#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:29:40 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252917 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157487.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_7157487 loop_ _publ_author_name 'Sreedharan, Ramdas' 'Rajeshwaran, Purushothaman' 'Panyam, Pradeep Kumar Reddy' 'Yadav, Saurabh' 'Nagaraja, C. M.' 'Gandhi, Thirumanavelan' _publ_section_title ; Acylation of oxindoles using methyl/phenyl esters via the mixed Claisen condensation - an access to 3-alkylideneoxindoles. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3843 _journal_page_last 3847 _journal_paper_doi 10.1039/d0ob00789g _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C17 H14 N O3' _chemical_formula_weight 280.29 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-10-18 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.1920(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.1312(4) _cell_length_b 8.2115(4) _cell_length_c 16.7219(7) _cell_measurement_temperature 273(2) _cell_volume 1443.50(11) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.992 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_unetI/netI 0.0443 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14276 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.390 _diffrn_reflns_theta_min 2.579 _exptl_absorpt_coefficient_mu 0.089 _exptl_crystal_density_diffrn 1.290 _exptl_crystal_F_000 588 _refine_diff_density_max 0.469 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2941 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0607 _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^)+(0.0954P)^2^+0.4481P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1766 _refine_ls_wR_factor_ref 0.1844 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2496 _reflns_number_total 2941 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00789g2.cif _cod_data_source_block shelx_CCDC1 _cod_depositor_comments 'Adding full bibliography for 7157486--7157487.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7157487 _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 SIR92 run in space group P 21/c CELL 0.71073 11.1312 8.2115 16.7219 90.000 109.192 90.000 ZERR 4.00 0.0004 0.0004 0.0007 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 68 56 4 12 MERG 2 FMAP 2 PLAN 25 ACTA CONF L.S. 10 TEMP 0.00 WGHT 0.095400 0.448100 FVAR 0.48073 O2 4 0.955076 0.097574 0.617732 11.00000 0.06950 0.05798 = 0.06922 -0.00399 0.03401 -0.01219 O3 4 0.793607 0.343744 0.679302 11.00000 0.08263 0.04330 = 0.07488 -0.00258 0.00554 0.01416 O1 4 0.852682 -0.062736 0.472513 11.00000 0.09158 0.07323 = 0.05428 0.00293 0.03782 -0.00374 N1 3 0.662403 -0.186177 