#------------------------------------------------------------------------------ #$Date: 2018-05-25 17:24:38 +0300 (Fri, 25 May 2018) $ #$Revision: 207983 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549466.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1549466 loop_ _publ_author_name 'Inagaki, Yuki' 'Mutoh, Katsuya' 'Abe, Jiro' _publ_section_title ; Stepwise Photochromism of Bisnaphthopyrans Exhibiting Excitation Intensity-Dependent Color Change ; _journal_name_full 'Photochemical & Photobiological Sciences' _journal_paper_doi 10.1039/C8PP00205C _journal_year 2018 _chemical_formula_sum 'C38 H22.2 O2' _chemical_formula_weight 510.76 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2018-03-24 deposited with the CCDC. 2018-05-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.039(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.538(2) _cell_length_b 9.367(3) _cell_length_c 18.374(5) _cell_measurement_reflns_used 1954 _cell_measurement_temperature 90.0 _cell_measurement_theta_max 26.3816 _cell_measurement_theta_min 2.4485 _cell_volume 1277.5(6) _computing_cell_refinement 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_data_collection 'Bruker SMART APEXII' _computing_data_reduction 'SAINT V8.32B (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'XSHELL V6.3.1 (Bruker AXS)' _computing_publication_material 'Generate Report (Bruker AXS)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 90.0 _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 goniometer' _diffrn_measurement_method 'omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6578 _diffrn_reflns_theta_full 26.44 _diffrn_reflns_theta_max 26.44 _diffrn_reflns_theta_min 2.25 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.543 _refine_diff_density_min -0.499 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 60 _refine_ls_number_reflns 2616 _refine_ls_number_restraints 150 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0740 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0865P)^2^+1.9110P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1853 _refine_ls_wR_factor_ref 0.2043 _reflns_number_gt 1934 _reflns_number_total 2616 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8pp00205c3.cif _cod_data_source_block I _cod_original_formula_sum 'C38 H22.20 O2' _cod_database_code 1549466 _shelx_res_file ; TITL p2_1_c in P2(1)/c CELL 0.71073 7.53770 9.36700 18.37420 90.0000 100.0386 90.0000 ZERR 2.00 0.00210 0.00260 0.00520 0.0000 0.0037 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O UNIT 76 44.4 4 L.S. 10 ACTA BOND $h FMAP 2 PLAN 10 size 0.2 0.1 0.01 SIMU 0.005 C1B C2B C3B C4B C5B C6B C7B SIMU 0.005 C8B C9B C10B C11B C12B C13B O1B ISOR 0.01 C1B C2B C3B