#------------------------------------------------------------------------------ #$Date: 2024-07-05 20:53:39 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159929.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_7159929 loop_ _publ_author_name 'You, Pengyuan' 'Liu, Minjie' 'Zhang, Ke' 'Yang, Fan' 'Tan, Zequn' 'Chen, Fener' _publ_section_title ; Highly enantio- and diastereoselective construction of spirocyclic oxindoles via a palladium-catalyzed decarboxylative asymmetric [4 + 2] annulation strategy. ; _journal_issue 22 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4466 _journal_page_last 4471 _journal_paper_doi 10.1039/d4ob00518j _journal_volume 22 _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_sum 'C24 H25 N O4' _chemical_formula_weight 391.45 _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 geom _audit_block_doi 10.5517/ccdc.csd.cc2h9ffp _audit_creation_method SHELXL-2019/2 _audit_update_record ; 2023-10-23 deposited with the CCDC. 2024-04-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.7150(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.0358(3) _cell_length_b 10.9125(4) _cell_length_c 12.2549(5) _cell_measurement_reflns_used 3056 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 51.50 _cell_measurement_theta_min 3.93 _cell_volume 1074.56(7) _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-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 15052 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.927 _diffrn_reflns_theta_min 4.788 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.210 _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.321 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details ; Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.09(5) _refine_ls_extinction_coef 0.0100(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 4049 _refine_ls_number_restraints 44 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0295 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.1669P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.0793 _reflns_Friedel_coverage 0.888 _reflns_Friedel_fraction_full 0.986 _reflns_Friedel_fraction_max 0.986 _reflns_number_gt 3944 _reflns_number_total 4049 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00518j2.cif _cod_data_source_block ga_230417b_a _cod_depositor_comments 'Adding full bibliography for 7159929.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7159929 _shelx_shelxl_version_number 2019/2 _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 0.917 _shelx_estimated_absorpt_t_max 0.943 _shelx_res_file ; TITL ga_230417b_a.res in P2(1) ga_230417b_a.res created by SHELXL-2019/2 at 11:37:18 on 18-Apr-2023 CELL 1.34139 8.0358 10.9125 12.2549 90.000 90.715 90.000 ZERR 2.000 0.0003 0.0004 0.0005 0.000 0.001 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N O UNIT 48 50 2 8 OMIT 0 0 1 OMIT 1 -1 2 L.S. 6 ACTA BOND FMAP 2 PLAN 1 CONF SIMU 0.02 0.05 2.0 C22 C22' ISOR 0.02 C22 C23 C24 C22' C23' C24' DFIX 1.53 0.02 C21 C23' SIZE 0.14 0.18 0.21 TEMP -100.150 WGHT 0.039300 0.166900 EXTI 0.010010 FVAR 1.56474 0.56138 N1 3 0.746732 0.494725 0.241226 11.00000 0.02899 0.03201 = 0.03024 -0.00093 0.00205 0.00095 O1 4 0.765374 0.312562 0.341346 11.00000 0.05446 0.03151 = 0.04338 0.00054 0.00098 0.00985 O2 4 0.530482 0.554578 0.576856 11.00000 0.03781 0.04482 = 0.02878 -0.00386 0.00272 -0.00013 O3 4 0.705432 0.339339 0.126382 11.00000 0.08804 0.04140 = 0.03567 -0.01036 0.00982 -0.01143 O4 4 0.799678 0.516388 0.060277 11.00000 0.12952 0.06251 = 0.03441 -0.00254 0.01071 -0.03195 C1 1 0.750188 0.422569 0.336683 11.00000 0.02840 0.03230 = 0.03420 0.00122 0.00120 0.00426 C2 1 0.554051 0.481081 0.482894 11.00000 0.03352 0.03043 = 0.02780 0.00193 0.00133 -0.00188 AFIX 13 H2 2 0.550211 0.393029 0.505324 11.00000 -1.20000 AFIX 0 C3 1 0.729546 0.507798 0.433662 11.00000 0.02695 0.03100 = 0.03078 -0.00012 -0.00075 0.00243 C4 1 0.862771 0.480289 0.522393 11.00000 0.03396 0.03832 = 0.03660 0.00458 -0.00601 0.00344 AFIX 23 H4A 2 0.871309 0.390573 0.533067 11.00000 -1.20000 H4B 2 0.972253 0.510452 0.497761 11.00000 -1.20000 AFIX 0 C5 1 0.820505 0.540322 0.629215 11.00000 0.04654 0.04129 = 0.03595 0.00248 -0.01149 0.00111 C6 1 0.644089 0.519638 0.662653 11.00000 0.05182 0.05485 = 0.02712 0.00038 -0.00184 -0.00200 AFIX 23 H6A 2 0.627863 0.431985 0.680430 11.00000 -1.20000 H6B 2 0.620742 0.568225 0.728944 11.00000 -1.20000 AFIX 0 C7 1 0.740805 0.632724 0.383077 11.00000 0.02034 0.03233 = 0.03317 0.00118 0.00036 0.00063 C8 1 0.748812 0.621514 0.270090 11.00000 0.02314 0.03285 = 0.03328 -0.00023 -0.00004 0.00155 C9 1 0.760523 0.722488 0.202599 11.00000 0.03442 0.03963 = 0.03528 0.00660 -0.00087 0.00066 AFIX 43 H9 2 0.765472 0.713754 0.125579 11.00000 -1.20000 AFIX 0 C10 1 0.764791 0.837319 0.251619 11.00000 0.03918 0.03396 = 0.04690 0.00950 -0.00024 0.00104 AFIX 43 H10 2 0.772114 0.908343 0.207109 11.00000 -1.20000 AFIX 0 C11 1 0.758596 0.850554 0.364084 11.00000 0.02999 0.02956 = 0.05168 -0.00031 0.00066 