# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/248 data_98kcm12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H16 F52 S4 Sn' _chemical_formula_weight 1635.38 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' 'S' 'S' 0.1246 0.1234 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 46.295(5) _cell_length_b 5.3340(10) _cell_length_c 20.156(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.110(10) _cell_angle_gamma 90.00 _cell_volume 4964.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3160 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4619 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4369 _reflns_number_gt 3482 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0735P)^2^+0.7971P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00004(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4369 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.000 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.0000 0.07000(6) 0.2500 0.01936(12) Uani 1 2 d S . . S1 S 0.020248(18) -0.21013(16) 0.33385(4) 0.0252(2) Uani 1 1 d . . . S2 S 0.035422(17) 0.32373(16) 0.20227(4) 0.0249(2) Uani 1 1 d . . . F1 F 0.10369(4) -0.3094(4) 0.21508(11) 0.0353(5) Uani 1 1 d . . . F2 F 0.12404(4) 0.0285(4) 0.18122(9) 0.0347(5) Uani 1 1 d . . . F3 F 0.12541(4) -0.2418(4) 0.33871(9) 0.0343(5) Uani 1 1 d . . . F4 F 0.14002(4) 0.1343(4) 0.31712(10) 0.0339(5) Uani 1 1 d . . . F5 F 0.16001(4) -0.4072(4) 0.23527(10) 0.0364(5) Uani 1 1 d . . . F6 F 0.17756(4) -0.0286(5) 0.23523(10) 0.0394(6) Uani 1 1 d . . . F7 F 0.17679(4) -0.4738(4) 0.36148(10) 0.0356(5) Uani 1 1 d . . . F8 F 0.18733(4) -0.0815(4) 0.37601(9) 0.0325(5) Uani 1 1 d . . . F9 F 0.22941(5) -0.1050(5) 0.29487(13) 0.0598(8) Uani 1 1 d . . . F10 F 0.21695(5) -0.4815(7) 0.26307(12) 0.0743(10) Uani 1 1 d . . . F11 F 0.22999(6) -0.6468(5) 0.38943(18) 0.0786(10) Uani 1 1 d . . . F12 F 0.24000(5) -0.2785(6) 0.42124(11) 0.0557(7) Uani 1 1 d . . . F13 F 0.26466(5) -0.4478(6) 0.34856(12) 0.0558(7) Uani 1 1 d . . . F14 F 0.02738(4) 0.4164(4) 0.49250(10) 0.0380(5) Uani 1 1 d . . . F15 F 0.04857(4) 0.0849(4) 0.53592(9) 0.0319(5) Uani 1 1 d . . . F16 F 0.07438(4) 0.5247(5) 0.56420(11) 0.0479(6) Uani 1 1 d . . . F17 F 0.07762(5) 0.6052(4) 0.45893(12) 0.0429(6) Uani 1 1 d . . . F18 F 0.10605(4) 0.0884(4) 0.54674(10) 0.0335(5) Uani 1 1 d . . . F19 F 0.11100(4) 0.2040(4) 0.44500(9) 0.0352(5) Uani 1 1 d . . . F20 F 0.12966(4) 0.5421(4) 0.59071(10) 0.0359(5) Uani 1 1 d . . . F21 F 0.13503(4) 0.6427(4) 0.48732(10) 0.0334(5) Uani 1 1 d . . . F22 F 0.16239(4) 0.1259(4) 0.57849(11) 0.0391(5) Uani 1 1 d . . . F23 F 0.16732(4) 0.2147(4) 0.47435(10) 0.0350(5) Uani 1 1 d . . . F24 F 0.19211(4) 0.6655(4) 0.51403(11) 0.0408(5) Uani 1 1 d . . . F25 F 0.21313(5) 0.3381(5) 0.55383(13) 0.0530(7) Uani 1 1 d . . . F26 F 0.18778(5) 0.5665(6) 0.61528(11) 0.0601(8) Uani 1 1 d . . . C1 C 0.06332(7) 0.0854(6) 0.19165(15) 0.0224(7) Uani 1 1 d . . . H1A H 0.0540 -0.0809 0.1860 0.027 Uiso 1 1 calc R . . H1B H 0.0731 0.1225 0.1507 0.027 Uiso 1 1 calc R . . C2 C 0.08594(6) 0.0756(7) 0.25089(15) 0.0228(7) Uani 1 1 d . . . H2A H 0.0920 0.2481 0.2635 0.027 Uiso 1 1 calc R . . H2B H 0.0773 -0.0017 0.2895 0.027 Uiso 1 1 calc R . . C3 C 0.11183(7) -0.0736(6) 0.23383(15) 0.0220(7) Uani 1 1 d . . . C4 C 0.13565(7) -0.0955(6) 0.29103(15) 0.0209(7) Uani 1 1 d . . . C5 C 0.16509(7) -0.2008(7) 0.27215(15) 0.0246(7) Uani 1 1 d . . . C6 C 0.18658(7) -0.2692(7) 0.33213(15) 0.0236(7) Uani 1 1 d . . . C7 C 0.21780(7) -0.3195(8) 0.31323(17) 0.0325(8) Uani 1 1 d . . . C8 C 0.23848(7) -0.4271(8) 0.3692(2) 0.0368(9) Uani 1 1 d . . . C9 C 0.01986(7) -0.0138(7) 0.40852(15) 0.0245(7) Uani 1 1 d . . . H9A H 0.0032 0.1029 0.4038 0.029 Uiso 1 1 calc R . . H9B H 0.0174 -0.1214 0.4477 0.029 Uiso 1 1 calc R . . C10 C 0.04790(7) 0.1360(6) 0.41941(15) 0.0210(7) Uani 1 1 d . . . H10A H 0.0646 0.0228 0.4154 0.025 Uiso 1 1 calc R . . H10B H 0.0485 0.2663 0.3846 0.025 Uiso 1 1 calc R . . C11 C 0.05024(7) 0.2584(7) 0.48681(15) 0.0242(7) Uani 1 1 d . . . C12 C 0.07738(7) 0.4205(6) 0.50454(16) 0.0249(7) Uani 1 1 d . . . C13 C 0.10697(7) 0.2872(6) 0.50671(14) 0.0202(7) Uani 1 1 d . . . C14 C 0.13352(7) 0.4505(6) 0.53004(15) 0.0223(7) Uani 1 1 d . . . C15 C 0.16302(7) 0.3121(7) 0.53413(15) 0.0248(7) Uani 1 1 d . . . C16 C 0.18967(7) 0.4753(7) 0.55508(17) 0.0308(8) 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 Sn1 0.01741(17) 0.02145(19) 0.01896(17) 0.000 -0.00042(11) 0.000 S1 0.0297(4) 0.0206(4) 0.0242(4) 0.0016(3) -0.0061(3) -0.0039(4) S2 0.0213(4) 0.0204(4) 0.0334(4) 0.0050(3) 0.0053(3) 0.0022(3) F1 0.0319(11) 0.0226(11) 0.0497(12) -0.0138(10) -0.0087(9) 0.0043(9) F2 0.0271(10) 0.0574(14) 0.0204(9) 0.0134(9) 0.0081(8) 0.0071(10) F3 0.0284(10) 0.0502(14) 0.0252(10) 0.0156(10) 0.0080(8) 0.0054(10) F4 0.0304(11) 0.0301(11) 0.0400(11) -0.0132(9) -0.0049(9) 0.0033(9) F5 0.0309(11) 0.0449(14) 0.0325(11) -0.0187(10) -0.0045(8) 0.0134(10) F6 0.0254(10) 0.0565(15) 0.0372(11) 0.0228(11) 0.0091(9) 0.0020(10) F7 0.0300(11) 0.0353(12) 0.0407(12) 0.0154(10) -0.0032(9) -0.0049(9) F8 0.0299(10) 0.0383(12) 0.0287(10) -0.0116(9) -0.0020(8) 0.0029(9) F9 0.0272(12) 0.086(2) 0.0676(16) 0.0452(16) 0.0100(11) 0.0004(13) F10 0.0365(13) 0.132(3) 0.0523(15) -0.0526(17) -0.0110(11) 0.0419(16) F11 0.0410(15) 0.0489(17) 0.141(3) 0.0375(19) -0.0274(16) -0.0032(13) F12 0.0377(13) 0.086(2) 0.0416(13) -0.0116(14) -0.0101(10) 0.0120(14) F13 0.0244(11) 0.090(2) 0.0526(14) -0.0007(14) 0.0002(10) 0.0184(13) F14 0.0247(10) 0.0463(14) 0.0428(12) -0.0158(10) 0.0006(9) 0.0116(10) F15 0.0291(10) 0.0478(13) 0.0189(9) 0.0066(9) 0.0018(7) -0.0045(10) F16 0.0324(11) 0.0631(16) 0.0478(13) -0.0407(12) 0.0000(10) 0.0088(11) F17 0.0377(12) 0.0217(11) 0.0666(15) 0.0133(10) -0.0148(11) 0.0014(9) F18 0.0265(10) 0.0251(11) 0.0485(12) 0.0146(9) 0.0003(9) -0.0003(9) F19 0.0288(10) 0.0500(14) 0.0269(10) -0.0220(10) 0.0039(8) -0.0003(10) F20 0.0342(11) 0.0443(13) 0.0288(10) -0.0174(10) -0.0002(8) -0.0014(10) F21 0.0305(11) 0.0238(11) 0.0455(12) 0.0151(9) 0.0001(9) -0.0009(9) F22 0.0296(11) 0.0366(13) 0.0507(13) 0.0237(10) 0.0002(9) 0.0015(9) F23 0.0306(11) 0.0387(13) 0.0360(11) -0.0093(10) 0.0044(9) 0.0059(10) F24 0.0302(11) 0.0398(13) 0.0522(13) 0.0140(11) 0.0016(9) -0.0080(10) F25 0.0243(11) 0.0534(16) 0.0799(18) 0.0192(14) -0.0067(11) 0.0027(11) F26 0.0485(14) 0.098(2) 0.0331(12) -0.0138(14) -0.0011(10) -0.0298(15) C1 0.0219(16) 0.0238(17) 0.0215(15) 0.0005(14) 0.0022(12) 0.0053(14) C2 0.0215(15) 0.0256(18) 0.0215(15) -0.0016(14) 0.0028(12) 0.0029(14) C3 0.0254(16) 0.0238(17) 0.0169(14) -0.0007(13) 0.0031(12) -0.0004(15) C4 0.0246(16) 0.0199(17) 0.0184(14) 0.0019(13) 0.0035(12) -0.0015(14) C5 0.0249(17) 0.031(2) 0.0188(15) -0.0011(14) 0.0052(13) -0.0004(15) C6 0.0224(16) 0.0280(19) 0.0208(16) -0.0014(14) 0.0033(13) -0.0020(15) C7 0.0249(18) 0.044(2) 0.0292(18) -0.0018(17) 0.0049(14) 0.0039(17) C8 0.0231(18) 0.037(2) 0.049(2) 0.0013(19) -0.0021(16) 0.0015(17) C9 0.0224(16) 0.0311(19) 0.0197(15) 0.0043(14) -0.0001(12) -0.0022(14) C10 0.0224(15) 0.0227(17) 0.0178(15) 0.0023(13) 0.0015(12) -0.0004(14) C11 0.0210(16) 0.0280(18) 0.0240(16) 0.0000(14) 0.0036(12) 0.0068(15) C12 0.0276(17) 0.0193(17) 0.0273(16) -0.0090(14) -0.0017(13) 0.0035(15) C13 0.0260(16) 0.0190(16) 0.0155(14) -0.0022(13) 0.0018(12) 0.0002(14) C14 0.0262(16) 0.0223(17) 0.0182(15) -0.0020(14) 0.0015(12) 0.0013(14) C15 0.0247(17) 0.0275(19) 0.0223(16) 0.0040(14) 0.0020(13) -0.0004(15) C16 0.0255(18) 0.037(2) 0.0295(18) 0.0055(16) 0.0005(14) -0.0039(16) _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 S2 2.3817(8) 2 ? Sn1 S2 2.3817(9) . ? Sn1 S1 2.3960(9) 2 ? Sn1 S1 2.3960(9) . ? S1 C9 1.834(3) . ? S2 C1 1.836(3) . ? F1 C3 1.359(4) . ? F2 C3 1.352(4) . ? F3 C4 1.350(4) . ? F4 C4 1.343(4) . ? F5 C5 1.340(4) . ? F6 C5 1.339(4) . ? F7 C6 1.336(4) . ? F8 C6 1.335(4) . ? F9 C7 1.328(5) . ? F10 C7 1.329(4) . ? F11 C8 1.310(5) . ? F12 C8 1.312(5) . ? F13 C8 1.314(4) . ? F14 C11 1.364(4) . ? F15 C11 1.361(4) . ? F16 C12 1.341(4) . ? F17 C12 1.348(4) . ? F18 C13 1.335(4) . ? F19 C13 1.346(3) . ? F20 C14 1.341(4) . ? F21 C14 1.344(4) . ? F22 C15 1.338(4) . ? F23 C15 1.340(4) . ? F24 C16 1.319(4) . ? F25 C16 1.311(4) . ? F26 C16 1.316(4) . ? C1 C2 1.532(4) . ? C2 C3 1.499(4) . ? C3 C4 1.542(4) . ? C4 C5 1.547(4) . ? C5 C6 1.553(4) . ? C6 C7 1.544(4) . ? C7 C8 1.538(5) . ? C9 C10 1.527(4) . ? C10 C11 1.504(4) . ? C11 C12 1.546(5) . ? C12 C13 1.541(4) . ? C13 C14 1.552(4) . ? C14 C15 1.549(4) . ? C15 C16 1.544(5) . ? 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 S2 Sn1 S2 110.74(4) 2 . ? S2 Sn1 S1 113.17(3) 2 2 ? S2 Sn1 S1 108.38(3) . 2 ? S2 Sn1 S1 108.38(3) 2 . ? S2 Sn1 S1 113.17(3) . . ? S1 Sn1 S1 102.84(4) 2 . ? C9 S1 Sn1 101.33(11) . . ? C1 S2 Sn1 99.45(11) . . ? C2 C1 S2 112.3(2) . . ? C3 C2 C1 110.6(3) . . ? F2 C3 F1 106.2(3) . . ? F2 C3 C2 110.6(3) . . ? F1 C3 C2 110.2(3) . . ? F2 C3 C4 107.5(3) . . ? F1 C3 C4 107.9(3) . . ? C2 C3 C4 114.2(3) . . ? F4 C4 F3 107.4(2) . . ? F4 C4 C3 107.7(3) . . ? F3 C4 C3 107.9(3) . . ? F4 C4 C5 108.5(3) . . ? F3 C4 C5 109.0(3) . . ? C3 C4 C5 116.1(3) . . ? F6 C5 F5 108.7(3) . . ? F6 C5 C4 108.1(3) . . ? F5 C5 C4 108.2(3) . . ? F6 C5 C6 108.4(3) . . ? F5 C5 C6 108.4(3) . . ? C4 C5 C6 114.9(3) . . ? F8 C6 F7 108.2(2) . . ? F8 C6 C7 108.3(3) . . ? F7 C6 C7 108.7(3) . . ? F8 C6 C5 108.9(3) . . ? F7 C6 C5 108.5(3) . . ? C7 C6 C5 114.0(3) . . ? F9 C7 F10 109.8(3) . . ? F9 C7 C8 106.4(3) . . ? F10 C7 C8 107.4(3) . . ? F9 C7 C6 108.9(3) . . ? F10 C7 C6 108.9(3) . . ? C8 C7 C6 115.3(3) . . ? F11 C8 F12 107.0(4) . . ? F11 C8 F13 109.1(3) . . ? F12 C8 F13 107.8(3) . . ? F11 C8 C7 112.1(3) . . ? F12 C8 C7 110.8(3) . . ? F13 C8 C7 109.8(3) . . ? C10 C9 S1 111.0(2) . . ? C11 C10 C9 111.3(3) . . ? F15 C11 F14 105.9(2) . . ? F15 C11 C10 110.9(3) . . ? F14 C11 C10 109.8(3) . . ? F15 C11 C12 107.4(3) . . ? F14 C11 C12 105.0(3) . . ? C10 C11 C12 117.1(3) . . ? F16 C12 F17 108.4(3) . . ? F16 C12 C13 108.3(3) . . ? F17 C12 C13 107.8(3) . . ? F16 C12 C11 107.7(3) . . ? F17 C12 C11 107.3(3) . . ? C13 C12 C11 117.1(3) . . ? F18 C13 F19 108.0(3) . . ? F18 C13 C12 108.5(3) . . ? F19 C13 C12 107.9(2) . . ? F18 C13 C14 108.8(2) . . ? F19 C13 C14 107.8(2) . . ? C12 C13 C14 115.7(3) . . ? F20 C14 F21 108.8(3) . . ? F20 C14 C15 107.5(3) . . ? F21 C14 C15 108.1(2) . . ? F20 C14 C13 109.0(2) . . ? F21 C14 C13 108.1(2) . . ? C15 C14 C13 115.1(3) . . ? F22 C15 F23 108.9(3) . . ? F22 C15 C16 106.9(3) . . ? F23 C15 C16 107.3(3) . . ? F22 C15 C14 109.1(3) . . ? F23 C15 C14 108.9(3) . . ? C16 C15 C14 115.5(3) . . ? F25 C16 F26 109.5(3) . . ? F25 C16 F24 108.0(3) . . ? F26 C16 F24 108.0(3) . . ? F25 C16 C15 109.1(3) . . ? F26 C16 C15 110.9(3) . . ? F24 C16 C15 111.4(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.569 _refine_diff_density_min -0.737 _refine_diff_density_rms 0.078