#------------------------------------------------------------------------------ #$Date: 2020-01-03 03:51:21 +0200 (Fri, 03 Jan 2020) $ #$Revision: 246447 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125713.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_7125713 loop_ _publ_author_name 'You, Yong' 'Li, Ting-Ting' 'Yuan, Shu-Pei' 'Xie, Ke-Xin' 'Wang, Zhen-Hua' 'Zhao, Jian-Qiang' 'Zhou, Ming-Qiang' 'Yuan, Wei-Cheng' _publ_section_title ; Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes. ; _journal_issue 3 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 439 _journal_page_last 442 _journal_paper_doi 10.1039/c9cc08316b _journal_volume 56 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C35 H32 O2, C2 H6 O S' _chemical_formula_sum 'C37 H38 O3 S' _chemical_formula_weight 562.73 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-06-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-08-16 deposited with the CCDC. 2019-12-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.43565(16) _cell_length_b 16.9768(3) _cell_length_c 19.2055(3) _cell_measurement_reflns_used 4430 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.0820 _cell_measurement_theta_min 5.1990 _cell_volume 3076.47(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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 1.000 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -44.00 -3.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 57.0000 120.0000 82 #__ type_ start__ end____ width___ exp.time_ 2 omega -97.00 -68.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 -30.0000 58 #__ type_ start__ end____ width___ exp.time_ 3 omega -1.00 34.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 57.0000 120.0000 70 #__ type_ start__ end____ width___ exp.time_ 4 omega 33.00 76.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 -60.0000 86 #__ type_ start__ end____ width___ exp.time_ 5 omega -4.00 24.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 -60.0000 56 #__ type_ start__ end____ width___ exp.time_ 6 omega 19.00 106.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 150.0000 174 #__ type_ start__ end____ width___ exp.time_ 7 omega 78.00 104.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -120.0000 52 #__ type_ start__ end____ width___ exp.time_ 8 omega 62.00 91.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 9 omega 58.00 89.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 90.0000 62 #__ type_ start__ end____ width___ exp.time_ 10 omega 18.00 53.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -120.0000 70 #__ type_ start__ end____ width___ exp.time_ 11 omega 12.00 55.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 0.0000 86 #__ type_ start__ end____ width___ exp.time_ 12 omega 150.00 178.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 56 #__ type_ start__ end____ width___ exp.time_ 13 omega 63.00 99.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -30.0000 72 #__ type_ start__ end____ width___ exp.time_ 14 omega 78.00 109.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -120.0000 62 #__ type_ start__ end____ width___ exp.time_ 15 omega 46.00 98.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -90.0000 104 #__ type_ start__ end____ width___ exp.time_ 16 omega 38.00 63.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 120.0000 50 #__ type_ start__ end____ width___ exp.time_ 17 omega 107.00 178.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -150.0000 142 #__ type_ start__ end____ width___ exp.time_ 18 omega 73.00 99.