# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound1 _database_code_depnum_ccdc_archive 'CCDC 874087' #TrackingRef 'compound1_2_4_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 F8 Sn' _chemical_formula_sum 'C14 H8 F8 Sn' _chemical_formula_weight 446.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.4580(15) _cell_length_b 10.2400(10) _cell_length_c 9.3710(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.291(9) _cell_angle_gamma 90.00 _cell_volume 1479.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 127 _cell_measurement_theta_min 4.470 _cell_measurement_theta_max 21.293 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6130 _exptl_absorpt_correction_T_max 0.7607 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35391 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4315 _reflns_number_gt 3657 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+1.1859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4315 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0507 _refine_ls_wR_factor_gt 0.0457 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.253365(7) 0.476582(12) 0.546437(13) 0.02106(4) Uani 1 1 d . . . F1 F 0.28915(7) 0.77966(11) 0.60394(13) 0.0320(3) Uani 1 1 d . . . F2 F 0.40492(8) 0.95277(11) 0.52062(14) 0.0326(3) Uani 1 1 d . . . F3 F 0.54052(8) 0.61967(12) 0.26850(13) 0.0341(3) Uani 1 1 d . . . F4 F 0.42361(7) 0.44676(11) 0.35003(12) 0.0285(2) Uani 1 1 d . . . F5 F 0.06655(7) 0.62633(12) 0.58983(11) 0.0291(2) Uani 1 1 d . . . F6 F -0.06337(7) 0.70778(13) 0.40365(14) 0.0357(3) Uani 1 1 d . . . F7 F 0.08893(10) 0.55286(17) 0.02061(13) 0.0516(4) Uani 1 1 d . . . F8 F 0.21687(8) 0.46599(13) 0.20688(14) 0.0389(3) Uani 1 1 d . . . C1 C 0.35315(11) 0.60701(17) 0.48130(18) 0.0200(3) Uani 1 1 d . . . C2 C 0.35149(11) 0.73737(17) 0.52130(19) 0.0220(3) Uani 1 1 d . . . C3 C 0.41064(12) 0.82741(17) 0.4780(2) 0.0235(3) Uani 1 1 d . . . C4 C 0.47487(12) 0.79063(18) 0.39191(19) 0.0250(4) Uani 1 1 d . . . H4 H 0.5157 0.8521 0.3616 0.030 Uiso 1 1 calc R . . C5 C 0.47770(11) 0.66143(19) 0.35131(18) 0.0234(3) Uani 1 1 d . . . C6 C 0.41763(11) 0.57242(17) 0.39453(18) 0.0207(3) Uani 1 1 d . . . C7 C 0.14559(12) 0.54303(17) 0.40455(19) 0.0225(3) Uani 1 1 d . . . C8 C 0.07360(12) 0.60598(17) 0.44844(19) 0.0224(3) Uani 1 1 d . . . C9 C 0.00678(12) 0.64850(19) 0.3533(2) 0.0273(4) Uani 1 1 d . . . C10 C 0.00987(13) 0.6302(2) 0.2086(2) 0.0324(4) Uani 1 1 d . . . H10 H -0.0360 0.6589 0.1430 0.039 Uiso 1 1 calc R . . C11 C 0.08174(14) 0.5691(2) 0.1621(2) 0.0343(5) Uani 1 1 d . . . C12 C 0.14768(13) 0.5259(2) 0.2578(2) 0.0285(4) Uani 1 1 d . . . C13 C 0.23088(14) 0.5138(2) 0.7635(2) 0.0307(4) Uani 1 1 d . . . H13A H 0.1802 0.4640 0.7892 0.046 Uiso 1 1 calc R . . H13B H 0.2202 0.6072 0.7763 0.046 Uiso 1 1 calc R . . H13C H 0.2818 0.4872 0.8252 0.046 Uiso 1 1 calc R . . C14 C 0.27967(14) 0.27903(19) 0.4954(3) 0.0383(5) Uani 1 1 d . . . H14A H 0.3283 0.2470 0.5588 0.057 Uiso 1 1 calc R . . H14B H 0.2946 0.2734 0.3957 0.057 Uiso 1 1 calc R . . H14C H 0.2282 0.2256 0.5080 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.02021(6) 0.01716(6) 0.02638(7) -0.00006(4) 0.00549(4) -0.00341(4) F1 0.0294(6) 0.0245(6) 0.0436(7) -0.0085(5) 0.0134(5) -0.0012(5) F2 0.0333(6) 0.0176(5) 0.0464(7) -0.0045(5) 0.0002(5) -0.0061(4) F3 0.0290(6) 0.0414(7) 0.0336(6) -0.0027(5) 0.0150(5) -0.0052(5) F4 0.0318(6) 0.0223(5) 0.0327(6) -0.0065(4) 0.0097(5) -0.0014(4) F5 0.0303(6) 0.0332(6) 0.0240(5) -0.0046(4) 0.0035(4) 0.0030(5) F6 0.0254(6) 0.0385(7) 0.0425(7) 0.0024(5) -0.0014(5) 0.0045(5) F7 0.0491(8) 0.0850(11) 0.0211(6) -0.0037(6) 0.0048(5) -0.0229(8) F8 0.0357(7) 0.0482(8) 0.0348(6) -0.0131(5) 0.0148(5) -0.0067(6) C1 0.0193(7) 0.0193(8) 0.0215(8) 0.0004(6) 0.0014(6) -0.0032(6) C2 0.0202(8) 0.0217(8) 0.0242(8) -0.0030(6) 0.0023(6) -0.0012(6) C3 0.0237(8) 0.0178(8) 0.0281(9) -0.0001(6) -0.0038(7) -0.0041(6) C4 0.0220(8) 0.0263(9) 0.0262(9) 0.0053(7) -0.0015(7) -0.0092(7) C5 0.0197(8) 0.0306(9) 0.0202(8) 0.0011(7) 0.0038(6) -0.0025(7) C6 0.0229(8) 0.0176(7) 0.0214(8) -0.0012(6) -0.0002(6) -0.0012(6) C7 0.0233(8) 0.0203(8) 0.0239(8) -0.0014(6) 0.0028(6) -0.0075(6) C8 0.0245(8) 0.0203(8) 0.0227(8) -0.0006(6) 0.0025(6) -0.0053(6) C9 0.0246(9) 0.0252(9) 0.0320(10) 0.0027(7) 0.0005(7) -0.0057(7) C10 0.0302(10) 0.0374(11) 0.0286(9) 0.0089(8) -0.0050(8) -0.0139(8) C11 0.0373(11) 0.0460(12) 0.0198(9) 0.0000(8) 0.0026(8) -0.0194(9) C12 0.0279(9) 0.0313(10) 0.0272(9) -0.0055(8) 0.0079(7) -0.0105(8) C13 0.0299(9) 0.0391(11) 0.0234(9) 0.0030(8) 0.0037(7) -0.0057(8) C14 0.0324(10) 0.0190(9) 0.0648(15) -0.0021(9) 0.0120(10) -0.0033(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C13 2.123(2) . ? Sn1 C14 2.125(2) . ? Sn1 C7 2.1622(19) . ? Sn1 C1 2.1625(17) . ? F1 C2 1.352(2) . ? F2 C3 1.349(2) . ? F3 C5 1.357(2) . ? F4 C6 1.358(2) . ? F5 C8 1.354(2) . ? F6 C9 1.358(2) . ? F7 C11 1.349(2) . ? F8 C12 1.351(2) . ? C1 C6 1.379(2) . ? C1 C2 1.387(2) . ? C2 C3 1.381(2) . ? C3 C4 1.378(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C7 C8 1.375(3) . ? C7 C12 1.389(3) . ? C8 C9 1.383(3) . ? C9 C10 1.373(3) . ? C10 C11 1.374(3) . ? C10 H10 0.9500 . ? C11 C12 1.380(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 Sn1 C14 115.74(9) . . ? C13 Sn1 C7 111.02(8) . . ? C14 Sn1 C7 108.22(8) . . ? C13 Sn1 C1 109.33(7) . . ? C14 Sn1 C1 111.83(7) . . ? C7 Sn1 C1 99.50(6) . . ? C6 C1 C2 115.80(16) . . ? C6 C1 Sn1 124.76(13) . . ? C2 C1 Sn1 119.34(13) . . ? F1 C2 C3 118.06(16) . . ? F1 C2 C1 119.43(15) . . ? C3 C2 C1 122.50(17) . . ? F2 C3 C4 119.96(16) . . ? F2 C3 C2 119.28(17) . . ? C4 C3 C2 120.76(17) . . ? C3 C4 C5 117.60(16) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? F3 C5 C4 119.96(16) . . ? F3 C5 C6 118.99(17) . . ? C4 C5 C6 121.05(17) . . ? F4 C6 C1 119.56(15) . . ? F4 C6 C5 118.16(16) . . ? C1 C6 C5 122.28(17) . . ? C8 C7 C12 115.76(17) . . ? C8 C7 Sn1 124.55(13) . . ? C12 C7 Sn1 119.67(14) . . ? F5 C8 C7 119.41(16) . . ? F5 C8 C9 118.14(16) . . ? C7 C8 C9 122.45(17) . . ? F6 C9 C10 119.46(18) . . ? F6 C9 C8 119.59(17) . . ? C10 C9 C8 120.94(19) . . ? C11 C10 C9 117.65(19) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? F7 C11 C10 119.7(2) . . ? F7 C11 C12 119.2(2) . . ? C10 C11 C12 121.00(18) . . ? F8 C12 C11 118.79(18) . . ? F8 C12 C7 119.02(18) . . ? C11 C12 C7 122.18(19) . . ? Sn1 C13 H13A 109.5 . . ? Sn1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Sn1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Sn1 C14 H14A 109.5 . . ? Sn1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Sn1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.437 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.086 data_compound2 _database_code_depnum_ccdc_archive 'CCDC 874088' #TrackingRef 'compound1_2_4_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H2 B Cl F8' _chemical_formula_sum 'C12 H2 B Cl F8' _chemical_formula_weight 344.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0378(3) _cell_length_b 6.25680(10) _cell_length_c 26.9402(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2366.20(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 59796 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.934 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8849 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40848 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3441 _reflns_number_gt 2787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.6084P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3441 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.33693(2) 0.04311(6) 0.345767(12) 0.02680(9) Uani 1 1 d . . . F1 F 0.62281(5) 0.23889(13) 0.40359(3) 0.02372(17) Uani 1 1 d . . . F2 F 0.78553(5) 0.17188(14) 0.35632(3) 0.02777(18) Uani 1 1 d . . . F3 F 0.61853(6) 