#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:49:19 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294475 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572010.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_1572010 loop_ _publ_author_name 'Wang, Xia' 'Wang, Shao-Jie' 'Xin, Xiaolan' 'An, Hao' 'Tu, Zhifeng' 'Yang, Hui' 'Wong, Ming Wah' 'Lu, Shenci' _publ_section_title ; Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis. ; _journal_issue 33 _journal_name_full 'Chemical science' _journal_page_first 13240 _journal_page_last 13249 _journal_paper_doi 10.1039/d4sc03190c _journal_volume 15 _journal_year 2024 _chemical_formula_sum 'C36 H42 N4 O11' _chemical_formula_weight 706.73 _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_method SHELXL-2018/3 _audit_update_record ; 2023-03-22 deposited with the CCDC. 2024-06-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.9652(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.78147(11) _cell_length_b 14.09396(13) _cell_length_c 16.78114(12) _cell_measurement_temperature 301(2) _cell_volume 3686.92(5) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 301(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.951 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_unetI/netI 0.0221 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 71352 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.415 _diffrn_reflns_theta_min 4.117 _exptl_absorpt_coefficient_mu 0.792 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_F_000 1496 _refine_diff_density_max 0.411 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.0024(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 476 _refine_ls_number_reflns 7355 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0489 _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^)+(0.0670P)^2^+1.1021P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1350 _refine_ls_wR_factor_ref 0.1379 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6676 _reflns_number_total 7355 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03190c2.cif _cod_data_source_block zhailele_0320_auto _cod_depositor_comments 'Adding full bibliography for 1572009--1572010.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1572010 _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_res_file ; TITL zhailele_0320_auto_a.res in P2(1)/c zhailele_0320_auto.res created by SHELXL-2018/3 at 08:17:37 on 21-Mar-2023 REM Old TITL zhailele_0320_auto in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.206, Rweak 0.052, Alpha 0.034 REM 1.062 for 315 systematic absences, Orientation as input REM Formula found by SHELXT: C37 N4 O10 CELL 1.54184 15.781466 14.093964 16.781136 90 98.9652 90 ZERR 4 0.000112 0.000129 0.000115 0 0.0007 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 144 168 16 44 L.S. 4 0 0 PLAN 20 TEMP 28 BOND list 4 fmap 2 53 acta OMIT 1 0 2 OMIT 0 4 0 OMIT 1 0 0 OMIT 1 2 1 REM REM REM WGHT 0.067000 1.102100 EXTI 0.002396 FVAR 0.58848 O1 4 0.400884 0.586815 0.483393 11.00000 0.07046 0.04981 = 0.04799 -0.00253 -0.00522 -0.00141 O2 4 0.068873 0.472702 0.719500 11.00000 0.12958 0.16319 = 0.06875 0.02425 0.04838 0.00067 O3 4 0.014841 0.359891 0.639910 11.00000 0.11429 0.09295 = 0.15116 0.03780 0.07395 -0.00648 O4 4 0.178692 0.503062 0.222512 11.00000 0.06166 0.04940 = 0.06111 -0.00027 -0.01141 0.01240 O5 4 0.257263 0.368486 0.225053 11.00000 0.06173 0.04390 = 0.03937 -0.00224 0.00302 0.00804 O6 4 0.288041 0.858863 0.290772 11.00000 0.06585 0.03767 = 0.06158 0.00995 0.00397 0.00385 O7 4 0.356952 0.766654 0.390472 11.00000 0.07662 0.03937 = 0.05673 0.00265 -0.01334 -0.00120 O8 4 0.014620 0.738368 0.089087 11.00000 0.06189 0.19967 = 0.09846 0.01989 -0.01830 0.01821 O9 4 0.135037 0.677288 0.056797 11.00000 0.09259 0.10047 = 0.05291 -0.00468 -0.01766 0.01269 O10 4 0.420588 0.653658 0.233728 11.00000 0.05560 0.05968 = 0.06535 0.02023 0.02323 0.00429 O11 4 0.428312 0.517321 0.305513 11.00000 0.04641 0.04657 = 0.05659 0.00927 0.02076 0.01039 N1 3 0.263749 0.455939 0.337392 11.00000 0.04510 0.03343 = 0.03898 0.00174 0.00736 0.00297 N2 3 0.061384 0.428712 0.655767 11.00000 0.07004 0.08724 = 0.08305 0.03665 0.03498 0.01804 N3 3 0.318228 0.614285 0.309929 11.00000 0.04185 0.03380 = 0.04021 0.00617 0.00938 0.00520 N4 3 0.274905 0.698533 0.284869 11.00000 0.04736 0.03505 = 0.03866 0.00554 0.00547 0.00515 C1 1 0.288125 0.551852 0.369871 11.00000 0.04374 0.03439 = 0.03606 0.00197 0.00903 0.00217 C2 1 0.361281 0.526996 0.441413 11.00000 0.04881 0.04466 = 0.03630 0.00183 0.00689 0.00368 C3 1 0.363635 0.425283 0.447592 11.00000 0.05813 0.04368 = 0.04033 0.00662 0.00384 0.00884 AFIX 43 H3 2 0.398235 0.391162 0.487548 11.00000 -1.20000 AFIX 0 C4 1 0.308455 0.386702 0.387106 11.00000 0.05079 0.03731 = 0.04015 0.00560 0.01322 0.00706 C5 1 0.213691 0.599815 0.403187 11.00000 0.05142 0.03914 = 0.04742 0.00322 0.01708 0.00669 AFIX 23 H5A 2 0.232340 0.662183 0.423163 11.00000 -1.20000 H5B 2 0.166723 0.608729 0.359136 11.00000 -1.20000 AFIX 0 C6 1 0.180423 0.546510 0.469872 11.00000 0.04632 0.03836 = 0.04914 0.00164 0.01711 0.00602 C7 1 0.204927 0.574071 0.549929 11.00000 0.06120 0.05297 = 0.05103 -0.00436 0.01803 -0.00366 AFIX 43 H7 2 0.247361 0.619886 0.562218 11.00000 -1.20000 AFIX 0 C8 1 0.167619 0.534885 0.611274 11.00000 0.06642 0.06747 = 0.04800 0.00348 0.01745 0.00798 AFIX 43 H8 2 0.182844 0.555158 0.664312 11.00000 -1.20000 AFIX 0 C9 1 0.107344 0.465068 0.591747 11.00000 0.05443 0.05814 = 0.06050 0.01888 0.02396 0.01442 C10 1 0.084495 0.431664 0.514388 11.00000 0.04870 0.04782 = 0.08097 0.00694 0.02131 -0.00073 AFIX 43 H10 2 0.045614 0.382010 0.503437 11.00000 -1.20000 AFIX 0 C11 1 0.120886 0.473870 0.452998 11.00000 0.04799 0.05115 = 0.05645 -0.00381 0.01504 0.00233 AFIX 43 H11 2 0.105230 0.453286 0.400099 11.00000 -1.20000 AFIX 0 C12 1 0.288088 0.284866 0.375158 11.00000 0.06531 0.03652 = 0.04111 0.00467 0.01331 0.00573 C13 1 0.354167 0.219493 0.376526 11.00000 0.07311 0.04530 = 0.06128 0.00854 0.01430 0.01311 AFIX 43 H13 2 0.410970 0.239650 0.385524 11.00000 -1.20000 AFIX 0 C14 1 0.335071 0.124101 0.364422 11.00000 0.10513 0.04282 = 0.07409 