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -150.0000 52 #__ type_ start__ end____ width___ exp.time_ 19 omega 42.00 85.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 0.0000 86 #__ type_ start__ end____ width___ exp.time_ 20 omega 38.00 94.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 60.0000 112 #__ type_ start__ end____ width___ exp.time_ 21 omega 40.00 125.00 0.5000 25.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 150.0000 170 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0252629000 _diffrn_orient_matrix_UB_12 0.0440868000 _diffrn_orient_matrix_UB_13 0.0690112000 _diffrn_orient_matrix_UB_21 0.0171071000 _diffrn_orient_matrix_UB_22 0.0792937000 _diffrn_orient_matrix_UB_23 -0.0380719000 _diffrn_orient_matrix_UB_31 -0.1604069000 _diffrn_orient_matrix_UB_32 0.0015570000 _diffrn_orient_matrix_UB_33 -0.0149072000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0437 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 11706 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.895 _diffrn_reflns_theta_min 3.475 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.200 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.215 _exptl_crystal_description prism _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.340 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 1870 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.006(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 376 _refine_ls_number_reflns 5806 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0490 _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^)+(0.0765P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1287 _refine_ls_wR_factor_ref 0.1375 _reflns_Friedel_coverage 0.749 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.961 _reflns_number_gt 5075 _reflns_number_total 5806 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201906158.res created by SHELXL-2014/7 TITL 201906158 in P212121 #19 REM reset to P212121 #19 CELL 1.54184 9.435652 16.976822 19.205544 90 90 90 ZERR 4 0.000162 0.000325 0.000345 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H O S UNIT 148 152 12 4 EQIV $1 1.5-X,1-Y,0.5+Z L.S. 4 0 0 PLAN 20 SIZE 0.09 0.1 0.19 MPLA C14 C15 C16 C17 C18 C19 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 MPLA C20 C21 C22 C23 C24 C25 MPLA C26 C27 C28 C29 C30 C31 HTAB O1 O3_$1 BOND $h conf fmap 2 acta REM REM REM WGHT 0.076500 0.200600 FVAR 5.07659 C1 1 0.980370 1.003588 0.710362 11.00000 0.05223 0.04907 = 0.06917 -0.00411 -0.01965 -0.00704 AFIX 43 H1 2 0.981011 1.047679 0.739097 11.00000 -1.20000 AFIX 0 C2 1 1.016960 1.011768 0.641988 11.00000 0.05719 0.06108 = 0.07859 0.01575 -0.01765 -0.01973 AFIX 43 H2 2 1.044211 1.060500 0.624383 11.00000 -1.20000 AFIX 0 C3 1 1.012641 0.945498 0.599030 11.00000 0.04519 0.07986 = 0.05849 0.01497 0.00085 -0.01536 AFIX 43 H3 2 1.039392 0.950507 0.552635 11.00000 -1.20000 AFIX 0 C4 1 0.970554 0.873900 0.622918 11.00000 0.03271 0.06483 = 0.04596 -0.00315 -0.00094 -0.00289 AFIX 43 H4 2 0.967168 0.831469 0.592335 11.00000 -1.20000 AFIX 0 C5 1 0.931474 0.862478 0.693903 11.00000 0.02736 0.04719 = 0.04261 -0.00310 -0.00565 0.00302 C6 1 0.941464 0.929670 0.738647 11.00000 0.03503 0.04502 = 0.05189 -0.00492 -0.01010 -0.00102 C7 1 0.915287 0.920085 0.810353 11.00000 0.04700 0.05135 = 0.05257 -0.01983 -0.00553 -0.00046 AFIX 43 H7 2 0.920642 0.963615 0.839633 11.00000 -1.20000 AFIX 0 C8 1 0.882469 0.848742 0.837530 11.00000 0.05043 0.06087 = 0.03570 -0.01172 -0.00311 0.00143 AFIX 43 H8 2 0.868074 0.843474 0.885208 11.00000 -1.20000 AFIX 0 C9 1 0.870016 0.782112 0.793490 11.00000 0.04494 0.04806 = 0.04002 -0.00087 -0.00771 0.00211 C10 1 0.888308 0.788537 0.722451 11.00000 0.03344 0.04122 = 0.03836 -0.00690 -0.00608 0.00723 C11 1 0.866193 0.715707 0.678027 11.00000 0.03507 0.04134 = 0.03873 -0.00659 -0.00533 0.00422 AFIX 13 H11 2 0.847381 0.671382 0.709382 11.00000 -1.20000 AFIX 0 C12 1 0.744297 0.719556 0.624787 11.00000 0.03158 0.04112 = 0.03613 -0.00017 -0.00420 0.00239 AFIX 13 H12 2 0.768418 0.760763 0.591074 11.00000 -1.20000 AFIX 0 C13 1 0.736330 0.639975 0.583846 11.00000 0.03013 0.04347 = 0.03353 -0.00382 -0.00115 0.00015 AFIX 13 H13 2 0.682773 0.650500 0.541128 11.00000 -1.20000 AFIX 0 C14 1 0.882893 0.614414 0.561635 11.00000 0.03090 0.04339 = 0.03427 -0.00331 -0.00028 0.00027 C15 1 1.002983 0.645865 0.592044 11.00000 0.03420 0.04401 = 0.04124 -0.00755 -0.00346 0.00572 C16 1 1.137007 0.623277 0.569191 11.00000 0.03208 0.05302 = 0.05464 -0.01426 -0.00325 0.00008 AFIX 43 H16 2 1.217488 0.644982 0.589521 11.00000 -1.20000 AFIX 0 C17 1 1.150383 0.568651 0.516342 11.00000 0.03104 0.05414 = 0.04861 -0.00817 0.00327 0.00270 AFIX 43 H17 2 1.240426 0.554459 0.501163 11.00000 -1.20000 AFIX 0 C18 1 1.031914 0.534188 0.485123 11.00000 0.04023 0.03985 = 0.03407 -0.00110 0.00511 -0.00107 C19 1 0.899915 0.558370 0.508860 11.00000 0.03630 0.04368 = 0.03376 -0.00573 0.00150 -0.00679 AFIX 43 H19 2 0.819367 0.536385 0.488832 11.00000 -1.20000 AFIX 0 C20 1 0.600917 0.740411 0.655236 11.00000 0.03244 0.03395 = 0.04587 -0.00722 -0.00244 0.00191 C21 1 0.556512 0.715448 0.720102 11.00000 0.04401 0.06577 = 0.04508 -0.00301 0.00150 0.00719 AFIX 43 H21 2 0.619080 0.688600 0.749028 11.00000 -1.20000 AFIX 0 C22 1 0.419464 0.730123 0.742358 11.00000 0.05548 0.08444 = 0.05406 -0.01658 0.01465 -0.00033 AFIX 43 H22 2 0.391324 0.713053 0.786244 11.00000 -1.20000 AFIX 0 C23 1 0.324320 0.769385 0.700888 11.00000 0.03592 0.06347 = 0.08916 -0.02532 0.00573 0.00085 AFIX 43 H23 2 0.232159 0.778391 0.716098 11.00000 -1.20000 AFIX 0 C24 1 0.367665 0.795101 0.636588 11.00000 0.03704 0.05294 = 0.09848 0.00016 -0.01083 0.00776 AFIX 43 H24 2 0.304696 0.822184 0.608046 11.00000 -1.20000 AFIX 0 C25 1 0.504682 0.780942 0.613968 11.00000 0.03734 0.04347 = 0.06685 0.00650 -0.00586 0.00084 AFIX 43 H25 2 0.532707 0.798913 0.570345 11.00000 -1.20000 AFIX 0 C26 1 0.657462 0.575089 0.622492 11.00000 0.03357 0.04178 = 0.03797 -0.01137 0.00129 -0.00155 C27 1 0.513551 0.563717 0.610491 11.00000 0.03491 0.05559 = 0.05837 -0.00796 0.00102 -0.00273 AFIX 43 H27 2 0.467075 0.594947 0.577913 11.00000 -1.20000 AFIX 0 C28 1 0.439132 0.507078 0.646027 11.00000 0.04430 0.06919 = 0.07475 -0.01046 0.01399 -0.01371 AFIX 43 H28 2 0.343294 0.499804 0.636728 11.00000 -1.20000 AFIX 0 C29 1 0.504569 0.461185 0.695020 11.00000 0.08415 0.06259 = 0.05809 -0.01353 0.02695 -0.02420 AFIX 43 H29 2 0.453206 0.423358 0.719312 11.00000 -1.20000 AFIX 0 C30 1 0.647463 0.471381 0.708193 11.00000 0.08490 0.05249 = 0.04636 0.00305 0.00028 -0.00565 AFIX 43 H30 2 0.692603 0.440777 0.741677 11.00000 -1.20000 AFIX 0 C31 1 0.722970 0.527480 0.671192 11.00000 0.05174 0.04790 = 0.04704 -0.00253 -0.00445 -0.00188 AFIX 43 H31 2 0.819599 0.533211 0.679283 11.00000 -1.20000 AFIX 0 C32 1 1.051785 0.474984 0.425421 11.00000 0.04672 0.04302 = 0.04307 -0.00801 0.00548 -0.00008 C33 1 0.912139 0.441282 0.399233 11.00000 0.06395 0.08609 = 0.06865 -0.03912 0.01717 -0.02229 AFIX 137 H33A 2 0.865245 0.414088 0.436515 11.00000 -1.50000 H33B 2 0.930252 0.405170 0.361811 11.00000 -1.50000 H33C 2 0.852839 0.483330 0.382855 11.00000 -1.50000 AFIX 0 C34 1 1.149403 0.408039 0.449010 11.00000 0.11394 0.05124 = 0.06176 -0.00904 -0.00263 0.02120 AFIX 137 H34A 2 1.236173 0.429717 0.466732 11.00000 -1.50000 H34B 2 1.169791 0.374306 0.410163 11.00000 -1.50000 H34C 2 1.103440 0.378129 0.484921 11.00000 -1.50000 AFIX 0 C35 1 1.122402 0.516657 0.363876 11.00000 0.06322 0.06559 = 0.04184 -0.00749 0.01178 -0.00150 AFIX 137 H35A 2 1.063903 0.559699 0.348877 11.00000 -1.50000 H35B 2 1.134221 0.480060 0.326216 11.00000 -1.50000 H35C 2 1.213383 0.536356 0.377925 11.00000 -1.50000 AFIX 0 O1 3 0.836201 0.710946 0.821545 11.00000 0.09346 0.05497 = 0.03863 0.00407 -0.00908 -0.00791 AFIX 147 H1A 2 0.843917 0.713113 0.864029 11.00000 -1.50000 AFIX 0 O2 3 0.999813 0.701063 0.643886 11.00000 0.03047 0.06427 = 0.05823 -0.02892 -0.00856 0.00668 C36 1 0.749363 0.325710 0.578846 11.00000 0.08946 0.12289 = 0.07547 -0.03084 0.00724 -0.02202 AFIX 137 H36A 2 0.751140 0.270730 0.590503 11.00000 -1.50000 H36B 2 0.730337 0.356066 0.619969 11.00000 -1.50000 H36C 2 0.839497 0.340861 0.559920 11.00000 -1.50000 AFIX 0 C37 1 0.470192 0.305461 0.565741 11.00000 0.08338 0.08794 = 0.08400 -0.02792 0.00529 0.00207 AFIX 137 H37A 2 0.385695 0.306956 0.537929 11.00000 -1.50000 H37B 2 0.457005 0.337057 0.606686 11.00000 -1.50000 H37C 2 0.489735 0.252068 0.579113 11.00000 -1.50000 AFIX 0 O3 3 0.640591 0.283209 0.460595 11.00000 0.13390 0.09595 = 0.04318 -0.00937 0.01012 -0.00232 S1 4 0.615229 0.343142 0.516542 11.00000 0.10595 0.05609 = 0.05938 -0.00002 0.00679 -0.00401 HKLF 4 REM 201906158 in P212121 #19 REM R1 = 0.0490 for 5075 Fo > 4sig(Fo) and 0.0567 for all 5806 data REM 376 parameters refined using 0 restraints END WGHT 0.0765 0.2006 REM Highest difference peak 0.340, deepest hole -0.218, 1-sigma level 0.041 Q1 1 0.6317 0.2841 0.5254 11.00000 0.05 0.34 Q2 1 0.5801 0.4005 0.5174 11.00000 0.05 0.21 Q3 1 0.9515 0.7817 0.7607 11.00000 0.05 0.19 Q4 1 0.5223 0.3796 0.5273 11.00000 0.05 0.17 Q5 1 0.4995 0.3446 0.5238 11.00000 0.05 0.16 Q6 1 0.5836 0.3303 0.4561 11.00000 0.05 0.16 Q7 1 0.5314 0.2950 0.5173 11.00000 0.05 0.15 Q8 1 0.9407 0.6069 0.5929 11.00000 0.05 0.15 Q9 1 0.6733 0.5383 0.6287 11.00000 0.05 0.15 Q10 1 0.7141 0.3856 0.5136 11.00000 0.05 0.15 Q11 1 0.8638 0.8967 0.7136 11.00000 0.05 0.14 Q12 1 0.6939 0.3295 0.4736 11.00000 0.05 0.14 Q13 1 0.8436 0.8733 0.8158 11.00000 0.05 0.14 Q14 1 0.8051 0.6336 0.5742 11.00000 0.05 0.14 Q15 1 1.0227 0.4999 0.4569 11.00000 0.05 0.14 Q16 1 0.8466 0.7877 0.7571 11.00000 0.05 0.14 Q17 1 0.6024 0.5564 0.6007 11.00000 0.05 0.13 Q18 1 0.6554 0.5756 0.6610 11.00000 0.05 0.13 Q19 1 0.5290 0.2375 0.4366 11.00000 0.05 0.13 Q20 1 0.8981 0.8244 0.7207 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0490 for 5075 Fo > 4sig(Fo) and 0.0567 for all 11743 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.34, deepest hole -0.22 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0567 REM R1_gt = 0.0490 REM wR_ref = 0.1375 REM GOOF = 1.033 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11743 REM Reflections_gt = 5075 REM Parameters = n/a REM Hole = -0.22 REM Peak = 0.34 REM Flack = 0.006(15) ; _cod_data_source_file c9cc08316b2.cif _cod_data_source_block 201906158 _cod_original_cell_volume 3076.49(10) _cod_database_code 7125713 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C20H20N4O1 _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 0.900 _shelx_estimated_absorpt_t_min 0.804 _reflns_odcompleteness_completeness 99.90 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C11(H11), C12(H12), C13(H13) 2.b Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C16(H16), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B, H36C), C37(H37A,H37B,H37C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn C1 C 0.9804(4) 1.0036(2) 0.7104(2) 0.0568(10) Uani 1 1 d . H1 H 0.9810 1.0477 0.7391 0.068 Uiso 1 1 calc R C2 C 1.0170(5) 1.0118(3) 0.6420(3) 0.0656(12) Uani 1 1 d . H2 H 1.0442 1.0605 0.6244 0.079 Uiso 1 1 calc R C3 C 1.0126(5) 0.9455(3) 0.5990(2) 0.0612(11) Uani 1 1 d . H3 H 1.0394 0.9505 0.5526 0.073 Uiso 1 1 calc R C4 C 0.9706(4) 0.8739(3) 0.62292(19) 0.0478(8) Uani 1 1 d . H4 H 0.9672 0.8315 0.5923 0.057 Uiso 1 1 calc R C5 C 0.9315(3) 0.8625(2) 0.69390(17) 0.0391(7) Uani 1 1 d . C6 C 0.9415(4) 0.9297(2) 0.73865(19) 0.0440(7) Uani 1 1 d . C7 C 0.9153(4) 0.9201(2) 0.8104(2) 0.0503(9) Uani 1 1 d . H7 H 0.9206 0.9636 0.8396 0.060 Uiso 1 1 calc R C8 C 0.8825(4) 0.8487(2) 0.83753(17) 0.0490(8) Uani 1 1 d . H8 H 0.8681 0.8435 0.8852 0.059 Uiso 1 1 calc R C9 C 0.8700(4) 0.7821(2) 0.79349(17) 0.0443(7) Uani 1 1 d . C10 C 0.8883(3) 0.78854(19) 0.72245(16) 0.0377(6) Uani 1 1 d . C11 C 0.8662(4) 0.71571(19) 0.67803(16) 0.0384(7) Uani 1 1 d . H11 H 0.8474 0.6714 0.7094 0.046 Uiso 1 1 calc R C12 C 0.7443(3) 0.71956(19) 0.62479(16) 0.0363(6) Uani 1 1 d . H12 H 0.7684 0.7608 0.5911 0.044 Uiso 1 1 calc R C13 C 0.7363(3) 0.63998(19) 0.58385(16) 0.0357(6) Uani 1 1 d . H13 H 0.6828 0.6505 0.5411 0.043 Uiso 1 1 calc R C14 C 0.8829(3) 0.61441(19) 0.56163(16) 0.0362(6) Uani 1 1 d . C15 C 1.0030(4) 0.6459(2) 0.59204(17) 0.0398(7) Uani 1 1 d . C16 C 1.1370(4) 0.6233(2) 0.56919(19) 0.0466(8) Uani 1 1 d . H16 H 1.2175 0.6450 0.5895 0.056 Uiso 1 1 calc R C17 C 1.1504(3) 0.5687(2) 0.51634(18) 0.0446(7) Uani 1 1 d . H17 H 1.2404 0.5545 0.5012 0.054 Uiso 1 1 calc R C18 C 1.0319(3) 0.53419(19) 0.48512(17) 0.0380(6) Uani 1 1 d . C19 C 0.8999(3) 0.55837(19) 0.50886(16) 0.0379(6) Uani 1 1 d . H19 H 0.8194 0.5364 0.4888 0.045 Uiso 1 1 calc R C20 C 0.6009(3) 0.74041(17) 0.65524(17) 0.0374(6) Uani 1 1 d . C21 C 0.5565(4) 0.7154(3) 0.72010(19) 0.0516(9) Uani 1 1 d . H21 H 0.6191 0.6886 0.7490 0.062 Uiso 1 1 calc R C22 C 0.4195(5) 0.7301(3) 0.7424(2) 0.0647(11) Uani 1 1 d . H22 H 0.3913 0.7131 0.7862 0.078 Uiso 1 1 calc R C23 C 0.3243(4) 0.7694(3) 0.7009(3) 0.0629(11) Uani 1 1 d . H23 H 0.2322 0.7784 0.7161 0.075 Uiso 1 1 calc R C24 C 0.3677(4) 0.7951(2) 0.6366(3) 0.0628(11) Uani 1 1 d . H24 H 0.3047 0.8222 0.6080 0.075 Uiso 1 1 calc R C25 C 0.5047(4) 0.7809(2) 0.6140(2) 0.0492(8) Uani 1 1 d . H25 H 0.5327 0.7989 0.5703 0.059 Uiso 1 1 calc R C26 C 0.6575(3) 0.57509(19) 0.62249(16) 0.0378(7) Uani 1 1 d . C27 C 0.5136(4) 0.5637(2) 0.6105(2) 0.0496(8) Uani 1 1 d . H27 H 0.4671 0.5949 0.5779 0.060 Uiso 1 1 calc R C28 C 0.4391(5) 0.5071(3) 0.6460(3) 0.0627(11) Uani 1 1 d . H28 H 0.3433 0.4998 0.6367 0.075 Uiso 1 1 calc R C29 C 0.5046(6) 0.4612(3) 0.6950(2) 0.0683(13) Uani 1 1 d . H29 H 0.4532 0.4234 0.7193 0.082 Uiso 1 1 calc R C30 C 0.6475(6) 0.4714(3) 0.7082(2) 0.0613(10) Uani 1 1 d . H30 H 0.6926 0.4408 0.7417 0.074 Uiso 1 1 calc R C31 C 0.7230(4) 0.5275(2) 0.67119(19) 0.0489(8) Uani 1 1 d . H31 H 0.8196 0.5332 0.6793 0.059 Uiso 1 1 calc R C32 C 1.0518(4) 0.4750(2) 0.42542(18) 0.0443(8) Uani 1 1 d . C33 C 0.9121(5) 0.4413(3) 0.3992(3) 0.0729(14) Uani 1 1 d . H33A H 0.8652 0.4141 0.4365 0.109 Uiso 1 1 calc GR H33B H 0.9303 0.4052 0.3618 0.109 Uiso 1 1 calc GR H33C H 0.8528 0.4833 0.3829 0.109 Uiso 1 1 calc GR C34 C 1.1494(7) 0.4080(3) 0.4490(3) 0.0756(15) Uani 1 1 d . H34A H 1.2362 0.4297 0.4667 0.113 Uiso 1 1 calc GR H34B H 1.1698 0.3743 0.4102 0.113 Uiso 1 1 calc GR H34C H 1.1034 0.3781 0.4849 0.113 Uiso 1 1 calc GR C35 C 1.1224(5) 0.5167(3) 0.36388(19) 0.0569(9) Uani 1 1 d . H35A H 1.0639 0.5597 0.3489 0.085 Uiso 1 1 calc GR H35B H 1.1342 0.4801 0.3262 0.085 Uiso 1 1 calc GR H35C H 1.2134 0.5364 0.3779 0.085 Uiso 1 1 calc GR O1 O 0.8362(4) 0.71095(17) 0.82154(13) 0.0624(8) Uani 1 1 d . H1A H 0.8439 0.7131 0.8640 0.094 Uiso 1 1 calc GR O2 O 0.9998(2) 0.70106(16) 0.64389(14) 0.0510(6) Uani 1 1 d . C36 C 0.7494(7) 0.3257(5) 0.5788(3) 0.0959(19) Uani 1 1 d . H36A H 0.7511 0.2707 0.5905 0.144 Uiso 1 1 calc GR H36B H 0.7303 0.3561 0.6200 0.144 Uiso 1 1 calc GR H36C H 0.8395 0.3409 0.5599 0.144 Uiso 1 1 calc GR C37 C 0.4702(6) 0.3055(4) 0.5657(3) 0.0851(16) Uani 1 1 d . H37A H 0.3857 0.3070 0.5379 0.128 Uiso 1 1 calc GR H37B H 0.4570 0.3371 0.6067 0.128 Uiso 1 1 calc GR H37C H 0.4897 0.2521 0.5791 0.128 Uiso 1 1 calc GR O3 O 0.6406(5) 0.2832(2) 0.46059(16) 0.0910(12) Uani 1 1 d . S1 S 0.61523(16) 0.34314(7) 0.51654(6) 0.0738(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 0.052(2) 0.0491(19) 0.069(2) -0.0041(18) -0.0196(19) -0.0070(17) C2 0.057(2) 0.061(2) 0.079(3) 0.016(2) -0.018(2) -0.020(2) C3 0.045(2) 0.080(3) 0.058(2) 0.015(2) 0.0009(17) -0.015(2) C4 0.0327(16) 0.065(2) 0.0460(18) -0.0032(16) -0.0009(14) -0.0029(15) C5 0.0274(13) 0.0472(18) 0.0426(16) -0.0031(13) -0.0057(12) 0.0030(13) C6 0.0350(15) 0.0450(17) 0.0519(19) -0.0049(15) -0.0101(14) -0.0010(14) C7 0.0470(19) 0.051(2) 0.053(2) -0.0198(16) -0.0055(16) -0.0005(16) C8 0.050(2) 0.061(2) 0.0357(16) -0.0117(15) -0.0031(14) 0.0014(18) C9 0.0449(18) 0.0481(18) 0.0400(16) -0.0009(14) -0.0077(14) 0.0021(16) C10 0.0334(14) 0.0412(15) 0.0384(15) -0.0069(12) -0.0061(12) 0.0072(13) C11 0.0351(15) 0.0413(15) 0.0387(15) -0.0066(12) -0.0053(13) 0.0042(13) C12 0.0316(14) 0.0411(16) 0.0361(15) -0.0002(12) -0.0042(12) 0.0024(13) C13 0.0301(14) 0.0435(17) 0.0335(14) -0.0038(12) -0.0012(11) 0.0001(13) C14 0.0309(14) 0.0434(16) 0.0343(14) -0.0033(12) -0.0003(12) 0.0003(13) C15 0.0342(16) 0.0440(16) 0.0412(16) -0.0076(13) -0.0035(13) 0.0057(14) C16 0.0321(16) 0.0530(19) 0.055(2) -0.0143(16) -0.0033(14) 0.0001(15) C17 0.0310(15) 0.0541(19) 0.0486(17) -0.0082(16) 0.0033(14) 0.0027(14) C18 0.0402(16) 0.0398(15) 0.0341(14) -0.0011(13) 0.0051(13) -0.0011(13) C19 0.0363(16) 0.0437(16) 0.0338(14) -0.0057(13) 0.0015(12) -0.0068(13) C20 0.0324(15) 0.0340(13) 0.0459(16) -0.0072(12) -0.0024(13) 0.0019(12) C21 0.0440(18) 0.066(2) 0.0451(18) -0.0030(16) 0.0015(15) 0.0072(18) C22 0.055(2) 0.084(3) 0.054(2) -0.017(2) 0.0146(19) 0.000(2) C23 0.0359(18) 0.063(2) 0.089(3) -0.025(2) 0.0057(19) 0.0008(17) C24 0.0370(18) 0.053(2) 0.098(3) 0.000(2) -0.011(2) 0.0078(17) C25 0.0373(17) 0.0435(17) 0.067(2) 0.0065(16) -0.0059(16) 0.0008(15) C26 0.0336(15) 0.0418(16) 0.0380(15) -0.0114(13) 0.0013(12) -0.0015(13) C27 0.0349(17) 0.056(2) 0.058(2) -0.0080(17) 0.0010(15) -0.0027(16) C28 0.044(2) 0.069(3) 0.075(3) -0.010(2) 0.014(2) -0.0137(19) C29 0.084(3) 0.063(2) 0.058(2) -0.014(2) 0.027(2) -0.024(2) C30 0.085(3) 0.052(2) 0.046(2) 0.0031(17) 0.000(2) -0.006(2) C31 0.052(2) 0.0479(18) 0.0470(18) -0.0025(15) -0.0044(15) -0.0019(16) C32 0.0467(18) 0.0430(17) 0.0431(18) -0.0080(14) 0.0055(14) -0.0001(15) C33 0.064(3) 0.086(3) 0.069(3) -0.039(3) 0.017(2) -0.022(2) C34 0.114(4) 0.051(2) 0.062(2) -0.0090(19) -0.003(3) 0.021(3) C35 0.063(2) 0.066(2) 0.0418(18) -0.0075(16) 0.0118(18) -0.002(2) O1 0.093(2) 0.0550(15) 0.0386(12) 0.0041(11) -0.0091(14) -0.0079(15) O2 0.0305(11) 0.0643(15) 0.0582(15) -0.0289(13) -0.0086(10) 0.0067(11) C36 0.089(4) 0.123(5) 0.075(3) -0.031(3) 0.007(3) -0.022(4) C37 0.083(4) 0.088(4) 0.084(3) -0.028(3) 0.005(3) 0.002(3) O3 0.134(3) 0.096(3) 0.0432(15) -0.0094(16) 0.0101(19) -0.002(3) S1 0.1060(10) 0.0561(6) 0.0594(6) 0.0000(5) 0.0068(6) -0.0040(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' S S 0.3331 0.5567 '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 C2 C1 H1 119.2 C2 C1 C6 121.7(4) C6 C1 H1 119.2 C1 C2 H2 120.7 C1 C2 C3 118.6(4) C3 C2 H2 120.7 C2 C3 H3 119.0 C4 C3 C2 122.0(4) C4 C3 H3 119.0 C3 C4 H4 119.3 C3 C4 C5 121.4(4) C5 C4 H4 119.3 C4 C5 C6 116.7(3) C4 C5 C10 124.1(3) C10 C5 C6 119.2(3) C1 C6 C5 119.5(3) C7 C6 C1 121.5(3) C7 C6 C5 118.9(3) C6 C7 H7 119.3 C8 C7 C6 121.3(3) C8 C7 H7 119.3 C7 C8 H8 119.9 C7 C8 C9 120.2(3) C9 C8 H8 119.9 C10 C9 C8 121.1(3) O1 C9 C8 119.5(3) O1 C9 C10 119.4(3) C5 C10 C11 122.6(3) C9 C10 C5 119.0(3) C9 C10 C11 118.3(3) C10 C11 H11 107.8 C10 C11 C12 116.2(3) C12 C11 H11 107.8 O2 C11 C10 106.0(3) O2 C11 H11 107.8 O2 C11 C12 111.0(2) C11 C12 H12 107.2 C11 C12 C13 109.4(2) C13 C12 H12 107.2 C20 C12 C11 114.8(3) C20 C12 H12 107.2 C20 C12 C13 110.6(2) C12 C13 H13 106.7 C14 C13 C12 110.2(3) C14 C13 H13 106.7 C14 C13 C26 112.2(3) C26 C13 C12 113.8(2) C26 C13 H13 106.7 C15 C14 C13 121.3(3) C15 C14 C19 118.3(3) C19 C14 C13 120.3(3) C14 C15 C16 120.3(3) O2 C15 C14 123.7(3) O2 C15 C16 116.0(3) C15 C16 H16 120.0 C17 C16 C15 120.0(3) C17 C16 H16 120.0 C16 C17 H17 119.2 C16 C17 C18 121.6(3) C18 C17 H17 119.2 C17 C18 C32 119.8(3) C19 C18 C17 116.9(3) C19 C18 C32 123.2(3) C14 C19 H19 118.6 C18 C19 C14 122.8(3) C18 C19 H19 118.6 C21 C20 C12 123.2(3) C21 C20 C25 118.0(3) C25 C20 C12 118.6(3) C20 C21 H21 119.8 C20 C21 C22 120.4(4) C22 C21 H21 119.8 C21 C22 H22 119.4 C23 C22 C21 121.3(4) C23 C22 H22 119.4 C22 C23 H23 120.6 C24 C23 C22 118.8(4) C24 C23 H23 120.6 C23 C24 H24 119.8 C23 C24 C25 120.4(4) C25 C24 H24 119.8 C20 C25 H25 119.4 C24 C25 C20 121.2(4) C24 C25 H25 119.4 C27 C26 C13 119.8(3) C31 C26 C13 122.3(3) C31 C26 C27 117.9(3) C26 C27 H27 119.5 C28 C27 C26 121.0(4) C28 C27 H27 119.5 C27 C28 H28 119.7 C29 C28 C27 120.7(4) C29 C28 H28 119.7 C28 C29 H29 120.2 C28 C29 C30 119.6(4) C30 C29 H29 120.2 C29 C30 H30 120.2 C29 C30 C31 119.6(4) C31 C30 H30 120.2 C26 C31 C30 121.3(4) C26 C31 H31 119.4 C30 C31 H31 119.4 C33 C32 C18 112.8(3) C33 C32 C34 109.8(4) C33 C32 C35 107.2(3) C34 C32 C18 109.8(3) C35 C32 C18 109.1(3) C35 C32 C34 108.0(4) C32 C33 H33A 109.5 C32 C33 H33B 109.5 C32 C33 H33C 109.5 H33A C33 H33B 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 C32 C34 H34A 109.5 C32 C34 H34B 109.5 C32 C34 H34C 109.5 H34A C34 H34B 109.5 H34A C34 H34C 109.5 H34B C34 H34C 109.5 C32 C35 H35A 109.5 C32 C35 H35B 109.5 C32 C35 H35C 109.5 H35A C35 H35B 109.5 H35A C35 H35C 109.5 H35B C35 H35C 109.5 C9 O1 H1A 109.5 C15 O2 C11 117.9(3) H36A C36 H36B 109.5 H36A C36 H36C 109.5 H36B C36 H36C 109.5 S1 C36 H36A 109.5 S1 C36 H36B 109.5 S1 C36 H36C 109.5 H37A C37 H37B 109.5 H37A C37 H37C 109.5 H37B C37 H37C 109.5 S1 C37 H37A 109.5 S1 C37 H37B 109.5 S1 C37 H37C 109.5 C36 S1 C37 97.5(3) O3 S1 C36 104.9(3) O3 S1 C37 105.0(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 