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Acta Cryst. (2007). E63, m2955    [ doi:10.1107/S1600536807055249 ]

(5-Bromosalicylato)triphenyltin(IV)

H. Wang, H. Yin and D. Wang

Abstract top

The title compound, [Sn(C6H5)3(C7H4BrO3)], crystallizes with two independent molecules in the asymmetric unit, the molecular conformations of which are almost identical. In each molecule, the Sn atom is coordinated by one O and three C atoms in a distorted tetrahedral geometry [Sn-O = 2.045 (4) and 2.087 (4) Å; Sn-C = 2.082 (7)-2.117 (7)Å]. The hydroxy groups are involved in intramolecular O-H...O hydrogen bonds.

Comment top

Organotin esters of carboxylic acids are widely used as biocides, as fungicides and in industry as homogeneous catalysts. We have therefore synthesized the title compound, (I), and present its crystal structure here.

In (I) (Fig. 1), the tin atoms are four-coordinated by the three C atoms from phenyls and the oxygen atom of the monodentate carboxyl group. Thus, the geometry of the tin centers displays a distorted tetrahedral coordinated sphere with six angles ranging from 95.2 (2) ° to 125.0 (3) °. The Sn1—O1 distance of 2.045 (4) Å is close to the reported values for triorganotin carboxylates (Ma et al., 2006).

Related literature top

A series of new triorganotin(IV) pyridinedicarboxylates has been synthesized by the reaction of trimethyltin(IV), triphenyltin(IV) or tribenzyltin(IV) chloride with 2,6(3,5 or 2,5)-H2pdc (pdc = pyridinedicarboxylate), see: Ma et al. (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. 5-Bromosalicylic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of benzene in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1) (yield 80%; m.p. 427 K). Analysis, calculated (%) for C25H19BrO3Sn (Mr = 566.00): C, 53.05; H, 3.39. found: C, 53.36; H, 3.23.

Refinement top

H atoms were positioned geometrically, with O—H =0.82 Å and C—H = 0.93 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,O) The residual peak of 1.49 e Å3 situated 0.45 Å at atom Br2.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit of (I), with atomic numbering and 50% probability displacement ellipsoids for non-H atoms.
(5-Bromosalicylato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C7H4BrO3)]Z = 4
Mr = 566.00F000 = 1112
Triclinic, P1Dx = 1.644 Mg m−3
a = 11.434 (7) ÅMo Kα radiation
λ = 0.71073 Å
b = 14.233 (9) ÅCell parameters from 2851 reflections
c = 15.453 (10) Åθ = 2.4–22.2º
α = 113.920 (7)ºµ = 2.89 mm−1
β = 92.418 (8)ºT = 298 (2) K
γ = 93.818 (9)ºBlock, colourless
V = 2287 (3) Å30.52 × 0.47 × 0.41 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		7898 independent reflections
Radiation source: fine-focus sealed tube4460 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 298(2) Kθmax = 25.0º
phi and ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→13
Tmin = 0.315, Tmax = 0.384k = −16→16
11810 measured reflectionsl = −18→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
7898 reflectionsΔρmax = 1.49 e Å−3
541 parametersΔρmin = −1.08 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sn(C6H5)3(C7H4BrO3)]γ = 93.818 (9)º
Mr = 566.00V = 2287 (3) Å3
Triclinic, P1Z = 4
a = 11.434 (7) ÅMo Kα
b = 14.233 (9) ŵ = 2.89 mm−1
c = 15.453 (10) ÅT = 298 (2) K
α = 113.920 (7)º0.52 × 0.47 × 0.41 mm
β = 92.418 (8)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		7898 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4460 reflections with I > 2σ(I)
Tmin = 0.315, Tmax = 0.384Rint = 0.042
11810 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.104H-atom parameters constrained
S = 1.00Δρmax = 1.49 e Å−3
7898 reflectionsΔρmin = −1.08 e Å−3
541 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.73602 (4)0.56543 (3)0.32221 (3)0.04496 (16)
Sn20.84682 (4)0.90686 (4)0.12077 (3)0.04421 (16)
O10.7057 (4)0.5070 (3)0.1778 (3)0.0520 (12)
O20.6858 (4)0.6686 (4)0.1996 (3)0.0572 (13)
O30.6488 (4)0.7113 (3)0.0540 (3)0.0632 (14)
H30.65990.72390.11050.095*
O40.9747 (4)1.0319 (3)0.1780 (3)0.0536 (13)
O51.0545 (4)0.9425 (4)0.2486 (4)0.0734 (16)
O61.2595 (6)1.0097 (6)0.3379 (5)0.122 (3)
H61.20340.96750.31050.183*
Br10.63956 (9)0.25806 (6)−0.18809 (6)0.0788 (3)
Br21.19838 (15)1.41108 (11)0.30941 (9)0.1746 (7)
C10.6843 (6)0.5753 (6)0.1463 (5)0.0467 (18)
C20.6638 (5)0.5393 (5)0.0428 (5)0.0411 (17)
C30.6493 (6)0.6095 (6)0.0026 (5)0.0518 (19)
C40.6349 (7)0.5739 (6)−0.0959 (6)0.066 (2)
H40.62810.6204−0.12380.079*
C50.6308 (7)0.4693 (6)−0.1519 (5)0.064 (2)
H50.61940.4453−0.21760.077*
C60.6433 (6)0.4013 (5)−0.1114 (5)0.0469 (18)
C70.6595 (5)0.4357 (5)−0.0149 (5)0.0478 (18)
H70.66770.38860.01200.057*
C80.7657 (6)0.4229 (5)0.3271 (5)0.0499 (19)
C90.7073 (8)0.3321 (6)0.2696 (6)0.089 (3)
H90.64960.33150.22510.107*
