#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:27:53 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252908 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157455.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_7157455 loop_ _publ_author_name 'Wu, Xinjie' 'Jia, Ming' 'Huang, Mengmeng' 'Kim, Jung Keun' 'Zhao, Zheng' 'Liu, Junkai' 'Xi, Jinhu' 'Li, Yabo' 'Wu, Yangjie' _publ_section_title ; A visible-light-induced "on-off" one-pot synthesis of 3-arylacetylene coumarins with AIE properties. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3346 _journal_page_last 3353 _journal_paper_doi 10.1039/d0ob00479k _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C23 H14 O2' _chemical_formula_sum 'C23 H14 O2' _chemical_formula_weight 322.34 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-11-08 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-20 deposited with the CCDC. 2020-04-06 downloaded from the CCDC. ; _cell_angle_alpha 87.690(5) _cell_angle_beta 77.763(5) _cell_angle_gamma 71.943(6) _cell_formula_units_Z 4 _cell_length_a 10.9195(8) _cell_length_b 11.7513(7) _cell_length_c 14.2060(6) _cell_measurement_reflns_used 3391 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.5420 _cell_measurement_theta_min 3.9470 _cell_volume 1693.10(19) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -102.00 -15.00 1.00 1.00 -- -33.50 -57.00 30.00 87 2 \w -105.00 38.00 1.00 1.00 -- -33.50 0.00 90.00 143 3 \w -108.00 -32.00 1.00 1.00 -- -33.50 178.00 -90.00 76 4 \w -52.00 -18.00 1.00 1.00 -- -33.50 0.00 90.00 34 5 \w 35.00 72.00 1.00 1.00 -- 36.47 -99.00 -60.00 37 6 \w 11.00 72.00 1.00 1.00 -- 36.47 -99.00 90.00 61 7 \w -4.00 73.00 1.00 1.00 -- 36.47 -99.00-150.00 77 8 \w 26.00 62.00 1.00 1.00 -- 36.47 -77.00 90.00 36 9 \w 71.00 96.00 1.00 1.00 -- 36.47 178.00 0.00 25 10 \w -27.00 19.00 1.00 1.00 -- 36.47 -77.00 90.00 46 11 \w -31.00 46.00 1.00 1.00 -- 36.47 -37.00 120.00 77 12 \w 64.00 108.00 1.00 1.00 -- 36.47 178.00 90.00 44 13 \w 86.00 136.00 1.00 7.00 -- 108.00 30.00 0.00 50 14 \w 39.00 132.00 1.00 7.00 -- 108.00 -77.00 60.00 93 15 \w 38.00 125.00 1.00 7.00 -- 108.00 -30.00 0.00 87 16 \w 100.00 178.00 1.00 7.00 -- 108.00 30.00 90.00 78 17 \w 39.00 127.00 1.00 7.00 -- 108.00 -45.00 -90.00 88 18 \w 37.00 85.00 1.00 7.00 -- 108.00 -30.00 120.00 48 19 \w 54.00 100.00 1.00 7.00 -- 108.00 -94.00 -30.00 46 20 \w 38.00 116.00 1.00 7.00 -- 108.00 -45.00-180.00 78 21 \w 94.00 120.00 1.00 7.00 -- 108.00 45.00 -90.00 26 22 \w 60.00 93.00 1.00 7.00 -- 108.00 -94.00 -90.00 33 23 \w 84.00 111.00 1.00 7.00 -- 108.00-111.00-180.00 27 24 \w 114.00 177.00 1.00 7.00 -- 108.00 15.00-150.00 63 25 \w 40.00 66.00 1.00 7.00 -- 108.00-111.00-180.00 26 26 \w 58.00 110.00 1.00 7.00 -- 108.00 -94.00 30.00 52 27 \w 64.00 95.00 1.00 7.00 -- 108.00 15.00-150.00 31 28 \w 37.00 112.00 1.00 7.00 -- 108.00-111.00-120.00 75 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0784980000 _diffrn_orient_matrix_UB_12 -0.1280965000 _diffrn_orient_matrix_UB_13 0.0219370000 _diffrn_orient_matrix_UB_21 0.1280679000 _diffrn_orient_matrix_UB_22 0.0344724000 _diffrn_orient_matrix_UB_23 -0.0230228000 _diffrn_orient_matrix_UB_31 -0.0217286000 _diffrn_orient_matrix_UB_32 0.0378166000 _diffrn_orient_matrix_UB_33 0.1063547000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_unetI/netI 0.0328 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11792 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.079 _diffrn_reflns_theta_max 67.079 _diffrn_reflns_theta_min 3.958 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.265 _exptl_crystal_description block _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.204 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.032 _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 452 _refine_ls_number_reflns 5950 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0473 _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^)+(0.0717P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.1428 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4481 _reflns_number_total 5950 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201911284.res created by SHELXL-2014/7 TITL 201911284 in P-1 #2 REM reset to P-1 #2 CELL 1.54184 10.919533 11.751349 14.205973 87.6895 77.7632 71.9433 ZERR 4 0.000761 0.000731 0.000649 0.0045 0.0049 0.0059 LATT 1 SFAC C H O UNIT 92 56 8 L.S. 4 0 0 PLAN 20 SIZE 0.1 0.12 0.16 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 O2 MPLA C10 C11 C12 C13 C14 C15 MPLA C18 C19 C20 C21 C22 C23 MPLA C1' C2' C3' C4' C5' C6' C7' C8' C9' O2' MPLA C10' C11' C12' C13' C14' C15' MPLA C18' C19' C20' C21' C22' C23' BOND $h conf fmap 2 acta REM REM REM WGHT 0.071700 0.112500 EXTI 0.001916 FVAR 4.40632 C1 1 1.245140 0.511388 0.595818 11.00000 0.05954 0.06020 = 0.05816 0.00605 -0.01280 -0.01202 C2 1 1.103862 0.576859 0.613467 11.00000 0.05598 0.05463 = 0.04950 0.00073 -0.01236 -0.01536 C3 1 1.058417 0.698431 0.614376 11.00000 0.05298 0.05461 = 0.04706 0.00013 -0.01229 -0.01623 C4 1 1.152369 0.764976 0.595373 11.00000 0.05363 0.05856 = 0.05326 0.00103 -0.01277 -0.01952 C5 1 1.285927 0.700968 0.580854 11.00000 0.05574 0.06781 = 0.05899 0.00471 -0.01838 -0.02019 C6 1 1.382133 0.757516 0.560799 11.00000 0.05415 0.09108 = 0.09241 0.00807 -0.02099 -0.02865 AFIX 43 H6 2 1.470792 0.713178 0.551559 11.00000 -1.20000 AFIX 0 C7 1 1.344912 0.879702 0.554753 11.00000 0.07350 0.09044 = 0.10479 0.00862 -0.02023 -0.04637 AFIX 43 H7 2 1.408844 0.918487 0.541948 11.00000 -1.20000 AFIX 0 C8 1 1.213673 0.945756 0.567454 11.00000 0.08351 0.06613 = 0.10274 0.00323 -0.01517 -0.03765 AFIX 43 H8 2 1.189803 1.028576 0.562580 11.00000 -1.20000 AFIX 0 C9 1 1.117682 0.889768 0.587326 11.00000 0.06079 0.06030 = 0.07949 0.00136 -0.01153 -0.02064 AFIX 43 H9 2 1.029410 0.934961 0.595449 11.00000 -1.20000 AFIX 0 C10 1 0.914223 0.763101 0.633990 11.00000 0.05016 0.04797 = 0.06252 0.00142 -0.00997 -0.01726 C11 1 0.854615 0.840125 0.713407 11.00000 0.06186 0.06075 = 0.07163 -0.00679 -0.01107 -0.01970 AFIX 43 H11 2 0.905216 0.853800 0.754183 11.00000 -1.20000 AFIX 0 C12 1 0.719863 0.896810 0.732226 11.00000 0.06341 0.06964 = 0.08977 -0.01543 0.00278 -0.01648 AFIX 43 H12 2 0.680052 0.947173 0.786298 11.00000 -1.20000 AFIX 0 C13 1 0.644728 0.878799 0.671115 11.00000 0.04483 0.07557 = 0.12089 -0.00644 -0.00576 -0.01513 AFIX 43 H13 2 0.554401 0.917350 0.683496 11.00000 -1.20000 AFIX 0 C14 1 0.704121 0.803308 0.591472 11.00000 0.05649 0.07482 = 0.10250 -0.00184 -0.02467 -0.02350 AFIX 43 H14 2 0.653677 0.791733 0.549732 11.00000 -1.20000 AFIX 0 C15 1 0.837573 0.744927 0.573279 11.00000 0.05742 0.05918 = 0.07230 -0.00294 -0.01611 -0.01927 AFIX 43 H15 2 0.876467 0.693062 0.520014 11.00000 -1.20000 AFIX 0 C16 1 1.018921 0.503931 0.630038 11.00000 0.06252 0.05029 = 0.05459 0.00108 -0.01053 -0.01429 C17 1 0.946509 0.443338 0.641967 11.00000 0.06414 0.05224 = 0.05415 0.00094 -0.01025 -0.01578 C18 1 0.858370 0.373834 0.651002 11.00000 0.06185 0.05745 = 0.04570 -0.00128 -0.00656 -0.01779 C19 1 0.726969 0.427823 0.646338 11.00000 0.06511 0.06647 = 0.06601 -0.00090 -0.00832 -0.01285 AFIX 43 H19 2 0.695447 0.510045 0.638739 11.00000 -1.20000 AFIX 0 C20 1 0.643191 0.358687 0.653051 11.00000 0.05683 0.11085 = 0.07844 -0.00660 -0.00729 -0.02695 AFIX 43 H20 2 0.555752 0.394777 0.649031 11.00000 -1.20000 AFIX 0 C21 1 0.688043 0.237726 0.665550 11.00000 0.08386 0.09553 = 0.06926 -0.00567 0.00145 -0.04998 AFIX 43 H21 2 0.631011 0.192132 0.670588 11.00000 -1.20000 AFIX 0 C22 1 0.817008 0.184108 0.670607 11.00000 0.09711 0.06300 = 0.06464 0.00065 -0.00274 -0.03662 AFIX 43 H22 2 0.847264 0.102001 0.679173 11.00000 -1.20000 AFIX 0 C23 1 0.902651 0.251120 0.663074 11.00000 0.06868 0.05942 = 0.05739 0.00298 -0.00930 -0.01841 AFIX 43 H23 2 0.990239 0.213792 0.666112 11.00000 -1.20000 AFIX 0 O1 3 1.292962 0.404555 0.592114 11.00000 0.07025 0.05771 = 0.10193 0.00845 -0.01142 -0.00381 O2 3 1.329449 0.578452 0.582478 11.00000 0.05168 0.06767 = 0.07633 0.00799 -0.01703 -0.01298 C1' 1 1.203632 0.843755 0.097875 11.00000 0.06116 0.07495 = 0.05464 0.00944 -0.01638 -0.02538 C2' 1 1.062183 0.861553 0.109462 11.00000 0.05577 0.06153 = 0.04805 0.00493 -0.01357 -0.01704 C3' 1 1.014313 0.767339 0.108554 11.00000 0.05212 0.05904 = 0.04742 0.00435 -0.01249 -0.01471 C4' 1 1.105695 0.647494 0.096780 11.00000 0.05495 0.06112 = 0.04981 0.00177 -0.01350 -0.01235 C5' 1 1.239210 0.632371 0.087838 11.00000 0.05701 0.07085 = 0.05228 -0.00026 -0.01383 -0.01146 C6' 1 1.332575 0.520997 0.077455 11.00000 0.05755 0.08695 = 0.07907 -0.00565 -0.01813 0.00008 AFIX 43 H6' 2 1.420879 0.513597 0.073244 11.00000 -1.20000 AFIX 0 C7' 1 1.293744 0.420838 0.073382 11.00000 0.08280 0.06853 = 0.10413 -0.01111 -0.02793 0.00855 AFIX 43 H7' 2 1.355994 0.345267 0.066542 11.00000 -1.20000 AFIX 0 C8' 1 1.163045 0.432251 0.079407 11.00000 0.09145 0.05775 = 0.11154 -0.00591 -0.02879 -0.00986 AFIX 43 H8' 2 1.137300 0.364509 0.075458 11.00000 -1.20000 AFIX 0 C9' 1 1.070454 0.543664 0.091257 11.00000 0.06774 0.06347 = 0.08101 -0.00157 -0.01986 -0.01439 AFIX 43 H9' 2 0.982339 0.550118 0.095703 11.00000 -1.20000 AFIX 0 C10' 1 0.870444 0.787410 0.119791 11.00000 0.05060 0.05064 = 0.06379 0.00219 -0.01277 -0.01203 C11' 1 0.801634 0.740670 0.196980 11.00000 0.06097 0.06495 = 0.07599 0.01382 -0.01163 -0.01578 AFIX 43 H11' 2 0.845528 0.695942 0.242157 11.00000 -1.20000 AFIX 0 C12' 1 0.667674 0.760584 0.206780 11.00000 0.05651 0.08047 = 0.10337 0.01855 -0.00242 -0.02093 AFIX 43 H12' 2 0.621889 0.729680 0.258950 11.00000 -1.20000 AFIX 0 C13' 1 0.601724 0.825691 0.140005 11.00000 0.04997 0.07880 = 0.12209 0.00530 -0.01637 -0.01585 AFIX 43 H13' 2 0.511980 0.837948 0.146473 11.00000 -1.20000 AFIX 0 C14' 1 0.669884 0.872778 0.063189 11.00000 0.06027 0.07009 = 0.09537 0.00800 -0.02873 -0.00983 AFIX 43 H14' 2 0.625575 0.916787 0.017928 11.00000 -1.20000 AFIX 0 C15' 1 0.803560 0.854971 0.053067 11.00000 0.05849 0.06141 = 0.07257 0.00876 -0.01784 -0.01591 AFIX 43 H15' 2 0.848430 0.888065 0.001849 11.00000 -1.20000 AFIX 0 C16' 1 0.978820 0.982115 0.125406 11.00000 0.06232 0.06090 = 0.05609 0.00429 -0.01387 -0.02220 C17' 1 0.904535 1.081785 0.140043 11.00000 0.06617 0.06301 = 0.05733 0.00382 -0.01317 -0.02223 C18' 1 0.809739 1.198585 0.155928 11.00000 0.06489 0.06448 = 0.05177 0.00088 -0.01452 -0.01463 C19' 1 0.676558 1.211288 0.176159 11.00000 0.07104 0.08822 = 0.08396 0.00193 -0.01906 -0.02178 AFIX 43 H19' 2 0.648596 1.143837 0.179294 11.00000 -1.20000 AFIX 0 C20' 1 0.584671 1.324022 0.191767 11.00000 0.06379 0.12197 = 0.09617 -0.00692 -0.01842 0.00036 AFIX 43 H20' 2 0.495232 1.331928 0.206195 11.00000 -1.20000 AFIX 0 C21' 1 0.624909 1.424024 0.186053 11.00000 0.09855 0.08383 = 0.08287 -0.01128 -0.02483 0.01162 AFIX 43 H21' 2 0.562935 1.499696 0.195636 11.00000 -1.20000 AFIX 0 C22' 1 0.755851 1.412279 0.166310 11.00000 0.11272 0.06195 = 0.07359 -0.00446 -0.02183 -0.01403 AFIX 43 H22' 2 0.782998 1.480190 0.163148 11.00000 -1.20000 AFIX 0 C23' 1 0.848570 1.300630 0.150961 11.00000 0.07726 0.06524 = 0.06786 0.00061 -0.01264 -0.01942 AFIX 43 H23' 2 0.937748 1.293777 0.137186 11.00000 -1.20000 AFIX 0 O1' 3 1.252921 0.922405 0.097208 11.00000 0.07505 0.09090 = 0.09823 0.01777 -0.02973 -0.04360 O2' 3 1.285499 0.728868 0.087937 11.00000 0.04982 0.08113 = 0.07171 0.00251 -0.01458 -0.01720 HKLF 4 REM 201911284 in P-1 #2 REM R1 = 0.0473 for 4481 Fo > 4sig(Fo) and 0.0637 for all 5950 data REM 452 parameters refined using 0 restraints END WGHT 0.0717 0.1126 REM Highest difference peak 0.204, deepest hole -0.164, 1-sigma level 0.032 Q1 1 1.0803 0.6380 0.6436 11.00000 0.05 0.20 Q2 1 1.1262 0.8376 0.6319 11.00000 0.05 0.18 Q3 1 1.0840 0.6264 0.5799 11.00000 0.05 0.18 Q4 1 0.9619 1.0521 0.1693 11.00000 0.05 0.16 Q5 1 0.9465 0.5212 0.6217 11.00000 0.05 0.16 Q6 1 1.1549 0.5541 0.6173 11.00000 0.05 0.15 Q7 1 1.2796 0.4585 0.6425 11.00000 0.05 0.15 Q8 1 1.0365 0.4282 0.6220 11.00000 0.05 0.13 Q9 1 0.8888 0.3089 0.6347 11.00000 0.05 0.13 Q10 1 1.1600 1.0380 0.6150 11.00000 0.05 0.13 Q11 1 0.6675 0.8057 0.6522 11.00000 0.05 0.13 Q12 1 0.8761 0.3203 0.6775 11.00000 0.05 0.13 Q13 1 1.4979 0.6698 0.5067 11.00000 0.05 0.12 Q14 1 0.9987 0.7243 0.6289 11.00000 0.05 0.12 Q15 1 0.8382 0.8551 0.1134 11.00000 0.05 0.12 Q16 1 1.0424 0.9240 0.1092 11.00000 0.05 0.12 Q17 1 1.0390 0.8074 0.1482 11.00000 0.05 0.12 Q18 1 1.1002 0.4842 0.1318 11.00000 0.05 0.12 Q19 1 1.3179 0.6405 0.6140 11.00000 0.05 0.11 Q20 1 1.3522 0.8234 0.6009 11.00000 0.05 0.11 REM The information below was added by Olex2. REM REM R1 = 0.0473 for 4481 Fo > 4sig(Fo) and 0.0637 for all 11792 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.20, deepest hole -0.16 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0637 REM R1_gt = 0.0473 REM wR_ref = 0.1428 REM GOOF = 1.018 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11792 REM Reflections_gt = 4481 REM Parameters = n/a REM Hole = -0.16 REM Peak = 0.20 REM Flack = n/a ; _cod_data_source_file d0ob00479k2.cif _cod_data_source_block 201911284 _cod_depositor_comments 'Adding full bibliography for 7157451--7157455.cif.' _cod_original_cell_volume 1693.11(19) _cod_database_code 7157455 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C40H40O2N4 _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 0.939 _shelx_estimated_absorpt_t_min 0.905 _reflns_odcompleteness_completeness 98.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23') ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.448 _oxdiff_exptl_absorpt_empirical_full_min 0.872 loop_ _space_group_symop_operation_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_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 C1 C 1.2451(2) 0.51139(17) 0.59582(13) 0.0609(4) Uani 1 1 d . . . . . C2 C 1.10386(18) 0.57686(15) 0.61347(12) 0.0535(4) Uani 1 1 d . . . . . C3 C 1.05842(17) 0.69843(15) 0.61438(11) 0.0513(4) Uani 1 1 d . . . . . C4 C 1.15237(18) 0.76498(16) 0.59537(12) 0.0544(4) Uani 1 1 d . . . . . C5 C 1.28593(19) 0.70097(18) 0.58085(13) 0.0597(4) Uani 1 1 d . . . . . C6 C 1.3821(2) 0.7575(2) 0.56080(17) 0.0770(6) Uani 1 1 d . . . . . H6 H 1.4708 0.7132 0.5516 0.092 Uiso 1 1 calc R . . . . C7 C 1.3449(2) 0.8797(2) 0.55475(19) 0.0846(7) Uani 1 1 d . . . . . H7 H 1.4088 0.9185 0.5419 0.101 Uiso 1 1 calc R . . . . C8 C 1.2137(3) 0.9458(2) 0.56745(19) 0.0814(6) Uani 1 1 d . . . . . H8 H 1.1898 1.0286 0.5626 0.098 Uiso 1 1 calc R . . . . C9 C 1.1177(2) 0.88977(18) 0.58733(15) 0.0669(5) Uani 1 1 d . . . . . H9 H 1.0294 0.9350 0.5954 0.080 Uiso 1 1 calc R . . . . C10 C 0.91422(17) 0.76310(15) 0.63399(13) 0.0533(4) Uani 1 1 d . . . . . C11 C 0.8546(2) 0.84013(17) 0.71341(15) 0.0648(5) Uani 1 1 d . . . . . H11 H 0.9052 0.8538 0.7542 0.078 Uiso 1 1 calc R . . . . C12 C 0.7199(2) 0.8968(2) 0.73223(18) 0.0777(6) Uani 1 1 d . . . . . H12 H 0.6801 0.9472 0.7863 0.093 Uiso 1 1 calc R . . . . C13 C 0.6447(2) 0.8788(2) 0.6711(2) 0.0828(7) Uani 1 1 d . . . . . H13 H 0.5544 0.9173 0.6835 0.099 Uiso 1 1 calc R . . . . C14 C 0.7041(2) 0.8033(2) 0.59147(19) 0.0758(6) Uani 1 1 d . . . . . H14 H 0.6537 0.7917 0.5497 0.091 Uiso 1 1 calc R . . . . C15 C 0.83757(19) 0.74493(17) 0.57328(15) 0.0621(4) Uani 1 1 d . . . . . H15 H 0.8765 0.6931 0.5200 0.075 Uiso 1 1 calc R . . . . C16 C 1.01892(19) 0.50393(15) 0.63004(13) 0.0568(4) Uani 1 1 d . . . . . C17 C 0.9465(2) 0.44334(16) 0.64197(13) 0.0577(4) Uani 1 1 d . . . . . C18 C 0.85837(19) 0.37383(16) 0.65100(12) 0.0558(4) Uani 1 1 d . . . . . C19 C 0.7270(2) 0.42782(19) 0.64634(15) 0.0684(5) Uani 1 1 d . . . . . H19 H 0.6954 0.5100 0.6387 0.082 Uiso 1 1 calc R . . . . C20 C 0.6432(2) 0.3587(3) 0.65305(17) 0.0826(6) Uani 1 1 d . . . . . H20 H 0.5558 0.3948 0.6490 0.099 Uiso 1 1 calc R . . . . C21 C 0.6880(3) 0.2377(2) 0.66555(16) 0.0802(6) Uani 1 1 d . . . . . H21 H 0.6310 0.1921 0.6706 0.096 Uiso 1 1 calc R . . . . C22 C 0.8170(3) 0.18411(19) 0.67061(15) 0.0743(6) Uani 1 1 d . . . . . H22 H 0.8473 0.1020 0.6792 0.089 Uiso 1 1 calc R . . . . C23 C 0.9027(2) 0.25112(17) 0.66307(13) 0.0628(5) Uani 1 1 d . . . . . H23 H 0.9902 0.2138 0.6661 0.075 Uiso 1 1 calc R . . . . O1 O 1.29296(16) 0.40455(13) 0.59211(13) 0.0816(4) Uani 1 1 d . . . . . O2 O 1.32945(13) 0.57845(12) 0.58248(10) 0.0661(3) Uani 1 1 d . . . . . C1' C 1.2036(2) 0.84375(18) 0.09788(13) 0.0621(5) Uani 1 1 d . . . . . C2' C 1.06218(18) 0.86155(16) 0.10946(12) 0.0550(4) Uani 1 1 d . . . . . C3' C 1.01431(18) 0.76734(16) 0.10855(12) 0.0532(4) Uani 1 1 d . . . . . C4' C 1.10570(18) 0.64749(16) 0.09678(12) 0.0562(4) Uani 1 1 d . . . . . C5' C 1.2392(2) 0.63237(18) 0.08784(13) 0.0616(5) Uani 1 1 d . . . . . C6' C 1.3326(2) 0.5210(2) 0.07745(16) 0.0789(6) Uani 1 1 d . . . . . H6' H 1.4209 0.5136 0.0732 0.095 Uiso 1 1 calc R . . . . C7' C 1.2937(3) 0.4208(2) 0.0734(2) 0.0909(8) Uani 1 1 d . . . . . H7' H 1.3560 0.3453 0.0665 0.109 Uiso 1 1 calc R . . . . C8' C 1.1630(3) 0.4323(2) 0.0794(2) 0.0886(7) Uani 1 1 d . . . . . H8' H 1.1373 0.3645 0.0755 0.106 Uiso 1 1 calc R . . . . C9' C 1.0705(2) 0.54366(19) 0.09126(16) 0.0714(5) Uani 1 1 d . . . . . H9' H 0.9823 0.5501 0.0957 0.086 Uiso 1 1 calc R . . . . C10' C 0.87044(18) 0.78741(15) 0.11979(13) 0.0557(4) Uani 1 1 d . . . . . C11' C 0.8016(2) 0.74067(18) 0.19698(16) 0.0689(5) Uani 1 1 d . . . . . H11' H 0.8455 0.6959 0.2422 0.083 Uiso 1 1 calc R . . . . C12' C 0.6677(2) 0.7606(2) 0.20678(19) 0.0829(7) Uani 1 1 d . . . . . H12' H 0.6219 0.7297 0.2590 0.099 Uiso 1 1 calc R . . . . C13' C 0.6017(2) 0.8257(2) 0.1400(2) 0.0849(7) Uani 1 1 d . . . . . H13' H 0.5120 0.8379 0.1465 0.102 Uiso 1 1 calc R . . . . C14' C 0.6699(2) 0.8728(2) 0.06319(18) 0.0759(6) Uani 1 1 d . . . . . H14' H 0.6256 0.9168 0.0179 0.091 Uiso 1 1 calc R . . . . C15' C 0.8036(2) 0.85497(17) 0.05307(15) 0.0643(5) Uani 1 1 d . . . . . H15' H 0.8484 0.8881 0.0018 0.077 Uiso 1 1 calc R . . . . C16' C 0.97882(19) 0.98211(17) 0.12541(13) 0.0589(4) Uani 1 1 d . . . . . C17' C 0.9045(2) 1.08179(18) 0.14004(13) 0.0617(4) Uani 1 1 d . . . . . C18' C 0.8097(2) 1.19858(17) 0.15593(13) 0.0613(4) Uani 1 1 d . . . . . C19' C 0.6766(2) 1.2113(2) 0.17616(18) 0.0813(6) Uani 1 1 d . . . . . H19' H 0.6486 1.1438 0.1793 0.098 Uiso 1 1 calc R . . . . C20' C 0.5847(3) 1.3240(3) 0.1918(2) 0.1002(9) Uani 1 1 d . . . . . H20' H 0.4952 1.3319 0.2062 0.120 Uiso 1 1 calc R . . . . C21' C 0.6249(3) 1.4240(3) 0.18605(19) 0.0964(9) Uani 1 1 d . . . . . H21' H 0.5629 1.4997 0.1956 0.116 Uiso 1 1 calc R . . . . C22' C 0.7559(3) 1.4123(2) 0.16631(17) 0.0852(7) Uani 1 1 d . . . . . H22' H 0.7830 1.4802 0.1631 0.102 Uiso 1 1 calc R . . . . C23' C 0.8486(2) 1.30063(18) 0.15096(15) 0.0711(5) Uani 1 1 d . . . . . H23' H 0.9377 1.2938 0.1372 0.085 Uiso 1 1 calc R . . . . O1' O 1.25292(17) 0.92240(15) 0.09721(13) 0.0825(4) Uani 1 1 d . . . . . O2' O 1.28550(13) 0.72887(13) 0.08794(10) 0.0680(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 C1 0.0595(11) 0.0602(11) 0.0582(10) 0.0060(8) -0.0128(8) -0.0120(8) C2 0.0560(10) 0.0546(9) 0.0495(8) 0.0007(7) -0.0124(7) -0.0154(8) C3 0.0530(9) 0.0546(9) 0.0471(8) 0.0001(7) -0.0123(7) -0.0162(7) C4 0.0536(9) 0.0586(10) 0.0533(9) 0.0010(7) -0.0128(7) -0.0195(8) C5 0.0557(10) 0.0678(11) 0.0590(10) 0.0047(8) -0.0184(8) -0.0202(8) C6 0.0542(11) 0.0911(16) 0.0924(15) 0.0081(12) -0.0210(11) -0.0287(10) C7 0.0735(14) 0.0904(16) 0.1048(17) 0.0086(13) -0.0202(13) -0.0464(13) C8 0.0835(15) 0.0661(12) 0.1027(17) 0.0032(11) -0.0152(13) -0.0376(11) C9 0.0608(11) 0.0603(11) 0.0795(12) 0.0014(9) -0.0115(9) -0.0206(9) C10 0.0502(9) 0.0480(8) 0.0625(10) 0.0014(7) -0.0100(7) -0.0173(7) C11 0.0619(11) 0.0607(11) 0.0716(11) -0.0068(9) -0.0111(9) -0.0197(9) C12 0.0634(12) 0.0696(12) 0.0898(14) -0.0154(11) 0.0028(11) -0.0165(10) C13 0.0448(10) 0.0756(13) 0.1209(19) -0.0064(13) -0.0058(11) -0.0151(9) C14 0.0565(11) 0.0748(13) 0.1025(16) -0.0018(11) -0.0247(11) -0.0235(10) C15 0.0574(10) 0.0592(10) 0.0723(11) -0.0029(8) -0.0161(9) -0.0193(8) C16 0.0625(10) 0.0503(9) 0.0546(9) 0.0011(7) -0.0105(8) -0.0143(8) C17 0.0641(11) 0.0522(9) 0.0542(9) 0.0009(7) -0.0102(8) -0.0158(8) C18 0.0618(10) 0.0575(10) 0.0457(8) -0.0013(7) -0.0066(7) -0.0178(8) C19 0.0651(12) 0.0665(11) 0.0660(11) -0.0009(9) -0.0083(9) -0.0129(9) C20 0.0568(12) 0.1108(19) 0.0784(14) -0.0066(13) -0.0073(10) -0.0269(12) C21 0.0839(16) 0.0955(17) 0.0693(12) -0.0057(11) 0.0015(11) -0.0500(13) C22 0.0971(17) 0.0630(11) 0.0646(11) 0.0006(9) -0.0027(11) -0.0366(11) C23 0.0687(12) 0.0594(10) 0.0574(10) 0.0030(8) -0.0093(9) -0.0184(9) O1 0.0702(9) 0.0577(8) 0.1019(11) 0.0084(7) -0.0114(8) -0.0038(7) O2 0.0517(7) 0.0677(8) 0.0763(8) 0.0080(6) -0.0170(6) -0.0130(6) C1' 0.0612(11) 0.0749(12) 0.0546(9) 0.0094(8) -0.0164(8) -0.0254(10) C2' 0.0558(10) 0.0615(10) 0.0480(8) 0.0049(7) -0.0136(7) -0.0170(8) C3' 0.0521(9) 0.0590(10) 0.0474(8) 0.0043(7) -0.0125(7) -0.0147(7) C4' 0.0549(10) 0.0611(10) 0.0498(8) 0.0018(7) -0.0135(7) -0.0124(8) C5' 0.0570(10) 0.0708(11) 0.0523(9) -0.0003(8) -0.0138(8) -0.0115(9) C6' 0.0576(12) 0.0870(15) 0.0791(13) -0.0057(11) -0.0181(10) 0.0001(11) C7' 0.0828(16) 0.0685(14) 0.1041(18) -0.0111(12) -0.0279(14) 0.0086(12) C8' 0.0914(17) 0.0577(12) 0.1115(19) -0.0059(12) -0.0288(15) -0.0099(11) C9' 0.0677(12) 0.0635(11) 0.0810(13) -0.0016(9) -0.0199(10) -0.0144(9) C10' 0.0506(9) 0.0506(9) 0.0638(10) 0.0022(7) -0.0128(8) -0.0120(7) C11' 0.0610(11) 0.0650(11) 0.0760(12) 0.0138(9) -0.0116(10) -0.0158(9) C12' 0.0565(12) 0.0805(14) 0.1034(17) 0.0185(12) -0.0024(11) -0.0209(10) C13' 0.0500(11) 0.0788(14) 0.122(2) 0.0053(13) -0.0164(12) -0.0159(10) C14' 0.0603(12) 0.0701(12) 0.0954(15) 0.0080(11) -0.0287(11) -0.0098(10) C15' 0.0585(11) 0.0614(10) 0.0726(11) 0.0088(9) -0.0178(9) -0.0159(8) C16' 0.0623(11) 0.0609(11) 0.0561(9) 0.0043(8) -0.0139(8) -0.0222(9) C17' 0.0662(11) 0.0630(11) 0.0573(10) 0.0038(8) -0.0132(8) -0.0222(9) C18' 0.0649(11) 0.0645(11) 0.0518(9) 0.0009(8) -0.0145(8) -0.0146(9) C19' 0.0710(14) 0.0882(16) 0.0840(14) 0.0019(12) -0.0191(11) -0.0218(12) C20' 0.0638(14) 0.122(2) 0.0962(18) -0.0069(16) -0.0184(13) 0.0004(14) C21' 0.099(2) 0.0838(17) 0.0829(15) -0.0113(13) -0.0248(14) 0.0116(15) C22' 0.113(2) 0.0619(12) 0.0736(13) -0.0045(10) -0.0218(13) -0.0140(13) C23' 0.0773(13) 0.0652(12) 0.0679(11) 0.0006(9) -0.0126(10) -0.0194(10) O1' 0.0750(10) 0.0909(11) 0.0982(11) 0.0178(9) -0.0297(8) -0.0436(9) O2' 0.0498(7) 0.0811(9) 0.0717(8) 0.0025(7) -0.0146(6) -0.0172(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 O1 C1 C2 125.8(2) . . ? O1 C1 O2 117.33(19) . . ? O2 C1 C2 116.86(16) . . ? C3 C2 C1 121.82(17) . . ? C3 C2 C16 122.95(17) . . ? C16 C2 C1 115.23(16) . . ? C2 C3 C4 119.00(16) . . ? C2 C3 C10 120.86(16) . . ? C4 C3 C10 120.14(15) . . ? C5 C4 C3 118.12(17) . . ? C5 C4 C9 117.70(18) . . ? C9 C4 C3 124.14(17) . . ? C6 C5 C4 121.78(19) . . ? O2 C5 C4 121.86(17) . . ? O2 C5 C6 116.33(18) . . ? C5 C6 H6 120.5 . . ? C7 C6 C5 119.1(2) . . ? C7 C6 H6 120.5 . . ? C6 C7 H7 119.7 . . ? C6 C7 C8 120.7(2) . . ? C8 C7 H7 119.7 . . ? C7 C8 H8 119.8 . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C4 C9 H9 119.8 . . ? C8 C9 C4 120.4(2) . . ? C8 C9 H9 119.8 . . ? C11 C10 C3 120.91(17) . . ? C15 C10 C3 119.95(16) . . ? C15 C10 C11 119.14(18) . . ? C10 C11 H11 119.9 . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C11 C12 H12 119.9 . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.6(2) . . ? C14 C13 H13 120.2 . . ? C13 C14 H14 119.8 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.8 . . ? C10 C15 H15 119.8 . . ? C14 C15 C10 120.31(19) . . ? C14 C15 H15 119.8 . . ? C17 C16 C2 178.5(2) . . ? C16 C17 C18 176.68(19) . . ? C19 C18 C17 120.50(17) . . ? C23 C18 C17 120.58(18) . . ? C23 C18 C19 118.92(19) . . ? C18 C19 H19 120.1 . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C19 C20 H20 119.7 . . ? C21 C20 C19 120.6(2) . . ? C21 C20 H20 119.7 . . ? C20 C21 H21 120.1 . . ? C22 C21 C20 119.9(2) . . ? C22 C21 H21 120.1 . . ? C21 C22 H22 119.7 . . ? C21 C22 C23 120.5(2) . . ? C23 C22 H22 119.7 . . ? C18 C23 H23 119.9 . . ? C22 C23 C18 120.3(2) . . ? C22 C23 H23 119.9 . . ? C1 O2 C5 122.24(15) . . ? O1' C1' C2' 125.3(2) . . ? O1' C1' O2' 117.49(19) . . ? O2' C1' C2' 117.25(17) . . ? C3' C2' C1' 121.59(17) . . ? C3' C2' C16' 122.59(18) . . ? C16' C2' C1' 115.77(17) . . ? C2' C3' C4' 118.82(17) . . ? C2' C3' C10' 120.74(16) . . ? C4' C3' C10' 120.44(16) . . ? C5' C4' C3' 118.71(18) . . ? C5' C4' C9' 116.62(18) . . ? C9' C4' C3' 124.66(19) . . ? C6' C5' C4' 122.3(2) . . ? O2' C5' C4' 121.48(17) . . ? O2' C5' C6' 116.2(2) . . ? C5' C6' H6' 120.4 . . ? C7' C6' C5' 119.3(2) . . ? C7' C6' H6' 120.4 . . ? C6' C7' H7' 119.9 . . ? C8' C7' C6' 120.1(2) . . ? C8' C7' H7' 119.9 . . ? C7' C8' H8' 120.0 . . ? C9' C8' C7' 120.1(2) . . ? C9' C8' H8' 120.0 . . ? C4' C9' H9' 119.2 . . ? C8' C9' C4' 121.5(2) . . ? C8' C9' H9' 119.2 . . ? C11' C10' C3' 120.69(17) . . ? C11' C10' C15' 119.47(18) . . ? C15' C10' C3' 119.83(17) . . ? C10' C11' H11' 120.0 . . ? C12' C11' C10' 120.1(2) . . ? C12' C11' H11' 120.0 . . ? C11' C12' H12' 119.7 . . ? C13' C12' C11' 120.6(2) . . ? C13' C12' H12' 119.7 . . ? C12' C13' H13' 120.2 . . ? C12' C13' C14' 119.5(2) . . ? C14' C13' H13' 120.2 . . ? C13' C14' H14' 119.7 . . ? C13' C14' C15' 120.6(2) . . ? C15' C14' H14' 119.7 . . ? C10' C15' H15' 120.1 . . ? C14' C15' C10' 119.8(2) . . ? C14' C15' H15' 120.1 . . ? C17' C16' C2' 177.4(2) . . ? C16' C17' C18' 176.6(2) . . ? C19' C18' C17' 120.1(2) . . ? C19' C18' C23' 118.6(2) . . ? C23' C18' C17' 121.3(2) . . ? C18' C19' H19' 119.9 . . ? C18' C19' C20' 120.3(3) . . ? C20' C19' H19' 119.9 . . ? C19' C20' H20' 119.9 . . ? C21' C20' C19' 120.3(3) . . ? C21' C20' H20' 119.9 . . ? C20' C21' H21' 120.1 . . ? C22' C21' C20' 119.8(2) . . ? C22' C21' H21' 120.1 . . ? C21' C22' H22' 119.7 . . ? C21' C22' C23' 120.6(3) . . ? C23' C22' H22' 119.7 . . ? C18' C23' H23' 119.8 . . ? C22' C23' C18' 120.4(2) . . ? C22' C23' H23' 119.8 . . ? C1' O2' C5' 122.14(16) . . ? 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 C1 C2 1.466(3) . ? C1 O1 1.200(2) . ? C1 O2 1.367(3) . ? C2 C3 1.359(2) . ? C2 C16 1.426(3) . ? C3 C4 1.449(2) . ? C3 C10 1.491(2) . ? C4 C5 1.393(3) . ? C4 C9 1.403(3) . ? C5 C6 1.385(3) . ? C5 O2 1.370(2) . ? C6 H6 0.9300 . ? C6 C7 1.370(3) . ? C7 H7 0.9300 . ? C7 C8 1.379(4) . ? C8 H8 0.9300 . ? C8 C9 1.378(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 C15 1.386(3) . ? C11 H11 0.9300 . ? C11 C12 1.386(3) . ? C12 H12 0.9300 . ? C12 C13 1.377(4) . ? C13 H13 0.9300 . ? C13 C14 1.379(3) . ? C14 H14 0.9300 . ? C14 C15 1.377(3) . ? C15 H15 0.9300 . ? C16 C17 1.201(3) . ? C17 C18 1.427(3) . ? C18 C19 1.392(3) . ? C18 C23 1.388(3) . ? C19 H19 0.9300 . ? C19 C20 1.387(3) . ? C20 H20 0.9300 . ? C20 C21 1.370(4) . ? C21 H21 0.9300 . ? C21 C22 1.369(4) . ? C22 H22 0.9300 . ? C22 C23 1.383(3) . ? C23 H23 0.9300 . ? C1' C2' 1.467(3) . ? C1' O1' 1.204(3) . ? C1' O2' 1.362(3) . ? C2' C3' 1.365(3) . ? C2' C16' 1.423(3) . ? C3' C4' 1.444(3) . ? C3' C10' 1.489(3) . ? C4' C5' 1.391(3) . ? C4' C9' 1.398(3) . ? C5' C6' 1.378(3) . ? C5' O2' 1.377(3) . ? C6' H6' 0.9300 . ? C6' C7' 1.376(4) . ? C7' H7' 0.9300 . ? C7' C8' 1.376(4) . ? C8' H8' 0.9300 . ? C8' C9' 1.375(3) . ? C9' H9' 0.9300 . ? C10' C11' 1.388(3) . ? C10' C15' 1.391(3) . ? C11' H11' 0.9300 . ? C11' C12' 1.385(3) . ? C12' H12' 0.9300 . ? C12' C13' 1.376(3) . ? C13' H13' 0.9300 . ? C13' C14' 1.383(4) . ? C14' H14' 0.9300 . ? C14' C15' 1.385(3) . ? C15' H15' 0.9300 . ? C16' C17' 1.197(3) . ? C17' C18' 1.432(3) . ? C18' C19' 1.383(3) . ? C18' C23' 1.385(3) . ? C19' H19' 0.9300 . ? C19' C20' 1.384(4) . ? C20' H20' 0.9300 . ? C20' C21' 1.370(5) . ? C21' H21' 0.9300 . ? C21' C22' 1.361(4) . ? C22' H22' 0.9300 . ? C22' C23' 1.378(3) . ? C23' H23' 0.9300 . ? 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 C1 C2 C3 C4 1.3(2) . . . . ? C1 C2 C3 C10 -179.05(16) . . . . ? C2 C1 O2 C5 -3.1(3) . . . . ? C2 C3 C4 C5 -2.6(2) . . . . ? C2 C3 C4 C9 175.08(17) . . . . ? C2 C3 C10 C11 118.0(2) . . . . ? C2 C3 C10 C15 -60.9(2) . . . . ? C3 C4 C5 C6 178.96(18) . . . . ? C3 C4 C5 O2 1.2(3) . . . . ? C3 C4 C9 C8 -178.87(19) . . . . ? C3 C10 C11 C12 -178.08(19) . . . . ? C3 C10 C15 C14 179.30(19) . . . . ? C4 C3 C10 C11 -62.3(2) . . . . ? C4 C3 C10 C15 118.78(19) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C4 C5 O2 C1 1.8(3) . . . . ? C5 C4 C9 C8 -1.2(3) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C5 O2 C1 -176.13(18) . . . . ? C6 C7 C8 C9 0.6(4) . . . . ? C7 C8 C9 C4 0.3(4) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C9 C4 C5 O2 -176.69(17) . . . . ? C10 C3 C4 C5 177.74(15) . . . . ? C10 C3 C4 C9 -4.6(3) . . . . ? C10 C11 C12 C13 -1.3(3) . . . . ? C11 C10 C15 C14 0.4(3) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? C13 C14 C15 C10 -1.2(3) . . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C16 C2 C3 C4 -179.12(16) . . . . ? C16 C2 C3 C10 0.5(3) . . . . ? C17 C18 C19 C20 178.54(18) . . . . ? C17 C18 C23 C22 -179.21(17) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? C19 C18 C23 C22 -0.2(3) . . . . ? C19 C20 C21 C22 -0.6(4) . . . . ? C20 C21 C22 C23 -0.1(3) . . . . ? C21 C22 C23 C18 0.5(3) . . . . ? C23 C18 C19 C20 -0.5(3) . . . . ? O1 C1 C2 C3 -178.54(19) . . . . ? O1 C1 C2 C16 1.9(3) . . . . ? O1 C1 O2 C5 176.97(17) . . . . ? O2 C1 C2 C3 1.5(3) . . . . ? O2 C1 C2 C16 -178.12(15) . . . . ? O2 C5 C6 C7 177.7(2) . . . . ? C1' C2' C3' C4' 0.6(3) . . . . ? C1' C2' C3' C10' -179.59(16) . . . . ? C2' C1' O2' C5' 0.5(2) . . . . ? C2' C3' C4' C5' 0.7(2) . . . . ? C2' C3' C4' C9' -177.68(18) . . . . ? C2' C3' C10' C11' -118.7(2) . . . . ? C2' C3' C10' C15' 60.5(2) . . . . ? C3' C4' C5' C6' 179.26(18) . . . . ? C3' C4' C5' O2' -1.4(3) . . . . ? C3' C4' C9' C8' 179.6(2) . . . . ? C3' C10' C11' C12' 179.7(2) . . . . ? C3' C10' C15' C14' 179.49(19) . . . . ? C4' C3' C10' C11' 61.2(2) . . . . ? C4' C3' C10' C15' -119.68(19) . . . . ? C4' C5' C6' C7' 1.6(3) . . . . ? C4' C5' O2' C1' 0.8(3) . . . . ? C5' C4' C9' C8' 1.2(3) . . . . ? C5' C6' C7' C8' 0.2(4) . . . . ? C6' C5' O2' C1' -179.83(17) . . . . ? C6' C7' C8' C9' -1.2(4) . . . . ? C7' C8' C9' C4' 0.5(4) . . . . ? C9' C4' C5' C6' -2.2(3) . . . . ? C9' C4' C5' O2' 177.10(17) . . . . ? C10' C3' C4' C5' -179.12(16) . . . . ? C10' C3' C4' C9' 2.5(3) . . . . ? C10' C11' C12' C13' 0.6(4) . . . . ? C11' C10' C15' C14' -1.3(3) . . . . ? C11' C12' C13' C14' -0.8(4) . . . . ? C12' C13' C14' C15' 0.0(4) . . . . ? C13' C14' C15' C10' 1.1(3) . . . . ? C15' C10' C11' C12' 0.5(3) . . . . ? C16' C2' C3' C4' -176.84(15) . . . . ? C16' C2' C3' C10' 3.0(3) . . . . ? C17' C18' C19' C20' 179.9(2) . . . . ? C17' C18' C23' C22' 179.89(19) . . . . ? C18' C19' C20' C21' 0.9(4) . . . . ? C19' C18' C23' C22' 0.2(3) . . . . ? C19' C20' C21' C22' -1.0(4) . . . . ? C20' C21' C22' C23' 0.7(4) . . . . ? C21' C22' C23' C18' -0.3(3) . . . . ? C23' C18' C19' C20' -0.5(3) . . . . ? O1' C1' C2' C3' 179.41(18) . . . . ? O1' C1' C2' C16' -3.0(3) . . . . ? O1' C1' O2' C5' 179.94(17) . . . . ? O2' C1' C2' C3' -1.2(3) . . . . ? O2' C1' C2' C16' 176.40(15) . . . . ? O2' C5' C6' C7' -177.8(2) . . . . ?