#------------------------------------------------------------------------------ #$Date: 2020-05-16 04:58:38 +0300 (Sat, 16 May 2020) $ #$Revision: 252069 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240535.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_7240535 loop_ _publ_author_name 'Surov, Artem Olegovich' 'Vasilev, Nikita' 'Voronin, Alexander P.' 'Andrei, Churakov' 'Emmerling, Franziska' 'Perlovich, German L.' _publ_section_title ; Ciprofloxacin salts with benzoic acid derivatives: structural aspects, solid-state properties and solubility performance ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00514B _journal_year 2020 _chemical_formula_moiety 'C17 H19 F N3 O3, C7 H5 O5, 2.167(H2 O)' _chemical_formula_sum 'C24 H28.33 F N3 O10.17' _chemical_formula_weight 540.47 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2020-03-29 deposited with the CCDC. 2020-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 93.365(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.1210(7) _cell_length_b 27.264(2) _cell_length_c 10.3393(8) _cell_measurement_reflns_used 7185 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.490 _cell_measurement_theta_min 2.475 _cell_volume 2566.7(3) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 28802 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 2.36 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1134.7 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.388 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 475 _refine_ls_number_reflns 6829 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0430 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.9557P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0973 _refine_ls_wR_factor_ref 0.1060 _reflns_number_gt 5346 _reflns_number_total 6829 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL a in P2(1)/n CELL 0.71073 9.1210 27.2645 10.3393 90.000 93.365 90.000 ZERR 4.000 0.0007 0.0022 0.0008 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O F UNIT 96 113.33 12 40.66 4 TEMP -123 SIZE .40 .20 .05 EQIV $1 0.5-X, -0.5+Y, 0.5-Z EQIV $2 -1+X, Y, -1+Z EQIV $3 -X, 1-Y, -Z EQIV $4 -0.5+X, 1.5-Y, -0.5+Z EQIV $5 1-X, 1-Y, 2-Z EQIV $6 0.5+X, 1.5-Y, 0.5+Z EQIV $7 1-X, 1-Y, 2-Z HTAB O3 O1 HTAB N3 O21_$1 HTAB N3 O2_$2 HTAB N3 O24_$3 HTAB O24 O22_$4 HTAB O25 O1 HTAB O26 O10 HTAB O10 O2_$5 HTAB O10 O11 HTAB O10 O12 HTAB O11 O22 HTAB O12 O22 HTAB O11 O21_$6 HTAB O12 O21_$6 HTAB O13 O2 HTAB O13 O11_$7 L.S. 10 BOND $H ACTA CONF FMAP 2 PLAN 8 OMIT -2 58 OMIT 0 2 0 OMIT 0 1 1 OMIT 6 2 7 WGHT 0.048600 0.955700 FVAR 0.14335 0.42431 0.16749 F1 5 0.031212 0.506158 0.167718 11.00000 0.02941 0.02378 = 0.01563 0.00807 -0.00743 -0.00682 O1 4 0.358615 0.510325 0.578162 11.00000 0.02064 0.02052 = 0.02093 0.00065 -0.00671 -0.00545 O2 4 0.386088 0.427396 0.907895 11.00000 0.02447 0.04865 = 0.01601 0.00838 -0.00690 0.00211 O3 4 0.473808 0.489780 0.798635 11.00000 0.02322 0.02991 = 0.02040 -0.00279 -0.00992 -0.00131 N1 3 0.069380 0.396843 0.616653 11.00000 0.01764 0.01998 = 0.01342 0.00258 -0.00142 -0.00229 N2 3 -0.161042 0.426987 0.187489 11.00000 0.01493 0.02107 = 0.01120 -0.00150 -0.00255 -0.00275 N3 3 -0.342340 0.380819 -0.012504 11.00000 0.01815 0.01862 = 0.01344 -0.00363 -0.00634 0.00191 C1 1 0.269347 0.475441 0.587773 11.00000 0.01339 0.01611 = 0.01375 -0.00248 -0.00180 0.00259 C2 1 0.271028 0.445376 0.701479 11.00000 0.01591 0.02101 = 0.01263 -0.00148 -0.00293 0.00322 C3 1 0.171352 0.408277 0.710637 11.00000 0.01962 0.02343 = 0.01221 0.00248 -0.00100 0.00188 C4 1 0.380537 0.453447 0.810977 11.00000 0.01612 0.02790 = 0.01571 -0.00214 -0.00389 0.00542 C5 1 -0.041207 0.359535 0.639772 11.00000 0.02212 0.02854 = 0.01890 0.00465 0.00260 -0.00728 C6 1 0.006807 0.313233 0.707151 11.00000 0.03937 0.03742 = 0.04065 0.02090 -0.00469 -0.01239 C7 1 -0.041586 0.312233 0.566237 11.00000 0.03587 0.02439 = 0.03630 0.00279 0.00169 -0.00768 C8 1 0.159337 0.463023 0.486226 11.00000 0.01362 0.01546 = 0.01152 -0.00152 -0.00176 0.00109 C9 1 0.148163 0.490085 0.369917 11.00000 0.01572 0.01521 = 0.01514 0.00079 -0.00114 -0.00118 C10 1 0.043876 0.477711 0.275929 11.00000 0.01802 0.01615 = 0.01078 0.00209 -0.00122 0.00083 C11 1 -0.053738 0.437723 0.286244 11.00000 0.01223 0.01806 = 0.01204 -0.00251 -0.00120 0.00091 C12 1 -0.043058 0.411721 0.401866 11.00000 0.01470 0.01704 = 0.01357 -0.00052 -0.00085 -0.00342 C13 1 0.061719 0.424024 0.501118 11.00000 0.01544 0.01629 = 0.01028 0.00052 -0.00026 0.00095 C14 1 -0.109836 0.420489 0.055488 11.00000 0.01770 0.02312 = 0.01129 -0.00048 -0.00118 -0.00186 C15 1 -0.239051 0.420914 -0.043470 11.00000 0.02398 0.01994 = 0.01293 -0.00019 -0.00363 -0.00090 C16 1 -0.265164 0.388345 0.218915 11.00000 0.01419 0.02289 = 0.01297 -0.00134 -0.00172 -0.00364 C17 1 -0.394678 0.387856 0.119933 11.00000 0.01537 0.02212 = 0.01605 -0.00435 -0.00323 -0.00096 H3 2 0.170957 0.387778 0.786398 11.00000 0.02100 H5 2 -0.135194 0.372629 0.659346 11.00000 0.02725 H9 2 0.212832 0.517960 0.358650 11.00000 0.02085 H10 2 -0.105033 0.384914 0.415798 11.00000 0.02226 H30 2 0.455534 0.502557 0.714277 11.00000 0.05498 H31 2 -0.291641 0.350432 -0.014838 11.00000 0.03612 H32 2 -0.418082 0.380802 -0.070178 11.00000 0.02286 H61 2 -0.054524 0.301278 0.768885 11.00000 0.05545 H62 2 0.107733 0.309087 0.723557 11.00000 0.04277 H71 2 -0.136856 0.298858 0.543431 11.00000 0.04504 H72 2 0.034722 0.308573 0.503283 11.00000 0.03605 H141 2 -0.055439 0.389145 0.049527 11.00000 0.02363 H142 2 -0.041882 0.445624 0.034421 11.00000 0.02272 H151 2 -0.206972 0.415436 -0.127153 11.00000 0.02594 H152 2 -0.296352 0.451333 -0.044089 11.00000 0.02074 H161 2 -0.305741 0.396616 0.303882 11.00000 0.01824 H162 2 -0.215948 0.355777 0.223144 11.00000 0.02264 H171 2 -0.460758 0.361119 0.137382 11.00000 0.02298 H172 2 -0.446591 0.418492 0.120212 11.00000 0.01435 O21 4 0.694737 0.794348 0.498499 11.00000 0.02842 0.01673 = 0.02384 0.00252 -0.00834 -0.00392 O22 4 0.823159 0.753744 0.655018 11.00000 0.03130 0.01812 = 0.02652 -0.00045 -0.01532 -0.00416 O24 4 0.399376 0.661512 0.256399 11.00000 0.03868 0.01586 = 0.01823 0.00059 -0.01672 -0.00170 O25 4 0.404481 0.585206 0.416097 11.00000 0.02645 0.01549 = 0.02041 0.00137 -0.01018 -0.00567 O26 4 0.575982 0.585754 0.644415 11.00000 0.01881 0.01748 = 0.01537 0.00357 -0.00448 -0.00362 C21 1 0.729414 0.755497 0.559807 11.00000 0.01908 0.01652 = 0.01728 -0.00175 -0.00274 -0.00189 C22 1 0.651388 0.709051 0.518945 11.00000 0.01742 0.01614 = 0.01533 -0.00237 -0.00308 -0.00135 C23 1 0.568301 0.706741 0.400926 11.00000 0.02259 0.01507 = 0.01462 0.00060 -0.00404 0.00026 H23 2 0.572183 0.734013 0.342401 11.00000 0.02311 C24 1 0.485654 0.665269 0.368756 11.00000 0.01981 0.01679 = 0.01295 -0.00250 -0.00526 0.00083 C25 1 0.488023 0.624889 0.452324 11.00000 0.01586 0.01413 = 0.01528 -0.00311 -0.00168 0.00013 C26 1 0.576037 0.626579 0.567723 11.00000 0.01481 0.01572 = 0.01242 0.00076 0.00002 0.00183 C27 1 0.656265 0.668586 0.601083 11.00000 0.01784 0.01689 = 0.01379 -0.00152 -0.00429 -0.00001 H27 2 0.712077 0.669541 0.679425 11.00000 0.01648 H24 2 0.379330 0.691983 0.224351 11.00000 0.05164 H25 2 0.409884 0.563001 0.477563 11.00000 0.04271 H26 2 0.636934 0.590542 0.710704 11.00000 0.03953 O10 4 0.754704 0.597454 0.862316 11.00000 0.02035 0.03460 = 0.02002 0.00236 -0.00242 -0.00553 H1 2 0.719410 0.590882 0.935066 11.00000 0.04958 H2 2 0.801675 0.624344 0.871413 11.00000 0.04845 O11 4 0.880832 0.691374 0.891096 21.00000 0.04634 0.03725 = 0.05244 0.00560 -0.01087 -0.01781 O12 4 0.925799 0.681680 0.848499 -21.00000 0.04658 0.02688 = 0.06427 0.01560 -0.03769 -0.01257 H11 2 0.885308 0.705654 0.798868 11.00000 0.09138 H12 2 0.988999 0.693795 0.905779 11.00000 0.07189 O13 4 0.382920 0.310423 0.945219 31.00000 0.05235 0.02899 = 0.05868 -0.00325 0.01876 -0.01127 AFIX 3 H13 2 0.384000 0.341363 0.935169 31.00000 -1.50000 H14 2 0.308750 0.309813 0.991269 31.00000 -1.50000 HKLF 4 REM a in P2(1)/n REM R1 = 0.0430 for 5346 Fo > 4sig(Fo) and 0.0612 for all 6829 data REM 475 parameters refined using 0 restraints END WGHT 0.0486 0.9570 REM Highest difference peak 0.388, deepest hole -0.239, 1-sigma level 0.049 Q1 1 0.2173 0.4679 0.5329 11.00000 0.05 0.39 Q2 1 0.5980 0.7077 0.4652 11.00000 0.05 0.36 Q3 1 0.3161 0.4503 0.7510 11.00000 0.05 0.36 Q4 1 0.0229 0.4507 0.2616 11.00000 0.05 0.36 Q5 1 0.6806 0.7322 0.5415 11.00000 0.05 0.36 Q6 1 0.2756 0.4578 0.6422 11.00000 0.05 0.35 Q7 1 0.0824 0.4858 0.3333 11.00000 0.05 0.35 Q8 1 0.1551 0.4726 0.4269 11.00000 0.05 0.34 ; _cod_data_source_file d0ce00514b2.cif _cod_data_source_block a_CCDC1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240535 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.03121(9) 0.50616(3) 0.16772(8) 0.02329(19) Uani 1 1 d . . . O1 O 0.35861(11) 0.51033(4) 0.57816(9) 0.0210(2) Uani 1 1 d . . . O2 O 0.38609(12) 0.42740(5) 0.90790(10) 0.0300(3) Uani 1 1 d . . . O3 O 0.47381(11) 0.48978(4) 0.79863(10) 0.0250(2) Uani 1 1 d . . . N1 N 0.06938(12) 0.39684(4) 0.61665(10) 0.0171(2) Uani 1 1 d . . . N2 N -0.16104(12) 0.42699(4) 0.18749(10) 0.0159(2) Uani 1 1 d . . . N3 N -0.34234(13) 0.38082(4) -0.01250(11) 0.0170(2) Uani 1 1 d . . . C1 C 0.26935(14) 0.47544(5) 0.58777(12) 0.0145(2) Uani 1 1 d . . . C2 C 0.27103(14) 0.44538(5) 0.70148(12) 0.0167(3) Uani 1 1 d . . . C3 C 0.17135(15) 0.40828(5) 0.71064(13) 0.0185(3) Uani 1 1 d . . . C4 C 0.38054(15) 0.45345(5) 0.81098(13) 0.0201(3) Uani 1 1 d . . . C5 C -0.04121(16) 0.35954(6) 0.63977(14) 0.0231(3) Uani 1 1 d . . . C6 C 0.0068(2) 0.31323(7) 0.70715(19) 0.0394(4) Uani 1 1 d . . . C7 C -0.0416(2) 0.31223(6) 0.56624(18) 0.0322(4) Uani 1 1 d . . . C8 C 0.15934(13) 0.46302(5) 0.48623(12) 0.0136(2) Uani 1 1 d . . . C9 C 0.14816(14) 0.49009(5) 0.36992(12) 0.0154(3) Uani 1 1 d . . . C10 C 0.04388(14) 0.47771(5) 0.27593(12) 0.0151(3) Uani 1 1 d . . . C11 C -0.05374(13) 0.43772(5) 0.28624(12) 0.0142(2) Uani 1 1 d . . . C12 C -0.04306(14) 0.41172(5) 0.40187(12) 0.0152(3) Uani 1 1 d . . . C13 C 0.06172(14) 0.42402(5) 0.50112(12) 0.0140(2) Uani 1 1 d . . . C14 C -0.10984(15) 0.42049(5) 0.05549(12) 0.0175(3) Uani 1 1 d . . . C15 C -0.23905(16) 0.42091(5) -0.04347(13) 0.0191(3) Uani 1 1 d . . . C16 C -0.26516(14) 0.38834(5) 0.21892(13) 0.0168(3) Uani 1 1 d . . . C17 C -0.39468(15) 0.38786(5) 0.11993(13) 0.0180(3) Uani 1 1 d . . . H3 H 0.1710(18) 0.3878(6) 0.7864(16) 0.021(4) Uiso 1 1 d . . . H5 H -0.135(2) 0.3726(6) 0.6593(17) 0.027(4) Uiso 1 1 d . . . H9 H 0.2128(18) 0.5180(6) 0.3587(16) 0.021(4) Uiso 1 1 d . . . H10 H -0.1050(18) 0.3849(6) 0.4158(16) 0.022(4) Uiso 1 1 d . . . H30 H 0.456(3) 0.5026(8) 0.714(2) 0.055(7) Uiso 1 1 d . . . H31 H -0.292(2) 0.3504(7) -0.0148(18) 0.036(5) Uiso 1 1 d . . . H32 H -0.4181(19) 0.3808(6) -0.0702(17) 0.023(4) Uiso 1 1 d . . . H61 H -0.055(3) 0.3013(8) 0.769(2) 0.055(7) Uiso 1 1 d . . . H62 H 0.108(2) 0.3091(8) 0.724(2) 0.043(6) Uiso 1 1 d . . . H71 H -0.137(2) 0.2989(7) 0.543(2) 0.045(6) Uiso 1 1 d . . . H72 H 0.035(2) 0.3086(7) 0.5033(19) 0.036(5) Uiso 1 1 d . . . H141 H -0.0554(18) 0.3891(6) 0.0495(16) 0.024(4) Uiso 1 1 d . . . H142 H -0.0419(19) 0.4456(6) 0.0344(16) 0.023(4) Uiso 1 1 d . . . H151 H -0.2070(19) 0.4154(6) -0.1272(18) 0.026(4) Uiso 1 1 d . . . H152 H -0.2964(18) 0.4513(6) -0.0441(16) 0.021(4) Uiso 1 1 d . . . H161 H -0.3057(17) 0.3966(6) 0.3039(16) 0.018(4) Uiso 1 1 d . . . H162 H -0.2159(18) 0.3558(6) 0.2231(16) 0.023(4) Uiso 1 1 d . . . H171 H -0.4608(19) 0.3611(6) 0.1374(16) 0.023(4) Uiso 1 1 d . . . H172 H -0.4466(17) 0.4185(6) 0.1202(15) 0.014(4) Uiso 1 1 d . . . O21 O 0.69474(12) 0.79435(4) 0.49850(10) 0.0234(2) Uani 1 1 d . . . O22 O 0.82316(12) 0.75374(4) 0.65502(10) 0.0260(2) Uani 1 1 d . . . O24 O 0.39938(12) 0.66151(4) 0.25640(10) 0.0250(2) Uani 1 1 d . . . O25 O 0.40448(11) 0.58521(4) 0.41610(10) 0.0212(2) Uani 1 1 d . . . O26 O 0.57598(11) 0.58575(3) 0.64442(9) 0.0174(2) Uani 1 1 d . . . C21 C 0.72941(15) 0.75550(5) 0.55981(13) 0.0178(3) Uani 1 1 d . . . C22 C 0.65139(14) 0.70905(5) 0.51894(12) 0.0165(3) Uani 1 1 d . . . C23 C 0.56830(15) 0.70674(5) 0.40093(13) 0.0176(3) Uani 1 1 d . . . H23 H 0.5722(18) 0.7340(6) 0.3424(16) 0.023(4) Uiso 1 1 d . . . C24 C 0.48565(15) 0.66527(5) 0.36876(12) 0.0168(3) Uani 1 1 d . . . C25 C 0.48802(14) 0.62489(5) 0.45232(12) 0.0152(3) Uani 1 1 d . . . C26 C 0.57604(14) 0.62658(5) 0.56772(12) 0.0143(2) Uani 1 1 d . . . C27 C 0.65627(15) 0.66859(5) 0.60108(13) 0.0164(3) Uani 1 1 d . . . H27 H 0.7121(17) 0.6695(6) 0.6794(16) 0.016(4) Uiso 1 1 d . . . H24 H 0.379(2) 0.6920(9) 0.224(2) 0.052(6) Uiso 1 1 d . . . H25 H 0.410(2) 0.5630(8) 0.478(2) 0.043(6) Uiso 1 1 d . . . H26 H 0.637(2) 0.5905(7) 0.711(2) 0.040(5) Uiso 1 1 d . . . O10 O 0.75470(12) 0.59745(5) 0.86232(11) 0.0251(2) Uani 1 1 d . . . H1 H 0.719(2) 0.5909(8) 0.935(2) 0.050(6) Uiso 1 1 d . . . H2 H 0.802(2) 0.6243(9) 0.871(2) 0.048(6) Uiso 1 1 d . . . O11 O 0.8808(19) 0.6914(6) 0.8911(15) 0.046(2) Uani 0.42(4) 1 d P . . O12 O 0.9258(17) 0.6817(3) 0.8485(18) 0.048(3) Uani 0.58(4) 1 d P . . H11 H 0.885(3) 0.7057(11) 0.799(3) 0.091(10) Uiso 1 1 d . . . H12 H 0.989(3) 0.6938(10) 0.906(3) 0.072(8) Uiso 1 1 d . . . O13 O 0.3829(9) 0.3104(3) 0.9452(8) 0.046(3) Uani 0.167(4) 1 d P . . H13 H 0.3840 0.3414 0.9352 0.069 Uiso 0.167(4) 1 d PR . . H14 H 0.3087 0.3098 0.9913 0.069 Uiso 0.167(4) 1 d PR . . 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 F1 0.0294(4) 0.0238(4) 0.0156(4) 0.0081(3) -0.0074(3) -0.0068(3) O1 0.0206(5) 0.0205(5) 0.0209(5) 0.0007(4) -0.0067(4) -0.0054(4) O2 0.0245(5) 0.0486(7) 0.0160(5) 0.0084(5) -0.0069(4) 0.0021(5) O3 0.0232(5) 0.0299(6) 0.0204(5) -0.0028(4) -0.0099(4) -0.0013(4) N1 0.0176(5) 0.0200(6) 0.0134(5) 0.0026(4) -0.0014(4) -0.0023(4) N2 0.0149(5) 0.0211(6) 0.0112(5) -0.0015(4) -0.0026(4) -0.0027(4) N3 0.0181(5) 0.0186(6) 0.0134(5) -0.0036(4) -0.0063(4) 0.0019(4) C1 0.0134(6) 0.0161(6) 0.0137(6) -0.0025(5) -0.0018(5) 0.0026(5) C2 0.0159(6) 0.0210(7) 0.0126(6) -0.0015(5) -0.0029(5) 0.0032(5) C3 0.0196(6) 0.0234(7) 0.0122(6) 0.0025(5) -0.0010(5) 0.0019(5) C4 0.0161(6) 0.0279(7) 0.0157(6) -0.0021(5) -0.0039(5) 0.0054(5) C5 0.0221(7) 0.0285(8) 0.0189(7) 0.0046(6) 0.0026(5) -0.0073(6) C6 0.0394(10) 0.0374(10) 0.0406(10) 0.0209(8) -0.0047(8) -0.0124(8) C7 0.0359(9) 0.0244(8) 0.0363(9) 0.0028(7) 0.0017(7) -0.0077(7) C8 0.0136(6) 0.0155(6) 0.0115(6) -0.0015(5) -0.0018(4) 0.0011(5) C9 0.0157(6) 0.0152(6) 0.0151(6) 0.0008(5) -0.0011(5) -0.0012(5) C10 0.0180(6) 0.0161(6) 0.0108(6) 0.0021(5) -0.0012(5) 0.0008(5) C11 0.0122(6) 0.0181(6) 0.0120(6) -0.0025(5) -0.0012(4) 0.0009(5) C12 0.0147(6) 0.0170(6) 0.0136(6) -0.0005(5) -0.0009(5) -0.0034(5) C13 0.0154(6) 0.0163(6) 0.0103(6) 0.0005(5) -0.0003(5) 0.0010(5) C14 0.0177(6) 0.0231(7) 0.0113(6) -0.0005(5) -0.0012(5) -0.0019(5) C15 0.0240(7) 0.0199(7) 0.0129(6) -0.0002(5) -0.0036(5) -0.0009(5) C16 0.0142(6) 0.0229(7) 0.0130(6) -0.0013(5) -0.0017(5) -0.0036(5) C17 0.0154(6) 0.0221(7) 0.0160(6) -0.0044(5) -0.0032(5) -0.0010(5) O21 0.0284(5) 0.0167(5) 0.0238(5) 0.0025(4) -0.0083(4) -0.0039(4) O22 0.0313(6) 0.0181(5) 0.0265(5) -0.0004(4) -0.0153(4) -0.0042(4) O24 0.0387(6) 0.0159(5) 0.0182(5) 0.0006(4) -0.0167(4) -0.0017(4) O25 0.0264(5) 0.0155(5) 0.0204(5) 0.0014(4) -0.0102(4) -0.0057(4) O26 0.0188(5) 0.0175(5) 0.0154(4) 0.0036(4) -0.0045(4) -0.0036(4) C21 0.0191(6) 0.0165(6) 0.0173(6) -0.0017(5) -0.0027(5) -0.0019(5) C22 0.0174(6) 0.0161(6) 0.0153(6) -0.0024(5) -0.0031(5) -0.0014(5) C23 0.0226(7) 0.0151(6) 0.0146(6) 0.0006(5) -0.0040(5) 0.0003(5) C24 0.0198(6) 0.0168(6) 0.0130(6) -0.0025(5) -0.0053(5) 0.0008(5) C25 0.0159(6) 0.0141(6) 0.0153(6) -0.0031(5) -0.0017(5) 0.0001(5) C26 0.0148(6) 0.0157(6) 0.0124(6) 0.0008(5) 0.0000(5) 0.0018(5) C27 0.0178(6) 0.0169(6) 0.0138(6) -0.0015(5) -0.0043(5) 0.0000(5) O10 0.0203(5) 0.0346(6) 0.0200(5) 0.0024(5) -0.0024(4) -0.0055(5) O11 0.046(4) 0.037(3) 0.052(4) 0.006(3) -0.011(4) -0.018(3) O12 0.047(4) 0.027(2) 0.064(6) 0.016(2) -0.038(4) -0.013(2) O13 0.052(5) 0.029(4) 0.059(6) -0.003(4) 0.019(4) -0.011(4) 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' F F 0.0171 0.0103 '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 C4 O3 H30 106.7(14) . . ? C3 N1 C13 119.43(11) . . ? C3 N1 C5 119.92(11) . . ? C13 N1 C5 120.40(11) . . ? C11 N2 C16 114.93(10) . . ? C11 N2 C14 116.87(11) . . ? C16 N2 C14 111.21(10) . . ? C17 N3 C15 110.12(10) . . ? C17 N3 H31 108.6(12) . . ? C15 N3 H31 108.6(12) . . ? C17 N3 H32 109.9(11) . . ? C15 N3 H32 109.5(11) . . ? H31 N3 H32 110.1(16) . . ? O1 C1 C2 121.39(11) . . ? O1 C1 C8 122.85(12) . . ? C2 C1 C8 115.75(11) . . ? C3 C2 C1 120.34(11) . . ? C3 C2 C4 118.57(12) . . ? C1 C2 C4 121.09(12) . . ? N1 C3 C2 123.87(12) . . ? N1 C3 H3 114.8(10) . . ? C2 C3 H3 121.4(10) . . ? O2 C4 O3 121.25(12) . . ? O2 C4 C2 122.13(13) . . ? O3 C4 C2 116.62(12) . . ? N1 C5 C6 118.53(13) . . ? N1 C5 C7 119.83(14) . . ? C6 C5 C7 60.07(12) . . ? N1 C5 H5 114.1(11) . . ? C6 C5 H5 117.1(11) . . ? C7 C5 H5 116.8(11) . . ? C5 C6 C7 60.03(11) . . ? C5 C6 H61 116.3(14) . . ? C7 C6 H61 120.4(14) . . ? C5 C6 H62 116.5(13) . . ? C7 C6 H62 114.0(13) . . ? H61 C6 H62 117.3(19) . . ? C5 C7 C6 59.90(12) . . ? C5 C7 H71 115.3(12) . . ? C6 C7 H71 117.2(13) . . ? C5 C7 H72 116.2(11) . . ? C6 C7 H72 117.7(11) . . ? H71 C7 H72 117.6(17) . . ? C13 C8 C9 118.45(11) . . ? C13 C8 C1 121.01(11) . . ? C9 C8 C1 120.54(12) . . ? C10 C9 C8 119.45(12) . . ? C10 C9 H9 120.7(10) . . ? C8 C9 H9 119.8(10) . . ? F1 C10 C9 117.88(11) . . ? F1 C10 C11 118.52(11) . . ? C9 C10 C11 123.58(12) . . ? C12 C11 N2 122.06(12) . . ? C12 C11 C10 116.46(11) . . ? N2 C11 C10 121.38(11) . . ? C11 C12 C13 121.24(12) . . ? C11 C12 H10 121.1(10) . . ? C13 C12 H10 117.7(10) . . ? C8 C13 C12 120.77(11) . . ? C8 C13 N1 119.59(11) . . ? C12 C13 N1 119.63(12) . . ? N2 C14 C15 110.31(11) . . ? N2 C14 H141 110.3(10) . . ? C15 C14 H141 109.7(10) . . ? N2 C14 H142 111.6(10) . . ? C15 C14 H142 109.2(10) . . ? H141 C14 H142 105.6(14) . . ? N3 C15 C14 109.02(11) . . ? N3 C15 H151 108.4(11) . . ? C14 C15 H151 110.4(11) . . ? N3 C15 H152 106.2(10) . . ? C14 C15 H152 113.8(10) . . ? H151 C15 H152 108.8(14) . . ? N2 C16 C17 110.20(11) . . ? N2 C16 H161 108.1(9) . . ? C17 C16 H161 106.3(9) . . ? N2 C16 H162 110.8(10) . . ? C17 C16 H162 110.7(9) . . ? H161 C16 H162 110.6(13) . . ? N3 C17 C16 110.04(11) . . ? N3 C17 H171 108.1(10) . . ? C16 C17 H171 110.4(10) . . ? N3 C17 H172 107.4(9) . . ? C16 C17 H172 110.8(9) . . ? H171 C17 H172 110.0(13) . . ? C24 O24 H24 109.5(14) . . ? C25 O25 H25 110.0(14) . . ? C26 O26 H26 108.3(13) . . ? O21 C21 O22 123.96(12) . . ? O21 C21 C22 117.70(11) . . ? O22 C21 C22 118.31(12) . . ? C27 C22 C23 119.52(12) . . ? C27 C22 C21 119.97(11) . . ? C23 C22 C21 120.46(12) . . ? C24 C23 C22 120.27(12) . . ? C24 C23 H23 121.3(10) . . ? C22 C23 H23 118.4(10) . . ? O24 C24 C23 122.78(12) . . ? O24 C24 C25 116.92(11) . . ? C23 C24 C25 120.29(11) . . ? O25 C25 C24 117.83(11) . . ? O25 C25 C26 122.95(12) . . ? C24 C25 C26 119.21(12) . . ? O26 C26 C27 123.00(11) . . ? O26 C26 C25 116.63(11) . . ? C27 C26 C25 120.37(12) . . ? C22 C27 C26 120.25(12) . . ? C22 C27 H27 120.3(10) . . ? C26 C27 H27 119.4(10) . . ? H1 O10 H2 107(2) . . ? H11 O11 H12 91(3) . . ? H11 O12 H12 110(3) . . ? H13 O13 H14 95.9 . . ? 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 F1 C10 1.3607(14) . ? O1 C1 1.2597(16) . ? O2 C4 1.2269(17) . ? O3 C4 1.3168(18) . ? O3 H30 0.94(2) . ? N1 C3 1.3418(16) . ? N1 C13 1.4040(16) . ? N1 C5 1.4620(18) . ? N2 C11 1.4031(15) . ? N2 C16 1.4676(17) . ? N2 C14 1.4789(17) . ? N3 C17 1.4888(17) . ? N3 C15 1.4901(18) . ? N3 H31 0.95(2) . ? N3 H32 0.886(17) . ? C1 C2 1.4325(18) . ? C1 C8 1.4492(16) . ? C2 C3 1.3670(19) . ? C2 C4 1.4816(17) . ? C3 H3 0.962(17) . ? C5 C6 1.495(2) . ? C5 C7 1.497(2) . ? C5 H5 0.961(18) . ? C6 C7 1.498(3) . ? C6 H61 0.93(2) . ? C6 H62 0.93(2) . ? C7 H71 0.96(2) . ? C7 H72 0.99(2) . ? C8 C13 1.4011(18) . ? C8 C9 1.4095(18) . ? C9 C10 1.3618(17) . ? C9 H9 0.973(17) . ? C10 C11 1.4156(18) . ? C11 C12 1.3883(18) . ? C12 C13 1.4014(17) . ? C12 H10 0.940(17) . ? C14 C15 1.5147(18) . ? C14 H141 0.992(17) . ? C14 H142 0.958(18) . ? C15 H151 0.941(18) . ? C15 H152 0.980(17) . ? C16 C17 1.5169(17) . ? C16 H161 0.999(16) . ? C16 H162 0.995(17) . ? C17 H171 0.970(17) . ? C17 H172 0.960(16) . ? O21 C21 1.2650(16) . ? O22 C21 1.2664(16) . ? O24 C24 1.3682(15) . ? O24 H24 0.91(2) . ? O25 C25 1.3631(15) . ? O25 H25 0.88(2) . ? O26 C26 1.3667(15) . ? O26 H26 0.87(2) . ? C21 C22 1.5011(18) . ? C22 C27 1.3914(19) . ? C22 C23 1.3995(17) . ? C23 C24 1.3885(18) . ? C23 H23 0.961(17) . ? C24 C25 1.3989(19) . ? C25 C26 1.3992(17) . ? C26 C27 1.3916(18) . ? C27 H27 0.931(16) . ? O10 H1 0.85(2) . ? O10 H2 0.85(2) . ? O11 H11 1.03(3) . ? O11 H12 0.99(3) . ? O12 H11 0.90(3) . ? O12 H12 0.87(3) . ? O13 H13 0.8501 . ? O13 H14 0.8500 . ? 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 O3 H30 O1 0.94(2) 1.63(2) 2.5165(14) 154(2) . N3 H31 O21 0.95(2) 1.77(2) 2.7145(15) 173.1(18) 2_545 N3 H32 O2 0.886(17) 2.193(17) 2.8612(16) 131.9(14) 1_454 N3 H32 O24 0.886(17) 2.260(17) 2.7942(15) 118.6(14) 3_565 O24 H24 O22 0.91(2) 1.71(2) 2.6144(14) 173(2) 4_575 O25 H25 O1 0.88(2) 1.85(2) 2.6895(14) 160(2) . O26 H26 O10 0.87(2) 1.86(2) 2.7210(14) 174(2) . O10 H1 O2 0.85(2) 2.00(2) 2.8480(16) 173(2) 3_667 O10 H2 O11 0.85(2) 1.97(3) 2.816(10) 171(2) . O10 H2 O12 0.85(2) 1.95(3) 2.785(6) 165(2) . O11 H11 O22 1.03(3) 2.04(3) 2.996(7) 153(3) . O12 H11 O22 0.90(3) 2.04(3) 2.919(5) 167(3) . O11 H12 O21 0.99(3) 2.08(3) 3.035(11) 161(3) 4_676 O12 H12 O21 0.87(3) 2.08(3) 2.899(4) 157(3) 4_676 O13 H13 O2 0.85 2.36 3.213(8) 179.7 . O13 H14 O11 0.85 2.17 3.02(2) 179.7 3_667 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 O1 C1 C2 C3 178.83(13) . . . . ? C8 C1 C2 C3 -1.19(18) . . . . ? O1 C1 C2 C4 -1.5(2) . . . . ? C8 C1 C2 C4 178.45(12) . . . . ? C13 N1 C3 C2 -0.2(2) . . . . ? C5 N1 C3 C2 -174.36(13) . . . . ? C1 C2 C3 N1 1.2(2) . . . . ? C4 C2 C3 N1 -178.46(13) . . . . ? C3 C2 C4 O2 1.4(2) . . . . ? C1 C2 C4 O2 -178.24(13) . . . . ? C3 C2 C4 O3 -179.51(12) . . . . ? C1 C2 C4 O3 0.84(19) . . . . ? C3 N1 C5 C6 -43.6(2) . . . . ? C13 N1 C5 C6 142.24(15) . . . . ? C3 N1 C5 C7 -113.57(16) . . . . ? C13 N1 C5 C7 72.29(18) . . . . ? N1 C5 C6 C7 -109.89(16) . . . . ? N1 C5 C7 C6 107.77(16) . . . . ? O1 C1 C8 C13 -179.73(12) . . . . ? C2 C1 C8 C13 0.28(18) . . . . ? O1 C1 C8 C9 0.2(2) . . . . ? C2 C1 C8 C9 -179.78(12) . . . . ? C13 C8 C9 C10 -0.06(19) . . . . ? C1 C8 C9 C10 -179.99(12) . . . . ? C8 C9 C10 F1 176.69(12) . . . . ? C8 C9 C10 C11 -1.8(2) . . . . ? C16 N2 C11 C12 3.30(18) . . . . ? C14 N2 C11 C12 -129.77(14) . . . . ? C16 N2 C11 C10 -172.86(12) . . . . ? C14 N2 C11 C10 54.08(17) . . . . ? F1 C10 C11 C12 -175.91(12) . . . . ? C9 C10 C11 C12 2.5(2) . . . . ? F1 C10 C11 N2 0.45(19) . . . . ? C9 C10 C11 N2 178.90(12) . . . . ? N2 C11 C12 C13 -177.85(12) . . . . ? C10 C11 C12 C13 -1.52(19) . . . . ? C9 C8 C13 C12 1.00(19) . . . . ? C1 C8 C13 C12 -179.07(12) . . . . ? C9 C8 C13 N1 -179.25(12) . . . . ? C1 C8 C13 N1 0.68(19) . . . . ? C11 C12 C13 C8 -0.2(2) . . . . ? C11 C12 C13 N1 -179.91(12) . . . . ? C3 N1 C13 C8 -0.77(19) . . . . ? C5 N1 C13 C8 173.39(12) . . . . ? C3 N1 C13 C12 178.98(12) . . . . ? C5 N1 C13 C12 -6.86(19) . . . . ? C11 N2 C14 C15 -166.92(11) . . . . ? C16 N2 C14 C15 58.37(14) . . . . ? C17 N3 C15 C14 59.27(14) . . . . ? N2 C14 C15 N3 -58.64(15) . . . . ? C11 N2 C16 C17 167.08(11) . . . . ? C14 N2 C16 C17 -57.27(14) . . . . ? C15 N3 C17 C16 -58.84(14) . . . . ? N2 C16 C17 N3 57.32(15) . . . . ? O21 C21 C22 C27 -163.56(13) . . . . ? O22 C21 C22 C27 14.8(2) . . . . ? O21 C21 C22 C23 13.7(2) . . . . ? O22 C21 C22 C23 -167.90(13) . . . . ? C27 C22 C23 C24 3.1(2) . . . . ? C21 C22 C23 C24 -174.18(13) . . . . ? C22 C23 C24 O24 178.21(13) . . . . ? C22 C23 C24 C25 -1.8(2) . . . . ? O24 C24 C25 O25 -0.23(19) . . . . ? C23 C24 C25 O25 179.82(13) . . . . ? O24 C24 C25 C26 179.14(12) . . . . ? C23 C24 C25 C26 -0.8(2) . . . . ? O25 C25 C26 O26 0.46(19) . . . . ? C24 C25 C26 O26 -178.87(12) . . . . ? O25 C25 C26 C27 -178.44(13) . . . . ? C24 C25 C26 C27 2.22(19) . . . . ? C23 C22 C27 C26 -1.7(2) . . . . ? C21 C22 C27 C26 175.60(12) . . . . ? O26 C26 C27 C22 -179.80(12) . . . . ? C25 C26 C27 C22 -1.0(2) . . . . ?