# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1529 data_Murph22_Patro _publ_requested_journal 'Chem. Commun.' _publ_contact_author ; Alan Kennedy Dept of P & A Chemistry University of Strathclyde 295 Cathedral St Glasgow G1 1 XL ; _publ_contact_letter ; "Unprecedented Elecrophilic Behaviour ofTetrathiafulvalenium Salts" by O Callaghan, X Frank & JA Murphy Chem. Commun., 1997, 1923-1924. The following file details the X-ray structural work that underpins the new identities of two compounds. If possible could you pass the cif on to the Cambridge Database when appropriate. ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 0141 548 2016 or 4241 ' _publ_contact_author_fax ' 0141 552 0876 ' _publ_contact_author_email ' a.r.kennedy@strath.ac.uk' #----------------------------------------------------------------------- _audit_creation_date 'Thu Nov 11 21:59:04 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record 'line edit 5/1/00' #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'SIR/texsan' _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' #----------------------------------------------------------------------- _cell_length_a 8.418(6) _cell_length_b 8.477(4) _cell_length_c 11.823(5) _cell_angle_alpha 85.75(4) _cell_angle_beta 78.14(4) _cell_angle_gamma 66.95(4) _cell_volume 759.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 19 _cell_measurement_theta_min 6.45 _cell_measurement_theta_max 20.10 #----------------------------------------------------------------------- _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #----------------------------------------------------------------------- _exptl_crystal_description 'sliver' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_meas 0.000 _chemical_formula_weight 336.50 _chemical_formula_analytical ? _chemical_formula_sum 'C15 H12 O S4 ' _chemical_formula_moiety 'C15 H12 O S4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 348.00 _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details psi-scan _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_correction_T_min 0.735 #----------------------------------------------------------------------- _diffrn_special_details none _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device 'Rigaku AFC7S diffractometer' _diffrn_measurement_method 'omega/theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.64 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 4302 _reflns_number_total 4041 _reflns_number_observed 3320 _reflns_observed_criterion 'I>2\s(I)' _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.99 