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Acta Cryst. (2009). E65, m1614    [ doi:10.1107/S1600536809048314 ]

Tricyclohexyl[2-(2,3-dimethylanilino)benzoato-[kappa]O]tin(IV)

M. Danish, M. N. Tahir, N. Ahmad, S. Ali and A. Badshah

Abstract top

In the title compound, [Sn(C6H11)3(C15H14NO2)], the SnIV atom adopts a distorted tetrahedral SnOC3 arrangement. The dihedral angle between the benzene rings in the mefanamic acid molecule is 82.16 (17)° and intramolecular N-H...O and C-H...O hydrogen bonds help to establish the conformation. Two of the cyclohexyl rings are disordered over two sets of sites with equal occupancies.

Comment top

We reported the crystal structures of (II) {2-[(2,3-Dimethylphenyl)amino]benzoato-O:O'}-trimethyltin(IV) (Tahir et al., 1997a), (III) (Ketoprofenato)trimethyltin(IV) (Tahir et al., 1997b) and recently (IV) Bis(µ3-Oxo)-bis(µ2-2- ((3-thiophene)acetato-O,O')-octa-methyl(2-((3-thiophene)acetato-O)- tetra-tin(IV) (Danish et al., 2009). In continuation of interest with tin chemistry, the title compound (I, Fig. 1) is being reported.

The tricyclohexyltin complexes of carboxylates have tetrahedral coordination such as (2-((E)-2-(2-Hydroxy-5-methylphenyl)-1-diazenyl)benzoato)-tricyclohexyl -tin (Willem et al., 1998). The title compound (I) also have distorted tetrahedral coordination. Due to the bulky and twisted ligand of mefenamic acid, the cyclohexyl moieties are disordered. The dihedral angle between the benzene rings A (C1–C6) and B (C8–C13) is 82.16 (17)°. The molecules are stabilized in the form of monomers with two intramolecular H-bondings (Table 1).

Related literature top

For the synthesis, see: Danish et al. (1997). For related structures, see: Danish et al. (1997, 2009); Tahir et al. (1997a,b); Willem et al. (1998).

Experimental top

The title compound was prepared according to the method described already (Danish et al., 1997) to yield colourless prisms of (I).

Refinement top

The disorder in the cyclohexyl rings occurs as the C–C bond distances become shorter when refined isotropically or anisotropically. The higher peak remains present to the Sn-atom if refined without consideration of disorder also. However, lower R-values convinced to submit the crystal structure in the present form.

All the cyclohexyl rings were refined with equal occupancy ratio and using EADP for the individual rings.

The coordinates of H1 attached to N1 were refined. The other H-atoms were positioned geometrically (C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) with the atom numbering scheme having one part of disordered cyclohexyl rings. The displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of (I) with the atom numbering scheme having other part of disordered cyclohexyl rings. The displacement ellipsoids are drawn at the 30% probability level.
Tricyclohexyl[2-(2,3-dimethylanilino)benzoato-κO]tin(IV) top
Crystal data top
[Sn(C6H11)3(C15H14NO2)]Z = 2
Mr = 608.41F(000) = 636
Triclinic, P1Dx = 1.298 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6093 (2) ÅCell parameters from 7684 reflections
b = 12.0104 (3) Åθ = 2.3–28.3°
c = 15.5241 (4) ŵ = 0.85 mm−1
α = 109.872 (1)°T = 296 K
β = 90.616 (2)°Prism, colourless
γ = 110.548 (1)°0.28 × 0.22 × 0.20 mm
V = 1560.47 (6) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer		7684 independent reflections
Radiation source: fine-focus sealed tube5308 reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.3°
ω scansh = −12→8
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −15→15
Tmin = 0.797, Tmax = 0.841l = −20→20
31924 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0862P)2 + 1.3991P]
where P = (Fo2 + 2Fc2)/3
7684 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 1.37 e Å−3
33 restraintsΔρmin = −0.49 e Å−3
Crystal data top
[Sn(C6H11)3(C15H14NO2)]γ = 110.548 (1)°
Mr = 608.41V = 1560.47 (6) Å3
Triclinic, P1Z = 2
a = 9.6093 (2) ÅMo Kα radiation
b = 12.0104 (3) ŵ = 0.85 mm−1
c = 15.5241 (4) ÅT = 296 K
α = 109.872 (1)°0.28 × 0.22 × 0.20 mm
β = 90.616 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		7684 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5308 reflections with I > 2σ(I)
Tmin = 0.797, Tmax = 0.841Rint = 0.030
31924 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166Δρmax = 1.37 e Å−3
S = 1.02Δρmin = −0.49 e Å−3
7684 reflectionsAbsolute structure: ?
307 parametersFlack parameter: ?
33 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn0.36022 (4)0.37096 (3)0.16644 (2)0.06337 (15)
O10.2926 (4)0.4860 (3)0.1161 (2)0.0701 (8)
O20.3934 (5)0.6278 (3)0.2549 (2)0.0815 (10)
N10.3785 (6)0.8571 (4)0.3012 (3)0.0864 (14)
H10.413 (7)0.803 (6)0.314 (5)0.104*
C10.2665 (5)0.6839 (4)0.1546 (3)0.0565 (10)
C20.2909 (6)0.8087 (4)0.2175 (3)0.0622 (11)
C30.2220 (7)0.8792 (5)0.1918 (4)0.0785 (14)
H30.23500.96050.23280.094*
C40.1360 (8)0.8315 (6)0.1077 (4)0.0930 (18)
H40.09120.88090.09260.112*
C50.1136 (8)0.7119 (6)0.0446 (4)0.097 (2)
H50.05580.6808−0.01310.116*
C60.1779 (6)0.6405 (5)0.0685 (3)0.0740 (13)
H60.16270.55940.02610.089*
C70.3235 (5)0.5990 (4)0.1789 (3)0.0604 (10)
C80.3998 (7)0.9770 (5)0.3718 (3)0.0735 (13)
C90.5116 (9)1.0862 (6)0.3712 (5)0.103 (2)
H90.56961.08270.32350.124*
C100.5363 (10)1.1996 (6)0.4415 (6)0.118 (2)
H100.60941.27450.44090.141*
C110.4540 (10)1.2034 (6)0.5126 (5)0.106 (2)
H110.47651.28060.56190.127*
C120.3412 (7)1.0990 (6)0.5138 (4)0.0885 (17)
C130.3121 (6)0.9806 (5)0.4406 (4)0.0790 (14)
C140.2511 (10)1.1074 (10)0.5923 (6)0.147 (4)
H14A0.26211.19460.62400.220*
H14B0.28641.07730.63470.220*
H14C0.14711.05560.56860.220*
