#------------------------------------------------------------------------------ #$Date: 2020-06-05 13:17:51 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252733 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557926.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_1557926 loop_ _publ_author_name 'Curbet, Idriss' 'Colombel-Rouen, Sophie' 'Manguin, Romane' 'Clermont, Anthony' 'Quelhas, Alexandre' 'M\"uller, Daniel S.' 'Roisnel, Thierry' 'Basl\'e, Olivier' 'Trolez, Yann' 'Mauduit, Marc' _publ_section_title ; Expedient synthesis of conjugated triynes via alkyne metathesis ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 4934 _journal_paper_doi 10.1039/D0SC01124J _journal_volume 11 _journal_year 2020 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C34 H26' _chemical_formula_sum 'C34 H26' _chemical_formula_weight 434.55 _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 dual _atom_sites_solution_secondary difmap _audit_update_record ; 2019-06-04 deposited with the CCDC. 2020-04-27 downloaded from the CCDC. ; _cell_angle_alpha 94.453(3) _cell_angle_beta 104.612(3) _cell_angle_gamma 98.456(3) _cell_formula_units_Z 2 _cell_length_a 8.5611(8) _cell_length_b 10.3957(10) _cell_length_c 14.5334(13) _cell_measurement_reflns_used 9937 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.5185 _cell_measurement_theta_min 2.4961 _cell_measurement_wavelength 0.71073 _cell_volume 1229.1(2) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'SAINT (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2019)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (G. Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector '(CMOS) PHOTON 100' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_unetI/netI 0.0366 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 22961 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.482 _diffrn_reflns_theta_min 2.914 _diffrn_source_current 1.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.174 _exptl_crystal_description plate _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.321 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 310 _refine_ls_number_reflns 5570 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0479 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.6251P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1201 _refine_ls_wR_factor_ref 0.1302 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4477 _reflns_number_total 5570 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d0sc01124j2.cif _cod_data_source_block IC726F2 _cod_depositor_comments 'Adding full bibliography for 1557923--1557928.cif.' _cod_database_code 1557926 _shelx_res_file ; TITL import_a.res in P-1 (created by CRYSCALC) job.res created by SHELXL-2018/3 at 09:17:03 on 28-May-2019 CELL 0.71073 8.5611 10.3957 14.5334 94.453 104.612 98.456 ZERR 2.00 0.0008 0.0010 0.0013 0.003 0.003 0.003 LATT 1 SFAC C H UNIT 68 52 MERG 2 FMAP 2 PLAN 20 SIZE 0.06 0.24 0.35 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.049600 0.625100 FVAR 0.97375 C1 1 0.153463 0.774781 0.604174 11.00000 0.01838 0.01962 = 0.02203 0.00594 0.00456 0.00549 C2 1 0.206982 0.785166 0.510978 11.00000 0.01601 0.02663 = 0.02179 0.00570 0.00359 0.00680 C3 1 0.193507 0.670990 0.449846 11.00000 0.03126 0.02740 = 0.02826 0.00510 0.00768 0.00875 AFIX 43 H3 2 0.154263 0.588313 0.466842 11.00000 -1.20000 AFIX 0 C4 1 0.237248 0.677981 0.364425 11.00000 0.03929 0.04046 = 0.02731 0.00126 0.01040 0.01546 AFIX 43 H4 2 0.226609 0.600160 0.322851 11.00000 -1.20000 AFIX 0 C5 1 0.296212 0.797696 0.339616 11.00000 0.03211 0.05166 = 0.02571 0.00687 0.01175 0.01136 AFIX 43 H5 2 0.325669 0.802185 0.281003 11.00000 -1.20000 AFIX 0 C6 1 0.312191 0.910606 0.400124 11.00000 0.02637 0.04199 = 0.03086 0.01191 0.00840 0.00106 AFIX 43 H6 2 0.354008 0.992730 0.383387 11.00000 -1.20000 AFIX 0 C7 1 0.267340 0.904967 0.485733 11.00000 0.02300 0.02814 = 0.02519 0.00447 0.00510 0.00261 AFIX 43 H7 2 0.278082 0.983217 0.526880 11.00000 -1.20000 AFIX 0 C8 1 0.202576 0.907419 0.668979 11.00000 0.02219 0.02040 = 0.01978 0.00574 0.00601 0.00286 C9 1 0.362551 0.947142 0.726099 11.00000 0.02266 0.02894 = 0.02487 0.00575 0.00544 0.00377 AFIX 43 H9 2 0.441326 0.891652 0.725961 11.00000 -1.20000 AFIX 0 C10 1 0.407751 1.066666 0.783027 11.00000 0.02878 0.03372 = 0.02612 0.00265 0.00416 -0.00355 AFIX 43 H10 2 0.517081 1.092412 0.821853 11.00000 -1.20000 AFIX 0 C11 1 0.294623 1.148953 0.783747 11.00000 0.04199 0.02390 = 0.03223 -0.00169 0.01066 -0.00149 AFIX 43 H11 2 0.325685 1.230576 0.823346 11.00000 -1.20000 AFIX 0 C12 1 0.136262 1.111459 0.726451 11.00000 0.03740 0.02527 = 0.03973 0.00314 0.01038 0.00959 AFIX 43 H12 2 0.058452 1.167961 0.726067 11.00000 -1.20000 AFIX 0 C13 1 0.090262 0.991179 0.669268 11.00000 0.02557 0.02504 = 0.03006 0.00431 0.00372 0.00627 AFIX 43 H13 2 -0.018913 0.966141 0.630087 11.00000 -1.20000 AFIX 0 C14 1 -0.033050 0.727617 0.584026 11.00000 0.02017 0.01870 = 0.03193 0.00111 0.00751 0.00415 C15 1 -0.140279 0.730208 0.495448 11.00000 0.02299 0.03532 = 0.03663 0.00350 0.00378 0.00693 AFIX 43 H15 2 -0.098889 0.754928 0.443397 11.00000 -1.20000 AFIX 0 C16 1 -0.309208 0.696561 0.482410 11.00000 0.02183 0.04701 = 0.05668 -0.00342 -0.00193 0.00739 AFIX 43 H16 2 -0.382269 0.696891 0.421223 11.00000 -1.20000 AFIX 0 C17 1 -0.370013 0.662948 0.557969 11.00000 0.02027 0.03830 = 0.07775 -0.01022 0.01520 0.00031 AFIX 43 H17 2 -0.484981 0.641524 0.549216 11.00000 -1.20000 AFIX 0 C18 1 -0.263988 0.660402 0.646314 11.00000 0.03387 0.03641 = 0.06217 0.00151 0.02893 0.00048 AFIX 43 H18 2 -0.306098 0.637362 0.698467 11.00000 -1.20000 AFIX 0 C19 1 -0.095364 0.691451 0.659502 11.00000 0.02964 0.03075 = 0.03845 0.00295 0.01510 0.00180 AFIX 43 H19 2 -0.022756 0.687893 0.720266 11.00000 -1.20000 AFIX 0 C20 1 0.240673 0.678888 0.657197 11.00000 0.02319 0.02324 = 0.02460 0.00562 0.00778 0.00527 C21 1 0.320166 0.608944 0.703949 11.00000 0.02748 0.02633 = 0.02761 0.00777 0.00911 0.00770 C22 1 0.420668 0.536700 0.759176 11.00000 0.02922 0.02470 = 0.02864 0.00837 0.00966 0.00784 C23 1 0.517396 0.480729 0.808890 11.00000 0.03015 0.02423 = 0.02794 0.00711 0.00915 0.00735 C24 1 0.629860 0.417495 0.863922 11.00000 0.03056 0.02388 = 0.02640 0.00528 0.00722 0.00706 C25 1 0.729328 0.361519 0.911313 11.00000 0.03189 0.02312 = 0.02247 -0.00024 0.00331 0.00735 C26 1 0.844629 0.292968 0.967905 11.00000 0.03377 0.02491 = 0.02094 -0.00251 -0.00075 0.01234 C27 1 0.795521 0.214047 1.033798 11.00000 0.04155 0.03131 = 0.02103 0.00030 0.00165 0.01371 C28 1 0.909183 0.147016 1.087657 11.00000 0.05274 0.03849 = 0.02204 0.00468 0.00113 0.02103 AFIX 43 H28 2 0.877148 0.092595 1.131623 11.00000 -1.20000 AFIX 0 C29 1 1.068095 0.157925 1.078552 11.00000 0.05074 0.04547 = 0.02621 -0.00253 -0.00469 0.02836 C30 1 1.114183 0.238065 1.014241 11.00000 0.03521 0.04833 = 0.03459 -0.00784 -0.00104 0.02079 AFIX 43 H30 2 1.223212 0.246359 1.008488 11.00000 -1.20000 AFIX 0 C31 1 1.005539 0.306679 0.957899 11.00000 0.03435 0.03087 = 0.02564 -0.00806 0.00128 0.01051 C32 1 0.625652 0.203455 1.046908 11.00000 0.04762 0.05114 = 0.02886 0.01196 0.01073 0.01560 AFIX 137 H32A 2 0.545950 0.158243 0.988401 11.00000 -1.50000 H32B 2 0.601997 0.291390 1.060130 11.00000 -1.50000 H32C 2 0.618255 0.153825 1.100742 11.00000 -1.50000 AFIX 0 C33 1 1.187645 0.082583 1.137753 11.00000 0.06898 0.07114 = 0.03840 0.00273 -0.00758 0.04793 AFIX 137 H33A 2 1.153047 -0.011340 1.116082 11.00000 -1.50000 H33B 2 1.189737 0.099228 1.205392 11.00000 -1.50000 H33C 2 1.297448 0.111146 1.130062 11.00000 -1.50000 AFIX 0 C34 1 1.058149 0.392876 0.888978 11.00000 0.03660 0.04049 = 0.03854 -0.00485 0.00753 0.00706 AFIX 137 H34A 2 1.177730 0.406060 0.901665 11.00000 -1.50000 H34B 2 1.023286 0.477746 0.897075 11.00000 -1.50000 H34C 2 1.007747 0.351045 0.823239 11.00000 -1.50000 AFIX 0 HKLF 4 REM import_a.res in P-1 (created by CRYSCALC) REM wR2 = 0.1302, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0479 for 4477 Fo > 4sig(Fo) and 0.0628 for all 5570 data REM 310 parameters refined using 0 restraints END WGHT 0.0471 0.6553 REM Highest difference peak 0.321, deepest hole -0.215, 1-sigma level 0.042 Q1 1 0.1817 0.8413 0.6362 11.00000 0.05 0.32 Q2 1 0.1946 0.7827 0.5586 11.00000 0.05 0.25 Q3 1 1.2435 0.0361 1.1022 11.00000 0.05 0.24 Q4 1 -0.3118 0.6193 0.5942 11.00000 0.05 0.23 Q5 1 1.2725 0.1440 1.1827 11.00000 0.05 0.21 Q6 1 0.1435 0.9294 0.6876 11.00000 0.05 0.21 Q7 1 0.2038 0.7409 0.6368 11.00000 0.05 0.21 Q8 1 0.2741 0.8430 0.5113 11.00000 0.05 0.19 Q9 1 0.3557 1.1204 0.7519 11.00000 0.05 0.19 Q10 1 0.5356 0.2468 0.9927 11.00000 0.05 0.18 Q11 1 0.2761 0.9278 0.6885 11.00000 0.05 0.18 Q12 1 0.6418 0.3360 0.9654 11.00000 0.05 0.18 Q13 1 0.2908 0.6811 0.7185 11.00000 0.05 0.18 Q14 1 0.3868 1.0135 0.7326 11.00000 0.05 0.18 Q15 1 -0.1882 0.7126 0.6574 11.00000 0.05 0.18 Q16 1 0.2922 0.8961 0.4423 11.00000 0.05 0.18 Q17 1 0.2207 0.7283 0.4858 11.00000 0.05 0.18 Q18 1 1.1364 0.0275 1.1877 11.00000 0.05 0.17 Q19 1 1.2612 0.1459 1.1042 11.00000 0.05 0.17 Q20 1 0.2683 0.8640 0.3598 11.00000 0.05 0.17 ; _shelx_res_checksum 82664 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 0.15346(15) 0.77478(13) 0.60417(9) 0.0197(3) Uani 1 1 d . . . . . C2 C 0.20698(15) 0.78517(13) 0.51098(10) 0.0213(3) Uani 1 1 d . . . . . C3 C 0.19351(18) 0.67099(15) 0.44985(11) 0.0285(3) Uani 1 1 d . . . . . H3 H 0.154263 0.588313 0.466842 0.034 Uiso 1 1 calc R U . . . C4 C 0.2372(2) 0.67798(17) 0.36442(11) 0.0347(4) Uani 1 1 d . . . . . H4 H 0.226609 0.600160 0.322851 0.042 Uiso 1 1 calc R U . . . C5 C 0.29621(19) 0.79770(18) 0.33962(11) 0.0352(4) Uani 1 1 d . . . . . H5 H 0.325669 0.802185 0.281003 0.042 Uiso 1 1 calc R U . . . C6 C 0.31219(18) 0.91061(17) 0.40012(11) 0.0330(3) Uani 1 1 d . . . . . H6 H 0.354008 0.992730 0.383387 0.040 Uiso 1 1 calc R U . . . C7 C 0.26734(17) 0.90497(14) 0.48573(10) 0.0258(3) Uani 1 1 d . . . . . H7 H 0.278082 0.983217 0.526880 0.031 Uiso 1 1 calc R U . . . C8 C 0.20258(16) 0.90742(13) 0.66898(9) 0.0206(3) Uani 1 1 d . . . . . C9 C 0.36255(17) 0.94714(14) 0.72610(10) 0.0256(3) Uani 1 1 d . . . . . H9 H 0.441326 0.891652 0.725961 0.031 Uiso 1 1 calc R U . . . C10 C 0.40775(19) 1.06667(15) 0.78303(11) 0.0311(3) Uani 1 1 d . . . . . H10 H 0.517081 1.092412 0.821853 0.037 Uiso 1 1 calc R U . . . C11 C 0.2946(2) 1.14895(15) 0.78375(11) 0.0336(3) Uani 1 1 d . . . . . H11 H 0.325685 1.230576 0.823346 0.040 Uiso 1 1 calc R U . . . C12 C 0.1363(2) 1.11146(15) 0.72645(12) 0.0337(3) Uani 1 1 d . . . . . H12 H 0.058452 1.167961 0.726067 0.040 Uiso 1 1 calc R U . . . C13 C 0.09026(18) 0.99118(14) 0.66927(11) 0.0273(3) Uani 1 1 d . . . . . H13 H -0.018913 0.966141 0.630087 0.033 Uiso 1 1 calc R U . . . C14 C -0.03305(16) 0.72762(13) 0.58403(10) 0.0235(3) Uani 1 1 d . . . . . C15 C -0.14028(18) 0.73021(16) 0.49545(12) 0.0323(3) Uani 1 1 d . . . . . H15 H -0.098889 0.754928 0.443397 0.039 Uiso 1 1 calc R U . . . C16 C -0.3092(2) 0.69656(18) 0.48241(15) 0.0445(4) Uani 1 1 d . . . . . H16 H -0.382269 0.696891 0.421223 0.053 Uiso 1 1 calc R U . . . C17 C -0.3700(2) 0.66295(17) 0.55797(16) 0.0465(5) Uani 1 1 d . . . . . H17 H -0.484981 0.641524 0.549216 0.056 Uiso 1 1 calc R U . . . C18 C -0.2640(2) 0.66040(17) 0.64631(15) 0.0420(4) Uani 1 1 d . . . . . H18 H -0.306098 0.637362 0.698467 0.050 Uiso 1 1 calc R U . . . C19 C -0.09536(19) 0.69145(15) 0.65950(12) 0.0323(3) Uani 1 1 d . . . . . H19 H -0.022756 0.687893 0.720266 0.039 Uiso 1 1 calc R U . . . C20 C 0.24067(17) 0.67889(13) 0.65720(10) 0.0231(3) Uani 1 1 d . . . . . C21 C 0.32017(18) 0.60894(14) 0.70395(10) 0.0263(3) Uani 1 1 d . . . . . C22 C 0.42067(18) 0.53670(14) 0.75918(11) 0.0266(3) Uani 1 1 d . . . . . C23 C 0.51740(18) 0.48073(14) 0.80889(10) 0.0267(3) Uani 1 1 d . . . . . C24 C 0.62986(18) 0.41749(14) 0.86392(10) 0.0266(3) Uani 1 1 d . . . . . C25 C 0.72933(18) 0.36152(14) 0.91131(10) 0.0264(3) Uani 1 1 d . . . . . C26 C 0.84463(19) 0.29297(14) 0.96790(10) 0.0275(3) Uani 1 1 d . . . . . C27 C 0.7955(2) 0.21405(15) 1.03380(10) 0.0319(3) Uani 1 1 d . . . . . C28 C 0.9092(2) 0.14702(17) 1.08766(11) 0.0380(4) Uani 1 1 d . . . . . H28 H 0.877148 0.092595 1.131623 0.046 Uiso 1 1 calc R U . . . C29 C 1.0681(2) 0.15792(18) 1.07855(12) 0.0418(4) Uani 1 1 d . . . . . C30 C 1.1142(2) 0.23807(18) 1.01424(12) 0.0406(4) Uani 1 1 d . . . . . H30 H 1.223212 0.246359 1.008488 0.049 Uiso 1 1 calc R U . . . C31 C 1.00554(19) 0.30668(15) 0.95790(11) 0.0316(3) Uani 1 1 d . . . . . C32 C 0.6257(2) 0.20345(19) 1.04691(12) 0.0413(4) Uani 1 1 d . . . . . H32A H 0.545950 0.158243 0.988401 0.062 Uiso 1 1 calc R U . . . H32B H 0.601997 0.291390 1.060130 0.062 Uiso 1 1 calc R U . . . H32C H 0.618255 0.153825 1.100742 0.062 Uiso 1 1 calc R U . . . C33 C 1.1876(3) 0.0826(2) 1.13775(14) 0.0600(6) Uani 1 1 d . . . . . H33A H 1.153047 -0.011340 1.116082 0.090 Uiso 1 1 calc R U . . . H33B H 1.189737 0.099228 1.205392 0.090 Uiso 1 1 calc R U . . . H33C H 1.297448 0.111146 1.130062 0.090 Uiso 1 1 calc R U . . . C34 C 1.0581(2) 0.39288(17) 0.88898(13) 0.0395(4) Uani 1 1 d . . . . . H34A H 1.177730 0.406060 0.901665 0.059 Uiso 1 1 calc R U . . . H34B H 1.023286 0.477746 0.897075 0.059 Uiso 1 1 calc R U . . . H34C H 1.007747 0.351045 0.823239 0.059 Uiso 1 1 calc R U . . . 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 0.0184(6) 0.0196(6) 0.0220(6) 0.0059(5) 0.0046(5) 0.0055(5) C2 0.0160(6) 0.0266(7) 0.0218(6) 0.0057(5) 0.0036(5) 0.0068(5) C3 0.0313(7) 0.0274(7) 0.0283(7) 0.0051(6) 0.0077(6) 0.0087(6) C4 0.0393(9) 0.0405(9) 0.0273(8) 0.0013(7) 0.0104(7) 0.0155(7) C5 0.0321(8) 0.0517(10) 0.0257(8) 0.0069(7) 0.0118(6) 0.0114(7) C6 0.0264(7) 0.0420(9) 0.0309(8) 0.0119(7) 0.0084(6) 0.0011(6) C7 0.0230(7) 0.0281(7) 0.0252(7) 0.0045(6) 0.0051(5) 0.0026(5) C8 0.0222(6) 0.0204(6) 0.0198(6) 0.0057(5) 0.0060(5) 0.0029(5) C9 0.0227(7) 0.0289(7) 0.0249(7) 0.0057(6) 0.0054(5) 0.0038(5) C10 0.0288(7) 0.0337(8) 0.0261(7) 0.0027(6) 0.0042(6) -0.0036(6) C11 0.0420(9) 0.0239(7) 0.0322(8) -0.0017(6) 0.0107(7) -0.0015(6) C12 0.0374(8) 0.0253(7) 0.0397(9) 0.0031(6) 0.0104(7) 0.0096(6) C13 0.0256(7) 0.0250(7) 0.0301(8) 0.0043(6) 0.0037(6) 0.0063(6) C14 0.0202(6) 0.0187(6) 0.0319(7) 0.0011(5) 0.0075(5) 0.0041(5) C15 0.0230(7) 0.0353(8) 0.0366(8) 0.0035(7) 0.0038(6) 0.0069(6) C16 0.0218(8) 0.0470(10) 0.0567(11) -0.0034(9) -0.0019(7) 0.0074(7) C17 0.0203(7) 0.0383(9) 0.0778(14) -0.0102(9) 0.0152(8) 0.0003(7) C18 0.0339(9) 0.0364(9) 0.0622(12) 0.0015(8) 0.0289(9) 0.0005(7) C19 0.0296(8) 0.0307(8) 0.0385(9) 0.0029(6) 0.0151(7) 0.0018(6) C20 0.0232(6) 0.0232(7) 0.0246(7) 0.0056(5) 0.0078(5) 0.0053(5) C21 0.0275(7) 0.0263(7) 0.0276(7) 0.0078(6) 0.0091(6) 0.0077(6) C22 0.0292(7) 0.0247(7) 0.0286(7) 0.0084(6) 0.0097(6) 0.0078(6) C23 0.0301(7) 0.0242(7) 0.0279(7) 0.0071(6) 0.0092(6) 0.0074(6) C24 0.0306(7) 0.0239(7) 0.0264(7) 0.0053(6) 0.0072(6) 0.0071(6) C25 0.0319(7) 0.0231(7) 0.0225(7) -0.0002(5) 0.0033(6) 0.0073(6) C26 0.0338(8) 0.0249(7) 0.0209(7) -0.0025(5) -0.0007(6) 0.0123(6) C27 0.0415(9) 0.0313(8) 0.0210(7) 0.0003(6) 0.0017(6) 0.0137(7) C28 0.0527(10) 0.0385(9) 0.0220(7) 0.0047(6) 0.0011(7) 0.0210(8) C29 0.0507(10) 0.0455(10) 0.0262(8) -0.0025(7) -0.0047(7) 0.0284(8) C30 0.0352(9) 0.0483(10) 0.0346(9) -0.0078(7) -0.0010(7) 0.0208(8) C31 0.0344(8) 0.0309(8) 0.0256(7) -0.0081(6) 0.0013(6) 0.0105(6) C32 0.0476(10) 0.0511(10) 0.0289(8) 0.0120(7) 0.0107(7) 0.0156(8) C33 0.0690(14) 0.0711(14) 0.0384(10) 0.0027(9) -0.0076(9) 0.0479(12) C34 0.0366(9) 0.0405(9) 0.0385(9) -0.0049(7) 0.0075(7) 0.0071(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C20 C1 C2 107.83(10) . . ? C20 C1 C14 108.79(11) . . ? C2 C1 C14 111.95(11) . . ? C20 C1 C8 107.62(11) . . ? C2 C1 C8 111.18(11) . . ? C14 C1 C8 109.34(10) . . ? C7 C2 C3 119.05(13) . . ? C7 C2 C1 121.81(12) . . ? C3 C2 C1 119.14(12) . . ? C4 C3 C2 120.27(14) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.27(15) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 119.86(15) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.40(15) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.14(14) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C13 C8 C9 118.61(13) . . ? C13 C8 C1 120.95(12) . . ? C9 C8 C1 120.41(12) . . ? C10 C9 C8 120.63(14) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.42(14) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.50(14) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.24(14) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 120.60(14) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C19 119.27(14) . . ? C15 C14 C1 122.04(13) . . ? C19 C14 C1 118.49(13) . . ? C14 C15 C16 120.18(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.17(17) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.92(15) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.28(17) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C14 C19 C18 120.16(16) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C1 175.07(15) . . ? C20 C21 C22 175.71(16) . . ? C23 C22 C21 175.47(16) . . ? C22 C23 C24 178.58(16) . . ? C25 C24 C23 179.20(16) . . ? C24 C25 C26 178.74(17) . . ? C31 C26 C27 121.15(13) . . ? C31 C26 C25 119.59(14) . . ? C27 C26 C25 119.25(14) . . ? C28 C27 C26 118.41(15) . . ? C28 C27 C32 120.54(15) . . ? C26 C27 C32 121.05(13) . . ? C29 C28 C27 121.57(17) . . ? C29 C28 H28 119.2 . . ? C27 C28 H28 119.2 . . ? C28 C29 C30 118.87(14) . . ? C28 C29 C33 120.00(18) . . ? C30 C29 C33 121.13(18) . . ? C29 C30 C31 122.14(17) . . ? C29 C30 H30 118.9 . . ? C31 C30 H30 118.9 . . ? C30 C31 C26 117.84(16) . . ? C30 C31 C34 121.21(15) . . ? C26 C31 C34 120.94(14) . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C33 H33A 109.5 . . ? C29 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C29 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 C20 1.4809(17) . ? C1 C2 1.5419(18) . ? C1 C14 1.5451(18) . ? C1 C8 1.5470(19) . ? C2 C7 1.389(2) . ? C2 C3 1.398(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.379(2) . ? C5 H5 0.9500 . ? C6 C7 1.394(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.3894(19) . ? C8 C9 1.3936(19) . ? C9 C10 1.384(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 C19 1.389(2) . ? C15 C16 1.397(2) . ? C15 H15 0.9500 . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.377(3) . ? C17 H17 0.9500 . ? C18 C19 1.392(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.2010(19) . ? C21 C22 1.3725(19) . ? C22 C23 1.205(2) . ? C23 C24 1.3704(19) . ? C24 C25 1.204(2) . ? C25 C26 1.4307(19) . ? C26 C31 1.409(2) . ? C26 C27 1.411(2) . ? C27 C28 1.395(2) . ? C27 C32 1.503(2) . ? C28 C29 1.389(3) . ? C28 H28 0.9500 . ? C29 C30 1.391(3) . ? C29 C33 1.516(2) . ? C30 C31 1.395(2) . ? C30 H30 0.9500 . ? C31 C34 1.502(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 C1 C2 C7 -127.00(13) . . . . ? C14 C1 C2 C7 113.37(14) . . . . ? C8 C1 C2 C7 -9.25(17) . . . . ? C20 C1 C2 C3 53.40(16) . . . . ? C14 C1 C2 C3 -66.24(15) . . . . ? C8 C1 C2 C3 171.15(12) . . . . ? C7 C2 C3 C4 -1.1(2) . . . . ? C1 C2 C3 C4 178.49(13) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C3 C2 C7 C6 0.6(2) . . . . ? C1 C2 C7 C6 -179.03(12) . . . . ? C5 C6 C7 C2 0.4(2) . . . . ? C20 C1 C8 C13 -144.23(13) . . . . ? C2 C1 C8 C13 97.89(14) . . . . ? C14 C1 C8 C13 -26.22(17) . . . . ? C20 C1 C8 C9 37.87(16) . . . . ? C2 C1 C8 C9 -80.01(15) . . . . ? C14 C1 C8 C9 155.88(12) . . . . ? C13 C8 C9 C10 1.0(2) . . . . ? C1 C8 C9 C10 178.95(13) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C9 C8 C13 C12 -0.9(2) . . . . ? C1 C8 C13 C12 -178.79(13) . . . . ? C11 C12 C13 C8 0.0(2) . . . . ? C20 C1 C14 C15 -135.41(14) . . . . ? C2 C1 C14 C15 -16.34(18) . . . . ? C8 C1 C14 C15 107.32(15) . . . . ? C20 C1 C14 C19 49.77(16) . . . . ? C2 C1 C14 C19 168.83(12) . . . . ? C8 C1 C14 C19 -67.51(15) . . . . ? C19 C14 C15 C16 -0.1(2) . . . . ? C1 C14 C15 C16 -174.88(14) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? C15 C16 C17 C18 -1.1(3) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C15 C14 C19 C18 -1.1(2) . . . . ? C1 C14 C19 C18 173.88(14) . . . . ? C17 C18 C19 C14 1.2(2) . . . . ? C31 C26 C27 C28 -1.5(2) . . . . ? C25 C26 C27 C28 179.40(14) . . . . ? C31 C26 C27 C32 177.75(14) . . . . ? C25 C26 C27 C32 -1.4(2) . . . . ? C26 C27 C28 C29 0.9(2) . . . . ? C32 C27 C28 C29 -178.34(16) . . . . ? C27 C28 C29 C30 0.2(3) . . . . ? C27 C28 C29 C33 -179.48(16) . . . . ? C28 C29 C30 C31 -0.7(3) . . . . ? C33 C29 C30 C31 178.95(16) . . . . ? C29 C30 C31 C26 0.1(2) . . . . ? C29 C30 C31 C34 179.91(15) . . . . ? C27 C26 C31 C30 1.0(2) . . . . ? C25 C26 C31 C30 -179.90(13) . . . . ? C27 C26 C31 C34 -178.82(14) . . . . ? C25 C26 C31 C34 0.3(2) . . . . ?