C4B C6B C7B ISOR 0.012 C8B C9B C10B C11B C12B C13B O1B ISOR 0.005 C5B TEMP -183.000 WGHT 0.086500 1.911000 FVAR 0.17911 0.89960 PART 2 AFIX 66 MOLE 1 O1B 3 0.239335 0.323100 0.023053 -21.00000 0.04421 0.03242 = 0.02455 0.00202 0.00913 -0.01265 C5B 1 0.414441 0.371399 0.046214 -21.00000 0.02530 0.02303 = 0.02359 0.00869 0.00788 -0.00303 C4B 1 0.511249 0.327487 0.113902 -21.00000 0.03059 0.02688 = 0.02618 0.01227 0.00800 -0.00684 AFIX 43 H4B 2 0.630926 0.360497 0.129731 -21.00000 -1.20000 AFIX 65 C3B 1 0.432951 0.235276 0.158430 -21.00000 0.02922 0.02548 = 0.02550 0.00781 0.00609 -0.00525 AFIX 43 H3B 2 0.499116 0.205264 0.204691 -21.00000 -1.20000 AFIX 65 C2B 1 0.257845 0.186977 0.135270 -21.00000 0.02716 0.02538 = 0.02610 0.00233 0.00532 -0.00264 C1B 1 0.161035 0.230888 0.067582 -21.00000 0.02483 0.02384 = 0.02633 0.00147 0.00823 -0.00325 AFIX 1 C6B 1 0.149306 0.096126 0.178176 -21.00000 0.02875 0.02875 = 0.02875 0.00000 0.00501 0.00000 C7B 1 0.264786 0.056163 0.246993 -21.00000 0.05015 0.05015 = 0.05015 0.00000 0.00874 0.00000 AFIX 43 H7B 2 0.385625 0.088172 0.260555 -21.00000 -1.20000 AFIX 1 C8B 1 0.166966 -0.048831 0.298625 -21.00000 0.03417 0.03417 = 0.03417 0.00000 0.00596 0.00000 AFIX 43 H8B 2 0.220270 -0.085697 0.345522 -21.00000 -1.20000 AFIX 1 C9B 1 -0.123557 -0.039449 0.199802 -21.00000 0.02198 0.02198 = 0.02198 0.00000 0.00383 0.00000 AFIX 43 H9B 2 -0.244791 -0.071200 0.187545 -21.00000 -1.20000 AFIX 1 C10B 1 -0.038075 0.058784 0.150378 -21.00000 0.04330 0.04330 = 0.04330 0.00000 0.00755 0.00000 C11B 1 -0.017665 -0.076826 0.260355 -21.00000 0.01720 0.01720 = 0.01720 0.00000 0.00300 0.00000 AFIX 43 H11B 2 -0.077106 -0.141205 0.288034 -21.00000 -1.20000 AFIX 1 C12B 1 -0.129600 0.100878 0.084421 -21.00000 0.04212 0.04212 = 0.04212 0.00000 0.00734 0.00000 AFIX 43 H12B 2 -0.251393 0.074852 0.066956 -21.00000 -1.20000 AFIX 1 C13B 1 -0.007100 0.205990 0.034345 -21.00000 0.05437 0.05437 = 0.05437 0.00000 0.00948 0.00000 AFIX 43 H13B 2 -0.055698 0.243055 -0.013071 -21.00000 -1.20000 PART 1 AFIX 1 C1A 1 -0.079453 -0.076729 0.242424 21.00000 0.03130 0.03130 = 0.03130 0.00000 0.00546 0.00000 AFIX 43 H1A 2 -0.140037 -0.136608 0.271892 21.00000 -1.20000 AFIX 1 C2A 1 0.097742 -0.035352 0.267903 21.00000 0.02825 0.02825 = 0.02825 0.00000 0.00492 0.00000 AFIX 43 H2A 2 0.158571 -0.067914 0.314607 21.00000 -1.20000 AFIX 1 C3A 1 -0.168636 -0.029673 0.172930 21.00000 0.03069 0.03069 = 0.03069 0.00000 0.00535 0.00000 AFIX 43 H3A 2 -0.289579 -0.058436 0.155834 21.00000 -1.20000 AFIX 1 C4A 1 -0.083663 0.057604 0.129052 21.00000 0.02678 0.02678 = 0.02678 0.00000 0.00467 0.00000 C5A 1 0.096059 0.103259 0.152759 21.00000 0.01928 0.01928 = 0.01928 0.00000 0.00336 0.00000 C6A 1 0.187359 