C100.7293 (12)0.2403 (6)0.2739 (7)0.123 (4)
H100.68700.17900.23320.148*
C110.8125 (11)0.2406 (8)0.3374 (8)0.102 (4)
H110.82680.17900.34170.122*
C120.8754 (8)0.3279 (8)0.3948 (8)0.095 (3)
H120.93480.32650.43700.114*
C130.8525 (7)0.4185 (6)0.3914 (6)0.070 (2)
H130.89550.47910.43270.084*
C140.5805 (6)0.6271 (5)0.3818 (4)0.0397 (17)
C150.5098 (7)0.5749 (5)0.4219 (5)0.054 (2)
H150.52900.51200.42070.064*
C160.4100 (7)0.6182 (7)0.4639 (5)0.070 (2)
H160.36250.58430.49170.084*
C170.3814 (7)0.7104 (8)0.4645 (5)0.072 (2)
H170.31450.73890.49250.086*
C180.4490 (7)0.7589 (6)0.4251 (5)0.061 (2)
H180.42850.82110.42540.073*
C190.5483 (6)0.7192 (5)0.3841 (5)0.0512 (19)
H190.59470.75510.35740.061*
C200.8909 (6)0.6673 (6)0.3631 (5)0.0533 (19)
C210.9877 (8)0.6457 (7)0.3116 (6)0.079 (3)
H210.98420.58520.25660.095*
C221.0898 (8)0.7106 (9)0.3383 (7)0.099 (3)
H221.15560.69240.30380.118*
C231.0931 (8)0.8006 (8)0.4151 (8)0.083 (3)
H231.16020.84670.43090.099*
C241.0017 (9)0.8253 (7)0.4694 (7)0.084 (3)
H241.00720.88650.52390.101*
C250.8973 (7)0.7585 (6)0.4437 (6)0.067 (2)
H250.83340.77560.48060.080*
C261.0539 (6)1.0204 (7)0.2325 (5)0.056 (2)
C271.1469 (6)1.1072 (7)0.2778 (5)0.062 (2)
C281.2458 (8)1.0956 (9)0.3280 (6)0.085 (3)
C291.3333 (12)1.1784 (11)0.3673 (9)0.129 (6)
H291.40111.17180.39900.155*
C301.3190 (12)1.2661 (13)0.3590 (9)0.144 (7)
H301.37821.32000.38540.173*
C311.2216 (10)1.2814 (8)0.3137 (6)0.107 (4)
C321.1341 (7)1.2010 (7)0.2719 (5)0.074 (3)
H321.06761.20960.24020.089*
C330.7522 (6)0.9299 (5)0.2414 (5)0.0499 (19)
C340.8015 (7)0.9261 (5)0.3224 (5)0.062 (2)
H340.87730.90620.32300.075*
C350.7407 (10)0.9510 (6)0.4028 (6)0.082 (3)
H350.77620.94970.45750.098*
C360.6303 (11)0.9772 (7)0.4019 (8)0.097 (4)
H360.58980.99440.45640.116*
C370.5765 (9)0.9790 (7)0.3219 (9)0.104 (4)
H370.49900.99490.32110.124*
C380.6395 (7)0.9566 (6)0.2412 (6)0.072 (2)
H380.60460.96000.18720.087*
C390.7617 (6)0.9608 (5)0.0278 (4)0.0469 (18)
C400.6655 (8)0.9063 (7)−0.0313 (6)0.087 (3)
H400.63580.8444−0.03020.104*
C410.6120 (8)0.9415 (8)−0.0922 (7)0.103 (3)
H410.54700.9030−0.13190.124*
C420.6530 (8)1.0315 (8)−0.0950 (6)0.085 (3)
H420.61581.0554−0.13580.102*
C430.7477 (8)1.0857 (7)−0.0385 (7)0.091 (3)
H430.77681.1474−0.04030.110*
C440.8026 (7)1.0501 (6)0.0228 (6)0.079 (3)
H440.86871.08830.06120.095*
C450.9356 (6)0.7777 (5)0.0486 (5)0.0478 (18)
C460.9812 (7)0.7202 (6)0.0937 (6)0.076 (2)
H460.97000.73810.15750.091*
C471.0421 (9)0.6379 (7)0.0463 (8)0.101 (3)
H471.07190.59970.07740.121*
C481.0587 (8)0.6121 (7)−0.0455 (9)0.104 (4)
H481.10130.5563−0.07760.125*
C491.0150 (8)0.6655 (8)−0.0921 (7)0.110 (4)
H491.02710.6468−0.15590.132*
C500.9517 (6)0.7488 (6)−0.0443 (6)0.069 (2)
H500.92000.7851−0.07660.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0528 (3)0.0453 (3)0.0366 (3)−0.0001 (3)−0.0015 (2)0.0178 (2)
Sn20.0393 (3)0.0503 (3)0.0422 (3)0.0039 (2)−0.0069 (2)0.0191 (2)
O10.071 (3)0.050 (3)0.038 (3)0.010 (3)0.001 (2)0.020 (2)
