#------------------------------------------------------------------------------ #$Date: 2021-11-18 03:20:32 +0200 (Thu, 18 Nov 2021) $ #$Revision: 270742 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061067.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_7061067 loop_ _publ_author_name 'Shatokhin, Stanislav S.' 'Tuskaev, Vladislav A.' 'Gagieva, Svetlana Chermenovna' 'Markova, Alina' 'Pozdnyakov, Dmitry I.' 'Denisov, Gleb' 'Melnikova, Elizaveta Konstantinovna' 'Oganesyan, Eduard T.' 'Bulychev, Boris M.' _publ_section_title ; SYNTHESIS, CYTOTOXIC AND ANTIOXIDANT ACTIVITY OF NEW 1,3-DIMETHYL-8-(CHROMON-3-YL)-XANTHINE DERIVATIVES CONTAINING 2,6-DI-TERT-BUTYLPHENOL FRAGMENT ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03726A _journal_year 2021 _chemical_formula_moiety 'C30 H32 N4 O5, 0.25(H2 O)' _chemical_formula_sum 'C30 H32.5 N4 O5.25' _chemical_formula_weight 533.10 _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' _atom_sites_solution_hydrogens mixed _audit_creation_date 2021-03-13 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-13 deposited with the CCDC. 2021-10-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.420(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7391(8) _cell_length_b 25.2387(19) _cell_length_c 11.2459(9) _cell_measurement_reflns_used 2488 _cell_measurement_temperature 120 _cell_measurement_theta_max 22.64 _cell_measurement_theta_min 2.24 _cell_volume 2759.3(4) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 120 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0967 _diffrn_reflns_av_unetI/netI 0.0940 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 31316 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.495 _diffrn_reflns_theta_min 1.985 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0693 before and 0.0612 after correction. The Ratio of minimum to maximum transmission is 0.8862. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.283 _exptl_crystal_description prism _exptl_crystal_F_000 1130 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.301 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 403 _refine_ls_number_reflns 8343 _refine_ls_number_restraints 60 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.1344 _refine_ls_R_factor_gt 0.0647 _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^)+(0.0536P)^2^+0.7361P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1319 _refine_ls_wR_factor_ref 0.1593 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4584 _reflns_number_total 8343 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03726a2.cif _cod_data_source_block Shat70 _cod_original_formula_sum 'C30 H32.50 N4 O5.25' _cod_database_code 7061067 _shelxl_version_number 2014/6 _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_max 0.989 _shelx_estimated_absorpt_t_min 0.980 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All O(H) groups, All O(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(O4) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2 Uanis(O4') = Uanis(O4) Uanis(C8') = Uanis(C8) Uanis(C16') = Uanis(C16) Uanis(C9') = Uanis(C9) Uanis(O3') = Uanis(O3) Uanis(C15) = Uanis(C15') Uanis(C10') = Uanis(C10) Uanis(C14) = Uanis(C14') Uanis(C11') = Uanis(C11) Uanis(C13) = Uanis(C13') Uanis(C12) = Uanis(C12') 3. Others