0.054785 0.224615 21.00000 0.02164 0.02164 = 0.02164 0.00000 0.00377 0.00000 C7A 1 0.369054 0.099313 0.250166 21.00000 0.02408 0.02408 = 0.02408 0.00000 0.00420 0.00000 AFIX 43 H7A 2 0.430386 0.068032 0.297038 21.00000 -1.20000 AFIX 1 C8A 1 0.455317 0.186261 0.207949 21.00000 0.02101 0.02101 = 0.02101 0.00000 0.00366 0.00000 AFIX 43 H8A 2 0.575886 0.215516 0.225440 21.00000 -1.20000 AFIX 1 C9A 1 0.364225 0.232691 0.137917 21.00000 0.01679 0.01679 = 0.01679 0.00000 0.00293 0.00000 C10A 1 0.190096 0.191778 0.109953 21.00000 0.01728 0.01728 = 0.01728 0.00000 0.00301 0.00000 C11A 1 0.111756 0.244623 0.036183 21.00000 0.02175 0.02175 = 0.02175 0.00000 0.00379 0.00000 AFIX 43 H11A 2 -0.006035 0.215235 0.014170 21.00000 -1.20000 AFIX 1 C12A 1 0.202628 0.332793 -0.000335 21.00000 0.02078 0.02078 = 0.02078 0.00000 0.00362 0.00000 AFIX 43 H12A 2 0.148166 0.361749 -0.048629 21.00000 -1.20000 AFIX 1 C13A 1 0.388657 0.389823 0.030838 21.00000 0.01733 0.01733 = 0.01733 0.00000 0.00302 0.00000 O1A 3 0.467041 0.317251 0.100839 21.00000 0.02000 0.02000 = 0.02000 0.00000 0.00349 0.00000 PART 0 C8 1 0.518835 0.352322 -0.020284 11.00000 0.01823 0.01823 = 0.01823 0.00000 0.00318 0.00000 C9 1 0.620526 0.455041 -0.049245 11.00000 0.01816 0.01816 = 0.01816 0.00000 0.00317 0.00000 C17 1 0.736724 0.413185 -0.097563 11.00000 0.02301 0.02301 = 0.02301 0.00000 0.00401 0.00000 C18 1 0.534726 0.209575 -0.039930 11.00000 0.02633 0.02633 = 0.02633 0.00000 0.00459 0.00000 C19 1 0.649032 0.168255 -0.088073 11.00000 0.02969 0.02969 = 0.02969 0.00000 0.00518 0.00000 C20 1 0.750717 0.271324 -0.116867 11.00000 0.02730 0.02730 = 0.02730 0.00000 0.00476 0.00000 AFIX 0 H10 2 0.808029 0.474501 -0.114130 11.00000 0.03282 H7 2 0.464485 0.140006 -0.019727 11.00000 0.03148 H8 2 0.650767 0.058609 -0.100957 11.00000 0.04515 H20 2 0.838157 0.241376 -0.150186 11.00000 0.03235 HKLF 4 REM p2_1_c in P2(1)/c REM R1 = 0.0740 for 1934 Fo > 4sig(Fo) and 0.0993 for all 2616 data REM 60 parameters refined using 150 restraints END WGHT 0.0862 1.9158 REM Highest difference peak 0.543, deepest hole -0.499, 1-sigma level 0.069 Q1 1 0.6960 0.2222 -0.1131 11.00000 0.05 0.49 Q2 1 0.0388 -0.0193 0.2544 11.00000 0.05 0.49 Q3 1 0.1525 0.0783 0.1987 11.00000 0.05 0.45 Q4 1 -0.1282 -0.0573 0.2194 11.00000 0.05 0.43 Q5 1 0.4689 0.2741 0.0805 11.00000 0.05 0.38 Q6 1 0.6182 0.1521 -0.0687 11.00000 0.05 0.33 Q7 1 -0.2131 0.0010 0.1503 11.00000 0.05 0.33 Q8 1 0.4845 0.2191 -0.0675 11.00000 0.05 0.30 Q9 1 0.0345 0.0844 0.1441 11.00000 0.05 0.30 Q10 1 -0.0088 0.1812 0.0527 11.00000 0.05 0.26 ; _shelx_res_checksum 18288 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1B 0.2393(18) 0.3231(16) 0.0231(7) 0.033(5) Uani d U P G 0.100(4) A 2 C C5B 0.4144(19) 0.3714(17) 0.0462(8) 0.024(4) Uani d U P G 0.100(4) A 2 C C4B 0.5112(17) 0.3275(19) 0.1139(9) 0.028(3) Uani d U P G 0.100(4) A 2 H H4B 0.6309 0.3605 0.1297 0.033 Uiso calc U P R 0.100(4) A 2 C C3B 0.433(2) 0.2353(19) 0.1584(7) 0.027(3) Uani d U P G 0.100(4) A 2 H H3B 0.4991 0.2053 0.2047 0.032 Uiso calc U P R 0.100(4) A 2 C C2B 0.258(2) 0.1870(17) 0.1353(8) 0.026(2) Uani d U P G 0.100(4) A 2 C C1B 0.1610(16) 0.2309(17) 0.0676(8) 0.025(3) Uani d U P G 0.100(4) A 2 C C6B 0.1493 0.0961 0.1782 0.029 Uani d U P . 0.1004 A 2 C C7B 0.2648 0.0562 0.247 0.05 Uani d U P . 0.1004 A 2 H H7B 0.3856 0.0882 0.2606 0.06 Uiso calc U P R 0.100(4) A 2 C C8B 0.167 -0.0488 0.2986 0.034 Uani d U P . 0.1004 A 2 H H8B 0.2203 -0.0857 0.3455 0.041 Uiso calc U P R 0.100(4) A 2 C C9B -0.1236 -0.0394 0.1998 0.022 Uani d U P . 0.1004 A 2 H H9B -0.2448 -0.0712 0.1875 0.026 Uiso calc U P R 0.100(4) A 2 C C10B -0.0381 0.0588 0.1504 0.043 Uani d U P . 0.1004 A 2 C C11B -0.0177 -0.0768 0.2604 0.017 Uani d U P . 0.1004 A 2 H H11B -0.0771 -0.1412 0.288 0.021 Uiso calc U P R 0.100(4) A 2 C C12B -0.1296 0.1009 0.0844 0.042 Uani d U P . 0.1004 A 2 H H12B -0.2514 0.0749 0.067 0.051 Uiso calc U P R 0.100(4) A 2 C C13B -0.0071 0.206 0.0343 0.054 Uani d U P . 0.1004 A 2 H H13B -0.0557 0.2431 -0.0131 0.065 Uiso calc U P R 0.100(4) A 2 C C1A -0.0795 -0.0767 0.2424 0.031 Uani d . P . 0.8996 A 1 H H1A -0.14 -0.1366 0.2719 0.038 Uiso calc U P R 0.900(4) A 1 C C2A 0.0977 -0.0354 0.2679 0.028 Uani d . P . 0.8996 A 1 H H2A 0.1586 -0.0679 0.3146 0.034 Uiso calc U P R 0.900(4) A 1 C C3A -0.1686 -0.0297 0.1729 0.031 Uani d . P . 0.8996 A 1 H H3A -0.2896 -0.0584 0.1558 0.037 Uiso calc U P R 0.900(4) A 1 C C4A -0.0837 0.0576 0.1291 0.027 Uani d . P . 0.8996 A 1 C C5A 0.0961 0.1033 0.1528 0.019 Uani d . P . 0.8996 A 1 C C6A 0.1874 0.0548 0.2246 0.022 Uani d . P . 0.8996 A 1 C C7A 0.3691 0.0993 0.2502 0.024 Uani d . P . 0.8996 A 1 H H7A 0.4304 0.068 0.297 0.029 Uiso calc U P R 0.900(4) A 1 C C8A 0.4553 0.1863 0.2079 0.021 Uani d . P . 0.8996 A 1 H H8A 0.5759 0.2155 0.2254 0.025 Uiso calc U P R 0.900(4) A 1 C C9A 0.3642 0.2327 0.1379 0.017 Uani d . P . 0.8996 A 1 C C10A 0.1901 0.1918 0.11 0.017 Uani d . P . 0.8996 A 1 C C11A 0.1118 0.2446 0.0362 0.022 Uani d . P . 0.8996 A 1 H H11A -0.006 0.2152 0.0142 0.026 Uiso calc U P R 0.900(4) A 1 C C12A 0.2026 0.3328 -0.0003 0.021 Uani d . P . 0.8996 A 1 H H12A 0.1482 0.3617 -0.0486 0.025 Uiso calc U P R 0.900(4) A 1 C C13A 0.3887 0.3898 0.0308 0.017 Uani d . P . 0.8996 A 1 O O1A 0.467 0.3173 0.1008 0.02 Uani d . P . 0.8996 A 1 C C8 0.5188 0.3523 -0.0203 0.018 Uani d . . . 1.0 . . C C9 0.6205 0.455 -0.0492 0.018 Uani d . . . 1.0 . . C C17 0.7367 0.4132 -0.0976 0.023 Uani d . . . 