#------------------------------------------------------------------------------ #$Date: 2020-04-24 03:51:16 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157481.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_7157481 loop_ _publ_author_name 'Roy, Biswajit' 'Das, Eshani' 'Roy, Avijit' 'Mal, Dipak Ranjan' _publ_section_title ; Ni(II)-catalyzed vinylic C-H functionalization of 2-acetamido-3-arylacrylates to access isotetronic acids ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00557F _journal_year 2020 _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-10-08 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.23(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.570(2) _cell_length_b 9.753(2) _cell_length_c 13.656(3) _cell_measurement_reflns_used 1174 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.3 _cell_measurement_theta_min 1.7 _cell_volume 985.3(4) _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 ( Bruker, 2003)' _computing_molecular_graphics 'Diamond 2.1e' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution SIR-97 _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_unetI/netI 0.0910 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12210 _diffrn_reflns_point_group_measured_fraction_full 0.917 _diffrn_reflns_point_group_measured_fraction_max 0.892 _diffrn_reflns_theta_full 25.500 _diffrn_reflns_theta_max 26.390 _diffrn_reflns_theta_min 1.526 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_correction_T_min 0.9887 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.174 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details ; Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.1(10) _refine_ls_extinction_coef 0.026(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 3610 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.951 _refine_ls_R_factor_all 0.1115 _refine_ls_R_factor_gt 0.0552 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1277 _refine_ls_wR_factor_ref 0.1542 _reflns_Friedel_coverage 0.700 _reflns_Friedel_fraction_full 0.825 _reflns_Friedel_fraction_max 0.782 _reflns_number_gt 1975 _reflns_number_total 3610 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00557f2.cif _cod_data_source_block 9k _cod_original_cell_volume 985.4(4) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7157481 _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_res_file ; shelx.res created by SHELXL-2014/7 TITL dm_br_ME_a.res in P2(1) CELL 0.71073 7.5704 9.7532 13.6555 90.000 102.226 90.000 ZERR 4.00 0.0020 0.0020 0.0030 0.030 0.030 0.030 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 44 40 0 12 MERG 2 DFIX 0.89 0.01 O5 H5A FMAP 2 PLAN 3 ACTA 51.00 BOND $H LIST 6 L.S. 1 WGHT 0.065200 EXTI 0.025539 FVAR 0.73767 O5 4 0.448406 0.696027 0.682428 11.00000 0.10611 0.06144 = 0.04503 -0.00529 0.01772 -0.01733 O4 4 0.543858 0.717034 0.952437 11.00000 0.08759 0.06295 = 0.04512 