metal-organic compounds
Tricyclohexyl[2-(2,3-dimethylanilino)benzoato-κO]tin(IV)
aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and cDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
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.
Related literature
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
Crystal data
|
Refinement
|
|
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536809048314/hb5223sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809048314/hb5223Isup2.hkl
The title compound was prepared according to the method described already (Danish et al., 1997) to yield colourless prisms of (I).
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
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).
Data collection: APEX2 (Bruker, 2007); cell
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).[Sn(C6H11)3(C15H14NO2)] | Z = 2 |
Mr = 608.41 | F(000) = 636 |
Triclinic, P1 | Dx = 1.298 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6093 (2) Å | Cell parameters from 7684 reflections |
b = 12.0104 (3) Å | θ = 2.3–28.3° |
c = 15.5241 (4) Å | µ = 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 |
Bruker Kappa APEXII CCD diffractometer | 7684 independent reflections |
Radiation source: fine-focus sealed tube | 5308 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 7.40 pixels mm-1 | θmax = 28.3°, θmin = 2.3° |
ω scans | h = −12→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→15 |
Tmin = 0.797, Tmax = 0.841 | l = −20→20 |
31924 measured reflections |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H 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 parameters | Δρmax = 1.37 e Å−3 |
33 restraints | Δρmin = −0.49 e Å−3 |
[Sn(C6H11)3(C15H14NO2)] | γ = 110.548 (1)° |
Mr = 608.41 | V = 1560.47 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6093 (2) Å | Mo Kα radiation |
b = 12.0104 (3) Å | µ = 0.85 mm−1 |
c = 15.5241 (4) Å | T = 296 K |
α = 109.872 (1)° | 0.28 × 0.22 × 0.20 mm |
β = 90.616 (2)° |
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 = 0.841 | Rint = 0.030 |
31924 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 33 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 1.37 e Å−3 |
7684 reflections | Δρmin = −0.49 e Å−3 |
307 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn | 0.36022 (4) | 0.37096 (3) | 0.16644 (2) | 0.06337 (15) | |
O1 | 0.2926 (4) | 0.4860 (3) | 0.1161 (2) | 0.0701 (8) | |
O2 | 0.3934 (5) | 0.6278 (3) | 0.2549 (2) | 0.0815 (10) | |
N1 | 0.3785 (6) | 0.8571 (4) | 0.3012 (3) | 0.0864 (14) | |
H1 | 0.413 (7) | 0.803 (6) | 0.314 (5) | 0.104* | |
C1 | 0.2665 (5) | 0.6839 (4) | 0.1546 (3) | 0.0565 (10) | |
C2 | 0.2909 (6) | 0.8087 (4) | 0.2175 (3) | 0.0622 (11) | |
C3 | 0.2220 (7) | 0.8792 (5) | 0.1918 (4) | 0.0785 (14) | |
H3 | 0.2350 | 0.9605 | 0.2328 | 0.094* | |
C4 | 0.1360 (8) | 0.8315 (6) | 0.1077 (4) | 0.0930 (18) | |
H4 | 0.0912 | 0.8809 | 0.0926 | 0.112* | |
C5 | 0.1136 (8) | 0.7119 (6) | 0.0446 (4) | 0.097 (2) | |
H5 | 0.0558 | 0.6808 | −0.0131 | 0.116* | |
C6 | 0.1779 (6) | 0.6405 (5) | 0.0685 (3) | 0.0740 (13) | |
H6 | 0.1627 | 0.5594 | 0.0261 | 0.089* | |
C7 | 0.3235 (5) | 0.5990 (4) | 0.1789 (3) | 0.0604 (10) | |
C8 | 0.3998 (7) | 0.9770 (5) | 0.3718 (3) | 0.0735 (13) | |
C9 | 0.5116 (9) | 1.0862 (6) | 0.3712 (5) | 0.103 (2) | |
H9 | 0.5696 | 1.0827 | 0.3235 | 0.124* | |
C10 | 0.5363 (10) | 1.1996 (6) | 0.4415 (6) | 0.118 (2) | |
H10 | 0.6094 | 1.2745 | 0.4409 | 0.141* | |
C11 | 0.4540 (10) | 1.2034 (6) | 0.5126 (5) | 0.106 (2) | |
H11 | 0.4765 | 1.2806 | 0.5619 | 0.127* | |
C12 | 0.3412 (7) | 1.0990 (6) | 0.5138 (4) | 0.0885 (17) | |
C13 | 0.3121 (6) | 0.9806 (5) | 0.4406 (4) | 0.0790 (14) | |
C14 | 0.2511 (10) | 1.1074 (10) | 0.5923 (6) | 0.147 (4) | |
H14A | 0.2621 | 1.1946 | 0.6240 | 0.220* | |
H14B | 0.2864 | 1.0773 | 0.6347 | 0.220* | |
H14C | 0.1471 | 1.0556 | 0.5686 | 0.220* | |
C15 | 0.1874 (8) | 0.8636 (7) | 0.4391 (6) | 0.116 (2) | |
H15A | 0.0980 | 0.8815 | 0.4500 | 0.174* | |
H15B | 0.2139 | 0.8371 | 0.4866 | 0.174* | |
H15C | 0.1697 | 0.7966 | 0.3798 | 0.174* | |
C16 | 0.5928 (6) | 0.4556 (6) | 0.2219 (5) | 0.0889 (16) | |
H16 | 0.5985 | 0.5098 | 0.2864 | 0.107* | |
C19 | 0.9166 (8) | 0.5092 (8) | 0.2374 (7) | 0.1222 (16) | |
H19A | 1.0163 | 0.5592 | 0.2728 | 0.147* | |
H19B | 0.9249 | 0.4457 | 0.1812 | 0.147* | |
C17A | 0.666 (2) | 0.360 (2) | 0.227 (2) | 0.1222 (16) | 0.50 |
H17A | 0.6016 | 0.2988 | 0.2509 | 0.147* | 0.50 |
H17B | 0.6830 | 0.3142 | 0.1656 | 0.147* | 0.50 |
C18A | 0.8174 (18) | 0.4443 (17) | 0.2926 (13) | 0.1222 (16) | 0.50 |
H18A | 0.8035 | 0.5062 | 0.3476 | 0.147* | 0.50 |
H18B | 0.8593 | 0.3918 | 0.3111 | 0.147* | 0.50 |
C20A | 0.856 (3) | 0.594 (2) | 0.2134 (18) | 0.1222 (16) | 0.50 |
H20A | 0.9105 | 0.6189 | 0.1666 | 0.147* | 0.50 |
H20B | 0.8791 | 0.6707 | 0.2680 | 0.147* | 0.50 |
C21A | 0.687 (2) | 0.544 (5) | 0.178 (4) | 0.1222 (16) | 0.50 |
H21A | 0.6568 | 0.6164 | 0.1906 | 0.147* | 0.50 |
H21B | 0.6704 | 0.4997 | 0.1112 | 0.147* | 0.50 |
C17B | 0.6452 (19) | 0.363 (2) | 0.237 (2) | 0.1222 (16) | 0.50 |
H17C | 0.6101 | 0.2864 | 0.1815 | 0.147* | 0.50 |
H17D | 0.5954 | 0.3392 | 0.2862 | 0.147* | 0.50 |
C18B | 0.8160 (16) | 0.3987 (15) | 0.2633 (14) | 0.1222 (16) | 0.50 |
H18C | 0.8381 | 0.4214 | 0.3296 | 0.147* | 0.50 |
H18D | 0.8404 | 0.3243 | 0.2326 | 0.147* | 0.50 |
C20B | 0.860 (3) | 0.615 (2) | 0.2389 (18) | 0.1222 (16) | 0.50 |
H20C | 0.9265 | 0.6702 | 0.2111 | 0.147* | 0.50 |
H20D | 0.8580 | 0.6656 | 0.3021 | 0.147* | 0.50 |
C21B | 0.701 (2) | 0.548 (5) | 0.183 (4) | 0.1222 (16) | 0.50 |
H21C | 0.6621 | 0.6125 | 0.1834 | 0.147* | 0.50 |
H21D | 0.7066 | 0.5014 | 0.1194 | 0.147* | 0.50 |
C22 | 0.2180 (7) | 0.3375 (5) | 0.2686 (4) | 0.0855 (15) | |
H22 | 0.1377 | 0.3585 | 0.2470 | 0.103* | |
C25 | 0.1326 (12) | 0.2839 (8) | 0.4341 (6) | 0.152 (3) | |
H25A | 0.0785 | 0.2655 | 0.4832 | 0.182* | |
H25B | 0.2288 | 0.2752 | 0.4385 | 0.182* | |
C23A | 0.263 (3) | 0.441 (3) | 0.3636 (15) | 0.152 (3) | 0.50 |
H23A | 0.2702 | 0.5215 | 0.3583 | 0.182* | 0.50 |
H23B | 0.3610 | 0.4525 | 0.3900 | 0.182* | 0.50 |
C24A | 0.146 (3) | 0.4080 (17) | 0.4296 (17) | 0.152 (3) | 0.50 |
H24A | 0.1786 | 0.4741 | 0.4910 | 0.182* | 0.50 |
H24B | 0.0488 | 0.4029 | 0.4060 | 0.182* | 0.50 |
C26A | 0.040 (2) | 0.207 (2) | 0.3386 (10) | 0.152 (3) | 0.50 |
H26A | −0.0338 | 0.2430 | 0.3327 | 0.182* | 0.50 |
H26B | −0.0142 | 0.1207 | 0.3356 | 0.182* | 0.50 |
C27A | 0.123 (2) | 0.1990 (16) | 0.2542 (13) | 0.152 (3) | 0.50 |
H27A | 0.1858 | 0.1504 | 0.2513 | 0.182* | 0.50 |
H27B | 0.0520 | 0.1588 | 0.1974 | 0.182* | 0.50 |
C23B | 0.307 (2) | 0.418 (2) | 0.3655 (12) | 0.152 (3) | 0.50 |
H23C | 0.3851 | 0.3867 | 0.3737 | 0.182* | 0.50 |
H23D | 0.3563 | 0.5053 | 0.3696 | 0.182* | 0.50 |
C24B | 0.216 (2) | 0.4165 (16) | 0.4436 (16) | 0.152 (3) | 0.50 |
H24C | 0.2819 | 0.4627 | 0.5025 | 0.182* | 0.50 |
H24D | 0.1465 | 0.4582 | 0.4418 | 0.182* | 0.50 |
C26B | 0.094 (3) | 0.1719 (17) | 0.3434 (11) | 0.152 (3) | 0.50 |
H26C | −0.0102 | 0.1438 | 0.3175 | 0.182* | 0.50 |
H26D | 0.1099 | 0.1009 | 0.3524 | 0.182* | 0.50 |
C27B | 0.199 (3) | 0.220 (2) | 0.2790 (14) | 0.152 (3) | 0.50 |
H27C | 0.2975 | 0.2250 | 0.2992 | 0.182* | 0.50 |
H27D | 0.1646 | 0.1533 | 0.2178 | 0.182* | 0.50 |
C28 | 0.2913 (7) | 0.2114 (5) | 0.0371 (4) | 0.0813 (15) | |
H28 | 0.1818 | 0.1731 | 0.0324 | 0.098* | |
C29A | 0.317 (3) | 0.2527 (16) | −0.0469 (10) | 0.122 (2) | 0.50 |
H29A | 0.2636 | 0.3084 | −0.0453 | 0.146* | 0.50 |
H29B | 0.4233 | 0.3010 | −0.0428 | 0.146* | 0.50 |
C30A | 0.265 (3) | 0.1407 (16) | −0.1369 (12) | 0.122 (2) | 0.50 |
H30A | 0.2995 | 0.1704 | −0.1865 | 0.146* | 0.50 |
H30B | 0.1557 | 0.1059 | −0.1479 | 0.146* | 0.50 |
C31A | 0.318 (3) | 0.0348 (17) | −0.1409 (10) | 0.122 (2) | 0.50 |
H31A | 0.2743 | −0.0370 | −0.1989 | 0.146* | 0.50 |
H31B | 0.4265 | 0.0650 | −0.1371 | 0.146* | 0.50 |
C32A | 0.273 (3) | −0.0041 (18) | −0.0648 (10) | 0.122 (2) | 0.50 |
H32A | 0.3045 | −0.0733 | −0.0672 | 0.146* | 0.50 |
H32B | 0.1643 | −0.0355 | −0.0699 | 0.146* | 0.50 |
C33A | 0.341 (3) | 0.1060 (18) | 0.0271 (11) | 0.122 (2) | 0.50 |
H33A | 0.3130 | 0.0755 | 0.0772 | 0.146* | 0.50 |
H33B | 0.4498 | 0.1373 | 0.0320 | 0.146* | 0.50 |
C29B | 0.370 (2) | 0.2433 (15) | −0.0391 (10) | 0.122 (2) | 0.50 |
H29C | 0.4776 | 0.2706 | −0.0222 | 0.146* | 0.50 |
H29D | 0.3509 | 0.3136 | −0.0469 | 0.146* | 0.50 |
C30B | 0.317 (3) | 0.1273 (16) | −0.1317 (11) | 0.122 (2) | 0.50 |
H30C | 0.2114 | 0.1038 | −0.1520 | 0.146* | 0.50 |
H30D | 0.3737 | 0.1487 | −0.1790 | 0.146* | 0.50 |
C31B | 0.341 (3) | 0.0201 (16) | −0.1169 (10) | 0.122 (2) | 0.50 |
H31C | 0.2969 | −0.0548 | −0.1731 | 0.146* | 0.50 |
H31D | 0.4482 | 0.0400 | −0.1091 | 0.146* | 0.50 |
C32B | 0.283 (3) | −0.0146 (17) | −0.0404 (9) | 0.122 (2) | 0.50 |
H32C | 0.3212 | −0.0761 | −0.0331 | 0.146* | 0.50 |
H32D | 0.1743 | −0.0555 | −0.0545 | 0.146* | 0.50 |
C33B | 0.324 (3) | 0.0971 (18) | 0.0484 (11) | 0.122 (2) | 0.50 |
H33C | 0.4304 | 0.1255 | 0.0705 | 0.146* | 0.50 |
H33D | 0.2681 | 0.0713 | 0.0945 | 0.146* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn | 0.0761 (2) | 0.04922 (19) | 0.0596 (2) | 0.02397 (15) | 0.00460 (15) | 0.01359 (14) |
O1 | 0.093 (2) | 0.0494 (16) | 0.0617 (18) | 0.0339 (16) | 0.0004 (16) | 0.0063 (14) |
O2 | 0.114 (3) | 0.063 (2) | 0.064 (2) | 0.046 (2) | −0.0145 (19) | 0.0064 (16) |
N1 | 0.129 (4) | 0.063 (3) | 0.059 (2) | 0.051 (3) | −0.018 (2) | −0.0025 (19) |
C1 | 0.068 (3) | 0.049 (2) | 0.049 (2) | 0.0225 (19) | 0.0083 (19) | 0.0147 (18) |
C2 | 0.080 (3) | 0.048 (2) | 0.052 (2) | 0.024 (2) | 0.006 (2) | 0.0105 (18) |
C3 | 0.114 (4) | 0.056 (3) | 0.064 (3) | 0.039 (3) | 0.001 (3) | 0.013 (2) |
C4 | 0.135 (5) | 0.071 (3) | 0.080 (4) | 0.051 (3) | −0.013 (3) | 0.023 (3) |
C5 | 0.140 (5) | 0.075 (4) | 0.069 (3) | 0.045 (4) | −0.025 (3) | 0.016 (3) |
C6 | 0.099 (4) | 0.059 (3) | 0.052 (3) | 0.029 (3) | 0.001 (2) | 0.007 (2) |
C7 | 0.071 (3) | 0.050 (2) | 0.054 (2) | 0.024 (2) | 0.008 (2) | 0.0098 (19) |
C8 | 0.099 (4) | 0.056 (3) | 0.056 (3) | 0.036 (3) | −0.011 (3) | 0.002 (2) |
C9 | 0.133 (6) | 0.071 (4) | 0.084 (4) | 0.024 (4) | 0.013 (4) | 0.018 (3) |
C10 | 0.142 (6) | 0.059 (3) | 0.113 (6) | 0.010 (4) | −0.012 (5) | 0.015 (4) |
C11 | 0.142 (6) | 0.068 (4) | 0.085 (4) | 0.049 (4) | −0.030 (4) | −0.008 (3) |
C12 | 0.099 (4) | 0.090 (4) | 0.066 (3) | 0.052 (4) | −0.012 (3) | −0.002 (3) |
C13 | 0.082 (3) | 0.069 (3) | 0.072 (3) | 0.034 (3) | −0.012 (3) | 0.005 (2) |
C14 | 0.140 (7) | 0.189 (9) | 0.102 (6) | 0.098 (7) | 0.017 (5) | 0.005 (6) |
C15 | 0.088 (4) | 0.106 (5) | 0.124 (6) | 0.018 (4) | 0.013 (4) | 0.025 (4) |
C16 | 0.079 (3) | 0.086 (4) | 0.109 (5) | 0.033 (3) | 0.012 (3) | 0.043 (4) |
C19 | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C17A | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C18A | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C20A | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C21A | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C17B | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C18B | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C20B | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C21B | 0.084 (2) | 0.127 (3) | 0.165 (4) | 0.040 (2) | 0.014 (3) | 0.064 (3) |
C22 | 0.101 (4) | 0.071 (3) | 0.077 (3) | 0.026 (3) | 0.014 (3) | 0.025 (3) |
C25 | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C23A | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C24A | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C26A | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C27A | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C23B | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C24B | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C26B | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C27B | 0.179 (7) | 0.136 (4) | 0.112 (3) | 0.021 (4) | 0.057 (4) | 0.050 (3) |
C28 | 0.112 (4) | 0.056 (3) | 0.068 (3) | 0.034 (3) | 0.019 (3) | 0.011 (2) |
C29A | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C30A | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C31A | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C32A | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C33A | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C29B | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C30B | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C31B | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C32B | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
C33B | 0.228 (6) | 0.086 (3) | 0.072 (3) | 0.084 (3) | 0.038 (4) | 0.029 (2) |
Sn—O1 | 2.073 (3) | C21B—H21C | 0.9700 |
Sn—C16 | 2.130 (6) | C21B—H21D | 0.9700 |
Sn—C28 | 2.147 (5) | C22—C27B | 1.43 (2) |
Sn—C22 | 2.153 (6) | C22—C23A | 1.51 (2) |
O1—C7 | 1.300 (5) | C22—C27A | 1.526 (15) |
O2—C7 | 1.228 (5) | C22—C23B | 1.527 (17) |
N1—C2 | 1.362 (6) | C22—H22 | 0.9800 |
N1—C8 | 1.425 (6) | C25—C24B | 1.464 (15) |
N1—H1 | 0.90 (7) | C25—C24A | 1.478 (16) |
C1—C6 | 1.405 (6) | C25—C26B | 1.510 (15) |
C1—C2 | 1.417 (6) | C25—C26A | 1.519 (16) |
C1—C7 | 1.460 (6) | C25—H25A | 0.9700 |
C2—C3 | 1.390 (7) | C25—H25B | 0.9700 |
C3—C4 | 1.360 (8) | C23A—C24A | 1.57 (3) |
C3—H3 | 0.9300 | C23A—H23A | 0.9700 |
C4—C5 | 1.375 (8) | C23A—H23B | 0.9700 |
C4—H4 | 0.9300 | C24A—H24A | 0.9700 |
C5—C6 | 1.356 (8) | C24A—H24B | 0.9700 |
C5—H5 | 0.9300 | C26A—C27A | 1.531 (16) |
C6—H6 | 0.9300 | C26A—H26A | 0.9700 |
C8—C13 | 1.366 (8) | C26A—H26B | 0.9700 |
C8—C9 | 1.376 (9) | C27A—H27A | 0.9700 |
C9—C10 | 1.364 (9) | C27A—H27B | 0.9700 |
C9—H9 | 0.9300 | C23B—C24B | 1.505 (17) |
C10—C11 | 1.362 (11) | C23B—H23C | 0.9700 |
C10—H10 | 0.9300 | C23B—H23D | 0.9700 |
C11—C12 | 1.346 (10) | C24B—H24C | 0.9700 |
C11—H11 | 0.9300 | C24B—H24D | 0.9700 |
C12—C13 | 1.417 (7) | C26B—C27B | 1.531 (16) |
C12—C14 | 1.499 (11) | C26B—H26C | 0.9700 |
C13—C15 | 1.485 (9) | C26B—H26D | 0.9700 |
C14—H14A | 0.9600 | C27B—H27C | 0.9700 |
C14—H14B | 0.9600 | C27B—H27D | 0.9700 |
C14—H14C | 0.9600 | C28—C33A | 1.465 (15) |
C15—H15A | 0.9600 | C28—C29B | 1.498 (14) |
C15—H15B | 0.9600 | C28—C29A | 1.539 (14) |
C15—H15C | 0.9600 | C28—C33B | 1.576 (14) |
C16—C17B | 1.461 (16) | C28—H28 | 0.9800 |
C16—C21A | 1.503 (17) | C29A—C30A | 1.500 (15) |
C16—C21B | 1.527 (17) | C29A—H29A | 0.9700 |
C16—C17A | 1.560 (15) | C29A—H29B | 0.9700 |
C16—H16 | 0.9800 | C30A—C31A | 1.513 (14) |
C19—C20A | 1.477 (16) | C30A—H30A | 0.9700 |
C19—C18A | 1.483 (15) | C30A—H30B | 0.9700 |
C19—C18B | 1.525 (14) | C31A—C32A | 1.429 (14) |
C19—C20B | 1.534 (16) | C31A—H31A | 0.9700 |
C19—H19A | 0.9700 | C31A—H31B | 0.9700 |
C19—H19B | 0.9700 | C32A—C33A | 1.52 (2) |
C17A—C18A | 1.557 (18) | C32A—H32A | 0.9700 |
C17A—H17A | 0.9700 | C32A—H32B | 0.9700 |
C17A—H17B | 0.9700 | C33A—H33A | 0.9700 |
C18A—H18A | 0.9700 | C33A—H33B | 0.9700 |
C18A—H18B | 0.9700 | C29B—C30B | 1.546 (15) |
C20A—C21A | 1.535 (17) | C29B—H29C | 0.9700 |
C20A—H20A | 0.9700 | C29B—H29D | 0.9700 |
C20A—H20B | 0.9700 | C30B—C31B | 1.474 (12) |
C21A—H21A | 0.9700 | C30B—H30C | 0.9700 |
C21A—H21B | 0.9700 | C30B—H30D | 0.9700 |
C17B—C18B | 1.553 (16) | C31B—C32B | 1.442 (15) |
C17B—H17C | 0.9700 | C31B—H31C | 0.9700 |
C17B—H17D | 0.9700 | C31B—H31D | 0.9700 |
C18B—H18C | 0.9700 | C32B—C33B | 1.488 (16) |
C18B—H18D | 0.9700 | C32B—H32C | 0.9700 |
C20B—C21B | 1.540 (17) | C32B—H32D | 0.9700 |
C20B—H20C | 0.9700 | C33B—H33C | 0.9700 |
C20B—H20D | 0.9700 | C33B—H33D | 0.9700 |
O1—Sn—C16 | 112.38 (18) | C27A—C22—Sn | 117.5 (7) |
O1—Sn—C28 | 94.52 (17) | C23B—C22—Sn | 109.6 (9) |
C16—Sn—C28 | 117.4 (3) | C27B—C22—H22 | 125.4 |
O1—Sn—C22 | 105.4 (2) | C23A—C22—H22 | 97.1 |
C16—Sn—C22 | 112.4 (2) | C27A—C22—H22 | 97.1 |
C28—Sn—C22 | 112.7 (2) | C23B—C22—H22 | 119.7 |
C7—O1—Sn | 111.7 (3) | Sn—C22—H22 | 97.1 |
C2—N1—C8 | 124.6 (4) | C24B—C25—C26B | 123.4 (13) |
C2—N1—H1 | 115 (4) | C24A—C25—C26B | 117.1 (14) |
C8—N1—H1 | 120 (4) | C24B—C25—C26A | 110.5 (14) |
C6—C1—C2 | 117.8 (4) | C24A—C25—C26A | 93.7 (15) |
C6—C1—C7 | 120.1 (4) | C24B—C25—H25A | 120.1 |
C2—C1—C7 | 122.0 (4) | C24A—C25—H25A | 113.0 |
N1—C2—C3 | 121.2 (4) | C26B—C25—H25A | 115.0 |
N1—C2—C1 | 120.5 (4) | C26A—C25—H25A | 113.0 |
C3—C2—C1 | 118.2 (4) | C24B—C25—H25B | 87.4 |
C4—C3—C2 | 121.3 (5) | C24A—C25—H25B | 113.0 |
C4—C3—H3 | 119.4 | C26B—C25—H25B | 85.3 |
C2—C3—H3 | 119.4 | C26A—C25—H25B | 113.0 |
C3—C4—C5 | 121.6 (5) | H25A—C25—H25B | 110.4 |
C3—C4—H4 | 119.2 | C22—C23A—C24A | 111.2 (19) |
C5—C4—H4 | 119.2 | C22—C23A—H23A | 109.4 |
C6—C5—C4 | 118.3 (5) | C24A—C23A—H23A | 109.4 |
C6—C5—H5 | 120.8 | C22—C23A—H23B | 109.4 |
C4—C5—H5 | 120.8 | C24A—C23A—H23B | 109.4 |
C5—C6—C1 | 122.7 (5) | H23A—C23A—H23B | 108.0 |
C5—C6—H6 | 118.6 | C25—C24A—C23A | 108.5 (17) |
C1—C6—H6 | 118.6 | C25—C24A—H24A | 110.0 |
O2—C7—O1 | 119.8 (4) | C23A—C24A—H24A | 110.0 |
O2—C7—C1 | 123.5 (4) | C25—C24A—H24B | 110.0 |
O1—C7—C1 | 116.7 (4) | C23A—C24A—H24B | 110.0 |
C13—C8—C9 | 121.3 (5) | H24A—C24A—H24B | 108.4 |
C13—C8—N1 | 119.2 (5) | C25—C26A—C27A | 118.1 (15) |
C9—C8—N1 | 119.5 (6) | C25—C26A—H26A | 107.8 |
C10—C9—C8 | 119.1 (7) | C27A—C26A—H26A | 107.8 |
C10—C9—H9 | 120.4 | C25—C26A—H26B | 107.8 |
C8—C9—H9 | 120.4 | C27A—C26A—H26B | 107.8 |
C11—C10—C9 | 120.1 (7) | H26A—C26A—H26B | 107.1 |
C11—C10—H10 | 119.9 | C22—C27A—C26A | 104.8 (14) |
C9—C10—H10 | 119.9 | C22—C27A—H27A | 110.8 |
C12—C11—C10 | 122.0 (6) | C26A—C27A—H27A | 110.8 |
C12—C11—H11 | 119.0 | C22—C27A—H27B | 110.8 |
C10—C11—H11 | 119.0 | C26A—C27A—H27B | 110.8 |
C11—C12—C13 | 118.6 (6) | H27A—C27A—H27B | 108.9 |
C11—C12—C14 | 120.5 (7) | C24B—C23B—C22 | 115.1 (17) |
C13—C12—C14 | 120.8 (7) | C24B—C23B—H23C | 108.5 |
C8—C13—C12 | 118.7 (6) | C22—C23B—H23C | 108.5 |
C8—C13—C15 | 121.2 (5) | C24B—C23B—H23D | 108.5 |
C12—C13—C15 | 120.1 (6) | C22—C23B—H23D | 108.5 |
C12—C14—H14A | 109.5 | H23C—C23B—H23D | 107.5 |
C12—C14—H14B | 109.5 | C25—C24B—C23B | 109.0 (17) |
H14A—C14—H14B | 109.5 | C25—C24B—H24C | 109.9 |
C12—C14—H14C | 109.5 | C23B—C24B—H24C | 109.9 |
H14A—C14—H14C | 109.5 | C25—C24B—H24D | 109.9 |
H14B—C14—H14C | 109.5 | C23B—C24B—H24D | 109.9 |
C13—C15—H15A | 109.5 | H24C—C24B—H24D | 108.3 |
C13—C15—H15B | 109.5 | C25—C26B—C27B | 106.1 (14) |
H15A—C15—H15B | 109.5 | C25—C26B—H26C | 110.5 |
C13—C15—H15C | 109.5 | C27B—C26B—H26C | 110.5 |
H15A—C15—H15C | 109.5 | C25—C26B—H26D | 110.5 |
H15B—C15—H15C | 109.5 | C27B—C26B—H26D | 110.5 |
C17B—C16—C21A | 119 (2) | H26C—C26B—H26D | 108.7 |
C17B—C16—C21B | 115.7 (19) | C22—C27B—C26B | 121.4 (18) |
C21A—C16—C17A | 110 (2) | C22—C27B—H27C | 107.0 |
C21B—C16—C17A | 107 (2) | C26B—C27B—H27C | 107.0 |
C17B—C16—Sn | 111.2 (9) | C22—C27B—H27D | 107.0 |
C21A—C16—Sn | 114.0 (11) | C26B—C27B—H27D | 107.0 |
C21B—C16—Sn | 119.1 (10) | H27C—C27B—H27D | 106.7 |
C17A—C16—Sn | 115.2 (8) | C33A—C28—C29B | 93.9 (10) |
C17B—C16—H16 | 99.3 | C33A—C28—C29A | 111.0 (9) |
C21A—C16—H16 | 105.4 | C29B—C28—C33B | 108.4 (9) |
C21B—C16—H16 | 103.0 | C29A—C28—C33B | 125.4 (9) |
C17A—C16—H16 | 105.4 | C33A—C28—Sn | 118.3 (9) |
Sn—C16—H16 | 105.4 | C29B—C28—Sn | 112.6 (7) |
C20A—C19—C18A | 110.5 (14) | C29A—C28—Sn | 112.6 (7) |
C20A—C19—C18B | 121.2 (14) | C33B—C28—Sn | 109.8 (7) |
C18A—C19—C20B | 103.6 (14) | C33A—C28—H28 | 104.4 |
C18B—C19—C20B | 118.9 (13) | C29B—C28—H28 | 123.6 |
C20A—C19—H19A | 109.5 | C29A—C28—H28 | 104.4 |
C18A—C19—H19A | 109.5 | C33B—C28—H28 | 96.6 |
C18B—C19—H19A | 117.6 | Sn—C28—H28 | 104.4 |
C20B—C19—H19A | 101.4 | C30A—C29A—C28 | 112.1 (12) |
C20A—C19—H19B | 109.5 | C30A—C29A—H29A | 109.2 |
C18A—C19—H19B | 109.5 | C28—C29A—H29A | 109.2 |
C18B—C19—H19B | 87.6 | C30A—C29A—H29B | 109.2 |
C20B—C19—H19B | 123.9 | C28—C29A—H29B | 109.2 |
H19A—C19—H19B | 108.1 | H29A—C29A—H29B | 107.9 |
C18A—C17A—C16 | 105.3 (15) | C29A—C30A—C31A | 114.3 (13) |
C18A—C17A—H17A | 110.7 | C29A—C30A—H30A | 108.7 |
C16—C17A—H17A | 110.7 | C31A—C30A—H30A | 108.7 |
C18A—C17A—H17B | 110.7 | C29A—C30A—H30B | 108.7 |
C16—C17A—H17B | 110.7 | C31A—C30A—H30B | 108.7 |
H17A—C17A—H17B | 108.8 | H30A—C30A—H30B | 107.6 |
C19—C18A—C17A | 104.7 (15) | C32A—C31A—C30A | 108.4 (13) |
C19—C18A—H18A | 110.8 | C32A—C31A—H31A | 110.0 |
C17A—C18A—H18A | 110.8 | C30A—C31A—H31A | 110.0 |
C19—C18A—H18B | 110.8 | C32A—C31A—H31B | 110.0 |
C17A—C18A—H18B | 110.8 | C30A—C31A—H31B | 110.0 |
H18A—C18A—H18B | 108.9 | H31A—C31A—H31B | 108.4 |
C19—C20A—C21A | 119 (2) | C31A—C32A—C33A | 111.3 (15) |
C19—C20A—H20A | 107.5 | C31A—C32A—H32A | 109.4 |
C21A—C20A—H20A | 107.5 | C33A—C32A—H32A | 109.4 |
C19—C20A—H20B | 107.5 | C31A—C32A—H32B | 109.4 |
C21A—C20A—H20B | 107.5 | C33A—C32A—H32B | 109.4 |
H20A—C20A—H20B | 107.0 | H32A—C32A—H32B | 108.0 |
C16—C21A—C20A | 112 (2) | C28—C33A—C32A | 112.1 (16) |
C16—C21A—H21A | 109.1 | C28—C33A—H33A | 109.2 |
C20A—C21A—H21A | 109.1 | C32A—C33A—H33A | 109.2 |
C16—C21A—H21B | 109.1 | C28—C33A—H33B | 109.2 |
C20A—C21A—H21B | 109.1 | C32A—C33A—H33B | 109.2 |
H21A—C21A—H21B | 107.9 | H33A—C33A—H33B | 107.9 |
C16—C17B—C18B | 119.5 (15) | C28—C29B—C30B | 111.6 (13) |
C16—C17B—H17C | 107.4 | C28—C29B—H29C | 109.3 |
C18B—C17B—H17C | 107.4 | C30B—C29B—H29C | 109.3 |
C16—C17B—H17D | 107.4 | C28—C29B—H29D | 109.3 |
C18B—C17B—H17D | 107.4 | C30B—C29B—H29D | 109.3 |
H17C—C17B—H17D | 107.0 | H29C—C29B—H29D | 108.0 |
C19—C18B—C17B | 114.2 (13) | C31B—C30B—C29B | 108.2 (12) |
C19—C18B—H18C | 108.7 | C31B—C30B—H30C | 110.1 |
C17B—C18B—H18C | 108.7 | C29B—C30B—H30C | 110.1 |
C19—C18B—H18D | 108.7 | C31B—C30B—H30D | 110.1 |
C17B—C18B—H18D | 108.7 | C29B—C30B—H30D | 110.1 |
H18C—C18B—H18D | 107.6 | H30C—C30B—H30D | 108.4 |
C19—C20B—C21B | 107 (2) | C32B—C31B—C30B | 118.5 (14) |
C19—C20B—H20C | 110.3 | C32B—C31B—H31C | 107.7 |
C21B—C20B—H20C | 110.3 | C30B—C31B—H31C | 107.7 |
C19—C20B—H20D | 110.3 | C32B—C31B—H31D | 107.7 |
C21B—C20B—H20D | 110.3 | C30B—C31B—H31D | 107.7 |
H20C—C20B—H20D | 108.5 | H31C—C31B—H31D | 107.1 |
C16—C21B—C20B | 113 (2) | C31B—C32B—C33B | 112.9 (13) |
C16—C21B—H21C | 109.0 | C31B—C32B—H32C | 109.0 |
C20B—C21B—H21C | 109.0 | C33B—C32B—H32C | 109.0 |
C16—C21B—H21D | 109.0 | C31B—C32B—H32D | 109.0 |
C20B—C21B—H21D | 109.0 | C33B—C32B—H32D | 109.0 |
H21C—C21B—H21D | 107.8 | H32C—C32B—H32D | 107.8 |
C27B—C22—C23A | 108.1 (14) | C32B—C33B—C28 | 111.8 (12) |
C23A—C22—C27A | 121.5 (13) | C32B—C33B—H33C | 109.3 |
C27B—C22—C23B | 93.1 (14) | C28—C33B—H33C | 109.3 |
C27A—C22—C23B | 114.6 (13) | C32B—C33B—H33D | 109.3 |
C27B—C22—Sn | 112.3 (9) | C28—C33B—H33D | 109.3 |
C23A—C22—Sn | 116.5 (10) | H33C—C33B—H33D | 107.9 |
C16—Sn—O1—C7 | −55.7 (4) | C16—Sn—C22—C27B | −84.3 (11) |
C28—Sn—O1—C7 | −177.9 (3) | C28—Sn—C22—C27B | 51.1 (11) |
C22—Sn—O1—C7 | 67.1 (4) | O1—Sn—C22—C23A | −81.6 (13) |
C8—N1—C2—C3 | 4.6 (9) | C16—Sn—C22—C23A | 41.1 (13) |
C8—N1—C2—C1 | −174.8 (5) | C28—Sn—C22—C23A | 176.6 (13) |
C6—C1—C2—N1 | −178.5 (5) | O1—Sn—C22—C27A | 121.8 (12) |
C7—C1—C2—N1 | 4.8 (7) | C16—Sn—C22—C27A | −115.5 (12) |
C6—C1—C2—C3 | 2.0 (7) | C28—Sn—C22—C27A | 20.0 (13) |
C7—C1—C2—C3 | −174.6 (5) | O1—Sn—C22—C23B | −105.1 (12) |
N1—C2—C3—C4 | 179.2 (6) | C16—Sn—C22—C23B | 17.6 (12) |
C1—C2—C3—C4 | −1.4 (9) | C28—Sn—C22—C23B | 153.1 (12) |
C2—C3—C4—C5 | −0.2 (11) | C27B—C22—C23A—C24A | −55 (2) |
C3—C4—C5—C6 | 1.0 (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—C24A | 177.1 (13) |
C7—C1—C6—C5 | 175.5 (6) | C24B—C25—C24A—C23A | 56 (3) |
Sn—O1—C7—O2 | 4.3 (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—C25 | 57 (2) |
C2—C1—C7—O2 | 1.3 (7) | C24B—C25—C26A—C27A | 59 (2) |
C6—C1—C7—O1 | 2.5 (7) | C24A—C25—C26A—C27A | 79 (2) |
C2—C1—C7—O1 | 179.1 (4) | C26B—C25—C26A—C27A | −63 (2) |
C2—N1—C8—C13 | 95.1 (7) | C27B—C22—C27A—C26A | 92 (3) |
C2—N1—C8—C9 | −87.1 (8) | C23A—C22—C27A—C26A | 23 (3) |
C13—C8—C9—C10 | 0.9 (10) | C23B—C22—C27A—C26A | 47 (2) |
N1—C8—C9—C10 | −176.7 (6) | Sn—C22—C27A—C26A | 178.1 (11) |
C8—C9—C10—C11 | 2.0 (12) | C25—C26A—C27A—C22 | −52 (2) |
C9—C10—C11—C12 | −4.0 (12) | C27B—C22—C23B—C24B | −73 (2) |
C10—C11—C12—C13 | 2.9 (10) | C23A—C22—C23B—C24B | 60 (4) |
C10—C11—C12—C14 | −178.8 (7) | C27A—C22—C23B—C24B | −53 (2) |
C9—C8—C13—C12 | −2.0 (8) | Sn—C22—C23B—C24B | 172.4 (16) |
N1—C8—C13—C12 | 175.7 (5) | C24A—C25—C24B—C23B | −107 (4) |
C9—C8—C13—C15 | 177.5 (6) | C26B—C25—C24B—C23B | −23 (3) |
N1—C8—C13—C15 | −4.8 (8) | C26A—C25—C24B—C23B | −54 (2) |
C11—C12—C13—C8 | 0.1 (8) | C22—C23B—C24B—C25 | 54 (3) |
C14—C12—C13—C8 | −178.2 (6) | C24B—C25—C26B—C27B | 18 (3) |
C11—C12—C13—C15 | −179.4 (6) | C24A—C25—C26B—C27B | 48 (2) |
C14—C12—C13—C15 | 2.3 (9) | C26A—C25—C26B—C27B | 90 (3) |
O1—Sn—C16—C17B | −167.1 (14) | C23A—C22—C27B—C26B | 54 (2) |
C28—Sn—C16—C17B | −59.1 (15) | C27A—C22—C27B—C26B | −69 (3) |
C22—Sn—C16—C17B | 74.1 (15) | C23B—C22—C27B—C26B | 71 (2) |
O1—Sn—C16—C21A | −29 (3) | Sn—C22—C27B—C26B | −176.1 (15) |
C28—Sn—C16—C21A | 79 (3) | C25—C26B—C27B—C22 | −48 (3) |
C22—Sn—C16—C21A | −148 (3) | O1—Sn—C28—C33A | 167.8 (12) |
O1—Sn—C16—C21B | −29 (3) | C16—Sn—C28—C33A | 49.7 (12) |
C28—Sn—C16—C21B | 79 (3) | C22—Sn—C28—C33A | −83.4 (12) |
C22—Sn—C16—C21B | −147 (3) | O1—Sn—C28—C29B | 59.9 (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—C29B | 168.7 (9) |
C22—Sn—C16—C17A | 83.3 (13) | O1—Sn—C28—C29A | 36.1 (10) |
C17B—C16—C17A—C18A | −98 (12) | C16—Sn—C28—C29A | −82.0 (10) |
C21A—C16—C17A—C18A | 64 (3) | C22—Sn—C28—C29A | 144.9 (10) |
C21B—C16—C17A—C18A | 60 (3) | O1—Sn—C28—C33B | −179.2 (11) |
Sn—C16—C17A—C18A | −164.7 (11) | C16—Sn—C28—C33B | 62.7 (11) |
C20A—C19—C18A—C17A | 63.2 (17) | C22—Sn—C28—C33B | −70.4 (11) |
C18B—C19—C18A—C17A | −60 (3) | C33A—C28—C29A—C30A | 46 (2) |
C20B—C19—C18A—C17A | 76.4 (16) | C29B—C28—C29A—C30A | 87 (3) |
C16—C17A—C18A—C19 | −73.9 (19) | C33B—C28—C29A—C30A | 43 (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—C32A | 55 (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—C16 | 34 (6) | C33B—C28—C33A—C32A | 118 (9) |
C21A—C16—C17B—C18B | 35 (4) | Sn—C28—C33A—C32A | 175.2 (11) |
C21B—C16—C17B—C18B | 31 (4) | C31A—C32A—C33A—C28 | 62 (2) |
C17A—C16—C17B—C18B | 54 (10) | C33A—C28—C29B—C30B | 57.8 (16) |
Sn—C16—C17B—C18B | 170.8 (19) | C29A—C28—C29B—C30B | −85 (3) |
C18A—C19—C18B—C17B | 81 (4) | C33B—C28—C29B—C30B | 59.0 (18) |
C20B—C19—C18B—C17B | 32 (2) | Sn—C28—C29B—C30B | −179.2 (10) |
C16—C17B—C18B—C19 | −21 (3) | C28—C29B—C30B—C31B | −56 (2) |
C20A—C19—C20B—C21B | 53 (7) | C29B—C30B—C31B—C32B | 51 (3) |
C18A—C19—C20B—C21B | −67 (2) | C30B—C31B—C32B—C33B | −49 (3) |
C18B—C19—C20B—C21B | −50 (3) | C31B—C32B—C33B—C28 | 49 (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—C20B | 172 (2) | C29A—C28—C33B—C32B | −39 (3) |
C19—C20B—C21B—C16 | 58 (5) | Sn—C28—C33B—C32B | −178.2 (14) |
O1—Sn—C22—C27B | 152.9 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.90 (7) | 1.93 (7) | 2.656 (6) | 137 (6) |
C23A—H23A···O2 | 0.97 | 2.45 | 3.17 (3) | 132 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H11)3(C15H14NO2)] |
Mr | 608.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.6093 (2), 12.0104 (3), 15.5241 (4) |
α, β, γ (°) | 109.872 (1), 90.616 (2), 110.548 (1) |
V (Å3) | 1560.47 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.85 |
Crystal size (mm) | 0.28 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.797, 0.841 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31924, 7684, 5308 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.166, 1.02 |
No. of reflections | 7684 |
No. of parameters | 307 |
No. of restraints | 33 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.37, −0.49 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.90 (7) | 1.93 (7) | 2.656 (6) | 137 (6) |
C23A—H23A···O2 | 0.97 | 2.45 | 3.17 (3) | 132 |
References
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Danish, M., Ali, S., Badshah, A., Mazhar, M., Masood, H., Malik, A. & Kehr, G. (1997). Synth. React. Inorg. Met. Org. Chem. 27, 863–885. CrossRef CAS Web of Science Google Scholar
Danish, M., Tahir, M. N., Ahmad, N., Raza, A. R. & Ibrahim, M. (2009). Acta Cryst. E65, m609–m610. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Ülkü, D., Ali, S., Masood, T., Danish, M. & Mazhar, M. (1997b). Acta Cryst. C53, 1574–1576. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Tahir, M. N., Ülkü, D., Danish, M., Ali, S., Badshah, A. & Mazhar, M. (1997a). Acta Cryst. C53, 183–185. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Basu Baul, T. S. & Tiekink, E. R. T. (1998). Organometallics 17, 5758–5766. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).