#------------------------------------------------------------------------------ #$Date: 2019-05-23 06:35:04 +0300 (Thu, 23 May 2019) $ #$Revision: 215437 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/28/7232811.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_7232811 loop_ _publ_author_name 'Hirao, Yasukazu' 'Hamamoto, Yosuke' 'Nagamachi, Nobuhiro' 'Kubo, Takashi' _publ_section_title ; Solvent Viscosity-Dependent Isomerization Equilibrium of Tetramethoxy-Substituted Bianthrone ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/C9CP01836K _journal_year 2019 _chemical_formula_sum 'C32 H24 O6' _chemical_formula_weight 504.51 _chemical_name_common 3,3',6,6'-tetramethoxybianthrone _chemical_name_systematic ; 3,3',6,6'-tetramethoxy-10H,10'H-[9,9'-bianthracenylidene]-10,10'-dione ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2018-10-09 deposited with the CCDC. 2019-05-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.103(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5969(5) _cell_length_b 13.4458(6) _cell_length_c 15.9778(9) _cell_measurement_reflns_used 9036 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.46 _cell_measurement_theta_min 2.38 _cell_volume 2381.2(2) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _computing_molecular_graphics ; Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009) ; _computing_publication_material ; Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009) ; _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution Sir2014 _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type ; Rigaku MicroMax-007HF,VariMax-Mo and RAPID II ; _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_unetI/netI 0.0191 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11314 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.458 _diffrn_reflns_theta_min 2.381 _diffrn_source 'micro-focus rotating anode' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Empirical Absorption Correction March 2001 T. Higashi Rigaku Corporation, Tokyo, Japan ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Platelet _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.315 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2727 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0399 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+1.3489P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.1070 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2179 _reflns_number_total 2727 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cp01836k2.cif _cod_data_source_block TMBA _cod_database_code 7232811 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.981 _shelx_estimated_absorpt_t_max 0.998 _shelx_res_file ; TITL ydkr.res created by SHELXL-2016/6 at 10:39:17 on 06-Oct-2018 REM Yadorkari-X generated CELL 0.71075 11.5969 13.4458 15.9778 90.0000 107.1031 90.0000 ZERR 4.0 0.0005 0.0006 0.0009 0.0000 0.0075 0.0000 LATT 7 SYMM -X, +Y, 1/2-Z REM SPGR C2/c monoclinic SFAC C H O UNIT 128 96 24 SIZE 0.20 0.20 0.02 TEMP -123.0 L.S. 100 FMAP 2 PLAN -25 ACTA CONF LIST 4 BOND $H WGHT 0.057000 1.348900 FVAR 2.91407 C1 1 0.290576 0.478490 0.102805 11.00000 0.02838 0.01942 = 0.02593 -0.00403 0.01293 0.00021 C2 1 0.302189 0.387817 0.158090 11.00000 0.02512 0.02087 = 0.02468 -0.00148 0.01069 0.00021 C3 1 0.339819 0.399658 0.249165 11.00000 0.02724 0.02152 = 0.02615 -0.00410 0.00997 -0.00105 AFIX 43 H1 2 0.370518 0.461708 0.274561 11.00000 -1.20000 AFIX 0 C4 1 0.331687 0.319831 0.301612 11.00000 0.02809 0.02595 = 0.02247 -0.00128 0.00940 0.00305 C5 1 0.285962 0.228721 0.263321 11.00000 0.03224 0.02087 = 0.02913 0.00312 0.01320 0.00176 AFIX 43 H2 2 0.275734 0.175147 0.299246 11.00000 -1.20000 AFIX 0 C6 1 0.255791 0.216466 0.173900 11.00000 0.02861 0.01930 = 0.02943 -0.00197 0.01238 -0.00027 AFIX 43 H3 2 0.228099 0.153494 0.149071 11.00000 -1.20000 AFIX 0 C7 1 0.265235 0.295271 0.118919 11.00000 0.02529 0.01978 = 0.02453 -0.00169 0.01014 0.00197 C8 1 0.232636 0.288232 0.021684 11.00000 0.02521 0.01830 = 0.02493 -0.00200 0.01001 -0.00244 C9 1 0.164960 0.377287 -0.022141 11.00000 0.02683 0.01900 = 0.02450 -0.00183 0.01256 0.00061 C10 1 0.066173 0.373552 -0.097816 11.00000 0.02797 0.02246 = 0.02747 -0.00486 0.01110 -0.00092 AFIX 43 H4 2 0.037076 0.310942 -0.122779 11.00000 -1.20000 AFIX 0 C11 1 0.010525 0.459716 -0.136607 11.00000 0.02759 0.02859 = 0.02677 -0.00136 0.00916 0.00136 AFIX 43 H5 2 -0.057430 0.455549 -0.187176 11.00000 -1.20000 AFIX 0 C12 1 0.052952 0.553116 -0.102381 11.00000 0.02842 0.02349 = 0.02949 0.00250 0.01378 0.00484 C13 1 0.146738 0.558652 -0.025205 11.00000 0.03011 0.01824 = 0.02852 -0.00180 0.01382 -0.00029 AFIX 43 H6 2 0.174513 0.621463 -0.000038 11.00000 -1.20000 AFIX 0 C14 1 0.200067 0.471182 0.015254 11.00000 0.02599 0.02073 = 0.02439 -0.00131 0.01231 0.00039 O1 3 0.343554 0.556128 0.130515 11.00000 0.04128 0.02018 = 0.02960 -0.00300 0.00905 -0.00571 O2 3 0.363070 0.322639 0.391106 11.00000 0.04393 0.02856 = 0.02303 -0.00065 0.00999 -0.00074 C15 1 0.417406 0.412203 0.431832 11.00000 0.04236 0.03471 = 0.02552 -0.00618 0.01148 -0.00504 AFIX 137 H7 2 0.491957 0.424576 0.416459 11.00000 -1.50000 H8 2 0.436082 0.405823 0.495529 11.00000 -1.50000 H9 2 0.361556 0.467820 0.411524 11.00000 -1.50000 AFIX 0 O3 3 -0.005072 0.632725 -0.148032 11.00000 0.03545 0.02506 = 0.03580 0.00531 0.00698 0.00534 C16 1 0.043745 0.728472 -0.119341 11.00000 0.03641 0.02282 = 0.05093 0.00744 0.00998 0.00293 AFIX 137 H10 2 0.033139 0.742996 -0.061952 11.00000 -1.50000 H11 2 0.001737 0.778927 -0.161624 11.00000 -1.50000 H12 2 0.129893 0.729262 -0.114739 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0399 for 2179 Fo > 4sig(Fo) and 0.0533 for all 2727 data REM 174 parameters refined using 0 restraints END WGHT 0.0570 1.3489 REM Highest difference peak 0.315, deepest hole -0.142, 1-sigma level 0.047 Q1 1 0.3118 0.4270 0.1310 11.00000 0.05 0.32 Q2 1 0.2549 0.4716 0.0519 11.00000 0.05 0.31 Q3 1 0.3107 0.3613 0.2726 11.00000 0.05 0.31 Q4 1 0.3213 0.3897 0.2036 11.00000 0.05 0.29 Q5 1 0.3510 0.3537 0.2792 11.00000 0.05 0.29 Q6 1 0.2547 0.2871 0.0727 11.00000 0.05 0.29 Q7 1 0.1943 0.3322 -0.0069 11.00000 0.05 0.28 Q8 1 0.1002 0.5515 -0.0662 11.00000 0.05 0.28 Q9 1 0.2999 0.3398 0.1401 11.00000 0.05 0.27 Q10 1 0.1986 0.4277 -0.0070 11.00000 0.05 0.26 Q11 1 0.2924 0.2792 0.2812 11.00000 0.05 0.25 Q12 1 0.1322 0.3751 -0.0700 11.00000 0.05 0.25 Q13 1 0.3436 0.3271 0.3392 11.00000 0.05 0.25 Q14 1 0.1658 0.4223 0.0081 11.00000 0.05 0.25 Q15 1 0.1578 0.5136 -0.0031 11.00000 0.05 0.24 Q16 1 0.0571 0.5075 -0.1346 11.00000 0.05 0.24 Q17 1 0.0230 0.5060 -0.1075 11.00000 0.05 0.23 Q18 1 0.2876 0.2503 0.1455 11.00000 0.05 0.23 Q19 1 0.0305 0.5908 -0.1235 11.00000 0.05 0.22 Q20 1 0.2776 0.2301 0.2185 11.00000 0.05 0.22 Q21 1 0.0254 0.4189 -0.1026 11.00000 0.05 0.21 Q22 1 0.0577 0.4188 -0.1292 11.00000 0.05 0.21 Q23 1 0.2190 0.2407 -0.0043 11.00000 0.05 0.19 Q24 1 0.2967 0.5191 0.1345 11.00000 0.05 0.18 Q25 1 -0.0188 0.4654 -0.1796 11.00000 0.05 0.15 ; _shelx_res_checksum 68808 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1 C 0.29058(12) 0.47849(9) 0.10280(8) 0.0235(3) Uani 1 1 d . . C2 C 0.30219(11) 0.38782(9) 0.15809(8) 0.0228(3) Uani 1 1 d . . C3 C 0.33982(12) 0.39966(10) 0.24917(9) 0.0245(3) Uani 1 1 d . . H1 H 0.370518 0.461708 0.274561 0.029 Uiso 1 1 calc R U C4 C 0.33169(12) 0.31983(10) 0.30161(9) 0.0251(3) Uani 1 1 d . . C5 C 0.28596(12) 0.22872(10) 0.26332(9) 0.0265(3) Uani 1 1 d . . H2 H 0.275734 0.175147 0.299246 0.032 Uiso 1 1 calc R U C6 C 0.25579(12) 0.21647(10) 0.17390(9) 0.0250(3) Uani 1 1 d . . H3 H 0.228099 0.153494 0.149071 0.030 Uiso 1 1 calc R U C7 C 0.26523(11) 0.29527(9) 0.11892(8) 0.0226(3) Uani 1 1 d . . C8 C 0.23264(11) 0.28823(9) 0.02168(8) 0.0222(3) Uani 1 1 d . . C9 C 0.16496(12) 0.37729(9) -0.02214(8) 0.0224(3) Uani 1 1 d . . C10 C 0.06617(12) 0.37355(10) -0.09782(9) 0.0253(3) Uani 1 1 d . . H4 H 0.037076 0.310942 -0.122779 0.030 Uiso 1 1 calc R U C11 C 0.01052(12) 0.45972(10) -0.13661(9) 0.0274(3) Uani 1 1 d . . H5 H -0.057430 0.455549 -0.187176 0.033 Uiso 1 1 calc R U C12 C 0.05295(12) 0.55312(10) -0.10238(9) 0.0260(3) Uani 1 1 d . . C13 C 0.14674(12) 0.55865(9) -0.02521(9) 0.0245(3) Uani 1 1 d . . H6 H 0.174513 0.621463 -0.000038 0.029 Uiso 1 1 calc R U C14 C 0.20007(11) 0.47118(9) 0.01525(8) 0.0227(3) Uani 1 1 d . . O1 O 0.34355(9) 0.55613(7) 0.13051(6) 0.0307(2) Uani 1 1 d . . O2 O 0.36307(9) 0.32264(7) 0.39111(6) 0.0318(2) Uani 1 1 d . . C15 C 0.41741(14) 0.41220(11) 0.43183(9) 0.0339(3) Uani 1 1 d . . H7 H 0.491957 0.424576 0.416459 0.051 Uiso 1 1 calc R U H8 H 0.436082 0.405823 0.495529 0.051 Uiso 1 1 calc R U H9 H 0.361556 0.467820 0.411524 0.051 Uiso 1 1 calc R U O3 O -0.00507(9) 0.63273(7) -0.14803(7) 0.0329(3) Uani 1 1 d . . C16 C 0.04375(14) 0.72847(11) -0.11934(11) 0.0373(4) Uani 1 1 d . . H10 H 0.033139 0.742996 -0.061952 0.056 Uiso 1 1 calc R U H11 H 0.001737 0.778927 -0.161624 0.056 Uiso 1 1 calc R U H12 H 0.129893 0.729262 -0.114739 0.056 Uiso 1 1 calc R U 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 C1 0.0284(6) 0.0194(6) 0.0259(6) -0.0040(5) 0.0129(5) 0.0002(5) C2 0.0251(6) 0.0209(6) 0.0247(6) -0.0015(5) 0.0107(5) 0.0002(5) C3 0.0272(6) 0.0215(6) 0.0262(7) -0.0041(5) 0.0100(5) -0.0011(5) C4 0.0281(6) 0.0260(6) 0.0225(6) -0.0013(5) 0.0094(5) 0.0031(5) C5 0.0322(7) 0.0209(6) 0.0291(7) 0.0031(5) 0.0132(5) 0.0018(6) C6 0.0286(7) 0.0193(6) 0.0294(7) -0.0020(5) 0.0124(5) -0.0003(5) C7 0.0253(6) 0.0198(6) 0.0245(6) -0.0017(5) 0.0101(5) 0.0020(5) C8 0.0252(6) 0.0183(6) 0.0249(6) -0.0020(5) 0.0100(5) -0.0024(5) C9 0.0268(6) 0.0190(6) 0.0245(6) -0.0018(5) 0.0126(5) 0.0006(5) C10 0.0280(6) 0.0225(6) 0.0275(7) -0.0049(5) 0.0111(5) -0.0009(5) C11 0.0276(6) 0.0286(7) 0.0268(7) -0.0014(5) 0.0092(5) 0.0014(6) C12 0.0284(6) 0.0235(6) 0.0295(7) 0.0025(5) 0.0138(5) 0.0048(5) C13 0.0301(7) 0.0182(6) 0.0285(7) -0.0018(5) 0.0138(5) -0.0003(5) C14 0.0260(6) 0.0207(6) 0.0244(6) -0.0013(5) 0.0123(5) 0.0004(5) O1 0.0413(6) 0.0202(5) 0.0296(5) -0.0030(4) 0.0090(4) -0.0057(4) O2 0.0439(6) 0.0286(5) 0.0230(5) -0.0007(4) 0.0100(4) -0.0007(4) C15 0.0424(8) 0.0347(8) 0.0255(7) -0.0062(6) 0.0115(6) -0.0050(7) O3 0.0355(5) 0.0251(5) 0.0358(6) 0.0053(4) 0.0070(4) 0.0053(4) C16 0.0364(8) 0.0228(7) 0.0509(9) 0.0074(6) 0.0100(7) 0.0029(6) 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 _geom_angle_site_symmetry_1 O1 C1 C14 122.47(12) . O1 C1 C2 122.34(12) . C14 C1 C2 114.87(11) . C3 C2 C7 121.72(12) . C3 C2 C1 118.03(11) . C7 C2 C1 119.98(11) . C4 C3 C2 119.08(12) . C4 C3 H1 120.5 . C2 C3 H1 120.5 . O2 C4 C3 124.59(12) . O2 C4 C5 115.49(11) . C3 C4 C5 119.91(12) . C6 C5 C4 120.35(12) . C6 C5 H2 119.8 . C4 C5 H2 119.8 . C5 C6 C7 121.14(12) . C5 C6 H3 119.4 . C7 C6 H3 119.4 . C6 C7 C2 117.47(12) . C6 C7 C8 124.27(11) . C2 C7 C8 118.18(11) . C8 C8 C9 124.08(15) 7 C8 C8 C7 123.70(15) 7 C9 C8 C7 112.10(10) . C10 C9 C14 117.42(12) . C10 C9 C8 124.15(11) . C14 C9 C8 118.42(11) . C11 C10 C9 120.86(12) . C11 C10 H4 119.6 . C9 C10 H4 119.6 . C10 C11 C12 120.86(12) . C10 C11 H5 119.6 . C12 C11 H5 119.6 . O3 C12 C13 124.84(12) . O3 C12 C11 115.84(12) . C13 C12 C11 119.31(12) . C12 C13 C14 119.46(12) . C12 C13 H6 120.3 . C14 C13 H6 120.3 . C13 C14 C9 121.78(12) . C13 C14 C1 118.34(11) . C9 C14 C1 119.76(11) . C4 O2 C15 116.53(10) . O2 C15 H7 109.5 . O2 C15 H8 109.5 . H7 C15 H8 109.5 . O2 C15 H9 109.5 . H7 C15 H9 109.5 . H8 C15 H9 109.5 . C12 O3 C16 116.86(11) . O3 C16 H10 109.5 . O3 C16 H11 109.5 . H10 C16 H11 109.5 . O3 C16 H12 109.5 . H10 C16 H12 109.5 . H11 C16 H12 109.5 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 O1 1.2261(15) . C1 C14 1.4848(18) . C1 C2 1.4882(17) . C2 C3 1.3999(18) . C2 C7 1.4021(17) . C3 C4 1.3819(18) . C3 H1 0.9500 . C4 O2 1.3684(16) . C4 C5 1.4019(18) . C5 C6 1.3773(19) . C5 H2 0.9500 . C6 C7 1.4011(18) . C6 H3 0.9500 . C7 C8 1.4900(17) . C8 C8 1.365(2) 7 C8 C9 1.4889(17) . C9 C10 1.4008(18) . C9 C14 1.4048(17) . C10 C11 1.3811(18) . C10 H4 0.9500 . C11 C12 1.4000(19) . C11 H5 0.9500 . C12 O3 1.3572(16) . C12 C13 1.3857(19) . C13 C14 1.3959(17) . C13 H6 0.9500 . O2 C15 1.4246(17) . C15 H7 0.9800 . C15 H8 0.9800 . C15 H9 0.9800 . O3 C16 1.4267(17) . C16 H10 0.9800 . C16 H11 0.9800 . C16 H12 0.9800 . 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_4 O1 C1 C2 C3 21.59(18) . . C14 C1 C2 C3 -152.00(12) . . O1 C1 C2 C7 -164.26(12) . . C14 C1 C2 C7 22.15(17) . . C7 C2 C3 C4 -4.98(19) . . C1 C2 C3 C4 169.06(12) . . C2 C3 C4 O2 -178.55(12) . . C2 C3 C4 C5 -0.15(19) . . O2 C4 C5 C6 -177.56(12) . . C3 C4 C5 C6 3.9(2) . . C4 C5 C6 C7 -2.6(2) . . C5 C6 C7 C2 -2.32(19) . . C5 C6 C7 C8 -179.05(12) . . C3 C2 C7 C6 6.16(19) . . C1 C2 C7 C6 -167.76(12) . . C3 C2 C7 C8 -176.90(12) . . C1 C2 C7 C8 9.17(18) . . C6 C7 C8 C8 -46.3(2) . 7 C2 C7 C8 C8 136.94(16) . 7 C6 C7 C8 C9 137.40(12) . . C2 C7 C8 C9 -39.31(16) . . C8 C8 C9 C10 44.2(2) 7 . C7 C8 C9 C10 -139.54(13) . . C8 C8 C9 C14 -137.16(16) 7 . C7 C8 C9 C14 39.07(15) . . C14 C9 C10 C11 3.72(19) . . C8 C9 C10 C11 -177.65(12) . . C9 C10 C11 C12 1.3(2) . . C10 C11 C12 O3 177.08(12) . . C10 C11 C12 C13 -4.5(2) . . O3 C12 C13 C14 -179.36(12) . . C11 C12 C13 C14 2.32(19) . . C12 C13 C14 C9 2.90(19) . . C12 C13 C14 C1 -173.14(12) . . C10 C9 C14 C13 -5.88(18) . . C8 C9 C14 C13 175.41(11) . . C10 C9 C14 C1 170.10(11) . . C8 C9 C14 C1 -8.60(18) . . O1 C1 C14 C13 -19.88(19) . . C2 C1 C14 C13 153.71(11) . . O1 C1 C14 C9 164.00(12) . . C2 C1 C14 C9 -22.42(17) . . C3 C4 O2 C15 -5.68(19) . . C5 C4 O2 C15 175.85(12) . . C13 C12 O3 C16 7.50(19) . . C11 C12 O3 C16 -174.13(12) . .