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The structure of the title di­methyl­tin(IV) complex, [2-(5-bromo-2-oxido­benzyl­idene­amino)­benzoato-κ3O,N,O′]di­methyl­tin(IV), [Sn(CH3)2(C14H8BrNO3)], features centrosymmetric dimers disposed about a central Sn2O2 core. Each Sn centre has seven-coordinate pentagonal–bipyramidal geometry, taking into account two moderately long Sn—O contacts about an inversion centre [2.679 (4) and 2.981 (4) Å]. The methyl groups are in an axial orientation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102003530/gg1098sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102003530/gg1098Isup2.hkl
Contains datablock I

CCDC reference: 184482

Computing details top

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

[2-(5-bromo-2-oxidobenzylideneamino)benzoato-κ3O,N,O']dimethyltin(IV) top
Crystal data top
[Sn(C14H8BrNO3)(CH3)2]F(000) = 904
Mr = 466.89Dx = 1.892 Mg m3
Monoclinic, P21/nMelting point > 517 K
Hall symbol: P2ynMo Kα radiation, λ = 0.71073 Å
a = 8.8719 (17) ÅCell parameters from 29 reflections
b = 12.0961 (17) Åθ = 5.2–12.5°
c = 15.323 (4) ŵ = 4.01 mm1
β = 94.702 (16)°T = 293 K
V = 1638.8 (5) Å3Rectangular_block, yellow
Z = 40.96 × 0.56 × 0.28 mm
Data collection top
Bruker P4
diffractometer
2411 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 101
Absorption correction: ψ scan
(North et al., 1968)
k = 114
Tmin = 0.081, Tmax = 0.326l = 1818
3818 measured reflections3 standard reflections every 97 reflections
2875 independent reflections intensity decay: none
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0679P)2]
where P = (Fo2 + 2Fc2)/3
2875 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 1.55 e Å3
0 restraintsΔρmin = 1.34 e Å3
Special details top

