# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Dr Pei Yu' _publ_contact_author_address ; Institut de Chimie Moleculaire et des Materiaux d'Orsay Universite Paris-Sud Laboratoire de Chimie Inorganique ORSAY Cedex 91405 FRANCE ; _publ_contact_author_email YUPEI@ICMO.U-PSUD.FR _publ_section_title ; Syntheses and photochromism of two new 1,2-bis(thiazolyl) perfluorocyclopentenes with chelating sites. ; loop_ _publ_author_name 'Pei Yu' 'Michele Cesario' 'Marie France Charlot' 'Marion Giraud' 'Elena Ishow' 'Anne Leaustic' ; K.Nakatani ; 'Robert Pansu' 'Christian Philouze' data_ORSAY _database_code_depnum_ccdc_archive 'CCDC 231160' #------------------------------------------------------------------------------ _audit_creation_date 2004-01-29 _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #------------------------------------------------------------------------------ _computing_data_collection 'EnrafNonius CAD4' _computing_cell_refinement 'EnrafNonius CAD' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 10.902(1) _cell_length_b 12.360(1) _cell_length_c 17.546(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2364.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293.0 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.4 _cell_measurement_theta_max 25.1 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_Int_Tables_number 60 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2-y,1/2+z '1/2+x,1/2-y, -z' ' -x, +y,1/2-z' ' -x, -y, -z' 1/2+x,1/2+y,1/2-z '1/2-x,1/2+y, +z' ' +x, -y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description prism _exptl_crystal_colour yellow-green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 262.25 _chemical_formula_analytical ? _chemical_formula_sum 'C11.50 H7 F3 N2 S ' _chemical_formula_moiety 'C11.50 H7 F3 N2 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1064.00 _exptl_absorpt_coefficient_mu 2.655 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.0 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method \w _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% -4.61 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 0 0 -6 0 0 _diffrn_reflns_number 10046 _reflns_number_total 10046 _reflns_number_gt 2056 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 74.90 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.05926 _diffrn_orient_matrix_UB_12 0.03523 _diffrn_orient_matrix_UB_13 0.03571 _diffrn_orient_matrix_UB_21 0.01776 _diffrn_orient_matrix_UB_22 -0.05669 _diffrn_orient_matrix_UB_23 0.03914 _diffrn_orient_matrix_UB_31 0.06771 _diffrn_orient_matrix_UB_32 0.04572 _diffrn_orient_matrix_UB_33 0.02101 #------------------------------------------------------------------------------ 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 92 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 56 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 