0.464930 11.00000 0.07966 0.05575 = 0.04080 -0.00315 0.01220 -0.00144 C4 1 0.648118 -0.119999 0.594283 11.00000 0.04986 0.04069 = 0.04525 0.00688 0.00921 0.00669 C10 1 0.857769 0.040487 0.640007 11.00000 0.05298 0.03756 = 0.04999 0.00345 0.01900 0.00430 C5 1 0.586802 -0.199063 0.517339 11.00000 0.06082 0.04539 = 0.05057 0.00584 0.00512 0.00273 C11 1 0.864675 0.083873 0.727637 11.00000 0.04307 0.04445 = 0.04843 -0.00531 0.01205 0.00061 C3 1 0.765401 -0.053231 0.587479 11.00000 0.05514 0.03979 = 0.03979 0.00398 0.01472 0.00502 C16 1 0.835209 0.240715 0.746771 11.00000 0.04188 0.04674 = 0.05929 -0.00988 0.00699 0.00220 C2 1 0.769182 -0.097235 0.503705 11.00000 0.06928 0.04412 = 0.04308 0.00474 0.01740 0.00412 C9 1 0.589866 -0.118047 0.656145 11.00000 0.05552 0.06295 = 0.05816 0.00907 0.01839 0.00946 AFIX 43 H9 2 0.628610 -0.066590 0.707766 11.00000 -1.20000 AFIX 0 C12 1 0.903859 -0.029970 0.790982 11.00000 0.06850 0.05471 = 0.05224 0.00180 0.01678 0.01008 AFIX 43 H12 2 0.921790 -0.135289 0.777839 11.00000 -1.20000 AFIX 0 C6 1 0.470882 -0.273583 0.500876 11.00000 0.06472 0.06541 = 0.07415 0.00013 -0.00251 -0.00702 AFIX 43 H6 2 0.431542 -0.325303 0.449414 11.00000 -1.20000 AFIX 0 C8 1 0.472860 -0.194227 0.639552 11.00000 0.05479 0.08721 = 0.08887 0.01732 0.02806 0.00606 AFIX 43 H8 2 0.433379 -0.194469 0.680682 11.00000 -1.20000 AFIX 0 C15 1 0.848485 0.280014 0.830154 11.00000 0.05694 0.06864 = 0.07062 -0.02935 0.01413 0.00418 AFIX 43 H15 2 0.828799 0.384350 0.843591 11.00000 -1.20000 AFIX 0 C7 1 0.414458 -0.269490 0.562926 11.00000 0.05301 0.08360 = 0.10656 0.01469 0.01137 -0.00795 AFIX 43 H7 2 0.335514 -0.318435 0.552881 11.00000 -1.20000 AFIX 0 C14 1 0.890505 0.165163 0.892391 11.00000 0.07598 0.10144 = 0.04925 -0.01647 0.01309 0.00774 AFIX 43 H14 2 0.901204 0.193356 0.948175 11.00000 -1.20000 AFIX 0 C13 1 0.917254 0.008660 0.874020 11.00000 0.08355 0.08647 = 0.05003 0.00407 0.01356 0.01165 AFIX 43 H13 2 0.943756 -0.069426 0.916496 11.00000 -1.20000 AFIX 0 C1 1 0.628993 -0.249323 0.378997 11.00000 0.12387 0.07766 = 0.04860 -0.01596 0.01465 -0.00379 AFIX 33 H1A 2 0.550157 -0.307922 0.365139 11.00000 -1.50000 H1B 2 0.619947 -0.160485 0.340134 11.00000 -1.50000 H1C 2 0.694849 -0.321190 0.375070 11.00000 -1.50000 AFIX 0 C17 1 0.763212 0.506419 0.694256 11.00000 0.10041 0.04814 = 0.11666 -0.00951 -0.00373 0.02216 AFIX 33 H17A 2 0.735428 0.564966 0.641655 11.00000 -1.50000 H17B 2 0.696480 0.505832 0.718843 11.00000 -1.50000 H17C 2 0.837183 0.558422 0.732380 11.00000 -1.50000 AFIX 0 HKLF 4 REM SIR92 run in space group P 21/c REM R1 = 0.0607 for 2496 Fo > 4sig(Fo) and 0.0686 for all 2941 data REM 190 parameters refined using 0 restraints END WGHT 0.0951 0.4505 REM Highest difference peak 0.469, deepest hole -0.187, 1-sigma level 0.041 Q1 1 0.9418 0.0468 0.5624 11.00000 0.05 0.47 Q2 1 0.6185 -0.3744 0.3829 11.00000 0.05 0.27 Q3 1 0.5348 -0.1844 0.3439 11.00000 0.05 0.26 Q4 1 0.7174 -0.2054 0.3578 11.00000 0.05 0.23 Q5 1 0.7671 0.5406 0.6299 11.00000 0.05 0.16 Q6 1 0.7741 0.0340 0.5966 11.00000 0.05 0.16 Q7 1 0.7650 -0.0645 0.4351 11.00000 0.05 0.16 Q8 1 0.8799 0.2824 0.7868 11.00000 0.05 0.16 Q9 1 0.8244 -0.0674 0.6175 11.00000 0.05 0.16 Q10 1 0.8629 0.0745 0.8622 11.00000 0.05 0.15 Q11 1 0.5994 -0.1800 0.4749 11.00000 0.05 0.14 Q12 1 0.8486 0.0573 0.6841 11.00000 0.05 0.14 Q13 1 0.8070 0.3530 0.6273 11.00000 0.05 0.14 Q14 1 0.8224 0.5524 0.7509 11.00000 0.05 0.13 Q15 1 0.8233 0.1408 0.7337 11.00000 0.05 0.13 Q16 1 0.6817 0.5351 0.6585 11.00000 0.05 0.13 Q17 1 0.7349 -0.1190 0.6102 11.00000 0.05 0.12 Q18 1 0.7734 -0.0725 0.5563 11.00000 0.05 0.12 Q19 1 0.6985 -0.0385 0.5888 11.00000 0.05 0.12 Q20 1 0.6625 -0.2076 0.4329 11.00000 0.05 0.11 Q21 1 0.6028 -0.1354 0.5531 11.00000 0.05 0.10 Q22 1 0.7576 0.2860 0.6192 11.00000 0.05 0.10 Q23 1 0.8456 0.2972 0.7121 11.00000 0.05 0.10 Q24 1 0.8957 0.1728 0.7440 11.00000 0.05 0.10 Q25 1 0.9217 0.0634 0.7536 11.00000 0.05 0.10 ; _shelx_res_checksum 61455 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 O2 O 0.95508(15) 0.09757(18) 0.61773(10) 0.0628(4) Uani 1 1 d . . . . . O3 O 0.79361(16) 0.34374(17) 0.67930(10) 0.0719(5) Uani 1 1 d . . . . . O1 O 0.85268(17) -0.0627(2) 0.47251(10) 0.0696(5) Uani 1 1 d . . . . . N1 N 0.66240(18) -0.1862(2) 0.46493(10) 0.0606(5) Uani 1 1 d . . . . . C4 C 0.64812(17) -0.1200(2) 0.59428(11) 0.0468(4) Uani 1 1 d . . . . . C10 C 0.85777(18) 0.0405(2) 0.64001(12) 0.0463(4) Uani 1 1 d . . . . . C5 C 0.5868(2) -0.1991(2) 0.51734(12) 0.0555(5) Uani 1 1 d . . . . . C11 C 0.86468(17) 0.0839(2) 0.72764(11) 0.0461(4) Uani 1 1 d . . . . . C3 C 0.76540(18) -0.0532(2) 0.58748(11) 0.0451(4) Uani 1 1 d . . . . . C16 C 0.83521(17) 0.2407(2) 0.74677(13) 0.0517(5) Uani 1 1 d . . . . . C2 C 0.7692(2) -0.0972(2) 0.50370(12) 0.0524(5) Uani 1 1 d . . . . . C9 C 0.5899(2) -0.1180(3) 0.65614(14) 0.0589(5) Uani 1 1 d . . . . . H9 H 0.6286 -0.0666 0.7078 0.071 Uiso 1 1 calc R U . . . C12 C 0.9039(2) -0.0300(3) 0.79098(13) 0.0592(5) Uani 1 1 d . . . . . H12 H 0.9218 -0.1353 0.7778 0.071 Uiso 1 1 calc R U . . . C6 C 0.4709(2) -0.2736(3) 0.50088(17) 0.0743(7) Uani 1 1 d . . . . . H6 H 0.4315 -0.3253 0.4494 0.089 Uiso 1 1 calc R U . . . C8 C 0.4729(2) -0.1942(3) 0.63955(18) 0.0759(7) Uani 1 1 d . . . . . H8 H 0.4334 -0.1945 0.6807 0.091 Uiso 1 1 calc R U . . . C15 C 0.8485(2) 0.2800(3) 0.83015(15) 0.0671(6) Uani 1 1 d . . . . . H15 H 0.8288 0.3843 0.8436 0.080 Uiso 1 1 calc