# 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 loop_ _publ_author_name _publ_author_address 'Sung Yang.' ;College of Environment and Applied Chemistry, Kyung Hee University, Yongin, 449-701, Republic of Korea ; 'Kwang-Hyun Ahn.' '' 'Yong-Chul Jeong.' '' 'Eunkyoung Kim.' '' ; Dae-Gue Park ; '' _publ_contact_author_name 'Sung Yang' _publ_contact_author_address ; College of Environment and Applied Chemistry Kyung Hee University 1 Seochun-dong Yongin 449-701 SOUTH KOREA ; _publ_contact_author_email SIYANG@KHU.AC.KR _publ_section_title ; Fatigue-resistant photochromic dithienylethenes by controlling the oxidation state ; _publ_contact_author_fax 82-31-202-7337 _publ_contact_author_phone 82-31-201-3735 data_f6 _database_code_depnum_ccdc_archive 'CCDC 297166' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H14 F6 O2 S2' _chemical_formula_weight 500.46 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' 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' _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 8.1239(14) _cell_length_b 10.7442(19) _cell_length_c 13.125(2) _cell_angle_alpha 86.419(15) _cell_angle_beta 76.057(13) _cell_angle_gamma 74.297(13) _cell_volume 1070.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 12.32 _exptl_crystal_description 'BLOCK ' _exptl_crystal_colour 'COLORLESS ' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6710 _exptl_absorpt_correction_T_max 0.9051 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4004 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3714 _reflns_number_gt 1976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0534P)^2^+1.7038P] 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 0.0051(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3714 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1469 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.1782 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.3993(2) 0.74058(16) 0.96685(13) 0.0629(5) Uani 1 1 d . . . S2 S 0.2095(2) 1.02268(15) 0.58237(12) 0.0660(5) Uani 1 1 d . . . O1 O 0.4785(6) 0.8429(4) 0.9237(4) 0.0807(14) Uani 1 1 d . . . O2 O 0.4746(6) 0.6589(5) 1.0432(4) 0.0915(15) Uani 1 1 d . . . F1 F 0.2898(7) 0.3942(4) 0.7924(5) 0.139(2) Uani 1 1 d . . . F2 F 0.0157(7) 0.4670(4) 0.8524(3) 0.1190(18) Uani 1 1 d . . . F3 F 0.2300(11) 0.3712(5) 0.6159(4) 0.195(4) Uani 1 1 d . . . F4 F -0.0342(9) 0.4232(6) 0.6868(5) 0.168(3) Uani 1 1 d . . . F5 F 0.2041(6) 