#------------------------------------------------------------------------------ #$Date: 2024-07-05 21:01:53 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293285 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159923.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_7159923 loop_ _publ_author_name 'Liu, Yan' 'Yang, Qin' 'Wang, Wei' 'Fu, Yang' 'Ding, Qiuping' 'Peng, Yiyuan' _publ_section_title ; Visible-light-induced three-component reactions of α-diazoesters, quinazolinones and cyclic ethers toward quinazoline-based hybrids. ; _journal_issue 21 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4332 _journal_page_last 4346 _journal_paper_doi 10.1039/d4ob00295d _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C28 H28 N2 O4' _chemical_formula_sum 'C28 H28 N2 O4' _chemical_formula_weight 456.52 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-01-08 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2024-01-09 deposited with the CCDC. 2024-04-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.359(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.1921(6) _cell_length_b 11.9580(15) _cell_length_c 32.979(4) _cell_measurement_reflns_used 5310 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.6130 _cell_measurement_theta_min 3.9350 _cell_volume 2441.2(5) _computing_cell_refinement 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0353 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -42.00 11.00 1.00 4.86 -- -15.92 -77.00 0.00 53 2 \w -42.00 11.00 1.00 4.86 -- -15.92 -77.00 -60.00 53 3 \w -52.00 86.00 1.00 4.86 -- 16.85 0.00 -90.00 138 4 \w -42.00 44.00 1.00 4.86 -- 16.85 -77.00-180.00 86 5 \w -35.00 53.00 1.00 4.86 -- -15.92 37.00 -60.00 88 6 \w -52.00 36.00 1.00 4.86 -- 16.85 -37.00 60.00 88 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0234535000 _diffrn_orient_matrix_UB_12 0.0328577000 _diffrn_orient_matrix_UB_13 0.0174726000 _diffrn_orient_matrix_UB_21 0.0097351000 _diffrn_orient_matrix_UB_22 0.0480670000 _diffrn_orient_matrix_UB_23 -0.0123817000 _diffrn_orient_matrix_UB_31 -0.1117864000 _diffrn_orient_matrix_UB_32 0.0110572000 _diffrn_orient_matrix_UB_33 0.0020959000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1183 _diffrn_reflns_av_unetI/netI 0.0796 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 25025 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 3.334 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53457 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.242 _exptl_crystal_description irregular _exptl_crystal_F_000 968 _exptl_crystal_preparation synthesized _exptl_crystal_recrystallization_method 'slow evaporation' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.256 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 4981 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.1700 _refine_ls_R_factor_gt 0.1175 _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^)+(0.0866P)^2^+4.0216P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2527 _refine_ls_wR_factor_ref 0.2823 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2898 _reflns_number_total 4981 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00295d2.cif _cod_data_source_block ly-0510-1_auto _cod_depositor_comments 'Adding full bibliography for 7159923.cif.' _cod_original_cell_volume 2441.3(5) _cod_database_code 7159923 _shelxl_version_number 2014-1 _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 0.992 _shelx_estimated_absorpt_t_min 0.975 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C20(H20) 2.b Secondary CH2 refined with riding coordinates: C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C14(H14), C24(H24), C26(H26), C13(H13), C25(H25), C28(H28), C27(H27), C4(H4), C7(H7), C6(H6), C5(H5) 2.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C22(H22A,H22B,H22C) ; _shelx_res_file ; TITL ly-0510-1_auto_a.res in P2(1)/n REM Old TITL REM SHELXT solution in P2(1)/n REM R1 0.249, Rweak 0.219, Alpha 0.083, Orientation as input REM Formula found by SHELXT: C28 N3 O3 CELL 0.71073 6.1921 11.958 32.9795 90 91.359 90 ZERR 4 0.0006 0.0015 0.0037 0 0.01 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 112 112 8 16 L.S. 20 PLAN 20 SIZE 0.1 0.13 0.3 TEMP 19.85 BOND $H list 4 fmap 2 acta SHEL 999 0.8 OMIT 4 5 11 REM REM REM WGHT 0.086600 4.021600 FVAR 0.27394 O1 4 0.575705 0.635086 0.626898 11.00000 0.05324 0.05024 = 0.05806 -0.00714 0.02154 0.00374 O2 4 0.018791 0.520994 0.738434 11.00000 0.04833 0.07746 = 0.04273 -0.00823 0.00877 -0.01216 N2 3 0.813378 0.537439 0.587440 11.00000 0.04537 0.04562 = 0.03461 -0.00292 0.00568 0.00327 O4 4 -0.472209 0.423085 0.775100 11.00000 0.04753 0.06798 = 0.10360 -0.00336 0.01221 -0.00818 N1 3 1.119464 0.629716 0.559293 11.00000 0.05336 0.05249 = 0.04008 0.00221 0.01010 -0.00415 O3 4 -0.155639 0.335647 0.779329 11.00000 0.06128 0.07462 = 0.10369 0.01396 0.01032 0.00299 C9 1 1.072729 0.432967 0.548476 11.00000 0.04597 0.04587 = 0.02983 0.00134 0.00358 -0.00117 C1 1 0.999631 0.541358 0.565463 11.00000 0.04335 0.04783 = 0.02748 0.00136 0.00177 -0.00057 C10 1 0.951203 0.337583 0.552029 11.00000 0.04827 0.05003 = 0.04464 -0.00067 0.01280 0.00220 AFIX 43 H10 2 0.818096 0.341133 0.564449 11.00000 -1.20000 AFIX 0 C2 1 0.749202 0.631155 0.603100 11.00000 0.04450 0.05578 = 0.02855 0.00055 0.00267 0.00670 C11 1 1.024310 0.235777 0.537326 11.00000 0.06556 0.04176 = 0.05641 0.00432 0.01297 0.00187 AFIX 43 H11 2 0.938671 0.172407 0.539919 11.00000 -1.20000 AFIX 0 C21 1 -0.261170 0.418962 0.773137 11.00000 0.05242 0.05902 = 0.04902 -0.00589 0.00782 -0.00145 C20 1 -0.165756 0.532837 0.761863 11.00000 0.04147 0.06073 = 0.04944 0.00715 0.00704 -0.00059 AFIX 13 H20 2 -0.274675 0.574802 0.746098 11.00000 -1.20000 AFIX 0 C16 1 0.466332 0.531403 0.635300 11.00000 0.04370 0.05376 = 0.04394 -0.00317 0.00704 0.00530 AFIX 23 H16A 2 0.567244 0.477082 