#------------------------------------------------------------------------------ #$Date: 2024-10-03 03:47:25 +0300 (Thu, 03 Oct 2024) $ #$Revision: 295000 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160165.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_7160165 loop_ _publ_author_name 'Budnikov, Alexander' 'Krylov, Igor' 'Shevchenko, Mikhail I.' "Sokova, Lyubov' Sokova L." 'Liu, Yan' 'Yu, Bing' 'Terent'ev, Alexander Olegovich' _publ_section_title ; Synthesis of \w-functionalized ketones from strained cyclic alcohols by ring-opening and cross-recombination between alkyl and N-oxyl radicals ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01490A _journal_year 2024 _chemical_absolute_configuration unk _chemical_formula_moiety 'C18 H15 N O4' _chemical_formula_sum 'C18 H15 N O4' _chemical_formula_weight 309.31 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-07-30 deposited with the CCDC. 2024-10-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.22790(10) _cell_length_b 13.8547(4) _cell_length_c 20.1340(6) _cell_measurement_reflns_used 9876 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.44 _cell_measurement_theta_min 2.50 _cell_volume 1458.33(7) _computing_cell_refinement 'SAINT (Bruker, 2019)' _computing_data_collection 'APEX3 (Bruker, 2019)' _computing_data_reduction 'SAINT (Bruker, 2019)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker AXS D8 QUEST, Photon III detector' _diffrn_measurement_method '\f and \w shutterless scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_unetI/netI 0.0169 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 45414 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.528 _diffrn_reflns_theta_min 1.784 _diffrn_source 'sealed X-Ray tube' _diffrn_source_current 30 _diffrn_source_power 50 _diffrn_source_size '0.6 mm, fine-focus' _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.7121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.590 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.302 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Flack x determined using 1750 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 4467 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0316 _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^)+(0.0490P)^2^+0.3091P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.0845 _reflns_Friedel_coverage 0.728 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 4249 _reflns_number_total 4467 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01490a3.cif _cod_data_source_block BUD _cod_database_code 7160165 _shelx_shelxl_version_number 2018/3 _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 0.943 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL BUD_a.res in P2(1)2(1)2(1) BUD.res created by SHELXL-2018/3 at 14:11:27 on 21-Jan-2022 CELL 0.71073 5.2279 13.8547 20.1340 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0004 0.0006 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 