0.00770 0.02566 0.02174 AFIX 43 H14 2 0.379359 0.080525 0.364644 11.00000 -1.20000 AFIX 0 C15 1 0.251782 0.093227 0.352140 11.00000 0.11810 0.03747 = 0.06802 0.00074 0.02493 -0.00291 AFIX 43 H15 2 0.239633 0.029200 0.343125 11.00000 -1.20000 AFIX 0 C16 1 0.186125 0.157217 0.353177 11.00000 0.08953 0.04937 = 0.07388 -0.00028 0.02104 -0.01338 AFIX 43 H16 2 0.129594 0.136225 0.346541 11.00000 -1.20000 AFIX 0 C17 1 0.204223 0.252705 0.364087 11.00000 0.06965 0.04254 = 0.06511 0.00306 0.01767 0.00070 AFIX 43 H17 2 0.159577 0.295796 0.363986 11.00000 -1.20000 AFIX 0 C18 1 0.227702 0.445374 0.256516 11.00000 0.04312 0.03758 = 0.04381 0.00141 0.00458 -0.00050 C19 1 0.231865 0.343970 0.138740 11.00000 0.07752 0.06167 = 0.04405 -0.01176 -0.00424 0.00666 C20 1 0.270433 0.418799 0.089660 11.00000 0.13801 0.09980 = 0.05244 0.01154 0.02510 0.01404 AFIX 137 H20A 2 0.240807 0.477870 0.092666 11.00000 -1.50000 H20B 2 0.264755 0.398730 0.034416 11.00000 -1.50000 H20C 2 0.330058 0.426988 0.110948 11.00000 -1.50000 AFIX 0 C21 1 0.274649 0.248757 0.133632 11.00000 0.12666 0.07540 = 0.06934 -0.02645 0.00148 0.02350 AFIX 137 H21A 2 0.335333 0.255184 0.150633 11.00000 -1.50000 H21B 2 0.263979 0.226328 0.078969 11.00000 -1.50000 H21C 2 0.251823 0.204253 0.168049 11.00000 -1.50000 AFIX 0 C22 1 0.136642 0.335837 0.117447 11.00000 0.08051 0.11349 = 0.12380 -0.05213 -0.02650 -0.00293 AFIX 137 H22A 2 0.114891 0.297112 0.156764 11.00000 -1.50000 H22B 2 0.122461 0.307320 0.065115 11.00000 -1.50000 H22C 2 0.111382 0.397852 0.116781 11.00000 -1.50000 AFIX 0 C23 1 0.307433 0.782295 0.320109 11.00000 0.04419 0.03905 = 0.04511 0.00548 0.00926 0.00220 C24 1 0.395037 0.846827 0.437299 11.00000 0.08737 0.04688 = 0.07403 -0.00121 -0.02162 -0.00841 AFIX 13 H24 2 0.370685 0.906637 0.414356 11.00000 -1.20000 AFIX 0 C25 1 0.488371 0.842961 0.435134 11.00000 0.09716 0.21946 = 0.09752 -0.02475 0.01363 -0.07219 AFIX 137 H25A 2 0.512092 0.787014 0.462677 11.00000 -1.50000 H25B 2 0.515474 0.898158 0.461235 11.00000 -1.50000 H25C 2 0.498085 0.841204 0.380086 11.00000 -1.50000 AFIX 0 C26 1 0.376129 0.833663 0.522306 11.00000 0.12138 0.14395 = 0.09578 -0.05983 0.03259 -0.02240 AFIX 137 H26A 2 0.315182 0.832218 0.521488 11.00000 -1.50000 H26B 2 0.400433 0.885395 0.555453 11.00000 -1.50000 H26C 2 0.400780 0.775028 0.543893 11.00000 -1.50000 AFIX 0 C27 1 0.232763 0.703292 0.200332 11.00000 0.04970 0.04474 = 0.03806 0.00737 0.00690 0.00430 AFIX 23 H27A 2 0.239098 0.642402 0.174968 11.00000 -1.20000 H27B 2 0.261995 0.750333 0.172322 11.00000 -1.20000 AFIX 0 C28 1 0.138872 0.727934 0.190051 11.00000 0.04817 0.05384 = 0.05308 0.01506 0.00544 0.00113 C29 1 0.097849 0.760467 0.246553 11.00000 0.05499 0.08730 = 0.07065 0.01659 0.01629 0.01600 H29A 2 0.036944 0.778888 0.236012 11.00000 0.08265 H29B 2 0.126941 0.772363 0.302298 11.00000 0.08312 C30 1 0.088316 0.715756 0.108324 11.00000 0.05947 0.08913 = 0.06474 0.01451 -0.00675 -0.00117 C31 1 0.092366 0.662522 -0.025348 11.00000 0.20015 0.13626 = 0.06804 -0.02164 -0.06239 0.04113 AFIX 43 H31 2 0.058289 0.708719 -0.054088 11.00000 -1.20000 AFIX 0 C32 1 0.105239 0.580542 -0.055510 11.00000 0.27843 0.15355 = 0.09106 -0.04667 -0.07737 0.09627 AFIX 93 H32A 2 0.139750 0.536159 -0.024879 11.00000 -1.20000 H32B 2 0.080008 0.565832 -0.107883 11.00000 -1.20000 AFIX 0 C33 1 0.393641 0.599605 0.279380 11.00000 0.04420 0.04087 = 0.04199 0.00395 0.00928 0.00085 C34 1 0.508072 0.488043 0.278356 11.00000 0.04379 0.06307 = 0.04773 0.00120 0.01656 0.00938 AFIX 13 H34 2 0.503694 0.498670 0.220146 11.00000 -1.20000 AFIX 0 C35 1 0.582204 0.542358 0.321770 11.00000 0.05255 0.10494 = 0.08284 0.00336 0.00425 -0.00534 AFIX 137 H35A 2 0.574336 0.608718 0.309986 11.00000 -1.50000 H35B 2 0.634162 0.520938 0.304495 11.00000 -1.50000 H35C 2 0.585882 0.532415 0.378800 11.00000 -1.50000 AFIX 0 C36 1 0.514524 0.383401 0.295886 11.00000 0.07469 0.06386 = 0.09339 0.00470 0.03447 0.02536 AFIX 137 H36A 2 0.517618 0.373168 0.352824 11.00000 -1.50000 H36B 2 0.565183 0.358473 0.278417 11.00000 -1.50000 H36C 2 0.464888 0.351780 0.267604 11.00000 -1.50000 AFIX 0 HKLF 4 REM zhailele_0320_auto_a.res in P2(1)/c REM wR2 = 0.1379, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0489 for 6676 Fo > 4sig(Fo) and 0.0522 for all 7355 data REM 476 parameters refined using 0 restraints END WGHT 0.0670 1.1009 REM Highest difference peak 0.411, deepest hole -0.323, 1-sigma level 0.036 Q1 1 0.3485 0.8855 0.4767 11.00000 0.05 0.41 Q2 1 0.0875 0.3994 0.7049 11.00000 0.05 0.29 Q3 1 0.0567 0.5796 -0.0056 11.00000 0.05 0.27 Q4 1 0.2011 0.4155 0.0859 11.00000 0.05 0.22 Q5 1 0.4873 0.8057 0.4781 11.00000 0.05 0.21 Q6 1 0.1606 0.4769 0.5982 11.00000 0.05 0.20 Q7 1 0.3243 0.5437 0.4092 11.00000 0.05 0.18 Q8 1 0.0811 0.5668 -0.0760 11.00000 0.05 0.18 Q9 1 0.1383 0.5800 -0.0593 11.00000 0.05 0.18 Q10 1 0.2997 0.3359 0.3836 11.00000 0.05 0.18 Q11 1 -0.0123 0.3338 0.5808 11.00000 0.05 0.17 Q12 1 0.1818 0.7143 0.1937 11.00000 0.05 0.17 Q13 1 0.0675 0.3487 0.6600 11.00000 0.05 0.17 Q14 1 0.0732 0.7004 -0.0342 11.00000 0.05 0.17 Q15 1 0.3158 0.4160 0.4392 11.00000 0.05 0.17 Q16 1 0.1822 0.6784 -0.0637 11.00000 0.05 0.17 Q17 1 0.1232 0.6561 -0.0415 11.00000 0.05 0.17 Q18 1 0.0184 0.6635 0.1061 11.00000 0.05 0.16 Q19 1 0.1225 0.6264 0.0756 11.00000 0.05 0.16 Q20 1 0.3741 0.7723 0.3459 11.00000 0.05 0.16 ; _shelx_res_checksum 29101 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 O1 O 0.40088(8) 0.58682(9) 0.48339(7) 0.0576(3) Uani 1 1 d . . . . . O2 O 0.06887(15) 0.47270(19) 0.71950(11) 0.1170(7) Uani 1 1 d . . . . . O3 O 0.01484(14) 0.35989(15) 0.63991(14) 0.1138(7) Uani 1 1 d . . . . . O4 O 0.17869(8) 0.50306(8) 0.22251(7) 0.0596(3) Uani 1 1 d . . . . . O5 O 0.25726(7) 0.36849(8) 0.22505(6) 0.0489(3) Uani 1 1 d . . . . . O6 O 0.28804(8) 0.85886(8) 0.29077(7) 0.0557(3) Uani 1 1 d . . . . . O7 O 0.35695(8) 0.76665(8) 0.39047(7) 0.0601(3) Uani 1 1 d . . . . . O8 O 0.01462(11) 0.7384(2) 0.08909(12) 0.1233(8) Uani 1 1 d . . . . . O9 O 0.13504(11) 0.67729(13) 0.05680(8) 0.0851(5) Uani 1 1 d . . . . . O10 O 0.42059(8) 0.65366(9) 0.23373(8) 0.0587(3) Uani 1 1 d . . . . . O11 O 0.42831(7) 0.51732(8) 