#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $ #$Revision: 251829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240470.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_7240470 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 H16 N3 O, Cl, 2(H2 O)' _chemical_formula_sum 'C19 H20 Cl N3 O3' _chemical_formula_weight 373.83 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 90 _cell_angle_beta 97.563(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.0300(13) _cell_length_b 22.083(4) _cell_length_c 11.555(2) _cell_measurement_reflns_used 4394 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.302 _cell_measurement_theta_min 3.065 _cell_volume 1778.2(6) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type CCD _diffrn_measurement_method \w\k _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71076 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_unetI/netI 0.1074 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 18941 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.243 _diffrn_reflns_theta_max 28.302 _diffrn_reflns_theta_min 3.065 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ' Higashi, T. (1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.396 _exptl_crystal_description Needle _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.316 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 4394 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.1794 _refine_ls_R_factor_gt 0.0785 _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^)+(0.1062P)^2^+0.3860P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1827 _refine_ls_wR_factor_ref 0.2275 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2121 _reflns_number_total 4394 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00136h2.cif _cod_data_source_block DHEDHCl2H2O _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_sg_symbol_H-M 'P 21/n' _cod_database_code 7240470 _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 ; 20191114.res created by SHELXL-2014/7 TITL 20191114 in P21/n #14 REM TRY 4 FINAL CC 77.36 TIME 4 SECS REM Fragments: 23 2 1 1 REM reset to P21/n #14 CELL 0.71076 7.03 22.0826 11.5548 90 97.563 90 ZERR 4 0.0013 0.0041 0.0022 0 0.0057 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Cl UNIT 76 80 12 12 4 L.S. 4 0 0 PLAN 20 TEMP 23.43 HTAB HTAB N1 O2 HTAB O2 Cl1 HTAB O3 Cl1 HTAB O2 O3_$1 HTAB O3 Cl1_$2 EQIV $1 -x, -y, -z EQIV $2 -x+1, -y, -z BOND BOND $H ACTA fmap 2 53 REM REM REM WGHT 0.106200 0.386000 FVAR 0.68063 CL1 5 0.374496 0.035978 0.178576 11.00000 0.08580 0.06135 = 0.07321 0.00944 0.00103 -0.00005 N1 3 0.123986 0.222591 0.023578 11.00000 0.04329 0.02942 = 0.03036 0.00610 0.00610 -0.00262 N2 3 0.131824 0.245272 -0.292667 11.00000 0.04011 0.03710 = 0.02480 0.00629 -0.00139 -0.00151 N3 3 0.198937 0.152754 -0.196898 11.00000 0.04062 0.03579 = 0.02475 0.00122 -0.00016 0.00504 O1 4 0.116864 0.253017 -0.489476 11.00000 0.08653 0.06113 = 0.03135 0.01436 0.00381 -0.00331 O2 4 0.022388 0.119732 0.137672 11.00000 0.07346 0.04178 = 0.08523 -0.00048 0.03622 -0.00819 O3 4 0.281440 -0.053972 -0.037584 11.00000 0.08981 0.12741 = 0.11998 -0.04052 0.02679 -0.03537 C1 1 0.133650 0.270600 0.220810 11.00000 0.04450 0.03711 = 0.03555 0.00952 0.01310 0.00407 AFIX 43 H1B 2 0.108169 0.235569 0.260718 11.00000 -1.20000 AFIX 0 C2 1 0.166581 0.325127 0.277624 11.00000 0.05391 0.05203 = 0.03378 -0.00237 0.01160 0.00422 AFIX 43 H2A 2 0.168635 0.326603 0.358216 11.00000 -1.20000 AFIX 0 C3 1 0.197410 0.379032 0.216381 11.00000 0.05910 0.03521 = 0.04916 -0.00707 0.01261 -0.00010 AFIX 43 H3A 2 0.216308 0.415287 0.257231 11.00000 -1.20000 AFIX 0 C4 1 0.199877 0.378734 0.098941 11.00000 0.04960 0.03204 = 0.04159 0.00314 0.00927 -0.00186 AFIX 43 H4A 2 0.219106 0.414435 0.059392 11.00000 -1.20000 AFIX 0 C5 1 0.172788 0.323378 0.038035 11.00000 0.03317 0.02882 = 0.03486 0.00511 0.00466 0.00127 C6 1 0.140250 0.270241 0.100017 11.00000 0.03316 0.02658 = 0.03841 0.00375 0.00610 0.00481 C7 1 0.143090 0.244601 -0.086218 11.00000 0.03231 0.02997 = 0.02778 0.00503 -0.00050 0.00132 C8 1 0.171196 0.306695 -0.079726 11.00000 0.03258 0.03262 = 0.03374 0.00622 0.00267 -0.00019 C9 1 0.192343 0.342408 -0.186070 11.00000 0.05302 0.03118 = 0.03739 0.00794 0.00198 -0.00307 AFIX 23 H9A 2 0.326602 0.345176 -0.196827 11.00000 -1.20000 H9B 2 0.143127 0.383077 -0.178824 11.00000 -1.20000 AFIX 0 C10 1 0.080303 0.310510 -0.288690 11.00000 0.05389 0.03507 = 0.03554 0.01373 -0.00628 0.00398 AFIX 23 H10A 2 -0.055815 0.314208 -0.283535 11.00000 -1.20000 H10B 2 0.105502 0.329949 -0.360402 11.00000 -1.20000 AFIX 0 C11 1 0.156426 0.211783 -0.192334 11.00000 0.03272 0.03476 = 0.02640 0.00483 -0.00340 -0.00240 C12 1 0.198190 0.122072 -0.304076 11.00000 0.03568 0.04150 = 0.03187 -0.00216 0.00063 0.00209 C13 1 0.176835 0.155943 -0.407429 11.00000 0.02977 0.04988 = 0.03032 -0.00126 0.00101 -0.00290 C14 1 0.142093 0.220651 -0.404688 11.00000 0.04055 0.04986 = 0.02855 0.00676 0.00087 -0.00548 C15 1 0.185275 0.126769 -0.514299 11.00000 0.05291 0.06539 = 0.03153 -0.00116 0.00392 -0.00431 AFIX 43 H15A 2 0.173274 0.149184 -0.583014 