0.00117 0.00838 -0.01517 O1 4 0.160640 0.260024 0.543262 11.00000 0.08443 0.06332 = 0.04869 0.00680 0.00589 -0.01090 O2 4 0.245354 0.459974 0.624751 11.00000 0.10537 0.04652 = 0.06806 0.00798 0.01289 -0.01553 O3 4 0.216412 0.304474 0.810160 11.00000 0.11261 0.05358 = 0.04369 -0.00830 0.01777 -0.01681 O6 4 0.440012 0.528015 0.862266 11.00000 0.10500 0.05750 = 0.06176 0.00615 0.00882 -0.01934 C7 1 0.133640 0.120915 0.684381 11.00000 0.05621 0.04500 = 0.04724 0.00013 0.00966 0.00161 C21 1 0.498044 0.741898 0.779755 11.00000 0.06447 0.05147 = 0.03621 0.00153 0.00947 0.00166 C8 1 0.186417 0.251309 0.714790 11.00000 0.05547 0.04675 = 0.04646 0.00006 0.00705 0.00084 C15 1 0.596956 0.992438 0.762725 11.00000 0.04664 0.04427 = 0.05246 -0.00343 0.00942 -0.00554 C4 1 0.100826 -0.002574 0.741402 11.00000 0.05156 0.04324 = 0.04621 -0.00152 0.00321 0.00064 C18 1 0.562696 0.866400 0.815833 11.00000 0.04801 0.04808 = 0.04388 0.00126 0.00705 -0.00155 C9 1 0.204562 0.337197 0.627998 11.00000 0.06109 0.06281 = 0.04636 -0.00166 0.00280 -0.00296 C3 1 0.131320 -0.002366 0.847538 11.00000 0.06957 0.05086 = 0.05424 -0.00686 0.01500 -0.00051 AFIX 43 H3 2 0.171546 0.077118 0.882926 11.00000 -1.20000 AFIX 0 C12 1 0.666063 1.240016 0.662018 11.00000 0.06534 0.05144 = 0.06832 0.01014 0.01458 -0.00237 C16 1 0.591475 0.994227 0.658659 11.00000 0.07462 0.05375 = 0.05114 0.00068 0.00878 -0.00791 AFIX 43 H16 2 0.566168 0.913928 0.621615 11.00000 -1.20000 AFIX 0 C14 1 0.636403 1.118557 0.815505 11.00000 0.06678 0.05042 = 0.05818 -0.00130 0.00982 -0.00475 AFIX 43 H14 2 0.639559 1.121211 0.883932 11.00000 -1.20000 AFIX 0 C10 1 0.113490 0.119093 0.571136 11.00000 0.07670 0.05984 = 0.05527 -0.00497 0.01053 -0.00507 AFIX 23 H10A 2 0.194518 0.052166 0.551780 11.00000 -1.20000 H10B 2 -0.009562 0.096345 0.538338 11.00000 -1.20000 AFIX 0 C19 1 0.594247 0.857427 0.928103 11.00000 0.06931 0.05349 = 0.04543 -0.00175 0.00826 -0.00958 AFIX 23 H19A 2 0.720249 0.875079 0.957934 11.00000 -1.20000 H19B 2 0.520598 0.924387 0.953607 11.00000 -1.20000 AFIX 0 C20 1 0.487289 0.649797 0.864024 11.00000 0.07110 0.05152 = 0.04959 0.00675 0.00943 -0.00363 C13 1 0.670621 1.238969 0.766188 11.00000 0.07342 0.04492 = 0.07579 -0.00071 0.00763 -0.00167 AFIX 43 H13 2 0.696794 1.319619 0.802713 11.00000 -1.20000 AFIX 0 C17 1 0.624000 1.116552 0.610498 11.00000 0.07000 0.07575 = 0.05360 0.01812 0.01268 -0.00424 AFIX 43 H17 2 0.617199 1.115042 0.541704 11.00000 -1.20000 AFIX 0 C1 1 0.037761 -0.243545 0.848825 11.00000 0.06404 0.04547 = 0.06924 0.00691 0.01578 0.00489 C5 1 0.038652 -0.123951 0.692558 11.00000 0.08532 0.05997 = 0.04645 -0.00531 0.00542 -0.00973 AFIX 43 H5 2 0.015596 -0.126173 0.622921 11.00000 -1.20000 AFIX 0 C2 1 0.101092 -0.121702 0.899681 11.00000 0.07897 0.05405 = 0.06337 0.00266 0.02225 0.00173 AFIX 43 H2 2 0.123470 -0.120012 0.969313 11.00000 -1.20000 AFIX 0 C6 1 0.009394 -0.243281 