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ISSN: 2056-9890

catena-Poly[[tri­benzyl­tin(IV)]-μ-(E)-3-(2-fur­yl)prop-2-enoato-κ2O:O′]

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 31 May 2011; accepted 18 June 2011; online 25 June 2011)

In the title carboxyl­ate-bridged polymer, [Sn(C7H7)3(C7H5O3)]n, the SnIV atom exists in a distorted trans-C3SnO2 trigonal–bipyramidal geometry. The polymer propagates as a chain along the a axis. There are two independent formula units in the asymmetric unit; the furyl ring of one of the anions is disordered over two positions in a 0.630 (8):0.370 (8) ratio. The crystal studied was a non-merohedral twin with a minor twin domain of 37.3 (1)%.

Related literature

For a related tribenzyl­tin cinnamate, see: Lo & Ng (2011[Lo, K. M. & Ng, S. W. (2011). Acta Cryst. E67, m744-m745.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C7H7)3(C7H5O3)]

  • Mr = 529.18

  • Triclinic, [P \overline 1]

  • a = 10.5744 (1) Å

  • b = 10.8946 (1) Å

  • c = 21.4199 (3) Å

  • α = 101.7132 (6)°

  • β = 90.6861 (6)°

  • γ = 101.2031 (6)°

  • V = 2366.83 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.11 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (TWINABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.574, Tmax = 0.746

  • 40884 measured reflections

  • 11649 independent reflections

  • 10010 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.106

  • S = 1.07

  • 11649 reflections

  • 603 parameters

  • 56 restraints

  • H-atom parameters constrained

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

We have reported tribenzyltin 3-phenylprop-2-enoate recently; the compound exists as a carboxyate bridged polymer whose repeat distance is half the b-axial length (Lo & Ng, 2011). Replacing the phenyl unit by a furyl unit gives the corresponding polymeric compound (Scheme I). The SnIV atom in [Sn(C7H7)3(C7H5O2)]n exists in a trans-C3SnO2 trigonal-bipyramidal geometry (Fig. 1). The polymer propagates as a chain along the a-axis with a repeat distance that is half the a-axial length.

Related literature top

For a related tribenzyltin cinnamate, see: Lo & Ng (2011).

Experimental top

Tribenzyltin hydroxide (0.4 g, 1 mmol) and furylacrylic acid (0.14 g, 1 mmol) were heated in ethanol (50 ml) for 2 h. The solution was filtered; evaporation of the solvent gave colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