0.30551(7) 0.0485(3) Uani 1 1 d . . . . . N1 N 0.26375(8) 0.45594(8) 0.33739(7) 0.0391(3) Uani 1 1 d . . . . . N2 N 0.06138(12) 0.42871(15) 0.65577(12) 0.0777(5) Uani 1 1 d . . . . . N3 N 0.31823(7) 0.61428(8) 0.30993(7) 0.0383(3) Uani 1 1 d . . . . . N4 N 0.27490(8) 0.69853(8) 0.28487(7) 0.0405(3) Uani 1 1 d . . . . . C1 C 0.28813(9) 0.55185(10) 0.36987(8) 0.0378(3) Uani 1 1 d . . . . . C2 C 0.36128(10) 0.52700(11) 0.44141(8) 0.0432(3) Uani 1 1 d . . . . . C3 C 0.36364(11) 0.42528(11) 0.44759(9) 0.0478(4) Uani 1 1 d . . . . . H3 H 0.398235 0.391162 0.487548 0.057 Uiso 1 1 calc R U . . . C4 C 0.30845(10) 0.38670(10) 0.38711(8) 0.0421(3) Uani 1 1 d . . . . . C5 C 0.21369(10) 0.59982(11) 0.40319(9) 0.0450(3) Uani 1 1 d . . . . . H5A H 0.232340 0.662183 0.423163 0.054 Uiso 1 1 calc R U . . . H5B H 0.166723 0.608729 0.359136 0.054 Uiso 1 1 calc R U . . . C6 C 0.18042(10) 0.54651(11) 0.46987(9) 0.0436(3) Uani 1 1 d . . . . . C7 C 0.20493(12) 0.57407(13) 0.54993(10) 0.0541(4) Uani 1 1 d . . . . . H7 H 0.247361 0.619886 0.562218 0.065 Uiso 1 1 calc R U . . . C8 C 0.16762(12) 0.53488(14) 0.61127(11) 0.0597(4) Uani 1 1 d . . . . . H8 H 0.182844 0.555158 0.664312 0.072 Uiso 1 1 calc R U . . . C9 C 0.10734(11) 0.46507(13) 0.59175(11) 0.0561(4) Uani 1 1 d . . . . . C10 C 0.08450(11) 0.43166(13) 0.51439(12) 0.0580(4) Uani 1 1 d . . . . . H10 H 0.045614 0.382010 0.503437 0.070 Uiso 1 1 calc R U . . . C11 C 0.12089(10) 0.47387(12) 0.45300(11) 0.0511(4) Uani 1 1 d . . . . . H11 H 0.105230 0.453286 0.400099 0.061 Uiso 1 1 calc R U . . . C12 C 0.28809(11) 0.28487(11) 0.37516(9) 0.0471(4) Uani 1 1 d . . . . . C13 C 0.35417(13) 0.21949(12) 0.37653(11) 0.0595(4) Uani 1 1 d . . . . . H13 H 0.410970 0.239650 0.385524 0.071 Uiso 1 1 calc R U . . . C14 C 0.33507(17) 0.12410(14) 0.36442(13) 0.0728(6) Uani 1 1 d . . . . . H14 H 0.379359 0.080525 0.364644 0.087 Uiso 1 1 calc R U . . . C15 C 0.25178(17) 0.09323(14) 0.35214(13) 0.0734(6) Uani 1 1 d . . . . . H15 H 0.239633 0.029200 0.343125 0.088 Uiso 1 1 calc R U . . . C16 C 0.18613(15) 0.15722(14) 0.35318(13) 0.0700(5) Uani 1 1 d . . . . . H16 H 0.129594 0.136225 0.346541 0.084 Uiso 1 1 calc R U . . . C17 C 0.20422(13) 0.25271(12) 0.36409(11) 0.0583(4) Uani 1 1 d . . . . . H17 H 0.159577 0.295796 0.363986 0.070 Uiso 1 1 calc R U . . . C18 C 0.22770(9) 0.44537(10) 0.25652(9) 0.0417(3) Uani 1 1 d . . . . . C19 C 0.23186(13) 0.34397(14) 0.13874(10) 0.0625(5) Uani 1 1 d . . . . . C20 C 0.2704(2) 0.4188(2) 0.08966(13) 0.0957(8) Uani 1 1 d . . . . . H20A H 0.240807 0.477870 0.092666 0.143 Uiso 1 1 calc R U . . . H20B H 0.264755 0.398730 0.034416 0.143 Uiso 1 1 calc R U . . . H20C H 0.330058 0.426988 0.110948 0.143 Uiso 1 1 calc R U . . . C21 C 0.2746(2) 0.24876(18) 0.13363(14) 0.0919(8) Uani 1 1 d . . . . . H21A H 0.335333 0.255184 0.150633 0.138 Uiso 1 1 calc R U . . . H21B H 0.263979 0.226328 0.078969 0.138 Uiso 1 1 calc R U . . . H21C H 0.251823 0.204253 0.168049 0.138 Uiso 1 1 calc R U . . . C22 C 0.13664(17) 0.3358(2) 0.1174(2) 0.1104(10) Uani 1 1 d . . . . . H22A H 0.114891 0.297112 0.156764 0.166 Uiso 1 1 calc R U . . . H22B H 0.122461 0.307320 0.065115 0.166 Uiso 1 1 calc R U . . . H22C H 0.111382 0.397852 0.116781 0.166 Uiso 1 1 calc R U . . . C23 C 0.30743(9) 0.78230(10) 0.32011(9) 0.0425(3) Uani 1 1 d . . . . . C24 C 0.39504(15) 0.84683(14) 0.43730(13) 0.0731(6) Uani 1 1 d . . . . . H24 H 0.370685 0.906637 0.414356 0.088 Uiso 1 1 calc R U . . . C25 C 0.4884(2) 0.8430(3) 0.4351(2) 0.1382(15) Uani 1 1 d . . . . . H25A H 0.512092 0.787014 0.462677 0.207 Uiso 1 1 calc R U . . . H25B H 0.515474 0.898158 0.461235 0.207 Uiso 1 1 calc R U . . . H25C H 0.498085 0.841204 0.380086 0.207 Uiso 1 1 calc R U . . . C26 C 0.3761(2) 0.8337(3) 0.52231(18) 0.1187(11) Uani 1 1 d . . . . . H26A H 0.315182 0.832218 0.521488 0.178 Uiso 1 1 calc R U . . . H26B H 0.400433 0.885395 0.555453 0.178 Uiso 1 1 calc R U . . . H26C H 0.400780 0.775028 0.543893 0.178 Uiso 1 1 calc R U . . . C27 C 0.23276(10) 0.70329(11) 0.20033(9) 0.0442(3) Uani 1 1 d . . . . . H27A H 0.239098 0.642402 0.174968 0.053 Uiso 1 1 calc R U . . . H27B H 0.261995 0.750333 0.172322 0.053 Uiso 1 1 calc R U . . . C28 C 0.13887(10) 0.72793(12) 0.19005(10) 0.0520(4) Uani 1 1 d . . . . . C29 C 0.09785(14) 0.76047(17) 0.24655(14) 0.0703(5) Uani 1 1 d . . . . . H29A H 0.0369(16) 0.7789(17) 0.2360(14) 0.083(7) Uiso 1 1 d . . . . . H29B H 0.1269(16) 0.7724(17) 0.3023(16) 0.083(7) Uiso 1 1 d . . . . . C30 C 0.08832(13) 0.71576(18) 0.10832(13) 0.0729(6) Uani 1 1 d . . . . . C31 C 0.0924(3) 0.6625(3) -0.02535(17) 0.1437(16) Uani 1 1 d . . . . . H31 H 0.058289 0.708719 -0.054088 0.172 Uiso 1 1 calc R U . . . C32 C 0.1052(4) 0.5805(3) -0.0555(2) 0.186(3) Uani 1 1 d . . . . . H32A H 0.139750 0.536159 -0.024879 0.223 Uiso 1 1 calc R U . . . H32B H 0.080008 0.565832 -0.107883 0.223 Uiso 1 1 calc R U . . . C33 C 0.39364(9) 0.59961(11) 0.27938(9) 0.0421(3) Uani 1 1 d . . . . . C34 C 0.50807(10) 0.48804(13) 0.27836(10) 0.0505(4) Uani 1 1 d . . . . . H34 H 0.503694 0.498670 0.220146 0.061 Uiso 1 1 calc R U . . . C35 C 0.58220(13) 0.54236(19) 0.32177(15) 0.0808(6) Uani 1 1 d . . . . . H35A H 0.574336 0.608718 0.309986 0.121 Uiso 1 1 calc R U . . . H35B H 0.634162 0.520938 0.304495 0.121 Uiso 1 1 calc R U . . . H35C H 0.585882 0.532415 0.378800 0.121 Uiso 1 1 calc R U . . . C36 C 0.51452(14) 0.38340(15) 0.29589(15) 0.0750(6) Uani 1 1 d . . . . . H36A H 0.517618 0.373168 0.352824 0.113 Uiso 1 1 calc R U . . . H36B H 0.565183 0.358473 0.278417 0.113 Uiso 1 1 calc R U . . . H36C H 0.464888 0.351780 0.267604 0.113 Uiso 1 1 calc R U . . . 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 0.0705(7) 0.0498(7) 0.0480(6) -0.0025(5) -0.0052(5) -0.0014(5) O2 0.1296(17) 0.163(2) 0.0687(11) 0.0242(12) 0.0484(11) 0.0007(14) O3 0.1143(14) 0.0929(13) 0.1512(18) 0.0378(12) 0.0740(14) -0.0065(11) O4 0.0617(7) 0.0494(7) 0.0611(7) -0.0003(5) -0.0114(5) 0.0124(5) O5 0.0617(6) 0.0439(6) 0.0394(5) -0.0022(4) 0.0030(4) 0.0080(5) O6 0.0659(7) 0.0377(6) 0.0616(7) 0.0099(5) 0.0040(5) 0.0039(5) O7 0.0766(8) 0.0394(6) 0.0567(7) 0.0027(5) -0.0133(6) -0.0012(5) O8 0.0619(10) 0.200(2) 0.0985(13) 