Experimental. A large collimator (1.5 mm) was used in this experiment

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.07632 (4)0.83956 (3)0.98368 (2)0.02925 (15)
Br10.62844 (7)0.44430 (5)1.19032 (4)0.04488 (19)
O30.2377 (5)1.1790 (3)0.9619 (3)0.0450 (10)
N10.3177 (5)0.8352 (3)0.9486 (3)0.0284 (9)
C220.4206 (7)1.0956 (5)0.8371 (4)0.0383 (12)
H220.40151.17120.83790.046*
O10.1084 (4)0.6629 (3)0.9791 (2)0.0349 (9)
O20.1407 (4)1.0157 (3)0.9839 (3)0.0394 (9)
C130.4653 (6)0.5115 (4)1.1220 (3)0.0318 (11)
C210.3491 (6)1.0270 (4)0.8943 (3)0.0304 (11)
C200.2390 (6)1.0784 (4)0.9507 (3)0.0312 (11)
C140.4893 (6)0.6101 (4)1.0811 (3)0.0298 (11)
H140.58540.64151.08560.036*
C160.4099 (6)0.7609 (4)0.9852 (3)0.0303 (11)
H160.51260.77190.98030.036*
C100.2235 (6)0.6157 (4)1.0237 (3)0.0313 (11)
C150.3690 (6)0.6644 (4)1.0322 (3)0.0286 (10)
C110.2059 (7)0.5114 (4)1.0646 (4)0.0378 (12)
H110.11210.47661.05870.045*
C120.3228 (6)0.4614 (4)1.1122 (4)0.0372 (12)
H120.30790.39341.13840.045*
C260.3816 (6)0.9123 (4)0.8921 (3)0.0281 (10)
C240.5466 (8)0.9440 (5)0.7769 (4)0.0495 (15)
H240.61140.91610.73750.059*
C250.4785 (7)0.8737 (5)0.8328 (4)0.0393 (12)
H250.49840.79830.83050.047*
C230.5181 (8)1.0552 (5)0.7799 (4)0.0466 (14)
H230.56471.10320.74310.056*
C1010.1064 (8)0.8372 (5)1.1209 (4)0.0451 (14)
H10D0.08450.90901.14330.068*
H10E0.20910.81771.13910.068*
H10F0.03930.78371.14310.068*
C1020.0435 (8)0.8364 (5)0.8597 (4)0.0440 (15)
H10A0.11550.77700.85730.066*
H10B0.02590.82550.81560.066*
H10C0.09570.90530.84950.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0260 (2)0.0224 (2)0.0394 (2)0.00248 (13)0.00318 (15)0.00010 (13)
Br10.0502 (4)0.0415 (3)0.0415 (3)0.0087 (3)0.0046 (3)0.0072 (2)
O10.0305 (19)0.0239 (19)0.049 (2)0.0022 (15)0.0025 (17)0.0021 (15)
O20.034 (2)0.0225 (18)0.064 (3)0.0039 (16)0.0181 (19)0.0047 (16)
O30.042 (2)0.0241 (19)0.071 (3)0.0077 (17)0.015 (2)0.0064 (18)
N10.024 (2)0.023 (2)0.039 (2)0.0026 (17)0.0076 (18)0.0008 (16)
C100.036 (3)0.021 (2)0.037 (3)0.001 (2)0.004 (2)0.003 (2)
C110.035 (3)0.028 (3)0.052 (3)0.007 (2)0.004 (3)0.001 (2)
C120.038 (3)0.028 (3)0.047 (3)0.004 (2)0.010 (3)0.005 (2)
C130.037 (3)0.031 (3)0.028 (2)0.005 (2)0.004 (2)0.000 (2)
C140.028 (3)0.028 (3)0.034 (3)0.002 (2)0.002 (2)0.002 (2)
C150.028 (3)0.025 (2)0.034 (2)0.001 (2)0.009 (2)0.0012 (19)
C160.025 (2)0.026 (2)0.040 (3)0.006 (2)0.003 (2)0.000 (2)
C200.026 (3)0.023 (3)0.045 (3)0.003 (2)0.003 (2)0.000 (2)
C210.025 (3)0.026 (2)0.039 (3)0.007 (2)0.001 (2)0.001 (2)
C220.040 (3)0.027 (3)0.048 (3)0.004 (2)0.002 (3)0.006 (2)
C230.052 (4)0.041 (3)0.048 (3)0.011 (3)0.015 (3)0.012 (3)
C240.054 (4)0.046 (3)0.052 (3)0.003 (3)0.025 (3)0.007 (3)
C250.041 (3)0.028 (3)0.051 (3)0.004 (2)0.014 (3)0.005 (2)
C260.025 (2)0.023 (2)0.036 (3)0.003 (2)0.000 (2)0.0043 (19)
C1010.045 (4)0.046 (3)0.045 (3)0.005 (3)0.008 (3)0.000 (2)
C1020.049 (4)0.039 (3)0.042 (3)0.008 (3)0.013 (3)0.005 (2)
Geometric parameters (Å, º) top
Sn1—C1012.098 (6)C14—H140.9300
Sn1—C1022.100 (5)C16—C151.433 (7)
Sn1—O12.158 (3)C16—H160.9300
Sn1—O22.206 (4)C10—C151.415 (7)
Sn1—O2i2.679 (4)C10—C111.423 (7)
Sn1—O3i2.981 (4)C11—C121.360 (8)
Sn1—N12.251 (4)C11—H110.9300
Br1—C131.898 (5)C12—H120.9300
O3—C201.230 (6)C26—C251.382 (8)
N1—C161.309 (6)C24—C231.370 (9)
N1—C261.422 (6)C24—C251.382 (8)
C22—C231.371 (9)C24—H240.9300
C22—C211.396 (7)C25—H250.9300
C22—H220.9300C23—H230.9300
O1—C101.312 (6)C101—H10D0.9600
O2—C201.291 (6)C101—H10E0.9600
C13—C141.372 (7)C101—H10F0.9600
C13—C121.399 (8)C102—H10A0.9600
C21—C261.418 (7)C102—H10B0.9600
C21—C201.492 (7)C102—H10C0.9600
C14—C151.415 (7)
C101—Sn1—C102156.9 (3)C15—C10—C11117.5 (5)
C101—Sn1—O190.71 (19)C14—C15—C10119.9 (4)
C102—Sn1—O190.65 (18)C14—C15—C16115.7 (5)
C101—Sn1—O290.0 (2)C10—C15—C16124.0 (5)
C102—Sn1—O297.5 (2)C12—C11—C10121.6 (5)
O1—Sn1—O2157.21 (15)C12—C11—H11119.2
C101—Sn1—N1101.2 (2)C10—C11—H11119.2
C102—Sn1—N1101.8 (2)C11—C12—C13120.6 (5)
O1—Sn1—N180.70 (14)C11—C12—H12119.7
O2—Sn1—N176.81 (14)C13—C12—H12119.7
C16—N1—C26116.4 (4)C25—C26—C21119.0 (5)
C16—N1—Sn1119.1 (3)C25—C26—N1118.6 (4)
C26—N1—Sn1124.3 (3)C21—C26—N1122.4 (5)
C23—C22—C21122.1 (5)C23—C24—C25119.5 (6)
C23—C22—H22118.9C23—C24—H24120.3
C21—C22—H22118.9C25—C24—H24120.3
C10—O1—Sn1120.9 (3)C24—C25—C26121.8 (5)
C20—O2—Sn1138.6 (3)C24—C25—H25119.1
C14—C13—C12120.0 (5)C26—C25—H25119.1
C14—C13—Br1118.9 (4)C24—C23—C22120.0 (5)
C12—C13—Br1121.1 (4)C24—C23—H23120.0
C22—C21—C26117.6 (5)C22—C23—H23120.0
C22—C21—C20117.9 (5)Sn1—C101—H10D109.5
C26—C21—C20124.4 (4)Sn1—C101—H10E109.5
O3—C20—O2120.8 (5)H10D—C101—H10E109.5
O3—C20—C21120.5 (5)Sn1—C101—H10F109.5
O2—C20—C21118.6 (4)H10D—C101—H10F109.5
C13—C14—C15120.5 (5)H10E—C101—H10F109.5
C13—C14—H14119.8Sn1—C102—H10A109.5
C15—C14—H14119.8Sn1—C102—H10B109.5
N1—C16—C15126.8 (5)H10A—C102—H10B109.5
N1—C16—H16116.6Sn1—C102—H10C109.5
C15—C16—H16116.6H10A—C102—H10C109.5
O1—C10—C15122.1 (4)H10B—C102—H10C109.5
O1—C10—C11120.4 (5)
C101—Sn1—N1—C1649.5 (4)Sn1—O1—C10—C1538.7 (6)
C102—Sn1—N1—C16128.1 (4)Sn1—O1—C10—C11142.1 (4)
O1—Sn1—N1—C1639.4 (4)C13—C14—C15—C101.3 (7)
O2—Sn1—N1—C16136.9 (4)C13—C14—C15—C16174.1 (5)
C101—Sn1—N1—C26126.9 (4)O1—C10—C15—C14179.9 (4)
C102—Sn1—N1—C2655.5 (4)C11—C10—C15—C141.0 (7)
O1—Sn1—N1—C26144.3 (4)O1—C10—C15—C168.0 (8)
O2—Sn1—N1—C2639.5 (4)C11—C10—C15—C16171.1 (5)
C101—Sn1—O1—C1049.0 (4)N1—C16—C15—C14167.0 (5)
C102—Sn1—O1—C10154.1 (4)N1—C16—C15—C1020.5 (8)
O2—Sn1—O1—C1042.7 (6)O1—C10—C11—C12179.1 (5)
N1—Sn1—O1—C1052.2 (4)C15—C10—C11—C121.8 (8)
C101—Sn1—O2—C20123.8 (6)C10—C11—C12—C130.2 (9)
C102—Sn1—O2—C2078.1 (6)C14—C13—C12—C112.2 (8)
O1—Sn1—O2—C2032.0 (8)Br1—C13—C12—C11178.6 (4)
N1—Sn1—O2—C2022.4 (5)C22—C21—C26—C251.5 (7)
C23—C22—C21—C260.6 (8)C20—C21—C26—C25175.7 (5)
C23—C22—C21—C20176.9 (5)C22—C21—C26—N1178.7 (5)
Sn1—O2—C20—O3176.4 (4)C20—C21—C26—N14.1 (8)
Sn1—O2—C20—C210.3 (8)C16—N1—C26—C2544.2 (7)
C22—C21—C20—O316.8 (8)Sn1—N1—C26—C25139.3 (4)
C26—C21—C20—O3165.9 (5)C16—N1—C26—C21136.0 (5)
C22—C21—C20—O2159.9 (5)Sn1—N1—C26—C2140.5 (6)
C26—C21—C20—O217.4 (8)C23—C24—C25—C260.0 (10)
C12—C13—C14—C153.0 (8)C21—C26—C25—C241.2 (9)
Br1—C13—C14—C15177.8 (4)N1—C26—C25—C24178.9 (6)
C26—N1—C16—C15168.7 (5)C25—C24—C23—C221.0 (11)
Sn1—N1—C16—C1514.6 (7)C21—C22—C23—C240.7 (10)
Symmetry code: (i) x, y+2, z+2.
 

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