0.646628 11.00000 -1.20000 H16B 2 0.401920 0.500805 0.610604 11.00000 -1.20000 AFIX 0 C12 1 1.222597 0.226889 0.518855 11.00000 0.06201 0.05121 = 0.04290 -0.00001 0.00765 0.00883 C14 1 1.271282 0.424815 0.529502 11.00000 0.04885 0.05571 = 0.04581 -0.00351 0.01080 -0.00349 AFIX 43 H14 2 1.355630 0.488510 0.526538 11.00000 -1.20000 AFIX 0 C23 1 -0.110296 0.597721 0.800049 11.00000 0.05257 0.04700 = 0.03719 0.00266 0.00474 -0.00133 C17 1 0.293285 0.558242 0.665465 11.00000 0.05120 0.05964 = 0.04174 -0.00671 0.00917 0.00348 AFIX 23 H17A 2 0.359953 0.589829 0.689790 11.00000 -1.20000 H17B 2 0.195341 0.613624 0.653901 11.00000 -1.20000 AFIX 0 C8 1 1.048967 0.728908 0.575395 11.00000 0.06255 0.05159 = 0.04087 -0.00327 0.00832 -0.00813 C24 1 -0.263641 0.665540 0.817426 11.00000 0.05444 0.06826 = 0.05560 0.00437 0.00608 0.00867 AFIX 43 H24 2 -0.400643 0.671449 0.805444 11.00000 -1.20000 AFIX 0 C3 1 0.857199 0.735456 0.597584 11.00000 0.06301 0.04842 = 0.03633 0.00085 0.00475 -0.00242 C26 1 -0.014868 0.717278 0.870839 11.00000 0.08667 0.05059 = 0.04442 -0.00520 0.00176 0.00301 AFIX 43 H26 2 0.016277 0.756013 0.894721 11.00000 -1.20000 AFIX 0 C13 1 1.344055 0.323856 0.515113 11.00000 0.04644 0.05931 = 0.05056 -0.00316 0.01707 0.00530 AFIX 43 H13 2 1.477063 0.320519 0.502650 11.00000 -1.20000 AFIX 0 C25 1 -0.214516 0.724669 0.852530 11.00000 0.07221 0.05286 = 0.06070 -0.00412 0.00665 0.01362 AFIX 43 H25 2 -0.319079 0.770131 0.863823 11.00000 -1.20000 AFIX 0 C18 1 0.167985 0.455282 0.676416 11.00000 0.07626 0.06639 = 0.04477 -0.00744 0.01659 -0.01038 AFIX 23 H18A 2 0.260607 0.406979 0.692831 11.00000 -1.20000 H18B 2 0.129990 0.415111 0.651710 11.00000 -1.20000 AFIX 0 C19 1 -0.035350 0.478172 0.699196 11.00000 0.07304 0.09116 = 0.04139 -0.00633 0.00860 -0.02300 AFIX 23 H19A 2 -0.123797 0.531999 0.684361 11.00000 -1.20000 H19B 2 -0.117769 0.409656 0.701756 11.00000 -1.20000 AFIX 0 C28 1 0.093372 0.590916 0.818350 11.00000 0.05859 0.05403 = 0.06349 -0.00833 0.00629 0.01196 AFIX 43 H28 2 0.199078 0.545844 0.807226 11.00000 -1.20000 AFIX 0 C27 1 0.138320 0.651852 0.853387 11.00000 0.06725 0.06390 = 0.06330 -0.00845 -0.00970 0.00530 AFIX 43 H27 2 0.275863 0.648065 0.865260 11.00000 -1.20000 AFIX 0 C4 1 0.787980 0.838150 0.613746 11.00000 0.08389 0.05747 = 0.04789 -0.00361 0.01384 0.00242 AFIX 43 H4 2 0.660279 0.842135 0.627961 11.00000 -1.20000 AFIX 0 C7 1 1.172169 0.826620 0.570755 11.00000 0.09620 0.06369 = 0.06173 -0.00589 0.02600 -0.02197 AFIX 43 H7 2 1.300438 0.824350 0.556669 11.00000 -1.20000 AFIX 0 C6 1 1.102751 0.924770 0.587004 11.00000 0.13918 0.05600 = 0.07353 -0.00888 0.02999 -0.02737 AFIX 43 H6 2 1.185326 0.989019 0.583870 11.00000 -1.20000 AFIX 0 C5 1 0.909553 0.931135 0.608355 11.00000 0.12810 0.05131 = 0.07221 -0.01263 0.02369 -0.00400 AFIX 43 H5 2 0.864818 0.999294 0.618829 11.00000 -1.20000 AFIX 0 C15 1 1.305626 0.116558 0.503341 11.00000 0.10000 0.05651 = 