., Yin, H. & Wang, D. (2007). Acta Cryst. E63, m2955.]); Willem et al. (1998[Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Baul, T. S. B. & Tiekink, E. R. T. (1998). Organometallics, 17, 5758-5766.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H11)3(C7H3Br2O3)]

  • Mr = 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[Bruker (2002). SADABS, SAINT, SMART and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.506, Tmax = 0.694

  • 19711 measured reflections

  • 5000 independent reflections

  • 3416 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 1.18 e Å−3

  • Δρmin = −0.93 e Å−3

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SAINT, SMART and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SAINT, SMART and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Bruker, 2002[Bruker (2002). SADABS, SAINT, SMART and XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


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%.

Refinement top

The bonds C15—C16 and C16—C17 were restrained to 1.52 Å. Atoms C3, C9 and C17 were also restrained to be approximately isotropic using the ISOR instruction in SHELXL97 (Sheldrick, 2008). H atoms were placed in calculated positions (C—H = 0.93–0.98 Å and O—H = 0.82 Å) and refined as riding to their carrier atoms with Uiso(H) = 1.2Ueq(carrier C) and Uiso(H3) = 1.5Ueq(O3).

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
[Figure 1] 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
Mr = 663.05Dx = 1.637 Mg m3
Monoclinic, P21/cMelting point: 392 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.4912 (13) ÅCell parameters from 3561 reflections
b = 17.640 (2) Åθ = 2.4–21.4°
c = 18.0655 (18) ŵ = 3.94 mm1
β = 117.200 (5)°T = 295 K
V = 2690.1 (5) Å3Block, colourless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
5000 independent reflections
Radiation source: fine-focus sealed tube3416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω and ϕ scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1111
Tmin = 0.506, Tmax = 0.694k = 2121
19711 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0654P)2 + 2.5252P]
where P = (Fo2 + 2Fc2)/3
5000 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 1.18 e Å3
20 restraintsΔρmin = 0.93 e Å3
0 constraints
Crystal data top
[Sn(C6H11)3(C7H3Br2O3)]V = 2690.1 (5) Å3
Mr = 663.05Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.4912 (13) ŵ = 3.94 mm1
b = 17.640 (2) ÅT = 295 K
c = 18.0655 (18) Å0.20 × 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)
Tmin = 0.506, Tmax = 0.694Rint = 0.050
19711 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04820 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.03Δρmax = 1.18 e Å3
5000 reflectionsΔρmin = 0.93 e Å3
280 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.02284 (5)0.03487 (2)0.17370 (2)0.05127 (16)
Br10.05150 (12)0.16443 (5)0.55475 (5)0.0916 (3)
Br20.41868 (12)0.10396 (7)0.46748 (6)0.1157 (4)
O10.2363 (6)0.0418 (3)0.2289 (3)0.0745 (13)
O20.0590 (5)0.0504 (2)0.2783 (2)0.0581 (11)
O30.3647 (6)0.0922 (3)0.3169 (3)0.0827 (15)
H30.34680.08970.27670.124*
C10.2443 (7)0.0635 (4)0.0695 (3)0.0531 (14)
H10.31990.02340.06400.064*
C20.3114 (9)0.1376 (4)0.0826 (5)0.088 (2)
H2A0.33200.13300.13030.105*
H2B0.23450.17790.09400.105*
C30.4648 (11)0.1577 (5)0.0055 (6)0.111 (3)
H3A0.49610.20860.01180.134*
H3B0.54760.12340.00180.134*
C40.4523 (11)0.1535 (6)0.0729 (6)0.112 (3)
H4A0.55650.16140.11920.135*
H4B0.38430.19430.07370.135*
C50.3877 (9)0.0797 (6)0.0853 (5)0.095 (3)
H5A0.37370.08180.13520.113*
H5B0.46080.03880.09150.113*
C60.2316 (9)0.0658 (5)0.0107 (4)0.086 (2)
H6A0.18870.01800.01770.103*
H6B0.15820.10550.00710.103*
C70.0607 (8)0.0785 (3)0.1761 (4)0.0616 (17)
H70.13600.07500.15310.074*
C80.0656 (9)0.1329 (4)0.1204 (5)0.081 (2)
H8A0.15120.13340.13570.097*
H8B0.10830.11570.06320.097*
C90.0006 (12)0.2130 (5)0.1271 (6)0.105 (3)
H9A0.06680.21460.09980.126*
H9B0.08830.24750.09780.126*
C100.0909 (11)0.2395 (4)0.2135 (6)0.100 (3)
H10A0.02000.24560.23830.120*
H10B0.13620.28880.21330.120*
C110.2194 (11)0.1868 (4)0.2650 (6)0.099 (3)
H11A0.27200.20510.32190.118*
H11B0.29710.18480.24410.118*
C120.1548 (9)0.1075 (4)0.2636 (4)0.079 (2)
H12A0.24220.07320.29420.095*
H12B0.08770.10840.29110.095*
C130.1573 (8)0.1191 (4)0.2083 (4)0.0667 (18)
H130.11410.16650.21780.080*
C140.3015 (12)0.0985 (6)0.2890 (6)0.128 (4)
H14A0.34490.05110.28110.154*
H14B0.26850.09040.33190.154*
C150.4288 (14)0.1575 (7)0.3182 (7)0.156 (5)
H15A0.52000.13980.36780.188*
H15B0.39050.20370.33200.188*
C160.4755 (12)0.1732 (8)0.2513 (8)0.162 (5)
H16A0.55120.21460.26890.194*
H16B0.52800.12870.24390.194*
C170.3380 (14)0.1934 (7)0.1690 (8)0.157 (5)
H17A0.29550.24210.17390.189*
H17B0.37520.19830.12730.189*
C180.2065 (12)0.1340 (6)0.1403 (6)0.125 (4)
H18A0.24350.08730.12680.150*
H18B0.11580.15170.09040.150*
C190.1639 (8)0.0060 (4)0.2822 (4)0.0560 (15)
C200.1898 (7)0.0157 (3)0.3567 (3)0.0498 (14)
C210.1200 (7)0.0745 (4)0.4126 (4)0.0539 (15)
H210.05640.10920.40310.065*
C220.1430 (8)0.0821 (4)0.4808 (4)0.0580 (16)
C230.2333 (8)0.0288 (4)0.4974 (4)0.0690 (19)
H230.24590.03290.54540.083*
