#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:31:29 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270482 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060968.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_7060968 loop_ _publ_author_name 'Zhang, Yunan' 'Duan, Yu' 'Su, Jin' 'Liu, Lixin' 'Feng, Yanru' 'Wu, Lili' 'Zhang, Lei' 'Zhang, Yunjie' 'Zou, Dongyu' 'Liu, Yingli' _publ_section_title ; Inspiration for revival of old drugs: improving solubility and avoiding hygroscopicity of pipemidic acid by forming two pharmaceutical salts based on charge-assisted hydrogen bond recognitions ; _journal_issue 42 _journal_name_full 'New Journal of Chemistry' _journal_page_first 19704 _journal_page_last 19713 _journal_paper_doi 10.1039/D1NJ03314J _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C14 H18 N5 O3, C7 H5 O4, 2(H2 O)' _chemical_formula_sum 'C21 H27 N5 O9' _chemical_formula_weight 493.48 _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 ; 2021-09-20 deposited with the CCDC. 2021-09-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.673(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.3506(8) _cell_length_b 18.9562(17) _cell_length_c 12.9324(11) _cell_measurement_reflns_used 2123 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.3930 _cell_measurement_theta_min 3.8930 _cell_volume 2259.7(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 16.1213 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.848 _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_unetI/netI 0.0863 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.848 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 15896 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.848 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.713 _diffrn_reflns_theta_min 3.372 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.37777 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.451 _exptl_crystal_description block _exptl_crystal_F_000 1040.0 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.207 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 6411 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.1444 _refine_ls_R_factor_gt 0.0611 _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^)+(0.0533P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1204 _refine_ls_wR_factor_ref 0.1577 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2644 _reflns_number_total 5439 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03314j2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7060968--7060969.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060968 _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 ; shelx.res created by SHELXL-2014/7 TITL SIR97 run in space group P 21/n CELL 0.71073 9.3506 18.9562 12.9324 90.000 99.673 90.000 ZERR 4.00 0.0008 0.0017 0.0011 0.000 0.009 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 45 45 45 45 MERG 2 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 10 TEMP 25.00 WGHT 0.053300 FVAR 0.46561 AFIX 6 O1 4 0.176767 -0.013775 0.556170 11.00000 0.06283 0.04530 = 0.05434 0.00502 0.00271 -0.00323 H1A 2 0.216073 -0.054260 0.557175 11.00000 -1.50000 H1B 2 0.235424 0.015031 0.591398 11.00000 -1.50000 AFIX 0 N1 3 0.602146 0.054830 0.866793 11.00000 0.03744 0.04105 = 0.04379 -0.00635 0.01230 0.00046 N2 3 0.670287 -0.015629 0.738482 11.00000 0.03396 0.05264 = 0.04891 -0.01672 0.01513 -0.00462 O2 4 0.214945 0.354498 0.926108 11.00000 0.07146 0.05024 = 0.06427 -0.00766 0.03475 -0.00265 N3 3 0.527960 0.125886 0.993925 11.00000 0.03748 0.04652 = 0.04269 -0.00840 0.01199 -0.00098 O3 4 0.115201 0.045435 0.930076 11.00000 0.03859 0.10066 = 0.06431 -0.01834 0.01820 -0.00610 N4 3 0.437163 -0.028492 0.769529 11.00000 0.03642 0.05117 = 0.05010 -0.00936 0.01110 -0.00449 N5 3 0.888635 -0.064331 0.626994 11.00000 0.04850 0.04777 = 0.03991 0.00506 0.01302 0.01350 AFIX 23 H5A 2 0.875012 -0.035938 0.571396 11.00000 -1.20000 H5B 2 0.961535 -0.093372 0.620876 11.00000 -1.20000 AFIX 0 O4 4 0.433115 0.223530 0.749723 11.00000 0.04567 0.06975 = 0.08873 -0.03283 0.02496 -0.01350 AFIX 147 H4 2 0.461720 0.260244 0.779819 11.00000 -1.50000 AFIX 0 C1 1 0.289830 0.216502 0.748815 11.00000 0.03932 0.04290 = 0.04306 0.00396 0.00831 -0.00850 O5 4 0.296942 0.119825 0.629494 11.00000 0.08045 0.05591 = 0.06277 -0.01939 0.02779 -0.01771 AFIX 147 H5 2 0.375982 0.137661 0.626326 11.00000 -1.50000 AFIX 0 C2 1 0.567602 0.005075 0.793182 11.00000 0.03624 0.03989 = 0.04343 -0.00274 0.00937 0.00160 C3 1 0.354720 0.047309 0.895306 11.00000 0.03382 0.04498 = 0.03510 0.00158 0.00942 0.00056 C4 1 0.495227 0.075124 0.916434 11.00000 0.03754 0.03783 = 0.03393 0.00245 0.00852 0.00553 O6 4 0.040953 0.132242 1.059208 11.00000 0.04687 0.10778 = 0.06794 -0.01163 0.02251 0.00862 AFIX 147 H6 2 0.039935 0.099064 1.018405 11.00000 -1.50000 AFIX 0 C5 1 0.211144 0.259142 0.806263 11.00000 0.04245 0.03352 = 0.04493 0.00477 0.01071 -0.00556 O7 4 0.414769 0.330747 0.862092 11.00000 0.04809 0.06727 = 0.10187 -0.03632 0.02673 -0.01783 O8 4 0.201701 0.206351 1.143344 11.00000 0.06950 0.07555 = 0.06551 -0.01158 0.02643 0.01655 C6 1 0.336574 -0.006427 0.820441 11.00000 0.03728 0.05498 = 0.04056 -0.00223 0.00685 -0.00494 AFIX 43 H6A 2 0.246177 -0.028071 0.805797 11.00000 -1.20000 AFIX 0 C7 1 0.280548 0.127613 1.021664 11.00000 0.03982 0.05406 = 0.03740 0.00691 0.01280 0.00997 C8 1 0.240805 0.071406 0.947655 11.00000 0.03665 0.05869 = 0.03948 0.00723 0.00973 0.00575 C9 1 0.419979 0.150449 1.041336 11.00000 0.04981 0.04576 = 0.04150 -0.00116 0.01288 0.00969 AFIX 43 H9 2 0.442884 0.185738 1.091332 11.00000 -1.20000 AFIX 0 C10 1 0.926985 -0.021382 0.724399 11.00000 0.03892 0.05990 = 0.04605 -0.00167 0.01256 -0.00192 AFIX 23 H10A 2 1.011137 0.007472 0.719148 11.00000 -1.20000 H10B 2 0.952125 -0.052588 0.784132 11.00000 -1.20000 AFIX 0 C11 1 0.284051 0.318863 0.870629 11.00000 0.05292 0.03782 = 0.05027 0.00357 0.01611 -0.00153 C12 1 0.754919 -0.106005 0.629609 11.00000 0.05257 0.04585 = 0.04317 -0.00627 0.01534 -0.00268 AFIX 23 H12A 2 0.772206 -0.139550 0.686992 11.00000 -1.20000 H12B 2 0.730103 -0.132286 0.564715 11.00000 -1.20000 AFIX 0 C13 1 0.631181 -0.058693 0.643468 11.00000 0.04484 0.05565 = 0.04676 -0.01379 0.01430 -0.00439 AFIX 23 H13A 2 0.607509 -0.028178 0.582796 11.00000 -1.20000 H13B 2 0.546343 -0.086954 0.649078 11.00000 -1.20000 AFIX 0 C14 1 0.678632 0.152230 1.024775 11.00000 0.04546 0.05382 = 0.05169 -0.01046 0.00717 -0.00516 AFIX 23 H14A 2 0.745908 0.114133 1.018525 11.00000 -1.20000 H14B 2 0.692994 0.166714 1.097726 11.00000 -1.20000 AFIX 0 C15 1 0.063421 0.247501 0.799963 11.00000 0.04726 0.04131 = 0.08441 0.00113 0.02314 -0.00481 AFIX 43 H15 2 0.010158 0.274758 0.839687 11.00000 -1.20000 AFIX 0 C16 1 0.803390 0.025339 0.741588 11.00000 0.03884 0.05751 = 0.06166 -0.01785 0.01678 -0.00664 AFIX 23 H16A 2 0.827420 0.048585 0.809094 11.00000 -1.20000 H16B 2 0.788153 0.061439 0.687699 11.00000 -1.20000 AFIX 0 C17 1 0.172887 0.159040 1.079598 11.00000 0.05062 0.06864 = 0.04406 0.00879 0.01633 0.01357 AFIX 6 O18 4 0.436080 -0.153918 0.407541 11.00000 0.09786 0.09011 = 0.10096 -0.03248 0.06066 -0.02414 H18A 2 0.395916 -0.152878 0.461811 11.00000 -1.50000 H18B 2 0.412236 -0.191666 0.373505 11.00000 -1.50000 AFIX 0 C19 1 0.073991 0.154307 0.676934 11.00000 0.05855 0.05366 = 0.07536 -0.00380 0.00069 -0.01953 AFIX 43 H19 2 0.026664 0.120229 0.631962 11.00000 -1.20000 AFIX 0 C20 1 0.221119 0.162796 0.684658 11.00000 0.05424 0.03990 = 0.04411 0.00320 0.00977 -0.00749 C21 1 0.712072 0.213296 0.958769 11.00000 0.05843 0.06746 = 0.09003 0.00440 0.01543 -0.01146 AFIX 137 H21A 2 0.703296 0.198556 0.886961 11.00000 -1.50000 H21B 2 0.809226 0.229374 0.983217 11.00000 -1.50000 H21C 2 0.645066 0.250987 0.963944 11.00000 -1.50000 AFIX 0 C22 1 -0.004559 0.195520 0.734810 11.00000 0.04129 0.06291 = 0.11553 -0.00276 0.01232 -0.00876 AFIX 43 H22 2 -0.103838 0.188309 0.729993 11.00000 -1.20000 AFIX 0 HKLF 4 REM SIR97 run in space group P 21/n REM R1 = 0.0611 for 2644 Fo > 4sig(Fo) and 0.1444 for all 5439 data REM 326 parameters