# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Junfa Wei' _publ_contact_author_email WEIJF@SNNU.EDU.CN _publ_section_title ; Synthesis Of 1,4,5,8,9,12-Hexabromododecahydrotriphenylene And Its Application In Constructing Polycyclic Thioaromatics ; loop_ _publ_author_name 'Junfa Wei.' 'Zhanguo Chen.' 'Xiaowei Jia.' 'Xianying Shi.' 'Jun Yu.' ; Congjie Zhang ; # Attachment 'xb1103.cif' data_xb1103 _database_code_depnum_ccdc_archive 'CCDC 723162' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 Br6' _chemical_formula_sum 'C18 H18 Br6' _chemical_formula_weight 713.78 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 10.724(2) _cell_length_b 10.724(2) _cell_length_c 36.099(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4151(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1590 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 20.76 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2688 _exptl_absorpt_coefficient_mu 11.605 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.3899 _exptl_absorpt_correction_T_max 0.4215 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10290 _diffrn_reflns_av_R_equivalents 0.0904 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.09 _reflns_number_total 1849 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0480P)^2^+8.1682P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00038(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1849 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Br1 Br 0.52715(7) 0.46286(8) 0.05213(2) 0.0580(3) Uani 1 1 d . . . Br2 Br 0.15061(7) 0.36164(8) 0.16165(2) 0.0551(3) Uani 1 1 d . . . Br3 Br 0.50796(8) 0.51838(8) 0.22184(2) 0.0600(3) Uani 1 1 d . . . C1 C 0.4533(6) 0.2966(6) 0.11096(15) 0.0311(14) Uani 1 1 d . . . C2 C 0.4027(6) 0.3469(6) 0.07483(17) 0.0404(16) Uani 1 1 d . . . H2 H 0.3900 0.2767 0.0579 0.049 Uiso 1 1 calc R . . C3 C 0.2813(6) 0.4176(6) 0.07811(18) 0.0418(17) Uani 1 1 d . . . H3A H 0.2644 0.4604 0.0550 0.050 Uiso 1 1 calc R . . H3B H 0.2139 0.3591 0.0825 0.050 Uiso 1 1 calc R . . C4 C 0.2856(7) 0.5112(6) 0.10920(19) 0.0461(18) Uani 1 1 d . . . H4A H 0.2068 0.5555 0.1105 0.055 Uiso 1 1 calc R . . H4B H 0.3510 0.5716 0.1045 0.055 Uiso 1 1 calc R . . C5 C 0.3104(6) 0.4448(6) 0.14584(18) 0.0401(16) Uani 1 1 d . . . H5 H 0.3335 0.5071 0.1645 0.048 Uiso 1 1 calc R . . C6 C 0.4099(6) 0.3449(6) 0.14469(16) 0.0317(14) Uani 1 1 d . . . C7 C 0.4571(6) 0.2988(6) 0.17888(16) 0.0326(14) Uani 1 1 d . . . C8 C 0.4144(7) 0.3570(6) 0.21487(17) 0.0433(17) Uani 1 1 d . . . H8 H 0.3253 0.3760 0.2129 0.052 Uiso 1 1 calc R . . C9 C 0.4344(7) 0.2766(8) 0.24859(17) 0.053(2) Uani 1 1 d . . . H9A H 0.3742 0.2091 0.2487 0.063 Uiso 1 1 calc R . . H9B H 0.4217 0.3260 0.2708 0.063 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 Br1 0.0554(5) 0.0715(6) 0.0470(5) 0.0242(4) -0.0012(4) -0.0103(4) Br2 0.0385(5) 0.0726(6) 0.0540(5) 0.0025(4) 0.0046(3) 0.0051(4) Br3 0.0696(6) 0.0603(6) 0.0501(5) -0.0186(4) 0.0009(4) -0.0042(4) C1 0.034(4) 0.035(4) 0.024(3) 0.003(3) -0.002(3) -0.006(3) C2 0.046(4) 0.047(4) 0.028(3) -0.004(3) -0.003(3) 0.000(3) C3 0.042(4) 0.044(4) 0.039(4) 0.010(3) -0.014(3) 0.003(3) C4 0.050(5) 0.037(4) 0.051(5) 0.004(3) -0.005(3) 0.007(3) C5 0.043(4) 0.039(4) 0.038(4) -0.005(3) -0.005(3) 0.001(3) C6 0.031(3) 0.036(4) 0.028(3) -0.001(3) -0.004(3) 0.000(3) C7 0.027(3) 0.046(4) 0.025(3) -0.003(3) 0.007(3) -0.001(3) C8 0.039(4) 0.058(5) 0.032(4) -0.007(3) 0.004(3) 0.004(3) C9 0.056(5) 0.074(6) 0.028(4) -0.007(4) 0.011(3) 0.007(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 Br1 C2 2.000(7) . ? Br2 C5 2.014(7) . ? Br3 C8 2.015(7) . ? C1 C6 1.403(8) . ? C1 C1 1.415(12) 6_554 ? C1 C2 1.512(8) . ? C2 C3 1.511(9) . ? C2 H2 0.9800 . ? C3 C4 1.507(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.525(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.513(9) . ? C5 H5 0.9800 . ? C6 C7 1.423(8) . ? C7 C7 1.394(12) 6_554 ? C7 C8 1.513(8) . ? C8 C9 1.507(9) . ? C8 H8 0.9800 . ? C9 C9 1.518(14) 6_554 ? C9 H9A 0.9700 . ? C9 H9B 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 C6 C1 C1 119.7(3) . 6_554 ? C6 C1 C2 119.9(6) . . ? C1 C1 C2 120.4(4) 6_554 . ? C3 C2 C1 114.9(5) . . ? C3 C2 Br1 107.2(5) . . ? C1 C2 Br1 109.6(4) . . ? C3 C2 H2 108.3 . . ? C1 C2 H2 108.3 . . ? Br1 C2 H2 108.3 . . ? C4 C3 C2 111.5(5) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 109.9(6) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 C5 C4 115.5(5) . . ? C6 C5 Br2 107.1(4) . . ? C4 C5 Br2 107.7(4) . . ? C6 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? Br2 C5 H5 108.8 . . ? C1 C6 C7 120.4(5) . . ? C1 C6 C5 121.3(5) . . ? C7 C6 C5 118.3(5) . . ? C7 C7 C6 119.7(3) 6_554 . ? C7 C7 C8 120.7(4) 6_554 . ? C6 C7 C8 119.6(5) . . ? C9 C8 C7 114.5(6) . . ? C9 C8 Br3 108.6(5) . . ? C7 C8 Br3 108.1(4) . . ? C9 C8 H8 108.5 . . ? C7 C8 H8 108.5 . . ? Br3 C8 H8 108.5 . . ? C8 C9 C9 110.3(5) . 6_554 ? C8 C9 H9A 109.6 . . ? C9 C9 H9A 109.6 6_554 . ? C8 C9 H9B 109.6 . . ? C9 C9 H9B 109.6 6_554 . ? H9A C9 H9B 108.1 . . ? 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 C6 C1 C2 C3 -18.0(8) . . . . ? C1 C1 C2 C3 163.7(7) 6_554 . . . ? C6 C1 C2 Br1 102.7(6) . . . . ? C1 C1 C2 Br1 -75.5(8) 6_554 . . . ? C1 C2 C3 C4 47.6(8) . . . . ? Br1 C2 C3 C4 -74.5(6) . . . . ? C2 C3 C4 C5 -59.7(7) . . . . ? C3 C4 C5 C6 43.4(8) . . . . ? C3 C4 C5 Br2 -76.2(6) . . . . ? C1 C1 C6 C7 -1.4(11) 6_554 . . . ? C2 C1 C6 C7 -179.7(6) . . . . ? C1 C1 C6 C5 179.9(7) 6_554 . . . ? C2 C1 C6 C5 1.6(9) . . . . ? C4 C5 C6 C1 -14.9(9) . . . . ? Br2 C5 C6 C1 105.0(6) . . . . ? C4 C5 C6 C7 166.4(6) . . . . ? Br2 C5 C6 C7 -73.7(6) . . . . ? C1 C6 C7 C7 -2.9(11) . . . 6_554 ? C5 C6 C7 C7 175.8(7) . . . 6_554 ? C1 C6 C7 C8 176.6(6) . . . . ? C5 C6 C7 C8 -4.6(9) . . . . ? C7 C7 C8 C9 -20.1(10) 6_554 . . . ? C6 C7 C8 C9 160.4(6) . . . . ? C7 C7 C8 Br3 101.1(8) 6_554 . . . ? C6 C7 C8 Br3 -78.4(6) . . . . ? C7 C8 C9 C9 47.2(10) . . . 6_554 ? Br3 C8 C9 C9 -73.7(8) . . . 6_554 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.622 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.125 # Attachment 'xb1677.cif' data_xb1677 _database_code_depnum_ccdc_archive 'CCDC 723163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H6 S5' _chemical_formula_sum 'C18 H6 S5' _chemical_formula_weight 382.53 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 Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 6.9134(5) _cell_length_b 19.5698(14) _cell_length_c 10.8775(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1471.66(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2740 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 26.70 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7884 _exptl_absorpt_correction_T_max 0.8919 _exptl_absorpt_process_details '(SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6868 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1343 _reflns_number_gt 1201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0800P)^2^+1.0936P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1343 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 S1 S 0.16891(14) 0.7500 0.58329(7) 0.0463(3) Uani 1 2 d S . . S2 S 0.26294(14) 0.55496(4) 1.03421(8) 0.0656(3) Uani 1 1 d . . . S3 S 0.05875(14) 0.59122(4) 1.15363(8) 0.0644(3) Uani 1 1 d . . . C1 C 0.1695(3) 0.68567(13) 0.6952(2) 0.0390(6) Uani 1 1 d . . . C2 C 0.1936(4) 0.61605(15) 0.6831(3) 0.0496(7) Uani 1 1 d . . . H2 H 0.1989 0.5957 0.6058 0.059 Uiso 1 1 calc R . . C3 C 0.2098(4) 0.57713(14) 0.7893(3) 0.0520(7) Uani 1 1 d . . . H3 H 0.2275 0.5302 0.7819 0.062 Uiso 1 1 calc R . . C4 C 0.2006(4) 0.60554(13) 0.9063(2) 0.0427(6) Uani 1 1 d . . . C5 C 0.1672(3) 0.67603(13) 0.9213(2) 0.0338(5) Uani 1 1 d . . . C6 C 0.1566(3) 0.71391(12) 0.8134(2) 0.0330(5) Uani 1 1 d . . . C7 C 0.1481(3) 0.71364(13) 1.0376(2) 0.0330(5) Uani 1 1 d . . . C8 C 0.1123(4) 0.67924(14) 1.1496(2) 0.0419(6) Uani 1 1 d . . . C9 C 0.0891(4) 0.71474(15) 1.2583(2) 0.0502(7) Uani 1 1 d . . . H9 H 0.0733 0.6911 1.3317 0.060 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 S1 0.0440(5) 0.0699(7) 0.0251(5) 0.000 -0.0003(3) 0.000 S2 0.0849(7) 0.0441(5) 0.0679(6) 0.0147(3) 0.0025(4) 0.0125(4) S3 0.0809(6) 0.0528(5) 0.0594(5) 0.0190(4) 0.0105(4) -0.0088(4) C1 0.0350(12) 0.0513(15) 0.0306(12) -0.0062(11) 0.0006(9) -0.0026(11) C2 0.0471(14) 0.0561(16) 0.0455(15) -0.0217(13) 0.0025(12) -0.0031(13) C3 0.0520(16) 0.0385(14) 0.0657(18) -0.0141(13) 0.0026(14) -0.0020(12) C4 0.0446(13) 0.0359(13) 0.0476(14) 0.0010(11) 0.0003(11) 0.0002(11) C5 0.0320(11) 0.0366(12) 0.0329(12) 0.0004(10) -0.0004(9) -0.0016(10) C6 0.0296(11) 0.0391(12) 0.0302(12) -0.0034(10) -0.0005(9) -0.0003(9) C7 0.0305(11) 0.0407(13) 0.0278(11) 0.0021(9) -0.0013(9) 0.0001(10) C8 0.0397(13) 0.0494(15) 0.0366(13) 0.0102(11) -0.0023(10) -0.0023(11) C9 0.0474(15) 0.0783(18) 0.0249(11) 0.0082(12) 0.0017(10) -0.0028(13) _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 C1 1.751(3) 7_575 ? S1 C1 1.751(3) . ? S2 C4 1.761(3) . ? S2 S3 2.0455(13) . ? S3 C8 1.762(3) . ? C1 C2 1.379(4) . ? C1 C6 1.402(3) . ? C2 C3 1.388(4) . ? C2 H2 0.9300 . ? C3 C4 1.391(4) . ? C3 H3 0.9300 . ? C4 C5 1.408(4) . ? C5 C6 1.390(3) . ? C5 C7 1.469(3) . ? C6 C6 1.413(5) 7_575 ? C7 C8 1.414(3) . ? C7 C7 1.423(5) 7_575 ? C8 C9 1.381(4) . ? C9 C9 1.380(6) 7_575 ? C9 H9 0.9300 . ? 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 C1 S1 C1 91.91(16) 7_575 . ? C4 S2 S3 97.92(10) . . ? C8 S3 S2 100.27(9) . . ? C2 C1 C6 119.0(2) . . ? C2 C1 S1 130.1(2) . . ? C6 C1 S1 110.73(19) . . ? C1 C2 C3 118.2(2) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C2 C3 C4 122.6(2) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C3 C4 C5 120.4(2) . . ? C3 C4 S2 119.2(2) . . ? C5 C4 S2 119.93(19) . . ? C6 C5 C4 115.6(2) . . ? C6 C5 C7 117.1(2) . . ? C4 C5 C7 127.3(2) . . ? C5 C6 C1 124.1(2) . . ? C5 C6 C6 122.21(14) . 7_575 ? C1 C6 C6 113.21(14) . 7_575 ? C8 C7 C7 118.43(15) . 7_575 ? C8 C7 C5 121.3(2) . . ? C7 C7 C5 120.06(13) 7_575 . ? C9 C8 C7 121.3(2) . . ? C9 C8 S3 116.48(19) . . ? C7 C8 S3 121.57(19) . . ? C8 C9 C9 120.21(16) . 7_575 ? C8 C9 H9 119.9 . . ? C9 C9 H9 119.9 7_575 . ? 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 S2 S3 C8 -56.20(13) . . . . ? C1 S1 C1 C2 -170.9(2) 7_575 . . . ? C1 S1 C1 C6 4.1(2) 7_575 . . . ? C6 C1 C2 C3 -1.8(4) . . . . ? S1 C1 C2 C3 172.7(2) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 2.2(4) . . . . ? C2 C3 C4 S2 -169.4(2) . . . . ? S3 S2 C4 C3 -142.3(2) . . . . ? S3 S2 C4 C5 46.1(2) . . . . ? C3 C4 C5 C6 -3.7(4) . . . . ? S2 C4 C5 C6 167.84(18) . . . . ? C3 C4 C5 C7 178.2(2) . . . . ? S2 C4 C5 C7 -10.3(4) . . . . ? C4 C5 C6 C1 2.5(3) . . . . ? C7 C5 C6 C1 -179.1(2) . . . . ? C4 C5 C6 C6 -169.08(16) . . . 7_575 ? C7 C5 C6 C6 9.3(2) . . . 7_575 ? C2 C1 C6 C5 0.2(4) . . . . ? S1 C1 C6 C5 -175.37(19) . . . . ? C2 C1 C6 C6 172.50(19) . . . 7_575 ? S1 C1 C6 C6 -3.08(18) . . . 7_575 ? C6 C5 C7 C8 165.3(2) . . . . ? C4 C5 C7 C8 -16.6(4) . . . . ? C6 C5 C7 C7 -9.1(2) . . . 7_575 ? C4 C5 C7 C7 169.1(2) . . . 7_575 ? C7 C7 C8 C9 -3.8(3) 7_575 . . . ? C5 C7 C8 C9 -178.2(2) . . . . ? C7 C7 C8 S3 166.35(12) 7_575 . . . ? C5 C7 C8 S3 -8.0(3) . . . . ? S2 S3 C8 C9 -144.76(19) . . . . ? S2 S3 C8 C7 44.7(2) . . . . ? C7 C8 C9 C9 3.8(3) . . . 7_575 ? S3 C8 C9 C9 -166.77(10) . . . 7_575 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.898 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.061