R U . . . C7 C 0.4145(2) -0.2695(4) 0.5629(2) 0.0847(8) Uani 1 1 d . . . . . H7 H 0.3355 -0.3184 0.5529 0.102 Uiso 1 1 calc R U . . . C14 C 0.8905(2) 0.1652(4) 0.89239(15) 0.0774(7) Uani 1 1 d . . . . . H14 H 0.9012 0.1934 0.9482 0.093 Uiso 1 1 calc R U . . . C13 C 0.9173(3) 0.0087(3) 0.87402(15) 0.0754(7) Uani 1 1 d . . . . . H13 H 0.9438 -0.0694 0.9165 0.090 Uiso 1 1 calc R U . . . C1 C 0.6290(3) -0.2493(4) 0.37900(15) 0.0867(9) Uani 1 1 d . . . . . H1A H 0.5502 -0.3079 0.3651 0.130 Uiso 1 1 calc R U . . . H1B H 0.6199 -0.1605 0.3401 0.130 Uiso 1 1 calc R U . . . H1C H 0.6948 -0.3212 0.3751 0.130 Uiso 1 1 calc R U . . . C17 C 0.7632(3) 0.5064(3) 0.6943(2) 0.0981(10) Uani 1 1 d . . . . . H17A H 0.7354 0.5650 0.6417 0.147 Uiso 1 1 calc R U . . . H17B H 0.6965 0.5058 0.7188 0.147 Uiso 1 1 calc R U . . . H17C H 0.8372 0.5584 0.7324 0.147 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 O2 0.0695(9) 0.0580(8) 0.0692(9) -0.0040(7) 0.0340(8) -0.0122(7) O3 0.0826(11) 0.0433(8) 0.0749(10) -0.0026(7) 0.0055(8) 0.0142(7) O1 0.0916(11) 0.0732(10) 0.0543(9) 0.0029(7) 0.0378(8) -0.0037(8) N1 0.0797(12) 0.0558(10) 0.0408(9) -0.0031(7) 0.0122(8) -0.0014(8) C4 0.0499(10) 0.0407(9) 0.0452(9) 0.0069(7) 0.0092(8) 0.0067(7) C10 0.0530(10) 0.0376(8) 0.0500(10) 0.0034(7) 0.0190(8) 0.0043(7) C5 0.0608(11) 0.0454(10) 0.0506(11) 0.0058(8) 0.0051(9) 0.0027(8) C11 0.0431(9) 0.0445(9) 0.0484(10) -0.0053(7) 0.0120(7) 0.0006(7) C3 0.0551(10) 0.0398(9) 0.0398(9) 0.0040(7) 0.0147(7) 0.0050(7) C16 0.0419(9) 0.0467(10) 0.0593(11) -0.0099(8) 0.0070(8) 0.0022(7) C2 0.0693(12) 0.0441(9) 0.0431(10) 0.0047(7) 0.0174(9) 0.0041(8) C9 0.0555(11) 0.0630(12) 0.0582(12) 0.0091(10) 0.0184(9) 0.0095(9) C12 0.0685(13) 0.0547(11) 0.0522(11) 0.0018(9) 0.0168(9) 0.0101(9) C6 0.0647(14) 0.0654(14) 0.0741(15) 0.0001(12) -0.0025(12) -0.0070(11) C8 0.0548(12) 0.0872(17) 0.0889(17) 0.0173(14) 0.0281(12) 0.0061(12) C15 0.0569(12) 0.0686(14) 0.0706(14) -0.0294(11) 0.0141(10) 0.0042(10) C7 0.0530(13) 0.0836(18) 0.107(2) 0.0147(16) 0.0114(14) -0.0079(12) C14 0.0760(15) 0.101(2) 0.0492(12) -0.0165(12) 0.0131(11) 0.0077(14) C13 0.0836(16) 0.0865(17) 0.0500(12) 0.0041(11) 0.0136(11) 0.0116(13) C1 0.124(2) 0.0777(17) 0.0486(12) -0.0160(12) 0.0146(13) -0.0038(15) C17 0.100(2) 0.0481(13) 0.117(2) -0.0095(14) -0.0037(17) 0.0222(13) 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 C16 O3 C17 118.3(2) . . ? C2 N1 C5 110.55(16) . . ? C2 N1 C1 124.0(2) . . ? C5 N1 C1 125.3(2) . . ? C9 C4 C5 118.88(19) . . ? C9 C4 C3 134.77(18) . . ? C5 C4 C3 106.35(16) . . ? O2 C10 C3 122.01(17) . . ? O2 C10 C11 113.94(16) . . ? C3 C10 C11 124.01(17) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 N1 128.7(2) . . ? C4 C5 N1 109.09(17) . . ? C12 C11 C16 119.48(18) . . ? C12 C11 C10 119.90(16) . . ? C16 C11 C10 120.60(17) . . ? C10 C3 C4 132.40(17) . . ? C10 C3 C2 120.56(17) . . ? C4 C3 C2 106.94(16) . . ? O3 C16 C15 125.50(19) . . ? O3 C16 C11 115.18(17) . . ? C15 C16 C11 119.32(19) . . ? O1 C2 N1 125.42(18) . . ? O1 C2 C3 127.54(19) . . ? N1 C2 C3 107.04(17) . . ? C8 C9 C4 118.9(2) . . ? C11 C12 C13 121.4(2) . . ? C5 C6 C7 118.0(2) . . ? C7 C8 C9 120.9(2) . . ? C14 C15 C16 120.0(2) . . ? C8 C7 C6 121.2(2) . . ? C15 C14 C13 121.3(2) . . ? C14 C13 C12 118.6(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 O2 C10 1.341(2) . ? O3 C16 1.364(3) . ? O3 C17 1.420(3) . ? O1 C2 1.239(3) . ? N1 C2 1.364(3) . ? N1 C5 1.404(3) . ? N1 C1 1.456(3) . ? C4 C9 1.390(3) . ? C4 C5 1.402(3) . ? C4 C3 1.454(3) . ? C10 C3 1.352(3) . ? C10 C11 1.485(3) . ? C5 C6 1.372(3) . ? C11 C12 1.372(3) . ? C11 C16 1.392(3) . ? C3 C2 1.461(3) . ? C16 C15 1.391(3) . ? C9 C8 1.388(3) . ? C12 C13 1.384(3) . ? C6 C7 1.379(4) . ? C8 C7 1.378(4) . ? C15 C14 1.368(4) . ? C14 C13 1.376(4) . ? 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 C9 C4 C5 C6 0.4(3) . . . . ? C3 C4 C5 C6 -178.56(19) . . . . ? C9 C4 C5 N1 -179.85(16) . . . . ? C3 C4 C5 N1 1.1(2) . . . . ? C2 N1 C5 C6 177.8(2) . . . . ? C1 N1 C5 C6 1.4(4) . . . . ? C2 N1 C5 C4 -1.9(2) . . . . ? C1 N1 C5 C4 -178.2(2) . . . . ? O2 C10 C11 C12 -102.4(2) . . . . ? C3 C10 C11 C12 75.2(2) . . . . ? O2 C10 C11 C16 75.8(2) . . . . ? C3 C10 C11 C16 -106.7(2) . . . . ? O2 C10 C3 C4 -175.40(17) . . . . ? C11 C10 C3 C4 7.3(3) . . . . ? O2 C10 C3 C2 0.5(3) . . . . ? C11 C10 C3 C2 -176.79(16) . . . . ? C9 C4 C3 C10 -2.5(4) . . . . ? C5 C4 C3 C10 176.25(19) . . . . ? C9 C4 C3 C2 -178.9(2) . . . . ? C5 C4 C3 C2 -0.09(19) . . . . ? C17 O3 C16 C15 1.4(3) . . . . ? C17 O3 C16 C11 -179.3(2) . . . . ? C12 C11 C16 O3 -178.14(18) . . . . ? C10 C11 C16 O3 3.7(3) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C10 C11 C16 C15 -176.89(18) . . . . ? C5 N1 C2 O1 -178.63(19) . . . . ? C1 N1 C2 O1 -2.2(3) . . . . ? C5 N1 C2 C3 1.8(2) . . . . ? C1 N1 C2 C3 178.2(2) . . . . ? C10 C3 C2 O1 2.5(3) . . . . ? C4 C3 C2 O1 179.38(19) . . . . ? C10 C3 C2 N1 -177.87(16) . . . . ? C4 C3 C2 N1 -1.0(2) . . . . ? C5 C4 C9 C8 -0.1(3) . . . . ? C3 C4 C9 C8 178.5(2) . . . . ? C16 C11 C12 C13 -1.3(3) . . . . ? C10 C11 C12 C13 176.8(2) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? N1 C5 C6 C7 -179.8(2) . . . . ? C4 C9 C8 C7 -0.6(3) . . . . ? O3 C16 C15 C14 179.5(2) . . . . ? C11 C16 C15 C14 0.2(3) . . . . ? C9 C8 C7 C6 0.9(4) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C16 C15 C14 C13 -1.7(4) . . . . ? C15 C14 C13 C12 1.6(4) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ?