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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055249/cv2335sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055249/cv2335Isup2.hkl
Contains datablock I

CCDC reference: 672620

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.050
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.80 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.06 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C37 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C41 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C49 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C39 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C39 -C44 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C45 -C50 1.36 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.797 Tmax scaled 0.306 Tmin scaled 0.251 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 16 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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 = 566.00F(000) = 1112
Triclinic, P1Dx = 1.644 Mg m3
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 = 2.4–22.2°
α = 113.920 (7)°µ = 2.89 mm1
β = 92.418 (8)°T = 298 K
γ = 93.818 (9)°Block, 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)
Graphite monochromatorRint = 0.042
phi and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 813
Tmin = 0.315, Tmax = 0.384k = 1616
11810 measured reflectionsl = 1818
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.03P)2]
where P = (Fo2 + 2Fc2)/3
7898 reflections(Δ/σ)max = 0.001
541 parametersΔρmax = 1.49 e Å3
1 restraintΔρmin = 1.08 e Å3
Crystal data top
[Sn(C6H5)3(C7H4BrO3)]γ = 93.818 (9)°
Mr = 566.00V = 2287 (3) Å3
Triclinic, P1Z = 4
a = 11.434 (7) ÅMo Kα radiation
b = 14.233 (9) ŵ = 2.89 mm1
c = 15.453 (10) ÅT = 298 K
α = 113.920 (7)°0.52 × 0.47 × 0.41 mm
β = 92.418 (8)°
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 Å3
7898 reflectionsΔρmin = 1.08 e Å3
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)
H40.62810.62040.12380.079*
C50.6308 (7)0.4693 (6)0.1519 (5)0.064 (2)
H50.61940.44530.21760.077*
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)
H400.63580.84440.03020.104*
C410.6120 (8)0.9415 (8)0.0922 (7)0.103 (3)
H410.54700.90300.13190.124*
C420.6530 (8)1.0315 (8)0.0950 (6)0.085 (3)
H420.61581.05540.13580.102*
C430.7477 (8)1.0857 (7)0.0385 (7)0.091 (3)
H430.77681.14740.04030.110*
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)
H481.10130.55630.07760.125*
C491.0150 (8)0.6655 (8)0.0921 (7)0.110 (4)
H491.02710.64680.15590.132*
C500.9517 (6)0.7488 (6)0.0443 (6)0.069 (2)
H500.92000.78510.07660.083*
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, º) 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, º) 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

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C7H4BrO3)]
Mr566.00
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)11.434 (7), 14.233 (9), 15.453 (10)
α, β, γ (°)113.920 (7), 92.418 (8), 93.818 (9)
V3)2287 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.89
Crystal size (mm)0.52 × 0.47 × 0.41
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.315, 0.384
No. of measured, independent and
observed [I > 2σ(I)] reflections
11810, 7898, 4460
Rint0.042
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.104, 1.00
No. of reflections7898
No. of parameters541
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.49, 1.08

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) 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
 

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