# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Lam, Yu-Lin' 'Chen, Wang' 'Huang, Hsing Hua' 'Liang, Eping' 'Wong, Ming Wah' _publ_contact_author_name 'Dr Yu-Lin Lam' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive 3 117543 SINGAPORE ; _publ_contact_author_email 'CHMLAMYL@NUS.EDU.SG' _publ_section_title ; Gauche/trans equilibria of 2,2'-Bi-1,3-dioxolanyl, 2,2'-dimethyl-2,2'-bi-1,3-dioxolanyl,2,2'-Bi-1,3-dithiolanyl and 2,2'-dimethyl-2,2'-bi-1,3-dithiolanyl in different media - theory and experiment ; data_2,2'-Dimethyl-2,2'-bi-1,3-dioxolanyl _database_code_CSD 186624 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-Dimethyl-2,2'-bi-1,3-dioxolanyl ; _chemical_name_common ? _chemical_melting_point '31 C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 O4' _chemical_formula_weight 174.19 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 5.6870(9) _cell_length_b 11.0509(17) _cell_length_c 6.8521(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.624(3) _cell_angle_gamma 90.00 _cell_volume 420.22(11) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3512 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 30.0 _exptl_crystal_description 'rectangular shape, cut' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type 'sadabs (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.510869 _exptl_absorpt_correction_T_max 0.921249 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3404 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 29.99 _reflns_number_total 1219 _reflns_number_gt 999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _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^)+(0.1214P)^2^+0.0832P] 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 none _refine_ls_extinction_coef none _refine_ls_number_reflns 1219 _refine_ls_number_parameters 56 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1963 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 O1 O 1.05401(19) 0.64564(9) 0.39836(16) 0.0268(3) Uani 1 1 d . . . O2 O 0.7617(2) 0.50674(9) 0.27140(17) 0.0256(3) Uani 1 1 d . . . C1 C 1.1727(3) 0.44837(15) 0.2979(2) 0.0287(4) Uani 1 1 d . . . H2A H 1.1736 0.4812 0.1684 0.043 Uiso 1 1 calc R . . H2B H 1.1225 0.3653 0.2844 0.043 Uiso 1 1 calc R . . H2C H 1.3318 0.4533 0.3812 0.043 Uiso 1 1 calc R . . C2 C 0.9996(2) 0.51985(11) 0.3922(2) 0.0215(3) Uani 1 1 d . . . C3 C 0.8973(3) 0.69916(14) 0.2274(2) 0.0306(4) Uani 1 1 d . . . H3A H 0.9641 0.6924 0.1092 0.037 Uiso 1 1 calc R . . H3B H 0.8669 0.7837 0.2508 0.037 Uiso 1 1 calc R . . C4 C 0.6712(3) 0.62436(14) 0.2075(3) 0.0291(4) Uani 1 1 d . . . H4A H 0.5693 0.6555 0.2924 0.035 Uiso 1 1 calc R . . H4B H 0.5803 0.6228 0.0701 0.035 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 O1 0.0316(6) 0.0151(5) 0.0303(6) 0.0025(3) -0.0010(4) -0.0053(4) O2 0.0245(6) 0.0166(5) 0.0317(6) 0.0019(3) -0.0027(4) -0.0016(4) C1 0.0297(8) 0.0290(8) 0.0284(8) -0.0032(5) 0.0083(6) 0.0011(6) C2 0.0215(7) 0.0144(6) 0.0275(7) -0.0001(4) 0.0028(5) -0.0020(4) C3 0.0402(9) 0.0186(7) 0.0295(8) 0.0046(5) -0.0001(6) -0.0028(6) C4 0.0297(8) 0.0209(7) 0.0330(8) 0.0047(5) -0.0013(6) 0.0039(5) _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 O1 C2 1.4228(15) . ? O1 C3 1.4351(18) . ? O2 C2 1.4306(18) . ? O2 C4 1.4310(17) . ? C1 C2 1.513(2) . ? C2 C2 1.540(3) 3_766 ? C3 C4 1.509(2) . ? 