#------------------------------------------------------------------------------ #$Date: 2021-11-09 04:23:29 +0200 (Tue, 09 Nov 2021) $ #$Revision: 270539 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243876.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_7243876 loop_ _publ_author_name 'Goel, Narender' 'Gajbhiye, Rahul L.' 'Saha, Moumita' 'Nagendra, Chennuru' 'Reddy, Araveeti Madhusudhana' 'Ravichandiran, V.' 'Das Saha, Krishna' 'Jaisankar, Parasuraman' _publ_section_title ; A comparative assessment of in vitro cytotoxic activity and phytochemical profiling of Andrographis nallamalayana J.L.Ellis and Andrographis paniculata (Burm. f.) Nees using UPLC-QTOF-MS/MS approach ; _journal_issue 57 _journal_name_full 'RSC Advances' _journal_page_first 35918 _journal_page_last 35936 _journal_paper_doi 10.1039/D1RA07496B _journal_volume 11 _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C H4 O, C22 H22 O11' _chemical_formula_sum 'C23 H26 O12' _chemical_formula_weight 494.44 _chemical_name_systematic '5,2?,6?-trihydroxy-7-methoxyflavone 2?-O-\b-D-glucopyranoside' _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 geom _atom_sites_solution_primary dual _audit_creation_date 2021-03-24 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-24 deposited with the CCDC. 2021-10-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.495(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5283(7) _cell_length_b 8.0352(5) _cell_length_c 24.3766(15) _cell_measurement_reflns_used 9881 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 66.4 _cell_measurement_theta_min 3.94 _cell_volume 2195.7(2) _computing_cell_refinement 'Bruker SAINT V8.38A (Bruker AXS)' _computing_data_collection 'Bruker APEX3 ver.2018.7-2(Bruker AXS)' _computing_data_reduction 'Bruker SAINT V8.38A (Bruker AXS)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.0 _diffrn_detector 'CPAD area detector' _diffrn_detector_area_resol_mean 7.407 _diffrn_detector_type 'Bruker Photon III' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX3_IMuS Diamond_Photon III' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation '0.5 mm double-pinhole' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 75053 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.349 _diffrn_reflns_theta_max 67.349 _diffrn_reflns_theta_min 1.864 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Incoatec I\ms Diamond' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_T_max 0.3593 _exptl_absorpt_correction_T_min 0.2656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1549 before and 0.1102 after correction. The Ratio of minimum to maximum transmission is 0.7451. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.496 _exptl_crystal_description needle _exptl_crystal_F_000 1040 _exptl_crystal_preparation 'Slow Evaporation' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: methanol' _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.461 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.108 _refine_ls_abs_structure_details ; Twinning involves inversion, so Flack parameter cannot be determined ; _refine_ls_extinction_coef 0.0199(18) _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 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 653 _refine_ls_number_reflns 7767 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.090 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0695 _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^)+(0.1310P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1774 _refine_ls_wR_factor_ref 0.1815 _reflns_Friedel_coverage 0.856 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 7303 _reflns_number_total 7767 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra07496b2.cif _cod_data_source_block anm_28_ml_25_0m_a _cod_database_code 7243876 _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 0.959 _shelx_estimated_absorpt_t_min 0.940 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.8(3) 0.20(4) 0.1(3) -0.11(4) 2. 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, All O(H) groups 3.a Ternary CH refined with riding coordinates: C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21) 3.b Secondary CH2 refined with riding coordinates: C22(H22A,H22B), C22(H22A,H22B) 3.c Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6), C8(H8A), C13(H13), C14(H14), C15(H15), C2(H2), C6(H6), C8(H8A), C13(H13), C14(H14), C15(H15) 3.d Idealised Me refined as rotating group: C0AA(H0AB,H0AC,H0AD), C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C10(H10A,H10B,H10C) 3.e Idealised tetrahedral OH refined as rotating group: O0AA(H0AA), O1(H1), O3(H3), O5(H5), O8(H8), O9(H9), O10(H10), O11(H11), O3(H3), O5(H5), O8(H8), O9(H9), O10(H10), O11(H11) ; _shelx_res_file ; TITL anm_28_ml_25_0m_a_a.res in P2(1) anm_28_ml_25_0m_a.res created by SHELXL-2018/3 at 14:25:48 on 24-Mar-2021 REM Old TITL ANM_28_ML_25_0m_a.res in P2(1) REM SHELXT solution in P2(1): R1 0.115, Rweak 0.060, Alpha 0.005 REM 1.156 for 5 systematic absences, Orientation as input REM Flack x = 0.138 ( 0.180 ) from 2948 Parsons' quotients REM Formula found by SHELXT: C46 O24 CELL 1.54178 11.5283 8.0352 24.3766 90 103.495 90 ZERR 4 0.0007 0.0005 0.0015 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 92 104 48 L.S. 99 PLAN 10 SIZE 0.04 0.05 0.06 TEMP -173.