(5-Bromo­salicylato)triphenyl­tin(IV)

Wang, H.; Yin, H.; Wang, D.

doi:10.1107/S1600536807055249

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(5-Bromosalicylato)triphenyltin(IV)

H. Wang, H. Yin and D. Wang

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055249/cv2335sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055249/cv2335Isup2.hkl Contains datablock I

CCDC reference: 672620

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (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.

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

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
M_r = 566.00	F(000) = 1112
Triclinic, P1	D_x = 1.644 Mg m⁻³
a = 11.434 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.233 (9) Å	Cell parameters from 2851 reflections
c = 15.453 (10) Å	θ = 2.4–22.2°
α = 113.920 (7)°	µ = 2.89 mm⁻¹
β = 92.418 (8)°	T = 298 K
γ = 93.818 (9)°	Block, colourless
V = 2287 (3) Å³	0.52 × 0.47 × 0.41 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7898 independent reflections
Radiation source: fine-focus sealed tube	4460 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
phi and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→13
T_min = 0.315, T_max = 0.384	k = −16→16
11810 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.03P)²] where P = (F_o² + 2F_c²)/3
7898 reflections	(Δ/σ)_max = 0.001
541 parameters	Δρ_max = 1.49 e Å⁻³
1 restraint	Δρ_min = −1.08 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₇H₄BrO₃)]	γ = 93.818 (9)°
M_r = 566.00	V = 2287 (3) Å³
Triclinic, P1	Z = 4
a = 11.434 (7) Å	Mo Kα radiation
b = 14.233 (9) Å	µ = 2.89 mm⁻¹
c = 15.453 (10) Å	T = 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)
T_min = 0.315, T_max = 0.384	R_int = 0.042
11810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.104	H-atom parameters constrained
S = 1.00	Δρ_max = 1.49 e Å⁻³
7898 reflections	Δρ_min = −1.08 e Å⁻³
541 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.73602 (4)	0.56543 (3)	0.32221 (3)	0.04496 (16)
Sn2	0.84682 (4)	0.90686 (4)	0.12077 (3)	0.04421 (16)
O1	0.7057 (4)	0.5070 (3)	0.1778 (3)	0.0520 (12)
O2	0.6858 (4)	0.6686 (4)	0.1996 (3)	0.0572 (13)
O3	0.6488 (4)	0.7113 (3)	0.0540 (3)	0.0632 (14)
H3	0.6599	0.7239	0.1105	0.095*
O4	0.9747 (4)	1.0319 (3)	0.1780 (3)	0.0536 (13)
O5	1.0545 (4)	0.9425 (4)	0.2486 (4)	0.0734 (16)
O6	1.2595 (6)	1.0097 (6)	0.3379 (5)	0.122 (3)
H6	1.2034	0.9675	0.3105	0.183*
Br1	0.63956 (9)	0.25806 (6)	−0.18809 (6)	0.0788 (3)
Br2	1.19838 (15)	1.41108 (11)	0.30941 (9)	0.1746 (7)
C1	0.6843 (6)	0.5753 (6)	0.1463 (5)	0.0467 (18)
C2	0.6638 (5)	0.5393 (5)	0.0428 (5)	0.0411 (17)
C3	0.6493 (6)	0.6095 (6)	0.0026 (5)	0.0518 (19)
C4	0.6349 (7)	0.5739 (6)	−0.0959 (6)	0.066 (2)
H4	0.6281	0.6204	−0.1238	0.079*
C5	0.6308 (7)	0.4693 (6)	−0.1519 (5)	0.064 (2)
H5	0.6194	0.4453	−0.2176	0.077*
C6	0.6433 (6)	0.4013 (5)	−0.1114 (5)	0.0469 (18)
C7	0.6595 (5)	0.4357 (5)	−0.0149 (5)	0.0478 (18)
H7	0.6677	0.3886	0.0120	0.057*
C8	0.7657 (6)	0.4229 (5)	0.3271 (5)	0.0499 (19)
C9	0.7073 (8)	0.3321 (6)	0.2696 (6)	0.089 (3)
H9	0.6496	0.3315	0.2251	0.107*
C10	0.7293 (12)	0.2403 (6)	0.2739 (7)	0.123 (4)
H10	0.6870	0.1790	0.2332	0.148*
C11	0.8125 (11)	0.2406 (8)	0.3374 (8)	0.102 (4)
H11	0.8268	0.1790	0.3417	0.122*
C12	0.8754 (8)	0.3279 (8)	0.3948 (8)	0.095 (3)
H12	0.9348	0.3265	0.4370	0.114*
C13	0.8525 (7)	0.4185 (6)	0.3914 (6)	0.070 (2)
H13	0.8955	0.4791	0.4327	0.084*
C14	0.5805 (6)	0.6271 (5)	0.3818 (4)	0.0397 (17)
C15	0.5098 (7)	0.5749 (5)	0.4219 (5)	0.054 (2)
H15	0.5290	0.5120	0.4207	0.064*
C16	0.4100 (7)	0.6182 (7)	0.4639 (5)	0.070 (2)
H16	0.3625	0.5843	0.4917	0.084*
C17	0.3814 (7)	0.7104 (8)	0.4645 (5)	0.072 (2)
H17	0.3145	0.7389	0.4925	0.086*
C18	0.4490 (7)	0.7589 (6)	0.4251 (5)	0.061 (2)
H18	0.4285	0.8211	0.4254	0.073*
C19	0.5483 (6)	0.7192 (5)	0.3841 (5)	0.0512 (19)
H19	0.5947	0.7551	0.3574	0.061*
C20	0.8909 (6)	0.6673 (6)	0.3631 (5)	0.0533 (19)
C21	0.9877 (8)	0.6457 (7)	0.3116 (6)	0.079 (3)
H21	0.9842	0.5852	0.2566	0.095*
C22	1.0898 (8)	0.7106 (9)	0.3383 (7)	0.099 (3)
H22	1.1556	0.6924	0.3038	0.118*
C23	1.0931 (8)	0.8006 (8)	0.4151 (8)	0.083 (3)
H23	1.1602	0.8467	0.4309	0.099*
C24	1.0017 (9)	0.8253 (7)	0.4694 (7)	0.084 (3)
H24	1.0072	0.8865	0.5239	0.101*
C25	0.8973 (7)	0.7585 (6)	0.4437 (6)	0.067 (2)
H25	0.8334	0.7756	0.4806	0.080*
C26	1.0539 (6)	1.0204 (7)	0.2325 (5)	0.056 (2)
C27	1.1469 (6)	1.1072 (7)	0.2778 (5)	0.062 (2)
C28	1.2458 (8)	1.0956 (9)	0.3280 (6)	0.085 (3)
C29	1.3333 (12)	1.1784 (11)	0.3673 (9)	0.129 (6)
H29	1.4011	1.1718	0.3990	0.155*
C30	1.3190 (12)	1.2661 (13)	0.3590 (9)	0.144 (7)
H30	1.3782	1.3200	0.3854	0.173*
C31	1.2216 (10)	1.2814 (8)	0.3137 (6)	0.107 (4)
C32	1.1341 (7)	1.2010 (7)	0.2719 (5)	0.074 (3)
H32	1.0676	1.2096	0.2402	0.089*
C33	0.7522 (6)	0.9299 (5)	0.2414 (5)	0.0499 (19)
C34	0.8015 (7)	0.9261 (5)	0.3224 (5)	0.062 (2)
H34	0.8773	0.9062	0.3230	0.075*
C35	0.7407 (10)	0.9510 (6)	0.4028 (6)	0.082 (3)
H35	0.7762	0.9497	0.4575	0.098*
C36	0.6303 (11)	0.9772 (7)	0.4019 (8)	0.097 (4)
H36	0.5898	0.9944	0.4564	0.116*
C37	0.5765 (9)	0.9790 (7)	0.3219 (9)	0.104 (4)
H37	0.4990	0.9949	0.3211	0.124*
C38	0.6395 (7)	0.9566 (6)	0.2412 (6)	0.072 (2)
H38	0.6046	0.9600	0.1872	0.087*
C39	0.7617 (6)	0.9608 (5)	0.0278 (4)	0.0469 (18)
C40	0.6655 (8)	0.9063 (7)	−0.0313 (6)	0.087 (3)
H40	0.6358	0.8444	−0.0302	0.104*
C41	0.6120 (8)	0.9415 (8)	−0.0922 (7)	0.103 (3)
H41	0.5470	0.9030	−0.1319	0.124*
C42	0.6530 (8)	1.0315 (8)	−0.0950 (6)	0.085 (3)
H42	0.6158	1.0554	−0.1358	0.102*
C43	0.7477 (8)	1.0857 (7)	−0.0385 (7)	0.091 (3)
H43	0.7768	1.1474	−0.0403	0.110*
C44	0.8026 (7)	1.0501 (6)	0.0228 (6)	0.079 (3)
H44	0.8687	1.0883	0.0612	0.095*
C45	0.9356 (6)	0.7777 (5)	0.0486 (5)	0.0478 (18)
C46	0.9812 (7)	0.7202 (6)	0.0937 (6)	0.076 (2)
H46	0.9700	0.7381	0.1575	0.091*
C47	1.0421 (9)	0.6379 (7)	0.0463 (8)	0.101 (3)
H47	1.0719	0.5997	0.0774	0.121*
C48	1.0587 (8)	0.6121 (7)	−0.0455 (9)	0.104 (4)
H48	1.1013	0.5563	−0.0776	0.125*
C49	1.0150 (8)	0.6655 (8)	−0.0921 (7)	0.110 (4)
H49	1.0271	0.6468	−0.1559	0.132*
C50	0.9517 (6)	0.7488 (6)	−0.0443 (6)	0.069 (2)
H50	0.9200	0.7851	−0.0766	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0528 (3)	0.0453 (3)	0.0366 (3)	−0.0001 (3)	−0.0015 (2)	0.0178 (2)
Sn2	0.0393 (3)	0.0503 (3)	0.0422 (3)	0.0039 (2)	−0.0069 (2)	0.0191 (2)
O1	0.071 (3)	0.050 (3)	0.038 (3)	0.010 (3)	0.001 (2)	0.020 (2)
O2	0.072 (4)	0.054 (3)	0.042 (3)	0.001 (3)	0.000 (3)	0.017 (3)
O3	0.078 (4)	0.056 (3)	0.064 (4)	0.013 (3)	0.008 (3)	0.032 (3)
O4	0.043 (3)	0.062 (3)	0.050 (3)	−0.013 (3)	−0.018 (2)	0.022 (3)
O5	0.062 (4)	0.092 (4)	0.071 (4)	0.007 (3)	−0.009 (3)	0.040 (3)
O6	0.090 (5)	0.179 (8)	0.080 (5)	0.020 (5)	−0.037 (4)	0.038 (5)
Br1	0.1071 (7)	0.0675 (5)	0.0490 (5)	−0.0003 (5)	−0.0052 (5)	0.0131 (4)
Br2	0.2350 (17)	0.1388 (11)	0.1236 (11)	−0.1209 (12)	−0.0456 (10)	0.0531 (9)
C1	0.048 (5)	0.051 (5)	0.043 (5)	−0.001 (4)	0.011 (4)	0.022 (4)
C2	0.039 (4)	0.052 (4)	0.037 (4)	0.000 (4)	0.002 (3)	0.024 (4)
C3	0.054 (5)	0.060 (5)	0.046 (5)	0.000 (4)	0.004 (4)	0.026 (4)
C4	0.084 (6)	0.076 (6)	0.057 (6)	0.014 (5)	0.005 (5)	0.046 (5)
C5	0.077 (6)	0.080 (6)	0.035 (5)	0.000 (5)	−0.001 (4)	0.024 (5)
C6	0.043 (4)	0.050 (4)	0.050 (5)	−0.005 (4)	−0.005 (4)	0.025 (4)
C7	0.050 (5)	0.062 (5)	0.038 (4)	0.005 (4)	0.002 (3)	0.028 (4)
C8	0.069 (5)	0.045 (4)	0.037 (4)	0.002 (4)	0.008 (4)	0.018 (4)
C9	0.128 (8)	0.054 (5)	0.080 (7)	−0.005 (6)	−0.035 (6)	0.028 (5)
C10	0.230 (14)	0.036 (5)	0.099 (9)	0.012 (7)	−0.017 (9)	0.028 (6)
C11	0.149 (11)	0.080 (8)	0.109 (10)	0.051 (8)	0.047 (8)	0.062 (7)
C12	0.093 (8)	0.095 (7)	0.126 (9)	0.014 (7)	−0.007 (6)	0.074 (7)