0.07708 -0.00126 0.03264 0.01863 AFIX 137 H15A 2 1.434087 0.095967 0.518410 11.00000 -1.50000 H15B 2 1.338201 0.123547 0.475139 11.00000 -1.50000 H15C 2 1.197387 0.060003 0.506607 11.00000 -1.50000 AFIX 0 C22 1 -0.583131 0.319254 0.785301 11.00000 0.06935 0.07794 = 0.12187 -0.00394 0.01994 -0.02513 AFIX 137 H22A 2 -0.555772 0.263892 0.764977 11.00000 -1.50000 H22B 2 -0.735681 0.332821 0.786414 11.00000 -1.50000 H22C 2 -0.530773 0.292869 0.811209 11.00000 -1.50000 AFIX 0 HKLF 4 REM ly-0510-1_auto_a.res in P2(1)/n REM R1 = 0.1175 for 2898 Fo > 4sig(Fo) and 0.1700 for all 4981 data REM 309 parameters refined using 0 restraints END WGHT 0.0867 4.0090 REM Highest difference peak 0.256, deepest hole -0.230, 1-sigma level 0.060 Q1 1 0.3511 0.6324 0.5985 11.00000 0.05 0.26 Q2 1 1.2608 0.7335 0.6004 11.00000 0.05 0.25 Q3 1 -0.1921 0.4511 0.7100 11.00000 0.05 0.24 Q4 1 0.2442 0.6680 0.8121 11.00000 0.05 0.24 Q5 1 0.0356 0.3352 0.7965 11.00000 0.05 0.23 Q6 1 0.1739 0.3780 0.7388 11.00000 0.05 0.23 Q7 1 0.2502 0.5218 0.7429 11.00000 0.05 0.22 Q8 1 0.2766 0.5394 0.5956 11.00000 0.05 0.22 Q9 1 -0.3285 0.5847 0.7951 11.00000 0.05 0.21 Q10 1 -0.7057 0.4361 0.7700 11.00000 0.05 0.21 Q11 1 1.5355 0.4435 0.5504 11.00000 0.05 0.20 Q12 1 0.3712 0.6351 0.6197 11.00000 0.05 0.20 Q13 1 0.3563 0.6654 0.8761 11.00000 0.05 0.20 Q14 1 0.1495 0.6265 0.6119 11.00000 0.05 0.20 Q15 1 0.3241 0.6555 0.7833 11.00000 0.05 0.20 Q16 1 1.4268 0.3477 0.4746 11.00000 0.05 0.20 Q17 1 1.0931 0.2751 0.5902 11.00000 0.05 0.19 Q18 1 0.2458 0.4919 0.7010 11.00000 0.05 0.19 Q19 1 0.6346 0.5256 0.5922 11.00000 0.05 0.19 Q20 1 1.4113 0.6241 0.5558 11.00000 0.05 0.19 ; _shelx_res_checksum 33358 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.284 _oxdiff_exptl_absorpt_empirical_full_min 0.385 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_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 O1 O 0.5757(5) 0.6351(3) 0.62690(10) 0.0535(9) Uani 1 1 d . . . . . O2 O 0.0188(5) 0.5210(3) 0.73843(9) 0.0561(9) Uani 1 1 d . . . . . N2 N 0.8134(5) 0.5374(3) 0.58744(10) 0.0418(8) Uani 1 1 d . . . . . O4 O -0.4722(5) 0.4231(3) 0.77510(13) 0.0729(11) Uani 1 1 d . . . . . N1 N 1.1195(6) 0.6297(3) 0.55929(11) 0.0485(9) Uani 1 1 d . . . . . O3 O -0.1556(6) 0.3356(4) 0.77933(13) 0.0797(12) Uani 1 1 d . . . . . C9 C 1.0727(7) 0.4330(4) 0.54848(12) 0.0405(10) Uani 1 1 d . . . . . C1 C 0.9996(6) 0.5414(4) 0.56546(11) 0.0395(10) Uani 1 1 d . . . . . C10 C 0.9512(7) 0.3376(4) 0.55203(13) 0.0475(11) Uani 1 1 d . . . . . H10 H 0.8181 0.3411 0.5644 0.057 Uiso 1 1 calc R . . . . C2 C 0.7492(7) 0.6312(4) 0.60310(12) 0.0429(10) Uani 1 1 d . . . . . C11 C 1.0243(8) 0.2358(4) 0.53733(14) 0.0544(12) Uani 1 1 d . . . . . H11 H 0.9387 0.1724 0.5399 0.065 Uiso 1 1 calc R . . . . C21 C -0.2612(8) 0.4190(4) 0.77314(14) 0.0534(12) Uani 1 1 d . . . . . C20 C -0.1658(7) 0.5328(4) 0.76186(14) 0.0505(12) Uani 1 1 d . . . . . H20 H -0.2747 0.5748 0.7461 0.061 Uiso 1 1 calc R . . . . C16 C 0.4663(7) 0.5314(4) 0.63530(13) 0.0470(11) Uani 1 1 d . . . . . H16A H 0.5672 0.4771 0.6466 0.056 Uiso 1 1 calc R . . . . H16B H 0.4019 0.5008 0.6106 0.056 Uiso 1 1 calc R . . . . C12 C 1.2226(8) 0.2269(4) 0.51886(13) 0.0519(12) Uani 1 1 d . . . . . C14 C 1.2713(7) 0.4248(4) 0.52950(13) 0.0500(11) Uani 1 1 d . . . . . H14 H 1.3556 0.4885 0.5265 0.060 Uiso 1 1 calc R . . . . C23 C -0.1103(7) 0.5977(4) 0.80005(13) 0.0455(11) Uani 1 1 d . . . . . C17 C 0.2933(7) 0.5582(4) 0.66547(13) 0.0507(12) Uani 1 1 d . . . . . H17A H 0.3600 0.5898 0.6898 0.061 Uiso 1 1 calc R . . . . H17B H 0.1953 0.6136 0.6539 0.061 Uiso 1 1 calc R . . . . C8 C 1.0490(8) 0.7289(4) 0.57539(13) 0.0516(12) Uani 1 1 d . . . . . C24 C -0.2636(8) 0.6655(4) 0.81743(15) 0.0594(13) Uani 1 1 d . . . . . H24 H -0.4006 0.6714 0.8054 0.071 Uiso 1 1 calc R . . . . C3 C 0.8572(8) 0.7355(4) 0.59758(13) 0.0492(11) Uani 1 1 d . . . . . C26 C -0.0149(9) 0.7173(4) 0.87084(15) 0.0606(13) Uani 1 1 d . . . . . H26 H 0.0163 0.7560 0.8947 0.073 Uiso 1 1 calc R . . . . C13 C 1.3441(7) 0.3239(4) 0.51511(14) 0.0519(12) Uani 1 1 d . . . . . H13 H 1.4771 0.3205 0.5027 0.062 Uiso 1 1 calc R . . . . C25 C -0.2145(9) 0.7247(4) 0.85253(16) 0.0618(13) Uani 1 1 d . . . . . H25 H -0.3191 0.7701 0.8638 0.074 Uiso 1 1 calc R . . . . C18 C 0.1680(8) 0.4553(4) 0.67642(15) 0.0622(14) Uani 1 1 d . . . . . H18A H 0.2606 0.4070 0.6928 0.075 Uiso 1 1 calc R . . . . H18B H 0.1300 0.4151 0.6517 0.075 Uiso 1 1 calc R . . . . C19 C -0.0353(9) 0.4782(5) 0.69920(14) 0.0684(15) Uani 1 1 d . . . . . H19A H -0.1238 0.5320 0.6844 0.082 Uiso 1 1 calc R . . . . H19B H -0.1178 0.4097 0.7018 0.082 Uiso 1 1 calc R . . . . C28 C 0.0934(8) 0.5909(4) 0.81835(16) 0.0586(13) Uani 1 1 d . . . . . H28 H 0.1991 0.5458 0.8072 0.070 Uiso 1 1 calc R . . . . C27 C 0.1383(9) 0.6519(5) 0.85339(16) 0.0650(14) Uani 1 1 d . . . . . H27 H 0.2759 0.6481 0.8653 0.078 Uiso 1 1 calc R . . . . C4 C 0.7880(9) 0.8382(4) 0.61375(15) 0.0629(14) Uani 1 1 d . . . . . H4 H 0.6603 0.8421 0.6280 0.075 Uiso 1 1 calc R . . . . C7 C 1.1722(10) 0.8266(5) 0.57075(17) 0.0735(17) Uani 1 1 d . . . . . H7 H 1.3004 0.8243 0.5567 0.088 Uiso 1 1 calc R . . . . C6 C 1.1028(12) 0.9248(5) 0.58700(18) 0.089(2) Uani 1 1 d . . . . . H6 H 1.1853 0.9890 0.5839 0.107 Uiso 1 1 calc R . . . . C5 C 0.9096(11) 0.9311(5) 0.60835(18) 0.0835(19) Uani 1 1 d . . . . . H5 H 0.8648 0.9993 0.6188 0.100 Uiso 1 1 calc R . . . . C15 C 1.3056(10) 0.1166(5) 0.50334(18) 0.0774(18) Uani 1 1 d . . . . . H15A H 1.4341 0.0960 0.5184 0.116 Uiso 1 1 calc GR . . . . H15B H 1.3382 0.1235 0.4751 0.116 Uiso 1 1 calc GR . . . . H15C H 1.1974 0.0600 0.5066 0.116 Uiso 1 1 calc GR . . . . C22 C -0.5831(9) 0.3193(5) 0.7853(2) 0.089(2) Uani 1 1 d . . . . . H22A H -0.5558 0.2639 0.7650 0.134 Uiso 1 1 calc GR . . . . H22B H -0.7357 0.3328 0.7864 0.134 Uiso 1 1 calc GR . . . . H22C H -0.5308 0.2929 0.8112 0.134 Uiso 1 1 calc GR . . . . 