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The structure at 298 K described here, [Sn(C6H5)3(C7H4NO4)], completely confirms the results at 173 K obtained previously [Weng, Das & Robinson (1990), Malays. J. Sci. 12, 57]. In both structures, weak interaction between Sn and the carbonyl O atom of the benzoate group provides a distorted trigonal-pyramidal environment at the Sn atom derived from its pseudo-tetrahedral primary coordination in both mol­ecules of the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004510/qa0261sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004510/qa0261Isup2.hkl
Contains datablock I

CCDC reference: 145628

Comment top

It was only upon completion of the solution and refinement of the 298 K structure reported here that a search of the Cambridge Structural Database (Allen & Kennard, 1993) by means of the CSSR component of the EPSRC's Chemical Database Service at Daresbury (Fletcher et al., 1996) revealed the existence of the 173 K structure described by Weng et al. (1990; CSD No. 170773, CODEN RACFUW.). Aside from the reversal in direction of cell edges a and b and the increased cell dimensions and thermal parameters at 298 K, the two structures are identical. Thus, making due allowance for the diffent labelling schemes, the description of the 298 K structure which follows applies equally to both structures.

The asymmetric unit consists of two independent molecules, A and B, whose atoms are labelled in an identical manner and distinguished by suffix A or B except for the Sn atoms, which are distinguished by number (1 or 2). As a consequence, geometric parameters are given below in pairs with those for molecule A preceding the corresponding value in square brackets for molecule B.

With a few exceptions, the bond lengths and angles observed are unremarkable. However, in the p-nitrobenzoate groups, both the carboxylate and nitro substituents are rotated around the C—X bond (X = C or N) by 26.8 (6) [13.4 (6)°] and 19.2 (7)° [16.0 (7)°], respectively, to displace O from the plane of the benzene ring. Also of interest is the coordination of Sn (Table 1). The primary coordination by O1, C8, C14 and C20 is tetrahedral in nature but highly distorted, as evidenced for example by the O1—Sn—C20 angle. The distortion is perceived to be of the order of 11.7° [15.2°] towards a trigonal-bipyramidal configuration with the introduction of O2 axial and trans to C20, and O1, C8 and C14 equatorial. In molecule A, the axial Sn—C20 bond is appreciably longer than the equatorial Sn—C bonds, but a similar effect is not apparent in molecule B. With the inclusion of the Sn—O2 contact, the benzoate carboxylate group now acts in a bidentate manner, but with a bite angle of only 50.10 (11)° [51.78 (12)°] which, despite amelioration by the length of the Sn—O2 bond, renders the bipyramid extremely distorted also.

The two molecules in the asymmetric unit are clearly generally quite similar. However, comparison of the values given pairwise above and in Table 1 clearly shows that they are not identical. The differences between them are attributed to packing effects rather than fundamental structural differences.

Experimental top

The title compound was prepared from bis(triphenyl)tin oxide and p-nitrobenzoic acid (1:2 molar ratio) in toluene using a Dean–Stark separator. The residue, after removal of solvent, was recrystallized from chloroform/petroleum ether (333–353 K).

Computing details top

Data collection: Nicolet P3 Software (Nicolet, 1980); cell refinement: Nicolet P3 Software; data reduction: RDNIC (Howie, 1980); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

p-Nitrobenzoato-triphenyl-tin top
Crystal data top
[Sn(C6H5)3(C7H4NO4)]Z = 4
Mr = 516.10F(000) = 1032
Triclinic, P1Dx = 1.550 Mg m3
a = 8.949 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.302 (16) ÅCell parameters from 14 reflections
c = 17.530 (16) Åθ = 10.0–11.5°
α = 94.89 (8)°µ = 1.19 mm1
β = 83.79 (8)°T = 298 K
γ = 96.24 (9)°Block, colourless
V = 2211 (4) Å30.50 × 0.40 × 0.20 mm
Data collection top
Nicolet P3
diffractometer
7111 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.6°, θmin = 1.2°
θ–2θ scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 1818
Tmin = 0.471, Tmax = 0.598l = 2222
10232 measured reflections2 standard reflections every 50 reflections
10230 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0345P)2 + 1.0146P]
where P = (Fo2 + 2Fc2)/3
10230 reflections(Δ/σ)max = 0.001
559 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
[Sn(C6H5)3(C7H4NO4)]γ = 96.24 (9)°
Mr = 516.10V = 2211 (4) Å3
Triclinic, P1Z = 4
a = 8.949 (11) ÅMo Kα radiation
b = 14.302 (16) ŵ = 1.19 mm1
c = 17.530 (16) ÅT = 298 K
α = 94.89 (8)°0.50 × 0.40 × 0.20 mm
β = 83.79 (8)°
Data collection top
Nicolet P3
diffractometer
7111 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.055
Tmin = 0.471, Tmax = 0.5982 standard reflections every 50 reflections
10232 measured reflections intensity decay: none
10230 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.02Δρmax = 0.55 e Å3
10230 reflectionsΔρmin = 0.58 e Å3
559 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