0.04057(13) 0.20780(3) 0.02785(18) Uani 1 1 d . . . F4 F 0.45379(5) 0.10465(13) 0.25409(3) 0.02631(17) Uani 1 1 d . . . F5 F 0.32681(6) 0.13808(12) 0.45336(3) 0.02626(18) Uani 1 1 d . . . F6 F 0.30730(6) 0.42364(14) 0.52494(3) 0.02835(19) Uani 1 1 d . . . F7 F 0.50196(6) 0.90771(12) 0.43674(3) 0.02487(17) Uani 1 1 d . . . F8 F 0.52146(5) 0.62452(12) 0.36403(3) 0.02321(16) Uani 1 1 d . . . B1 B 0.43502(10) 0.2036(2) 0.36123(5) 0.0200(3) Uani 1 1 d . . . C1 C 0.53016(9) 0.17253(19) 0.33157(5) 0.0192(2) Uani 1 1 d . . . C2 C 0.61827(9) 0.1897(2) 0.35507(4) 0.0197(2) Uani 1 1 d . . . C3 C 0.70360(9) 0.1560(2) 0.33083(5) 0.0210(2) Uani 1 1 d . . . C4 C 0.70590(9) 0.1063(2) 0.28081(5) 0.0226(3) Uani 1 1 d . . . H4 H 0.7645 0.0852 0.2638 0.027 Uiso 1 1 calc R . . C5 C 0.61965(9) 0.0885(2) 0.25665(5) 0.0217(3) Uani 1 1 d . . . C6 C 0.53443(9) 0.1198(2) 0.28118(5) 0.0206(2) Uani 1 1 d . . . C7 C 0.42367(8) 0.3685(2) 0.40466(5) 0.0193(2) Uani 1 1 d . . . C8 C 0.36959(9) 0.3289(2) 0.44716(5) 0.0202(2) Uani 1 1 d . . . C9 C 0.35971(9) 0.4760(2) 0.48511(5) 0.0215(2) Uani 1 1 d . . . C10 C 0.40266(9) 0.6746(2) 0.48234(5) 0.0214(2) Uani 1 1 d . . . H10 H 0.3951 0.7775 0.5080 0.026 Uiso 1 1 calc R . . C11 C 0.45704(9) 0.71721(19) 0.44077(5) 0.0199(2) Uani 1 1 d . . . C12 C 0.46764(8) 0.5696(2) 0.40319(4) 0.0191(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02140(15) 0.02976(17) 0.02924(17) -0.00396(12) -0.00053(12) -0.00706(12) F1 0.0218(3) 0.0304(4) 0.0189(3) -0.0021(3) -0.0014(3) -0.0010(3) F2 0.0169(3) 0.0348(4) 0.0316(4) 0.0004(3) -0.0031(3) 0.0013(3) F3 0.0330(4) 0.0308(4) 0.0198(4) -0.0051(3) 0.0039(3) -0.0011(3) F4 0.0230(4) 0.0325(4) 0.0234(4) -0.0049(3) -0.0049(3) -0.0006(3) F5 0.0254(4) 0.0215(4) 0.0318(4) 0.0018(3) 0.0070(3) -0.0048(3) F6 0.0308(4) 0.0317(4) 0.0226(4) 0.0028(3) 0.0093(3) 0.0002(3) F7 0.0274(4) 0.0185(3) 0.0288(4) -0.0018(3) 0.0013(3) -0.0040(3) F8 0.0229(4) 0.0236(4) 0.0231(4) 0.0007(3) 0.0068(3) -0.0034(3) B1 0.0183(6) 0.0201(6) 0.0218(6) 0.0015(5) -0.0016(5) 0.0002(5) C1 0.0191(5) 0.0167(5) 0.0217(6) 0.0003(4) -0.0002(5) 0.0001(4) C2 0.0214(6) 0.0185(5) 0.0190(6) 0.0002(4) -0.0002(4) 0.0001(5) C3 0.0175(5) 0.0194(6) 0.0262(6) 0.0015(5) -0.0015(5) -0.0001(4) C4 0.0221(6) 0.0194(6) 0.0263(6) 0.0009(5) 0.0054(5) 0.0008(5) C5 0.0275(6) 0.0182(5) 0.0194(6) -0.0009(5) 0.0024(5) 0.0001(5) C6 0.0202(5) 0.0185(5) 0.0231(6) -0.0011(5) -0.0024(5) -0.0005(5) C7 0.0158(5) 0.0198(5) 0.0222(6) 0.0003(4) 0.0003(4) 0.0005(4) C8 0.0168(5) 0.0186(5) 0.0252(6) 0.0023(5) 0.0012(5) -0.0003(4) C9 0.0189(5) 0.0257(6) 0.0199(6) 0.0031(5) 0.0024(4) 0.0032(5) C10 0.0217(6) 0.0226(6) 0.0200(6) -0.0008(5) -0.0010(5) 0.0031(5) C11 0.0192(5) 0.0171(5) 0.0235(6) 0.0016(5) -0.0021(4) -0.0008(4) C12 0.0159(5) 0.0218(6) 0.0195(5) 0.0027(4) 0.0019(4) -0.0003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 B1 1.7546(14) . ? F1 C2 1.3445(14) . ? F2 C3 1.3432(14) . ? F3 C5 1.3499(15) . ? F4 C6 1.3502(14) . ? F5 C8 1.3469(14) . ? F6 C9 1.3416(14) . ? F7 C11 1.3528(14) . ? F8 C12 1.3423(14) . ? B1 C7 1.5679(19) . ? B1 C1 1.5684(18) . ? C1 C2 1.3936(17) . ? C1 C6 1.3984(17) . ? C2 C3 1.3804(17) . ? C3 C4 1.3833(18) . ? C4 C5 1.3793(19) . ? C4 H4 0.9500 . ? C5 C6 1.3807(18) . ? C7 C8 1.3958(17) . ? C7 C12 1.4021(17) . ? C8 C9 1.3828(18) . ? C9 C10 1.3832(19) . ? C10 C11 1.3814(17) . ? C10 H10 0.9500 . ? C11 C12 1.3785(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 B1 C1 123.26(11) . . ? C7 B1 Cl1 118.30(9) . . ? C1 B1 Cl1 118.44(10) . . ? C2 C1 C6 114.91(11) . . ? C2 C1 B1 120.98(11) . . ? C6 C1 B1 124.08(11) . . ? F1 C2 C3 116.99(11) . . ? F1 C2 C1 120.09(11) . . ? C3 C2 C1 122.92(12) . . ? F2 C3 C2 119.33(11) . . ? F2 C3 C4 119.64(11) . . ? C2 C3 C4 121.03(12) . . ? C5 C4 C3 117.22(12) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? F3 C5 C4 119.23(11) . . ? F3 C5 C6 119.22(11) . . ? C4 C5 C6 121.55(12) . . ? F4 C6 C5 117.24(11) . . ? F4 C6 C1 120.36(11) . . ? C5 C6 C1 122.36(12) . . ? C8 C7 C12 114.95(11) . . ? C8 C7 B1 123.41(11) . . ? C12 C7 B1 121.64(11) . . ? F5 C8 C9 116.97(11) . . ? F5 C8 C7 120.10(11) . . ? C9 C8 C7 122.89(12) . . ? F6 C9 C8 118.93(12) . . ? F6 C9 C10 120.11(11) . . ? C8 C9 C10 120.96(12) . . ? C11 C10 C9 117.25(11) . . ? C11 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? F7 C11 C12 118.75(11) . . ? F7 C11 C10 119.51(11) . . ? C12 C11 C10 121.73(11) . . ? F8 C12 C11 117.80(11) . . ? F8 C12 C7 119.99(11) . . ? C11 C12 C7 122.21(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.365 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.054 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 874089' #TrackingRef 'compound1_2_4_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H6 F8 N2 Sn' _chemical_formula_sum 'C12 H6 F8 N2 Sn' _chemical_formula_weight 448.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5845(2) _cell_length_b 10.1094(2) _cell_length_c 14.2700(4) _cell_angle_alpha 90.00 _cell_angle_beta 89.9819(12) _cell_angle_gamma 90.00 _cell_volume 1382.67(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 28307 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6977 _exptl_absorpt_correction_T_max 0.8297 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33346 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4026 _reflns_number_gt 3513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.2191P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4026 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.179872(13) 0.777898(12) 0.028361(8) 0.01417(5) Uani 1 1 d . . . F1 F 0.17453(13) 0.63540(12) 0.23588(8) 0.0253(3) Uani 1 1 d . . . F2 F 0.34962(14) 0.64521(13) 0.38163(8) 0.0279(3) Uani 1 1 d . . . F3 F 0.61409(13) 0.96045(13) 0.24499(9) 0.0270(3) Uani 1 1 d . . . F4 F 0.45265(12) 0.96360(12) 0.09031(8) 0.0221(3) Uani 1 1 d . . . F5 F 0.36777(16) 0.76199(13) -0.17133(10) 0.0286(3) Uani 1 1 d . . . F6 F 0.50027(14) 0.55910(13) -0.25367(8) 0.0288(3) Uani 1 1 d . . . F7 F 0.37556(16) 0.27507(11) -0.02455(11) 0.0280(3) Uani 1 1 d . . . F8 F 0.24653(12) 0.46817(12) 0.07383(8) 0.0226(3) Uani 1 1 d . . . N1 N 0.48140(18) 0.80420(18) 0.31320(12) 0.0199(3) Uani 1 1 d . . . N2 N 0.43547(18) 0.41818(18) -0.13959(12) 0.0212(4) Uani 1 1 d . . . C1 C 0.3045(2) 0.79937(19) 0.15466(14) 0.0155(4) Uani 1 1 d . . . C2 C 0.2821(2) 0.72063(18) 0.23260(15) 0.0177(4) Uani 1 1 d . . . C3 C 0.3719(2) 0.72526(19) 0.30797(14) 0.0192(4) Uani 1 1 d . . . C4 C 0.5030(2) 0.8804(2) 0.24038(14) 0.0186(4) Uani 1 1 d . . . C5 C 0.4188(2) 0.88178(19) 0.16116(13) 0.0166(4) Uani 1 1 d . . . C6 C 0.29785(19) 0.6249(2) -0.04459(13) 0.0163(4) Uani 1 1 d . . . C7 C 0.3655(2) 0.6433(2) -0.12931(14) 0.0192(4) Uani 1 1 d . . . C8 C 0.4324(2) 0.5390(2) -0.17242(14) 0.0209(4) Uani 1 1 d . . . C9 C 0.3716(2) 0.3984(2) -0.05909(15) 0.0197(4) Uani 1 1 d . . . C10 C 0.30500(19) 0.4976(2) -0.00967(14) 0.0172(4) Uani 1 1 d . . . C11 C 0.1832(2) 0.95208(19) -0.05418(14) 0.0194(4) Uani 1 1 d . . . H11A H 0.1536 0.9310 -0.1182 0.029 Uiso 1 1 calc R . . H11B H 0.2781 0.9882 -0.0554 0.029 Uiso 1 1 calc R . . H11C H 0.1195 1.0176 -0.0271 0.029 Uiso 1 1 calc R . . C12 C -0.0151(2) 0.6946(2) 0.06735(15) 0.0206(4) Uani 1 1 d . . . H12A H -0.0512 0.7407 0.1227 0.031 Uiso 1 1 calc R . . H12B H -0.0027 0.6006 0.0819 0.031 Uiso 1 1 calc R . . H12C H -0.0813 0.7041 0.0155 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.01486(8) 0.01470(8) 0.01294(8) -0.00042(4) -0.00070(5) -0.00002(4) F1 0.0269(6) 0.0284(7) 0.0206(6) 0.0058(5) -0.0025(5) -0.0109(5) F2 0.0346(7) 0.0332(7) 0.0160(6) 0.0074(5) -0.0015(5) -0.0036(6) F3 0.0247(6) 0.0301(7) 0.0264(7) 0.0029(5) -0.0080(5) -0.0098(5) F4 0.0233(6) 0.0236(6) 0.0193(6) 0.0071(5) -0.0018(5) -0.0043(5) F5 0.0407(8) 0.0225(6) 0.0224(7) 0.0061(5) 0.0092(6) 0.0057(6) F6 0.0348(7) 0.0329(7) 0.0187(6) -0.0030(5) 0.0076(5) 0.0047(6) F7 0.0283(7) 0.0151(6) 0.0406(8) 0.0031(5) 0.0033(6) 0.0031(5) F8 0.0246(6) 0.0211(6) 0.0221(6) 0.0033(5) 0.0039(5) -0.0006(5) N1 0.0214(8) 0.0238(9) 0.0145(8) -0.0026(7) -0.0018(6) 0.0028(7) N2 0.0188(8) 0.0204(8) 0.0244(9) -0.0050(7) -0.0016(7) 0.0024(7) C1 0.0176(9) 0.0156(9) 0.0135(8) -0.0013(7) -0.0001(7) 0.0022(7) C2 0.0186(9) 0.0170(9) 0.0175(9) -0.0013(7) 0.0006(7) -0.0005(7) C3 0.0248(10) 0.0199(10) 0.0129(9) 0.0016(7) 0.0018(8) 0.0035(8) C4 0.0174(9) 0.0193(9) 0.0190(9) -0.0026(8) -0.0012(7) -0.0007(7) C5 0.0192(9) 0.0166(9) 0.0139(8) 0.0006(7) 0.0011(7) 0.0019(7) C6 0.0142(8) 0.0185(9) 0.0163(8) -0.0034(7) -0.0015(7) -0.0010(7) C7 0.0213(9) 0.0175(9) 0.0187(9) 0.0007(7) -0.0014(7) 0.0010(7) C8 0.0195(9) 0.0269(10) 0.0164(9) -0.0037(8) -0.0009(7) 0.0019(8) C9 0.0153(8) 0.0169(9) 0.0270(10) -0.0017(8) -0.0041(8) -0.0014(7) C10 0.0135(8) 0.0217(10) 0.0164(8) -0.0006(8) -0.0012(7) -0.0015(7) C11 0.0213(9) 0.0178(9) 0.0189(9) 0.0030(8) -0.0015(7) 0.0010(8) C12 0.0168(9) 0.0249(10) 0.0201(9) 0.0024(8) -0.0003(7) -0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C11 2.1187(19) . ? Sn1 C12 2.123(2) . ? Sn1 C1 2.174(2) . ? Sn1 C6 2.1801(19) . ? F1 C2 1.345(2) . ? F2 C3 1.343(2) . ? F3 C4 1.339(2) . ? F4 C5 1.346(2) . ? F5 C7 1.342(2) . ? F6 C8 1.345(2) . ? F7 C9 1.342(2) . ? F8 C10 1.350(2) . ? N1 C4 1.310(3) . ? N1 C3 1.321(3) . ? N2 C8 1.308(3) . ? N2 C9 1.317(3) . ? C1 C5 1.379(3) . ? C1 C2 1.384(3) . ? C2 C3 1.378(3) . ? C4 C5 1.389(3) . ? C6 C10 1.382(3) . ? C6 C7 1.384(3) . ? C7 C8 1.379(3) . ? C9 C10 1.382(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Sn1 C12 119.22(8) . . ? C11 Sn1 C1 111.70(7) . . ? C12 Sn1 C1 107.83(8) . . ? C11 Sn1 C6 108.44(8) . . ? C12 Sn1 C6 107.46(8) . . ? C1 Sn1 C6 100.46(7) . . ? C4 N1 C3 115.86(17) . . ? C8 N2 C9 116.33(18) . . ? C5 C1 C2 114.60(18) . . ? C5 C1 Sn1 123.56(14) . . ? C2 C1 Sn1 121.57(14) . . ? F1 C2 C3 118.26(18) . . ? F1 C2 C1 121.01(18) . . ? C3 C2 C1 120.71(19) . . ? N1 C3 F2 116.48(18) . . ? N1 C3 C2 124.11(19) . . ? F2 C3 C2 119.41(19) . . ? N1 C4 F3 116.24(17) . . ? N1 C4 C5 124.01(18) . . ? F3 C4 C5 119.75(18) . . ? F4 C5 C1 120.79(17) . . ? F4 C5 C4 118.52(17) . . ? C1 C5 C4 120.68(18) . . ? C10 C6 C7 114.60(18) . . ? C10 C6 Sn1 120.95(14) . . ? C7 C6 Sn1 124.39(15) . . ? F5 C7 C8 118.51(18) . . ? F5 C7 C6 121.17(18) . . ? C8 C7 C6 120.33(19) . . ? N2 C8 F6 116.05(18) . . ? N2 C8 C7 124.36(19) . . ? F6 C8 C7 119.59(19) . . ? N2 C9 F7 116.63(18) . . ? N2 C9 C10 123.37(19) . . ? F7 C9 C10 119.99(19) . . ? F8 C10 C9 118.86(18) . . ? F8 C10 C6 120.18(18) . . ? C9 C10 C6 120.97(18) . . ? Sn1 C11 H11A 109.5 . . ? Sn1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Sn1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Sn1 C12 H12A 109.5 . . ? Sn1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Sn1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.469 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.104 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 874090' #TrackingRef 'compound1_2_4_5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H6 F10 Sn' _chemical_formula_sum 'C14 H6 F10 Sn' _chemical_formula_weight 482.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.78790(10) _cell_length_b 11.8729(2) _cell_length_c 20.1503(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.2741(8) _cell_angle_gamma 90.00 _cell_volume 3058.65(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 84546 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 1.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6269 _exptl_absorpt_correction_T_max 0.8151 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 85715 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8907 _reflns_number_gt 7622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+2.0976P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8907 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.007874(10) 0.706410(12) 0.150778(6) 0.02367(4) Uani 1 1 d . . . F1 F -0.04696(10) 0.96192(12) 0.10951(7) 0.0356(3) Uani 1 1 d . . . F2 F -0.13536(10) 1.06013(12) 0.00077(7) 0.0405(3) Uani 1 1 d . . . F3 F -0.19245(10) 0.93146(14) -0.10571(7) 0.0419(4) Uani 1 1 d . . . F4 F -0.16920(11) 0.70479(13) -0.10135(6) 0.0409(3) Uani 1 1 d . . . F5 F -0.08421(10) 0.60555(12) 0.00775(6) 0.0351(3) Uani 1 1 d . . . F6 F 0.08524(10) 0.90900(12) 0.25434(6) 0.0364(3) Uani 1 1 d . . . F7 F 0.27373(12) 0.99781(12) 0.28431(6) 0.0412(3) Uani 1 1 d . . . F8 F 0.44391(10) 0.93377(13) 0.21544(8) 0.0445(4) Uani 1 1 d . . . F9 F 0.42366(11) 0.78495(14) 0.11382(9) 0.0513(4) Uani 1 1 d . . . F10 F 0.23496(11) 0.69444(13) 0.08334(8) 0.0431(4) Uani 1 1 d . . . C1 C -0.06038(14) 0.78074(19) 0.06180(10) 0.0243(4) Uani 1 1 d . . . C2 C -0.07590(15) 0.89584(19) 0.05756(10) 0.0279(4) Uani 1 1 d . . . C3 C -0.11993(15) 0.9484(2) 0.00240(11) 0.0308(5) Uani 1 1 d . . . C4 C -0.14947(15) 0.8829(2) -0.05156(10) 0.0318(5) Uani 1 1 d . . . C5 C -0.13707(16) 0.7682(2) -0.04910(10) 0.0307(5) Uani 1 1 d . . . C6 C -0.09327(16) 0.71883(19) 0.00695(10) 0.0274(4) Uani 1 1 d . . . C7 C 0.15281(15) 0.79749(17) 0.16818(10) 0.0229(4) Uani 1 1 d . . . C8 C 0.16712(15) 0.87671(18) 0.21793(9) 0.0250(4) Uani 1 1 d . . . C9 C 0.26316(17) 0.92361(18) 0.23412(10) 0.0293(4) Uani 1 1 d . . . C10 C 0.34923(16) 0.8917(2) 0.19903(12) 0.0322(5) Uani 1 1 d . . . C11 C 0.33904(16) 0.8152(2) 0.14804(13) 0.0336(5) Uani 1 1 d . . . C12 C 0.24183(16) 0.76977(19) 0.13352(11) 0.0283(4) Uani 1 1 d . . . C13 C 0.0465(2) 0.5356(2) 0.13328(11) 0.0360(5) Uani 1 1 d . . . H13A H 0.0853 0.5055 0.1718 0.054 Uiso 1 1 calc R . . H13B H 0.0898 0.5304 0.0939 0.054 Uiso 1 1 calc R . . H13C H -0.0178 0.4919 0.1260 0.054 Uiso 1 1 calc R . . C14 C -0.09830(18) 0.7382(3) 0.22806(11) 0.0420(6) Uani 1 1 d . . . H14A H -0.1627 0.6951 0.2199 0.063 Uiso 1 1 calc R . . H14B H -0.1148 0.8188 0.2293 0.063 Uiso 1 1 calc R . . H14C H -0.0665 0.7154 0.2707 0.063 Uiso 1 1 calc R . . Sn2 Sn 0.537268(10) 0.807636(11) 0.366054(6) 0.02059(4) Uani 1 1 d . . . F11 F 0.38375(11) 0.63301(12) 0.27578(6) 0.0376(3) Uani 1 1 d . . . F12 F 0.17626(12) 0.58999(14) 0.27866(7) 0.0471(4) Uani 1 1 d . . . F13 F 0.05453(10) 0.69838(14) 0.36710(8) 0.0466(4) Uani 1 1 d . . . F14 F 0.14047(11) 0.84449(14) 0.45558(8) 0.0458(4) Uani 1 1 d . . . F15 F 0.34881(10) 0.88368(12) 0.45530(6) 0.0362(3) Uani 1 1 d . . . F16 F 0.56520(9) 0.54836(11) 0.41021(6) 0.0293(3) Uani 1 1 d . . . F17 F 0.63268(10) 0.44451(11) 0.52263(7) 0.0375(3) Uani 1 1 d . . . F18 F 0.69038(10) 0.56889(14) 0.63071(6) 0.0426(4) Uani 1 1 d . . . F19 F 0.68591(12) 0.79736(13) 0.62466(6) 0.0426(4) Uani 1 1 d . . . F20 F 0.62304(11) 0.90111(11) 0.51241(6) 0.0364(3) Uani 1 1 d . . . C15 C 0.37326(14) 0.76187(17) 0.36477(9) 0.0223(4) Uani 1 1 d . . . C16 C 0.32589(17) 0.68671(18) 0.32144(10) 0.0272(4) Uani 1 1 d . . . C17 C 0.21937(18) 0.6633(2) 0.32206(11) 0.0327(5) Uani 1 1 d . . . C18 C 0.15823(16) 0.7177(2) 0.36743(12) 0.0330(5) Uani 1 1 d . . . C19 C 0.20156(16) 0.79208(19) 0.41179(12) 0.0311(5) Uani 1 1 d . . . C20 C 0.30832(16) 0.81172(17) 0.41049(11) 0.0262(4) Uani 1 1 d . . . C21 C 0.59067(14) 0.72843(17) 0.45743(9) 0.0213(4) Uani 1 1 d . . . C22 C 0.59438(14) 0.61255(17) 0.46315(9) 0.0227(4) Uani 1 1 d . . . C23 C 0.62741(15) 0.55710(18) 0.52023(11) 0.0272(4) Uani 1 1 d . . . C24 C 0.65734(15) 0.6202(2) 0.57488(10) 0.0293(5) Uani 1 1 d . . . C25 C 0.65539(15) 0.7359(2) 0.57172(10) 0.0285(4) Uani 1 1 d . . . C26 C 0.62247(16) 0.78802(18) 0.51341(10) 0.0250(4) Uani 1 1 d . . . C27 C 0.61685(18) 0.7335(2) 0.28579(11) 0.0362(5) Uani 1 1 d . . . H27A H 0.5954 0.7708 0.2443 0.054 Uiso 1 1 calc R . . H27B H 0.5994 0.6532 0.2831 0.054 Uiso 1 1 calc R . . H27C H 0.6925 0.7422 0.2929 0.054 Uiso 1 1 calc R . . C28 C 0.55293(19) 0.98501(19) 0.37161(12) 0.0348(5) Uani 1 1 d . . . H28A H 0.6271 1.0048 0.3764 0.052 Uiso 1 1 calc R . . H28B H 0.5152 1.0132 0.4100 0.052 Uiso 1 1 calc R . . H28C H 0.5237 1.0192 0.3310 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.02146(7) 0.03119(8) 0.01835(6) -0.00118(5) 0.00045(5) -0.00365(5) F1 0.0307(6) 0.0345(8) 0.0413(7) -0.0078(6) -0.0032(5) -0.0009(5) F2 0.0288(6) 0.0351(8) 0.0577(9) 0.0095(7) 0.0025(6) 0.0047(6) F3 0.0300(6) 0.0610(10) 0.0346(7) 0.0188(7) -0.0013(5) 0.0087(6) F4 0.0430(8) 0.0570(10) 0.0225(6) -0.0052(6) -0.0066(5) 0.0089(7) F5 0.0441(7) 0.0340(8) 0.0268(6) -0.0051(5) -0.0071(5) 0.0043(6) F6 0.0393(7) 0.0366(8) 0.0338(7) -0.0091(6) 0.0098(5) -0.0015(6) F7 0.0581(9) 0.0327(8) 0.0322(7) -0.0017(6) -0.0094(6) -0.0146(7) F8 0.0279(6) 0.0417(9) 0.0632(9) 0.0152(7) -0.0170(6) -0.0119(6) F9 0.0231(6) 0.0485(10) 0.0831(12) -0.0027(8) 0.0161(7) 0.0024(6) F10 0.0355(7) 0.0449(9) 0.0494(8) -0.0182(7) 0.0145(6) -0.0030(6) C1 0.0163(8) 0.0338(11) 0.0229(9) 0.0005(8) 0.0009(7) -0.0011(7) C2 0.0179(8) 0.0343(12) 0.0318(10) -0.0016(9) 0.0021(7) -0.0019(8) C3 0.0176(8) 0.0339(12) 0.0411(12) 0.0057(9) 0.0040(8) 0.0022(8) C4 0.0195(9) 0.0477(14) 0.0282(10) 0.0114(9) 0.0033(7) 0.0048(9) C5 0.0240(9) 0.0471(14) 0.0210(9) -0.0002(9) 0.0011(7) 0.0025(9) C6 0.0238(9) 0.0346(12) 0.0239(9) -0.0001(8) 0.0011(7) 0.0026(8) C7 0.0208(8) 0.0248(10) 0.0231(9) 0.0024(7) -0.0005(7) -0.0003(7) C8 0.0274(9) 0.0246(10) 0.0228(9) 0.0038(7) -0.0008(7) 0.0012(8) C9 0.0377(11) 0.0226(10) 0.0270(10) 0.0061(8) -0.0087(8) -0.0051(8) C10 0.0241(9) 0.0291(12) 0.0430(12) 0.0133(9) -0.0113(8) -0.0051(8) C11 0.0197(9) 0.0328(12) 0.0482(13) 0.0057(10) 0.0030(9) 0.0029(8) C12 0.0252(9) 0.0271(11) 0.0326(10) -0.0015(8) 0.0007(8) 0.0015(8) C13 0.0510(14) 0.0287(12) 0.0280(10) 0.0018(9) -0.0064(9) -0.0037(10) C14 0.0284(11) 0.0723(19) 0.0255(10) -0.0064(11) 0.0080(8) -0.0087(12) Sn2 0.02029(6) 0.02302(7) 0.01854(6) 0.00047(5) 0.00205(4) 0.00174(5) F11 0.0481(8) 0.0367(8) 0.0279(6) -0.0099(6) 0.0012(5) -0.0031(6) F12 0.0515(8) 0.0514(10) 0.0377(7) 0.0016(7) -0.0164(6) -0.0220(7) F13 0.0232(6) 0.0570(10) 0.0592(10) 0.0224(7) -0.0075(6) -0.0077(6) F14 0.0307(7) 0.0487(9) 0.0587(9) 0.0031(7) 0.0168(6) 0.0086(6) F15 0.0367(7) 0.0329(7) 0.0394(7) -0.0135(6) 0.0108(5) -0.0038(6) F16 0.0282(6) 0.0260(7) 0.0336(6) -0.0059(5) -0.0026(5) -0.0024(5) F17 0.0309(6) 0.0281(7) 0.0534(8) 0.0137(6) 0.0022(6) 0.0036(5) F18 0.0373(7) 0.0599(10) 0.0302(7) 0.0194(7) -0.0033(5) 0.0066(7) F19 0.0478(8) 0.0586(10) 0.0210(6) -0.0080(6) -0.0051(6) -0.0019(7) F20 0.0535(8) 0.0256(7) 0.0300(6) -0.0062(5) -0.0004(6) -0.0013(6) C15 0.0220(8) 0.0220(10) 0.0230(9) 0.0033(7) -0.0010(7) 0.0011(7) C16 0.0332(10) 0.0267(11) 0.0217(9) 0.0031(8) -0.0018(8) 0.0006(8) C17 0.0397(12) 0.0310(12) 0.0268(10) 0.0091(9) -0.0119(8) -0.0102(9) C18 0.0216(9) 0.0379(13) 0.0393(12) 0.0185(10) -0.0049(8) -0.0008(9) C19 0.0244(10) 0.0298(12) 0.0392(12) 0.0087(9) 0.0052(8) 0.0053(8) C20 0.0255(9) 0.0221(10) 0.0313(10) 0.0030(8) 0.0026(8) 0.0020(7) C21 0.0180(8) 0.0252(10) 0.0206(8) 0.0009(7) 0.0009(6) 0.0004(7) C22 0.0161(8) 0.0256(10) 0.0265(9) -0.0004(7) 0.0006(6) -0.0006(7) C23 0.0176(8) 0.0277(11) 0.0364(11) 0.0090(8) 0.0028(7) 0.0013(7) C24 0.0198(9) 0.0439(13) 0.0242(9) 0.0110(9) 0.0014(7) 0.0041(8) C25 0.0233(9) 0.0420(13) 0.0203(9) -0.0015(8) 0.0005(7) -0.0001(9) C26 0.0262(9) 0.0257(10) 0.0233(9) -0.0017(7) 0.0030(7) 0.0001(8) C27 0.0344(11) 0.0488(15) 0.0258(10) -0.0042(10) 0.0084(8) 0.0082(10) C28 0.0426(12) 0.0242(11) 0.0376(12) 0.0046(9) 0.0010(9) -0.0058(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 C13 2.119(2) . ? Sn1 C14 2.122(2) . ? Sn1 C1 2.165(2) . ? Sn1 C7 2.1676(19) . ? F1 C2 1.353(2) . ? F2 C3 1.342(3) . ? F3 C4 1.341(2) . ? F4 C5 1.351(3) . ? F5 C6 1.350(3) . ? F6 C8 1.348(2) . ? F7 C9 1.346(2) . ? F8 C10 1.344(2) . ? F9 C11 1.345(3) . ? F10 C12 1.351(3) . ? C1 C2 1.383(3) . ? C1 C6 1.385(3) . ? C2 C3 1.383(3) . ? C3 C4 1.382(3) . ? C4 C5 1.371(3) . ? C5 C6 1.380(3) . ? C7 C8 1.384(3) . ? C7 C12 1.388(3) . ? C8 C9 1.381(3) . ? C9 C10 1.374(3) . ? C10 C11 1.376(3) . ? C11 C12 1.380(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? Sn2 C28 2.118(2) . ? Sn2 C27 2.121(2) . ? Sn2 C21 2.1646(19) . ? Sn2 C15 2.1662(19) . ? F11 C16 1.353(2) . ? F12 C17 1.343(3) . ? F13 C18 1.346(2) . ? F14 C19 1.344(3) . ? F15 C20 1.339(2) . ? F16 C22 1.357(2) . ? F17 C23 1.339(3) . ? F18 C24 1.340(2) . ? F19 C25 1.343(2) . ? F20 C26 1.343(2) . ? C15 C16 1.379(3) . ? C15 C20 1.387(3) . ? C16 C17 1.391(3) . ? C17 C18 1.377(3) . ? C18 C19 1.365(3) . ? C19 C20 1.386(3) . ? C21 C22 1.381(3) . ? C21 C26 1.385(3) . ? C22 C23 1.383(3) . ? C23 C24 1.379(3) . ? C24 C25 1.375(3) . ? C25 C26 1.385(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 Sn1 C14 116.59(11) . . ? C13 Sn1 C1 110.10(8) . . ? C14 Sn1 C1 106.40(9) . . ? C13 Sn1 C7 107.63(9) . . ? C14 Sn1 C7 110.56(9) . . ? C1 Sn1 C7 104.96(7) . . ? C2 C1 C6 115.75(19) . . ? C2 C1 Sn1 120.57(15) . . ? C6 C1 Sn1 123.66(16) . . ? F1 C2 C1 119.25(19) . . ? F1 C2 C3 117.4(2) . . ? C1 C2 C3 123.4(2) . . ? F2 C3 C4 120.0(2) . . ? F2 C3 C2 121.5(2) . . ? C4 C3 C2 118.5(2) . . ? F3 C4 C5 120.1(2) . . ? F3 C4 C3 119.9(2) . . ? C5 C4 C3 120.0(2) . . ? F4 C5 C4 119.50(19) . . ? F4 C5 C6 120.8(2) . . ? C4 C5 C6 119.7(2) . . ? F5 C6 C5 117.79(19) . . ? F5 C6 C1 119.66(18) . . ? C5 C6 C1 122.5(2) . . ? C8 C7 C12 115.39(18) . . ? C8 C7 Sn1 123.72(14) . . ? C12 C7 Sn1 120.54(15) . . ? F6 C8 C9 117.03(18) . . ? F6 C8 C7 119.73(17) . . ? C9 C8 C7 123.21(19) . . ? F7 C9 C10 119.91(19) . . ? F7 C9 C8 121.0(2) . . ? C10 C9 C8 119.1(2) . . ? F8 C10 C9 119.9(2) . . ? F8 C10 C11 119.9(2) . . ? C9 C10 C11 120.15(19) . . ? F9 C11 C10 119.7(2) . . ? F9 C11 C12 121.2(2) . . ? C10 C11 C12 119.1(2) . . ? F10 C12 C11 117.41(19) . . ? F10 C12 C7 119.53(18) . . ? C11 C12 C7 123.1(2) . . ? Sn1 C13 H13A 109.5 . . ? Sn1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Sn1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Sn1 C14 H14A 109.5 . . ? Sn1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Sn1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C28 Sn2 C27 113.98(10) . . ? C28 Sn2 C21 111.06(8) . . ? C27 Sn2 C21 108.70(8) . . ? C28 Sn2 C15 109.90(8) . . ? C27 Sn2 C15 111.57(9) . . ? C21 Sn2 C15 100.85(7) . . ? C16 C15 C20 115.83(18) . . ? C16 C15 Sn2 125.55(15) . . ? C20 C15 Sn2 118.63(15) . . ? F11 C16 C15 119.75(19) . . ? F11 C16 C17 117.54(19) . . ? C15 C16 C17 122.7(2) . . ? F12 C17 C18 120.4(2) . . ? F12 C17 C16 120.8(2) . . ? C18 C17 C16 118.9(2) . . ? F13 C18 C19 120.0(2) . . ? F13 C18 C17 119.4(2) . . ? C19 C18 C17 120.7(2) . . ? F14 C19 C18 119.7(2) . . ? F14 C19 C20 121.4(2) . . ? C18 C19 C20 118.8(2) . . ? F15 C20 C19 117.45(19) . . ? F15 C20 C15 119.47(18) . . ? C19 C20 C15 123.1(2) . . ? C22 C21 C26 115.59(18) . . ? C22 C21 Sn2 120.88(14) . . ? C26 C21 Sn2 123.52(15) . . ? F16 C22 C21 119.05(17) . . ? F16 C22 C23 117.39(18) . . ? C21 C22 C23 123.56(19) . . ? F17 C23 C24 120.05(19) . . ? F17 C23 C22 121.3(2) . . ? C24 C23 C22 118.6(2) . . ? F18 C24 C25 119.9(2) . . ? F18 C24 C23 120.0(2) . . ? C25 C24 C23 120.09(19) . . ? F19 C25 C24 120.07(19) . . ? F19 C25 C26 120.6(2) . . ? C24 C25 C26 119.35(19) . . ? F20 C26 C21 120.01(18) . . ? F20 C26 C25 117.24(19) . . ? C21 C26 C25 122.7(2) . . ? Sn2 C27 H27A 109.5 . . ? Sn2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? Sn2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Sn2 C28 H28A 109.5 . . ? Sn2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? Sn2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.632 _refine_diff_density_min -0.958 _refine_diff_density_rms 0.084 #===END