#------------------------------------------------------------------------------ #$Date: 2019-11-17 15:28:34 +0200 (Sun, 17 Nov 2019) $ #$Revision: 230884 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156040.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_7156040 loop_ _publ_author_name 'Shoji, Taku' 'Tanaka, Miwa' 'Takagaki, Sho' 'Miura, Kota' 'Ohta, Akira' 'Sekiguchi, Ryuta' 'Ito, Shunji' 'Mori, Shigeki' 'Okujima, Tetsuo' _publ_section_title ; Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties. ; _journal_issue 3 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 480 _journal_page_last 489 _journal_paper_doi 10.1039/c7ob02861j _journal_volume 16 _journal_year 2018 _chemical_formula_moiety 'C23 H20 O3' _chemical_formula_sum 'C23 H20 O3' _chemical_formula_weight 344.39 _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_creation_method SHELXL-2016/6 _audit_update_record ; 2017-04-18 deposited with the CCDC. 2017-12-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.038(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.4555(7) _cell_length_b 5.3900(3) _cell_length_c 22.7358(10) _cell_measurement_reflns_used 10863 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.26 _cell_measurement_theta_min 1.81 _cell_volume 1744.35(15) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'CrystalStructure 4.2.4 (Rigaku, 2016)' _computing_publication_material 'CrystalStructure 4.2.4' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 28315 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.999 _diffrn_reflns_theta_min 1.819 _diffrn_source 'Varimax 50 kV 24 mA Rotating anode' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.233 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 4205 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0520 _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^)+(0.0487P)^2^+0.5208P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1085 _refine_ls_wR_factor_ref 0.1202 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3060 _reflns_number_total 4205 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02861j2.cif _cod_data_source_block shelxl _cod_depositor_comments 'Adding full bibliography for 7156040--7156045.cif.' _cod_database_code 7156040 _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 0.975 _shelx_estimated_absorpt_t_max 0.998 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2016/6 at 22:34:55 on 04-Apr-2017 CELL 0.71075 14.45550 5.39000 22.73580 90.00000 100.03800 90.00000 ZERR 4 0.00070 0.00030 0.00100 0.00000 0.00400 0.00000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H O UNIT 92 80 12 SHEL 99999.000000 0.756965 L.S. 10 FMAP 2 PLAN 3 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.300 0.020 0.020 WGHT 0.048700 0.520800 FVAR 0.53356 O1 3 0.678065 0.395761 0.474512 11.00000 0.02999 0.03159 = 0.02306 0.00385 0.00935 0.00925 O2 3 0.787757 0.176527 0.438302 11.00000 0.02301 0.02273 = 0.02449 0.00457 0.00523 0.00500 O3 3 0.808702 0.867379 0.209388 11.00000 0.03595 0.02312 = 0.03172 0.00306 0.02026 0.00303 C1 1 0.726894 0.520233 0.383380 11.00000 0.01518 0.02141 = 0.01915 -0.00167 0.00057 -0.00052 C2 1 0.790026 0.491571 0.344114 11.00000 0.01523 0.02327 = 0.02257 -0.00293 0.00091 -0.00106 AFIX 43 H2 2 0.837994 0.369197 0.347884 11.00000 -1.20000 AFIX 0 C3 1 0.773078 0.667951 0.298304 11.00000 0.01749 0.02166 = 0.01953 -0.00313 0.00239 -0.00248 C4 1 0.696166 0.817217 0.308487 11.00000 0.01543 0.01970 = 0.01766 -0.00319 0.00131 -0.00346 C5 1 0.658271 1.020211 0.275067 11.00000 0.02131 0.02255 = 0.01672 -0.00084 0.00391 -0.00398 AFIX 43 H5 2 0.688094 1.063885 0.242454 11.00000 -1.20000 AFIX 0 C6 1 0.582816 1.167573 0.282904 11.00000 0.02661 0.01869 = 0.01697 0.00182 0.00353 0.00198 AFIX 43 H6 2 0.569781 1.301634 0.255590 11.00000 -1.20000 AFIX 0 C7 1 0.523274 1.149528 0.324546 11.00000 0.02100 0.01941 = 0.01849 -0.00180 0.00073 0.00233 AFIX 43 H7 2 0.474875 1.270776 0.320422 11.00000 -1.20000 AFIX 0 C8 1 0.522851 0.982102 0.371582 11.00000 0.01679 0.01858 = 0.01593 -0.00294 0.00113 -0.00210 C9 1 0.588775 0.793275 0.388066 11.00000 0.01750 0.01831 = 0.01626 -0.00071 0.00115 -0.00268 AFIX 43 H9 2 0.579733 0.700751 0.422174 11.00000 -1.20000 AFIX 0 C10 1 0.665226 0.718458 0.362908 11.00000 0.01670 0.01817 = 0.01709 -0.00270 -0.00062 -0.00324 C11 1 0.725754 0.365920 0.436358 11.00000 0.01565 0.02058 = 0.02098 -0.00178 0.00028 -0.00011 C12 1 0.793036 0.011778 0.488670 11.00000 0.02729 0.02534 = 0.02456 0.00385 -0.00010 0.00314 AFIX 137 H12A 2 0.818749 0.101356 0.525398 11.00000 -1.20000 H12B 2 0.833942 -0.128799 0.483643 11.00000 -1.20000 H12C 2 0.730006 -0.049297 0.491231 11.00000 -1.20000 AFIX 0 C13 1 0.442989 1.006060 0.407263 11.00000 0.02047 0.02172 = 0.01593 0.00167 0.00399 0.00218 AFIX 13 H13 2 0.455498 0.885399 0.441129 11.00000 -1.20000 AFIX 0 C14 1 0.349108 0.935956 0.368935 11.00000 0.02035 0.03889 = 0.02682 -0.00170 0.00482 -0.00120 AFIX 137 H14A 2 0.298972 0.951568 0.392687 11.00000 -1.20000 H14B 2 0.351953 0.764280 0.355167 11.00000 -1.20000 H14C 2 0.336146 1.047026 0.334351 11.00000 -1.20000 AFIX 0 C15 