Sof(C12')=Sof(H12')=Sof(C13')=Sof(H13')=Sof(C10')=Sof(C15')=Sof(C14')= Sof(H14')=Sof(C11')=Sof(H11')=Sof(C16')=Sof(C8')=Sof(O4')=Sof(O3')=Sof(C9')= Sof(H9')=1-FVAR(1) Sof(O4)=Sof(C15)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(C10)=Sof(C16)=Sof(C11)=Sof(H11)= Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(O3)=FVAR(1) Fixed Sof: O1W(0.25) H1WA(0.25) H1WB(0.25) 4.a Riding coordinates: O5(H5), O1W(H1WA,H1WB) 4.b Aromatic/amide H refined with riding coordinates: C22(H22), C18(H18), C9(H9), C11(H11), C14(H14), C12(H12), C13(H13), C12'(H12'), C13'(H13'), C14'(H14'), C11'(H11'), C9'(H9') 4.c Idealised Me refined as rotating group: C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C25(H25A,H25B,H25C), C7(H7A,H7B, H7C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C6(H6A,H6B,H6C), C24(H24A,H24B, H24C) ; _shelx_res_file ; TITL a_a.res in P2(1)/c REM Old TITL a in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.170, Rweak 0.011, Alpha 0.033, Orientation as input REM Formula found by SHELXT: C30 N5 O4 CELL 0.71073 9.7391 25.2387 11.2459 90 93.42 90 ZERR 4 0.0008 0.0019 0.0009 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 120 130 16 21 ISOR O4 C15 C9 C8 C10 C16 C11 C14 C12 C13 EADP O4' O4 EADP C8' C8 EADP C16' C16 EADP C9' C9 EADP O3' O3 EADP C15 C15' EADP C10' C10 EADP C14 C14' EADP C11' C11 EADP C13 C13' EADP C12 C12' L.S. 10 PLAN 20 SIZE 0.23 0.15 0.12 TEMP -153.15 LIST 6 fmap 2 acta REM REM REM WGHT 0.053600 0.736100 FVAR 0.44015 0.89923 O5 4 0.257320 0.207155 0.284753 11.00000 0.03049 0.01252 = 0.03453 -0.00691 -0.00043 0.00018 AFIX 3 H5 2 0.216210 0.188555 0.231313 11.00000 -1.20000 AFIX 0 O2 4 0.126663 0.375183 0.638787 11.00000 0.04852 0.01876 = 0.03243 0.00333 0.00483 0.00538 O1 4 0.064458 0.548265 0.747136 11.00000 0.03430 0.02682 = 0.03217 -0.01022 0.00163 0.00751 N3 3 0.159028 0.534078 0.569876 11.00000 0.02755 0.01295 = 0.03122 -0.00421 0.00160 0.00294 N1 3 0.234229 0.420463 0.405288 11.00000 0.03018 0.01286 = 0.02456 -0.00127 0.00030 0.00360 N2 3 0.250136 0.508789 0.381019 11.00000 0.03199 0.01556 = 0.03064 0.00020 0.00330 0.00273 PART 1 O4 4 0.552949 0.448743 0.294510 21.00000 0.03670 0.05564 = 0.03059 -0.00438 -0.00575 -0.00015 PART 0 N4 3 0.095057 0.462303 0.690328 11.00000 0.02830 0.01902 = 0.02542 -0.00142 0.00214 0.00503 C21 1 0.358908 0.281654 0.378954 11.00000 0.02155 0.01497 = 0.02284 0.00173 0.00468 0.00287 C20 1 0.247356 0.260215 0.309099 11.00000 0.02462 0.01437 = 0.02197 -0.00184 0.00601 0.00050 C17 1 0.237791 0.364816 0.374472 11.00000 0.02714 0.01243 = 0.02180 -0.00074 0.00229 0.00221 C22 1 0.350335 0.334984 0.411351 11.00000 0.02800 0.01444 = 0.02139 -0.00019 0.00194 -0.00113 AFIX 43 H22 2 0.422950 0.350709 0.459261 11.00000 -1.20000 AFIX 0 C2 1 0.199191 0.497425 0.487946 11.00000 0.02122 0.01516 = 0.02692 -0.00426 -0.00250 0.00234 C19 1 0.132615 0.290809 0.268176 11.00000 0.02191 0.01933 = 0.02188 -0.00374 0.00385 0.00166 C18 1 0.131045 0.343858 0.303706 11.00000 0.02696 0.01643 = 0.02453 -0.00173 0.00308 0.00658 AFIX 43 H18 2 0.055356 0.365733 0.278706 11.00000 -1.20000 AFIX 0 C3 1 0.104397 0.517121 0.673003 11.00000 0.02140 0.02091 = 0.02936 -0.00372 -0.00445 0.00523 C4 1 0.137159 0.422213 0.612391 11.00000 0.02677 0.01958 = 0.02333 -0.00180 -0.00197 0.00599 C5 1 0.187174 0.444001 0.507391 11.00000 0.02769 0.01342 = 0.02351 -0.00194 -0.00089 0.00433 C27 1 0.485717 0.248515 0.421189 11.00000 0.02286 0.01802 = 0.02648 0.00152 0.00211 0.00248 C1 1 0.269948 0.460704 0.333736 11.00000 0.03112 0.01677 = 0.02614 0.00026 0.00285 0.00336 C29 1 0.442450 0.206353 0.511421 11.00000 0.03193 0.01979 = 0.02983 0.00294 0.00113 0.00425 AFIX 137 H29A 2 0.404795 0.223977 0.579973 11.00000 -1.50000 H29B 2 0.522820 0.185227 0.538349 11.00000 -1.50000 H29C 2 0.372311 0.183132 0.473133 11.00000 -1.50000 AFIX 0 C23 1 0.013138 0.268684 0.186334 11.00000 0.02473 0.02435 = 0.02953 -0.00850 -0.00090 0.00240 C30 1 0.552962 0.222485 0.316036 11.00000 0.02326 0.02651 = 0.03658 0.00299 0.00538 0.00540 AFIX 137 H30A 2 0.487878 0.197759 0.275947 11.00000 -1.50000 H30B 2 0.635517 0.203192 0.345318 11.00000 -1.50000 H30C 2 0.578467 0.249869 0.259641 11.00000 -1.50000 AFIX 0 PART 1 C15 1 0.514517 0.435727 0.085678 21.00000 0.03200 0.01492 = 0.02712 0.00190 0.00148 -0.00060 PART 0 C25 1 0.066614 0.249986 0.067350 11.00000 0.03335 0.02591 = 0.02634 -0.00294 -0.00019 -0.00045 AFIX 137 H25A 2 0.100887 0.280504 0.024119 11.00000 -1.50000 H25B 2 -0.008373 0.233079 0.019296 11.00000 -1.50000 H25C 2 0.141388 0.224467 0.082853 11.00000 -1.50000 AFIX 0 PART 1 C9 1 0.237107 0.445991 0.117902 21.00000 0.02940 0.02636 = 0.03049 -0.00226 0.00335 0.00423 AFIX 43 H9 2 0.141303 0.448900 0.128262 21.00000 -1.20000 AFIX 0 C8 1 0.323015 0.450659 0.215426 21.00000 0.02994 0.01450 = 0.02458 -0.00002 0.00025 0.00131 C10 1 0.415039 0.432947 -0.008535 21.00000 0.02907 0.01603 = 0.03020 0.00246 -0.00132 0.00029 PART 0 C7 1 0.029406 0.444983 0.798106 11.00000 0.03403 0.03257 = 0.02975 0.00075 0.00551 0.00637 AFIX 137 H7A 2 0.059277 0.467943 0.865009 11.00000 -1.50000 H7B 2 0.055955 0.408307 0.816573 11.00000 -1.50000 H7C 2 -0.070777 0.447153 0.784579 11.00000 -1.50000 AFIX 0 C28 1 0.596895 0.283644 0.484593 11.00000 0.02663 0.02313 = 0.04200 0.00260 -0.00577 0.00297 AFIX 137 H28A 2 0.623546 0.311737 0.430397 11.00000 -1.50000 H28B 2 0.677527 0.261987 0.508064 11.00000 -1.50000 H28C 2 0.560313 0.299550 0.555639 11.00000 -1.50000 AFIX 0 PART 1 C16 1 0.471768 0.445485 0.207172 21.00000 0.03174 0.01890 = 0.02984 0.00187 -0.00234 0.00007 PART 0 C26 1 -0.062576 0.223495 0.247922 11.00000 0.02706 0.03895 = 0.03622 -0.01098 0.00553 -0.00496 AFIX 137 H26A 2 0.003718 0.196086 0.274276 11.00000 -1.50000 H26B 2 -0.132174 0.208097 0.191602 11.00000 -1.50000 H26C 2 -0.107318 0.237627 0.316970 11.00000 -1.50000 AFIX 0 C6 1 0.180088 0.590935 0.551765 11.00000 0.03696 0.01610 = 0.03937 -0.00471 0.00183 0.00266 AFIX 137 H6A 2 0.231076 0.596378 0.480225 11.00000 -1.50000 H6B 2 0.232592 0.605730 0.621044 11.00000 -1.50000 H6C 2 0.090679 0.608716 0.541915 11.00000 -1.50000 AFIX 0 PART 1 C11 1 0.451300 0.425031 -0.125933 21.00000 0.04883 0.02378 = 0.02825 0.00226 0.00047 -0.00164 AFIX 43 H11 2 0.382879 0.423531 -0.189686 21.00000 -1.20000 AFIX 0 PART 0 C24 1 -0.094900 0.311773 0.154779 11.00000 0.03467 0.04063 = 0.05123 -0.01708 -0.01448 0.00988 AFIX 137 H24A 2 -0.133761 0.324625 0.227827 11.00000 -1.50000 H24B 2 -0.168432 0.296844 0.101679 11.00000 -1.50000 H24C 2 -0.051264 0.341273 0.114750 11.00000 -1.50000 AFIX 0 PART 1 C14 1 0.652126 0.429036 0.062228 21.00000 0.03402 0.02613 = 0.03863 0.00129 0.00441 -0.00190 AFIX 43 H14 2 0.721255 0.430160 0.125452 21.00000 -1.20000 AFIX 0 C12 1 0.589252 0.419445 -0.146812 21.00000 0.05468 0.02137 = 0.03414 0.00079 0.01670 -0.00216 AFIX 43 H12 2 0.616488 0.414674 -0.225823 21.00000 -1.20000 AFIX 0 C13 1 0.687570 0.420804 -0.052655 21.00000 0.04464 0.02780 = 0.04395 0.00033 0.01510 -0.00485 AFIX 43 H13 2 0.781632 0.415931 -0.067910 21.00000 -1.20000 AFIX 0 PART 0 O1W 4 0.506732 0.563207 0.446914 10.25000 0.03097 0.04626 = 0.03380 -0.00314 -0.00173 -0.01433 AFIX 3 H1WA 2 0.484242 0.557997 0.520424 10.25000 -1.20000 H1WB 2 0.443382 0.544427 0.403914 10.25000 -1.20000 AFIX 0 PART 2 C12' 1 0.642636 0.420290 -0.118852 -21.00000 0.05468 0.02137 = 0.03414 0.00079 0.01670 -0.00216 AFIX 43 H12' 2 0.711544 0.411669 -0.171979 -21.00000 -1.20000 AFIX 0 C13' 1 0.499695 0.421334 -0.159434 -21.00000 0.04464 0.02780 = 0.04395 0.00033 0.01510 -0.00485 AFIX 43 H13' 2 0.476425 0.417086 -0.242126 -21.00000 -1.20000 AFIX 0 C10' 1 0.570196 0.439293 0.071235 -21.00000 0.02907 0.01603 = 0.03020 0.00246 -0.00132 0.00029 C15' 1 0.449677 0.436861 0.036681 -21.00000 0.03200 0.01492 = 0.02712 0.00190 0.00148 -0.00060 C14' 1 0.397794 0.428048 -0.085548 -21.00000 0.03402 0.02613 = 0.03863 0.00129 0.00441 -0.00190 AFIX 43 H14' 2 0.302837 0.427143 -0.110292 -21.00000 -1.20000 AFIX 0 C11' 1 0.676634 0.431828 -0.003665 -21.00000 0.04883 0.02378 = 0.02825 0.00226 0.00047 -0.00164 AFIX 43 H11' 2 0.770055 0.434731 0.025068 -21.00000 -1.20000 AFIX 0 C16' 1 0.318747 0.445378 0.125176 -21.00000 0.03174 0.01890 = 0.02984 0.00187 -0.00234 0.00007 C8' 1 0.373267 0.455149 0.242853 -21.00000 0.02994 0.01450 = 0.02458 -0.00002 0.00025 0.00131 PART 0 PART 1 O3 4 0.276164 0.437543 0.007080 21.00000 0.03526 0.03472 = 0.02546 -0.00301 -0.00232 0.00390 PART 0 PART 2 O4' 4 0.192736 0.445101 0.095927 -21.00000 0.03670 0.05564 = 0.03059 -0.00438 -0.00575 -0.00015 O3' 4 0.613126 0.448599 0.191139 -21.00000 0.03526 0.03472 = 0.02546 -0.00301 -0.00232 0.00390 C9' 1 0.516667 0.455422 0.262337 -21.00000 0.02940 0.02636 = 0.03049 -0.00226 0.00335 0.00423 AFIX 43 H9' 2 0.548038 0.461805 0.342668 -21.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in P2(1)/c REM R1 = 0.0647 for 4584 Fo > 4sig(Fo) and 0.1344 for all 8343 data REM 403 parameters refined using 60 restraints END WGHT 0.0537 0.7314 REM Highest difference peak 0.301, deepest hole -0.368, 1-sigma level 0.056 Q1 1 0.1607 0.4689 0.4924 11.00000 0.05 0.30 Q2 1 0.0668 0.2752 0.2326 11.00000 0.05 0.23 Q3 1 -0.0159 0.5707 0.7809 11.00000 0.05 0.23 Q4 1 0.3601 0.3100 0.3801 11.00000 0.05 0.22 Q5 1 -0.0680 0.4139 0.7566 11.00000 0.05 0.22 Q6 1 0.8367 0.4190 -0.0573 11.00000 0.05 0.22 Q7 1 0.2566 0.3928 0.3822 11.00000 0.05 0.22 Q8 1 -0.2199 0.2686 0.2348 11.00000 0.05 0.21 Q9 1 0.6175 0.1624 0.5027 11.00000 0.05 0.21 Q10 1 0.2307 0.4741 0.5217 11.00000 0.05 0.20 Q11 1 0.1932 0.6186 0.7393 11.00000 0.05 0.20 Q12 1 0.3018 0.4845 0.3783 11.00000 0.05 0.20 Q13 1 0.6866 0.4188 0.1764 11.00000 0.05 0.20 Q14 1 0.1055 0.5788 0.7283 11.00000 0.05 0.19 Q15 1 0.0343 0.3789 0.7234 11.00000 0.05 0.19 Q16 1 0.3075 0.2733 0.3481 11.00000 0.05 0.19 Q17 1 0.5013 0.4954 0.3580 11.00000 0.05 0.19 Q18 1 0.1918 0.5602 0.5593 11.00000 0.05 0.19 Q19 1 0.9349 0.4216 -0.0378 11.00000 0.05 0.19 Q20 1 0.4743 0.4539 0.0124 11.00000 0.05 0.19 ; _shelx_res_checksum 74829 _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.25732(15) 0.20715(5) 0.28475(13) 0.0259(3) Uani 1 1 d . . . . . H5 H 0.2162 0.1886 0.2313 0.031 Uiso 1 1 d R . . . . O2 O 0.12666(17) 0.37518(5) 0.63879(14) 0.0331(4) Uani 1 1 d . . . . . O1 O 0.06446(17) 0.54827(6) 0.74714(14) 0.0311(4) Uani 1 1 d . . . . . N3 N 0.15903(18) 0.53408(6) 0.56988(16) 0.0239(4) Uani 1 1 d . . . . . N1 N 0.23423(18) 0.42046(6) 0.40529(15) 0.0226(4) Uani 1 1 d . . . . . N2 N 0.25014(19) 0.50879(6) 0.38102(16) 0.0260(4) Uani 1 1 d . . . . . O4 O 0.5529(3) 0.44874(11) 0.29451(19) 0.0413(7) Uani 0.899(2) 1 d . U P A 1 N4 N 0.09506(19) 0.46230(6) 0.69033(15) 0.0242(4) Uani 1 1 d . . . . . C21 C 0.3589(2) 0.28165(7) 0.37895(17) 0.0197(4) Uani 1 1 d . . . . . C20 C 0.2474(2) 0.26021(7) 0.30910(17) 0.0201(4) Uani 1 1 d . . . . . C17 C 0.2378(2) 0.36482(7) 0.37447(17) 0.0204(4) Uani 1 1 d . . . . . C22 C 0.3503(2) 0.33498(7) 0.41135(18) 0.0213(4) Uani 1 1 d . . . . . H22 H 0.4230 0.3507 0.4593 0.026 Uiso 1 1 calc R . . . . C2 C 0.1992(2) 0.49742(7) 0.48795(18) 0.0213(4) Uani 1 1 d . . . . . C19 C 0.1326(2) 0.29081(7) 0.26818(18) 0.0209(4) Uani 1 1 d . . . . . C18 C 0.1310(2) 0.34386(7) 0.30371(18) 0.0226(4) Uani 1 1 d . . . . . H18 H 0.0554 0.3657 0.2787 0.027 Uiso 1 1 calc R . . . . C3 C 0.1044(2) 0.51712(8) 0.6730(2) 0.0241(5) Uani 1 1 d . . . . . C4 C 0.1372(2) 0.42221(8) 0.61239(18) 0.0234(4) Uani 1 1 d . . . . . C5 C 0.1872(2) 0.44400(7) 0.50739(18) 0.0216(4) Uani 1 1 d . . . . . C27 C 0.4857(2) 0.24852(7) 0.42119(19) 0.0224(4) Uani 1 1 d . . . . . C1 C 0.2699(2) 0.46070(7) 0.33374(19) 0.0246(5) Uani 1 1 d . . . . . C29 C 0.4424(2) 0.20635(8) 0.51142(19) 0.0272(5) Uani 1 1 d . . . . . H29A H 0.4048 0.2240 0.5800 0.041 Uiso 1 1 calc GR . . . . H29B H 0.5228 0.1852 0.5383 0.041 Uiso 1 1 calc GR . . . . H29C H 0.3723 0.1831 0.4731 0.041 Uiso 1 1 calc GR . . . . C23 C 0.0131(2) 0.26868(8) 0.1863(2) 0.0263(5) Uani 1 1 d . . . . . C30 C 0.5530(2) 0.22249(8) 0.3160(2) 0.0286(5) Uani 1 1 d . . . . . H30A H 0.4879 0.1978 0.2759 0.043 Uiso 1 1 calc GR . . . . H30B H 0.6355 0.2032 0.3453 0.043 Uiso 1 1 calc GR . . . . H30C H 0.5785 0.2499 0.2596 0.043 Uiso 1 1 calc GR . . . . C15 C 0.5145(4) 0.43573(10) 0.0857(3) 0.0247(7) Uani 0.899(2) 1 d . U P A 1 C25 C 0.0666(2) 0.24999(8) 0.06735(19) 0.0286(5) Uani 1 1 d . . . . . H25A H 0.1009 0.2805 0.0241 0.043 Uiso 1 1 calc GR . . . . H25B H -0.0084 0.2331 0.0193 0.043 Uiso 1 1 calc GR . . . . H25C H 0.1414 0.2245 0.0829 0.043 Uiso 1 1 calc GR . . . . C9 C 0.2371(3) 0.44599(12) 0.1179(3) 0.0287(7) Uani 0.899(2) 1 d . U P A 1 H9 H 0.1413 0.4489 0.1283 0.034 Uiso 0.899(2) 1 calc R . P A 1 C8 C 0.3230(3) 0.45066(10) 0.2154(2) 0.0231(6) Uani 0.899(2) 1 d . U P A 1 C10 C 0.4150(3) 0.43295(9) -0.0085(3) 0.0252(6) Uani 0.899(2) 1 d . U P A 1 C7 C 0.0294(3) 0.44498(9) 0.7981(2) 0.0320(5) Uani 1 1 d . . . . . H7A H 0.0593 0.4679 0.8650 0.048 Uiso 1 1 calc GR . . . . H7B H 0.0560 0.4083 0.8166 0.048 Uiso 1 1 calc GR . . . . H7C H -0.0708 0.4472 0.7846 0.048 Uiso 1 1 calc GR . . . . C28 C 0.5969(2) 0.28364(8) 0.4846(2) 0.0309(5) Uani 1 1 d . . . . . H28A H 0.6235 0.3117 0.4304 0.046 Uiso 1 1 calc GR . . . . H28B H 0.6775 0.2620 0.5081 0.046 Uiso 1 1 calc GR . . . . H28C H 0.5603 0.2995 0.5556 0.046 Uiso 1 1 calc GR . . . . C16 C 0.4718(3) 0.44549(9) 0.2072(3) 0.0270(6) Uani 0.899(2) 1 d . U P A 1 C26 C -0.0626(2) 0.22349(9) 0.2479(2) 0.0339(5) Uani 1 1 d . . . . . H26A H 0.0037 0.1961 0.2743 0.051 Uiso 1 1 calc GR . . . . H26B H -0.1322 0.2081 0.1916 0.051 Uiso 1 1 calc GR . . . . H26C H -0.1073 0.2376 0.3170 0.051 Uiso 1 1 calc GR . . . . C6 C 0.1801(2) 0.59093(8) 0.5518(2) 0.0308(5) Uani 1 1 d . . . . . H6A H 0.2311 0.5964 0.4802 0.046 Uiso 1 1 calc GR . . . . H6B H 0.2326 0.6057 0.6210 0.046 Uiso 1 1 calc GR . . . . H6C H 0.0907 0.6087 0.5419 0.046 Uiso 1 1 calc GR . . . . C11 C 0.4513(4) 0.42503(10) -0.1259(3) 0.0337(7) Uani 0.899(2) 1 d . U P A 1 H11 H 0.3829 0.4235 -0.1897 0.040 Uiso 0.899(2) 1 calc R . P A 1 C24 C -0.0949(3) 0.31177(10) 0.1548(2) 0.0429(7) Uani 1 1 d . . . . . H24A H -0.1338 0.3246 0.2278 0.064 Uiso 1 1 calc GR . . . . H24B H -0.1684 0.2968 0.1017 0.064 Uiso 1 1 calc GR . . . . H24C H -0.0513 0.3413 0.1148 0.064 Uiso 1 1 calc GR . . . . C14 C 0.6521(4) 0.42904(10) 0.0622(3) 0.0328(6) Uani 0.899(2) 1 d . U P A 1 H14 H 0.7213 0.4302 0.1255 0.039 Uiso 0.899(2) 1 calc R . P A 1 C12 C 0.5893(5) 0.41944(12) -0.1468(3) 0.0362(10) Uani 0.899(2) 1 d . U P A 1 H12 H 0.6165 0.4147 -0.2258 0.043 Uiso 0.899(2) 1 calc R . P A 1 C13 C 0.6876(4) 0.42080(12) -0.0527(4) 0.0383(8) Uani 0.899(2) 1 d . U P A 1 H13 H 0.7816 0.4159 -0.0679 0.046 Uiso 0.899(2) 1 calc R . P A 1 O1W O 0.5067(7) 0.5632(3) 0.4469(6) 0.0372(16) Uani 0.25 1 d . . P . . H1WA H 0.4842 0.5580 0.5204 0.045 Uiso 0.25 1 d R . P . . H1WB H 0.4434 0.5444 0.4039 0.045 Uiso 0.25 1 d R . P . . C12' C 0.643(5) 0.4203(15) -0.119(5) 0.0362(10) Uani 0.101(2) 1 d . . P A 2 H12' H 0.7115 0.4117 -0.1720 0.043 Uiso 0.101(2) 1 calc R . P A 2 C13' C 0.500(5) 0.4213(13) -0.159(4) 0.0383(8) Uani 0.101(2) 1 d . . P A 2 H13' H 0.4764 0.4171 -0.2421 0.046 Uiso 0.101(2) 1 calc R . P A 2 C10' C 0.570(5) 0.4393(11) 0.071(3) 0.0252(6) Uani 0.101(2) 1 d . . P A 2 C15' C 0.450(4) 0.4369(10) 0.037(3) 0.0247(7) Uani 0.101(2) 1 d . . P A 2 C14' C 0.398(3) 0.4280(10) -0.086(4) 0.0328(6) Uani 0.101(2) 1 d . . P A 2 H14' H 0.3028 0.4271 -0.1103 0.039 Uiso 0.101(2) 1 calc R . P A 2 C11' C 0.677(4) 0.4318(11) -0.004(4) 0.0337(7) Uani 0.101(2) 1 d . . P A 2 H11' H 0.7701 0.4347 0.0251 0.040 Uiso 0.101(2) 1 calc R . P A 2 C16' C 0.319(3) 0.4454(8) 0.125(2) 0.0270(6) Uani 0.101(2) 1 d . . P A 2 C8' C 0.373(3) 0.4551(10) 0.243(3) 0.0231(6) Uani 0.101(2) 1 d . . P A 2 O3 O 0.27616(19) 0.43754(7) 0.00708(15) 0.0320(4) Uani 0.899(2) 1 d . . P A 1 O4' O 0.193(3) 0.4451(12) 0.096(2) 0.0413(7) Uani 0.101(2) 1 d . . P A 2 O3' O 0.6131(17) 0.4486(6) 0.1911(14) 0.0320(4) Uani 0.101(2) 1 d . . P A 2 C9' C 0.517(4) 0.4554(14) 0.262(4) 0.0287(7) Uani 0.101(2) 1 d . . P A 2 H9' H 0.5480 0.4618 0.3427 0.034 Uiso 0.101(2) 1 calc R . P A 2 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 O5 0.0305(9) 0.0125(6) 0.0345(9) -0.0069(6) -0.0004(7) 0.0002(6) O2 0.0485(11) 0.0188(7) 0.0324(9) 0.0033(6) 0.0048(8) 0.0054(7) O1 0.0343(10) 0.0268(8) 0.0322(9) -0.0102(6) 0.0016(7) 0.0075(7) N3 0.0276(11) 0.0130(8) 0.0312(10) -0.0042(7) 0.0016(8) 0.0029(7) N1 0.0302(11) 0.0129(7) 0.0246(9) -0.0013(6) 0.0003(8) 0.0036(7) N2 0.0320(11) 0.0156(8) 0.0306(10) 0.0002(7) 0.0033(8) 0.0027(7) O4 0.0367(16) 0.0556(14) 0.0306(14) -0.0044(10) -0.0057(9) -0.0001(11) N4 0.0283(11) 0.0190(8) 0.0254(9) -0.0014(7) 0.0021(8) 0.0050(7) C21 0.0216(11) 0.0150(9) 0.0228(10) 0.0017(7) 0.0047(8) 0.0029(7) C20 0.0246(12) 0.0144(9) 0.0220(10) -0.0018(7) 0.0060(9) 0.0005(7) C17 0.0271(12) 0.0124(8) 0.0218(10) -0.0007(7) 0.0023(9) 0.0022(8) C22 0.0280(12) 0.0144(9) 0.0214(10) -0.0002(7) 0.0019(9) -0.0011(8) C2 0.0212(12) 0.0152(9) 0.0269(11) -0.0043(7) -0.0025(9) 0.0023(7) C19 0.0219(12) 0.0193(9) 0.0219(10) -0.0037(7) 0.0038(8) 0.0017(8) C18 0.0270(12) 0.0164(9) 0.0245(11) -0.0017(7) 0.0031(9) 0.0066(8) C3 0.0214(12) 0.0209(10) 0.0294(12) -0.0037(8) -0.0044(9) 0.0052(8) C4 0.0268(12) 0.0196(10) 0.0233(11) -0.0018(8) -0.0020(9) 0.0060(8) C5 0.0277(12) 0.0134(9) 0.0235(10) -0.0019(7) -0.0009(9) 0.0043(8) C27 0.0229(12) 0.0180(9) 0.0265(11) 0.0015(8) 0.0021(9) 0.0025(8) C1 0.0311(13) 0.0168(9) 0.0261(11) 0.0003(8) 0.0028(9) 0.0034(8) C29 0.0319(13) 0.0198(10) 0.0298(12) 0.0029(8) 0.0011(10) 0.0043(9) C23 0.0247(13) 0.0244(10) 0.0295(12) -0.0085(8) -0.0009(10) 0.0024(8) C30 0.0233(13) 0.0265(11) 0.0366(13) 0.0030(9) 0.0054(10) 0.0054(9) C15 0.032(2) 0.0149(11) 0.0271(15) 0.0019(9) 0.0015(14) -0.0006(12) C25 0.0333(14) 0.0259(11) 0.0263(11) -0.0029(8) -0.0002(10) -0.0005(9) C9 0.029(2) 0.0264(12) 0.0305(18) -0.0023(11) 0.0033(14) 0.0042(14) C8 0.0299(19) 0.0145(10) 0.0246(15) 0.0000(9) 0.0002(11) 0.0013(11) C10 0.0291(17) 0.0160(11) 0.0302(17) 0.0025(10) -0.0013(12) 0.0003(9) C7 0.0340(14) 0.0326(12) 0.0298(12) 0.0008(9) 0.0055(10) 0.0064(10) C28 0.0266(13) 0.0231(11) 0.0420(14) 0.0026(9) -0.0058(10) 0.0030(9) C16 0.0317(16) 0.0189(11) 0.0298(14) 0.0019(9) -0.0023(12) 0.0001(10) C26 0.0271(14) 0.0389(13) 0.0362(13) -0.0110(10) 0.0055(11) -0.0050(10) C6 0.0370(15) 0.0161(10) 0.0394(13) -0.0047(9) 0.0018(11) 0.0027(9) C11 0.049(3) 0.0238(13) 0.0282(19) 0.0023(12) 0.0005(13) -0.0016(14) C24 0.0347(16) 0.0406(14) 0.0512(16) -0.0171(12) -0.0145(13) 0.0099(11) C14 0.034(2) 0.0261(13) 0.0386(19) 0.0013(11) 0.0044(14) -0.0019(12) C12 0.055(3) 0.0214(12) 0.034(2) 0.0008(12) 0.0167(18) -0.0022(18) C13 0.045(2) 0.0278(15) 0.044(2) 0.0003(14) 0.0151(17) -0.0048(12) O1W 0.031(4) 0.046(4) 0.034(4) -0.003(3) -0.002(3) -0.014(3) C12' 0.055(3) 0.0214(12) 0.034(2) 0.0008(12) 0.0167(18) -0.0022(18) C13' 0.045(2) 0.0278(15) 0.044(2) 0.0003(14) 0.0151(17) -0.0048(12) C10' 0.0291(17) 0.0160(11) 0.0302(17) 0.0025(10) -0.0013(12) 0.0003(9) C15' 0.032(2) 0.0149(11) 0.0271(15) 0.0019(9) 0.0015(14) -0.0006(12) C14' 0.034(2) 0.0261(13) 0.0386(19) 0.0013(11) 0.0044(14) -0.0019(12) C11' 0.049(3) 0.0238(13) 0.0282(19) 0.0023(12) 0.0005(13) -0.0016(14) C16' 0.0317(16) 0.0189(11) 0.0298(14) 0.0019(9) -0.0023(12) 0.0001(10) C8' 0.0299(19) 0.0145(10) 0.0246(15) 0.0000(9) 0.0002(11) 0.0013(11) O3 0.0353(12) 0.0347(10) 0.0255(10) -0.0030(7) -0.0023(8) 0.0039(8) O4' 0.0367(16) 0.0556(14) 0.0306(14) -0.0044(10) -0.0057(9) -0.0001(11) O3' 0.0353(12) 0.0347(10) 0.0255(10) -0.0030(7) -0.0023(8) 0.0039(8) C9' 0.029(2) 0.0264(12) 0.0305(18) -0.0023(11) 0.0033(14) 0.0042(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N3 C6 121.10(18) . . ? C3 N3 C2 119.68(16) . . ? C3 N3 C6 119.15(17) . . ? C5 N1 C17 128.63(16) . . ? C1 N1 C17 125.09(17) . . ? C1 N1 C5 106.17(15) . . ? C1 N2 C2 103.19(16) . . ? C3 N4 C4 126.61(18) . . ? C3 N4 C7 116.32(17) . . ? C4 N4 C7 117.02(17) . . ? C20 C21 C27 122.65(16) . . ? C22 C21 C20 117.29(18) . . ? C22 C21 C27 120.05(18) . . ? O5 C20 C21 115.12(17) . . ? O5 C20 C19 122.19(18) . . ? C21 C20 C19 122.68(17) . . ? C22 C17 N1 119.32(18) . . ? C22 C17 C18 121.70(17) . . ? C18 C17 N1 118.89(17) . . ? C17 C22 C21 120.53(19) . . ? N2 C2 N3 125.67(17) . . ? N2 C2 C5 112.81(17) . . ? C5 C2 N3 121.50(19) . . ? C20 C19 C23 123.35(17) . . ? C18 C19 C20 116.90(18) . . ? C18 C19 C23 119.74(18) . . ? C17 C18 C19 120.84(18) . . ? O1 C3 N3 121.96(19) . . ? O1 C3 N4 120.8(2) . . ? N3 C3 N4 117.19(17) . . ? O2 C4 N4 120.63(19) . . ? O2 C4 C5 127.91(19) . . ? C5 C4 N4 111.46(17) . . ? N1 C5 C4 131.91(17) . . ? C2 C5 N1 104.60(17) . . ? C2 C5 C4 123.49(18) . . ? C21 C27 C29 109.31(17) . . ? C30 C27 C21 111.45(17) . . ? C30 C27 C29 110.91(16) . . ? C30 C27 C28 106.42(18) . . ? C28 C27 C21 110.98(16) . . ? C28 C27 C29 107.68(17) . . ? N1 C1 C8 121.50(18) . . ? N1 C1 C8' 123.2(10) . . ? N2 C1 N1 113.22(18) . . ? N2 C1 C8 125.28(19) . . ? N2 C1 C8' 118.5(10) . . ? C19 C23 C26 111.26(18) . . ? C25 C23 C19 110.31(18) . . ? C25 C23 C26 111.04(17) . . ? C25 C23 C24 106.16(19) . . ? C24 C23 C19 111.23(17) . . ? C24 C23 C26 106.7(2) . . ? C10 C15 C16 119.4(3) . . ? C14 C15 C10 118.9(3) . . ? C14 C15 C16 121.7(3) . . ? O3 C9 C8 125.1(3) . . ? C9 C8 C1 121.0(3) . . ? C9 C8 C16 120.7(3) . . ? C16 C8 C1 118.2(2) . . ? C15 C10 C11 121.4(3) . . ? O3 C10 C15 122.8(3) . . ? O3 C10 C11 115.9(4) . . ? O4 C16 C15 123.4(3) . . ? O4 C16 C8 122.5(3) . . ? C8 C16 C15 114.2(3) . . ? C12 C11 C10 118.4(3) . . ? C13 C14 C15 119.7(3) . . ? C11 C12 C13 120.1(3) . . ? C14 C13 C12 121.5(3) . . ? C11' C12' C13' 119(4) . . ? C14' C13' C12' 123(4) . . ? C15' C10' C11' 123(3) . . ? C15' C10' O3' 123(4) . . ? C11' C10' O3' 114(4) . . ? C10' C15' C14' 126(3) . . ? C10' C15' C16' 124(4) . . ? C14' C15' C16' 110(3) . . ? C13' C14' C15' 112(4) . . ? C12' C11' C10' 118(4) . . ? C8' C16' C15' 109(3) . . ? O4' C16' C15' 128(3) . . ? O4' C16' C8' 124(3) . . ? C16' C8' C1 115(2) . . ? C9' C8' C1 127(3) . . ? C9' C8' C16' 117(3) . . ? C9 O3 C10 117.8(2) . . ? C9' O3' C10' 116(3) . . ? O3' C9' C8' 132(4) . . ? 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 O5 C20 1.371(2) . ? O2 C4 1.229(2) . ? O1 C3 1.226(2) . ? N3 C2 1.379(2) . ? N3 C3 1.373(3) . ? N3 C6 1.466(3) . ? N1 C17 1.447(2) . ? N1 C5 1.394(3) . ? N1 C1 1.354(3) . ? N2 C2 1.359(3) . ? N2 C1 1.344(2) . ? O4 C16 1.226(3) . ? N4 C3 1.401(3) . ? N4 C4 1.415(3) . ? N4 C7 1.470(3) . ? C21 C20 1.410(3) . ? C21 C22 1.398(3) . ? C21 C27 1.543(3) . ? C20 C19 1.413(3) . ? C17 C22 1.373(3) . ? C17 C18 1.377(3) . ? C2 C5 1.372(3) . ? C19 C18 1.398(3) . ? C19 C23 1.544(3) . ? C4 C5 1.415(3) . ? C27 C29 1.546(3) . ? C27 C30 1.533(3) . ? C27 C28 1.541(3) . ? C1 C8 1.478(3) . ? C1 C8' 1.48(3) . ? C23 C25 1.539(3) . ? C23 C26 1.544(3) . ? C23 C24 1.540(3) . ? C15 C10 1.394(4) . ? C15 C16 1.473(4) . ? C15 C14 1.392(4) . ? C9 C8 1.344(4) . ? C9 O3 1.342(4) . ? C8 C16 1.463(4) . ? C10 C11 1.401(4) . ? C10 O3 1.379(3) . ? C11 C12 1.385(5) . ? C14 C13 1.373(4) . ? C12 C13 1.385(5) . ? C12' C13' 1.44(6) . ? C12' C11' 1.35(5) . ? C13' C14' 1.34(4) . ? C10' C15' 1.22(5) . ? C10' C11' 1.39(5) . ? C10' O3' 1.41(4) . ? C15' C14' 1.45(4) . ? C15' C16' 1.68(4) . ? C16' C8' 1.42(3) . ? C16' O4' 1.25(3) . ? C8' C9' 1.40(5) . ? O3' C9' 1.28(4) . ?