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 O1 0.0532(18) 0.0502(19) 0.0581(19) -0.0071(16) 0.0215(15) 0.0037(15) O2 0.0483(18) 0.077(2) 0.0427(17) -0.0082(17) 0.0088(14) -0.0122(17) N2 0.045(2) 0.046(2) 0.0346(18) -0.0029(16) 0.0057(15) 0.0033(17) O4 0.048(2) 0.068(2) 0.104(3) -0.003(2) 0.0122(19) -0.0082(18) N1 0.053(2) 0.052(2) 0.0401(19) 0.0022(18) 0.0101(17) -0.0041(19) O3 0.061(2) 0.075(3) 0.104(3) 0.014(2) 0.010(2) 0.003(2) C9 0.046(2) 0.046(2) 0.030(2) 0.0013(18) 0.0036(17) -0.001(2) C1 0.043(2) 0.048(2) 0.0275(19) 0.0014(18) 0.0018(16) -0.001(2) C10 0.048(3) 0.050(3) 0.045(2) -0.001(2) 0.013(2) 0.002(2) C2 0.044(2) 0.056(3) 0.029(2) 0.0005(19) 0.0027(17) 0.007(2) C11 0.066(3) 0.042(3) 0.056(3) 0.004(2) 0.013(2) 0.002(2) C21 0.052(3) 0.059(3) 0.049(3) -0.006(2) 0.008(2) -0.001(3) C20 0.041(2) 0.061(3) 0.049(3) 0.007(2) 0.007(2) -0.001(2) C16 0.044(2) 0.054(3) 0.044(2) -0.003(2) 0.0070(19) 0.005(2) C12 0.062(3) 0.051(3) 0.043(2) 0.000(2) 0.008(2) 0.009(2) C14 0.049(3) 0.056(3) 0.046(2) -0.004(2) 0.011(2) -0.003(2) C23 0.053(3) 0.047(3) 0.037(2) 0.003(2) 0.0047(19) -0.001(2) C17 0.051(3) 0.060(3) 0.042(2) -0.007(2) 0.009(2) 0.003(2) C8 0.063(3) 0.052(3) 0.041(2) -0.003(2) 0.008(2) -0.008(2) C24 0.054(3) 0.068(3) 0.056(3) 0.004(3) 0.006(2) 0.009(3) C3 0.063(3) 0.048(3) 0.036(2) 0.001(2) 0.005(2) -0.002(2) C26 0.087(4) 0.051(3) 0.044(3) -0.005(2) 0.002(3) 0.003(3) C13 0.046(2) 0.059(3) 0.051(3) -0.003(2) 0.017(2) 0.005(2) C25 0.072(3) 0.053(3) 0.061(3) -0.004(3) 0.007(3) 0.014(3) C18 0.076(3) 0.066(3) 0.045(3) -0.007(3) 0.017(2) -0.010(3) C19 0.073(3) 0.091(4) 0.041(3) -0.006(3) 0.009(2) -0.023(3) C28 0.059(3) 0.054(3) 0.063(3) -0.008(3) 0.006(2) 0.012(2) C27 0.067(3) 0.064(3) 0.063(3) -0.008(3) -0.010(3) 0.005(3) C4 0.084(4) 0.057(3) 0.048(3) -0.004(2) 0.014(3) 0.002(3) C7 0.096(4) 0.064(4) 0.062(3) -0.006(3) 0.026(3) -0.022(3) C6 0.139(6) 0.056(4) 0.074(4) -0.009(3) 0.030(4) -0.027(4) C5 0.128(5) 0.051(3) 0.072(4) -0.013(3) 0.024(4) -0.004(4) C15 0.100(4) 0.057(3) 0.077(4) -0.001(3) 0.033(3) 0.019(3) C22 0.069(4) 0.078(4) 0.122(6) -0.004(4) 0.020(4) -0.025(3) 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 O1 C16 117.8(3) . . ? C20 O2 C19 111.1(3) . . ? C2 N2 C1 116.6(4) . . ? C21 O4 C22 117.0(4) . . ? C1 N1 C8 116.7(4) . . ? C10 C9 C1 121.3(4) . . ? C10 C9 C14 118.1(4) . . ? C14 C9 C1 120.6(4) . . ? N2 C1 C9 115.8(4) . . ? N1 C1 N2 126.4(4) . . ? N1 C1 C9 117.8(3) . . ? C9 C10 H10 119.5 . . ? C9 C10 C11 120.9(4) . . ? C11 C10 H10 119.5 . . ? O1 C2 C3 115.2(4) . . ? N2 C2 O1 121.2(4) . . ? N2 C2 C3 123.6(4) . . ? C10 C11 H11 119.4 . . ? C12 C11 C10 121.3(4) . . ? C12 C11 H11 119.4 . . ? O4 C21 C20 111.6(4) . . ? O3 C21 O4 124.0(5) . . ? O3 C21 C20 124.3(4) . . ? O2 C20 C21 111.6(4) . . ? O2 C20 H20 108.6 . . ? O2 C20 C23 109.8(4) . . ? C21 C20 H20 108.6 . . ? C23 C20 C21 109.6(4) . . ? C23 C20 H20 108.6 . . ? O1 C16 H16A 110.4 . . ? O1 C16 H16B 110.4 . . ? O1 C16 C17 106.7(4) . . ? H16A C16 H16B 108.6 . . ? C17 C16 H16A 110.4 . . ? C17 C16 H16B 110.4 . . ? C11 C12 C13 117.5(4) . . ? C11 C12 C15 121.9(5) . . ? C13 C12 C15 120.7(4) . . ? C9 C14 H14 119.5 . . ? C13 C14 C9 121.0(4) . . ? C13 C14 H14 119.5 . . ? C24 C23 C20 120.1(4) . . ? C24 C23 C28 118.7(4) . . ? C28 C23 C20 121.2(4) . . ? C16 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C18 C17 C16 111.2(4) . . ? C18 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? N1 C8 C3 121.8(4) . . ? N1 C8 C7 119.8(4) . . ? C7 C8 C3 118.4(4) . . ? C23 C24 H24 119.8 . . ? C23 C24 C25 120.4(5) . . ? C25 C24 H24 119.8 . . ? C8 C3 C2 114.8(4) . . ? C4 C3 C2 124.4(4) . . ? C4 C3 C8 120.8(4) . . ? C25 C26 H26 120.6 . . ? C25 C26 C27 118.7(5) . . ? C27 C26 H26 120.6 . . ? C12 C13 H13 119.4 . . ? C14 C13 C12 121.3(4) . . ? C14 C13 H13 119.4 . . ? C24 C25 H25 119.5 . . ? C26 C25 C24 121.0(5) . . ? C26 C25 H25 119.5 . . ? C17 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C17 C18 C19 114.4(4) . . ? H18A C18 H18B 107.6 . . ? C19 C18 H18A 108.7 . . ? C19 C18 H18B 108.7 . . ? O2 C19 C18 109.7(4) . . ? O2 C19 H19A 109.7 . . ? O2 C19 H19B 109.7 . . ? C18 C19 H19A 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C23 C28 H28 120.2 . . ? C23 C28 C27 119.6(4) . . ? C27 C28 H28 120.2 . . ? C26 C27 C28 121.5(5) . . ? C26 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? C3 C4 H4 120.3 . . ? C5 C4 C3 119.3(5) . . ? C5 C4 H4 120.3 . . ? C8 C7 H7 120.1 . . ? C6 C7 C8 119.7(5) . . ? C6 C7 H7 120.1 . . ? C7 C6 H6 119.2 . . ? C7 C6 C5 121.6(5) . . ? C5 C6 H6 119.2 . . ? C4 C5 C6 120.2(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 O1 C2 1.346(5) . ? O1 C16 1.443(5) . ? O2 C20 1.402(5) . ? O2 C19 1.424(6) . ? N2 C1 1.377(5) . ? N2 C2 1.300(5) . ? O4 C21 1.311(6) . ? O4 C22 1.462(6) . ? N1 C1 1.310(5) . ? N1 C8 1.375(6) . ? O3 C21 1.206(6) . ? C9 C1 1.487(6) . ? C9 C10 1.373(6) . ? C9 C14 1.396(5) . ? C10 H10 0.9300 . ? C10 C11 1.390(6) . ? C2 C3 1.429(6) . ? C11 H11 0.9300 . ? C11 C12 1.388(6) . ? C21 C20 1.534(7) . ? C20 H20 0.9800 . ? C20 C23 1.512(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.514(5) . ? C12 C13 1.389(7) . ? C12 C15 1.510(7) . ? C14 H14 0.9300 . ? C14 C13 1.377(6) . ? C23 C24 1.383(6) . ? C23 C28 1.388(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.504(7) . ? C8 C3 1.412(6) . ? C8 C7 1.406(7) . ? C24 H24 0.9300 . ? C24 C25 1.384(7) . ? C3 C4 1.410(7) . ? C26 H26 0.9300 . ? C26 C25 1.366(7) . ? C26 C27 1.367(7) . ? C13 H13 0.9300 . ? C25 H25 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 C19 1.506(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C28 H28 0.9300 . ? C28 C27 1.389(7) . ? C27 H27 0.9300 . ? C4 H4 0.9300 . ? C4 C5 1.357(8) . ? C7 H7 0.9300 . ? C7 C6 1.364(8) . ? C6 H6 0.9300 . ? C6 C5 1.405(8) . ? C5 H5 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ?