#------------------------------------------------------------------------------ #$Date: 2019-08-20 05:33:50 +0300 (Tue, 20 Aug 2019) $ #$Revision: 217604 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058764.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_7058764 loop_ _publ_author_name 'Ribeiro, N\'adia' 'Galv\~ao, Adelino M.' 'Gomes, Clara S. B.' 'Ramos, Helena' 'Pinheiro, Rute' 'Saraiva, Lucilia' 'Ntungwee, Epole' 'Isca, Vera M.S.' 'Rijo, Patr\'icia' 'Cavaco, Isabel' 'Ramilo-Gomes, Filipa' 'Guedes, Rita Cardoso' 'Pessoa, Jo\~ao Costa' 'Correia, Isabel' _publ_section_title ; Naphthoylhydrazones: coordination to metal ions and biological screening ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ01816F _journal_year 2019 _chemical_formula_moiety 'C16 H12 N2 O3' _chemical_formula_sum 'C16 H12 N2 O3' _chemical_formula_weight 280.28 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-03-20 deposited with the CCDC. 2019-08-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.231(11) _cell_angle_gamma 90 _cell_formula_units_Z 12 _cell_length_a 12.099(3) _cell_length_b 17.373(6) _cell_length_c 20.130(6) _cell_measurement_reflns_used 2829 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 18.62 _cell_measurement_theta_min 2.34 _cell_volume 4228(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution SIR2019 _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_unetI/netI 0.0832 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 28193 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.704 _diffrn_reflns_theta_min 2.317 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_correction_T_min 0.7110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/5' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1752 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.238 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 540 _refine_ls_number_reflns 8014 _refine_ls_number_restraints 45 _refine_ls_restrained_S_all 0.940 _refine_ls_R_factor_all 0.1746 _refine_ls_R_factor_gt 0.0670 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1049P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1754 _refine_ls_wR_factor_ref 0.2128 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3258 _reflns_number_total 8014 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj01816f2.cif _cod_data_source_block HL2 _cod_database_code 7058764 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_min 0.964 _shelx_estimated_absorpt_t_max 0.982 _shelx_res_file ; TITL SIR2018 run in space group P 21/c shelx.res created by SHELXL-2018/3 at 15:43:17 on 19-Mar-2019 CELL 0.71073 12.0986 17.3730 20.1304 90.000 92.231 90.000 ZERR 12.00 0.0030 0.0056 0.0057 0.000 0.011 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 192 144 24 36 MERG 2 OMIT 0.00 180.00 OMIT 0 1 1 OMIT 0 0 2 OMIT 1 1 0 OMIT 1 0 0 OMIT -1 1 1 OMIT 0 2 0 EQIV $1 x-1, y, z HTAB C5A O2C_$1 HTAB C5B O2A HTAB C5C O2B DFIX 0.870 0.020 H20A N2A DFIX 0.870 0.020 H20B N2B SIMU 0.040 0.080 1.700 C4A C3A EADP C4A C3A ISOR 0.10 0.20 O1A DELU 0.010 0.010 O1A C4A C1A SIMU 0.040 0.080 1.700 O1A C4A C1A DFIX 0.900 0.020 H9C C9C DFIX 0.900 0.020 C12A H12A SIMU 0.040 0.080 1.700 C13A C11A C12A EADP C13A C11A C12A FMAP 2 PLAN 25 SIZE 0.200 0.200 0.400 ACTA BOND $H CONF BUMP 0.04000 L.S. 10 TEMP 23.00 WGHT 0.104900 FVAR 0.08535 O1A 4 0.018598 0.169042 0.686862 11.00000 0.09576 0.09982 = 0.10324 0.01129 -0.00594 -0.02361 O2A 4 -0.005614 -0.017251 0.865548 11.00000 0.05076 0.10669 = 0.07804 0.00506 -0.00838 -0.00877 O3A 4 -0.042361 -0.081296 0.978015 11.00000 0.08491 0.12548 = 0.07981 0.01473 -0.02999 -0.01346 AFIX 83 H30A 2 -0.012307 -0.051941 0.952418 11.00000 -1.50000 AFIX 0 N1A 3 -0.083435 0.050883 0.756566 11.00000 0.06192 0.06475 = 0.06258 0.00047 0.00088 -0.00528 N2A 3 9.853133 9.998872 10.790627 11.00000 0.05270 0.06939 = 0.06493 0.00765 -0.00150 -0.00653 C1A 1 -0.080312 0.138617 0.665622 11.00000 0.08384 0.07483 = 0.06945 -0.00371 -0.01480 -0.01789 C2A 1 -0.119285 0.176049 0.611667 11.00000 0.14243 