#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $ #$Revision: 251829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240467.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_7240467 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, C H4 O, Cl' _chemical_formula_sum 'C20 H20 Cl N3 O2' _chemical_formula_weight 369.84 _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 99.8600(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.9435(3) _cell_length_b 21.8674(9) _cell_length_c 11.8018(5) _cell_measurement_reflns_used 18275 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.708 _cell_measurement_theta_min 3.120 _cell_volume 1765.47(13) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _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 0.0330 _diffrn_reflns_av_unetI/netI 0.0277 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 18275 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.708 _diffrn_reflns_theta_min 3.120 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ' Higashi, T. (1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.391 _exptl_crystal_description Needle _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.388 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 4116 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0466 _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^)+(0.0498P)^2^+1.0171P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1141 _refine_ls_wR_factor_ref 0.1241 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3183 _reflns_number_total 4116 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00136h2.cif _cod_data_source_block DHEDHClCH3OH _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 7240467 _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 ; 191220.res created by SHELXL-2014/7 TITL 191220.INS in P2(1)/n CELL 0.71073 6.9435 21.8674 11.8018 90 99.86 90 ZERR 4 0.0003 0.0009 0.0005 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Cl UNIT 80 80 12 8 4 L.S. 4 PLAN 20 TEMP 22.34 BOND ACTA HTAB HTAB O2 Cl1 HTAB N1 Cl1_$1 EQIV $1 x-1/2, -y+1/2, z-1/2 BOND $H fmap 2 REM REM REM WGHT 0.049800 1.017100 FVAR 0.82769 CL1 5 0.806204 0.093746 0.100302 11.00000 0.05189 0.04179 = 0.07899 0.01560 0.02017 0.00200 N1 3 0.559979 0.286756 -0.427134 11.00000 0.03537 0.02819 = 0.03666 -0.00648 0.01067 0.00093 N2 3 0.586620 0.260864 -0.733087 11.00000 0.02813 0.02917 = 0.03276 -0.00676 0.00238 0.00232 N3 3 0.658805 0.354020 -0.636888 11.00000 0.02936 0.02906 = 0.03309 -0.00696 0.00601 -0.00099 O1 4 0.570357 0.253300 -0.926913 11.00000 0.06168 0.04729 = 0.03381 -0.01142 0.00428 0.00405 O2 4 1.193312 0.088413 0.272568 11.00000 0.09371 0.06735 = 0.07408 -0.00279 -0.00745 -0.00645 C1 1 0.569460 0.241274 -0.231166 11.00000 0.03155 0.04289 = 0.03870 -0.00940 0.01182 -0.00649 AFIX 43 H1B 2 0.538153 0.276994 -0.195593 11.00000 -1.20000 AFIX 0 C2 1 0.609111 0.188003 -0.170268 11.00000 0.03363 0.05363 = 0.03433 -0.00171 0.00813 -0.00754 AFIX 43 H2A 2 0.607523 0.188044 -0.091632 11.00000 -1.20000 AFIX 0 C3 1 0.652163 0.133247 -0.223587 11.00000 0.03435 0.04482 = 0.04366 0.00739 0.00668 -0.00268 AFIX 43 H3A 2 0.677781 0.097961 -0.179600 11.00000 -1.20000 AFIX 0 C4 1 0.656994 0.131018 -0.339196 11.00000 0.03208 0.03267 = 0.04421 0.00040 0.00705 -0.00044 AFIX 43 H4A 2 0.683749 0.094561 -0.373999 11.00000 -1.20000 AFIX 0 C5 1 0.620515 0.185201 -0.404200 11.00000 0.02471 0.03280 = 0.03642 -0.00483 0.00575 -0.00190 C6 1 0.577867 0.239907 -0.349270 11.00000 0.02533 0.03358 = 0.03811 -0.00520 0.00736 -0.00339 C7 1 0.587169 0.262577 -0.531716 11.00000 0.02721 0.03103 = 0.03320 -0.00678 0.00492 0.00058 C8 1 0.621377 0.200309 -0.521192 11.00000 0.02581 0.02872 = 0.03674 -0.00430 0.00443 -0.00054 C9 1 0.651614 0.163682 -0.622865 11.00000 0.03931 0.02826 = 0.03960 -0.00480 0.00714 0.00547 AFIX 23 H9A 2 0.603637 0.122369 -0.616651 11.00000 -1.20000 H9B 2 0.789804 0.161606 -0.626949 11.00000 -1.20000 AFIX 0 C10 1 0.541424 0.194220 -0.729615 11.00000 0.03982 0.02792 = 0.03705 -0.00893 0.00237 -0.00051 AFIX 23 H10A 2 0.575401 0.174529 -0.797158 11.00000 -1.20000 H10B 2 0.402142 0.188934 -0.731758 11.00000 -1.20000 AFIX 0 C11 1 0.609394 0.294907 -0.634655 11.00000 0.02306 0.02899 = 0.03275 -0.00566 0.00323 0.00333 C12 1 0.660444 0.384591 -0.741534 11.00000 0.02464 0.03222 = 0.03790 -0.00042 0.00518 0.00285 C13 1 0.637645 0.351047 -0.842961 11.00000 0.02524 0.03744 = 0.03459 0.00030 0.00148 0.00542 C14 1 0.598155 0.285546 -0.842465 11.00000 0.02792 0.03912 = 0.03089 -0.00422 0.00189 0.00646 C15 1 0.648671 0.380267 -0.946955 11.00000 0.03652 0.05224 = 0.03556 0.00169 0.00128 0.00551 AFIX 43 H15A 2 0.637982 0.357623 -1.014446 11.00000 -1.20000 AFIX 0 C16 1 0.675298 0.442438 -0.949408 11.00000 0.05092 0.05370 = 0.05036 0.01759 0.00517 0.00540 AFIX 43 H16A 2 0.684448 0.462010 -1.018246 11.00000 -1.20000 AFIX 0 C17 1 0.688480 0.475918 -0.848222 11.00000 0.05095 0.03630 = 0.06206 0.00972 0.00461 0.00188 AFIX 43 H17A 2 0.701072 0.518209 -0.850978 11.00000 -1.20000 AFIX 0 C18 1 0.683429 0.448328 -0.744628 11.00000 0.04342 0.03279 = 0.05021 -0.00171 0.00812 0.00259 AFIX 43 H18A 2 0.695005 0.471372 -0.677572 11.00000 -1.20000 AFIX 0 C19 1 0.739795 0.387253 -0.529628 11.00000 0.05204 0.03747 = 0.03787 -0.01295 0.00817 -0.01394 AFIX 137 H19A 2 0.845253 0.413081 -0.543287 11.00000 -1.50000 H19B 2 0.787363 0.358335 -0.470195 11.00000 -1.50000 H19C 2 0.639152 0.411837 -0.506025 11.00000 -1.50000 AFIX 0 C20 1 1.297097 0.038700 0.239657 11.00000 0.07769 0.06671 = 0.09037 0.01968 -0.00456 -0.00079 AFIX 137 H20A 2 1.398399 0.053184 0.200380 11.00000 -1.50000 H20B 2 1.209852 0.012660 0.189259 11.00000 -1.50000 H20C 2 1.354429 0.016061 0.306693 11.00000 -1.50000 AFIX 0 H1A 2 0.497468 0.319950 -0.421929 11.00000 0.05284 H2B 2 1.067948 0.090724 0.236555 11.00000 0.10646 HKLF 4 REM 191220.INS in P2(1)/n REM R1 = 0.0466 for 3183 Fo > 4sig(Fo) and 0.0645 for all 4116 data REM 245 parameters refined using 0 restraints END WGHT 0.0459 1.0351 REM Instructions for potential hydrogen bonds EQIV $2 x, y, z-1 HTAB C10 Cl1_$2 EQIV $3 x-1, y, z-1 HTAB C10 O2_$3 EQIV $4 -x+3/2, y+1/2, -z-1/2 HTAB C18 Cl1_$4 HTAB C19 N1 HTAB C19 Cl1_$1 HTAB N1 Cl1_$1 HTAB O2 Cl1 REM Highest difference peak 0.388, deepest hole -0.460, 1-sigma level 0.044 Q1 1 0.8903 0.0973 0.1685 11.00000 0.05 0.39 Q2 1 0.8672 0.0694 0.0537 11.00000 0.05 0.24 Q3 1 0.6010 0.2794 -0.5784 11.00000 0.05 0.22 Q4 1 0.5758 0.2302 -0.5395 11.00000 0.05 0.22 Q5 1 0.5348 0.2376 -0.2971 11.00000 0.05 0.22 Q6 1 0.6069 0.1842 -0.4684 11.00000 0.05 0.21 Q7 1 0.6091 0.3249 -0.8402 11.00000 0.05 0.21 Q8 1 0.6496 0.2362 -0.5232 11.00000 0.05 0.21 Q9 1 0.6019 0.3706 -0.7960 11.00000 0.05 0.21 Q10 1 0.5811 0.2084 -0.3769 11.00000 0.05 0.20 Q11 1 0.6931 0.4145 -0.7402 11.00000 0.05 0.20 Q12 1 0.5965 0.1762 -0.6806 11.00000 0.05 0.19 Q13 1 1.2252 0.0063 0.2475 11.00000 0.05 0.19 Q14 1 0.5369 0.2098 -0.2054 11.00000 0.05 0.18 Q15 1 0.6043 0.1570 -0.3786 11.00000 0.05 0.18 Q16 1 0.6049 0.1635 -0.2125 11.00000 0.05 0.18 Q17 1 0.6452 0.2782 -0.6796 11.00000 0.05 0.17 Q18 1 0.9229 0.1251 0.0759 11.00000 0.05 0.17 Q19 1 0.5775 0.2776 -0.6832 11.00000 0.05 0.16 Q20 1 0.7557 0.4542 -0.8918 11.00000 0.05 0.16 ; _shelx_res_checksum 30471 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 0.80620(8) 0.09375(2) 0.10030(6) 0.05650(19) Uani 1 1 d . . . . . N1 N 0.5600(2) 0.28676(7) -0.42713(13) 0.0329(3) Uani 1 1 d . . . . . N2 N 0.5866(2) 0.26086(6) -0.73309(12) 0.0304(3) Uani 1 1 d . . . . . N3 N 0.6588(2) 0.35402(6) -0.63689(12) 0.0304(3) Uani 1 1 d . . . . . O1 O 0.5704(2) 0.25330(7) -0.92691(12) 0.0481(4) Uani 1 1 d . . . . . O2 O 1.1933(4) 0.08841(10) 0.27257(19) 0.0809(6) Uani 1 1 d . . . . . C1 C 0.5695(3) 0.24127(9) -0.23117(16) 0.0370(4) Uani 1 1 d . . . . . H1B H 0.5382 0.2770 -0.1956 0.044 Uiso 1 1 calc R U . . . C2 C 0.6091(3) 0.18800(9) -0.17027(17) 0.0403(4) Uani 1 1 d . . . . . H2A H 0.6075 0.1880 -0.0916 0.048 Uiso 1 1 calc R U . . . C3 C 0.6522(3) 0.13325(9) -0.22359(17) 0.0409(4) Uani 1 1 d . . . . . H3A H 0.6778 0.0980 -0.1796 0.049 Uiso 1 1 calc R U . . . C4 C 0.6570(3) 0.13102(8) -0.33920(17) 0.0363(4) Uani 1 1 d . . . . . H4A H 0.6837 0.0946 -0.3740 0.044 Uiso 1 1 calc R U . . . C5 C 0.6205(2) 0.18520(8) -0.40420(15) 0.0312(4) Uani 1 1 d . . . . . C6 C 0.5779(2) 0.23991(8) -0.34927(16) 0.0321(4) Uani 1 1 d . . . . . C7 C 0.5872(2) 0.26258(8) -0.53172(15) 0.0305(4) Uani 1 1 d . . . . . C8 C 0.6214(2) 0.20031(8) -0.52119(15) 0.0305(4) Uani 1 1 d . . . . . C9 C 0.6516(3) 0.16368(8) -0.62286(16) 0.0357(4) Uani 1 1 d . . . . . H9A H 0.6036 0.1224 -0.6167 0.043 Uiso 1 1 calc R U . . . H9B H 0.7898 0.1616 -0.6269 0.043 Uiso 1 1 calc R U . . . C10 C 0.5414(3) 0.19422(8) -0.72961(16) 0.0354(4) Uani 1 1 d . . . . . H10A H 0.5754 0.1745 -0.7972 0.043 Uiso 1 1 calc R U . . . H10B H 0.4021 0.1889 -0.7318 0.043 Uiso 1 1 calc R U . . . C11 C 0.6094(2) 0.29491(8) -0.63465(15) 0.0284(3) Uani 1 1 d . . . . . C12 C 0.6604(2) 0.38459(8) -0.74153(15) 0.0316(4) Uani 1 1 d . . . . . C13 C 0.6376(2) 0.35105(8) -0.84296(15) 0.0329(4) Uani 1 1 d . . . . . C14 C 0.5982(3) 0.28555(9) -0.84247(15) 0.0330(4) Uani 1 1 d . . . . . C15 C 0.6487(3) 0.38027(10) -0.94695(17) 0.0420(5) Uani 1 1 d . . . . . H15A H 0.6380 0.3576 -1.0144 0.050 Uiso 1 1 calc R U . . . C16 C 0.6753(3) 0.44244(11) -0.9494(2) 0.0521(5) Uani 1 1 d . . . . . H16A H 0.6844 0.4620 -1.0182 0.062 Uiso 1 1 calc R U . . . C17 C 0.6885(3) 0.47592(10) -0.8482(2) 0.0504(5) Uani 1 1 d . . . . . H17A H 0.7011 0.5182 -0.8510 0.060 Uiso 1 1 calc R U . . . C18 C 0.6834(3) 0.44833(9) -0.74463(18) 0.0421(5) Uani 1 1 d . . . . . H18A H 0.6950 0.4714 -0.6776 0.051 Uiso 1 1 calc R U . . . C19 C 0.7398(3) 0.38725(9) -0.52963(17) 0.0424(5) Uani 1 1 d . . . . . H19A H 0.8453 0.4131 -0.5433 0.064 Uiso 1 1 calc R U . . . H19B H 0.7874 0.3583 -0.4702 0.064 Uiso 1 1 calc R U . . . H19C H 0.6392 0.4118 -0.5060 0.064 Uiso 1 1 calc R U . . . C20 C 1.2971(5) 0.03870(14) 0.2397(3) 0.0805(9) Uani 1 1 d . . . . . H20A H 1.3984 0.0532 0.2004 0.121 Uiso 1 1 calc R U . . . H20B H 1.2099 0.0127 0.1893 0.121 Uiso 1 1 calc R U . . . H20C H 1.3544 0.0161 0.3067 0.121 Uiso 1 1 calc R U . . . H1A H 0.497(3) 0.3199(11) -0.422(2) 0.053(7) Uiso 1 1 d . . . . . H2B H 1.068(6) 0.0907(16) 0.237(3) 0.106(13) 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 0.0519(3) 0.0418(3) 0.0790(4) 0.0156(3) 0.0202(3) 0.0020(2) N1 0.0354(8) 0.0282(7) 0.0367(8) -0.0065(6) 0.0107(7) 0.0009(6) N2 0.0281(7) 0.0292(7) 0.0328(8) -0.0068(6) 0.0024(6) 0.0023(6) N3 0.0294(7) 0.0291(7) 0.0331(8) -0.0070(6) 0.0060(6) -0.0010(6) O1 0.0617(9) 0.0473(8) 0.0338(7) -0.0114(6) 0.0043(6) 0.0040(7) O2 0.0937(17) 0.0674(13) 0.0741(13) -0.0028(10) -0.0074(12) -0.0065(12) C1 0.0316(9) 0.0429(10) 0.0387(10) -0.0094(8) 0.0118(8) -0.0065(8) C2 0.0336(9) 0.0536(12) 0.0343(10) -0.0017(9) 0.0081(8) -0.0075(9) C3 0.0344(10) 0.0448(11) 0.0437(11) 0.0074(9) 0.0067(8) -0.0027(8) C4 0.0321(9) 0.0327(9) 0.0442(11) 0.0004(8) 0.0071(8) -0.0004(7) C5 0.0247(8) 0.0328(9) 0.0364(9) -0.0048(7) 0.0058(7) -0.0019(7) C6 0.0253(8) 0.0336(9) 0.0381(9) -0.0052(7) 0.0074(7) -0.0034(7) C7 0.0272(8) 0.0310(8) 0.0332(9) -0.0068(7) 0.0049(7) 0.0006(7) C8 0.0258(8) 0.0287(8) 0.0367(9) -0.0043(7) 0.0044(7) -0.0005(7) C9 0.0393(10) 0.0283(8) 0.0396(10) -0.0048(7) 0.0071(8) 0.0055(7) C10 0.0398(10) 0.0279(8) 0.0370(10) -0.0089(7) 0.0024(8) -0.0005(7) C11 0.0231(7) 0.0290(8) 0.0327(9) -0.0057(7) 0.0032(7) 0.0033(6) C12 0.0246(8) 0.0322(8) 0.0379(9) -0.0004(7) 0.0052(7) 0.0029(7) C13 0.0252(8) 0.0374(9) 0.0346(9) 0.0003(7) 0.0015(7) 0.0054(7) C14 0.0279(8) 0.0391(9) 0.0309(9) -0.0042(7) 0.0019(7) 0.0065(7) C15 0.0365(10) 0.0522(12) 0.0356(10) 0.0017(9) 0.0013(8) 0.0055(9) C16 0.0509(12) 0.0537(13) 0.0504(12) 0.0176(10) 0.0052(10) 0.0054(10) C17 0.0510(12) 0.0363(10) 0.0621(14) 0.0097(10) 0.0046(11) 0.0019(9) C18 0.0434(11) 0.0328(9) 0.0502(11) -0.0017(8) 0.0081(9) 0.0026(8) C19 0.0520(12) 0.0375(10) 0.0379(10) -0.0129(8) 0.0082(9) -0.0139(9) C20 0.078(2) 0.0667(18) 0.090(2) 0.0197(16) -0.0046(17) -0.0008(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' 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 107.59(15) . . ? C6 N1 H1A 125.3(16) . . ? C7 N1 H1A 122.5(16) . . ? C11 N2 C14 123.50(15) . . ? C11 N2 C10 120.20(15) . . ? C14 N2 C10 116.28(14) . . ? C11 N3 C12 121.13(14) . . ? C11 N3 C19 121.12(15) . . ? C12 N3 C19 117.22(15) . . ? C20 O2 H2B 115(2) . . ? C2 C1 C6 117.58(17) . . ? C2 C1 H1B 121.2 . . ? C6 C1 H1B 121.2 . . ? C1 C2 C3 121.79(18) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C2 121.20(18) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C3 C4 C5 118.59(17) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C4 C5 C6 119.52(17) . . ? C4 C5 C8 133.92(17) . . ? C6 C5 C8 106.53(15) . . ? N1 C6 C1 129.50(17) . . ? N1 C6 C5 109.11(15) . . ? C1 C6 C5 121.30(17) . . ? C8 C7 N1 110.06(16) . . ? C8 C7 C11 121.22(15) . . ? N1 C7 C11 128.06(16) . . ? C7 C8 C5 106.66(15) . . ? C7 C8 C9 120.21(16) . . ? C5 C8 C9 133.12(16) . . ? C8 C9 C10 108.24(14) . . ? C8 C9 H9A 110.0 . . ? C10 C9 H9A 110.0 . . ? C8 C9 H9B 110.0 . . ? C10 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C9 112.03(14) . . ? 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 120.15(15) . . ? N3 C11 C7 123.84(15) . . ? N2 C11 C7 115.94(15) . . ? C13 C12 C18 119.89(17) . . ? C13 C12 N3 119.26(16) . . ? C18 C12 N3 120.85(17) . . ? C12 C13 C15 119.99(17) . . ? C12 C13 C14 120.58(16) . . ? C15 C13 C14 119.42(17) . . ? O1 C14 N2 120.26(17) . . ? O1 C14 C13 124.96(17) . . ? N2 C14 C13 114.74(15) . . ? C16 C15 C13 119.9(2) . . ? C16 C15 H15A 120.0 . . ? C13 C15 H15A 120.0 . . ? C15 C16 C17 119.5(2) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C18 C17 C16 121.8(2) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C17 C18 C12 118.75(19) . . ? C17 C18 H18A 120.6 . . ? C12 C18 H18A 120.6 . . ? 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 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 N1 C6 1.368(2) . ? N1 C7 1.385(2) . ? N1 H1A 0.85(2) . ? N2 C11 1.366(2) . ? N2 C14 1.414(2) . ? N2 C10 1.493(2) . ? N3 C11 1.339(2) . ? N3 C12 1.406(2) . ? N3 C19 1.484(2) . ? O1 C14 1.209(2) . ? O2 C20 1.396(4) . ? O2 H2B 0.90(4) . ? C1 C2 1.372(3) . ? C1 C6 1.405(3) . ? C1 H1B 0.9300 . ? C2 C3 1.408(3) . ? C2 H2A 0.9300 . ? C3 C4 1.371(3) . ? C3 H3A 0.9300 . ? C4 C5 1.411(3) . ? C4 H4A 0.9300 . ? C5 C6 1.416(2) . ? C5 C8 1.421(3) . ? C7 C8 1.384(2) . ? C7 C11 1.437(2) . ? C8 C9 1.487(2) . ? C9 C10 1.513(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.390(2) . ? C12 C18 1.404(3) . ? C13 C15 1.397(3) . ? C13 C14 1.459(3) . ? C15 C16 1.373(3) . ? C15 H15A 0.9300 . ? C16 C17 1.390(3) . ? C16 H16A 0.9300 . ? C17 C18 1.369(3) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 O2 H2B Cl1 0.90(4) 2.21(4) 3.082(2) 162(3) . N1 H1A Cl1 0.85(2) 2.35(2) 3.1990(16) 175(2) 4_565