#------------------------------------------------------------------------------ #$Date: 2016-03-21 05:35:49 +0200 (Mon, 21 Mar 2016) $ #$Revision: 178486 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/07/4030715.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_4030715 loop_ _publ_author_name 'Sharma, Mukesh K.' 'Banwell, Martin Gerhardt' 'Willis, Anthony Creswick' _publ_section_title ; Chemoenzymatic Routes to Enantiomerically Enriched and Polyoxygenated Perhydro-3,5a-methanoindeno[4,5-c]furans Related to the Tashironin Class of Sesquiterpene. ; _journal_name_full 'The Journal of organic chemistry' _journal_page_first 150224113214000 _journal_paper_doi 10.1021/acs.joc.5b00303 _journal_year 2015 _chemical_compound_source local _chemical_formula_moiety 'C20 H30 O4' _chemical_formula_sum 'C20 H30 O4' _chemical_formula_weight 334.46 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 12-02-03 _audit_creation_method CRYSTALS_ver_14.11 _audit_update_record ; 2012-02-03 - Report on C20 H30 O4 by Anthony C. Willis for Mukesh Sharma and Martin Banwell 2012-02-03 - passes checkcif tests with no warnings ; _cell_angle_alpha 101.830(2) _cell_angle_beta 92.394(2) _cell_angle_gamma 98.705(3) _cell_formula_units_Z 2 _cell_length_a 7.1052(2) _cell_length_b 8.8559(3) _cell_length_c 15.3747(6) _cell_measurement_reflns_used 16972 _cell_measurement_temperature 200 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.6 _cell_volume 933.31(6) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 200 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 20013 _diffrn_reflns_theta_full 27.504 _diffrn_reflns_theta_max 27.504 _diffrn_reflns_theta_min 2.715 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 364 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.29 _refine_diff_density_min -0.35 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9721 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0464 _refine_ls_shift/su_max 0.0148758 _refine_ls_shift/su_mean 0.0010617 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.26P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1038 _refine_ls_wR_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.1038 _reflns_limit_h_max 9 _reflns_limit_h_min -9 _reflns_limit_k_max 11 _reflns_limit_k_min -11 _reflns_limit_l_max 19 _reflns_limit_l_min 0 _reflns_number_gt 3086 _reflns_number_total 4289 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.10 _oxford_diffrn_Wilson_scale 1.19 _oxford_refine_ls_r_factor_ref 0.0729 _oxford_refine_ls_scale 0.947(3) _oxford_reflns_number_all 4289 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title '2031602 ban1149' _cod_data_source_file jo5b00303_si_002.cif _cod_data_source_block ban1149 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P -1 ' _cod_database_code 4030715 #BEGIN Tags that were not found in dictionaries: _iucr_refine_instruction_details_constraints ; BLOCK CONT SCALE CONT O ( 1 ,X'S,U'S) UNTIL C ( 20 ) CONT H ( 11 ,X'S) UNTIL H ( 203 ) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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_occupancy _atom_site_adp_type O1 O 0.86831(13) 0.61351(11) 0.34694(6) 0.0386 1.0000 Uani O2 O 0.32090(14) 0.01966(11) 0.19458(6) 0.0384 1.0000 Uani O3 O 0.15572(14) 0.13339(11) 0.10389(7) 0.0406 1.0000 Uani O4 O 0.83720(19) 0.75649(15) 0.48139(8) 0.0667 1.0000 Uani C1 C 0.6964(2) 0.50540(17) 0.35463(9) 0.0357 1.0000 Uani C2 C 0.7341(3) 0.37679(19) 0.40356(11) 0.0461 1.0000 Uani C3 C 0.6396(2) 0.22012(17) 0.34256(10) 0.0378 1.0000 Uani C4 C 0.50015(19) 0.26905(15) 0.27866(9) 0.0309 1.0000 Uani C5 C 0.3155(2) 0.31026(17) 0.31493(10) 0.0370 1.0000 Uani C6 C 0.2152(2) 0.37528(17) 0.26279(10) 0.0385 1.0000 Uani C7 C 0.29928(19) 0.39913(15) 0.17680(9) 0.0342 1.0000 Uani C8 C 0.33406(19) 0.23635(15) 0.12687(9) 0.0322 1.0000 Uani C9 C 0.4480(2) 0.15791(15) 0.18752(9) 0.0315 1.0000 Uani C10 C 0.5005(2) 0.50633(15) 0.20303(9) 0.0342 1.0000 Uani C11 C 0.61636(19) 0.42079(15) 0.26063(9) 0.0309 1.0000 Uani C12 C 0.1794(2) -0.01494(16) 0.12158(10) 0.0379 1.0000 Uani C13 C -0.0065(3) -0.0872(2) 0.15067(15) 0.0542 1.0000 Uani C14 C 0.2460(3) -0.1166(2) 0.04095(12) 0.0480 1.0000 Uani C15 C 0.1640(2) 0.4629(2) 0.11863(13) 0.0469 1.0000 Uani C16 C 0.6104(3) 0.5287(2) 0.12126(11) 0.0453 1.0000 Uani C17 C 0.4747(3) 0.66949(19) 0.25343(13) 0.0502 1.0000 Uani C18 C 0.5543(3) 0.0963(2) 0.39206(12) 0.0525 1.0000 Uani C19 C 0.9195(2) 0.73744(17) 0.41463(9) 0.0400 1.0000 Uani C20 C 1.0874(3) 0.8449(2) 0.39641(13) 0.0571 1.0000 Uani H11 H 0.605(2) 0.5714(18) 0.3854(10) 0.0407 1.0000 Uiso H21 H 0.875(3) 0.381(2) 0.4175(11) 0.0552 1.0000 Uiso H22 H 0.674(2) 0.394(2) 0.4606(12) 0.0549 1.0000 Uiso H31 H 0.741(2) 0.1812(18) 0.3030(10) 0.0441 1.0000 Uiso H51 H 0.277(2) 0.2897(18) 0.3730(11) 0.0432 1.0000 Uiso H61 H 0.090(2) 0.4105(18) 0.2761(10) 0.0460 1.0000 Uiso H81 H 0.400(2) 0.2453(17) 0.0702(10) 0.0365 1.0000 Uiso H91 H 0.569(2) 0.1266(17) 0.1588(9) 0.0363 1.0000 Uiso H111 H 0.729(2) 0.3911(17) 0.2280(10) 0.0352 1.0000 Uiso H131 H -0.105(3) -0.112(2) 0.0996(15) 0.0803 1.0000 Uiso H132 H 0.010(3) -0.190(3) 0.1663(14) 0.0791 1.0000 Uiso H133 H -0.041(3) -0.014(3) 0.2025(15) 0.0800 1.0000 Uiso H141 H 0.151(3) -0.135(2) -0.0101(14) 0.0718 1.0000 Uiso H142 H 0.263(3) -0.219(2) 0.0558(13) 0.0709 1.0000 Uiso H143 H 0.372(3) -0.061(2) 0.0248(13) 0.0716 1.0000 Uiso H151 H 0.218(3) 0.477(2) 0.0593(14) 0.0693 1.0000 Uiso H152 H 0.131(3) 0.564(2) 0.1514(13) 0.0702 1.0000 Uiso H153 H 0.040(3) 0.389(2) 0.1043(12) 0.0686 1.0000 Uiso H161 H 0.737(3) 0.598(2) 0.1424(12) 0.0662 1.0000 Uiso H162 H 0.539(3) 0.581(2) 0.0824(13) 0.0669 1.0000 Uiso H163 H 0.642(3) 0.424(2) 0.0850(13) 0.0664 1.0000 Uiso H171 H 0.601(3) 0.734(2) 0.2748(13) 0.0726 1.0000 Uiso H172 H 0.397(3) 0.664(2) 0.3051(14) 0.0723 1.0000 Uiso H173 H 0.412(3) 0.725(2) 0.2144(13) 0.0733 1.0000 Uiso H181 H 0.478(3) 0.001(3) 0.3500(14) 0.0781 1.0000 Uiso H182 H 0.657(3) 0.063(2) 0.4250(14) 0.0784 1.0000 Uiso H183 H 0.465(3) 0.140(2) 0.4377(15) 0.0780 1.0000 Uiso H201 H 1.098(3) 0.947(3) 0.4308(15) 0.0867 1.0000 Uiso H202 H 1.207(3) 0.813(3) 0.4164(15) 0.0881 1.0000 Uiso H203 H 1.105(3) 0.838(3) 0.3363(17) 0.0851 1.0000 Uiso 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 0.0363(5) 0.0361(5) 0.0358(5) -0.0037(4) 0.0026(4) -0.0025(4) O2 0.0438(6) 0.0281(5) 0.0414(6) 0.0095(4) -0.0080(4) -0.0003(4) O3 0.0371(5) 0.0288(5) 0.0539(6) 0.0129(4) -0.0123(5) -0.0024(4) O4 0.0831(9) 0.0591(8) 0.0405(7) -0.0110(6) 0.0184(6) -0.0171(7) C1 0.0339(7) 0.0354(8) 0.0328(7) 0.0009(6) 0.0028(6) -0.0008(6) C2 0.0540(10) 0.0449(9) 0.0349(8) 0.0072(7) -0.0075(7) -0.0015(8) C3 0.0414(8) 0.0374(8) 0.0342(7) 0.0071(6) -0.0034(6) 0.0073(6) C4 0.0330(7) 0.0283(7) 0.0305(7) 0.0050(5) 0.0011(5) 0.0045(5) C5 0.0379(8) 0.0356(8) 0.0366(8) 0.0066(6) 0.0073(6) 0.0031(6) C6 0.0329(7) 0.0345(8) 0.0479(9) 0.0056(7) 0.0085(6) 0.0076(6) C7 0.0318(7) 0.0290(7) 0.0425(8) 0.0091(6) 0.0001(6) 0.0062(6) C8 0.0318(7) 0.0287(7) 0.0350(7) 0.0075(6) -0.0019(6) 0.0014(6) C9 0.0334(7) 0.0259(7) 0.0341(7) 0.0050(5) 0.0004(6) 0.0039(5) C10 0.0374(7) 0.0259(7) 0.0384(8) 0.0067(6) 0.0005(6) 0.0030(6) C11 0.0303(7) 0.0305(7) 0.0300(7) 0.0028(5) 0.0026(5) 0.0038(5) C12 0.0393(8) 0.0281(7) 0.0449(8) 0.0108(6) -0.0073(6) 0.0003(6) C13 0.0467(10) 0.0435(10) 0.0711(12) 0.0194(9) -0.0008(9) -0.0047(8) C14 0.0579(11) 0.0359(9) 0.0451(9) 0.0032(7) -0.0075(8) 0.0019(8) C15 0.0439(9) 0.0376(9) 0.0614(11) 0.0156(8) -0.0069(8) 0.0100(7) C16 0.0449(9) 0.0449(9) 0.0455(9) 0.0183(7) -0.0002(7) -0.0051(7) C17 0.0585(11) 0.0294(8) 0.0599(11) 0.0037(7) -0.0063(9) 0.0089(7) C18 0.0666(12) 0.0434(9) 0.0476(10) 0.0179(8) -0.0120(9) 0.0022(8) C19 0.0465(9) 0.0363(8) 0.0314(8) -0.0009(6) -0.0012(6) 0.0006(6) C20 0.0595(11) 0.0517(11) 0.0469(10) -0.0027(8) 0.0057(9) -0.0144(9) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.130 0 -1 0 0.130 0 0 1 0.100 0 0 -1 0.090 1 0 -1 0.097 -1 0 1 0.119 -1 0 6 0.082 1 -1 -1 0.050 -1 1 1 0.097 -1 3 -6 0.032 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 O1 C19 116.97(11) yes C9 O2 C12 107.66(10) yes C8 O3 C12 108.06(10) yes O1 C1 C2 113.49(12) yes O1 C1 C11 107.88(11) yes C2 C1 C11 105.87(11) yes O1 C1 H11 106.3(9) no C2 C1 H11 112.2(9) no C11 C1 H11 111.1(9) no C1 C2 C3 106.20(12) yes C1 C2 H21 111.3(10) no C3 C2 H21 112.6(10) no C1 C2 H22 108.6(10) no C3 C2 H22 110.5(10) no H21 C2 H22 107.5(14) no C2 C3 C4 103.61(12) yes C2 C3 C18 114.54(13) yes C4 C3 C18 116.04(13) yes C2 C3 H31 106.8(9) no C4 C3 H31 103.9(9) no C18 C3 H31 111.0(9) no C3 C4 C5 116.72(12) yes C3 C4 C9 116.41(11) yes C5 C4 C9 107.05(11) yes C3 C4 C11 102.16(11) yes C5 C4 C11 107.21(11) yes C9 C4 C11 106.33(10) yes C4 C5 C6 114.16(13) yes C4 C5 H51 121.4(9) no C6 C5 H51 124.5(9) no C5 C6 C7 116.66(13) yes C5 C6 H61 125.3(9) no C7 C6 H61 118.1(9) no C6 C7 C8 106.24(11) yes C6 C7 C10 107.00(11) yes C8 C7 C10 107.57(11) yes C6 C7 C15 112.01(13) yes C8 C7 C15 109.55(12) yes C10 C7 C15 114.08(12) yes C7 C8 O3 109.67(11) yes C7 C8 C9 111.37(11) yes O3 C8 C9 104.66(10) yes C7 C8 H81 110.4(8) no O3 C8 H81 109.1(8) no C9 C8 H81 111.5(8) no C8 C9 C4 109.54(11) yes C8 C9 O2 104.59(10) yes C4 C9 O2 111.45(11) yes C8 C9 H91 111.1(8) no C4 C9 H91 110.7(8) no O2 C9 H91 109.3(8) no C7 C10 C11 106.11(10) yes C7 C10 C16 112.58(12) yes C11 C10 C16 108.77(12) yes C7 C10 C17 109.84(12) yes C11 C10 C17 112.63(12) yes C16 C10 C17 106.99(13) yes C4 C11 C1 101.41(11) yes C4 C11 C10 113.49(11) yes C1 C11 C10 119.39(12) yes C4 C11 H111 107.5(8) no C1 C11 H111 105.8(8) no C10 C11 H111 108.4(8) no O3 C12 O2 105.08(10) yes O3 C12 C13 107.94(13) yes O2 C12 C13 109.06(13) yes O3 C12 C14 110.64(12) yes O2 C12 C14 110.65(12) yes C13 C12 C14 113.11(14) yes C12 C13 H131 109.2(12) no C12 C13 H132 109.0(12) no H131 C13 H132 106.4(17) no C12 C13 H133 108.5(12) no H131 C13 H133 112.8(17) no H132 C13 H133 110.9(17) no C12 C14 H141 110.2(12) no C12 C14 H142 108.6(11) no H141 C14 H142 109.6(16) no C12 C14 H143 108.9(11) no H141 C14 H143 108.8(16) no H142 C14 H143 110.8(16) no C7 C15 H151 112.8(11) no C7 C15 H152 111.0(11) no H151 C15 H152 109.9(15) no C7 C15 H153 109.8(11) no H151 C15 H153 107.7(15) no H152 C15 H153 105.4(15) no C10 C16 H161 108.7(10) no C10 C16 H162 111.0(11) no H161 C16 H162 107.9(15) no C10 C16 H163 112.3(10) no H161 C16 H163 106.0(15) no H162 C16 H163 110.7(15) no C10 C17 H171 110.0(12) no C10 C17 H172 111.9(12) no H171 C17 H172 109.1(16) no C10 C17 H173 111.4(12) no H171 C17 H173 106.6(16) no H172 C17 H173 107.7(16) no C3 C18 H181 112.0(12) no C3 C18 H182 109.8(12) no H181 C18 H182 109.0(16) no C3 C18 H183 111.1(12) no H181 C18 H183 107.5(16) no H182 C18 H183 107.2(17) no O1 C19 O4 122.88(14) yes O1 C19 C20 112.10(13) yes O4 C19 C20 125.02(14) yes C19 C20 H201 113.3(13) no C19 C20 H202 110.0(13) no H201 C20 H202 101.9(18) no C19 C20 H203 114.4(14) no H201 C20 H203 115.2(19) no H202 C20 H203 100.4(19) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.4583(16) yes O1 C19 1.3413(16) yes O2 C9 1.4332(16) yes O2 C12 1.4268(16) yes O3 C8 1.4292(16) yes O3 C12 1.4274(16) yes O4 C19 1.1970(18) yes C1 C2 1.537(2) yes C1 C11 1.5271(19) yes C1 H11 1.009(16) no C2 C3 1.545(2) yes C2 H21 1.011(18) no C2 H22 0.984(18) no C3 C4 1.5358(19) yes C3 C18 1.526(2) yes C3 H31 1.018(16) no C4 C5 1.5126(19) yes C4 C9 1.5330(18) yes C4 C11 1.5493(18) yes C5 C6 1.322(2) yes C5 H51 0.988(16) no C6 C7 1.514(2) yes C6 H61 1.000(16) no C7 C8 1.5487(19) yes C7 C10 1.5785(19) yes C7 C15 1.531(2) yes C8 C9 1.5427(19) yes C8 H81 1.018(15) no C9 H91 1.032(15) no C10 C11 1.5617(19) yes C10 C16 1.538(2) yes C10 C17 1.535(2) yes C11 H111 1.001(15) no C12 C13 1.505(2) yes C12 C14 1.514(2) yes C13 H131 1.00(2) no C13 H132 1.01(2) no C13 H133 0.98(2) no C14 H141 0.99(2) no C14 H142 1.00(2) no C14 H143 1.02(2) no C15 H151 1.03(2) no C15 H152 1.00(2) no C15 H153 1.00(2) no C16 H161 1.01(2) no C16 H162 1.00(2) no C16 H163 1.04(2) no C17 H171 1.00(2) no C17 H172 0.99(2) no C17 H173 0.98(2) no C18 H181 1.01(2) no C18 H182 0.98(2) no C18 H183 1.02(2) no C19 C20 1.484(2) yes C20 H201 0.94(2) no C20 H202 0.99(2) no C20 H203 0.93(2) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C6 3.595(2) 1_655 no O3 C14 3.512(2) 2 no O4 C5 3.490(2) 2_666 no O4 C20 3.592(2) 2_776 no 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_publ_flag O1 C1 C2 C3 -128.6(1) no O1 C1 C11 C4 156.1(1) no O1 C1 C11 C10 -78.4(2) no O2 C9 C4 C3 73.7(2) no O2 C9 C4 C5 -58.9(2) no O2 C9 C4 C11 -173.3(1) no O2 C9 C8 O3 -1.3(1) no O2 C9 C8 C7 117.2(1) no O2 C12 O3 C8 30.6(1) no O3 C8 C7 C6 64.0(1) no O3 C8 C7 C10 178.3(1) no O3 C8 C7 C15 -57.1(2) no O3 C8 C9 C4 -120.8(1) no O3 C12 O2 C9 -31.4(1) no O4 C19 O1 C1 4.4(2) no C1 O1 C19 C20 -175.7(1) no C1 C2 C3 C4 -17.9(2) no C1 C2 C3 C18 -145.3(2) no C1 C11 C4 C3 -45.5(1) no C1 C11 C4 C5 77.8(1) no C1 C11 C4 C9 -168.0(1) no C1 C11 C10 C7 -122.9(1) no C1 C11 C10 C16 115.8(1) no C1 C11 C10 C17 -2.7(2) no C2 C1 O1 C19 -87.6(2) no C2 C1 C11 C4 34.3(1) no C2 C1 C11 C10 159.8(1) no C2 C3 C4 C5 -77.4(1) no C2 C3 C4 C9 154.5(1) no C2 C3 C4 C11 39.1(1) no C3 C2 C1 C11 -10.5(2) no C3 C4 C5 C6 169.6(1) no C3 C4 C9 C8 -171.0(1) no C3 C4 C11 C10 -174.8(1) no C4 C5 C6 C7 -0.4(2) no C4 C9 O2 C12 138.2(1) no C4 C9 C8 C7 -2.4(2) no C4 C11 C10 C7 -3.4(1) no C4 C11 C10 C16 -124.8(1) no C4 C11 C10 C17 116.8(1) no C5 C4 C3 C18 49.0(2) no C5 C4 C9 C8 56.3(1) no C5 C4 C11 C10 -51.5(1) no C5 C6 C7 C8 55.9(1) no C5 C6 C7 C10 -58.8(2) no C5 C6 C7 C15 175.4(1) no C6 C5 C4 C9 -57.9(2) no C6 C5 C4 C11 55.9(1) no C6 C7 C8 C9 -51.3(1) no C6 C7 C10 C11 56.2(1) no C6 C7 C10 C16 175.0(1) no C6 C7 C10 C17 -65.8(2) no C7 C8 O3 C12 -137.4(1) no C8 O3 C12 C13 146.9(1) no C8 O3 C12 C14 -88.8(1) no C8 C7 C10 C11 -57.6(1) no C8 C7 C10 C16 61.2(2) no C8 C7 C10 C17 -179.6(1) no C8 C9 O2 C12 20.0(1) no C8 C9 C4 C11 -58.0(1) no C9 O2 C12 C13 -146.9(1) no C9 O2 C12 C14 88.0(1) no C9 C4 C3 C18 -79.1(2) no C9 C4 C11 C10 62.7(1) no C9 C8 O3 C12 -17.9(1) no C9 C8 C7 C10 63.0(1) no C9 C8 C7 C15 -172.5(1) no C11 C1 O1 C19 155.5(1) no C11 C4 C3 C18 165.6(1) no C11 C10 C7 C15 -179.4(1) no C15 C7 C10 C16 -60.5(2) no C15 C7 C10 C17 58.6(2) no