#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $ #$Revision: 251829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240466.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_7240466 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, 3(H2 O) ' _chemical_formula_sum 'C19 H22 Cl N3 O4' _chemical_formula_weight 391.84 _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 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 98.9720(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.1708(2) _cell_length_b 17.5834(6) _cell_length_c 14.7293(5) _cell_measurement_reflns_used 5419 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 30.190 _cell_measurement_theta_min 2.800 _cell_volume 1834.45(10) _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 0.995 _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 0.0324 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 22958 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.190 _diffrn_reflns_theta_min 2.800 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ' Higashi, T. (1995)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.419 _exptl_crystal_description Bulk _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.338 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 5419 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0468 _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^)+(0.0825P)^2^+0.3670P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1295 _refine_ls_wR_factor_ref 0.1451 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4090 _reflns_number_total 5419 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00136h2.cif _cod_data_source_block DHEDHCl3H2O _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/c' _cod_database_code 7240466 _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 ; 1910253.res created by SHELXL-2014/7 TITL 1910253.INS in P2(1)/c CELL 0.71073 7.1708 17.5834 14.7293 90 98.972 90 ZERR 4 0.0002 0.0006 0.0005 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O Cl UNIT 76 88 12 16 4 L.S. 20 PLAN 10 TEMP 22.71 FMAP 2 acta htab O2 Cl1 htab O2 Cl1_$1 htab O3 O2 htab O3 Cl1_$2 htab O4 Cl1 htab O4 O1_$3 htab N1 O3_$4 EQIV $1 -x+1, -y+1, -z+1 EQIV $2 -x, -y+1, -z+1 EQIV $3 x, y, z-1 EQIV $4 -x, y+1/2, -z+3/2 bond bond $h HTAB REM REM REM WGHT 0.082500 0.367000 FVAR 0.92140 CL1 5 0.354922 0.451015 0.347906 11.00000 0.06795 0.05171 = 0.04961 -0.00092 0.01610 -0.00013 O1 4 0.289165 0.504395 1.024323 11.00000 0.07449 0.02530 = 0.04769 0.00792 0.00068 -0.00650 O2 4 0.272855 0.461289 0.556190 11.00000 0.07473 0.11349 = 0.04964 0.00989 0.01284 -0.02174 O3 4 -0.055701 0.420142 0.620438 11.00000 0.06685 0.03682 = 0.09548 0.01129 0.02062 -0.00207 O4 4 0.340095 0.373832 0.147128 11.00000 0.08101 0.05040 = 0.04738 0.00470 0.00069 0.00386 N1 3 0.137902 0.785468 0.801353 11.00000 0.03563 0.02816 = 0.02991 0.00358 0.00267 0.00408 N2 3 0.256849 0.607402 0.930463 11.00000 0.03333 0.02149 = 0.02973 -0.00035 0.00356 -0.00137 N3 3 0.375356 0.726824 0.980481 11.00000 0.02843 0.02272 = 0.02489 0.00133 0.00312 -0.00006 C1 1 -0.004081 0.845490 0.653331 11.00000 0.03465 0.04949 = 0.04492 0.01933 0.00602 0.00497 AFIX 43 H1B 2 -0.006519 0.894744 0.676126 11.00000 -1.20000 AFIX 0 C2 1 -0.068369 0.829037 0.562651 11.00000 0.03329 0.07748 = 0.04153 0.02682 0.00305 0.00266 AFIX 43 H2A 2 -0.115653 0.868204 0.523237 11.00000 -1.20000 AFIX 0 C3 1 -0.064781 0.754885 0.527765 11.00000 0.03402 0.09438 = 0.02980 0.01363 0.00100 -0.00719 AFIX 43 H3A 2 -0.109289 0.746257 0.465885 11.00000 -1.20000 AFIX 0 C4 1 0.003181 0.694389 0.583008 11.00000 0.03460 0.06749 = 0.02953 -0.00244 0.00234 -0.00896 AFIX 43 H4A 2 0.005066 0.645400 0.559369 11.00000 -1.20000 AFIX 0 C5 1 0.069500 0.709435 0.676328 11.00000 0.02728 0.04477 = 0.02768 0.00152 0.00244 -0.00232 C6 1 0.065400 0.784341 0.709820 11.00000 0.02692 0.04076 = 0.03066 0.00809 0.00362 0.00119 C7 1 0.186399 0.711276 0.827547 11.00000 0.03029 0.02567 = 0.02680 0.00110 0.00278 0.00123 C8 1 0.144097 0.663355 0.752373 11.00000 0.02992 0.03373 = 0.02905 -0.00237 0.00231 -0.00104 C9 1 0.177937 0.580388 0.762470 11.00000 0.04370 0.03224 = 0.03548 -0.00929 0.00033 0.00020 AFIX 23 H9A 2 0.306032 0.568310 0.753904 11.00000 -1.20000 H9B 2 0.091356 0.552786 0.716939 11.00000 -1.20000 AFIX 0 C10 1 0.146884 0.558492 0.858148 11.00000 0.04387 0.02612 = 0.04126 -0.00404 0.00000 -0.00810 AFIX 23 H10A 2 0.013552 0.562715 0.862184 11.00000 -1.20000 H10B 2 0.183660 0.505834 0.869455 11.00000 -1.20000 AFIX 0 C11 1 0.276200 0.683600 0.915481 11.00000 0.02670 0.02288 = 0.02682 0.00072 0.00544 0.00133 C12 1 0.441571 0.697890 1.068958 11.00000 0.02709 0.02795 = 0.02454 0.00142 0.00503 0.00251 C13 1 0.418659 0.620742 1.086076 11.00000 0.03147 0.02755 = 0.02949 0.00340 0.00630 0.00408 C14 1 0.321547 0.571771 1.014778 11.00000 0.03637 0.02540 = 0.03325 0.00452 0.00565 0.00262 C15 1 0.483595 0.590844 1.173419 11.00000 0.04466 0.03557 = 0.03331 0.00904 0.00577 0.00838 AFIX 43 H15A 2 0.466282 0.539556 1.185089 11.00000 -1.20000 AFIX 0 C16 1 0.572754 0.637088 1.241844 11.00000 0.04805 0.04982 = 0.02720 0.00529 0.00326 0.01247 AFIX 43 H16A 2 0.619616 0.617018 1.299297 11.00000 -1.20000 AFIX 0 C17 1 0.592400 0.714104 1.224564 11.00000 0.04041 0.04759 = 0.02847 -0.00394 0.00047 0.00316 AFIX 43 H17A 2 0.650821 0.745368 1.271477 11.00000 -1.20000 AFIX 0 C18 1 0.527442 0.745463 1.139532 11.00000 0.03773 0.03283 = 0.03018 -0.00241 0.00300 0.00092 AFIX 43 H18A 2 0.540515 0.797251 1.129344 11.00000 -1.20000 AFIX 0 C19 1 0.430158 0.805368 0.961009 11.00000 0.04405 0.02637 = 0.03529 0.00543 -0.00023 -0.00953 AFIX 137 H19A 2 0.556821 0.814766 0.990924 11.00000 -1.50000 H19B 2 0.345681 0.840500 0.983556 11.00000 -1.50000 H19C 2 0.423609 0.811916 0.895882 11.00000 -1.50000 AFIX 0 H4B 2 0.328122 0.416278 0.112097 11.00000 0.07324 H4C 2 0.337621 0.392925 0.200440 11.00000 0.08100 H3C 2 0.029134 0.435252 0.598104 11.00000 0.07604 H2B 2 0.284572 0.463503 0.503815 11.00000 0.10203 H2C 2 0.331607 0.494549 0.574330 11.00000 0.09869 H3B 2 -0.129368 0.453226 0.627610 11.00000 0.07525 H1A 2 0.124769 0.823916 0.834947 11.00000 0.04399 HKLF 4 REM 1910253.INS in P2(1)/c REM R1 = 0.0468 for 4090 Fo > 4sig(Fo) and 0.0671 for all 5419 data REM 273 parameters refined using 0 restraints END WGHT 0.0806 0.3809 REM Instructions for potential hydrogen bonds EQIV $5 -x+1, y+1/2, -z+3/2 HTAB C18 Cl1_$5 HTAB C19 N1 HTAB O4 O1_$3 HTAB O4 Cl1 HTAB O3 O2 HTAB O2 Cl1 HTAB O2 Cl1_$1 HTAB O3 Cl1_$2 HTAB N1 O3_$4 REM Highest difference peak 0.338, deepest hole -0.309, 1-sigma level 0.072 Q1 1 0.3287 0.4924 0.3415 11.00000 0.05 0.34 Q2 1 0.0048 0.8134 0.6774 11.00000 0.05 0.33 Q3 1 0.5006 0.7197 1.1018 11.00000 0.05 0.31 Q4 1 0.4179 0.7117 1.0236 11.00000 0.05 0.28 Q5 1 0.4306 0.6572 1.0777 11.00000 0.05 0.27 Q6 1 -0.0519 0.8324 0.6085 11.00000 0.05 0.27 Q7 1 0.5563 0.7287 1.1794 11.00000 0.05 0.26 Q8 1 0.3783 0.5976 1.0542 11.00000 0.05 0.26 Q9 1 0.4614 0.6081 1.1328 11.00000 0.05 0.26 Q10 1 0.2327 0.5044 0.5491 11.00000 0.05 0.26 ; _shelx_res_checksum 90946 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 Cl1 Cl 0.35492(7) 0.45102(3) 0.34791(3) 0.05568(15) Uani 1 1 d . . . . . O1 O 0.28917(19) 0.50439(6) 1.02432(8) 0.0501(3) Uani 1 1 d . . . . . O2 O 0.2729(3) 0.46129(14) 0.55619(14) 0.0790(6) Uani 1 1 d . . . . . O3 O -0.0557(3) 0.42014(8) 0.62044(13) 0.0655(4) Uani 1 1 d . . . . . O4 O 0.3401(2) 0.37383(9) 0.14713(11) 0.0606(4) Uani 1 1 d . . . . . N1 N 0.13790(17) 0.78547(7) 0.80135(8) 0.0315(2) Uani 1 1 d . . . . . N2 N 0.25685(16) 0.60740(6) 0.93046(8) 0.0283(2) Uani 1 1 d . . . . . N3 N 0.37536(15) 0.72682(6) 0.98048(7) 0.0255(2) Uani 1 1 d . . . . . C1 C -0.0041(2) 0.84549(10) 0.65333(11) 0.0430(4) Uani 1 1 d . . . . . H1B H -0.0065 0.8947 0.6761 0.052 Uiso 1 1 calc R U . . . C2 C -0.0684(2) 0.82904(12) 0.56265(12) 0.0511(5) Uani 1 1 d . . . . . H2A H -0.1157 0.8682 0.5232 0.061 Uiso 1 1 calc R U . . . C3 C -0.0648(2) 0.75489(13) 0.52777(11) 0.0532(5) Uani 1 1 d . . . . . H3A H -0.1093 0.7463 0.4659 0.064 Uiso 1 1 calc R U . . . C4 C 0.0032(2) 0.69439(11) 0.58301(10) 0.0442(4) Uani 1 1 d . . . . . H4A H 0.0051 0.6454 0.5594 0.053 Uiso 1 1 calc R U . . . C5 C 0.06950(19) 0.70943(9) 0.67633(9) 0.0334(3) Uani 1 1 d . . . . . C6 C 0.06540(19) 0.78434(8) 0.70982(9) 0.0329(3) Uani 1 1 d . . . . . C7 C 0.18640(18) 0.71128(7) 0.82755(9) 0.0278(3) Uani 1 1 d . . . . . C8 C 0.14410(19) 0.66336(8) 0.75237(9) 0.0311(3) Uani 1 1 d . . . . . C9 C 0.1779(2) 0.58039(8) 0.76247(10) 0.0378(3) Uani 1 1 d . . . . . H9A H 0.3060 0.5683 0.7539 0.045 Uiso 1 1 calc R U . . . H9B H 0.0914 0.5528 0.7169 0.045 Uiso 1 1 calc R U . . . C10 C 0.1469(2) 0.55849(8) 0.85815(10) 0.0378(3) Uani 1 1 d . . . . . H10A H 0.0136 0.5627 0.8622 0.045 Uiso 1 1 calc R U . . . H10B H 0.1837 0.5058 0.8695 0.045 Uiso 1 1 calc R U . . . C11 C 0.27620(17) 0.68360(7) 0.91548(8) 0.0253(2) Uani 1 1 d . . . . . C12 C 0.44157(18) 0.69789(7) 1.06896(8) 0.0264(2) Uani 1 1 d . . . . . C13 C 0.41866(19) 0.62074(7) 1.08608(9) 0.0293(3) Uani 1 1 d . . . . . C14 C 0.3215(2) 0.57177(7) 1.01478(9) 0.0316(3) Uani 1 1 d . . . . . C15 C 0.4836(2) 0.59084(9) 1.17342(10) 0.0379(3) Uani 1 1 d . . . . . H15A H 0.4663 0.5396 1.1851 0.045 Uiso 1 1 calc R U . . . C16 C 0.5728(2) 0.63709(10) 1.24184(10) 0.0420(3) Uani 1 1 d . . . . . H16A H 0.6196 0.6170 1.2993 0.050 Uiso 1 1 calc R U . . . C17 C 0.5924(2) 0.71410(9) 1.22456(10) 0.0393(3) Uani 1 1 d . . . . . H17A H 0.6508 0.7454 1.2715 0.047 Uiso 1 1 calc R U . . . C18 C 0.5274(2) 0.74546(8) 1.13953(9) 0.0338(3) Uani 1 1 d . . . . . H18A H 0.5405 0.7973 1.1293 0.041 Uiso 1 1 calc R U . . . C19 C 0.4302(2) 0.80537(8) 0.96101(10) 0.0359(3) Uani 1 1 d . . . . . H19A H 0.5568 0.8148 0.9909 0.054 Uiso 1 1 calc R U . . . H19B H 0.3457 0.8405 0.9836 0.054 Uiso 1 1 calc R U . . . H19C H 0.4236 0.8119 0.8959 0.054 Uiso 1 1 calc R U . . . H4B H 0.328(3) 0.4163(16) 0.1121(18) 0.073(7) Uiso 1 1 d . . . . . H4C H 0.338(4) 0.3929(15) 0.200(2) 0.081(8) Uiso 1 1 d . . . . . H3C H 0.029(4) 0.4353(15) 0.5981(19) 0.076(8) Uiso 1 1 d . . . . . H2B H 0.285(5) 0.4635(19) 0.504(3) 0.102(11) Uiso 1 1 d . . . . . H2C H 0.332(5) 0.495(2) 0.574(2) 0.099(13) Uiso 1 1 d . . . . . H3B H -0.129(4) 0.4532(16) 0.6276(19) 0.075(8) Uiso 1 1 d . . . . . H1A H 0.125(3) 0.8239(11) 0.8349(13) 0.044(5) 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 0.0679(3) 0.0517(3) 0.0496(3) -0.00092(18) 0.0161(2) -0.0001(2) O1 0.0745(8) 0.0253(5) 0.0477(6) 0.0079(4) 0.0007(6) -0.0065(5) O2 0.0747(11) 0.1135(17) 0.0496(9) 0.0099(9) 0.0128(8) -0.0217(11) O3 0.0669(10) 0.0368(7) 0.0955(12) 0.0113(7) 0.0206(9) -0.0021(7) O4 0.0810(10) 0.0504(8) 0.0474(8) 0.0047(6) 0.0007(7) 0.0039(7) N1 0.0356(6) 0.0282(6) 0.0299(6) 0.0036(4) 0.0027(5) 0.0041(4) N2 0.0333(6) 0.0215(5) 0.0297(5) -0.0003(4) 0.0036(4) -0.0014(4) N3 0.0284(5) 0.0227(5) 0.0249(5) 0.0013(4) 0.0031(4) -0.0001(4) C1 0.0347(7) 0.0495(9) 0.0449(8) 0.0193(7) 0.0060(6) 0.0050(6) C2 0.0333(8) 0.0775(13) 0.0415(8) 0.0268(8) 0.0031(6) 0.0027(8) C3 0.0340(8) 0.0944(15) 0.0298(7) 0.0136(8) 0.0010(6) -0.0072(8) C4 0.0346(7) 0.0675(11) 0.0295(7) -0.0024(7) 0.0023(6) -0.0090(7) C5 0.0273(6) 0.0448(8) 0.0277(6) 0.0015(5) 0.0024(5) -0.0023(5) C6 0.0269(6) 0.0408(7) 0.0307(6) 0.0081(5) 0.0036(5) 0.0012(5) C7 0.0303(6) 0.0257(6) 0.0268(6) 0.0011(4) 0.0028(5) 0.0012(5) C8 0.0299(6) 0.0337(7) 0.0291(6) -0.0024(5) 0.0023(5) -0.0010(5) C9 0.0437(8) 0.0322(7) 0.0355(7) -0.0093(5) 0.0003(6) 0.0002(6) C10 0.0439(8) 0.0261(6) 0.0413(8) -0.0040(5) 0.0000(6) -0.0081(5) C11 0.0267(6) 0.0229(5) 0.0268(5) 0.0007(4) 0.0054(5) 0.0013(4) C12 0.0271(6) 0.0279(6) 0.0245(6) 0.0014(4) 0.0050(5) 0.0025(4) C13 0.0315(6) 0.0275(6) 0.0295(6) 0.0034(5) 0.0063(5) 0.0041(5) C14 0.0364(7) 0.0254(6) 0.0333(7) 0.0045(5) 0.0057(5) 0.0026(5) C15 0.0447(8) 0.0356(7) 0.0333(7) 0.0090(5) 0.0058(6) 0.0084(6) C16 0.0481(9) 0.0498(9) 0.0272(7) 0.0053(6) 0.0033(6) 0.0125(7) C17 0.0404(8) 0.0476(9) 0.0285(6) -0.0039(6) 0.0005(6) 0.0032(6) C18 0.0377(7) 0.0328(7) 0.0302(6) -0.0024(5) 0.0030(5) 0.0009(5) C19 0.0440(8) 0.0264(6) 0.0353(7) 0.0054(5) -0.0002(6) -0.0095(5) 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 H2B O2 H2C 100(3) . . ? H3C O3 H3B 112(3) . . ? H4B O4 H4C 101(2) . . ? C6 N1 C7 107.48(12) . . ? C6 N1 H1A 121.7(13) . . ? C7 N1 H1A 129.0(13) . . ? C11 N2 C14 123.49(11) . . ? C11 N2 C10 120.26(11) . . ? C14 N2 C10 116.01(11) . . ? C11 N3 C12 121.42(10) . . ? C11 N3 C19 121.38(10) . . ? C12 N3 C19 117.10(11) . . ? C2 C1 C6 116.71(17) . . ? C2 C1 H1B 121.6 . . ? C6 C1 H1B 121.6 . . ? C1 C2 C3 121.94(16) . . ? C1 C2 H2A 119.0 . . ? C3 C2 H2A 119.0 . . ? C4 C3 C2 121.66(16) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 117.71(17) . . ? C3 C4 H4A 121.1 . . ? C5 C4 H4A 121.1 . . ? C4 C5 C6 119.70(14) . . ? C4 C5 C8 133.82(15) . . ? C6 C5 C8 106.48(12) . . ? N1 C6 C1 128.25(15) . . ? N1 C6 C5 109.48(12) . . ? C1 C6 C5 122.28(14) . . ? C8 C7 N1 109.55(12) . . ? C8 C7 C11 121.66(12) . . ? N1 C7 C11 128.71(12) . . ? C7 C8 C5 106.99(12) . . ? C7 C8 C9 120.38(12) . . ? C5 C8 C9 132.63(13) . . ? C8 C9 C10 107.38(12) . . ? 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 112.34(12) . . ? N2 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? N2 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? N3 C11 N2 119.81(11) . . ? N3 C11 C7 124.47(11) . . ? N2 C11 C7 115.72(11) . . ? C13 C12 C18 119.85(12) . . ? C13 C12 N3 119.07(11) . . ? C18 C12 N3 121.08(11) . . ? C12 C13 C15 119.98(13) . . ? C12 C13 C14 120.25(11) . . ? C15 C13 C14 119.73(12) . . ? O1 C14 N2 119.53(13) . . ? O1 C14 C13 124.90(13) . . ? N2 C14 C13 115.53(11) . . ? C16 C15 C13 120.14(14) . . ? C16 C15 H15A 119.9 . . ? C13 C15 H15A 119.9 . . ? C15 C16 C17 119.46(14) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 121.72(14) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C17 C18 C12 118.81(13) . . ? 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 . . ? 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 1.2196(17) . ? O2 H2B 0.79(4) . ? O2 H2C 0.75(3) . ? O3 H3C 0.78(3) . ? O3 H3B 0.80(3) . ? O4 H4B 0.90(3) . ? O4 H4C 0.86(3) . ? N1 C6 1.3674(18) . ? N1 C7 1.3892(16) . ? N1 H1A 0.85(2) . ? N2 C11 1.3684(16) . ? N2 C14 1.4037(17) . ? N2 C10 1.4946(17) . ? N3 C11 1.3370(16) . ? N3 C12 1.4105(15) . ? N3 C19 1.4762(16) . ? C1 C2 1.374(2) . ? C1 C6 1.403(2) . ? C1 H1B 0.9300 . ? C2 C3 1.403(3) . ? C2 H2A 0.9300 . ? C3 C4 1.381(3) . ? C3 H3A 0.9300 . ? C4 C5 1.408(2) . ? C4 H4A 0.9300 . ? C5 C6 1.408(2) . ? C5 C8 1.4179(19) . ? C7 C8 1.3868(18) . ? C7 C11 1.4384(17) . ? C8 C9 1.483(2) . ? C9 C10 1.511(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.3941(18) . ? C12 C18 1.3999(18) . ? C13 C15 1.4005(18) . ? C13 C14 1.4495(19) . ? C15 C16 1.373(2) . ? C15 H15A 0.9300 . ? C16 C17 1.389(2) . ? C16 H16A 0.9300 . ? C17 C18 1.381(2) . ? 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 O2 H2B Cl1 0.79(4) 2.44(4) 3.218(2) 170(3) . O2 H2C Cl1 0.75(3) 2.55(3) 3.213(2) 150(3) 3_666 O3 H3C O2 0.78(3) 2.00(3) 2.769(3) 170(3) . O3 H3B Cl1 0.80(3) 2.40(3) 3.2040(19) 178(3) 3_566 O4 H4C Cl1 0.86(3) 2.39(3) 3.2405(17) 175(3) . O4 H4B O1 0.90(3) 2.01(3) 2.9103(19) 175(2) 1_554 N1 H1A O3 0.85(2) 1.91(2) 2.7375(19) 164.2(18) 2_556