#------------------------------------------------------------------------------ #$Date: 2021-07-13 06:57:07 +0300 (Tue, 13 Jul 2021) $ #$Revision: 267483 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158168.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_7158168 loop_ _publ_author_name 'Lai, Huifang' 'Xu, Jiexin' 'Lin, Jin' 'Zha, Daijun' _publ_section_title ; Copper-promoted Direct Amidation of Isoindolinone Scaffolds by Sodium Persulfate ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01054A _journal_year 2021 _chemical_formula_moiety 'C16 H12 N2 O2' _chemical_formula_sum 'C16 H12 N2 O2' _chemical_formula_weight 264.28 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _audit_creation_date 2021-01-20 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2021-03-01 deposited with the CCDC. 2021-07-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.006(6) _cell_length_b 6.157(2) _cell_length_c 27.288(10) _cell_measurement_reflns_used 5896 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 27.4894 _cell_measurement_theta_min 2.0169 _cell_volume 2521.2(16) _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 173.15 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_unetI/netI 0.0677 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 14357 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.478 _diffrn_reflns_theta_min 2.986 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.392 _exptl_crystal_description Prism _exptl_crystal_F_000 1104 _refine_diff_density_max 0.214 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2798 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0511 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0737P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1295 _refine_ls_wR_factor_ref 0.1475 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1836 _reflns_number_total 2798 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01054a2.cif _cod_data_source_block biisoindoline _cod_original_cell_volume 2521.3(16) _cod_database_code 7158168 _shelxl_version_number 2014/6 _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, All N(H) groups 2.a Ternary CH refined with riding coordinates: C14(H14) 2.b Secondary CH2 refined with riding coordinates: C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: N2(H2), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20) ; _shelx_res_file ; TITL a in Pbca CELL 0.71073 15.0062 6.1571 27.2881 90 90 90 ZERR 8 0.0055 0.0022 0.01 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 128 96 16 16 L.S. 4 PLAN 5 TEMP -100 CONF GRID BOND MORE -1 BOND $H fmap 2 acta MERG 2 REM REM REM WGHT 0.073700 FVAR 0.42437 O1 4 0.819417 -0.017594 0.347947 11.00000 0.07578 0.03998 = 0.05280 -0.00110 0.00542 0.01321 N2 3 0.838059 -0.566098 0.417488 11.00000 0.04273 0.04979 = 0.05365 0.01149 -0.00828 -0.00336 AFIX 43 H2 2 0.780331 -0.572213 0.411984 11.00000 -1.20000 AFIX 0 O3 4 0.849930 -0.887593 0.460045 11.00000 0.07846 0.04955 = 0.06457 0.01535 -0.00941 -0.01483 N4 3 0.889729 -0.352669 0.348523 11.00000 0.05487 0.03636 = 0.04425 0.00113 -0.00320 0.00641 C5 1 0.850911 -0.176039 0.326777 11.00000 0.04572 0.03380 = 0.04664 0.00166 0.00074 -0.00061 C6 1 0.983793 -0.454378 0.419116 11.00000 0.04613 0.04513 = 0.03712 -0.00399 -0.00082 -0.00306 C7 1 0.977397 -0.653341 0.442373 11.00000 0.04720 0.04776 = 0.03835 -0.00390 -0.00356 0.00534 C8 1 0.856138 -0.215194 0.273377 11.00000 0.03766 0.03799 = 0.04582 0.00335 0.00126 -0.00129 C9 1 0.894152 -0.417074 0.265156 11.00000 0.04253 0.03867 = 0.04825 -0.00125 -0.00027 0.00106 C10 1 0.882451 -0.723742 0.441725 11.00000 0.05572 0.03833 = 0.04182 0.00121 -0.00458 -0.00123 C11 1 0.827645 -0.083529 0.235310 11.00000 0.04763 0.04453 = 0.05117 0.00832 0.00428 0.00259 AFIX 43 H11 2 0.801611 0.054397 0.241519 11.00000 -1.20000 AFIX 0 C12 1 0.838351 -0.159547 0.187892 11.00000 0.05912 0.06371 = 0.04475 0.01041 0.00332 0.00131 AFIX 43 H12 2 0.818921 -0.073457 0.161050 11.00000 -1.20000 AFIX 0 C13 1 0.915209 -0.521984 0.313364 11.00000 0.05592 0.03917 = 0.05292 -0.00159 -0.00289 0.00976 AFIX 23 H13A 2 0.879754 -0.655845 0.318244 11.00000 -1.20000 H13B 2 0.979372 -0.557544 0.315976 11.00000 -1.20000 AFIX 0 C14 1 0.892808 -0.386033 0.401236 11.00000 0.05291 0.03743 = 0.04147 0.00185 -0.00204 -0.00143 AFIX 13 H14 2 0.874011 -0.250100 0.418422 11.00000 -1.20000 AFIX 0 C15 1 0.877125 -0.359891 0.179317 11.00000 0.06246 0.06798 = 0.04510 -0.00282 0.00875 -0.00066 AFIX 43 H15 2 0.884255 -0.408685 0.146523 11.00000 -1.20000 AFIX 0 C16 1 0.905843 -0.491210 0.217538 11.00000 0.05476 0.05142 = 0.05676 -0.00610 0.00634 0.00514 AFIX 43 H16 2 0.932763 -0.628078 0.211280 11.00000 -1.20000 AFIX 0 C17 1 1.051787 -0.748962 0.463619 11.00000 0.06161 0.06924 = 0.04712 -0.00406 -0.00582 0.02195 AFIX 43 H17 2 1.047410 -0.886178 0.479355 11.00000 -1.20000 AFIX 0 C18 1 1.063789 -0.345823 0.416440 11.00000 0.06002 0.07381 = 0.04863 -0.00787 0.00403 -0.01938 AFIX 43 H18 2 1.068307 -0.209524 0.400314 11.00000 -1.20000 AFIX 0 C19 1 1.132043 -0.640816 0.461410 11.00000 0.05055 0.11835 = 0.04586 -0.01196 -0.00363 0.02201 AFIX 43 H19 2 1.183479 -0.703417 0.475985 11.00000 -1.20000 AFIX 0 C20 1 1.138328 -0.442660 0.438244 11.00000 0.04478 0.12369 = 0.05394 -0.02126 0.00292 -0.01813 AFIX 43 H20 2 1.194222 -0.370409 0.437037 11.00000 -1.20000 AFIX 0 HKLF 4 REM a in Pbca REM R1 = 0.0511 for 1836 Fo > 4sig(Fo) and 0.0898 for all 2798 data REM 181 parameters refined using 0 restraints END WGHT 0.0737 0.0000 REM Highest difference peak 0.214, deepest hole -0.189, 1-sigma level 0.042 Q1 1 0.8835 -0.0030 0.3474 11.00000 0.05 0.16 Q2 1 0.8595 -0.2438 0.4089 11.00000 0.05 0.14 Q3 1 0.8543 -0.3277 0.3433 11.00000 0.05 0.14 Q4 1 0.9777 -0.5326 0.4390 11.00000 0.05 0.14 Q5 1 0.8988 -0.4565 0.2790 11.00000 0.05 0.13 ; _shelx_res_checksum 23543 _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -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 O1 O 0.81942(10) -0.0176(2) 0.34795(5) 0.0562(4) Uani 1 1 d . . . . . N2 N 0.83806(10) -0.5661(2) 0.41749(6) 0.0487(4) Uani 1 1 d . . . . . H2 H 0.7803 -0.5722 0.4120 0.058 Uiso 1 1 calc R U . . . O3 O 0.84993(11) -0.8876(2) 0.46004(5) 0.0642(5) Uani 1 1 d . . . . . N4 N 0.88973(10) -0.3527(2) 0.34852(6) 0.0452(4) Uani 1 1 d . . . . . C5 C 0.85091(12) -0.1760(3) 0.32678(7) 0.0421(4) Uani 1 1 d . . . . . C6 C 0.98379(12) -0.4544(3) 0.41912(6) 0.0428(4) Uani 1 1 d . . . . . C7 C 0.97740(12) -0.6533(3) 0.44237(6) 0.0444(4) Uani 1 1 d . . . . . C8 C 0.85614(11) -0.2152(3) 0.27338(7) 0.0405(4) Uani 1 1 d . . . . . C9 C 0.89415(12) -0.4171(3) 0.26516(7) 0.0431(4) Uani 1 1 d . . . . . C10 C 0.88245(13) -0.7237(3) 0.44172(7) 0.0453(5) Uani 1 1 d . . . . . C11 C 0.82764(13) -0.0835(3) 0.23531(7) 0.0478(5) Uani 1 1 d . . . . . H11 H 0.8016 0.0544 0.2415 0.057 Uiso 1 1 calc R U . . . C12 C 0.83835(14) -0.1595(4) 0.18789(7) 0.0559(5) Uani 1 1 d . . . . . H12 H 0.8189 -0.0735 0.1611 0.067 Uiso 1 1 calc R U . . . C13 C 0.91521(14) -0.5220(3) 0.31336(7) 0.0493(5) Uani 1 1 d . . . . . H13A H 0.8798 -0.6558 0.3182 0.059 Uiso 1 1 calc R U . . . H13B H 0.9794 -0.5575 0.3160 0.059 Uiso 1 1 calc R U . . . C14 C 0.89281(12) -0.3860(3) 0.40124(7) 0.0439(4) Uani 1 1 d . . . . . H14 H 0.8740 -0.2501 0.4184 0.053 Uiso 1 1 calc R U . . . C15 C 0.87713(15) -0.3599(4) 0.17932(8) 0.0585(6) Uani 1 1 d . . . . . H15 H 0.8843 -0.4087 0.1465 0.070 Uiso 1 1 calc R U . . . C16 C 0.90584(13) -0.4912(3) 0.21754(7) 0.0543(5) Uani 1 1 d . . . . . H16 H 0.9328 -0.6281 0.2113 0.065 Uiso 1 1 calc R U . . . C17 C 1.05179(15) -0.7490(4) 0.46362(7) 0.0593(6) Uani 1 1 d . . . . . H17 H 1.0474 -0.8862 0.4794 0.071 Uiso 1 1 calc R U . . . C18 C 1.06379(14) -0.3458(4) 0.41644(7) 0.0608(6) Uani 1 1 d . . . . . H18 H 1.0683 -0.2095 0.4003 0.073 Uiso 1 1 calc R U . . . C19 C 1.13204(15) -0.6408(5) 0.46141(8) 0.0716(7) Uani 1 1 d . . . . . H19 H 1.1835 -0.7034 0.4760 0.086 Uiso 1 1 calc R U . . . C20 C 1.13833(15) -0.4427(5) 0.43824(9) 0.0741(7) Uani 1 1 d . . . . . H20 H 1.1942 -0.3704 0.4370 0.089 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 O1 0.0758(10) 0.0400(8) 