1.0 . . C C18 0.5347 0.2096 -0.0399 0.026 Uani d . . . 1.0 . . C C19 0.649 0.1683 -0.0881 0.03 Uani d . . . 1.0 . . C C20 0.7507 0.2713 -0.1169 0.027 Uani d . . . 1.0 . . H H10 0.8080(15) 0.4745(12) -0.1141(6) 0.033(8) Uiso d . . . 1.0 . . H H7 0.464(4) 0.140(3) -0.0197(16) 0.031(8) Uiso d . . . 1.0 . . H H8 0.651(4) 0.059(4) -0.1010(19) 0.045(9) Uiso d . . . 1.0 . . H H20 0.838(4) 0.241(3) -0.1502(17) 0.032(8) Uiso d . . . 1.0 . . 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 O1B 0.044(9) 0.032(9) 0.025(8) -0.013(7) 0.009(7) 0.002(7) C5B 0.025(5) 0.023(5) 0.024(5) -0.003(4) 0.008(4) 0.009(4) C4B 0.031(5) 0.027(5) 0.026(5) -0.007(4) 0.008(4) 0.012(4) C3B 0.029(5) 0.025(5) 0.026(5) -0.005(4) 0.006(4) 0.008(4) C2B 0.027(4) 0.025(4) 0.026(4) -0.003(3) 0.005(3) 0.002(3) C1B 0.025(5) 0.024(5) 0.026(5) -0.003(5) 0.008(5) 0.001(5) C6B 0.029 0.029 0.029 0 0.005 0 C7B 0.05 0.05 0.05 0 0.009 0 C8B 0.034 0.034 0.034 0 0.006 0 C9B 0.022 0.022 0.022 0 0.004 0 C10B 0.043 0.043 0.043 0 0.008 0 C11B 0.017 0.017 0.017 0 0.003 0 C12B 0.042 0.042 0.042 0 0.007 0 C13B 0.054 0.054 0.054 0 0.009 0 C1A 0.031 0.031 0.031 0 0.005 0 C2A 0.028 0.028 0.028 0 0.005 0 C3A 0.031 0.031 0.031 0 0.005 0 C4A 0.027 0.027 0.027 0 0.005 0 C5A 0.019 0.019 0.019 0 0.003 0 C6A 0.022 0.022 0.022 0 0.004 0 C7A 0.024 0.024 0.024 0 0.004 0 C8A 0.021 0.021 0.021 0 0.004 0 C9A 0.017 0.017 0.017 0 0.003 0 C10A 0.017 0.017 0.017 0 0.003 0 C11A 0.022 0.022 0.022 0 0.004 0 C12A 0.021 0.021 0.021 0 0.004 0 C13A 0.017 0.017 0.017 0 0.003 0 O1A 0.02 0.02 0.02 0 0.003 0 C8 0.018 0.018 0.018 0 0.003 0 C9 0.018 0.018 0.018 0 0.003 0 C17 0.023 0.023 0.023 0 0.004 0 C18 0.026 0.026 0.026 0 0.005 0 C19 0.03 0.03 0.03 0 0.005 0 C20 0.027 0.027 0.027 0 0.005 0 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C5B O1B C1B . . 120.0 C4B C5B O1B . . 120.0 C4B C5B C8 . . 113.9(9) O1B C5B C8 . . 107.6(9) C4B C5B C9 . 3_665 108.9(8) O1B C5B C9 . 3_665 100.5(9) C8 C5B C9 . 3_665 104.0(6) C5B C4B C3B . . 120.0 C5B C4B H4B . . 120.0 C3B C4B H4B . . 120.0 C2B C3B C4B . . 120.0 C2B C3B H3B . . 120.0 C4B C3B H3B . . 120.0 C1B C2B C3B . . 120.0 C1B C2B C6B . . 112.9(9) C3B C2B C6B . . 126.9(9) C13B C1B C2B . . 132.0(9) C13B C1B O1B . . 107.9(9) C2B C1B O1B . . 120.0 C7B C6B C10B . . 129.8 C7B C6B C2B . . 107.8(6) C10B C6B C2B . . 122.5(6) C6B C7B C8B . . 113.5 C6B C7B H7B . . 123.2 C8B C7B H7B . . 123.2 C11B C8B C7B . . 108.4 C11B C8B H8B . . 125.8 C7B C8B H8B . . 125.8 C11B C9B C10B . . 114.5 C11B C9B H9B . . 122.7 C10B C9B H9B . . 122.7 C12B C10B C6B . . 124.0 C12B C10B C9B . . 120.9 C6B C10B C9B . . 115.0 C9B C11B C8B . . 138.7 C9B C11B H11B . . 110.7 C8B C11B H11B . . 110.7 C10B C12B C13B . . 114.2 C10B C12B H12B . . 122.9 C13B C12B H12B . . 122.9 C1B C13B C12B . . 114.4(6) C1B C13B H13B . . 122.8 C12B C13B H13B . . 122.8 C2A C1A C3A . . 119.8 C2A C1A H1A . . 120.1 C3A C1A H1A . . 120.1 C1A C2A C6A . . 120.2 C1A C2A H2A . . 119.9 C6A C2A H2A . . 119.9 C4A C3A C1A . . 121.2 C4A C3A H3A . . 119.4 C1A C3A H3A . . 119.4 C3A C4A C5A . . 121.0 C4A C5A C10A . . 123.5 C4A C5A C6A . . 117.5 C10A C5A C6A . . 119.0 C2A C6A C7A . . 121.0 C2A C6A C5A . . 120.2 C7A C6A C5A . . 118.8 C8A C7A C6A . . 120.7 C8A C7A H7A . . 119.6 C6A C7A H7A . . 119.6 C7A C8A C9A . . 119.7 C7A C8A H8A . . 120.1 C9A C8A H8A . . 120.1 O1A C9A C10A . . 124.1 O1A C9A C8A . . 113.7 C10A C9A C8A . . 122.2 C9A C10A C5A . . 119.5 C9A C10A C11A . . 117.0 C5A C10A C11A . . 123.5 C12A C11A C10A . . 121.1 C12A C11A H11A . . 119.4 C10A C11A H11A . . 119.4 C11A C12A C13A . . 123.6 C11A C12A H12A . . 118.2 C13A C12A H12A . . 118.2 O1A C13A C9 . 3_665 106.0 O1A C13A C8 . . 103.2 C9 C13A C8 3_665 . 115.2 O1A C13A C12A . . 111.6 C9 C13A C12A 3_665 . 110.6 C8 C13A C12A . . 109.9 C9A O1A C13A . . 121.5 C9 C8 C18 . . 119.0 C9 C8 C13A . . 122.4 C18 C8 C13A . . 118.5 C9 C8 C5B . . 126.9(5) C18 C8 C5B . . 112.7(5) C8 C9 C17 . . 119.6 C8 C9 C13A . 3_665 122.3 C17 C9 C13A . 3_665 118.1 C8 C9 C5B . 3_665 124.5(11) C17 C9 C5B . 3_665 114.6(11) C20 C17 C9 . . 120.8 C20 C17 H10 . . 117.5(7) C9 C17 H10 . . 121.6(7) C19 C18 C8 . . 121.4 C19 C18 H7 . . 120.2(18) C8 C18 H7 . . 118.4(18) C18 C19 C20 . . 119.4 C18 C19 H8 . . 116.5(17) C20 C19 H8 . . 124.1(17) C17 C20 C19 . . 119.8 C17 C20 H20 . . 120.5(17) C19 C20 H20 . . 119.7(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1B C5B . 1.39 O1B C1B . 1.39 C5B C4B . 1.39 C5B C8 . 1.575(15) C5B C9 3_665 1.649(17) C4B C3B . 1.39 C4B H4B . 0.95 C3B C2B . 1.39 C3B H3B . 0.95 C2B C1B . 1.39 C2B C6B . 1.497(10) C1B C13B . 1.328(11) C6B C7B . 1.4536 C6B C10B . 1.4583 C7B C8B . 1.6294 C7B H7B . 0.95 C8B C11B . 1.4693 C8B H8B . 0.95 C9B C11B . 1.2992 C9B C10B . 1.5135 C9B H9B . 0.95 C10B C12B . 1.3449 C11B H11B . 0.95 C12B C13B . 1.7219 C12B H12B . 0.95 C13B H13B . 0.95 C1A C2A . 1.3912 C1A C3A . 1.4062 C1A H1A . 0.95 C2A C6A . 1.4104 C2A H2A . 0.95 C3A C4A . 1.3815 C3A H3A . 0.95 C4A C5A . 1.415 C5A C10A . 1.4152 C5A C6A . 1.4513 C6A C7A . 1.4304 C7A C8A . 1.3652 C7A H7A . 0.95 C8A C9A . 1.4172 C8A H8A . 0.95 C9A O1A . 1.3697 C9A C10A . 1.3779 C10A C11A . 1.467 C11A C12A . 1.3273 C11A H11A . 0.95 C12A C13A . 1.5165 C12A H12A . 0.95 C13A O1A . 1.4834 C13A C9 3_665 1.4964 C13A C8 . 1.5132 C8 C9 . 1.3924 C8 C18 . 1.3956 C9 C17 . 1.4072 C9 C13A 3_665 1.4963 C9 C5B 3_665 1.65(4) C17 C20 . 1.3841 C17 H10 . 0.877(11) C18 C19 . 1.393 C18 H7 . 0.95(3) C19 C20 . 1.3931 C19 H8 . 1.05(3) C20 H20 . 1.01(3)