O20.072 (4)0.054 (3)0.042 (3)0.001 (3)0.000 (3)0.017 (3)
O30.078 (4)0.056 (3)0.064 (4)0.013 (3)0.008 (3)0.032 (3)
O40.043 (3)0.062 (3)0.050 (3)−0.013 (3)−0.018 (2)0.022 (3)
O50.062 (4)0.092 (4)0.071 (4)0.007 (3)−0.009 (3)0.040 (3)
O60.090 (5)0.179 (8)0.080 (5)0.020 (5)−0.037 (4)0.038 (5)
Br10.1071 (7)0.0675 (5)0.0490 (5)−0.0003 (5)−0.0052 (5)0.0131 (4)
Br20.2350 (17)0.1388 (11)0.1236 (11)−0.1209 (12)−0.0456 (10)0.0531 (9)
C10.048 (5)0.051 (5)0.043 (5)−0.001 (4)0.011 (4)0.022 (4)
C20.039 (4)0.052 (4)0.037 (4)0.000 (4)0.002 (3)0.024 (4)
C30.054 (5)0.060 (5)0.046 (5)0.000 (4)0.004 (4)0.026 (4)
C40.084 (6)0.076 (6)0.057 (6)0.014 (5)0.005 (5)0.046 (5)
C50.077 (6)0.080 (6)0.035 (5)0.000 (5)−0.001 (4)0.024 (5)
C60.043 (4)0.050 (4)0.050 (5)−0.005 (4)−0.005 (4)0.025 (4)
C70.050 (5)0.062 (5)0.038 (4)0.005 (4)0.002 (3)0.028 (4)
C80.069 (5)0.045 (4)0.037 (4)0.002 (4)0.008 (4)0.018 (4)
C90.128 (8)0.054 (5)0.080 (7)−0.005 (6)−0.035 (6)0.028 (5)
C100.230 (14)0.036 (5)0.099 (9)0.012 (7)−0.017 (9)0.028 (6)
C110.149 (11)0.080 (8)0.109 (10)0.051 (8)0.047 (8)0.062 (7)
C120.093 (8)0.095 (7)0.126 (9)0.014 (7)−0.007 (6)0.074 (7)
C130.070 (6)0.061 (5)0.093 (7)−0.002 (5)−0.004 (5)0.049 (5)
C140.042 (4)0.048 (4)0.029 (4)0.000 (4)−0.005 (3)0.018 (3)
C150.060 (5)0.060 (5)0.040 (5)−0.010 (4)−0.007 (4)0.024 (4)
C160.047 (5)0.112 (8)0.064 (6)−0.014 (5)0.005 (4)0.053 (6)
C170.046 (5)0.113 (8)0.049 (5)0.021 (6)−0.003 (4)0.025 (5)
C180.065 (6)0.073 (6)0.050 (5)0.017 (5)0.006 (4)0.029 (4)
C190.054 (5)0.052 (5)0.044 (5)−0.006 (4)0.006 (4)0.018 (4)
C200.046 (5)0.069 (5)0.051 (5)−0.001 (4)−0.006 (4)0.033 (4)
C210.065 (6)0.097 (7)0.060 (6)0.001 (6)0.003 (5)0.019 (5)
C220.056 (7)0.134 (9)0.096 (8)−0.010 (7)0.015 (6)0.038 (7)
C230.059 (7)0.090 (8)0.114 (9)−0.020 (6)−0.017 (6)0.064 (7)
C240.087 (7)0.062 (6)0.088 (7)−0.007 (6)−0.024 (6)0.020 (5)
C250.052 (5)0.066 (5)0.071 (6)0.002 (5)0.001 (4)0.018 (5)
C260.039 (5)0.080 (6)0.036 (5)−0.009 (5)0.003 (4)0.013 (4)
C270.043 (5)0.099 (7)0.030 (4)−0.008 (5)−0.003 (4)0.015 (5)
C280.051 (6)0.142 (10)0.043 (6)0.008 (7)−0.007 (4)0.018 (6)
C290.062 (8)0.207 (16)0.062 (7)−0.005 (11)−0.026 (6)0.003 (10)
C300.072 (10)0.237 (18)0.057 (8)−0.067 (12)−0.010 (6)0.005 (11)
C310.117 (9)0.132 (9)0.044 (6)−0.073 (8)−0.017 (6)0.021 (6)
C320.069 (6)0.100 (7)0.040 (5)−0.034 (6)−0.009 (4)0.022 (5)
C330.047 (5)0.034 (4)0.054 (5)−0.005 (4)−0.012 (4)0.006 (4)
C340.066 (6)0.070 (5)0.054 (5)0.009 (5)0.009 (5)0.027 (4)
C350.105 (8)0.072 (6)0.059 (6)−0.010 (6)0.023 (6)0.019 (5)
C360.114 (10)0.063 (6)0.087 (8)−0.012 (7)0.049 (7)0.004 (6)
C370.061 (7)0.080 (7)0.147 (11)0.008 (6)0.054 (8)0.019 (8)
C380.058 (6)0.061 (5)0.090 (7)0.004 (5)0.003 (5)0.024 (5)
C390.046 (5)0.054 (4)0.041 (4)0.003 (4)−0.007 (4)0.020 (4)
C400.090 (7)0.082 (6)0.095 (7)−0.017 (6)−0.041 (6)0.052 (6)
C410.089 (8)0.099 (8)0.116 (9)−0.038 (6)−0.042 (6)0.050 (7)
C420.078 (7)0.117 (8)0.079 (7)−0.005 (6)−0.015 (5)0.065 (6)
C430.098 (8)0.093 (7)0.107 (8)−0.012 (6)−0.025 (6)0.070 (6)
C440.078 (6)0.085 (6)0.084 (7)−0.020 (5)−0.031 (5)0.051 (5)
C450.043 (4)0.047 (4)0.043 (5)−0.002 (4)0.002 (4)0.009 (4)
C460.082 (6)0.069 (6)0.076 (6)0.026 (5)−0.005 (5)0.028 (5)
C470.113 (8)0.072 (7)0.098 (8)0.026 (6)−0.030 (7)0.016 (6)
C480.062 (6)0.089 (7)0.111 (10)0.036 (5)−0.017 (6)−0.012 (7)
C490.083 (7)0.147 (10)0.062 (7)0.034 (7)0.012 (6)0.001 (7)
C500.059 (5)0.076 (6)0.063 (6)0.015 (5)0.008 (4)0.017 (5)
Geometric parameters (Å, °) top
Sn1—O12.045 (4)C21—C221.376 (11)
Sn1—C82.110 (7)C21—H210.9300
Sn1—C202.112 (7)C22—C231.344 (11)
Sn1—C142.115 (7)C22—H220.9300
Sn2—C452.082 (7)C23—C241.344 (11)
Sn2—O42.087 (4)C23—H230.9300
Sn2—C332.116 (7)C24—C251.411 (10)
Sn2—C392.117 (7)C24—H240.9300
O1—C11.283 (7)C25—H250.9300
O2—C11.246 (7)C26—C271.486 (10)
O3—C31.340 (7)C27—C321.390 (10)
O3—H30.8200C27—C281.401 (11)
O4—C261.274 (8)C28—C291.404 (15)
O5—C261.231 (8)C29—C301.325 (17)
O6—C281.311 (11)C29—H290.9300
O6—H60.8200C30—C311.366 (16)
Br1—C61.894 (7)C30—H300.9300
Br2—C311.910 (11)C31—C321.386 (11)
C1—C21.470 (9)C32—H320.9300
C2—C71.375 (8)C33—C381.368 (10)
C2—C31.390 (9)C33—C341.373 (9)
C3—C41.394 (9)C34—C351.379 (10)
C4—C51.383 (9)C34—H340.9300
C4—H40.9300C35—C361.341 (12)
C5—C61.361 (9)C35—H350.9300
C5—H50.9300C36—C371.368 (13)
C6—C71.366 (8)C36—H360.9300
C7—H70.9300C37—C381.400 (11)
C8—C91.344 (9)C37—H370.9300
C8—C131.396 (9)C38—H380.9300
C9—C101.374 (11)C39—C441.358 (9)
C9—H90.9300C39—C401.368 (9)
C10—C111.336 (13)C40—C411.372 (10)
C10—H100.9300C40—H400.9300
C11—C121.334 (12)C41—C421.353 (10)
C11—H110.9300C41—H410.9300
C12—C131.354 (10)C42—C431.340 (10)
C12—H120.9300C42—H420.9300
C13—H130.9300C43—C441.388 (10)
C14—C191.372 (8)C43—H430.9300
C14—C151.387 (8)C44—H440.9300
C15—C161.391 (10)C45—C501.348 (9)
C15—H150.9300C45—C461.384 (9)
C16—C171.370 (10)C46—C471.360 (11)
C16—H160.9300C46—H460.9300
C17—C181.324 (10)C47—C481.339 (12)
C17—H170.9300C47—H470.9300
C18—C191.366 (9)C48—C491.347 (12)
C18—H180.9300C48—H480.9300
C19—H190.9300C49—C501.387 (11)
C20—C211.369 (10)C49—H490.9300
C20—C251.381 (9)C50—H500.9300
O1—Sn1—C895.4 (2)C24—C23—H23119.3
O1—Sn1—C20108.9 (2)C22—C23—H23119.3
C8—Sn1—C20111.4 (3)C23—C24—C25120.0 (8)
O1—Sn1—C14107.4 (2)C23—C24—H24120.0
C8—Sn1—C14114.5 (3)C25—C24—H24120.0
C20—Sn1—C14116.8 (3)C20—C25—C24119.3 (7)
C45—Sn2—O4106.3 (2)C20—C25—H25120.3
C45—Sn2—C33125.0 (3)C24—C25—H25120.3
O4—Sn2—C33100.3 (2)O5—C26—O4122.8 (7)
C45—Sn2—C39112.4 (3)O5—C26—C27120.7 (8)
O4—Sn2—C3995.2 (2)O4—C26—C27116.6 (8)
C33—Sn2—C39112.0 (3)C32—C27—C28120.0 (9)
C1—O1—Sn1113.8 (4)C32—C27—C26119.7 (8)
C3—O3—H3109.5C28—C27—C26120.3 (9)
C26—O4—Sn2113.3 (5)O6—C28—C27122.0 (10)
C28—O6—H6109.5O6—C28—C29119.5 (10)
O2—C1—O1122.2 (7)C27—C28—C29118.5 (11)
O2—C1—C2120.8 (7)C30—C29—C28119.7 (15)
O1—C1—C2116.9 (6)C30—C29—H29120.1
C7—C2—C3119.5 (6)C28—C29—H29120.1
C7—C2—C1120.2 (6)C29—C30—C31123.2 (16)
C3—C2—C1120.3 (6)C29—C30—H30118.4
O3—C3—C2123.2 (7)C31—C30—H30118.4
O3—C3—C4117.6 (7)C30—C31—C32119.0 (12)
C2—C3—C4119.2 (7)C30—C31—Br2122.5 (10)
C5—C4—C3119.7 (7)C32—C31—Br2118.4 (9)
C5—C4—H4120.1C31—C32—C27119.4 (9)
C3—C4—H4120.1C31—C32—H32120.3
C6—C5—C4120.3 (7)C27—C32—H32120.3
C6—C5—H5119.9C38—C33—C34118.5 (7)
C4—C5—H5119.9C38—C33—Sn2118.5 (6)
C5—C6—C7120.3 (7)C34—C33—Sn2122.9 (6)
C5—C6—Br1120.3 (6)C33—C34—C35121.2 (8)
C7—C6—Br1119.4 (5)C33—C34—H34119.4
C6—C7—C2120.9 (6)C35—C34—H34119.4
C6—C7—H7119.6C36—C35—C34119.9 (10)
C2—C7—H7119.6C36—C35—H35120.1
C9—C8—C13115.9 (7)C34—C35—H35120.1
C9—C8—Sn1124.1 (6)C35—C36—C37120.8 (10)
C13—C8—Sn1120.1 (5)C35—C36—H36119.6
C8—C9—C10122.7 (9)C37—C36—H36119.6
C8—C9—H9118.6C36—C37—C38119.2 (10)
C10—C9—H9118.6C36—C37—H37120.4
C11—C10—C9119.0 (10)C38—C37—H37120.4
C11—C10—H10120.5C33—C38—C37120.3 (9)
C9—C10—H10120.5C33—C38—H38119.8
C12—C11—C10121.0 (9)C37—C38—H38119.8
C12—C11—H11119.5C44—C39—C40117.3 (7)
C10—C11—H11119.5C44—C39—Sn2121.0 (6)
C11—C12—C13120.0 (9)C40—C39—Sn2121.7 (6)
C11—C12—H12120.0C39—C40—C41121.1 (8)
C13—C12—H12120.0C39—C40—H40119.4
C12—C13—C8121.4 (8)C41—C40—H40119.4
C12—C13—H13119.3C42—C41—C40120.7 (9)
C8—C13—H13119.3C42—C41—H41119.7
C19—C14—C15118.6 (6)C40—C41—H41119.7
C19—C14—Sn1121.8 (5)C43—C42—C41119.3 (9)
C15—C14—Sn1119.6 (5)C43—C42—H42120.4
C14—C15—C16119.0 (7)C41—C42—H42120.4
C14—C15—H15120.5C42—C43—C44120.2 (8)
C16—C15—H15120.5C42—C43—H43119.9
C17—C16—C15120.4 (7)C44—C43—H43119.9
C17—C16—H16119.8C39—C44—C43121.4 (8)
C15—C16—H16119.8C39—C44—H44119.3
C18—C17—C16120.0 (8)C43—C44—H44119.3
C18—C17—H17120.0C50—C45—C46118.1 (7)
C16—C17—H17120.0C50—C45—Sn2120.1 (6)
C17—C18—C19121.3 (8)C46—C45—Sn2121.8 (6)
C17—C18—H18119.4C47—C46—C45121.1 (9)
C19—C18—H18119.4C47—C46—H46119.4
C18—C19—C14120.8 (7)C45—C46—H46119.4
C18—C19—H19119.6C48—C47—C46119.6 (10)
C14—C19—H19119.6C48—C47—H47120.2
C21—C20—C25117.9 (7)C46—C47—H47120.2
C21—C20—Sn1121.6 (6)C47—C48—C49121.1 (10)
C25—C20—Sn1120.4 (6)C47—C48—H48119.4
C20—C21—C22122.2 (8)C49—C48—H48119.4
C20—C21—H21118.9C48—C49—C50119.5 (9)
C22—C21—H21118.9C48—C49—H49120.3
C23—C22—C21119.0 (9)C50—C49—H49120.3
C23—C22—H22120.5C45—C50—C49120.6 (8)
C21—C22—H22120.5C45—C50—H50119.7
C24—C23—C22121.4 (9)C49—C50—H50119.7
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.862.583 (8)146
O6—H6···O50.821.862.583 (9)147
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.862.583 (8)146
O6—H6···O50.821.862.583 (9)147
Acknowledgements top

We acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University.

references
References top

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Sheldrick, G. M. (1996). SADABS.University of Göttingen, Germany.

Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen,Germany.

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Siemens (1996). SMART and SAINT. Siemens Analytical X-Ray Instruments Inc., Madison, Wisconsin, USA.