0.5790(4) 0.5191(3) 0.1025(15) Uani 1 1 d . . . F6 F -0.0678(6) 0.6320(4) 0.5965(4) 0.1085(16) Uani 1 1 d . . . C1 C 0.5597(10) 0.5735(10) 0.7936(7) 0.080(2) Uani 1 1 d . . . C2 C 0.3910(8) 0.6503(6) 0.8604(5) 0.0591(16) Uani 1 1 d . . . C3 C 0.1708(7) 0.7954(5) 1.0082(4) 0.0507(14) Uani 1 1 d . . . C4 C 0.0724(10) 0.8724(6) 1.0943(5) 0.0653(18) Uani 1 1 d . . . C5 C -0.1081(10) 0.9029(7) 1.1126(5) 0.0655(17) Uani 1 1 d . . . H5 H -0.180(8) 0.968(6) 1.167(5) 0.075(19) Uiso 1 1 d . . . C6 C -0.1872(9) 0.8576(6) 1.0464(5) 0.0617(16) Uani 1 1 d . . . H6 H -0.312(8) 0.880(6) 1.056(4) 0.073(19) Uiso 1 1 d . . . C7 C -0.0894(8) 0.7819(5) 0.9601(5) 0.0524(15) Uani 1 1 d . . . C8 C 0.0919(7) 0.7500(5) 0.9402(4) 0.0448(13) Uani 1 1 d . . . C9 C 0.2225(7) 0.6698(5) 0.8550(4) 0.0462(13) Uani 1 1 d . . . C10 C 0.1714(6) 0.6174(5) 0.7693(4) 0.0423(12) Uani 1 1 d . . . C11 C 0.1543(9) 0.4804(6) 0.7733(5) 0.0621(16) Uani 1 1 d . . . C12 C 0.1144(9) 0.4608(6) 0.6698(5) 0.0652(17) Uani 1 1 d . . . C13 C 0.0944(8) 0.5898(5) 0.6136(4) 0.0559(15) Uani 1 1 d . . . C14 C 0.1300(6) 0.6793(5) 0.6842(4) 0.0425(12) Uani 1 1 d . . . C15 C 0.1217(7) 0.8160(5) 0.6556(4) 0.0433(13) Uani 1 1 d . . . C16 C -0.0402(7) 0.9167(5) 0.6714(4) 0.0449(13) Uani 1 1 d . . . C17 C -0.2112(8) 0.9124(6) 0.7179(5) 0.0554(15) Uani 1 1 d . . . H17 H -0.234(7) 0.840(6) 0.742(4) 0.064(19) Uiso 1 1 d . . . C18 C -0.3460(10) 1.0225(7) 0.7267(5) 0.0709(19) Uani 1 1 d . . . C19 C -0.3130(13) 1.1389(7) 0.6894(6) 0.079(2) Uani 1 1 d . . . C20 C -0.1487(12) 1.1474(7) 0.6429(5) 0.0681(18) Uani 1 1 d . . . C21 C -0.0128(8) 1.0370(5) 0.6349(4) 0.0491(14) Uani 1 1 d . . . C22 C 0.2646(8) 0.8589(5) 0.6085(4) 0.0531(15) Uani 1 1 d . . . C23 C 0.4526(10) 0.7841(9) 0.5744(8) 0.079(2) Uani 1 1 d . . . H7 H -0.146(7) 0.753(5) 0.918(4) 0.054(16) Uiso 1 1 d . . . H19 H -0.406(7) 1.207(6) 0.697(4) 0.054(17) Uiso 1 1 d . . . H4 H 0.132(7) 0.902(5) 1.135(4) 0.070(18) Uiso 1 1 d . . . H18 H -0.459(8) 1.019(6) 0.752(5) 0.06(2) Uiso 1 1 d . . . H20 H -0.130(9) 1.233(7) 0.619(5) 0.10(2) Uiso 1 1 d . . . H23A H 0.519(13) 0.803(9) 0.504(8) 0.17(4) Uiso 1 1 d . . . H1B H 0.527(11) 0.526(8) 0.727(7) 0.16(4) Uiso 1 1 d . . . H23B H 0.467(8) 0.689(7) 0.586(5) 0.09(2) Uiso 1 1 d . . . H1A H 0.618(10) 0.636(7) 0.768(6) 0.11(3) Uiso 1 1 d . . . H23C H 0.514(10) 0.799(7) 0.616(6) 0.10(3) Uiso 1 1 d . . . H1C H 0.616(10) 0.520(7) 0.828(6) 0.10(3) 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 