C240.3028 (8)0.0290 (4)0.4433 (4)0.0684 (19)
C250.2866 (8)0.0358 (4)0.3710 (4)0.0625 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0568 (3)0.0573 (3)0.0429 (2)0.0012 (2)0.0256 (2)0.00025 (19)
Br10.1340 (8)0.0825 (5)0.0670 (5)0.0002 (5)0.0536 (5)0.0160 (4)
Br20.1133 (8)0.1531 (9)0.0973 (7)0.0402 (7)0.0625 (6)0.0059 (6)
O10.079 (3)0.093 (4)0.052 (3)0.026 (3)0.031 (2)0.024 (2)
O20.068 (3)0.068 (3)0.045 (2)0.006 (2)0.031 (2)0.0053 (19)
O30.081 (3)0.101 (4)0.064 (3)0.037 (3)0.031 (3)0.013 (3)
C10.051 (4)0.062 (4)0.042 (3)0.004 (3)0.018 (3)0.001 (3)
C20.073 (5)0.082 (5)0.081 (5)0.016 (4)0.012 (4)0.015 (4)
C30.094 (6)0.108 (6)0.107 (6)0.035 (5)0.024 (5)0.012 (5)
C40.085 (6)0.129 (8)0.081 (6)0.011 (6)0.002 (5)0.046 (6)
C50.066 (5)0.155 (9)0.051 (4)0.007 (5)0.017 (4)0.025 (5)
C60.072 (5)0.135 (7)0.050 (4)0.000 (5)0.029 (4)0.008 (4)
C70.075 (5)0.060 (4)0.064 (4)0.011 (3)0.044 (4)0.005 (3)
C80.085 (5)0.075 (5)0.070 (5)0.008 (4)0.024 (4)0.018 (4)
C90.118 (6)0.085 (5)0.100 (6)0.004 (5)0.040 (5)0.031 (4)
C100.129 (8)0.063 (5)0.108 (7)0.008 (5)0.055 (6)0.004 (5)
C110.110 (7)0.068 (5)0.097 (6)0.016 (5)0.029 (5)0.012 (5)
C120.090 (5)0.058 (4)0.067 (5)0.005 (4)0.017 (4)0.006 (3)
C130.064 (4)0.065 (4)0.080 (5)0.010 (3)0.040 (4)0.006 (4)
C140.113 (7)0.138 (8)0.080 (6)0.068 (7)0.003 (5)0.012 (6)
C150.123 (9)0.152 (11)0.138 (10)0.069 (8)0.011 (8)0.000 (8)
C160.079 (7)0.166 (12)0.223 (15)0.022 (7)0.054 (9)0.046 (10)
C170.151 (7)0.163 (7)0.171 (7)0.039 (6)0.085 (6)0.036 (6)
C180.118 (8)0.169 (10)0.093 (7)0.061 (7)0.051 (6)0.007 (6)
C190.056 (4)0.068 (4)0.044 (4)0.002 (3)0.023 (3)0.002 (3)
C200.048 (3)0.061 (4)0.040 (3)0.005 (3)0.020 (3)0.007 (3)
C210.050 (4)0.062 (4)0.049 (3)0.012 (3)0.023 (3)0.004 (3)
C220.063 (4)0.069 (4)0.042 (3)0.012 (3)0.025 (3)0.001 (3)
C230.065 (4)0.099 (6)0.047 (4)0.014 (4)0.029 (3)0.002 (4)
C240.062 (4)0.096 (5)0.054 (4)0.007 (4)0.032 (3)0.006 (4)
C250.054 (4)0.081 (5)0.050 (4)0.003 (4)0.022 (3)0.003 (3)
Geometric parameters (Å, º) top
Sn1—O22.086 (4)C9—H9B0.9700
Sn1—C132.132 (6)C10—C111.477 (11)
Sn1—C72.144 (6)C10—H10A0.9700
Sn1—C12.144 (6)C10—H10B0.9700
Br1—C221.894 (6)C11—C121.523 (10)
Br2—C241.894 (7)C11—H11A0.9700
O1—C191.227 (7)C11—H11B0.9700
O2—C191.294 (7)C12—H12A0.9700
O3—C251.353 (8)C12—H12B0.9700
O3—H30.8200C13—C141.519 (11)
C1—C61.508 (9)C13—C181.524 (10)
C1—C21.520 (9)C13—H130.9800
C1—H10.9800C14—C151.496 (12)
C2—C31.527 (11)C14—H14A0.9700
C2—H2A0.9700C14—H14B0.9700
C2—H2B0.9700C15—C161.492 (9)
C3—C41.476 (13)C15—H15A0.9700
C3—H3A0.9700C15—H15B0.9700
