#------------------------------------------------------------------------------ #$Date: 2019-06-22 03:14:26 +0300 (Sat, 22 Jun 2019) $ #$Revision: 216486 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/18/1551853.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_1551853 loop_ _publ_author_name 'Sun, Fengna' 'Yang, Wan-Chun' 'Chen, Xiao-Bing' 'Sun, Yuli' 'Cao, Jian' 'Xu, Zheng' 'Xu, Li-Wen' _publ_section_title ; Enantioselective Palladium/Copper-Catalyzed C-C Bond Activation Synergized with Sonogashira-Type C(sp3)-C(sp) Cross-Coupling Alkynylation ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02431J _journal_year 2019 _chemical_formula_moiety 'C19 H16 O' _chemical_formula_sum 'C19 H16 O' _chemical_formula_weight 260.32 _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' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-03-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-04-15 deposited with the CCDC. 2019-06-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.9220(2) _cell_length_b 18.8611(4) _cell_length_c 19.2017(5) _cell_measurement_reflns_used 3055 _cell_measurement_temperature 293.15 _cell_measurement_theta_max 70.61 _cell_measurement_theta_min 38.71 _cell_volume 2869.07(12) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293.15 _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_Laue_measured_fraction_full 0.959 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 15461 _diffrn_reflns_point_group_measured_fraction_full 0.958 _diffrn_reflns_point_group_measured_fraction_max 0.942 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.831 _diffrn_reflns_theta_min 5.169 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8893 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0808 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8893. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.205 _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.105 _refine_diff_density_min -0.096 _refine_diff_density_rms 0.022 _refine_ls_abs_structure_details ; Flack x determined using 2134 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.10(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 5208 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0317 _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^)+(0.0548P)^2^+0.1323P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0867 _refine_ls_wR_factor_ref 0.0876 _reflns_Friedel_coverage 0.744 _reflns_Friedel_fraction_full 0.957 _reflns_Friedel_fraction_max 0.930 _reflns_number_gt 5090 _reflns_number_total 5208 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02431j2.cif _cod_data_source_block cu_190326a_0m _cod_database_code 1551853 _shelx_shelxl_version_number 2014/7 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C31(H31A,H31B), C12(H12A,H12B), C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C22(H22), C24(H24), C34(H34), C15(H15), C30(H30), C11(H11), C5(H5), C23(H23), C3(H3), C19(H19), C18(H18), C38(H38), C35(H35), C36(H36), C17(H17), C16(H16), C37(H37), C4(H4) 2.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C32(H32A,H32B,H32C) ; _shelx_res_file ; cu_190326a_0m.res created by SHELXL-2014/7 TITL cu_190326a_0m_a.res in P2(1)2(1)2(1) REM Old TITL cu_190326a_0m in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.132, Rweak 0.033, Alpha 0.007, Orientation as input REM Flack x = 0.135 ( 0.087 ) from Parsons' quotients REM Formula found by SHELXT: C36 N2 O2 CELL 1.54178 7.922 18.8611 19.2017 90 90 90 ZERR 8 0.0002 0.0004 0.0005 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O UNIT 152 128 8 L.S. 20 PLAN 5 TEMP 23 BOND $H list 4 fmap 2 ACTA OMIT 0 0 14 REM REM REM WGHT 0.054800 0.132300 FVAR 1.60386 O2 3 0.380283 0.229093 0.591826 11.00000 0.07896 0.06932 = 0.08874 0.00858 -0.00470 0.02935 C25 1 0.752410 0.032502 0.624754 11.00000 0.04182 0.03866 = 0.04204 -0.00162 -0.00186 -0.00407 C7 1 0.182335 0.513958 0.608969 11.00000 0.04691 0.03811 = 0.04121 -0.00328 0.00151 0.00096 C6 1 0.333229 0.548327 0.623773 11.00000 0.04545 0.03751 = 0.04487 0.00005 0.00165 0.00191 C14 1 0.481288 0.670249 0.630957 11.00000 0.04821 0.03762 = 0.05043 0.00202 0.00010 0.00053 C26 1 0.694704 0.101105 0.611673 11.00000 0.04321 0.03893 = 0.04106 -0.00044 -0.00370 -0.00382 C2 1 0.161927 0.441676 0.616738 11.00000 0.06271 0.03943 = 0.05177 -0.00327 0.00446 -0.00376 C10 1 0.345094 0.624110 0.603436 11.00000 0.05274 0.03844 = 0.04594 0.00207 -0.00166 -0.00236 O1 3 -0.070009 0.364509 0.587540 11.00000 0.11306 0.06146 = 0.14025 0.00584 -0.02776 -0.03997 C22 1 0.409306 0.071987 0.643654 11.00000 0.03825 0.05993 = 0.05795 -0.00686 -0.00161 0.00062 AFIX 43 H22 2 0.296759 0.084760 0.649343 11.00000 -1.20000 AFIX 0 C21 1 0.528022 0.120221 0.617852 11.00000 0.04782 0.04495 = 0.04729 -0.00455 -0.00602 0.00269 C33 1 1.013647 -0.049473 0.627698 11.00000 0.03993 0.04146 = 0.05782 -0.00482 0.00051 -0.00376 C24 1 0.632897 -0.015456 0.650198 11.00000 0.04719 0.03875 = 0.05571 0.00072 -0.00018 -0.00495 AFIX 43 H24 2 0.665556 -0.061631 0.660547 11.00000 -1.20000 AFIX 0 C29 1 0.927722 0.016126 0.603788 11.00000 0.04158 0.04540 = 0.04655 -0.00269 -0.00059 -0.00100 C34 1 1.013675 -0.068234 0.697944 11.00000 0.04929 0.04477 = 0.06172 0.00079 0.00059 -0.00097 AFIX 43 H34 2 0.951509 -0.041570 0.729599 11.00000 -1.20000 AFIX 0 C8 1 0.026582 0.550776 0.582367 11.00000 0.04777 0.04606 = 0.05774 -0.00253 -0.01135 0.00051 C15 1 0.520676 0.670204 0.701712 11.00000 0.05581 0.05118 = 0.05265 0.00413 -0.00127 -0.00783 AFIX 43 H15 2 0.465217 0.639088 0.731513 11.00000 -1.20000 AFIX 0 C27 1 0.807628 0.161246 0.588588 11.00000 0.05293 0.04053 = 0.05668 0.00997 -0.00472 -0.00654 C30 1 1.007287 0.062057 0.561423 11.00000 0.04622 0.06222 = 0.05090 0.00431 0.00638 -0.00317 AFIX 43 H30 2 1.115061 0.050073 0.546254 11.00000 -1.20000 AFIX 0 C11 1 0.228283 0.649818 0.559658 11.00000 0.07288 0.04076 = 0.05866 0.00911 -0.01690 -0.00654 AFIX 43 H11 2 0.236666 0.697166 0.546587 11.00000 -1.20000 AFIX 0 C5 1 0.461771 0.506543 0.651394 11.00000 0.04743 0.05042 = 0.06570 0.00143 -0.00355 0.00675 AFIX 43 H5 2 0.564440 0.527374 0.662922 11.00000 -1.20000 AFIX 0 C23 1 0.464984 0.004920 0.660334 11.00000 0.04540 0.05344 = 0.06083 0.00008 0.00186 -0.01269 AFIX 43 H23 2 0.388992 -0.027623 0.678800 11.00000 -1.20000 AFIX 0 C3 1 0.290962 0.400306 0.644256 11.00000 0.08184 0.03509 = 0.06915 0.00239 0.00112 0.00403 AFIX 43 H3 2 0.277631 0.351717 0.650394 11.00000 -1.20000 AFIX 0 C28 1 0.677691 0.215078 0.560307 11.00000 0.07001 0.04621 = 0.07337 0.01532 -0.00804 -0.00045 AFIX 23 H28A 2 0.707031 0.262821 0.574665 11.00000 -1.20000 H28B 2 0.673996 0.213456 0.509839 11.00000 -1.20000 AFIX 0 C31 1 0.934647 0.131539 0.536712 11.00000 0.05797 0.06578 = 0.05838 0.02022 0.00525 -0.00634 AFIX 23 H31A 2 0.879665 0.124542 0.492102 11.00000 -1.20000 H31B 2 1.025333 0.165454 0.530207 11.00000 -1.20000 AFIX 0 C20 1 0.508737 0.193523 0.590799 11.00000 0.06499 0.04900 = 0.05759 0.00031 -0.01015 0.01093 C19 1 0.568822 0.716887 0.587650 11.00000 0.06375 0.04916 = 0.05710 0.00737 -0.00038 -0.00705 AFIX 43 H19 2 0.546116 0.717396 0.540134 11.00000 -1.20000 AFIX 0 C13 1 -0.066054 0.584866 0.644136 11.00000 0.04871 0.06984 = 0.08987 -0.01551 -0.00380 0.01240 AFIX 137 H13A 2 -0.096452 0.548832 0.677143 11.00000 -1.50000 H13B 2 -0.166193 0.608171 0.627743 11.00000 -1.50000 H13C 2 0.006577 0.618904 0.666131 11.00000 -1.50000 AFIX 0 C12 1 0.084090 0.606965 0.530201 11.00000 0.08052 0.05352 = 0.06672 0.01103 -0.03106 -0.00759 AFIX 23 H12A 2 0.119833 0.584124 0.487410 11.00000 -1.20000 H12B 2 -0.009555 0.638193 0.519322 11.00000 -1.20000 AFIX 0 C18 1 0.688967 0.762344 0.614678 11.00000 0.07243 0.05450 = 0.08085 0.01123 0.00362 -0.02011 AFIX 43 H18 2 0.745840 0.793424 0.585297 11.00000 -1.20000 AFIX 0 C38 1 1.103946 -0.091624 0.581183 11.00000 0.06247 0.05257 = 0.07254 -0.01231 0.01150 0.00159 AFIX 43 H38 2 1.102826 -0.080924 0.533906 11.00000 -1.20000 AFIX 0 C9 1 -0.077016 0.488258 0.552829 11.00000 0.06177 0.06253 = 0.07093 -0.00598 -0.01701 -0.01247 AFIX 23 H9A 2 -0.195649 0.493622 0.564170 11.00000 -1.20000 H9B 2 -0.065218 0.485635 0.502614 11.00000 -1.20000 AFIX 0 C35 1 1.105584 -0.126326 0.721116 11.00000 0.05933 0.05215 = 0.08219 0.01553 -0.00668 -0.00221 AFIX 43 H35 2 1.105770 -0.138090 0.768150 11.00000 -1.20000 AFIX 0 C36 1 1.196815 -0.166667 0.674228 11.00000 0.06177 0.04299 = 0.12248 0.00898 -0.00106 0.00765 AFIX 43 H36 2 1.259020 -0.205440 0.689611 11.00000 -1.20000 AFIX 0 C1 1 -0.004837 0.422298 0.587119 11.00000 0.07356 0.05121 = 0.07102 -0.00678 -0.00103 -0.01840 C17 1 0.724803 0.761908 0.684472 11.00000 0.06932 0.05685 = 0.08981 -0.00454 -0.01164 -0.01986 AFIX 43 H17 2 0.805558 0.792684 0.702414 11.00000 -1.20000 AFIX 0 C32 1 0.898410 0.191538 0.652598 11.00000 0.07623 0.04861 = 0.07791 0.00215 -0.01570 -0.01868 AFIX 137 H32A 2 0.816460 0.208567 0.685410 11.00000 -1.50000 H32B 2 0.970264 0.229937 0.638523 11.00000 -1.50000 H32C 2 0.965306 0.155062 0.673908 11.00000 -1.50000 AFIX 0 C16 1 0.640933 0.715771 0.728018 11.00000 0.07100 0.06340 = 0.06104 -0.00578 -0.01048 -0.00994 AFIX 43 H16 2 0.665535 0.715356 0.775374 11.00000 -1.20000 AFIX 0 C37 1 1.195044 -0.149159 0.604850 11.00000 0.06979 0.04786 = 0.11359 -0.01379 0.01920 0.00783 AFIX 43 H37 2 1.256093 -0.176451 0.573342 11.00000 -1.20000 AFIX 0 C4 1 0.439231 0.433833 0.662103 11.00000 0.07080 0.04786 = 0.07747 0.00608 -0.00936 0.01832 AFIX 43 H4 2 0.526350 0.407505 0.681728 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_190326a_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0317 for 5090 Fo > 4sig(Fo) and 0.0325 for all 5208 data REM 363 parameters refined using 0 restraints END WGHT 0.0548 0.1323 REM Highest difference peak 0.105, deepest hole -0.096, 1-sigma level 0.022 Q1 1 0.9640 -0.0200 0.6167 11.00000 0.05 0.11 Q2 1 0.0954 0.5359 0.6000 11.00000 0.05 0.10 Q3 1 0.9423 0.0185 0.5633 11.00000 0.05 0.10 Q4 1 0.3405 0.5874 0.6140 11.00000 0.05 0.09 Q5 1 -0.0367 0.5192 0.5662 11.00000 0.05 0.09 ; _shelx_res_checksum 84702 _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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O2 O 0.3803(2) 0.22909(8) 0.59183(9) 0.0790(4) Uani 1 1 d . C25 C 0.75241(19) 0.03250(8) 0.62475(8) 0.0408(3) Uani 1 1 d . C7 C 0.1823(2) 0.51396(8) 0.60897(8) 0.0421(3) Uani 1 1 d . C6 C 0.3332(2) 0.54833(8) 0.62377(8) 0.0426(3) Uani 1 1 d . C14 C 0.4813(2) 0.67025(8) 0.63096(8) 0.0454(3) Uani 1 1 d . C26 C 0.6947(2) 0.10111(8) 0.61167(8) 0.0411(3) Uani 1 1 d . C2 C 0.1619(2) 0.44168(8) 0.61674(9) 0.0513(4) Uani 1 1 d . C10 C 0.3451(2) 0.62411(8) 0.60344(8) 0.0457(3) Uani 1 1 d . O1 O -0.0700(3) 0.36451(9) 0.58754(12) 0.1049(7) Uani 1 1 d . C22 C 0.4093(2) 0.07199(10) 0.64365(9) 0.0520(4) Uani 1 1 d . H22 H 0.2968 0.0848 0.6493 0.062 Uiso 1 1 calc R C21 C 0.5280(2) 0.12022(8) 0.61785(8) 0.0467(4) Uani 1 1 d . C33 C 1.0136(2) -0.04947(8) 0.62770(9) 0.0464(3) Uani 1 1 d . C24 C 0.6329(2) -0.01546(8) 0.65020(9) 0.0472(3) Uani 1 1 d . H24 H 0.6656 -0.0616 0.6605 0.057 Uiso 1 1 calc R C29 C 0.9277(2) 0.01613(8) 0.60379(8) 0.0445(3) Uani 1 1 d . C34 C 1.0137(2) -0.06823(9) 0.69794(9) 0.0519(4) Uani 1 1 d . H34 H 0.9515 -0.0416 0.7296 0.062 Uiso 1 1 calc R C8 C 0.0266(2) 0.55078(9) 0.58237(9) 0.0505(4) Uani 1 1 d . C15 C 0.5207(2) 0.67020(9) 0.70171(9) 0.0532(4) Uani 1 1 d . H15 H 0.4652 0.6391 0.7315 0.064 Uiso 1 1 calc R C27 C 0.8076(2) 0.16125(8) 0.58859(9) 0.0500(4) Uani 1 1 d . C30 C 1.0073(2) 0.06206(10) 0.56142(8) 0.0531(4) Uani 1 1 d . H30 H 1.1151 0.0501 0.5463 0.064 Uiso 1 1 calc R C11 C 0.2283(3) 0.64982(9) 0.55966(10) 0.0574(4) Uani 1 1 d . H11 H 0.2367 0.6972 0.5466 0.069 Uiso 1 1 calc R C5 C 0.4618(2) 0.50654(9) 0.65139(10) 0.0545(4) Uani 1 1 d . H5 H 0.5644 0.5274 0.6629 0.065 Uiso 1 1 calc R C23 C 0.4650(2) 0.00492(9) 0.66033(9) 0.0532(4) Uani 1 1 d . H23 H 0.3890 -0.0276 0.6788 0.064 Uiso 1 1 calc R C3 C 0.2910(3) 0.40031(9) 0.64426(10) 0.0620(5) Uani 1 1 d . H3 H 0.2776 0.3517 0.6504 0.074 Uiso 1 1 calc R C28 C 0.6777(3) 0.21508(10) 0.56031(11) 0.0632(5) Uani 1 1 d . H28A H 0.7070 0.2628 0.5747 0.076 Uiso 1 1 calc R H28B H 0.6740 0.2135 0.5098 0.076 Uiso 1 1 calc R C31 C 0.9346(3) 0.13154(10) 0.53671(10) 0.0607(5) Uani 1 1 d . H31A H 0.8797 0.1245 0.4921 0.073 Uiso 1 1 calc R H31B H 1.0253 0.1655 0.5302 0.073 Uiso 1 1 calc R C20 C 0.5087(3) 0.19352(9) 0.59080(10) 0.0572(4) Uani 1 1 d . C19 C 0.5688(2) 0.71689(9) 0.58765(10) 0.0567(4) Uani 1 1 d . H19 H 0.5461 0.7174 0.5401 0.068 Uiso 1 1 calc R C13 C -0.0661(3) 0.58487(12) 0.64414(12) 0.0695(5) Uani 1 1 d . H13A H -0.0965 0.5488 0.6771 0.104 Uiso 1 1 calc GR H13B H -0.1662 0.6082 0.6277 0.104 Uiso 1 1 calc GR H13C H 0.0066 0.6189 0.6661 0.104 Uiso 1 1 calc GR C12 C 0.0841(3) 0.60696(10) 0.53020(11) 0.0669(5) Uani 1 1 d . H12A H 0.1198 0.5841 0.4874 0.080 Uiso 1 1 calc R H12B H -0.0096 0.6382 0.5193 0.080 Uiso 1 1 calc R C18 C 0.6890(3) 0.76234(11) 0.61468(12) 0.0693(5) Uani 1 1 d . H18 H 0.7458 0.7934 0.5853 0.083 Uiso 1 1 calc R C38 C 1.1039(3) -0.09162(10) 0.58118(11) 0.0625(5) Uani 1 1 d . H38 H 1.1028 -0.0809 0.5339 0.075 Uiso 1 1 calc R C9 C -0.0770(3) 0.48826(10) 0.55283(11) 0.0651(5) Uani 1 1 d . H9A H -0.1956 0.4936 0.5642 0.078 Uiso 1 1 calc R H9B H -0.0652 0.4856 0.5026 0.078 Uiso 1 1 calc R C35 C 1.1056(3) -0.12633(10) 0.72112(12) 0.0646(5) Uani 1 1 d . H35 H 1.1058 -0.1381 0.7682 0.077 Uiso 1 1 calc R C36 C 1.1968(3) -0.16667(10) 0.67423(15) 0.0757(6) Uani 1 1 d . H36 H 1.2590 -0.2054 0.6896 0.091 Uiso 1 1 calc R C1 C -0.0048(3) 0.42230(10) 0.58712(11) 0.0653(5) Uani 1 1 d . C17 C 0.7248(3) 0.76191(11) 0.68447(13) 0.0720(6) Uani 1 1 d . H17 H 0.8056 0.7927 0.7024 0.086 Uiso 1 1 calc R C32 C 0.8984(3) 0.19154(10) 0.65260(12) 0.0676(5) Uani 1 1 d . H32A H 0.8165 0.2086 0.6854 0.101 Uiso 1 1 calc GR H32B H 0.9703 0.2299 0.6385 0.101 Uiso 1 1 calc GR H32C H 0.9653 0.1551 0.6739 0.101 Uiso 1 1 calc GR C16 C 0.6409(3) 0.71577(11) 0.72802(11) 0.0651(5) Uani 1 1 d . H16 H 0.6655 0.7154 0.7754 0.078 Uiso 1 1 calc R C37 C 1.1950(3) -0.14916(11) 0.60485(15) 0.0771(6) Uani 1 1 d . H37 H 1.2561 -0.1765 0.5733 0.092 Uiso 1 1 calc R C4 C 0.4392(3) 0.43383(10) 0.66210(11) 0.0654(5) Uani 1 1 d . H4 H 0.5263 0.4075 0.6817 0.078 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0790(11) 0.0693(8) 0.0887(10) 0.0086(8) -0.0047(8) 0.0294(8) C25 0.0418(8) 0.0387(7) 0.0420(7) -0.0016(6) -0.0019(6) -0.0041(6) C7 0.0469(9) 0.0381(7) 0.0412(7) -0.0033(6) 0.0015(6) 0.0010(6) C6 0.0455(8) 0.0375(7) 0.0449(7) 0.0000(6) 0.0017(6) 0.0019(6) C14 0.0482(9) 0.0376(7) 0.0504(8) 0.0020(6) 0.0001(7) 0.0005(6) C26 0.0432(8) 0.0389(7) 0.0411(7) -0.0004(6) -0.0037(6) -0.0038(6) C2 0.0627(10) 0.0394(8) 0.0518(9) -0.0033(7) 0.0045(8) -0.0038(7) C10 0.0527(9) 0.0384(7) 0.0459(8) 0.0021(6) -0.0017(7) -0.0024(6) O1 0.1131(16) 0.0615(9) 0.1403(17) 0.0058(10) -0.0278(13) -0.0400(10) C22 0.0382(8) 0.0599(9) 0.0579(9) -0.0069(8) -0.0016(7) 0.0006(7) C21 0.0478(9) 0.0449(8) 0.0473(8) -0.0046(6) -0.0060(7) 0.0027(6) C33 0.0399(8) 0.0415(7) 0.0578(9) -0.0048(6) 0.0005(6) -0.0038(6) C24 0.0472(9) 0.0388(7) 0.0557(8) 0.0007(6) -0.0002(7) -0.0050(6) C29 0.0416(8) 0.0454(7) 0.0466(7) -0.0027(6) -0.0006(6) -0.0010(6) C34 0.0493(9) 0.0448(8) 0.0617(9) 0.0008(7) 0.0006(7) -0.0010(7) C8 0.0478(9) 0.0461(8) 0.0577(9) -0.0025(7) -0.0114(7) 0.0005(7) C15 0.0558(10) 0.0512(9) 0.0527(9) 0.0041(7) -0.0013(7) -0.0078(7) C27 0.0529(10) 0.0405(7) 0.0567(9) 0.0100(7) -0.0047(7) -0.0065(7) C30 0.0462(9) 0.0622(10) 0.0509(8) 0.0043(8) 0.0064(7) -0.0032(7) C11 0.0729(12) 0.0408(8) 0.0587(9) 0.0091(7) -0.0169(9) -0.0065(8) C5 0.0474(9) 0.0504(9) 0.0657(10) 0.0014(8) -0.0035(8) 0.0067(7) C23 0.0454(9) 0.0534(9) 0.0608(10) 0.0001(7) 0.0019(7) -0.0127(7) C3 0.0818(13) 0.0351(8) 0.0691(11) 0.0024(8) 0.0011(10) 0.0040(8) C28 0.0700(13) 0.0462(9) 0.0734(12) 0.0153(8) -0.0080(10) -0.0005(8) C31 0.0580(11) 0.0658(11) 0.0584(10) 0.0202(8) 0.0053(8) -0.0063(9) C20 0.0650(11) 0.0490(8) 0.0576(10) 0.0003(8) -0.0102(8) 0.0109(8) C19 0.0638(11) 0.0492(9) 0.0571(9) 0.0074(8) -0.0004(8) -0.0071(8) C13 0.0487(11) 0.0698(11) 0.0899(14) -0.0155(11) -0.0038(10) 0.0124(9) C12 0.0805(14) 0.0535(9) 0.0667(11) 0.0110(9) -0.0311(10) -0.0076(9) C18 0.0724(13) 0.0545(10) 0.0809(13) 0.0112(10) 0.0036(11) -0.0201(9) C38 0.0625(12) 0.0526(9) 0.0725(12) -0.0123(8) 0.0115(9) 0.0016(8) C9 0.0618(12) 0.0625(11) 0.0709(12) -0.0060(9) -0.0170(9) -0.0125(9) C35 0.0593(11) 0.0522(9) 0.0822(13) 0.0155(9) -0.0067(9) -0.0022(8) C36 0.0618(12) 0.0430(9) 0.122(2) 0.0090(11) -0.0011(12) 0.0076(8) C1 0.0736(13) 0.0512(9) 0.0710(11) -0.0068(9) -0.0010(10) -0.0184(9) C17 0.0693(14) 0.0569(10) 0.0898(14) -0.0045(10) -0.0116(11) -0.0199(10) C32 0.0762(13) 0.0486(9) 0.0779(13) 0.0022(9) -0.0157(10) -0.0187(9) C16 0.0710(13) 0.0634(11) 0.0610(10) -0.0058(9) -0.0105(9) -0.0099(9) C37 0.0698(14) 0.0479(9) 0.1136(18) -0.0138(11) 0.0192(13) 0.0078(9) C4 0.0708(13) 0.0479(9) 0.0775(12) 0.0061(9) -0.0094(10) 0.0183(9) 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 C26 C25 C24 116.18(14) C26 C25 C29 116.90(14) C24 C25 C29 126.60(14) C6 C7 C8 124.02(13) C2 C7 C6 122.64(16) C2 C7 C8 113.34(15) C7 C6 C10 116.74(14) C7 C6 C5 116.30(14) C5 C6 C10 126.78(15) C15 C14 C10 120.64(14) C15 C14 C19 118.04(16) C19 C14 C10 121.27(15) C25 C26 C27 123.71(14) C21 C26 C25 122.87(14) C21 C26 C27 113.41(14) C7 C2 C3 120.60(17) C7 C2 C1 107.82(16) C3 C2 C1 131.45(16) C14 C10 C6 121.14(14) C11 C10 C6 117.99(15) C11 C10 C14 120.87(14) C21 C22 H22 121.2 C23 C22 H22 121.2 C23 C22 C21 117.66(16) C26 C21 C22 120.40(15) C26 C21 C20 108.24(15) C22 C21 C20 131.31(16) C34 C33 C29 120.70(15) C38 C33 C29 120.83(16) C38 C33 C34 118.37(16) C25 C24 H24 119.5 C25 C24 C23 121.01(15) C23 C24 H24 119.5 C25 C29 C33 121.36(14) C30 C29 C25 118.05(15) C30 C29 C33 120.58(15) C33 C34 H34 119.7 C35 C34 C33 120.68(18) C35 C34 H34 119.7 C7 C8 C13 108.83(14) C7 C8 C12 107.34(16) C7 C8 C9 102.00(13) C13 C8 C9 110.44(17) C12 C8 C13 111.00(16) C12 C8 C9 116.57(15) C14 C15 H15 119.6 C16 C15 C14 120.75(17) C16 C15 H15 119.6 C26 C27 C28 101.66(14) C26 C27 C31 107.87(13) C26 C27 C32 108.78(14) C31 C27 C28 116.89(16) C31 C27 C32 110.57(17) C32 C27 C28 110.44(16) C29 C30 H30 117.6 C29 C30 C31 124.83(16) C31 C30 H30 117.6 C10 C11 H11 117.8 C10 C11 C12 124.30(15) C12 C11 H11 117.8 C6 C5 H5 119.4 C6 C5 C4 121.18(18) C4 C5 H5 119.4 C22 C23 C24 121.65(16) C22 C23 H23 119.2 C24 C23 H23 119.2 C2 C3 H3 121.2 C4 C3 C2 117.64(15) C4 C3 H3 121.2 C27 C28 H28A 110.5 C27 C28 H28B 110.5 H28A C28 H28B 108.7 C20 C28 C27 106.04(14) C20 C28 H28A 110.5 C20 C28 H28B 110.5 C27 C31 H31A 109.3 C27 C31 H31B 109.3 C30 C31 C27 111.48(14) C30 C31 H31A 109.3 C30 C31 H31B 109.3 H31A C31 H31B 108.0 O2 C20 C21 126.3(2) O2 C20 C28 126.55(17) C21 C20 C28 107.09(15) C14 C19 H19 119.7 C18 C19 C14 120.64(18) C18 C19 H19 119.7 C8 C13 H13A 109.5 C8 C13 H13B 109.5 C8 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C8 C12 H12A 109.5 C8 C12 H12B 109.5 C11 C12 C8 110.58(14) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 108.1 C19 C18 H18 119.8 C17 C18 C19 120.42(19) C17 C18 H18 119.8 C33 C38 H38 119.8 C37 C38 C33 120.4(2) C37 C38 H38 119.8 C8 C9 H9A 110.7 C8 C9 H9B 110.7 H9A C9 H9B 108.8 C1 C9 C8 105.43(15) C1 C9 H9A 110.7 C1 C9 H9B 110.7 C34 C35 H35 120.0 C36 C35 C34 120.0(2) C36 C35 H35 120.0 C35 C36 H36 120.2 C37 C36 C35 119.62(19) C37 C36 H36 120.2 C2 C1 C9 107.43(15) O1 C1 C2 126.9(2) O1 C1 C9 125.6(2) C18 C17 H17 120.1 C18 C17 C16 119.84(19) C16 C17 H17 120.1 C27 C32 H32A 109.5 C27 C32 H32B 109.5 C27 C32 H32C 109.5 H32A C32 H32B 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 C15 C16 H16 119.8 C17 C16 C15 120.30(19) C17 C16 H16 119.8 C38 C37 H37 119.5 C36 C37 C38 120.9(2) C36 C37 H37 119.5 C5 C4 H4 119.2 C3 C4 C5 121.51(17) C3 C4 H4 119.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C20 1.219(2) C25 C26 1.395(2) C25 C24 1.398(2) C25 C29 1.479(2) C7 C6 1.389(2) C7 C2 1.381(2) C7 C8 1.505(2) C6 C10 1.485(2) C6 C5 1.393(2) C14 C10 1.483(2) C14 C15 1.394(2) C14 C19 1.395(2) C26 C21 1.374(2) C26 C27 1.511(2) C2 C3 1.390(3) C2 C1 1.484(3) C10 C11 1.341(2) O1 C1 1.206(2) C22 H22 0.9300 C22 C21 1.399(2) C22 C23 1.377(3) C21 C20 1.485(2) C33 C29 1.485(2) C33 C34 1.394(2) C33 C38 1.393(2) C24 H24 0.9300 C24 C23 1.398(3) C29 C30 1.345(2) C34 H34 0.9300 C34 C35 1.389(2) C8 C13 1.536(3) C8 C12 1.528(3) C8 C9 1.545(2) C15 H15 0.9300 C15 C16 1.379(3) C27 C28 1.544(2) C27 C31 1.523(3) C27 C32 1.534(3) C30 H30 0.9300 C30 C31 1.508(3) C11 H11 0.9300 C11 C12 1.509(3) C5 H5 0.9300 C5 C4 1.398(3) C23 H23 0.9300 C3 H3 0.9300 C3 C4 1.377(3) C28 H28A 0.9700 C28 H28B 0.9700 C28 C20 1.516(3) C31 H31A 0.9700 C31 H31B 0.9700 C19 H19 0.9300 C19 C18 1.382(3) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C12 H12A 0.9700 C12 H12B 0.9700 C18 H18 0.9300 C18 C17 1.370(3) C38 H38 0.9300 C38 C37 1.380(3) C9 H9A 0.9700 C9 H9B 0.9700 C9 C1 1.519(3) C35 H35 0.9300 C35 C36 1.383(3) C36 H36 0.9300 C36 C37 1.373(4) C17 H17 0.9300 C17 C16 1.378(3) C32 H32A 0.9600 C32 H32B 0.9600 C32 H32C 0.9600 C16 H16 0.9300 C37 H37 0.9300 C4 H4 0.9300