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta TWIN -1 0 0 0 -1 0 1 0 1 -4 OMIT -3 -3 2 OMIT -3 3 2 REM REM REM WGHT 0.131000 EXTI 0.019895 BASF 0.19727 0.08685 -0.10804 FVAR 0.66304 O0AA 3 0.232580 0.120832 0.187399 11.00000 0.05040 0.07275 = 0.04303 -0.01969 0.01794 -0.01966 AFIX 147 H0AA 2 0.233078 0.196372 0.211274 11.00000 -1.50000 AFIX 0 C0AA 1 0.127496 0.024098 0.181543 11.00000 0.05062 0.05197 = 0.04050 -0.00711 0.01221 -0.01637 AFIX 137 H0AB 2 0.111943 -0.035912 0.145566 11.00000 -1.50000 H0AC 2 0.059929 0.097300 0.182366 11.00000 -1.50000 H0AD 2 0.138003 -0.055938 0.212651 11.00000 -1.50000 AFIX 0 O1 3 -0.446547 0.975639 0.362625 11.00000 0.03787 0.04195 = 0.03496 0.00239 0.00120 0.00366 AFIX 147 H1 2 -0.463925 0.966990 0.394106 11.00000 -1.50000 AFIX 0 C1 1 -0.523240 0.871467 0.322699 11.00000 0.06494 0.05222 = 0.04663 -0.00543 0.00770 -0.00813 AFIX 137 H1A 2 -0.524928 0.910554 0.284439 11.00000 -1.50000 H1B 2 -0.603997 0.875373 0.329129 11.00000 -1.50000 H1C 2 -0.493574 0.756788 0.327053 11.00000 -1.50000 AFIX 0 RESI 1 O1 3 0.496788 0.250911 -0.018461 11.00000 0.03340 0.03425 = 0.02402 -0.00074 0.00448 0.00255 O2 3 0.163211 0.450750 -0.070862 11.00000 0.03097 0.03155 = 0.03842 -0.00146 0.00638 0.00117 O3 3 0.165491 0.371072 -0.173111 11.00000 0.02891 0.04294 = 0.03450 -0.00299 0.00170 0.00522 AFIX 147 H3 2 0.143384 0.425804 -0.148008 11.00000 -1.50000 AFIX 0 O4 3 0.510444 0.125677 -0.207674 11.00000 0.03321 0.04718 = 0.02898 -0.00647 0.00441 0.00323 O5 3 0.325538 0.154372 0.098015 11.00000 0.03463 0.04537 = 0.02665 -0.00392 0.00344 -0.00950 AFIX 147 H5 2 0.298490 0.129439 0.126097 11.00000 -1.50000 AFIX 0 O6 3 0.675245 0.397172 0.060615 11.00000 0.03011 0.03233 = 0.02881 0.00468 0.00434 -0.00042 O7 3 0.858329 0.477722 0.113179 11.00000 0.02597 0.03200 = 0.03428 0.00007 0.00159 -0.00302 O8 3 1.143157 0.574402 0.078428 11.00000 0.02469 0.03720 = 0.04018 0.00314 0.00289 -0.00083 AFIX 147 H8 2 1.163601 0.669207 0.069617 11.00000 -1.50000 AFIX 0 O9 3 0.972895 0.566972 -0.031895 11.00000 0.03075 0.03946 = 0.03137 0.00444 0.00463 -0.00084 AFIX 147 H9 2 1.036742 0.537455 -0.040037 11.00000 -1.50000 AFIX 0 O10 3 0.770631 0.360139 -0.035424 11.00000 0.03012 0.03346 = 0.03141 -0.00106 0.00027 -0.00046 AFIX 147 H10 2 0.729120 0.419849 -0.060877 11.00000 -1.50000 AFIX 0 O11 3 1.015536 0.451728 0.222559 11.00000 0.04197 0.05187 = 0.03270 0.00422 0.00931 -0.00081 AFIX 147 H11 2 0.950059 0.480870 0.229062 11.00000 -1.50000 AFIX 0 C1 1 0.435571 0.306921 0.020348 11.00000 0.03199 0.02930 = 0.03523 -0.00752 0.00509 -0.00228 C2 1 0.327637 0.377717 0.004614 11.00000 0.02845 0.02962 = 0.03410 -0.00019 0.00637 -0.00263 AFIX 43 H2 2 0.290981 0.421176 0.032653 11.00000 -1.20000 AFIX 0 C3 1 0.265935 0.389342 -0.053979 11.00000 0.02989 0.02279 = 0.03169 0.00312 0.00660 -0.00037 C4 1 0.328434 0.321163 -0.094096 11.00000 0.03136 0.02581 = 0.03239 -0.00222 0.00812 -0.00257 C5 1 0.275586 0.311608 -0.152357 11.00000 0.03048 0.02999 = 0.03128 -0.00109 0.00292 -0.00291 C6 1 0.338511 0.241068 -0.188408 11.00000 0.03188 0.03793 = 0.02994 0.00184 0.00331 0.00168 AFIX 43 H6 2 0.301998 0.229576 -0.227402 11.00000 -1.20000 AFIX 0 C7 1 0.455804 0.186695 -0.167476 11.00000 0.03665 0.03250 = 0.02895 -0.00532 0.00504 -0.00230 C8 1 0.511065 0.193114 -0.110649 11.00000 0.02915 0.03443 = 0.03005 -0.00275 -0.00015 -0.00154 AFIX 43 H8A 2 0.590583 0.155244 -0.096799 11.00000 -1.20000 AFIX 0 C9 1 0.444293 0.257916 -0.074695 11.00000 0.03116 0.02644 = 0.02838 0.00083 0.00056 0.00012 C10 1 0.633244 0.083698 -0.189067 11.00000 0.03324 0.05561 = 0.04394 -0.00859 0.00603 0.00942 AFIX 137 H10A 2 0.665174 0.053996 -0.221665 11.00000 -1.50000 H10B 2 0.641849 -0.011080 -0.163126 11.00000 -1.50000 H10C 2 0.677299 0.179261 -0.169592 11.00000 -1.50000 AFIX 0 C11 1 0.502986 0.269224 0.078291 11.00000 0.03012 0.02522 = 0.03049 -0.00119 0.00273 -0.00101 C12 1 0.624697 0.301386 0.096511 11.00000 0.03685 0.02538 = 0.02807 0.00178 0.00621 -0.00173 C13 1 0.689523 0.249457 0.149222 11.00000 0.03055 0.03349 = 0.03474 0.00032 -0.00018 -0.00314 AFIX 43 H13 2 0.772605 0.271313 0.161061 11.00000 -1.20000 AFIX 0 C14 1 0.629710 0.164501 0.184323 11.00000 0.03791 0.03401 = 0.02965 0.00062 0.00317 -0.00224 AFIX 43 H14 2 0.673547 0.126189 0.220030 11.00000 -1.20000 AFIX 0 C15 1 0.509716 0.134982 0.168669 11.00000 0.04171 0.03103 = 0.02539 0.00096 0.00385 -0.00325 AFIX 43 H15 2 0.470468 0.079404 0.193619 11.00000 -1.20000 AFIX 0 C16 1 0.445033 0.187639 0.115331 11.00000 0.03314 0.02983 = 0.03699 -0.00258 0.00720 -0.00165 C17 1 0.798693 0.385749 0.064948 11.00000 0.02858 0.03232 = 0.02994 -0.00583 0.00080 -0.00471 AFIX 13 H17 2 0.824698 0.266725 0.068581 11.00000 -1.20000 AFIX 0 C18 1 0.824312 0.461944 0.011881 11.00000 0.03198 0.02640 = 0.03305 -0.00158 0.00674 -0.00133 AFIX 13 H18 2 0.787630 0.575295 0.006329 11.00000 -1.20000 AFIX 0 C19 1 0.958586 0.478084 0.016969 11.00000 0.02981 0.03055 = 0.03011 0.00687 0.00218 0.00118 AFIX 13 H19 2 0.994671 0.364782 0.017388 11.00000 -1.20000 AFIX 0 C20 1 1.015991 0.569225 0.071004 11.00000 0.02885 0.02843 = 0.03748 0.00285 0.00477 -0.00255 AFIX 13 H20 2 0.983601 0.684947 0.069870 11.00000 -1.20000 AFIX 0 C21 1 0.985863 0.472976 0.120012 11.00000 0.02818 0.02694 = 0.03515 0.00263 0.00404 -0.00105 AFIX 13 H21 2 1.013302 0.355027 0.119565 11.00000 -1.20000 AFIX 0 C22 1 1.039557 0.551127 0.176618 11.00000 0.03076 0.03603 = 0.03401 -0.00056 0.00298 -0.00601 AFIX 23 H22A 2 1.126857 0.562159 0.181308 11.00000 -1.20000 H22B 2 1.005990 0.664047 0.177979 11.00000 -1.20000 AFIX 0 RESI 2 O1 3 0.024528 0.695337 0.521199 11.00000 0.02885 0.03636 = 0.02653 -0.00198 0.00105 -0.00243 O2 3 -0.254717 0.471612 0.569548 11.00000 0.02896 0.03976 = 0.03502 -0.00196 0.00371 -0.00186 O3 3 -0.148634 0.528549 0.674541 