One of the furan rings is disordered over two positions. The furan ring was refined subject to the atoms being restrained to a bonding distance of 1.35±0.01 Å. The ring was restrained to near planarity. Because the ring is disordered so that the O atom overlapped with a C atom, the temperature factors of O3 were set to those of C47. Those of O3' were set to those of C47'. Additionally the temperature factors of the disordered atoms were restrained to be nearly isotropic. In view of the twinned nature of the crystal, this treatment was considered adequate.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the polymeric chain structure of [Sn(C7H7)3(C7H5O3)]n at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the furyl rings is not shown.
catena-Poly[[tribenzyltin(IV)]-µ-(E)-3-(2-furyl)prop-2- enoato-κ2O:O'] top
Crystal data top
[Sn(C7H7)3(C7H5O2)]Z = 4
Mr = 529.18F(000) = 1072
Triclinic, P1Dx = 1.485 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5744 (1) ÅCell parameters from 4375 reflections
b = 10.8946 (1) Åθ = 2.4–28.2°
c = 21.4199 (3) ŵ = 1.11 mm1
α = 101.7132 (6)°T = 100 K
β = 90.6861 (6)°Block, colorless
γ = 101.2031 (6)°0.30 × 0.20 × 0.10 mm
V = 2366.83 (5) Å3
Data collection top
Bruker SMART APEX
diffractometer
11649 independent reflections
Radiation source: fine-focus sealed tube10010 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 28.3°, θmin = 1.0°
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)
h = 1414
Tmin = 0.574, Tmax = 0.746k = 1414
40884 measured reflectionsl = 028
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0595P)2 + 1.754P]
where P = (Fo2 + 2Fc2)/3
11649 reflections(Δ/σ)max = 0.001
603 parametersΔρmax = 0.80 e Å3
56 restraintsΔρmin = 0.58 e Å3
Crystal data top
[Sn(C7H7)3(C7H5O2)]γ = 101.2031 (6)°
Mr = 529.18V = 2366.83 (5) Å3
Triclinic, P1Z = 4
a = 10.5744 (1) ÅMo Kα radiation
b = 10.8946 (1) ŵ = 1.11 mm1
c = 21.4199 (3) ÅT = 100 K
α = 101.7132 (6)°0.30 × 0.20 × 0.10 mm
β = 90.6861 (6)°
Data collection top
Bruker SMART APEX
diffractometer
11649 independent reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)
10010 reflections with I > 2σ(I)
Tmin = 0.574, Tmax = 0.746Rint = 0.030
40884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03356 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.07Δρmax = 0.80 e Å3
11649 reflectionsΔρmin = 0.58 e Å3
603 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.42162 (2)0.46489 (2)0.738222 (11)0.01823 (7)
Sn20.90414 (2)0.38862 (2)0.779954 (10)0.01697 (6)
O10.5896 (2)0.5262 (2)0.68649 (12)0.0240 (5)
O20.7317 (2)0.4722 (2)0.74811 (12)0.0237 (5)
O30.8566 (8)0.6995 (6)0.5163 (3)0.0385 (11)0.630 (8)
O3'1.0107 (8)0.6534 (10)0.5614 (5)0.0320 (15)0.370 (8)
O41.0461 (2)0.2949 (2)0.81974 (11)0.0219 (5)
O51.2189 (2)0.4037 (2)0.78297 (13)0.0252 (5)
O61.4103 (3)0.2200 (3)0.95100 (14)0.0347 (6)
C10.4418 (3)0.2674 (3)0.72014 (17)0.0227 (7)
H1A0.53330.26300.71300.027*
H1B0.41680.23090.75800.027*
C20.3595 (4)0.1903 (3)0.66322 (17)0.0237 (7)
C30.3951 (4)0.2041 (4)0.60194 (18)0.0292 (8)
H30.47090.26370.59710.035*
C40.3213 (4)0.1319 (4)0.5482 (2)0.0361 (9)
H40.34740.14210.50700.043*
C50.2106 (4)0.0457 (4)0.5541 (2)0.0407 (11)
H50.16070.00440.51720.049*
C60.1734 (4)0.0332 (4)0.6138 (2)0.0456 (12)
H60.09640.02530.61820.055*
C70.2461 (4)0.1045 (4)0.6682 (2)0.0374 (10)
H70.21800.09460.70920.045*
C80.2893 (3)0.5092 (4)0.67325 (18)0.0238 (7)
H8A0.24560.42730.64550.029*
H8B0.22220.54410.69900.029*
C90.3369 (3)0.6001 (3)0.63018 (18)0.0224 (7)
C100.3693 (4)0.5560 (4)0.56875 (19)0.0322 (8)
H100.36830.46730.55450.039*
C110.4031 (4)0.6374 (4)0.52738 (19)0.0352 (9)
H110.42570.60480.48530.042*
C120.4040 (4)0.7672 (4)0.5474 (2)0.0359 (9)
H120.42400.82360.51880.043*
C130.3752 (4)0.8130 (4)0.6098 (2)0.0337 (9)
H130.37760.90180.62440.040*
C140.3431 (3)0.7301 (4)0.65082 (18)0.0266 (7)
H140.32510.76280.69360.032*
C150.4923 (4)0.6006 (3)0.82487 (18)0.0253 (7)
H15A0.44480.57400.86100.030*
H15B0.58480.60100.83300.030*
C160.4768 (3)0.7330 (3)0.82155 (17)0.0235 (7)
C170.3733 (4)0.7818 (4)0.84802 (19)0.0296 (8)
H170.31040.73010.86810.036*
C180.3602 (5)0.9046 (4)0.8456 (2)0.0430 (11)
H180.28920.93700.86450.052*
C190.4491 (6)0.9797 (4)0.8162 (2)0.0505 (13)
H190.44041.06440.81500.061*
C200.5514 (5)0.9321 (4)0.7882 (2)0.0463 (12)
H200.61250.98340.76710.056*
C210.5648 (4)0.8086 (4)0.7909 (2)0.0352 (9)
H210.63510.77590.77150.042*
C220.9459 (3)0.3131 (4)0.68307 (17)0.0238 (7)
H22A0.92910.37060.65500.029*
H22B1.03770.30590.68090.029*
C230.8606 (3)0.1845 (3)0.66224 (15)0.0217 (7)
C240.7443 (3)0.1658 (4)0.62716 (17)0.0258 (7)
H240.71960.23640.61410.031*
C250.6641 (4)0.0466 (4)0.61101 (18)0.0308 (8)
H250.58530.03610.58690.037*
C260.6981 (4)0.0582 (4)0.62976 (19)0.0315 (8)
H260.64290.14020.61870.038*
C270.8137 (4)0.0412 (4)0.66493 (19)0.0306 (8)
H270.83860.11220.67760.037*
C280.8928 (4)0.0788 (4)0.68148 (18)0.0278 (8)
H280.97050.08960.70650.033*
C290.7597 (3)0.2648 (3)0.82037 (16)0.0225 (7)
H29A0.67390.26010.79990.027*
H29B0.77820.17740.81210.027*
C300.7579 (3)0.3144 (3)0.89148 (17)0.0223 (7)
C310.8265 (4)0.2693 (4)0.93461 (17)0.0257 (7)
H310.87080.20200.91950.031*
C320.8310 (4)0.3213 (4)0.99948 (18)0.0341 (9)
H320.87810.28951.02850.041*
C330.7671 (5)0.4195 (4)1.02212 (19)0.0390 (10)
H330.77130.45571.06650.047*
C340.6977 (5)0.4647 (4)0.9803 (2)0.0379 (10)
H340.65350.53190.99580.045*
C350.6922 (4)0.4123 (4)0.91577 (19)0.0303 (8)
H350.64300.44330.88730.036*
C360.9931 (4)0.5649 (3)0.84266 (18)0.0262 (8)
H36A0.96270.56040.88580.031*
H36B1.08710.56690.84480.031*
C370.9757 (3)0.6910 (3)0.82988 (16)0.0212 (6)
C380.8917 (4)0.7590 (4)0.8639 (2)0.0316 (8)
H380.83970.72270.89400.038*
C390.8824 (5)0.8794 (4)0.8546 (2)0.0393 (10)
H390.82420.92450.87830.047*
C400.9565 (5)0.9337 (4)0.8116 (2)0.0404 (10)
H400.95181.01730.80630.048*
C411.0376 (4)0.8667 (4)0.7762 (2)0.0416 (10)
H411.08720.90280.74530.050*
C421.0476 (4)0.7459 (4)0.7853 (2)0.0329 (9)
H421.10450.70050.76060.040*
C430.7049 (3)0.5203 (3)0.70187 (17)0.0211 (7)
C440.8079 (3)0.5711 (3)0.66284 (18)0.0255 (7)
H440.89510.57660.67630.031*
C450.7842 (3)0.6097 (3)0.60954 (17)0.0225 (7)
H450.69710.61010.59830.027*
C460.8821 (3)0.6510 (3)0.56786 (16)0.0246 (7)
C471.0034 (7)0.6364 (8)0.5815 (4)0.0320 (15)0.630 (8)
H471.03610.60470.61520.038*0.630 (8)
C481.0654 (10)0.6819 (9)0.5313 (5)0.069 (3)0.630 (8)
H481.15480.68660.52470.083*0.630 (8)
C490.9835 (10)0.7188 (9)0.4930 (4)0.047 (3)0.630 (8)
H491.00680.75240.45630.057*0.630 (8)
C47'0.8439 (17)0.6976 (12)0.5179 (5)0.0385 (11)0.37
H47'0.75780.70690.51050.046*0.370 (8)
C48'0.9424 (11)0.7300 (13)0.4793 (6)0.020 (3)0.370 (8)
H48'0.93790.76410.44200.025*0.370 (8)
C49'1.0479 (11)0.7022 (10)0.5062 (5)0.022 (3)0.370 (8)
H49'1.13220.71360.49070.027*0.370 (8)
C501.1687 (3)0.3309 (3)0.81872 (17)0.0214 (7)
C511.2508 (3)0.2870 (3)0.86180 (17)0.0225 (7)
H511.34180.31300.86130.027*
C521.2036 (4)0.2129 (3)0.90133 (16)0.0240 (7)
H521.11270.18340.89940.029*
C531.2796 (4)0.1736 (4)0.94699 (18)0.0281 (8)
C541.2487 (5)0.0981 (5)0.9901 (2)0.0388 (10)
H541.16500.05460.99740.047*
C551.3673 (5)0.0976 (5)1.0223 (2)0.0429 (11)
H551.37820.05371.05540.051*
C561.4594 (5)0.1702 (5)0.9971 (2)0.0439 (11)
H561.54860.18551.00960.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01931 (11)0.01664 (11)0.02035 (12)0.00686 (9)0.00117 (9)0.00464 (8)
Sn20.01779 (11)0.01694 (11)0.01666 (11)0.00366 (8)0.00037 (8)0.00452 (8)
O10.0204 (11)0.0277 (13)0.0273 (13)0.0075 (10)0.0007 (10)0.0113 (10)
O20.0196 (11)0.0230 (12)0.0298 (13)0.0056 (10)0.0013 (10)0.0074 (10)
O30.041 (2)0.046 (2)0.0266 (17)0.0009 (17)0.0004 (15)0.0138 (15)
O3'0.0221 (19)0.044 (3)0.036 (5)0.003 (2)0.003 (3)0.026 (3)
O40.0210 (11)0.0227 (12)0.0245 (12)0.0057 (10)0.0002 (10)0.0094 (10)
O50.0206 (11)0.0269 (13)0.0316 (14)0.0073 (10)0.0030 (10)0.0118 (11)
O60.0325 (14)0.0387 (16)0.0363 (15)0.0159 (12)0.0065 (12)0.0079 (13)
C10.0270 (17)0.0193 (16)0.0240 (17)0.0076 (14)0.0034 (14)0.0066 (13)
C20.0279 (17)0.0168 (15)0.0281 (18)0.0094 (14)0.0057 (15)0.0040 (13)
C30.0285 (18)0.0301 (19)0.0282 (19)0.0051 (15)0.0001 (15)0.0054 (15)
C40.040 (2)0.039 (2)0.028 (2)0.0118 (18)0.0046 (17)0.0014 (17)
C50.033 (2)0.039 (2)0.042 (2)0.0119 (18)0.0027 (18)0.0136 (19)
C60.027 (2)0.035 (2)0.061 (3)0.0046 (18)0.010 (2)0.011 (2)
C70.035 (2)0.028 (2)0.042 (2)0.0002 (17)0.0119 (18)0.0042 (17)
C80.0175 (15)0.0278 (18)0.0281 (18)0.0049 (14)0.0012 (14)0.0100 (14)
C90.0166 (15)0.0241 (17)0.0289 (18)0.0038 (13)0.0047 (13)0.0118 (14)
C100.044 (2)0.0256 (19)0.0279 (19)0.0109 (17)0.0025 (17)0.0039 (15)
C110.045 (2)0.037 (2)0.0227 (19)0.0069 (19)0.0018 (17)0.0079 (16)
C120.035 (2)0.034 (2)0.040 (2)0.0020 (18)0.0051 (18)0.0197 (18)
C130.036 (2)0.0196 (18)0.045 (2)0.0017 (15)0.0015 (18)0.0097 (17)
C140.0256 (17)0.0260 (18)0.0277 (18)0.0050 (14)0.0021 (14)0.0046 (14)
C150.0278 (17)0.0216 (18)0.0275 (19)0.0091 (14)0.0025 (14)0.0036 (14)
C160.0265 (17)0.0215 (17)0.0222 (16)0.0045 (14)0.0070 (14)0.0049 (13)
C170.035 (2)0.0263 (19)0.029 (2)0.0102 (16)0.0051 (15)0.0043 (15)
C180.059 (3)0.034 (2)0.040 (2)0.027 (2)0.004 (2)0.0014 (19)
C190.093 (4)0.020 (2)0.038 (2)0.015 (2)0.010 (3)0.0038 (17)
C200.075 (3)0.023 (2)0.033 (2)0.004 (2)0.005 (2)0.0032 (17)
C210.041 (2)0.026 (2)0.032 (2)0.0016 (17)0.0015 (18)0.0019 (16)
C220.0238 (16)0.0285 (19)0.0199 (16)0.0044 (14)0.0005 (13)0.0079 (14)
C230.0233 (16)0.0262 (17)0.0155 (15)0.0054 (14)0.0008 (13)0.0031 (12)
C240.0279 (17)0.0284 (19)0.0223 (17)0.0102 (15)0.0009 (14)0.0038 (14)
C250.0307 (19)0.033 (2)0.0280 (19)0.0125 (16)0.0058 (15)0.0006 (15)
C260.033 (2)0.0251 (19)0.031 (2)0.0031 (15)0.0066 (16)0.0036 (15)
C270.034 (2)0.0262 (19)0.0311 (19)0.0120 (16)0.0054 (16)0.0006 (15)
C280.0276 (18)0.033 (2)0.0232 (18)0.0110 (15)0.0019 (14)0.0015 (15)
C290.0225 (16)0.0270 (18)0.0181 (16)0.0055 (14)0.0027 (13)0.0047 (13)
C300.0219 (16)0.0207 (16)0.0257 (17)0.0030 (13)0.0025 (14)0.0092 (13)
C310.0265 (17)0.0274 (18)0.0243 (18)0.0090 (15)0.0002 (14)0.0044 (14)
C320.047 (2)0.037 (2)0.0212 (18)0.0135 (19)0.0035 (17)0.0076 (16)
C330.060 (3)0.037 (2)0.0212 (19)0.015 (2)0.0035 (19)0.0045 (16)
C340.050 (2)0.034 (2)0.035 (2)0.0215 (19)0.0165 (19)0.0049 (17)
C350.034 (2)0.030 (2)0.034 (2)0.0153 (16)0.0045 (16)0.0132 (16)
C360.0299 (18)0.0206 (17)0.0274 (18)0.0061 (14)0.0094 (15)0.0030 (14)
C370.0187 (15)0.0189 (16)0.0248 (17)0.0020 (13)0.0037 (13)0.0042 (13)
C380.033 (2)0.031 (2)0.033 (2)0.0118 (16)0.0045 (16)0.0064 (16)
C390.052 (3)0.033 (2)0.036 (2)0.023 (2)0.005 (2)0.0003 (18)
C400.061 (3)0.0235 (19)0.036 (2)0.009 (2)0.019 (2)0.0058 (16)
C410.043 (2)0.038 (2)0.043 (3)0.0029 (19)0.002 (2)0.017 (2)
C420.0307 (19)0.030 (2)0.040 (2)0.0078 (16)0.0094 (17)0.0111 (17)
C430.0220 (16)0.0176 (16)0.0239 (17)0.0029 (13)0.0036 (13)0.0058 (13)
C440.0213 (16)0.0223 (17)0.0323 (19)0.0028 (14)0.0040 (14)0.0064 (14)
C450.0196 (15)0.0220 (17)0.0258 (17)0.0049 (13)0.0009 (13)0.0045 (13)
C460.0242 (17)0.0251 (18)0.0242 (17)0.0029 (14)0.0038 (14)0.0070 (14)
C470.0221 (19)0.044 (3)0.036 (5)0.003 (2)0.003 (3)0.026 (3)
C480.039 (5)0.074 (6)0.081 (7)0.008 (4)0.018 (5)0.002 (6)
C490.070 (7)0.044 (5)0.022 (5)0.010 (5)0.008 (5)0.012 (4)
C47'0.041 (2)0.046 (2)0.0266 (17)0.0009 (17)0.0004 (15)0.0138 (15)
C48'0.019 (5)0.036 (5)0.010 (5)0.006 (4)0.006 (4)0.015 (4)
C49'0.024 (5)0.027 (5)0.020 (5)0.002 (4)0.007 (4)0.019 (4)
C500.0224 (16)0.0197 (16)0.0220 (17)0.0067 (13)0.0009 (13)0.0021 (13)
C510.0218 (16)0.0200 (16)0.0257 (17)0.0086 (13)0.0019 (13)0.0009 (13)
C520.0263 (17)0.0269 (18)0.0203 (16)0.0125 (14)0.0000 (13)0.0013 (13)
C530.0319 (19)0.032 (2)0.0254 (18)0.0171 (16)0.0036 (15)0.0071 (15)
C540.045 (2)0.049 (3)0.031 (2)0.022 (2)0.0010 (18)0.0159 (19)
C550.054 (3)0.055 (3)0.030 (2)0.031 (2)0.0021 (19)0.014 (2)
C560.042 (2)0.055 (3)0.040 (2)0.027 (2)0.013 (2)0.006 (2)
Geometric parameters (Å, º) top
Sn1—C152.148 (4)C23—C281.397 (5)
Sn1—C82.149 (3)C24—C251.381 (5)
Sn1—C12.160 (3)C24—H240.9500
Sn1—O12.171 (2)C25—C261.391 (6)
Sn1—O5i2.390 (3)C25—H250.9500
Sn2—C362.144 (4)C26—C271.390 (5)
Sn2—C292.147 (4)C26—H260.9500
Sn2—C222.156 (4)C27—C281.384 (5)
Sn2—O42.223 (2)C27—H270.9500
Sn2—O22.342 (2)C28—H280.9500
O1—C431.276 (4)C29—C301.511 (5)
O2—C431.264 (4)C29—H29A0.9900
O3—C461.362 (6)C29—H29B0.9900
O3—C491.428 (8)C30—C311.388 (5)
O3'—C461.365 (8)C30—C351.401 (5)
O3'—C49'1.422 (8)C31—C321.387 (5)
O4—C501.281 (4)C31—H310.9500
O5—C501.261 (4)C32—C331.383 (6)
O5—Sn1ii2.390 (2)C32—H320.9500
O6—C561.361 (5)C33—C341.374 (6)
O6—C531.371 (5)C33—H330.9500
C1—C21.491 (5)C34—C351.381 (6)
C1—H1A0.9900C34—H340.9500
C1—H1B0.9900C35—H350.9500
C2—C71.389 (5)C36—C371.498 (5)
C2—C31.399 (5)C36—H36A0.9900
C3—C41.388 (5)C36—H36B0.9900
C3—H30.9500C37—C421.386 (5)
C4—C51.375 (6)C37—C381.386 (5)
C4—H40.9500C38—C391.387 (6)
C5—C61.369 (7)C38—H380.9500
C5—H50.9500C39—C401.369 (7)
C6—C71.389 (6)C39—H390.9500
C6—H60.9500C40—C411.370 (7)
C7—H70.9500C40—H400.9500
C8—C91.508 (5)C41—C421.392 (6)
C8—H8A0.9900C41—H410.9500
C8—H8B0.9900C42—H420.9500
C9—C101.377 (5)C43—C441.472 (5)
C9—C141.384 (5)C44—C451.331 (5)
C10—C111.379 (5)C44—H440.9500
C10—H100.9500C45—C461.440 (5)
C11—C121.390 (6)C45—H450.9500
C11—H110.9500C46—C471.358 (7)
C12—C131.388 (6)C46—C47'1.363 (10)
C12—H120.9500C47—C481.392 (8)
C13—C141.383 (5)C47—H470.9500
C13—H130.9500C48—C491.356 (9)
C14—H140.9500C48—H480.9500
C15—C161.499 (5)C49—H490.9500
C15—H15A0.9900C47'—C48'1.375 (10)
C15—H15B0.9900C47'—H47'0.9500
C16—C211.383 (5)C48'—C49'1.362 (9)
C16—C171.386 (5)C48'—H48'0.9500
C17—C181.382 (6)C49'—H49'0.9500
C17—H170.9500C50—C511.468 (5)
C18—C191.371 (7)C51—C521.323 (5)
C18—H180.9500C51—H510.9500
C19—C201.381 (8)C52—C531.439 (5)
C19—H190.9500C52—H520.9500
C20—C211.392 (6)C53—C541.359 (6)
C20—H200.9500C54—C551.426 (6)
C21—H210.9500C54—H540.9500
C22—C231.491 (5)C55—C561.324 (7)
C22—H22A0.9900C55—H550.9500
C22—H22B0.9900C56—H560.9500
C23—C241.392 (5)
C15—Sn1—C8119.95 (14)C26—C25—H25119.8
C15—Sn1—C1123.54 (13)C27—C26—C25119.1 (4)
C8—Sn1—C1115.20 (14)C27—C26—H26120.5
C15—Sn1—O193.66 (13)C25—C26—H26120.5
C8—Sn1—O193.66 (11)C28—C27—C26120.1 (4)
C1—Sn1—O194.08 (12)C28—C27—H27119.9
C15—Sn1—O5i91.05 (12)C26—C27—H27119.9
C8—Sn1—O5i78.06 (11)C27—C28—C23121.4 (3)
C1—Sn1—O5i88.99 (12)C27—C28—H28119.3
O1—Sn1—O5i171.70 (9)C23—C28—H28119.3
C36—Sn2—C29115.80 (14)C30—C29—Sn2110.3 (2)
C36—Sn2—C22129.12 (15)C30—C29—H29A109.6
C29—Sn2—C22115.00 (13)Sn2—C29—H29A109.6
C36—Sn2—O488.38 (11)C30—C29—H29B109.6
C29—Sn2—O486.08 (11)Sn2—C29—H29B109.6
C22—Sn2—O492.31 (11)H29A—C29—H29B108.1
C36—Sn2—O293.58 (11)C31—C30—C35117.9 (3)
C29—Sn2—O285.24 (11)C31—C30—C29121.2 (3)
C22—Sn2—O293.18 (12)C35—C30—C29120.8 (3)
O4—Sn2—O2171.09 (9)C32—C31—C30120.7 (3)
C43—O1—Sn1124.6 (2)C32—C31—H31119.6
C43—O2—Sn2136.2 (2)C30—C31—H31119.6
C46—O3—C4998.6 (6)C33—C32—C31120.3 (4)
C46—O3'—C49'108.3 (7)C33—C32—H32119.9
C50—O4—Sn2123.8 (2)C31—C32—H32119.9
C50—O5—Sn1ii139.3 (2)C34—C33—C32120.0 (4)
C56—O6—C53106.0 (3)C34—C33—H33120.0
C2—C1—Sn1111.2 (2)C32—C33—H33120.0
C2—C1—H1A109.4C33—C34—C35119.9 (4)
Sn1—C1—H1A109.4C33—C34—H34120.1
C2—C1—H1B109.4C35—C34—H34120.1
Sn1—C1—H1B109.4C34—C35—C30121.3 (4)
H1A—C1—H1B108.0C34—C35—H35119.4
C7—C2—C3117.6 (4)C30—C35—H35119.4
C7—C2—C1122.6 (3)C37—C36—Sn2121.0 (2)
C3—C2—C1119.8 (3)C37—C36—H36A107.1
C4—C3—C2120.9 (4)Sn2—C36—H36A107.1
C4—C3—H3119.5C37—C36—H36B107.1
C2—C3—H3119.5Sn2—C36—H36B107.1
C5—C4—C3120.6 (4)H36A—C36—H36B106.8
C5—C4—H4119.7C42—C37—C38117.8 (3)
C3—C4—H4119.7C42—C37—C36120.8 (3)
C6—C5—C4119.0 (4)C38—C37—C36121.4 (3)
C6—C5—H5120.5C37—C38—C39121.0 (4)
C4—C5—H5120.5C37—C38—H38119.5
C5—C6—C7121.2 (4)C39—C38—H38119.5
C5—C6—H6119.4C40—C39—C38120.5 (4)
C7—C6—H6119.4C40—C39—H39119.7
C6—C7—C2120.6 (4)C38—C39—H39119.7
C6—C7—H7119.7C39—C40—C41119.4 (4)
C2—C7—H7119.7C39—C40—H40120.3
C9—C8—Sn1120.5 (2)C41—C40—H40120.3
C9—C8—H8A107.2C40—C41—C42120.4 (4)