16 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S 0 8 0.319 0.557 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; F 0 24 0.069 0.053 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.18749(5) -0.09922(4) 0.11135(3) 0.0517(2) 1.000 . Uani d ? F(8) -0.0829(2) -0.4445(2) 0.2185(2) 0.1509(8) 1.000 . Uani d ? F(71) 0.0182(3) -0.3304(2) 0.1206(1) 0.1204(7) 1.000 . Uani d ? F(72) 0.1796(2) -0.3243(1) 0.1871(1) 0.1063(6) 1.000 . Uani d ? N(4) 0.0309(2) 0.0544(2) 0.09730(9) 0.0518(4) 1.000 . Uani d ? N(15) 0.3207(2) 0.0330(2) -0.0002(1) 0.0602(5) 1.000 . Uani d ? C(2) 0.0543(2) -0.1044(2) 0.1650(1) 0.0453(4) 1.000 . Uani d ? C(3) -0.0183(2) -0.0169(2) 0.1491(1) 0.0480(5) 1.000 . Uani d ? C(5) 0.1375(2) 0.0211(2) 0.0731(1) 0.0490(5) 1.000 . Uani d ? C(6) 0.0271(2) -0.1952(2) 0.2151(1) 0.0440(4) 1.000 . Uani d ? C(7) 0.0576(2) -0.3076(2) 0.1906(1) 0.0588(6) 1.000 . Uani d ? C(8) 0.0000 -0.3829(3) 0.2500 0.0582(8) 0.500 ST Uani d ? C(9) -0.1429(2) 0.0068(2) 0.1798(1) 0.0599(6) 1.000 . Uani d ? C(10) 0.2138(2) 0.0809(2) 0.0180(1) 0.0503(5) 1.000 . Uani d ? C(11) 0.1764(3) 0.1800(2) -0.0097(1) 0.0653(7) 1.000 . Uani d ? C(12) 0.2551(3) 0.2350(2) -0.0585(1) 0.0779(8) 1.000 . Uani d ? C(13) 0.3655(3) 0.1876(2) -0.0777(2) 0.0754(7) 1.000 . Uani d ? C(14) 0.3939(2) 0.0874(2) -0.0479(2) 0.0700(7) 1.000 . Uani d ? H(11) 0.0992 0.2098 0.0041 0.078 1.000 . Uiso c ? H(12) 0.2333 0.3039 -0.0782 0.094 1.000 . Uiso c ? H(13) 0.4209 0.2234 -0.1110 0.091 1.000 . Uiso c ? H(14) 0.4697 0.0553 -0.0620 0.084 1.000 . Uiso c ? H(91) -0.1907 0.0412 0.1416 0.072 1.000 . Uiso c ? H(92) -0.1359 0.0531 0.2228 0.072 1.000 . Uiso c ? H(93) -0.1813 -0.0589 0.1946 0.072 1.000 . Uiso c ? 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) 0.0515(3) 0.0533(3) 0.0503(3) 0.0089(2) 0.0103(2) 0.0050(2) F(8) 0.130(1) 0.173(2) 0.149(1) -0.096(1) 0.054(1) -0.097(1) F(71) 0.235(3) 0.067(1) 0.0599(8) 0.025(1) -0.030(1) -0.0160(7) F(72) 0.078(1) 0.068(1) 0.173(2) 0.0229(8) 0.0581(9) 0.021(1) N(4) 0.0554(9) 0.053(1) 0.0471(7) 0.0077(8) -0.0006(7) 0.0044(7) N(15) 0.061(1) 0.068(1) 0.0523(9) -0.0034(9) 0.0047(7) 0.0048(8) C(2) 0.046(1) 0.049(1) 0.0409(8) 0.0031(8) 0.0041(7) -0.0003(7) C(3) 0.048(1) 0.054(1) 0.0422(8) 0.0061(8) -0.0016(7) 0.0009(7) C(5) 0.055(1) 0.049(1) 0.0424(8) 0.0011(8) -0.0024(8) 0.0002(7) C(6) 0.0433(9) 0.0439(9) 0.0448(8) 0.0030(7) 0.0009(7) -0.0007(7) C(7) 0.072(1) 0.052(1) 0.052(1) 0.015(1) 0.0070(9) -0.0015(8) C(8) 0.058(2) 0.040(1) 0.076(2) 0.0000 0.002(1) 0.0000 C(9) 0.051(1) 0.069(1) 0.060(1) 0.015(1) 0.0034(9) 0.008(1) C(10) 0.056(1) 0.054(1) 0.0410(8) -0.0052(9) -0.0031(8) 0.0009(8) C(11) 0.078(2) 0.060(1) 0.059(1) 0.001(1) 0.006(1) 0.008(1) C(12) 0.103(2) 0.057(1) 0.074(1) -0.009(1) 0.004(1) 0.016(1) C(13) 0.077(2) 0.083(2) 0.066(1) -0.027(1) 0.005(1) 0.013(1) C(14) 0.060(1) 0.085(2) 0.065(1) -0.011(1) 0.006(1) 0.006(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00203|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.000005(2) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2056 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_all 0.1183 _refine_ls_wR_factor_ref 0.1183 _refine_ls_goodness_of_fit_all 1.987 _refine_ls_goodness_of_fit_ref 1.987 _refine_ls_shift/su_max 0.0059 _refine_ls_shift/su_mean 0.0006 _refine_diff_density_min -0.35 _refine_diff_density_max 0.35 #------------------------------------------------------------------------------ _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(2) 1.732(2) . . yes S(1) C(5) 1.720(2) . . yes F(8) C(8) 1.305(3) . . yes F(71) C(7) 1.331(3) . . yes F(72) C(7) 1.347(3) . . yes N(4) C(3) 1.375(3) . . yes N(4) C(5) 1.304(3) . . yes N(15) C(10) 1.346(3) . . yes N(15) C(14) 1.338(3) . . yes C(2) C(3) 1.370(3) . . yes C(2) C(6) 1.455(3) . . yes C(3) C(9) 1.490(3) . . yes C(5) C(10) 1.474(3) . . yes C(6) C(6) 1.361(4) . 4 yes C(6) C(7) 1.493(3) . . yes C(7) C(8) 1.533(3) . . yes C(9) H(91) 0.95 . . no C(9) H(92) 0.95 . . no C(9) H(93) 0.95 . . no C(10) C(11) 1.380(3) . . yes C(11) C(12) 1.389(4) . . yes C(11) H(11) 0.95 . . no C(12) C(13) 1.380(4) . . yes C(12) H(12) 0.95 . . no C(13) C(14) 1.380(4) . . yes C(13) H(13) 0.95 . . no C(14) H(14) 0.95 . . no H(91) H(92) 1.55 . . no H(91) H(93) 1.55 . . no H(92) H(93) 1.55 . . no #------------------------------------------------------------------------------ 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(2) S(1) C(5) 88.8(1) . . . yes C(3) N(4) C(5) 111.1(2) . . . yes C(10) N(15) C(14) 116.4(2) . . . yes S(1) C(2) C(3) 110.2(1) . . . yes S(1) C(2) C(6) 121.9(1) . . . yes C(3) C(2) C(6) 127.9(2) . . . yes N(4) C(3) C(2) 114.5(2) . . . yes N(4) C(3) C(9) 118.0(2) . . . yes C(2) C(3) C(9) 127.5(2) . . . yes S(1) C(5) N(4) 115.4(2) . . . yes S(1) C(5) C(10) 120.7(2) . . . yes N(4) C(5) C(10) 123.9(2) . . . yes C(2) C(6) C(6) 129.2(1) . . 4 yes C(2) C(6) C(7) 119.9(2) . . . yes C(6) C(6) C(7) 110.9(1) 4 . . yes F(71) C(7) F(72) 104.2(2) . . . yes F(71) C(7) C(6) 113.0(2) . . . yes F(71) C(7) C(8) 111.5(2) . . . yes F(72) C(7) C(6) 112.1(2) . . . yes F(72) C(7) C(8) 110.0(2) . . . yes C(6) C(7) C(8) 106.1(2) . . . yes F(8) C(8) F(8) 108.6(4) . . 4 yes F(8) C(8) C(7) 110.5(2) . . . yes F(8) C(8) C(7) 111.0(1) . . 4 yes F(8) C(8) C(7) 111.0(1) 4 . . yes F(8) C(8) C(7) 110.5(2) 4 . 4 yes C(7) C(8) C(7) 105.2(2) . . 4 yes C(3) C(9) H(91) 109.5 . . . no C(3) C(9) H(92) 109.5 . . . no C(3) C(9) H(93) 109.5 . . . no H(91) C(9) H(92) 109.5 . . . no H(91) C(9) H(93) 109.5 . . . no H(92) C(9) H(93) 109.5 . . . no N(15) C(10) C(5) 115.1(2) . . . yes N(15) C(10) C(11) 124.2(2) . . . yes C(5) C(10) C(11) 120.6(2) . . . yes C(10) C(11) C(12) 118.0(2) . . . yes C(10) C(11) H(11) 121.0 . . . no C(12) C(11) H(11) 121.0 . . . no C(11) C(12) C(13) 118.8(3) . . . yes C(11) C(12) H(12) 120.6 . . . no C(13) C(12) H(12) 120.6 . . . no C(12) C(13) C(14) 118.9(2) . . . yes C(12) C(13) H(13) 120.6 . . . no C(14) C(13) H(13) 120.6 . . . no N(15) C(14) C(13) 123.7(3) . . . yes N(15) C(14) H(14) 118.1 . . . no C(13) C(14) H(14) 118.1 . . . no H(91) H(92) H(93) 60.0 . . . no H(91) H(93) H(92) 60.0 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(8) C(9) 3.124(3) . 7_445 no F(8) C(14) 3.485(4) . 3_445 no F(71) N(15) 3.230(3) . 7_545 no F(71) C(14) 3.269(3) . 7_545 no F(71) C(12) 3.385(4) . 5 no F(71) C(11) 3.427(3) . 5 no F(72) C(10) 3.396(3) . 7_545 no F(72) C(5) 3.410(3) . 7_545 no N(15) C(14) 3.552(4) . 5_655 no C(14) C(14) 3.585(6) . 5_655 no C(3) C(3) 3.563(4) . 4 no #------------------------------------------------------------------------------ data_photochromic_compound _database_code_depnum_ccdc_archive 'CCDC 235922' _audit_creation_method SHELXL #_chemical_absolute_configuration _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'C23 H14 F6 N4 S2' _chemical_formula_analytical ? _chemical_formula_sum 'C23 H14 F6 N4 S2' _chemical_formula_weight 524.50 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' 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' N N 0.0061 0.0033 '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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 16.492(6) _cell_length_b 8.379(3) _cell_length_c 16.790(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.52(4) _cell_angle_gamma 90.00 _cell_volume 2315.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9136 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method ? _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius kappaCCD diffractometer' _diffrn_measurement_method 'phi scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10909 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 29.15 _reflns_number_total 5695 _reflns_number_gt 4078 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft,1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft,1998)' ; _computing_data_reduction 'HKL package (Otwinowski & Minor,1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'R3M (Riche,1983) ORTEP (Johnson,1965)' _computing_publication_material SHELXL-93) _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.1028P)^2^+1.0702P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5694 _refine_ls_number_parameters 352 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_all 0.1698 _refine_ls_wR_factor_ref 0.1401 _refine_ls_goodness_of_fit_all 0.869 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.893 _refine_ls_restrained_S_obs 0.879 _refine_ls_shift/su_max 1.100 _refine_ls_shift/esd_mean 0.049 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1A S 0.25602(4) 0.00852(7) 0.89048(4) 0.0621(2) Uani 1 d . . C2A C 0.31461(12) 0.1391(3) 0.83964(13) 0.0526(5) Uani 1 d . . C3A C 0.34590(12) 0.2528(3) 0.89187(12) 0.0473(4) Uani 1 d . . N4A N 0.32377(10) 0.2387(2) 0.96968(10) 0.0504(4) Uani 1 d . . C5A C 0.27741(12) 0.1154(3) 0.97716(13) 0.0511(5) Uani 1 d . . C9A C 0.3243(2) 0.1179(4) 0.75237(14) 0.0715(7) Uani 1 d . . H9A1 H 0.2788 0.0590 0.7291 0.093 Uiso 1 calc R . H9A2 H 0.3735 0.0604 0.74470 0.093 Uiso 1 calc R . H9A3 H 0.3266 0.2206 0.7273 0.093 Uiso 1 calc R . C10A C 0.24402(12) 0.0637(3) 1.05211(14) 0.0569(5) Uani 1 d . . C11A C 0.25371(15) 0.1539(4) 1.12058(15) 0.0668(6) Uani 1 d . . H11A H 0.28136 0.2506 1.12069 0.080 Uiso 1 calc R . C12A C 0.2214(2) 0.0973(4) 1.1891(2) 0.0804(8) Uani 1 d . . H12A H 0.2271 0.1551 1.2364 0.096 Uiso 1 calc R . C13A C 0.1810(2) -0.0442(5) 1.1862(2) 0.0911(10) Uani 1 d . . H13A H 0.1589 -0.0848 1.2316 0.109 Uiso 1 calc R . C14A C 0.1735(2) -0.1257(4) 1.1159(2) 0.0935(10) Uani 1 d . . H14A H 0.1453 -0.2218 1.1151 0.112 Uiso 1 calc R . N15A N 0.20408(14) -0.0765(3) 1.04785(15) 0.0773(6) Uani 1 d . . S1B S 0.57901(4) 0.04786(8) 0.73786(4) 0.0633(2) Uani 1 d . . C2B C 0.53607(13) 0.1569(3) 0.81147(13) 0.0539(5) Uani 1 d . . C3B C 0.49570(12) 0.2840(3) 0.77718(12) 0.0490(5) Uani 1 d . . N4B N 0.49939(11) 0.2992(2) 0.69550(10) 0.0527(4) Uani 1 d . . C5B C 0.54105(12) 0.1824(3) 0.66731(12) 0.0532(5) Uani 1 d . . C9B C 0.5487(2) 0.1144(3) 0.89815(14) 0.0711(7) Uani 1 d . . H9B1 H 0.5898 0.1822 0.9230 0.092 Uiso 1 calc R . H9B2 H 0.5657 0.0051 0.90311 0.092 Uiso 1 calc R . H9B3 H 0.4988 0.1287 0.9238 0.092 Uiso 1 calc R . C10B C 0.55967(13) 0.1668(3) 0.58298(14) 0.0599(6) Uani 1 d . . C11B C 0.5324(2) 0.2775(4) 0.52705(15) 0.0743(7) Uani 1 d . . H11B H 0.4991 0.3616 0.54062 0.089 Uiso 1 calc R . C12B C 0.5560(2) 0.2594(5) 0.4499(2) 0.0921(10) Uani 1 d . . H12B H 0.5389 0.3322 0.4105 0.111 Uiso 1 calc R . C13B C 0.6040(2) 0.1359(5) 0.4320(2) 0.1013(13) Uani 1 d . . H13B H 0.6211 0.1233 0.3806 0.122 Uiso 1 calc R . C14B C 0.6268(2) 0.0301(5) 0.4906(2) 0.0965(11) Uani 1 d . . H14B H 0.6587 -0.0563 0.4771 0.116 Uiso 1 calc R . N15B N 0.60639(14) 0.0421(3) 0.56677(15) 0.0781(7) Uani 1 d . . C6A C 0.39427(12) 0.3920(2) 0.87198(11) 0.0451(4) Uani 1 d D . C6B C 0.45327(12) 0.4075(3) 0.82061(11) 0.0464(4) Uani 1 d D . C7A C 0.37796(13) 0.5497(3) 0.91107(12) 0.0515(5) Uani 1 d D . F7A1 F 0.3003(4) 0.5840(10) 0.9144(4) 0.076(2) Uani 0.80 d PD . F7A2 F 0.4137(2) 0.5561(3) 0.98552(14) 0.0693(6) Uani 0.80 d PD . G7A1 F 0.3865(6) 0.5536(17) 0.9917(7) 0.067(3) Uiso 0.20 d PD . G7A2 F 0.2941(14) 0.5821(33) 0.9099(13) 0.045(3) Uiso 0.20 d PD . C7B C 0.47995(14) 0.5779(3) 0.81517(13) 0.0567(5) Uani 1 d D . F7B1 F 0.48990(13) 0.6331(2) 0.74139(10) 0.0669(5) Uani 0.80 d PD . F7B2 F 0.55655(10) 0.5976(2) 0.85392(14) 0.0707(5) Uani 0.80 d PD . G7B1 F 0.4321(8) 0.6288(16) 0.7414(7) 0.120(4) Uiso 0.20 d PD . G7B2 F 0.5460(7) 0.6101(15) 0.8083(8) 0.106(4) Uiso 0.20 d PD . C8 C 0.4170(2) 0.6711(4) 0.8570(3) 0.0566(8) Uani 0.80 d PD . C8' C 0.4387(10) 0.6640(22) 0.8807(10) 0.063(5) Uiso 0.20 d PD . F81 F 0.4454(2) 0.8016(2) 0.8964(2) 0.0921(8) Uani 0.80 d PD . F82 F 0.36117(12) 0.7282(2) 0.80071(13) 0.0784(6) Uani 0.80 d PD . G81 F 0.4950(5) 0.7127(11) 0.9344(5) 0.082(2) Uiso 0.20 d PD . G82 F 0.3977(7) 0.7870(16) 0.8506(7) 0.096(3) Uiso 0.20 d PD . 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 S1A 0.0611(3) 0.0510(4) 0.0751(4) -0.0103(3) 0.0113(3) -0.0080(2) C2A 0.0515(10) 0.0496(13) 0.0568(11) -0.0062(9) 0.0037(8) 0.0007(9) C3A 0.0478(9) 0.0458(12) 0.0487(10) -0.0029(8) 0.0062(8) 0.0017(8) N4A 0.0513(9) 0.0488(10) 0.0521(9) -0.0025(7) 0.0118(7) -0.0012(8) C5A 0.0476(10) 0.0467(12) 0.0597(12) 0.0011(9) 0.0098(8) 0.0041(9) C9A 0.078(2) 0.082(2) 0.0544(13) -0.0145(12) 0.0004(11) -0.0089(14) C10A 0.0462(10) 0.0570(14) 0.0691(13) 0.0082(11) 0.0153(9) 0.0072(9) C11A 0.0626(13) 0.072(2) 0.0671(14) 0.0065(12) 0.0175(11) 0.0057(12) C12A 0.072(2) 0.102(2) 0.070(2) 0.014(2) 0.0231(13) 0.016(2) C13A 0.070(2) 0.117(3) 0.090(2) 0.038(2) 0.0344(15) 0.014(2) C14A 0.085(2) 0.083(2) 0.117(3) 0.029(2) 0.036(2) -0.011(2) N15A 0.0739(13) 0.068(2) 0.093(2) 0.0130(12) 0.0236(11) -0.0089(11) S1B 0.0637(3) 0.0539(4) 0.0731(4) -0.0115(3) 0.0105(3) 0.0120(3) C2B 0.0560(11) 0.0502(13) 0.0562(11) -0.0039(9) 0.0074(9) 0.0036(9) C3B 0.0516(10) 0.0483(12) 0.0481(10) -0.0043(8) 0.0108(8) 0.0036(8) N4B 0.0572(9) 0.0539(11) 0.0482(9) -0.0037(8) 0.0141(7) 0.0018(8) C5B 0.0512(10) 0.0538(13) 0.0559(11) -0.0119(9) 0.0146(8) -0.0039(9) C9B 0.090(2) 0.061(2) 0.0608(14) 0.0031(11) -0.0033(12) 0.0120(13) C10B 0.0567(11) 0.065(2) 0.0606(12) -0.0205(11) 0.0218(9) -0.0158(11) C11B 0.085(2) 0.083(2) 0.0565(13) -0.0116(13) 0.0191(12) -0.0106(14) C12B 0.109(2) 0.116(3) 0.0543(14) -0.017(2) 0.0254(15) -0.031(2) C13B 0.107(2) 0.131(3) 0.071(2) -0.048(2) 0.047(2) -0.050(2) C14B 0.090(2) 0.101(3) 0.105(2) -0.051(2) 0.052(2) -0.019(2) N15B 0.0737(13) 0.075(2) 0.090(2) -0.0308(12) 0.0372(11) -0.0080(11) C6A 0.0492(10) 0.0439(11) 0.0423(9) -0.0037(8) 0.0048(7) 0.0022(8) C6B 0.0519(10) 0.0448(11) 0.0431(9) -0.0009(8) 0.0069(7) 0.0043(8) C7A 0.0550(11) 0.0524(13) 0.0483(10) -0.0080(9) 0.0123(8) 0.0010(9) F7A1 0.062(2) 0.069(2) 0.101(3) -0.007(2) 0.031(2) 0.012(2) F7A2 0.078(2) 0.0783(15) 0.0508(11) -0.0237(9) 0.0014(11) -0.0045(14) C7B 0.0653(13) 0.0555(14) 0.0511(11) -0.0006(9) 0.0181(9) -0.0042(10) F7B1 0.0960(14) 0.0519(10) 0.0561(9) 0.0081(7) 0.0304(9) 0.0022(9) F7B2 0.0546(9) 0.0773(13) 0.0800(13) -0.0008(10) 0.0028(9) -0.0166(8) C8 0.065(2) 0.039(2) 0.067(2) -0.0093(15) 0.017(2) 0.0011(14) F81 0.118(2) 0.0554(13) 0.109(2) -0.0385(11) 0.054(2) -0.0331(12) F82 0.0817(12) 0.0661(13) 0.0892(13) 0.0231(10) 0.0202(11) 0.0206(10) _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 S1A C2A 1.721(2) . ? S1A C5A 1.727(2) . ? C2A C3A 1.374(3) . ? C2A C9A 1.494(3) . ? C3A N4A 1.383(3) . ? C3A C6A 1.463(3) . ? N4A C5A 1.296(3) . ? C5A C10A 1.470(3) . ? C10A N15A 1.347(3) . ? C10A C11A 1.377(4) . ? C11A C12A 1.381(4) . ? C12A C13A 1.359(5) . ? C13A C14A 1.362(5) . ? C14A N15A 1.342(4) . ? S1B C2B 1.724(2) . ? S1B C5B 1.725(3) . ? C2B C3B 1.364(3) . ? C2B C9B 1.500(3) . ? C3B N4B 1.382(3) . ? C3B C6B 1.468(3) . ? N4B C5B 1.301(3) . ? C5B C10B 1.473(3) . ? C10B N15B 1.336(3) . ? C10B C11B 1.375(4) . ? C11B C12B 1.385(3) . ? C12B C13B 1.347(6) . ? C13B C14B 1.360(6) . ? C14B N15B 1.347(4) . ? C6A C6B 1.346(3) . ? C6A C7A 1.507(3) . ? C6B C7B 1.498(3) . ? C7A F7A1 1.317(7) . ? C7A G7A1 1.353(12) . ? C7A F7A2 1.350(3) . ? C7A G7A2 1.41(2) . ? C7A C8' 1.50(2) . ? C7A C8 1.532(4) . ? C7B G7B2 1.135(12) . ? C7B F7B1 1.342(3) . ? C7B F7B2 1.395(3) . ? C7B C8 1.507(4) . ? C7B G7B1 1.490(12) . ? C7B C8' 1.51(2) . ? F7B1 G7B1 0.954(13) . ? F7B1 G7B2 1.423(13) . ? F7B2 G7B2 0.782(12) . ? G7B1 F82 1.788(14) . ? C8 C8' 0.522(15) . ? C8 G82 1.025(12) . ? C8 F81 1.347(4) . ? C8 F82 1.365(5) . ? C8 G81 1.805(9) . ? C8' F81 1.19(2) . ? C8' G81 1.32(2) . ? C8' G82 1.32(2) . ? C8' F82 1.88(2) . ? F81 G82 1.073(12) . ? F81 G81 1.251(9) . ? F82 G82 1.116(13) . ? 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 C2A S1A C5A 89.79(11) . . ? C3A C2A C9A 130.6(2) . . ? C3A C2A S1A 108.9(2) . . ? C9A C2A S1A 120.5(2) . . ? C2A C3A N4A 115.7(2) . . ? C2A C3A C6A 126.6(2) . . ? N4A C3A C6A 117.6(2) . . ? C5A N4A C3A 110.6(2) . . ? N4A C5A C10A 124.9(2) . . ? N4A C5A S1A 115.0(2) . . ? C10A C5A S1A 120.0(2) . . ? N15A C10A C11A 123.7(2) . . ? N15A C10A C5A 114.8(2) . . ? C11A C10A C5A 121.5(2) . . ? C10A C11A C12A 118.4(3) . . ? C13A C12A C11A 118.9(3) . . ? C12A C13A C14A 119.1(3) . . ? N15A C14A C13A 124.4(3) . . ? C14A N15A C10A 115.5(3) . . ? C2B S1B C5B 89.89(11) . . ? C3B C2B C9B 129.0(2) . . ? C3B C2B S1B 108.8(2) . . ? C9B C2B S1B 122.0(2) . . ? C2B C3B N4B 116.1(2) . . ? C2B C3B C6B 125.1(2) . . ? N4B C3B C6B 118.7(2) . . ? C5B N4B C3B 110.4(2) . . ? N4B C5B C10B 124.2(2) . . ? N4B C5B S1B 114.8(2) . . ? C10B C5B S1B 120.9(2) . . ? N15B C10B C11B 123.8(2) . . ? N15B C10B C5B 115.0(2) . . ? C11B C10B C5B 121.2(2) . . ? C10B C11B C12B 117.8(3) . . ? C13B C12B C11B 119.7(4) . . ? C12B C13B C14B 118.7(3) . . ? N15B C14B C13B 124.3(3) . . ? C10B N15B C14B 115.7(3) . . ? C6B C6A C3A 130.5(2) . . ? C6B C6A C7A 110.5(2) . . ? C3A C6A C7A 119.0(2) . . ? C6A C6B C3B 129.5(2) . . ? C6A C6B C7B 111.0(2) . . ? C3B C6B C7B 119.4(2) . . ? F7A1 C7A G7A1 89.6(6) . . ? F7A1 C7A F7A2 108.8(4) . . ? G7A1 C7A F7A2 19.9(5) . . ? F7A1 C7A G7A2 3.6(13) . . ? G7A1 C7A G7A2 92.9(10) . . ? F7A2 C7A G7A2 112.2(9) . . ? F7A1 C7A C8' 123.2(8) . . ? G7A1 C7A C8' 107.1(8) . . ? F7A2 C7A C8' 91.5(6) . . ? G7A2 C7A C8' 123.3(13) . . ? F7A1 C7A C6A 114.2(4) . . ? G7A1 C7A C6A 116.6(6) . . ? F7A2 C7A C6A 111.0(2) . . ? G7A2 C7A C6A 111.4(12) . . ? C8' C7A C6A 105.8(7) . . ? F7A1 C7A C8 109.0(4) . . ? G7A1 C7A C8 123.7(6) . . ? F7A2 C7A C8 110.3(3) . . ? G7A2 C7A C8 108.2(10) . . ? C8' C7A C8 19.8(6) . . ? C6A C7A C8 103.4(2) . . ? G7B2 C7B F7B1 69.6(7) . . ? G7B2 C7B F7B2 34.1(6) . . ? F7B1 C7B F7B2 103.4(2) . . ? G7B2 C7B C6B 121.4(7) . . ? F7B1 C7B C6B 116.0(2) . . ? F7B2 C7B C6B 110.2(2) . . ? G7B2 C7B C8 128.1(7) . . ? F7B1 C7B C8 112.2(3) . . ? F7B2 C7B C8 110.6(2) . . ? C6B C7B C8 104.6(2) . . ? G7B2 C7B G7B1 108.0(9) . . ? F7B1 C7B G7B1 38.9(5) . . ? F7B2 C7B G7B1 140.6(6) . . ? C6B C7B G7B1 100.4(6) . . ? C8 C7B G7B1 83.9(6) . . ? G7B2 C7B C8' 115.9(9) . . ? F7B1 C7B C8' 126.4(7) . . ? F7B2 C7B C8' 92.2(6) . . ? C6B C7B C8' 105.3(7) . . ? C8 C7B C8' 19.9(6) . . ? G7B1 C7B C8' 103.3(8) . . ? G7B1 F7B1 C7B 79.0(8) . . ? G7B1 F7B1 G7B2 126.6(9) . . ? C7B F7B1 G7B2 48.3(5) . . ? G7B2 F7B2 C7B 54.4(9) . . ? F7B1 G7B1 C7B 62.1(7) . . ? F7B1 G7B1 F82 132.1(11) . . ? C7B G7B1 F82 90.1(6) . . ? F7B2 G7B2 C7B 91.5(12) . . ? F7B2 G7B2 F7B1 152.4(14) . . ? C7B G7B2 F7B1 62.1(6) . . ? C8' C8 G82 112.5(24) . . ? C8' C8 F81 61.1(22) . . ? G82 C8 F81 51.7(7) . . ? C8' C8 F82 165.8(23) . . ? G82 C8 F82 53.4(8) . . ? F81 C8 F82 104.8(3) . . ? C8' C8 C7B 80.6(22) . . ? G82 C8 C7B 131.3(7) . . ? F81 C8 C7B 114.9(3) . . ? F82 C8 C7B 108.3(3) . . ? C8' C8 C7A 76.4(22) . . ? G82 C8 C7A 123.5(7) . . ? F81 C8 C7A 113.2(3) . . ? F82 C8 C7A 110.7(3) . . ? C7B C8 C7A 105.0(2) . . ? C8' C8 G81 17.9(22) . . ? G82 C8 G81 95.5(9) . . ? F81 C8 G81 43.9(3) . . ? F82 C8 G81 148.4(4) . . ? C7B C8 G81 87.4(4) . . ? C7A C8 G81 90.5(4) . . ? C8 C8' F81 96.2(25) . . ? C8 C8' G81 155.1(30) . . ? F81 C8' G81 59.7(9) . . ? C8 C8' G82 46.0(19) . . ? F81 C8' G82 50.5(9) . . ? G81 C8' G82 110.1(15) . . ? C8 C8' C7A 83.7(22) . . ? F81 C8' C7A 127.0(14) . . ? G81 C8' C7A 115.1(12) . . ? G82 C8' C7A 107.0(12) . . ? C8 C8' C7B 79.4(21) . . ? F81 C8' C7B 125.8(14) . . ? G81 C8' C7B 108.4(12) . . ? G82 C8' C7B 109.7(12) . . ? C7A C8' C7B 106.4(11) . . ? C8 C8' F82 10.3(17) . . ? F81 C8' F82 86.0(10) . . ? G81 C8' F82 145.2(14) . . ? G82 C8' F82 35.8(8) . . ? C7A C8' F82 89.2(8) . . ? C7B C8' F82 86.1(7) . . ? G82 F81 C8' 71.1(9) . . ? G82 F81 G81 136.5(8) . . ? C8' F81 G81 65.4(8) . . ? G82 F81 C8 48.5(6) . . ? C8' F81 C8 22.7(7) . . ? G81 F81 C8 87.9(5) . . ? G82 F82 C8 47.5(6) . . ? G82 F82 G7B1 106.4(7) . . ? C8 F82 G7B1 77.7(4) . . ? G82 F82 C8' 43.6(8) . . ? C8 F82 C8' 3.9(6) . . ? G7B1 F82 C8' 79.9(7) . . ? F81 G81 C8' 54.9(9) . . ? F81 G81 C8 48.2(3) . . ? C8' G81 C8 7.0(9) . . ? C8 G82 F81 79.8(8) . . ? C8 G82 F82 79.1(11) . . ? F81 G82 F82 157.9(13) . . ? C8 G82 C8' 21.5(8) . . ? F81 G82 C8' 58.4(9) . . ? F82 G82 C8' 100.6(13) . . ? _refine_diff_density_max 0.273 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.037