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.09192 _diffrn_orient_matrix_UB_12 0.02369 _diffrn_orient_matrix_UB_13 -0.05861 _diffrn_orient_matrix_UB_21 0.01788 _diffrn_orient_matrix_UB_22 0.06673 _diffrn_orient_matrix_UB_23 0.05914 _diffrn_orient_matrix_UB_31 0.09240 _diffrn_orient_matrix_UB_32 -0.10688 _diffrn_orient_matrix_UB_33 0.02320 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 30 0.003 0.002 'International Tables' H 0 24 0.000 0.000 'International Tables' O 0 2 0.011 0.006 'International Tables' S 0 8 0.125 0.123 'International Tables' #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.55083(7) 0.02113(7) 0.21500(5) 0.0337 Uij ? ? S(2) 0.51027(7) 0.27474(7) 0.02874(4) 0.0321 Uij ? ? S(3) 0.93335(7) 0.00308(7) 0.21929(5) 0.0377 Uij ? ? S(4) 0.88787(8) 0.27439(8) 0.02831(5) 0.0380 Uij ? ? O(1) 0.6729(3) 0.1361(2) 0.5975(1) 0.0538 Uij ? ? C(1) 0.3611(3) 0.0840(3) 0.1568(2) 0.0341 Uij ? ? C(2) 0.3437(3) 0.1979(3) 0.0725(2) 0.0348 Uij ? ? C(3) 0.6435(3) 0.1474(3) 0.1234(2) 0.0293 Uij ? ? C(4) 0.8030(3) 0.1466(3) 0.1278(2) 0.0331 Uij ? ? C(5) 0.9178(3) 0.1451(3) 0.3334(2) 0.0367 Uij ? ? C(6) 0.7329(3) 0.2351(3) 0.4035(2) 0.0351 Uij ? ? C(7) 0.6617(4) 0.1137(4) 0.4792(2) 0.0477 Uij ? ? C(8) 0.7022(3) 0.2831(3) 0.6014(2) 0.0398 Uij ? ? C(9) 0.7349(3) 0.3511(3) 0.4937(2) 0.0373 Uij ? ? C(10) 0.7694(5) 0.4975(4) 0.4844(2) 0.0571 Uij ? ? C(11) 0.7741(4) 0.5728(4) 0.5838(3) 0.0600 Uij ? ? C(12) 0.7422(4) 0.5012(4) 0.6907(2) 0.0549 Uij ? ? C(13) 0.7048(4) 0.3569(4) 0.7015(2) 0.0546 Uij ? ? C(14) 0.8529(3) 0.4434(3) 0.1111(2) 0.0437 Uij ? ? C(15) 0.8381(6) 0.5626(4) 0.1621(3) 0.0760 Uij ? ? H(1) 0.289(4) 0.030(3) 0.188(2) 0.047(7) Uij ? ? H(2) 0.250(3) 0.241(3) 0.037(2) 0.042(7) Uij ? ? H(3) 0.999(4) 0.069(4) 0.386(2) 0.054(8) Uij ? ? H(4) 0.970(3) 0.224(3) 0.296(2) 0.040(7) Uij ? ? H(5) 0.655(3) 0.300(3) 0.352(2) 0.031(6) Uij ? ? H(6) 0.735(4) -0.013(4) 0.461(3) 0.08(1) Uij ? ? H(7) 0.540(5) 0.141(4) 0.477(3) 0.072(10) Uij ? ? H(8) 0.790(5) 0.547(4) 0.418(3) 0.08(1) Uij ? ? H(9) 0.795(5) 0.677(4) 0.576(3) 0.08(1) Uij ? ? H(10) 0.759(4) 0.553(3) 0.763(2) 0.053(8) Uij ? ? H(11) 0.682(4) 0.311(4) 0.766(3) 0.066(9) Uij ? ? H(12) 0.830(6) 0.644(5) 0.198(3) 0.11(1) Uij ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0360(3) 0.0362(3) 0.0341(3) -0.0186(2) -0.0096(2) 0.0046(2) S(2) 0.0346(3) 0.0367(3) 0.0286(3) -0.0159(2) -0.0096(2) 0.0019(2) S(3) 0.0332(3) 0.0414(3) 0.0395(3) -0.0123(2) -0.0128(2) -0.0011(2) S(4) 0.0384(3) 0.0489(3) 0.0333(3) -0.0256(3) -0.0021(2) -0.0032(2) O(1) 0.074(1) 0.055(1) 0.0335(9) -0.031(1) -0.0050(9) 0.0101(8) C(1) 0.031(1) 0.040(1) 0.036(1) -0.0186(9) -0.0050(8) -0.0055(9) C(2) 0.030(1) 0.042(1) 0.035(1) -0.0146(9) -0.0099(9) -0.0049(9) C(3) 0.033(1) 0.0313(10) 0.0263(9) -0.0134(8) -0.0073(8) -0.0013(8) C(4) 0.031(1) 0.040(1) 0.0308(10) -0.0155(9) -0.0074(8) -0.0008(8) C(5) 0.035(1) 0.047(1) 0.033(1) -0.019(1) -0.0127(9) 0.0026(9) C(6) 0.037(1) 0.042(1) 0.030(1) -0.0186(10) -0.0104(9) 0.0041(9) C(7) 0.054(2) 0.058(2) 0.041(1) -0.033(1) -0.009(1) 0.008(1) C(8) 0.037(1) 0.044(1) 0.032(1) -0.0095(10) -0.0056(9) 0.0027(9) C(9) 0.040(1) 0.045(1) 0.030(1) -0.018(1) -0.0075(9) 0.0010(9) C(10) 0.082(2) 0.063(2) 0.039(1) -0.044(2) -0.007(1) 0.001(1) C(11) 0.069(2) 0.060(2) 0.058(2) -0.031(2) -0.006(1) -0.016(1) C(12) 0.051(2) 0.062(2) 0.043(1) -0.009(1) -0.009(1) -0.019(1) C(13) 0.060(2) 0.062(2) 0.028(1) -0.010(1) -0.006(1) 0.000(1) C(14) 0.052(1) 0.038(1) 0.037(1) -0.015(1) -0.007(1) 0.0054(10) C(15) 0.141(4) 0.041(2) 0.041(2) -0.033(2) -0.010(2) 0.003(1) #----------------------------------------------------------------------- _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '1/\s^2^(F)' _refine_ls_hydrogen_treatment 'ISOTROPIC' _refine_ls_extinction_method none _refine_ls_number_reflns 3320 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_obs 0.0423 _refine_ls_wR_factor_all 0.0534 _refine_ls_wR_factor_obs 0.0501 _refine_ls_goodness_of_fit_obs 1.586 _refine_ls_shift/esd_max 0.0030 _refine_diff_density_min -0.37 _refine_diff_density_max 0.40 #----------------------------------------------------------------------- _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(1) C(1) 1.743(2) ? ? yes S(1) C(3) 1.750(2) ? ? yes S(2) C(2) 1.739(2) ? ? yes S(2) C(3) 1.750(2) ? ? yes S(3) C(4) 1.761(2) ? ? yes S(3) C(5) 1.826(2) ? ? yes S(4) C(4) 1.772(2) ? ? yes S(4) C(14) 1.690(3) ? ? yes O(1) C(7) 1.453(3) ? ? yes O(1) C(8) 1.367(3) ? ? yes C(1) C(2) 1.325(3) ? ? yes C(3) C(4) 1.352(3) ? ? yes C(5) C(6) 1.525(3) ? ? yes C(6) C(7) 1.532(3) ? ? yes C(6) C(9) 1.510(3) ? ? yes C(8) C(9) 1.379(3) ? ? yes C(8) C(13) 1.387(4) ? ? yes C(9) C(10) 1.373(4) ? ? yes C(10) C(11) 1.393(4) ? ? yes C(11) C(12) 1.383(4) ? ? yes C(12) C(13) 1.369(4) ? ? yes C(14) C(15) 1.167(4) ? ? yes #----------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) S(1) C(3) 95.4(1) ? ? ? yes C(2) S(2) C(3) 95.3(1) ? ? ? yes C(4) S(3) C(5) 102.2(1) ? ? ? yes C(4) S(4) C(14) 102.2(1) ? ? ? yes C(7) O(1) C(8) 107.2(2) ? ? ? yes S(1) C(1) C(2) 117.3(2) ? ? ? yes S(2) C(2) C(1) 117.8(2) ? ? ? yes S(1) C(3) S(2) 114.0(1) ? ? ? yes S(1) C(3) C(4) 122.1(2) ? ? ? yes S(2) C(3) C(4) 123.8(2) ? ? ? yes S(3) C(4) S(4) 