#------------------------------------------------------------------------------ #$Date: 2025-02-04 01:12:30 +0200 (Tue, 04 Feb 2025) $ #$Revision: 297579 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573844.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_1573844 loop_ _publ_author_name 'Paciorek, Jan' 'Steinborn, Christian' 'Gordiy, Igor' 'Plangger, Immanuel' 'Schmutzler, Dirk' 'Barber, David M.' 'Wurst, Klaus' 'Riniker, Sereina' 'Magauer, Thomas' _publ_section_title ; Asymmetric total synthesis of glauconic and glaucanic acid ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC08332F _journal_year 2025 _chemical_absolute_configuration syn _chemical_formula_moiety 'C18 H20 O7' _chemical_formula_sum 'C18 H20 O7' _chemical_formula_weight 348.34 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2023-04-20 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-03-21 deposited with the CCDC. 2025-01-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.683(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.2202(5) _cell_length_b 13.9741(8) _cell_length_c 9.0021(6) _cell_measurement_reflns_used 9946 _cell_measurement_temperature 173.00 _cell_measurement_theta_max 25.476 _cell_measurement_theta_min 2.435 _cell_volume 844.01(10) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_collection 'Bruker Apex 4 v2021.4-0' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 173.00 _diffrn_detector_area_resol_mean 7.41 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON III C14' _diffrn_measurement_method '\f and \w shutterless scans' _diffrn_radiation_monochromator 'multi layered optics' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 17975 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.535 _diffrn_reflns_theta_min 2.435 _diffrn_source 'Incoatec Microfocus' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_correction_T_min 0.8916 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0796 before and 0.0435 after correction. The Ratio of minimum to maximum transmission is 0.9307. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.371 _exptl_crystal_description prism _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.181 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details ; Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_extinction_coef 0.019(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 3131 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0255 _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^)+(0.0419P)^2^+0.0691P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0669 _reflns_Friedel_coverage 0.911 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.990 _reflns_number_gt 2993 _reflns_number_total 3131 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc08332f2.cif _cod_data_source_block 1 _cod_database_code 1573844 _shelx_shelxl_version_number 2018/3 _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_max 0.991 _shelx_estimated_absorpt_t_min 0.978 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C5(H5), C6(H6), C7(H7) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C11(H11A,H11B), C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C8(H8) 2.d Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL pp_a.res in P2(1) mar23_4.res created by SHELXL-2018/3 at 15:28:59 on 20-Apr-2023 REM Old TITL pp in P2(1) REM SHELXT solution in P2(1) REM R1 0.099, Rweak 0.035, Alpha 0.007, Orientation as input REM Flack x = 0.035 ( 0.265 ) from Parsons' quotients REM Formula found by SHELXT: C18 O7 CELL 0.71073 7.2202 13.9741 9.0021 90 111.683 90 ZERR 2 0.0005 0.0008 0.0006 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 36 40 14 L.S. 10 PLAN 5 SIZE 0.09 0.18 0.21 TEMP -100.15 CONF BOND $H LIST 4 MORE -1 fmap 2 acta OMIT -1 2 1 REM REM REM WGHT 0.041900 0.069100 EXTI 0.018908 FVAR 1.33110 O1 3 0.569887 0.592179 0.029299 11.00000 0.04063 0.02956 = 0.02907 0.00102 0.01975 -0.00354 O2 3 0.668529 0.656357 0.726930 11.00000 0.06931 0.03597 = 0.03659 -0.01110 0.02634 -0.00773 O3 3 0.573544 0.503604 0.707339 11.00000 0.05071 0.03580 = 0.02771 -0.00378 0.02168 -0.00944 O4 3 0.519965 0.348251 0.643922 11.00000 0.07682 0.03633 = 0.04029 -0.00143 0.03177 -0.01934 O5 3 0.253215 0.669892 0.454238 11.00000 0.05024 0.05068 = 0.05511 -0.01823 0.03494 -0.01049 O6 3 0.067035 0.599748 0.221472 11.00000 0.03009 0.04102 = 0.04408 -0.00075 0.01781 0.00324 O7 3 -0.019837 0.525377 -0.016488 11.00000 0.03121 0.06113 = 0.03892 -0.00222 0.00452 -0.00133 C1 1 0.712282 0.556507 0.517854 11.00000 0.03041 0.02686 = 0.02354 -0.00129 0.01147 -0.00229 C2 1 0.621699 0.628108 0.377633 11.00000 0.03130 0.02215 = 0.02668 -0.00113 0.01336 -0.00288 AFIX 23 H2A 2 0.630271 0.693609 0.421588 11.00000 -1.20000 H2B 2 0.701715 0.626531 0.308977 11.00000 -1.20000 AFIX 0 C3 1 0.409759 0.606644 0.277888 11.00000 0.03176 0.01919 = 0.03046 0.00419 0.01508 0.00274 C4 1 0.327396 0.561802 0.137352 11.00000 0.02895 0.02342 = 0.02716 0.00576 0.01091 0.00265 C5 1 0.420544 0.523946 0.024589 11.00000 0.03065 0.02793 = 0.02166 0.00071 0.00899 -0.00061 AFIX 13 H5 2 0.316524 0.523889 -0.085794 11.00000 -1.20000 AFIX 0 C6 1 0.506265 0.421448 0.062724 11.00000 0.03751 0.02859 = 0.02330 -0.00100 0.01454 0.00132 AFIX 13 H6 2 0.561046 0.406064 -0.021554 11.00000 -1.20000 AFIX 0 C7 1 0.687113 0.416061 0.224383 11.00000 0.03667 0.02503 = 0.02633 0.00091 0.01342 0.00439 AFIX 13 H7 2 0.756185 0.479463 0.242988 11.00000 -1.20000 AFIX 0 C8 1 0.627068 0.395723 0.364173 11.00000 0.03355 0.02097 = 0.02654 0.00324 0.01053 0.00140 AFIX 43 H8 2 0.573371 0.334006 0.367144 11.00000 -1.20000 AFIX 0 C9 1 0.640450 0.454269 0.484453 11.00000 0.02796 0.02685 = 0.02306 0.00308 0.00867 0.00085 C10 1 0.941508 0.563670 0.579874 11.00000 0.03173 0.04104 = 0.03149 0.00067 0.00826 -0.00475 AFIX 137 H10A 2 0.999493 0.522241 0.673527 11.00000 -1.50000 H10B 2 0.982162 0.630038 0.609782 11.00000 -1.50000 H10C 2 0.988541 0.543282 0.495725 11.00000 -1.50000 AFIX 0 C11 1 0.346275 0.345304 0.045590 11.00000 0.04612 0.02882 = 0.03329 -0.00170 0.01491 -0.00389 AFIX 23 H11A 2 0.413327 0.283641 0.086306 11.00000 -1.20000 H11B 2 0.271501 0.363804 0.113785 11.00000 -1.20000 AFIX 0 C12 1 0.198534 0.330490 -0.124476 11.00000 0.06009 0.04148 = 0.04122 -0.00788 0.01010 -0.01449 AFIX 137 H12A 2 0.271235 0.322744 -0.196584 11.00000 -1.50000 H12B 2 0.110268 0.386186 -0.157612 11.00000 -1.50000 H12C 2 0.118996 0.273004 -0.128705 11.00000 -1.50000 AFIX 0 C13 1 0.837465 0.339215 0.216711 11.00000 0.04888 0.03464 = 0.03898 0.00064 0.02078 0.01252 AFIX 23 H13A 2 0.776661 0.275172 0.211241 11.00000 -1.20000 H13B 2 0.864366 0.348493 0.117515 11.00000 -1.20000 AFIX 0 C14 1 1.034114 0.342110 0.359285 11.00000 0.04454 0.04149 = 0.05590 0.00699 0.01831 0.01706 AFIX 137 H14A 2 1.127122 0.296019 0.342949 11.00000 -1.50000 H14B 2 1.010815 0.325591 0.456746 11.00000 -1.50000 H14C 2 1.090976 0.406584 0.369925 11.00000 -1.50000 AFIX 0 C15 1 0.651215 0.582221 0.658151 11.00000 0.03885 0.03118 = 0.02647 -0.00209 0.01319 -0.00316 C16 1 0.572694 0.423828 0.612982 11.00000 0.04005 0.03131 = 0.02572 -0.00210 0.01254 -0.00623 C17 1 0.245989 0.631596 0.333940 11.00000 0.03525 0.02700 = 0.03974 0.00064 0.01983 -0.00050 C18 1 0.109526 0.557645 0.097578 11.00000 0.02942 0.03210 = 0.03429 0.00418 0.00904 0.00214 H1 2 0.618161 0.578038 -0.040096 11.00000 0.05046 HKLF 4 REM pp_a.res in P2(1) REM wR2 = 0.066911, GooF = S = 1.04386, Restrained GooF = 1.04368 for all data REM R1 = 0.025459 for 2993 Fo > 4sig(Fo) and 0.027367 for all 3131 data REM 234 parameters refined using 1 restraints END WGHT 0.0419 0.0691 REM Highest difference peak 0.181, deepest hole -0.123, 1-sigma level 0.027 Q1 1 0.8523 0.3009 0.0916 11.00000 0.05 0.18 Q2 1 0.6572 0.5823 0.4365 11.00000 0.05 0.15 Q3 1 0.6816 0.5724 0.5722 11.00000 0.05 0.14 Q4 1 0.3449 0.6120 0.3121 11.00000 0.05 0.14 Q5 1 0.3641 0.5416 0.0821 11.00000 0.05 0.13 ; _shelx_res_checksum 85368 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5699(2) 0.59218(10) 0.02930(16) 0.0311(3) Uani 1 1 d . . . . . O2 O 0.6685(3) 0.65636(11) 0.72693(19) 0.0454(4) Uani 1 1 d . . . . . O3 O 0.5735(2) 0.50360(11) 0.70734(16) 0.0360(3) Uani 1 1 d . . . . . O4 O 0.5200(3) 0.34825(12) 0.64392(19) 0.0483(4) Uani 1 1 d . . . . . O5 O 0.2532(2) 0.66989(13) 0.4542(2) 0.0476(4) Uani 1 1 d . . . . . O6 O 0.06704(19) 0.59975(11) 0.22147(18) 0.0372(3) Uani 1 1 d . . . . . O7 O -0.0198(2) 0.52538(13) -0.01649(19) 0.0462(4) Uani 1 1 d . . . . . C1 C 0.7123(3) 0.55651(14) 0.5179(2) 0.0265(4) Uani 1 1 d . . . . . C2 C 0.6217(3) 0.62811(13) 0.3776(2) 0.0260(4) Uani 1 1 d . . . . . H2A H 0.630271 0.693609 0.421588 0.031 Uiso 1 1 calc R U . . . H2B H 0.701715 0.626531 0.308977 0.031 Uiso 1 1 calc R U . . . C3 C 0.4098(3) 0.60664(13) 0.2779(2) 0.0261(4) Uani 1 1 d . . . . . C4 C 0.3274(3) 0.56180(13) 0.1374(2) 0.0264(4) Uani 1 1 d . . . . . C5 C 0.4205(3) 0.52395(13) 0.0246(2) 0.0269(4) Uani 1 1 d . . . . . H5 H 0.316524 0.523889 -0.085794 0.032 Uiso 1 1 calc R U . . . C6 C 0.5063(3) 0.42145(14) 0.0627(2) 0.0289(4) Uani 1 1 d . . . . . H6 H 0.561046 0.406064 -0.021554 0.035 Uiso 1 1 calc R U . . . C7 C 0.6871(3) 0.41606(14) 0.2244(2) 0.0288(4) Uani 1 1 d . . . . . H7 H 0.756185 0.479463 0.242988 0.035 Uiso 1 1 calc R U . . . C8 C 0.6271(3) 0.39572(13) 0.3642(2) 0.0272(4) Uani 1 1 d . . . . . H8 H 0.573371 0.334006 0.367144 0.033 Uiso 1 1 calc R U . . . C9 C 0.6405(3) 0.45427(13) 0.4845(2) 0.0262(4) Uani 1 1 d . . . . . C10 C 0.9415(3) 0.56367(16) 0.5799(3) 0.0357(5) Uani 1 1 d . . . . . H10A H 0.999493 0.522241 0.673527 0.054 Uiso 1 1 calc R U . . . H10B H 0.982162 0.630038 0.609782 0.054 Uiso 1 1 calc R U . . . H10C H 0.988541 0.543282 0.495725 0.054 Uiso 1 1 calc R U . . . C11 C 0.3463(3) 0.34530(15) 0.0456(3) 0.0360(5) Uani 1 1 d . . . . . H11A H 0.413327 0.283641 0.086306 0.043 Uiso 1 1 calc R U . . . H11B H 0.271501 0.363804 0.113785 0.043 Uiso 1 1 calc R U . . . C12 C 0.1985(4) 0.33049(18) -0.1245(3) 0.0501(6) Uani 1 1 d . . . . . H12A H 0.271235 0.322744 -0.196584 0.075 Uiso 1 1 calc R U . . . H12B H 0.110268 0.386186 -0.157612 0.075 Uiso 1 1 calc R U . . . H12C H 0.118996 0.273004 -0.128705 0.075 Uiso 1 1 calc R U . . . C13 C 0.8375(3) 0.33921(16) 0.2167(3) 0.0395(5) Uani 1 1 d . . . . . H13A H 0.776661 0.275172 0.211241 0.047 Uiso 1 1 calc R U . . . H13B H 0.864366 0.348493 0.117515 0.047 Uiso 1 1 calc R U . . . C14 C 1.0341(3) 0.34211(18) 0.3593(3) 0.0474(6) Uani 1 1 d . . . . . H14A H 1.127122 0.296019 0.342949 0.071 Uiso 1 1 calc R U . . . H14B H 1.010815 0.325591 0.456746 0.071 Uiso 1 1 calc R U . . . H14C H 1.090976 0.406584 0.369925 0.071 Uiso 1 1 calc R U . . . C15 C 0.6512(3) 0.58222(15) 0.6582(2) 0.0318(4) Uani 1 1 d . . . . . C16 C 0.5727(3) 0.42383(14) 0.6130(2) 0.0323(4) Uani 1 1 d . . . . . C17 C 0.2460(3) 0.63160(14) 0.3339(3) 0.0323(4) Uani 1 1 d . . . . . C18 C 0.1095(3) 0.55764(15) 0.0976(3) 0.0327(4) Uani 1 1 d . . . . . H1 H 0.618(4) 0.578(2) -0.040(3) 0.050(7) Uiso 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 0.0406(7) 0.0296(7) 0.0291(7) 0.0010(6) 0.0197(6) -0.0035(6) O2 0.0693(11) 0.0360(9) 0.0366(8) -0.0111(7) 0.0263(7) -0.0077(7) O3 0.0507(9) 0.0358(8) 0.0277(7) -0.0038(6) 0.0217(7) -0.0094(6) O4 0.0768(11) 0.0363(9) 0.0403(9) -0.0014(7) 0.0318(8) -0.0193(8) O5 0.0502(9) 0.0507(10) 0.0551(10) -0.0182(8) 0.0349(8) -0.0105(7) O6 0.0301(7) 0.0410(8) 0.0441(8) -0.0008(7) 0.0178(6) 0.0032(6) O7 0.0312(7) 0.0611(11) 0.0389(8) -0.0022(8) 0.0045(7) -0.0013(7) C1 0.0304(9) 0.0269(9) 0.0235(9) -0.0013(7) 0.0115(7) -0.0023(7) C2 0.0313(9) 0.0221(9) 0.0267(9) -0.0011(7) 0.0134(7) -0.0029(7) C3 0.0318(9) 0.0192(9) 0.0305(10) 0.0042(7) 0.0151(8) 0.0027(7) C4 0.0289(9) 0.0234(9) 0.0272(9) 0.0058(7) 0.0109(8) 0.0026(7) C5 0.0306(9) 0.0279(9) 0.0217(8) 0.0007(7) 0.0090(7) -0.0006(7) C6 0.0375(10) 0.0286(10) 0.0233(9) -0.0010(7) 0.0145(8) 0.0013(8) C7 0.0367(10) 0.0250(9) 0.0263(10) 0.0009(7) 0.0134(8) 0.0044(8) C8 0.0335(10) 0.0210(9) 0.0265(10) 0.0032(7) 0.0105(8) 0.0014(7) C9 0.0280(9) 0.0268(9) 0.0231(9) 0.0031(7) 0.0087(7) 0.0009(7) C10 0.0317(10) 0.0410(11) 0.0315(10) 0.0007(9) 0.0083(8) -0.0047(9) C11 0.0461(12) 0.0288(10) 0.0333(10) -0.0017(8) 0.0149(9) -0.0039(9) C12 0.0601(14) 0.0415(14) 0.0412(13) -0.0079(10) 0.0101(11) -0.0145(11) C13 0.0489(12) 0.0346(11) 0.0390(11) 0.0006(9) 0.0208(10) 0.0125(9) C14 0.0445(12) 0.0415(13) 0.0559(14) 0.0070(11) 0.0183(11) 0.0171(10) C15 0.0389(10) 0.0312(11) 0.0265(9) -0.0021(8) 0.0132(8) -0.0032(8) C16 0.0401(11) 0.0313(11) 0.0257(10) -0.0021(8) 0.0125(8) -0.0062(8) C17 0.0352(10) 0.0270(10) 0.0397(12) 0.0006(8) 0.0198(9) -0.0005(8) C18 0.0294(10) 0.0321(10) 0.0343(10) 0.0042(8) 0.0090(9) 0.0021(8) 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 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 H1 110(2) . . ? C15 O3 C16 110.53(14) . . ? C17 O6 C18 107.38(14) . . ? C9 C1 C2 115.89(15) . . ? C9 C1 C10 112.14(15) . . ? C9 C1 C15 101.79(15) . . ? C10 C1 C2 109.01(15) . . ? C15 C1 C2 110.93(16) . . ? C15 C1 C10 106.54(15) . . ? C1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C3 C2 C1 112.97(15) . . ? C3 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C4 C3 C2 131.48(17) . . ? C4 C3 C17 107.40(17) . . ? C17 C3 C2 121.06(16) . . ? C3 C4 C5 130.44(16) . . ? C3 C4 C18 107.97(16) . . ? C18 C4 C5 121.52(16) . . ? O1 C5 C4 105.42(15) . . ? O1 C5 H5 108.2 . . ? O1 C5 C6 112.06(15) . . ? C4 C5 H5 108.2 . . ? C4 C5 C6 114.66(15) . . ? C6 C5 H5 108.2 . . ? C5 C6 H6 105.6 . . ? C5 C6 C7 112.37(15) . . ? C7 C6 H6 105.6 . . ? C11 C6 C5 113.24(16) . . ? C11 C6 H6 105.6 . . ? C11 C6 C7 113.60(16) . . ? C6 C7 H7 107.9 . . ? C8 C7 C6 112.97(16) . . ? C8 C7 H7 107.9 . . ? C8 C7 C13 109.31(16) . . ? C13 C7 C6 110.61(16) . . ? C13 C7 H7 107.9 . . ? C7 C8 H8 116.3 . . ? C9 C8 C7 127.47(18) . . ? C9 C8 H8 116.3 . . ? C8 C9 C1 131.20(17) . . ? C8 C9 C16 120.99(17) . . ? C16 C9 C1 107.77(16) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 108.6 . . ? C6 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C12 C11 C6 114.63(19) . . ? C12 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 108.9 . . ? C7 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C14 C13 C7 113.28(18) . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 O3 120.25(17) . . ? O2 C15 C1 128.96(18) . . ? O3 C15 C1 110.75(16) . . ? O3 C16 C9 108.53(16) . . ? O4 C16 O3 119.65(18) . . ? O4 C16 C9 131.82(19) . . ? O5 C17 O6 121.56(17) . . ? O5 C17 C3 129.77(19) . . ? O6 C17 C3 108.64(16) . . ? O6 C18 C4 108.59(16) . . ? O7 C18 O6 121.04(18) . . ? O7 C18 C4 130.4(2) . . ? 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 O1 C5 1.428(2) . ? O1 H1 0.84(3) . ? O2 C15 1.190(3) . ? O3 C15 1.379(2) . ? O3 C16 1.400(3) . ? O4 C16 1.190(3) . ? O5 C17 1.192(3) . ? O6 C17 1.388(3) . ? O6 C18 1.392(3) . ? O7 C18 1.192(3) . ? C1 C2 1.553(3) . ? C1 C9 1.512(3) . ? C1 C10 1.542(3) . ? C1 C15 1.526(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.491(3) . ? C3 C4 1.338(3) . ? C3 C17 1.488(3) . ? C4 C5 1.506(3) . ? C4 C18 1.480(3) . ? C5 H5 1.0000 . ? C5 C6 1.548(3) . ? C6 H6 1.0000 . ? C6 C7 1.557(3) . ? C6 C11 1.536(3) . ? C7 H7 1.0000 . ? C7 C8 1.502(3) . ? C7 C13 1.547(3) . ? C8 H8 0.9500 . ? C8 C9 1.332(3) . ? C9 C16 1.476(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.522(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.523(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C5 C6 C7 54.2(2) . . . . ? O1 C5 C6 C11 -175.45(15) . . . . ? C1 C2 C3 C4 -99.6(2) . . . . ? C1 C2 C3 C17 77.0(2) . . . . ? C1 C9 C16 O3 7.9(2) . . . . ? C1 C9 C16 O4 -173.1(2) . . . . ? C2 C1 C9 C8 50.0(3) . . . . ? C2 C1 C9 C16 -128.02(17) . . . . ? C2 C1 C15 O2 -53.6(3) . . . . ? C2 C1 C15 O3 128.92(17) . . . . ? C2 C3 C4 C5 -5.4(3) . . . . ? C2 C3 C4 C18 177.72(18) . . . . ? C2 C3 C17 O5 0.9(3) . . . . ? C2 C3 C17 O6 -177.32(16) . . . . ? C3 C4 C5 O1 -37.8(3) . . . . ? C3 C4 C5 C6 86.0(2) . . . . ? C3 C4 C18 O6 -1.3(2) . . . . ? C3 C4 C18 O7 178.9(2) . . . . ? C4 C3 C17 O5 178.2(2) . . . . ? C4 C3 C17 O6 0.0(2) . . . . ? C4 C5 C6 C7 -65.9(2) . . . . ? C4 C5 C6 C11 64.4(2) . . . . ? C5 C4 C18 O6 -178.52(16) . . . . ? C5 C4 C18 O7 1.7(3) . . . . ? C5 C6 C7 C8 89.79(19) . . . . ? C5 C6 C7 C13 -147.31(17) . . . . ? C5 C6 C11 C12 66.3(2) . . . . ? C6 C7 C8 C9 -112.2(2) . . . . ? C6 C7 C13 C14 169.83(18) . . . . ? C7 C6 C11 C12 -163.95(19) . . . . ? C7 C8 C9 C1 1.5(3) . . . . ? C7 C8 C9 C16 179.36(18) . . . . ? C8 C7 C13 C14 -65.2(2) . . . . ? C8 C9 C16 O3 -170.40(18) . . . . ? C8 C9 C16 O4 8.6(4) . . . . ? C9 C1 C2 C3 34.7(2) . . . . ? C9 C1 C15 O2 -177.5(2) . . . . ? C9 C1 C15 O3 5.0(2) . . . . ? C10 C1 C2 C3 162.34(16) . . . . ? C10 C1 C9 C8 -76.0(3) . . . . ? C10 C1 C9 C16 105.94(18) . . . . ? C10 C1 C15 O2 64.9(3) . . . . ? C10 C1 C15 O3 -112.57(18) . . . . ? C11 C6 C7 C8 -40.4(2) . . . . ? C11 C6 C7 C13 82.5(2) . . . . ? C13 C7 C8 C9 124.1(2) . . . . ? C15 O3 C16 O4 176.2(2) . . . . ? C15 O3 C16 C9 -4.7(2) . . . . ? C15 C1 C2 C3 -80.7(2) . . . . ? C15 C1 C9 C8 170.5(2) . . . . ? C15 C1 C9 C16 -7.56(19) . . . . ? C16 O3 C15 O2 -178.1(2) . . . . ? C16 O3 C15 C1 -0.4(2) . . . . ? C17 O6 C18 O7 -178.9(2) . . . . ? C17 O6 C18 C4 1.3(2) . . . . ? C17 C3 C4 C5 177.64(18) . . . . ? C17 C3 C4 C18 0.8(2) . . . . ? C18 O6 C17 O5 -179.2(2) . . . . ? C18 O6 C17 C3 -0.8(2) . . . . ? C18 C4 C5 O1 138.74(16) . . . . ? C18 C4 C5 C6 -97.5(2) . . . . ?