H1 0.9300 C1 C2 1.365(7) C1 C6 1.416(5) C2 H2 0.9300 C2 C3 1.396(7) C3 H3 0.9300 C3 C4 1.359(6) C4 H4 0.9300 C4 C5 1.426(5) C5 C6 1.431(5) C5 C10 1.429(5) C6 C7 1.409(5) C7 H7 0.9300 C7 C8 1.355(6) C8 H8 0.9300 C8 C9 1.417(5) C9 C10 1.380(5) C9 O1 1.361(5) C10 C11 1.517(4) C11 H11 0.9800 C11 C12 1.540(4) C11 O2 1.443(4) C12 H12 0.9800 C12 C13 1.565(4) C12 C20 1.516(4) C13 H13 0.9800 C13 C14 1.511(4) C13 C26 1.523(5) C14 C15 1.382(4) C14 C19 1.399(4) C15 C16 1.392(5) C15 O2 1.368(4) C16 H16 0.9300 C16 C17 1.381(5) C17 H17 0.9300 C17 C18 1.397(5) C18 C19 1.388(4) C18 C32 1.536(4) C19 H19 0.9300 C20 C21 1.381(5) C20 C25 1.388(5) C21 H21 0.9300 C21 C22 1.385(6) C22 H22 0.9300 C22 C23 1.373(7) C23 H23 0.9300 C23 C24 1.372(7) C24 H24 0.9300 C24 C25 1.385(6) C25 H25 0.9300 C26 C27 1.391(5) C26 C31 1.382(5) C27 H27 0.9300 C27 C28 1.372(6) C28 H28 0.9300 C28 C29 1.369(7) C29 H29 0.9300 C29 C30 1.383(7) C30 H30 0.9300 C30 C31 1.386(6) C31 H31 0.9300 C32 C33 1.522(6) C32 C34 1.531(6) C32 C35 1.530(5) C33 H33A 0.9600 C33 H33B 0.9600 C33 H33C 0.9600 C34 H34A 0.9600 C34 H34B 0.9600 C34 H34C 0.9600 C35 H35A 0.9600 C35 H35B 0.9600 C35 H35C 0.9600 O1 H1A 0.8200 C36 H36A 0.9600 C36 H36B 0.9600 C36 H36C 0.9600 C36 S1 1.767(7) C37 H37A 0.9600 C37 H37B 0.9600 C37 H37C 0.9600 C37 S1 1.782(6) O3 S1 1.499(4) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O3 0.82 1.86 2.681(4) 179.1 2_665 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 C1 C2 C3 C4 1.3(7) C1 C6 C7 C8 -177.9(4) C2 C1 C6 C5 -3.9(6) C2 C1 C6 C7 174.6(4) C2 C3 C4 C5 -1.4(6) C3 C4 C5 C6 -1.1(5) C3 C4 C5 C10 -179.1(3) C4 C5 C6 C1 3.7(5) C4 C5 C6 C7 -174.9(3) C4 C5 C10 C9 171.9(3) C4 C5 C10 C11 -6.0(5) C5 C6 C7 C8 0.7(6) C5 C10 C11 C12 -65.2(4) C5 C10 C11 O2 58.7(4) C6 C1 C2 C3 1.4(6) C6 C5 C10 C9 -5.9(5) C6 C5 C10 C11 176.1(3) C6 C7 C8 C9 -1.7(6) C7 C8 C9 C10 -1.2(6) C7 C8 C9 O1 -179.6(4) C8 C9 C10 C5 5.0(5) C8 C9 C10 C11 -177.0(3) C9 C10 C11 C12 116.9(3) C9 C10 C11 O2 -119.3(3) C10 C5 C6 C1 -178.3(3) C10 C5 C6 C7 3.2(5) C10 C11 C12 C13 -179.9(3) C10 C11 C12 C20 -54.7(4) C10 C11 O2 C15 -169.8(3) C11 C12 C13 C14 -45.2(3) C11 C12 C13 C26 81.8(3) C11 C12 C20 C21 -35.9(5) C11 C12 C20 C25 149.6(3) C12 C11 O2 C15 -42.8(4) C12 C13 C14 C15 17.3(4) C12 C13 C14 C19 -162.1(3) C12 C13 C26 C27 93.6(3) C12 C13 C26 C31 -84.7(4) C12 C20 C21 C22 -173.9(4) C12 C20 C25 C24 173.9(3) C13 C12 C20 C21 88.6(4) C13 C12 C20 C25 -85.9(4) C13 C14 C15 C16 -177.9(3) C13 C14 C15 O2 0.4(5) C13 C14 C19 C18 178.3(3) C13 C26 C27 C28 -178.2(3) C13 C26 C31 C30 176.8(3) C14 C13 C26 C27 -140.4(3) C14 C13 C26 C31 41.3(4) C14 C15 C16 C17 -0.6(6) C14 C15 O2 C11 12.7(5) C15 C14 C19 C18 -1.1(5) C15 C16 C17 C18 -0.7(6) C16 C15 O2 C11 -168.8(3) C16 C17 C18 C19 1.1(5) C16 C17 C18 C32 178.7(3) C17 C18 C19 C14 -0.1(5) C17 C18 C32 C33 178.1(4) C17 C18 C32 C34 55.3(5) C17 C18 C32 C35 -62.9(4) C19 C14 C15 C16 1.5(5) C19 C14 C15 O2 179.9(3) C19 C18 C32 C33 -4.4(5) C19 C18 C32 C34 -127.3(4) C19 C18 C32 C35 114.5(4) C20 C12 C13 C14 -172.7(3) C20 C12 C13 C26 -45.8(3) C20 C21 C22 C23 0.2(7) C21 C20 C25 C24 -0.9(6) C21 C22 C23 C24 -0.8(7) C22 C23 C24 C25 0.5(7) C23 C24 C25 C20 0.3(6) C25 C20 C21 C22 0.6(6) C26 C13 C14 C15 -110.6(3) C26 C13 C14 C19 70.0(4) C26 C27 C28 C29 1.0(6) C27 C26 C31 C30 -1.5(5) C27 C28 C29 C30 -0.8(7) C28 C29 C30 C31 -0.6(6) C29 C30 C31 C26 1.7(6) C31 C26 C27 C28 0.1(5) C32 C18 C19 C14 -177.7(3) O1 C9 C10 C5 -176.6(3) O1 C9 C10 C11 1.5(5) O2 C11 C12 C13 58.9(3) O2 C11 C12 C20 -175.9(3) O2 C15 C16 C17 -179.1(3)