11.00000 -1.20000 AFIX 0 C16 1 0.211065 0.065527 -0.517943 11.00000 0.07406 0.06695 = 0.04595 -0.01735 0.00284 0.00554 AFIX 43 H16A 2 0.220906 0.046258 -0.588476 11.00000 -1.20000 AFIX 0 C19 1 0.270891 0.118213 -0.090242 11.00000 0.06759 0.03583 = 0.03353 0.00352 -0.00047 0.01623 AFIX 137 H19A 2 0.366601 0.089845 -0.107704 11.00000 -1.50000 H19B 2 0.166480 0.096749 -0.063184 11.00000 -1.50000 H19C 2 0.326243 0.145652 -0.030687 11.00000 -1.50000 AFIX 0 C17 1 0.222426 0.032356 -0.415173 11.00000 0.09227 0.05354 = 0.04853 -0.00986 -0.00434 0.01043 AFIX 43 H17A 2 0.233812 -0.009549 -0.418411 11.00000 -1.20000 AFIX 0 C18 1 0.217315 0.059723 -0.308813 11.00000 0.07000 0.04327 = 0.03977 -0.00153 -0.00148 0.00646 AFIX 43 H18A 2 0.226574 0.036689 -0.240921 11.00000 -1.20000 AFIX 0 H1A 2 0.087007 0.188718 0.044701 11.00000 0.03495 H2B 2 -0.079601 0.098685 0.103677 11.00000 0.06428 H2C 2 0.119569 0.101820 0.167736 11.00000 0.05677 H3B 2 0.355457 -0.046824 -0.075201 11.00000 0.07177 H3C 2 0.277207 -0.034801 0.011524 11.00000 0.09937 HKLF 4 REM 20191114 in P21/n #14 REM R1 = 0.0785 for 2121 Fo > 4sig(Fo) and 0.1794 for all 4394 data REM 256 parameters refined using 0 restraints END WGHT 0.1068 0.3676 REM Instructions for potential hydrogen bonds EQIV $3 x+1/2, -y+1/2, z-1/2 HTAB C9 O2_$3 EQIV $4 x-1/2, -y+1/2, z-1/2 HTAB C9 Cl1_$4 HTAB C19 N1 HTAB N1 O2 HTAB O2 O3_$1 HTAB O2 Cl1 HTAB O3 Cl1_$2 HTAB O3 Cl1 REM Highest difference peak 0.316, deepest hole -0.337, 1-sigma level 0.063 Q1 1 0.2341 -0.0402 -0.1998 11.00000 0.05 0.32 Q2 1 -0.0336 0.0389 0.1769 11.00000 0.05 0.29 Q3 1 0.4164 -0.0424 -0.1803 11.00000 0.05 0.28 Q4 1 0.1768 0.0368 0.1990 11.00000 0.05 0.27 Q5 1 -0.0473 0.1428 -0.3985 11.00000 0.05 0.24 Q6 1 0.1340 0.1791 -0.1954 11.00000 0.05 0.22 Q7 1 0.3672 0.2941 -0.2006 11.00000 0.05 0.22 Q8 1 0.1052 0.3796 -0.3575 11.00000 0.05 0.21 Q9 1 0.0589 0.2516 -0.5646 11.00000 0.05 0.21 Q10 1 0.0421 0.2818 -0.4687 11.00000 0.05 0.20 Q11 1 0.1488 0.2435 0.0757 11.00000 0.05 0.20 Q12 1 0.1320 0.1289 -0.3775 11.00000 0.05 0.20 Q13 1 0.2478 0.2019 -0.5687 11.00000 0.05 0.20 Q14 1 0.1813 0.2001 0.2149 11.00000 0.05 0.20 Q15 1 0.2537 0.1792 -0.4430 11.00000 0.05 0.20 Q16 1 0.2136 0.1177 0.1160 11.00000 0.05 0.19 Q17 1 0.1570 0.4432 0.1896 11.00000 0.05 0.19 Q18 1 0.0813 0.1035 -0.0791 11.00000 0.05 0.19 Q19 1 0.2166 0.2758 -0.0869 11.00000 0.05 0.19 Q20 1 0.0530 0.1432 -0.2342 11.00000 0.05 0.19 ; _shelx_res_checksum 94223 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 Cl 0.37450(19) 0.03598(5) 0.17858(11) 0.0743(4) Uani 