The structure was solved by the heavy-atom method and refined in the usual manner. H atoms were placed in calculated positions and refined with a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.05234 (3)0.481014 (18)0.156345 (14)0.04181 (8)
O1A0.2042 (3)0.55346 (18)0.07880 (15)0.0519 (7)
O2A0.1688 (3)0.6766 (2)0.16208 (16)0.0601 (7)
O3A0.6557 (5)0.8245 (3)0.1700 (3)0.1213 (17)
O4A0.6041 (5)0.9502 (3)0.1042 (3)0.1112 (15)
N1A0.5943 (5)0.8655 (3)0.1152 (3)0.0776 (12)
C1A0.2261 (4)0.6429 (3)0.1011 (2)0.0474 (9)
C2A0.3266 (4)0.7011 (3)0.0461 (2)0.0428 (8)
C3A0.4361 (5)0.6621 (3)0.0048 (2)0.0553 (10)
H3A0.44940.59860.00410.066*
C4A0.5252 (5)0.7161 (3)0.0565 (3)0.0636 (12)
H4A0.59950.69010.09050.076*
C5A0.5023 (4)0.8086 (3)0.0569 (2)0.0540 (10)
C6A0.3979 (5)0.8506 (3)0.0082 (3)0.0655 (12)
H6A0.38500.91400.01020.079*
C7A0.3104 (5)0.7959 (3)0.0449 (2)0.0610 (11)
H7A0.23990.82350.08020.073*
C8A0.1552 (4)0.5419 (3)0.1731 (2)0.0434 (8)
C9A0.2806 (5)0.4915 (3)0.1457 (2)0.0535 (10)
H9A0.27000.43470.11660.064*
C10A0.4231 (5)0.5235 (4)0.1604 (3)0.0655 (12)
H10A0.50700.48790.14220.079*
C11A0.4383 (5)0.6076 (3)0.2018 (3)0.0630 (12)
H11A0.53290.63000.21130.076*
C12A0.3150 (5)0.6595 (3)0.2294 (3)0.0646 (12)
H12A0.32610.71680.25750.078*
C13A0.1739 (4)0.6268 (3)0.2155 (2)0.0546 (10)
H13A0.09090.66220.23480.066*
C14A0.1651 (4)0.4712 (3)0.2544 (2)0.0444 (8)
C15A0.2306 (5)0.3888 (3)0.2624 (3)0.0618 (11)
H15A0.22380.33940.22450.074*
C16A0.3055 (6)0.3797 (4)0.3257 (3)0.0823 (16)
H16A0.34810.32420.33020.099*
C17A0.3174 (6)0.4523 (5)0.3822 (3)0.0845 (17)
H17A0.36860.44650.42470.101*
C18A0.2529 (6)0.5332 (4)0.3750 (3)0.0782 (15)
H18A0.25980.58230.41320.094*
C19A0.1775 (4)0.5430 (3)0.3116 (2)0.0553 (10)
H19A0.13480.59870.30760.066*
C20A0.0441 (4)0.3500 (3)0.0893 (2)0.0458 (9)
C21A0.0172 (5)0.2664 (3)0.1196 (2)0.0658 (12)
H21A0.06470.26850.16950.079*
C22A0.0105 (6)0.1806 (3)0.0788 (3)0.0807 (15)
H22A0.05350.12590.10090.097*
C23A0.0597 (6)0.1756 (3)0.0055 (3)0.0795 (15)
H23A0.06630.11740.02200.095*
C24A0.1203 (6)0.2566 (4)0.0271 (3)0.0743 (14)
H24A0.16800.25360.07690.089*
C25A0.1104 (5)0.3429 (3)0.0142 (2)0.0601 (11)
H25A0.14930.39760.00910.072*
Sn20.03142 (3)0.172177 (17)0.435676 (15)0.04193 (8)
O1B0.1942 (3)0.10630 (19)0.51250 (15)0.0530 (7)
O2B0.1489 (3)0.2426 (2)0.57969 (17)0.0615 (8)
O3B0.7025 (5)0.0567 (3)0.8029 (2)0.1067 (14)
O4B0.6732 (5)0.0762 (3)0.8687 (2)0.1086 (14)
N1B0.6460 (5)0.0242 (4)0.8126 (3)0.0768 (12)
C1B0.2171 (4)0.1638 (3)0.5732 (2)0.0478 (9)
C2B0.3329 (4)0.1274 (2)0.6348 (2)0.0421 (8)
C3B0.4298 (5)0.0480 (3)0.6206 (2)0.0558 (10)
