# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Bernard Jousseaume' _publ_contact_author_address ; Laboratoire de Chimie Organique et Organometallique Universite de Bordeaux I 351, Cours de la Liberation Talence cedex 33405 FRANCE ; _publ_contact_author_email B.JOUSSEAUME@LCOO.U-BORDEAUX1.FR _publ_section_title ; A Doubly Folded Spacer in a Self-Assembled Hybrid Material ; loop_ _publ_author_name 'Bernard Jousseaume' 'Hassan Allouchi' 'Monique Biesemans' 'Hicham Elhamzaoui' 'Thierry Toupance' ; R.Willem ; 'Cecile Zakri' data_tpcl3 _database_code_depnum_ccdc_archive 'CCDC 288987' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Cl3 O Sn' _chemical_formula_sum 'C22 H28 Cl6 O2 Sn2' _chemical_formula_weight 774.57 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' O O 0.0106 0.0060 '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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0738(2) _cell_length_b 7.4590(2) _cell_length_c 14.2470(6) _cell_angle_alpha 101.473(1) _cell_angle_beta 91.444(1) _cell_angle_gamma 105.224(1) _cell_volume 708.46(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.815 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 2.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_absorpt_correction_T_min 0.5915 _exptl_absorpt_correction_T_max 0.7992 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5004 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.70 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3192 _reflns_number_gt 2901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa-CCD; COLLECT(Nonius, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Miror, 1997)and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson,1996)' _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^)+(0.0118P)^2^+0.3663P] 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 SHELXL _refine_ls_extinction_coef 0.0104(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3192 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0557 _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 0.29215(2) 0.40991(2) 0.337336(12) 0.04283(9) Uani 1 1 d . . . Cl1 Cl 0.60743(9) 0.40407(10) 0.29799(6) 0.05731(18) Uani 1 1 d . . . Cl2 Cl 0.11022(10) 0.46891(10) 0.21438(6) 0.05674(18) Uani 1 1 d . . . Cl3 Cl 0.39201(14) 0.72806(11) 0.42829(8) 0.0824(3) Uani 1 1 d . . . O1 O 0.2118(2) 0.0922(2) 0.22887(12) 0.0389(4) Uani 1 1 d . . . C1 C 0.4632(3) -0.4158(3) 0.01964(16) 0.0369(5) Uani 1 1 d . . . C2 C 0.5486(4) -0.2897(4) 0.1045(2) 0.0617(8) Uani 1 1 d . . . H2 H 0.6519 -0.3118 0.1378 0.074 Uiso 1 1 calc R . . C3 C 0.4844(4) -0.1322(4) 0.1406(2) 0.0645(9) Uani 1 1 d . . . H3 H 0.5449 -0.0507 0.1978 0.077 Uiso 1 1 calc R . . C4 C 0.3324(4) -0.0938(3) 0.09350(18) 0.0412(5) Uani 1 1 d . . . C5 C 0.2431(5) -0.2209(4) 0.0114(2) 0.0611(8) Uani 1 1 d . . . H5 H 0.1369 -0.2008 -0.0206 0.073 Uiso 1 1 calc R . . C6 C 0.3078(5) -0.3795(4) -0.0250(2) 0.0603(8) Uani 1 1 d . . . H6 H 0.2440 -0.4630 -0.0811 0.072 Uiso 1 1 calc R . . C7 C 0.2688(4) 0.0834(3) 0.13151(19) 0.0468(6) Uani 1 1 d . . . H7A H 0.3760 0.1945 0.1300 0.056 Uiso 1 1 calc R . . H7B H 0.1588 0.0857 0.0902 0.056 Uiso 1 1 calc R . . C8 C 0.0206(4) -0.0386(4) 0.2287(2) 0.0529(6) Uani 1 1 d . . . H8A H 0.0177 -0.1613 0.1891 0.063 Uiso 1 1 calc R . . H8B H -0.0785 0.0081 0.2008 0.063 Uiso 1 1 calc R . . C9 C -0.0273(4) -0.0622(4) 0.3279(2) 0.0605(8) Uani 1 1 d . . . H9A H 0.0769 -0.1018 0.3563 0.073 Uiso 1 1 calc R . . H9B H -0.1474 -0.1640 0.3230 0.073 Uiso 1 1 calc R . . C10 C -0.0531(4) 0.1117(4) 0.3949(2) 0.0567(7) Uani 1 1 d . . . H10A H -0.1250 0.0721 0.4477 0.068 Uiso 1 1 calc R . . H10B H -0.1330 0.1695 0.3606 0.068 Uiso 1 1 calc R . . C11 C 0.1359(5) 0.2604(5) 0.4359(2) 0.0651(8) Uani 1 1 d . . . H11A H 0.2216 0.1989 0.4636 0.078 Uiso 1 1 calc R . . H11B H 0.1057 0.3521 0.4876 0.078 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 0.03973(12) 0.04344(12) 0.04464(13) 0.00389(7) 0.00418(7) 0.01419(7) Cl1 0.0363(3) 0.0611(4) 0.0731(5) 0.0092(3) 0.0038(3) 0.0147(3) Cl2 0.0585(4) 0.0538(4) 0.0640(4) 0.0144(3) -0.0025(3) 0.0254(3) Cl3 0.0791(6) 0.0572(4) 0.0947(7) -0.0239(4) -0.0121(5) 0.0226(4) O1 0.0360(8) 0.0366(8) 0.0427(9) 0.0049(7) 0.0077(7) 0.0099(6) C1 0.0333(11) 0.0404(11) 0.0340(12) 0.0017(9) 0.0068(9) 0.0092(9) C2 0.0477(15) 0.0547(15) 0.072(2) -0.0187(14) -0.0206(14) 0.0221(12) C3 0.0537(17) 0.0543(15) 0.072(2) -0.0226(14) -0.0198(14) 0.0201(13) C4 0.0428(13) 0.0405(12) 0.0402(13) 0.0046(10) 0.0097(10) 0.0135(10) C5 0.0720(19) 0.0726(18) 0.0432(15) -0.0063(13) -0.0126(14) 0.0429(15) C6 0.0720(19) 0.0682(17) 0.0401(15) -0.0140(13) -0.0157(13) 0.0390(15) C7 0.0572(15) 0.0441(13) 0.0413(14) 0.0066(10) 0.0098(12) 0.0190(11) C8 0.0396(13) 0.0468(13) 0.0641(18) 0.0019(12) 0.0087(12) 0.0047(10) C9 0.0541(16) 0.0508(15) 0.081(2) 0.0239(14) 0.0235(15) 0.0136(12) C10 0.0538(16) 0.0678(17) 0.0582(18) 0.0239(14) 0.0224(13) 0.0236(13) C11 0.075(2) 0.0759(19) 0.0423(16) 0.0134(14) 0.0126(14) 0.0149(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 C11 2.119(3) . ? Sn1 Cl1 2.3225(7) . ? Sn1 Cl2 2.3257(7) . ? Sn1 Cl3 2.3791(7) . ? Sn1 O1 2.4735(15) . ? O1 C8 1.445(3) . ? O1 C7 1.448(3) . ? C1 C6 1.370(3) . ? C1 C2 1.387(3) . ? C1 C1 1.497(4) 2_645 ? C2 C3 1.379(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(4) . ? C3 H3 0.9300 . ? C4 C5 1.368(4) . ? C4 C7 1.510(3) . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.495(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.506(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.511(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 Cl1 124.25(10) . . ? C11 Sn1 Cl2 117.70(10) . . ? Cl1 Sn1 Cl2 112.48(3) . . ? C11 Sn1 Cl3 102.33(9) . . ? Cl1 Sn1 Cl3 94.39(3) . . ? Cl2 Sn1 Cl3 96.51(3) . . ? C11 Sn1 O1 84.05(10) . . ? Cl1 Sn1 O1 81.15(4) . . ? Cl2 Sn1 O1 81.05(4) . . ? Cl3 Sn1 O1 173.57(4) . . ? C8 O1 C7 109.98(19) . . ? C8 O1 Sn1 119.21(14) . . ? C7 O1 Sn1 117.12(13) . . ? C6 C1 C2 116.6(2) . . ? C6 C1 C1 122.2(3) . 2_645 ? C2 C1 C1 121.2(3) . 2_645 ? C3 C2 C1 121.7(3) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 117.5(2) . . ? C5 C4 C7 121.9(2) . . ? C3 C4 C7 120.6(2) . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 121.5(2) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O1 C7 C4 111.9(2) . . ? O1 C7 H7A 109.2 . . ? C4 C7 H7A 109.2 . . ? O1 C7 H7B 109.2 . . ? C4 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O1 C8 C9 111.7(2) . . ? O1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? O1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 115.6(2) . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C8 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 114.9(2) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 Sn1 115.8(2) . . ? C10 C11 H11A 108.3 . . ? Sn1 C11 H11A 108.3 . . ? C10 C11 H11B 108.3 . . ? Sn1 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 Sn1 O1 C8 39.0(2) . . . . ? Cl1 Sn1 O1 C8 165.07(18) . . . . ? Cl2 Sn1 O1 C8 -80.33(17) . . . . ? Cl3 Sn1 O1 C8 -148.5(3) . . . . ? C11 Sn1 O1 C7 175.56(18) . . . . ? Cl1 Sn1 O1 C7 -58.36(15) . . . . ? Cl2 Sn1 O1 C7 56.24(15) . . . . ? Cl3 Sn1 O1 C7 -11.9(5) . . . . ? C6 C1 C2 C3 -1.9(5) . . . . ? C1 C1 C2 C3 178.9(3) 2_645 . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C2 C3 C4 C5 2.2(5) . . . . ? C2 C3 C4 C7 -177.4(3) . . . . ? C3 C4 C5 C6 -2.2(5) . . . . ? C7 C4 C5 C6 177.4(3) . . . . ? C2 C1 C6 C5 1.9(5) . . . . ? C1 C1 C6 C5 -178.9(3) 2_645 . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C8 O1 C7 C4 -75.3(3) . . . . ? Sn1 O1 C7 C4 144.38(16) . . . . ? C5 C4 C7 O1 122.6(3) . . . . ? C3 C4 C7 O1 -57.8(3) . . . . ? C7 O1 C8 C9 169.0(2) . . . . ? Sn1 O1 C8 C9 -51.6(3) . . . . ? O1 C8 C9 C10 66.2(3) . . . . ? C8 C9 C10 C11 -77.2(3) . . . . ? C9 C10 C11 Sn1 70.1(3) . . . . ? Cl1 Sn1 C11 C10 -118.0(2) . . . . ? Cl2 Sn1 C11 C10 33.6(3) . . . . ? Cl3 Sn1 C11 C10 137.9(2) . . . . ? O1 Sn1 C11 C10 -43.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.468 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.062 # Attachment 'Compound_6.cif' data_nanny _database_code_depnum_ccdc_archive 'CCDC 288988' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Cl3 Sn' _chemical_formula_weight 357.24 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' Cl Cl 0.1484 0.1585 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.665(3) _cell_length_b 8.907(11) _cell_length_c 10.679(8) _cell_angle_alpha 90.05(4) _cell_angle_beta 89.12(5) _cell_angle_gamma 81.93(5) _cell_volume 627.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.890 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 2.634 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 9788 _diffrn_reflns_av_R_equivalents 0.0898 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 37.76 _reflns_number_total 2386 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0415P)^2^+10.6353P] 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 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2386 _refine_ls_number_parameters 128 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1592 _refine_ls_wR_factor_gt 0.1493 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.125 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 1.41637(9) 0.78421(6) 0.08063(7) 0.0247(2) Uani 1 1 d D . . Cl2 Cl 1.7106(4) 0.7521(3) -0.0227(3) 0.0357(6) Uani 1 1 d . . . Cl3 Cl 1.2469(4) 0.5958(2) 0.0493(3) 0.0400(7) Uani 1 1 d . . . Cl4 Cl 1.2175(4) 0.9118(3) -0.0979(3) 0.0403(7) Uani 1 1 d . . . C4 C 1.4596(11) 0.8639(11) 0.2742(6) 0.060(5) Uani 1 1 d D . . H4A H 1.5071 0.7768 0.3256 0.072 Uiso 1 1 calc R . . H4B H 1.5646 0.9291 0.2724 0.072 Uiso 1 1 calc R . . C5 C 1.2748(12) 0.9478(8) 0.3337(10) 0.027(2) Uani 1 1 d D . . H5A H 1.2365 1.0403 0.2868 0.033 Uiso 1 1 calc R . . H5B H 1.3087 0.9770 0.4175 0.033 Uiso 1 1 calc R . . C6 C 1.0947(11) 0.8660(9) 0.3434(9) 0.025(2) Uani 1 1 d D . . H6A H 1.0815 0.8086 0.2675 0.030 Uiso 1 1 calc R . . H6B H 0.9721 0.9374 0.3559 0.030 Uiso 1 1 calc R . . C7 C 1.1286(13) 0.7610(10) 0.4540(10) 0.033(2) Uani 1 1 d D . . H7A H 1.1459 0.8177 0.5298 0.040 Uiso 1 1 calc R . . H7B H 1.2480 0.6868 0.4405 0.040 Uiso 1 1 calc R . . C8 C 0.9355(11) 0.6822(9) 0.4645(7) 0.029(2) Uani 1 1 d D . . C9 C 0.8422(12) 0.6909(10) 0.5855(8) 0.034(2) Uani 1 1 d D . . H9 H 0.8926 0.7409 0.6520 0.040 Uiso 1 1 calc R . . C10 C 0.6680(12) 0.6185(10) 0.5975(8) 0.034(2) Uani 1 1 d D . . H10 H 0.5993 0.6210 0.6742 0.041 Uiso 1 1 calc R . . C11 C 0.5953(11) 0.5415(8) 0.4943(7) 0.024(2) Uani 1 1 d D . . C12 C 0.6879(11) 0.5334(9) 0.3732(8) 0.029(2) Uani 1 1 d D . . H12 H 0.6372 0.4836 0.3066 0.034 Uiso 1 1 calc R . . C13 C 0.8618(11) 0.6063(8) 0.3611(9) 0.033(3) Uani 1 1 d D . . H13 H 0.9295 0.6046 0.2842 0.040 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 0.0259(3) 0.0109(2) 0.0365(5) -0.0009(2) 0.0100(2) -0.00043(17) Cl2 0.0309(11) 0.0238(10) 0.0512(18) -0.0092(10) 0.0179(11) -0.0023(8) Cl3 0.0369(12) 0.0146(8) 0.069(2) -0.0023(10) 0.0129(12) -0.0051(7) Cl4 0.0418(13) 0.0208(10) 0.057(2) 0.0090(11) -0.0003(12) 0.0008(8) C4 0.022(5) 0.025(5) 0.131(15) 0.023(7) 0.024(6) -0.002(3) C5 0.029(4) 0.009(3) 0.044(7) -0.001(3) 0.013(4) -0.002(3) C6 0.015(4) 0.016(3) 0.042(6) 0.007(4) 0.001(4) 0.002(2) C7 0.020(4) 0.022(4) 0.057(8) 0.009(4) 0.008(4) -0.001(3) C8 0.020(4) 0.016(3) 0.051(7) 0.011(4) 0.013(4) 0.001(3) C9 0.031(5) 0.021(4) 0.049(7) 0.006(4) 0.005(4) -0.005(3) C10 0.032(5) 0.021(4) 0.049(7) 0.000(4) 0.018(4) -0.004(3) C11 0.023(4) 0.010(3) 0.039(6) 0.003(3) 0.014(4) 0.000(2) C12 0.025(4) 0.015(3) 0.045(7) 0.001(4) 0.010(4) 0.000(3) C13 0.029(4) 0.008(3) 0.060(8) 0.000(4) 0.022(4) 0.001(3) _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 Cl3 2.179(3) . ? Sn1 Cl2 2.218(2) . ? Sn1 C4 2.221(5) . ? Sn1 Cl4 2.518(3) . ? C4 C5 1.482(5) . ? C5 C6 1.491(11) . ? C6 C7 1.507(5) . ? C7 C8 1.553(11) . ? C8 C9 1.423(5) . ? C8 C13 1.423(5) . ? C9 C10 1.409(5) . ? C10 C11 1.424(5) . ? C11 C12 1.422(5) . ? C11 C11 1.560(14) 2_666 ? C12 C13 1.410(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 Cl3 Sn1 Cl2 111.56(11) . . ? Cl3 Sn1 C4 120.1(3) . . ? Cl2 Sn1 C4 109.9(2) . . ? Cl3 Sn1 Cl4 85.85(12) . . ? Cl2 Sn1 Cl4 95.02(12) . . ? C4 Sn1 Cl4 130.8(3) . . ? C5 C4 Sn1 114.4(6) . . ? C4 C5 C6 116.5(7) . . ? C5 C6 C7 106.7(7) . . ? C6 C7 C8 105.4(7) . . ? C9 C8 C13 123.5(7) . . ? C9 C8 C7 114.3(7) . . ? C13 C8 C7 122.1(7) . . ? C10 C9 C8 115.3(7) . . ? C9 C10 C11 121.1(7) . . ? C12 C11 C10 123.6(6) . . ? C12 C11 C11 114.3(7) . 2_666 ? C10 C11 C11 122.1(7) . 2_666 ? C13 C12 C11 115.3(7) . . ? C12 C13 C8 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.354 _diffrn_reflns_theta_full 37.76 _diffrn_measured_fraction_theta_full 0.354 _refine_diff_density_max 2.763 _refine_diff_density_min -2.750 _refine_diff_density_rms 0.206