0.00074 AFIX 43 H11 2 0.762828 0.929980 0.395733 11.00000 -1.20000 AFIX 0 C12 1 0.746194 0.747701 0.430628 11.00000 0.02796 0.03345 = 0.03716 -0.00189 0.00267 0.00203 AFIX 43 H12 2 0.741490 0.756306 0.507668 11.00000 -1.20000 AFIX 0 C13 1 0.412623 0.504602 0.403081 11.00000 0.02777 0.03123 = 0.03132 0.00537 0.00372 -0.00366 C14 1 0.322129 0.613221 0.405143 11.00000 0.03173 0.03438 = 0.04203 0.00174 0.00338 -0.00145 AFIX 43 H14 2 0.346142 0.673324 0.459164 11.00000 -1.20000 AFIX 0 C15 1 0.196297 0.634000 0.328079 11.00000 0.03320 0.04412 = 0.05405 0.00956 0.00156 0.00411 AFIX 43 H15 2 0.134496 0.708174 0.329803 11.00000 -1.20000 AFIX 0 C16 1 0.161158 0.546956 0.249120 11.00000 0.02990 0.05823 = 0.04136 0.01423 -0.00254 -0.00610 AFIX 43 H16 2 0.076930 0.562079 0.195723 11.00000 -1.20000 AFIX 0 C17 1 0.248506 0.438089 0.247918 11.00000 0.04085 0.05289 = 0.03665 0.00024 -0.00271 -0.00966 AFIX 43 H17 2 0.223223 0.377848 0.194260 11.00000 -1.20000 AFIX 0 C18 1 0.373371 0.416348 0.325003 11.00000 0.03757 0.03663 = 0.03635 0.00186 -0.00188 -0.00200 AFIX 43 H18 2 0.432200 0.340845 0.324364 11.00000 -1.20000 AFIX 0 C19 1 0.926633 0.605892 0.687976 11.00000 0.05660 0.05645 = 0.05595 -0.00867 -0.01689 0.00134 AFIX 93 H19A 2 0.892111 0.642190 0.754419 11.00000 -1.20000 H19B 2 1.037532 0.616783 0.663822 11.00000 -1.20000 AFIX 0 C20 1 0.753538 0.452338 0.133403 11.00000 0.03629 0.04197 = 0.03160 -0.00338 0.00164 -0.00154 C21 1 0.726288 0.268367 0.024288 11.00000 0.07090 0.04548 = 0.03519 -0.01251 -0.00480 0.00414 PART 1 21 C22 1 0.638089 0.322061 -0.072910 21.00000 0.07120 0.05732 = 0.04598 -0.01756 -0.02198 0.00860 AFIX 137 H22A 2 0.525501 0.346840 -0.052416 21.00000 -1.50000 H22B 2 0.631459 0.260711 -0.131201 21.00000 -1.50000 H22C 2 0.699598 0.393764 -0.098707 21.00000 -1.50000 AFIX 0 C23 1 0.903112 0.248848 0.014326 21.00000 0.08622 0.15495 = 0.07108 -0.06058 -0.02599 0.06339 AFIX 137 H23A 2 0.956846 0.325763 -0.006747 21.00000 -1.50000 H23B 2 0.923314 0.186490 -0.041510 21.00000 -1.50000 H23C 2 0.949225 0.221040 0.084471 21.00000 -1.50000 AFIX 0 C24 1 0.622352 0.150691 0.050660 21.00000 0.15603 0.04537 = 0.05301 -0.01011 -0.00711 -0.01955 AFIX 137 H24A 2 0.665649 0.112886 0.117765 21.00000 -1.50000 H24B 2 0.630975 0.092355 -0.009805 21.00000 -1.50000 H24C 2 0.505462 0.173271 0.060504 21.00000 -1.50000 PART 2 -21 AFIX 0 C24' 1 0.717952 0.139053 0.061675 -21.00000 0.16468 0.05179 = 0.06046 -0.01935 -0.01285 -0.02090 AFIX 137 H24D 2 0.807228 0.123686 0.115143 -21.00000 -1.50000 H24E 2 0.731152 0.084175 -0.000923 -21.00000 -1.50000 H24F 2 0.609976 0.123984 0.095471 -21.00000 -1.50000 AFIX 0 C23' 1 0.903603 0.287501 -0.024185 -21.00000 0.06099 0.11769 = 0.09365 -0.07750 0.01359 -0.00395 AFIX 137 H23D 2 0.917785 0.373733 -0.044375 -21.00000 -1.50000 H23E 2 0.915963 0.235930 -0.089049 -21.00000 -1.50000 H23F 2 0.988125 0.264825 0.030506 -21.00000 -1.50000 AFIX 0 C22' 1 0.597296 0.319363 -0.050044 -21.00000 0.08161 0.16509 = 0.07028 -0.05802 -0.02219 0.01771 AFIX 137 H22D 2 0.489839 0.320144 -0.013104 -21.00000 -1.50000 H22E 2 0.588978 0.268521 -0.115805 -21.00000 -1.50000 H22F 2 0.627657 0.403193 -0.070445 -21.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM ga_230417b_a.res in P2(1) REM wR2 = 0.0793, GooF = S = 1.059, Restrained GooF = 1.058 for all data REM R1 = 0.0295 for 3944 Fo > 4sig(Fo) and 0.0305 for all 4049 data REM 297 parameters refined using 44 restraints END WGHT 0.0387 0.1694 REM Highest difference peak 0.321, deepest hole -0.186, 1-sigma level 0.027 Q1 1 0.6816 0.5142 0.0627 11.00000 0.05 0.32 ; _shelx_res_checksum 96809 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 N1 N 0.74673(18) 0.49473(15) 0.24123(13) 0.0304(3) Uani 1 1 d . . . . . O1 O 0.76537(19) 0.31256(13) 0.34135(13) 0.0431(4) Uani 1 1 d . . . . . O2 O 0.53048(16) 0.55458(14) 0.57686(11) 0.0371(3) Uani 1 1 d . . . . . O3 O 0.7054(2) 0.33934(15) 0.12638(13) 0.0550(4) Uani 1 1 d . . . . . O4 O 0.7997(3) 0.51639(19) 0.06028(14) 0.0754(7) Uani 1 1 d . . . . . C1 C 0.7502(2) 0.42257(18) 0.33668(16) 0.0316(4) Uani 1 1 d . . . . . C2 C 0.5541(2) 0.48108(17) 0.48289(15) 0.0306(4) Uani 1 1 d . . . . . H2 H 0.550211 0.393029 0.505324 0.037 Uiso 1 1 calc R U . . . C3 C 0.7295(2) 0.50780(17) 0.43366(15) 0.0296(4) Uani 1 1 d . . . . . C4 C 0.8628(2) 0.48029(19) 0.52239(16) 0.0363(4) Uani 1 1 d . . . . . H4A H 0.871309 0.390573 0.533067 0.044 Uiso 1 1 calc R U . . . H4B H 0.972253 0.510452 0.497761 0.044 Uiso 1 1 calc R U . . . C5 C 0.8205(3) 0.5403(2) 0.62921(17) 0.0414(5) Uani 1 1 d . . . . . C6 C 0.6441(3) 0.5196(2) 0.66265(17) 0.0446(5) Uani 1 1 d . . . . . H6A H 0.627863 0.431985 0.680430 0.054 Uiso 1 1 calc R U . . . H6B H 0.620742 0.568225 0.728944 0.054 Uiso 1 1 calc R U . . . C7 C 0.7408(2) 0.63272(18) 0.38308(15) 0.0286(4) Uani 1 1 d . . . . . C8 C 0.7488(2) 0.62151(18) 0.27009(15) 0.0298(4) Uani 1 1 d . . . . . C9 C 0.7605(2) 0.72249(19) 0.20260(17) 0.0365(4) Uani 1 1 d . . . . . H9 H 0.765472 0.713754 0.125579 0.044 Uiso 1 1 calc R U . . . C10 C 0.7648(2) 0.8373(2) 0.25162(18) 0.0400(5) Uani 1 1 d . . . . . H10 H 0.772114 0.908343 0.207109 0.048 Uiso 1 1 calc R U . . . C11 C 0.7586(2) 0.85055(19) 0.36408(18) 0.0371(4) Uani 1 1 d . . . . . H11 H 0.762828 0.929980 0.395733 0.044 Uiso 1 1 calc R U . . . C12 C 0.7462(2) 0.74770(17) 0.43063(17) 0.0328(4) Uani 1 1 d . . . . . H12 H 0.741490 0.756306 0.507668 0.039 Uiso 1 1 calc R U . . . C13 C 0.4126(2) 0.50460(17) 0.40308(15) 0.0301(4) Uani 1 1 d . . . . . C14 C 0.3221(2) 0.61322(19) 0.40514(17) 0.0360(4) Uani 1 1 d . . . . . H14 H 0.346142 0.673324 0.459164 0.043 Uiso 1 1 calc R U . . . C15 C 0.1963(3) 0.6340(2) 0.32808(19) 0.0438(5) Uani 1 1 d . . . . . H15 H 0.134496 0.708174 0.329803 0.053 Uiso 1 1 calc R U . . . C16 C 0.1612(2) 0.5470(2) 0.24912(18) 0.0432(5) Uani 1 1 d . . . . . H16 H 0.076930 0.562079 0.195723 0.052 Uiso 1 1 calc R U . . . C17 C 0.2485(3) 0.4381(2) 0.24792(18) 0.0435(5) Uani 1 1 d . . . . . H17 H 0.223223 0.377848 0.194260 0.052 Uiso 1 1 calc R U . . . C18 C 0.3734(3) 0.41635(19) 0.32500(16) 0.0369(4) Uani 1 1 d . . . . . H18 H 0.432200 0.340845 0.324364 0.044 Uiso 1 1 calc R U . . . C19 C 0.9266(3) 0.6059(3) 0.6880(2) 0.0565(6) Uani 1 1 d . . . . . H19A H 0.892111 0.642190 0.754419 0.068 Uiso 1 1 calc R U . . . H19B H 1.037532 0.616783 0.663822 0.068 Uiso 1 1 calc R U . . . C20 C 0.7535(3) 0.4523(2) 0.13340(17) 0.0366(4) Uani 1 1 d . . . . . C21 C 0.7263(3) 0.2684(2) 0.02429(19) 0.0506(6) Uani 1 1 d D . . . . C22 C 0.6381(17) 0.3221(9) -0.0729(11) 0.058(2) Uani 0.56(3) 1 d . U P A 1 H22A H 0.525501 0.346840 -0.052416 0.088 Uiso 0.56(3) 1 calc R U P A 1 H22B H 0.631459 0.260711 -0.131201 0.088 Uiso 0.56(3) 1 calc R U P A 1 H22C H 0.699598 0.393764 -0.098707 0.088 Uiso 0.56(3) 1 calc R U P A 1 C23 C 0.903(2) 0.2488(19) 0.0143(13) 0.104(6) Uani 0.56(3) 1 d . U P A 1 H23A H 0.956846 0.325763 -0.006747 0.156 Uiso 0.56(3) 1 calc R U P A 1 H23B H 0.923314 0.186490 -0.041510 0.156 Uiso 0.56(3) 1 calc R U P A 1 H23C H 0.949225 0.221040 0.084471 0.156 Uiso 0.56(3) 1 calc R U P A 1 C24 C 0.622(3) 0.1507(10) 0.0507(9) 0.085(3) Uani 0.56(3) 1 d . U P A 1 H24A H 0.665649 0.112886 0.117765 0.127 Uiso 0.56(3) 1 calc R U P A 1 H24B H 0.630975 0.092355 -0.009805 0.127 Uiso 0.56(3) 1 calc R U P A 1 H24C H 0.505462 0.173271 0.060504 0.127 Uiso 0.56(3) 1 calc R U P A 1 C24' C 0.718(4) 0.1391(14) 0.0617(12) 0.092(5) Uani 0.44(3) 1 d . U P A 2 H24D H 0.807228 0.123686 0.115143 0.139 Uiso 0.44(3) 1 calc R U P A 2 H24E H 0.731152 0.084175 -0.000923 0.139 Uiso 0.44(3) 1 calc R U P A 2 H24F H 0.609976 0.123984 0.095471 0.139 Uiso 0.44(3) 1 calc R U P A 2 C23' C 0.904(2) 0.288(2) -0.0242(19) 0.091(6) Uani 0.44(3) 1 d D U P A 2 H23D H 0.917785 0.373733 -0.044375 0.136 Uiso 0.44(3) 1 calc R U P A 2 H23E H 0.915963 0.235930 -0.089049 0.136 Uiso 0.44(3) 1 calc R U P A 2 H23F H 0.988125 0.264825 0.030506 0.136 Uiso 0.44(3) 1 calc R U P A 2 C22' C 0.597(3) 0.319(2) -0.0500(19) 0.106(7) Uani 0.44(3) 1 d . U P A 2 H22D H 0.489839 0.320144 -0.013104 0.159 Uiso 0.44(3) 1 calc R U P A 2 H22E H 0.588978 0.268521 -0.115805 0.159 Uiso 0.44(3) 1 calc R U P A 2 H22F H 0.627657 0.403193 -0.070445 0.159 Uiso 0.44(3) 1 calc R U P A 2 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 N1 0.0290(8) 0.0320(8) 0.0302(8) -0.0009(7) 0.0021(6) 0.0009(6) O1 0.0545(9) 0.0315(8) 0.0434(8) 0.0005(6) 0.0010(7) 0.0099(6) O2 0.0378(7) 0.0448(8) 0.0288(7) -0.0039(6) 0.0027(5) -0.0001(6) O3 0.0880(12) 0.0414(9) 0.0357(8) -0.0104(7) 0.0098(8) -0.0114(8) O4 0.1295(19) 0.0625(12) 0.0344(9) -0.0025(8) 0.0107(10) -0.0320(12) C1 0.0284(9) 0.0323(11) 0.0342(10) 0.0012(8) 0.0012(7) 0.0043(7) C2 0.0335(9) 0.0304(9) 0.0278(9) 0.0019(7) 0.0013(7) -0.0019(7) C3 0.0269(8) 0.0310(9) 0.0308(9) -0.0001(8) -0.0008(7) 0.0024(7) C4 0.0340(10) 0.0383(11) 0.0366(10) 0.0046(8) -0.0060(8) 0.0034(8) C5 0.0465(11) 0.0413(11) 0.0360(10) 0.0025(9) -0.0115(9) 0.0011(9) C6 0.0518(12) 0.0548(13) 0.0271(9) 0.0004(9) -0.0018(8) -0.0020(10) C7 0.0203(7) 0.0323(9) 0.0332(9) 0.0012(8) 0.0004(6) 0.0006(7) C8 0.0231(8) 0.0328(10) 0.0333(9) -0.0002(8) 0.0000(6) 0.0016(7) C9 0.0344(10) 0.0396(11) 0.0353(10) 0.0066(9) -0.0009(8) 0.0007(8) C10 0.0392(10) 0.0340(10) 0.0469(12) 0.0095(9) -0.0002(8) 0.0010(8) C11 0.0300(9) 0.0296(10) 0.0517(12) -0.0003(9) 0.0007(8) 0.0007(8) C12 0.0280(9) 0.0334(10) 0.0372(10) -0.0019(8) 0.0027(7) 0.0020(8) C13 0.0278(8) 0.0312(9) 0.0313(9) 0.0054(8) 0.0037(7) -0.0037(7) C14 0.0317(9) 0.0344(10) 0.0420(11) 0.0017(8) 0.0034(8) -0.0014(8) C15 0.0332(10) 0.0441(12) 0.0541(13) 0.0096(10) 0.0016(9) 0.0041(9) C16 0.0299(9) 0.0582(13) 0.0414(11) 0.0142(10) -0.0025(8) -0.0061(9) C17 0.0408(11) 0.0529(13) 0.0366(11) 0.0002(9) -0.0027(9) -0.0097(9) C18 0.0376(10) 0.0366(10) 0.0363(10) 0.0019(8) -0.0019(8) -0.0020(8) C19 0.0566(14) 0.0565(15) 0.0560(15) -0.0087(12) -0.0169(11) 0.0013(11) C20 0.0363(10) 0.0420(11) 0.0316(10) -0.0034(8) 0.0016(8) -0.0015(8) C21 0.0709(15) 0.0455(12) 0.0352(12) -0.0125(10) -0.0048(10) 0.0041(11) C22 0.071(6) 0.057(4) 0.046(4) -0.018(3) -0.022(4) 0.009(3) C23 0.086(6) 0.155(12) 0.071(7) -0.061(7) -0.026(5) 0.063(7) C24 0.156(10) 0.045(4) 0.053(4) -0.010(3) -0.007(6) -0.020(6) C24' 0.165(16) 0.052(5) 0.060(5) -0.019(4) -0.013(8) -0.021(9) C23' 0.061(6) 0.118(11) 0.094(12) -0.078(10) 0.014(7) -0.004(7) C22' 0.082(10) 0.165(15) 0.070(10) -0.058(8) -0.022(7) 0.018(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 N1 C1 126.67(17) . . ? C20 N1 C8 123.55(16) . . ? C1 N1 C8 109.60(15) . . ? C2 O2 C6 110.76(15) . . ? C20 O3 C21 121.11(18) . . ? O1 C1 N1 126.52(18) . . ? O1 C1 C3 125.67(18) . . ? N1 C1 C3 107.81(15) . . ? O2 C2 C13 108.81(15) . . ? O2 C2 C3 109.70(14) . . ? C13 C2 C3 113.07(15) . . ? C7 C3 C1 103.01(15) . . ? C7 C3 C4 114.97(15) . . ? C1 C3 C4 110.48(15) . . ? C7 C3 C2 112.76(14) . . ? C1 C3 C2 107.13(15) . . ? C4 C3 C2 108.15(15) . . ? C5 C4 C3 111.42(16) . . ? C19 C5 C6 122.7(2) . . ? C19 C5 C4 124.0(2) . . ? C6 C5 C4 113.37(17) . . ? O2 C6 C5 110.80(17) . . ? C12 C7 C8 119.79(18) . . ? C12 C7 C3 130.65(17) . . ? C8 C7 C3 109.56(16) . . ? C9 C8 C7 121.98(18) . . ? C9 C8 N1 128.68(18) . . ? C7 C8 N1 109.32(16) . . ? C8 C9 C10 117.50(19) . . ? C11 C10 C9 121.5(2) . . ? C10 C11 C12 120.1(2) . . ? C7 C12 C11 119.12(19) . . ? C18 C13 C14 119.23(18) . . ? C18 C13 C2 119.31(17) . . ? C14 C13 C2 121.45(17) . . ? C13 C14 C15 120.09(19) . . ? C16 C15 C14 120.2(2) . . ? C17 C16 C15 119.96(19) . . ? C16 C17 C18 120.2(2) . . ? C17 C18 C13 120.3(2) . . ? O4 C20 O3 126.9(2) . . ? O4 C20 N1 121.9(2) . . ? O3 C20 N1 111.21(18) . . ? C23 C21 O3 105.7(6) . . ? C22' C21 O3 103.7(9) . . ? C22' C21 C24' 120.9(12) . . ? O3 C21 C24' 103.3(6) . . ? C23 C21 C22 116.6(7) . . ? O3 C21 C22 114.2(5) . . ? C22' C21 C23' 110.5(10) . . ? O3 C21 C23' 111.3(6) . . ? C24' C21 C23' 106.8(10) . . ? C23 C21 C24 115.1(8) . . ? O3 C21 C24 100.8(4) . . ? C22 C21 C24 103.7(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 N1 C20 1.402(3) . ? N1 C1 1.410(2) . ? N1 C8 1.428(2) . ? O1 C1 1.208(2) . ? O2 C2 1.418(2) . ? O2 C6 1.435(2) . ? O3 C20 1.295(3) . ? O3 C21 1.483(3) . ? O4 C20 1.199(3) . ? C1 C3 1.520(3) . ? C2 C13 1.512(3) . ? C2 C3 1.568(2) . ? C3 C7 1.501(3) . ? C3 C4 1.546(2) . ? C4 C5 1.506(3) . ? C5 C19 1.320(3) . ? C5 C6 1.498(3) . ? C7 C12 1.384(3) . ? C7 C8 1.392(3) . ? C8 C9 1.382(3) . ? C9 C10 1.390(3) . ? C10 C11 1.387(3) . ? C11 C12 1.392(3) . ? C13 C18 1.391(3) . ? C13 C14 1.391(3) . ? C14 C15 1.394(3) . ? C15 C16 1.383(3) . ? C16 C17 1.380(3) . ? C17 C18 1.390(3) . ? C21 C23 1.443(16) . ? C21 C22' 1.48(2) . ? C21 C24' 1.485(16) . ? C21 C22 1.498(12) . ? C21 C23' 1.565(15) . ? C21 C24 1.568(13) . ? 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 N1 C1 O1 2.8(3) . . . . ? C8 N1 C1 O1 -172.50(18) . . . . ? C20 N1 C1 C3 -176.68(16) . . . . ? C8 N1 C1 C3 8.06(19) . . . . ? C6 O2 C2 C13 169.62(15) . . . . ? C6 O2 C2 C3 -66.21(19) . . . . ? O1 C1 C3 C7 172.32(18) . . . . ? N1 C1 C3 C7 -8.24(18) . . . . ? O1 C1 C3 C4 49.0(3) . . . . ? N1 C1 C3 C4 -131.53(16) . . . . ? O1 C1 C3 C2 -68.5(2) . . . . ? N1 C1 C3 C2 110.89(16) . . . . ? O2 C2 C3 C7 -69.82(19) . . . . ? C13 C2 C3 C7 51.8(2) . . . . ? O2 C2 C3 C1 177.55(14) . . . . ? C13 C2 C3 C1 -60.80(19) . . . . ? O2 C2 C3 C4 58.45(19) . . . . ? C13 C2 C3 C4 -179.90(15) . . . . ? C7 C3 C4 C5 78.0(2) . . . . ? C1 C3 C4 C5 -165.91(17) . . . . ? C2 C3 C4 C5 -49.0(2) . . . . ? C3 C4 C5 C19 -131.5(2) . . . . ? C3 C4 C5 C6 47.9(2) . . . . ? C2 O2 C6 C5 62.8(2) . . . . ? C19 C5 C6 O2 126.2(2) . . . . ? C4 C5 C6 O2 -53.2(2) . . . . ? C1 C3 C7 C12 -173.36(17) . . . . ? C4 C3 C7 C12 -53.1(2) . . . . ? C2 C3 C7 C12 71.5(2) . . . . ? C1 C3 C7 C8 5.66(18) . . . . ? C4 C3 C7 C8 125.91(17) . . . . ? C2 C3 C7 C8 -109.48(16) . . . . ? C12 C7 C8 C9 -0.6(2) . . . . ? C3 C7 C8 C9 -179.78(16) . . . . ? C12 C7 C8 N1 178.05(15) . . . . ? C3 C7 C8 N1 -1.09(19) . . . . ? C20 N1 C8 C9 -1.3(3) . . . . ? C1 N1 C8 C9 174.10(17) . . . . ? C20 N1 C8 C7 -179.91(16) . . . . ? C1 N1 C8 C7 -4.48(19) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? N1 C8 C9 C10 -178.17(18) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? C8 C7 C12 C11 0.4(2) . . . . ? C3 C7 C12 C11 179.31(18) . . . . ? C10 C11 C12 C7 0.2(3) . . . . ? O2 C2 C13 C18 -157.21(16) . . . . ? C3 C2 C13 C18 80.6(2) . . . . ? O2 C2 C13 C14 23.6(2) . . . . ? C3 C2 C13 C14 -98.6(2) . . . . ? C18 C13 C14 C15 -1.5(3) . . . . ? C2 C13 C14 C15 177.75(17) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C17 1.3(3) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C13 -0.8(3) . . . . ? C14 C13 C18 C17 1.9(3) . . . . ? C2 C13 C18 C17 -177.30(18) . . . . ? C21 O3 C20 O4 9.3(4) . . . . ? C21 O3 C20 N1 -170.42(19) . . . . ? C1 N1 C20 O4 -157.0(2) . . . . ? C8 N1 C20 O4 17.6(3) . . . . ? C1 N1 C20 O3 22.7(3) . . . . ? C8 N1 C20 O3 -162.68(17) . . . . ? C20 O3 C21 C23 69.6(9) . . . . ? C20 O3 C21 C22' -73.7(11) . . . . ? C20 O3 C21 C24' 159.4(12) . . . . ? C20 O3 C21 C22 -59.8(6) . . . . ? C20 O3 C21 C23' 45.2(13) . . . . ? C20 O3 C21 C24 -170.2(8) . . . . ?