120.7(1) ? ? ? yes S(3) C(4) C(3) 120.3(2) ? ? ? yes S(4) C(4) C(3) 118.6(2) ? ? ? yes S(3) C(5) C(6) 114.7(2) ? ? ? yes C(5) C(6) C(7) 113.7(2) ? ? ? yes C(5) C(6) C(9) 110.2(2) ? ? ? yes C(7) C(6) C(9) 101.2(2) ? ? ? yes O(1) C(7) C(6) 107.5(2) ? ? ? yes O(1) C(8) C(9) 113.2(2) ? ? ? yes O(1) C(8) C(13) 124.8(2) ? ? ? yes C(9) C(8) C(13) 122.0(2) ? ? ? yes C(6) C(9) C(8) 108.7(2) ? ? ? yes C(6) C(9) C(10) 131.8(2) ? ? ? yes C(8) C(9) C(10) 119.5(2) ? ? ? yes C(9) C(10) C(11) 119.4(3) ? ? ? yes C(10) C(11) C(12) 120.0(3) ? ? ? yes C(11) C(12) C(13) 121.3(3) ? ? ? yes C(8) C(13) C(12) 117.8(2) ? ? ? yes S(4) C(14) C(15) 174.9(3) ? ? ? yes #----------------------------------------------------------------------- #===END #----------------------------------------------------------------------- #-------------------2nd-CIF-FILE----------------------------------- #----------------------------------------------------------------------- data_m23 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O6 S5' _chemical_formula_weight 573.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _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 8.8511(19) _cell_length_b 9.931(3) _cell_length_c 16.478(4) _cell_angle_alpha 83.20(2) _cell_angle_beta 75.04(2) _cell_angle_gamma 70.00(2) _cell_volume 1314.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 24.26 _cell_measurement_theta_max 24.94 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type 'psi scans' _exptl_absorpt_correction_T_min 0.6856 _exptl_absorpt_correction_T_max 0.8693 _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 'Rigaku AFC7S' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5709 _diffrn_reflns_av_R_equivalents 0.0092 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.54 _reflns_number_total 5381 _reflns_number_gt 4994 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'texsan' _computing_structure_solution 'SAPI/texsan' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP' _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 w=1/[\s^2^(Fo^2^)+(0.0139P)^2^+1.3865P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5381 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.73470(6) -0.26898(6) -0.36168(3) 0.02543(12) Uani 1 d . . . S2 S 0.02870(7) -0.01336(7) -0.34358(4) 0.03802(16) Uani 1 d . . . S3 S 0.02825(6) 0.17368(5) -0.19337(3) 0.02090(11) Uani 1 d . . . S4 S 0.41385(6) 0.11146(5) -0.23060(3) 0.02500(12) Uani 1 d . . . S5 S 0.36874(6) 0.36177(5) -0.13693(3) 0.02494(12) Uani 1 d . . . O1 O 0.89542(18) -0.3009(2) -0.41705(11) 0.0373(4) Uani 1 d . . . O2 O 0.68251(19) -0.16211(17) -0.29997(10) 0.0330(4) Uani 1 d . . . O3 O 0.0128(2) 0.57273(17) -0.22130(9) 0.0319(3) Uani 1 d . . . O4 O -0.09549(19) 0.66009(15) -0.09164(9) 0.0256(3) Uani 1 d . . . O5 O -0.29333(17) 0.46026(17) -0.09617(9) 0.0284(3) Uani 1 d . . . O6 O -0.18152(17) 0.31053(16) 0.00201(9) 0.0274(3) Uani 1 d . . . N1 N 0.6004(2) -0.21651(19) -0.42046(11) 0.0258(4) Uani 1 d . . . C1 C 0.6083(2) -0.2957(2) -0.48942(12) 0.0214(4) Uani 1 d . . . C2 C 0.7409(3) -0.4024(2) -0.53360(14) 0.0291(4) Uani 1 d . . . H2 H 0.8450 -0.4353 -0.5190 0.035 Uiso 1 calc R . . C3 C 0.7153(3) -0.4596(2) -0.60032(13) 0.0282(4) Uani 1 d . . . H3 H 0.8039 -0.5326 -0.6321 0.034 Uiso 1 calc R . . C4 C 0.5645(3) -0.4125(3) -0.62094(14) 0.0333(5) Uani 1 d . . . H4 H 0.5496 -0.4536 -0.6663 0.040 Uiso 1 calc R . . C5 C 0.4331(3) -0.3046(3) -0.57571(16) 0.0465(7) Uani 1 d . . . H5 H 0.3293 -0.2709 -0.5905 0.056 Uiso 1 calc R A 1 C6 C 0.4561(3) -0.2474(3) -0.50920(14) 0.0337(5) Uani 1 d . B 1 C7 C 0.3417(3) -0.1207(3) -0.45401(18) 0.0219(9) Uani 0.723(9) d P B 1 H7 H 0.3527 -0.0308 -0.4855 0.026 Uiso 0.723(9) calc PR B 1 C8 C 0.4228(3) -0.1425(3) -0.38264(16) 0.0372(6) Uani 1 d . B 1 H8A H 0.4071 -0.0496 -0.3598 0.045 Uiso 1 calc R B 1 H8B H 0.3780 -0.2026 -0.3370 0.045 Uiso 1 calc R B 1 C9 C 0.7153(3) -0.4299(3) -0.30995(16) 0.0382(5) Uani 1 d . . . H9A H 0.7918 -0.4643 -0.2726 0.057 Uiso 1 calc R . . H9B H 0.7417 -0.5021 -0.3516 0.057 Uiso 1 calc R . . H9C H 0.6017 -0.4128 -0.2768 0.057 Uiso 1 calc R . . C10 C 0.1634(3) -0.1108(3) -0.43615(16) 0.0353(5) Uani 1 d . B 1 H10A H 0.1575 -0.2093 -0.4299 0.042 Uiso 1 calc R B 1 H10B H 0.1197 -0.0642 -0.4856 0.042 Uiso 1 calc R B 1 C11 C 0.0635(3) 0.1518(2) -0.36170(14) 0.0284(4) Uani 1 d . . . H11 H 0.0868 0.1876 -0.4180 0.034 Uiso 1 calc R . . C12 C 0.0590(2) 0.2299(2) -0.30008(13) 0.0241(4) Uani 1 d . . . H12 H 0.0732 0.3210 -0.3146 0.029 Uiso 1 calc R . . C13 C 0.1087(2) 0.2844(2) -0.15266(12) 0.0194(4) Uani 1 d . . . C14 C 0.2738(2) 0.2560(2) -0.17058(12) 0.0194(4) Uani 1 d . . . C15 C 0.5905(2) 0.1456(2) -0.22432(14) 0.0276(4) Uani 1 d . . . H15 H 0.6975 0.0851 -0.2502 0.033 Uiso 1 calc R . . C16 C 0.5712(2) 0.2588(2) -0.18227(14) 0.0275(4) Uani 1 d . . . H16 H 0.6634 0.2826 -0.1771 0.033 Uiso 1 calc R . . C17 C -0.0055(2) 0.4103(2) -0.09942(11) 0.0180(4) Uani 1 d . . . H17 H 0.0420 0.4106 -0.0506 0.022 Uiso 1 calc R . . C18 C -0.0257(2) 0.5554(2) -0.14657(12) 0.0204(4) Uani 1 d . . . C19 C -0.1329(3) 0.8068(2) -0.12712(14) 0.0333(5) Uani 1 d . . . H19A H -0.2067 0.8225 -0.1658 0.040 Uiso 1 calc R . . H19B H -0.0299 0.8250 -0.1588 0.040 Uiso 1 calc R . . C20 C -0.2158(5) 0.9042(3) -0.05499(18) 0.0579(9) Uani 1 d . . . H20A H -0.3166 0.8841 -0.0238 0.087 Uiso 1 calc R . . H20B H -0.2446 1.0041 -0.0761 0.087 Uiso 1 calc R . . H20C H -0.1408 0.8885 -0.0177 0.087 Uiso 1 calc R . . C21 C -0.1779(2) 0.3985(2) -0.06511(12) 0.0210(4) Uani 1 d . . . C22 C -0.3417(3) 0.2909(3) 0.04072(15) 0.0338(5) Uani 1 d . . . H22A H -0.3675 0.2326 0.0048 0.041 Uiso 1 calc R . . H22B H -0.4305 0.3849 0.0482 0.041 Uiso 1 calc R . . C23 C -0.3281(4) 0.2159(4) 0.1240(2) 0.0579(9) Uani 1 d . . . H23A H -0.2406 0.1227 0.1156 0.087 Uiso 1 calc R . . H23B H -0.4336 0.2015 0.1524 0.087 Uiso 1 calc R . . H23C H -0.3014 0.2743 0.1586 0.087 Uiso 1 calc R . . C24 C 0.3210(9) -0.1902(9) -0.4251(5) 0.021(2) Uiso 0.277(9) d P B 2 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 0.0184(2) 0.0271(3) 0.0302(3) -0.0093(2) -0.00647(19) -0.00318(19) S2 0.0258(3) 0.0431(3) 0.0465(3) -0.0277(3) 0.0106(2) -0.0182(2) S3 0.0207(2) 0.0205(2) 0.0223(2) -0.00485(18) -0.00057(18) -0.00953(18) S4 0.0171(2) 0.0201(2) 0.0348(3) -0.0115(2) 0.00148(19) -0.00438(18) S5 0.0206(2) 0.0238(3) 0.0317(3) -0.0102(2) -0.00401(19) -0.00744(19) O1 0.0188(7) 0.0480(10) 0.0423(9) -0.0137(8) -0.0036(7) -0.0060(7) O2 0.0270(8) 0.0327(9) 0.0400(9) -0.0164(7) -0.0116(7) -0.0025(6) O3 0.0401(9) 0.0281(8) 0.0189(7) -0.0012(6) -0.0010(6) -0.0044(7) O4 0.0380(8) 0.0156(7) 0.0194(7) -0.0030(5) -0.0056(6) -0.0040(6) O5 0.0196(7) 0.0316(8) 0.0310(8) -0.0034(6) -0.0048(6) -0.0047(6) O6 0.0206(7) 0.0273(8) 0.0275(7) 0.0017(6) 0.0026(6) -0.0061(6) N1 0.0193(8) 0.0278(9) 0.0272(9) -0.0109(7) -0.0051(7) -0.0006(7) C1 0.0239(9) 0.0205(9) 0.0184(9) -0.0004(7) -0.0021(7) -0.0076(8) C2 0.0236(10) 0.0291(11) 0.0299(11) -0.0072(9) -0.0012(8) -0.0043(8) C3 0.0312(11) 0.0232(10) 0.0240(10) -0.0056(8) 0.0049(8) -0.0077(8) C4 0.0382(12) 0.0379(13) 0.0232(10) -0.0115(9) -0.0028(9) -0.0114(10) C5 0.0309(12) 0.0668(19) 0.0379(13) -0.0265(13) -0.0123(10) 0.0002(12) C6 0.0249(11) 0.0419(13) 0.0287(11) -0.0151(10) -0.0059(9) 0.0005(9) C7 0.0218(14) 0.0192(16) 0.0235(15) -0.0045(12) -0.0043(11) -0.0045(11) C8 0.0184(10) 0.0472(14) 0.0423(13) -0.0261(11) -0.0064(9) 0.0016(9) C9 0.0460(14) 0.0331(13) 0.0391(13) -0.0015(10) -0.0180(11) -0.0111(11) C10 0.0223(10) 0.0426(13) 0.0407(13) -0.0256(11) -0.0057(9) -0.0035(9) C11 0.0253(10) 0.0311(11) 0.0265(10) -0.0070(9) -0.0051(8) -0.0049(8) C12 0.0255(10) 0.0205(10) 0.0238(10) -0.0010(8) -0.0044(8) -0.0051(8) C13 0.0185(9) 0.0184(9) 0.0203(9) -0.0048(7) -0.0016(7) -0.0057(7) C14 0.0206(9) 0.0159(9) 0.0207(9) -0.0047(7) -0.0024(7) -0.0054(7) C15 0.0157(9) 0.0284(11) 0.0349(11) -0.0042(9) -0.0021(8) -0.0042(8) C16 0.0177(9) 0.0317(11) 0.0340(11) -0.0038(9) -0.0055(8) -0.0085(8) C17 0.0170(8) 0.0179(9) 0.0171(8) -0.0043(7) -0.0016(7) -0.0036(7) C18 0.0191(9) 0.0212(9) 0.0196(9) -0.0039(7) -0.0030(7) -0.0049(7) C19 0.0505(14) 0.0175(10) 0.0288(11) 0.0019(8) -0.0121(10) -0.0061(9) C20 0.101(3) 0.0189(12) 0.0372(14) -0.0051(10) -0.0163(15) 0.0025(13) C21 0.0189(9) 0.0196(9) 0.0208(9) -0.0071(7) 0.0002(7) -0.0032(7) C22 0.0229(10) 0.0318(12) 0.0398(13) -0.0021(10) 0.0067(9) -0.0101(9) C23 0.0426(15) 0.0540(18) 0.0585(18) 0.0246(15) 0.0078(13) -0.0155(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 O1 1.4305(17) . ? S1 O2 1.4323(16) . ? S1 N1 1.6354(18) . ? S1 C9 1.760(3) . ? S2 C11 1.749(2) . ? S2 C10 1.818(2) . ? S3 C12 1.761(2) . ? S3 C13 1.7674(19) . ? S4 C15 1.739(2) . ? S4 C14 1.750(2) . ? S5 C16 1.747(2) . ? S5 C14 1.7600(19) . ? O3 C18 1.198(2) . ? O4 C18 1.333(2) . ? O4 C19 1.464(2) . ? O5 C21 1.204(2) . ? O6 C21 1.326(2) . ? O6 C22 1.465(2) . ? N1 C1 1.431(3) . ? N1 C8 1.487(3) . ? C1 C6 1.378(3) . ? C1 C2 1.386(3) . ? C2 C3 1.396(3) . ? C3 C4 1.373(3) . ? C4 C5 1.395(3) . ? C5 C6 1.380(3) . ? C6 C7 1.536(3) . ? C7 C8 1.488(4) . ? C7 C10 1.499(3) . ? C11 C12 1.333(3) . ? C13 C14 1.348(3) . ? C13 C17 1.513(3) . ? C15 C16 1.328(3) . ? C17 C21 1.525(3) . ? C17 C18 1.531(3) . ? C19 C20 1.491(3) . ? C22 C23 1.494(4) . ? 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 O1 S1 O2 120.02(10) . . ? O1 S1 N1 107.05(10) . . ? O2 S1 N1 106.17(9) . . ? O1 S1 C9 108.05(12) . . ? O2 S1 C9 108.30(12) . . ? N1 S1 C9 106.51(11) . . ? C11 S2 C10 102.20(12) . . ? C12 S3 C13 101.01(10) . . ? C15 S4 C14 95.69(10) . . ? C16 S5 C14 95.63(10) . . ? C18 O4 C19 116.31(16) . . ? C21 O6 C22 115.77(17) . . ? C1 N1 C8 107.52(16) . . ? C1 N1 S1 123.50(14) . . ? C8 N1 S1 120.24(15) . . ? C6 C1 C2 122.18(19) . . ? C6 C1 N1 108.57(17) . . ? C2 C1 N1 129.24(19) . . ? C1 C2 C3 117.3(2) . . ? C4 C3 C2 121.2(2) . . ? C3 C4 C5 120.4(2) . . ? C6 C5 C4 119.1(2) . . ? C1 C6 C5 119.8(2) . . ? C1 C6 C7 109.22(19) . . ? C5 C6 C7 130.7(2) . . ? C8 C7 C10 119.1(2) . . ? C8 C7 C6 101.8(2) . . ? C10 C7 C6 112.6(2) . . ? N1 C8 C7 103.94(19) . . ? C7 C10 S2 116.21(17) . . ? C12 C11 S2 122.99(18) . . ? C11 C12 S3 123.73(17) . . ? C14 C13 C17 120.34(17) . . ? C14 C13 S3 118.90(15) . . ? C17 C13 S3 120.75(13) . . ? C13 C14 S4 123.05(15) . . ? C13 C14 S5 123.28(15) . . ? S4 C14 S5 113.67(11) . . ? C16 C15 S4 117.96(16) . . ? C15 C16 S5 117.04(16) . . ? C13 C17 C21 111.84(15) . . ? C13 C17 C18 113.48(15) . . ? C21 C17 C18 107.27(15) . . ? O3 C18 O4 125.12(19) . . ? O3 C18 C17 125.44(18) . . ? O4 C18 C17 109.42(15) . . ? O4 C19 C20 106.77(18) . . ? O5 C21 O6 125.41(18) . . ? O5 C21 C17 123.75(18) . . ? O6 C21 C17 110.83(16) . . ? O6 C22 C23 106.8(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 O1 S1 N1 C1 51.29(19) . . . . ? O2 S1 N1 C1 -179.37(16) . . . . ? C9 S1 N1 C1 -64.1(2) . . . . ? O1 S1 N1 C8 -165.22(18) . . . . ? O2 S1 N1 C8 -35.9(2) . . . . ? C9 S1 N1 C8 79.4(2) . . . . ? C8 N1 C1 C6 15.0(2) . . . . ? S1 N1 C1 C6 162.37(17) . . . . ? C8 N1 C1 C2 -166.0(2) . . . . ? S1 N1 C1 C2 -18.6(3) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? N1 C1 C2 C3 -178.4(2) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -1.0(4) . . . . ? C2 C1 C6 C5 -0.9(4) . . . . ? N1 C1 C6 C5 178.2(2) . . . . ? C2 C1 C6 C7 -175.0(2) . . . . ? N1 C1 C6 C7 4.1(3) . . . . ? C4 C5 C6 C1 1.1(4) . . . . ? C4 C5 C6 C7 173.8(3) . . . . ? C1 C6 C7 C8 -21.0(3) . . . . ? C5 C6 C7 C8 165.7(3) . . . . ? C1 C6 C7 C10 -149.7(2) . . . . ? C5 C6 C7 C10 37.0(4) . . . . ? C1 N1 C8 C7 -28.1(3) . . . . ? S1 N1 C8 C7 -176.74(18) . . . . ? C10 C7 C8 N1 153.1(2) . . . . ? C6 C7 C8 N1 28.6(3) . . . . ? C8 C7 C10 S2 38.8(3) . . . . ? C6 C7 C10 S2 157.85(19) . . . . ? C11 S2 C10 C7 54.6(2) . . . . ? C10 S2 C11 C12 -146.95(19) . . . . ? S2 C11 C12 S3 3.4(3) . . . . ? C13 S3 C12 C11 159.56(18) . . . . ? C12 S3 C13 C14 -73.29(18) . . . . ? C12 S3 C13 C17 105.96(16) . . . . ? C17 C13 C14 S4 179.23(14) . . . . ? S3 C13 C14 S4 -1.5(2) . . . . ? C17 C13 C14 S5 -1.5(3) . . . . ? S3 C13 C14 S5 177.73(11) . . . . ? C15 S4 C14 C13 -179.36(18) . . . . ? C15 S4 C14 S5 1.32(13) . . . . ? C16 S5 C14 C13 179.48(18) . . . . ? C16 S5 C14 S4 -1.21(13) . . . . ? C14 S4 C15 C16 -1.0(2) . . . . ? S4 C15 C16 S5 0.3(3) . . . . ? C14 S5 C16 C15 0.6(2) . . . . ? C14 C13 C17 C21 -163.05(18) . . . . ? S3 C13 C17 C21 17.7(2) . . . . ? C14 C13 C17 C18 75.4(2) . . . . ? S3 C13 C17 C18 -103.80(17) . . . . ? C19 O4 C18 O3 2.6(3) . . . . ? C19 O4 C18 C17 -176.39(17) . . . . ? C13 C17 C18 O3 15.1(3) . . . . ? C21 C17 C18 O3 -109.0(2) . . . . ? C13 C17 C18 O4 -165.97(15) . . . . ? C21 C17 C18 O4 69.99(19) . . . . ? C18 O4 C19 C20 177.6(2) . . . . ? C22 O6 C21 O5 -0.9(3) . . . . ? C22 O6 C21 C17 179.87(16) . . . . ? C13 C17 C21 O5 -98.8(2) . . . . ? C18 C17 C21 O5 26.2(2) . . . . ? C13 C17 C21 O6 80.4(2) . . . . ? C18 C17 C21 O6 -154.53(16) . . . . ? C21 O6 C22 C23 -167.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.54 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.582 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.060 #===END