1 0.438189 1.264693 0.433993 11.00000 0.03007 0.02711 = 0.02747 -0.00277 0.01312 0.00147 AFIX 137 H15A 2 0.389955 1.267167 0.459400 11.00000 -1.20000 H15B 2 0.422265 1.386188 0.401750 11.00000 -1.20000 H15C 2 0.499267 1.306693 0.457983 11.00000 -1.20000 AFIX 0 C16 1 0.826778 0.676216 0.250213 11.00000 0.01654 0.02406 = 0.02010 -0.00061 -0.00012 -0.00505 C17 1 0.893365 0.523244 0.235830 11.00000 0.02025 0.03753 = 0.02218 0.00078 0.00203 0.00607 AFIX 43 H17 2 0.917847 0.379427 0.257212 11.00000 -1.20000 AFIX 0 C18 1 0.920250 0.617586 0.182483 11.00000 0.01393 0.03419 = 0.02420 -0.00743 0.00114 -0.00388 C19 1 0.984151 0.550126 0.145426 11.00000 0.01795 0.04814 = 0.03060 -0.01010 0.00344 0.00276 AFIX 43 H19 2 1.022732 0.407388 0.153874 11.00000 -1.20000 AFIX 0 C20 1 0.989488 0.696873 0.096290 11.00000 0.01986 0.04688 = 0.02881 -0.01509 0.01151 -0.00968 AFIX 43 H20 2 1.032450 0.653446 0.070777 11.00000 -1.20000 AFIX 0 C21 1 0.933958 0.905102 0.083312 11.00000 0.05001 0.03427 = 0.03966 -0.00283 0.02831 -0.00979 AFIX 43 H21 2 0.939339 1.001506 0.049091 11.00000 -1.20000 AFIX 0 C22 1 0.870788 0.975375 0.119251 11.00000 0.06078 0.02842 = 0.04820 0.00587 0.03455 0.00519 AFIX 43 H22 2 0.832280 1.118198 0.110711 11.00000 -1.20000 AFIX 0 C23 1 0.866483 0.827992 0.168040 11.00000 0.02650 0.02551 = 0.02995 -0.00579 0.01609 -0.00470 HKLF 4 REM xcalibur REM R1 = 0.0520 for 3060 Fo > 4sig(Fo) and 0.0800 for all 4205 data REM 238 parameters refined using 0 restraints END WGHT 0.0488 0.5209 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.233, deepest hole -0.274, 1-sigma level 0.052 Q1 1 0.6775 0.8072 0.3380 11.00000 0.05 0.23 Q2 1 0.4865 1.0099 0.3913 11.00000 0.05 0.23 Q3 1 0.7340 0.7494 0.2995 11.00000 0.05 0.21 ; _shelx_res_checksum 12827 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_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 O1 O 0.67806(8) 0.3958(2) 0.47451(5) 0.0276(3) Uani 1 1 d . . O2 O 0.78776(8) 0.1765(2) 0.43830(5) 0.0233(3) Uani 1 1 d . . O3 O 0.80870(8) 0.8674(2) 0.20939(5) 0.0285(3) Uani 1 1 d . . C1 C 0.72689(10) 0.5202(3) 0.38338(7) 0.0189(3) Uani 1 1 d . . C2 C 0.79003(11) 0.4916(3) 0.34411(7) 0.0206(3) Uani 1 1 d . . H2 H 0.837994 0.369197 0.347884 0.025 Uiso 1 1 calc R U C3 C 0.77308(11) 0.6680(3) 0.29830(7) 0.0197(3) Uani 1 1 d . . C4 C 0.69617(10) 0.8172(3) 0.30849(7) 0.0178(3) Uani 1 1 d . . C5 C 0.65827(11) 1.0202(3) 0.27507(7) 0.0201(3) Uani 1 1 d . . H5 H 0.688094 1.063885 0.242454 0.024 Uiso 1 1 calc R U C6 C 0.58282(11) 1.1676(3) 0.28290(7) 0.0208(3) Uani 1 1 d . . H6 H 0.569781 1.301634 0.255590 0.025 Uiso 1 1 calc R U C7 C 0.52327(11) 1.1495(3) 0.32455(7) 0.0200(3) Uani 1 1 d . . H7 H 0.474875 1.270776 0.320422 0.024 Uiso 1 1 calc R U C8 C 0.52285(10) 0.9821(3) 0.37158(6) 0.0173(3) Uani 1 1 d . . C9 C 0.58878(10) 0.7933(3) 0.38807(7) 0.0176(3) Uani 1 1 d . . H9 H 0.579733 0.700751 0.422174 0.021 Uiso 1 1 calc R U C10 C 0.66523(10) 0.7185(3) 0.36291(7) 0.0177(3) Uani 1 1 d . . C11 C 0.72575(11) 0.3659(3) 0.43636(7) 0.0194(3) Uani 1 1 d . . C12 C 0.79304(12) 0.0118(3) 0.48867(7) 0.0263(4) Uani 1 1 d . . H12A H 0.818749 0.101356 0.525398 0.032 Uiso 1 1 calc R U H12B H 0.833942 -0.128799 0.483643 0.032 Uiso 1 1 calc R U H12C H 0.730006 -0.049297 0.491231 0.032 Uiso 1 1 calc R U C13 C 0.44299(11) 1.0061(3) 0.40726(7) 0.0193(3) Uani 1 1 d . . H13 H 0.455498 0.885399 0.441129 0.023 Uiso 1 1 calc R U C14 C 0.34911(11) 0.9360(4) 0.36893(8) 0.0286(4) Uani 1 1 d . . H14A H 0.298972 0.951568 0.392687 0.034 Uiso 1 1 calc R U H14B H 0.351953 0.764280 0.355167 0.034 Uiso 1 1 calc R U H14C H 0.336146 1.047026 0.334351 0.034 Uiso 1 1 calc R U C15 C 0.43819(12) 1.2647(3) 0.43399(8) 0.0272(4) Uani 1 1 d . . H15A H 0.389955 1.267167 0.459400 0.033 Uiso 1 1 calc R U H15B H 0.422265 1.386188 0.401750 0.033 Uiso 1 1 calc R U H15C H 0.499267 1.306693 0.457983 0.033 Uiso 1 1 calc R U C16 C 0.82678(11) 0.6762(3) 0.25021(7) 0.0206(3) Uani 1 1 d . . C17 C 0.89336(11) 0.5232(3) 0.23583(7) 0.0269(4) Uani 1 1 d . . H17 H 0.917847 0.379427 0.257212 0.032 Uiso 1 1 calc R U C18 C 0.92025(11) 0.6176(3) 0.18248(7) 0.0244(4) Uani 1 1 d . . C19 C 0.98415(12) 0.5501(4) 0.14543(8) 0.0323(4) Uani 1 1 d . . H19 H 1.022732 0.407388 0.153874 0.039 Uiso 1 1 calc R U C20 C 0.98949(12) 0.6969(4) 0.09629(8) 0.0310(4) Uani 1 1 d . . H20 H 1.032450 0.653446 0.070777 0.037 Uiso 1 1 calc R U C21 C 0.93396(14) 0.9051(4) 0.08331(9) 0.0389(5) Uani 1 1 d . . H21 H 0.939339 1.001506 0.049091 0.047 Uiso 1 1 calc R U C22 C 0.87079(16) 0.9754(4) 0.11925(9) 0.0428(5) Uani 1 1 d . . H22 H 0.832280 1.118198 0.110711 0.051 Uiso 1 1 calc R U C23 C 0.86648(12) 0.8280(3) 0.16804(8) 0.0260(4) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0300(6) 0.0316(7) 0.0231(6) 0.0038(5) 0.0093(5) 0.0093(5) O2 0.0230(6) 0.0227(6) 0.0245(6) 0.0046(5) 0.0052(5) 0.0050(5) O3 0.0360(7) 0.0231(7) 0.0317(7) 0.0031(5) 0.0203(6) 0.0030(5) C1 0.0152(7) 0.0214(8) 0.0192(7) -0.0017(7) 0.0006(6) -0.0005(6) C2 0.0152(7) 0.0233(8) 0.0226(8) -0.0029(7) 0.0009(6) -0.0011(7) C3 0.0175(8) 0.0217(8) 0.0195(7) -0.0031(7) 0.0024(6) -0.0025(7) C4 0.0154(7) 0.0197(8) 0.0177(7) -0.0032(7) 0.0013(6) -0.0035(6) C5 0.0213(8) 0.0226(9) 0.0167(7) -0.0008(7) 0.0039(6) -0.0040(7) C6 0.0266(8) 0.0187(8) 0.0170(7) 0.0018(6) 0.0035(6) 0.0020(7) C7 0.0210(8) 0.0194(8) 0.0185(7) -0.0018(6) 0.0007(6) 0.0023(6) C8 0.0168(7) 0.0186(8) 0.0159(7) -0.0029(6) 0.0011(6) -0.0021(6) C9 0.0175(7) 0.0183(8) 0.0163(7) -0.0007(6) 0.0011(6) -0.0027(6) C10 0.0167(7) 0.0182(8) 0.0171(7) -0.0027(6) -0.0006(6) -0.0032(6) C11 0.0157(7) 0.0206(9) 0.0210(8) -0.0018(7) 0.0003(6) -0.0001(6) C12 0.0273(9) 0.0253(9) 0.0246(8) 0.0038(7) -0.0001(7) 0.0031(7) C13 0.0205(8) 0.0217(8) 0.0159(7) 0.0017(6) 0.0040(6) 0.0022(7) C14 0.0203(8) 0.0389(11) 0.0268(9) -0.0017(8) 0.0048(7) -0.0012(8) C15 0.0301(9) 0.0271(9) 0.0275(9) -0.0028(8) 0.0131(7) 0.0015(8) C16 0.0165(7) 0.0241(9) 0.0201(8) -0.0006(7) -0.0001(6) -0.0050(7) C17 0.0203(8) 0.0375(10) 0.0222(8) 0.0008(8) 0.0020(7) 0.0061(8) C18 0.0139(8) 0.0342(10) 0.0242(8) -0.0074(7) 0.0011(6) -0.0039(7) C19 0.0180(8) 0.0481(12) 0.0306(9) -0.0101(9) 0.0034(7) 0.0028(8) C20 0.0199(8) 0.0469(12) 0.0288(9) -0.0151(9) 0.0115(7) -0.0097(8) C21 0.0500(12) 0.0343(11) 0.0397(11) -0.0028(9) 0.0283(10) -0.0098(10) C22 0.0608(14) 0.0284(11) 0.0482(12) 0.0059(9) 0.0345(11) 0.0052(10) C23 0.0265(9) 0.0255(9) 0.0300(9) -0.0058(8) 0.0161(7) -0.0047(7) 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 C11 O2 C12 115.70(12) C23 O3 C16 106.10(13) C2 C1 C10 108.56(14) C2 C1 C11 124.50(14) C10 C1 C11 126.94(14) C1 C2 C3 110.64(14) C1 C2 H2 124.7 C3 C2 H2 124.7 C2 C3 C4 107.65(14) C2 C3 C16 122.38(14) C4 C3 C16 129.95(15) C5 C4 C3 126.93(14) C5 C4 C10 126.19(14) C3 C4 C10 106.86(13) C6 C5 C4 128.71(15) C6 C5 H5 115.6 C4 C5 H5 115.6 C5 C6 C7 129.98(15) C5 C6 H6 115.0 C7 C6 H6 115.0 C6 C7 C8 130.63(15) C6 C7 H7 114.7 C8 C7 H7 114.7 C7 C8 C9 125.43(14) C7 C8 C13 117.09(13) C9 C8 C13 117.48(13) C10 C9 C8 130.83(15) C10 C9 H9 114.6 C8 C9 H9 114.6 C9 C10 C1 125.69(14) C9 C10 C4 127.97(14) C1 C10 C4 106.27(13) O1 C11 O2 122.26(14) O1 C11 C1 127.11(15) O2 C11 C1 110.63(13) O2 C12 H12A 109.5 O2 C12 H12B 109.5 H12A C12 H12B 109.5 O2 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C14 C13 C15 110.82(14) C14 C13 C8 110.78(12) C15 C13 C8 112.30(13) C14 C13 H13 107.6 C15 C13 H13 107.6 C8 C13 H13 107.6 C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 H15A C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C17 C16 O3 110.62(14) C17 C16 C3 131.52(16) O3 C16 C3 117.84(14) C16 C17 C18 107.39(16) C16 C17 H17 126.3 C18 C17 H17 126.3 C23 C18 C19 118.18(16) C23 C18 C17 105.58(14) C19 C18 C17 136.24(17) C20 C19 C18 118.21(18) C20 C19 H19 120.9 C18 C19 H19 120.9 C21 C20 C19 121.70(16) C21 C20 H20 119.2 C19 C20 H20 119.2 C22 C21 C20 121.08(18) C22 C21 H21 119.5 C20 C21 H21 119.5 C23 C22 C21 116.54(19) C23 C22 H22 121.7 C21 C22 H22 121.7 C22 C23 O3 125.41(16) C22 C23 C18 124.29(16) O3 C23 C18 110.30(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C11 1.2092(18) O2 C11 1.3541(18) O2 C12 1.4406(19) O3 C23 1.3785(19) O3 C16 1.3809(19) C1 C2 1.392(2) C1 C10 1.417(2) C1 C11 1.466(2) C2 C3 1.400(2) C2 H2 0.9500 C3 C4 1.424(2) C3 C16 1.448(2) C4 C5 1.389(2) C4 C10 1.486(2) C5 C6 1.386(2) C5 H5 0.9500 C6 C7 1.390(2) C6 H6 0.9500 C7 C8 1.400(2) C7 H7 0.9500 C8 C9 1.400(2) C8 C13 1.528(2) C9 C10 1.390(2) C9 H9 0.9500 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C14 1.527(2) C13 C15 1.527(2) C13 H13 1.0000 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 C17 1.350(2) C17 C18 1.430(2) C17 H17 0.9500 C18 C23 1.382(2) C18 C19 1.402(2) C19 C20 1.382(3) C19 H19 0.9500 C20 C21 1.382(3) C20 H20 0.9500 C21 C22 1.380(3) C21 H21 0.9500 C22 C23 1.375(3) C22 H22 0.9500 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 C10 C1 C2 C3 0.85(18) C11 C1 C2 C3 -179.74(14) C1 C2 C3 C4 0.23(18) C1 C2 C3 C16 -178.19(14) C2 C3 C4 C5 177.43(15) C16 C3 C4 C5 -4.3(3) C2 C3 C4 C10 -1.17(17) C16 C3 C4 C10 177.10(15) C3 C4 C5 C6 178.91(16) C10 C4 C5 C6 -2.8(3) C4 C5 C6 C7 -2.1(3) C5 C6 C7 C8 1.7(3) C6 C7 C8 C9 2.5(3) C6 C7 C8 C13 -176.67(16) C7 C8 C9 C10 -2.6(3) C13 C8 C9 C10 176.55(15) C8 C9 C10 C1 -179.12(15) C8 C9 C10 C4 -2.5(3) C2 C1 C10 C9 175.65(14) C11 C1 C10 C9 -3.7(3) C2 C1 C10 C4 -1.53(17) C11 C1 C10 C4 179.07(14) C5 C4 C10 C9 5.9(3) C3 C4 C10 C9 -175.44(15) C5 C4 C10 C1 -176.95(15) C3 C4 C10 C1 1.66(17) C12 O2 C11 O1 0.3(2) C12 O2 C11 C1 179.89(13) C2 C1 C11 O1 173.20(16) C10 C1 C11 O1 -7.5(3) C2 C1 C11 O2 -6.4(2) C10 C1 C11 O2 172.91(14) C7 C8 C13 C14 67.68(18) C9 C8 C13 C14 -111.57(16) C7 C8 C13 C15 -56.83(18) C9 C8 C13 C15 123.92(15) C23 O3 C16 C17 0.41(18) C23 O3 C16 C3 -178.31(13) C2 C3 C16 C17 5.8(3) C4 C3 C16 C17 -172.28(17) C2 C3 C16 O3 -175.83(14) C4 C3 C16 O3 6.1(2) O3 C16 C17 C18 -0.37(19) C3 C16 C17 C18 178.13(16) C16 C17 C18 C23 0.17(19) C16 C17 C18 C19 179.47(19) C23 C18 C19 C20 -0.4(2) C17 C18 C19 C20 -179.61(18) C18 C19 C20 C21 0.0(3) C19 C20 C21 C22 0.2(3) C20 C21 C22 C23 0.0(3) C21 C22 C23 O3 179.55(17) C21 C22 C23 C18 -0.4(3) C16 O3 C23 C22 179.74(18) C16 O3 C23 C18 -0.30(18) C19 C18 C23 C22 0.6(3) C17 C18 C23 C22 -179.95(18) C19 C18 C23 O3 -179.37(14) C17 C18 C23 O3 0.08(19)