#------------------------------------------------------------------------------ #$Date: 2020-05-16 04:58:38 +0300 (Sat, 16 May 2020) $ #$Revision: 252069 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240534.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_7240534 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 H6 N O2, H2 O' _chemical_formula_sum 'C24 H27 F N4 O6' _chemical_formula_weight 486.50 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _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 90.013(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.457(2) _cell_length_b 14.4489(15) _cell_length_c 7.3700(8) _cell_measurement_reflns_used 4486 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.250 _cell_measurement_theta_min 2.365 _cell_volume 2284.9(4) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 23168 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 1.90 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_correction_T_min 0.9580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.364 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 424 _refine_ls_number_reflns 5512 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0566P)^2^+1.5604P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1247 _refine_ls_wR_factor_ref 0.1339 _reflns_number_gt 4282 _reflns_number_total 5512 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL a in P2(1)/c CELL 0.71073 21.4567 14.4489 7.3700 90.000 90.013 90.000 ZERR 4.000 0.0022 0.0015 0.0008 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O F UNIT 96 108 16 24 4 TEMP -123 SIZE .40 .20 .05 EQIV $1 1-X, 1-Y, -Z EQIV $2 -1+X, Y, Z EQIV $3 -1+X, 1.5-Y, -0.5+Z EQIV $4 X, 1.5-Y, 0.5+Z HTAB O3 O1 HTAB N3 O22 HTAB N3 O22_$1 HTAB N21 O2_$2 HTAB N21 O2_$3 HTAB O10 O21 HTAB O10 O21_$4 L.S. 10 BOND $H ACTA CONF FMAP 2 PLAN 6 OMIT -2 56 OMIT 1 0 0 OMIT 3 0 2 OMIT 2 3 0 WGHT 0.056600 1.560400 FVAR 0.10771 F1 5 0.674702 0.829826 0.185562 11.00000 0.01606 0.02133 = 0.02469 0.00295 -0.00309 0.00415 O1 4 0.891994 0.911643 0.371179 11.00000 0.02068 0.01776 = 0.03390 0.00187 -0.00360 -0.00192 O2 4 1.040693 0.762752 0.569326 11.00000 0.01652 0.02980 = 0.04466 -0.00226 -0.00768 0.00018 O3 4 1.000746 0.900425 0.508946 11.00000 0.01853 0.02334 = 0.04368 -0.00090 -0.00538 -0.00552 H33 2 0.962874 0.922104 0.457988 11.00000 0.04897 N1 3 0.878233 0.629305 0.412501 11.00000 0.01354 0.01539 = 0.02310 0.00044 -0.00125 0.00086 N2 3 0.657939 0.645046 0.249125 11.00000 0.01224 0.02053 = 0.01974 0.00229 -0.00278 -0.00190 N3 3 0.545802 0.545936 0.176227 11.00000 0.01524 0.02150 = 0.02449 -0.00386 -0.00150 -0.00198 H31 2 0.501845 0.540852 0.187257 11.00000 0.04886 H32 2 0.559049 0.502016 0.103346 11.00000 0.03353 C1 1 0.887680 0.825228 0.385970 11.00000 0.01542 0.01995 = 0.01821 -0.00005 0.00164 -0.00135 C2 1 0.937491 0.768107 0.451996 11.00000 0.01339 0.02137 = 0.02121 -0.00134 0.00100 -0.00080 C3 1 0.930377 0.674298 0.460511 11.00000 0.01239 0.02129 = 0.02138 0.00043 -0.00163 0.00303 C4 1 0.997403 0.808774 0.513701 11.00000 0.01728 0.02498 = 0.02350 -0.00227 0.00031 -0.00244 C5 1 0.874910 0.529162 0.435572 11.00000 0.01623 0.01585 = 0.02559 0.00189 -0.00141 0.00163 C6 1 0.928456 0.472145 0.368361 11.00000 0.02020 0.02055 = 0.04021 0.00028 0.00289 0.00478 C7 1 0.867080 0.469930 0.269903 11.00000 0.02842 0.02083 = 0.02997 -0.00286 -0.00266 -0.00003 C8 1 0.830887 0.775980 0.338172 11.00000 0.01458 0.01851 = 0.01744 0.00031 0.00080 -0.00050 C9 1 0.778743 0.825534 0.277248 11.00000 0.01877 0.01570 = 0.01980 0.00172 0.00096 0.00099 C10 1 0.724873 0.780086 0.240039 11.00000 0.01448 0.01977 = 0.01682 0.00071 -0.00031 0.00370 C11 1 0.717249 0.683640 0.265933 11.00000 0.01504 0.01918 = 0.01608 -0.00032 0.00013 -0.00059 C12 1 0.769179 0.634251 0.321626 11.00000 0.01451 0.01778 = 0.02003 -0.00104 -0.00049 0.00016 C13 1 0.825943 0.679659 0.355868 11.00000 0.01421 0.01868 = 0.01575 0.00021 -0.00003 0.00165 C14 1 0.627360 0.652709 0.070118 11.00000 0.01728 0.02216 = 0.01752 0.00052 -0.00156 -0.00037 C15 1 0.558189 0.636977 0.087606 11.00000 0.01732 0.02529 = 0.02242 0.00127 -0.00420 -0.00033 C16 1 0.646826 0.554224 0.331046 11.00000 0.01823 0.01765 = 0.02282 0.00203 -0.00373 -0.00141 C17 1 0.577205 0.541027 0.355811 11.00000 0.01960 0.02132 = 0.02176 0.00115 -0.00232 -0.00442 H3 2 0.961244 0.636667 0.503502 11.00000 0.01792 H5 2 0.857682 0.514566 0.548023 11.00000 0.01339 H9 2 0.779833 0.883474 0.268771 11.00000 0.03006 H12 2 0.765874 0.564592 0.337534 11.00000 0.02704 H61 2 0.962785 0.504465 0.304490 11.00000 0.03646 H62 2 0.940234 0.418855 0.442142 11.00000 0.02702 H71 2 0.865465 0.502550 0.150955 11.00000 0.03138 H72 2 0.838228 0.413609 0.285672 11.00000 0.03127 H141 2 0.645261 0.605602 -0.010188 11.00000 0.02238 H142 2 0.632899 0.713307 0.020157 11.00000 0.01551 H151 2 0.539196 0.687515 0.165597 11.00000 0.02291 H152 2 0.538831 0.637252 -0.029229 11.00000 0.02582 H161 2 0.663951 0.505785 0.253142 11.00000 0.03527 H162 2 0.666062 0.554124 0.450574 11.00000 0.01866 H171 2 0.560977 0.587258 0.430194 11.00000 0.02546 H172 2 0.567381 0.482252 0.410489 11.00000 0.03370 N21 3 0.140612 0.669065 0.334263 11.00000 0.02098 0.04160 = 0.04476 0.00268 0.00270 0.00691 H21 2 0.129164 0.713061 0.415652 11.00000 0.04264 H22 2 0.118722 0.658808 0.238339 11.00000 0.04179 O21 4 0.438154 0.649602 0.367251 11.00000 0.02238 0.02708 = 0.02684 -0.00122 -0.00243 -0.00244 O22 4 0.419819 0.539570 0.163117 11.00000 0.01971 0.02876 = 0.03146 -0.00702 0.00243 0.00044 C21 1 0.401497 0.601708 0.271707 11.00000 0.02115 0.02050 = 0.02020 0.00319 0.00062 -0.00182 C22 1 0.332688 0.617546 0.289058 11.00000 0.02038 0.01887 = 0.02289 0.00129 0.00074 0.00073 C23 1 0.309244 0.675420 0.423867 11.00000 0.02504 0.03279 = 0.03070 -0.00939 -0.00050 -0.00052 C24 1 0.246261 0.691042 0.440619 11.00000 0.02821 0.03463 = 0.03609 -0.01076 0.00643 0.00410 C25 1 0.203757 0.651578 0.319753 11.00000 0.02011 0.02186 = 0.03276 0.00767 0.00440 0.00266 C26 1 0.226894 0.591777 0.186787 11.00000 0.02426 0.02721 = 0.02978 0.00022 -0.00390 -0.00262 C27 1 0.290391 0.575933 0.172908 11.00000 0.02599 0.02320 = 0.02617 -0.00467 0.00118 0.00260 H23 2 0.335109 0.703976 0.512739 11.00000 0.03907 H24 2 0.231631 0.731790 0.533995 11.00000 0.05236 H26 2 0.200050 0.563746 0.102328 11.00000 0.03922 H27 2 0.304373 0.535328 0.080281 11.00000 0.03598 O10 4 0.454980 0.664909 0.748853 11.00000 0.08044 0.02967 = 0.03685 -0.00761 -0.02498 0.01531 H10 2 0.450300 0.673528 0.629177 11.00000 0.05545 H11 2 0.447638 0.717261 0.794719 11.00000 0.05709 HKLF 4 REM a in P2(1)/c REM R1 = 0.0486 for 4282 Fo > 4sig(Fo) and 0.0652 for all 5512 data REM 424 parameters refined using 0 restraints END WGHT 0.0566 1.5604 REM Highest difference peak 0.364, deepest hole -0.233, 1-sigma level 0.055 Q1 1 0.9660 0.7874 0.4653 11.00000 0.05 0.36 Q2 1 0.3900 0.5413 0.0558 11.00000 0.05 0.34 Q3 1 0.8564 0.7988 0.3608 11.00000 0.05 0.34 Q4 1 0.8576 0.5131 0.3406 11.00000 0.05 0.33 Q5 1 0.9181 0.7956 0.4145 11.00000 0.05 0.30 Q6 1 0.8289 0.7308 0.3449 11.00000 0.05 0.29 ; _cod_data_source_file d0ce00514b2.cif _cod_data_source_block a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240534 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.67470(5) 0.82983(7) 0.18556(14) 0.0207(2) Uani 1 1 d . . . O1 O 0.89199(6) 0.91164(9) 0.37118(18) 0.0241(3) Uani 1 1 d . . . O2 O 1.04069(6) 0.76275(10) 0.5693(2) 0.0303(3) Uani 1 1 d . . . O3 O 1.00075(6) 0.90043(9) 0.5089(2) 0.0285(3) Uani 1 1 d . . . H33 H 0.9629(14) 0.9221(19) 0.458(4) 0.049(8) Uiso 1 1 d . . . N1 N 0.87823(7) 0.62930(10) 0.4125(2) 0.0173(3) Uani 1 1 d . . . N2 N 0.65794(6) 0.64505(10) 0.24912(19) 0.0175(3) Uani 1 1 d . . . N3 N 0.54580(7) 0.54594(11) 0.1762(2) 0.0204(3) Uani 1 1 d . . . H31 H 0.5018(14) 0.5409(19) 0.187(4) 0.049(7) Uiso 1 1 d . . . H32 H 0.5590(11) 0.5020(17) 0.103(3) 0.034(6) Uiso 1 1 d . . . C1 C 0.88768(8) 0.82523(12) 0.3860(2) 0.0179(3) Uani 1 1 d . . . C2 C 0.93749(8) 0.76811(12) 0.4520(2) 0.0187(3) Uani 1 1 d . . . C3 C 0.93038(8) 0.67430(12) 0.4605(2) 0.0184(3) Uani 1 1 d . . . C4 C 0.99740(8) 0.80877(13) 0.5137(2) 0.0219(4) Uani 1 1 d . . . C5 C 0.87491(8) 0.52916(12) 0.4356(3) 0.0192(4) Uani 1 1 d . . . C6 C 0.92846(9) 0.47215(14) 0.3684(3) 0.0270(4) Uani 1 1 d . . . C7 C 0.86708(9) 0.46993(14) 0.2699(3) 0.0264(4) Uani 1 1 d . . . C8 C 0.83089(8) 0.77598(12) 0.3382(2) 0.0168(3) Uani 1 1 d . . . C9 C 0.77874(8) 0.82553(13) 0.2772(2) 0.0181(3) Uani 1 1 d . . . C10 C 0.72487(8) 0.78009(12) 0.2400(2) 0.0170(3) Uani 1 1 d . . . C11 C 0.71725(8) 0.68364(12) 0.2659(2) 0.0168(3) Uani 1 1 d . . . C12 C 0.76918(8) 0.63425(12) 0.3216(2) 0.0174(3) Uani 1 1 d . . . C13 C 0.82594(8) 0.67966(12) 0.3559(2) 0.0162(3) Uani 1 1 d . . . C14 C 0.62736(8) 0.65271(13) 0.0701(2) 0.0190(3) Uani 1 1 d . . . C15 C 0.55819(8) 0.63698(13) 0.0876(3) 0.0217(4) Uani 1 1 d . . . C16 C 0.64683(8) 0.55422(12) 0.3310(3) 0.0196(4) Uani 1 1 d . . . C17 C 0.57721(8) 0.54103(13) 0.3558(2) 0.0209(4) Uani 1 1 d . . . H3 H 0.9612(10) 0.6367(14) 0.504(3) 0.018(5) Uiso 1 1 d . . . H5 H 0.8577(9) 0.5146(13) 0.548(3) 0.013(5) Uiso 1 1 d . . . H9 H 0.7798(11) 0.8835(17) 0.269(3) 0.030(6) Uiso 1 1 d . . . H12 H 0.7659(10) 0.5646(16) 0.338(3) 0.027(6) Uiso 1 1 d . . . H61 H 0.9628(12) 0.5045(17) 0.304(3) 0.036(6) Uiso 1 1 d . . . H62 H 0.9402(10) 0.4189(16) 0.442(3) 0.027(6) Uiso 1 1 d . . . H71 H 0.8655(11) 0.5026(16) 0.151(3) 0.031(6) Uiso 1 1 d . . . H72 H 0.8382(11) 0.4136(17) 0.286(3) 0.031(6) Uiso 1 1 d . . . H141 H 0.6453(10) 0.6056(15) -0.010(3) 0.022(5) Uiso 1 1 d . . . H142 H 0.6329(9) 0.7133(14) 0.020(3) 0.016(5) Uiso 1 1 d . . . H151 H 0.5392(10) 0.6875(15) 0.166(3) 0.023(5) Uiso 1 1 d . . . H152 H 0.5388(10) 0.6373(15) -0.029(3) 0.026(5) Uiso 1 1 d . . . H161 H 0.6640(11) 0.5058(17) 0.253(3) 0.035(6) Uiso 1 1 d . . . H162 H 0.6661(10) 0.5541(14) 0.451(3) 0.019(5) Uiso 1 1 d . . . H171 H 0.5610(10) 0.5873(16) 0.430(3) 0.025(6) Uiso 1 1 d . . . H172 H 0.5674(11) 0.4823(17) 0.410(3) 0.034(6) Uiso 1 1 d . . . N21 N 0.14061(8) 0.66906(15) 0.3343(3) 0.0358(4) Uani 1 1 d . . . H21 H 0.1292(12) 0.713(2) 0.416(4) 0.043(7) Uiso 1 1 d . . . H22 H 0.1187(13) 0.6588(18) 0.238(4) 0.042(7) Uiso 1 1 d . . . O21 O 0.43815(6) 0.64960(9) 0.36725(18) 0.0254(3) Uani 1 1 d . . . O22 O 0.41982(6) 0.53957(10) 0.16312(18) 0.0266(3) Uani 1 1 d . . . C21 C 0.40150(8) 0.60171(12) 0.2717(2) 0.0206(4) Uani 1 1 d . . . C22 C 0.33269(8) 0.61755(12) 0.2891(2) 0.0207(4) Uani 1 1 d . . . C23 C 0.30924(10) 0.67542(15) 0.4239(3) 0.0295(4) Uani 1 1 d . . . C24 C 0.24626(10) 0.69104(16) 0.4406(3) 0.0330(5) Uani 1 1 d . . . C25 C 0.20376(9) 0.65158(13) 0.3198(3) 0.0249(4) Uani 1 1 d . . . C26 C 0.22689(9) 0.59178(14) 0.1868(3) 0.0271(4) Uani 1 1 d . . . C27 C 0.29039(9) 0.57593(13) 0.1729(3) 0.0251(4) Uani 1 1 d . . . H23 H 0.3351(12) 0.7040(18) 0.513(3) 0.039(7) Uiso 1 1 d . . . H24 H 0.2316(13) 0.732(2) 0.534(4) 0.052(8) Uiso 1 1 d . . . H26 H 0.2001(12) 0.5637(18) 0.102(3) 0.039(7) Uiso 1 1 d . . . H27 H 0.3044(11) 0.5353(17) 0.080(3) 0.036(6) Uiso 1 1 d . . . O10 O 0.45498(10) 0.66491(12) 0.7489(3) 0.0490(5) Uani 1 1 d . . . H10 H 0.4503(14) 0.674(2) 0.629(4) 0.055(8) Uiso 1 1 d . . . H11 H 0.4476(14) 0.717(2) 0.795(4) 0.057(9) 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 F1 0.0161(5) 0.0213(5) 0.0247(5) 0.0030(4) -0.0031(4) 0.0041(4) O1 0.0207(6) 0.0178(6) 0.0339(7) 0.0019(5) -0.0036(5) -0.0019(5) O2 0.0165(6) 0.0298(8) 0.0447(8) -0.0023(6) -0.0077(6) 0.0002(5) O3 0.0185(7) 0.0233(7) 0.0437(8) -0.0009(6) -0.0054(6) -0.0055(5) N1 0.0135(7) 0.0154(7) 0.0231(7) 0.0004(5) -0.0013(5) 0.0009(5) N2 0.0122(7) 0.0205(7) 0.0197(7) 0.0023(6) -0.0028(5) -0.0019(5) N3 0.0152(7) 0.0215(8) 0.0245(8) -0.0039(6) -0.0015(6) -0.0020(6) C1 0.0154(8) 0.0200(8) 0.0182(8) 0.0000(6) 0.0016(6) -0.0014(6) C2 0.0134(8) 0.0214(9) 0.0212(8) -0.0013(7) 0.0010(6) -0.0008(6) C3 0.0124(8) 0.0213(9) 0.0214(8) 0.0004(7) -0.0016(6) 0.0030(7) C4 0.0173(8) 0.0250(9) 0.0235(9) -0.0023(7) 0.0003(7) -0.0024(7) C5 0.0162(8) 0.0158(8) 0.0256(9) 0.0019(7) -0.0014(7) 0.0016(6) C6 0.0202(9) 0.0206(9) 0.0402(11) 0.0003(8) 0.0029(8) 0.0048(7) C7 0.0284(10) 0.0208(9) 0.0300(10) -0.0029(8) -0.0027(8) 0.0000(8) C8 0.0146(8) 0.0185(8) 0.0174(8) 0.0003(6) 0.0008(6) -0.0005(6) C9 0.0188(8) 0.0157(8) 0.0198(8) 0.0017(6) 0.0010(6) 0.0010(6) C10 0.0145(8) 0.0198(8) 0.0168(8) 0.0007(6) -0.0003(6) 0.0037(6) C11 0.0150(8) 0.0192(8) 0.0161(7) -0.0003(6) 0.0001(6) -0.0006(6) C12 0.0145(8) 0.0178(8) 0.0200(8) -0.0010(6) -0.0005(6) 0.0002(6) C13 0.0142(8) 0.0187(8) 0.0158(7) 0.0002(6) 0.0000(6) 0.0017(6) C14 0.0173(8) 0.0222(9) 0.0175(8) 0.0005(7) -0.0016(6) -0.0004(7) C15 0.0173(8) 0.0253(9) 0.0224(9) 0.0013(7) -0.0042(7) -0.0003(7) C16 0.0182(8) 0.0177(8) 0.0228(9) 0.0020(7) -0.0037(7) -0.0014(7) C17 0.0196(9) 0.0213(9) 0.0218(9) 0.0011(7) -0.0023(7) -0.0044(7) N21 0.0210(9) 0.0416(11) 0.0448(11) 0.0027(9) 0.0027(8) 0.0069(8) O21 0.0224(7) 0.0271(7) 0.0268(7) -0.0012(5) -0.0024(5) -0.0024(5) O22 0.0197(6) 0.0288(7) 0.0315(7) -0.0070(6) 0.0024(5) 0.0004(5) C21 0.0212(9) 0.0205(9) 0.0202(8) 0.0032(7) 0.0006(7) -0.0018(7) C22 0.0204(9) 0.0189(8) 0.0229(9) 0.0013(7) 0.0007(7) 0.0007(7) C23 0.0250(10) 0.0328(11) 0.0307(10) -0.0094(8) -0.0005(8) -0.0005(8) C24 0.0282(11) 0.0346(11) 0.0361(11) -0.0108(9) 0.0064(9) 0.0041(9) C25 0.0201(9) 0.0219(9) 0.0328(10) 0.0077(8) 0.0044(7) 0.0027(7) C26 0.0243(10) 0.0272(10) 0.0298(10) 0.0002(8) -0.0039(8) -0.0026(8) C27 0.0260(10) 0.0232(9) 0.0262(9) -0.0047(8) 0.0012(8) 0.0026(7) O10 0.0804(14) 0.0297(9) 0.0368(9) -0.0076(7) -0.0250(9) 0.0153(9) 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 H33 107.1(17) . . ? C3 N1 C13 119.66(14) . . ? C3 N1 C5 119.39(14) . . ? C13 N1 C5 120.72(14) . . ? C11 N2 C16 118.06(14) . . ? C11 N2 C14 117.02(14) . . ? C16 N2 C14 111.29(14) . . ? C17 N3 C15 110.54(14) . . ? C17 N3 H31 111.7(16) . . ? C15 N3 H31 106.4(17) . . ? C17 N3 H32 111.3(16) . . ? C15 N3 H32 108.1(16) . . ? H31 N3 H32 109(2) . . ? O1 C1 C2 123.08(16) . . ? O1 C1 C8 121.79(16) . . ? C2 C1 C8 115.12(15) . . ? C3 C2 C1 120.21(16) . . ? C3 C2 C4 118.40(16) . . ? C1 C2 C4 121.39(16) . . ? N1 C3 C2 124.21(16) . . ? N1 C3 H3 114.1(13) . . ? C2 C3 H3 121.7(13) . . ? O2 C4 O3 120.96(17) . . ? O2 C4 C2 123.31(17) . . ? O3 C4 C2 115.71(16) . . ? N1 C5 C6 118.00(16) . . ? N1 C5 C7 118.45(16) . . ? C6 C5 C7 60.20(13) . . ? N1 C5 H5 110.3(12) . . ? C6 C5 H5 118.3(12) . . ? C7 C5 H5 123.4(12) . . ? C5 C6 C7 59.98(13) . . ? C5 C6 H61 117.9(14) . . ? C7 C6 H61 115.6(14) . . ? C5 C6 H62 116.6(13) . . ? C7 C6 H62 118.6(13) . . ? H61 C6 H62 116.4(19) . . ? C5 C7 C6 59.82(12) . . ? C5 C7 H71 116.8(14) . . ? C6 C7 H71 116.4(14) . . ? C5 C7 H72 115.2(13) . . ? C6 C7 H72 119.3(13) . . ? H71 C7 H72 116.9(19) . . ? C13 C8 C9 118.45(15) . . ? C13 C8 C1 121.78(15) . . ? C9 C8 C1 119.75(15) . . ? C10 C9 C8 119.81(16) . . ? C10 C9 H9 119.4(16) . . ? C8 C9 H9 120.7(16) . . ? F1 C10 C9 118.66(15) . . ? F1 C10 C11 118.04(14) . . ? C9 C10 C11 123.18(16) . . ? C12 C11 N2 123.65(16) . . ? C12 C11 C10 117.00(15) . . ? N2 C11 C10 119.14(15) . . ? C11 C12 C13 120.62(16) . . ? C11 C12 H12 119.2(13) . . ? C13 C12 H12 120.1(12) . . ? N1 C13 C8 118.87(15) . . ? N1 C13 C12 120.32(15) . . ? C8 C13 C12 120.80(15) . . ? N2 C14 C15 110.46(14) . . ? N2 C14 H141 108.2(12) . . ? C15 C14 H141 109.4(12) . . ? N2 C14 H142 110.9(12) . . ? C15 C14 H142 107.1(12) . . ? H141 C14 H142 110.7(17) . . ? N3 C15 C14 110.23(15) . . ? N3 C15 H151 108.3(12) . . ? C14 C15 H151 109.6(12) . . ? N3 C15 H152 108.7(13) . . ? C14 C15 H152 110.5(13) . . ? H151 C15 H152 109.4(18) . . ? N2 C16 C17 108.83(14) . . ? N2 C16 H161 109.8(14) . . ? C17 C16 H161 110.6(14) . . ? N2 C16 H162 107.8(12) . . ? C17 C16 H162 108.0(12) . . ? H161 C16 H162 111.8(18) . . ? N3 C17 C16 109.45(15) . . ? N3 C17 H171 108.7(13) . . ? C16 C17 H171 110.4(14) . . ? N3 C17 H172 108.4(14) . . ? C16 C17 H172 112.1(14) . . ? H171 C17 H172 107.7(19) . . ? C25 N21 H21 116.4(17) . . ? C25 N21 H22 116.1(18) . . ? H21 N21 H22 121(2) . . ? O21 C21 O22 123.24(17) . . ? O21 C21 C22 118.83(16) . . ? O22 C21 C22 117.92(16) . . ? C27 C22 C23 117.71(17) . . ? C27 C22 C21 121.75(16) . . ? C23 C22 C21 120.55(17) . . ? C24 C23 C22 121.17(19) . . ? C24 C23 H23 116.1(15) . . ? C22 C23 H23 122.7(15) . . ? C23 C24 C25 121.14(19) . . ? C23 C24 H24 119.1(17) . . ? C25 C24 H24 119.7(17) . . ? N21 C25 C24 121.06(19) . . ? N21 C25 C26 121.0(2) . . ? C24 C25 C26 117.88(18) . . ? C27 C26 C25 120.22(18) . . ? C27 C26 H26 118.9(16) . . ? C25 C26 H26 120.9(16) . . ? C22 C27 C26 121.80(18) . . ? C22 C27 H27 120.4(15) . . ? C26 C27 H27 117.8(15) . . ? H10 O10 H11 104(3) . . ? 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 1.3551(18) . ? O1 C1 1.257(2) . ? O2 C4 1.214(2) . ? O3 C4 1.327(2) . ? O3 H33 0.95(3) . ? N1 C3 1.341(2) . ? N1 C13 1.401(2) . ? N1 C5 1.459(2) . ? N2 C11 1.395(2) . ? N2 C16 1.464(2) . ? N2 C14 1.477(2) . ? N3 C17 1.487(2) . ? N3 C15 1.493(2) . ? N3 H31 0.95(3) . ? N3 H32 0.88(3) . ? C1 C2 1.435(2) . ? C1 C8 1.454(2) . ? C2 C3 1.365(2) . ? C2 C4 1.485(2) . ? C3 H3 0.91(2) . ? C5 C6 1.498(3) . ? C5 C7 1.500(3) . ? C5 H5 0.93(2) . ? C6 C7 1.504(3) . ? C6 H61 0.99(3) . ? C6 H62 0.98(2) . ? C7 H71 1.00(2) . ? C7 H72 1.03(2) . ? C8 C13 1.402(2) . ? C8 C9 1.402(2) . ? C9 C10 1.357(2) . ? C9 H9 0.84(2) . ? C10 C11 1.416(2) . ? C11 C12 1.385(2) . ? C12 C13 1.406(2) . ? C12 H12 1.02(2) . ? C14 C15 1.507(2) . ? C14 H141 0.98(2) . ? C14 H142 0.96(2) . ? C15 H151 1.01(2) . ? C15 H152 0.96(2) . ? C16 C17 1.517(2) . ? C16 H161 0.98(2) . ? C16 H162 0.97(2) . ? C17 H171 0.93(2) . ? C17 H172 0.96(3) . ? N21 C25 1.382(3) . ? N21 H21 0.91(3) . ? N21 H22 0.86(3) . ? O21 C21 1.262(2) . ? O22 C21 1.265(2) . ? C21 C22 1.500(2) . ? C22 C27 1.385(3) . ? C22 C23 1.393(3) . ? C23 C24 1.376(3) . ? C23 H23 0.95(3) . ? C24 C25 1.396(3) . ? C24 H24 0.96(3) . ? C25 C26 1.398(3) . ? C26 C27 1.385(3) . ? C26 H26 0.94(3) . ? C27 H27 0.95(3) . ? O10 H10 0.90(3) . ? O10 H11 0.84(3) . ? 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 H33 O1 0.95(3) 1.66(3) 2.5497(19) 155(3) . N3 H31 O22 0.95(3) 1.77(3) 2.706(2) 169(2) . N3 H32 O22 0.88(3) 2.10(3) 2.886(2) 148(2) 3_665 N21 H21 O2 0.91(3) 2.32(3) 3.071(2) 139(2) 1_455 N21 H22 O2 0.86(3) 2.37(3) 3.062(2) 137(2) 4_475 O10 H10 O21 0.90(3) 1.98(3) 2.844(2) 162(3) . O10 H11 O21 0.84(3) 2.01(4) 2.842(2) 170(3) 4_576 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 -178.35(17) . . . . ? C8 C1 C2 C3 2.2(2) . . . . ? O1 C1 C2 C4 2.1(3) . . . . ? C8 C1 C2 C4 -177.33(15) . . . . ? C13 N1 C3 C2 -2.6(3) . . . . ? C5 N1 C3 C2 -177.07(17) . . . . ? C1 C2 C3 N1 -0.9(3) . . . . ? C4 C2 C3 N1 178.59(16) . . . . ? C3 C2 C4 O2 0.9(3) . . . . ? C1 C2 C4 O2 -179.55(17) . . . . ? C3 C2 C4 O3 -177.47(16) . . . . ? C1 C2 C4 O3 2.1(2) . . . . ? C3 N1 C5 C6 -47.8(2) . . . . ? C13 N1 C5 C6 137.72(17) . . . . ? C3 N1 C5 C7 -117.23(18) . . . . ? C13 N1 C5 C7 68.3(2) . . . . ? N1 C5 C6 C7 -108.50(18) . . . . ? N1 C5 C7 C6 107.76(18) . . . . ? O1 C1 C8 C13 -179.55(16) . . . . ? C2 C1 C8 C13 -0.1(2) . . . . ? O1 C1 C8 C9 -1.3(3) . . . . ? C2 C1 C8 C9 178.14(15) . . . . ? C13 C8 C9 C10 1.1(2) . . . . ? C1 C8 C9 C10 -177.17(16) . . . . ? C8 C9 C10 F1 178.42(14) . . . . ? C8 C9 C10 C11 2.4(3) . . . . ? C16 N2 C11 C12 13.8(2) . . . . ? C14 N2 C11 C12 -123.42(18) . . . . ? C16 N2 C11 C10 -160.70(15) . . . . ? C14 N2 C11 C10 62.1(2) . . . . ? F1 C10 C11 C12 180.00(14) . . . . ? C9 C10 C11 C12 -4.0(3) . . . . ? F1 C10 C11 N2 -5.2(2) . . . . ? C9 C10 C11 N2 170.85(16) . . . . ? N2 C11 C12 C13 -172.57(15) . . . . ? C10 C11 C12 C13 2.0(2) . . . . ? C3 N1 C13 C8 4.6(2) . . . . ? C5 N1 C13 C8 179.00(15) . . . . ? C3 N1 C13 C12 -173.96(16) . . . . ? C5 N1 C13 C12 0.5(2) . . . . ? C9 C8 C13 N1 178.50(15) . . . . ? C1 C8 C13 N1 -3.3(2) . . . . ? C9 C8 C13 C12 -3.0(2) . . . . ? C1 C8 C13 C12 175.28(15) . . . . ? C11 C12 C13 N1 179.87(15) . . . . ? C11 C12 C13 C8 1.4(2) . . . . ? C11 N2 C14 C15 -161.69(15) . . . . ? C16 N2 C14 C15 58.37(19) . . . . ? C17 N3 C15 C14 56.6(2) . . . . ? N2 C14 C15 N3 -55.4(2) . . . . ? C11 N2 C16 C17 160.26(15) . . . . ? C14 N2 C16 C17 -60.26(18) . . . . ? C15 N3 C17 C16 -58.9(2) . . . . ? N2 C16 C17 N3 60.20(19) . . . . ? O21 C21 C22 C27 171.84(17) . . . . ? O22 C21 C22 C27 -9.2(3) . . . . ? O21 C21 C22 C23 -8.0(3) . . . . ? O22 C21 C22 C23 170.96(18) . . . . ? C27 C22 C23 C24 -0.3(3) . . . . ? C21 C22 C23 C24 179.58(19) . . . . ? C22 C23 C24 C25 -1.9(3) . . . . ? C23 C24 C25 N21 -178.5(2) . . . . ? C23 C24 C25 C26 3.3(3) . . . . ? N21 C25 C26 C27 179.23(19) . . . . ? C24 C25 C26 C27 -2.5(3) . . . . ? C23 C22 C27 C26 1.0(3) . . . . ? C21 C22 C27 C26 -178.85(18) . . . . ? C25 C26 C27 C22 0.4(3) . . . . ?