C13	0.070 (6)	0.061 (5)	0.093 (7)	−0.002 (5)	−0.004 (5)	0.049 (5)
C14	0.042 (4)	0.048 (4)	0.029 (4)	0.000 (4)	−0.005 (3)	0.018 (3)
C15	0.060 (5)	0.060 (5)	0.040 (5)	−0.010 (4)	−0.007 (4)	0.024 (4)
C16	0.047 (5)	0.112 (8)	0.064 (6)	−0.014 (5)	0.005 (4)	0.053 (6)
C17	0.046 (5)	0.113 (8)	0.049 (5)	0.021 (6)	−0.003 (4)	0.025 (5)
C18	0.065 (6)	0.073 (6)	0.050 (5)	0.017 (5)	0.006 (4)	0.029 (4)
C19	0.054 (5)	0.052 (5)	0.044 (5)	−0.006 (4)	0.006 (4)	0.018 (4)
C20	0.046 (5)	0.069 (5)	0.051 (5)	−0.001 (4)	−0.006 (4)	0.033 (4)
C21	0.065 (6)	0.097 (7)	0.060 (6)	0.001 (6)	0.003 (5)	0.019 (5)
C22	0.056 (7)	0.134 (9)	0.096 (8)	−0.010 (7)	0.015 (6)	0.038 (7)
C23	0.059 (7)	0.090 (8)	0.114 (9)	−0.020 (6)	−0.017 (6)	0.064 (7)
C24	0.087 (7)	0.062 (6)	0.088 (7)	−0.007 (6)	−0.024 (6)	0.020 (5)
C25	0.052 (5)	0.066 (5)	0.071 (6)	0.002 (5)	0.001 (4)	0.018 (5)
C26	0.039 (5)	0.080 (6)	0.036 (5)	−0.009 (5)	0.003 (4)	0.013 (4)
C27	0.043 (5)	0.099 (7)	0.030 (4)	−0.008 (5)	−0.003 (4)	0.015 (5)
C28	0.051 (6)	0.142 (10)	0.043 (6)	0.008 (7)	−0.007 (4)	0.018 (6)
C29	0.062 (8)	0.207 (16)	0.062 (7)	−0.005 (11)	−0.026 (6)	0.003 (10)
C30	0.072 (10)	0.237 (18)	0.057 (8)	−0.067 (12)	−0.010 (6)	0.005 (11)
C31	0.117 (9)	0.132 (9)	0.044 (6)	−0.073 (8)	−0.017 (6)	0.021 (6)
C32	0.069 (6)	0.100 (7)	0.040 (5)	−0.034 (6)	−0.009 (4)	0.022 (5)
C33	0.047 (5)	0.034 (4)	0.054 (5)	−0.005 (4)	−0.012 (4)	0.006 (4)
C34	0.066 (6)	0.070 (5)	0.054 (5)	0.009 (5)	0.009 (5)	0.027 (4)
C35	0.105 (8)	0.072 (6)	0.059 (6)	−0.010 (6)	0.023 (6)	0.019 (5)
C36	0.114 (10)	0.063 (6)	0.087 (8)	−0.012 (7)	0.049 (7)	0.004 (6)
C37	0.061 (7)	0.080 (7)	0.147 (11)	0.008 (6)	0.054 (8)	0.019 (8)
C38	0.058 (6)	0.061 (5)	0.090 (7)	0.004 (5)	0.003 (5)	0.024 (5)
C39	0.046 (5)	0.054 (4)	0.041 (4)	0.003 (4)	−0.007 (4)	0.020 (4)
C40	0.090 (7)	0.082 (6)	0.095 (7)	−0.017 (6)	−0.041 (6)	0.052 (6)
C41	0.089 (8)	0.099 (8)	0.116 (9)	−0.038 (6)	−0.042 (6)	0.050 (7)
C42	0.078 (7)	0.117 (8)	0.079 (7)	−0.005 (6)	−0.015 (5)	0.065 (6)
C43	0.098 (8)	0.093 (7)	0.107 (8)	−0.012 (6)	−0.025 (6)	0.070 (6)
C44	0.078 (6)	0.085 (6)	0.084 (7)	−0.020 (5)	−0.031 (5)	0.051 (5)
C45	0.043 (4)	0.047 (4)	0.043 (5)	−0.002 (4)	0.002 (4)	0.009 (4)
C46	0.082 (6)	0.069 (6)	0.076 (6)	0.026 (5)	−0.005 (5)	0.028 (5)
C47	0.113 (8)	0.072 (7)	0.098 (8)	0.026 (6)	−0.030 (7)	0.016 (6)
C48	0.062 (6)	0.089 (7)	0.111 (10)	0.036 (5)	−0.017 (6)	−0.012 (7)
C49	0.083 (7)	0.147 (10)	0.062 (7)	0.034 (7)	0.012 (6)	0.001 (7)
C50	0.059 (5)	0.076 (6)	0.063 (6)	0.015 (5)	0.008 (4)	0.017 (5)

Geometric parameters (Å, º) top

Sn1—O1	2.045 (4)	C21—C22	1.376 (11)
Sn1—C8	2.110 (7)	C21—H21	0.9300
Sn1—C20	2.112 (7)	C22—C23	1.344 (11)
Sn1—C14	2.115 (7)	C22—H22	0.9300
Sn2—C45	2.082 (7)	C23—C24	1.344 (11)
Sn2—O4	2.087 (4)	C23—H23	0.9300
Sn2—C33	2.116 (7)	C24—C25	1.411 (10)
Sn2—C39	2.117 (7)	C24—H24	0.9300
O1—C1	1.283 (7)	C25—H25	0.9300
O2—C1	1.246 (7)	C26—C27	1.486 (10)
O3—C3	1.340 (7)	C27—C32	1.390 (10)
O3—H3	0.8200	C27—C28	1.401 (11)
O4—C26	1.274 (8)	C28—C29	1.404 (15)
O5—C26	1.231 (8)	C29—C30	1.325 (17)
O6—C28	1.311 (11)	C29—H29	0.9300
O6—H6	0.8200	C30—C31	1.366 (16)
Br1—C6	1.894 (7)	C30—H30	0.9300
Br2—C31	1.910 (11)	C31—C32	1.386 (11)
C1—C2	1.470 (9)	C32—H32	0.9300
C2—C7	1.375 (8)	C33—C38	1.368 (10)
C2—C3	1.390 (9)	C33—C34	1.373 (9)
C3—C4	1.394 (9)	C34—C35	1.379 (10)
C4—C5	1.383 (9)	C34—H34	0.9300
C4—H4	0.9300	C35—C36	1.341 (12)
C5—C6	1.361 (9)	C35—H35	0.9300
C5—H5	0.9300	C36—C37	1.368 (13)
C6—C7	1.366 (8)	C36—H36	0.9300
C7—H7	0.9300	C37—C38	1.400 (11)
C8—C9	1.344 (9)	C37—H37	0.9300
C8—C13	1.396 (9)	C38—H38	0.9300
C9—C10	1.374 (11)	C39—C44	1.358 (9)
C9—H9	0.9300	C39—C40	1.368 (9)
C10—C11	1.336 (13)	C40—C41	1.372 (10)
C10—H10	0.9300	C40—H40	0.9300
C11—C12	1.334 (12)	C41—C42	1.353 (10)
C11—H11	0.9300	C41—H41	0.9300
C12—C13	1.354 (10)	C42—C43	1.340 (10)
C12—H12	0.9300	C42—H42	0.9300
C13—H13	0.9300	C43—C44	1.388 (10)
C14—C19	1.372 (8)	C43—H43	0.9300
C14—C15	1.387 (8)	C44—H44	0.9300
C15—C16	1.391 (10)	C45—C50	1.348 (9)
C15—H15	0.9300	C45—C46	1.384 (9)
C16—C17	1.370 (10)	C46—C47	1.360 (11)
C16—H16	0.9300	C46—H46	0.9300
C17—C18	1.324 (10)	C47—C48	1.339 (12)
C17—H17	0.9300	C47—H47	0.9300
C18—C19	1.366 (9)	C48—C49	1.347 (12)
C18—H18	0.9300	C48—H48	0.9300
C19—H19	0.9300	C49—C50	1.387 (11)
C20—C21	1.369 (10)	C49—H49	0.9300
C20—C25	1.381 (9)	C50—H50	0.9300

O1—Sn1—C8	95.4 (2)	C24—C23—H23	119.3
O1—Sn1—C20	108.9 (2)	C22—C23—H23	119.3
C8—Sn1—C20	111.4 (3)	C23—C24—C25	120.0 (8)
O1—Sn1—C14	107.4 (2)	C23—C24—H24	120.0
C8—Sn1—C14	114.5 (3)	C25—C24—H24	120.0
C20—Sn1—C14	116.8 (3)	C20—C25—C24	119.3 (7)
C45—Sn2—O4	106.3 (2)	C20—C25—H25	120.3
C45—Sn2—C33	125.0 (3)	C24—C25—H25	120.3
O4—Sn2—C33	100.3 (2)	O5—C26—O4	122.8 (7)
C45—Sn2—C39	112.4 (3)	O5—C26—C27	120.7 (8)
O4—Sn2—C39	95.2 (2)	O4—C26—C27	116.6 (8)
C33—Sn2—C39	112.0 (3)	C32—C27—C28	120.0 (9)
C1—O1—Sn1	113.8 (4)	C32—C27—C26	119.7 (8)
C3—O3—H3	109.5	C28—C27—C26	120.3 (9)
C26—O4—Sn2	113.3 (5)	O6—C28—C27	122.0 (10)
C28—O6—H6	109.5	O6—C28—C29	119.5 (10)
O2—C1—O1	122.2 (7)	C27—C28—C29	118.5 (11)
O2—C1—C2	120.8 (7)	C30—C29—C28	119.7 (15)
O1—C1—C2	116.9 (6)	C30—C29—H29	120.1
C7—C2—C3	119.5 (6)	C28—C29—H29	120.1
C7—C2—C1	120.2 (6)	C29—C30—C31	123.2 (16)
C3—C2—C1	120.3 (6)	C29—C30—H30	118.4
O3—C3—C2	123.2 (7)	C31—C30—H30	118.4
O3—C3—C4	117.6 (7)	C30—C31—C32	119.0 (12)
C2—C3—C4	119.2 (7)	C30—C31—Br2	122.5 (10)
C5—C4—C3	119.7 (7)	C32—C31—Br2	118.4 (9)
C5—C4—H4	120.1	C31—C32—C27	119.4 (9)
C3—C4—H4	120.1	C31—C32—H32	120.3
C6—C5—C4	120.3 (7)	C27—C32—H32	120.3
C6—C5—H5	119.9	C38—C33—C34	118.5 (7)
C4—C5—H5	119.9	C38—C33—Sn2	118.5 (6)
C5—C6—C7	120.3 (7)	C34—C33—Sn2	122.9 (6)
C5—C6—Br1	120.3 (6)	C33—C34—C35	121.2 (8)
C7—C6—Br1	119.4 (5)	C33—C34—H34	119.4
C6—C7—C2	120.9 (6)	C35—C34—H34	119.4
C6—C7—H7	119.6	C36—C35—C34	119.9 (10)
C2—C7—H7	119.6	C36—C35—H35	120.1
C9—C8—C13	115.9 (7)	C34—C35—H35	120.1
C9—C8—Sn1	124.1 (6)	C35—C36—C37	120.8 (10)
C13—C8—Sn1	120.1 (5)	C35—C36—H36	119.6
C8—C9—C10	122.7 (9)	C37—C36—H36	119.6
C8—C9—H9	118.6	C36—C37—C38	119.2 (10)
C10—C9—H9	118.6	C36—C37—H37	120.4
C11—C10—C9	119.0 (10)	C38—C37—H37	120.4
C11—C10—H10	120.5	C33—C38—C37	120.3 (9)
C9—C10—H10	120.5	C33—C38—H38	119.8
C12—C11—C10	121.0 (9)	C37—C38—H38	119.8
C12—C11—H11	119.5	C44—C39—C40	117.3 (7)
C10—C11—H11	119.5	C44—C39—Sn2	121.0 (6)
C11—C12—C13	120.0 (9)	C40—C39—Sn2	121.7 (6)
C11—C12—H12	120.0	C39—C40—C41	121.1 (8)
C13—C12—H12	120.0	C39—C40—H40	119.4
C12—C13—C8	121.4 (8)	C41—C40—H40	119.4
C12—C13—H13	119.3	C42—C41—C40	120.7 (9)
C8—C13—H13	119.3	C42—C41—H41	119.7
C19—C14—C15	118.6 (6)	C40—C41—H41	119.7
C19—C14—Sn1	121.8 (5)	C43—C42—C41	119.3 (9)
C15—C14—Sn1	119.6 (5)	C43—C42—H42	120.4
C14—C15—C16	119.0 (7)	C41—C42—H42	120.4
C14—C15—H15	120.5	C42—C43—C44	120.2 (8)
C16—C15—H15	120.5	C42—C43—H43	119.9
C17—C16—C15	120.4 (7)	C44—C43—H43	119.9
C17—C16—H16	119.8	C39—C44—C43	121.4 (8)
C15—C16—H16	119.8	C39—C44—H44	119.3
C18—C17—C16	120.0 (8)	C43—C44—H44	119.3
C18—C17—H17	120.0	C50—C45—C46	118.1 (7)
C16—C17—H17	120.0	C50—C45—Sn2	120.1 (6)
C17—C18—C19	121.3 (8)	C46—C45—Sn2	121.8 (6)
C17—C18—H18	119.4	C47—C46—C45	121.1 (9)
C19—C18—H18	119.4	C47—C46—H46	119.4
C18—C19—C14	120.8 (7)	C45—C46—H46	119.4
C18—C19—H19	119.6	C48—C47—C46	119.6 (10)
C14—C19—H19	119.6	C48—C47—H47	120.2
C21—C20—C25	117.9 (7)	C46—C47—H47	120.2
C21—C20—Sn1	121.6 (6)	C47—C48—C49	121.1 (10)
C25—C20—Sn1	120.4 (6)	C47—C48—H48	119.4
C20—C21—C22	122.2 (8)	C49—C48—H48	119.4
C20—C21—H21	118.9	C48—C49—C50	119.5 (9)
C22—C21—H21	118.9	C48—C49—H49	120.3
C23—C22—C21	119.0 (9)	C50—C49—H49	120.3
C23—C22—H22	120.5	C45—C50—C49	120.6 (8)
C21—C22—H22	120.5	C45—C50—H50	119.7
C24—C23—C22	121.4 (9)	C49—C50—H50	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.583 (8)	146
O6—H6···O5	0.82	1.86	2.583 (9)	147

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₇H₄BrO₃)]
M_r	566.00
Crystal system, space group	Triclinic, 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)
V (Å³)	2287 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.89
Crystal size (mm)	0.52 × 0.47 × 0.41

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.315, 0.384
No. of measured, independent and observed [I > 2σ(I)] reflections	11810, 7898, 4460
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.104, 1.00
No. of reflections	7898
No. of parameters	541
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.583 (8)	146
O6—H6···O5	0.82	1.86	2.583 (9)	147

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