C3—H3B0.9700C16—C171.506 (9)
C4—C51.499 (13)C16—H16A0.9700
C4—H4A0.9700C16—H16B0.9700
C4—H4B0.9700C17—C181.527 (13)
C5—C61.498 (10)C17—H17A0.9700
C5—H5A0.9700C17—H17B0.9700
C5—H5B0.9700C18—H18A0.9700
C6—H6A0.9700C18—H18B0.9700
C6—H6B0.9700C19—C201.484 (8)
C7—C121.505 (9)C20—C211.387 (8)
C7—C81.506 (9)C20—C251.398 (8)
C7—H70.9800C21—C221.353 (8)
C8—C91.525 (10)C21—H210.9300
C8—H8A0.9700C22—C231.394 (9)
C8—H8B0.9700C23—C241.357 (9)
C9—C101.473 (12)C23—H230.9300
C9—H9A0.9700C24—C251.389 (9)
O2—Sn1—C1394.9 (2)C10—C11—H11A109.4
O2—Sn1—C7108.4 (2)C12—C11—H11A109.4
C13—Sn1—C7113.9 (3)C10—C11—H11B109.4
O2—Sn1—C1105.2 (2)C12—C11—H11B109.4
C13—Sn1—C1115.2 (3)H11A—C11—H11B108.0
C7—Sn1—C1116.2 (2)C7—C12—C11111.8 (6)
C19—O2—Sn1114.8 (4)C7—C12—H12A109.3
C25—O3—H3109.5C11—C12—H12A109.3
C6—C1—C2110.5 (6)C7—C12—H12B109.3
C6—C1—Sn1111.9 (4)C11—C12—H12B109.3
C2—C1—Sn1112.2 (4)H12A—C12—H12B107.9
C6—C1—H1107.3C14—C13—C18109.9 (7)
C2—C1—H1107.3C14—C13—Sn1111.4 (5)
Sn1—C1—H1107.3C18—C13—Sn1112.6 (5)
C1—C2—C3110.4 (6)C14—C13—H13107.6
C1—C2—H2A109.6C18—C13—H13107.6
C3—C2—H2A109.6Sn1—C13—H13107.6
C1—C2—H2B109.6C15—C14—C13113.6 (8)
C3—C2—H2B109.6C15—C14—H14A108.8
H2A—C2—H2B108.1C13—C14—H14A108.8
C4—C3—C2113.8 (8)C15—C14—H14B108.8
C4—C3—H3A108.8C13—C14—H14B108.8
C2—C3—H3A108.8H14A—C14—H14B107.7
C4—C3—H3B108.8C16—C15—C14109.5 (9)
C2—C3—H3B108.8C16—C15—H15A109.8
H3A—C3—H3B107.7C14—C15—H15A109.8
C3—C4—C5113.8 (7)C16—C15—H15B109.8
C3—C4—H4A108.8C14—C15—H15B109.8
C5—C4—H4A108.8H15A—C15—H15B108.2
C3—C4—H4B108.8C15—C16—C17113.5 (9)
C5—C4—H4B108.8C15—C16—H16A108.9
H4A—C4—H4B107.7C17—C16—H16A108.9
C6—C5—C4108.2 (8)C15—C16—H16B108.9
C6—C5—H5A110.1C17—C16—H16B108.9
C4—C5—H5A110.1H16A—C16—H16B107.7
C6—C5—H5B110.1C16—C17—C18112.2 (9)
C4—C5—H5B110.1C16—C17—H17A109.2
H5A—C5—H5B108.4C18—C17—H17A109.2
C5—C6—C1112.8 (6)C16—C17—H17B109.2
C5—C6—H6A109.0C18—C17—H17B109.2
C1—C6—H6A109.0H17A—C17—H17B107.9
C5—C6—H6B109.0C13—C18—C17110.4 (8)
C1—C6—H6B109.0C13—C18—H18A109.6
H6A—C6—H6B107.8C17—C18—H18A109.6
C12—C7—C8113.2 (6)C13—C18—H18B109.6
C12—C7—Sn1112.0 (4)C17—C18—H18B109.6
C8—C7—Sn1114.0 (5)H18A—C18—H18B108.1
C12—C7—H7105.6O1—C19—O2122.8 (6)
C8—C7—H7105.6O1—C19—C20121.7 (6)
Sn1—C7—H7105.6O2—C19—C20115.5 (6)
C7—C8—C9111.6 (7)C21—C20—C25119.1 (6)
C7—C8—H8A109.3C21—C20—C19121.7 (6)
C9—C8—H8A109.3C25—C20—C19119.2 (6)
C7—C8—H8B109.3C22—C21—C20121.1 (6)
C9—C8—H8B109.3C22—C21—H21119.5
H8A—C8—H8B108.0C20—C21—H21119.5
C10—C9—C8113.6 (7)C21—C22—C23120.0 (6)
C10—C9—H9A108.9C21—C22—Br1120.4 (5)
C8—C9—H9A108.9C23—C22—Br1119.6 (5)
C10—C9—H9B108.9C24—C23—C22119.8 (6)