refined using 0 restraints END WGHT 0.0533 0.0000 REM Highest difference peak 0.207, deepest hole -0.206, 1-sigma level 0.047 Q1 1 0.3641 0.3577 0.8119 11.00000 0.05 0.21 Q2 1 0.2400 0.1152 0.9738 11.00000 0.05 0.19 Q3 1 0.4112 0.0908 0.8801 11.00000 0.05 0.18 Q4 1 0.7791 -0.0482 0.8370 11.00000 0.05 0.17 Q5 1 0.7611 0.0297 1.0149 11.00000 0.05 0.16 Q6 1 0.1808 0.0468 0.6215 11.00000 0.05 0.16 Q7 1 0.8198 -0.1702 0.6207 11.00000 0.05 0.16 Q8 1 0.7213 0.0891 0.8761 11.00000 0.05 0.15 Q9 1 0.2784 -0.0155 0.5155 11.00000 0.05 0.15 Q10 1 0.7939 0.0853 1.0640 11.00000 0.05 0.15 Q11 1 0.1046 0.2264 1.2024 11.00000 0.05 0.15 Q12 1 0.4034 0.0129 0.5586 11.00000 0.05 0.15 Q13 1 0.3475 0.0150 0.9892 11.00000 0.05 0.15 Q14 1 0.1744 0.1001 1.1587 11.00000 0.05 0.15 Q15 1 0.6226 0.3303 0.9375 11.00000 0.05 0.15 Q16 1 1.0569 -0.0208 0.6218 11.00000 0.05 0.14 Q17 1 0.4631 0.2048 1.1405 11.00000 0.05 0.14 Q18 1 0.8901 -0.1747 0.7431 11.00000 0.05 0.14 Q19 1 0.3136 0.1149 0.7343 11.00000 0.05 0.14 Q20 1 0.5895 0.1005 0.7967 11.00000 0.05 0.14 Q21 1 0.3984 0.3225 0.8823 11.00000 0.05 0.14 Q22 1 0.7449 0.1578 0.8674 11.00000 0.05 0.14 Q23 1 0.3673 0.0754 0.5530 11.00000 0.05 0.14 Q24 1 0.8152 0.0121 0.8792 11.00000 0.05 0.14 Q25 1 0.6144 -0.1344 0.7678 11.00000 0.05 0.14 ; _shelx_res_checksum 8374 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 O1 O 0.1768(2) -0.01377(9) 0.55617(14) 0.0550(5) Uani 1 1 d G . . . . H1A H 0.2161 -0.0543 0.5572 0.082 Uiso 1 1 d G U . . . H1B H 0.2354 0.0150 0.5914 0.082 Uiso 1 1 d G U . . . N1 N 0.6021(2) 0.05483(10) 0.86679(14) 0.0401(5) Uani 1 1 d . . . . . N2 N 0.6703(2) -0.01563(10) 0.73848(15) 0.0442(5) Uani 1 1 d . . . . . O2 O 0.2149(2) 0.35450(9) 0.92611(14) 0.0593(5) Uani 1 1 d . . . . . N3 N 0.5280(2) 0.12589(10) 0.99393(14) 0.0416(5) Uani 1 1 d . . . . . O3 O 0.1152(2) 0.04544(11) 0.93008(14) 0.0668(6) Uani 1 1 d . . . . . N4 N 0.4372(2) -0.02849(11) 0.76953(15) 0.0455(5) Uani 1 1 d . . . . . N5 N 0.8886(2) -0.06433(10) 0.62699(14) 0.0448(5) Uani 1 1 d . . . . . H5A H 0.8750 -0.0359 0.5714 0.054 Uiso 1 1 calc R U . . . H5B H 0.9615 -0.0934 0.6209 0.054 Uiso 1 1 calc R U . . . O4 O 0.4331(2) 0.22353(11) 0.74972(17) 0.0665(6) Uani 1 1 d . . . . . H4 H 0.4617 0.2602 0.7798 0.100 Uiso 1 1 calc R U . . . C1 C 0.2898(3) 0.21650(13) 0.74882(18) 0.0416(6) Uani 1 1 d . . . . . O5 O 0.2969(2) 0.11982(10) 0.62949(15) 0.0646(6) Uani 1 1 d . . . . . H5 H 0.3760 0.1377 0.6263 0.097 Uiso 1 1 calc R U . . . C2 C 0.5676(3) 0.00507(12) 0.79318(18) 0.0395(6) Uani 1 1 d . . . . . C3 C 0.3547(3) 0.04731(12) 0.89531(17) 0.0375(6) Uani 1 1 d . . . . . C4 C 0.4952(3) 0.07512(12) 0.91643(17) 0.0361(6) Uani 1 1 d . . . . . O6 O 0.0410(2) 0.13224(12) 1.05921(16) 0.0727(6) Uani 1 1 d . . . . . H6 H 0.0399 0.0991 1.0184 0.109 Uiso 1 1 calc R U . . . C5 C 0.2111(3) 0.25914(12) 0.80626(18) 0.0399(6) Uani 1 1 d . . . . . O7 O 0.4148(2) 0.33075(10) 0.86209(17) 0.0708(6) Uani 1 1 d . . . . . O8 O 0.2017(2) 0.20635(11) 1.14334(15) 0.0684(6) Uani 1 1 d . . . . . C6 C 0.3366(3) -0.00643(13) 0.82044(17) 0.0442(6) Uani 1 1 d . . . . . H6A H 0.2462 -0.0281 0.8058 0.053 Uiso 1 1 calc R U . . . C7 C 0.2805(3) 0.12761(13) 1.02166(17) 0.0430(6) Uani 1 1 d . . . . . C8 C 0.2408(3) 0.07141(14) 0.94765(18) 0.0446(6) Uani 1 1 d . . . . . C9 C 0.4200(3) 0.15045(13) 1.04134(18) 0.0451(6) Uani 1 1 d . . . . . H9 H 0.4429 0.1857 1.0913 0.054 Uiso 1 1 calc R U . . . C10 C 0.9270(3) -0.02138(14) 0.72440(19) 0.0477(7) Uani 1 1 d . . . . . H10A H 1.0111 0.0075 0.7191 0.057 Uiso 1 1 calc R U . . . H10B H 0.9521 -0.0526 0.7841 0.057 Uiso 1 1 calc R U . . . C11 C 0.2841(3) 0.31886(13) 0.8706(2) 0.0461(7) Uani 1 1 d . . . . . C12 C 0.7549(3) -0.10601(13) 0.62961(19) 0.0464(7) Uani 1 1 d . . . . . H12A H 0.7722 -0.1396 0.6870 0.056 Uiso 1 1 calc R U . . . H12B H 0.7301 -0.1323 0.5647 0.056 Uiso 1 1 calc R U . . . C13 C 0.6312(3) -0.05869(13) 0.64347(19) 0.0483(7) Uani 1 1 d . . . . . H13A H 0.6075 -0.0282 0.5828 0.058 Uiso 1 1 calc R U . . . H13B H 0.5463 -0.0870 0.6491 0.058 Uiso 1 1 calc R U . . . C14 C 0.6786(3) 0.15223(13) 1.0248(2) 0.0504(7) Uani 1 1 d . . . . . H14A H 0.7459 0.1141 1.0185 0.061 Uiso 1 1 calc R U . . . H14B H 0.6930 0.1667 1.0977 0.061 Uiso 1 1 calc R U . . . C15 C 0.0634(3) 0.24750(13) 0.8000(2) 0.0563(7) Uani 1 1 d . . . . . H15 H 0.0102 0.2748 0.8397 0.068 Uiso 1 1 calc R U . . . C16 C 0.8034(3) 0.02534(14) 0.7416(2) 0.0517(7) Uani 1 1 d . . . . . H16A H 0.8274 0.0486 0.8091 0.062 Uiso 1 1 calc R U . . . H16B H 0.7882 0.0614 0.6877 0.062 Uiso 1 1 calc R U . . . C17 C 0.1729(3) 0.15904(16) 1.0796(2) 0.0535(7) Uani 1 1 d . . . . . O18 O 0.4361(3) -0.15392(12) 0.40754(19) 0.0912(8) Uani 1 1 d G . . . . H18A H 0.3959 -0.1529 0.4618 0.137 Uiso 1 1 d G U . . . H18B H 0.4122 -0.1917 0.3735 0.137 Uiso 1 1 d G U . . . C19 C 0.0740(3) 0.15431(15) 0.6769(2) 0.0637(8) Uani 1 1 d . . . . . H19 H 0.0267 0.1202 0.6320 0.076 Uiso 1 1 calc R U . . . C20 C 0.2211(3) 0.16280(13) 0.68466(19) 0.0459(7) Uani 1 1 d . . . . . C21 C 0.7121(3) 0.21330(15) 0.9588(3) 0.0716(9) Uani 1 1 d . . . . . H21A H 0.7033 0.1986 0.8870 0.107 Uiso 1 1 calc R U . . . H21B H 0.8092 0.2294 0.9832 0.107 Uiso 1 1 calc R U . . . H21C H 0.6451 0.2510 0.9639 0.107 Uiso 1 1 calc R U . . . C22 C -0.0046(3) 0.19552(16) 0.7348(3) 0.0733(9) Uani 1 1 d . . . . . H22 H -0.1038 0.1883 0.7300 0.088 Uiso 1 1 calc R U . . . 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 0.0628(13) 0.0453(11) 0.0543(11) 0.0050(9) 0.0027(10) -0.0032(10) N1 0.0374(12) 0.0411(12) 0.0438(11) -0.0064(9) 0.0123(10) 0.0005(10) N2 0.0340(12) 0.0526(13) 0.0489(12) -0.0167(10) 0.0151(10) -0.0046(10) O2 0.0715(14) 0.0502(11) 0.0643(12) -0.0077(9) 0.0348(11) -0.0026(10) N3 0.0375(12) 0.0465(12) 0.0427(11) -0.0084(9) 0.0120(10) -0.0010(10) O3 0.0386(11) 0.1007(16) 0.0643(12) -0.0183(11) 0.0182(10) -0.0061(11) N4 0.0364(13) 0.0512(13) 0.0501(12) -0.0094(10) 0.0111(11) -0.0045(11) N5 0.0485(13) 0.0478(13) 0.0399(11) 0.0051(9) 0.0130(10) 0.0135(11) O4 0.0457(12) 0.0697(14) 0.0887(15) -0.0328(11) 0.0250(11) -0.0135(10) C1 0.0393(15) 0.0429(15) 0.0431(13) 0.0040(11) 0.0083(12) -0.0085(12) O5 0.0805(16) 0.0559(12) 0.0628(12) -0.0194(9) 0.0278(12) -0.0177(11) C2 0.0362(15) 0.0399(14) 0.0434(14) -0.0027(11) 0.0094(12) 0.0016(12) C3 0.0338(14) 0.0450(15) 0.0351(12) 0.0016(10) 0.0094(11) 0.0006(12) C4 0.0375(15) 0.0378(14) 0.0339(12) 0.0025(10) 0.0085(11) 0.0055(11) O6 0.0469(13) 0.1078(19) 0.0679(14) -0.0116(12) 0.0225(11) 0.0086(13) C5 0.0424(16) 0.0335(14) 0.0449(13) 0.0048(11) 0.0107(12) -0.0056(12) O7 0.0481(12) 0.0673(14) 0.1019(16) -0.0363(11) 0.0267(12) -0.0178(11) O8 0.0695(15) 0.0756(14) 0.0655(13) -0.0116(11) 0.0264(11) 0.0166(12) C6 0.0373(15) 0.0550(16) 0.0406(13) -0.0022(11) 0.0068(12) -0.0049(13) C7 0.0398(16) 0.0541(16) 0.0374(13) 0.0069(11) 0.0128(12) 0.0100(13) C8 0.0366(15) 0.0587(17) 0.0395(13) 0.0072(12) 0.0097(12) 0.0058(13) C9 0.0498(17) 0.0458(15) 0.0415(13) -0.0012(11) 0.0129(13) 0.0097(13) C10 0.0389(16) 0.0599(17) 0.0461(14) -0.0017(12) 0.0126(13) -0.0019(13) C11 0.0529(19) 0.0378(15) 0.0503(15) 0.0036(12) 0.0161(14) -0.0015(13) C12 0.0526(17) 0.0459(16) 0.0432(14) -0.0063(11) 0.0153(13) -0.0027(14) C13 0.0448(16) 0.0557(17) 0.0468(14) -0.0138(12) 0.0143(13) -0.0044(14) C14 0.0455(17) 0.0538(17) 0.0517(15) -0.0105(12) 0.0072(13) -0.0052(13) C15 0.0473(18) 0.0413(16) 0.084(2) 0.0011(14) 0.0231(16) -0.0048(13) C16 0.0388(16) 0.0575(17) 0.0617(17) -0.0179(13) 0.0168(14) -0.0066(14) C17 0.0506(19) 0.069(2) 0.0441(15) 0.0088(14) 0.0163(15) 0.0136(16) O18 0.0979(19) 0.0901(18) 0.1010(18) -0.0325(13) 0.0607(16) -0.0241(15) C19 0.059(2) 0.0537(19) 0.075(2) -0.0038(15) 0.0007(17) -0.0195(16) C20 0.0542(18) 0.0399(15) 0.0441(14) 0.0032(11) 0.0098(13) -0.0075(13) C21 0.058(2) 0.067(2) 0.090(2) 0.0044(17) 0.0154(18) -0.0115(17) C22 0.0413(17) 0.063(2) 0.116(3) -0.0028(19) 0.0123(19) -0.0088(16) 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 H1A O1 H1B 109.5 . . ? C4 N1 C2 115.8(2) . . ? C2 N2 C16 120.7(2) . . ? C2 N2 C13 120.2(2) . . ? C16 N2 C13 114.16(19) . . ? C9 N3 C4 118.5(2) . . ? C9 N3 C14 120.7(2) . . ? C4 N3 C14 120.8(2) . . ? C6 N4 C2 115.5(2) . . ? C12 N5 C10 110.80(18) . . ? C12 N5 H5A 109.5 . . ? C10 N5 H5A 109.5 . . ? C12 N5 H5B 109.5 . . ? C10 N5 H5B 109.5 . . ? H5A N5 H5B 108.1 . . ? C1 O4 H4 109.5 . . ? O4 C1 C5 123.7(2) . . ? O4 C1 C20 115.8(2) . . ? C5 C1 C20 120.6(2) . . ? C20 O5 H5 109.5 . . ? N1 C2 N2 118.1(2) . . ? N1 C2 N4 126.0(2) . . ? N2 C2 N4 115.9(2) . . ? C6 C3 C4 114.3(2) . . ? C6 C3 C8 123.2(2) . . ? C4 C3 C8 122.5(2) . . ? N1 C4 N3 117.2(2) . . ? N1 C4 C3 123.6(2) . . ? N3 C4 C3 119.3(2) . . ? C17 O6 H6 109.5 . . ? C15 C5 C1 119.2(2) . . ? C15 C5 C11 120.5(2) . . ? C1 C5 C11 120.3(2) . . ? N4 C6 C3 124.8(2) . . ? N4 C6 H6A 117.6 . . ? C3 C6 H6A 117.6 . . ? C9 C7 C8 119.6(2) . . ? C9 C7 C17 119.4(3) . . ? C8 C7 C17 120.9(2) . . ? O3 C8 C3 122.4(2) . . ? O3 C8 C7 122.6(2) . . ? C3 C8 C7 115.0(2) . . ? N3 C9 C7 125.0(2) . . ? N3 C9 H9 117.5 . . ? C7 C9 H9 117.5 . . ? N5 C10 C16 111.4(2) . . ? N5 C10 H10A 109.3 . . ? C16 C10 H10A 109.3 . . ? N5 C10 H10B 109.3 . . ? C16 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? O2 C11 O7 123.8(2) . . ? O2 C11 C5 119.9(2) . . ? O7 C11 C5 116.2(2) . . ? N5 C12 C13 110.8(2) . . ? N5 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N5 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N2 C13 C12 110.1(2) . . ? N2 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? N2 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? N3 C14 C21 112.7(2) . . ? N3 C14 H14A 109.1 . . ? C21 C14 H14A 109.1 . . ? N3 C14 H14B 109.1 . . ? C21 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C22 C15 C5 120.1(3) . . ? C22 C15 H15 120.0 . . ? C5 C15 H15 120.0 . . ? N2 C16 C10 110.8(2) . . ? N2 C16 H16A 109.5 . . ? C10 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O8 C17 O6 120.8(3) . . ? O8 C17 C7 123.3(3) . . ? O6 C17 C7 115.9(3) . . ? H18A O18 H18B 109.5 . . ? C20 C19 C22 120.9(3) . . ? C20 C19 H19 119.5 . . ? C22 C19 H19 119.5 . . ? O5 C20 C19 119.8(2) . . ? O5 C20 C1 121.3(2) . . ? C19 C20 C1 118.9(3) . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 C15 120.3(3) . . ? C19 C22 H22 119.9 . . ? C15 C22 H22 119.9 . . ? 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 H1A 0.8501 . ? O1 H1B 0.8500 . ? N1 C4 1.332(3) . ? N1 C2 1.340(3) . ? N2 C2 1.343(3) . ? N2 C16 1.462(3) . ? N2 C13 1.469(3) . ? O2 C11 1.243(3) . ? N3 C9 1.349(3) . ? N3 C4 1.386(3) . ? N3 C14 1.485(3) . ? O3 C8 1.258(3) . ? N4 C6 1.304(3) . ? N4 C2 1.364(3) . ? N5 C12 1.484(3) . ? N5 C10 1.492(3) . ? N5 H5A 0.8900 . ? N5 H5B 0.8900 . ? O4 C1 1.344(3) . ? O4 H4 0.8200 . ? C1 C5 1.389(3) . ? C1 C20 1.399(3) . ? O5 C20 1.358(3) . ? O5 H5 0.8200 . ? C3 C6 1.396(3) . ? C3 C4 1.399(3) . ? C3 C8 1.430(3) . ? O6 C17 1.319(3) . ? O6 H6 0.8200 . ? C5 C15 1.388(3) . ? C5 C11 1.500(3) . ? O7 C11 1.266(3) . ? O8 C17 1.217(3) . ? C6 H6A 0.9300 . ? C7 C9 1.357(3) . ? C7 C8 1.439(4) . ? C7 C17 1.478(4) . ? C9 H9 0.9300 . ? C10 C16 1.502(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.498(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C21 1.502(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C22 1.380(4) . ? C15 H15 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O18 H18A 0.8501 . ? O18 H18B 0.8500 . ? C19 C20 1.372(4) . ? C19 C22 1.377(4) . ? C19 H19 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C2 N2 177.9(2) . . . . ? C4 N1 C2 N4 -3.8(3) . . . . ? C16 N2 C2 N1 -13.7(3) . . . . ? C13 N2 C2 N1 -167.5(2) . . . . ? C16 N2 C2 N4 167.8(2) . . . . ? C13 N2 C2 N4 14.1(3) . . . . ? C6 N4 C2 N1 3.9(4) . . . . ? C6 N4 C2 N2 -177.8(2) . . . . ? C2 N1 C4 N3 179.22(19) . . . . ? C2 N1 C4 C3 0.2(3) . . . . ? C9 N3 C4 N1 176.2(2) . . . . ? C14 N3 C4 N1 -4.3(3) . . . . ? C9 N3 C4 C3 -4.7(3) . . . . ? C14 N3 C4 C3 174.8(2) . . . . ? C6 C3 C4 N1 2.8(3) . . . . ? C8 C3 C4 N1 -178.2(2) . . . . ? C6 C3 C4 N3 -176.2(2) . . . . ? C8 C3 C4 N3 2.8(3) . . . . ? O4 C1 C5 C15 -179.9(2) . . . . ? C20 C1 C5 C15 0.5(4) . . . . ? O4 C1 C5 C11 2.6(4) . . . . ? C20 C1 C5 C11 -176.9(2) . . . . ? C2 N4 C6 C3 -0.4(4) . . . . ? C4 C3 C6 N4 -2.7(4) . . . . ? C8 C3 C6 N4 178.3(2) . . . . ? C6 C3 C8 O3 0.3(4) . . . . ? C4 C3 C8 O3 -178.6(2) . . . . ? C6 C3 C8 C7 -179.6(2) . . . . ? C4 C3 C8 C7 1.5(3) . . . . ? C9 C7 C8 O3 176.2(2) . . . . ? C17 C7 C8 O3 -1.4(4) . . . . ? C9 C7 C8 C3 -3.9(3) . . . . ? C17 C7 C8 C3 178.4(2) . . . . ? C4 N3 C9 C7 2.3(4) . . . . ? C14 N3 C9 C7 -177.2(2) . . . . ? C8 C7 C9 N3 2.2(4) . . . . ? C17 C7 C9 N3 179.9(2) . . . . ? C12 N5 C10 C16 -55.6(3) . . . . ? C15 C5 C11 O2 6.3(4) . . . . ? C1 C5 C11 O2 -176.3(2) . . . . ? C15 C5 C11 O7 -171.9(2) . . . . ? C1 C5 C11 O7 5.5(3) . . . . ? C10 N5 C12 C13 57.3(2) . . . . ? C2 N2 C13 C12 -149.5(2) . . . . ? C16 N2 C13 C12 55.1(3) . . . . ? N5 C12 C13 N2 -56.0(3) . . . . ? C9 N3 C14 C21 -92.8(3) . . . . ? C4 N3 C14 C21 87.7(3) . . . . ? C1 C5 C15 C22 -2.0(4) . . . . ? C11 C5 C15 C22 175.5(2) . . . . ? C2 N2 C16 C10 151.3(2) . . . . ? C13 N2 C16 C10 -53.5(3) . . . . ? N5 C10 C16 N2 52.9(3) . . . . ? C9 C7 C17 O8 1.9(4) . . . . ? C8 C7 C17 O8 179.6(2) . . . . ? C9 C7 C17 O6 -177.5(2) . . . . ? C8 C7 C17 O6 0.2(4) . . . . ? C22 C19 C20 O5 177.7(3) . . . . ? C22 C19 C20 C1 -3.0(4) . . . . ? O4 C1 C20 O5 1.6(3) . . . . ? C5 C1 C20 O5 -178.8(2) . . . . ? O4 C1 C20 C19 -177.6(2) . . . . ? C5 C1 C20 C19 2.0(4) . . . . ? C20 C19 C22 C15 1.6(5) . . . . ? C5 C15 C22 C19 0.9(5) . . . . ?