#------------------------------------------------------------------------------ #$Date: 2024-06-28 12:32:51 +0300 (Fri, 28 Jun 2024) $ #$Revision: 292638 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157483.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_7157483 loop_ _publ_author_name 'Roy, Biswajit' 'Das, Eshani' 'Roy, Avijit' 'Mal, Dipakranjan' _publ_section_title ; Ni(ii)-Catalyzed vinylic C-H functionalization of 2-acetamido-3-arylacrylates to access isotetronic acids. ; _journal_issue 19 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3697 _journal_page_last 3706 _journal_paper_doi 10.1039/d0ob00557f _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C11 H7 N O3' _chemical_formula_weight 201.17 _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 _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 94.77 _cell_angle_beta 105.91 _cell_angle_gamma 108.25 _cell_formula_units_Z 4 _cell_length_a 8.009 _cell_length_b 9.607 _cell_length_c 13.044 _cell_measurement_reflns_used 350 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.609 _cell_measurement_theta_min 2.824 _cell_volume 900.812 _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 0.990 _diffrn_measured_fraction_theta_max 0.969 _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 0.0386 _diffrn_reflns_av_unetI/netI 0.0618 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8034 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 25.500 _diffrn_reflns_theta_max 26.609 _diffrn_reflns_theta_min 2.824 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.483 _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.562 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 3650 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.1281 _refine_ls_R_factor_gt 0.0748 _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^)+(0.1120P)^2^+0.5161P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1975 _refine_ls_wR_factor_ref 0.2304 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2118 _reflns_number_total 3650 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00557f2.cif _cod_data_source_block 9t _cod_depositor_comments ; Adding full bibliography for 7157480--7157483.cif. 2024-06-28 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C22 H14 N2 O6' _cod_original_formula_weight 402.35 _cod_original_formula_units_Z 2 _cod_original_cell_volume 900.8 _cod_database_code 7157483 _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 mo_psbrcn_a.res in P-1 CELL 0.71073 8.0089 9.6069 13.0440 94.775 105.909 108.247 ZERR 2.00 0.0000 0.0000 0.0000 0.000 0.000 0.000 LATT 1 SFAC C H N O UNIT 44 28 4 12 MERG 2 FMAP 2 PLAN 10 ACTA 51.00 BOND $H LIST 6 L.S. 10 WGHT 0.112000 0.516100 FVAR 0.40708 O3 4 0.280818 0.580805 -0.060036 11.00000 0.05509 0.04531 = 0.05225 0.01693 0.00347 -0.00984 AFIX 83 H3A 2 0.196023 0.503366 -0.064573 11.00000 -1.50000 AFIX 0 O6 4 0.921455 0.733991 0.442596 11.00000 0.05132 0.04893 = 0.05103 0.01800 -0.00025 -0.01025 AFIX 83 H6A 2 0.992522 0.814812 0.439081 11.00000 -1.50000 AFIX 0 O4 4 1.174135 0.748381 0.716532 11.00000 0.05294 0.06053 = 0.04837 0.00215 0.00410 -0.00352 O1 4 0.521270 0.592806 0.215761 11.00000 0.07685 0.05823 = 0.04965 0.02780 0.02059 0.00730 O5 4 1.252642 0.923761 0.620361 11.00000 0.05126 0.04793 = 0.08114 -0.00179 0.01304 -0.01197 O2 4 0.254769 0.414303 0.117841 11.00000 0.07596 0.04446 = 0.07838 0.02907 0.03186 -0.00039 C15 1 0.738750 0.453678 0.531375 11.00000 0.03904 0.03616 = 0.04254 0.00987 0.01663 0.00990 N1 3 0.953035 1.323224 -0.136732 11.00000 0.06073 0.04568 = 0.06949 0.02403 0.01600 0.00182 N2 3 0.120674 -0.023347 0.359177 11.00000 0.05547 0.05079 = 0.06759 0.01178 0.00530 -0.00408 C7 1 0.883279 1.222326 -0.104434 11.00000 0.03996 0.03490 = 0.04823 0.01184 0.01075 0.00259 C8 1 0.560321 0.735689 0.082333 11.00000 0.04415 0.03760 = 0.04339 0.00887 0.01464 0.01169 C1 1 0.802785 1.098527 -0.056759 11.00000 0.04780 0.03405 = 0.05082 0.01696 0.02356 0.01322 C4 1 0.643779 0.859927 0.030601 11.00000 0.03863 0.02978 = 0.04740 0.00723 0.01626 0.00781 C11 1 0.403502 0.618873 0.040449 11.00000 0.04591 0.03140 = 0.05045 0.00972 0.01872 0.00793 C21 1 0.979234 0.703161 0.541827 11.00000 0.03958 0.04018 = 0.04388 0.00539 0.01310 0.00644 C22 1 1.149787 0.806190 0.626831 11.00000 0.03969 0.04101 = 0.04964 0.00226 0.01318 0.00166 C3 1 0.805085 0.974733 0.094323 11.00000 0.04782 0.04450 = 0.03629 0.00896 0.00434 0.00707 AFIX 43 H3 2 0.859929 0.971291 0.166357 11.00000 -1.20000 AFIX 0 C12 1 0.420652 0.205161 0.441702 11.00000 0.03539 0.03845 = 0.05344 0.00307 0.01130 0.00583 C16 1 0.627141 0.439611 0.425902 11.00000 0.04171 0.04071 = 0.04749 0.01494 0.01029 0.00594 AFIX 43 H16 2 0.659486 0.514181 0.386361 11.00000 -1.20000 AFIX 0 C19 1 0.906905 0.585779 0.582524 11.00000 0.03987 0.04302 = 0.04401 0.00626 0.01339 0.01185 C10 1 0.377419 0.527228 0.124091 11.00000 0.05715 0.03694 = 0.04736 0.01666 0.01940 0.01046 C18 1 0.251994 0.078735 0.392044 11.00000 0.04264 0.03914 = 0.04625 0.01065 0.00927 0.00414 C5 1 0.563313 0.864196 -0.076301 11.00000 0.03971 0.03386 = 0.04879 0.00734 0.00664 0.00035 AFIX 43 H5 2 0.456242 0.786629 -0.118272 11.00000 -1.20000 AFIX 0 C17 1 0.467765 0.315234 0.379007 11.00000 0.03968 0.04036 = 0.05303 0.00941 0.01406 0.00535 AFIX 43 H17 2 0.393808 0.304668 0.308003 11.00000 -1.20000 AFIX 0 C6 1 0.641003 0.983396 -0.121638 11.00000 0.04928 0.03678 = 0.05485 0.01304 0.01663 0.00739 AFIX 43 H6 2 0.586891 0.986999 -0.193739 11.00000 -1.20000 AFIX 0 C13 1 0.529398 0.218191 0.544418 11.00000 0.04850 0.04694 = 0.04660 0.01811 0.01278 0.00564 AFIX 43 H13 2 0.496146 0.144181 0.584233 11.00000 -1.20000 AFIX 0 C2 1 0.882674 1.094135 0.048871 11.00000 0.04677 0.03534 = 0.05386 0.00658 0.01423 0.00033 AFIX 43 H2 2 0.989872 1.171639 0.090774 11.00000 -1.20000 AFIX 0 C14 1 0.690897 0.342003 0.590717 11.00000 0.04785 0.04909 = 0.04148 0.01202 0.00996 0.00713 AFIX 43 H14 2 0.766376 0.350049 0.660892 11.00000 -1.20000 AFIX 0 C20 1 1.027328 0.604889 0.696558 11.00000 0.05098 0.05711 = 0.04748 0.01045 0.01196 0.00514 AFIX 23 H20A 2 0.957459 0.604248 0.746738 11.00000 -1.20000 H20B 2 1.078110 0.525571 0.704497 11.00000 -1.20000 AFIX 0 C9 1 0.644760 0.726669 0.196682 11.00000 0.05493 0.05039 = 0.05059 0.01577 0.01470 0.00397 AFIX 23 H9A 2 0.767055 0.720826 0.207970 11.00000 -1.20000 H9B 2 0.655811 0.813550 0.245258 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_psbrcn_a.res in P-1 REM R1 = 0.0748 for 2118 Fo > 4sig(Fo) and 0.1281 for all 3650 data REM 271 parameters refined using 0 restraints END WGHT 0.1107 0.5275 REM Highest difference peak 0.562, deepest hole -0.256, 1-sigma level 0.063 Q1 1 0.2268 0.1497 0.3018 11.00000 0.05 0.48 Q2 1 0.7048 1.1452 -0.2022 11.00000 0.05 0.46 Q3 1 0.7225 0.5452 0.4312 11.00000 0.05 0.39 Q4 1 0.4692 0.7673 -0.0636 11.00000 0.05 0.37 Q5 1 0.6484 0.7757 0.1455 11.00000 0.05 0.29 Q6 1 0.7316 0.8805 0.1038 11.00000 0.05 0.26 Q7 1 0.9864 0.6781 0.5811 11.00000 0.05 0.24 Q8 1 0.4587 0.2842 0.4295 11.00000 0.05 0.24 Q9 1 0.5999 1.0174 -0.1760 11.00000 0.05 0.23 Q10 1 0.7253 1.0245 -0.0497 11.00000 0.05 0.23 ; _shelx_res_checksum 74383 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 O3 O 0.2808(3) 0.5808(3) -0.0600(2) 0.0601(8) Uani 1 1 d . . . . . H3A H 0.1960 0.5034 -0.0646 0.090 Uiso 1 1 calc R U . . . O6 O 0.9215(3) 0.7340(3) 0.4426(2) 0.0603(8) Uani 1 1 d . . . . . H6A H 0.9925 0.8148 0.4391 0.090 Uiso 1 1 calc R U . . . O4 O 1.1741(4) 0.7484(3) 0.7165(2) 0.0628(8) Uani 1 1 d . . . . . O1 O 0.5213(4) 0.5928(3) 0.2158(2) 0.0644(8) Uani 1 1 d . . . . . O5 O 1.2526(4) 0.9238(3) 0.6204(2) 0.0700(9) Uani 1 1 d . . . . . O2 O 0.2548(4) 0.4143(3) 0.1178(2) 0.0689(9) Uani 1 1 d . . . . . C15 C 0.7388(4) 0.4537(3) 0.5314(3) 0.0391(8) Uani 1 1 d . . . . . N1 N 0.9530(5) 1.3232(3) -0.1367(3) 0.0630(9) Uani 1 1 d . . . . . N2 N 0.1207(5) -0.0233(4) 0.3592(3) 0.0666(10) Uani 1 1 d . . . . . C7 C 0.8833(5) 1.2223(4) -0.1044(3) 0.0441(8) Uani 1 1 d . . . . . C8 C 0.5603(5) 0.7357(3) 0.0823(3) 0.0421(8) Uani 1 1 d . . . . . C1 C 0.8028(5) 1.0985(3) -0.0568(3) 0.0422(8) Uani 1 1 d . . . . . C4 C 0.6438(5) 0.8599(3) 0.0306(3) 0.0391(8) Uani 1 1 d . . . . . C11 C 0.4035(5) 0.6189(3) 0.0404(3) 0.0431(8) Uani 1 1 d . . . . . C21 C 0.9792(5) 0.7032(4) 0.5418(3) 0.0433(8) Uani 1 1 d . . . . . C22 C 1.1498(5) 0.8062(4) 0.6268(3) 0.0471(9) Uani 1 1 d . . . . . C3 C 0.8051(5) 0.9747(4) 0.0943(3) 0.0470(9) Uani 1 1 d . . . . . H3 H 0.8599 0.9713 0.1664 0.056 Uiso 1 1 calc R U . . . C12 C 0.4207(4) 0.2052(4) 0.4417(3) 0.0451(9) Uani 1 1 d . . . . . C16 C 0.6271(5) 0.4396(4) 0.4259(3) 0.0458(9) Uani 1 1 d . . . . . H16 H 0.6595 0.5142 0.3864 0.055 Uiso 1 1 calc R U . . . C19 C 0.9069(5) 0.5858(4) 0.5825(3) 0.0431(8) Uani 1 1 d . . . . . C10 C 0.3774(5) 0.5272(4) 0.1241(3) 0.0475(9) Uani 1 1 d . . . . . C18 C 0.2520(5) 0.0787(4) 0.3920(3) 0.0461(9) Uani 1 1 d . . . . . C5 C 0.5633(5) 0.8642(4) -0.0763(3) 0.0455(9) Uani 1 1 d . . . . . H5 H 0.4562 0.7866 -0.1183 0.055 Uiso 1 1 calc R U . . . C17 C 0.4678(5) 0.3152(4) 0.3790(3) 0.0466(9) Uani 1 1 d . . . . . H17 H 0.3938 0.3047 0.3080 0.056 Uiso 1 1 calc R U . . . C6 C 0.6410(5) 0.9834(4) -0.1216(3) 0.0486(9) Uani 1 1 d . . . . . H6 H 0.5869 0.9870 -0.1937 0.058 Uiso 1 1 calc R U . . . C13 C 0.5294(5) 0.2182(4) 0.5444(3) 0.0500(9) Uani 1 1 d . . . . . H13 H 0.4961 0.1442 0.5842 0.060 Uiso 1 1 calc R U . . . C2 C 0.8827(5) 1.0941(4) 0.0489(3) 0.0493(9) Uani 1 1 d . . . . . H2 H 0.9899 1.1716 0.0908 0.059 Uiso 1 1 calc R U . . . C14 C 0.6909(5) 0.3420(4) 0.5907(3) 0.0493(9) Uani 1 1 d . . . . . H14 H 0.7664 0.3500 0.6609 0.059 Uiso 1 1 calc R U . . . C20 C 1.0273(5) 0.6049(4) 0.6966(3) 0.0560(10) Uani 1 1 d . . . . . H20A H 0.9575 0.6042 0.7467 0.067 Uiso 1 1 calc R U . . . H20B H 1.0781 0.5256 0.7045 0.067 Uiso 1 1 calc R U . . . C9 C 0.6448(6) 0.7267(4) 0.1967(3) 0.0556(10) Uani 1 1 d . . . . . H9A H 0.7671 0.7208 0.2080 0.067 Uiso 1 1 calc R U . . . H9B H 0.6558 0.8135 0.2453 0.067 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 O3 0.0551(16) 0.0453(14) 0.0523(17) 0.0169(12) 0.0035(14) -0.0098(12) O6 0.0513(15) 0.0489(14) 0.0510(17) 0.0180(12) -0.0003(13) -0.0103(12) O4 0.0529(16) 0.0605(16) 0.0484(17) 0.0021(13) 0.0041(13) -0.0035(13) O1 0.0768(19) 0.0582(16) 0.0497(17) 0.0278(13) 0.0206(15) 0.0073(15) O5 0.0513(16) 0.0479(16) 0.081(2) -0.0018(14) 0.0130(15) -0.0120(13) O2 0.0760(19) 0.0445(15) 0.078(2) 0.0291(14) 0.0319(17) -0.0004(14) C15 0.0390(17) 0.0362(16) 0.043(2) 0.0099(14) 0.0166(16) 0.0099(15) N1 0.061(2) 0.0457(18) 0.069(2) 0.0240(16) 0.0160(18) 0.0018(16) N2 0.055(2) 0.0508(19) 0.068(2) 0.0118(16) 0.0053(18) -0.0041(17) C7 0.0400(18) 0.0349(17) 0.048(2) 0.0118(15) 0.0108(16) 0.0026(15) C8 0.0441(19) 0.0376(17) 0.043(2) 0.0089(15) 0.0146(16) 0.0117(16) C1 0.0478(19) 0.0340(17) 0.051(2) 0.0170(15) 0.0236(17) 0.0132(16) C4 0.0386(17) 0.0298(15) 0.047(2) 0.0072(14) 0.0163(16) 0.0078(14) C11 0.0459(19) 0.0314(16) 0.050(2) 0.0097(14) 0.0187(18) 0.0079(15) C21 0.0396(18) 0.0402(18) 0.044(2) 0.0054(15) 0.0131(16) 0.0064(16) C22 0.0397(19) 0.0410(18) 0.050(2) 0.0023(15) 0.0132(17) 0.0017(16) C3 0.048(2) 0.0445(19) 0.036(2) 0.0090(15) 0.0043(16) 0.0071(17) C12 0.0354(18) 0.0384(18) 0.053(2) 0.0031(15) 0.0113(17) 0.0058(15) C16 0.0417(19) 0.0407(18) 0.047(2) 0.0149(15) 0.0103(17) 0.0059(16) C19 0.0399(18) 0.0430(18) 0.044(2) 0.0063(15) 0.0134(16) 0.0119(16) C10 0.057(2) 0.0369(18) 0.047(2) 0.0167(16) 0.0194(19) 0.0105(17) C18 0.0426(19) 0.0391(19) 0.046(2) 0.0106(15) 0.0093(17) 0.0041(17) C5 0.0397(19) 0.0339(17) 0.049(2) 0.0073(15) 0.0066(16) 0.0004(15) C17 0.0397(18) 0.0404(18) 0.053(2) 0.0094(16) 0.0141(17) 0.0054(16) C6 0.049(2) 0.0368(18) 0.055(2) 0.0130(16) 0.0166(18) 0.0074(17) C13 0.049(2) 0.047(2) 0.047(2) 0.0181(16) 0.0128(18) 0.0056(17) C2 0.047(2) 0.0353(18) 0.054(2) 0.0066(16) 0.0142(18) 0.0003(16) C14 0.048(2) 0.049(2) 0.041(2) 0.0120(16) 0.0100(17) 0.0071(18) C20 0.051(2) 0.057(2) 0.047(2) 0.0104(17) 0.0120(19) 0.0051(19) C9 0.055(2) 0.050(2) 0.051(2) 0.0158(17) 0.0147(19) 0.0040(18) 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 C11 O3 H3A 109.5 . . ? C21 O6 H6A 109.5 . . ? C22 O4 C20 108.9(3) . . ? C10 O1 C9 109.0(3) . . ? C16 C15 C14 119.8(3) . . ? C16 C15 C19 121.1(3) . . ? C14 C15 C19 119.0(3) . . ? N1 C7 C1 176.4(4) . . ? C11 C8 C9 108.1(3) . . ? C11 C8 C4 129.0(3) . . ? C9 C8 C4 122.8(3) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 C7 120.5(3) . . ? C6 C1 C7 118.5(3) . . ? C5 C4 C3 120.5(3) . . ? C5 C4 C8 121.5(3) . . ? C3 C4 C8 118.0(3) . . ? C8 C11 O3 129.3(3) . . ? C8 C11 C10 109.0(3) . . ? O3 C11 C10 121.7(3) . . ? C19 C21 O6 129.8(3) . . ? C19 C21 C22 108.3(3) . . ? O6 C21 C22 121.8(3) . . ? O5 C22 O4 122.9(3) . . ? O5 C22 C21 127.9(4) . . ? O4 C22 C21 109.1(3) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C13 C12 C17 121.2(3) . . ? C13 C12 C18 121.5(3) . . ? C17 C12 C18 117.3(3) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C21 C19 C15 129.4(3) . . ? C21 C19 C20 108.4(3) . . ? C15 C19 C20 122.2(3) . . ? O2 C10 O1 122.6(3) . . ? O2 C10 C11 129.1(4) . . ? O1 C10 C11 108.2(3) . . ? N2 C18 C12 175.7(4) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C16 C17 C12 118.4(4) . . ? C16 C17 H17 120.8 . . ? C12 C17 H17 120.8 . . ? C5 C6 C1 118.7(3) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O4 C20 C19 105.2(3) . . ? O4 C20 H20A 110.7 . . ? C19 C20 H20A 110.7 . . ? O4 C20 H20B 110.7 . . ? C19 C20 H20B 110.7 . . ? H20A C20 H20B 108.8 . . ? O1 C9 C8 105.7(3) . . ? O1 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? O1 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? 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 O3 C11 1.344(4) . ? O3 H3A 0.8200 . ? O6 C21 1.341(4) . ? O6 H6A 0.8200 . ? O4 C22 1.329(4) . ? O4 C20 1.452(4) . ? O1 C10 1.349(5) . ? O1 C9 1.444(4) . ? O5 C22 1.197(4) . ? O2 C10 1.193(4) . ? C15 C16 1.389(5) . ? C15 C14 1.393(5) . ? C15 C19 1.472(5) . ? N1 C7 1.134(4) . ? N2 C18 1.135(4) . ? C7 C1 1.442(4) . ? C8 C11 1.332(5) . ? C8 C9 1.482(5) . ? C8 C4 1.486(4) . ? C1 C2 1.361(5) . ? C1 C6 1.401(5) . ? C4 C5 1.377(5) . ? C4 C3 1.394(5) . ? C11 C10 1.476(5) . ? C21 C19 1.322(5) . ? C21 C22 1.488(5) . ? C3 C2 1.386(5) . ? C3 H3 0.9300 . ? C12 C13 1.354(5) . ? C12 C17 1.412(5) . ? C12 C18 1.443(5) . ? C16 C17 1.388(5) . ? C16 H16 0.9300 . ? C19 C20 1.495(5) . ? C5 C6 1.384(5) . ? C5 H5 0.9300 . ? C17 H17 0.9300 . ? C6 H6 0.9300 . ? C13 C14 1.393(5) . ? C13 H13 0.9300 . ? C2 H2 0.9300 . ? C14 H14 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ?