# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1196 #========================================================= # Fatigue Resistant Property of Photochromic Dithienylethenes - # By-productFormation # # Masahiro Irie, Thorsten Lifka, Kingo Uchida, Seiya Kobatake and YurikoShindo # # Department of Chemistry and Biochemistry, Graduate School of Engineering, # Kyushu University, and CREST, Japan Science and Technology Corporation, # Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan #========================================================= #========================================================= data_global #========================================================= # 1. SUBMISSION DETAILS _publ_contact_author ; Prof. Masahiro Irie Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University 6-10-1 Hakozaki, Higashi-ku Fukuoka 812-8581, Japan ; _publ_contact_author_phone '+81-92-642-3556' _publ_contact_author_fax '+81-92-642-3568' _publ_contact_author_email irie@cstf.kyushu-u.ac.jp _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #========================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #========================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Fatigue Resistant Property of Photochromic Dithienyl ethenes - By-product Formation ; #The loop structure below should contain the names and addresses of all #authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Masahiro Irie' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; 'Thorsten Lifka' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; 'Kingo Uchida' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; 'Seiya Kobatake' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; 'Yuriko Shindo' ; Department of Chemistry and Biochemistry Graduate School of Engineering Kyushu University and CREST Japan Science and Technology Corporation Hakozaki 6-10-1, Higashi-ku Fukuoka 812-8581, Japan ; #========================================================= # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; All H atoms were located at ideal positions and were included in refinement, but restrained to ride on the atom to which they are bonded. There are disordered contributions (89:11) on the fluorinated cyclopentane ring. Two envelope conformers were solved with using several restraints in SHELXL-93. Only the major structure was drawn as ORTEP. ; _publ_section_references ; Altomare, M. C., Burla, M., Camalli, G., Cascarano, C., Giacovazzo, A., Guagliardi, G. & Polidori, J. (1994). SIR92. J. Appl. Cryst. 27, 435. Hall, S. R. & du Boulay, D. (1995). Xtal_GX. University of Western Australia, Australia. Sheldrick, G. M. (1993). SHELXL-93. University of G\"ottingen, Germany. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #========================================================= #========================================================= # 5. CRYSTAL DATA # 6. DATA COLLECTION data_compd3 _audit_creation_method SHELXL _chemical_name_systematic ; 11,11,12,12,13,13-Hexafluoro-5,15-dimethyl-3,7-diphenyl-4,6-dithia- tetracyclo[7.5.1.0<5,15>.0<10,14>]pentadeca-1(14),2,7,9(10)-tetraene ; _chemical_name_common ? _chemical_formula_moiety 'C27 H18 F6 S2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H18 F6 S2' _chemical_formula_weight 520.56 _chemical_melting_point 404 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' .0727 .0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .3331 .5567 '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 11.565(3) _cell_length_b 11.827(3) _cell_length_c 10.206(2) _cell_angle_alpha 95.45(2) _cell_angle_beta 100.68(2) _cell_angle_gamma 60.12(2) _cell_volume 1189.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 21 _cell_measurement_theta_max 42 _exptl_crystal_description plate _exptl_crystal_colour 'dark violet' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method ? _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 2.584 _exptl_absorpt_correction_type 'empirical via \y scans' _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius FR590' _diffrn_measurement_method \w/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 4741 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 69.93 _reflns_number_total 4506 _reflns_number_observed 2932 _reflns_observed_criterion >2\s(I) #========================================================= # 7. COMPUTING SOFTWARE _computing_data_collection 'CAD4 Enraf-Nonius software' _computing_cell_refinement 'CAD4 Enraf-Nonius software' _computing_data_reduction 'MolEN Enraf-Nonius software' _computing_structure_solution ; SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo, Guagliardi & Polidori, 1994) ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Xtal_GX (Hall & Boulay, 1995)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' #========================================================= # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+( 0.0869P)^2^+0.3425P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0004(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4506 _refine_ls_number_parameters 375 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_obs 0.0530 _refine_ls_wR_factor_all 0.1647 _refine_ls_wR_factor_obs 0.1356 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_goodness_of_fit_obs 1.078 _refine_ls_restrained_S_all 1.034 _refine_ls_restrained_S_obs 1.078 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max .448 _refine_diff_density_min -.336 #========================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S3 S 1.17482(8) 0.11484(10) 0.63487(9) 0.0618(3) Uani 1 d . . S4 S 0.89218(8) 0.17906(10) 0.53108(9) 0.0596(3) Uani 1 d . . C1 C 1.2094(3) 0.1640(3) 0.9058(3) 0.0540(8) Uani 1 d . . H1 H 1.2649(3) 0.1650(3) 0.9840(3) 0.065 Uiso 1 calc R . C2 C 1.2633(3) 0.1253(3) 0.7925(3) 0.0497(8) Uani 1 d . . C3a C 0.9993(3) 0.2154(3) 0.6662(3) 0.0520(8) Uani 1 d . . C5 C 0.7389(3) 0.2536(3) 0.5959(3) 0.0480(7) Uani 1 d . . C6 C 0.7298(3) 0.2848(4) 0.7255(3) 0.0538(8) Uani 1 d . . H6 H 0.6448(3) 0.3252(4) 0.7507(3) 0.065 Uiso 1 calc R . C6a C 0.8434(3) 0.2594(3) 0.8261(3) 0.0515(8) Uani 1 d . . C6b C 0.8534(3) 0.3040(4) 0.9527(3) 0.0532(8) Uani 1 d . . C7 C 0.7642(4) 0.3856(4) 1.0494(4) 0.0611(9) Uani 1 d D . C9 C 0.9993(4) 0.3275(4) 1.1389(4) 0.0622(9) Uani 1 d D . C9a C 0.9924(3) 0.2686(4) 1.0062(3) 0.0542(8) Uani 1 d . . C9b C 1.0730(3) 0.2033(3) 0.9129(3) 0.0520(8) Uani 1 d . . C9c C 0.9880(3) 0.1744(3) 0.7968(3) 0.0504(8) Uani 1 d . . C10 C 0.9589(4) 0.3591(4) 0.6618(4) 0.0637(10) Uani 1 d . . H10A H 0.9683(4) 0.3787(4) 0.5765(4) 0.096 Uiso 1 calc R . H10B H 1.0164(4) 0.3772(4) 0.7307(4) 0.096 Uiso 1 calc R . H10C H 0.8667(4) 0.4119(4) 0.6753(4) 0.096 Uiso 1 calc R . C11 C 1.0282(4) 0.0290(4) 0.8034(4) 0.0604(9) Uani 1 d . . H11A H 1.0183(4) 0.0108(4) 0.8891(4) 0.091 Uiso 1 calc R . H11B H 1.1205(4) -0.0245(4) 0.7903(4) 0.091 Uiso 1 calc R . H11C H 0.9707(4) 0.0105(4) 0.7350(4) 0.091 Uiso 1 calc R . C12 C 1.4052(3) 0.0903(3) 0.7899(4) 0.0541(8) Uani 1 d . . C13 C 1.4665(4) 0.1468(4) 0.8810(4) 0.0664(10) Uani 1 d . . H13 H 1.4181(4) 0.2073(4) 0.9426(4) 0.080 Uiso 1 calc R . C14 C 1.5999(4) 0.1135(4) 0.8808(5) 0.0763(12) Uani 1 d . . H14 H 1.6410(4) 0.1502(4) 0.9436(5) 0.092 Uiso 1 calc R . C15 C 1.6706(4) 0.0276(4) 0.7893(5) 0.0774(13) Uani 1 d . . H15 H 1.7594(4) 0.0067(4) 0.7888(5) 0.093 Uiso 1 calc R . C16 C 1.6116(4) -0.0282(4) 0.6979(5) 0.0796(13) Uani 1 d . . H16 H 1.6600(4) -0.0871(4) 0.6354(5) 0.095 Uiso 1 calc R . C17 C 1.4790(4) 0.0034(4) 0.6989(4) 0.0670(10) Uani 1 d . . H17 H 1.4393(4) -0.0350(4) 0.6367(4) 0.080 Uiso 1 calc R . C18 C 0.6183(3) 0.2815(3) 0.4946(3) 0.0521(8) Uani 1 d . . C19 C 0.5024(3) 0.2941(4) 0.5316(4) 0.0656(10) Uani 1 d . . H19 H 0.5018(3) 0.2808(4) 0.6198(4) 0.079 Uiso 1 calc R . C20 C 0.3888(4) 0.3262(4) 0.4380(4) 0.0737(12) Uani 1 d . . H20 H 0.3110(4) 0.3373(4) 0.4643(4) 0.088 Uiso 1 calc R . C21 C 0.3881(4) 0.3423(4) 0.3072(4) 0.0770(12) Uani 1 d . . H21 H 0.3113(4) 0.3624(4) 0.2444(4) 0.092 Uiso 1 calc R . C22 C 0.5018(4) 0.3283(5) 0.2701(4) 0.0875(14) Uani 1 d . . H22 H 0.5024(4) 0.3394(5) 0.1813(4) 0.105 Uiso 1 calc R . C23 C 0.6161(4) 0.2978(5) 0.3632(4) 0.0713(11) Uani 1 d . . H23 H 0.6930(4) 0.2882(5) 0.3361(4) 0.086 Uiso 1 calc R . C8 C 0.8501(4) 0.4327(5) 1.1457(5) 0.0620(12) Uani 0.889(6) d PD 1 F7\a F 0.6442(3) 0.4822(4) 0.9983(4) 0.0840(12) Uani 0.889(6) d P 1 F7\b F 0.7347(4) 0.3113(5) 1.1202(3) 0.0816(11) Uani 0.889(6) d P 1 F8\a F 0.8303(3) 0.5420(3) 1.0934(4) 0.0945(13) Uani 0.889(6) d PD 1 F8\b F 0.8201(7) 0.4587(6) 1.2687(5) 0.093(2) Uani 0.889(6) d PD 1 F9\a F 1.0825(4) 0.3757(5) 1.1648(5) 0.0901(13) Uani 0.889(6) d P 1 F9\b F 1.0370(4) 0.2401(3) 1.2405(3) 0.0830(11) Uani 0.889(6) d P 1 C8' C 0.8572(20) 0.3956(28) 1.1696(27) 0.0620(12) Uani 0.111(6) d PD 2 F7\a' F 0.6943(43) 0.5373(29) 1.0035(27) 0.120(16) Uani 0.111(6) d P 2 F7\b' F 0.6749(28) 0.3762(29) 1.0779(41) 0.088(10) Uani 0.111(6) d P 2 F8\a' F 0.8134(52) 0.5089(38) 1.2283(35) 0.107(19) Uani 0.111(6) d PD 2 F8\b' F 0.8835(30) 0.3002(33) 1.2507(26) 0.114(12) Uani 0.111(6) d PD 2 F9\a' F 1.0134(41) 0.4565(42) 1.1106(31) 0.099(11) Uani 0.111(6) d P 2 F9\b' F 1.0968(25) 0.2915(46) 1.2231(23) 0.107(12) Uani 0.111(6) d P 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 S3 0.0389(4) 0.0817(7) 0.0581(5) -0.0088(5) 0.0085(4) -0.0259(4) S4 0.0417(4) 0.0809(7) 0.0509(5) -0.0095(4) 0.0040(3) -0.0289(4) C1 0.042(2) 0.064(2) 0.056(2) 0.002(2) -0.0024(14) -0.029(2) C2 0.0367(15) 0.050(2) 0.057(2) 0.000(2) 0.0019(14) -0.0190(14) C3a 0.040(2) 0.062(2) 0.055(2) -0.006(2) 0.0067(14) -0.027(2) C5 0.038(2) 0.053(2) 0.055(2) 0.005(2) 0.0017(13) -0.0247(14) C6 0.043(2) 0.070(2) 0.054(2) 0.001(2) 0.0061(14) -0.033(2) C6a 0.044(2) 0.065(2) 0.051(2) 0.000(2) 0.0067(14) -0.031(2) C6b 0.042(2) 0.067(2) 0.051(2) 0.000(2) 0.0048(14) -0.028(2) C7 0.049(2) 0.083(3) 0.051(2) 0.001(2) 0.006(2) -0.032(2) C9 0.053(2) 0.073(3) 0.056(2) -0.003(2) 0.001(2) -0.030(2) C9a 0.043(2) 0.069(2) 0.050(2) 0.000(2) 0.0008(14) -0.030(2) C9b 0.045(2) 0.062(2) 0.047(2) 0.001(2) 0.0026(14) -0.027(2) C9c 0.040(2) 0.061(2) 0.052(2) -0.001(2) 0.0024(13) -0.027(2) C10 0.059(2) 0.058(2) 0.077(3) 0.008(2) 0.005(2) -0.031(2) C11 0.060(2) 0.058(2) 0.067(2) 0.005(2) 0.003(2) -0.034(2) C12 0.037(2) 0.051(2) 0.071(2) 0.011(2) -0.0018(15) -0.0210(15) C13 0.050(2) 0.072(3) 0.079(3) 0.001(2) 0.003(2) -0.033(2) C14 0.051(2) 0.086(3) 0.100(3) 0.013(3) -0.003(2) -0.042(2) C15 0.041(2) 0.079(3) 0.115(4) 0.023(3) 0.005(2) -0.031(2) C16 0.048(2) 0.079(3) 0.108(4) 0.003(3) 0.024(2) -0.024(2) C17 0.049(2) 0.070(3) 0.082(3) -0.006(2) 0.015(2) -0.028(2) C18 0.043(2) 0.056(2) 0.055(2) 0.005(2) -0.0020(14) -0.024(2) C19 0.046(2) 0.083(3) 0.069(2) 0.003(2) 0.004(2) -0.034(2) C20 0.040(2) 0.090(3) 0.084(3) 0.001(2) 0.001(2) -0.030(2) C21 0.050(2) 0.090(3) 0.075(3) 0.005(2) -0.014(2) -0.029(2) C22 0.060(2) 0.131(4) 0.062(2) 0.022(3) -0.016(2) -0.045(3) C23 0.053(2) 0.106(3) 0.056(2) 0.014(2) -0.005(2) -0.042(2) C8 0.059(2) 0.062(3) 0.065(3) -0.009(2) 0.012(2) -0.031(2) F7\a 0.0466(15) 0.098(3) 0.077(2) -0.002(2) 0.0019(12) -0.016(2) F7\b 0.094(3) 0.110(3) 0.071(2) -0.004(2) 0.030(2) -0.067(2) F8\a 0.079(2) 0.061(2) 0.139(3) 0.000(2) 0.005(2) -0.0348(15) F8\b 0.073(2) 0.130(4) 0.056(3) -0.027(2) 0.015(2) -0.038(2) F9\a 0.068(2) 0.113(4) 0.101(4) -0.034(3) 0.010(2) -0.060(2) F9\b 0.081(2) 0.089(2) 0.052(2) 0.0066(14) -0.0013(14) -0.025(2) C8' 0.059(2) 0.062(3) 0.065(3) -0.009(2) 0.012(2) -0.031(2) F7\a' 0.145(35) 0.067(19) 0.059(15) 0.002(13) 0.017(19) 0.014(18) F7\b' 0.053(15) 0.064(18) 0.146(30) 0.006(17) 0.056(17) -0.015(12) F8\a' 0.091(21) 0.166(42) 0.037(19) -0.075(25) 0.043(18) -0.044(29) F8\b' 0.129(25) 0.154(29) 0.086(17) 0.059(18) -0.003(15) -0.086(22) F9\a' 0.129(29) 0.135(30) 0.078(19) -0.033(19) 0.017(18) -0.103(25) F9\b' 0.062(15) 0.186(36) 0.046(13) 0.031(16) -0.036(11) -0.050(20) #========================================================= # 10. MOLECULAR GEOMETRY _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 S3 C2 1.769(3) . yes S3 C3a 1.844(3) . yes S4 C5 1.768(3) . yes S4 C3a 1.845(3) . yes C1 C2 1.348(5) . yes C1 C9b 1.420(4) . yes C2 C12 1.484(4) . yes C3a C9c 1.509(5) . yes C3a C10 1.524(5) . yes C5 C6 1.348(5) . yes C5 C18 1.481(4) . yes C6 C6a 1.427(4) . yes C6a C6b 1.355(5) . yes C6a C9c 1.534(4) . yes C6b C9a 1.451(4) . yes C6b C7 1.475(5) . yes C7 F7\b' 1.18(3) . yes C7 F7\a 1.330(5) . yes C7 F7\b 1.386(5) . yes C7 C8' 1.51(2) . yes C7 C8 1.532(6) . yes C7 F7\a' 1.63(3) . yes C9 F9\b' 1.19(2) . yes C9 F9\a 1.321(5) . yes C9 F9\b 1.386(5) . yes C9 C9a 1.471(5) . yes C9 C8' 1.51(2) . yes C9 C8 1.555(6) . yes C9 F9\a' 1.67(3) . yes C9a C9b 1.357(5) . yes C9b C9c 1.521(4) . yes C9c C11 1.547(5) . yes C12 C17 1.373(5) . yes C12 C13 1.387(5) . yes C13 C14 1.389(5) . yes C14 C15 1.360(6) . yes C15 C16 1.366(6) . yes C16 C17 1.387(5) . yes C18 C23 1.366(5) . yes C18 C19 1.393(5) . yes C19 C20 1.374(5) . yes C20 C21 1.364(6) . yes C21 C22 1.362(6) . yes C22 C23 1.380(5) . yes C8 F8\b 1.332(6) . yes C8 F8\a 1.342(6) . yes C8' F8\a' 1.30(2) . yes C8' F8\b' 1.34(2) . 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_3 _geom_angle_publ_flag C2 S3 C3a 100.2(2) . . yes C5 S4 C3a 100.3(2) . . yes C2 C1 C9b 123.9(3) . . yes C1 C2 C12 121.6(3) . . yes C1 C2 S3 124.7(2) . . yes C12 C2 S3 113.7(2) . . yes C9c C3a C10 113.7(3) . . yes C9c C3a S3 108.9(2) . . yes C10 C3a S3 109.2(2) . . yes C9c C3a S4 108.4(2) . . yes C10 C3a S4 109.7(2) . . yes S3 C3a S4 106.9(2) . . yes C6 C5 C18 121.9(3) . . yes C6 C5 S4 123.9(2) . . yes C18 C5 S4 114.2(2) . . yes C5 C6 C6a 123.7(3) . . yes C6b C6a C6 132.1(3) . . yes C6b C6a C9c 106.7(3) . . yes C6 C6a C9c 121.0(3) . . yes C6a C6b C9a 110.7(3) . . yes C6a C6b C7 139.0(3) . . yes C9a C6b C7 110.1(3) . . yes F7\a C7 F7\b 104.5(4) . . yes F7\b' C7 C6b 126.4(17) . . yes F7\a C7 C6b 116.0(3) . . yes F7\b C7 C6b 110.6(4) . . yes F7\b' C7 C8' 113.1(23) . . yes C6b C7 C8' 105.3(10) . . yes F7\a C7 C8 113.3(4) . . yes F7\b C7 C8 108.6(3) . . yes C6b C7 C8 103.8(3) . . yes F7\b' C7 F7\a' 104.4(21) . . yes C6b C7 F7\a' 107.5(12) . . yes C8' C7 F7\a' 95.7(18) . . yes F9\a C9 F9\b 106.0(4) . . yes F9\b' C9 C9a 126.2(16) . . yes F9\a C9 C9a 116.0(4) . . yes F9\b C9 C9a 112.2(3) . . yes F9\b' C9 C8' 123.1(18) . . yes C9a C9 C8' 105.7(10) . . yes F9\a C9 C8 112.6(4) . . yes F9\b C9 C8 106.1(3) . . yes C9a C9 C8 103.7(3) . . yes F9\b' C9 F9\a' 89.8(25) . . yes C9a C9 F9\a' 103.8(10) . . yes C8' C9 F9\a' 99.9(18) . . yes C9b C9a C6b 110.2(3) . . yes C9b C9a C9 139.5(3) . . yes C6b C9a C9 109.8(3) . . yes C9a C9b C1 133.2(3) . . yes C9a C9b C9c 107.2(3) . . yes C1 C9b C9c 119.6(3) . . yes C3a C9c C9b 111.0(3) . . yes C3a C9c C6a 109.6(3) . . yes C9b C9c C6a 103.5(3) . . yes C3a C9c C11 114.6(3) . . yes C9b C9c C11 108.3(3) . . yes C6a C9c C11 109.3(3) . . yes C17 C12 C13 118.2(3) . . yes C17 C12 C2 122.1(3) . . yes C13 C12 C2 119.7(3) . . yes C12 C13 C14 120.3(4) . . yes C15 C14 C13 120.4(4) . . yes C14 C15 C16 120.2(4) . . yes C15 C16 C17 119.7(4) . . yes C12 C17 C16 121.3(4) . . yes C23 C18 C19 118.0(3) . . yes C23 C18 C5 121.5(3) . . yes C19 C18 C5 120.5(3) . . yes C20 C19 C18 120.1(4) . . yes C21 C20 C19 121.2(4) . . yes C22 C21 C20 118.9(4) . . yes C21 C22 C23 120.6(4) . . yes C18 C23 C22 121.2(4) . . yes F8\b C8 F8\a 108.7(4) . . yes F8\b C8 C7 114.7(5) . . yes F8\a C8 C7 106.7(4) . . yes F8\b C8 C9 114.1(5) . . yes F8\a C8 C9 106.7(4) . . yes C7 C8 C9 105.4(4) . . yes F8\a' C8' F8\b' 113.0(33) . . yes F8\a' C8' C9 118.1(28) . . yes F8\b' C8' C9 92.9(18) . . yes F8\a' C8' C7 116.2(27) . . yes F8\b' C8' C7 104.6(20) . . yes C9 C8' C7 108.9(17) . . yes 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 C9b C1 C2 C12 177.5(3) . . . . yes C9b C1 C2 S3 -0.8(5) . . . . yes C3a S3 C2 C1 17.0(4) . . . . yes C3a S3 C2 C12 -161.5(2) . . . . yes C2 S3 C3a C9c -47.1(3) . . . . yes C2 S3 C3a C10 77.5(3) . . . . yes C2 S3 C3a S4 -163.9(2) . . . . yes C5 S4 C3a C9c 50.7(3) . . . . yes C5 S4 C3a C10 -73.9(3) . . . . yes C5 S4 C3a S3 167.9(2) . . . . yes C3a S4 C5 C6 -18.6(3) . . . . yes C3a S4 C5 C18 160.6(3) . . . . yes C18 C5 C6 C6a 179.9(3) . . . . yes S4 C5 C6 C6a -1.0(5) . . . . yes C5 C6 C6a C6b 165.3(4) . . . . yes C5 C6 C6a C9c -9.8(5) . . . . yes C6 C6a C6b C9a -169.0(4) . . . . yes C9c C6a C6b C9a 6.7(4) . . . . yes C6 C6a C6b C7 5.4(8) . . . . yes C9c C6a C6b C7 -178.9(4) . . . . yes C6a C6b C7 F7\b' 48.8(25) . . . . yes C9a C6b C7 F7\b' -136.8(24) . . . . yes C6a C6b C7 F7\a -32.4(7) . . . . yes C9a C6b C7 F7\a 142.0(4) . . . . yes C6a C6b C7 F7\b 86.4(6) . . . . yes C9a C6b C7 F7\b -99.2(4) . . . . yes C6a C6b C7 C8' -176.2(13) . . . . yes C9a C6b C7 C8' -1.8(12) . . . . yes C6a C6b C7 C8 -157.4(5) . . . . yes C9a C6b C7 C8 17.1(4) . . . . yes C6a C6b C7 F7\a' -75.0(19) . . . . yes C9a C6b C7 F7\a' 99.4(18) . . . . yes C6a C6b C9a C9b 1.4(5) . . . . yes C7 C6b C9a C9b -174.7(3) . . . . yes C6a C6b C9a C9 175.1(3) . . . . yes C7 C6b C9a C9 -0.9(4) . . . . yes F9\b' C9 C9a C9b -30.6(32) . . . . yes F9\a C9 C9a C9b 31.6(7) . . . . yes F9\b C9 C9a C9b -90.4(6) . . . . yes C8' C9 C9a C9b 174.2(13) . . . . yes C8 C9 C9a C9b 155.5(5) . . . . yes F9\a' C9 C9a C9b 69.5(16) . . . . yes F9\b' C9 C9a C6b 158.5(32) . . . . yes F9\a C9 C9a C6b -139.3(4) . . . . yes F9\b C9 C9a C6b 98.7(4) . . . . yes C8' C9 C9a C6b 3.3(13) . . . . yes C8 C9 C9a C6b -15.4(4) . . . . yes F9\a' C9 C9a C6b -101.4(15) . . . . yes C6b C9a C9b C1 169.5(4) . . . . yes C9 C9a C9b C1 -1.3(8) . . . . yes C6b C9a C9b C9c -9.0(4) . . . . yes C9 C9a C9b C9c -179.8(5) . . . . yes C2 C1 C9b C9a -164.5(4) . . . . yes C2 C1 C9b C9c 13.9(5) . . . . yes C10 C3a C9c C9b -57.1(4) . . . . yes S3 C3a C9c C9b 64.8(3) . . . . yes S4 C3a C9c C9b -179.3(2) . . . . yes C10 C3a C9c C6a 56.7(4) . . . . yes S3 C3a C9c C6a 178.6(2) . . . . yes S4 C3a C9c C6a -65.5(3) . . . . yes C10 C3a C9c C11 179.9(3) . . . . yes S3 C3a C9c C11 -58.2(3) . . . . yes S4 C3a C9c C11 57.7(3) . . . . yes C9a C9b C9c C3a 129.9(3) . . . . yes C1 C9b C9c C3a -48.9(4) . . . . yes C9a C9b C9c C6a 12.4(4) . . . . yes C1 C9b C9c C6a -166.4(3) . . . . yes C9a C9b C9c C11 -103.5(3) . . . . yes C1 C9b C9c C11 77.7(4) . . . . yes C6b C6a C9c C3a -130.0(3) . . . . yes C6 C6a C9c C3a 46.3(4) . . . . yes C6b C6a C9c C9b -11.5(4) . . . . yes C6 C6a C9c C9b 164.8(3) . . . . yes C6b C6a C9c C11 103.7(3) . . . . yes C6 C6a C9c C11 -80.0(4) . . . . yes C1 C2 C12 C17 152.4(4) . . . . yes S3 C2 C12 C17 -29.1(4) . . . . yes C1 C2 C12 C13 -27.9(5) . . . . yes S3 C2 C12 C13 150.6(3) . . . . yes C17 C12 C13 C14 -1.2(6) . . . . yes C2 C12 C13 C14 179.1(4) . . . . yes C12 C13 C14 C15 1.6(6) . . . . yes C13 C14 C15 C16 -1.0(7) . . . . yes C14 C15 C16 C17 0.1(7) . . . . yes C13 C12 C17 C16 0.4(6) . . . . yes C2 C12 C17 C16 -180.0(4) . . . . yes C15 C16 C17 C12 0.2(7) . . . . yes C6 C5 C18 C23 154.5(4) . . . . yes S4 C5 C18 C23 -24.7(5) . . . . yes C6 C5 C18 C19 -24.4(5) . . . . yes S4 C5 C18 C19 156.4(3) . . . . yes C23 C18 C19 C20 -2.1(6) . . . . yes C5 C18 C19 C20 176.8(4) . . . . yes C18 C19 C20 C21 2.1(7) . . . . yes C19 C20 C21 C22 -1.2(7) . . . . yes C20 C21 C22 C23 0.3(8) . . . . yes C19 C18 C23 C22 1.2(7) . . . . yes C5 C18 C23 C22 -177.7(4) . . . . yes C21 C22 C23 C18 -0.3(8) . . . . yes F7\b' C7 C8 F8\b 2.4(19) . . . . yes F7\a C7 C8 F8\b 81.1(6) . . . . yes F7\b C7 C8 F8\b -34.6(6) . . . . yes C6b C7 C8 F8\b -152.3(5) . . . . yes C8' C7 C8 F8\b -55.3(33) . . . . yes F7\a' C7 C8 F8\b 102.2(14) . . . . yes F7\b' C7 C8 F8\a -118.0(19) . . . . yes F7\a C7 C8 F8\a -39.3(5) . . . . yes F7\b C7 C8 F8\a -154.9(4) . . . . yes C6b C7 C8 F8\a 87.3(4) . . . . yes C8' C7 C8 F8\a -175.7(34) . . . . yes F7\a' C7 C8 F8\a -18.1(14) . . . . yes F7\b' C7 C8 C9 128.7(19) . . . . yes F7\a C7 C8 C9 -152.5(4) . . . . yes F7\b C7 C8 C9 91.8(5) . . . . yes C6b C7 C8 C9 -25.9(4) . . . . yes C8' C7 C8 C9 71.1(32) . . . . yes F7\a' C7 C8 C9 -131.4(14) . . . . yes F9\b' C9 C8 F8\b -21.4(34) . . . . yes F9\a C9 C8 F8\b -81.7(6) . . . . yes F9\b C9 C8 F8\b 33.9(6) . . . . yes C9a C9 C8 F8\b 152.2(5) . . . . yes C8' C9 C8 F8\b 53.5(33) . . . . yes F9\a' C9 C8 F8\b -105.2(11) . . . . yes F9\b' C9 C8 F8\a 98.6(34) . . . . yes F9\a C9 C8 F8\a 38.3(5) . . . . yes F9\b C9 C8 F8\a 153.9(3) . . . . yes C9a C9 C8 F8\a -87.8(4) . . . . yes C8' C9 C8 F8\a 173.5(35) . . . . yes F9\a' C9 C8 F8\a 14.8(11) . . . . yes F9\b' C9 C8 C7 -148.1(34) . . . . yes F9\a C9 C8 C7 151.6(4) . . . . yes F9\b C9 C8 C7 -92.9(4) . . . . yes C9a C9 C8 C7 25.4(4) . . . . yes C8' C9 C8 C7 -73.3(33) . . . . yes F9\a' C9 C8 C7 128.0(11) . . . . yes F9\b' C9 C8' F8\a' 63.9(42) . . . . yes F9\a C9 C8' F8\a' -1.5(34) . . . . yes F9\b C9 C8' F8\a' 107.3(28) . . . . yes C9a C9 C8' F8\a' -139.9(27) . . . . yes C8 C9 C8' F8\a' -53.8(31) . . . . yes F9\a' C9 C8' F8\a' -32.4(31) . . . . yes F9\b' C9 C8' F8\b' -54.1(38) . . . . yes F9\a C9 C8' F8\b' -119.5(17) . . . . yes F9\b C9 C8' F8\b' -10.7(17) . . . . yes C9a C9 C8' F8\b' 102.1(18) . . . . yes C8 C9 C8' F8\b' -171.9(45) . . . . yes F9\a' C9 C8' F8\b' -150.4(20) . . . . yes F9\b' C9 C8' C7 -160.6(33) . . . . yes F9\a C9 C8' C7 134.0(12) . . . . yes F9\b C9 C8' C7 -117.2(16) . . . . yes C9a C9 C8' C7 -4.4(20) . . . . yes C8 C9 C8' C7 81.6(33) . . . . yes F9\a' C9 C8' C7 103.1(20) . . . . yes F7\b' C7 C8' F8\a' -78.0(32) . . . . yes F7\a C7 C8' F8\a' 1.2(35) . . . . yes F7\b C7 C8' F8\a' -107.9(29) . . . . yes C6b C7 C8' F8\a' 140.3(28) . . . . yes C8 C7 C8' F8\a' 52.5(30) . . . . yes F7\a' C7 C8' F8\a' 30.4(32) . . . . yes F7\b' C7 C8' F8\b' 47.3(27) . . . . yes F7\a C7 C8' F8\b' 126.4(18) . . . . yes F7\b C7 C8' F8\b' 17.4(20) . . . . yes C6b C7 C8' F8\b' -94.4(20) . . . . yes C8 C7 C8' F8\b' 177.8(47) . . . . yes F7\a' C7 C8' F8\b' 155.7(24) . . . . yes F7\b' C7 C8' C9 145.6(21) . . . . yes F7\a C7 C8' C9 -135.3(12) . . . . yes F7\b C7 C8' C9 115.7(16) . . . . yes C6b C7 C8' C9 3.9(19) . . . . yes C8 C7 C8' C9 -83.9(34) . . . . yes F7\a' C7 C8' C9 -106.1(22) . . . . yes #=END