#------------------------------------------------------------------------------ #$Date: 2020-04-16 08:17:59 +0300 (Thu, 16 Apr 2020) $ #$Revision: 250838 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157467.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_7157467 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_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00579G _journal_year 2020 _chemical_formula_sum 'C19 H18 N4 O2' _chemical_formula_weight 334.37 _chemical_name_systematic 7ab _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 ; 2019-12-05 deposited with the CCDC. 2020-04-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.70(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6779(19) _cell_length_b 15.962(3) _cell_length_c 12.006(2) _cell_measurement_reflns_used 4008 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.459 _cell_measurement_theta_min 3.118 _cell_volume 1756.8(6) _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 0.995 _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 0.0350 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 16732 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.459 _diffrn_reflns_theta_min 3.118 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Rigaku Rapid Auto' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.264 _exptl_crystal_description Block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.175 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.034 _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 227 _refine_ls_number_reflns 4008 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0584 _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^)+(0.0631P)^2^+0.5194P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1333 _refine_ls_wR_factor_ref 0.1495 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2666 _reflns_number_total 4008 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00579g2.cif _cod_data_source_block P21c_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 ; _cod_original_cell_volume 1756.8(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7157467 _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 ; P21c_a.res created by SHELXL-2014/7 TITL P21c_a.res in P2(1)/c CELL 0.71073 9.6779 15.9623 12.0059 90.000 108.698 90.000 ZERR 4.000 0.0019 0.0032 0.0024 0.000 0.030 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 76 72 16 8 L.S. 24 ACTA BOND $H FMAP 2 PLAN 5 LIST 6 SIZE 0.28 0.28 0.14 TEMP 25 WGHT 0.063100 0.519400 FVAR 0.73069 C1 1 0.314657 0.613759 0.450230 11.00000 0.05737 0.03253 = 0.04050 0.00368 0.01798 -0.00004 C2 1 0.497703 0.684471 0.624525 11.00000 0.10782 0.04926 = 0.04200 -0.00641 0.01550 -0.00996 AFIX 23 H2A 2 0.578922 0.646339 0.634957 11.00000 -1.20000 H2B 2 0.448353 0.671218 0.681034 11.00000 -1.20000 AFIX 0 C3 1 0.545936 0.774302 0.633495 11.00000 0.15595 0.05947 = 0.06225 -0.00849 0.00626 -0.02446 AFIX 23 H3A 2 0.494172 0.807136 0.675433 11.00000 -1.20000 H3B 2 0.649843 0.778662 0.674472 11.00000 -1.20000 AFIX 0 C4 1 0.416350 0.750318 0.441463 11.00000 0.08527 0.04060 = 0.05263 0.00163 0.02485 -0.00898 C5 1 0.328459 0.556314 0.369717 11.00000 0.05504 0.03458 = 0.04048 0.00212 0.01419 -0.00105 C6 1 0.443148 0.543983 0.315747 11.00000 0.05228 0.03216 = 0.04036 0.00241 0.01644 0.00103 C7 1 0.586628 0.568645 0.370205 11.00000 0.05638 0.04625 = 0.04151 -0.00056 0.01134 -0.00056 AFIX 43 H7 2 0.611560 0.596673 0.441835 11.00000 -1.20000 AFIX 0 C8 1 0.692413 0.551950 0.319034 11.00000 0.04952 0.05882 = 0.05334 0.00866 0.01272 0.00047 AFIX 43 H8 2 0.787727 0.569243 0.356900 11.00000 -1.20000 AFIX 0 C9 1 0.660609 0.510225 0.213028 11.00000 0.06225 0.05452 = 0.05235 0.01308 0.02532 0.01163 C10 1 0.776867 0.491250 0.157905 11.00000 0.07887 0.11254 = 0.07897 0.00967 0.04430 0.01640 AFIX 137 H10A 2 0.785034 0.537358 0.109056 11.00000 -1.50000 H10B 2 0.751031 0.441445 0.110981 11.00000 -1.50000 H10C 2 0.868563 0.482865 0.218580 11.00000 -1.50000 AFIX 0 C11 1 0.517992 0.485508 0.159242 11.00000 0.07261 0.05450 = 0.04604 -0.00555 0.02409 0.00154 AFIX 43 H11 2 0.493944 0.456858 0.088126 11.00000 -1.20000 AFIX 0 C12 1 0.410704 0.502261 0.208360 11.00000 0.05723 0.05033 = 0.04600 -0.00744 0.01631 -0.00650 AFIX 43 H12 2 0.315310 0.485564 0.169493 11.00000 -1.20000 AFIX 0 C13 1 0.119581 0.633879 0.548572 11.00000 0.07412 0.05648 = 0.05907 0.01039 0.03827 0.01208 AFIX 23 H13A 2 0.189810 0.637653 0.626945 11.00000 -1.20000 H13B 2 0.039035 0.599414 0.553166 11.00000 -1.20000 AFIX 0 C14 1 0.063699 0.720161 0.507710 11.00000 0.05181 0.05613 = 0.05865 0.00694 0.02279 0.00775 C15 1 0.087039 0.784270 0.589440 11.00000 0.09022 0.07477 = 0.07450 -0.00691 0.02422 0.02409 AFIX 43 H15 2 0.136874 0.773027 0.668113 11.00000 -1.20000 AFIX 0 C16 1 0.038019 0.864039 0.556508 11.00000 0.10762 0.06859 = 0.12470 -0.01558 0.03202 0.02426 AFIX 43 H16 2 0.054965 0.906327 0.612576 11.00000 -1.20000 AFIX 0 C17 1 -0.035232 0.881161 0.442012 11.00000 0.07330 0.06206 = 0.14249 0.01074 0.02481 0.01551 AFIX 43 H17 2 -0.069938 0.935049 0.420198 11.00000 -1.20000 AFIX 0 C18 1 -0.058396 0.819973 0.358611 11.00000 0.07352 0.09074 = 0.09144 0.03486 0.00513 0.00382 AFIX 43 H18 2 -0.107913 0.832218 0.280196 11.00000 -1.20000 AFIX 0 C19 1 -0.007061 0.738371 0.391799 11.00000 0.08055 0.06455 = 0.06925 0.00814 0.01256 -0.00095 AFIX 43 H19 2 -0.021106 0.696709 0.335092 11.00000 -1.20000 AFIX 0 N1 3 0.210398 0.504392 0.344295 11.00000 0.05947 0.04839 = 0.05358 -0.00494 0.02229 -0.00876 N2 3 0.126683 0.526986 0.406340 11.00000 0.06171 0.05179 = 0.06232 -0.00093 0.02493 -0.00709 N3 3 0.188724 0.593407 0.470445 11.00000 0.06321 0.04117 = 0.05252 0.00453 0.02759 0.00194 N4 3 0.397707 0.682851 0.504210 11.00000 0.07178 0.03341 = 0.03980 -0.00045 0.01927 -0.00161 O1 4 0.511656 0.802986 0.514049 11.00000 0.13979 0.04993 = 0.07015 -0.00265 0.01891 -0.03555 O2 4 0.360191 0.762992 0.339023 11.00000 0.12265 0.06511 = 0.05465 0.01722 0.01871 -0.02065 HKLF 4 REM P21c_a.res in P2(1)/c REM R1 = 0.0584 for 2666 Fo > 4sig(Fo) and 0.0959 for all 4008 data REM 227 parameters refined using 0 restraints END WGHT 0.0631 0.5194 REM Highest difference peak 0.175, deepest hole -0.207, 1-sigma level 0.034 Q1 1 0.3495 0.5773 0.4215 11.00000 0.05 0.18 Q2 1 0.6483 0.7610 0.5946 11.00000 0.05 0.16 Q3 1 -0.0757 0.7759 0.3010 11.00000 0.05 0.16 Q4 1 0.7494 0.4950 0.0716 11.00000 0.05 0.15 Q5 1 -0.1353 0.8159 0.3957 11.00000 0.05 0.15 ; _shelx_res_checksum 29365 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 C1 C 0.3147(2) 0.61376(11) 0.45023(16) 0.0429(4) Uani 1 1 d . . . . . C2 C 0.4977(3) 0.68447(14) 0.62452(18) 0.0684(7) Uani 1 1 d . . . . . H2A H 0.5789 0.6463 0.6350 0.082 Uiso 1 1 calc R U . . . H2B H 0.4484 0.6712 0.6810 0.082 Uiso 1 1 calc R U . . . C3 C 0.5459(4) 0.77430(17) 0.6335(2) 0.0994(10) Uani 1 1 d . . . . . H3A H 0.4942 0.8071 0.6754 0.119 Uiso 1 1 calc R U . . . H3B H 0.6498 0.7787 0.6745 0.119 Uiso 1 1 calc R U . . . C4 C 0.4163(3) 0.75032(13) 0.44146(19) 0.0588(6) Uani 1 1 d . . . . . C5 C 0.3285(2) 0.55631(11) 0.36972(16) 0.0436(4) Uani 1 1 d . . . . . C6 C 0.4431(2) 0.54398(11) 0.31575(15) 0.0412(4) Uani 1 1 d . . . . . C7 C 0.5866(2) 0.56864(12) 0.37021(17) 0.0491(5) Uani 1 1 d . . . . . H7 H 0.6116 0.5967 0.4418 0.059 Uiso 1 1 calc R U . . . C8 C 0.6924(2) 0.55195(14) 0.31903(18) 0.0548(5) Uani 1 1 d . . . . . H8 H 0.7877 0.5692 0.3569 0.066 Uiso 1 1 calc R U . . . C9 C 0.6606(2) 0.51022(13) 0.21303(18) 0.0547(5) Uani 1 1 d . . . . . C10 C 0.7769(3) 0.4912(2) 0.1579(2) 0.0856(8) Uani 1 1 d . . . . . H10A H 0.7850 0.5374 0.1091 0.128 Uiso 1 1 calc R U . . . H10B H 0.7510 0.4414 0.1110 0.128 Uiso 1 1 calc R U . . . H10C H 0.8686 0.4829 0.2186 0.128 Uiso 1 1 calc R U . . . C11 C 0.5180(2) 0.48551(13) 0.15924(18) 0.0565(5) Uani 1 1 d . . . . . H11 H 0.4939 0.4569 0.0881 0.068 Uiso 1 1 calc R U . . . C12 C 0.4107(2) 0.50226(12) 0.20836(17) 0.0512(5) Uani 1 1 d . . . . . H12 H 0.3153 0.4856 0.1695 0.061 Uiso 1 1 calc R U . . . C13 C 0.1196(3) 0.63388(13) 0.5486(2) 0.0592(6) Uani 1 1 d . . . . . H13A H 0.1898 0.6377 0.6269 0.071 Uiso 1 1 calc R U . . . H13B H 0.0390 0.5994 0.5532 0.071 Uiso 1 1 calc R U . . . C14 C 0.0637(2) 0.72016(13) 0.50771(19) 0.0543(5) Uani 1 1 d . . . . . C15 C 0.0870(3) 0.78427(17) 0.5894(2) 0.0804(8) Uani 1 1 d . . . . . H15 H 0.1369 0.7730 0.6681 0.096 Uiso 1 1 calc R U . . . C16 C 0.0380(4) 0.86404(19) 0.5565(3) 0.1015(10) Uani 1 1 d . . . . . H16 H 0.0550 0.9063 0.6126 0.122 Uiso 1 1 calc R U . . . C17 C -0.0352(3) 0.88116(19) 0.4420(4) 0.0949(10) Uani 1 1 d . . . . . H17 H -0.0699 0.9350 0.4202 0.114 Uiso 1 1 calc R U . . . C18 C -0.0584(3) 0.8200(2) 0.3586(3) 0.0903(9) Uani 1 1 d . . . . . H18 H -0.1079 0.8322 0.2802 0.108 Uiso 1 1 calc R U . . . C19 C -0.0071(3) 0.73837(16) 0.3918(2) 0.0742(7) Uani 1 1 d . . . . . H19 H -0.0211 0.6967 0.3351 0.089 Uiso 1 1 calc R U . . . N1 N 0.21040(18) 0.50439(10) 0.34430(15) 0.0528(4) Uani 1 1 d . . . . . N2 N 0.12668(19) 0.52699(11) 0.40634(16) 0.0574(5) Uani 1 1 d . . . . . N3 N 0.18872(18) 0.59341(10) 0.47045(14) 0.0501(4) Uani 1 1 d . . . . . N4 N 0.39771(18) 0.68285(9) 0.50421(13) 0.0480(4) Uani 1 1 d . . . . . O1 O 0.5117(2) 0.80299(10) 0.51405(16) 0.0901(6) Uani 1 1 d . . . . . O2 O 0.3602(2) 0.76299(11) 0.33902(14) 0.0831(6) 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 0.0574(11) 0.0325(9) 0.0405(10) 0.0037(7) 0.0180(8) 0.0000(8) C2 0.1078(19) 0.0493(12) 0.0420(11) -0.0064(10) 0.0155(12) -0.0100(12) C3 0.156(3) 0.0595(16) 0.0623(16) -0.0085(13) 0.0063(17) -0.0245(17) C4 0.0853(15) 0.0406(11) 0.0526(13) 0.0016(9) 0.0249(11) -0.0090(10) C5 0.0550(11) 0.0346(9) 0.0405(10) 0.0021(8) 0.0142(8) -0.0010(8) C6 0.0523(11) 0.0322(9) 0.0404(10) 0.0024(7) 0.0164(8) 0.0010(8) C7 0.0564(12) 0.0462(11) 0.0415(10) -0.0006(8) 0.0113(9) -0.0006(9) C8 0.0495(11) 0.0588(13) 0.0533(12) 0.0087(10) 0.0127(9) 0.0005(10) C9 0.0622(13) 0.0545(12) 0.0524(12) 0.0131(10) 0.0253(10) 0.0116(10) C10 0.0789(17) 0.113(2) 0.0790(18) 0.0097(16) 0.0443(14) 0.0164(16) C11 0.0726(14) 0.0545(12) 0.0460(11) -0.0056(9) 0.0241(10) 0.0015(11) C12 0.0572(11) 0.0503(11) 0.0460(11) -0.0074(9) 0.0163(9) -0.0065(9) C13 0.0741(14) 0.0565(13) 0.0591(13) 0.0104(10) 0.0383(11) 0.0121(11) C14 0.0518(11) 0.0561(12) 0.0587(13) 0.0069(10) 0.0228(10) 0.0078(10) C15 0.0902(18) 0.0748(17) 0.0745(17) -0.0069(14) 0.0242(14) 0.0241(14) C16 0.108(2) 0.0686(18) 0.125(3) -0.0156(18) 0.032(2) 0.0243(17) C17 0.0733(18) 0.0621(17) 0.142(3) 0.0107(19) 0.0248(19) 0.0155(14) C18 0.0735(17) 0.091(2) 0.091(2) 0.0349(18) 0.0051(14) 0.0038(15) C19 0.0806(16) 0.0645(15) 0.0693(16) 0.0081(12) 0.0126(13) -0.0010(13) N1 0.0595(10) 0.0484(9) 0.0536(10) -0.0049(8) 0.0223(8) -0.0088(8) N2 0.0617(11) 0.0518(10) 0.0623(11) -0.0009(9) 0.0249(9) -0.0071(8) N3 0.0632(10) 0.0412(9) 0.0525(10) 0.0045(8) 0.0276(8) 0.0019(8) N4 0.0718(11) 0.0334(8) 0.0398(8) -0.0004(6) 0.0193(7) -0.0016(7) O1 0.1398(16) 0.0499(9) 0.0701(11) -0.0026(8) 0.0189(11) -0.0355(10) O2 0.1226(15) 0.0651(11) 0.0546(10) 0.0172(8) 0.0187(10) -0.0207(10) 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 N3 C1 C5 105.22(16) . . ? N3 C1 N4 121.53(17) . . ? C5 C1 N4 133.22(18) . . ? N4 C2 C3 100.39(18) . . ? N4 C2 H2A 111.7 . . ? C3 C2 H2A 111.7 . . ? N4 C2 H2B 111.7 . . ? C3 C2 H2B 111.7 . . ? H2A C2 H2B 109.5 . . ? O1 C3 C2 105.39(19) . . ? O1 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? O1 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? O2 C4 O1 123.7(2) . . ? O2 C4 N4 127.5(2) . . ? O1 C4 N4 108.79(18) . . ? N1 C5 C1 107.48(17) . . ? N1 C5 C6 121.17(16) . . ? C1 C5 C6 131.33(17) . . ? C7 C6 C12 117.74(18) . . ? C7 C6 C5 122.55(17) . . ? C12 C6 C5 119.64(17) . . ? C8 C7 C6 120.58(19) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.74(19) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C11 C9 C8 117.58(19) . . ? C11 C9 C10 120.8(2) . . ? C8 C9 C10 121.6(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C9 121.5(2) . . ? C12 C11 H11 119.2 . . ? C9 C11 H11 119.2 . . ? C11 C12 C6 120.82(19) . . ? C11 C12 H12 119.6 . . ? C6 C12 H12 119.6 . . ? N3 C13 C14 112.66(17) . . ? N3 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N3 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C19 C14 C15 118.5(2) . . ? C19 C14 C13 122.4(2) . . ? C15 C14 C13 119.1(2) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.6(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C14 C19 C18 120.0(3) . . ? C14 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? N2 N1 C5 109.30(16) . . ? N1 N2 N3 107.44(15) . . ? N2 N3 C1 110.55(16) . . ? N2 N3 C13 120.40(17) . . ? C1 N3 C13 129.04(17) . . ? C4 N4 C1 121.85(16) . . ? C4 N4 C2 111.78(17) . . ? C1 N4 C2 125.05(16) . . ? C4 O1 C3 109.79(18) . . ? 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 N3 1.356(2) . ? C1 C5 1.370(3) . ? C1 N4 1.396(2) . ? C2 N4 1.459(3) . ? C2 C3 1.501(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.439(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.192(3) . ? C4 O1 1.342(3) . ? C4 N4 1.359(2) . ? C5 N1 1.365(2) . ? C5 C6 1.467(3) . ? C6 C7 1.389(3) . ? C6 C12 1.395(3) . ? C7 C8 1.378(3) . ? C7 H7 0.9300 . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C11 1.381(3) . ? C9 C10 1.508(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.375(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N3 1.465(3) . ? C13 C14 1.503(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.371(3) . ? C14 C15 1.385(3) . ? C15 C16 1.372(4) . ? C15 H15 0.9300 . ? C16 C17 1.357(4) . ? C16 H16 0.9300 . ? C17 C18 1.365(4) . ? C17 H17 0.9300 . ? C18 C19 1.405(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? N1 N2 1.315(2) . ? N2 N3 1.334(2) . ?