11.00000 0.02979 0.04769 = 0.03514 0.00225 0.00389 -0.00220 AFIX 147 H3 2 -0.198478 0.485211 0.647640 11.00000 -1.50000 AFIX 0 O4 3 0.206028 0.834031 0.711452 11.00000 0.03844 0.04222 = 0.02787 -0.00316 0.00041 -0.00162 O5 3 -0.244583 0.835507 0.414387 11.00000 0.03620 0.05510 = 0.03347 -0.00002 0.00516 0.01654 AFIX 147 H5 2 -0.297484 0.883905 0.390080 11.00000 -1.50000 AFIX 0 O6 3 0.111896 0.529535 0.435776 11.00000 0.02699 0.03379 = 0.02993 0.00271 0.00195 0.00162 O7 3 0.240986 0.418441 0.386472 11.00000 0.03041 0.03563 = 0.03164 -0.00448 0.00413 -0.00315 O8 3 0.566599 0.383716 0.420586 11.00000 0.02844 0.03378 = 0.03854 0.00165 0.00516 0.00140 AFIX 147 H8 2 0.603646 0.295592 0.431982 11.00000 -1.50000 AFIX 0 O9 3 0.508410 0.431211 0.531900 11.00000 0.02661 0.03378 = 0.03195 0.00240 -0.00043 -0.00103 AFIX 147 H9 2 0.581297 0.443380 0.533026 11.00000 -1.50000 AFIX 0 O10 3 0.299435 0.620052 0.524237 11.00000 0.03063 0.03611 = 0.02900 -0.00422 0.00242 -0.00292 AFIX 147 H10 2 0.235472 0.603926 0.534324 11.00000 -1.50000 AFIX 0 O11 3 0.265855 0.348484 0.278499 11.00000 0.03251 0.04632 = 0.02842 0.00074 0.00343 0.00119 AFIX 147 H11 2 0.200436 0.361962 0.287485 11.00000 -1.50000 AFIX 0 C1 1 -0.073025 0.641707 0.482039 11.00000 0.02588 0.02777 = 0.02724 -0.00595 -0.00359 -0.00182 C2 1 -0.167292 0.567851 0.497091 11.00000 0.02744 0.02685 = 0.03074 -0.00075 0.00039 -0.00445 AFIX 43 H2 2 -0.233544 0.532373 0.468477 11.00000 -1.20000 AFIX 0 C3 1 -0.168877 0.542460 0.554951 11.00000 0.03039 0.02187 = 0.03460 -0.00223 0.00186 -0.00024 C4 1 -0.067787 0.607627 0.595216 11.00000 0.03124 0.03337 = 0.02619 -0.00143 0.00258 0.00098 C5 1 -0.062096 0.605356 0.654462 11.00000 0.02804 0.03931 = 0.02967 0.00101 0.00339 0.00465 C6 1 0.029911 0.681021 0.691852 11.00000 0.03704 0.03451 = 0.02801 0.00342 0.00202 0.00189 AFIX 43 H6 2 0.032378 0.680392 0.731079 11.00000 -1.20000 AFIX 0 C7 1 0.121146 0.760037 0.671601 11.00000 0.02873 0.02993 = 0.03528 -0.00198 -0.00130 0.00424 C8 1 0.123219 0.757836 0.614079 11.00000 0.02981 0.02605 = 0.03096 -0.00263 0.00301 0.00013 AFIX 43 H8A 2 0.187500 0.803344 0.600680 11.00000 -1.20000 AFIX 0 C9 1 0.025081 0.684746 0.578264 11.00000 0.03027 0.02812 = 0.02822 0.00172 -0.00020 0.00287 C10 1 0.309409 0.898886 0.695033 11.00000 0.03282 0.04604 = 0.03760 0.00097 0.00133 -0.00765 AFIX 137 H10A 2 0.285141 0.988883 0.667623 11.00000 -1.50000 H10B 2 0.347251 0.809864 0.677942 11.00000 -1.50000 H10C 2 0.366171 0.942036 0.728363 11.00000 -1.50000 AFIX 0 C11 1 -0.066688 0.680378 0.423824 11.00000 0.02632 0.02619 = 0.03160 -0.00160 0.00587 -0.00170 C12 1 0.025922 0.624421 0.400129 11.00000 0.02984 0.02963 = 0.02771 -0.00203 0.00056 -0.00077 C13 1 0.026849 0.658121 0.344601 11.00000 0.03090 0.03944 = 0.03167 -0.00189 0.00418 -0.00066 AFIX 43 H13 2 0.089753 0.617910 0.329041 11.00000 -1.20000 AFIX 0 C14 1 -0.065093 0.751319 0.311830 11.00000 0.03720 0.03457 = 0.03125 0.00290 0.00558 0.00061 AFIX 43 H14 2 -0.064982 0.773762 0.273579 11.00000 -1.20000 AFIX 0 C15 1 -0.157575 0.812533 0.334093 11.00000 0.03162 0.03381 = 0.03027 -0.00122 0.00152 0.00208 AFIX 43 H15 2 -0.219513 0.877499 0.311480 11.00000 -1.20000 AFIX 0 C16 1 -0.157797 0.777225 0.389649 11.00000 0.02907 0.03495 = 0.02806 -0.00224 0.00136 0.00118 C17 1 0.228494 0.539059 0.427276 11.00000 0.02955 0.02542 = 0.03519 -0.00218 0.00591 -0.00145 AFIX 13 H17 2 0.245104 0.653212 0.414663 11.00000 -1.20000 AFIX 0 C18 1 0.311489 0.497882 0.483312 11.00000 0.02901 0.02429 = 0.03539 -0.00180 0.00424 0.00035 AFIX 13 H18 2 0.288545 0.386938 0.496083 11.00000 -1.20000 AFIX 0 C19 1 0.438715 0.489375 0.478301 11.00000 0.03148 0.02692 = 0.03170 0.00218 0.00328 -0.00104 AFIX 13 H19 2 0.466082 0.603515 0.470883 11.00000 -1.20000 AFIX 0 C20 1 0.449118 0.374540 0.429695 11.00000 0.02509 0.03359 = 0.03263 -0.00027 0.00672 0.00003 AFIX 13 H20 2 0.433065 0.257533 0.439791 11.00000 -1.20000 AFIX 0 C21 1 0.357913 0.423753 0.376089 11.00000 0.02592 0.02825 = 0.03502 0.00281 0.00501 0.00297 AFIX 13 H21 2 0.375311 0.538836 0.364598 11.00000 -1.20000 AFIX 0 C22 1 0.356715 0.304266 0.328039 11.00000 0.03294 0.04006 = 0.02913 -0.00102 0.00457 0.00107 AFIX 23 H22A 2 0.435757 0.305279 0.318651 11.00000 -1.20000 H22B 2 0.341737 0.190068 0.339987 11.00000 -1.20000 AFIX 0 HKLF 4 REM anm_28_ml_25_0m_a_a.res in P2(1) REM wR2 = 0.1815, GooF = S = 1.090, Restrained GooF = 1.090 for all data REM R1 = 0.0695 for 7303 Fo > 4sig(Fo) and 0.0724 for all 7767 data REM 653 parameters refined using 1 restraints END WGHT 0.1310 0.0000 REM Highest difference peak 0.461, deepest hole -0.398, 1-sigma level 0.108 Q1 1 0.5250 0.1324 -0.1703 11.00000 0.05 0.38 Q2 1 -0.0224 0.6657 0.4921 11.00000 0.05 0.37 Q3 1 -0.0112 0.6786 0.5154 11.00000 0.05 0.37 Q4 1 0.0582 0.6486 0.4224 11.00000 0.05 0.36 Q5 1 0.7389 0.3347 0.1717 11.00000 0.05 0.36 Q6 1 0.3654 0.2927 -0.0796 11.00000 0.05 0.35 Q7 1 0.1383 0.4331 -0.1217 11.00000 0.05 0.35 Q8 1 0.4144 0.2555 -0.0810 11.00000 0.05 0.34 Q9 1 0.3402 0.1580 0.1830 11.00000 0.05 0.34 Q10 1 0.0439 0.4736 -0.0993 11.00000 0.05 0.33 ; _shelx_res_checksum 62620 _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 O0AA O 0.2326(5) 0.1208(8) 0.1874(2) 0.0542(15) Uani 1 1 d . . . . . H0AA H 0.233078 0.196372 0.211274 0.081 Uiso 1 1 calc GR . . . . C0AA C 0.1275(7) 0.0241(11) 0.1815(3) 0.0474(18) Uani 1 1 d . . . . . H0AB H 0.111943 -0.035912 0.145566 0.071 Uiso 1 1 calc GR . . . . H0AC H 0.059929 0.097300 0.182366 0.071 Uiso 1 1 calc GR . . . . H0AD H 0.138003 -0.055938 0.212651 0.071 Uiso 1 1 calc GR . . . . O1 O -0.4465(4) 0.9756(6) 0.3626(2) 0.0395(11) Uani 1 1 d . . . . . H1 H -0.463925 0.966990 0.394106 0.059 Uiso 1 1 calc GR . . . . C1 C -0.5232(8) 0.8715(11) 0.3227(4) 0.055(2) Uani 1 1 d . . . . . H1A H -0.524928 0.910554 0.284439 0.083 Uiso 1 1 calc GR . . . . H1B H -0.603997 0.875373 0.329129 0.083 Uiso 1 1 calc GR . . . . H1C H -0.493574 0.756788 0.327053 0.083 Uiso 1 1 calc GR . . . . O1_1 O 0.4968(4) 0.2509(6) -0.01846(17) 0.0309(9) Uani 1 1 d . . . . . O2_1 O 0.1632(4) 0.4507(5) -0.07086(19) 0.0339(10) Uani 1 1 d . . . . . O3_1 O 0.1655(4) 0.3711(6) -0.17311(19) 0.0364(10) Uani 1 1 d . . . . . H3_1 H 0.143384 0.425804 -0.148008 0.055 Uiso 1 1 calc GR . . . . O4_1 O 0.5104(4) 0.1257(6) -0.20767(18) 0.0369(10) Uani 1 1 d . . . . . O5_1 O 0.3255(4) 0.1544(6) 0.09801(18) 0.0362(10) Uani 1 1 d . . . . . H5_1 H 0.298490 0.129439 0.126097 0.054 Uiso 1 1 calc GR . . . . O6_1 O 0.6752(4) 0.3972(5) 0.06061(18) 0.0308(9) Uani 1 1 d . . . . . O7_1 O 0.8583(4) 0.4777(6) 0.11318(18) 0.0316(9) Uani 1 1 d . . . . . O8_1 O 1.1432(4) 0.5744(6) 0.0784(2) 0.0348(10) Uani 1 1 d . . . . . H8_1 H 1.163601 0.669207 0.069617 0.052 Uiso 1 1 calc GR . . . . O9_1 O 0.9729(4) 0.5670(6) -0.03189(18) 0.0343(10) Uani 1 1 d . . . . . H9_1 H 1.036742 0.537455 -0.040037 0.051 Uiso 1 1 calc GR . . . . O10_1 O 0.7706(4) 0.3601(5) -0.03542(19) 0.0328(10) Uani 1 1 d . . . . . H10_1 H 0.729120 0.419849 -0.060877 0.049 Uiso 1 1 calc GR . . . . O11_1 O 1.0155(4) 0.4517(7) 0.2226(2) 0.0421(11) Uani 1 1 d . . . . . H11_1 H 0.950059 0.480870 0.229062 0.063 Uiso 1 1 calc GR . . . . C1_1 C 0.4356(6) 0.3069(8) 0.0203(3) 0.0326(14) Uani 1 1 d . . . . . C2_1 C 0.3276(6) 0.3777(8) 0.0046(3) 0.0309(13) Uani 1 1 d . . . . . H2_1 H 0.290981 0.421176 0.032653 0.037 Uiso 1 1 calc R . . . . C3_1 C 0.2659(5) 0.3893(7) -0.0540(3) 0.0282(12) Uani 1 1 d . . . . . C4_1 C 0.3284(6) 0.3212(8) -0.0941(3) 0.0297(13) Uani 1 1 d . . . . . C5_1 C 0.2756(6) 0.3116(8) -0.1524(3) 0.0313(13) Uani 1 1 d . . . . . C6_1 C 0.3385(6) 0.2411(9) -0.1884(3) 0.0339(14) Uani 1 1 d . . . . . H6_1 H 0.301998 0.229576 -0.227402 0.041 Uiso 1 1 calc R . . . . C7_1 C 0.4558(6) 0.1867(8) -0.1675(3) 0.0331(14) Uani 1 1 d . . . . . C8_1 C 0.5111(6) 0.1931(8) -0.1106(3) 0.0324(13) Uani 1 1 d . . . . . H8A_1 H 0.590583 0.155244 -0.096799 0.039 Uiso 1 1 calc R . . . . C9_1 C 0.4443(6) 0.2579(8) -0.0747(3) 0.0297(13) Uani 1 1 d . . . . . C10_1 C 0.6332(6) 0.0837(11) -0.1891(3) 0.0448(17) Uani 1 1 d . . . . . H10A_1 H 0.665174 0.053996 -0.221665 0.067 Uiso 1 1 calc GR . . . . H10B_1 H 0.641849 -0.011080 -0.163126 0.067 Uiso 1 1 calc GR . . . . H10C_1 H 0.677299 0.179261 -0.169592 0.067 Uiso 1 1 calc GR . . . . C11_1 C 0.5030(6) 0.2692(7) 0.0783(3) 0.0293(13) Uani 1 1 d . . . . . C12_1 C 0.6247(6) 0.3014(7) 0.0965(3) 0.0303(13) Uani 1 1 d . . . . . C13_1 C 0.6895(6) 0.2495(8) 0.1492(3) 0.0342(14) Uani 1 1 d . . . . . H13_1 H 0.772605 0.271313 0.161061 0.041 Uiso 1 1 calc R . . . . C14_1 C 0.6297(6) 0.1645(8) 0.1843(3) 0.0346(14) Uani 1 1 d . . . . . H14_1 H 0.673547 0.126189 0.220030 0.042 Uiso 1 1 calc R . . . . C15_1 C 0.5097(6) 0.1350(8) 0.1687(3) 0.0334(14) Uani 1 1 d . . . . . H15_1 H 0.470468 0.079404 0.193619 0.040 Uiso 1 1 calc R . . . . C16_1 C 0.4450(6) 0.1876(8) 0.1153(3) 0.0335(14) Uani 1 1 d . . . . . C17_1 C 0.7987(5) 0.3857(8) 0.0649(3) 0.0313(13) Uani 1 1 d . . . . . H17_1 H 0.824698 0.266725 0.068581 0.038 Uiso 1 1 calc R . . . . C18_1 C 0.8243(5) 0.4619(8) 0.0119(3) 0.0306(13) Uani 1 1 d . . . . . H18_1 H 0.787630 0.575295 0.006329 0.037 Uiso 1 1 calc R . . . . C19_1 C 0.9586(5) 0.4781(8) 0.0170(3) 0.0309(13) Uani 1 1 d . . . . . H19_1 H 0.994671 0.364782 0.017388 0.037 Uiso 1 1 calc R . . . . C20_1 C 1.0160(6) 0.5692(8) 0.0710(3) 0.0321(13) Uani 1 1 d . . . . . H20_1 H 0.983601 0.684947 0.069870 0.038 Uiso 1 1 calc R . . . . C21_1 C 0.9859(5) 0.4730(8) 0.1200(3) 0.0306(13) Uani 1 1 d . . . . . H21_1 H 1.013302 0.355027 0.119565 0.037 Uiso 1 1 calc R . . . . C22_1 C 1.0396(6) 0.5511(9) 0.1766(3) 0.0344(14) Uani 1 1 d . . . . . H22A_1 H 1.126857 0.562159 0.181308 0.041 Uiso 1 1 calc R . . . . H22B_1 H 1.005990 0.664047 0.177979 0.041 Uiso 1 1 calc R . . . . O1_2 O 0.0245(4) 0.6953(6) 0.52120(17) 0.0315(10) Uani 1 1 d . . . . . O2_2 O -0.2547(4) 0.4716(6) 0.56955(19) 0.0352(10) Uani 1 1 d . . . . . O3_2 O -0.1486(4) 0.5285(6) 0.67454(19) 0.0381(11) Uani 1 1 d . . . . . H3_2 H -0.198478 0.485211 0.647640 0.057 Uiso 1 1 calc GR . . . . O4_2 O 0.2060(4) 0.8340(6) 0.71145(19) 0.0374(11) Uani 1 1 d . . . . . O5_2 O -0.2446(4) 0.8355(7) 0.4144(2) 0.0421(12) Uani 1 1 d . . . . . H5_2 H -0.297484 0.883905 0.390080 0.063 Uiso 1 1 calc GR . . . . O6_2 O 0.1119(4) 0.5295(5) 0.43578(18) 0.0310(9) Uani 1 1 d . . . . . O7_2 O 0.2410(4) 0.4184(6) 0.38647(18) 0.0331(10) Uani 1 1 d . . . . . O8_2 O 0.5666(4) 0.3837(6) 0.42059(19) 0.0340(10) Uani 1 1 d . . . . . H8_2 H 0.603646 0.295592 0.431982 0.051 Uiso 1 1 calc GR . . . . O9_2 O 0.5084(4) 0.4312(6) 0.53190(18) 0.0320(10) Uani 1 1 d . . . . . H9_2 H 0.581297 0.443380 0.533026 0.048 Uiso 1 1 calc GR . . . . O10_2 O 0.2994(4) 0.6201(6) 0.52424(18) 0.0327(10) Uani 1 1 d . . . . . H10_2 H 0.235472 0.603926 0.534324 0.049 Uiso 1 1 calc GR . . . . O11_2 O 0.2659(4) 0.3485(6) 0.27850(18) 0.0364(10) Uani 1 1 d . . . . . H11_2 H 0.200436 0.361962 0.287485 0.055 Uiso 1 1 calc GR . . . . C1_2 C -0.0730(5) 0.6417(7) 0.4820(3) 0.0286(13) Uani 1 1 d . . . . . C2_2 C -0.1673(5) 0.5679(8) 0.4971(3) 0.0294(13) Uani 1 1 d . . . . . H2_2 H -0.233544 0.532373 0.468477 0.035 Uiso 1 1 calc R . . . . C3_2 C -0.1689(5) 0.5425(7) 0.5550(3) 0.0299(13) Uani 1 1 d . . . . . C4_2 C -0.0678(6) 0.6076(8) 0.5952(3) 0.0309(13) Uani 1 1 d . . . . . C5_2 C -0.0621(6) 0.6054(8) 0.6545(3) 0.0329(14) Uani 1 1 d . . . . . C6_2 C 0.0299(6) 0.6810(8) 0.6919(3) 0.0341(14) Uani 1 1 d . . . . . H6_2 H 0.032378 0.680392 0.731079 0.041 Uiso 1 1 calc R . . . . C7_2 C 0.1211(6) 0.7600(8) 0.6716(3) 0.0328(13) Uani 1 1 d . . . . . C8_2 C 0.1232(6) 0.7578(8) 0.6141(3) 0.0296(13) Uani 1 1 d . . . . . H8A_2 H 0.187500 0.803344 0.600680 0.036 Uiso 1 1 calc R . . . . C9_2 C 0.0251(6) 0.6847(8) 0.5783(3) 0.0300(13) Uani 1 1 d . . . . . C10_2 C 0.3094(6) 0.8989(10) 0.6950(3) 0.0400(16) Uani 1 1 d . . . . . H10A_2 H 0.285141 0.988883 0.667623 0.060 Uiso 1 1 calc GR . . . . H10B_2 H 0.347251 0.809864 0.677942 0.060 Uiso 1 1 calc GR . . . . H10C_2 H 0.366171 0.942036 0.728363 0.060 Uiso 1 1 calc GR . . . . C11_2 C -0.0667(5) 0.6804(8) 0.4238(3) 0.0282(12) Uani 1 1 d . . . . . C12_2 C 0.0259(6) 0.6244(8) 0.4001(3) 0.0301(13) Uani 1 1 d . . . . . C13_2 C 0.0268(6) 0.6581(9) 0.3446(3) 0.0345(14) Uani 1 1 d . . . . . H13_2 H 0.089753 0.617910 0.329041 0.041 Uiso 1 1 calc R . . . . C14_2 C -0.0651(6) 0.7513(9) 0.3118(3) 0.0347(14) Uani 1 1 d . . . . . H14_2 H -0.064982 0.773762 0.273579 0.042 Uiso 1 1 calc R . . . . C15_2 C -0.1576(6) 0.8125(8) 0.3341(3) 0.0328(14) Uani 1 1 d . . . . . H15_2 H -0.219513 0.877499 0.311480 0.039 Uiso 1 1 calc R . . . . C16_2 C -0.1578(6) 0.7772(8) 0.3896(3) 0.0316(13) Uani 1 1 d . . . . . C17_2 C 0.2285(5) 0.5391(8) 0.4273(3) 0.0303(13) Uani 1 1 d . . . . . H17_2 H 0.245104 0.653212 0.414663 0.036 Uiso 1 1 calc R . . . . C18_2 C 0.3115(5) 0.4979(8) 0.4833(3) 0.0301(13) Uani 1 1 d . . . . . H18_2 H 0.288545 0.386938 0.496083 0.036 Uiso 1 1 calc R . . . . C19_2 C 0.4387(6) 0.4894(8) 0.4783(3) 0.0307(13) Uani 1 1 d . . . . . H19_2 H 0.466082 0.603515 0.470883 0.037 Uiso 1 1 calc R . . . . C20_2 C 0.4491(5) 0.3745(8) 0.4297(3) 0.0304(13) Uani 1 1 d . . . . . H20_2 H 0.433065 0.257533 0.439791 0.037 Uiso 1 1 calc R . . . . C21_2 C 0.3579(5) 0.4238(8) 0.3761(3) 0.0301(13) Uani 1 1 d . . . . . H21_2 H 0.375311 0.538836 0.364598 0.036 Uiso 1 1 calc R . . . . C22_2 C 0.3567(6) 0.3043(9) 0.3280(3) 0.0345(14) Uani 1 1 d . . . . . H22A_2 H 0.435757 0.305279 0.318651 0.041 Uiso 1 1 calc R . . . . H22B_2 H 0.341737 0.190068 0.339987 0.041 Uiso 1 1 calc R . . . . 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 O0AA 0.050(3) 0.073(4) 0.043(3) -0.020(3) 0.018(2) -0.020(3) C0AA 0.051(5) 0.052(4) 0.041(4) -0.007(3) 0.012(3) -0.016(3) O1 0.038(3) 0.042(3) 0.035(3) 0.002(2) 0.001(2) 0.004(2) C1 0.065(5) 0.052(5) 0.047(5) -0.005(4) 0.008(4) -0.008(4) O1_1 0.033(2) 0.034(2) 0.024(2) -0.0007(17) 0.0045(18) 0.0026(18) O2_1 0.031(2) 0.032(2) 0.038(3) -0.0015(18) 0.0064(19) 0.0012(18) O3_1 0.029(2) 0.043(3) 0.034(2) -0.0030(19) 0.0017(19) 0.0052(19) O4_1 0.033(2) 0.047(3) 0.029(2) -0.0065(19) 0.0044(19) 0.003(2) O5_1 0.035(2) 0.045(3) 0.027(2) -0.0039(19) 0.0034(18) -0.009(2) O6_1 0.030(2) 0.032(2) 0.029(2) 0.0047(17) 0.0043(18) -0.0004(17) O7_1 0.026(2) 0.032(2) 0.034(2) 0.0001(17) 0.0016(18) -0.0030(17) O8_1 0.025(2) 0.037(2) 0.040(2) 0.0031(19) 0.0029(18) -0.0008(18) O9_1 0.031(2) 0.039(2) 0.031(2) 0.0044(18) 0.0046(18) -0.0008(19) O10_1 0.030(2) 0.033(2) 0.031(2) -0.0011(18) 0.0003(18) -0.0005(18) O11_1 0.042(3) 0.052(3) 0.033(3) 0.004(2) 0.009(2) -0.001(2) C1_1 0.032(3) 0.029(3) 0.035(4) -0.008(2) 0.005(3) -0.002(3) C2_1 0.028(3) 0.030(3) 0.034(3) 0.000(2) 0.006(3) -0.003(2) C3_1 0.030(3) 0.023(3) 0.032(3) 0.003(2) 0.007(3) 0.000(2) C4_1 0.031(3) 0.026(3) 0.032(3) -0.002(2) 0.008(3) -0.003(2) C5_1 0.030(3) 0.030(3) 0.031(3) -0.001(2) 0.003(3) -0.003(2) C6_1 0.032(3) 0.038(3) 0.030(3) 0.002(3) 0.003(3) 0.002(3) C7_1 0.037(3) 0.033(3) 0.029(3) -0.005(2) 0.005(3) -0.002(3) C8_1 0.029(3) 0.034(3) 0.030(3) -0.003(2) 0.000(3) -0.002(2) C9_1 0.031(3) 0.026(3) 0.028(3) 0.001(2) 0.001(3) 0.000(2) C10_1 0.033(4) 0.056(5) 0.044(4) -0.009(3) 0.006(3) 0.009(3) C11_1 0.030(3) 0.025(3) 0.030(3) -0.001(2) 0.003(3) -0.001(2) C12_1 0.037(3) 0.025(3) 0.028(3) 0.002(2) 0.006(3) -0.002(2) C13_1 0.031(3) 0.033(3) 0.035(3) 0.000(3) 0.000(3) -0.003(3) C14_1 0.038(4) 0.034(3) 0.030(3) 0.001(3) 0.003(3) -0.002(3) C15_1 0.042(4) 0.031(3) 0.025(3) 0.001(2) 0.004(3) -0.003(3) C16_1 0.033(3) 0.030(3) 0.037(4) -0.003(3) 0.007(3) -0.002(3) C17_1 0.029(3) 0.032(3) 0.030(3) -0.006(2) 0.001(3) -0.005(2) C18_1 0.032(3) 0.026(3) 0.033(3) -0.002(2) 0.007(3) -0.001(2) C19_1 0.030(3) 0.031(3) 0.030(3) 0.007(2) 0.002(3) 0.001(3) C20_1 0.029(3) 0.028(3) 0.037(3) 0.003(2) 0.005(3) -0.003(2) C21_1 0.028(3) 0.027(3) 0.035(3) 0.003(2) 0.004(3) -0.001(2) C22_1 0.031(3) 0.036(3) 0.034(3) -0.001(3) 0.003(3) -0.006(3) O1_2 0.029(2) 0.036(2) 0.027(2) -0.0020(17) 0.0010(17) -0.0024(17) O2_2 0.029(2) 0.040(2) 0.035(2) -0.0020(19) 0.0037(19) -0.0019(19) O3_2 0.030(2) 0.048(3) 0.035(3) 0.002(2) 0.004(2) -0.0022(19) O4_2 0.038(3) 0.042(3) 0.028(2) -0.0032(19) 0.0004(19) -0.002(2) O5_2 0.036(3) 0.055(3) 0.033(3) 0.000(2) 0.005(2) 0.017(2) O6_2 0.027(2) 0.034(2) 0.030(2) 0.0027(17) 0.0020(17) 0.0016(17) O7_2 0.030(2) 0.036(2) 0.032(2) -0.0045(18) 0.0041(18) -0.0031(18) O8_2 0.028(2) 0.034(2) 0.039(3) 0.0017(19) 0.0052(19) 0.0014(18) O9_2 0.027(2) 0.034(2) 0.032(2) 0.0024(17) -0.0004(18) -0.0010(17) O10_2 0.031(2) 0.036(2) 0.029(2) -0.0042(18) 0.0024(18) -0.0029(18) O11_2 0.033(2) 0.046(3) 0.028(2) 0.0007(19) 0.0034(18) 0.001(2) C1_2 0.026(3) 0.028(3) 0.027(3) -0.006(2) -0.004(2) -0.002(2) C2_2 0.027(3) 0.027(3) 0.031(3) -0.001(2) 0.000(2) -0.004(2) C3_2 0.030(3) 0.022(3) 0.035(3) -0.002(2) 0.002(3) 0.000(2) C4_2 0.031(3) 0.033(3) 0.026(3) -0.001(2) 0.003(2) 0.001(2) C5_2 0.028(3) 0.039(4) 0.030(3) 0.001(3) 0.003(3) 0.005(3) C6_2 0.037(4) 0.035(3) 0.028(3) 0.003(3) 0.002(3) 0.002(3) C7_2 0.029(3) 0.030(3) 0.035(4) -0.002(3) -0.001(3) 0.004(2) C8_2 0.030(3) 0.026(3) 0.031(3) -0.003(2) 0.003(2) 0.000(2) C9_2 0.030(3) 0.028(3) 0.028(3) 0.002(2) 0.000(2) 0.003(2) C10_2 0.033(3) 0.046(4) 0.038(4) 0.001(3) 0.001(3) -0.008(3) C11_2 0.026(3) 0.026(3) 0.032(3) -0.002(2) 0.006(2) -0.002(2) C12_2 0.030(3) 0.030(3) 0.028(3) -0.002(2) 0.001(3) -0.001(2) C13_2 0.031(3) 0.039(4) 0.032(3) -0.002(3) 0.004(3) -0.001(3) C14_2 0.037(3) 0.035(3) 0.031(3) 0.003(3) 0.006(3) 0.001(3) C15_2 0.032(3) 0.034(3) 0.030(3) -0.001(3) 0.002(3) 0.002(3) C16_2 0.029(3) 0.035(3) 0.028(3) -0.002(2) 0.001(3) 0.001(2) C17_2 0.030(3) 0.025(3) 0.035(3) -0.002(2) 0.006(3) -0.001(2) C18_2 0.029(3) 0.024(3) 0.035(3) -0.002(2) 0.004(3) 0.000(2) C19_2 0.031(3) 0.027(3) 0.032(3) 0.002(2) 0.003(3) -0.001(2) C20_2 0.025(3) 0.034(3) 0.033(3) 0.000(2) 0.007(3) 0.000(2) C21_2 0.026(3) 0.028(3) 0.035(3) 0.003(2) 0.005(2) 0.003(2) C22_2 0.033(3) 0.040(4) 0.029(3) -0.001(3) 0.005(3) 0.001(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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 C0AA O0AA H0AA 109.5 . . ? O0AA C0AA H0AB 109.5 . . ? O0AA C0AA H0AC 109.5 . . ? O0AA C0AA H0AD 109.5 . . ? H0AB C0AA H0AC 109.5 . . ? H0AB C0AA H0AD 109.5 . . ? H0AC C0AA H0AD 109.5 . . ? C1 O1 H1 109.5 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C9_1 O1_1 C1_1 119.8(5) . . ? C5_1 O3_1 H3_1 109.5 . . ? C7_1 O4_1 C10_1 116.4(5) . . ? C16_1 O5_1 H5_1 109.5 . . ? C12_1 O6_1 C17_1 118.8(5) . . ? C17_1 O7_1 C21_1 111.4(5) . . ? C20_1 O8_1 H8_1 109.5 . . ? C19_1 O9_1 H9_1 109.5 . . ? C18_1 O10_1 H10_1 109.5 . . ? C22_1 O11_1 H11_1 109.5 . . ? O1_1 C1_1 C11_1 110.5(5) . . ? C2_1 C1_1 O1_1 122.1(6) . . ? C2_1 C1_1 C11_1 127.4(6) . . ? C1_1 C2_1 H2_1 119.3 . . ? C1_1 C2_1 C3_1 121.4(6) . . ? C3_1 C2_1 H2_1 119.3 . . ? O2_1 C3_1 C2_1 123.9(6) . . ? O2_1 C3_1 C4_1 120.3(6) . . ? C2_1 C3_1 C4_1 115.8(5) . . ? C5_1 C4_1 C3_1 122.2(6) . . ? C9_1 C4_1 C3_1 119.5(6) . . ? C9_1 C4_1 C5_1 118.2(6) . . ? O3_1 C5_1 C4_1 120.6(6) . . ? O3_1 C5_1 C6_1 119.8(6) . . ? C6_1 C5_1 C4_1 119.6(6) . . ? C5_1 C6_1 H6_1 120.0 . . ? C5_1 C6_1 C7_1 120.1(6) . . ? C7_1 C6_1 H6_1 120.0 . . ? O4_1 C7_1 C6_1 114.6(6) . . ? O4_1 C7_1 C8_1 123.2(6) . . ? C8_1 C7_1 C6_1 122.2(6) . . ? C7_1 C8_1 H8A_1 121.6 . . ? C7_1 C8_1 C9_1 116.7(6) . . ? C9_1 C8_1 H8A_1 121.6 . . ? O1_1 C9_1 C4_1 121.2(6) . . ? O1_1 C9_1 C8_1 115.8(5) . . ? C8_1 C9_1 C4_1 123.0(6) . . ? O4_1 C10_1 H10A_1 109.5 . . ? O4_1 C10_1 H10B_1 109.5 . . ? O4_1 C10_1 H10C_1 109.5 . . ? H10A_1 C10_1 H10B_1 109.5 . . ? H10A_1 C10_1 H10C_1 109.5 . . ? H10B_1 C10_1 H10C_1 109.5 . . ? C12_1 C11_1 C1_1 122.2(6) . . ? C12_1 C11_1 C16_1 118.4(6) . . ? C16_1 C11_1 C1_1 119.2(6) . . ? O6_1 C12_1 C11_1 116.1(5) . . ? O6_1 C12_1 C13_1 122.2(6) . . ? C13_1 C12_1 C11_1 121.5(6) . . ? C12_1 C13_1 H13_1 120.8 . . ? C12_1 C13_1 C14_1 118.5(6) . . ? C14_1 C13_1 H13_1 120.8 . . ? C13_1 C14_1 H14_1 119.1 . . ? C15_1 C14_1 C13_1 121.7(6) . . ? C15_1 C14_1 H14_1 119.1 . . ? C14_1 C15_1 H15_1 120.3 . . ? C14_1 C15_1 C16_1 119.3(6) . . ? C16_1 C15_1 H15_1 120.3 . . ? O5_1 C16_1 C11_1 119.2(6) . . ? O5_1 C16_1 C15_1 120.3(6) . . ? C11_1 C16_1 C15_1 120.4(6) . . ? O6_1 C17_1 O7_1 108.3(5) . . ? O6_1 C17_1 H17_1 110.3 . . ? O6_1 C17_1 C18_1 107.7(5) . . ? O7_1 C17_1 H17_1 110.3 . . ? O7_1 C17_1 C18_1 110.0(5) . . ? C18_1 C17_1 H17_1 110.3 . . ? O10_1 C18_1 C17_1 108.8(5) . . ? O10_1 C18_1 H18_1 108.8 . . ? O10_1 C18_1 C19_1 110.7(5) . . ? C17_1 C18_1 H18_1 108.8 . . ? C17_1 C18_1 C19_1 111.0(5) . . ? C19_1 C18_1 H18_1 108.8 . . ? O9_1 C19_1 C18_1 106.6(5) . . ? O9_1 C19_1 H19_1 109.5 . . ? O9_1 C19_1 C20_1 111.7(5) . . ? C18_1 C19_1 H19_1 109.5 . . ? C20_1 C19_1 C18_1 109.8(5) . . ? C20_1 C19_1 H19_1 109.5 . . ? O8_1 C20_1 C19_1 110.4(5) . . ? O8_1 C20_1 H20_1 109.9 . . ? O8_1 C20_1 C21_1 109.1(5) . . ? C19_1 C20_1 H20_1 109.9 . . ? C19_1 C20_1 C21_1 107.5(5) . . ? C21_1 C20_1 H20_1 109.9 . . ? O7_1 C21_1 C20_1 107.9(5) . . ? O7_1 C21_1 H21_1 109.9 . . ? O7_1 C21_1 C22_1 106.5(5) . . ? C20_1 C21_1 H21_1 109.9 . . ? C22_1 C21_1 C20_1 112.6(5) . . ? C22_1 C21_1 H21_1 109.9 . . ? O11_1 C22_1 C21_1 111.4(5) . . ? O11_1 C22_1 H22A_1 109.4 . . ? O11_1 C22_1 H22B_1 109.4 . . ? C21_1 C22_1 H22A_1 109.4 . . ? C21_1 C22_1 H22B_1 109.4 . . ? H22A_1 C22_1 H22B_1 108.0 . . ? C1_2 O1_2 C9_2 119.4(5) . . ? C5_2 O3_2 H3_2 109.5 . . ? C7_2 O4_2 C10_2 117.9(5) . . ? C16_2 O5_2 H5_2 109.5 . . ? C12_2 O6_2 C17_2 116.5(5) . . ? C17_2 O7_2 C21_2 111.0(5) . . ? C20_2 O8_2 H8_2 109.5 . . ? C19_2 O9_2 H9_2 109.5 . . ? C18_2 O10_2 H10_2 109.5 . . ? C22_2 O11_2 H11_2 109.5 . . ? O1_2 C1_2 C11_2 112.9(5) . . ? C2_2 C1_2 O1_2 121.9(6) . . ? C2_2 C1_2 C11_2 125.1(5) . . ? C1_2 C2_2 H2_2 119.2 . . ? C1_2 C2_2 C3_2 121.5(6) . . ? C3_2 C2_2 H2_2 119.2 . . ? O2_2 C3_2 C2_2 122.3(6) . . ? O2_2 C3_2 C4_2 122.4(6) . . ? C2_2 C3_2 C4_2 115.3(6) . . ? C5_2 C4_2 C3_2 121.6(6) . . ? C9_2 C4_2 C3_2 121.4(6) . . ? C9_2 C4_2 C5_2 116.9(6) . . ? O3_2 C5_2 C4_2 120.4(6) . . ? O3_2 C5_2 C6_2 118.8(6) . . ? C6_2 C5_2 C4_2 120.8(6) . . ? C5_2 C6_2 H6_2 120.3 . . ? C5_2 C6_2 C7_2 119.4(6) . . ? C7_2 C6_2 H6_2 120.3 . . ? O4_2 C7_2 C6_2 114.9(6) . . ? O4_2 C7_2 C8_2 123.1(6) . . ? C8_2 C7_2 C6_2 122.0(6) . . ? C7_2 C8_2 H8A_2 122.2 . . ? C9_2 C8_2 C7_2 115.5(6) . . ? C9_2 C8_2 H8A_2 122.2 . . ? C4_2 C9_2 O1_2 120.2(5) . . ? C4_2 C9_2 C8_2 125.2(6) . . ? C8_2 C9_2 O1_2 114.6(6) . . ? O4_2 C10_2 H10A_2 109.5 . . ? O4_2 C10_2 H10B_2 109.5 . . ? O4_2 C10_2 H10C_2 109.5 . . ? H10A_2 C10_2 H10B_2 109.5 . . ? H10A_2 C10_2 H10C_2 109.5 . . ? H10B_2 C10_2 H10C_2 109.5 . . ? C12_2 C11_2 C1_2 123.0(5) . . ? C12_2 C11_2 C16_2 117.8(6) . . ? C16_2 C11_2 C1_2 119.2(5) . . ? O6_2 C12_2 C11_2 114.9(5) . . ? C13_2 C12_2 O6_2 123.7(6) . . ? C13_2 C12_2 C11_2 121.4(6) . . ? C12_2 C13_2 H13_2 120.3 . . ? C12_2 C13_2 C14_2 119.3(6) . . ? C14_2 C13_2 H13_2 120.3 . . ? C13_2 C14_2 H14_2 119.4 . . ? C13_2 C14_2 C15_2 121.1(6) . . ? C15_2 C14_2 H14_2 119.4 . . ? C14_2 C15_2 H15_2 120.5 . . ? C16_2 C15_2 C14_2 119.0(6) . . ? C16_2 C15_2 H15_2 120.5 . . ? O5_2 C16_2 C11_2 116.7(6) . . ? O5_2 C16_2 C15_2 122.0(6) . . ? C15_2 C16_2 C11_2 121.3(6) . . ? O6_2 C17_2 O7_2 108.8(5) . . ? O6_2 C17_2 H17_2 110.7 . . ? O6_2 C17_2 C18_2 106.3(5) . . ? O7_2 C17_2 H17_2 110.7 . . ? O7_2 C17_2 C18_2 109.7(5) . . ? C18_2 C17_2 H17_2 110.7 . . ? O10_2 C18_2 C17_2 109.7(5) . . ? O10_2 C18_2 H18_2 108.6 . . ? O10_2 C18_2 C19_2 110.1(5) . . ? C17_2 C18_2 H18_2 108.6 . . ? C19_2 C18_2 C17_2 111.2(5) . . ? C19_2 C18_2 H18_2 108.6 . . ? O9_2 C19_2 C18_2 106.8(5) . . ? O9_2 C19_2 H19_2 109.2 . . ? O9_2 C19_2 C20_2 112.3(5) . . ? C18_2 C19_2 H19_2 109.2 . . ? C18_2 C19_2 C20_2 110.2(5) . . ? C20_2 C19_2 H19_2 109.2 . . ? O8_2 C20_2 C19_2 109.8(5) . . ? O8_2 C20_2 H20_2 108.9 . . ? O8_2 C20_2 C21_2 110.1(5) . . ? C19_2 C20_2 H20_2 108.9 . . ? C21_2 C20_2 C19_2 110.1(5) . . ? C21_2 C20_2 H20_2 108.9 . . ? O7_2 C21_2 C20_2 109.3(5) . . ? O7_2 C21_2 H21_2 109.7 . . ? O7_2 C21_2 C22_2 106.2(5) . . ? C20_2 C21_2 H21_2 109.7 . . ? C22_2 C21_2 C20_2 112.3(5) . . ? C22_2 C21_2 H21_2 109.7 . . ? O11_2 C22_2 C21_2 111.4(5) . . ? O11_2 C22_2 H22A_2 109.3 . . ? O11_2 C22_2 H22B_2 109.3 . . ? C21_2 C22_2 H22A_2 109.3 . . ? C21_2 C22_2 H22B_2 109.3 . . ? H22A_2 C22_2 H22B_2 108.0 . . ? 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 O0AA H0AA 0.8400 . ? O0AA C0AA 1.418(9) . ? C0AA H0AB 0.9800 . ? C0AA H0AC 0.9800 . ? C0AA H0AD 0.9800 . ? O1 H1 0.8400 . ? O1 C1 1.424(9) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O1_1 C1_1 1.381(8) . ? O1_1 C9_1 1.364(8) . ? O2_1 C3_1 1.260(7) . ? O3_1 H3_1 0.8400 . ? O3_1 C5_1 1.340(8) . ? O4_1 C7_1 1.373(8) . ? O4_1 C10_1 1.423(8) . ? O5_1 H5_1 0.8400 . ? O5_1 C16_1 1.370(8) . ? O6_1 C12_1 1.391(7) . ? O6_1 C17_1 1.405(7) . ? O7_1 C17_1 1.423(7) . ? O7_1 C21_1 1.441(7) . ? O8_1 H8_1 0.8400 . ? O8_1 C20_1 1.435(7) . ? O9_1 H9_1 0.8400 . ? O9_1 C19_1 1.431(7) . ? O10_1 H10_1 0.8400 . ? O10_1 C18_1 1.431(7) . ? O11_1 H11_1 0.8400 . ? O11_1 C22_1 1.454(8) . ? C1_1 C2_1 1.340(9) . ? C1_1 C11_1 1.476(9) . ? C2_1 H2_1 0.9500 . ? C2_1 C3_1 1.442(9) . ? C3_1 C4_1 1.451(9) . ? C4_1 C5_1 1.411(9) . ? C4_1 C9_1 1.404(9) . ? C5_1 C6_1 1.385(9) . ? C6_1 H6_1 0.9500 . ? C6_1 C7_1 1.399(9) . ? C7_1 C8_1 1.384(9) . ? C8_1 H8A_1 0.9500 . ? C8_1 C9_1 1.395(9) . ? C10_1 H10A_1 0.9800 . ? C10_1 H10B_1 0.9800 . ? C10_1 H10C_1 0.9800 . ? C11_1 C12_1 1.394(9) . ? C11_1 C16_1 1.405(9) . ? C12_1 C13_1 1.391(9) . ? C13_1 H13_1 0.9500 . ? C13_1 C14_1 1.396(9) . ? C14_1 H14_1 0.9500 . ? C14_1 C15_1 1.367(9) . ? C15_1 H15_1 0.9500 . ? C15_1 C16_1 1.405(9) . ? C17_1 H17_1 1.0000 . ? C17_1 C18_1 1.521(9) . ? C18_1 H18_1 1.0000 . ? C18_1 C19_1 1.529(8) . ? C19_1 H19_1 1.0000 . ? C19_1 C20_1 1.517(9) . ? C20_1 H20_1 1.0000 . ? C20_1 C21_1 1.530(9) . ? C21_1 H21_1 1.0000 . ? C21_1 C22_1 1.511(9) . ? C22_1 H22A_1 0.9900 . ? C22_1 H22B_1 0.9900 . ? O1_2 C1_2 1.364(7) . ? O1_2 C9_2 1.392(8) . ? O2_2 C3_2 1.263(8) . ? O3_2 H3_2 0.8400 . ? O3_2 C5_2 1.358(8) . ? O4_2 C7_2 1.346(8) . ? O4_2 C10_2 1.440(8) . ? O5_2 H5_2 0.8400 . ? O5_2 C16_2 1.366(8) . ? O6_2 C12_2 1.384(7) . ? O6_2 C17_2 1.409(7) . ? O7_2 C17_2 1.420(7) . ? O7_2 C21_2 1.429(7) . ? O8_2 H8_2 0.8400 . ? O8_2 C20_2 1.425(7) . ? O9_2 H9_2 0.8400 . ? O9_2 C19_2 1.443(7) . ? O10_2 H10_2 0.8400 . ? O10_2 C18_2 1.429(7) . ? O11_2 H11_2 0.8400 . ? O11_2 C22_2 1.446(8) . ? C1_2 C2_2 1.362(9) . ? C1_2 C11_2 1.471(9) . ? C2_2 H2_2 0.9500 . ? C2_2 C3_2 1.429(9) . ? C3_2 C4_2 1.436(9) . ? C4_2 C5_2 1.430(9) . ? C4_2 C9_2 1.381(9) . ? C5_2 C6_2 1.369(9) . ? C6_2 H6_2 0.9500 . ? C6_2 C7_2 1.413(10) . ? C7_2 C8_2 1.408(9) . ? C8_2 H8A_2 0.9500 . ? C8_2 C9_2 1.388(9) . ? C10_2 H10A_2 0.9800 . ? C10_2 H10B_2 0.9800 . ? C10_2 H10C_2 0.9800 . ? C11_2 C12_2 1.401(9) . ? C11_2 C16_2 1.412(9) . ? C12_2 C13_2 1.383(9) . ? C13_2 H13_2 0.9500 . ? C13_2 C14_2 1.388(9) . ? C14_2 H14_2 0.9500 . ? C14_2 C15_2 1.394(9) . ? C15_2 H15_2 0.9500 . ? C15_2 C16_2 1.384(9) . ? C17_2 H17_2 1.0000 . ? C17_2 C18_2 1.510(9) . ? C18_2 H18_2 1.0000 . ? C18_2 C19_2 1.501(8) . ? C19_2 H19_2 1.0000 . ? C19_2 C20_2 1.528(9) . ? C20_2 H20_2 1.0000 . ? C20_2 C21_2 1.526(8) . ? C21_2 H21_2 1.0000 . ? C21_2 C22_2 1.512(9) . ? C22_2 H22A_2 0.9900 . ? C22_2 H22B_2 0.9900 . ? 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_1 C1_1 C2_1 C3_1 4.2(10) . . . . ? O1_1 C1_1 C11_1 C12_1 46.6(8) . . . . ? O1_1 C1_1 C11_1 C16_1 -128.9(6) . . . . ? O2_1 C3_1 C4_1 C5_1 -3.7(9) . . . . ? O2_1 C3_1 C4_1 C9_1 178.0(5) . . . . ? O3_1 C5_1 C6_1 C7_1 176.6(6) . . . . ? O4_1 C7_1 C8_1 C9_1 -179.8(6) . . . . ? O6_1 C12_1 C13_1 C14_1 175.2(6) . . . . ? O6_1 C17_1 C18_1 O10_1 -66.4(6) . . . . ? O6_1 C17_1 C18_1 C19_1 171.6(5) . . . . ? O7_1 C17_1 C18_1 O10_1 175.8(5) . . . . ? O7_1 C17_1 C18_1 C19_1 53.8(7) . . . . ? O7_1 C21_1 C22_1 O11_1 65.3(7) . . . . ? O8_1 C20_1 C21_1 O7_1 176.8(5) . . . . ? O8_1 C20_1 C21_1 C22_1 59.6(7) . . . . ? O9_1 C19_1 C20_1 O8_1 -66.2(6) . . . . ? O9_1 C19_1 C20_1 C21_1 174.8(5) . . . . ? O10_1 C18_1 C19_1 O9_1 65.3(6) . . . . ? O10_1 C18_1 C19_1 C20_1 -173.4(5) . . . . ? C1_1 O1_1 C9_1 C4_1 -0.1(9) . . . . ? C1_1 O1_1 C9_1 C8_1 -177.8(5) . . . . ? C1_1 C2_1 C3_1 O2_1 178.1(6) . . . . ? C1_1 C2_1 C3_1 C4_1 -0.5(9) . . . . ? C1_1 C11_1 C12_1 O6_1 10.9(9) . . . . ? C1_1 C11_1 C12_1 C13_1 -173.2(6) . . . . ? C1_1 C11_1 C16_1 O5_1 -4.1(9) . . . . ? C1_1 C11_1 C16_1 C15_1 173.5(6) . . . . ? C2_1 C1_1 C11_1 C12_1 -136.5(7) . . . . ? C2_1 C1_1 C11_1 C16_1 48.1(10) . . . . ? C2_1 C3_1 C4_1 C5_1 174.9(6) . . . . ? C2_1 C3_1 C4_1 C9_1 -3.3(8) . . . . ? C3_1 C4_1 C5_1 O3_1 2.2(10) . . . . ? C3_1 C4_1 C5_1 C6_1 -178.2(6) . . . . ? C3_1 C4_1 C9_1 O1_1 3.7(9) . . . . ? C3_1 C4_1 C9_1 C8_1 -178.8(6) . . . . ? C4_1 C5_1 C6_1 C7_1 -2.9(10) . . . . ? C5_1 C4_1 C9_1 O1_1 -174.6(6) . . . . ? C5_1 C4_1 C9_1 C8_1 2.9(9) . . . . ? C5_1 C6_1 C7_1 O4_1 -177.3(6) . . . . ? C5_1 C6_1 C7_1 C8_1 3.2(10) . . . . ? C6_1 C7_1 C8_1 C9_1 -0.4(10) . . . . ? C7_1 C8_1 C9_1 O1_1 175.0(6) . . . . ? C7_1 C8_1 C9_1 C4_1 -2.7(10) . . . . ? C9_1 O1_1 C1_1 C2_1 -3.9(9) . . . . ? C9_1 O1_1 C1_1 C11_1 173.2(5) . . . . ? C9_1 C4_1 C5_1 O3_1 -179.6(6) . . . . ? C9_1 C4_1 C5_1 C6_1 0.0(9) . . . . ? C10_1 O4_1 C7_1 C6_1 174.3(6) . . . . ? C10_1 O4_1 C7_1 C8_1 -6.3(10) . . . . ? C11_1 C1_1 C2_1 C3_1 -172.5(6) . . . . ? C11_1 C12_1 C13_1 C14_1 -0.5(10) . . . . ? C12_1 O6_1 C17_1 O7_1 -76.7(6) . . . . ? C12_1 O6_1 C17_1 C18_1 164.4(5) . . . . ? C12_1 C11_1 C16_1 O5_1 -179.7(6) . . . . ? C12_1 C11_1 C16_1 C15_1 -2.2(9) . . . . ? C12_1 C13_1 C14_1 C15_1 -1.5(10) . . . . ? C13_1 C14_1 C15_1 C16_1 1.6(10) . . . . ? C14_1 C15_1 C16_1 O5_1 177.8(6) . . . . ? C14_1 C15_1 C16_1 C11_1 0.3(10) . . . . ? C16_1 C11_1 C12_1 O6_1 -173.7(5) . . . . ? C16_1 C11_1 C12_1 C13_1 2.3(9) . . . . ? C17_1 O6_1 C12_1 C11_1 -157.4(5) . . . . ? C17_1 O6_1 C12_1 C13_1 26.7(8) . . . . ? C17_1 O7_1 C21_1 C20_1 67.3(6) . . . . ? C17_1 O7_1 C21_1 C22_1 -171.5(5) . . . . ? C17_1 C18_1 C19_1 O9_1 -173.8(5) . . . . ? C17_1 C18_1 C19_1 C20_1 -52.5(7) . . . . ? C18_1 C19_1 C20_1 O8_1 175.7(5) . . . . ? C18_1 C19_1 C20_1 C21_1 56.7(6) . . . . ? C19_1 C20_1 C21_1 O7_1 -63.4(6) . . . . ? C19_1 C20_1 C21_1 C22_1 179.4(5) . . . . ? C20_1 C21_1 C22_1 O11_1 -176.6(5) . . . . ? C21_1 O7_1 C17_1 O6_1 -179.4(5) . . . . ? C21_1 O7_1 C17_1 C18_1 -62.0(6) . . . . ? O1_2 C1_2 C2_2 C3_2 -0.1(10) . . . . ? O1_2 C1_2 C11_2 C12_2 58.4(8) . . . . ? O1_2 C1_2 C11_2 C16_2 -122.1(6) . . . . ? O2_2 C3_2 C4_2 C5_2 -4.1(9) . . . . ? O2_2 C3_2 C4_2 C9_2 -180.0(6) . . . . ? O3_2 C5_2 C6_2 C7_2 179.4(6) . . . . ? O4_2 C7_2 C8_2 C9_2 -176.3(6) . . . . ? O6_2 C12_2 C13_2 C14_2 178.4(6) . . . . ? O6_2 C17_2 C18_2 O10_2 -63.0(6) . . . . ? O6_2 C17_2 C18_2 C19_2 175.0(5) . . . . ? O7_2 C17_2 C18_2 O10_2 179.6(5) . . . . ? O7_2 C17_2 C18_2 C19_2 57.6(6) . . . . ? O7_2 C21_2 C22_2 O11_2 57.8(6) . . . . ? O8_2 C20_2 C21_2 O7_2 -178.4(5) . . . . ? O8_2 C20_2 C21_2 C22_2 64.0(7) . . . . ? O9_2 C19_2 C20_2 O8_2 -68.5(6) . . . . ? O9_2 C19_2 C20_2 C21_2 170.1(5) . . . . ? O10_2 C18_2 C19_2 O9_2 64.7(6) . . . . ? O10_2 C18_2 C19_2 C20_2 -173.2(5) . . . . ? C1_2 O1_2 C9_2 C4_2 5.5(8) . . . . ? C1_2 O1_2 C9_2 C8_2 -173.8(5) . . . . ? C1_2 C2_2 C3_2 O2_2 -178.8(6) . . . . ? C1_2 C2_2 C3_2 C4_2 3.0(9) . . . . ? C1_2 C11_2 C12_2 O6_2 -0.1(9) . . . . ? C1_2 C11_2 C12_2 C13_2 177.7(6) . . . . ? C1_2 C11_2 C16_2 O5_2 2.8(9) . . . . ? C1_2 C11_2 C16_2 C15_2 -178.0(6) . . . . ? C2_2 C1_2 C11_2 C12_2 -124.8(7) . . . . ? C2_2 C1_2 C11_2 C16_2 54.8(9) . . . . ? C2_2 C3_2 C4_2 C5_2 174.1(6) . . . . ? C2_2 C3_2 C4_2 C9_2 -1.8(9) . . . . ? C3_2 C4_2 C5_2 O3_2 5.4(9) . . . . ? C3_2 C4_2 C5_2 C6_2 -174.2(6) . . . . ? C3_2 C4_2 C9_2 O1_2 -2.4(9) . . . . ? C3_2 C4_2 C9_2 C8_2 176.9(6) . . . . ? C4_2 C5_2 C6_2 C7_2 -1.0(10) . . . . ? C5_2 C4_2 C9_2 O1_2 -178.5(5) . . . . ? C5_2 C4_2 C9_2 C8_2 0.8(10) . . . . ? C5_2 C6_2 C7_2 O4_2 178.5(6) . . . . ? C5_2 C6_2 C7_2 C8_2 -2.6(10) . . . . ? C6_2 C7_2 C8_2 C9_2 4.9(9) . . . . ? C7_2 C8_2 C9_2 O1_2 175.3(5) . . . . ? C7_2 C8_2 C9_2 C4_2 -4.1(9) . . . . ? C9_2 O1_2 C1_2 C2_2 -4.3(9) . . . . ? C9_2 O1_2 C1_2 C11_2 172.7(5) . . . . ? C9_2 C4_2 C5_2 O3_2 -178.5(6) . . . . ? C9_2 C4_2 C5_2 C6_2 1.9(9) . . . . ? C10_2 O4_2 C7_2 C6_2 172.4(6) . . . . ? C10_2 O4_2 C7_2 C8_2 -6.4(9) . . . . ? C11_2 C1_2 C2_2 C3_2 -176.7(6) . . . . ? C11_2 C12_2 C13_2 C14_2 0.9(10) . . . . ? C12_2 O6_2 C17_2 O7_2 -87.8(6) . . . . ? C12_2 O6_2 C17_2 C18_2 154.1(5) . . . . ? C12_2 C11_2 C16_2 O5_2 -177.6(6) . . . . ? C12_2 C11_2 C16_2 C15_2 1.6(9) . . . . ? C12_2 C13_2 C14_2 C15_2 0.6(10) . . . . ? C13_2 C14_2 C15_2 C16_2 -0.9(10) . . . . ? C14_2 C15_2 C16_2 O5_2 178.9(6) . . . . ? C14_2 C15_2 C16_2 C11_2 -0.2(10) . . . . ? C16_2 C11_2 C12_2 O6_2 -179.7(5) . . . . ? C16_2 C11_2 C12_2 C13_2 -1.9(9) . . . . ? C17_2 O6_2 C12_2 C11_2 -149.6(5) . . . . ? C17_2 O6_2 C12_2 C13_2 32.7(8) . . . . ? C17_2 O7_2 C21_2 C20_2 64.5(6) . . . . ? C17_2 O7_2 C21_2 C22_2 -174.1(5) . . . . ? C17_2 C18_2 C19_2 O9_2 -173.6(5) . . . . ? C17_2 C18_2 C19_2 C20_2 -51.4(7) . . . . ? C18_2 C19_2 C20_2 O8_2 172.6(5) . . . . ? C18_2 C19_2 C20_2 C21_2 51.2(7) . . . . ? C19_2 C20_2 C21_2 O7_2 -57.1(6) . . . . ? C19_2 C20_2 C21_2 C22_2 -174.7(5) . . . . ? C20_2 C21_2 C22_2 O11_2 177.2(5) . . . . ? C21_2 O7_2 C17_2 O6_2 179.7(5) . . . . ? C21_2 O7_2 C17_2 C18_2 -64.5(6) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.8(3) 2 0.20(4) 3 0.1(3) 4 -0.11(4)