0.11650 = 0.08614 0.02378 -0.05155 -0.02991 AFIX 43 H2A 2 -0.186215 0.167784 0.588472 11.00000 -1.20000 AFIX 0 C3A 1 -0.036215 0.231568 0.597119 11.00000 0.15939 0.10305 = 0.10359 0.03401 0.00840 -0.03573 AFIX 43 H3A 2 -0.037384 0.265039 0.561045 11.00000 -1.20000 AFIX 0 C4A 1 0.041500 0.226608 0.643777 11.00000 0.15939 0.10305 = 0.10359 0.03401 0.00840 -0.03573 AFIX 43 H4A 2 0.103720 0.258016 0.647069 11.00000 -1.20000 AFIX 0 C5A 1 -0.130540 0.079659 0.705118 11.00000 0.07309 0.07644 = 0.07257 0.00117 -0.00956 -0.01973 AFIX 43 H5A 2 -0.200691 0.062058 0.692133 11.00000 -1.20000 AFIX 0 C6A 1 -0.102302 -0.032461 0.845997 11.00000 0.04488 0.07179 = 0.05858 -0.01007 0.00232 -0.00017 C7A 1 -0.170176 -0.087645 0.882625 11.00000 0.04926 0.06568 = 0.05493 0.00413 0.00015 0.00877 C8A 1 -0.135842 -0.109800 0.948293 11.00000 0.06503 0.08134 = 0.07136 0.00712 -0.00329 0.00368 C9A 1 -0.197210 -0.159417 0.982867 11.00000 0.09488 0.10466 = 0.07913 0.02467 -0.00503 0.00153 AFIX 43 H9A 2 -0.173062 -0.173513 1.025575 11.00000 -1.20000 AFIX 0 C10A 1 -0.296164 -0.190277 0.956297 11.00000 0.09124 0.09551 = 0.09917 0.03236 0.00306 -0.01211 C11A 1 -0.360697 -0.242174 0.992032 11.00000 0.15210 0.20776 = 0.17303 0.08638 -0.00969 -0.08111 AFIX 43 H11A 2 -0.338398 -0.257848 1.034649 11.00000 -1.20000 AFIX 0 C12A 1 9.543859 9.731251 10.962811 11.00000 0.15210 0.20776 = 0.17303 0.08638 -0.00969 -0.08111 C13A 1 -0.492172 -0.250191 0.898203 11.00000 0.15210 0.20776 = 0.17303 0.08638 -0.00969 -0.08111 AFIX 43 H13A 2 -0.556944 -0.271142 0.879534 11.00000 -1.20000 AFIX 0 C14A 1 -0.430012 -0.200681 0.863348 11.00000 0.08603 0.11898 = 0.11998 0.02537 -0.01225 -0.03661 AFIX 43 H14A 2 -0.452848 -0.187303 0.820235 11.00000 -1.20000 AFIX 0 C15A 1 -0.331613 -0.169181 0.891204 11.00000 0.06250 0.08323 = 0.08872 0.01526 -0.00025 -0.00604 C16A 1 -0.265494 -0.118402 0.855928 11.00000 0.05344 0.07189 = 0.06597 0.00674 -0.00242 0.00297 AFIX 43 H16A 2 -0.287564 -0.105216 0.812643 11.00000 -1.20000 AFIX 0 O1B 4 0.366696 -0.136440 0.734458 11.00000 0.07930 0.08299 = 0.11068 -0.01325 0.00936 0.00702 O2B 4 0.331383 0.133899 0.788186 11.00000 0.05755 0.08145 = 0.10416 -0.00688 0.01050 -0.01147 O3B 4 0.297574 0.277644 0.782274 11.00000 0.11357 0.08556 = 0.15044 0.00099 0.01747 -0.02605 AFIX 83 H30B 2 0.329752 0.236794 0.776474 11.00000 -1.50000 AFIX 0 N1B 3 0.256450 -0.008721 0.783262 11.00000 0.05615 0.06860 = 0.07171 -0.00402 -0.00040 0.00071 N2B 3 10.190413 10.051650 10.802823 11.00000 0.04894 0.06341 = 0.07997 -0.00667 0.00308 0.00216 C1B 1 0.265199 -0.142133 0.760253 11.00000 0.06690 0.07607 = 0.07892 -0.00329 0.00429 -0.00195 C2B 1 0.230397 -0.214955 0.756188 11.00000 0.10242 0.06792 = 0.14631 -0.00346 0.01026 0.00220 AFIX 43 H2B 2 0.162563 -0.233538 0.769350 11.00000 -1.20000 AFIX 0 C3B 1 0.314662 -0.258248 0.728493 11.00000 0.14450 0.07731 = 0.14364 -0.01346 -0.01446 0.00918 AFIX 43 H3B 2 0.314650 -0.311059 0.720937 11.00000 -1.20000 AFIX 0 C4B 1 0.393299 -0.209685 0.715381 11.00000 0.10296 0.10738 = 0.11383 -0.02440 0.00016 0.04058 AFIX 43 H4B 2 0.458841 -0.223058 0.695659 11.00000 -1.20000 AFIX 0 C5B 1 0.210502 -0.074029 0.781545 11.00000 0.05985 0.06974 = 0.07630 0.00044 0.00386 0.00130 AFIX 43 H5B 2 0.137888 -0.077974 0.794713 11.00000 -1.20000 AFIX 0 C6B 1 0.233966 0.122330 0.803842 11.00000 0.05329 0.06989 = 0.05732 -0.00071 -0.00936 -0.00239 C7B 1 0.163916 0.186703 0.823533 11.00000 0.06180 0.06514 = 0.05840 -0.00601 -0.01497 0.00567 C8B 1 0.200480 0.263898 0.809342 11.00000 0.09291 0.06685 = 0.08202 -0.00769 -0.02295 0.00612 C9B 1 0.132933 0.323501 0.823464 11.00000 0.11427 0.08376 = 0.12263 -0.01182 -0.03690 0.01146 AFIX 43 H9B 2 0.155318 0.372961 0.812516 11.00000 -1.20000 AFIX 0 C10B 1 0.033536 0.314880 0.852968 11.00000 0.10578 0.08142 = 0.11086 -0.04135 -0.05478 0.03477 C11B 1 -0.037892 0.376338 0.868502 11.00000 0.14681 0.12030 = 0.18236 -0.06863 -0.08795 0.06252 AFIX 43 H11B 2 -0.019934 0.426667 0.857459 11.00000 -1.20000 AFIX 0 C12B 1 -0.133901 0.360766 0.900034 11.00000 0.12772 0.21737 = 0.19554 -0.12078 -0.06434 0.09336 AFIX 43 H12B 2 -0.178535 0.402170 0.910779 11.00000 -1.20000 AFIX 0 C13B 1 -0.168888 0.288009 0.916922 11.00000 0.10428 0.23102 = 0.17531 -0.08808 -0.02593 0.05773 AFIX 43 H13B 2 -0.235576 0.280573 0.937478 11.00000 -1.20000 AFIX 0 C14B 1 -0.101458 0.226493 0.902257 11.00000 0.08174 0.18278 = 0.11911 -0.05543 -0.00912 0.04434 AFIX 43 H14B 2 -0.121929 0.176813 0.913818 11.00000 -1.20000 AFIX 0 C15B 1 -0.002141 0.238850 0.869951 11.00000 0.06816 0.11961 = 0.07387 -0.03307 -0.02769 0.03136 C16B 1 0.065409 0.176412 0.853890 11.00000 0.06649 0.08164 = 0.06716 -0.01192 -0.01307 0.00928 AFIX 43 H16B 2 0.042814 0.126775 0.864089 11.00000 -1.20000 AFIX 0 O1C 4 0.712517 0.059165 0.937805 11.00000 0.08018 0.18931 = 0.10431 -0.05262 -0.02448 0.03149 O2C 4 0.651862 -0.027334 0.707951 11.00000 0.05146 0.09698 = 0.07397 -0.01253 -0.00244 0.00777 O3C 4 0.577095 -0.113774 0.609064 11.00000 0.13585 0.20511 = 0.14665 -0.10147 -0.05291 0.08821 AFIX 83 H30C 2 0.612325 -0.106598 0.644142 11.00000 -1.50000 AFIX 0 N1C 3 0.589762 0.039921 0.819320 11.00000 0.05386 0.08659 = 0.06564 -0.01153 -0.00335 0.00459 N2C 3 10.518730 10.032743 10.764248 11.00000 0.04919 0.09869 = 0.05804 -0.01055 -0.00412 0.00283 C1C 1 0.604515 0.070733 0.933944 11.00000 0.06632 0.17282 = 0.06886 -0.02422 -0.00931 0.02739 C2C 1 0.569369 0.089902 0.994347 11.00000 0.10103 0.36756 = 0.07400 -0.05287 -0.01264 0.06048 AFIX 43 H2C 2 0.497102 0.101706 1.004778 11.00000 -1.20000 AFIX 0 C3C 1 0.743990 0.069626 1.003573 11.00000 0.12207 0.24996 = 0.11466 -0.07368 -0.06156 0.06432 AFIX 43 H3C 2 0.815866 0.063664 1.020894 11.00000 -1.20000 AFIX 0 C4C 1 0.660490 0.088835 1.038127 11.00000 0.15514 0.34479 = 0.08468 -0.06422 -0.03852 0.08273 AFIX 43 H4C 2 0.661430 0.099760 1.083372 11.00000 -1.20000 AFIX 0 C5C 1 0.545871 0.060448 0.872089 11.00000 0.05947 0.15063 = 0.07432 -0.01517 -0.00511 0.02515 AFIX 43 H5C 2 0.470049 0.069485 0.870505 11.00000 -1.20000 AFIX 0 C6C 1 0.556526 -0.000273 0.709140 11.00000 0.04560 0.06629 = 0.06843 0.00344 0.00423 -0.00739 C7C 1 0.480567 -0.003066 0.650000 11.00000 0.04897 0.07426 = 0.05735 -0.00164 0.00236 -0.00795 C8C 1 0.495780 -0.058758 0.601653 11.00000 0.07199 0.12627 = 0.10165 -0.04091 -0.00653 0.02403 C9C 1 10.426435 9.939601 10.546068 11.00000 0.12389 0.18243 = 0.10214 -0.07326 -0.04620 0.04677 C10C 1 0.339467 -0.010219 0.536681 11.00000 0.07020 0.11025 = 0.08085 -0.00680 -0.01378 -0.00647 C11C 1 0.267176 -0.013325 0.479974 11.00000 0.12306 0.16945 = 0.10392 -0.03643 -0.04981 0.01817 AFIX 43 H11C 2 0.280755 -0.048290 0.446273 11.00000 -1.20000 AFIX 0 C12C 1 0.180251 0.032905 0.474129 11.00000 0.11745 0.17684 = 0.09707 0.00716 -0.04044 0.00198 AFIX 43 H12C 2 0.132223 0.028968 0.437077 11.00000 -1.20000 AFIX 0 C13C 1 0.160668 0.086015 0.521796 11.00000 0.12650 0.20865 = 0.11896 0.00909 -0.03856 0.06119 AFIX 43 H13C 2 0.099629 0.118421 0.517465 11.00000 -1.20000 AFIX 0 C14C 1 0.231382 0.091374 0.576086 11.00000 0.13006 0.19502 = 0.09898 -0.01398 -0.04443 0.07688 AFIX 43 H14C 2 0.218665 0.128791 0.607933 11.00000 -1.20000 AFIX 0 C15C 1 0.321046 0.043075 0.585198 11.00000 0.07328 0.09599 = 0.06533 0.00319 -0.00586 0.00502 C16C 1 0.395398 0.045462 0.640669 11.00000 0.07057 0.09278 = 0.06911 -0.01129 -0.00870 0.01434 AFIX 43 H16C 2 0.384755 0.082970 0.672756 11.00000 -1.20000 AFIX 0 H20B 2 10.110600 10.040100 10.815500 11.00000 0.11792 H20C 2 10.433900 10.042200 10.766300 11.00000 0.13706 H20A 2 9.769900 9.987800 10.775900 11.00000 0.16798 H12A 2 9.505400 9.718102 10.990100 11.00000 0.33969 H9C 2 10.453100 9.906195 10.501305 11.00000 0.25519 HKLF 4 REM SIR2018 run in space group P 21/c REM wR2 = 0.2128, GooF = S = 0.922, Restrained GooF = 0.940 for all data REM R1 = 0.0670 for 3258 Fo > 4sig(Fo) and 0.1746 for all 8014 data REM 540 parameters refined using 45 restraints END WGHT 0.1063 0.0000 REM Highest difference peak 0.238, deepest hole -0.314, 1-sigma level 0.041 Q1 1 -0.2031 0.1745 0.6282 11.00000 0.05 0.24 Q2 1 -0.1245 0.2246 0.5959 11.00000 0.05 0.22 Q3 1 0.6222 -0.0623 0.5943 11.00000 0.05 0.21 Q4 1 -0.5015 -0.2581 0.9217 11.00000 0.05 0.20 Q5 1 -0.3840 -0.2799 0.9701 11.00000 0.05 0.19 Q6 1 -0.0863 0.1552 0.6133 11.00000 0.05 0.18 Q7 1 0.2546 -0.0838 0.4799 11.00000 0.05 0.18 Q8 1 -0.1293 0.1396 0.5783 11.00000 0.05 0.17 Q9 1 -0.4699 -0.3057 0.9221 11.00000 0.05 0.16 Q10 1 0.0208 0.0792 0.5110 11.00000 0.05 0.16 Q11 1 0.5413 -0.1221 0.6184 11.00000 0.05 0.16 Q12 1 -0.2257 0.2492 0.5885 11.00000 0.05 0.15 Q13 1 0.0075 0.2799 0.8824 11.00000 0.05 0.15 Q14 1 0.1544 0.3350 0.8251 11.00000 0.05 0.13 Q15 1 -0.4292 -0.2172 0.8068 11.00000 0.05 0.13 Q16 1 0.5235 0.0793 0.6362 11.00000 0.05 0.13 Q17 1 0.7089 0.1574 1.0798 11.00000 0.05 0.13 Q18 1 -0.5143 -0.2123 0.8834 11.00000 0.05 0.13 Q19 1 0.4549 -0.0132 0.8762 11.00000 0.05 0.12 Q20 1 -0.2217 0.0179 0.8111 11.00000 0.05 0.12 Q21 1 0.6790 -0.0448 0.6537 11.00000 0.05 0.12 Q22 1 0.6194 -0.1908 0.5894 11.00000 0.05 0.12 Q23 1 0.6428 0.0702 1.1067 11.00000 0.05 0.12 Q24 1 -0.4682 -0.3468 0.9801 11.00000 0.05 0.12 Q25 1 0.0936 0.1011 0.7142 11.00000 0.05 0.12 ; _shelx_res_checksum 82600 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1A O 0.0186(2) 0.16904(17) 0.68686(14) 0.0999(8) Uani 1 1 d . U O2A O -0.00561(17) -0.01725(15) 0.86555(11) 0.0788(7) Uani 1 1 d . . O3A O -0.0424(2) -0.08130(17) 0.97801(12) 0.0976(9) Uani 1 1 d . . H30A H -0.012307 -0.051941 0.952418 0.146 Uiso 1 1 calc R U N1A N -0.0834(2) 0.05088(16) 0.75657(14) 0.0631(7) Uani 1 1 d . . N2A N -0.146867(17) -0.001128(16) 0.790627(15) 0.0624(7) Uani 1 1 d D . C1A C -0.0803(3) 0.1386(2) 0.66562(19) 0.0765(10) Uani 1 1 d . U C2A C -0.1193(4) 0.1760(3) 0.6117(2) 0.1165(16) Uani 1 1 d . . H2A H -0.186215 0.167784 0.588472 0.140 Uiso 1 1 calc R U C3A C -0.0362(4) 0.2316(3) 0.5971(3) 0.1219(13) Uani 1 1 d . U H3A H -0.037384 0.265039 0.561045 0.146 Uiso 1 1 calc R U C4A C 0.0415(4) 0.2266(3) 0.6438(2) 0.1219(13) Uani 1 1 d . U H4A H 0.103720 0.258016 0.647069 0.146 Uiso 1 1 calc R U C5A C -0.1305(3) 0.0797(2) 0.70512(19) 0.0744(10) Uani 1 1 d . . H5A H -0.200691 0.062058 0.692133 0.089 Uiso 1 1 calc R U C6A C -0.1023(2) -0.03246(19) 0.84600(16) 0.0584(8) Uani 1 1 d . . C7A C -0.1702(2) -0.08765(19) 0.88262(15) 0.0567(8) Uani 1 1 d . . C8A C -0.1358(3) -0.1098(2) 0.94829(18) 0.0727(10) Uani 1 1 d . . C9A C -0.1972(3) -0.1594(3) 0.9829(2) 0.0931(12) Uani 1 1 d . . H9A H -0.173062 -0.173513 1.025575 0.112 Uiso 1 1 calc R U C10A C -0.2962(3) -0.1903(2) 0.9563(2) 0.0953(13) Uani 1 1 d . . C11A C -0.3607(4) -0.2422(4) 0.9920(3) 0.1780(16) Uani 1 1 d . U H11A H -0.338398 -0.257848 1.034649 0.214 Uiso 1 1 calc R U C12A C -0.456141(17) -0.268749(16) 0.962811(17) 0.1780(16) Uani 1 1 d D U C13A C -0.4922(5) -0.2502(4) 0.8982(3) 0.1780(16) Uani 1 1 d . U H13A H -0.556944 -0.271142 0.879534 0.214 Uiso 1 1 calc R U C14A C -0.4300(3) -0.2007(3) 0.8633(2) 0.1088(15) Uani 1 1 d . . H14A H -0.452848 -0.187303 0.820235 0.131 Uiso 1 1 calc R U C15A C -0.3316(3) -0.1692(2) 0.8912(2) 0.0782(10) Uani 1 1 d . . C16A C -0.2655(2) -0.11840(19) 0.85593(17) 0.0639(9) Uani 1 1 d . . H16A H -0.287564 -0.105216 0.812643 0.077 Uiso 1 1 calc R U O1B O 0.3667(2) -0.13644(16) 0.73446(14) 0.0908(8) Uani 1 1 d . . O2B O 0.33138(17) 0.13390(14) 0.78819(12) 0.0809(7) Uani 1 1 d . . O3B O 0.2976(2) 0.27764(17) 0.78227(16) 0.1162(10) Uani 1 1 d . . H30B H 0.329752 0.236794 0.776474 0.174 Uiso 1 1 calc R U N1B N 0.2565(2) -0.00872(18) 0.78326(13) 0.0656(8) Uani 1 1 d . . N2B N 0.190413(17) 0.051650(16) 0.802823(15) 0.0641(7) Uani 1 1 d D . C1B C 0.2652(3) -0.1421(2) 0.76025(18) 0.0739(10) Uani 1 1 d . . C2B C 0.2304(4) -0.2150(3) 0.7562(2) 0.1054(14) Uani 1 1 d . . H2B H 0.162563 -0.233538 0.769350 0.126 Uiso 1 1 calc R U C3B C 0.3147(5) -0.2582(3) 0.7285(3) 0.1223(17) Uani 1 1 d . . H3B H 0.314650 -0.311059 0.720937 0.147 Uiso 1 1 calc R U C4B C 0.3933(4) -0.2097(3) 0.7154(2) 0.1082(15) Uani 1 1 d . . H4B H 0.458841 -0.223058 0.695659 0.130 Uiso 1 1 calc R U C5B C 0.2105(3) -0.0740(2) 0.78154(17) 0.0686(10) Uani 1 1 d . . H5B H 0.137888 -0.077974 0.794713 0.082 Uiso 1 1 calc R U C6B C 0.2340(3) 0.1223(2) 0.80384(15) 0.0605(9) Uani 1 1 d . . C7B C 0.1639(3) 0.1867(2) 0.82353(16) 0.0622(9) Uani 1 1 d . . C8B C 0.2005(3) 0.2639(2) 0.80934(19) 0.0813(11) Uani 1 1 d . . C9B C 0.1329(4) 0.3235(3) 0.8235(2) 0.1080(14) Uani 1 1 d . . H9B H 0.155318 0.372961 0.812516 0.130 Uiso 1 1 calc R U C10B C 0.0335(4) 0.3149(3) 0.8530(2) 0.1009(15) Uani 1 1 d . . C11B C -0.0379(5) 0.3763(3) 0.8685(3) 0.152(3) Uani 1 1 d . . H11B H -0.019934 0.426667 0.857459 0.183 Uiso 1 1 calc R U C12B C -0.1339(6) 0.3608(5) 0.9000(4) 0.182(4) Uani 1 1 d . . H12B H -0.178535 0.402170 0.910779 0.218 Uiso 1 1 calc R U C13B C -0.1689(5) 0.2880(5) 0.9169(4) 0.171(3) Uani 1 1 d . . H13B H -0.235576 0.280573 0.937478 0.205 Uiso 1 1 calc R U C14B C -0.1015(4) 0.2265(3) 0.9023(2) 0.1282(19) Uani 1 1 d . . H14B H -0.121929 0.176813 0.913818 0.154 Uiso 1 1 calc R U C15B C -0.0021(3) 0.2389(3) 0.86995(18) 0.0880(13) Uani 1 1 d . . C16B C 0.0654(3) 0.1764(2) 0.85389(16) 0.0722(10) Uani 1 1 d . . H16B H 0.042814 0.126775 0.864089 0.087 Uiso 1 1 calc R U O1C O 0.7125(2) 0.0592(2) 0.93781(15) 0.1253(12) Uani 1 1 d . . O2C O 0.65186(17) -0.02733(14) 0.70795(11) 0.0743(7) Uani 1 1 d . . O3C O 0.5771(3) -0.1138(2) 0.60906(18) 0.1641(17) Uani 1 1 d . . H30C H 0.612325 -0.106598 0.644142 0.246 Uiso 1 1 calc R U N1C N 0.5898(2) 0.03992(17) 0.81932(14) 0.0688(8) Uani 1 1 d . . N2C N 0.518730(18) 0.032743(16) 0.764248(17) 0.0688(8) Uani 1 1 d . . C1C C 0.6045(3) 0.0707(3) 0.9339(2) 0.1030(15) Uani 1 1 d . . C2C C 0.5694(4) 0.0899(5) 0.9943(3) 0.181(3) Uani 1 1 d . . H2C H 0.497102 0.101706 1.004778 0.218 Uiso 1 1 calc R U C3C C 0.7440(5) 0.0696(4) 1.0036(3) 0.164(3) Uani 1 1 d . . H3C H 0.815866 0.063664 1.020894 0.197 Uiso 1 1 calc R U C4C C 0.6605(5) 0.0888(5) 1.0381(3) 0.196(4) Uani 1 1 d . . H4C H 0.661430 0.099760 1.083372 0.235 Uiso 1 1 calc R U C5C C 0.5459(3) 0.0604(3) 0.8721(2) 0.0950(14) Uani 1 1 d . . H5C H 0.470049 0.069485 0.870505 0.114 Uiso 1 1 calc R U C6C C 0.5565(2) -0.00027(19) 0.70914(17) 0.0601(9) Uani 1 1 d . . C7C C 0.4806(2) -0.0031(2) 0.65000(16) 0.0602(9) Uani 1 1 d . . C8C C 0.4958(3) -0.0588(3) 0.6017(2) 0.1002(14) Uani 1 1 d . . C9C C 0.426435(16) -0.060399(15) 0.546068(17) 0.137(2) Uani 1 1 d D . C10C C 0.3395(3) -0.0102(3) 0.5367(2) 0.0875(12) Uani 1 1 d . . C11C C 0.2672(5) -0.0133(4) 0.4800(2) 0.1336(19) Uani 1 1 d . . H11C H 0.280755 -0.048290 0.446273 0.160 Uiso 1 1 calc R U C12C C 0.1803(5) 0.0329(4) 0.4741(3) 0.1316(19) Uani 1 1 d . . H12C H 0.132223 0.028968 0.437077 0.158 Uiso 1 1 calc R U C13C C 0.1607(4) 0.0860(4) 0.5218(3) 0.152(2) Uani 1 1 d . . H13C H 0.099629 0.118421 0.517465 0.183 Uiso 1 1 calc R U C14C C 0.2314(4) 0.0914(4) 0.5761(2) 0.143(2) Uani 1 1 d . . H14C H 0.218665 0.128791 0.607933 0.171 Uiso 1 1 calc R U C15C C 0.3210(3) 0.0431(2) 0.58520(19) 0.0784(11) Uani 1 1 d . . C16C C 0.3954(3) 0.0455(2) 0.64067(18) 0.0778(10) Uani 1 1 d . . H16C H 0.384755 0.082970 0.672756 0.093 Uiso 1 1 calc R U H20B H 0.110600 0.040100 0.815500 0.118(13) Uiso 1 1 d D . H20C H 0.433900 0.042200 0.766300 0.137(15) Uiso 1 1 d . . H20A H -0.230100 -0.012200 0.775900 0.168(19) Uiso 1 1 d D . H12A H -0.494600 -0.281898 0.990100 0.34(4) Uiso 1 1 d D . H9C H 0.453100 -0.093805 0.501305 0.26(3) Uiso 1 1 d 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 0.0958(18) 0.100(2) 0.103(2) 0.0113(17) -0.0059(16) -0.0236(16) O2A 0.0508(13) 0.107(2) 0.0780(16) 0.0051(14) -0.0084(11) -0.0088(13) O3A 0.0849(17) 0.125(2) 0.0798(17) 0.0147(16) -0.0300(14) -0.0135(16) N1A 0.0619(16) 0.0647(19) 0.0626(19) 0.0005(15) 0.0009(14) -0.0053(14) N2A 0.0527(16) 0.069(2) 0.0649(18) 0.0077(15) -0.0015(13) -0.0065(14) C1A 0.084(2) 0.075(3) 0.069(2) -0.004(2) -0.015(2) -0.018(2) C2A 0.142(4) 0.117(4) 0.086(3) 0.024(3) -0.052(3) -0.030(3) C3A 0.159(4) 0.103(2) 0.104(3) 0.034(2) 0.008(2) -0.036(3) C4A 0.159(4) 0.103(2) 0.104(3) 0.034(2) 0.008(2) -0.036(3) C5A 0.073(2) 0.076(3) 0.073(2) 0.001(2) -0.0096(19) -0.020(2) C6A 0.0449(18) 0.072(2) 0.059(2) -0.0101(18) 0.0023(16) -0.0002(16) C7A 0.0493(18) 0.066(2) 0.055(2) 0.0041(17) 0.0002(15) 0.0088(16) C8A 0.065(2) 0.081(3) 0.071(2) 0.007(2) -0.0033(19) 0.004(2) C9A 0.095(3) 0.105(3) 0.079(3) 0.025(3) -0.005(2) 0.002(3) C10A 0.091(3) 0.096(3) 0.099(3) 0.032(3) 0.003(3) -0.012(2) C11A 0.152(3) 0.208(4) 0.173(3) 0.086(3) -0.010(3) -0.081(3) C12A 0.152(3) 0.208(4) 0.173(3) 0.086(3) -0.010(3) -0.081(3) C13A 0.152(3) 0.208(4) 0.173(3) 0.086(3) -0.010(3) -0.081(3) C14A 0.086(3) 0.119(4) 0.120(4) 0.025(3) -0.012(2) -0.037(3) C15A 0.062(2) 0.083(3) 0.089(3) 0.015(2) 0.000(2) -0.006(2) C16A 0.0534(19) 0.072(2) 0.066(2) 0.0067(18) -0.0024(16) 0.0030(17) O1B 0.0793(17) 0.083(2) 0.111(2) -0.0133(16) 0.0094(15) 0.0070(15) O2B 0.0575(14) 0.0814(19) 0.1042(19) -0.0069(14) 0.0105(13) -0.0115(12) O3B 0.114(2) 0.086(2) 0.150(3) 0.0010(19) 0.017(2) -0.0261(17) N1B 0.0561(16) 0.069(2) 0.0717(18) -0.0040(16) -0.0004(13) 0.0007(15) N2B 0.0489(15) 0.063(2) 0.0800(19) -0.0067(16) 0.0031(13) 0.0022(15) C1B 0.067(2) 0.076(3) 0.079(3) -0.003(2) 0.0043(19) -0.002(2) C2B 0.102(3) 0.068(3) 0.146(4) -0.003(3) 0.010(3) 0.002(3) C3B 0.145(4) 0.077(3) 0.144(5) -0.013(3) -0.014(4) 0.009(4) C4B 0.103(3) 0.107(4) 0.114(4) -0.024(3) 0.000(3) 0.041(3) C5B 0.060(2) 0.070(3) 0.076(2) 0.000(2) 0.0039(17) 0.001(2) C6B 0.053(2) 0.070(3) 0.057(2) -0.0007(18) -0.0094(15) -0.0024(18) C7B 0.062(2) 0.065(3) 0.058(2) -0.0060(18) -0.0150(16) 0.0057(18) C8B 0.093(3) 0.067(3) 0.082(3) -0.008(2) -0.023(2) 0.006(3) C9B 0.114(4) 0.084(4) 0.123(4) -0.012(3) -0.037(3) 0.011(3) C10B 0.106(3) 0.081(4) 0.111(4) -0.041(3) -0.055(3) 0.035(3) C11B 0.147(5) 0.120(5) 0.182(6) -0.069(4) -0.088(5) 0.063(4) C12B 0.128(6) 0.217(9) 0.196(8) -0.121(8) -0.064(5) 0.093(7) C13B 0.104(4) 0.231(9) 0.175(6) -0.088(7) -0.026(4) 0.058(6) C14B 0.082(3) 0.183(6) 0.119(4) -0.055(4) -0.009(3) 0.044(3) C15B 0.068(2) 0.120(4) 0.074(3) -0.033(3) -0.0277(19) 0.031(3) C16B 0.066(2) 0.082(3) 0.067(2) -0.012(2) -0.0131(17) 0.009(2) O1C 0.0802(19) 0.189(4) 0.104(2) -0.053(2) -0.0245(16) 0.0315(19) O2C 0.0515(13) 0.0970(19) 0.0740(15) -0.0125(13) -0.0024(11) 0.0078(12) O3C 0.136(3) 0.205(4) 0.147(3) -0.101(3) -0.053(2) 0.088(3) N1C 0.0539(15) 0.087(2) 0.0656(19) -0.0115(16) -0.0033(14) 0.0046(14) N2C 0.0492(16) 0.099(2) 0.0580(18) -0.0106(16) -0.0041(13) 0.0028(15) C1C 0.066(3) 0.173(5) 0.069(3) -0.024(3) -0.009(2) 0.027(3) C2C 0.101(4) 0.368(10) 0.074(3) -0.053(5) -0.013(3) 0.060(5) C3C 0.122(4) 0.250(8) 0.115(4) -0.074(5) -0.062(4) 0.064(4) C4C 0.155(5) 0.345(11) 0.085(4) -0.064(5) -0.039(4) 0.083(6) C5C 0.059(2) 0.151(4) 0.074(3) -0.015(3) -0.005(2) 0.025(2) C6C 0.0456(18) 0.066(2) 0.068(2) 0.0034(18) 0.0042(16) -0.0074(17) C7C 0.0490(18) 0.074(2) 0.057(2) -0.0016(19) 0.0024(15) -0.0080(18) C8C 0.072(2) 0.126(4) 0.102(3) -0.041(3) -0.007(2) 0.024(3) C9C 0.124(4) 0.182(6) 0.102(4) -0.073(4) -0.046(3) 0.047(4) C10C 0.070(2) 0.110(4) 0.081(3) -0.007(3) -0.014(2) -0.006(2) C11C 0.123(4) 0.169(6) 0.104(4) -0.036(4) -0.050(3) 0.018(4) C12C 0.117(4) 0.177(6) 0.097(4) 0.007(4) -0.040(3) 0.002(4) C13C 0.127(4) 0.209(7) 0.119(5) 0.009(5) -0.039(4) 0.061(4) C14C 0.130(4) 0.195(6) 0.099(4) -0.014(4) -0.044(3) 0.077(4) C15C 0.073(2) 0.096(3) 0.065(2) 0.003(2) -0.0059(19) 0.005(2) C16C 0.071(2) 0.093(3) 0.069(2) -0.011(2) -0.0087(18) 0.014(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4A O1A C1A 106.5(4) C8A O3A H30A 109.5 C5A N1A N2A 115.0(3) C6A N2A N1A 117.77(17) C6A N2A H20A 120.64 N1A N2A H20A 121.38 C2A C1A O1A 110.1(4) C2A C1A C5A 130.5(4) O1A C1A C5A 119.1(3) C1A C2A C3A 105.4(4) C1A C2A H2A 127.3 C3A C2A H2A 127.3 C4A C3A C2A 107.5(4) C4A C3A H3A 126.3 C2A C3A H3A 126.3 C3A C4A O1A 110.4(5) C3A C4A H4A 124.8 O1A C4A H4A 124.8 N1A C5A C1A 123.0(3) N1A C5A H5A 118.5 C1A C5A H5A 118.5 O2A C6A N2A 121.3(3) O2A C6A C7A 120.8(3) N2A C6A C7A 117.8(2) C16A C7A C8A 118.2(3) C16A C7A C6A 122.4(3) C8A C7A C6A 119.4(3) C9A C8A O3A 118.3(3) C9A C8A C7A 120.4(3) O3A C8A C7A 121.4(3) C8A C9A C10A 121.9(4) C8A C9A H9A 119.1 C10A C9A H9A 119.1 C9A C10A C11A 122.2(4) C9A C10A C15A 118.7(3) C11A C10A C15A 119.1(4) C12A C11A C10A 118.4(5) C12A C11A H11A 120.8 C10A C11A H11A 120.8 C11A C12A C13A 123.8(3) C11A C12A H12A 108.7 C13A C12A H12A 124.1 C14A C13A C12A 118.0(5) C14A C13A H13A 121.0 C12A C13A H13A 121.0 C13A C14A C15A 121.2(5) C13A C14A H14A 119.4 C15A C14A H14A 119.4 C16A C15A C14A 122.2(4) C16A C15A C10A 118.3(3) C14A C15A C10A 119.4(4) C7A C16A C15A 122.5(3) C7A C16A H16A 118.7 C15A C16A H16A 118.7 C1B O1B C4B 105.4(3) C8B O3B H30B 109.5 C5B N1B N2B 115.5(2) C6B N2B N1B 117.96(18) C6B N2B H20B 123.32 N1B N2B H20B 118.72 C2B C1B O1B 109.5(3) C2B C1B C5B 130.9(4) O1B C1B C5B 119.4(3) C1B C2B C3B 107.5(4) C1B C2B H2B 126.2 C3B C2B H2B 126.2 C4B C3B C2B 106.3(4) C4B C3B H3B 126.8 C2B C3B H3B 126.8 C3B C4B O1B 111.2(4) C3B C4B H4B 124.4 O1B C4B H4B 124.4 N1B C5B C1B 122.9(3) N1B C5B H5B 118.6 C1B C5B H5B 118.6 O2B C6B N2B 121.3(3) O2B C6B C7B 120.4(3) N2B C6B C7B 118.2(3) C16B C7B C8B 119.2(3) C16B C7B C6B 122.8(3) C8B C7B C6B 118.0(3) O3B C8B C9B 119.7(4) O3B C8B C7B 121.9(3) C9B C8B C7B 118.4(4) C8B C9B C10B 123.6(5) C8B C9B H9B 118.2 C10B C9B H9B 118.2 C9B C10B C11B 124.5(6) C9B C10B C15B 118.8(4) C11B C10B C15B 116.7(5) C12B C11B C10B 119.2(7) C12B C11B H11B 120.4 C10B C11B H11B 120.4 C11B C12B C13B 124.6(7) C11B C12B H12B 117.7 C13B C12B H12B 117.7 C12B C13B C14B 117.8(7) C12B C13B H13B 121.1 C14B C13B H13B 121.1 C13B C14B C15B 120.2(6) C13B C14B H14B 119.9 C15B C14B H14B 119.9 C16B C15B C14B 120.3(5) C16B C15B C10B 118.2(4) C14B C15B C10B 121.4(4) C7B C16B C15B 121.7(4) C7B C16B H16B 119.1 C15B C16B H16B 119.1 C1C O1C C3C 105.8(3) C8C O3C H30C 109.5 C5C N1C N2C 115.7(2) C6C N2C N1C 118.66(17) C6C N2C H20C 117.85 N1C N2C H20C 122.47 O1C C1C C2C 109.3(4) O1C C1C C5C 119.4(3) C2C C1C C5C 131.2(4) C1C C2C C4C 107.5(4) C1C C2C H2C 126.3 C4C C2C H2C 126.3 C4C C3C O1C 111.1(4) C4C C3C H3C 124.5 O1C C3C H3C 124.5 C3C C4C C2C 106.3(5) C3C C4C H4C 126.9 C2C C4C H4C 126.9 N1C C5C C1C 124.3(3) N1C C5C H5C 117.9 C1C C5C H5C 117.9 O2C C6C N2C 121.4(3) O2C C6C C7C 121.3(3) N2C C6C C7C 117.3(2) C16C C7C C8C 117.5(3) C16C C7C C6C 123.0(3) C8C C7C C6C 119.5(3) C9C C8C O3C 119.1(3) C9C C8C C7C 119.5(3) O3C C8C C7C 121.4(4) C8C C9C C10C 122.7(3) C8C C9C H9C 118.47 C10C C9C H9C 117.22 C15C C10C C9C 118.4(3) C15C C10C C11C 119.3(4) C9C C10C C11C 122.3(4) C12C C11C C10C 120.9(5) C12C C11C H11C 119.6 C10C C11C H11C 119.6 C11C C12C C13C 120.6(5) C11C C12C H12C 119.7 C13C C12C H12C 119.7 C12C C13C C14C 119.4(5) C12C C13C H13C 120.3 C14C C13C H13C 120.3 C13C C14C C15C 122.1(5) C13C C14C H14C 119.0 C15C C14C H14C 119.0 C10C C15C C14C 117.7(4) C10C C15C C16C 118.0(4) C14C C15C C16C 124.3(4) C7C C16C C15C 123.9(4) C7C C16C H16C 118.1 C15C C16C H16C 118.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1A C4A 1.359(5) O1A C1A 1.362(4) O2A C6A 1.248(3) O3A C8A 1.353(4) O3A H30A 0.8200 N1A C5A 1.265(4) N1A N2A 1.384(3) N2A C6A 1.335(3) N2A H20A 1.0563 C1A C2A 1.336(5) C1A C5A 1.445(5) C2A C3A 1.431(6) C2A H2A 0.9300 C3A C4A 1.306(6) C3A H3A 0.9300 C4A H4A 0.9300 C5A H5A 0.9300 C6A C7A 1.478(4) C7A C16A 1.362(4) C7A C8A 1.423(4) C8A C9A 1.349(5) C9A C10A 1.399(5) C9A H9A 0.9300 C10A C11A 1.408(6) C10A C15A 1.411(5) C11A C12A 1.356(6) C11A H11A 0.9300 C12A C13A 1.393(6) C12A H12A 0.76835 C13A C14A 1.356(6) C13A H13A 0.9300 C14A C15A 1.407(5) C14A H14A 0.9300 C15A C16A 1.402(4) C16A H16A 0.9300 O1B C1B 1.355(4) O1B C4B 1.371(5) O2B C6B 1.248(3) O3B C8B 1.336(4) O3B H30B 0.8200 N1B C5B 1.263(4) N1B N2B 1.385(3) N2B C6B 1.336(3) N2B H20B 1.0281 C1B C2B 1.335(5) C1B C5B 1.430(5) C2B C3B 1.400(6) C2B H2B 0.9300 C3B C4B 1.306(6) C3B H3B 0.9300 C4B H4B 0.9300 C5B H5B 0.9300 C6B C7B 1.467(4) C7B C16B 1.372(4) C7B C8B 1.444(5) C8B C9B 1.356(5) C9B C10B 1.370(6) C9B H9B 0.9300 C10B C11B 1.416(6) C10B C15B 1.435(6) C11B C12B 1.372(9) C11B H11B 0.9300 C12B C13B 1.380(10) C12B H12B 0.9300 C13B C14B 1.383(7) C13B H13B 0.9300 C14B C15B 1.405(6) C14B H14B 0.9300 C15B C16B 1.403(5) C16B H16B 0.9300 O1C C1C 1.321(4) O1C C3C 1.375(5) O2C C6C 1.247(3) O3C C8C 1.376(5) O3C H30C 0.8200 N1C C5C 1.258(4) N1C N2C 1.382(3) N2C C6C 1.345(3) N2C H20C 1.0418 C1C C2C 1.346(6) C1C C5C 1.420(5) C2C C4C 1.384(6) C2C H2C 0.9300 C3C C4C 1.292(6) C3C H3C 0.9300 C4C H4C 0.9300 C5C H5C 0.9300 C6C C7C 1.476(4) C7C C16C 1.339(4) C7C C8C 1.390(5) C8C C9C 1.372(4) C9C C10C 1.374(4) C9C H9C 1.1294 C10C C15C 1.370(5) C10C C11C 1.412(6) C11C C12C 1.325(7) C11C H11C 0.9300 C12C C13C 1.359(7) C12C H12C 0.9300 C13C C14C 1.365(7) C13C H13C 0.9300 C14C C15C 1.378(5) C14C H14C 0.9300 C15C C16C 1.407(5) C16C H16C 0.9300 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 _geom_hbond_publ_flag C5A H5A O2C 0.93 2.40 3.225(4) 148.4 1_455 yes C5B H5B O2A 0.93 2.52 3.319(4) 144.1 . yes C5C H5C O2B 0.93 2.57 3.298(5) 135.6 . yes 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 C5A N1A N2A C6A -178.9(3) C4A O1A C1A C2A -0.7(5) C4A O1A C1A C5A -175.2(4) O1A C1A C2A C3A 2.4(5) C5A C1A C2A C3A 176.0(4) C1A C2A C3A C4A -3.2(6) C2A C3A C4A O1A 2.9(7) C1A O1A C4A C3A -1.4(6) N2A N1A C5A C1A 175.8(3) C2A C1A C5A N1A -178.1(4) O1A C1A C5A N1A -5.0(6) N1A N2A C6A O2A -2.0(4) N1A N2A C6A C7A 179.6(2) O2A C6A C7A C16A -165.4(3) N2A C6A C7A C16A 12.9(4) O2A C6A C7A C8A 14.8(5) N2A C6A C7A C8A -166.9(3) C16A C7A C8A C9A -0.6(5) C6A C7A C8A C9A 179.3(3) C16A C7A C8A O3A -179.7(3) C6A C7A C8A O3A 0.1(5) O3A C8A C9A C10A 178.6(4) C7A C8A C9A C10A -0.5(6) C8A C9A C10A C11A 179.9(5) C8A C9A C10A C15A 0.6(7) C9A C10A C11A C12A 179.3(4) C15A C10A C11A C12A -1.4(9) C10A C11A C12A C13A 2.7(9) C11A C12A C13A C14A -2.3(9) C12A C13A C14A C15A 0.4(9) C13A C14A C15A C16A 179.4(5) C13A C14A C15A C10A 0.9(7) C9A C10A C15A C16A 0.3(6) C11A C10A C15A C16A -179.0(5) C9A C10A C15A C14A 179.0(4) C11A C10A C15A C14A -0.4(7) C8A C7A C16A C15A 1.6(5) C6A C7A C16A C15A -178.2(3) C14A C15A C16A C7A 179.9(3) C10A C15A C16A C7A -1.5(5) C5B N1B N2B C6B -178.3(3) C4B O1B C1B C2B -1.0(5) C4B O1B C1B C5B -176.4(3) O1B C1B C2B C3B 1.9(5) C5B C1B C2B C3B 176.6(4) C1B C2B C3B C4B -2.0(6) C2B C3B C4B O1B 1.5(6) C1B O1B C4B C3B -0.3(5) N2B N1B C5B C1B 177.7(3) C2B C1B C5B N1B 179.0(4) O1B C1B C5B N1B -6.7(5) N1B N2B C6B O2B -0.5(4) N1B N2B C6B C7B 179.1(2) O2B C6B C7B C16B -166.3(3) N2B C6B C7B C16B 14.0(4) O2B C6B C7B C8B 14.4(4) N2B C6B C7B C8B -165.2(3) C16B C7B C8B O3B 177.3(3) C6B C7B C8B O3B -3.4(5) C16B C7B C8B C9B -3.4(5) C6B C7B C8B C9B 175.8(3) O3B C8B C9B C10B -178.0(4) C7B C8B C9B C10B 2.7(6) C8B C9B C10B C11B 179.6(4) C8B C9B C10B C15B -0.2(6) C9B C10B C11B C12B -177.9(5) C15B C10B C11B C12B 1.8(7) C10B C11B C12B C13B -1.7(11) C11B C12B C13B C14B 1.4(13) C12B C13B C14B C15B -1.3(10) C13B C14B C15B C16B -178.8(5) C13B C14B C15B C10B 1.7(7) C9B C10B C15B C16B -1.6(6) C11B C10B C15B C16B 178.6(4) C9B C10B C15B C14B 177.9(4) C11B C10B C15B C14B -1.9(6) C8B C7B C16B C15B 1.7(5) C6B C7B C16B C15B -177.5(3) C14B C15B C16B C7B -178.7(3) C10B C15B C16B C7B 0.8(5) C5C N1C N2C C6C -169.8(3) C3C O1C C1C C2C 1.7(7) C3C O1C C1C C5C -177.0(5) O1C C1C C2C C4C -1.0(8) C5C C1C C2C C4C 177.5(6) C1C O1C C3C C4C -1.8(8) O1C C3C C4C C2C 1.1(10) C1C C2C C4C C3C -0.1(10) N2C N1C C5C C1C 179.7(4) O1C C1C C5C N1C 0.7(8) C2C C1C C5C N1C -177.7(6) N1C N2C C6C O2C 3.3(4) N1C N2C C6C C7C -176.6(2) O2C C6C C7C C16C -156.9(3) N2C C6C C7C C16C 23.0(4) O2C C6C C7C C8C 23.9(5) N2C C6C C7C C8C -156.2(3) C16C C7C C8C C9C 2.1(5) C6C C7C C8C C9C -178.8(3) C16C C7C C8C O3C -176.1(4) C6C C7C C8C O3C 3.0(6) O3C C8C C9C C10C 176.3(4) C7C C8C C9C C10C -1.9(5) C8C C9C C10C C15C -0.6(5) C8C C9C C10C C11C -178.7(4) C15C C10C C11C C12C -2.1(8) C9C C10C C11C C12C 176.0(5) C10C C11C C12C C13C 2.0(9) C11C C12C C13C C14C -0.1(10) C12C C13C C14C C15C -1.8(10) C9C C10C C15C C14C -177.9(4) C11C C10C C15C C14C 0.2(7) C9C C10C C15C C16C 2.7(5) C11C C10C C15C C16C -179.1(4) C13C C14C C15C C10C 1.6(8) C13C C14C C15C C16C -179.0(5) C8C C7C C16C C15C 0.1(5) C6C C7C C16C C15C -179.0(3) C10C C15C C16C C7C -2.6(6) C14C C15C C16C C7C 178.1(4)