H3B0.42540.01700.57170.067*
C4B0.5338 (5)0.0137 (3)0.6784 (3)0.0634 (12)
H4B0.59920.04020.66910.076*
C5B0.5375 (4)0.0615 (3)0.7496 (2)0.0500 (9)
C6B0.4462 (5)0.1415 (3)0.7645 (2)0.0585 (11)
H6B0.45380.17340.81310.070*
C7B0.3420 (5)0.1751 (3)0.7072 (2)0.0579 (11)
H7B0.27800.22950.71690.069*
C8B0.1788 (4)0.2141 (3)0.4804 (2)0.0450 (9)
C9B0.3030 (4)0.1728 (3)0.4436 (3)0.0593 (11)
H9B0.28940.12510.40470.071*
C10B0.4466 (5)0.2014 (4)0.4640 (3)0.0751 (14)
H10B0.52870.17300.43890.090*
C11B0.4686 (5)0.2714 (3)0.5209 (3)0.0698 (13)
H11B0.56550.29080.53430.084*
C12B0.3465 (5)0.3131 (3)0.5584 (3)0.0677 (12)
H12B0.36080.36050.59740.081*
C13B0.2024 (5)0.2842 (3)0.5378 (2)0.0548 (10)
H13B0.12050.31280.56320.066*
C14B0.1344 (4)0.2800 (3)0.3921 (2)0.0440 (8)
C15B0.2183 (5)0.2595 (3)0.3296 (2)0.0563 (10)
H15B0.22580.19870.30580.068*
C16B0.2910 (5)0.3287 (4)0.3023 (3)0.0723 (14)
H16B0.34810.31380.26080.087*
C17B0.2796 (5)0.4181 (4)0.3356 (3)0.0711 (14)
H17B0.32870.46430.31720.085*
C18B0.1951 (6)0.4396 (3)0.3966 (3)0.0705 (13)
H18B0.18670.50070.41950.085*
C19B0.1222 (5)0.3710 (3)0.4242 (3)0.0590 (11)
H19B0.06410.38690.46520.071*
C20B0.0186 (4)0.0533 (2)0.3544 (2)0.0429 (8)
C21B0.0591 (5)0.0622 (3)0.2820 (2)0.0647 (12)
H21B0.10650.12080.26950.078*
C22B0.0679 (6)0.0131 (3)0.2286 (3)0.0772 (14)
H22B0.12090.00530.18050.093*
C23B0.0015 (6)0.1000 (3)0.2458 (3)0.0696 (13)
H23B0.00420.15150.20980.084*
C24B0.0794 (5)0.1100 (3)0.3167 (3)0.0673 (12)
H24B0.12730.16870.32860.081*
C25B0.0880 (5)0.0353 (3)0.3703 (2)0.0559 (10)
H25B0.14120.04400.41820.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03884 (14)0.04461 (15)0.04168 (15)0.00362 (11)0.00133 (11)0.00569 (11)
O1A0.0545 (16)0.0475 (16)0.0501 (16)0.0056 (12)0.0024 (13)0.0071 (12)
O2A0.0629 (18)0.0642 (18)0.0485 (17)0.0025 (14)0.0075 (14)0.0045 (14)
O3A0.149 (4)0.076 (3)0.121 (3)0.012 (3)0.081 (3)0.024 (2)
O4A0.127 (3)0.056 (2)0.137 (4)0.009 (2)0.046 (3)0.025 (2)
N1A0.073 (3)0.061 (3)0.092 (3)0.003 (2)0.028 (2)0.019 (2)
C1A0.041 (2)0.056 (2)0.045 (2)0.0031 (17)0.0086 (17)0.0096 (18)
C2A0.0419 (19)0.047 (2)0.0378 (19)0.0029 (16)0.0046 (15)0.0006 (16)
C3A0.059 (2)0.042 (2)0.062 (3)0.0035 (18)0.006 (2)0.0054 (19)
C4A0.062 (3)0.053 (3)0.070 (3)0.005 (2)0.019 (2)0.009 (2)
C5A0.051 (2)0.047 (2)0.060 (3)0.0051 (18)0.0077 (19)0.0071 (19)
C6A0.073 (3)0.039 (2)0.080 (3)0.004 (2)0.014 (2)0.011 (2)
C7A0.065 (3)0.054 (3)0.060 (3)0.011 (2)0.014 (2)0.004 (2)
C8A0.0398 (19)0.052 (2)0.041 (2)0.0056 (16)0.0021 (15)0.0138 (17)
C9A0.057 (2)0.059 (3)0.045 (2)0.008 (2)0.0075 (19)0.0015 (19)
C10A0.043 (2)0.080 (3)0.074 (3)0.000 (2)0.012 (2)0.008 (3)
C11A0.044 (2)0.084 (3)0.064 (3)0.021 (2)0.002 (2)0.008 (2)
C12A0.053 (3)0.066 (3)0.074 (3)0.018 (2)0.001 (2)0.004 (2)
C13A0.046 (2)0.054 (2)0.064 (3)0.0048 (18)0.0092 (19)0.004 (2)
C14A0.0320 (17)0.049 (2)0.052 (2)0.0024 (15)0.0005 (15)0.0101 (17)
C15A0.052 (2)0.068 (3)0.068 (3)0.012 (2)0.001 (2)0.019 (2)
C16A0.066 (3)0.100 (4)0.091 (4)0.019 (3)0.006 (3)0.049 (3)
C17A0.063 (3)0.133 (5)0.063 (3)0.005 (3)0.023 (3)0.037 (3)
C18A0.068 (3)0.108 (4)0.056 (3)0.013 (3)0.017 (2)0.007 (3)
C19A0.052 (2)0.060 (3)0.054 (2)0.0016 (19)0.0086 (19)0.007 (2)
C20A0.043 (2)0.048 (2)0.045 (2)0.0014 (16)0.0032 (16)0.0052 (17)
C21A0.083 (3)0.061 (3)0.046 (2)0.008 (2)0.013 (2)0.005 (2)
C22A0.104 (4)0.052 (3)0.078 (3)0.015 (3)0.007 (3)0.010 (2)
C23A0.090 (4)0.056 (3)0.085 (4)0.001 (3)0.002 (3)0.017 (3)
C24A0.090 (4)0.077 (3)0.048 (3)0.003 (3)0.009 (2)0.007 (2)
C25A0.076 (3)0.059 (3)0.040 (2)0.003 (2)0.004 (2)0.0060 (19)
Sn20.03729 (14)0.04042 (15)0.04778 (16)0.00518 (11)0.00154 (11)0.00719 (11)
O1B0.0506 (15)0.0532 (16)0.0528 (16)0.0060 (13)0.0100 (13)0.0089 (13)
O2B0.0531 (16)0.0516 (17)0.077 (2)0.0004 (14)0.0098 (15)0.0133 (15)
O3B0.105 (3)0.101 (3)0.097 (3)0.033 (2)0.031 (2)0.018 (2)
O4B0.107 (3)0.128 (4)0.076 (3)0.008 (3)0.047 (2)0.003 (2)
N1B0.060 (2)0.093 (3)0.073 (3)0.002 (2)0.019 (2)0.022 (2)
C1B0.0369 (19)0.053 (2)0.056 (2)0.0130 (17)0.0030 (17)0.0151 (19)
C2B0.0387 (19)0.041 (2)0.047 (2)0.0093 (15)0.0001 (16)0.0046 (16)
C3B0.062 (3)0.053 (2)0.048 (2)0.000 (2)0.0045 (19)0.0027 (19)
C4B0.060 (3)0.058 (3)0.065 (3)0.013 (2)0.007 (2)0.004 (2)
C5B0.045 (2)0.056 (2)0.048 (2)0.0092 (18)0.0064 (17)0.0092 (19)
C6B0.067 (3)0.060 (3)0.044 (2)0.004 (2)0.006 (2)0.0058 (19)
C7B0.054 (2)0.054 (2)0.061 (3)0.0054 (19)0.002 (2)0.002 (2)
C8B0.0386 (19)0.042 (2)0.056 (2)0.0035 (15)0.0008 (16)0.0153 (17)
C9B0.046 (2)0.060 (3)0.073 (3)0.0095 (19)0.005 (2)0.004 (2)
C10B0.045 (2)0.081 (3)0.100 (4)0.013 (2)0.001 (2)0.008 (3)
C11B0.049 (3)0.066 (3)0.099 (4)0.001 (2)0.023 (3)0.012 (3)
C12B0.066 (3)0.052 (3)0.087 (3)0.007 (2)0.025 (3)0.007 (2)
C13B0.049 (2)0.052 (2)0.063 (3)0.0031 (18)0.0009 (19)0.004 (2)
C14B0.0392 (19)0.044 (2)0.049 (2)0.0064 (15)0.0066 (16)0.0116 (17)
C15B0.058 (2)0.062 (3)0.049 (2)0.004 (2)0.004 (2)0.008 (2)
C16B0.071 (3)0.094 (4)0.057 (3)0.012 (3)0.014 (2)0.025 (3)
C17B0.064 (3)0.078 (3)0.077 (3)0.025 (3)0.008 (3)0.036 (3)
C18B0.079 (3)0.050 (3)0.084 (3)0.017 (2)0.001 (3)0.015 (2)
C19B0.058 (3)0.056 (3)0.066 (3)0.012 (2)0.010 (2)0.013 (2)
C20B0.0431 (19)0.041 (2)0.044 (2)0.0063 (16)0.0024 (16)0.0059 (16)
C21B0.074 (3)0.052 (3)0.059 (3)0.009 (2)0.019 (2)0.007 (2)
C22B0.092 (4)0.071 (3)0.059 (3)0.001 (3)0.025 (3)0.001 (2)
C23B0.092 (4)0.058 (3)0.057 (3)0.016 (3)0.001 (3)0.011 (2)
C24B0.083 (3)0.044 (2)0.072 (3)0.002 (2)0.003 (3)0.004 (2)
C25B0.064 (3)0.054 (2)0.050 (2)0.005 (2)0.002 (2)0.012 (2)
Geometric parameters (Å, º) top
Sn1—O1A2.074 (3)Sn2—O1B2.077 (3)
Sn1—C14A2.106 (4)Sn2—C14B2.115 (4)
Sn1—C8A2.117 (4)Sn2—C8B2.123 (4)
Sn1—C20A2.125 (4)Sn2—C20B2.128 (4)
Sn1—O2A2.874 (4)Sn2—O2B2.778 (4)
O1A—C1A1.305 (5)O1B—C1B1.301 (5)
O2A—C1A1.219 (5)O2B—C1B1.224 (5)
O3A—N1A1.195 (5)O3B—N1B1.218 (6)
O4A—N1A1.205 (5)O4B—N1B1.201 (5)
N1A—C5A1.482 (5)N1B—C5B1.483 (5)
C1A—C2A1.489 (5)C1B—C2B1.499 (5)
C2A—C7A1.382 (6)C2B—C3B1.374 (5)
C2A—C3A1.383 (5)C2B—C7B1.386 (5)
C3A—C4A1.372 (6)C3B—C4B1.383 (6)
C4A—C5A1.362 (6)C4B—C5B1.371 (6)
C5A—C6A1.351 (6)C5B—C6B1.356 (6)
C6A—C7A1.387 (6)C6B—C7B1.376 (6)
C8A—C9A1.375 (5)C8B—C13B1.375 (6)
C8A—C13A1.385 (5)C8B—C9B1.387 (5)
C9A—C10A1.392 (6)C9B—C10B1.381 (6)
C10A—C11A1.363 (6)C10B—C11B1.365 (7)
C11A—C12A1.371 (6)C11B—C12B1.378 (7)
C12A—C13A1.383 (6)C12B—C13B1.387 (6)
C14A—C19A1.377 (6)C14B—C19B1.371 (6)
C14A—C15A1.396 (6)C14B—C15B1.388 (6)
C15A—C16A1.379 (7)C15B—C16B1.386 (6)
C16A—C17A1.376 (8)C16B—C17B1.358 (7)
C17A—C18A1.369 (8)C17B—C18B1.370 (7)
C18A—C19A1.386 (6)C18B—C19B1.382 (6)
C20A—C25A1.384 (5)C20B—C25B1.386 (5)
C20A—C21A1.384 (6)C20B—C21B1.388 (5)
C21A—C22A1.370 (6)C21B—C22B1.369 (6)
C22A—C23A1.367 (7)C22B—C23B1.370 (7)
C23A—C24A1.368 (7)C23B—C24B1.369 (6)
C24A—C25A1.382 (6)C24B—C25B1.364 (6)
O1A—Sn1—C14A106.84 (14)O1B—Sn2—C14B106.41 (14)
O1A—Sn1—C8A110.64 (14)O1B—Sn2—C8B114.31 (15)
C14A—Sn1—C8A117.42 (15)C14B—Sn2—C8B115.88 (16)
O1A—Sn1—C20A95.64 (15)O1B—Sn2—C20B95.45 (15)
C14A—Sn1—C20A109.71 (16)C14B—Sn2—C20B111.12 (16)
C8A—Sn1—C20A114.19 (17)C8B—Sn2—C20B111.76 (16)
O1A—Sn1—O2A50.10 (11)O1B—Sn2—O2B51.78 (12)
C14A—Sn1—O2A86.81 (14)C14B—Sn2—O2B85.70 (14)
C8A—Sn1—O2A81.19 (15)C8B—Sn2—O2B83.20 (15)
C20A—Sn1—O2A145.61 (12)C20B—Sn2—O2B146.96 (12)
C1A—O1A—Sn1111.5 (2)C1B—O1B—Sn2108.6 (2)
C1A—O2A—Sn175.5 (2)C1B—O2B—Sn277.4 (3)
O3A—N1A—O4A123.9 (4)O4B—N1B—O3B124.9 (4)
O3A—N1A—C5A118.0 (4)O4B—N1B—C5B117.8 (5)
O4A—N1A—C5A118.2 (4)O3B—N1B—C5B117.3 (4)
O2A—C1A—O1A122.8 (4)O2B—C1B—O1B122.2 (4)
O2A—C1A—C2A122.3 (4)O2B—C1B—C2B122.1 (4)
O1A—C1A—C2A114.8 (3)O1B—C1B—C2B115.6 (3)
C7A—C2A—C3A118.7 (4)C3B—C2B—C7B119.7 (4)
C7A—C2A—C1A119.9 (4)C3B—C2B—C1B121.1 (4)
C3A—C2A—C1A121.4 (4)C7B—C2B—C1B119.2 (4)
C4A—C3A—C2A120.7 (4)C2B—C3B—C4B120.6 (4)
C5A—C4A—C3A118.4 (4)C5B—C4B—C3B118.1 (4)
C6A—C5A—C4A123.5 (4)C6B—C5B—C4B122.4 (4)
C6A—C5A—N1A118.4 (4)C6B—C5B—N1B119.0 (4)
C4A—C5A—N1A118.1 (4)C4B—C5B—N1B118.6 (4)
C5A—C6A—C7A117.7 (4)C5B—C6B—C7B119.4 (4)
C2A—C7A—C6A120.9 (4)C6B—C7B—C2B119.7 (4)
C9A—C8A—C13A118.0 (4)C13B—C8B—C9B118.3 (4)
C9A—C8A—Sn1118.5 (3)C13B—C8B—Sn2125.0 (3)
C13A—C8A—Sn1123.2 (3)C9B—C8B—Sn2116.5 (3)
C8A—C9A—C10A121.6 (4)C10B—C9B—C8B120.8 (4)
C11A—C10A—C9A119.3 (4)C11B—C10B—C9B120.3 (5)
C10A—C11A—C12A120.3 (4)C10B—C11B—C12B119.7 (4)
C11A—C12A—C13A120.3 (4)C11B—C12B—C13B119.9 (5)
C12A—C13A—C8A120.5 (4)C8B—C13B—C12B121.0 (4)
C19A—C14A—C15A118.0 (4)C19B—C14B—C15B118.0 (4)
C19A—C14A—Sn1122.8 (3)C19B—C14B—Sn2122.0 (3)
C15A—C14A—Sn1119.2 (3)C15B—C14B—Sn2120.0 (3)
C16A—C15A—C14A120.9 (5)C16B—C15B—C14B120.6 (4)
C17A—C16A—C15A120.4 (5)C17B—C16B—C15B120.5 (5)
C18A—C17A—C16A119.0 (5)C16B—C17B—C18B119.4 (4)
C17A—C18A—C19A121.0 (5)C17B—C18B—C19B120.5 (5)
C14A—C19A—C18A120.6 (4)C14B—C19B—C18B121.0 (4)
C25A—C20A—C21A116.3 (4)C25B—C20B—C21B117.2 (4)
C25A—C20A—Sn1121.3 (3)C25B—C20B—Sn2122.2 (3)
C21A—C20A—Sn1122.2 (3)C21B—C20B—Sn2120.6 (3)
C22A—C21A—C20A122.4 (4)C22B—C21B—C20B121.7 (4)
C23A—C22A—C21A119.8 (4)C21B—C22B—C23B120.0 (4)
C22A—C23A—C24A119.7 (5)C24B—C23B—C22B119.1 (4)
C23A—C24A—C25A119.9 (4)C25B—C24B—C23B121.1 (4)
C24A—C25A—C20A121.8 (4)C24B—C25B—C20B120.9 (4)
C14A—Sn1—O1A—C1A72.4 (3)C14B—Sn2—O1B—C1B70.5 (3)
C8A—Sn1—O1A—C1A56.5 (3)C8B—Sn2—O1B—C1B58.7 (3)
C20A—Sn1—O1A—C1A175.0 (3)C20B—Sn2—O1B—C1B175.6 (2)
O2A—Sn1—O1A—C1A1.6 (2)O2B—Sn2—O1B—C1B0.1 (2)
O1A—Sn1—O2A—C1A1.7 (2)O1B—Sn2—O2B—C1B0.1 (2)
C14A—Sn1—O2A—C1A116.8 (3)C14B—Sn2—O2B—C1B114.7 (3)
C8A—Sn1—O2A—C1A124.8 (3)C8B—Sn2—O2B—C1B128.6 (2)
C20A—Sn1—O2A—C1A4.3 (3)C20B—Sn2—O2B—C1B8.5 (3)
Sn1—O2A—C1A—O1A2.4 (3)Sn2—O2B—C1B—O1B0.2 (3)
Sn1—O2A—C1A—C2A177.5 (4)Sn2—O2B—C1B—C2B179.7 (3)
Sn1—O1A—C1A—O2A3.5 (5)Sn2—O1B—C1B—O2B0.2 (4)
Sn1—O1A—C1A—C2A176.4 (2)Sn2—O1B—C1B—C2B179.6 (2)
O2A—C1A—C2A—C7A27.1 (6)O2B—C1B—C2B—C3B166.4 (4)
O1A—C1A—C2A—C7A152.8 (4)O1B—C1B—C2B—C3B13.4 (5)
O2A—C1A—C2A—C3A153.6 (4)O2B—C1B—C2B—C7B13.5 (6)
O1A—C1A—C2A—C3A26.5 (5)O1B—C1B—C2B—C7B166.7 (3)
C7A—C2A—C3A—C4A1.1 (6)C7B—C2B—C3B—C4B1.7 (6)
C1A—C2A—C3A—C4A178.3 (4)C1B—C2B—C3B—C4B178.4 (4)
C2A—C3A—C4A—C5A0.6 (7)C2B—C3B—C4B—C5B0.3 (7)
C3A—C4A—C5A—C6A1.1 (7)C3B—C4B—C5B—C6B1.6 (7)
C3A—C4A—C5A—N1A177.3 (4)C3B—C4B—C5B—N1B178.6 (4)
O3A—N1A—C5A—C6A160.4 (5)O4B—N1B—C5B—C6B16.4 (7)
O4A—N1A—C5A—C6A20.4 (7)O3B—N1B—C5B—C6B164.5 (5)
O3A—N1A—C5A—C4A18.1 (7)O4B—N1B—C5B—C4B163.4 (5)
O4A—N1A—C5A—C4A161.1 (5)O3B—N1B—C5B—C4B15.6 (6)
C4A—C5A—C6A—C7A0.2 (7)C4B—C5B—C6B—C7B2.1 (7)
N1A—C5A—C6A—C7A178.6 (4)N1B—C5B—C6B—C7B178.1 (4)
C3A—C2A—C7A—C6A2.5 (6)C5B—C6B—C7B—C2B0.7 (7)
C1A—C2A—C7A—C6A176.9 (4)C3B—C2B—C7B—C6B1.2 (6)
C5A—C6A—C7A—C2A2.0 (7)C1B—C2B—C7B—C6B178.9 (4)
O1A—Sn1—C8A—C9A111.3 (3)O1B—Sn2—C8B—C13B68.1 (3)
C14A—Sn1—C8A—C9A125.7 (3)C14B—Sn2—C8B—C13B56.2 (4)
C20A—Sn1—C8A—C9A4.8 (3)C20B—Sn2—C8B—C13B175.1 (3)
O2A—Sn1—C8A—C9A152.6 (3)O2B—Sn2—C8B—C13B25.7 (3)
O1A—Sn1—C8A—C13A73.9 (3)O1B—Sn2—C8B—C9B117.9 (3)
C14A—Sn1—C8A—C13A49.1 (4)C14B—Sn2—C8B—C9B117.7 (3)
C20A—Sn1—C8A—C13A179.6 (3)C20B—Sn2—C8B—C9B10.9 (3)
O2A—Sn1—C8A—C13A32.7 (3)O2B—Sn2—C8B—C9B160.4 (3)
C13A—C8A—C9A—C10A0.7 (6)C13B—C8B—C9B—C10B0.1 (6)
Sn1—C8A—C9A—C10A174.3 (3)Sn2—C8B—C9B—C10B174.3 (3)
C8A—C9A—C10A—C11A1.2 (7)C8B—C9B—C10B—C11B0.1 (7)
C9A—C10A—C11A—C12A0.9 (7)C9B—C10B—C11B—C12B0.4 (8)
C10A—C11A—C12A—C13A0.0 (7)C10B—C11B—C12B—C13B0.4 (7)
C11A—C12A—C13A—C8A0.5 (7)C9B—C8B—C13B—C12B0.1 (6)
C9A—C8A—C13A—C12A0.2 (6)Sn2—C8B—C13B—C12B173.8 (3)
Sn1—C8A—C13A—C12A175.0 (3)C11B—C12B—C13B—C8B0.2 (7)
O1A—Sn1—C14A—C19A82.6 (3)O1B—Sn2—C14B—C19B94.0 (3)
C8A—Sn1—C14A—C19A42.3 (4)C8B—Sn2—C14B—C19B34.3 (4)
C20A—Sn1—C14A—C19A174.9 (3)C20B—Sn2—C14B—C19B163.3 (3)
O2A—Sn1—C14A—C19A36.0 (3)O2B—Sn2—C14B—C19B46.0 (3)
O1A—Sn1—C14A—C15A97.4 (3)O1B—Sn2—C14B—C15B85.5 (3)
C8A—Sn1—C14A—C15A137.7 (3)C8B—Sn2—C14B—C15B146.2 (3)
C20A—Sn1—C14A—C15A5.2 (3)C20B—Sn2—C14B—C15B17.2 (3)
O2A—Sn1—C14A—C15A143.9 (3)O2B—Sn2—C14B—C15B133.5 (3)
C19A—C14A—C15A—C16A0.0 (6)C19B—C14B—C15B—C16B2.0 (6)
Sn1—C14A—C15A—C16A180.0 (3)Sn2—C14B—C15B—C16B177.6 (3)
C14A—C15A—C16A—C17A0.3 (7)C14B—C15B—C16B—C17B0.9 (7)
C15A—C16A—C17A—C18A0.6 (8)C15B—C16B—C17B—C18B0.2 (7)
C16A—C17A—C18A—C19A0.6 (8)C16B—C17B—C18B—C19B0.2 (7)
C15A—C14A—C19A—C18A0.0 (6)C15B—C14B—C19B—C18B1.9 (6)
Sn1—C14A—C19A—C18A180.0 (3)Sn2—C14B—C19B—C18B177.6 (3)
C17A—C18A—C19A—C14A0.3 (7)C17B—C18B—C19B—C14B0.9 (7)
O1A—Sn1—C20A—C25A9.3 (3)O1B—Sn2—C20B—C25B9.9 (3)
C14A—Sn1—C20A—C25A119.4 (3)C14B—Sn2—C20B—C25B119.8 (3)
C8A—Sn1—C20A—C25A106.4 (3)C8B—Sn2—C20B—C25B109.0 (3)
O2A—Sn1—C20A—C25A4.7 (5)O2B—Sn2—C20B—C25B3.3 (5)
O1A—Sn1—C20A—C21A165.8 (4)O1B—Sn2—C20B—C21B169.2 (3)
C14A—Sn1—C20A—C21A55.6 (4)C14B—Sn2—C20B—C21B59.3 (4)
C8A—Sn1—C20A—C21A78.5 (4)C8B—Sn2—C20B—C21B71.9 (4)
O2A—Sn1—C20A—C21A170.4 (3)O2B—Sn2—C20B—C21B175.8 (3)
C25A—C20A—C21A—C22A1.4 (7)C25B—C20B—C21B—C22B0.3 (7)
Sn1—C20A—C21A—C22A173.9 (4)Sn2—C20B—C21B—C22B179.5 (4)
C20A—C21A—C22A—C23A0.5 (8)C20B—C21B—C22B—C23B0.2 (8)
C21A—C22A—C23A—C24A1.2 (9)C21B—C22B—C23B—C24B0.2 (8)
C22A—C23A—C24A—C25A0.1 (8)C22B—C23B—C24B—C25B0.4 (8)
C23A—C24A—C25A—C20A1.9 (8)C23B—C24B—C25B—C20B0.3 (7)
C21A—C20A—C25A—C24A2.6 (7)C21B—C20B—C25B—C24B0.1 (6)
Sn1—C20A—C25A—C24A172.7 (4)Sn2—C20B—C25B—C24B179.2 (3)

Experimental details

Crystal data
Chemical formula[Sn(C6H5)3(C7H4NO4)]
Mr516.10
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.949 (11), 14.302 (16), 17.530 (16)
α, β, γ (°)94.89 (8), 83.79 (8), 96.24 (9)
V3)2211 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.19
Crystal size (mm)0.50 × 0.40 × 0.20
Data collection
DiffractometerNicolet P3
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.471, 0.598
No. of measured, independent and
observed [I > 2σ(I)] reflections
10232, 10230, 7111
Rint0.055
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.088, 1.02
No. of reflections10230
No. of parameters559
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.58

Computer programs: Nicolet P3 Software (Nicolet, 1980), Nicolet P3 Software, RDNIC (Howie, 1980), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

Selected geometric parameters (Å, º) top
Sn1—O1A2.074 (3)Sn2—O1B2.077 (3)
Sn1—C14A2.106 (4)Sn2—C14B2.115 (4)
Sn1—C8A2.117 (4)Sn2—C8B2.123 (4)
Sn1—C20A2.125 (4)Sn2—C20B2.128 (4)
Sn1—O2A2.874 (4)Sn2—O2B2.778 (4)
O1A—Sn1—C14A106.84 (14)O1B—Sn2—C14B106.41 (14)
O1A—Sn1—C8A110.64 (14)O1B—Sn2—C8B114.31 (15)
C14A—Sn1—C8A117.42 (15)C14B—Sn2—C8B115.88 (16)
O1A—Sn1—C20A95.64 (15)O1B—Sn2—C20B95.45 (15)
C14A—Sn1—C20A109.71 (16)C14B—Sn2—C20B111.12 (16)
C8A—Sn1—C20A114.19 (17)C8B—Sn2—C20B111.76 (16)
O1A—Sn1—O2A50.10 (11)O1B—Sn2—O2B51.78 (12)
C14A—Sn1—O2A86.81 (14)C14B—Sn2—O2B85.70 (14)
C8A—Sn1—O2A81.19 (15)C8B—Sn2—O2B83.20 (15)
C20A—Sn1—O2A145.61 (12)C20B—Sn2—O2B146.96 (12)
 

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