72 60 4 16 LIST 4 TEMP -173.150 SIZE 0.090 0.120 0.590 ACTA L.S. 4 FMAP 2 PLAN 5 HTAB BOND $H CONF WGHT 0.049000 0.309100 FVAR 0.75355 O1 4 0.495499 0.738064 0.349074 11.00000 0.01764 0.01598 = 0.01918 0.00172 -0.00440 -0.00445 O2 4 0.226928 0.769309 0.268497 11.00000 0.01934 0.01960 = 0.02463 -0.00219 -0.00589 -0.00239 O3 4 1.029461 0.862718 0.417212 11.00000 0.02371 0.02217 = 0.01855 0.00468 -0.00775 -0.00578 O4 4 0.581089 0.472937 0.434805 11.00000 0.02432 0.02329 = 0.01963 0.00440 -0.00691 -0.00431 N1 3 0.693782 0.768687 0.392214 11.00000 0.01795 0.01663 = 0.01515 0.00413 -0.00415 -0.00428 C1 1 0.847683 0.845535 0.380266 11.00000 0.01709 0.01358 = 0.01288 0.00073 -0.00004 -0.00078 C2 1 0.776388 0.906182 0.322802 11.00000 0.01412 0.01343 = 0.01177 0.00021 0.00030 0.00136 C3 1 0.922651 0.987594 0.308336 11.00000 0.01681 0.01442 = 0.01711 0.00034 0.00010 -0.00123 AFIX 43 H3 2 1.063142 1.004835 0.335810 11.00000 -1.20000 AFIX 0 C4 1 0.860620 1.043161 0.253328 11.00000 0.02045 0.01452 = 0.01865 0.00226 0.00191 0.00035 AFIX 43 H4 2 0.958999 1.098942 0.243306 11.00000 -1.20000 AFIX 0 C5 1 0.655066 1.017994 0.212506 11.00000 0.02239 0.01772 = 0.01671 0.00354 -0.00061 0.00367 AFIX 43 H5 2 0.616700 1.055935 0.174487 11.00000 -1.20000 AFIX 0 C6 1 0.506879 0.937830 0.227296 11.00000 0.01811 0.01830 = 0.01537 -0.00001 -0.00224 0.00251 AFIX 43 H6 2 0.365735 0.921018 0.199922 11.00000 -1.20000 AFIX 0 C7 1 0.567639 0.881970 0.283017 11.00000 0.01415 0.01301 = 0.01438 -0.00132 -0.00027 0.00093 C8 1 0.414389 0.796200 0.297891 11.00000 0.01671 0.01385 = 0.01547 -0.00188 0.00023 0.00132 C9 1 0.738724 0.695588 0.442880 11.00000 0.01810 0.01538 = 0.01331 0.00400 0.00185 -0.00068 AFIX 23 H9A 2 0.575101 0.662729 0.452952 11.00000 -1.20000 H9B 2 0.797714 0.727721 0.484040 11.00000 -1.20000 AFIX 0 C10 1 0.935682 0.620165 0.422456 11.00000 0.01631 0.01890 = 0.01969 0.00419 0.00336 -0.00025 AFIX 23 H10A 2 1.102509 0.651994 0.414608 11.00000 -1.20000 H10B 2 0.881215 0.589251 0.380442 11.00000 -1.20000 AFIX 0 C11 1 0.965943 0.543100 0.476254 11.00000 0.01389 0.01796 = 0.02322 0.00513 -0.00129 -0.00077 AFIX 23 H11A 2 1.126398 0.506965 0.468275 11.00000 -1.20000 H11B 2 0.980606 0.575133 0.520042 11.00000 -1.20000 AFIX 0 C12 1 0.744367 0.472611 0.478134 11.00000 0.01486 0.01389 = 0.01531 0.00028 0.00053 0.00108 C13 1 0.730654 0.400720 0.533635 11.00000 0.01423 0.01373 = 0.01418 -0.00055 -0.00078 0.00161 C14 1 0.527135 0.334882 0.534214 11.00000 0.01558 0.01682 = 0.01771 -0.00015 -0.00121 0.00007 AFIX 43 H14 2 0.404054 0.335944 0.499509 11.00000 -1.20000 AFIX 0 C15 1 0.504638 0.268005 0.585388 11.00000 0.01855 0.01726 = 0.02304 0.00184 0.00251 0.00025 AFIX 43 H15 2 0.365516 0.223896 0.585770 11.00000 -1.20000 AFIX 0 C16 1 0.685831 0.265606 0.636092 11.00000 0.02212 0.02052 = 0.01870 0.00511 0.00242 0.00445 AFIX 43 H16 2 0.668979 0.220464 0.671337 11.00000 -1.20000 AFIX 0 C17 1 0.891063 0.329199 0.635109 11.00000 0.01969 0.02352 = 0.01722 0.00171 -0.00312 0.00456 AFIX 43 H17 2 1.016509 0.326573 0.669198 11.00000 -1.20000 AFIX 0 C18 1 0.913479 0.396953 0.584168 11.00000 0.01514 0.01814 = 0.01712 -0.00015 -0.00194 0.00131 AFIX 43 H18 2 1.053500 0.440656 0.583849 11.00000 -1.20000 AFIX 0 HKLF 4 REM BUD_a.res in P2(1)2(1)2(1) REM wR2 = 0.084502, GooF = S = 1.02651, Restrained GooF = 1.02651 for all data REM R1 = 0.031646 for 4249 Fo > 4sig(Fo) and 0.034194 for all 4467 data REM 208 parameters refined using 0 restraints END WGHT 0.0490 0.3091 REM Instructions for potential hydrogen bonds HTAB C9 O4 EQIV $1 x+1, y, z HTAB C11 O4_$1 REM Highest difference peak 0.302, deepest hole -0.197, 1-sigma level 0.047 Q1 1 0.5838 0.9834 0.2255 11.00000 0.05 0.30 Q2 1 0.7360 0.4393 0.5077 11.00000 0.05 0.29 Q3 1 0.8101 0.8751 0.3510 11.00000 0.05 0.28 Q4 1 0.5218 0.9176 0.2607 11.00000 0.05 0.27 Q5 1 0.4972 0.8422 0.2910 11.00000 0.05 0.27 ; _shelx_res_checksum 78934 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, 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 0.4955(2) 0.73806(7) 0.34907(5) 0.0176(2) Uani 1 1 d . . . . . O2 O 0.2269(2) 0.76931(8) 0.26850(6) 0.0212(2) Uani 1 1 d . . . . . O3 O 1.0295(2) 0.86272(8) 0.41721(5) 0.0215(2) Uani 1 1 d . . . . . O4 O 0.5811(2) 0.47294(8) 0.43480(5) 0.0224(2) Uani 1 1 d . . . . . N1 N 0.6938(2) 0.76869(9) 0.39221(6) 0.0166(2) Uani 1 1 d . . . . . C1 C 0.8477(3) 0.84553(10) 0.38027(7) 0.0145(2) Uani 1 1 d . . . . . C2 C 0.7764(3) 0.90618(9) 0.32280(6) 0.0131(2) Uani 1 1 d . . . . . C3 C 0.9227(3) 0.98759(10) 0.30834(7) 0.0161(3) Uani 1 1 d . . . . . H3 H 1.063142 1.004835 0.335810 0.019 Uiso 1 1 calc R U . . . C4 C 0.8606(3) 1.04316(10) 0.25333(7) 0.0179(3) Uani 1 1 d . . . . . H4 H 0.958999 1.098942 0.243306 0.021 Uiso 1 1 calc R U . . . C5 C 0.6551(3) 1.01799(10) 0.21251(7) 0.0189(3) Uani 1 1 d . . . . . H5 H 0.616700 1.055935 0.174487 0.023 Uiso 1 1 calc R U . . . C6 C 0.5069(3) 0.93783(10) 0.22730(7) 0.0173(3) Uani 1 1 d . . . . . H6 H 0.365735 0.921018 0.199922 0.021 Uiso 1 1 calc R U . . . C7 C 0.5676(3) 0.88197(9) 0.28302(6) 0.0138(2) Uani 1 1 d . . . . . C8 C 0.4144(3) 0.79620(10) 0.29789(7) 0.0153(2) Uani 1 1 d . . . . . C9 C 0.7387(3) 0.69559(10) 0.44288(7) 0.0156(2) Uani 1 1 d . . . . . H9A H 0.575101 0.662729 0.452952 0.019 Uiso 1 1 calc R U . . . H9B H 0.797714 0.727721 0.484040 0.019 Uiso 1 1 calc R U . . . C10 C 0.9357(3) 0.62016(10) 0.42246(7) 0.0183(3) Uani 1 1 d . . . . . H10A H 1.102509 0.651994 0.414608 0.022 Uiso 1 1 calc R U . . . H10B H 0.881215 0.589251 0.380442 0.022 Uiso 1 1 calc R U . . . C11 C 0.9659(3) 0.54310(10) 0.47625(8) 0.0184(3) Uani 1 1 d . . . . . H11A H 1.126398 0.506965 0.468275 0.022 Uiso 1 1 calc R U . . . H11B H 0.980606 0.575133 0.520042 0.022 Uiso 1 1 calc R U . . . C12 C 0.7444(3) 0.47261(9) 0.47813(7) 0.0147(2) Uani 1 1 d . . . . . C13 C 0.7307(3) 0.40072(9) 0.53363(7) 0.0140(2) Uani 1 1 d . . . . . C14 C 0.5271(3) 0.33488(10) 0.53421(7) 0.0167(3) Uani 1 1 d . . . . . H14 H 0.404054 0.335944 0.499509 0.020 Uiso 1 1 calc R U . . . C15 C 0.5046(3) 0.26800(11) 0.58539(7) 0.0196(3) Uani 1 1 d . . . . . H15 H 0.365516 0.223896 0.585770 0.024 Uiso 1 1 calc R U . . . C16 C 0.6858(3) 0.26561(11) 0.63609(7) 0.0204(3) Uani 1 1 d . . . . . H16 H 0.668979 0.220464 0.671337 0.025 Uiso 1 1 calc R U . . . C17 C 0.8911(3) 0.32920(11) 0.63511(7) 0.0201(3) Uani 1 1 d . . . . . H17 H 1.016509 0.326573 0.669198 0.024 Uiso 1 1 calc R U . . . C18 C 0.9135(3) 0.39695(10) 0.58417(7) 0.0168(3) Uani 1 1 d . . . . . H18 H 1.053500 0.440656 0.583849 0.020 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 0.0176(5) 0.0160(4) 0.0192(5) 0.0017(4) -0.0044(4) -0.0044(4) O2 0.0193(5) 0.0196(5) 0.0246(5) -0.0022(4) -0.0059(4) -0.0024(4) O3 0.0237(5) 0.0222(5) 0.0186(5) 0.0047(4) -0.0078(4) -0.0058(4) O4 0.0243(5) 0.0233(5) 0.0196(5) 0.0044(4) -0.0069(4) -0.0043(4) N1 0.0180(5) 0.0166(5) 0.0151(5) 0.0041(4) -0.0041(4) -0.0043(4) C1 0.0171(6) 0.0136(6) 0.0129(5) 0.0007(4) 0.0000(5) -0.0008(5) C2 0.0141(5) 0.0134(5) 0.0118(5) 0.0002(4) 0.0003(4) 0.0014(5) C3 0.0168(6) 0.0144(6) 0.0171(6) 0.0003(5) 0.0001(5) -0.0012(5) C4 0.0205(6) 0.0145(6) 0.0186(6) 0.0023(5) 0.0019(5) 0.0004(5) C5 0.0224(7) 0.0177(6) 0.0167(6) 0.0035(5) -0.0006(5) 0.0037(5) C6 0.0181(6) 0.0183(6) 0.0154(6) 0.0000(5) -0.0022(5) 0.0025(5) C7 0.0142(5) 0.0130(5) 0.0144(5) -0.0013(4) -0.0003(4) 0.0009(5) C8 0.0167(6) 0.0139(5) 0.0155(6) -0.0019(5) 0.0002(5) 0.0013(5) C9 0.0181(6) 0.0154(6) 0.0133(6) 0.0040(4) 0.0018(5) -0.0007(5) C10 0.0163(6) 0.0189(6) 0.0197(6) 0.0042(5) 0.0034(5) -0.0002(5) C11 0.0139(6) 0.0180(6) 0.0232(6) 0.0051(5) -0.0013(5) -0.0008(5) C12 0.0149(5) 0.0139(5) 0.0153(6) 0.0003(4) 0.0005(4) 0.0011(5) C13 0.0142(5) 0.0137(5) 0.0142(5) -0.0005(4) -0.0008(5) 0.0016(4) C14 0.0156(6) 0.0168(6) 0.0177(6) -0.0002(5) -0.0012(5) 0.0001(5) C15 0.0186(6) 0.0173(6) 0.0230(6) 0.0018(5) 0.0025(5) 0.0003(5) C16 0.0221(7) 0.0205(6) 0.0187(6) 0.0051(5) 0.0024(5) 0.0044(6) C17 0.0197(7) 0.0235(7) 0.0172(6) 0.0017(5) -0.0031(5) 0.0046(5) C18 0.0151(6) 0.0181(6) 0.0171(6) -0.0001(5) -0.0019(5) 0.0013(5) 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 C8 O1 N1 120.63(10) . . ? C1 N1 O1 124.07(11) . . ? C1 N1 C9 125.06(12) . . ? O1 N1 C9 109.82(10) . . ? O3 C1 N1 120.20(12) . . ? O3 C1 C2 123.94(12) . . ? N1 C1 C2 115.83(12) . . ? C3 C2 C7 120.27(12) . . ? C3 C2 C1 119.05(12) . . ? C7 C2 C1 120.68(12) . . ? C4 C3 C2 119.20(13) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.73(13) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.22(13) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.23(13) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 120.33(12) . . ? C2 C7 C8 120.39(12) . . ? C6 C7 C8 119.25(12) . . ? O2 C8 O1 115.99(12) . . ? O2 C8 C7 126.59(13) . . ? O1 C8 C7 117.39(12) . . ? N1 C9 C10 113.38(11) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 110.96(11) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 112.86(12) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? O4 C12 C13 120.13(12) . . ? O4 C12 C11 120.95(12) . . ? C13 C12 C11 118.91(12) . . ? C18 C13 C14 119.28(12) . . ? C18 C13 C12 122.36(12) . . ? C14 C13 C12 118.37(12) . . ? C15 C14 C13 120.27(13) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.09(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.99(13) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.15(13) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.20(13) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? 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 C8 1.3750(17) . ? O1 N1 1.4174(15) . ? O2 C8 1.2040(17) . ? O3 C1 1.2301(17) . ? O4 C12 1.2205(17) . ? N1 C1 1.3560(17) . ? N1 C9 1.4565(17) . ? C1 C2 1.4777(18) . ? C2 C3 1.3935(19) . ? C2 C7 1.3947(18) . ? C3 C4 1.3873(19) . ? C3 H3 0.9500 . ? C4 C5 1.397(2) . ? C4 H4 0.9500 . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 C7 1.3995(18) . ? C6 H6 0.9500 . ? C7 C8 1.4641(19) . ? C9 C10 1.524(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5291(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5156(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.4986(18) . ? C13 C18 1.3969(18) . ? C13 C14 1.4015(19) . ? C14 C15 1.391(2) . ? C14 H14 0.9500 . ? C15 C16 1.393(2) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.395(2) . ? C17 H17 0.9500 . ? C18 H18 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 C8 O1 N1 C1 -12.68(19) . . . . ? C8 O1 N1 C9 178.52(12) . . . . ? O1 N1 C1 O3 -173.79(13) . . . . ? C9 N1 C1 O3 -6.7(2) . . . . ? O1 N1 C1 C2 8.08(19) . . . . ? C9 N1 C1 C2 175.17(12) . . . . ? O3 C1 C2 C3 0.6(2) . . . . ? N1 C1 C2 C3 178.66(12) . . . . ? O3 C1 C2 C7 179.88(13) . . . . ? N1 C1 C2 C7 -2.07(19) . . . . ? C7 C2 C3 C4 -1.1(2) . . . . ? C1 C2 C3 C4 178.19(13) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C3 C2 C7 C6 1.6(2) . . . . ? C1 C2 C7 C6 -177.70(12) . . . . ? C3 C2 C7 C8 179.69(13) . . . . ? C1 C2 C7 C8 0.43(19) . . . . ? C5 C6 C7 C2 -0.6(2) . . . . ? C5 C6 C7 C8 -178.77(13) . . . . ? N1 O1 C8 O2 -171.99(12) . . . . ? N1 O1 C8 C7 10.12(18) . . . . ? C2 C7 C8 O2 177.91(13) . . . . ? C6 C7 C8 O2 -3.9(2) . . . . ? C2 C7 C8 O1 -4.45(19) . . . . ? C6 C7 C8 O1 173.70(12) . . . . ? C1 N1 C9 C10 -79.39(17) . . . . ? O1 N1 C9 C10 89.27(14) . . . . ? N1 C9 C10 C11 -177.51(11) . . . . ? C9 C10 C11 C12 75.17(15) . . . . ? C10 C11 C12 O4 8.7(2) . . . . ? C10 C11 C12 C13 -172.37(11) . . . . ? O4 C12 C13 C18 179.59(13) . . . . ? C11 C12 C13 C18 0.69(19) . . . . ? O4 C12 C13 C14 -0.06(19) . . . . ? C11 C12 C13 C14 -178.96(12) . . . . ? C18 C13 C14 C15 1.4(2) . . . . ? C12 C13 C14 C15 -178.91(13) . . . . ? C13 C14 C15 C16 -0.6(2) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 1.4(2) . . . . ? C16 C17 C18 C13 -0.5(2) . . . . ? C14 C13 C18 C17 -0.9(2) . . . . ? C12 C13 C18 C17 179.43(13) . . . . ?