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 C2 O1 C3 106.63(11) . . ? C2 O2 C4 108.46(10) . . ? O1 C2 O2 106.74(10) . . ? O1 C2 C1 111.43(12) . . ? O2 C2 C1 108.75(12) . . ? O1 C2 C2 107.14(13) . 3_766 ? O2 C2 C2 109.28(14) . 3_766 ? C1 C2 C2 113.27(14) . 3_766 ? O1 C3 C4 102.30(12) . . ? O2 C4 C3 103.14(12) . . ? 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 C3 O1 C2 O2 -21.65(15) . . . . ? C3 O1 C2 C1 96.96(14) . . . . ? C3 O1 C2 C2 -138.62(15) . . . 3_766 ? C4 O2 C2 O1 -0.91(15) . . . . ? C4 O2 C2 C1 -121.25(13) . . . . ? C4 O2 C2 C2 114.64(14) . . . 3_766 ? C2 O1 C3 C4 34.23(15) . . . . ? C2 O2 C4 C3 21.59(16) . . . . ? O1 C3 C4 O2 -33.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.767 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.107 data_2,2'-Dimethyl-2,2'-bi-1,3-dithiolanyl _database_code_CSD 186625 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-Dimethyl-2,2'-bi-1,3-dithiolanyl ; _chemical_name_common ? _chemical_melting_point '85 C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 S4' _chemical_formula_weight 238.43 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' 'S' 'S' 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.486(6) _cell_length_b 7.358(7) _cell_length_c 12.386(12) _cell_angle_alpha 101.20(2) _cell_angle_beta 95.68(2) _cell_angle_gamma 106.40(2) _cell_volume 548.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4130 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 29.4 _exptl_crystal_description 'rectangular shape, cut' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.52 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.481921 _exptl_absorpt_correction_T_max 0.734837 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6540 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 30.44 _reflns_number_total 3032 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART' _computing_cell_refinement 'Bruker AXS, SAINT' _computing_data_reduction 'Bruker AXS, SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS, SHELXTL' _computing_publication_material 'Bruker AXS, SHELXTL' _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^)+(0.0706P)^2^+0.0000P] 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 0.000(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3032 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 8.638 _refine_ls_shift/su_mean 0.053 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 S1 S 0.30342(13) -0.11561(10) 0.18861(6) 0.0404(2) Uani 1 1 d . . . S2 S 0.13823(11) 0.27782(11) 0.19050(6) 0.0378(2) Uani 1 1 d . . . S3 S 0.26533(13) 0.12270(11) 0.40379(6) 0.0422(2) Uani 1 1 d . . . S4 S 0.55874(11) 0.28409(12) 0.11490(6) 0.0426(2) Uani 1 1 d . . . C1 C 0.6575(6) 0.1255(7) 0.3345(4) 0.0563(10) Uani 1 1 d . . . H1A H 0.659(5) 0.016(5) 0.367(3) 0.054(10) Uiso 1 1 d . . . H1B H 0.732(5) 0.241(5) 0.382(3) 0.039(9) Uiso 1 1 d . . . H1C H 0.742(7) 0.122(6) 0.284(4) 0.075(14) Uiso 1 1 d . . . C2 C 0.4266(4) 0.1185(4) 0.2899(2) 0.0321(6) Uani 1 1 d . . . C3 C 0.1271(7) -0.1358(5) 0.3718(3) 0.0525(9) Uani 1 1 d . . . H3A H 0.005(6) -0.140(5) 0.407(3) 0.061(11) Uiso 1 1 d . . . H3B H 0.229(7) -0.206(6) 0.396(3) 0.076(13) Uiso 1 1 d . . . C4 C 0.0640(6) -0.2021(5) 0.2472(3) 0.0496(8) Uani 1 1 d . . . H4A H -0.064(7) -0.155(6) 0.212(4) 0.082(13) Uiso 1 1 d . . . H4B H 0.021(7) -0.336(7) 0.231(4) 0.081(13) Uiso 1 1 d . . . C5 C 0.5368(7) 0.4894(5) 0.3195(3) 0.0544(9) Uani 1 1 d . . . H5A H 0.472(5) 0.492(5) 0.383(3) 0.048(10) Uiso 1 1 d . . . H5B H 0.686(7) 0.509(6) 0.336(3) 0.072(13) Uiso 1 1 d . . . H5C H 0.513(7) 0.587(6) 0.283(3) 0.077(13) Uiso 1 1 d . . . C6 C 0.4212(4) 0.2946(4) 0.2380(2) 0.0307(5) Uani 1 1 d . . . C7 C 0.1742(6) 0.3300(6) 0.0571(3) 0.0445(7) Uani 1 1 d . . . H7A H 0.217(7) 0.455(6) 0.068(3) 0.070(12) Uiso 1 1 d . . . H7B H 0.044(7) 0.292(6) 0.014(3) 0.070(12) Uiso 1 1 d . . . C8 C 0.3242(5) 0.2258(5) 0.0094(3) 0.0432(7) Uani 1 1 d . . . H8A H 0.372(6) 0.262(5) -0.051(3) 0.047(9) Uiso 1 1 d . . . H8B H 0.262(6) 0.082(6) -0.013(3) 0.068(11) Uiso 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 S1 0.0506(4) 0.0334(4) 0.0401(4) 0.0096(3) 0.0172(3) 0.0138(3) S2 0.0305(4) 0.0457(4) 0.0441(4) 0.0192(3) 0.0109(3) 0.0149(3) S3 0.0493(4) 0.0418(4) 0.0307(4) 0.0083(3) 0.0133(3) 0.0045(3) S4 0.0295(4) 0.0612(5) 0.0431(4) 0.0266(4) 0.0125(3) 0.0114(3) C1 0.0335(17) 0.076(3) 0.066(3) 0.038(2) 0.0046(17) 0.0129(17) C2 0.0279(13) 0.0372(14) 0.0299(13) 0.0093(11) 0.0027(10) 0.0076(10) C3 0.058(2) 0.0460(18) 0.051(2) 0.0165(16) 0.0242(17) 0.0033(16) C4 0.0483(18) 0.0388(16) 0.052(2) 0.0079(15) 0.0154(15) -0.0016(14) C5 0.062(2) 0.0360(17) 0.049(2) 0.0055(15) 0.0037(18) -0.0041(15) C6 0.0279(12) 0.0314(13) 0.0307(13) 0.0094(11) 0.0044(10) 0.0050(10) C7 0.0386(16) 0.053(2) 0.0463(18) 0.0231(16) 0.0039(14) 0.0149(14) C8 0.0419(16) 0.0524(19) 0.0352(16) 0.0141(15) 0.0048(13) 0.0124(14) _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 S1 C4 1.785(4) . ? S1 C2 1.834(3) . ? S2 C7 1.789(4) . ? S2 C6 1.833(3) . ? S3 C3 1.803(4) . ? S3 C2 1.838(3) . ? S4 C8 1.796(3) . ? S4 C6 1.840(3) . ? C1 C2 1.528(4) . ? C2 C6 1.562(4) . ? C3 C4 1.503(5) . ? C5 C6 1.522(4) . ? C7 C8 1.498(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 C4 S1 C2 98.45(15) . . ? C7 S2 C6 97.36(14) . . ? C3 S3 C2 96.47(15) . . ? C8 S4 C6 98.39(16) . . ? C1 C2 C6 112.8(2) . . ? C1 C2 S1 106.8(3) . . ? C6 C2 S1 112.09(19) . . ? C1 C2 S3 109.8(2) . . ? C6 C2 S3 107.44(19) . . ? S1 C2 S3 107.76(14) . . ? C4 C3 S3 107.2(2) . . ? C3 C4 S1 107.1(2) . . ? C5 C6 C2 112.2(3) . . ? C5 C6 S2 110.2(2) . . ? C2 C6 S2 109.71(17) . . ? C5 C6 S4 107.9(2) . . ? C2 C6 S4 109.24(19) . . ? S2 C6 S4 107.45(14) . . ? C8 C7 S2 107.9(2) . . ? C7 C8 S4 107.2(2) . . ? 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 C4 S1 C2 C1 125.8(2) . . . . ? C4 S1 C2 C6 -110.1(2) . . . . ? C4 S1 C2 S3 7.87(18) . . . . ? C3 S3 C2 C1 -99.4(3) . . . . ? C3 S3 C2 C6 137.6(2) . . . . ? C3 S3 C2 S1 16.61(19) . . . . ? C2 S3 C3 C4 -41.7(3) . . . . ? S3 C3 C4 S1 51.6(3) . . . . ? C2 S1 C4 C3 -36.1(3) . . . . ? C1 C2 C6 C5 -55.5(4) . . . . ? S1 C2 C6 C5 -176.2(2) . . . . ? S3 C2 C6 C5 65.6(3) . . . . ? C1 C2 C6 S2 -178.3(3) . . . . ? S1 C2 C6 S2 61.0(2) . . . . ? S3 C2 C6 S2 -57.2(2) . . . . ? C1 C2 C6 S4 64.1(3) . . . . ? S1 C2 C6 S4 -56.5(2) . . . . ? S3 C2 C6 S4 -174.73(12) . . . . ? C7 S2 C6 C5 101.7(3) . . . . ? C7 S2 C6 C2 -134.3(2) . . . . ? C7 S2 C6 S4 -15.65(18) . . . . ? C8 S4 C6 C5 -127.0(3) . . . . ? C8 S4 C6 C2 110.8(2) . . . . ? C8 S4 C6 S2 -8.20(17) . . . . ? C6 S2 C7 C8 40.6(3) . . . . ? S2 C7 C8 S4 -50.3(3) . . . . ? C6 S4 C8 C7 35.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 30.44 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.544 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.104