0.0528(8) -0.0011(6) 0.0054(7) 0.0132(7) N2 0.0427(9) 0.0498(9) 0.0536(10) 0.0115(8) -0.0083(7) -0.0034(7) O3 0.0785(11) 0.0496(9) 0.0646(10) 0.0153(7) -0.0094(8) -0.0148(7) N4 0.0549(10) 0.0364(8) 0.0443(9) 0.0011(7) -0.0032(7) 0.0064(7) C5 0.0457(10) 0.0338(9) 0.0466(11) 0.0017(8) 0.0007(8) -0.0006(8) C6 0.0461(10) 0.0451(10) 0.0371(9) -0.0040(8) -0.0008(7) -0.0031(8) C7 0.0472(10) 0.0478(10) 0.0384(10) -0.0039(8) -0.0036(8) 0.0053(9) C8 0.0377(9) 0.0380(9) 0.0458(10) 0.0034(8) 0.0013(7) -0.0013(8) C9 0.0425(10) 0.0387(10) 0.0482(11) -0.0013(8) -0.0003(8) 0.0011(8) C10 0.0557(11) 0.0383(10) 0.0418(10) 0.0012(8) -0.0046(8) -0.0012(9) C11 0.0476(11) 0.0445(11) 0.0512(12) 0.0083(9) 0.0043(8) 0.0026(9) C12 0.0591(13) 0.0637(13) 0.0448(11) 0.0104(10) 0.0033(9) 0.0013(11) C13 0.0559(12) 0.0392(10) 0.0529(12) -0.0016(8) -0.0029(9) 0.0098(9) C14 0.0529(11) 0.0374(9) 0.0415(10) 0.0018(8) -0.0020(8) -0.0014(8) C15 0.0625(13) 0.0680(14) 0.0451(12) -0.0028(10) 0.0088(9) -0.0007(11) C16 0.0548(12) 0.0514(12) 0.0568(13) -0.0061(9) 0.0063(9) 0.0051(10) C17 0.0616(14) 0.0692(14) 0.0471(12) -0.0041(10) -0.0058(9) 0.0220(11) C18 0.0600(13) 0.0738(14) 0.0486(12) -0.0079(10) 0.0040(10) -0.0194(11) C19 0.0506(13) 0.118(2) 0.0459(13) -0.0120(13) -0.0036(10) 0.0220(14) C20 0.0448(13) 0.124(2) 0.0539(14) -0.0213(15) 0.0029(10) -0.0181(14) 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 C10 N2 H2 122.6 . . ? C10 N2 C14 114.84(16) . . ? C14 N2 H2 122.6 . . ? C5 N4 C13 113.07(15) . . ? C5 N4 C14 123.69(15) . . ? C14 N4 C13 122.56(14) . . ? O1 C5 N4 126.21(18) . . ? O1 C5 C8 127.82(17) . . ? N4 C5 C8 105.96(15) . . ? C7 C6 C14 109.42(15) . . ? C18 C6 C7 121.01(18) . . ? C18 C6 C14 129.53(17) . . ? C6 C7 C10 108.59(15) . . ? C6 C7 C17 120.75(19) . . ? C17 C7 C10 130.58(19) . . ? C9 C8 C5 109.12(15) . . ? C11 C8 C5 128.83(17) . . ? C11 C8 C9 122.04(17) . . ? C8 C9 C13 109.34(16) . . ? C8 C9 C16 119.89(17) . . ? C16 C9 C13 130.76(17) . . ? N2 C10 C7 105.58(16) . . ? O3 C10 N2 126.46(18) . . ? O3 C10 C7 127.94(17) . . ? C8 C11 H11 121.1 . . ? C8 C11 C12 117.83(19) . . ? C12 C11 H11 121.1 . . ? C11 C12 H12 119.7 . . ? C15 C12 C11 120.52(19) . . ? C15 C12 H12 119.7 . . ? N4 C13 C9 102.28(14) . . ? N4 C13 H13A 111.3 . . ? N4 C13 H13B 111.3 . . ? C9 C13 H13A 111.3 . . ? C9 C13 H13B 111.3 . . ? H13A C13 H13B 109.2 . . ? N2 C14 N4 113.13(14) . . ? N2 C14 C6 101.57(14) . . ? N2 C14 H14 109.7 . . ? N4 C14 C6 112.82(15) . . ? N4 C14 H14 109.7 . . ? C6 C14 H14 109.7 . . ? C12 C15 H15 119.2 . . ? C12 C15 C16 121.51(19) . . ? C16 C15 H15 119.2 . . ? C9 C16 H16 120.9 . . ? C15 C16 C9 118.19(19) . . ? C15 C16 H16 120.9 . . ? C7 C17 H17 120.7 . . ? C19 C17 C7 118.7(2) . . ? C19 C17 H17 120.7 . . ? C6 C18 H18 121.1 . . ? C6 C18 C20 117.9(2) . . ? C20 C18 H18 121.1 . . ? C17 C19 H19 119.7 . . ? C17 C19 C20 120.5(2) . . ? C20 C19 H19 119.7 . . ? C18 C20 H20 119.4 . . ? C19 C20 C18 121.2(2) . . ? C19 C20 H20 119.4 . . ? 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 O1 C5 1.228(2) . ? N2 H2 0.8800 . ? N2 C10 1.350(2) . ? N2 C14 1.449(2) . ? O3 C10 1.227(2) . ? N4 C5 1.369(2) . ? N4 C13 1.467(2) . ? N4 C14 1.454(2) . ? C5 C8 1.479(2) . ? C6 C7 1.383(3) . ? C6 C14 1.510(3) . ? C6 C18 1.376(3) . ? C7 C10 1.489(3) . ? C7 C17 1.389(3) . ? C8 C9 1.386(2) . ? C8 C11 1.385(3) . ? C9 C13 1.499(3) . ? C9 C16 1.388(3) . ? C11 H11 0.9500 . ? C11 C12 1.385(3) . ? C12 H12 0.9500 . ? C12 C15 1.384(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14 1.0000 . ? C15 H15 0.9500 . ? C15 C16 1.388(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C17 C19 1.377(3) . ? C18 H18 0.9500 . ? C18 C20 1.400(3) . ? C19 H19 0.9500 . ? C19 C20 1.377(4) . ? C20 H20 0.9500 . ? 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 O1 C5 C8 C9 -178.18(18) . . . . ? O1 C5 C8 C11 0.4(3) . . . . ? N4 C5 C8 C9 2.58(19) . . . . ? N4 C5 C8 C11 -178.79(18) . . . . ? C5 N4 C13 C9 5.0(2) . . . . ? C5 N4 C14 N2 111.56(19) . . . . ? C5 N4 C14 C6 -133.83(17) . . . . ? C5 C8 C9 C13 0.5(2) . . . . ? C5 C8 C9 C16 179.73(15) . . . . ? C5 C8 C11 C12 -178.57(16) . . . . ? C6 C7 C10 N2 1.1(2) . . . . ? C6 C7 C10 O3 -177.49(19) . . . . ? C6 C7 C17 C19 0.5(3) . . . . ? C6 C18 C20 C19 0.4(3) . . . . ? C7 C6 C14 N2 0.38(19) . . . . ? C7 C6 C14 N4 -121.03(16) . . . . ? C7 C6 C18 C20 -0.3(3) . . . . ? C7 C17 C19 C20 -0.5(3) . . . . ? C8 C9 C13 N4 -3.1(2) . . . . ? C8 C9 C16 C15 -1.1(3) . . . . ? C8 C11 C12 C15 -0.6(3) . . . . ? C9 C8 C11 C12 -0.1(3) . . . . ? C10 N2 C14 N4 121.57(18) . . . . ? C10 N2 C14 C6 0.4(2) . . . . ? C10 C7 C17 C19 -175.71(19) . . . . ? C11 C8 C9 C13 -178.26(17) . . . . ? C11 C8 C9 C16 1.0(3) . . . . ? C11 C12 C15 C16 0.4(3) . . . . ? C12 C15 C16 C9 0.4(3) . . . . ? C13 N4 C5 O1 175.95(18) . . . . ? C13 N4 C5 C8 -4.8(2) . . . . ? C13 N4 C14 N2 -58.3(2) . . . . ? C13 N4 C14 C6 56.3(2) . . . . ? C13 C9 C16 C15 177.93(19) . . . . ? C14 N2 C10 O3 177.73(18) . . . . ? C14 N2 C10 C7 -0.9(2) . . . . ? C14 N4 C5 O1 5.2(3) . . . . ? C14 N4 C5 C8 -175.53(14) . . . . ? C14 N4 C13 C9 175.82(14) . . . . ? C14 C6 C7 C10 -0.9(2) . . . . ? C14 C6 C7 C17 -177.90(16) . . . . ? C14 C6 C18 C20 176.98(19) . . . . ? C16 C9 C13 N4 177.76(18) . . . . ? C17 C7 C10 N2 177.70(19) . . . . ? C17 C7 C10 O3 -0.9(3) . . . . ? C17 C19 C20 C18 0.1(3) . . . . ? C18 C6 C7 C10 176.89(16) . . . . ? C18 C6 C7 C17 -0.1(3) . . . . ? C18 C6 C14 N2 -177.19(18) . . . . ? C18 C6 C14 N4 61.4(2) . . . . ?