0.744477 11.00000 0.08147 0.04650 = 0.07949 -0.00596 0.01033 -0.00819 AFIX 43 H6 2 -0.029290 -0.322950 0.708934 11.00000 -1.20000 AFIX 0 C11 1 0.002299 -0.373740 0.905598 11.00000 0.08639 0.05817 = 0.11272 0.01986 0.03129 -0.00324 AFIX 33 H11A 2 0.028670 -0.355650 0.976304 11.00000 -1.50000 H11B 2 -0.122158 -0.400030 0.884459 11.00000 -1.50000 H11C 2 0.078288 -0.446665 0.891405 11.00000 -1.50000 AFIX 0 C22 1 0.704316 1.372671 0.608588 11.00000 0.08706 0.07083 = 0.11450 0.03711 0.02015 -0.00734 AFIX 33 H22A 2 0.730356 1.445853 0.656491 11.00000 -1.50000 H22B 2 0.806156 1.358609 0.578156 11.00000 -1.50000 H22C 2 0.600242 1.396105 0.557867 11.00000 -1.50000 AFIX 0 H3A 2 0.303169 0.383879 0.822382 11.00000 0.09133 H5A 2 0.395301 0.619460 0.697590 11.00000 0.40003 HKLF 4 REM dm_br_ME_a.res in P2(1) REM R1 = 0.0552 for 1975 Fo > 4sig(Fo) and 0.1115 for all 3610 data REM 262 parameters refined using 2 restraints END WGHT 0.0636 0.0000 REM Highest difference peak 0.174, deepest hole -0.199, 1-sigma level 0.048 Q1 1 0.6264 1.2358 0.5466 11.00000 0.05 0.17 Q2 1 0.6723 1.3340 0.4991 11.00000 0.05 0.16 Q3 1 0.2410 0.2386 0.6937 11.00000 0.05 0.16 ; _shelx_res_checksum 52397 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.4484(6) 0.6960(4) 0.6824(3) 0.0706(12) Uani 1 1 d D . . . . O4 O 0.5439(5) 0.7170(4) 0.9524(3) 0.0661(11) Uani 1 1 d . . . . . O1 O 0.1606(5) 0.2600(4) 0.5433(3) 0.0667(11) Uani 1 1 d . . . . . O2 O 0.2454(6) 0.4600(4) 0.6248(3) 0.0741(12) Uani 1 1 d . . . . . O3 O 0.2164(6) 0.3045(4) 0.8102(3) 0.0698(12) Uani 1 1 d . . . . . O6 O 0.4400(6) 0.5280(4) 0.8623(3) 0.0761(13) Uani 1 1 d . . . . . C7 C 0.1336(7) 0.1209(6) 0.6844(4) 0.0497(13) Uani 1 1 d . . . . . C21 C 0.4980(7) 0.7419(6) 0.7798(4) 0.0509(14) Uani 1 1 d . . . . . C8 C 0.1864(7) 0.2513(6) 0.7148(4) 0.0501(13) Uani 1 1 d . . . . . C15 C 0.5970(6) 0.9924(5) 0.7627(4) 0.0480(13) Uani 1 1 d . . . . . C4 C 0.1008(6) -0.0026(6) 0.7414(4) 0.0481(14) Uani 1 1 d . . . . . C18 C 0.5627(7) 0.8664(5) 0.8158(4) 0.0471(12) Uani 1 1 d . . . . . C9 C 0.2046(7) 0.3372(7) 0.6280(4) 0.0580(16) Uani 1 1 d . . . . . C3 C 0.1313(7) -0.0024(6) 0.8475(4) 0.0579(15) Uani 1 1 d . . . . . H3 H 0.1715 0.0771 0.8829 0.070 Uiso 1 1 calc R U . . . C12 C 0.6661(7) 1.2400(6) 0.6620(4) 0.0616(15) Uani 1 1 d . . . . . C16 C 0.5915(7) 0.9942(6) 0.6587(4) 0.0605(15) Uani 1 1 d . . . . . H16 H 0.5662 0.9139 0.6216 0.073 Uiso 1 1 calc R U . . . C14 C 0.6364(7) 1.1186(6) 0.8155(4) 0.0590(14) Uani 1 1 d . . . . . H14 H 0.6396 1.1212 0.8839 0.071 Uiso 1 1 calc R U . . . C10 C 0.1135(8) 0.1191(6) 0.5711(4) 0.0644(16) Uani 1 1 d . . . . . H10A H 0.1945 0.0522 0.5518 0.077 Uiso 1 1 calc R U . . . H10B H -0.0096 0.0963 0.5383 0.077 Uiso 1 1 calc R U . . . C19 C 0.5942(8) 0.8574(6) 0.9281(4) 0.0567(14) Uani 1 1 d . . . . . H19A H 0.7202 0.8751 0.9579 0.068 Uiso 1 1 calc R U . . . H19B H 0.5206 0.9244 0.9536 0.068 Uiso 1 1 calc R U . . . C20 C 0.4873(8) 0.6498(7) 0.8640(4) 0.0579(15) Uani 1 1 d . . . . . C13 C 0.6706(8) 1.2390(6) 0.7662(4) 0.0659(16) Uani 1 1 d . . . . . H13 H 0.6968 1.3196 0.8027 0.079 Uiso 1 1 calc R U . . . C17 C 0.6240(8) 1.1166(7) 0.6105(4) 0.0665(17) Uani 1 1 d . . . . . H17 H 0.6172 1.1150 0.5417 0.080 Uiso 1 1 calc R U . . . C1 C 0.0378(7) -0.2435(6) 0.8488(4) 0.0593(15) Uani 1 1 d . . . . . C5 C 0.0387(8) -0.1240(6) 0.6926(4) 0.0652(16) Uani 1 1 d . . . . . H5 H 0.0156 -0.1262 0.6229 0.078 Uiso 1 1 calc R U . . . C2 C 0.1011(8) -0.1217(6) 0.8997(4) 0.0644(16) Uani 1 1 d . . . . . H2 H 0.1235 -0.1200 0.9693 0.077 Uiso 1 1 calc R U . . . C6 C 0.0094(8) -0.2433(7) 0.7445(5) 0.0701(17) Uani 1 1 d . . . . . H6 H -0.0293 -0.3229 0.7089 0.084 Uiso 1 1 calc R U . . . C11 C 0.0023(9) -0.3737(7) 0.9056(5) 0.084(2) Uani 1 1 d . . . . . H11A H 0.0287 -0.3556 0.9763 0.126 Uiso 1 1 calc R U . . . H11B H -0.1222 -0.4000 0.8845 0.126 Uiso 1 1 calc R U . . . H11C H 0.0783 -0.4467 0.8914 0.126 Uiso 1 1 calc R U . . . C22 C 0.7043(9) 1.3727(7) 0.6086(5) 0.091(2) Uani 1 1 d . . . . . H22A H 0.7304 1.4459 0.6565 0.136 Uiso 1 1 calc R U . . . H22B H 0.8062 1.3586 0.5782 0.136 Uiso 1 1 calc R U . . . H22C H 0.6002 1.3961 0.5579 0.136 Uiso 1 1 calc R U . . . H3A H 0.303(8) 0.384(7) 0.822(4) 0.09(2) Uiso 1 1 d . . . . . H5A H 0.40(2) 0.619(10) 0.698(11) 0.40(10) Uiso 1 1 d 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 O5 0.106(3) 0.061(3) 0.045(2) -0.005(2) 0.018(2) -0.017(2) O4 0.088(3) 0.063(3) 0.045(2) 0.001(2) 0.0084(19) -0.015(2) O1 0.084(3) 0.063(3) 0.049(2) 0.007(2) 0.0059(19) -0.011(2) O2 0.105(3) 0.047(3) 0.068(3) 0.008(2) 0.013(2) -0.016(2) O3 0.113(3) 0.054(3) 0.044(2) -0.0083(19) 0.018(2) -0.017(2) O6 0.105(3) 0.057(3) 0.062(3) 0.006(2) 0.009(2) -0.019(2) C7 0.056(3) 0.045(3) 0.047(3) 0.000(3) 0.010(3) 0.002(3) C21 0.064(3) 0.051(4) 0.036(3) 0.002(3) 0.009(2) 0.002(3) C8 0.055(3) 0.047(4) 0.046(3) 0.000(3) 0.007(2) 0.001(3) C15 0.047(3) 0.044(3) 0.052(3) -0.003(3) 0.009(2) -0.006(3) C4 0.052(4) 0.043(3) 0.046(3) -0.002(3) 0.003(3) 0.001(3) C18 0.048(3) 0.048(3) 0.044(3) 0.001(3) 0.007(2) -0.002(3) C9 0.061(4) 0.063(5) 0.046(4) -0.002(3) 0.003(3) -0.003(3) C3 0.070(4) 0.051(4) 0.054(4) -0.007(3) 0.015(3) -0.001(3) C12 0.065(4) 0.051(4) 0.068(4) 0.010(3) 0.015(3) -0.002(3) C16 0.075(4) 0.054(4) 0.051(4) 0.001(3) 0.009(3) -0.008(3) C14 0.067(4) 0.050(4) 0.058(3) -0.001(3) 0.010(3) -0.005(3) C10 0.077(4) 0.060(4) 0.055(4) -0.005(3) 0.011(3) -0.005(3) C19 0.069(4) 0.053(4) 0.045(3) -0.002(3) 0.008(3) -0.010(3) C20 0.071(4) 0.052(4) 0.050(4) 0.007(3) 0.009(3) -0.004(3) C13 0.073(4) 0.045(4) 0.076(4) -0.001(3) 0.008(3) -0.002(3) C17 0.070(4) 0.076(5) 0.054(3) 0.018(4) 0.013(3) -0.004(4) C1 0.064(4) 0.045(4) 0.069(4) 0.007(3) 0.016(3) 0.005(3) C5 0.085(4) 0.060(4) 0.046(3) -0.005(3) 0.005(3) -0.010(3) C2 0.079(4) 0.054(4) 0.063(4) 0.003(3) 0.022(3) 0.002(3) C6 0.081(4) 0.046(4) 0.079(5) -0.006(4) 0.010(3) -0.008(3) C11 0.086(5) 0.058(4) 0.113(5) 0.020(4) 0.031(4) -0.003(4) C22 0.087(5) 0.071(5) 0.114(6) 0.037(4) 0.020(4) -0.007(4) 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' N N 0.0061 0.0033 '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 C21 O5 H5A 95(10) . . ? C20 O4 C19 107.1(4) . . ? C9 O1 C10 108.8(4) . . ? C8 O3 H3A 115(3) . . ? C8 C7 C4 131.7(5) . . ? C8 C7 C10 106.2(5) . . ? C4 C7 C10 122.1(5) . . ? C18 C21 O5 130.0(5) . . ? C18 C21 C20 109.6(4) . . ? O5 C21 C20 120.4(5) . . ? C7 C8 O3 128.0(5) . . ? C7 C8 C9 110.7(5) . . ? O3 C8 C9 121.3(5) . . ? C16 C15 C14 117.2(5) . . ? C16 C15 C18 122.2(5) . . ? C14 C15 C18 120.6(4) . . ? C5 C4 C3 117.2(5) . . ? C5 C4 C7 121.1(5) . . ? C3 C4 C7 121.7(5) . . ? C21 C18 C15 130.6(4) . . ? C21 C18 C19 106.5(5) . . ? C15 C18 C19 122.8(5) . . ? O2 C9 O1 121.4(5) . . ? O2 C9 C8 129.9(5) . . ? O1 C9 C8 108.7(5) . . ? C2 C3 C4 120.4(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C17 C12 C13 117.0(5) . . ? C17 C12 C22 122.0(6) . . ? C13 C12 C22 120.9(6) . . ? C17 C16 C15 120.6(6) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C13 C14 C15 121.3(5) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? O1 C10 C7 105.7(5) . . ? O1 C10 H10A 110.6 . . ? C7 C10 H10A 110.6 . . ? O1 C10 H10B 110.6 . . ? C7 C10 H10B 110.6 . . ? H10A C10 H10B 108.7 . . ? O4 C19 C18 106.9(4) . . ? O4 C19 H19A 110.3 . . ? C18 C19 H19A 110.3 . . ? O4 C19 H19B 110.3 . . ? C18 C19 H19B 110.3 . . ? H19A C19 H19B 108.6 . . ? O6 C20 O4 121.0(5) . . ? O6 C20 C21 129.2(5) . . ? O4 C20 C21 109.8(5) . . ? C14 C13 C12 121.3(6) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C12 C17 C16 122.6(5) . . ? C12 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? C6 C1 C2 117.7(6) . . ? C6 C1 C11 120.7(6) . . ? C2 C1 C11 121.7(6) . . ? C4 C5 C6 122.5(5) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C3 C2 C1 121.5(5) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C1 C6 C5 120.7(6) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 O5 C21 1.377(6) . ? O5 H5A 0.893(14) . ? O4 C20 1.361(6) . ? O4 C19 1.478(6) . ? O1 C9 1.361(7) . ? O1 C10 1.490(7) . ? O2 C9 1.240(7) . ? O3 C8 1.375(6) . ? O3 H3A 1.01(6) . ? O6 C20 1.239(7) . ? C7 C8 1.371(8) . ? C7 C4 1.483(7) . ? C7 C10 1.522(7) . ? C21 C18 1.362(8) . ? C21 C20 1.476(8) . ? C8 C9 1.481(8) . ? C15 C16 1.413(7) . ? C15 C14 1.425(7) . ? C15 C18 1.478(7) . ? C4 C5 1.391(8) . ? C4 C3 1.419(7) . ? C18 C19 1.503(7) . ? C3 C2 1.408(8) . ? C3 H3 0.9300 . ? C12 C17 1.397(8) . ? C12 C13 1.416(8) . ? C12 C22 1.543(8) . ? C16 C17 1.409(8) . ? C16 H16 0.9300 . ? C14 C13 1.405(8) . ? C14 H14 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C13 H13 0.9300 . ? C17 H17 0.9300 . ? C1 C6 1.395(8) . ? C1 C2 1.408(8) . ? C1 C11 1.541(8) . ? C5 C6 1.405(8) . ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ?