#------------------------------------------------------------------------------ #$Date: 2019-07-03 13:24:39 +0300 (Wed, 03 Jul 2019) $ #$Revision: 216710 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/73/1547307.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_1547307 loop_ _publ_author_name 'N.N. Golovnev' 'M.S. Molokeev' 'M.K. Lesnikov' 'I.V. Sterkhova' 'V.V. Atuchin' _publ_section_title ; Thiobarbiturate and barbiturate salts of pefloxacin drug: Growth, structure, thermal stability and IR-spectra ; _journal_issue 0 _journal_name_full 'Journal of Molecular Structure' _journal_page_first 367 _journal_page_last 372 _journal_paper_doi 10.1016/j.molstruc.2017.08.011 _journal_volume 1149 _journal_year 2017 _chemical_formula_moiety 'C17 H21 F N3 O3, C4 H3 N2 O3, 1.281(H2 O)' _chemical_formula_sum 'C21 H25 F N5 O7.28' _chemical_formula_weight 482.94 _chemical_name_systematic ; bis(pefloxacinium 2-thiobarbiturate) hydrate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _cell_angle_alpha 101.2430(10) _cell_angle_beta 92.5140(10) _cell_angle_gamma 109.4710(10) _cell_formula_units_Z 4 _cell_length_a 10.3252(3) _cell_length_b 13.8631(4) _cell_length_c 16.9586(3) _cell_measurement_reflns_used 24769 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.511 _cell_measurement_theta_min 2.107 _cell_volume 2229.09(10) _computing_cell_refinement 'APEX2 (Bruker, 2003-2008)' _computing_data_collection 'APEX2 (Bruker, 2003-2008)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2005)' _computing_publication_material 'publCIF (Westrip, 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_unetI/netI 0.0325 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 24769 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.511 _diffrn_reflns_theta_min 2.107 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004 ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.439 _exptl_crystal_description block _exptl_crystal_F_000 1013 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.626 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 637 _refine_ls_number_reflns 10127 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0550 _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^)+(0.1137P)^2^+0.3971P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1704 _refine_ls_wR_factor_ref 0.1891 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 7257 _reflns_number_total 10127 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file PefH2Hba2_2p5H2O.cif _cod_data_source_block p3 _cod_depositor_comments ; 2019-06-28 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C42 H50 F2 N10 O14.56' _cod_original_formula_weight 965.88 _cod_original_formula_moiety ; 2(C17 H21 F N3 O3), 2(C4 H3 N2 O3), H2 O, 1.563(O) ; _cod_original_formula_units_Z 2 _cod_database_code 1547307 _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 ; p3.res created by SHELXL-2014/7 TITL p_a.res in P-1 REM Old TITL p in P-1 REM SHELXT solution in P-1 REM R1 0.196, Rweak 0.005, Alpha 0.054, Orientation as input REM Formula found by SHELXT: C46 N10 O12 CELL 0.71073 10.3252 13.8631 16.9586 101.243 92.514 109.471 ZERR 2.000 0.0003 0.0004 0.0003 0.001 0.001 0.001 LATT 1 SFAC C H N O F UNIT 84 100 20 29.12 4 TEMP 23.000 L.S. 10 BOND $H LIST 6 EADP O3WA O3WB EADP O2WA O2WB OMIT -1 -1 1 OMIT 0 1 0 DFIX 0.9 0.01 O2C H2C DFIX 0.9 0.01 O2D H2D DFIX 0.9 0.01 O1W H11W DFIX 0.9 0.01 O1W H12W DFIX 1.5 0.01 H11W H12W ACTA 50 FMAP 2 PLAN 40 WGHT 0.113700 0.397100 FVAR 0.53807 0.50000 O1A 4 0.570009 1.090891 0.104709 11.00000 0.02693 0.03691 = 0.07331 0.00457 0.00426 0.01083 O2A 4 0.451897 0.737303 0.054090 11.00000 0.04521 0.04092 = 0.09462 0.01246 0.01417 0.02427 O3A 4 0.113264 0.898396 0.072487 11.00000 0.02456 0.03991 = 0.05976 0.01350 0.00675 0.01218 N1A 3 0.342246 0.991869 0.088723 11.00000 0.02555 0.03286 = 0.05154 0.00764 0.00507 0.01344 AFIX 43 H1A 2 0.320841 1.047591 0.096550 11.00000 -1.20000 AFIX 0 N3A 3 0.507878 0.913575 0.082160 11.00000 0.02516 0.03961 = 0.05237 0.00832 0.00374 0.01550 AFIX 43 H3A 2 0.593515 0.919251 0.087107 11.00000 -1.20000 AFIX 0 C2A 1 0.479081 1.003637 0.092677 11.00000 0.02685 0.03756 = 0.04038 0.00644 0.00323 0.01234 C4A 1 0.409314 0.812611 0.063959 11.00000 0.03675 0.03906 = 0.04914 0.01005 0.00828 0.01825 C5A 1 0.270693 0.806585 0.059652 11.00000 0.03145 0.03292 = 0.05245 0.00763 0.00668 0.01013 AFIX 43 H5A 2 0.200906 0.741035 0.047607 11.00000 -1.20000 AFIX 0 C6A 1 0.235548 0.895490 0.072848 11.00000 0.02515 0.03746 = 0.03854 0.00864 0.00400 0.01003 O1B 4 -0.186659 -0.028197 0.081979 11.00000 0.02661 0.04020 = 0.07200 0.01080 0.00150 0.00834 O2B 4 -0.094747 0.321843 0.158013 11.00000 0.05166 0.05110 = 0.10012 -0.01046 -0.00419 0.03047 O3B 4 0.263451 0.182801 0.117181 11.00000 0.02344 0.04237 = 0.06480 0.00448 -0.00180 0.00975 N1B 3 0.037666 0.080092 0.100362 11.00000 0.02424 0.03428 = 0.05082 0.00661 0.00058 0.01213 AFIX 43 H1B 2 0.064011 0.026794 0.089269 11.00000 -1.20000 AFIX 0 N3B 3 -0.137096 0.147955 0.119027 11.00000 0.02434 0.04378 = 0.04802 0.00415 0.00008 0.01559 AFIX 43 H3B 2 -0.223742 0.138216 0.119659 11.00000 -1.20000 AFIX 0 C2B 1 -0.100984 0.061648 0.098796 11.00000 0.02532 0.03948 = 0.04037 0.00784 -0.00012 0.01179 C4B 1 -0.045544 0.250735 0.138796 11.00000 0.03857 0.04483 = 0.04952 -0.00078 -0.00339 0.02090 C5B 1 0.094653 0.264228 0.137525 11.00000 0.03317 0.03412 = 0.05950 0.00106 -0.00430 0.00838 AFIX 43 H5B 2 0.159870 0.331770 0.149593 11.00000 -1.20000 AFIX 0 C6B 1 0.138584 0.179146 0.118671 11.00000 0.02523 0.03983 = 0.04221 0.00598 -0.00266 0.01054 F1 5 0.012147 0.895454 0.438681 11.00000 0.05826 0.08642 = 0.05935 0.01108 0.01347 0.03839 O1C 4 0.425959 0.941884 0.628449 11.00000 0.07778 0.07242 = 0.06374 0.00896 -0.01405 0.00975 O2C 4 0.654124 0.932122 0.683346 11.00000 0.08210 0.08464 = 0.08813 0.02696 -0.02975 0.00166 H2C 2 0.589081 0.959948 0.699170 11.00000 -1.20000 O3C 4 0.763967 0.848774 0.604205 11.00000 0.06770 0.13040 = 0.12502 0.04704 -0.02661 0.03406 N1C 3 -0.098339 0.770447 0.129749 11.00000 0.03385 0.04109 = 0.04985 0.01656 0.00459 0.01064 AFIX 13 H0C 2 -0.021302 0.813661 0.105890 11.00000 -1.20000 AFIX 0 N2C 3 0.047266 0.796620 0.286048 11.00000 0.04164 0.04484 = 0.04804 0.01272 0.00516 0.02120 N3C 3 0.484991 0.798076 0.404833 11.00000 0.05172 0.07975 = 0.06967 0.02597 0.00073 0.03372 C1C 1 0.009737 0.882438 0.264216 11.00000 0.05359 0.04545 = 0.05192 0.01160 0.00369 0.02496 AFIX 23 H1AC 2 0.085098 0.926333 0.240705 11.00000 -1.20000 H1BC 2 -0.006428 0.925591 0.312380 11.00000 -1.20000 AFIX 0 C2C 1 -0.118999 0.837417 0.204254 11.00000 0.04449 0.05386 = 0.05670 0.01599 0.00853 0.02676 AFIX 23 H2AC 2 -0.194960 0.796039 0.228885 11.00000 -1.20000 H2BC 2 -0.143401 0.894207 0.190151 11.00000 -1.20000 AFIX 0 C3C 1 -0.058380 0.685102 0.152660 11.00000 0.05290 0.04108 = 0.05407 0.01251 0.00504 0.01891 AFIX 23 H3AC 2 -0.039916 0.642894 0.104772 11.00000 -1.20000 H3BC 2 -0.134441 0.640011 0.174927 11.00000 -1.20000 AFIX 0 C4C 1 0.067788 0.729023 0.213967 11.00000 0.05035 0.04922 = 0.05042 0.01491 0.00814 0.02778 AFIX 23 H4AC 2 0.089362 0.671739 0.229274 11.00000 -1.20000 H4BC 2 0.145798 0.768939 0.189923 11.00000 -1.20000 AFIX 0 C5C 1 0.224557 0.899583 0.495748 11.00000 0.05394 0.04362 = 0.04807 0.01260 0.00770 0.01160 AFIX 43 H05C 2 0.208795 0.933342 0.545448 11.00000 -1.20000 AFIX 0 C6C 1 0.130712 0.874943 0.429596 11.00000 0.04296 0.04710 = 0.05368 0.01627 0.00962 0.01709 C7C 1 0.149266 0.825342 0.352363 11.00000 0.04005 0.04466 = 0.04811 0.01908 0.00681 0.01565 C8C 1 0.268091 0.800730 0.346254 11.00000 0.04746 0.06118 = 0.04989 0.02022 0.00765 0.02645 AFIX 43 H08C 2 0.283478 0.767548 0.296230 11.00000 -1.20000 AFIX 0 C9C 1 0.366036 0.824542 0.413600 11.00000 0.04395 0.05053 = 0.05721 0.02288 0.00462 0.01846 C10C 1 0.344749 0.874421 0.489459 11.00000 0.04604 0.04202 = 0.05675 0.02245 0.00088 0.00754 C11C 1 0.444221 0.896652 0.559897 11.00000 0.05683 0.04155 = 0.05744 0.01733 -0.00665 0.00051 C12C 1 0.560099 0.864461 0.545545 11.00000 0.04610 0.05119 = 0.08118 0.03177 -0.01191 0.00242 C13C 1 0.575694 0.818215 0.469310 11.00000 0.05147 0.07064 = 0.08048 0.03210 -0.00242 0.02131 AFIX 43 H13C 2 0.653927 0.799890 0.462221 11.00000 -1.20000 AFIX 0 C14C 1 0.669659 0.879750 0.612203 11.00000 0.06305 0.06908 = 0.08715 0.03456 -0.02004 0.00095 C15C 1 0.512951 0.749941 0.323388 11.00000 0.08654 0.15816 = 0.09052 0.02721 0.01066 0.09455 AFIX 23 H14C 2 0.584408 0.720286 0.330371 11.00000 -1.20000 H15C 2 0.429723 0.693205 0.296423 11.00000 -1.20000 AFIX 0 C16C 1 0.557373 0.826485 0.271855 11.00000 0.08932 0.15792 = 0.09787 0.03053 0.03152 0.06772 AFIX 33 H16C 2 0.574044 0.792197 0.220452 11.00000 -1.20000 H17C 2 0.486178 0.855018 0.263804 11.00000 -1.20000 H18C 2 0.640831 0.882094 0.297745 11.00000 -1.20000 AFIX 0 C17C 1 -0.222579 0.727608 0.068275 11.00000 0.04252 0.05436 = 0.06548 0.01630 -0.00632 0.00999 AFIX 137 H19C 2 -0.207524 0.680025 0.023392 11.00000 -1.20000 H20C 2 -0.238638 0.784187 0.049624 11.00000 -1.20000 H21C 2 -0.301651 0.691002 0.092186 11.00000 -1.20000 AFIX 0 F2 5 0.513588 0.398992 0.479925 11.00000 0.05283 0.07316 = 0.06331 0.00908 0.01210 0.03689 O1D 4 0.942944 0.458506 0.657698 11.00000 0.06707 0.06196 = 0.03912 0.00706 -0.00061 0.01688 O2D 4 1.171133 0.450232 0.709138 11.00000 0.06279 0.05767 = 0.04910 0.01552 -0.01319 0.00589 H2D 2 1.091945 0.465353 0.707904 11.00000 -1.20000 O3D 4 1.282628 0.372527 0.626416 11.00000 0.06435 0.08717 = 0.07699 0.00738 -0.02440 0.03336 N1D 3 0.477931 0.361743 0.168295 11.00000 0.03232 0.03624 = 0.05811 0.00283 -0.00339 0.01029 AFIX 13 H0D 2 0.390470 0.302581 0.152048 11.00000 -1.20000 AFIX 0 N2D 3 0.554141 0.319449 0.319912 11.00000 0.05059 0.06457 = 0.05230 -0.00606 -0.00958 0.03641 N3D 3 0.997842 0.325225 0.429992 11.00000 0.03586 0.04619 = 0.04212 0.01134 0.00112 0.01406 C1D 1 0.446169 0.364796 0.312755 11.00000 0.04850 0.07847 = 0.05485 0.00306 -0.00247 0.03870 AFIX 23 H1AD 2 0.446978 0.410570 0.364084 11.00000 -1.20000 H1BD 2 0.356568 0.308994 0.300432 11.00000 -1.20000 AFIX 0 C2D 1 0.466713 0.426202 0.247679 11.00000 0.04179 0.05052 = 0.06472 -0.00498 -0.00732 0.02623 AFIX 23 H2AD 2 0.389443 0.450205 0.241631 11.00000 -1.20000 H2BD 2 0.550266 0.487518 0.263602 11.00000 -1.20000 AFIX 0 C3D 1 0.590072 0.318038 0.177626 11.00000 0.03053 0.04393 = 0.05942 -0.00396 -0.00267 0.01395 AFIX 23 H3AD 2 0.678601 0.374665 0.193089 11.00000 -1.20000 H3BD 2 0.594281 0.273666 0.126668 11.00000 -1.20000 AFIX 0 C4D 1 0.560093 0.254821 0.242002 11.00000 0.04505 0.04857 = 0.05338 -0.00653 -0.01225 0.02466 AFIX 23 H4AD 2 0.472487 0.197434 0.225419 11.00000 -1.20000 H4BD 2 0.631705 0.224976 0.247775 11.00000 -1.20000 AFIX 0 C5D 1 0.732500 0.411028 0.528605 11.00000 0.04984 0.03639 = 0.04148 0.00791 0.00727 0.01461 AFIX 43 H05D 2 0.716473 0.440458 0.579719 11.00000 -1.20000 AFIX 0 C6D 1 0.635754 0.387297 0.464495 11.00000 0.03939 0.03641 = 0.05310 0.00859 0.00799 0.01599 C7D 1 0.654767 0.346793 0.384082 11.00000 0.04019 0.03379 = 0.04376 0.00601 -0.00020 0.01435 C8D 1 0.779177 0.329953 0.374577 11.00000 0.03830 0.03713 = 0.03862 0.00608 0.00190 0.01429 AFIX 43 H08D 2 0.797747 0.305775 0.322730 11.00000 -1.20000 AFIX 0 C9D 1 0.877579 0.348214 0.440568 11.00000 0.03527 0.03311 = 0.04027 0.01087 0.00233 0.00934 C10D 1 0.856466 0.391816 0.518934 11.00000 0.04215 0.03189 = 0.04077 0.01088 0.00220 0.00839 C11D 1 0.957825 0.414067 0.587458 11.00000 0.04961 0.03523 = 0.03984 0.01233 0.00007 0.00535 C12D 1 1.074574 0.383986 0.571384 11.00000 0.04318 0.03841 = 0.04690 0.01447 -0.00588 0.00541 C13D 1 1.088852 0.341365 0.494208 11.00000 0.03725 0.04552 = 0.05235 0.01556 -0.00179 0.01158 AFIX 43 H13D 2 1.166274 0.322387 0.485631 11.00000 -1.20000 AFIX 0 C14D 1 1.185481 0.400087 0.636686 11.00000 0.05281 0.04472 = 0.05488 0.01598 -0.01247 0.00625 C15D 1 1.025439 0.277715 0.349141 11.00000 0.04237 0.06670 = 0.04408 0.01316 0.00684 0.02558 AFIX 23 H14D 2 1.123917 0.291123 0.349740 11.00000 -1.20000 H15D 2 0.998572 0.310976 0.309123 11.00000 -1.20000 AFIX 0 C16D 1 0.948318 0.160786 0.324755 11.00000 0.06634 0.06538 = 0.04983 0.00565 0.00423 0.03264 AFIX 33 H16D 2 0.969336 0.133668 0.272267 11.00000 -1.20000 H17D 2 0.975966 0.127266 0.363555 11.00000 -1.20000 H18D 2 0.850641 0.147116 0.322945 11.00000 -1.20000 AFIX 0 C17D 1 0.498813 0.423076 0.103772 11.00000 0.06867 0.05190 = 0.07420 0.01903 0.00762 0.01846 AFIX 137 H19D 2 0.585862 0.480011 0.117118 11.00000 -1.20000 H20D 2 0.425388 0.450507 0.099801 11.00000 -1.20000 H21D 2 0.498619 0.378157 0.052900 11.00000 -1.20000 AFIX 0 O1W 4 0.256129 0.540064 0.048401 11.00000 0.12369 0.08101 = 0.23313 0.05046 0.06359 0.03195 H11W 2 0.259948 0.555206 0.105585 11.00000 -1.20000 H12W 2 0.314776 0.599787 0.035709 11.00000 -1.20000 O2WA 4 -0.016340 0.474977 0.099523 0.25545 0.11952 O2WB 4 -0.023803 0.461182 0.047392 0.45296 0.11952 O3WA 4 0.241739 0.544365 0.222791 0.47001 0.10393 O3WB 4 0.137769 0.504330 0.193539 0.38333 0.10393 HKLF 4 REM p_a.res in P-1 REM R1 = 0.0550 for 7257 Fo > 4sig(Fo) and 0.0747 for all 10127 data REM 637 parameters refined using 5 restraints END WGHT 0.1008 0.4647 REM Highest difference peak 0.626, deepest hole -0.373, 1-sigma level 0.051 Q1 1 -0.1908 0.4383 0.0470 11.00000 0.05 0.63 Q2 1 0.3118 0.5972 0.1581 11.00000 0.05 0.57 Q3 1 0.4676 0.6747 0.2813 11.00000 0.05 0.49 Q4 1 0.1749 0.4991 0.2229 11.00000 0.05 0.47 Q5 1 0.0834 0.5053 0.1652 11.00000 0.05 0.39 Q6 1 0.2628 0.5609 0.1849 11.00000 0.05 0.36 Q7 1 0.2402 0.5295 0.2530 11.00000 0.05 0.26 Q8 1 0.8426 0.3540 0.4080 11.00000 0.05 0.22 Q9 1 0.8603 0.3582 0.4932 11.00000 0.05 0.21 Q10 1 -0.0229 0.0790 0.0962 11.00000 0.05 0.21 Q11 1 0.5607 0.8416 0.5349 11.00000 0.05 0.21 Q12 1 0.1109 0.2347 0.1104 11.00000 0.05 0.21 Q13 1 0.6289 0.3535 0.3461 11.00000 0.05 0.19 Q14 1 0.7018 0.4252 0.4917 11.00000 0.05 0.19 Q15 1 0.0683 0.4939 0.1210 11.00000 0.05 0.18 Q16 1 0.1150 0.8253 0.3194 11.00000 0.05 0.18 Q17 1 1.0078 0.3087 0.4137 11.00000 0.05 0.18 Q18 1 0.5445 0.8264 0.3377 11.00000 0.05 0.17 Q19 1 0.1930 0.9090 0.4598 11.00000 0.05 0.17 Q20 1 0.1183 0.2278 0.1475 11.00000 0.05 0.17 Q21 1 0.3511 0.9729 0.6431 11.00000 0.05 0.17 Q22 1 0.7457 0.8859 0.6540 11.00000 0.05 0.17 Q23 1 0.4737 0.3963 0.1981 11.00000 0.05 0.17 Q24 1 1.1147 0.3971 0.6015 11.00000 0.05 0.17 Q25 1 0.9013 0.4017 0.5480 11.00000 0.05 0.16 Q26 1 -0.0244 0.4678 0.0698 11.00000 0.05 0.16 Q27 1 -0.0010 0.4484 0.0176 11.00000 0.05 0.16 Q28 1 0.6386 0.3487 0.4244 11.00000 0.05 0.15 Q29 1 0.8162 0.4256 0.5191 11.00000 0.05 0.15 Q30 1 0.5827 0.9207 0.6502 11.00000 0.05 0.15 Q31 1 0.2669 0.2350 0.1524 11.00000 0.05 0.15 Q32 1 0.5754 0.3325 0.3064 11.00000 0.05 0.15 Q33 1 0.5681 0.9352 0.6621 11.00000 0.05 0.14 Q34 1 0.1425 0.9618 0.0715 11.00000 0.05 0.14 Q35 1 0.5244 0.4378 0.1318 11.00000 0.05 0.14 Q36 1 0.2976 0.9109 0.4892 11.00000 0.05 0.14 Q37 1 0.1209 0.9690 0.1100 11.00000 0.05 0.14 Q38 1 0.3017 0.9515 0.0938 11.00000 0.05 0.14 Q39 1 0.5949 0.2976 0.2219 11.00000 0.05 0.14 Q40 1 0.2560 0.8451 0.0397 11.00000 0.05 0.14 ; _shelx_res_checksum 96678 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 O1A O 0.57001(12) 1.09089(10) 0.10471(9) 0.0470(3) Uani 1 1 d . . . . . O2A O 0.45190(15) 0.73730(11) 0.05409(11) 0.0580(4) Uani 1 1 d . . . . . O3A O 0.11326(11) 0.89840(10) 0.07249(8) 0.0408(3) Uani 1 1 d . . . . . N1A N 0.34225(13) 0.99187(11) 0.08872(9) 0.0360(3) Uani 1 1 d . . . . . H1A H 0.3208 1.0476 0.0965 0.043 Uiso 1 1 calc R U . . . N3A N 0.50788(14) 0.91358(11) 0.08216(9) 0.0383(3) Uani 1 1 d . . . . . H3A H 0.5935 0.9193 0.0871 0.046 Uiso 1 1 calc R U . . . C2A C 0.47908(16) 1.00364(13) 0.09268(10) 0.0350(4) Uani 1 1 d . . . . . C4A C 0.40931(18) 0.81261(14) 0.06396(11) 0.0402(4) Uani 1 1 d . . . . . C5A C 0.27069(18) 0.80658(14) 0.05965(11) 0.0394(4) Uani 1 1 d . . . . . H5A H 0.2009 0.7410 0.0476 0.047 Uiso 1 1 calc R U . . . C6A C 0.23555(16) 0.89549(13) 0.07285(10) 0.0339(3) Uani 1 1 d . . . . . O1B O -0.18666(12) -0.02820(10) 0.08198(9) 0.0475(3) Uani 1 1 d . . . . . O2B O -0.09475(16) 0.32184(12) 0.15801(11) 0.0688(5) Uani 1 1 d . . . . . O3B O 0.26345(12) 0.18280(10) 0.11718(8) 0.0453(3) Uani 1 1 d . . . . . N1B N 0.03767(13) 0.08009(11) 0.10036(9) 0.0365(3) Uani 1 1 d . . . . . H1B H 0.0640 0.0268 0.0893 0.044 Uiso 1 1 calc R U . . . N3B N -0.13710(14) 0.14796(12) 0.11903(9) 0.0388(3) Uani 1 1 d . . . . . H3B H -0.2237 0.1382 0.1197 0.047 Uiso 1 1 calc R U . . . C2B C -0.10098(16) 0.06165(14) 0.09880(10) 0.0352(4) Uani 1 1 d . . . . . C4B C -0.04554(19) 0.25074(15) 0.13880(12) 0.0446(4) Uani 1 1 d . . . . . C5B C 0.09465(19) 0.26423(14) 0.13752(12) 0.0448(4) Uani 1 1 d . . . . . H5B H 0.1599 0.3318 0.1496 0.054 Uiso 1 1 calc R U . . . C6B C 0.13858(16) 0.17915(14) 0.11867(10) 0.0366(4) Uani 1 1 d . . . . . F1 F 0.01215(14) 0.89545(12) 0.43868(8) 0.0651(4) Uani 1 1 d . . . . . O1C O 0.4260(2) 0.94188(15) 0.62845(11) 0.0772(5) Uani 1 1 d . . . . . O2C O 0.6541(2) 0.93212(18) 0.68335(14) 0.0922(7) Uani 1 1 d D . . . . H2C H 0.589(3) 0.960(3) 0.699(2) 0.111 Uiso 1 1 d D U . . . O3C O 0.7640(2) 0.8488(2) 0.60421(15) 0.1064(8) Uani 1 1 d . . . . . N1C N -0.09834(15) 0.77045(12) 0.12975(9) 0.0413(3) Uani 1 1 d . . . . . H0C H -0.0213 0.8137 0.1059 0.050 Uiso 1 1 calc R U . . . N2C N 0.04727(16) 0.79662(12) 0.28605(9) 0.0429(4) Uani 1 1 d . . . . . N3C N 0.4850(2) 0.79808(17) 0.40483(12) 0.0631(5) Uani 1 1 d . . . . . C1C C 0.0097(2) 0.88244(16) 0.26422(12) 0.0483(4) Uani 1 1 d . . . . . H1AC H 0.0851 0.9263 0.2407 0.058 Uiso 1 1 calc R U . . . H1BC H -0.0064 0.9256 0.3124 0.058 Uiso 1 1 calc R U . . . C2C C -0.1190(2) 0.83742(17) 0.20425(12) 0.0486(5) Uani 1 1 d . . . . . H2AC H -0.1950 0.7960 0.2289 0.058 Uiso 1 1 calc R U . . . H2BC H -0.1434 0.8942 0.1902 0.058 Uiso 1 1 calc R U . . . C3C C -0.0584(2) 0.68510(15) 0.15266(12) 0.0485(4) Uani 1 1 d . . . . . H3AC H -0.0399 0.6429 0.1048 0.058 Uiso 1 1 calc R U . . . H3BC H -0.1344 0.6400 0.1749 0.058 Uiso 1 1 calc R U . . . C4C C 0.0678(2) 0.72902(16) 0.21397(12) 0.0467(4) Uani 1 1 d . . . . . H4AC H 0.0894 0.6717 0.2293 0.056 Uiso 1 1 calc R U . . . H4BC H 0.1458 0.7689 0.1899 0.056 Uiso 1 1 calc R U . . . C5C C 0.2246(2) 0.89958(16) 0.49575(12) 0.0495(5) Uani 1 1 d . . . . . H05C H 0.2088 0.9333 0.5454 0.059 Uiso 1 1 calc R U . . . C6C C 0.1307(2) 0.87494(16) 0.42960(12) 0.0467(4) Uani 1 1 d . . . . . C7C C 0.14927(19) 0.82534(15) 0.35236(12) 0.0427(4) Uani 1 1 d . . . . . C8C C 0.2681(2) 0.80073(18) 0.34625(13) 0.0497(5) Uani 1 1 d . . . . . H08C H 0.2835 0.7675 0.2962 0.060 Uiso 1 1 calc R U . . . C9C C 0.3660(2) 0.82454(16) 0.41360(13) 0.0485(5) Uani 1 1 d . . . . . C10C C 0.3447(2) 0.87442(15) 0.48946(13) 0.0488(5) Uani 1 1 d . . . . . C11C C 0.4442(2) 0.89665(16) 0.55990(14) 0.0557(5) Uani 1 1 d . . . . . C12C C 0.5601(2) 0.86446(18) 0.54554(16) 0.0614(6) Uani 1 1 d . . . . . C13C C 0.5757(2) 0.8182(2) 0.46931(16) 0.0656(6) Uani 1 1 d . . . . . H13C H 0.6539 0.7999 0.4622 0.079 Uiso 1 1 calc R U . . . C14C C 0.6697(3) 0.8798(2) 0.61220(19) 0.0772(8) Uani 1 1 d . . . . . C15C C 0.5130(3) 0.7499(3) 0.3234(2) 0.0984(11) Uani 1 1 d . . . . . H14C H 0.5844 0.7203 0.3304 0.118 Uiso 1 1 calc R U . . . H15C H 0.4297 0.6932 0.2964 0.118 Uiso 1 1 calc R U . . . C16C C 0.5574(4) 0.8265(3) 0.2719(2) 0.1077(12) Uani 1 1 d . . . . . H16C H 0.5740 0.7922 0.2205 0.129 Uiso 1 1 calc R U . . . H17C H 0.4862 0.8550 0.2638 0.129 Uiso 1 1 calc R U . . . H18C H 0.6408 0.8821 0.2977 0.129 Uiso 1 1 calc R U . . . C17C C -0.2226(2) 0.72761(18) 0.06827(14) 0.0559(5) Uani 1 1 d . . . . . H19C H -0.2075 0.6800 0.0234 0.067 Uiso 1 1 calc R U . . . H20C H -0.2386 0.7842 0.0496 0.067 Uiso 1 1 calc R U . . . H21C H -0.3017 0.6910 0.0922 0.067 Uiso 1 1 calc R U . . . F2 F 0.51359(13) 0.39899(11) 0.47993(8) 0.0600(3) Uani 1 1 d . . . . . O1D O 0.94294(17) 0.45851(12) 0.65770(8) 0.0583(4) Uani 1 1 d . . . . . O2D O 1.17113(17) 0.45023(13) 0.70914(9) 0.0605(4) Uani 1 1 d D . . . . H2D H 1.0919(18) 0.465(2) 0.7079(17) 0.073 Uiso 1 1 d D U . . . O3D O 1.28263(19) 0.37253(16) 0.62642(11) 0.0770(5) Uani 1 1 d . . . . . N1D N 0.47793(15) 0.36174(12) 0.16830(10) 0.0440(4) Uani 1 1 d . . . . . H0D H 0.3905 0.3026 0.1520 0.053 Uiso 1 1 calc R U . . . N2D N 0.55414(18) 0.31945(15) 0.31991(10) 0.0549(5) Uani 1 1 d . . . . . N3D N 0.99784(15) 0.32523(12) 0.42999(9) 0.0413(3) Uani 1 1 d . . . . . C1D C 0.4462(2) 0.3648(2) 0.31276(13) 0.0583(6) Uani 1 1 d . . . . . H1AD H 0.4470 0.4106 0.3641 0.070 Uiso 1 1 calc R U . . . H1BD H 0.3566 0.3090 0.3004 0.070 Uiso 1 1 calc R U . . . C2D C 0.4667(2) 0.42620(17) 0.24768(13) 0.0527(5) Uani 1 1 d . . . . . H2AD H 0.3894 0.4502 0.2416 0.063 Uiso 1 1 calc R U . . . H2BD H 0.5503 0.4875 0.2636 0.063 Uiso 1 1 calc R U . . . C3D C 0.59007(19) 0.31804(16) 0.17763(13) 0.0469(4) Uani 1 1 d . . . . . H3AD H 0.6786 0.3747 0.1931 0.056 Uiso 1 1 calc R U . . . H3BD H 0.5943 0.2737 0.1267 0.056 Uiso 1 1 calc R U . . . C4D C 0.5601(2) 0.25482(16) 0.24200(12) 0.0500(5) Uani 1 1 d . . . . . H4AD H 0.4725 0.1974 0.2254 0.060 Uiso 1 1 calc R U . . . H4BD H 0.6317 0.2250 0.2478 0.060 Uiso 1 1 calc R U . . . C5D C 0.7325(2) 0.41103(14) 0.52861(11) 0.0427(4) Uani 1 1 d . . . . . H05D H 0.7165 0.4405 0.5797 0.051 Uiso 1 1 calc R U . . . C6D C 0.63575(19) 0.38730(14) 0.46449(12) 0.0424(4) Uani 1 1 d . . . . . C7D C 0.65477(19) 0.34679(14) 0.38408(11) 0.0394(4) Uani 1 1 d . . . . . C8D C 0.77918(18) 0.32995(14) 0.37458(11) 0.0382(4) Uani 1 1 d . . . . . H08D H 0.7977 0.3058 0.3227 0.046 Uiso 1 1 calc R U . . . C9D C 0.87758(18) 0.34821(13) 0.44057(10) 0.0366(4) Uani 1 1 d . . . . . C10D C 0.85647(19) 0.39182(13) 0.51893(11) 0.0391(4) Uani 1 1 d . . . . . C11D C 0.9578(2) 0.41407(14) 0.58746(11) 0.0436(4) Uani 1 1 d . . . . . C12D C 1.0746(2) 0.38399(15) 0.57138(12) 0.0447(4) Uani 1 1 d . . . . . C13D C 1.0889(2) 0.34137(15) 0.49421(12) 0.0453(4) Uani 1 1 d . . . . . H13D H 1.1663 0.3224 0.4856 0.054 Uiso 1 1 calc R U . . . C14D C 1.1855(2) 0.40009(17) 0.63669(13) 0.0535(5) Uani 1 1 d . . . . . C15D C 1.0254(2) 0.27772(17) 0.34914(12) 0.0492(5) Uani 1 1 d . . . . . H14D H 1.1239 0.2911 0.3497 0.059 Uiso 1 1 calc R U . . . H15D H 0.9986 0.3110 0.3091 0.059 Uiso 1 1 calc R U . . . C16D C 0.9483(3) 0.16079(19) 0.32475(13) 0.0591(5) Uani 1 1 d . . . . . H16D H 0.9693 0.1337 0.2723 0.071 Uiso 1 1 calc R U . . . H17D H 0.9760 0.1273 0.3636 0.071 Uiso 1 1 calc R U . . . H18D H 0.8506 0.1471 0.3229 0.071 Uiso 1 1 calc R U . . . C17D C 0.4988(3) 0.42308(19) 0.10377(16) 0.0649(6) Uani 1 1 d . . . . . H19D H 0.5859 0.4800 0.1171 0.078 Uiso 1 1 calc R U . . . H20D H 0.4254 0.4505 0.0998 0.078 Uiso 1 1 calc R U . . . H21D H 0.4986 0.3782 0.0529 0.078 Uiso 1 1 calc R U . . . O1W O 0.2561(3) 0.5401(2) 0.0484(3) 0.1433(12) Uani 1 1 d D . . . . H11W H 0.260(5) 0.555(3) 0.1056(7) 0.172 Uiso 1 1 d D U . . . H12W H 0.315(4) 0.600(2) 0.036(2) 0.172 Uiso 1 1 d D U . . . O2WA O -0.0163(12) 0.4750(9) 0.0995(9) 0.120(4) Uiso 0.255(3) 1 d . . . . . O2WB O -0.0238(7) 0.4612(5) 0.0474(5) 0.120(3) Uiso 0.453(8) 1 d . . . . . O3WA O 0.2417(6) 0.5444(4) 0.2228(3) 0.1039(16) Uiso 0.470(3) 1 d . . . . . O3WB O 0.1378(7) 0.5043(5) 0.1935(4) 0.104(3) Uiso 0.383(7) 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 O1A 0.0269(6) 0.0369(7) 0.0733(9) 0.0046(6) 0.0043(6) 0.0108(5) O2A 0.0452(8) 0.0409(7) 0.0946(11) 0.0125(7) 0.0142(7) 0.0243(6) O3A 0.0246(6) 0.0399(7) 0.0598(8) 0.0135(6) 0.0067(5) 0.0122(5) N1A 0.0255(7) 0.0329(7) 0.0515(8) 0.0076(6) 0.0051(6) 0.0134(6) N3A 0.0252(7) 0.0396(8) 0.0524(8) 0.0083(6) 0.0037(6) 0.0155(6) C2A 0.0268(8) 0.0376(9) 0.0404(9) 0.0064(7) 0.0032(6) 0.0123(7) C4A 0.0368(9) 0.0391(9) 0.0491(10) 0.0100(8) 0.0083(7) 0.0182(8) C5A 0.0315(8) 0.0329(9) 0.0525(10) 0.0076(7) 0.0067(7) 0.0101(7) C6A 0.0251(7) 0.0375(9) 0.0385(8) 0.0086(7) 0.0040(6) 0.0100(7) O1B 0.0266(6) 0.0402(7) 0.0720(9) 0.0108(6) 0.0015(6) 0.0083(5) O2B 0.0517(9) 0.0511(9) 0.1001(12) -0.0105(8) -0.0042(8) 0.0305(7) O3B 0.0234(6) 0.0424(7) 0.0648(8) 0.0045(6) -0.0018(5) 0.0097(5) N1B 0.0242(7) 0.0343(7) 0.0508(8) 0.0066(6) 0.0006(6) 0.0121(6) N3B 0.0243(7) 0.0438(8) 0.0480(8) 0.0042(6) 0.0001(6) 0.0156(6) C2B 0.0253(8) 0.0395(9) 0.0404(9) 0.0078(7) -0.0001(6) 0.0118(7) C4B 0.0386(9) 0.0448(10) 0.0495(10) -0.0008(8) -0.0034(8) 0.0209(8) C5B 0.0332(9) 0.0341(9) 0.0595(11) 0.0011(8) -0.0043(8) 0.0084(7) C6B 0.0252(8) 0.0398(9) 0.0422(9) 0.0060(7) -0.0027(6) 0.0105(7) F1 0.0583(8) 0.0864(10) 0.0594(7) 0.0111(7) 0.0135(6) 0.0384(7) O1C 0.0778(12) 0.0724(11) 0.0637(11) 0.0090(9) -0.0140(9) 0.0098(10) O2C 0.0821(14) 0.0846(15) 0.0881(15) 0.0270(12) -0.0298(12) 0.0017(11) O3C 0.0677(13) 0.130(2) 0.1250(19) 0.0470(15) -0.0266(12) 0.0341(13) N1C 0.0339(8) 0.0411(8) 0.0499(9) 0.0166(7) 0.0046(6) 0.0106(6) N2C 0.0416(8) 0.0448(9) 0.0480(8) 0.0127(7) 0.0052(7) 0.0212(7) N3C 0.0517(11) 0.0797(14) 0.0697(12) 0.0260(10) 0.0007(9) 0.0337(10) C1C 0.0536(11) 0.0454(10) 0.0519(11) 0.0116(8) 0.0037(9) 0.0250(9) C2C 0.0445(10) 0.0539(12) 0.0567(11) 0.0160(9) 0.0085(9) 0.0268(9) C3C 0.0529(11) 0.0411(10) 0.0541(11) 0.0125(8) 0.0050(9) 0.0189(9) C4C 0.0504(11) 0.0492(11) 0.0504(10) 0.0149(9) 0.0081(8) 0.0278(9) C5C 0.0539(12) 0.0436(10) 0.0481(11) 0.0126(8) 0.0077(9) 0.0116(9) C6C 0.0430(10) 0.0471(11) 0.0537(11) 0.0163(9) 0.0096(8) 0.0171(9) C7C 0.0401(10) 0.0447(10) 0.0481(10) 0.0191(8) 0.0068(8) 0.0157(8) C8C 0.0475(11) 0.0612(13) 0.0499(11) 0.0202(9) 0.0076(9) 0.0265(10) C9C 0.0439(10) 0.0505(11) 0.0572(12) 0.0229(9) 0.0046(9) 0.0185(9) C10C 0.0460(11) 0.0420(10) 0.0568(11) 0.0224(9) 0.0009(9) 0.0075(9) C11C 0.0568(13) 0.0415(11) 0.0574(13) 0.0173(9) -0.0067(10) 0.0005(9) C12C 0.0461(12) 0.0512(12) 0.0812(16) 0.0318(12) -0.0119(11) 0.0024(10) C13C 0.0515(13) 0.0706(16) 0.0805(17) 0.0321(13) -0.0024(11) 0.0213(12) C14C 0.0631(16) 0.0691(16) 0.087(2) 0.0346(15) -0.0200(14) 0.0009(13) C15C 0.087(2) 0.158(3) 0.091(2) 0.027(2) 0.0107(16) 0.095(2) C16C 0.089(2) 0.158(4) 0.098(2) 0.031(2) 0.0315(19) 0.068(2) C17C 0.0425(11) 0.0544(12) 0.0655(13) 0.0163(10) -0.0063(9) 0.0100(9) F2 0.0528(7) 0.0732(8) 0.0633(7) 0.0091(6) 0.0121(6) 0.0369(6) O1D 0.0671(10) 0.0620(9) 0.0391(7) 0.0071(6) -0.0006(6) 0.0169(8) O2D 0.0628(10) 0.0577(9) 0.0491(8) 0.0155(7) -0.0132(7) 0.0059(8) O3D 0.0644(11) 0.0872(13) 0.0770(11) 0.0074(9) -0.0244(9) 0.0334(10) N1D 0.0323(8) 0.0362(8) 0.0581(9) 0.0028(7) -0.0034(6) 0.0103(6) N2D 0.0506(10) 0.0646(11) 0.0523(9) -0.0061(8) -0.0096(8) 0.0364(9) N3D 0.0359(8) 0.0462(9) 0.0421(8) 0.0113(6) 0.0011(6) 0.0141(7) C1D 0.0485(11) 0.0785(15) 0.0549(12) 0.0031(11) -0.0025(9) 0.0387(11) C2D 0.0418(10) 0.0505(11) 0.0647(12) -0.0050(9) -0.0073(9) 0.0262(9) C3D 0.0305(9) 0.0439(10) 0.0594(11) -0.0040(8) -0.0027(8) 0.0139(8) C4D 0.0451(10) 0.0486(11) 0.0534(11) -0.0065(9) -0.0122(8) 0.0247(9) C5D 0.0498(11) 0.0364(9) 0.0415(9) 0.0079(7) 0.0073(8) 0.0146(8) C6D 0.0394(9) 0.0364(9) 0.0531(10) 0.0086(8) 0.0080(8) 0.0160(8) C7D 0.0402(9) 0.0338(9) 0.0438(9) 0.0060(7) -0.0002(7) 0.0144(7) C8D 0.0383(9) 0.0371(9) 0.0386(9) 0.0061(7) 0.0019(7) 0.0143(7) C9D 0.0353(9) 0.0331(8) 0.0403(9) 0.0109(7) 0.0023(7) 0.0093(7) C10D 0.0421(9) 0.0319(8) 0.0408(9) 0.0109(7) 0.0022(7) 0.0084(7) C11D 0.0496(11) 0.0352(9) 0.0398(9) 0.0123(7) 0.0001(8) 0.0054(8) C12D 0.0432(10) 0.0384(9) 0.0469(10) 0.0145(8) -0.0059(8) 0.0054(8) C13D 0.0373(9) 0.0455(10) 0.0523(11) 0.0156(8) -0.0018(8) 0.0116(8) C14D 0.0528(12) 0.0447(11) 0.0549(12) 0.0160(9) -0.0125(9) 0.0062(9) C15D 0.0424(10) 0.0667(13) 0.0441(10) 0.0132(9) 0.0068(8) 0.0256(10) C16D 0.0663(14) 0.0654(14) 0.0498(11) 0.0056(10) 0.0042(10) 0.0326(12) C17D 0.0687(15) 0.0519(13) 0.0742(15) 0.0190(11) 0.0076(12) 0.0185(11) O1W 0.124(2) 0.0810(17) 0.233(4) 0.050(2) 0.064(3) 0.0320(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' 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 C2A N1A C6A 123.98(14) . . C2A N1A H1A 118.0 . . C6A N1A H1A 118.0 . . C2A N3A C4A 125.05(14) . . C2A N3A H3A 117.5 . . C4A N3A H3A 117.5 . . O1A C2A N3A 122.57(15) . . O1A C2A N1A 121.56(15) . . N3A C2A N1A 115.87(15) . . O2A C4A N3A 117.63(16) . . O2A C4A C5A 126.55(17) . . N3A C4A C5A 115.82(15) . . C6A C5A C4A 121.56(16) . . C6A C5A H5A 119.2 . . C4A C5A H5A 119.2 . . O3A C6A C5A 126.34(16) . . O3A C6A N1A 116.02(15) . . C5A C6A N1A 117.64(14) . . C2B N1B C6B 124.20(14) . . C2B N1B H1B 117.9 . . C6B N1B H1B 117.9 . . C2B N3B C4B 125.26(14) . . C2B N3B H3B 117.4 . . C4B N3B H3B 117.4 . . O1B C2B N3B 122.66(15) . . O1B C2B N1B 121.63(15) . . N3B C2B N1B 115.68(15) . . O2B C4B N3B 117.63(17) . . O2B C4B C5B 126.19(19) . . N3B C4B C5B 116.15(16) . . C6B C5B C4B 121.45(17) . . C6B C5B H5B 119.3 . . C4B C5B H5B 119.3 . . O3B C6B N1B 116.38(15) . . O3B C6B C5B 126.38(16) . . N1B C6B C5B 117.23(15) . . C14C O2C H2C 132(3) . . C2C N1C C3C 108.64(14) . . C2C N1C C17C 112.44(15) . . C3C N1C C17C 111.47(15) . . C2C N1C H0C 108.0 . . C3C N1C H0C 108.0 . . C17C N1C H0C 108.0 . . C7C N2C C4C 115.36(15) . . C7C N2C C1C 116.18(16) . . C4C N2C C1C 110.47(15) . . C13C N3C C9C 119.6(2) . . C13C N3C C15C 119.6(2) . . C9C N3C C15C 120.75(18) . . N2C C1C C2C 109.68(16) . . N2C C1C H1AC 109.7 . . C2C C1C H1AC 109.7 . . N2C C1C H1BC 109.7 . . C2C C1C H1BC 109.7 . . H1AC C1C H1BC 108.2 . . N1C C2C C1C 111.28(15) . . N1C C2C H2AC 109.4 . . C1C C2C H2AC 109.4 . . N1C C2C H2BC 109.4 . . C1C C2C H2BC 109.4 . . H2AC C2C H2BC 108.0 . . N1C C3C C4C 111.10(16) . . N1C C3C H3AC 109.4 . . C4C C3C H3AC 109.4 . . N1C C3C H3BC 109.4 . . C4C C3C H3BC 109.4 . . H3AC C3C H3BC 108.0 . . N2C C4C C3C 111.61(16) . . N2C C4C H4AC 109.3 . . C3C C4C H4AC 109.3 . . N2C C4C H4BC 109.3 . . C3C C4C H4BC 109.3 . . H4AC C4C H4BC 108.0 . . C6C C5C C10C 120.36(19) . . C6C C5C H05C 119.8 . . C10C C5C H05C 119.8 . . F1 C6C C5C 118.81(18) . . F1 C6C C7C 118.45(17) . . C5C C6C C7C 122.70(18) . . C8C C7C N2C 121.83(18) . . C8C C7C C6C 116.84(17) . . N2C C7C C6C 121.21(17) . . C7C C8C C9C 121.63(19) . . C7C C8C H08C 119.2 . . C9C C8C H08C 119.2 . . N3C C9C C10C 120.11(18) . . N3C C9C C8C 119.82(19) . . C10C C9C C8C 120.07(18) . . C5C C10C C9C 118.39(18) . . C5C C10C C11C 121.4(2) . . C9C C10C C11C 120.2(2) . . O1C C11C C12C 123.7(2) . . O1C C11C C10C 120.6(2) . . C12C C11C C10C 115.7(2) . . C13C C12C C11C 120.9(2) . . C13C C12C C14C 117.2(2) . . C11C C12C C14C 122.0(3) . . N3C C13C C12C 123.5(2) . . N3C C13C H13C 118.2 . . C12C C13C H13C 118.2 . . O3C C14C O2C 121.4(3) . . O3C C14C C12C 124.5(3) . . O2C C14C C12C 114.1(3) . . C16C C15C N3C 112.4(3) . . C16C C15C H14C 109.1 . . N3C C15C H14C 109.1 . . C16C C15C H15C 109.1 . . N3C C15C H15C 109.1 . . H14C C15C H15C 107.8 . . C15C C16C H16C 109.5 . . C15C C16C H17C 109.5 . . H16C C16C H17C 109.5 . . C15C C16C H18C 109.5 . . H16C C16C H18C 109.5 . . H17C C16C H18C 109.5 . . N1C C17C H19C 109.5 . . N1C C17C H20C 109.5 . . H19C C17C H20C 109.5 . . N1C C17C H21C 109.5 . . H19C C17C H21C 109.5 . . H20C C17C H21C 109.5 . . C14D O2D H2D 111.2(18) . . C3D N1D C17D 111.76(17) . . C3D N1D C2D 110.12(14) . . C17D N1D C2D 111.56(16) . . C3D N1D H0D 107.7 . . C17D N1D H0D 107.7 . . C2D N1D H0D 107.7 . . C7D N2D C4D 122.11(15) . . C7D N2D C1D 126.52(16) . . C4D N2D C1D 110.29(15) . . C13D N3D C9D 119.96(16) . . C13D N3D C15D 118.39(16) . . C9D N3D C15D 121.57(14) . . N2D C1D C2D 111.57(18) . . N2D C1D H1AD 109.3 . . C2D C1D H1AD 109.3 . . N2D C1D H1BD 109.3 . . C2D C1D H1BD 109.3 . . H1AD C1D H1BD 108.0 . . N1D C2D C1D 111.67(17) . . N1D C2D H2AD 109.3 . . C1D C2D H2AD 109.3 . . N1D C2D H2BD 109.3 . . C1D C2D H2BD 109.3 . . H2AD C2D H2BD 107.9 . . N1D C3D C4D 108.77(16) . . N1D C3D H3AD 109.9 . . C4D C3D H3AD 109.9 . . N1D C3D H3BD 109.9 . . C4D C3D H3BD 109.9 . . H3AD C3D H3BD 108.3 . . N2D C4D C3D 111.46(17) . . N2D C4D H4AD 109.3 . . C3D C4D H4AD 109.3 . . N2D C4D H4BD 109.3 . . C3D C4D H4BD 109.3 . . H4AD C4D H4BD 108.0 . . C6D C5D C10D 120.87(17) . . C6D C5D H05D 119.6 . . C10D C5D H05D 119.6 . . C5D C6D F2 117.26(17) . . C5D C6D C7D 123.09(17) . . F2 C6D C7D 119.57(16) . . N2D C7D C8D 121.47(16) . . N2D C7D C6D 122.65(17) . . C8D C7D C6D 115.76(16) . . C7D C8D C9D 122.20(16) . . C7D C8D H08D 118.9 . . C9D C8D H08D 118.9 . . N3D C9D C8D 121.12(16) . . N3D C9D C10D 118.88(15) . . C8D C9D C10D 120.00(16) . . C5D C10D C9D 117.91(16) . . C5D C10D C11D 120.99(17) . . C9D C10D C11D 121.09(17) . . O1D C11D C12D 122.51(17) . . O1D C11D C10D 121.46(19) . . C12D C11D C10D 116.03(17) . . C13D C12D C11D 120.11(17) . . C13D C12D C14D 118.12(19) . . C11D C12D C14D 121.75(19) . . N3D C13D C12D 123.80(18) . . N3D C13D H13D 118.1 . . C12D C13D H13D 118.1 . . O3D C14D O2D 121.07(19) . . O3D C14D C12D 124.0(2) . . O2D C14D C12D 115.0(2) . . N3D C15D C16D 112.50(16) . . N3D C15D H14D 109.1 . . C16D C15D H14D 109.1 . . N3D C15D H15D 109.1 . . C16D C15D H15D 109.1 . . H14D C15D H15D 107.8 . . C15D C16D H16D 109.5 . . C15D C16D H17D 109.5 . . H16D C16D H17D 109.5 . . C15D C16D H18D 109.5 . . H16D C16D H18D 109.5 . . H17D C16D H18D 109.5 . . N1D C17D H19D 109.5 . . N1D C17D H20D 109.5 . . H19D C17D H20D 109.5 . . N1D C17D H21D 109.5 . . H19D C17D H21D 109.5 . . H20D C17D H21D 109.5 . . H11W O1W H12W 105.8(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1A C2A 1.231(2) . O2A C4A 1.247(2) . O3A C6A 1.2764(19) . N1A C2A 1.364(2) . N1A C6A 1.387(2) . N1A H1A 0.8600 . N3A C2A 1.358(2) . N3A C4A 1.394(2) . N3A H3A 0.8600 . C4A C5A 1.403(2) . C5A C6A 1.378(2) . C5A H5A 0.9300 . O1B C2B 1.233(2) . O2B C4B 1.249(2) . O3B C6B 1.275(2) . N1B C2B 1.366(2) . N1B C6B 1.385(2) . N1B H1B 0.8600 . N3B C2B 1.355(2) . N3B C4B 1.387(2) . N3B H3B 0.8600 . C4B C5B 1.398(3) . C5B C6B 1.386(3) . C5B H5B 0.9300 . F1 C6C 1.355(2) . O1C C11C 1.263(3) . O2C C14C 1.327(4) . O2C H2C 0.906(10) . O3C C14C 1.191(4) . N1C C2C 1.484(3) . N1C C3C 1.487(2) . N1C C17C 1.489(2) . N1C H0C 0.9800 . N2C C7C 1.405(2) . N2C C4C 1.458(2) . N2C C1C 1.473(2) . N3C C13C 1.329(3) . N3C C9C 1.400(3) . N3C C15C 1.497(4) . C1C C2C 1.507(3) . C1C H1AC 0.9700 . C1C H1BC 0.9700 . C2C H2AC 0.9700 . C2C H2BC 0.9700 . C3C C4C 1.501(3) . C3C H3AC 0.9700 . C3C H3BC 0.9700 . C4C H4AC 0.9700 . C4C H4BC 0.9700 . C5C C6C 1.360(3) . C5C C10C 1.400(3) . C5C H05C 0.9300 . C6C C7C 1.408(3) . C7C C8C 1.382(3) . C8C C9C 1.402(3) . C8C H08C 0.9300 . C9C C10C 1.400(3) . C10C C11C 1.454(3) . C11C C12C 1.424(4) . C12C C13C 1.368(4) . C12C C14C 1.496(3) . C13C H13C 0.9300 . C15C C16C 1.474(5) . C15C H14C 0.9700 . C15C H15C 0.9700 . C16C H16C 0.9600 . C16C H17C 0.9600 . C16C H18C 0.9600 . C17C H19C 0.9600 . C17C H20C 0.9600 . C17C H21C 0.9600 . F2 C6D 1.354(2) . O1D C11D 1.271(2) . O2D C14D 1.329(3) . O2D H2D 0.910(10) . O3D C14D 1.195(3) . N1D C3D 1.491(2) . N1D C17D 1.493(3) . N1D C2D 1.496(3) . N1D H0D 0.9800 . N2D C7D 1.373(2) . N2D C4D 1.461(3) . N2D C1D 1.462(2) . N3D C13D 1.339(2) . N3D C9D 1.392(2) . N3D C15D 1.484(2) . C1D C2D 1.501(3) . C1D H1AD 0.9700 . C1D H1BD 0.9700 . C2D H2AD 0.9700 . C2D H2BD 0.9700 . C3D C4D 1.509(3) . C3D H3AD 0.9700 . C3D H3BD 0.9700 . C4D H4AD 0.9700 . C4D H4BD 0.9700 . C5D C6D 1.354(3) . C5D C10D 1.402(3) . C5D H05D 0.9300 . C6D C7D 1.418(3) . C7D C8D 1.391(2) . C8D C9D 1.403(2) . C8D H08D 0.9300 . C9D C10D 1.407(3) . C10D C11D 1.442(3) . C11D C12D 1.422(3) . C12D C13D 1.363(3) . C12D C14D 1.486(3) . C13D H13D 0.9300 . C15D C16D 1.511(3) . C15D H14D 0.9700 . C15D H15D 0.9700 . C16D H16D 0.9600 . C16D H17D 0.9600 . C16D H18D 0.9600 . C17D H19D 0.9600 . C17D H20D 0.9600 . C17D H21D 0.9600 . O1W H11W 0.948(10) . O1W H12W 0.919(10) . O2WA O2WB 0.862(12) . O3WA O3WB 1.075(7) .