1 1 d . . . . . N1 N 0.1240(4) 0.22259(13) 0.0236(2) 0.0342(7) Uani 1 1 d . . . . . N2 N 0.1318(4) 0.24527(12) -0.2927(2) 0.0345(7) Uani 1 1 d . . . . . N3 N 0.1989(4) 0.15275(12) -0.1969(2) 0.0341(7) Uani 1 1 d . . . . . O1 O 0.1169(4) 0.25302(12) -0.4895(2) 0.0600(8) Uani 1 1 d . . . . . O2 O 0.0224(7) 0.11973(14) 0.1377(3) 0.0645(10) Uani 1 1 d . . . . . O3 O 0.2814(8) -0.0540(3) -0.0376(6) 0.1112(18) Uani 1 1 d . . . . . C1 C 0.1337(5) 0.27060(16) 0.2208(3) 0.0384(9) Uani 1 1 d . . . . . H1B H 0.1082 0.2356 0.2607 0.046 Uiso 1 1 calc R U . . . C2 C 0.1666(5) 0.32513(17) 0.2776(3) 0.0461(9) Uani 1 1 d . . . . . H2A H 0.1686 0.3266 0.3582 0.055 Uiso 1 1 calc R U . . . C3 C 0.1974(6) 0.37903(16) 0.2164(3) 0.0473(10) Uani 1 1 d . . . . . H3A H 0.2163 0.4153 0.2572 0.057 Uiso 1 1 calc R U . . . C4 C 0.1999(5) 0.37873(15) 0.0989(3) 0.0408(9) Uani 1 1 d . . . . . H4A H 0.2191 0.4144 0.0594 0.049 Uiso 1 1 calc R U . . . C5 C 0.1728(5) 0.32338(14) 0.0380(3) 0.0323(8) Uani 1 1 d . . . . . C6 C 0.1403(5) 0.27024(14) 0.1000(3) 0.0326(8) Uani 1 1 d . . . . . C7 C 0.1431(4) 0.24460(14) -0.0862(3) 0.0304(7) Uani 1 1 d . . . . . C8 C 0.1712(5) 0.30670(14) -0.0797(3) 0.0331(8) Uani 1 1 d . . . . . C9 C 0.1923(6) 0.34241(15) -0.1861(3) 0.0409(9) Uani 1 1 d . . . . . H9A H 0.3266 0.3452 -0.1968 0.049 Uiso 1 1 calc R U . . . H9B H 0.1431 0.3831 -0.1788 0.049 Uiso 1 1 calc R U . . . C10 C 0.0803(6) 0.31051(15) -0.2887(3) 0.0426(9) Uani 1 1 d . . . . . H10A H -0.0558 0.3142 -0.2835 0.051 Uiso 1 1 calc R U . . . H10B H 0.1055 0.3299 -0.3604 0.051 Uiso 1 1 calc R U . . . C11 C 0.1564(5) 0.21178(14) -0.1923(3) 0.0319(8) Uani 1 1 d . . . . . C12 C 0.1982(5) 0.12207(15) -0.3041(3) 0.0367(8) Uani 1 1 d . . . . . C13 C 0.1768(5) 0.15594(16) -0.4074(3) 0.0369(8) Uani 1 1 d . . . . . C14 C 0.1421(5) 0.22065(17) -0.4047(3) 0.0400(9) Uani 1 1 d . . . . . C15 C 0.1853(6) 0.12677(19) -0.5143(3) 0.0501(10) Uani 1 1 d . . . . . H15A H 0.1733 0.1492 -0.5830 0.060 Uiso 1 1 calc R U . . . C16 C 0.2111(6) 0.0655(2) -0.5179(4) 0.0628(12) Uani 1 1 d . . . . . H16A H 0.2209 0.0463 -0.5885 0.075 Uiso 1 1 calc R U . . . C19 C 0.2709(6) 0.11821(16) -0.0902(3) 0.0463(10) Uani 1 1 d . . . . . H19A H 0.3666 0.0898 -0.1077 0.069 Uiso 1 1 calc R U . . . H19B H 0.1665 0.0967 -0.0632 0.069 Uiso 1 1 calc R U . . . H19C H 0.3262 0.1457 -0.0307 0.069 Uiso 1 1 calc R U . . . C17 C 0.2224(7) 0.0324(2) -0.4152(4) 0.0660(13) Uani 1 1 d . . . . . H17A H 0.2338 -0.0095 -0.4184 0.079 Uiso 1 1 calc R U . . . C18 C 0.2173(6) 0.05972(17) -0.3088(3) 0.0518(10) Uani 1 1 d . . . . . H18A H 0.2266 0.0367 -0.2409 0.062 Uiso 1 1 calc R U . . . H1A H 0.087(5) 0.1887(15) 0.045(3) 0.035(10) Uiso 1 1 d . . . . . H2B H -0.080(7) 0.0987(19) 0.104(4) 0.064(15) Uiso 1 1 d . . . . . H2C H 0.120(6) 0.102(2) 0.168(4) 0.057(16) Uiso 1 1 d . . . . . H3B H 0.355(8) -0.047(2) -0.075(5) 0.07(2) Uiso 1 1 d . . . . . H3C H 0.277(10) -0.035(3) 0.012(5) 0.10(3) 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 Cl1 0.0858(9) 0.0614(8) 0.0732(9) 0.0094(6) 0.0010(7) -0.0001(6) N1 0.0433(18) 0.0294(16) 0.0304(16) 0.0061(12) 0.0061(13) -0.0026(14) N2 0.0401(17) 0.0371(16) 0.0248(15) 0.0063(11) -0.0014(13) -0.0015(13) N3 0.0406(16) 0.0358(16) 0.0248(15) 0.0012(11) -0.0002(12) 0.0050(13) O1 0.087(2) 0.0611(18) 0.0313(15) 0.0144(13) 0.0038(14) -0.0033(15) O2 0.073(3) 0.0418(18) 0.085(3) -0.0005(17) 0.036(2) -0.0082(19) O3 0.090(3) 0.127(4) 0.120(5) -0.041(4) 0.027(3) -0.035(3) C1 0.045(2) 0.0371(19) 0.036(2) 0.0095(15) 0.0131(17) 0.0041(16) C2 0.054(2) 0.052(2) 0.034(2) -0.0024(17) 0.0116(18) 0.0042(19) C3 0.059(3) 0.035(2) 0.049(3) -0.0071(16) 0.013(2) -0.0001(18) C4 0.050(2) 0.0320(19) 0.042(2) 0.0031(15) 0.0093(17) -0.0019(16) C5 0.0332(18) 0.0288(17) 0.0349(19) 0.0051(14) 0.0047(15) 0.0013(14) C6 0.0332(18) 0.0266(17) 0.038(2) 0.0038(14) 0.0061(15) 0.0048(14) C7 0.0323(18) 0.0300(18) 0.0278(18) 0.0050(13) -0.0005(14) 0.0013(14) C8 0.0326(18) 0.0326(18) 0.0337(19) 0.0062(14) 0.0027(15) -0.0002(14) C9 0.053(2) 0.0312(19) 0.037(2) 0.0079(14) 0.0020(17) -0.0031(16) C10 0.054(2) 0.035(2) 0.036(2) 0.0137(15) -0.0063(17) 0.0040(16) C11 0.0327(18) 0.0348(19) 0.0264(18) 0.0048(13) -0.0034(14) -0.0024(14) C12 0.0357(19) 0.042(2) 0.0319(19) -0.0022(15) 0.0006(15) 0.0021(16) C13 0.0298(19) 0.050(2) 0.0303(19) -0.0013(15) 0.0010(15) -0.0029(16) C14 0.041(2) 0.050(2) 0.029(2) 0.0068(16) 0.0009(16) -0.0055(17) C15 0.053(2) 0.065(3) 0.032(2) -0.0012(18) 0.0039(18) -0.004(2) C16 0.074(3) 0.067(3) 0.046(3) -0.017(2) 0.003(2) 0.006(2) C19 0.068(3) 0.036(2) 0.034(2) 0.0035(15) -0.0005(18) 0.0162(18) C17 0.092(4) 0.054(3) 0.049(3) -0.010(2) -0.004(2) 0.010(2) C18 0.070(3) 0.043(2) 0.040(2) -0.0015(17) -0.001(2) 0.006(2) 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' Cl Cl 0.1484 0.1585 '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 108.2(3) . . ? C6 N1 H1A 120(2) . . ? C7 N1 H1A 131(2) . . ? C11 N2 C14 123.5(3) . . ? C11 N2 C10 120.1(3) . . ? C14 N2 C10 116.3(3) . . ? C11 N3 C12 121.8(3) . . ? C11 N3 C19 121.5(3) . . ? C12 N3 C19 116.4(3) . . ? H2B O2 H2C 120(4) . . ? H3B O3 H3C 117(7) . . ? C2 C1 C6 117.0(3) . . ? C2 C1 H1B 121.5 . . ? C6 C1 H1B 121.5 . . ? C1 C2 C3 121.6(3) . . ? C1 C2 H2A 119.2 . . ? C3 C2 H2A 119.2 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C8 C5 C6 107.0(3) . . ? C8 C5 C4 133.8(3) . . ? C6 C5 C4 119.2(3) . . ? N1 C6 C1 129.5(3) . . ? N1 C6 C5 108.5(3) . . ? C1 C6 C5 122.0(3) . . ? N1 C7 C8 109.2(3) . . ? N1 C7 C11 129.1(3) . . ? C8 C7 C11 121.3(3) . . ? C7 C8 C5 107.1(3) . . ? C7 C8 C9 120.7(3) . . ? C5 C8 C9 132.2(3) . . ? C8 C9 C10 107.7(3) . . ? C8 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? C8 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? N2 C10 C9 111.9(3) . . ? N2 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N3 C11 N2 119.8(3) . . ? N3 C11 C7 124.3(3) . . ? N2 C11 C7 115.8(3) . . ? C18 C12 C13 119.8(3) . . ? C18 C12 N3 121.5(3) . . ? C13 C12 N3 118.7(3) . . ? C12 C13 C15 119.6(3) . . ? C12 C13 C14 120.5(3) . . ? C15 C13 C14 119.9(3) . . ? O1 C14 N2 119.7(3) . . ? O1 C14 C13 124.9(3) . . ? N2 C14 C13 115.3(3) . . ? C16 C15 C13 120.2(4) . . ? C16 C15 H15A 119.9 . . ? C13 C15 H15A 119.9 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? 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 . . ? C18 C17 C16 121.8(4) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C17 C18 C12 119.1(4) . . ? C17 C18 H18A 120.4 . . ? C12 C18 H18A 120.4 . . ? 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 N1 C6 1.369(4) . ? N1 C7 1.382(4) . ? N1 H1A 0.84(3) . ? N2 C11 1.367(4) . ? N2 C14 1.415(4) . ? N2 C10 1.488(4) . ? N3 C11 1.340(4) . ? N3 C12 1.411(4) . ? N3 C19 1.481(4) . ? O1 C14 1.207(4) . ? O2 H2B 0.90(4) . ? O2 H2C 0.83(4) . ? O3 H3B 0.74(5) . ? O3 H3C 0.71(6) . ? C1 C2 1.376(5) . ? C1 C6 1.403(5) . ? C1 H1B 0.9300 . ? C2 C3 1.416(5) . ? C2 H2A 0.9300 . ? C3 C4 1.359(5) . ? C3 H3A 0.9300 . ? C4 C5 1.411(5) . ? C4 H4A 0.9300 . ? C5 C8 1.408(5) . ? C5 C6 1.409(4) . ? C7 C8 1.386(4) . ? C7 C11 1.438(4) . ? C8 C9 1.484(4) . ? C9 C10 1.509(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C18 1.385(5) . ? C12 C13 1.400(5) . ? C13 C15 1.401(5) . ? C13 C14 1.451(5) . ? C15 C16 1.366(6) . ? C15 H15A 0.9300 . ? C16 C17 1.389(6) . ? C16 H16A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C17 C18 1.374(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? 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 N1 H1A O2 0.84(3) 1.95(3) 2.767(4) 164(3) . O2 H2C Cl1 0.83(4) 2.30(4) 3.076(5) 157(4) . O3 H3C Cl1 0.71(6) 2.51(6) 3.191(6) 162(7) . O2 H2B O3 0.90(4) 1.81(5) 2.713(6) 178(4) 3 O3 H3B Cl1 0.74(5) 2.38(5) 3.114(6) 171(6) 3_655