0.0588(10) 0.0768(11) 0.0669(10) 0.0121(8) -0.0336(8) -0.0271(9) S2 0.0898(13) 0.0630(10) 0.0560(10) 0.0113(7) -0.0157(9) -0.0420(9) O1 0.073(3) 0.085(3) 0.103(4) 0.011(3) -0.029(3) -0.047(3) O2 0.094(4) 0.106(4) 0.094(4) 0.026(3) -0.066(3) -0.026(3) F1 0.161(5) 0.048(2) 0.244(6) 0.021(3) -0.144(5) -0.008(3) F2 0.184(5) 0.103(3) 0.086(3) 0.006(2) 0.003(3) -0.096(3) F3 0.322(9) 0.083(3) 0.084(3) -0.027(3) -0.016(4) 0.085(5) F4 0.225(7) 0.201(6) 0.163(5) 0.078(5) -0.111(5) -0.159(6) F5 0.167(4) 0.100(3) 0.045(2) -0.019(2) 0.002(2) -0.063(3) F6 0.120(4) 0.074(3) 0.159(4) -0.024(3) -0.097(3) -0.010(2) C1 0.053(5) 0.089(6) 0.092(6) 0.014(5) -0.015(4) -0.010(4) C2 0.053(4) 0.064(4) 0.060(4) 0.012(3) -0.020(3) -0.013(3) C3 0.057(4) 0.062(4) 0.041(3) 0.005(3) -0.020(3) -0.023(3) C4 0.082(5) 0.080(5) 0.049(4) 0.003(3) -0.029(4) -0.035(4) C5 0.077(5) 0.072(4) 0.048(4) -0.012(3) -0.010(3) -0.022(4) C6 0.054(4) 0.070(4) 0.058(4) -0.003(3) -0.004(3) -0.018(3) C7 0.059(4) 0.055(4) 0.052(4) 0.005(3) -0.023(3) -0.021(3) C8 0.050(3) 0.047(3) 0.046(3) 0.012(3) -0.021(3) -0.021(3) C9 0.054(4) 0.047(3) 0.042(3) 0.011(2) -0.018(3) -0.018(3) C10 0.043(3) 0.039(3) 0.044(3) 0.000(2) -0.011(2) -0.009(2) C11 0.068(4) 0.047(3) 0.075(4) 0.005(3) -0.025(4) -0.016(3) C12 0.076(5) 0.053(4) 0.069(4) -0.018(3) -0.017(4) -0.017(3) C13 0.065(4) 0.054(4) 0.050(4) -0.003(3) -0.017(3) -0.015(3) C14 0.042(3) 0.040(3) 0.044(3) -0.003(2) -0.010(2) -0.008(2) C15 0.054(3) 0.044(3) 0.035(3) 0.001(2) -0.013(2) -0.016(3) C16 0.058(4) 0.046(3) 0.032(3) 0.000(2) -0.016(3) -0.010(3) C17 0.056(4) 0.056(4) 0.054(4) 0.005(3) -0.014(3) -0.014(4) C18 0.062(5) 0.074(5) 0.068(4) -0.007(4) -0.014(4) -0.002(4) C19 0.098(7) 0.055(5) 0.075(5) -0.009(4) -0.039(5) 0.015(5) C20 0.100(6) 0.055(4) 0.053(4) 0.004(3) -0.028(4) -0.018(4) C21 0.080(4) 0.041(3) 0.031(3) 0.004(2) -0.018(3) -0.019(3) C22 0.061(4) 0.059(4) 0.044(3) 0.005(3) -0.013(3) -0.026(3) C23 0.052(5) 0.087(6) 0.095(6) 0.009(5) -0.012(4) -0.021(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 S1 O2 1.430(4) . ? S1 O1 1.440(4) . ? S1 C3 1.746(6) . ? S1 C2 1.774(6) . ? S2 C22 1.728(6) . ? S2 C21 1.738(6) . ? F1 C11 1.298(7) . ? F2 C11 1.368(7) . ? F3 C12 1.259(7) . ? F4 C12 1.339(7) . ? F5 C13 1.333(6) . ? F6 C13 1.341(7) . ? C1 C2 1.493(10) . ? C2 C9 1.346(7) . ? C3 C4 1.387(8) . ? C3 C8 1.395(7) . ? C4 C5 1.376(9) . ? C5 C6 1.377(9) . ? C6 C7 1.381(8) . ? C7 C8 1.381(7) . ? C8 C9 1.474(7) . ? C9 C10 1.478(7) . ? C10 C14 1.330(7) . ? C10 C11 1.512(7) . ? C11 C12 1.510(8) . ? C12 C13 1.517(8) . ? C13 C14 1.503(7) . ? C14 C15 1.481(7) . ? C15 C22 1.361(7) . ? C15 C16 1.438(7) . ? C16 C17 1.388(8) . ? C16 C21 1.406(7) . ? C17 C18 1.367(9) . ? C18 C19 1.384(10) . ? C19 C20 1.353(10) . ? C20 C21 1.374(8) . ? C22 C23 1.493(9) . ? 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 O2 S1 O1 117.1(3) . . ? O2 S1 C3 111.9(3) . . ? O1 S1 C3 112.2(3) . . ? O2 S1 C2 111.8(3) . . ? O1 S1 C2 107.7(3) . . ? C3 S1 C2 93.6(3) . . ? C22 S2 C21 92.1(3) . . ? C9 C2 C1 132.0(6) . . ? C9 C2 S1 109.4(4) . . ? C1 C2 S1 118.6(5) . . ? C4 C3 C8 121.8(6) . . ? C4 C3 S1 128.3(5) . . ? C8 C3 S1 109.9(4) . . ? C5 C4 C3 118.3(6) . . ? C4 C5 C6 120.3(6) . . ? C5 C6 C7 121.5(6) . . ? C8 C7 C6 119.2(6) . . ? C7 C8 C3 118.8(5) . . ? C7 C8 C9 129.0(5) . . ? C3 C8 C9 112.1(5) . . ? C2 C9 C8 114.8(5) . . ? C2 C9 C10 122.9(5) . . ? C8 C9 C10 122.3(5) . . ? C14 C10 C9 127.3(5) . . ? C14 C10 C11 111.7(5) . . ? C9 C10 C11 120.9(4) . . ? F1 C11 F2 105.1(5) . . ? F1 C11 C12 113.7(6) . . ? F2 C11 C12 108.4(5) . . ? F1 C11 C10 114.0(5) . . ? F2 C11 C10 110.7(5) . . ? C12 C11 C10 104.9(5) . . ? F3 C12 F4 104.8(6) . . ? F3 C12 C11 112.6(6) . . ? F4 C12 C11 109.8(6) . . ? F3 C12 C13 112.4(6) . . ? F4 C12 C13 110.8(6) . . ? C11 C12 C13 106.5(5) . . ? F5 C13 F6 105.8(5) . . ? F5 C13 C14 112.0(5) . . ? F6 C13 C14 112.1(5) . . ? F5 C13 C12 111.4(5) . . ? F6 C13 C12 110.0(5) . . ? C14 C13 C12 105.7(4) . . ? C10 C14 C15 127.7(5) . . ? C10 C14 C13 110.8(5) . . ? C15 C14 C13 121.5(4) . . ? C22 C15 C16 112.9(5) . . ? C22 C15 C14 123.8(5) . . ? C16 C15 C14 123.2(5) . . ? C17 C16 C21 117.7(5) . . ? C17 C16 C15 130.3(5) . . ? C21 C16 C15 112.0(5) . . ? C18 C17 C16 120.1(7) . . ? C17 C18 C19 120.3(8) . . ? C20 C19 C18 121.6(7) . . ? C19 C20 C21 118.2(7) . . ? C20 C21 C16 122.1(6) . . ? C20 C21 S2 127.2(5) . . ? C16 C21 S2 110.6(4) . . ? C15 C22 C23 129.1(6) . . ? C15 C22 S2 112.3(4) . . ? C23 C22 S2 118.5(5) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.433 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.058 # Attachment 'DMTFO2.cif' data_x _database_code_depnum_ccdc_archive 'CCDC 297167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 F6 O2 S2' _chemical_formula_weight 428.40 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.078(3) _cell_length_b 6.433(2) _cell_length_c 22.410(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.828(17) _cell_angle_gamma 90.00 _cell_volume 1814.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 44 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 12.53 _exptl_crystal_description block _exptl_crystal_colour dark_red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2935 _exptl_absorpt_correction_T_max 0.3421 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4413 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3419 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1385P)^2^+5.6194P] 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 0.005(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3419 _refine_ls_number_parameters 245 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.2943 _refine_ls_wR_factor_gt 0.2718 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.109 _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 S1 S 0.05757(12) 0.9676(3) 0.38796(7) 0.0540(5) Uani 1 1 d . . . S2 S 0.19497(13) 0.9981(3) 0.15296(7) 0.0601(5) Uani 1 1 d . . . F1 F 0.3846(5) 0.5453(12) 0.4479(3) 0.150(3) Uani 1 1 d . . . F2 F 0.4573(6) 0.8305(12) 0.4662(3) 0.183(4) Uani 1 1 d . . . F3 F 0.5228(17) 0.443(2) 0.4096(5) 0.422(15) Uani 1 1 d D . . F4 F 0.5892(4) 0.702(4) 0.4158(4) 0.401(15) Uani 1 1 d D . . F5 F 0.5332(3) 0.7403(12) 0.3027(3) 0.149(3) Uani 1 1 d . . . F6 F 0.4550(5) 0.4542(9) 0.3027(3) 0.129(2) Uani 1 1 d . . . O1 O 0.0113(4) 0.8446(8) 0.4269(2) 0.0760(14) Uani 1 1 d . . . O2 O -0.0117(4) 1.0855(10) 0.3394(2) 0.0863(17) Uani 1 1 d . . . C1 C 0.1333(7) 1.3015(11) 0.4703(3) 0.075(2) Uani 1 1 d . . . H1A H 0.1976 1.3719 0.4916 0.113 Uiso 1 1 calc R . . H1B H 0.0995 1.2472 0.5000 0.113 Uiso 1 1 calc R . . H1C H 0.0863 1.3976 0.4433 0.113 Uiso 1 1 calc R . . C2 C 0.1592(5) 1.1252(9) 0.4323(3) 0.0524(14) Uani 1 1 d . . . C3 C 0.2499(5) 1.0625(9) 0.4243(3) 0.0543(14) Uani 1 1 d . . . H3A H 0.3143 1.1252 0.4441 0.065 Uiso 1 1 calc R . . C4 C 0.2423(4) 0.8831(9) 0.3810(2) 0.0454(12) Uani 1 1 d . . . C5 C 0.1435(4) 0.8120(9) 0.3573(2) 0.0461(12) Uani 1 1 d . . . C6 C 0.0985(5) 0.6446(11) 0.3137(3) 0.0655(17) Uani 1 1 d . . . H6A H 0.1545 0.5752 0.3014 0.098 Uiso 1 1 calc R . . H6B H 0.0488 0.7020 0.2777 0.098 Uiso 1 1 calc R . . H6C H 0.0625 0.5469 0.3333 0.098 Uiso 1 1 calc R . . C7 C 0.3371(4) 0.7938(9) 0.3684(2) 0.0452(12) Uani 1 1 d . . . C8 C 0.4233(5) 0.7097(12) 0.4215(3) 0.0643(17) Uani 1 1 d . . . C9 C 0.5026(6) 0.6230(16) 0.3937(3) 0.093(3) Uani 1 1 d D . . C10 C 0.4649(5) 0.6458(11) 0.3261(3) 0.0576(15) Uani 1 1 d . . . C11 C 0.3605(4) 0.7589(8) 0.3137(2) 0.0422(11) Uani 1 1 d . . . C12 C 0.3018(4) 0.8141(8) 0.2500(2) 0.0436(12) Uani 1 1 d . . . C13 C 0.3032(4) 0.6830(9) 0.1982(3) 0.0509(13) Uani 1 1 d . . . H13A H 0.3392 0.5568 0.2022 0.061 Uiso 1 1 calc R . . C14 C 0.2474(5) 0.7611(10) 0.1433(3) 0.0553(14) Uani 1 1 d . . . C15 C 0.2268(6) 0.6655(14) 0.0799(3) 0.077(2) Uani 1 1 d . . . H15A H 0.2619 0.5333 0.0831 0.115 Uiso 1 1 calc R . . H15B H 0.2536 0.7556 0.0535 0.115 Uiso 1 1 calc R . . H15C H 0.1517 0.6466 0.0626 0.115 Uiso 1 1 calc R . . C16 C 0.2463(4) 0.9937(9) 0.2318(3) 0.0501(13) Uani 1 1 d . . . C17 C 0.2289(7) 1.1765(10) 0.2685(3) 0.0721(19) Uani 1 1 d . . . H17A H 0.2622 1.1522 0.3117 0.108 Uiso 1 1 calc R . . H17B H 0.1541 1.1973 0.2623 0.108 Uiso 1 1 calc R . . H17C H 0.2593 1.2980 0.2552 0.108 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 0.0503(8) 0.0696(10) 0.0465(8) -0.0057(7) 0.0203(7) 0.0082(7) S2 0.0586(10) 0.0693(10) 0.0529(9) 0.0155(7) 0.0161(8) 0.0067(7) F1 0.100(4) 0.218(7) 0.131(5) 0.111(5) 0.029(4) 0.012(4) F2 0.159(6) 0.199(7) 0.121(5) -0.100(5) -0.081(4) 0.102(5) F3 0.79(3) 0.404(18) 0.151(8) 0.180(10) 0.264(14) 0.49(2) F4 0.047(3) 1.05(4) 0.104(5) -0.177(14) 0.018(3) -0.074(9) F5 0.059(2) 0.234(7) 0.174(5) 0.129(6) 0.064(3) 0.045(4) F6 0.115(4) 0.115(4) 0.126(4) -0.049(3) -0.021(3) 0.066(3) O1 0.073(3) 0.092(3) 0.079(3) -0.008(3) 0.047(3) -0.010(3) O2 0.075(3) 0.115(4) 0.064(3) 0.002(3) 0.011(3) 0.044(3) C1 0.098(5) 0.067(4) 0.073(4) -0.015(4) 0.044(4) 0.006(4) C2 0.066(4) 0.051(3) 0.045(3) -0.004(2) 0.026(3) 0.001(3) C3 0.061(3) 0.058(3) 0.046(3) -0.012(3) 0.018(3) -0.008(3) C4 0.049(3) 0.052(3) 0.036(3) -0.003(2) 0.014(2) 0.002(2) C5 0.048(3) 0.056(3) 0.037(3) -0.006(2) 0.016(2) 0.001(2) C6 0.056(3) 0.078(4) 0.065(4) -0.025(3) 0.020(3) -0.008(3) C7 0.041(3) 0.050(3) 0.047(3) -0.007(2) 0.015(2) -0.002(2) C8 0.062(4) 0.092(5) 0.036(3) -0.005(3) 0.007(3) 0.014(3) C9 0.060(4) 0.153(9) 0.057(4) 0.013(5) 0.003(3) 0.053(5) C10 0.049(3) 0.076(4) 0.052(3) 0.004(3) 0.022(3) 0.010(3) C11 0.040(2) 0.046(3) 0.042(3) 0.000(2) 0.013(2) -0.004(2) C12 0.042(3) 0.051(3) 0.041(3) 0.004(2) 0.016(2) 0.002(2) C13 0.050(3) 0.057(3) 0.047(3) 0.002(2) 0.016(3) 0.002(3) C14 0.052(3) 0.070(4) 0.046(3) 0.004(3) 0.016(3) -0.003(3) C15 0.080(5) 0.105(6) 0.043(3) -0.011(4) 0.012(3) -0.016(4) C16 0.046(3) 0.056(3) 0.050(3) 0.006(3) 0.017(3) -0.001(2) C17 0.104(5) 0.044(3) 0.078(5) 0.011(3) 0.040(4) 0.012(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 S1 O1 1.429(5) . ? S1 O2 1.429(5) . ? S1 C2 1.750(6) . ? S1 C5 1.777(5) . ? S2 C14 1.709(7) . ? S2 C16 1.710(6) . ? F1 C8 1.374(9) . ? F2 C8 1.251(8) . ? F3 C9 1.219(12) . ? F4 C9 1.218(11) . ? F5 C10 1.303(7) . ? F6 C10 1.331(8) . ? C1 C2 1.511(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.312(8) . ? C3 C4 1.492(8) . ? C3 H3A 0.9300 . ? C4 C5 1.337(8) . ? C4 C7 1.463(7) . ? C5 C6 1.466(8) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C11 1.361(7) . ? C7 C8 1.500(8) . ? C8 C9 1.457(9) . ? C9 C10 1.467(9) . ? C10 C11 1.505(8) . ? C11 C12 1.468(7) . ? C12 C16 1.367(8) . ? C12 C13 1.439(8) . ? C13 C14 1.344(8) . ? C13 H13A 0.9300 . ? C14 C15 1.504(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.488(8) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 118.2(3) . . ? O1 S1 C2 110.9(3) . . ? O2 S1 C2 110.5(4) . . ? O1 S1 C5 110.0(3) . . ? O2 S1 C5 109.9(3) . . ? C2 S1 C5 94.8(3) . . ? C14 S2 C16 93.3(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 131.2(6) . . ? C3 C2 S1 108.6(4) . . ? C1 C2 S1 120.2(5) . . ? C2 C3 C4 115.1(6) . . ? C2 C3 H3A 122.5 . . ? C4 C3 H3A 122.5 . . ? C5 C4 C7 124.5(5) . . ? C5 C4 C3 114.2(5) . . ? C7 C4 C3 121.3(5) . . ? C4 C5 C6 133.3(5) . . ? C4 C5 S1 107.3(4) . . ? C6 C5 S1 119.4(4) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C11 C7 C4 130.6(5) . . ? C11 C7 C8 110.5(5) . . ? C4 C7 C8 118.8(5) . . ? F2 C8 F1 103.0(7) . . ? F2 C8 C9 116.2(7) . . ? F1 C8 C9 106.2(7) . . ? F2 C8 C7 116.0(6) . . ? F1 C8 C7 109.5(6) . . ? C9 C8 C7 105.5(5) . . ? F4 C9 F3 100.1(14) . . ? F4 C9 C8 110.9(9) . . ? F3 C9 C8 111.2(9) . . ? F4 C9 C10 113.0(9) . . ? F3 C9 C10 112.5(9) . . ? C8 C9 C10 109.0(5) . . ? F5 C10 F6 106.1(6) . . ? F5 C10 C9 112.8(7) . . ? F6 C10 C9 106.4(6) . . ? F5 C10 C11 112.8(5) . . ? F6 C10 C11 112.9(5) . . ? C9 C10 C11 105.8(5) . . ? C7 C11 C12 130.6(5) . . ? C7 C11 C10 109.2(5) . . ? C12 C11 C10 120.3(4) . . ? C16 C12 C13 112.2(5) . . ? C16 C12 C11 126.0(5) . . ? C13 C12 C11 121.7(5) . . ? C14 C13 C12 113.3(5) . . ? C14 C13 H13A 123.4 . . ? C12 C13 H13A 123.4 . . ? C13 C14 C15 128.6(6) . . ? C13 C14 S2 110.8(5) . . ? C15 C14 S2 120.6(5) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 130.7(6) . . ? C12 C16 S2 110.4(4) . . ? C17 C16 S2 118.8(5) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C2 C3 113.3(5) . . . . ? O2 S1 C2 C3 -113.6(5) . . . . ? C5 S1 C2 C3 -0.3(5) . . . . ? O1 S1 C2 C1 -67.8(6) . . . . ? O2 S1 C2 C1 65.2(6) . . . . ? C5 S1 C2 C1 178.6(5) . . . . ? C1 C2 C3 C4 -178.2(6) . . . . ? S1 C2 C3 C4 0.5(7) . . . . ? C2 C3 C4 C5 -0.5(8) . . . . ? C2 C3 C4 C7 -178.9(5) . . . . ? C7 C4 C5 C6 -2.2(10) . . . . ? C3 C4 C5 C6 179.4(6) . . . . ? C7 C4 C5 S1 178.6(4) . . . . ? C3 C4 C5 S1 0.2(6) . . . . ? O1 S1 C5 C4 -114.3(4) . . . . ? O2 S1 C5 C4 113.9(5) . . . . ? C2 S1 C5 C4 0.0(4) . . . . ? O1 S1 C5 C6 66.4(6) . . . . ? O2 S1 C5 C6 -65.5(6) . . . . ? C2 S1 C5 C6 -179.3(5) . . . . ? C5 C4 C7 C11 55.7(9) . . . . ? C3 C4 C7 C11 -126.1(6) . . . . ? C5 C4 C7 C8 -119.5(7) . . . . ? C3 C4 C7 C8 58.7(8) . . . . ? C11 C7 C8 F2 131.1(8) . . . . ? C4 C7 C8 F2 -52.8(10) . . . . ? C11 C7 C8 F1 -113.0(6) . . . . ? C4 C7 C8 F1 63.1(8) . . . . ? C11 C7 C8 C9 0.9(8) . . . . ? C4 C7 C8 C9 177.0(6) . . . . ? F2 C8 C9 F4 -7.0(14) . . . . ? F1 C8 C9 F4 -120.8(12) . . . . ? C7 C8 C9 F4 123.1(11) . . . . ? F2 C8 C9 F3 103.5(14) . . . . ? F1 C8 C9 F3 -10.4(13) . . . . ? C7 C8 C9 F3 -126.5(12) . . . . ? F2 C8 C9 C10 -132.0(8) . . . . ? F1 C8 C9 C10 114.2(8) . . . . ? C7 C8 C9 C10 -2.0(9) . . . . ? F4 C9 C10 F5 2.2(14) . . . . ? F3 C9 C10 F5 -110.2(13) . . . . ? C8 C9 C10 F5 126.0(8) . . . . ? F4 C9 C10 F6 118.2(12) . . . . ? F3 C9 C10 F6 5.8(13) . . . . ? C8 C9 C10 F6 -118.0(8) . . . . ? F4 C9 C10 C11 -121.5(12) . . . . ? F3 C9 C10 C11 126.1(12) . . . . ? C8 C9 C10 C11 2.3(9) . . . . ? C4 C7 C11 C12 5.3(10) . . . . ? C8 C7 C11 C12 -179.2(6) . . . . ? C4 C7 C11 C10 -175.0(6) . . . . ? C8 C7 C11 C10 0.5(7) . . . . ? F5 C10 C11 C7 -125.5(6) . . . . ? F6 C10 C11 C7 114.2(6) . . . . ? C9 C10 C11 C7 -1.7(8) . . . . ? F5 C10 C11 C12 54.3(8) . . . . ? F6 C10 C11 C12 -66.0(7) . . . . ? C9 C10 C11 C12 178.0(6) . . . . ? C7 C11 C12 C16 37.9(9) . . . . ? C10 C11 C12 C16 -141.8(6) . . . . ? C7 C11 C12 C13 -146.2(6) . . . . ? C10 C11 C12 C13 34.1(8) . . . . ? C16 C12 C13 C14 -1.9(7) . . . . ? C11 C12 C13 C14 -178.3(5) . . . . ? C12 C13 C14 C15 -177.1(6) . . . . ? C12 C13 C14 S2 1.6(6) . . . . ? C16 S2 C14 C13 -0.8(5) . . . . ? C16 S2 C14 C15 178.0(5) . . . . ? C13 C12 C16 C17 -176.5(6) . . . . ? C11 C12 C16 C17 -0.3(10) . . . . ? C13 C12 C16 S2 1.2(6) . . . . ? C11 C12 C16 S2 177.4(4) . . . . ? C14 S2 C16 C12 -0.3(4) . . . . ? C14 S2 C16 C17 177.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 1.141 _refine_diff_density_min -1.153 _refine_diff_density_rms 0.099