C150.1874 (8)0.8636 (7)0.4391 (6)0.116 (2)
H15A0.09800.88150.45000.174*
H15B0.21390.83710.48660.174*
H15C0.16970.79660.37980.174*
C160.5928 (6)0.4556 (6)0.2219 (5)0.0889 (16)
H160.59850.50980.28640.107*
C190.9166 (8)0.5092 (8)0.2374 (7)0.1222 (16)
H19A1.01630.55920.27280.147*
H19B0.92490.44570.18120.147*
C17A0.666 (2)0.360 (2)0.227 (2)0.1222 (16)0.50
H17A0.60160.29880.25090.147*0.50
H17B0.68300.31420.16560.147*0.50
C18A0.8174 (18)0.4443 (17)0.2926 (13)0.1222 (16)0.50
H18A0.80350.50620.34760.147*0.50
H18B0.85930.39180.31110.147*0.50
C20A0.856 (3)0.594 (2)0.2134 (18)0.1222 (16)0.50
H20A0.91050.61890.16660.147*0.50
H20B0.87910.67070.26800.147*0.50
C21A0.687 (2)0.544 (5)0.178 (4)0.1222 (16)0.50
H21A0.65680.61640.19060.147*0.50
H21B0.67040.49970.11120.147*0.50
C17B0.6452 (19)0.363 (2)0.237 (2)0.1222 (16)0.50
H17C0.61010.28640.18150.147*0.50
H17D0.59540.33920.28620.147*0.50
C18B0.8160 (16)0.3987 (15)0.2633 (14)0.1222 (16)0.50
H18C0.83810.42140.32960.147*0.50
H18D0.84040.32430.23260.147*0.50
C20B0.860 (3)0.615 (2)0.2389 (18)0.1222 (16)0.50
H20C0.92650.67020.21110.147*0.50
H20D0.85800.66560.30210.147*0.50
C21B0.701 (2)0.548 (5)0.183 (4)0.1222 (16)0.50
H21C0.66210.61250.18340.147*0.50
H21D0.70660.50140.11940.147*0.50
C220.2180 (7)0.3375 (5)0.2686 (4)0.0855 (15)
H220.13770.35850.24700.103*
C250.1326 (12)0.2839 (8)0.4341 (6)0.152 (3)
H25A0.07850.26550.48320.182*
H25B0.22880.27520.43850.182*
C23A0.263 (3)0.441 (3)0.3636 (15)0.152 (3)0.50
H23A0.27020.52150.35830.182*0.50
H23B0.36100.45250.39000.182*0.50
C24A0.146 (3)0.4080 (17)0.4296 (17)0.152 (3)0.50
H24A0.17860.47410.49100.182*0.50
H24B0.04880.40290.40600.182*0.50
C26A0.040 (2)0.207 (2)0.3386 (10)0.152 (3)0.50
H26A−0.03380.24300.33270.182*0.50
H26B−0.01420.12070.33560.182*0.50
C27A0.123 (2)0.1990 (16)0.2542 (13)0.152 (3)0.50
H27A0.18580.15040.25130.182*0.50
H27B0.05200.15880.19740.182*0.50
C23B0.307 (2)0.418 (2)0.3655 (12)0.152 (3)0.50
H23C0.38510.38670.37370.182*0.50
H23D0.35630.50530.36960.182*0.50
C24B0.216 (2)0.4165 (16)0.4436 (16)0.152 (3)0.50
H24C0.28190.46270.50250.182*0.50
H24D0.14650.45820.44180.182*0.50
C26B0.094 (3)0.1719 (17)0.3434 (11)0.152 (3)0.50
H26C−0.01020.14380.31750.182*0.50
H26D0.10990.10090.35240.182*0.50
C27B0.199 (3)0.220 (2)0.2790 (14)0.152 (3)0.50
H27C0.29750.22500.29920.182*0.50
H27D0.16460.15330.21780.182*0.50
C280.2913 (7)0.2114 (5)0.0371 (4)0.0813 (15)
H280.18180.17310.03240.098*
C29A0.317 (3)0.2527 (16)−0.0469 (10)0.122 (2)0.50
H29A0.26360.3084−0.04530.146*0.50
H29B0.42330.3010−0.04280.146*0.50
C30A0.265 (3)0.1407 (16)−0.1369 (12)0.122 (2)0.50
H30A0.29950.1704−0.18650.146*0.50
H30B0.15570.1059−0.14790.146*0.50
C31A0.318 (3)0.0348 (17)−0.1409 (10)0.122 (2)0.50
H31A0.2743−0.0370−0.19890.146*0.50
H31B0.42650.0650−0.13710.146*0.50
C32A0.273 (3)−0.0041 (18)−0.0648 (10)0.122 (2)0.50
H32A0.3045−0.0733−0.06720.146*0.50
H32B0.1643−0.0355−0.06990.146*0.50
C33A0.341 (3)0.1060 (18)0.0271 (11)0.122 (2)0.50
H33A0.31300.07550.07720.146*0.50
H33B0.44980.13730.03200.146*0.50
C29B0.370 (2)0.2433 (15)−0.0391 (10)0.122 (2)0.50
H29C0.47760.2706−0.02220.146*0.50
H29D0.35090.3136−0.04690.146*0.50
C30B0.317 (3)0.1273 (16)−0.1317 (11)0.122 (2)0.50
H30C0.21140.1038−0.15200.146*0.50
H30D0.37370.1487−0.17900.146*0.50
C31B0.341 (3)0.0201 (16)−0.1169 (10)0.122 (2)0.50
H31C0.2969−0.0548−0.17310.146*0.50
H31D0.44820.0400−0.10910.146*0.50
C32B0.283 (3)−0.0146 (17)−0.0404 (9)0.122 (2)0.50
H32C0.3212−0.0761−0.03310.146*0.50
H32D0.1743−0.0555−0.05450.146*0.50
C33B0.324 (3)0.0971 (18)0.0484 (11)0.122 (2)0.50
H33C0.43040.12550.07050.146*0.50
H33D0.26810.07130.09450.146*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.0761 (2)0.04922 (19)0.0596 (2)0.02397 (15)0.00460 (15)0.01359 (14)
O10.093 (2)0.0494 (16)0.0617 (18)0.0339 (16)0.0004 (16)0.0063 (14)
O20.114 (3)0.063 (2)0.064 (2)0.046 (2)−0.0145 (19)0.0064 (16)
N10.129 (4)0.063 (3)0.059 (2)0.051 (3)−0.018 (2)−0.0025 (19)
C10.068 (3)0.049 (2)0.049 (2)0.0225 (19)0.0083 (19)0.0147 (18)
C20.080 (3)0.048 (2)0.052 (2)0.024 (2)0.006 (2)0.0105 (18)
C30.114 (4)0.056 (3)0.064 (3)0.039 (3)0.001 (3)0.013 (2)
C40.135 (5)0.071 (3)0.080 (4)0.051 (3)−0.013 (3)0.023 (3)
C50.140 (5)0.075 (4)0.069 (3)0.045 (4)−0.025 (3)0.016 (3)
C60.099 (4)0.059 (3)0.052 (3)0.029 (3)0.001 (2)0.007 (2)
C70.071 (3)0.050 (2)0.054 (2)0.024 (2)0.008 (2)0.0098 (19)
C80.099 (4)0.056 (3)0.056 (3)0.036 (3)−0.011 (3)0.002 (2)
C90.133 (6)0.071 (4)0.084 (4)0.024 (4)0.013 (4)0.018 (3)
C100.142 (6)0.059 (3)0.113 (6)0.010 (4)−0.012 (5)0.015 (4)
C110.142 (6)0.068 (4)0.085 (4)0.049 (4)−0.030 (4)−0.008 (3)
C120.099 (4)0.090 (4)0.066 (3)0.052 (4)−0.012 (3)−0.002 (3)
C130.082 (3)0.069 (3)0.072 (3)0.034 (3)−0.012 (3)0.005 (2)
C140.140 (7)0.189 (9)0.102 (6)0.098 (7)0.017 (5)0.005 (6)
C150.088 (4)0.106 (5)0.124 (6)0.018 (4)0.013 (4)0.025 (4)
C160.079 (3)0.086 (4)0.109 (5)0.033 (3)0.012 (3)0.043 (4)
C190.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C17A0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C18A0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C20A0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C21A0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C17B0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C18B0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C20B0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C21B0.084 (2)0.127 (3)0.165 (4)0.040 (2)0.014 (3)0.064 (3)
C220.101 (4)0.071 (3)0.077 (3)0.026 (3)0.014 (3)0.025 (3)
C250.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C23A0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C24A0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C26A0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C27A0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C23B0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C24B0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C26B0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C27B0.179 (7)0.136 (4)0.112 (3)0.021 (4)0.057 (4)0.050 (3)
C280.112 (4)0.056 (3)0.068 (3)0.034 (3)0.019 (3)0.011 (2)
C29A0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C30A0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C31A0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C32A0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C33A0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C29B0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C30B0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C31B0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C32B0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
