#------------------------------------------------------------------------------ #$Date: 2020-04-05 13:25:56 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250215 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557206.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_1557206 loop_ _publ_author_name 'Chen, Hang' 'Ye, Hebo' 'Hai, Yu' 'Zhang, Ling' 'You, Lei' _publ_section_title ; n \\rightarrow \p* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media ; _journal_issue 10 _journal_name_full 'Chemical Science' _journal_page_first 2707 _journal_paper_doi 10.1039/C9SC05698J _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C14 H16 N O2, C6 H14 N' _chemical_formula_sum 'C20 H30 N2 O2' _chemical_formula_weight 330.46 _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_date 2019-05-25 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-10 deposited with the CCDC. 2020-01-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.899(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.012(9) _cell_length_b 16.138(13) _cell_length_c 11.225(9) _cell_measurement_reflns_used 4414 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.1445 _cell_measurement_theta_min 2.2209 _cell_volume 1980(3) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_unetI/netI 0.0378 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13753 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.183 _diffrn_reflns_theta_min 2.221 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 720 _refine_diff_density_max 0.205 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3872 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0547 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0722P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1300 _refine_ls_wR_factor_ref 0.1445 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2845 _reflns_number_total 3872 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05698j2.cif _cod_data_source_block 2aocb _cod_depositor_comments 'Adding full bibliography for 1557206--1557207.cif.' _cod_database_code 1557206 _shelxl_version_number 2014/6 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C16(H16), C6(H6) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B), C5(H5A, H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C1(H1D,H1E) 2.c Aromatic/amide H refined with riding coordinates: C17(H17), C15(H15), C14(H14), C13(H13), C12(H12) 2.d Idealised Me refined as rotating group: N1(H1A,H1B,H1C) ; _shelx_res_file ; TITL zz in P2(1)/c CELL 0.71073 11.0116 16.1382 11.2249 90 96.899 90 ZERR 4 0.009 0.0129 0.0092 0 0.012 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 80 120 8 8 L.S. 4 PLAN 10 BOND fmap 2 acta REM REM REM WGHT 0.072200 FVAR 0.61007 N2 3 0.054689 0.210137 0.843221 11.00000 0.04475 0.03938 = 0.05400 0.00433 0.00333 -0.00043 O2 4 -0.217402 0.427389 0.555098 11.00000 0.06829 0.06856 = 0.04774 0.01604 0.01002 0.01788 C20 1 -0.196705 0.344825 0.731374 11.00000 0.04714 0.03245 = 0.04039 -0.00342 0.00201 -0.00164 C19 1 -0.143544 0.395794 0.635882 11.00000 0.05468 0.03442 = 0.04034 -0.00227 0.00268 0.00047 O1 4 -0.029782 0.403354 0.641949 11.00000 0.05822 0.07263 = 0.06616 0.02289 -0.00067 -0.01959 C18 1 -0.126336 0.293496 0.814263 11.00000 0.04676 0.03200 = 0.04593 0.00061 0.00487 -0.00164 C17 1 0.007751 0.280105 0.817446 11.00000 0.04875 0.03831 = 0.04994 0.00748 0.00475 -0.00312 AFIX 43 H17 2 0.057596 0.323946 0.800187 11.00000 -1.20000 AFIX 0 C16 1 0.189110 0.203350 0.857145 11.00000 0.04090 0.04083 = 0.05777 0.00725 0.00469 -0.00374 AFIX 13 H16 2 0.223915 0.254549 0.828766 11.00000 -1.20000 AFIX 0 C15 1 -0.322354 0.348994 0.735967 11.00000 0.04786 0.05283 = 0.05365 0.00353 -0.00153 0.00265 AFIX 43 H15 2 -0.369944 0.382130 0.680895 11.00000 -1.20000 AFIX 0 C14 1 -0.184665 0.251336 0.900216 11.00000 0.05814 0.04178 = 0.05733 0.01051 0.01152 0.00535 AFIX 43 H14 2 -0.137955 0.218971 0.957002 11.00000 -1.20000 AFIX 0 C13 1 -0.309265 0.256226 0.903454 11.00000 0.06245 0.05538 = 0.07083 0.01291 0.02286 -0.00270 AFIX 43 H13 2 -0.346208 0.227009 0.960790 11.00000 -1.20000 AFIX 0 C12 1 -0.378266 0.305259 0.820088 11.00000 0.04562 0.06874 = 0.07933 0.00819 0.01424 -0.00160 AFIX 43 H12 2 -0.462497 0.308832 0.820594 11.00000 -1.20000 AFIX 0 C11 1 0.233747 0.191615 0.989988 11.00000 0.05282 0.08202 = 0.05697 -0.00416 -0.00011 0.00108 AFIX 23 H11A 2 0.193483 0.143821 1.020002 11.00000 -1.20000 H11B 2 0.211934 0.239887 1.034318 11.00000 -1.20000 AFIX 0 C10 1 0.228756 0.130438 0.784843 11.00000 0.05454 0.06501 = 0.06139 -0.00581 0.00349 0.00331 AFIX 23 H10A 2 0.203676 0.140134 0.700176 11.00000 -1.20000 H10B 2 0.188477 0.080465 0.807787 11.00000 -1.20000 AFIX 0 C9 1 0.367213 0.118127 0.805523 11.00000 0.05567 0.07703 = 0.09327 -0.01289 0.01709 0.00702 AFIX 23 H9A 2 0.388944 0.069410 0.762106 11.00000 -1.20000 H9B 2 0.407249 0.165599 0.774339 11.00000 -1.20000 AFIX 0 C8 1 0.412386 0.107724 0.938281 11.00000 0.04315 0.07832 = 0.10521 0.01329 -0.00247 0.00417 AFIX 23 H8A 2 0.380607 0.056376 0.967089 11.00000 -1.20000 H8B 2 0.500979 0.104370 0.948902 11.00000 -1.20000 AFIX 0 C7 1 0.372256 0.179130 1.010852 11.00000 0.05309 0.09551 = 0.07065 0.00328 -0.00898 -0.00472 AFIX 23 H7A 2 0.412615 0.229384 0.989102 11.00000 -1.20000 H7B 2 0.396958 0.168711 1.095399 11.00000 -1.20000 AFIX 0 N1 3 0.908136 0.054686 0.857955 11.00000 0.04500 0.04556 = 0.04477 -0.00768 0.00353 -0.00073 AFIX 137 H1A 2 0.957521 0.098280 0.857047 11.00000 -1.20000 H1B 2 0.952423 0.008411 0.863200 11.00000 -1.20000 H1C 2 0.866301 0.058241 0.920853 11.00000 -1.20000 AFIX 0 C6 1 0.821164 0.053221 0.745152 11.00000 0.04586 0.04921 = 0.04598 -0.00188 -0.00005 0.00261 AFIX 13 H6 2 0.782259 0.107784 0.734813 11.00000 -1.20000 AFIX 0 C5 1 0.723077 -0.010173 0.755405 11.00000 0.05878 0.10608 = 0.05639 -0.00300 0.00632 -0.02858 AFIX 23 H5A 2 0.677571 0.004365 0.821223 11.00000 -1.20000 H5B 2 0.760209 -0.064054 0.772388 11.00000 -1.20000 AFIX 0 C4 1 0.889602 0.036822 0.637346 11.00000 0.06420 0.07578 = 0.04986 0.00271 0.01216 -0.00581 AFIX 23 H4A 2 0.936464 -0.013938 0.650545 11.00000 -1.20000 H4B 2 0.946519 0.081786 0.629359 11.00000 -1.20000 AFIX 0 C3 1 0.704302 -0.033700 0.533134 11.00000 0.10307 0.10844 = 0.06196 -0.01763 -0.02374 -0.01287 AFIX 23 H3A 2 0.740905 -0.088281 0.543693 11.00000 -1.20000 H3B 2 0.647452 -0.034394 0.460093 11.00000 -1.20000 AFIX 0 C2 1 0.802240 0.029091 0.521434 11.00000 0.09839 0.09995 = 0.04556 0.00452 0.00243 0.00566 AFIX 23 H2A 2 0.764776 0.082497 0.501505 11.00000 -1.20000 H2B 2 0.848045 0.013085 0.456490 11.00000 -1.20000 AFIX 0 C1 1 0.635915 -0.014273 0.638395 11.00000 0.07104 0.14445 = 0.08263 -0.00915 -0.01246 -0.03723 AFIX 23 H1D 2 0.574700 -0.056673 0.645227 11.00000 -1.20000 H1E 2 0.594113 0.038411 0.624932 11.00000 -1.20000 AFIX 0 HKLF 4 REM zz in P2(1)/c REM R1 = 0.0547 for 2845 Fo > 4sig(Fo) and 0.0813 for all 3872 data REM 218 parameters refined using 0 restraints END WGHT 0.0722 0.0000 REM Highest difference peak 0.205, deepest hole -0.155, 1-sigma level 0.032 Q1 1 0.0313 0.1511 0.8381 11.00000 0.05 0.21 Q2 1 0.7297 0.0617 0.7413 11.00000 0.05 0.19 Q3 1 -0.1458 0.3370 0.7930 11.00000 0.05 0.15 Q4 1 -0.0691 0.4413 0.6872 11.00000 0.05 0.14 Q5 1 0.0017 0.3950 0.6367 11.00000 0.05 0.14 Q6 1 0.8135 -0.0450 0.5374 11.00000 0.05 0.14 Q7 1 -0.1772 0.4802 0.5635 11.00000 0.05 0.13 Q8 1 -0.1691 0.2127 0.9092 11.00000 0.05 0.12 Q9 1 -0.0817 0.2806 0.7997 11.00000 0.05 0.11 Q10 1 0.2011 0.1619 0.8372 11.00000 0.05 0.11 ; _shelx_res_checksum 71524 _olex2_submission_special_instructions 'No special instructions were received' 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 N2 N 0.05469(12) 0.21014(8) 0.84322(13) 0.0463(4) Uani 1 1 d . O2 O -0.21740(12) 0.42739(8) 0.55510(11) 0.0613(4) Uani 1 1 d . C20 C -0.19671(14) 0.34482(9) 0.73137(14) 0.0403(4) Uani 1 1 d . C19 C -0.14354(15) 0.39579(10) 0.63588(14) 0.0434(4) Uani 1 1 d . O1 O -0.02978(12) 0.40335(8) 0.64195(12) 0.0663(4) Uani 1 1 d . C18 C -0.12634(14) 0.29350(9) 0.81426(14) 0.0416(4) Uani 1 1 d . C17 C 0.00775(15) 0.28011(10) 0.81745(15) 0.0458(4) Uani 1 1 d . H17 H 0.0576 0.3239 0.8002 0.055 Uiso 1 1 calc R C16 C 0.18911(14) 0.20335(10) 0.85715(16) 0.0466(4) Uani 1 1 d . H16 H 0.2239 0.2545 0.8288 0.056 Uiso 1 1 calc R C15 C -0.32235(15) 0.34899(11) 0.73597(16) 0.0521(4) Uani 1 1 d . H15 H -0.3699 0.3821 0.6809 0.062 Uiso 1 1 calc R C14 C -0.18466(16) 0.25134(11) 0.90022(16) 0.0520(5) Uani 1 1 d . H14 H -0.1380 0.2190 0.9570 0.062 Uiso 1 1 calc R C13 C -0.30926(17) 0.25623(12) 0.90345(18) 0.0617(5) Uani 1 1 d . H13 H -0.3462 0.2270 0.9608 0.074 Uiso 1 1 calc R C12 C -0.37827(17) 0.30526(13) 0.82009(19) 0.0640(5) Uani 1 1 d . H12 H -0.4625 0.3088 0.8206 0.077 Uiso 1 1 calc R C11 C 0.23375(17) 0.19161(14) 0.98999(17) 0.0645(5) Uani 1 1 d . H11A H 0.1935 0.1438 1.0200 0.077 Uiso 1 1 calc R H11B H 0.2119 0.2399 1.0343 0.077 Uiso 1 1 calc R C10 C 0.22876(16) 0.13044(13) 0.78484(18) 0.0606(5) Uani 1 1 d . H10A H 0.2037 0.1401 0.7002 0.073 Uiso 1 1 calc R H10B H 0.1885 0.0805 0.8078 0.073 Uiso 1 1 calc R C9 C 0.36721(18) 0.11813(15) 0.8055(2) 0.0747(6) Uani 1 1 d . H9A H 0.3889 0.0694 0.7621 0.090 Uiso 1 1 calc R H9B H 0.4072 0.1656 0.7743 0.090 Uiso 1 1 calc R C8 C 0.41239(17) 0.10772(14) 0.9383(2) 0.0765(7) Uani 1 1 d . H8A H 0.3806 0.0564 0.9671 0.092 Uiso 1 1 calc R H8B H 0.5010 0.1044 0.9489 0.092 Uiso 1 1 calc R C7 C 0.37226(18) 0.17913(15) 1.0109(2) 0.0744(6) Uani 1 1 d . H7A H 0.4126 0.2294 0.9891 0.089 Uiso 1 1 calc R H7B H 0.3970 0.1687 1.0954 0.089 Uiso 1 1 calc R N1 N 0.90814(12) 0.05469(8) 0.85796(12) 0.0453(4) Uani 1 1 d . H1A H 0.9575 0.0983 0.8570 0.054 Uiso 1 1 calc GR H1B H 0.9524 0.0084 0.8632 0.054 Uiso 1 1 calc GR H1C H 0.8663 0.0582 0.9209 0.054 Uiso 1 1 calc GR C6 C 0.82116(15) 0.05322(11) 0.74515(15) 0.0475(4) Uani 1 1 d . H6 H 0.7823 0.1078 0.7348 0.057 Uiso 1 1 calc R C5 C 0.72308(17) -0.01017(15) 0.75540(18) 0.0738(6) Uani 1 1 d . H5A H 0.6776 0.0044 0.8212 0.089 Uiso 1 1 calc R H5B H 0.7602 -0.0641 0.7724 0.089 Uiso 1 1 calc R C4 C 0.88960(18) 0.03682(14) 0.63735(17) 0.0628(5) Uani 1 1 d . H4A H 0.9365 -0.0139 0.6505 0.075 Uiso 1 1 calc R H4B H 0.9465 0.0818 0.6294 0.075 Uiso 1 1 calc R C3 C 0.7043(2) -0.03370(18) 0.5331(2) 0.0939(8) Uani 1 1 d . H3A H 0.7409 -0.0883 0.5437 0.113 Uiso 1 1 calc R H3B H 0.6475 -0.0344 0.4601 0.113 Uiso 1 1 calc R C2 C 0.8022(2) 0.02909(17) 0.52143(18) 0.0818(7) Uani 1 1 d . H2A H 0.7648 0.0825 0.5015 0.098 Uiso 1 1 calc R H2B H 0.8480 0.0131 0.4565 0.098 Uiso 1 1 calc R C1 C 0.6359(2) -0.0143(2) 0.6384(2) 0.1011(9) Uani 1 1 d . H1D H 0.5747 -0.0567 0.6452 0.121 Uiso 1 1 calc R H1E H 0.5941 0.0384 0.6249 0.121 Uiso 1 1 calc R 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 N2 0.0447(8) 0.0394(8) 0.0540(8) 0.0043(6) 0.0033(6) -0.0004(6) O2 0.0683(8) 0.0686(8) 0.0477(7) 0.0160(6) 0.0100(6) 0.0179(6) C20 0.0471(9) 0.0324(9) 0.0404(8) -0.0034(7) 0.0020(7) -0.0016(7) C19 0.0547(10) 0.0344(9) 0.0403(9) -0.0023(7) 0.0027(7) 0.0005(7) O1 0.0582(8) 0.0726(9) 0.0662(8) 0.0229(7) -0.0007(6) -0.0196(7) C18 0.0468(9) 0.0320(9) 0.0459(9) 0.0006(7) 0.0049(7) -0.0016(7) C17 0.0487(9) 0.0383(10) 0.0499(10) 0.0075(8) 0.0047(7) -0.0031(7) C16 0.0409(9) 0.0408(10) 0.0578(10) 0.0072(8) 0.0047(8) -0.0037(7) C15 0.0479(10) 0.0528(11) 0.0537(10) 0.0035(8) -0.0015(8) 0.0027(8) C14 0.0581(11) 0.0418(10) 0.0573(11) 0.0105(8) 0.0115(9) 0.0053(8) C13 0.0624(12) 0.0554(12) 0.0708(13) 0.0129(10) 0.0229(10) -0.0027(9) C12 0.0456(10) 0.0687(13) 0.0793(14) 0.0082(11) 0.0142(10) -0.0016(9) C11 0.0528(11) 0.0820(14) 0.0570(11) -0.0042(10) -0.0001(9) 0.0011(9) C10 0.0545(11) 0.0650(12) 0.0614(11) -0.0058(10) 0.0035(9) 0.0033(9) C9 0.0557(12) 0.0770(15) 0.0933(16) -0.0129(13) 0.0171(11) 0.0070(10) C8 0.0432(10) 0.0783(15) 0.1052(18) 0.0133(14) -0.0025(11) 0.0042(10) C7 0.0531(12) 0.0955(17) 0.0707(14) 0.0033(12) -0.0090(10) -0.0047(11) N1 0.0450(8) 0.0456(8) 0.0448(8) -0.0077(6) 0.0035(6) -0.0007(6) C6 0.0459(9) 0.0492(10) 0.0460(9) -0.0019(8) -0.0001(7) 0.0026(7) C5 0.0588(12) 0.1061(18) 0.0564(12) -0.0030(12) 0.0063(9) -0.0286(12) C4 0.0642(12) 0.0758(14) 0.0499(11) 0.0027(9) 0.0122(9) -0.0058(10) C3 0.1031(19) 0.108(2) 0.0620(15) -0.0176(13) -0.0237(13) -0.0129(15) C2 0.0984(18) 0.0999(18) 0.0456(11) 0.0045(11) 0.0024(11) 0.0057(14) C1 0.0710(15) 0.144(3) 0.0826(17) -0.0091(16) -0.0125(13) -0.0372(15) 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 C17 N2 C16 118.02(14) C18 C20 C19 123.77(15) C15 C20 C19 117.88(14) C15 C20 C18 118.35(15) O2 C19 C20 117.31(16) O2 C19 O1 123.95(16) O1 C19 C20 118.75(14) C20 C18 C17 124.57(14) C14 C18 C20 118.73(16) C14 C18 C17 116.70(15) N2 C17 C18 120.91(15) N2 C16 C11 108.34(14) N2 C16 C10 110.46(13) C10 C16 C11 110.23(15) C12 C15 C20 121.81(16) C13 C14 C18 122.09(16) C14 C13 C12 118.88(17) C13 C12 C15 120.11(18) C16 C11 C7 111.39(16) C16 C10 C9 111.37(15) C8 C9 C10 111.46(18) C7 C8 C9 111.22(17) C8 C7 C11 111.70(17) N1 C6 C5 109.86(15) N1 C6 C4 110.38(15) C5 C6 C4 111.80(16) C6 C5 C1 110.23(19) C6 C4 C2 111.70(17) C2 C3 C1 111.1(2) C3 C2 C4 111.54(19) C3 C1 C5 111.1(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N2 C17 1.261(2) N2 C16 1.474(2) O2 C19 1.252(2) C20 C19 1.523(2) C20 C18 1.407(2) C20 C15 1.392(2) C19 O1 1.252(2) C18 C17 1.488(2) C18 C14 1.398(2) C16 C11 1.525(3) C16 C10 1.523(3) C15 C12 1.381(3) C14 C13 1.379(3) C13 C12 1.381(3) C11 C7 1.528(3) C10 C9 1.527(3) C9 C8 1.523(3) C8 C7 1.508(3) N1 C6 1.493(2) C6 C5 1.502(3) C6 C4 1.524(3) C5 C1 1.532(3) C4 C2 1.527(3) C3 C2 1.497(4) C3 C1 1.508(4)