#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:31:20 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270481 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060998.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_7060998 loop_ _publ_author_name 'Xu, Feng-Shun' 'Yan, Chen' 'Sun, Jing' 'Yan, Chao-Guo' _publ_section_title ; Efficient synthesis of tetra- and penta-substituted benzenes via a domino annulation reaction of a pyridinium ylide and chalcone o-enolate ; _journal_issue 42 _journal_name_full 'New Journal of Chemistry' _journal_page_first 19666 _journal_page_last 19670 _journal_paper_doi 10.1039/D1NJ03772B _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C29 H24 O5' _chemical_formula_sum 'C29 H24 O5' _chemical_formula_weight 452.48 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-07-26 deposited with the CCDC. 2021-09-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.595(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.937(5) _cell_length_b 11.056(3) _cell_length_c 15.432(4) _cell_measurement_reflns_used 4914 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.73 _cell_measurement_theta_min 2.27 _cell_volume 2370.2(12) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_unetI/netI 0.0656 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 21664 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 2.354 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_description block _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.201 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 4644 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.1317 _refine_ls_R_factor_gt 0.0550 _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^)+(0.0565P)^2^+0.4804P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1106 _refine_ls_wR_factor_ref 0.1371 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2505 _reflns_number_total 4644 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03772b2.cif _cod_data_source_block 3a _cod_depositor_comments 'Adding full bibliography for 7060998--7060999.cif.' _cod_original_cell_volume 2370.3(12) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060998 _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. ; _shelx_estimated_absorpt_t_min 0.976 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; XFS20210102.res created by SHELXL-2014/7 TITL XFS20210102 in P2(1)/n CELL 0.71073 13.93690 11.05600 15.43230 90.0000 94.5953 90.0000 ZERR 4.00 0.00450 0.00300 0.00440 0.0000 0.0097 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O UNIT 116 96 20 OMIT -3 52 OMIT 0 1 1 OMIT 3 12 4 OMIT 0 1 1 OMIT 1 0 1 L.S. 20 ACTA HTAB O1 O2 BOND $H SIZE 0.28 0.22 0.18 FMAP 2 PLAN 20 TEMP 23 WGHT 0.056500 0.480400 FVAR 0.17601 MOLE 1 C1 1 0.283920 0.426711 -0.158520 11.00000 0.08312 0.08460 = 0.06807 0.01818 0.03865 0.02248 C2 1 0.267336 0.372687 -0.239181 11.00000 0.14572 0.11220 = 0.06354 0.01628 0.05455 0.04527 AFIX 43 H2 2 0.307707 0.389622 -0.282776 11.00000 -1.20000 AFIX 0 C3 1 0.192647 0.295258 -0.255066 11.00000 0.16447 0.09779 = 0.04858 -0.00563 0.01365 0.05442 AFIX 43 H3 2 0.183316 0.258137 -0.309162 11.00000 -1.20000 AFIX 0 C4 1 0.130311 0.270579 -0.192488 11.00000 0.11920 0.07022 = 0.05557 -0.00639 -0.00226 0.01484 AFIX 43 H4 2 0.078331 0.218834 -0.204488 11.00000 -1.20000 AFIX 0 C5 1 0.146052 0.323555 -0.112026 11.00000 0.07938 0.06204 = 0.04634 0.00312 0.01120 0.01004 AFIX 43 H5 2 0.104373 0.306680 -0.069459 11.00000 -1.20000 AFIX 0 C6 1 0.222965 0.401857 -0.092881 11.00000 0.05787 0.05878 = 0.04655 0.00808 0.02015 0.01332 C7 1 0.240656 0.459255 -0.008041 11.00000 0.04896 0.05988 = 0.05626 0.00792 0.01561 -0.00255 C8 1 0.179366 0.432552 0.064733 11.00000 0.04293 0.05446 = 0.04067 -0.00002 0.00736 -0.00614 C9 1 0.126182 0.524516 0.101699 11.00000 0.04096 0.05022 = 0.04187 -0.00214 0.00144 -0.00660 C10 1 0.121004 0.648477 0.063978 11.00000 0.04249 0.05117 = 0.04261 -0.00037 0.00597 -0.00554 C11 1 0.145986 0.748303 0.115228 11.00000 0.05922 0.05466 = 0.05055 -0.00437 0.00457 -0.00005 AFIX 43 H11 2 0.162674 0.738310 0.174355 11.00000 -1.20000 AFIX 0 C12 1 0.146249 0.862905 0.078908 11.00000 0.06825 0.05112 = 0.06781 -0.00856 0.01210 -0.00443 AFIX 43 H12 2 0.164220 0.928603 0.114188 11.00000 -1.20000 AFIX 0 C13 1 0.120444 0.882234 -0.008604 11.00000 0.05051 0.05679 = 0.06318 0.00742 0.01960 0.00134 C14 1 0.121451 1.008279 -0.046059 11.00000 0.09583 0.06271 = 0.09667 0.01952 0.03465 0.00386 AFIX 137 H14A 2 0.094459 1.006752 -0.105267 11.00000 -1.50000 H14B 2 0.186534 1.037219 -0.044081 11.00000 -1.50000 H14C 2 0.084002 1.061046 -0.012655 11.00000 -1.50000 AFIX 0 C15 1 0.092501 0.782999 -0.058554 11.00000 0.05692 0.06827 = 0.05027 0.01191 0.00494 -0.00480 AFIX 43 H15 2 0.072619 0.793769 -0.117017 11.00000 -1.20000 AFIX 0 C16 1 0.093412 0.667586 -0.023508 11.00000 0.05895 0.05917 = 0.04645 -0.00244 0.00280 -0.01269 AFIX 43 H16 2 0.075339 0.602095 -0.058957 11.00000 -1.20000 AFIX 0 C17 1 0.183619 0.319475 0.102788 11.00000 0.04550 0.05367 = 0.04534 -0.00722 0.01003 -0.00020 AFIX 43 H17 2 0.218863 0.258958 0.078036 11.00000 -1.20000 AFIX 0 C18 1 0.136922 0.292916 0.177001 11.00000 0.04068 0.04959 = 0.03839 -0.00138 0.00455 -0.00353 C19 1 0.149216 0.167710 0.211463 11.00000 0.04704 0.05850 = 0.03547 -0.00364 0.00690 0.00084 C20 1 0.078067 0.007737 0.285512 11.00000 0.08521 0.06755 = 0.07232 0.02424 0.02457 0.00150 AFIX 137 H20A 2 0.097574 -0.053579 0.246530 11.00000 -1.50000 H20B 2 0.017091 -0.013818 0.305966 11.00000 -1.50000 H20C 2 0.125341 0.014573 0.334041 11.00000 -1.50000 AFIX 0 C21 1 0.079996 0.496879 0.175568 11.00000 0.04538 0.05095 = 0.04063 -0.00559 0.00750 -0.00061 AFIX 43 H21 2 0.044788 0.557499 0.200242 11.00000 -1.20000 AFIX 0 C22 1 0.083443 0.383714 0.214683 11.00000 0.03922 0.05267 = 0.03743 -0.00182 0.00414 -0.00322 C23 1 0.033164 0.366401 0.295506 11.00000 0.04462 0.04947 = 0.03790 -0.00220 0.00738 -0.00134 C24 1 0.081216 0.328017 0.371937 11.00000 0.04483 0.10207 = 0.04816 0.00471 0.00716 0.00722 AFIX 43 H24 2 0.146386 0.309612 0.372641 11.00000 -1.20000 AFIX 0 C25 1 0.035371 0.315982 0.447873 11.00000 0.06143 0.10709 = 0.03912 0.01097 0.00630 0.00361 AFIX 43 H25 2 0.069557 0.290110 0.498732 11.00000 -1.20000 AFIX 0 C26 1 -0.060825 0.342506 0.447506 11.00000 0.05382 0.07236 = 0.04308 -0.00610 0.01629 -0.00877 C27 1 -0.063613 0.310971 0.600227 11.00000 0.09349 0.14743 = 0.04524 -0.00148 0.01900 -0.02729 AFIX 137 H27A 2 -0.035966 0.231416 0.600827 11.00000 -1.50000 H27B 2 -0.107310 0.316938 0.645067 11.00000 -1.50000 H27C 2 -0.013371 0.369908 0.610292 11.00000 -1.50000 AFIX 0 C28 1 -0.110092 0.381032 0.371698 11.00000 0.04572 0.08740 = 0.05532 0.00084 0.01405 0.00548 AFIX 43 H28 2 -0.175411 0.398644 0.370850 11.00000 -1.20000 AFIX 0 C29 1 -0.063111 0.393601 0.297153 11.00000 0.04901 0.07485 = 0.04388 0.00469 0.00792 0.00741 AFIX 43 H29 2 -0.097152 0.421109 0.246688 11.00000 -1.20000 AFIX 0 O1 3 0.358878 0.504047 -0.145039 11.00000 0.09585 0.13608 = 0.10920 0.02588 0.06332 -0.00748 AFIX 147 H1 2 0.363362 0.526041 -0.094130 11.00000 -1.50000 AFIX 0 O2 3 0.307744 0.531955 0.006792 11.00000 0.06760 0.10028 = 0.08249 0.00017 0.02301 -0.03004 O3 3 0.222817 0.111367 0.211093 11.00000 0.05866 0.06191 = 0.07676 0.00586 0.01778 0.01105 O4 3 0.069315 0.122371 0.240284 11.00000 0.05553 0.06051 = 0.06967 0.01658 0.01752 0.00017 O5 3 -0.114020 0.332567 0.518403 11.00000 0.06693 0.12886 = 0.04645 0.00096 0.02190 -0.01077 HKLF 4 REM XFS20210102 in P2(1)/n REM R1 = 0.0550 for 2505 Fo > 4sig(Fo) and 0.1317 for all 4644 data REM 311 parameters refined using 0 restraints END WGHT 0.0562 0.4836 REM Highest difference peak 0.201, deepest hole -0.184, 1-sigma level 0.039 Q1 1 0.1768 1.0164 -0.0986 11.00000 0.05 0.20 Q2 1 0.1547 -0.0346 0.2802 11.00000 0.05 0.18 Q3 1 0.0441 1.0343 -0.0655 11.00000 0.05 0.14 Q4 1 0.0166 -0.0602 0.2474 11.00000 0.05 0.13 Q5 1 0.1812 1.0656 0.0061 11.00000 0.05 0.13 Q6 1 -0.1017 0.2441 0.6517 11.00000 0.05 0.13 Q7 1 0.2020 0.6921 0.2031 11.00000 0.05 0.13 Q8 1 0.1179 -0.1769 0.2427 11.00000 0.05 0.12 Q9 1 -0.1241 0.3663 0.2244 11.00000 0.05 0.12 Q10 1 0.0445 0.0376 0.3465 11.00000 0.05 0.12 Q11 1 0.1281 0.4646 0.0612 11.00000 0.05 0.12 Q12 1 -0.2817 0.4158 0.3075 11.00000 0.05 0.11 Q13 1 0.0783 0.0538 0.3740 11.00000 0.05 0.11 Q14 1 0.1816 0.1265 0.1694 11.00000 0.05 0.11 Q15 1 0.0203 0.5198 -0.0318 11.00000 0.05 0.11 Q16 1 0.2233 0.2660 -0.0559 11.00000 0.05 0.11 Q17 1 0.2199 0.0136 0.2817 11.00000 0.05 0.11 Q18 1 0.2756 0.2931 -0.3777 11.00000 0.05 0.11 Q19 1 0.0603 0.4660 0.0198 11.00000 0.05 0.11 Q20 1 0.0352 0.0355 0.4467 11.00000 0.05 0.11 ; _shelx_res_checksum 37076 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2839(2) 0.4267(3) -0.15852(19) 0.0768(9) Uani 1 1 d . . . . . C2 C 0.2673(3) 0.3727(4) -0.2392(2) 0.1047(13) Uani 1 1 d . . . . . H2 H 0.3077 0.3896 -0.2828 0.126 Uiso 1 1 calc R U . . . C3 C 0.1926(3) 0.2953(3) -0.2551(2) 0.1033(12) Uani 1 1 d . . . . . H3 H 0.1833 0.2581 -0.3092 0.124 Uiso 1 1 calc R U . . . C4 C 0.1303(2) 0.2706(3) -0.19249(18) 0.0822(9) Uani 1 1 d . . . . . H4 H 0.0783 0.2188 -0.2045 0.099 Uiso 1 1 calc R U . . . C5 C 0.1461(2) 0.3236(2) -0.11203(16) 0.0623(7) Uani 1 1 d . . . . . H5 H 0.1044 0.3067 -0.0695 0.075 Uiso 1 1 calc R U . . . C6 C 0.22296(18) 0.4019(2) -0.09288(15) 0.0535(6) Uani 1 1 d . . . . . C7 C 0.24066(18) 0.4593(2) -0.00804(15) 0.0544(6) Uani 1 1 d . . . . . C8 C 0.17937(15) 0.4326(2) 0.06473(14) 0.0458(6) Uani 1 1 d . . . . . C9 C 0.12618(15) 0.52452(19) 0.10170(14) 0.0445(6) Uani 1 1 d . . . . . C10 C 0.12100(15) 0.64848(19) 0.06398(14) 0.0453(6) Uani 1 1 d . . . . . C11 C 0.14599(17) 0.7483(2) 0.11523(16) 0.0548(6) Uani 1 1 d . . . . . H11 H 0.1627 0.7383 0.1744 0.066 Uiso 1 1 calc R U . . . C12 C 0.14625(18) 0.8629(2) 0.07891(18) 0.0620(7) Uani 1 1 d . . . . . H12 H 0.1642 0.9286 0.1142 0.074 Uiso 1 1 calc R U . . . C13 C 0.12044(17) 0.8822(2) -0.00860(17) 0.0560(7) Uani 1 1 d . . . . . C14 C 0.1215(2) 1.0083(2) -0.04606(19) 0.0836(9) Uani 1 1 d . . . . . H14A H 0.0945 1.0068 -0.1053 0.125 Uiso 1 1 calc R U . . . H14B H 0.1865 1.0372 -0.0441 0.125 Uiso 1 1 calc R U . . . H14C H 0.0840 1.0610 -0.0127 0.125 Uiso 1 1 calc R U . . . C15 C 0.09250(17) 0.7830(2) -0.05855(16) 0.0585(7) Uani 1 1 d . . . . . H15 H 0.0726 0.7938 -0.1170 0.070 Uiso 1 1 calc R U . . . C16 C 0.09341(17) 0.6676(2) -0.02351(15) 0.0549(6) Uani 1 1 d . . . . . H16 H 0.0753 0.6021 -0.0590 0.066 Uiso 1 1 calc R U . . . C17 C 0.18362(15) 0.3195(2) 0.10279(14) 0.0478(6) Uani 1 1 d . . . . . H17 H 0.2189 0.2590 0.0780 0.057 Uiso 1 1 calc R U . . . C18 C 0.13692(15) 0.29292(19) 0.17700(13) 0.0428(5) Uani 1 1 d . . . . . C19 C 0.14922(17) 0.1677(2) 0.21146(13) 0.0468(6) Uani 1 1 d . . . . . C20 C 0.0781(2) 0.0077(2) 0.28551(18) 0.0740(8) Uani 1 1 d . . . . . H20A H 0.0976 -0.0536 0.2465 0.111 Uiso 1 1 calc R U . . . H20B H 0.0171 -0.0138 0.3060 0.111 Uiso 1 1 calc R U . . . H20C H 0.1253 0.0146 0.3340 0.111 Uiso 1 1 calc R U . . . C21 C 0.08000(15) 0.49688(19) 0.17557(13) 0.0454(6) Uani 1 1 d . . . . . H21 H 0.0448 0.5575 0.2002 0.055 Uiso 1 1 calc R U . . . C22 C 0.08344(15) 0.38371(19) 0.21468(13) 0.0430(5) Uani 1 1 d . . . . . C23 C 0.03316(15) 0.36640(19) 0.29551(14) 0.0438(5) Uani 1 1 d . . . . . C24 C 0.08122(18) 0.3280(2) 0.37194(16) 0.0648(7) Uani 1 1 d . . . . . H24 H 0.1464 0.3096 0.3726 0.078 Uiso 1 1 calc R U . . . C25 C 0.03537(19) 0.3160(3) 0.44787(15) 0.0691(8) Uani 1 1 d . . . . . H25 H 0.0696 0.2901 0.4987 0.083 Uiso 1 1 calc R U . . . C26 C -0.06083(17) 0.3425(2) 0.44751(15) 0.0558(6) Uani 1 1 d . . . . . C27 C -0.0636(2) 0.3110(3) 0.60023(17) 0.0947(10) Uani 1 1 d . . . . . H27A H -0.0360 0.2314 0.6008 0.142 Uiso 1 1 calc R U . . . H27B H -0.1073 0.3169 0.6451 0.142 Uiso 1 1 calc R U . . . H27C H -0.0134 0.3699 0.6103 0.142 Uiso 1 1 calc R U . . . C28 C -0.11009(18) 0.3810(2) 0.37170(16) 0.0623(7) Uani 1 1 d . . . . . H28 H -0.1754 0.3986 0.3709 0.075 Uiso 1 1 calc R U . . . C29 C -0.06311(17) 0.3936(2) 0.29715(15) 0.0557(6) Uani 1 1 d . . . . . H29 H -0.0972 0.4211 0.2467 0.067 Uiso 1 1 calc R U . . . O1 O 0.35888(18) 0.5040(2) -0.14504(15) 0.1107(8) Uani 1 1 d . . . . . H1 H 0.3634 0.5260 -0.0941 0.166 Uiso 1 1 calc R U . . . O2 O 0.30774(14) 0.53196(18) 0.00679(12) 0.0825(6) Uani 1 1 d . . . . . O3 O 0.22282(13) 0.11137(14) 0.21109(11) 0.0651(5) Uani 1 1 d . . . . . O4 O 0.06931(11) 0.12237(14) 0.24028(11) 0.0612(5) Uani 1 1 d . . . . . O5 O -0.11402(13) 0.33257(18) 0.51840(11) 0.0798(6) 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 0.083(2) 0.085(2) 0.068(2) 0.0182(17) 0.0386(17) 0.0225(17) C2 0.146(4) 0.112(3) 0.064(2) 0.016(2) 0.055(2) 0.045(3) C3 0.164(4) 0.098(3) 0.049(2) -0.0056(19) 0.014(2) 0.054(3) C4 0.119(3) 0.0702(19) 0.0556(19) -0.0064(16) -0.0023(18) 0.0148(17) C5 0.079(2) 0.0620(16) 0.0463(16) 0.0031(13) 0.0112(13) 0.0100(14) C6 0.0579(16) 0.0588(15) 0.0465(15) 0.0081(12) 0.0201(12) 0.0133(12) C7 0.0490(15) 0.0599(15) 0.0563(16) 0.0079(13) 0.0156(12) -0.0026(12) C8 0.0429(13) 0.0545(14) 0.0407(13) 0.0000(11) 0.0074(10) -0.0061(11) C9 0.0410(13) 0.0502(14) 0.0419(13) -0.0021(11) 0.0014(10) -0.0066(10) C10 0.0425(13) 0.0512(14) 0.0426(14) -0.0004(12) 0.0060(10) -0.0055(11) C11 0.0592(16) 0.0547(16) 0.0505(15) -0.0044(13) 0.0046(12) -0.0001(12) C12 0.0683(18) 0.0511(16) 0.0678(19) -0.0086(14) 0.0121(14) -0.0044(12) C13 0.0505(15) 0.0568(16) 0.0632(17) 0.0074(14) 0.0196(13) 0.0013(12) C14 0.096(2) 0.0627(18) 0.097(2) 0.0195(16) 0.0346(18) 0.0039(15) C15 0.0569(16) 0.0683(17) 0.0503(15) 0.0119(14) 0.0049(12) -0.0048(13) C16 0.0590(16) 0.0592(16) 0.0464(15) -0.0024(13) 0.0028(12) -0.0127(12) C17 0.0455(14) 0.0537(15) 0.0453(13) -0.0072(12) 0.0100(11) -0.0002(11) C18 0.0407(13) 0.0496(13) 0.0384(13) -0.0014(11) 0.0046(10) -0.0035(10) C19 0.0470(15) 0.0585(15) 0.0355(13) -0.0036(11) 0.0069(11) 0.0008(12) C20 0.085(2) 0.0675(18) 0.0723(18) 0.0242(15) 0.0246(16) 0.0015(14) C21 0.0454(13) 0.0509(14) 0.0406(13) -0.0056(11) 0.0075(11) -0.0006(10) C22 0.0392(13) 0.0527(14) 0.0374(12) -0.0018(11) 0.0041(10) -0.0032(10) C23 0.0446(14) 0.0495(13) 0.0379(13) -0.0022(11) 0.0074(11) -0.0013(10) C24 0.0448(14) 0.102(2) 0.0482(15) 0.0047(14) 0.0072(12) 0.0072(14) C25 0.0614(18) 0.107(2) 0.0391(14) 0.0110(14) 0.0063(12) 0.0036(15) C26 0.0538(16) 0.0724(16) 0.0431(15) -0.0061(13) 0.0163(13) -0.0088(13) C27 0.093(2) 0.147(3) 0.0452(18) -0.0015(18) 0.0190(16) -0.027(2) C28 0.0457(15) 0.0874(18) 0.0553(17) 0.0008(14) 0.0140(13) 0.0055(13) C29 0.0490(15) 0.0748(16) 0.0439(14) 0.0047(12) 0.0079(11) 0.0074(12) O1 0.0959(17) 0.136(2) 0.1092(18) 0.0259(16) 0.0633(15) -0.0075(15) O2 0.0676(13) 0.1003(14) 0.0825(14) 0.0002(11) 0.0230(10) -0.0300(11) O3 0.0587(11) 0.0619(10) 0.0768(12) 0.0059(9) 0.0178(9) 0.0110(9) O4 0.0555(11) 0.0605(10) 0.0697(11) 0.0166(9) 0.0175(9) 0.0002(8) O5 0.0669(12) 0.1289(17) 0.0464(11) 0.0010(10) 0.0219(9) -0.0108(11) 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' O O 0.0106 0.0060 '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 118.8(3) . . ? O1 C1 C6 121.2(3) . . ? C2 C1 C6 119.9(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.1(3) . . ? C5 C6 C7 122.2(2) . . ? C1 C6 C7 119.7(3) . . ? O2 C7 C6 121.2(2) . . ? O2 C7 C8 117.2(2) . . ? C6 C7 C8 121.6(2) . . ? C17 C8 C9 119.24(19) . . ? C17 C8 C7 119.4(2) . . ? C9 C8 C7 120.9(2) . . ? C21 C9 C8 117.9(2) . . ? C21 C9 C10 120.86(19) . . ? C8 C9 C10 121.19(18) . . ? C11 C10 C16 118.1(2) . . ? C11 C10 C9 120.5(2) . . ? C16 C10 C9 121.4(2) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.8(2) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C15 C13 C12 117.5(2) . . ? C15 C13 C14 122.1(2) . . ? C12 C13 C14 120.4(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 C16 121.4(2) . . ? C13 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C10 120.8(2) . . ? C15 C16 H16 119.6 . . ? C10 C16 H16 119.6 . . ? C8 C17 C18 122.3(2) . . ? C8 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C17 C18 C22 119.2(2) . . ? C17 C18 C19 116.23(19) . . ? C22 C18 C19 124.54(18) . . ? O3 C19 O4 123.0(2) . . ? O3 C19 C18 123.7(2) . . ? O4 C19 C18 113.2(2) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C21 C22 123.6(2) . . ? C9 C21 H21 118.2 . . ? C22 C21 H21 118.2 . . ? C21 C22 C18 117.73(18) . . ? C21 C22 C23 118.50(18) . . ? C18 C22 C23 123.74(19) . . ? C24 C23 C29 117.4(2) . . ? C24 C23 C22 121.8(2) . . ? C29 C23 C22 120.7(2) . . ? C23 C24 C25 121.9(2) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C26 C25 C24 119.5(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 O5 124.7(2) . . ? C25 C26 C28 119.4(2) . . ? O5 C26 C28 115.9(2) . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C26 120.3(2) . . ? C29 C28 H28 119.9 . . ? C26 C28 H28 119.9 . . ? C28 C29 C23 121.5(2) . . ? C28 C29 H29 119.2 . . ? C23 C29 H29 119.2 . . ? C1 O1 H1 109.5 . . ? C19 O4 C20 116.80(19) . . ? C26 O5 C27 117.6(2) . . ? 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 O1 1.353(4) . ? C1 C2 1.383(5) . ? C1 C6 1.400(3) . ? C2 C3 1.355(5) . ? C2 H2 0.9300 . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C5 1.375(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(4) . ? C5 H5 0.9300 . ? C6 C7 1.458(3) . ? C7 O2 1.240(3) . ? C7 C8 1.494(3) . ? C8 C17 1.380(3) . ? C8 C9 1.406(3) . ? C9 C21 1.387(3) . ? C9 C10 1.489(3) . ? C10 C11 1.386(3) . ? C10 C16 1.390(3) . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C12 H12 0.9300 . ? C13 C15 1.379(3) . ? C13 C14 1.509(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.393(3) . ? C17 H17 0.9300 . ? C18 C22 1.404(3) . ? C18 C19 1.488(3) . ? C19 O3 1.201(3) . ? C19 O4 1.330(3) . ? C20 O4 1.447(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.388(3) . ? C21 H21 0.9300 . ? C22 C23 1.491(3) . ? C23 C24 1.376(3) . ? C23 C29 1.377(3) . ? C24 C25 1.385(3) . ? C24 H24 0.9300 . ? C25 C26 1.372(3) . ? C25 H25 0.9300 . ? C26 O5 1.374(3) . ? C26 C28 1.376(3) . ? C27 O5 1.415(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.376(3) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O1 H1 0.8200 . ? 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 H1 O2 0.82 1.80 2.522(3) 146.8 .