#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/61/7116121.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_7116121 loop_ _publ_author_name 'RahulKumar Rajmani Singh' 'Rai-Shung Liu' _publ_section_title ; Gold-catalyzed 1,2-iminonitronation of electron-deficient alkynes with nitrosoarenes to afford alpha-imidoyl nitrones ; _journal_name_full Chem.Commun. _journal_page_first 15864 _journal_paper_doi 10.1039/C4cc06962E _journal_volume 50 _journal_year 2014 _chemical_formula_sum 'C20 H20 N2 O6' _chemical_formula_weight 384.38 _chemical_name_systematic ; ? ; _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _cell_angle_alpha 90 _cell_angle_beta 105.318(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.8424(8) _cell_length_b 10.9091(8) _cell_length_c 16.0091(11) _cell_measurement_reflns_used 9889 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.3804 _cell_measurement_theta_min 2.4586 _cell_volume 1994.7(2) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_unetI/netI 0.0407 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15944 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.402 _diffrn_reflns_theta_min 1.783 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.9485 _exptl_absorpt_correction_T_min 0.8871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/2 (Bruker AXS Inc.)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Tabullar _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.344 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.035 _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 255 _refine_ls_number_reflns 4076 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0480 _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^)+(0.0656P)^2^+0.2652P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1198 _refine_ls_wR_factor_ref 0.1396 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2546 _reflns_number_total 4076 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4cc06962e2.cif _cod_data_source_block mo_140816_0m_a _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 7116121 #BEGIN Tags that were not found in dictionaries: _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL mo_140816_0m in P2(1)/c CELL 0.71073 11.8424 10.9091 16.0091 90.000 105.318 90.000 ZERR 4.00 0.0008 0.0008 0.0011 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H O N UNIT 80 80 24 8 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 TEMP 23.000 WGHT 0.065600 0.265200 FVAR 0.76130 C1 1 0.301500 0.278745 0.504260 11.00000 0.05005 0.04485 = 0.03747 -0.00348 0.00922 0.00440 C2 1 0.394517 0.185828 0.536750 11.00000 0.05512 0.04412 = 0.03784 -0.00560 0.00471 0.00271 C3 1 0.599433 0.149097 0.583873 11.00000 0.05847 0.06442 = 0.08839 -0.00107 0.00299 0.02184 AFIX 23 H3A 2 0.598255 0.130406 0.642873 11.00000 -1.20000 H3B 2 0.594340 0.072771 0.552009 11.00000 -1.20000 AFIX 0 C4 1 0.705336 0.212655 0.583347 11.00000 0.05707 0.14346 = 0.21632 0.07315 0.02387 0.02398 AFIX 137 H4A 2 0.709224 0.223523 0.524665 11.00000 -1.50000 H4B 2 0.771551 0.165638 0.614664 11.00000 -1.50000 H4C 2 0.706081 0.291324 0.610361 11.00000 -1.50000 AFIX 0 C5 1 0.191506 0.240863 0.446664 11.00000 0.04683 0.04781 = 0.03810 -0.00310 0.00899 0.00314 C6 1 0.081272 0.278327 0.467376 11.00000 0.05357 0.05781 = 0.04784 -0.00733 0.01569 0.00096 C7 1 -0.116894 0.335646 0.409865 11.00000 0.05146 0.13501 = 0.10275 -0.02723 0.02334 0.02516 AFIX 23 H7A 2 -0.134158 0.284294 0.454397 11.00000 -1.20000 H7B 2 -0.116181 0.420432 0.428250 11.00000 -1.20000 AFIX 0 C8 1 -0.204476 0.318738 0.329694 11.00000 0.05532 0.21263 = 0.16857 -0.08723 0.00456 0.02501 AFIX 137 H8A 2 -0.182343 0.362682 0.284523 11.00000 -1.50000 H8B 2 -0.278214 0.349149 0.335254 11.00000 -1.50000 H8C 2 -0.211541 0.233057 0.315600 11.00000 -1.50000 AFIX 0 C9 1 0.401911 0.437536 0.603740 11.00000 0.05159 0.04269 = 0.04134 -0.00853 0.01062 0.00551 C10 1 0.418093 0.379319 0.681829 11.00000 0.07109 0.05822 = 0.04548 -0.00212 0.01430 -0.00642 AFIX 43 H10 2 0.372555 0.312014 0.687615 11.00000 -1.20000 AFIX 0 C11 1 0.503508 0.422888 0.751646 11.00000 0.08804 0.08373 = 0.04047 -0.00452 0.00878 -0.00570 AFIX 43 H11 2 0.515800 0.384986 0.805339 11.00000 -1.20000 AFIX 0 C12 1 0.570710 0.522364 0.742157 11.00000 0.07074 0.08975 = 0.05640 -0.02645 0.01020 -0.01006 AFIX 43 H12 2 0.629810 0.549697 0.789060 11.00000 -1.20000 AFIX 0 C13 1 0.550980 0.581339 0.663947 11.00000 0.07119 0.06473 = 0.06813 -0.02211 0.02563 -0.01503 AFIX 43 H13 2 0.595772 0.649326 0.658309 11.00000 -1.20000 AFIX 0 C14 1 0.464995 0.540133 0.593733 11.00000 0.06416 0.04854 = 0.04899 -0.00647 0.01980 0.00219 AFIX 43 H14 2 0.449862 0.580607 0.540802 11.00000 -1.20000 AFIX 0 C15 1 0.091634 0.104264 0.330810 11.00000 0.04603 0.04485 = 0.04385 -0.00590 0.00755 0.00355 C16 1 0.057018 0.120885 0.242754 11.00000 0.06128 0.05889 = 0.04391 -0.00540 0.00853 -0.00274 AFIX 43 H16 2 0.099471 0.171604 0.215514 11.00000 -1.20000 AFIX 0 C17 1 -0.041644 0.061190 0.195417 11.00000 0.07003 0.07783 = 0.05405 -0.01407 0.00022 -0.00062 AFIX 43 H17 2 -0.067377 0.072946 0.135859 11.00000 -1.20000 AFIX 0 C18 1 -0.101422 -0.014862 0.235645 11.00000 0.06721 0.07931 = 0.08284 -0.02861 0.00608 -0.01755 AFIX 43 H18 2 -0.168164 -0.054625 0.203288 11.00000 -1.20000 AFIX 0 C19 1 -0.064786 -0.033695 0.322995 11.00000 0.08234 0.06555 = 0.09218 -0.00894 0.03045 -0.02487 AFIX 43 H19 2 -0.105985 -0.086907 0.349525 11.00000 -1.20000 AFIX 0 C20 1 0.033512 0.026193 0.372180 11.00000 0.06818 0.05540 = 0.05373 0.00162 0.01398 -0.00536 AFIX 43 H20 2 0.059385 0.013779 0.431664 11.00000 -1.20000 AFIX 0 N1 4 0.311738 0.394575 0.529370 11.00000 0.05020 0.04614 = 0.04161 -0.00099 0.00633 0.00892 N2 4 0.194333 0.169369 0.380609 11.00000 0.04282 0.05195 = 0.03881 -0.00383 0.00870 0.00296 O1 3 0.289278 0.148939 0.359195 11.00000 0.04795 0.08004 = 0.05734 -0.01693 0.01763 0.00408 O2 3 0.075394 0.286121 0.540600 11.00000 0.07903 0.12417 = 0.05120 -0.00904 0.02847 0.01059 O3 3 -0.003421 0.303009 0.397488 11.00000 0.04723 0.07373 = 0.05671 -0.00824 0.01269 0.01451 O4 3 0.237165 0.475188 0.491569 11.00000 0.06835 0.05422 = 0.06692 -0.00278 -0.00051 0.02171 O5 3 0.371291 0.083171 0.553218 11.00000 0.07327 0.04595 = 0.06343 0.00570 0.00301 -0.00076 O6 3 0.500793 0.229072 0.543023 11.00000 0.04947 0.04672 = 0.06492 0.00069 0.00823 0.01046 HKLF 4 REM mo_140816_0m in P2(1)/c REM R1 = 0.0480 for 2546 Fo > 4sig(Fo) and 0.0857 for all 4076 data REM 255 parameters refined using 0 restraints END WGHT 0.0656 0.2652 REM Highest difference peak 0.344, deepest hole -0.230, 1-sigma level 0.035 Q1 1 -0.1998 0.2327 0.3958 11.00000 0.05 0.34 Q2 1 -0.1835 0.2906 0.2918 11.00000 0.05 0.15 Q3 1 0.7137 0.2994 0.5534 11.00000 0.05 0.14 Q4 1 0.5580 0.0509 0.5972 11.00000 0.05 0.13 Q5 1 -0.2965 0.3056 0.3477 11.00000 0.05 0.13 ; _shelx_res_checksum 46524 #END Tags that were not found in dictionaries 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 C1 C 0.30150(16) 0.27874(18) 0.50426(12) 0.0446(5) Uani 1 1 d . . C2 C 0.39452(18) 0.18583(19) 0.53675(12) 0.0471(5) Uani 1 1 d . . C3 C 0.59943(19) 0.1491(2) 0.58387(18) 0.0735(7) Uani 1 1 d . . H3A H 0.5983 0.1304 0.6429 0.088 Uiso 1 1 calc R U H3B H 0.5943 0.0728 0.5520 0.088 Uiso 1 1 calc R U C4 C 0.7053(2) 0.2127(4) 0.5833(3) 0.1413(16) Uani 1 1 d . . H4A H 0.7092 0.2235 0.5247 0.212 Uiso 1 1 calc R U H4B H 0.7716 0.1656 0.6147 0.212 Uiso 1 1 calc R U H4C H 0.7061 0.2913 0.6104 0.212 Uiso 1 1 calc R U C5 C 0.19151(16) 0.24086(18) 0.44666(12) 0.0447(5) Uani 1 1 d . . C6 C 0.08127(18) 0.2783(2) 0.46738(14) 0.0526(5) Uani 1 1 d . . C7 C -0.1169(2) 0.3356(3) 0.4099(2) 0.0958(10) Uani 1 1 d . . H7A H -0.1342 0.2843 0.4544 0.115 Uiso 1 1 calc R U H7B H -0.1162 0.4204 0.4282 0.115 Uiso 1 1 calc R U C8 C -0.2045(3) 0.3187(4) 0.3297(3) 0.1502(19) Uani 1 1 d . . H8A H -0.1823 0.3627 0.2845 0.225 Uiso 1 1 calc R U H8B H -0.2782 0.3491 0.3353 0.225 Uiso 1 1 calc R U H8C H -0.2115 0.2331 0.3156 0.225 Uiso 1 1 calc R U C9 C 0.40191(17) 0.43754(18) 0.60374(12) 0.0455(5) Uani 1 1 d . . C10 C 0.4181(2) 0.3793(2) 0.68183(14) 0.0585(6) Uani 1 1 d . . H10 H 0.3726 0.3120 0.6876 0.070 Uiso 1 1 calc R U C11 C 0.5035(2) 0.4229(3) 0.75165(15) 0.0723(7) Uani 1 1 d . . H11 H 0.5158 0.3850 0.8053 0.087 Uiso 1 1 calc R U C12 C 0.5707(2) 0.5224(3) 0.74216(17) 0.0735(7) Uani 1 1 d . . H12 H 0.6298 0.5497 0.7891 0.088 Uiso 1 1 calc R U C13 C 0.5510(2) 0.5813(2) 0.66395(16) 0.0666(6) Uani 1 1 d . . H13 H 0.5958 0.6493 0.6583 0.080 Uiso 1 1 calc R U C14 C 0.46500(18) 0.54013(19) 0.59373(14) 0.0530(5) Uani 1 1 d . . H14 H 0.4499 0.5806 0.5408 0.064 Uiso 1 1 calc R U C15 C 0.09163(16) 0.10426(18) 0.33081(13) 0.0457(5) Uani 1 1 d . . C16 C 0.05702(19) 0.1209(2) 0.24275(13) 0.0557(5) Uani 1 1 d . . H16 H 0.0995 0.1716 0.2155 0.067 Uiso 1 1 calc R U C17 C -0.0416(2) 0.0612(2) 0.19542(16) 0.0704(7) Uani 1 1 d . . H17 H -0.0674 0.0729 0.1359 0.084 Uiso 1 1 calc R U C18 C -0.1014(2) -0.0149(3) 0.2356(2) 0.0791(8) Uani 1 1 d . . H18 H -0.1682 -0.0546 0.2033 0.095 Uiso 1 1 calc R U C19 C -0.0648(2) -0.0337(2) 0.32299(19) 0.0786(8) Uani 1 1 d . . H19 H -0.1060 -0.0869 0.3495 0.094 Uiso 1 1 calc R U C20 C 0.0335(2) 0.0262(2) 0.37218(15) 0.0595(6) Uani 1 1 d . . H20 H 0.0594 0.0138 0.4317 0.071 Uiso 1 1 calc R U N1 N 0.31174(14) 0.39457(15) 0.52937(10) 0.0471(4) Uani 1 1 d . . N2 N 0.19433(13) 0.16937(15) 0.38061(10) 0.0449(4) Uani 1 1 d . . O1 O 0.28928(12) 0.14894(15) 0.35920(9) 0.0611(4) Uani 1 1 d . . O2 O 0.07539(15) 0.28612(19) 0.54060(11) 0.0827(6) Uani 1 1 d . . O3 O -0.00342(12) 0.30301(14) 0.39749(9) 0.0594(4) Uani 1 1 d . . O4 O 0.23716(13) 0.47519(14) 0.49157(10) 0.0666(5) Uani 1 1 d . . O5 O 0.37129(13) 0.08317(14) 0.55322(10) 0.0637(4) Uani 1 1 d . . O6 O 0.50079(12) 0.22907(13) 0.54302(9) 0.0550(4) Uani 1 1 d . . 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 C1 0.0500(11) 0.0448(11) 0.0375(11) -0.0035(9) 0.0092(9) 0.0044(9) C2 0.0551(12) 0.0441(12) 0.0378(11) -0.0056(9) 0.0047(9) 0.0027(10) C3 0.0585(14) 0.0644(16) 0.0884(19) -0.0011(13) 0.0030(13) 0.0218(12) C4 0.0571(18) 0.143(3) 0.216(4) 0.073(3) 0.024(2) 0.0240(19) C5 0.0468(11) 0.0478(12) 0.0381(11) -0.0031(9) 0.0090(8) 0.0031(9) C6 0.0536(12) 0.0578(13) 0.0478(13) -0.0073(10) 0.0157(10) 0.0010(10) C7 0.0515(14) 0.135(3) 0.103(2) -0.027(2) 0.0233(15) 0.0252(16) C8 0.0553(17) 0.213(5) 0.169(4) -0.087(4) 0.005(2) 0.025(2) C9 0.0516(11) 0.0427(11) 0.0413(11) -0.0085(9) 0.0106(9) 0.0055(9) C10 0.0711(14) 0.0582(14) 0.0455(13) -0.0021(11) 0.0143(11) -0.0064(11) C11 0.0880(17) 0.0837(18) 0.0405(13) -0.0045(12) 0.0088(12) -0.0057(15) C12 0.0707(15) 0.090(2) 0.0564(16) -0.0264(14) 0.0102(12) -0.0101(14) C13 0.0712(15) 0.0647(15) 0.0681(16) -0.0221(13) 0.0256(13) -0.0150(12) C14 0.0642(13) 0.0485(12) 0.0490(12) -0.0065(10) 0.0198(10) 0.0022(10) C15 0.0460(10) 0.0449(11) 0.0439(11) -0.0059(9) 0.0076(9) 0.0035(9) C16 0.0613(13) 0.0589(14) 0.0439(12) -0.0054(10) 0.0085(10) -0.0027(11) C17 0.0700(15) 0.0778(17) 0.0540(14) -0.0141(13) 0.0002(12) -0.0006(14) C18 0.0672(16) 0.0793(19) 0.083(2) -0.0286(15) 0.0061(14) -0.0175(14) C19 0.0823(17) 0.0656(16) 0.092(2) -0.0089(15) 0.0305(16) -0.0249(14) C20 0.0682(14) 0.0554(14) 0.0537(13) 0.0016(11) 0.0140(11) -0.0054(11) N1 0.0502(9) 0.0461(10) 0.0416(9) -0.0010(8) 0.0063(8) 0.0089(8) N2 0.0428(9) 0.0519(10) 0.0388(9) -0.0038(8) 0.0087(7) 0.0030(8) O1 0.0479(8) 0.0800(11) 0.0573(9) -0.0169(8) 0.0176(7) 0.0041(7) O2 0.0790(11) 0.1242(16) 0.0512(10) -0.0090(10) 0.0285(9) 0.0106(11) O3 0.0472(8) 0.0737(11) 0.0567(9) -0.0082(8) 0.0127(7) 0.0145(7) O4 0.0684(9) 0.0542(9) 0.0669(10) -0.0028(8) -0.0005(8) 0.0217(8) O5 0.0733(10) 0.0460(9) 0.0634(10) 0.0057(7) 0.0030(8) -0.0008(8) O6 0.0495(8) 0.0467(8) 0.0649(10) 0.0007(7) 0.0082(7) 0.0105(7) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C5 117.57(17) N1 C1 C2 123.07(17) C5 C1 C2 119.25(17) O5 C2 O6 125.83(19) O5 C2 C1 121.48(19) O6 C2 C1 112.69(17) C4 C3 O6 107.7(2) C4 C3 H3A 110.2 O6 C3 H3A 110.2 C4 C3 H3B 110.2 O6 C3 H3B 110.2 H3A C3 H3B 108.5 C3 C4 H4A 109.5 C3 C4 H4B 109.5 H4A C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 N2 C5 C1 118.09(16) N2 C5 C6 123.38(17) C1 C5 C6 118.44(17) O2 C6 O3 126.1(2) O2 C6 C5 121.4(2) O3 C6 C5 112.52(17) C8 C7 O3 108.8(2) C8 C7 H7A 109.9 O3 C7 H7A 109.9 C8 C7 H7B 109.9 O3 C7 H7B 109.9 H7A C7 H7B 108.3 C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C10 C9 C14 122.2(2) C10 C9 N1 119.62(18) C14 C9 N1 118.09(18) C9 C10 C11 118.4(2) C9 C10 H10 120.8 C11 C10 H10 120.8 C12 C11 C10 120.2(2) C12 C11 H11 119.9 C10 C11 H11 119.9 C13 C12 C11 120.4(2) C13 C12 H12 119.8 C11 C12 H12 119.8 C12 C13 C14 120.2(2) C12 C13 H13 119.9 C14 C13 H13 119.9 C13 C14 C9 118.5(2) C13 C14 H14 120.8 C9 C14 H14 120.8 C20 C15 C16 121.8(2) C20 C15 N2 119.57(18) C16 C15 N2 118.63(18) C15 C16 C17 118.9(2) C15 C16 H16 120.6 C17 C16 H16 120.6 C18 C17 C16 120.0(2) C18 C17 H17 120.0 C16 C17 H17 120.0 C17 C18 C19 120.9(2) C17 C18 H18 119.6 C19 C18 H18 119.6 C18 C19 C20 120.2(2) C18 C19 H19 119.9 C20 C19 H19 119.9 C15 C20 C19 118.2(2) C15 C20 H20 120.9 C19 C20 H20 120.9 O4 N1 C1 121.12(16) O4 N1 C9 115.62(15) C1 N1 C9 123.14(16) O1 N2 C5 121.83(16) O1 N2 C15 115.85(15) C5 N2 C15 122.25(16) C6 O3 C7 117.25(19) C2 O6 C3 116.84(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.322(2) C1 C5 1.443(3) C1 C2 1.486(3) C2 O5 1.199(2) C2 O6 1.323(2) C3 C4 1.435(4) C3 O6 1.466(2) C3 H3A 0.9700 C3 H3B 0.9700 C4 H4A 0.9600 C4 H4B 0.9600 C4 H4C 0.9600 C5 N2 1.322(2) C5 C6 1.487(3) C6 O2 1.196(2) C6 O3 1.318(3) C7 C8 1.433(4) C7 O3 1.453(3) C7 H7A 0.9700 C7 H7B 0.9700 C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C9 C10 1.370(3) C9 C14 1.378(3) C9 N1 1.451(2) C10 C11 1.379(3) C10 H10 0.9300 C11 C12 1.378(4) C11 H11 0.9300 C12 C13 1.372(4) C12 H12 0.9300 C13 C14 1.378(3) C13 H13 0.9300 C14 H14 0.9300 C15 C20 1.371(3) C15 C16 1.372(3) C15 N2 1.452(2) C16 C17 1.377(3) C16 H16 0.9300 C17 C18 1.358(4) C17 H17 0.9300 C18 C19 1.366(4) C18 H18 0.9300 C19 C20 1.385(3) C19 H19 0.9300 C20 H20 0.9300 N1 O4 1.280(2) N2 O1 1.2787(19)