Sn1—C8—H8A107.2C40—C41—H41119.8
C9—C8—H8B107.2C42—C41—H41119.8
Sn1—C8—H8B107.2C37—C42—C41120.8 (4)
H8A—C8—H8B106.8C37—C42—H42119.6
C10—C9—C14118.4 (3)C41—C42—H42119.6
C10—C9—C8121.3 (3)O2—C43—O1122.5 (3)
C14—C9—C8120.2 (3)O2—C43—C44120.3 (3)
C9—C10—C11121.6 (4)O1—C43—C44117.2 (3)
C9—C10—H10119.2C45—C44—C43122.9 (3)
C11—C10—H10119.2C45—C44—H44118.5
C10—C11—C12119.8 (4)C43—C44—H44118.5
C10—C11—H11120.1C44—C45—C46124.2 (3)
C12—C11—H11120.1C44—C45—H45117.9
C13—C12—C11118.9 (4)C46—C45—H45117.9
C13—C12—H12120.6C47—C46—O3120.5 (6)
C11—C12—H12120.6C47'—C46—O3'105.1 (9)
C14—C13—C12120.4 (4)C47—C46—C45116.4 (5)
C14—C13—H13119.8O3—C46—C45123.0 (4)
C12—C13—H13119.8C47'—C46—C45117.2 (8)
C9—C14—C13120.7 (4)O3'—C46—C45137.6 (5)
C9—C14—H14119.6C46—C47—C4899.0 (6)
C13—C14—H14119.6C46—C47—H47130.5
C16—C15—Sn1111.8 (2)C48—C47—H47130.5
C16—C15—H15A109.2C49—C48—C47112.1 (8)
Sn1—C15—H15A109.2C49—C48—H48124.0
C16—C15—H15B109.2C47—C48—H48124.0
Sn1—C15—H15B109.2C48—C49—O3109.8 (7)
H15A—C15—H15B107.9C48—C49—H49125.1
C21—C16—C17118.4 (4)O3—C49—H49125.1
C21—C16—C15120.5 (4)C46—C47'—C48'113.2 (13)
C17—C16—C15121.1 (3)C46—C47'—H47'123.4
C18—C17—C16120.9 (4)C48'—C47'—H47'123.4
C18—C17—H17119.5C49'—C48'—C47'104.7 (12)
C16—C17—H17119.5C49'—C48'—H48'127.7
C19—C18—C17120.2 (4)C47'—C48'—H48'127.7
C19—C18—H18119.9C48'—C49'—O3'108.6 (10)
C17—C18—H18119.9C48'—C49'—H49'125.7
C18—C19—C20119.9 (4)O3'—C49'—H49'125.7
C18—C19—H19120.1O5—C50—O4121.8 (3)
C20—C19—H19120.1O5—C50—C51120.2 (3)
C19—C20—C21119.8 (4)O4—C50—C51118.0 (3)
C19—C20—H20120.1C52—C51—C50122.9 (3)
C21—C20—H20120.1C52—C51—H51118.6
C16—C21—C20120.7 (4)C50—C51—H51118.6
C16—C21—H21119.6C51—C52—C53124.9 (3)
C20—C21—H21119.6C51—C52—H52117.6
C23—C22—Sn2107.6 (2)C53—C52—H52117.6
C23—C22—H22A110.2C54—C53—O6109.8 (3)
Sn2—C22—H22A110.2C54—C53—C52132.9 (4)
C23—C22—H22B110.2O6—C53—C52117.3 (3)
Sn2—C22—H22B110.2C53—C54—C55106.0 (4)
H22A—C22—H22B108.5C53—C54—H54127.0
C24—C23—C28117.7 (3)C55—C54—H54127.0
C24—C23—C22122.4 (3)C56—C55—C54106.7 (4)
C28—C23—C22119.7 (3)C56—C55—H55126.6
C25—C24—C23121.3 (3)C54—C55—H55126.6
C25—C24—H24119.4C55—C56—O6111.4 (4)
C23—C24—H24119.4C55—C56—H56124.3
C24—C25—C26120.4 (4)O6—C56—H56124.3
C24—C25—H25119.8
C15—Sn1—O1—C4361.3 (3)C35—C30—C31—C321.0 (6)
C8—Sn1—O1—C43178.3 (3)C29—C30—C31—C32175.8 (4)
C1—Sn1—O1—C4362.7 (3)C30—C31—C32—C330.1 (6)
C36—Sn2—O2—C4396.2 (3)C31—C32—C33—C340.8 (7)
C29—Sn2—O2—C43148.2 (3)C32—C33—C34—C350.3 (7)
C22—Sn2—O2—C4333.4 (3)C33—C34—C35—C300.9 (7)
C36—Sn2—O4—C5057.5 (3)C31—C30—C35—C341.5 (6)
C29—Sn2—O4—C50173.5 (3)C29—C30—C35—C34175.3 (4)
C22—Sn2—O4—C5071.6 (3)C29—Sn2—C36—C37115.0 (3)
C15—Sn1—C1—C2167.6 (2)C22—Sn2—C36—C3768.5 (4)
C8—Sn1—C1—C20.7 (3)O4—Sn2—C36—C37160.1 (3)
O1—Sn1—C1—C295.3 (2)O2—Sn2—C36—C3728.6 (3)
O5i—Sn1—C1—C277.0 (2)Sn2—C36—C37—C4279.8 (4)
Sn1—C1—C2—C7105.6 (4)Sn2—C36—C37—C38102.9 (4)
Sn1—C1—C2—C373.7 (4)C42—C37—C38—C391.6 (6)
C7—C2—C3—C41.7 (6)C36—C37—C38—C39175.8 (4)
C1—C2—C3—C4178.9 (3)C37—C38—C39—C400.1 (7)
C2—C3—C4—C50.5 (6)C38—C39—C40—C411.9 (7)
C3—C4—C5—C60.8 (7)C39—C40—C41—C422.0 (7)
C4—C5—C6—C70.9 (7)C38—C37—C42—C411.5 (6)
C5—C6—C7—C20.4 (7)C36—C37—C42—C41175.9 (4)
C3—C2—C7—C61.6 (6)C40—C41—C42—C370.3 (7)
C1—C2—C7—C6179.0 (4)Sn2—O2—C43—O1159.9 (2)
C15—Sn1—C8—C976.6 (3)Sn2—O2—C43—C4419.5 (5)
C1—Sn1—C8—C9116.0 (3)Sn1—O1—C43—O23.1 (5)
O1—Sn1—C8—C919.7 (3)Sn1—O1—C43—C44177.5 (2)
O5i—Sn1—C8—C9160.9 (3)O2—C43—C44—C45172.4 (3)
Sn1—C8—C9—C1094.1 (4)O1—C43—C44—C457.1 (5)
Sn1—C8—C9—C1489.0 (4)C43—C44—C45—C46175.2 (3)
C14—C9—C10—C112.2 (6)C49—O3—C46—C470.2 (4)
C8—C9—C10—C11174.8 (4)C49—O3—C46—C47'177 (8)
C9—C10—C11—C120.5 (7)C49—O3—C46—O3'0.4 (7)
C10—C11—C12—C132.4 (6)C49—O3—C46—C45178.2 (4)
C11—C12—C13—C141.6 (6)C49'—O3'—C46—C47179 (2)
C10—C9—C14—C133.0 (5)C49'—O3'—C46—O30.5 (8)
C8—C9—C14—C13174.0 (3)C49'—O3'—C46—C47'0.2 (4)
C12—C13—C14—C91.1 (6)C49'—O3'—C46—C45176.7 (6)
C8—Sn1—C15—C1619.5 (3)C44—C45—C46—C476.9 (6)
C1—Sn1—C15—C16174.2 (2)C44—C45—C46—O3174.7 (5)
O1—Sn1—C15—C1676.9 (3)C44—C45—C46—C47'174.8 (7)
O5i—Sn1—C15—C1696.3 (3)C44—C45—C46—O3'8.6 (10)
Sn1—C15—C16—C2180.7 (4)O3—C46—C47—C480.2 (2)
Sn1—C15—C16—C1798.1 (4)C47'—C46—C47—C480.1 (10)
C21—C16—C17—C182.0 (6)O3'—C46—C47—C481.5 (19)
C15—C16—C17—C18179.1 (4)C45—C46—C47—C48178.3 (4)
C16—C17—C18—C190.8 (7)C46—C47—C48—C490.0 (2)
C17—C18—C19—C200.7 (7)C47—C48—C49—O30.1 (4)
C18—C19—C20—C211.0 (7)C46—O3—C49—C480.1 (4)
C17—C16—C21—C201.7 (6)C47—C46—C47'—C48'0.6 (11)
C15—C16—C21—C20179.4 (4)O3—C46—C47'—C48'3 (8)
C19—C20—C21—C160.2 (7)O3'—C46—C47'—C48'0.1 (3)
C36—Sn2—C22—C23177.3 (2)C45—C46—C47'—C48'177.6 (4)
C29—Sn2—C22—C230.8 (3)C46—C47'—C48'—C49'0.1 (3)
O4—Sn2—C22—C2387.5 (2)C47'—C48'—C49'—O3'0.2 (4)
O2—Sn2—C22—C2385.4 (2)C46—O3'—C49'—C48'0.3 (6)
Sn2—C22—C23—C2496.7 (3)Sn1ii—O5—C50—O4160.6 (2)
Sn2—C22—C23—C2879.2 (4)Sn1ii—O5—C50—C5120.7 (5)
C28—C23—C24—C251.0 (5)Sn2—O4—C50—O516.0 (5)
C22—C23—C24—C25176.9 (3)Sn2—O4—C50—C51162.7 (2)
C23—C24—C25—C260.2 (6)O5—C50—C51—C52178.5 (3)
C24—C25—C26—C270.0 (6)O4—C50—C51—C520.2 (5)
C25—C26—C27—C280.7 (6)C50—C51—C52—C53176.2 (3)
C26—C27—C28—C231.6 (6)C56—O6—C53—C540.7 (4)
C24—C23—C28—C271.7 (5)C56—O6—C53—C52179.7 (3)
C22—C23—C28—C27177.7 (3)C51—C52—C53—C54179.2 (4)
C36—Sn2—C29—C308.7 (3)C51—C52—C53—O62.1 (5)
C22—Sn2—C29—C30168.4 (2)O6—C53—C54—C550.3 (5)
O4—Sn2—C29—C3077.7 (2)C52—C53—C54—C55179.1 (4)
O2—Sn2—C29—C30100.3 (2)C53—C54—C55—C560.2 (5)
Sn2—C29—C30—C3195.1 (3)C54—C55—C56—O60.7 (5)
Sn2—C29—C30—C3581.6 (4)C53—O6—C56—C550.9 (5)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Sn(C7H7)3(C7H5O2)]
Mr529.18
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.5744 (1), 10.8946 (1), 21.4199 (3)
α, β, γ (°)101.7132 (6), 90.6861 (6), 101.2031 (6)
V3)2366.83 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.11
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(TWINABS; Bruker, 2009)
Tmin, Tmax0.574, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
40884, 11649, 10010
Rint0.030
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.106, 1.07
No. of reflections11649
No. of parameters603
No. of restraints56
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.80, 0.58

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLo, K. M. & Ng, S. W. (2011). Acta Cryst. E67, m744–m745.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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