C8—C9—H9B108.9C24—C23—H23120.1
H9A—C9—H9B107.7C22—C23—H23120.1
C9—C10—C11112.6 (7)C23—C24—C25121.1 (6)
C9—C10—H10A109.1C23—C24—Br2120.1 (5)
C11—C10—H10A109.1C25—C24—Br2118.8 (5)
C9—C10—H10B109.1O3—C25—C24118.9 (6)
C11—C10—H10B109.1O3—C25—C20122.3 (6)
H10A—C10—H10B107.8C24—C25—C20118.8 (6)
C10—C11—C12111.0 (7)
C13—Sn1—O2—C19178.6 (5)O2—Sn1—C13—C18172.8 (6)
C7—Sn1—O2—C1961.4 (5)C7—Sn1—C13—C1874.6 (7)
C1—Sn1—O2—C1963.6 (5)C1—Sn1—C13—C1863.5 (7)
O2—Sn1—C1—C6172.0 (5)C18—C13—C14—C1557.2 (12)
C13—Sn1—C1—C669.0 (6)Sn1—C13—C14—C15177.3 (8)
C7—Sn1—C1—C668.0 (6)C13—C14—C15—C1655.9 (14)
O2—Sn1—C1—C247.2 (5)C14—C15—C16—C1753.6 (15)
C13—Sn1—C1—C255.9 (6)C15—C16—C17—C1853.7 (16)
C7—Sn1—C1—C2167.2 (5)C14—C13—C18—C1753.9 (11)
C6—C1—C2—C351.7 (9)Sn1—C13—C18—C17178.8 (7)
Sn1—C1—C2—C3177.3 (6)C16—C17—C18—C1353.0 (14)
C1—C2—C3—C449.6 (11)Sn1—O2—C19—O10.3 (8)
C2—C3—C4—C552.3 (11)Sn1—O2—C19—C20179.4 (4)
C3—C4—C5—C654.8 (10)O1—C19—C20—C21173.5 (6)
C4—C5—C6—C158.5 (10)O2—C19—C20—C217.4 (8)
C2—C1—C6—C558.7 (9)O1—C19—C20—C256.7 (9)
Sn1—C1—C6—C5175.5 (6)O2—C19—C20—C25172.4 (6)
O2—Sn1—C7—C1230.2 (6)C25—C20—C21—C220.6 (9)
C13—Sn1—C7—C1274.0 (6)C19—C20—C21—C22179.1 (6)
C1—Sn1—C7—C12148.5 (5)C20—C21—C22—C232.4 (9)
O2—Sn1—C7—C899.9 (5)C20—C21—C22—Br1178.2 (4)
C13—Sn1—C7—C8155.9 (5)C21—C22—C23—C242.5 (10)
C1—Sn1—C7—C818.3 (6)Br1—C22—C23—C24178.1 (5)
C12—C7—C8—C948.3 (9)C22—C23—C24—C250.5 (10)
Sn1—C7—C8—C9177.9 (6)C22—C23—C24—Br2177.4 (5)
C7—C8—C9—C1049.3 (11)C23—C24—C25—O3176.7 (6)
C8—C9—C10—C1153.8 (11)Br2—C24—C25—O35.3 (9)
C9—C10—C11—C1255.8 (11)C23—C24—C25—C203.5 (10)
C8—C7—C12—C1151.7 (9)Br2—C24—C25—C20174.5 (5)
Sn1—C7—C12—C11177.7 (6)C21—C20—C25—O3176.7 (6)
C10—C11—C12—C754.6 (10)C19—C20—C25—O33.6 (9)
O2—Sn1—C13—C1463.2 (7)C21—C20—C25—C243.5 (9)
C7—Sn1—C13—C1449.5 (7)C19—C20—C25—C24176.3 (6)
C1—Sn1—C13—C14172.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.821.842.564 (7)147

Experimental details

Crystal data
Chemical formula[Sn(C6H11)3(C7H3Br2O3)]
Mr663.05
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)9.4912 (13), 17.640 (2), 18.0655 (18)
β (°) 117.200 (5)
V3)2690.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)3.94
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.506, 0.694
No. of measured, independent and
observed [I > 2σ(I)] reflections
19711, 5000, 3416
Rint0.050
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.136, 1.03
No. of reflections5000
No. of parameters280
No. of restraints20
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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