#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $ #$Revision: 251829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240468.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_7240468 loop_ _publ_author_name 'Zhang, Guoshun' 'shang, xiaoqing' 'han, wei' 'zhang, lifeng' 'ren, guolian' 'Zhang, Shuqiu' _publ_section_title ; Synthesis, Structural Characterization, Physicochemical Properties and Transformations of Dehydroevodiamine and Its Hydrochloride Salts ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00136H _journal_year 2020 _chemical_formula_moiety 'C19 H17 N3 O2' _chemical_formula_sum 'C19 H17 N3 O2' _chemical_formula_weight 319.35 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-01-29 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 105.866(2) _cell_angle_beta 99.290(2) _cell_angle_gamma 96.696(2) _cell_formula_units_Z 2 _cell_length_a 6.9170(5) _cell_length_b 8.8668(7) _cell_length_c 14.1791(12) _cell_measurement_reflns_used 3946 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.326 _cell_measurement_theta_min 3.028 _cell_volume 813.61(11) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_device_type CCD _diffrn_measurement_method \w\k _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_unetI/netI 0.0373 _diffrn_reflns_Laue_measured_fraction_full 0.974 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8401 _diffrn_reflns_point_group_measured_fraction_full 0.974 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.326 _diffrn_reflns_theta_min 3.028 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ' Higashi, T. (1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.304 _exptl_crystal_description Bulk _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.211 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.034 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 3946 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0489 _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^)+(0.0617P)^2^+0.1472P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1180 _refine_ls_wR_factor_ref 0.1332 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2812 _reflns_number_total 3946 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00136h2.cif _cod_data_source_block DHED _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_database_code 7240468 _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 ; 20191105.res created by SHELXL-2014/7 TITL 20191105.INS in P-1 CELL 0.71073 6.917 8.8668 14.1791 105.866 99.29 96.696 ZERR 2 0.0005 0.0007 0.0012 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 38 34 6 4 L.S. 10 PLAN 20 TEMP 22.58 HTAB BOND $H acta BOND HTAB N3 O1 HTAB N1 O2_$1 EQIV $1 -x+1, -y, -z FMAP 2 REM REM REM WGHT 0.061700 0.147200 FVAR 1.69981 O1 4 -0.168695 0.323918 0.056765 11.00000 0.03952 0.10443 = 0.05904 0.00716 0.00889 0.02183 O2 4 0.288264 0.111908 0.041521 11.00000 0.05522 0.04826 = 0.03517 0.01444 -0.00058 0.02195 N1 3 0.374146 -0.043154 -0.150623 11.00000 0.04332 0.04210 = 0.03323 0.00970 -0.00009 0.01628 N2 3 0.042815 0.215918 -0.037657 11.00000 0.03731 0.03999 = 0.03956 0.01155 -0.00016 0.01225 N3 3 -0.016047 0.412504 0.260663 11.00000 0.06235 0.07061 = 0.04801 0.00545 0.01608 -0.00324 C1 1 0.507960 -0.164085 -0.302715 11.00000 0.05583 0.05170 = 0.04874 0.00227 0.00835 0.01299 AFIX 43 H1B 2 0.604821 -0.208258 -0.270987 11.00000 -1.20000 AFIX 0 C2 1 0.483559 -0.180275 -0.403035 11.00000 0.07629 0.06645 = 0.05111 -0.00146 0.02095 0.00965 AFIX 43 H2A 2 0.565888 -0.236473 -0.439842 11.00000 -1.20000 AFIX 0 C3 1 0.338701 -0.114810 -0.451427 11.00000 0.09346 0.07233 = 0.03639 0.00790 0.01164 0.00734 AFIX 43 H3B 2 0.325993 -0.128683 -0.519701 11.00000 -1.20000 AFIX 0 C4 1 0.215039 -0.030612 -0.400321 11.00000 0.07278 0.06086 = 0.03691 0.01320 -0.00434 0.00645 AFIX 43 H4A 2 0.119579 0.013119 -0.433355 11.00000 -1.20000 AFIX 0 C5 1 0.233689 -0.010831 -0.297316 11.00000 0.04613 0.03894 = 0.03668 0.01014 -0.00313 0.00251 C6 1 0.381827 -0.078735 -0.249988 11.00000 0.04404 0.03667 = 0.03656 0.00530 0.00023 0.00417 C7 1 0.227270 0.047078 -0.134488 11.00000 0.03740 0.03272 = 0.03684 0.01096 -0.00051 0.00875 C8 1 0.136414 0.068341 -0.222010 11.00000 0.03933 0.03575 = 0.03567 0.01226 -0.00351 0.00458 C9 1 -0.025578 0.165706 -0.222163 11.00000 0.04413 0.04671 = 0.04494 0.01900 -0.00732 0.01096 AFIX 23 H9A 2 -0.127863 0.117989 -0.282078 11.00000 -1.20000 H9B 2 0.027291 0.272105 -0.221892 11.00000 -1.20000 AFIX 0 C10 1 -0.113883 0.173866 -0.129879 11.00000 0.03594 0.04986 = 0.04788 0.01431 -0.00436 0.01151 AFIX 23 H10A 2 -0.200912 0.252745 -0.122950 11.00000 -1.20000 H10B 2 -0.193193 0.071667 -0.138176 11.00000 -1.20000 AFIX 0 C11 1 0.192748 0.123636 -0.035877 11.00000 0.03719 0.03172 = 0.03680 0.01193 -0.00006 0.00750 C12 1 0.155861 0.456690 0.231615 11.00000 0.04758 0.03346 = 0.04871 0.00730 0.00864 0.00974 C13 1 0.173716 0.408684 0.130146 11.00000 0.03979 0.03140 = 0.04669 0.00912 0.00808 0.01059 C14 1 0.003003 0.314007 0.051209 11.00000 0.03772 0.04376 = 0.04617 0.01437 0.00815 0.01285 C15 1 0.350762 0.459555 0.104575 11.00000 0.04801 0.04423 = 0.05782 0.01060 0.01434 0.00653 AFIX 43 H15A 2 0.361752 0.427843 0.037762 11.00000 -1.20000 AFIX 0 C16 1 0.509267 0.554803 0.174655 11.00000 0.04617 0.05647 = 0.08311 0.00769 0.01275 -0.00259 AFIX 43 H16A 2 0.625640 0.588556 0.155884 11.00000 -1.20000 AFIX 0 C17 1 0.492372 0.599476 0.273604 11.00000 0.05124 0.05337 = 0.07618 -0.00163 -0.00518 -0.00112 AFIX 43 H17A 2 0.598944 0.664083 0.321929 11.00000 -1.20000 AFIX 0 C18 1 0.321420 0.550538 0.302271 11.00000 0.06220 0.04494 = 0.05148 -0.00034 0.00227 0.01003 AFIX 43 H18A 2 0.315486 0.580237 0.369789 11.00000 -1.20000 AFIX 0 C19 1 -0.034988 0.450899 0.363747 11.00000 0.09486 0.09053 = 0.05692 0.00665 0.02990 -0.00630 AFIX 33 H19A 2 -0.166971 0.408915 0.367440 11.00000 -1.50000 H19B 2 0.059668 0.405059 0.399717 11.00000 -1.50000 H19C 2 -0.010300 0.564346 0.392873 11.00000 -1.50000 AFIX 0 H1A 2 0.464186 -0.064311 -0.103090 11.00000 0.05960 H3A 2 -0.122016 0.365659 0.211059 11.00000 0.08047 HKLF 4 REM 20191105.INS in P-1 REM R1 = 0.0489 for 2812 Fo > 4sig(Fo) and 0.0757 for all 3946 data REM 225 parameters refined using 0 restraints END WGHT 0.0561 0.1561 REM Instructions for potential hydrogen bonds EQIV $2 -x, -y, -z HTAB C10 O2_$2 HTAB N1 O2_$1 HTAB N3 O1 REM Highest difference peak 0.211, deepest hole -0.178, 1-sigma level 0.034 Q1 1 0.2305 0.1008 -0.0858 11.00000 0.05 0.21 Q2 1 0.2018 0.0593 -0.2612 11.00000 0.05 0.19 Q3 1 0.0331 0.2639 0.0053 11.00000 0.05 0.19 Q4 1 0.1444 0.0089 -0.2753 11.00000 0.05 0.19 Q5 1 0.2736 -0.0848 -0.2798 11.00000 0.05 0.18 Q6 1 0.1737 0.3877 0.1767 11.00000 0.05 0.17 Q7 1 0.3531 -0.0011 -0.2633 11.00000 0.05 0.17 Q8 1 0.5235 0.5148 0.2267 11.00000 0.05 0.17 Q9 1 0.1351 0.0270 -0.1818 11.00000 0.05 0.16 Q10 1 0.0618 0.1319 -0.0328 11.00000 0.05 0.16 Q11 1 0.1010 0.3480 0.0987 11.00000 0.05 0.16 Q12 1 -0.1156 0.4155 0.0633 11.00000 0.05 0.15 Q13 1 0.2188 0.1040 -0.1647 11.00000 0.05 0.15 Q14 1 0.3389 0.4536 0.0072 11.00000 0.05 0.13 Q15 1 0.4342 0.5274 0.3023 11.00000 0.05 0.13 Q16 1 0.0534 0.3408 0.2540 11.00000 0.05 0.13 Q17 1 0.3490 0.0277 0.0015 11.00000 0.05 0.12 Q18 1 0.1269 0.4594 0.1681 11.00000 0.05 0.12 Q19 1 -0.0222 0.1912 -0.0804 11.00000 0.05 0.12 Q20 1 0.2543 0.3890 0.1202 11.00000 0.05 0.12 ; _shelx_res_checksum 83143 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 O1 O -0.16869(18) 0.32392(18) 0.05677(10) 0.0705(4) Uani 1 1 d . . . . . O2 O 0.28826(16) 0.11191(12) 0.04152(7) 0.0458(3) Uani 1 1 d . . . . . N1 N 0.37415(19) -0.04315(14) -0.15062(9) 0.0400(3) Uani 1 1 d . . . . . N2 N 0.04282(18) 0.21592(14) -0.03766(9) 0.0395(3) Uani 1 1 d . . . . . N3 N -0.0160(3) 0.4125(2) 0.26066(12) 0.0635(4) Uani 1 1 d . . . . . C1 C 0.5080(3) -0.1641(2) -0.30271(13) 0.0546(4) Uani 1 1 d . . . . . H1B H 0.6048 -0.2083 -0.2710 0.066 Uiso 1 1 calc R U . . . C2 C 0.4836(3) -0.1803(2) -0.40304(14) 0.0677(5) Uani 1 1 d . . . . . H2A H 0.5659 -0.2365 -0.4398 0.081 Uiso 1 1 calc R U . . . C3 C 0.3387(4) -0.1148(3) -0.45143(14) 0.0698(6) Uani 1 1 d . . . . . H3B H 0.3260 -0.1287 -0.5197 0.084 Uiso 1 1 calc R U . . . C4 C 0.2150(3) -0.0306(2) -0.40032(12) 0.0594(5) Uani 1 1 d . . . . . H4A H 0.1196 0.0131 -0.4334 0.071 Uiso 1 1 calc R U . . . C5 C 0.2337(2) -0.01083(17) -0.29732(11) 0.0426(3) Uani 1 1 d . . . . . C6 C 0.3818(2) -0.07874(17) -0.24999(11) 0.0414(3) Uani 1 1 d . . . . . C7 C 0.2273(2) 0.04708(16) -0.13449(10) 0.0362(3) Uani 1 1 d . . . . . C8 C 0.1364(2) 0.06834(16) -0.22201(10) 0.0380(3) Uani 1 1 d . . . . . C9 C -0.0256(2) 0.16571(19) -0.22216(12) 0.0458(4) Uani 1 1 d . . . . . H9A H -0.1279 0.1180 -0.2821 0.055 Uiso 1 1 calc R U . . . H9B H 0.0273 0.2721 -0.2219 0.055 Uiso 1 1 calc R U . . . C10 C -0.1139(2) 0.17387(19) -0.12988(12) 0.0458(4) Uani 1 1 d . . . . . H10A H -0.2009 0.2527 -0.1230 0.055 Uiso 1 1 calc R U . . . H10B H -0.1932 0.0717 -0.1382 0.055 Uiso 1 1 calc R U . . . C11 C 0.1927(2) 0.12364(16) -0.03588(10) 0.0356(3) Uani 1 1 d . . . . . C12 C 0.1559(2) 0.45669(17) 0.23161(12) 0.0441(4) Uani 1 1 d . . . . . C13 C 0.1737(2) 0.40868(16) 0.13015(11) 0.0395(3) Uani 1 1 d . . . . . C14 C 0.0030(2) 0.31401(18) 0.05121(11) 0.0419(3) Uani 1 1 d . . . . . C15 C 0.3508(2) 0.45955(19) 0.10457(13) 0.0506(4) Uani 1 1 d . . . . . H15A H 0.3618 0.4278 0.0378 0.061 Uiso 1 1 calc R U . . . C16 C 0.5093(3) 0.5548(2) 0.17465(16) 0.0656(5) Uani 1 1 d . . . . . H16A H 0.6256 0.5886 0.1559 0.079 Uiso 1 1 calc R U . . . C17 C 0.4924(3) 0.5995(2) 0.27360(16) 0.0675(5) Uani 1 1 d . . . . . H17A H 0.5989 0.6641 0.3219 0.081 Uiso 1 1 calc R U . . . C18 C 0.3214(3) 0.5505(2) 0.30227(14) 0.0569(4) Uani 1 1 d . . . . . H18A H 0.3155 0.5802 0.3698 0.068 Uiso 1 1 calc R U . . . C19 C -0.0350(4) 0.4509(3) 0.36375(15) 0.0840(7) Uani 1 1 d . . . . . H19A H -0.1670 0.4089 0.3674 0.126 Uiso 1 1 calc R U . . . H19B H 0.0597 0.4051 0.3997 0.126 Uiso 1 1 calc R U . . . H19C H -0.0103 0.5643 0.3929 0.126 Uiso 1 1 calc R U . . . H1A H 0.464(3) -0.064(2) -0.1031(14) 0.060(5) Uiso 1 1 d . . . . . H3A H -0.122(3) 0.366(3) 0.2111(16) 0.080(7) Uiso 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 O1 0.0395(7) 0.1044(11) 0.0590(8) 0.0072(7) 0.0089(6) 0.0218(7) O2 0.0552(6) 0.0483(6) 0.0352(5) 0.0144(5) -0.0006(5) 0.0220(5) N1 0.0433(7) 0.0421(7) 0.0332(6) 0.0097(5) -0.0001(5) 0.0163(5) N2 0.0373(6) 0.0400(6) 0.0396(6) 0.0115(5) -0.0002(5) 0.0123(5) N3 0.0623(10) 0.0706(10) 0.0480(9) 0.0054(8) 0.0161(8) -0.0032(8) C1 0.0558(10) 0.0517(9) 0.0487(10) 0.0023(8) 0.0084(8) 0.0130(8) C2 0.0763(13) 0.0664(12) 0.0511(11) -0.0015(9) 0.0210(10) 0.0097(10) C3 0.0935(15) 0.0723(13) 0.0364(9) 0.0079(9) 0.0116(10) 0.0073(11) C4 0.0728(12) 0.0609(11) 0.0369(8) 0.0132(8) -0.0043(8) 0.0064(9) C5 0.0461(8) 0.0389(7) 0.0367(8) 0.0101(6) -0.0031(6) 0.0025(6) C6 0.0440(8) 0.0367(7) 0.0366(7) 0.0053(6) 0.0002(6) 0.0042(6) C7 0.0374(7) 0.0327(6) 0.0368(7) 0.0110(6) -0.0005(6) 0.0087(5) C8 0.0393(8) 0.0358(7) 0.0357(7) 0.0123(6) -0.0035(6) 0.0046(6) C9 0.0441(8) 0.0467(8) 0.0449(8) 0.0190(7) -0.0073(7) 0.0110(7) C10 0.0359(8) 0.0499(8) 0.0479(9) 0.0143(7) -0.0044(6) 0.0115(6) C11 0.0372(7) 0.0317(6) 0.0368(7) 0.0119(6) -0.0001(6) 0.0075(5) C12 0.0476(9) 0.0335(7) 0.0487(9) 0.0073(6) 0.0086(7) 0.0097(6) C13 0.0398(8) 0.0314(7) 0.0467(8) 0.0091(6) 0.0081(6) 0.0106(6) C14 0.0377(8) 0.0438(8) 0.0462(8) 0.0144(7) 0.0081(6) 0.0129(6) C15 0.0480(9) 0.0442(8) 0.0578(10) 0.0106(7) 0.0143(8) 0.0065(7) C16 0.0462(10) 0.0565(11) 0.0831(14) 0.0077(10) 0.0128(9) -0.0026(8) C17 0.0512(11) 0.0534(10) 0.0762(13) -0.0016(9) -0.0052(9) -0.0011(8) C18 0.0622(11) 0.0449(9) 0.0515(10) -0.0003(8) 0.0023(8) 0.0100(8) C19 0.0949(17) 0.0905(16) 0.0569(12) 0.0066(11) 0.0299(12) -0.0063(13) 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 C6 N1 C7 107.84(12) . . ? C6 N1 H1A 124.6(11) . . ? C7 N1 H1A 127.0(11) . . ? C11 N2 C14 121.60(12) . . ? C11 N2 C10 118.13(12) . . ? C14 N2 C10 117.71(12) . . ? C12 N3 C19 123.01(17) . . ? C12 N3 H3A 116.0(14) . . ? C19 N3 H3A 120.8(14) . . ? C2 C1 C6 117.42(18) . . ? C2 C1 H1B 121.3 . . ? C6 C1 H1B 121.3 . . ? C1 C2 C3 121.80(18) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C2 121.17(17) . . ? C4 C3 H3B 119.4 . . ? C2 C3 H3B 119.4 . . ? C3 C4 C5 119.28(17) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C4 C5 C6 118.43(15) . . ? C4 C5 C8 134.70(15) . . ? C6 C5 C8 106.86(12) . . ? N1 C6 C1 129.86(15) . . ? N1 C6 C5 108.23(13) . . ? C1 C6 C5 121.90(15) . . ? C8 C7 N1 110.72(13) . . ? C8 C7 C11 125.43(13) . . ? N1 C7 C11 123.46(12) . . ? C7 C8 C5 106.34(13) . . ? C7 C8 C9 120.14(14) . . ? C5 C8 C9 133.47(13) . . ? C8 C9 C10 109.13(12) . . ? C8 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C9 111.70(12) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N2 123.16(13) . . ? O2 C11 C7 123.58(13) . . ? N2 C11 C7 113.24(12) . . ? N3 C12 C18 120.67(16) . . ? N3 C12 C13 121.66(14) . . ? C18 C12 C13 117.67(15) . . ? C15 C13 C12 119.24(14) . . ? C15 C13 C14 120.07(14) . . ? C12 C13 C14 120.59(13) . . ? O1 C14 N2 118.68(14) . . ? O1 C14 C13 123.19(14) . . ? N2 C14 C13 117.97(12) . . ? C16 C15 C13 122.12(17) . . ? C16 C15 H15A 118.9 . . ? C13 C15 H15A 118.9 . . ? C15 C16 C17 118.49(17) . . ? C15 C16 H16A 120.8 . . ? C17 C16 H16A 120.8 . . ? C16 C17 C18 121.32(17) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C17 C18 C12 121.12(17) . . ? C17 C18 H18A 119.4 . . ? C12 C18 H18A 119.4 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C14 1.2146(18) . ? O2 C11 1.2231(16) . ? N1 C6 1.3684(19) . ? N1 C7 1.3744(18) . ? N1 H1A 0.916(19) . ? N2 C11 1.3952(17) . ? N2 C14 1.4102(19) . ? N2 C10 1.4850(18) . ? N3 C12 1.369(2) . ? N3 C19 1.439(2) . ? N3 H3A 0.90(2) . ? C1 C2 1.370(3) . ? C1 C6 1.396(2) . ? C1 H1B 0.9300 . ? C2 C3 1.394(3) . ? C2 H2A 0.9300 . ? C3 C4 1.367(3) . ? C3 H3B 0.9300 . ? C4 C5 1.405(2) . ? C4 H4A 0.9300 . ? C5 C6 1.416(2) . ? C5 C8 1.421(2) . ? C7 C8 1.3690(19) . ? C7 C11 1.449(2) . ? C8 C9 1.492(2) . ? C9 C10 1.519(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C18 1.400(2) . ? C12 C13 1.415(2) . ? C13 C15 1.392(2) . ? C13 C14 1.477(2) . ? C15 C16 1.370(2) . ? C15 H15A 0.9300 . ? C16 C17 1.378(3) . ? C16 H16A 0.9300 . ? C17 C18 1.372(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O1 0.90(2) 2.08(2) 2.769(2) 132.7(18) . N1 H1A O2 0.916(19) 1.94(2) 2.8105(16) 158.4(16) 2_655