C33B0.228 (6)0.086 (3)0.072 (3)0.084 (3)0.038 (4)0.029 (2)
Geometric parameters (Å, °) top
Sn—O12.073 (3)C21B—H21C0.9700
Sn—C162.130 (6)C21B—H21D0.9700
Sn—C282.147 (5)C22—C27B1.43 (2)
Sn—C222.153 (6)C22—C23A1.51 (2)
O1—C71.300 (5)C22—C27A1.526 (15)
O2—C71.228 (5)C22—C23B1.527 (17)
N1—C21.362 (6)C22—H220.9800
N1—C81.425 (6)C25—C24B1.464 (15)
N1—H10.90 (7)C25—C24A1.478 (16)
C1—C61.405 (6)C25—C26B1.510 (15)
C1—C21.417 (6)C25—C26A1.519 (16)
C1—C71.460 (6)C25—H25A0.9700
C2—C31.390 (7)C25—H25B0.9700
C3—C41.360 (8)C23A—C24A1.57 (3)
C3—H30.9300C23A—H23A0.9700
C4—C51.375 (8)C23A—H23B0.9700
C4—H40.9300C24A—H24A0.9700
C5—C61.356 (8)C24A—H24B0.9700
C5—H50.9300C26A—C27A1.531 (16)
C6—H60.9300C26A—H26A0.9700
C8—C131.366 (8)C26A—H26B0.9700
C8—C91.376 (9)C27A—H27A0.9700
C9—C101.364 (9)C27A—H27B0.9700
C9—H90.9300C23B—C24B1.505 (17)
C10—C111.362 (11)C23B—H23C0.9700
C10—H100.9300C23B—H23D0.9700
C11—C121.346 (10)C24B—H24C0.9700
C11—H110.9300C24B—H24D0.9700
C12—C131.417 (7)C26B—C27B1.531 (16)
C12—C141.499 (11)C26B—H26C0.9700
C13—C151.485 (9)C26B—H26D0.9700
C14—H14A0.9600C27B—H27C0.9700
C14—H14B0.9600C27B—H27D0.9700
C14—H14C0.9600C28—C33A1.465 (15)
C15—H15A0.9600C28—C29B1.498 (14)
C15—H15B0.9600C28—C29A1.539 (14)
C15—H15C0.9600C28—C33B1.576 (14)
C16—C17B1.461 (16)C28—H280.9800
C16—C21A1.503 (17)C29A—C30A1.500 (15)
C16—C21B1.527 (17)C29A—H29A0.9700
C16—C17A1.560 (15)C29A—H29B0.9700
C16—H160.9800C30A—C31A1.513 (14)
C19—C20A1.477 (16)C30A—H30A0.9700
C19—C18A1.483 (15)C30A—H30B0.9700
C19—C18B1.525 (14)C31A—C32A1.429 (14)
C19—C20B1.534 (16)C31A—H31A0.9700
C19—H19A0.9700C31A—H31B0.9700
C19—H19B0.9700C32A—C33A1.52 (2)
C17A—C18A1.557 (18)C32A—H32A0.9700
C17A—H17A0.9700C32A—H32B0.9700
C17A—H17B0.9700C33A—H33A0.9700
C18A—H18A0.9700C33A—H33B0.9700
C18A—H18B0.9700C29B—C30B1.546 (15)
C20A—C21A1.535 (17)C29B—H29C0.9700
C20A—H20A0.9700C29B—H29D0.9700
C20A—H20B0.9700C30B—C31B1.474 (12)
C21A—H21A0.9700C30B—H30C0.9700
C21A—H21B0.9700C30B—H30D0.9700
C17B—C18B1.553 (16)C31B—C32B1.442 (15)
C17B—H17C0.9700C31B—H31C0.9700
C17B—H17D0.9700C31B—H31D0.9700
C18B—H18C0.9700C32B—C33B1.488 (16)
C18B—H18D0.9700C32B—H32C0.9700
C20B—C21B1.540 (17)C32B—H32D0.9700
C20B—H20C0.9700C33B—H33C0.9700
C20B—H20D0.9700C33B—H33D0.9700
O1—Sn—C16112.38 (18)C27A—C22—Sn117.5 (7)
O1—Sn—C2894.52 (17)C23B—C22—Sn109.6 (9)
C16—Sn—C28117.4 (3)C27B—C22—H22125.4
O1—Sn—C22105.4 (2)C23A—C22—H2297.1
C16—Sn—C22112.4 (2)C27A—C22—H2297.1
C28—Sn—C22112.7 (2)C23B—C22—H22119.7
C7—O1—Sn111.7 (3)Sn—C22—H2297.1
C2—N1—C8124.6 (4)C24B—C25—C26B123.4 (13)
C2—N1—H1115 (4)C24A—C25—C26B117.1 (14)
C8—N1—H1120 (4)C24B—C25—C26A110.5 (14)
C6—C1—C2117.8 (4)C24A—C25—C26A93.7 (15)
C6—C1—C7120.1 (4)C24B—C25—H25A120.1
C2—C1—C7122.0 (4)C24A—C25—H25A113.0
N1—C2—C3121.2 (4)C26B—C25—H25A115.0
N1—C2—C1120.5 (4)C26A—C25—H25A113.0
C3—C2—C1118.2 (4)C24B—C25—H25B87.4
C4—C3—C2121.3 (5)C24A—C25—H25B113.0
C4—C3—H3119.4C26B—C25—H25B85.3
C2—C3—H3119.4C26A—C25—H25B113.0
C3—C4—C5121.6 (5)H25A—C25—H25B110.4
C3—C4—H4119.2C22—C23A—C24A111.2 (19)
C5—C4—H4119.2C22—C23A—H23A109.4
C6—C5—C4118.3 (5)C24A—C23A—H23A109.4
C6—C5—H5120.8C22—C23A—H23B109.4
C4—C5—H5120.8C24A—C23A—H23B109.4
C5—C6—C1122.7 (5)H23A—C23A—H23B108.0
C5—C6—H6118.6C25—C24A—C23A108.5 (17)
C1—C6—H6118.6C25—C24A—H24A110.0
O2—C7—O1119.8 (4)C23A—C24A—H24A110.0
O2—C7—C1123.5 (4)C25—C24A—H24B110.0
O1—C7—C1116.7 (4)C23A—C24A—H24B110.0
C13—C8—C9121.3 (5)H24A—C24A—H24B108.4
C13—C8—N1119.2 (5)C25—C26A—C27A118.1 (15)
C9—C8—N1119.5 (6)C25—C26A—H26A107.8
C10—C9—C8119.1 (7)C27A—C26A—H26A107.8
C10—C9—H9120.4C25—C26A—H26B107.8
C8—C9—H9120.4C27A—C26A—H26B107.8
C11—C10—C9120.1 (7)H26A—C26A—H26B107.1
C11—C10—H10119.9C22—C27A—C26A104.8 (14)
C9—C10—H10119.9C22—C27A—H27A110.8
C12—C11—C10122.0 (6)C26A—C27A—H27A110.8
C12—C11—H11119.0C22—C27A—H27B110.8
C10—C11—H11119.0C26A—C27A—H27B110.8
C11—C12—C13118.6 (6)H27A—C27A—H27B108.9
C11—C12—C14120.5 (7)C24B—C23B—C22115.1 (17)
C13—C12—C14120.8 (7)C24B—C23B—H23C108.5
C8—C13—C12118.7 (6)C22—C23B—H23C108.5
C8—C13—C15121.2 (5)C24B—C23B—H23D108.5
C12—C13—C15120.1 (6)C22—C23B—H23D108.5
C12—C14—H14A109.5H23C—C23B—H23D107.5
C12—C14—H14B109.5C25—C24B—C23B109.0 (17)
H14A—C14—H14B109.5C25—C24B—H24C109.9
C12—C14—H14C109.5C23B—C24B—H24C109.9
H14A—C14—H14C109.5C25—C24B—H24D109.9
H14B—C14—H14C109.5C23B—C24B—H24D109.9
C13—C15—H15A109.5H24C—C24B—H24D108.3
C13—C15—H15B109.5C25—C26B—C27B106.1 (14)
H15A—C15—H15B109.5C25—C26B—H26C110.5
C13—C15—H15C109.5C27B—C26B—H26C110.5
H15A—C15—H15C109.5C25—C26B—H26D110.5
H15B—C15—H15C109.5C27B—C26B—H26D110.5
C17B—C16—C21A119 (2)H26C—C26B—H26D108.7
C17B—C16—C21B115.7 (19)C22—C27B—C26B121.4 (18)
C21A—C16—C17A110 (2)C22—C27B—H27C107.0
C21B—C16—C17A107 (2)C26B—C27B—H27C107.0
C17B—C16—Sn111.2 (9)C22—C27B—H27D107.0
C21A—C16—Sn114.0 (11)C26B—C27B—H27D107.0
C21B—C16—Sn119.1 (10)H27C—C27B—H27D106.7
C17A—C16—Sn115.2 (8)C33A—C28—C29B93.9 (10)
C17B—C16—H1699.3C33A—C28—C29A111.0 (9)
C21A—C16—H16105.4C29B—C28—C33B108.4 (9)
C21B—C16—H16103.0C29A—C28—C33B125.4 (9)
C17A—C16—H16105.4C33A—C28—Sn118.3 (9)
Sn—C16—H16105.4C29B—C28—Sn112.6 (7)
C20A—C19—C18A110.5 (14)C29A—C28—Sn112.6 (7)
C20A—C19—C18B121.2 (14)C33B—C28—Sn109.8 (7)
C18A—C19—C20B103.6 (14)C33A—C28—H28104.4
C18B—C19—C20B118.9 (13)C29B—C28—H28123.6
C20A—C19—H19A109.5C29A—C28—H28104.4
C18A—C19—H19A109.5C33B—C28—H2896.6
C18B—C19—H19A117.6Sn—C28—H28104.4
C20B—C19—H19A101.4C30A—C29A—C28112.1 (12)
C20A—C19—H19B109.5C30A—C29A—H29A109.2
C18A—C19—H19B109.5C28—C29A—H29A109.2
C18B—C19—H19B87.6C30A—C29A—H29B109.2
C20B—C19—H19B123.9C28—C29A—H29B109.2
H19A—C19—H19B108.1H29A—C29A—H29B107.9
C18A—C17A—C16105.3 (15)C29A—C30A—C31A114.3 (13)
C18A—C17A—H17A110.7C29A—C30A—H30A108.7
C16—C17A—H17A110.7C31A—C30A—H30A108.7
C18A—C17A—H17B110.7C29A—C30A—H30B108.7
C16—C17A—H17B110.7C31A—C30A—H30B108.7
H17A—C17A—H17B108.8H30A—C30A—H30B107.6
C19—C18A—C17A104.7 (15)C32A—C31A—C30A108.4 (13)
C19—C18A—H18A110.8C32A—C31A—H31A110.0
C17A—C18A—H18A110.8C30A—C31A—H31A110.0
C19—C18A—H18B110.8C32A—C31A—H31B110.0
C17A—C18A—H18B110.8C30A—C31A—H31B110.0
H18A—C18A—H18B108.9H31A—C31A—H31B108.4
C19—C20A—C21A119 (2)C31A—C32A—C33A111.3 (15)
C19—C20A—H20A107.5C31A—C32A—H32A109.4
C21A—C20A—H20A107.5C33A—C32A—H32A109.4
C19—C20A—H20B107.5C31A—C32A—H32B109.4
C21A—C20A—H20B107.5C33A—C32A—H32B109.4
H20A—C20A—H20B107.0H32A—C32A—H32B108.0
C16—C21A—C20A112 (2)C28—C33A—C32A112.1 (16)
C16—C21A—H21A109.1C28—C33A—H33A109.2
C20A—C21A—H21A109.1C32A—C33A—H33A109.2
C16—C21A—H21B109.1C28—C33A—H33B109.2
C20A—C21A—H21B109.1C32A—C33A—H33B109.2
H21A—C21A—H21B107.9H33A—C33A—H33B107.9
C16—C17B—C18B119.5 (15)C28—C29B—C30B111.6 (13)
C16—C17B—H17C107.4C28—C29B—H29C109.3
C18B—C17B—H17C107.4C30B—C29B—H29C109.3
C16—C17B—H17D107.4C28—C29B—H29D109.3
C18B—C17B—H17D107.4C30B—C29B—H29D109.3
H17C—C17B—H17D107.0H29C—C29B—H29D108.0
C19—C18B—C17B114.2 (13)C31B—C30B—C29B108.2 (12)
C19—C18B—H18C108.7C31B—C30B—H30C110.1
C17B—C18B—H18C108.7C29B—C30B—H30C110.1
C19—C18B—H18D108.7C31B—C30B—H30D110.1
C17B—C18B—H18D108.7C29B—C30B—H30D110.1
H18C—C18B—H18D107.6H30C—C30B—H30D108.4
C19—C20B—C21B107 (2)C32B—C31B—C30B118.5 (14)
C19—C20B—H20C110.3C32B—C31B—H31C107.7
C21B—C20B—H20C110.3C30B—C31B—H31C107.7
C19—C20B—H20D110.3C32B—C31B—H31D107.7
C21B—C20B—H20D110.3C30B—C31B—H31D107.7
H20C—C20B—H20D108.5H31C—C31B—H31D107.1
C16—C21B—C20B113 (2)C31B—C32B—C33B112.9 (13)
C16—C21B—H21C109.0C31B—C32B—H32C109.0
C20B—C21B—H21C109.0C33B—C32B—H32C109.0
C16—C21B—H21D109.0C31B—C32B—H32D109.0
C20B—C21B—H21D109.0C33B—C32B—H32D109.0
H21C—C21B—H21D107.8H32C—C32B—H32D107.8
C27B—C22—C23A108.1 (14)C32B—C33B—C28111.8 (12)
C23A—C22—C27A121.5 (13)C32B—C33B—H33C109.3
C27B—C22—C23B93.1 (14)C28—C33B—H33C109.3
C27A—C22—C23B114.6 (13)C32B—C33B—H33D109.3
C27B—C22—Sn112.3 (9)C28—C33B—H33D109.3
C23A—C22—Sn116.5 (10)H33C—C33B—H33D107.9
C16—Sn—O1—C7−55.7 (4)C16—Sn—C22—C27B−84.3 (11)
C28—Sn—O1—C7−177.9 (3)C28—Sn—C22—C27B51.1 (11)
C22—Sn—O1—C767.1 (4)O1—Sn—C22—C23A−81.6 (13)
C8—N1—C2—C34.6 (9)C16—Sn—C22—C23A41.1 (13)
C8—N1—C2—C1−174.8 (5)C28—Sn—C22—C23A176.6 (13)
C6—C1—C2—N1−178.5 (5)O1—Sn—C22—C27A121.8 (12)
C7—C1—C2—N14.8 (7)C16—Sn—C22—C27A−115.5 (12)
C6—C1—C2—C32.0 (7)C28—Sn—C22—C27A20.0 (13)
C7—C1—C2—C3−174.6 (5)O1—Sn—C22—C23B−105.1 (12)
N1—C2—C3—C4179.2 (6)C16—Sn—C22—C23B17.6 (12)
C1—C2—C3—C4−1.4 (9)C28—Sn—C22—C23B153.1 (12)
C2—C3—C4—C5−0.2 (11)C27B—C22—C23A—C24A−55 (2)
C3—C4—C5—C61.0 (11)C27A—C22—C23A—C24A−27 (3)
C4—C5—C6—C1−0.3 (10)C23B—C22—C23A—C24A−106 (5)
C2—C1—C6—C5−1.3 (8)Sn—C22—C23A—C24A177.1 (13)
C7—C1—C6—C5175.5 (6)C24B—C25—C24A—C23A56 (3)
Sn—O1—C7—O24.3 (6)C26B—C25—C24A—C23A−55 (2)
Sn—O1—C7—C1−173.5 (3)C26A—C25—C24A—C23A−75.2 (18)
C6—C1—C7—O2−175.3 (5)C22—C23A—C24A—C2557 (2)
C2—C1—C7—O21.3 (7)C24B—C25—C26A—C27A59 (2)
C6—C1—C7—O12.5 (7)C24A—C25—C26A—C27A79 (2)
C2—C1—C7—O1179.1 (4)C26B—C25—C26A—C27A−63 (2)
C2—N1—C8—C1395.1 (7)C27B—C22—C27A—C26A92 (3)
C2—N1—C8—C9−87.1 (8)C23A—C22—C27A—C26A23 (3)
C13—C8—C9—C100.9 (10)C23B—C22—C27A—C26A47 (2)
N1—C8—C9—C10−176.7 (6)Sn—C22—C27A—C26A178.1 (11)
C8—C9—C10—C112.0 (12)C25—C26A—C27A—C22−52 (2)
C9—C10—C11—C12−4.0 (12)C27B—C22—C23B—C24B−73 (2)
C10—C11—C12—C132.9 (10)C23A—C22—C23B—C24B60 (4)
C10—C11—C12—C14−178.8 (7)C27A—C22—C23B—C24B−53 (2)
C9—C8—C13—C12−2.0 (8)Sn—C22—C23B—C24B172.4 (16)
N1—C8—C13—C12175.7 (5)C24A—C25—C24B—C23B−107 (4)
C9—C8—C13—C15177.5 (6)C26B—C25—C24B—C23B−23 (3)
N1—C8—C13—C15−4.8 (8)C26A—C25—C24B—C23B−54 (2)
C11—C12—C13—C80.1 (8)C22—C23B—C24B—C2554 (3)
C14—C12—C13—C8−178.2 (6)C24B—C25—C26B—C27B18 (3)
C11—C12—C13—C15−179.4 (6)C24A—C25—C26B—C27B48 (2)
C14—C12—C13—C152.3 (9)C26A—C25—C26B—C27B90 (3)
O1—Sn—C16—C17B−167.1 (14)C23A—C22—C27B—C26B54 (2)
C28—Sn—C16—C17B−59.1 (15)C27A—C22—C27B—C26B−69 (3)
C22—Sn—C16—C17B74.1 (15)C23B—C22—C27B—C26B71 (2)
O1—Sn—C16—C21A−29 (3)Sn—C22—C27B—C26B−176.1 (15)
C28—Sn—C16—C21A79 (3)C25—C26B—C27B—C22−48 (3)
C22—Sn—C16—C21A−148 (3)O1—Sn—C28—C33A167.8 (12)
O1—Sn—C16—C21B−29 (3)C16—Sn—C28—C33A49.7 (12)
C28—Sn—C16—C21B79 (3)C22—Sn—C28—C33A−83.4 (12)
C22—Sn—C16—C21B−147 (3)O1—Sn—C28—C29B59.9 (9)
O1—Sn—C16—C17A−158.0 (13)C16—Sn—C28—C29B−58.2 (9)
C28—Sn—C16—C17A−49.9 (14)C22—Sn—C28—C29B168.7 (9)
C22—Sn—C16—C17A83.3 (13)O1—Sn—C28—C29A36.1 (10)
C17B—C16—C17A—C18A−98 (12)C16—Sn—C28—C29A−82.0 (10)
C21A—C16—C17A—C18A64 (3)C22—Sn—C28—C29A144.9 (10)
C21B—C16—C17A—C18A60 (3)O1—Sn—C28—C33B−179.2 (11)
Sn—C16—C17A—C18A−164.7 (11)C16—Sn—C28—C33B62.7 (11)
C20A—C19—C18A—C17A63.2 (17)C22—Sn—C28—C33B−70.4 (11)
C18B—C19—C18A—C17A−60 (3)C33A—C28—C29A—C30A46 (2)
C20B—C19—C18A—C17A76.4 (16)C29B—C28—C29A—C30A87 (3)
C16—C17A—C18A—C19−73.9 (19)C33B—C28—C29A—C30A43 (2)
C18A—C19—C20A—C21A−45 (3)Sn—C28—C29A—C30A−178.4 (12)
C18B—C19—C20A—C21A−24 (4)C28—C29A—C30A—C31A−48 (2)
C20B—C19—C20A—C21A−108 (10)C29A—C30A—C31A—C32A55 (2)
C17B—C16—C21A—C20A−40 (5)C30A—C31A—C32A—C33A−60 (2)
C17A—C16—C21A—C20A−43 (5)C29B—C28—C33A—C32A−66.4 (18)
Sn—C16—C21A—C20A−175 (3)C29A—C28—C33A—C32A−52 (2)
C19—C20A—C21A—C1634 (6)C33B—C28—C33A—C32A118 (9)
C21A—C16—C17B—C18B35 (4)Sn—C28—C33A—C32A175.2 (11)
C21B—C16—C17B—C18B31 (4)C31A—C32A—C33A—C2862 (2)
C17A—C16—C17B—C18B54 (10)C33A—C28—C29B—C30B57.8 (16)
Sn—C16—C17B—C18B170.8 (19)C29A—C28—C29B—C30B−85 (3)
C18A—C19—C18B—C17B81 (4)C33B—C28—C29B—C30B59.0 (18)
C20B—C19—C18B—C17B32 (2)Sn—C28—C29B—C30B−179.2 (10)
C16—C17B—C18B—C19−21 (3)C28—C29B—C30B—C31B−56 (2)
C20A—C19—C20B—C21B53 (7)C29B—C30B—C31B—C32B51 (3)
C18A—C19—C20B—C21B−67 (2)C30B—C31B—C32B—C33B−49 (3)
C18B—C19—C20B—C21B−50 (3)C31B—C32B—C33B—C2849 (2)
C17B—C16—C21B—C20B−51 (5)C33A—C28—C33B—C32B−50 (7)
C17A—C16—C21B—C20B−55 (5)C29B—C28—C33B—C32B−55 (2)
Sn—C16—C21B—C20B172 (2)C29A—C28—C33B—C32B−39 (3)
C19—C20B—C21B—C1658 (5)Sn—C28—C33B—C32B−178.2 (14)
O1—Sn—C22—C27B152.9 (11)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.90 (7)1.93 (7)2.656 (6)137 (6)
C23A—H23A···O20.972.453.17 (3)132
Table 1
Selected geometric parameters (Å) top
Sn—O12.073 (3)Sn—C282.147 (5)
Sn—C162.130 (6)Sn—C222.153 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.90 (7)1.93 (7)2.656 (6)137 (6)
C23A—H23A···O20.972.453.17 (3)132
references
References top

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Danish, M., Ali, S., badshah, A., Mazhar, M., Masood, H., Malik, A. & Kehr, G. (1997). Synth. React. Inorg. Met. Org. Chem. 27, 863–885.

Danish, M., Tahir, M. N., Ahmad, N., Raza, A. R. & Ibrahim, M. (2009). Acta Cryst. E65, m609–m610.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Tahir, M. N., Ülkü, D., Ali, S., Masood, T., Danish, M. & Mazhar, M. (1997b). Acta Cryst. C53, 1574–1576.

Tahir, M. N., Ülkü, D., Danish, M., Ali, S., Badshah, A. & Mazhar, M. (1997a). Acta Cryst. C53, 183–185.

Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Basu Baul, T. S. & Tiekink, E. R. T. (1998). Organometallics 17, 5758–5766.