#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:27:29 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252906 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157468.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_7157468 loop_ _publ_author_name 'Kim, Woo Gyum' 'Baek, Seung-Yeol' 'Jeong, Seo Yeong' 'Nam, Dongsik' 'Jeon, Ji Hwan' 'Choe, Wonyoung' 'Baik, Mu-Hyun' 'Hong, Sung You' _publ_section_title ; Chemo- and regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3374 _journal_page_last 3381 _journal_paper_doi 10.1039/d0ob00579g _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C19 H18 N4 O3' _chemical_formula_weight 350.37 _chemical_name_systematic 7ae _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_method SHELXL-2014/7 _audit_update_record ; 2019-12-05 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.942(3) _cell_length_b 12.891(3) _cell_length_c 17.930(4) _cell_measurement_reflns_used 3956 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.466 _cell_measurement_theta_min 3.085 _cell_volume 3453.6(13) _computing_cell_refinement 'Rigaku Rapid Auto' _computing_data_collection 'Rigaku Rapid Auto' _computing_data_reduction 'Rigaku Rapid Auto' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution SHELXS _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'imaging plate' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 30009 _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 27.466 _diffrn_reflns_theta_min 3.085 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Rigaku Rapid Auto' _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.348 _exptl_crystal_description Block _exptl_crystal_F_000 1472 _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.168 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.027 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3956 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0512 _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^)+(0.0432P)^2^+0.7003P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.1121 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2672 _reflns_number_total 3956 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00579g2.cif _cod_data_source_block Pbca_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7157466--7157469.cif. ; _cod_original_cell_volume 3453.6(12) _cod_database_code 7157468 _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 ; Pbca_a.res created by SHELXL-2014/7 TITL Pbca_a.res in Pbca CELL 0.71073 14.9425 12.8905 17.9299 90.000 90.000 90.000 ZERR 8.000 0.0030 0.0026 0.0036 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N O UNIT 152 144 32 24 L.S. 24 ACTA BOND $H FMAP 2 PLAN 5 LIST 6 SIZE 0.23 0.22 0.22 TEMP 25 WGHT 0.043200 0.700300 FVAR 0.34860 C1 1 0.308293 0.717128 0.504676 11.00000 0.04676 0.03522 = 0.05329 -0.00075 -0.00430 0.00201 C2 1 0.220269 0.732791 0.615651 11.00000 0.04984 0.05344 = 0.07650 0.00466 0.00885 -0.00273 C3 1 0.154532 0.890687 0.600848 11.00000 0.05868 0.06210 = 0.09769 -0.00682 0.00313 0.01527 AFIX 23 H3A 2 0.164437 0.956959 0.625107 11.00000 -1.20000 H3B 2 0.093092 0.887755 0.583511 11.00000 -1.20000 AFIX 0 C4 1 0.218698 0.876156 0.536907 11.00000 0.06299 0.04727 = 0.07863 0.00245 -0.00079 0.01758 AFIX 23 H4A 2 0.190400 0.890333 0.489297 11.00000 -1.20000 H4B 2 0.271354 0.919523 0.542292 11.00000 -1.20000 AFIX 0 C5 1 0.394243 0.685903 0.520464 11.00000 0.04495 0.03395 = 0.05482 -0.00484 -0.00135 0.00304 C6 1 0.449449 0.685279 0.588443 11.00000 0.03993 0.03840 = 0.05042 0.00018 -0.00120 -0.00504 C7 1 0.507605 0.602181 0.599362 11.00000 0.04597 0.03909 = 0.05789 -0.00065 -0.00284 -0.00125 AFIX 43 H7 2 0.509504 0.549427 0.564016 11.00000 -1.20000 AFIX 0 C8 1 0.562272 0.595899 0.660879 11.00000 0.05057 0.04900 = 0.06424 0.00897 -0.00663 0.00126 AFIX 43 H8 2 0.600917 0.539927 0.666695 11.00000 -1.20000 AFIX 0 C9 1 0.559291 0.673028 0.713656 11.00000 0.05606 0.06133 = 0.05323 0.01066 -0.00970 -0.01050 AFIX 43 H9 2 0.595525 0.668635 0.755710 11.00000 -1.20000 AFIX 0 C10 1 0.503118 0.756806 0.704844 11.00000 0.05836 0.05266 = 0.05284 -0.00608 -0.00053 -0.01381 AFIX 43 H10 2 0.501858 0.808940 0.740683 11.00000 -1.20000 AFIX 0 C11 1 0.448360 0.763478 0.642477 11.00000 0.04479 0.03784 = 0.05605 -0.00090 0.00208 -0.00426 C12 1 0.392751 0.928947 0.680506 11.00000 0.07866 0.05224 = 0.09482 -0.02972 0.00260 0.00328 AFIX 137 H12A 2 0.374319 0.904306 0.728640 11.00000 -1.50000 H12B 2 0.352257 0.981957 0.663911 11.00000 -1.50000 H12C 2 0.452112 0.957042 0.683874 11.00000 -1.50000 AFIX 0 C13 1 0.212586 0.694442 0.387342 11.00000 0.06535 0.05400 = 0.06919 0.00231 -0.02367 0.00763 AFIX 23 H13A 2 0.227143 0.721555 0.338356 11.00000 -1.20000 H13B 2 0.170333 0.741540 0.410586 11.00000 -1.20000 AFIX 0 C14 1 0.170341 0.589223 0.379313 11.00000 0.05195 0.05206 = 0.05461 -0.00117 -0.01535 0.00953 C15 1 0.122351 0.546495 0.436598 11.00000 0.08221 0.07496 = 0.05934 -0.00117 -0.01056 -0.00194 AFIX 43 H15 2 0.115377 0.583396 0.480788 11.00000 -1.20000 AFIX 0 C16 1 0.084285 0.449849 0.429830 11.00000 0.08758 0.08585 = 0.08733 0.02282 -0.01706 -0.01374 AFIX 43 H16 2 0.052441 0.421730 0.469546 11.00000 -1.20000 AFIX 0 C17 1 0.092903 0.395391 0.365668 11.00000 0.08194 0.05702 = 0.12108 0.00326 -0.03325 -0.00223 AFIX 43 H17 2 0.066195 0.330542 0.361057 11.00000 -1.20000 AFIX 0 C18 1 0.140509 0.435526 0.308178 11.00000 0.08119 0.08126 = 0.10235 -0.03935 -0.01731 0.00666 AFIX 43 H18 2 0.147094 0.397809 0.264304 11.00000 -1.20000 AFIX 0 C19 1 0.179504 0.532986 0.314702 11.00000 0.06623 0.08223 = 0.06772 -0.01536 -0.00362 -0.00035 AFIX 43 H19 2 0.212009 0.560295 0.275065 11.00000 -1.20000 AFIX 0 N1 3 0.240465 0.765808 0.545230 11.00000 0.04505 0.04233 = 0.06305 0.00259 0.00023 0.00557 N2 3 0.294431 0.689005 0.432829 11.00000 0.05281 0.04498 = 0.06097 -0.00514 -0.01204 0.00711 N3 3 0.367178 0.643964 0.404068 11.00000 0.06566 0.05768 = 0.06027 -0.01142 -0.01065 0.01467 N4 3 0.427681 0.641402 0.457340 11.00000 0.05424 0.05092 = 0.05906 -0.01055 -0.00631 0.01152 O1 4 0.173071 0.806370 0.651269 11.00000 0.07224 0.07584 = 0.08441 0.00219 0.02483 0.01383 O2 4 0.239474 0.650817 0.643338 11.00000 0.08395 0.06384 = 0.09338 0.02455 0.02140 0.00370 O3 4 0.392103 0.845088 0.628662 11.00000 0.06381 0.04224 = 0.07143 -0.01479 -0.00613 0.00670 HKLF 4 REM Pbca_a.res in Pbca REM R1 = 0.0512 for 2672 Fo > 4sig(Fo) and 0.0887 for all 3956 data REM 236 parameters refined using 0 restraints END WGHT 0.0432 0.7015 REM Highest difference peak 0.168, deepest hole -0.129, 1-sigma level 0.027 Q1 1 0.4203 0.7047 0.6288 11.00000 0.05 0.17 Q2 1 0.1830 0.6438 0.6109 11.00000 0.05 0.15 Q3 1 0.4830 0.6187 0.4588 11.00000 0.05 0.14 Q4 1 0.3627 0.7341 0.5123 11.00000 0.05 0.13 Q5 1 0.5003 0.7733 0.6620 11.00000 0.05 0.13 ; _shelx_res_checksum 81720 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 C1 C 0.30829(10) 0.71713(11) 0.50468(9) 0.0451(4) Uani 1 1 d . . . . . C2 C 0.22027(12) 0.73279(15) 0.61565(11) 0.0599(5) Uani 1 1 d . . . . . C3 C 0.15453(13) 0.89069(16) 0.60085(12) 0.0728(6) Uani 1 1 d . . . . . H3A H 0.1644 0.9570 0.6251 0.087 Uiso 1 1 calc R U . . . H3B H 0.0931 0.8878 0.5835 0.087 Uiso 1 1 calc R U . . . C4 C 0.21870(13) 0.87616(14) 0.53691(11) 0.0630(5) Uani 1 1 d . . . . . H4A H 0.1904 0.8903 0.4893 0.076 Uiso 1 1 calc R U . . . H4B H 0.2714 0.9195 0.5423 0.076 Uiso 1 1 calc R U . . . C5 C 0.39424(10) 0.68590(11) 0.52046(9) 0.0446(4) Uani 1 1 d . . . . . C6 C 0.44945(10) 0.68528(12) 0.58844(9) 0.0429(4) Uani 1 1 d . . . . . C7 C 0.50760(10) 0.60218(12) 0.59936(9) 0.0476(4) Uani 1 1 d . . . . . H7 H 0.5095 0.5494 0.5640 0.057 Uiso 1 1 calc R U . . . C8 C 0.56227(12) 0.59590(14) 0.66088(10) 0.0546(4) Uani 1 1 d . . . . . H8 H 0.6009 0.5399 0.6667 0.066 Uiso 1 1 calc R U . . . C9 C 0.55929(12) 0.67303(14) 0.71366(10) 0.0569(5) Uani 1 1 d . . . . . H9 H 0.5955 0.6686 0.7557 0.068 Uiso 1 1 calc R U . . . C10 C 0.50312(12) 0.75681(14) 0.70484(9) 0.0546(4) Uani 1 1 d . . . . . H10 H 0.5019 0.8089 0.7407 0.066 Uiso 1 1 calc R U . . . C11 C 0.44836(10) 0.76348(12) 0.64248(9) 0.0462(4) Uani 1 1 d . . . . . C12 C 0.39275(15) 0.92895(15) 0.68051(12) 0.0752(6) Uani 1 1 d . . . . . H12A H 0.3743 0.9043 0.7286 0.113 Uiso 1 1 calc R U . . . H12B H 0.3523 0.9820 0.6639 0.113 Uiso 1 1 calc R U . . . H12C H 0.4521 0.9570 0.6839 0.113 Uiso 1 1 calc R U . . . C13 C 0.21259(12) 0.69444(14) 0.38734(11) 0.0628(5) Uani 1 1 d . . . . . H13A H 0.2271 0.7216 0.3384 0.075 Uiso 1 1 calc R U . . . H13B H 0.1703 0.7415 0.4106 0.075 Uiso 1 1 calc R U . . . C14 C 0.17034(12) 0.58922(13) 0.37931(10) 0.0529(4) Uani 1 1 d . . . . . C15 C 0.12235(15) 0.54649(17) 0.43660(11) 0.0722(6) Uani 1 1 d . . . . . H15 H 0.1154 0.5834 0.4808 0.087 Uiso 1 1 calc R U . . . C16 C 0.08429(16) 0.4498(2) 0.42983(15) 0.0869(7) Uani 1 1 d . . . . . H16 H 0.0524 0.4217 0.4695 0.104 Uiso 1 1 calc R U . . . C17 C 0.09290(17) 0.39539(18) 0.36567(17) 0.0867(7) Uani 1 1 d . . . . . H17 H 0.0662 0.3305 0.3611 0.104 Uiso 1 1 calc R U . . . C18 C 0.14051(17) 0.4355(2) 0.30818(16) 0.0883(7) Uani 1 1 d . . . . . H18 H 0.1471 0.3978 0.2643 0.106 Uiso 1 1 calc R U . . . C19 C 0.17950(14) 0.53299(17) 0.31470(12) 0.0721(6) Uani 1 1 d . . . . . H19 H 0.2120 0.5603 0.2751 0.086 Uiso 1 1 calc R U . . . N1 N 0.24046(9) 0.76581(10) 0.54523(8) 0.0501(3) Uani 1 1 d . . . . . N2 N 0.29443(9) 0.68900(11) 0.43283(8) 0.0529(4) Uani 1 1 d . . . . . N3 N 0.36718(10) 0.64396(12) 0.40407(8) 0.0612(4) Uani 1 1 d . . . . . N4 N 0.42768(9) 0.64140(11) 0.45734(8) 0.0547(4) Uani 1 1 d . . . . . O1 O 0.17307(9) 0.80637(11) 0.65127(8) 0.0775(4) Uani 1 1 d . . . . . O2 O 0.23947(10) 0.65082(11) 0.64334(8) 0.0804(4) Uani 1 1 d . . . . . O3 O 0.39210(8) 0.84509(9) 0.62866(7) 0.0592(3) 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 0.0468(9) 0.0352(8) 0.0533(10) -0.0008(7) -0.0043(8) 0.0020(7) C2 0.0498(10) 0.0534(11) 0.0765(13) 0.0047(10) 0.0088(9) -0.0027(8) C3 0.0587(11) 0.0621(12) 0.0977(16) -0.0068(11) 0.0031(12) 0.0153(9) C4 0.0630(11) 0.0473(11) 0.0786(13) 0.0025(9) -0.0008(10) 0.0176(8) C5 0.0449(8) 0.0340(8) 0.0548(9) -0.0048(7) -0.0014(8) 0.0030(7) C6 0.0399(8) 0.0384(8) 0.0504(9) 0.0002(7) -0.0012(7) -0.0050(7) C7 0.0460(9) 0.0391(8) 0.0579(10) -0.0007(7) -0.0028(8) -0.0013(7) C8 0.0506(9) 0.0490(10) 0.0642(11) 0.0090(9) -0.0066(9) 0.0013(8) C9 0.0561(10) 0.0613(12) 0.0532(10) 0.0107(9) -0.0097(9) -0.0105(9) C10 0.0584(10) 0.0527(11) 0.0528(10) -0.0061(8) -0.0005(9) -0.0138(9) C11 0.0448(8) 0.0378(9) 0.0561(10) -0.0009(7) 0.0021(8) -0.0043(7) C12 0.0787(13) 0.0522(11) 0.0948(15) -0.0297(11) 0.0026(12) 0.0033(10) C13 0.0654(11) 0.0540(11) 0.0692(12) 0.0023(9) -0.0237(10) 0.0076(9) C14 0.0519(10) 0.0521(10) 0.0546(10) -0.0012(8) -0.0153(9) 0.0095(8) C15 0.0822(14) 0.0750(14) 0.0593(12) -0.0012(10) -0.0106(11) -0.0019(12) C16 0.0876(16) 0.0858(17) 0.0873(16) 0.0228(14) -0.0171(14) -0.0137(13) C17 0.0819(16) 0.0570(13) 0.121(2) 0.0033(14) -0.0332(16) -0.0022(11) C18 0.0812(15) 0.0813(17) 0.1024(18) -0.0393(14) -0.0173(14) 0.0067(13) C19 0.0662(12) 0.0822(15) 0.0677(13) -0.0154(11) -0.0036(11) -0.0003(11) N1 0.0451(7) 0.0423(7) 0.0631(9) 0.0026(7) 0.0002(7) 0.0056(6) N2 0.0528(8) 0.0450(8) 0.0610(9) -0.0051(7) -0.0120(7) 0.0071(6) N3 0.0657(9) 0.0577(9) 0.0603(9) -0.0114(7) -0.0106(8) 0.0147(8) N4 0.0542(8) 0.0509(8) 0.0591(9) -0.0106(7) -0.0063(7) 0.0115(7) O1 0.0722(9) 0.0758(10) 0.0844(10) 0.0022(8) 0.0248(8) 0.0138(8) O2 0.0840(10) 0.0638(9) 0.0934(10) 0.0246(8) 0.0214(8) 0.0037(8) O3 0.0638(7) 0.0422(6) 0.0714(8) -0.0148(6) -0.0061(6) 0.0067(6) 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 N2 C1 C5 105.09(14) . . ? N2 C1 N1 120.31(14) . . ? C5 C1 N1 134.60(15) . . ? O2 C2 O1 123.34(18) . . ? O2 C2 N1 127.06(18) . . ? O1 C2 N1 109.59(16) . . ? O1 C3 C4 105.15(14) . . ? O1 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? O1 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? N1 C4 C3 100.62(15) . . ? N1 C4 H4A 111.6 . . ? C3 C4 H4A 111.6 . . ? N1 C4 H4B 111.6 . . ? C3 C4 H4B 111.6 . . ? H4A C4 H4B 109.4 . . ? N4 C5 C1 107.12(14) . . ? N4 C5 C6 118.66(13) . . ? C1 C5 C6 134.06(15) . . ? C7 C6 C11 117.66(15) . . ? C7 C6 C5 118.05(14) . . ? C11 C6 C5 124.29(14) . . ? C8 C7 C6 121.91(16) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C9 C8 C7 119.40(17) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.57(17) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 120.02(17) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? O3 C11 C10 123.72(15) . . ? O3 C11 C6 115.83(14) . . ? C10 C11 C6 120.44(15) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C14 111.05(14) . . ? N2 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N2 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C19 118.22(19) . . ? C15 C14 C13 120.76(17) . . ? C19 C14 C13 121.01(18) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.9(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C14 C19 C18 120.4(2) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C2 N1 C1 120.11(14) . . ? C2 N1 C4 110.31(15) . . ? C1 N1 C4 122.94(14) . . ? N3 N2 C1 111.05(13) . . ? N3 N2 C13 118.88(14) . . ? C1 N2 C13 129.91(15) . . ? N4 N3 N2 106.85(13) . . ? N3 N4 C5 109.89(13) . . ? C2 O1 C3 109.59(15) . . ? C11 O3 C12 117.41(14) . . ? 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 C1 N2 1.354(2) . ? C1 C5 1.375(2) . ? C1 N1 1.396(2) . ? C2 O2 1.202(2) . ? C2 O1 1.343(2) . ? C2 N1 1.366(2) . ? C3 O1 1.441(2) . ? C3 C4 1.506(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.467(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N4 1.364(2) . ? C5 C6 1.472(2) . ? C6 C7 1.393(2) . ? C6 C11 1.398(2) . ? C7 C8 1.375(2) . ? C7 H7 0.9300 . ? C8 C9 1.373(2) . ? C8 H8 0.9300 . ? C9 C10 1.377(3) . ? C9 H9 0.9300 . ? C10 C11 1.388(2) . ? C10 H10 0.9300 . ? C11 O3 1.3692(19) . ? C12 O3 1.426(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.472(2) . ? C13 C14 1.503(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.368(3) . ? C14 C19 1.373(3) . ? C15 C16 1.375(3) . ? C15 H15 0.9300 . ? C16 C17 1.354(3) . ? C16 H16 0.9300 . ? C17 C18 1.355(3) . ? C17 H17 0.9300 . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? N2 N3 1.3359(19) . ? N3 N4 1.3156(19) . ?