0.0199(14) -0.0183(9) 0.0182(12) O9 0.0926(11) 0.1005(12) 0.0529(8) -0.0047(7) -0.0177(7) 0.0127(9) O10 0.0556(7) 0.0597(7) 0.0654(7) 0.0202(6) 0.0232(5) 0.0043(5) O11 0.0464(6) 0.0466(6) 0.0566(6) 0.0093(5) 0.0208(5) 0.0104(4) N1 0.0451(6) 0.0334(6) 0.0390(6) 0.0017(5) 0.0074(5) 0.0030(5) N2 0.0700(11) 0.0872(13) 0.0831(13) 0.0366(10) 0.0350(9) 0.0180(10) N3 0.0419(6) 0.0338(6) 0.0402(6) 0.0062(5) 0.0094(5) 0.0052(5) N4 0.0474(6) 0.0351(6) 0.0387(6) 0.0055(5) 0.0055(5) 0.0051(5) C1 0.0437(7) 0.0344(7) 0.0361(6) 0.0020(5) 0.0090(5) 0.0022(5) C2 0.0488(8) 0.0447(8) 0.0363(7) 0.0018(6) 0.0069(6) 0.0037(6) C3 0.0581(9) 0.0437(8) 0.0403(7) 0.0066(6) 0.0038(6) 0.0088(7) C4 0.0508(8) 0.0373(8) 0.0401(7) 0.0056(6) 0.0132(6) 0.0071(6) C5 0.0514(8) 0.0391(8) 0.0474(8) 0.0032(6) 0.0171(6) 0.0067(6) C6 0.0463(7) 0.0384(8) 0.0491(8) 0.0016(6) 0.0171(6) 0.0060(6) C7 0.0612(9) 0.0530(10) 0.0510(9) -0.0044(7) 0.0180(7) -0.0037(7) C8 0.0664(10) 0.0675(11) 0.0480(9) 0.0035(8) 0.0175(8) 0.0080(9) C9 0.0544(9) 0.0581(10) 0.0605(10) 0.0189(8) 0.0240(8) 0.0144(8) C10 0.0487(9) 0.0478(9) 0.0810(12) 0.0069(8) 0.0213(8) -0.0007(7) C11 0.0480(8) 0.0511(9) 0.0565(9) -0.0038(7) 0.0150(7) 0.0023(7) C12 0.0653(9) 0.0365(8) 0.0411(7) 0.0047(6) 0.0133(7) 0.0057(7) C13 0.0731(11) 0.0453(9) 0.0613(10) 0.0085(7) 0.0143(8) 0.0131(8) C14 0.1051(17) 0.0428(10) 0.0741(12) 0.0077(9) 0.0257(11) 0.0217(10) C15 0.1181(19) 0.0375(9) 0.0680(12) 0.0007(8) 0.0249(11) -0.0029(10) C16 0.0895(14) 0.0494(11) 0.0739(12) -0.0003(9) 0.0210(10) -0.0134(9) C17 0.0696(11) 0.0425(9) 0.0651(10) 0.0031(7) 0.0177(8) 0.0007(8) C18 0.0431(7) 0.0376(7) 0.0438(7) 0.0014(6) 0.0046(6) -0.0005(6) C19 0.0775(12) 0.0617(11) 0.0441(8) -0.0118(8) -0.0042(8) 0.0067(9) C20 0.138(2) 0.0998(19) 0.0524(11) 0.0115(12) 0.0251(13) 0.0140(17) C21 0.127(2) 0.0754(15) 0.0693(13) -0.0264(11) 0.0015(13) 0.0235(14) C22 0.0805(16) 0.113(2) 0.124(2) -0.0521(18) -0.0265(15) -0.0029(15) C23 0.0442(7) 0.0390(8) 0.0451(7) 0.0055(6) 0.0093(6) 0.0022(6) C24 0.0874(14) 0.0469(10) 0.0740(12) -0.0012(9) -0.0216(10) -0.0084(9) C25 0.097(2) 0.219(4) 0.098(2) -0.025(2) 0.0136(16) -0.072(3) C26 0.121(2) 0.144(3) 0.096(2) -0.060(2) 0.0326(17) -0.022(2) C27 0.0497(8) 0.0447(8) 0.0381(7) 0.0074(6) 0.0069(6) 0.0043(6) C28 0.0482(8) 0.0538(10) 0.0531(9) 0.0151(7) 0.0054(7) 0.0011(7) C29 0.0550(10) 0.0873(15) 0.0706(13) 0.0166(11) 0.0163(9) 0.0160(10) C30 0.0595(11) 0.0891(15) 0.0647(12) 0.0145(11) -0.0068(9) -0.0012(10) C31 0.200(4) 0.136(3) 0.0680(16) -0.0216(18) -0.062(2) 0.041(3) C32 0.278(6) 0.154(4) 0.091(2) -0.047(2) -0.077(3) 0.096(4) C33 0.0442(7) 0.0409(8) 0.0420(7) 0.0040(6) 0.0093(6) 0.0009(6) C34 0.0438(8) 0.0631(10) 0.0477(8) 0.0012(7) 0.0166(6) 0.0094(7) C35 0.0526(10) 0.1049(18) 0.0828(14) 0.0034(13) 0.0043(10) -0.0053(11) C36 0.0747(13) 0.0639(13) 0.0934(15) 0.0047(11) 0.0345(11) 0.0254(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C18 O5 C19 121.52(12) . . ? C23 O7 C24 119.23(13) . . ? C30 O9 C31 116.9(2) . . ? C33 O11 C34 118.28(12) . . ? C18 N1 C4 126.59(12) . . ? C18 N1 C1 119.80(11) . . ? C4 N1 C1 109.74(11) . . ? O3 N2 O2 124.4(2) . . ? O3 N2 C9 117.6(2) . . ? O2 N2 C9 117.9(2) . . ? C33 N3 N4 115.04(11) . . ? C33 N3 C1 123.55(11) . . ? N4 N3 C1 121.19(11) . . ? C23 N4 N3 117.63(11) . . ? C23 N4 C27 117.08(12) . . ? N3 N4 C27 117.00(11) . . ? N3 C1 N1 112.73(11) . . ? N3 C1 C5 109.45(11) . . ? N1 C1 C5 111.43(12) . . ? N3 C1 C2 112.29(11) . . ? N1 C1 C2 101.25(11) . . ? C5 C1 C2 109.46(11) . . ? O1 C2 C3 130.43(14) . . ? O1 C2 C1 122.82(14) . . ? C3 C2 C1 106.58(13) . . ? C4 C3 C2 110.02(13) . . ? C3 C4 N1 112.00(13) . . ? C3 C4 C12 126.63(14) . . ? N1 C4 C12 121.14(13) . . ? C6 C5 C1 115.19(12) . . ? C11 C6 C7 118.63(14) . . ? C11 C6 C5 121.24(14) . . ? C7 C6 C5 119.99(14) . . ? C8 C7 C6 121.43(17) . . ? C9 C8 C7 118.02(17) . . ? C8 C9 C10 122.75(15) . . ? C8 C9 N2 118.38(18) . . ? C10 C9 N2 118.76(18) . . ? C9 C10 C11 118.40(17) . . ? C6 C11 C10 120.62(16) . . ? C17 C12 C13 119.00(16) . . ? C17 C12 C4 121.31(15) . . ? C13 C12 C4 119.68(16) . . ? C14 C13 C12 119.7(2) . . ? C15 C14 C13 120.80(19) . . ? C14 C15 C16 119.80(19) . . ? C15 C16 C17 120.0(2) . . ? C16 C17 C12 120.69(18) . . ? O4 C18 O5 127.26(14) . . ? O4 C18 N1 121.58(14) . . ? O5 C18 N1 111.11(12) . . ? O5 C19 C22 111.12(18) . . ? O5 C19 C21 101.97(15) . . ? C22 C19 C21 111.1(2) . . ? O5 C19 C20 107.29(17) . . ? C22 C19 C20 113.3(2) . . ? C21 C19 C20 111.4(2) . . ? O6 C23 O7 126.02(14) . . ? O6 C23 N4 122.40(14) . . ? O7 C23 N4 111.47(12) . . ? O7 C24 C25 106.7(2) . . ? O7 C24 C26 106.79(19) . . ? C25 C24 C26 111.2(2) . . ? N4 C27 C28 114.20(12) . . ? C29 C28 C30 116.96(18) . . ? C29 C28 C27 125.86(17) . . ? C30 C28 C27 117.17(16) . . ? O8 C30 O9 122.9(2) . . ? O8 C30 C28 125.2(2) . . ? O9 C30 C28 111.93(17) . . ? C32 C31 O9 115.0(3) . . ? O10 C33 O11 126.50(14) . . ? O10 C33 N3 123.43(14) . . ? O11 C33 N3 110.03(12) . . ? O11 C34 C35 110.54(15) . . ? O11 C34 C36 104.53(13) . . ? C35 C34 C36 112.59(18) . . ? 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 1.2085(19) . ? O2 N2 1.226(3) . ? O3 N2 1.221(3) . ? O4 C18 1.2031(18) . ? O5 C18 1.3219(18) . ? O5 C19 1.4823(19) . ? O6 C23 1.2057(18) . ? O7 C23 1.3289(19) . ? O7 C24 1.452(2) . ? O8 C30 1.201(3) . ? O9 C30 1.336(3) . ? O9 C31 1.452(3) . ? O10 C33 1.2040(18) . ? O11 C33 1.3273(18) . ? O11 C34 1.4633(17) . ? N1 C18 1.3954(18) . ? N1 C4 1.4009(18) . ? N1 C1 1.4856(18) . ? N2 C9 1.478(2) . ? N3 C33 1.3828(18) . ? N3 N4 1.4016(16) . ? N3 C1 1.4699(17) . ? N4 C23 1.3829(19) . ? N4 C27 1.4715(18) . ? C1 C5 1.5343(19) . ? C1 C2 1.570(2) . ? C2 C3 1.437(2) . ? C3 C4 1.345(2) . ? C4 C12 1.478(2) . ? C5 C6 1.508(2) . ? C6 C11 1.389(2) . ? C6 C7 1.394(2) . ? C7 C8 1.379(2) . ? C8 C9 1.372(3) . ? C9 C10 1.375(3) . ? C10 C11 1.389(2) . ? C12 C17 1.384(3) . ? C12 C13 1.389(2) . ? C13 C14 1.386(3) . ? C14 C15 1.369(3) . ? C15 C16 1.376(3) . ? C16 C17 1.382(3) . ? C19 C22 1.494(3) . ? C19 C21 1.511(3) . ? C19 C20 1.522(3) . ? C24 C25 1.480(4) . ? C24 C26 1.514(4) . ? C27 C28 1.505(2) . ? C28 C29 1.311(3) . ? C28 C30 1.485(3) . ? C31 C32 1.290(5) . ? C34 C35 1.490(3) . ? C34 C36 1.504(3) . ?