#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:22:07 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253925 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240449.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_7240449 loop_ _publ_author_name 'Ma, Xiao-Pan' 'Nong, Cai-Mei' 'Liang, Yu-Feng' 'Xu, Pei-Pei' 'Guo, Xiu-Yun' 'Liang, Cui' 'Pan, Cheng-Xue' 'Su, Gui-Fa' 'Mo, Dong-Liang' _publ_section_title ; An Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot to prepare oxazonine-fused endoperoxides ; _journal_issue 12 _journal_name_full 'Green Chemistry' _journal_page_first 3827 _journal_paper_doi 10.1039/D0GC00929F _journal_volume 22 _journal_year 2020 _chemical_formula_sum 'C35 H35 N O5' _chemical_formula_weight 549.64 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 95.037(7) _cell_angle_beta 96.282(6) _cell_angle_gamma 100.049(8) _cell_formula_units_Z 2 _cell_length_a 9.3207(8) _cell_length_b 10.8786(12) _cell_length_c 14.8658(10) _cell_measurement_reflns_used 2438 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.0330 _cell_measurement_theta_min 3.6650 _cell_volume 1466.5(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.844 _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_unetI/netI 0.0632 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.844 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11619 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.844 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.214 _diffrn_reflns_theta_min 3.538 _exptl_absorpt_coefficient_mu 0.083 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.245 _exptl_crystal_description block _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.157 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 372 _refine_ls_number_reflns 6710 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.1101 _refine_ls_R_factor_gt 0.0581 _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^)+(0.0504P)^2^+0.1918P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1216 _refine_ls_wR_factor_ref 0.1575 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3788 _reflns_number_total 6710 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc00929f2.cif _cod_data_source_block mp-9-50(2) _cod_depositor_comments 'Adding full bibliography for 7240449.cif.' _cod_database_code 7240449 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; mp-9-50(2).res created by SHELXL-2014/7 TITL MP-9-50 (2) in P-1 #2 REM reset to P-1 #2 CELL 0.71073 9.320655 10.878617 14.865762 95.0373 96.2819 100.0487 ZERR 2 0.000772 0.00123 0.001043 0.0074 0.0063 0.0081 LATT 1 SFAC C H N O UNIT 70 70 2 10 L.S. 20 PLAN 20 BOND $H HTAB CONF fmap 2 53 acta REM REM REM WGHT 0.050400 0.191800 FVAR 6.56364 O5 4 0.618066 0.755238 0.103512 11.00000 0.04316 0.04661 = 0.04574 0.01045 -0.00036 -0.00040 O4 4 0.548242 0.625826 0.066335 11.00000 0.04312 0.05156 = 0.03783 0.00179 0.00672 -0.00172 O3 4 0.326351 0.353422 0.197820 11.00000 0.03681 0.04781 = 0.05235 0.00015 0.00778 0.00197 O1 4 0.620386 0.602033 0.438165 11.00000 0.05005 0.05671 = 0.04206 -0.00201 0.00359 0.00869 O2 4 0.737001 0.455990 0.380059 11.00000 0.04904 0.05503 = 0.06028 0.01039 -0.00233 0.01873 C10 1 0.637295 0.513027 0.374108 11.00000 0.04208 0.03865 = 0.04068 0.01096 0.00744 0.00478 C11 1 0.518651 0.498890 0.294664 11.00000 0.03395 0.03720 = 0.04117 0.00458 0.00470 0.00693 AFIX 13 H11 2 0.436823 0.532668 0.317142 11.00000 -1.20000 AFIX 0 C29 1 0.744442 0.744834 0.164424 11.00000 0.03297 0.04539 = 0.04593 0.00873 0.00514 0.00389 AFIX 13 H29 2 0.817997 0.715168 0.130038 11.00000 -1.20000 AFIX 0 C19 1 0.324151 0.621383 0.148029 11.00000 0.03458 0.05045 = 0.03428 0.00356 0.00047 0.00922 AFIX 13 H19 2 0.333767 0.649606 0.213212 11.00000 -1.20000 AFIX 0 N1 3 0.211080 0.380318 0.249958 11.00000 0.03328 0.05452 = 0.05672 0.00380 0.01221 -0.00121 C12 1 0.458463 0.362751 0.256379 11.00000 0.03638 0.03977 = 0.04799 0.00593 0.00779 0.00386 C26 1 0.468419 0.570510 0.133899 11.00000 0.03423 0.04171 = 0.03814 0.00428 0.00640 0.00221 AFIX 13 H26 2 0.438072 0.480944 0.112479 11.00000 -1.20000 AFIX 0 C28 1 0.700062 0.655551 0.231435 11.00000 0.03513 0.04178 = 0.04092 0.00682 0.00166 0.00741 AFIX 43 H28 2 0.766099 0.653704 0.282725 11.00000 -1.20000 AFIX 0 C30 1 0.802343 0.877598 0.208183 11.00000 0.04114 0.04133 = 0.04863 0.01056 -0.00016 0.00347 C15 1 0.142685 0.457174 0.211519 11.00000 0.03152 0.05521 = 0.05197 0.00124 0.00592 -0.00044 C17 1 0.177379 0.521988 0.128015 11.00000 0.03228 0.06154 = 0.04626 0.00481 0.00359 0.00710 AFIX 13 H17 2 0.100058 0.571462 0.117119 11.00000 -1.20000 AFIX 0 C20 1 0.308148 0.736973 0.100329 11.00000 0.03825 0.05985 = 0.03914 0.00798 0.00310 0.01051 C6 1 1.121902 0.787130 0.450462 11.00000 0.05857 0.04656 = 0.04461 0.00485 -0.00306 0.00340 C14 1 0.473109 0.250757 0.305050 11.00000 0.05769 0.04246 = 0.07033 0.01462 0.00868 0.00469 AFIX 23 H14A 2 0.388835 0.182813 0.298555 11.00000 -1.20000 H14B 2 0.532582 0.264185 0.364057 11.00000 -1.20000 AFIX 0 C9 1 0.741210 0.638424 0.512245 11.00000 0.06778 0.07040 = 0.03870 -0.00130 -0.00247 0.00120 AFIX 23 H9A 2 0.776239 0.564283 0.530412 11.00000 -1.20000 H9B 2 0.706940 0.678895 0.564424 11.00000 -1.20000 AFIX 0 C35 1 0.926389 0.947293 0.182865 11.00000 0.05244 0.05617 = 0.06916 0.01512 0.00261 -0.00580 AFIX 43 H35 2 0.976457 0.912269 0.139418 11.00000 -1.20000 AFIX 0 C13 1 0.549967 0.274191 0.222729 11.00000 0.05183 0.04459 = 0.07634 -0.00178 0.01547 0.01094 AFIX 23 H13A 2 0.655773 0.301596 0.232162 11.00000 -1.20000 H13B 2 0.512061 0.220245 0.166676 11.00000 -1.20000 AFIX 0 C21 1 0.306578 0.848262 0.151815 11.00000 0.06483 0.05871 = 0.05152 0.00576 0.00432 0.01200 AFIX 43 H21 2 0.314561 0.850261 0.214857 11.00000 -1.20000 AFIX 0 C7 1 0.996260 0.705191 0.478076 11.00000 0.06729 0.05214 = 0.05467 0.00987 -0.00393 0.00580 AFIX 43 H7 2 1.013011 0.628182 0.495146 11.00000 -1.20000 AFIX 0 C5 1 1.113246 0.903835 0.420723 11.00000 0.05648 0.05728 = 0.06878 0.01394 0.00787 0.01605 AFIX 43 H5 2 1.023809 0.931098 0.416429 11.00000 -1.20000 AFIX 0 C25 1 0.294299 0.737647 0.005856 11.00000 0.07089 0.08379 = 0.04576 0.01630 0.00718 0.03052 AFIX 43 H25 2 0.295200 0.664632 -0.031475 11.00000 -1.20000 AFIX 0 C4 1 1.234492 0.978938 0.397735 11.00000 0.07310 0.05221 = 0.07257 0.01817 0.01395 0.01075 AFIX 43 H4 2 1.226560 1.056865 0.378578 11.00000 -1.20000 AFIX 0 C8 1 0.864095 0.726806 0.481681 11.00000 0.06328 0.05584 = 0.05197 -0.00012 -0.00400 0.00371 AFIX 43 H8 2 0.844263 0.802664 0.464007 11.00000 -1.20000 AFIX 0 C31 1 0.729851 0.931507 0.272718 11.00000 0.06053 0.04892 = 0.07410 0.00014 0.00584 0.00952 AFIX 43 H31 2 0.645622 0.885315 0.290080 11.00000 -1.20000 AFIX 0 C1 1 1.257767 0.750268 0.453476 11.00000 0.07191 0.05331 = 0.07332 0.01662 -0.00588 0.01705 AFIX 43 H1 2 1.267171 0.672369 0.472160 11.00000 -1.20000 AFIX 0 C2 1 1.378315 0.826040 0.429552 11.00000 0.05675 0.07749 = 0.08166 0.01246 -0.00168 0.01773 AFIX 43 H2 2 1.467819 0.799001 0.431748 11.00000 -1.20000 AFIX 0 C32 1 0.780925 1.052982 0.311678 11.00000 0.08761 0.05696 = 0.08238 -0.00692 -0.00665 0.01882 AFIX 43 H32 2 0.731398 1.088484 0.355218 11.00000 -1.20000 AFIX 0 C34 1 0.976822 1.070090 0.222270 11.00000 0.07105 0.06014 = 0.09725 0.02640 -0.01607 -0.01820 AFIX 43 H34 2 1.060277 1.117361 0.204810 11.00000 -1.20000 AFIX 0 C3 1 1.366922 0.940959 0.402559 11.00000 0.06255 0.06568 = 0.06331 0.00883 0.00265 0.00131 AFIX 43 H3 2 1.448932 0.993156 0.387523 11.00000 -1.20000 AFIX 0 C16 1 0.014728 0.488647 0.256180 11.00000 0.05208 0.08529 = 0.08133 0.01552 0.02840 0.01552 AFIX 137 H16A 2 -0.073267 0.465631 0.213686 11.00000 -1.50000 H16B 2 0.031590 0.577198 0.275084 11.00000 -1.50000 H16C 2 0.004082 0.443227 0.308314 11.00000 -1.50000 AFIX 0 C24 1 0.279234 0.847132 -0.032118 11.00000 0.08757 0.11333 = 0.05650 0.03675 0.01185 0.04423 AFIX 43 H24 2 0.267763 0.846031 -0.095138 11.00000 -1.20000 AFIX 0 C22 1 0.293441 0.957530 0.112459 11.00000 0.09211 0.05715 = 0.08939 0.01414 0.01520 0.01928 AFIX 43 H22 2 0.293294 1.031442 0.148962 11.00000 -1.20000 AFIX 0 C33 1 0.904414 1.121335 0.286332 11.00000 0.09994 0.04421 = 0.09315 0.00305 -0.03594 0.00480 AFIX 43 H33 2 0.939168 1.203244 0.312962 11.00000 -1.20000 AFIX 0 C23 1 0.280795 0.956113 0.020398 11.00000 0.09876 0.08451 = 0.08860 0.03889 0.02128 0.03838 AFIX 43 H23 2 0.273272 1.029197 -0.006416 11.00000 -1.20000 AFIX 0 C27 1 0.571120 0.578878 0.221285 11.00000 0.03212 0.03552 = 0.03914 0.00355 0.00343 0.00693 C18 1 0.159115 0.428743 0.042234 11.00000 0.04556 0.08028 = 0.05408 -0.00856 -0.00309 -0.00327 AFIX 137 H18A 2 0.167303 0.474002 -0.010139 11.00000 -1.50000 H18B 2 0.064337 0.375140 0.035850 11.00000 -1.50000 H18C 2 0.234266 0.378683 0.047262 11.00000 -1.50000 AFIX 0 HKLF 4 REM MP-9-50 (2) in P-1 #2 REM R1 = 0.0581 for 3788 Fo > 4sig(Fo) and 0.1101 for all 6710 data REM 372 parameters refined using 0 restraints END WGHT 0.0504 0.1918 REM Instructions for potential hydrogen bonds HTAB C26 O3 HTAB C14 O2 HTAB C13 O2 REM Highest difference peak 0.157, deepest hole -0.241, 1-sigma level 0.045 Q1 1 0.3550 0.6823 0.1229 11.00000 0.05 0.16 Q2 1 0.5741 0.3782 0.1229 11.00000 0.05 0.16 Q3 1 0.4651 0.4763 0.0933 11.00000 0.05 0.15 Q4 1 -0.0048 0.6931 0.2211 11.00000 0.05 0.15 Q5 1 0.3924 0.6211 0.3239 11.00000 0.05 0.15 Q6 1 0.4568 0.7201 0.3149 11.00000 0.05 0.15 Q7 1 1.0404 1.0042 0.4697 11.00000 0.05 0.15 Q8 1 0.2579 0.3766 0.0263 11.00000 0.05 0.14 Q9 1 0.2581 1.0745 0.0213 11.00000 0.05 0.14 Q10 1 0.8014 1.2601 0.3757 11.00000 0.05 0.14 Q11 1 0.5233 0.2756 0.0842 11.00000 0.05 0.14 Q12 1 1.4745 0.6795 0.3720 11.00000 0.05 0.14 Q13 1 0.9938 0.8257 0.1370 11.00000 0.05 0.14 Q14 1 0.4061 0.8639 0.2237 11.00000 0.05 0.14 Q15 1 0.6300 0.7576 0.0059 11.00000 0.05 0.13 Q16 1 0.4731 0.7795 0.2231 11.00000 0.05 0.13 Q17 1 0.2989 1.0324 0.2087 11.00000 0.05 0.13 Q18 1 0.6060 0.6890 0.3127 11.00000 0.05 0.13 Q19 1 0.8105 1.0971 0.3984 11.00000 0.05 0.13 Q20 1 0.4819 0.5101 0.2961 11.00000 0.05 0.13 ; _shelx_res_checksum 48235 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.61807(16) 0.75524(14) 0.10351(10) 0.0464(4) Uani 1 1 d . . . . . O4 O 0.54824(16) 0.62583(14) 0.06633(9) 0.0455(4) Uani 1 1 d . . . . . O3 O 0.32635(15) 0.35342(14) 0.19782(10) 0.0465(4) Uani 1 1 d . . . . . O1 O 0.62039(16) 0.60203(15) 0.43817(10) 0.0504(4) Uani 1 1 d . . . . . O2 O 0.73700(17) 0.45599(15) 0.38006(11) 0.0541(4) Uani 1 1 d . . . . . C10 C 0.6373(2) 0.5130(2) 0.37411(14) 0.0402(5) Uani 1 1 d . . . . . C11 C 0.5187(2) 0.49889(19) 0.29466(14) 0.0374(5) Uani 1 1 d . . . . . H11 H 0.4368 0.5327 0.3171 0.045 Uiso 1 1 calc R U . . . C29 C 0.7444(2) 0.7448(2) 0.16442(15) 0.0416(5) Uani 1 1 d . . . . . H29 H 0.8180 0.7152 0.1300 0.050 Uiso 1 1 calc R U . . . C19 C 0.3242(2) 0.6214(2) 0.14803(14) 0.0400(5) Uani 1 1 d . . . . . H19 H 0.3338 0.6496 0.2132 0.048 Uiso 1 1 calc R U . . . N1 N 0.21108(19) 0.38032(18) 0.24996(13) 0.0490(5) Uani 1 1 d . . . . . C12 C 0.4585(2) 0.3628(2) 0.25638(15) 0.0415(5) Uani 1 1 d . . . . . C26 C 0.4684(2) 0.5705(2) 0.13390(13) 0.0385(5) Uani 1 1 d . . . . . H26 H 0.4381 0.4809 0.1125 0.046 Uiso 1 1 calc R U . . . C28 C 0.7001(2) 0.65555(19) 0.23144(14) 0.0393(5) Uani 1 1 d . . . . . H28 H 0.7661 0.6537 0.2827 0.047 Uiso 1 1 calc R U . . . C30 C 0.8023(2) 0.8776(2) 0.20818(15) 0.0443(5) Uani 1 1 d . . . . . C15 C 0.1427(2) 0.4572(2) 0.21152(16) 0.0475(6) Uani 1 1 d . . . . . C17 C 0.1774(2) 0.5220(2) 0.12801(15) 0.0471(6) Uani 1 1 d . . . . . H17 H 0.1001 0.5715 0.1171 0.056 Uiso 1 1 calc R U . . . C20 C 0.3081(2) 0.7370(2) 0.10033(15) 0.0456(6) Uani 1 1 d . . . . . C6 C 1.1219(3) 0.7871(2) 0.45046(15) 0.0514(6) Uani 1 1 d . . . . . C14 C 0.4731(3) 0.2508(2) 0.30505(18) 0.0568(7) Uani 1 1 d . . . . . H14A H 0.3888 0.1828 0.2986 0.068 Uiso 1 1 calc R U . . . H14B H 0.5326 0.2642 0.3641 0.068 Uiso 1 1 calc R U . . . C9 C 0.7412(3) 0.6384(3) 0.51224(16) 0.0615(7) Uani 1 1 d . . . . . H9A H 0.7762 0.5643 0.5304 0.074 Uiso 1 1 calc R U . . . H9B H 0.7069 0.6789 0.5644 0.074 Uiso 1 1 calc R U . . . C35 C 0.9264(3) 0.9473(2) 0.18286(18) 0.0611(7) Uani 1 1 d . . . . . H35 H 0.9765 0.9123 0.1394 0.073 Uiso 1 1 calc R U . . . C13 C 0.5500(3) 0.2742(2) 0.22273(18) 0.0573(7) Uani 1 1 d . . . . . H13A H 0.6558 0.3016 0.2322 0.069 Uiso 1 1 calc R U . . . H13B H 0.5121 0.2202 0.1667 0.069 Uiso 1 1 calc R U . . . C21 C 0.3066(3) 0.8483(2) 0.15181(17) 0.0585(7) Uani 1 1 d . . . . . H21 H 0.3146 0.8503 0.2149 0.070 Uiso 1 1 calc R U . . . C7 C 0.9963(3) 0.7052(2) 0.47808(16) 0.0593(7) Uani 1 1 d . . . . . H7 H 1.0130 0.6282 0.4951 0.071 Uiso 1 1 calc R U . . . C5 C 1.1132(3) 0.9038(2) 0.42072(17) 0.0598(7) Uani 1 1 d . . . . . H5 H 1.0238 0.9311 0.4164 0.072 Uiso 1 1 calc R U . . . C25 C 0.2943(3) 0.7376(3) 0.00586(17) 0.0643(7) Uani 1 1 d . . . . . H25 H 0.2952 0.6646 -0.0315 0.077 Uiso 1 1 calc R U . . . C4 C 1.2345(3) 0.9789(3) 0.39774(18) 0.0650(7) Uani 1 1 d . . . . . H4 H 1.2266 1.0569 0.3786 0.078 Uiso 1 1 calc R U . . . C8 C 0.8641(3) 0.7268(2) 0.48168(16) 0.0591(7) Uani 1 1 d . . . . . H8 H 0.8443 0.8027 0.4640 0.071 Uiso 1 1 calc R U . . . C31 C 0.7299(3) 0.9315(2) 0.27272(19) 0.0619(7) Uani 1 1 d . . . . . H31 H 0.6456 0.8853 0.2901 0.074 Uiso 1 1 calc R U . . . C1 C 1.2578(3) 0.7503(3) 0.45348(18) 0.0661(7) Uani 1 1 d . . . . . H1 H 1.2672 0.6724 0.4722 0.079 Uiso 1 1 calc R U . . . C2 C 1.3783(3) 0.8260(3) 0.42955(19) 0.0719(8) Uani 1 1 d . . . . . H2 H 1.4678 0.7990 0.4317 0.086 Uiso 1 1 calc R U . . . C32 C 0.7809(4) 1.0530(3) 0.3117(2) 0.0772(8) Uani 1 1 d . . . . . H32 H 0.7314 1.0885 0.3552 0.093 Uiso 1 1 calc R U . . . C34 C 0.9768(3) 1.0701(3) 0.2223(2) 0.0808(9) Uani 1 1 d . . . . . H34 H 1.0603 1.1174 0.2048 0.097 Uiso 1 1 calc R U . . . C3 C 1.3669(3) 0.9410(3) 0.40256(18) 0.0654(7) Uani 1 1 d . . . . . H3 H 1.4489 0.9932 0.3875 0.079 Uiso 1 1 calc R U . . . C16 C 0.0147(3) 0.4886(3) 0.25618(19) 0.0707(8) Uani 1 1 d . . . . . H16A H -0.0733 0.4656 0.2137 0.106 Uiso 1 1 calc R U . . . H16B H 0.0316 0.5772 0.2751 0.106 Uiso 1 1 calc R U . . . H16C H 0.0041 0.4432 0.3083 0.106 Uiso 1 1 calc R U . . . C24 C 0.2792(3) 0.8471(3) -0.0321(2) 0.0808(10) Uani 1 1 d . . . . . H24 H 0.2678 0.8460 -0.0951 0.097 Uiso 1 1 calc R U . . . C22 C 0.2934(3) 0.9575(3) 0.1125(2) 0.0782(9) Uani 1 1 d . . . . . H22 H 0.2933 1.0314 0.1490 0.094 Uiso 1 1 calc R U . . . C33 C 0.9044(4) 1.1213(3) 0.2863(2) 0.0841(10) Uani 1 1 d . . . . . H33 H 0.9392 1.2032 0.3130 0.101 Uiso 1 1 calc R U . . . C23 C 0.2808(4) 0.9561(3) 0.0204(2) 0.0855(10) Uani 1 1 d . . . . . H23 H 0.2733 1.0292 -0.0064 0.103 Uiso 1 1 calc R U . . . C27 C 0.5711(2) 0.57888(19) 0.22129(14) 0.0356(5) Uani 1 1 d . . . . . C18 C 0.1591(3) 0.4287(3) 0.04223(17) 0.0635(7) Uani 1 1 d . . . . . H18A H 0.1673 0.4740 -0.0101 0.095 Uiso 1 1 calc R U . . . H18B H 0.0643 0.3751 0.0358 0.095 Uiso 1 1 calc R U . . . H18C H 0.2343 0.3787 0.0473 0.095 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 O5 0.0432(9) 0.0466(9) 0.0457(9) 0.0105(7) -0.0004(7) -0.0004(7) O4 0.0431(8) 0.0516(10) 0.0378(8) 0.0018(7) 0.0067(7) -0.0017(7) O3 0.0368(8) 0.0478(9) 0.0523(9) 0.0002(7) 0.0078(7) 0.0020(7) O1 0.0501(9) 0.0567(10) 0.0421(9) -0.0020(8) 0.0036(8) 0.0087(8) O2 0.0490(9) 0.0550(10) 0.0603(10) 0.0104(8) -0.0023(8) 0.0187(8) C10 0.0421(12) 0.0386(12) 0.0407(12) 0.0110(10) 0.0074(10) 0.0048(10) C11 0.0340(11) 0.0372(12) 0.0412(12) 0.0046(9) 0.0047(9) 0.0069(9) C29 0.0330(11) 0.0454(13) 0.0459(13) 0.0087(10) 0.0051(10) 0.0039(10) C19 0.0346(11) 0.0504(13) 0.0343(11) 0.0036(10) 0.0005(9) 0.0092(10) N1 0.0333(10) 0.0545(13) 0.0567(12) 0.0038(10) 0.0122(9) -0.0012(9) C12 0.0364(12) 0.0398(12) 0.0480(13) 0.0059(10) 0.0078(10) 0.0039(9) C26 0.0342(11) 0.0417(12) 0.0381(12) 0.0043(9) 0.0064(9) 0.0022(9) C28 0.0351(11) 0.0418(12) 0.0409(12) 0.0068(10) 0.0017(9) 0.0074(9) C30 0.0411(12) 0.0413(13) 0.0486(13) 0.0106(10) -0.0002(10) 0.0035(10) C15 0.0315(11) 0.0552(15) 0.0520(14) 0.0012(12) 0.0059(10) -0.0004(11) C17 0.0323(11) 0.0615(15) 0.0463(13) 0.0048(11) 0.0036(10) 0.0071(11) C20 0.0383(12) 0.0598(15) 0.0391(13) 0.0080(11) 0.0031(10) 0.0105(11) C6 0.0586(15) 0.0466(14) 0.0446(13) 0.0049(11) -0.0031(12) 0.0034(12) C14 0.0577(15) 0.0425(14) 0.0703(17) 0.0146(12) 0.0087(13) 0.0047(11) C9 0.0678(17) 0.0704(18) 0.0387(13) -0.0013(12) -0.0025(13) 0.0012(14) C35 0.0524(15) 0.0562(16) 0.0692(17) 0.0151(13) 0.0026(13) -0.0058(13) C13 0.0518(15) 0.0446(14) 0.0763(18) -0.0018(13) 0.0155(14) 0.0109(11) C21 0.0648(17) 0.0587(17) 0.0515(15) 0.0058(13) 0.0043(13) 0.0120(13) C7 0.0673(18) 0.0521(16) 0.0547(15) 0.0099(12) -0.0039(13) 0.0058(13) C5 0.0565(16) 0.0573(16) 0.0688(17) 0.0139(13) 0.0079(13) 0.0160(13) C25 0.0709(18) 0.084(2) 0.0458(15) 0.0163(14) 0.0072(13) 0.0305(15) C4 0.0731(19) 0.0522(16) 0.0726(18) 0.0182(14) 0.0140(15) 0.0108(14) C8 0.0633(17) 0.0558(16) 0.0520(15) -0.0001(12) -0.0040(13) 0.0037(13) C31 0.0605(16) 0.0489(16) 0.0741(18) 0.0001(13) 0.0058(14) 0.0095(13) C1 0.0719(19) 0.0533(16) 0.0733(18) 0.0166(14) -0.0059(15) 0.0171(14) C2 0.0567(17) 0.077(2) 0.082(2) 0.0125(17) -0.0017(15) 0.0177(16) C32 0.088(2) 0.0570(19) 0.082(2) -0.0069(16) -0.0066(18) 0.0188(17) C34 0.071(2) 0.060(2) 0.097(2) 0.0264(18) -0.0161(18) -0.0182(16) C3 0.0625(18) 0.0657(19) 0.0633(17) 0.0088(14) 0.0027(14) 0.0013(14) C16 0.0521(16) 0.085(2) 0.081(2) 0.0155(16) 0.0284(15) 0.0155(14) C24 0.088(2) 0.113(3) 0.0565(18) 0.0368(19) 0.0118(16) 0.044(2) C22 0.092(2) 0.0572(18) 0.089(2) 0.0141(16) 0.0152(19) 0.0193(16) C33 0.100(3) 0.0442(17) 0.093(2) 0.0030(17) -0.036(2) 0.0048(18) C23 0.099(2) 0.085(2) 0.089(2) 0.039(2) 0.021(2) 0.038(2) C27 0.0321(11) 0.0355(11) 0.0391(11) 0.0035(9) 0.0034(9) 0.0069(9) C18 0.0456(14) 0.080(2) 0.0541(15) -0.0086(14) -0.0031(12) -0.0033(13) 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 C29 O5 O4 106.19(14) . . ? C26 O4 O5 107.88(13) . . ? C12 O3 N1 109.87(15) . . ? C10 O1 C9 115.75(18) . . ? O2 C10 O1 123.4(2) . . ? O2 C10 C11 126.0(2) . . ? O1 C10 C11 110.59(18) . . ? C10 C11 C27 110.46(16) . . ? C10 C11 C12 113.56(17) . . ? C27 C11 C12 111.88(17) . . ? C10 C11 H11 106.8 . . ? C27 C11 H11 106.8 . . ? C12 C11 H11 106.8 . . ? O5 C29 C28 109.57(16) . . ? O5 C29 C30 104.15(17) . . ? C28 C29 C30 113.02(18) . . ? O5 C29 H29 110.0 . . ? C28 C29 H29 110.0 . . ? C30 C29 H29 110.0 . . ? C20 C19 C26 113.97(17) . . ? C20 C19 C17 110.06(18) . . ? C26 C19 C17 115.98(18) . . ? C20 C19 H19 105.2 . . ? C26 C19 H19 105.2 . . ? C17 C19 H19 105.2 . . ? C15 N1 O3 109.68(17) . . ? O3 C12 C13 111.67(19) . . ? O3 C12 C14 115.66(18) . . ? C13 C12 C14 60.73(15) . . ? O3 C12 C11 110.69(17) . . ? C13 C12 C11 124.11(18) . . ? C14 C12 C11 125.5(2) . . ? O4 C26 C27 109.23(15) . . ? O4 C26 C19 114.72(17) . . ? C27 C26 C19 113.09(16) . . ? O4 C26 H26 106.4 . . ? C27 C26 H26 106.4 . . ? C19 C26 H26 106.4 . . ? C27 C28 C29 123.1(2) . . ? C27 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? C35 C30 C31 119.0(2) . . ? C35 C30 C29 120.5(2) . . ? C31 C30 C29 120.5(2) . . ? N1 C15 C16 115.4(2) . . ? N1 C15 C17 127.8(2) . . ? C16 C15 C17 116.9(2) . . ? C15 C17 C18 112.3(2) . . ? C15 C17 C19 111.68(18) . . ? C18 C17 C19 116.94(17) . . ? C15 C17 H17 104.9 . . ? C18 C17 H17 104.9 . . ? C19 C17 H17 104.9 . . ? C21 C20 C25 117.2(2) . . ? C21 C20 C19 119.2(2) . . ? C25 C20 C19 123.7(2) . . ? C1 C6 C5 116.9(2) . . ? C1 C6 C7 120.3(2) . . ? C5 C6 C7 122.8(2) . . ? C12 C14 C13 59.45(15) . . ? C12 C14 H14A 117.8 . . ? C13 C14 H14A 117.8 . . ? C12 C14 H14B 117.8 . . ? C13 C14 H14B 117.8 . . ? H14A C14 H14B 115.0 . . ? O1 C9 C8 109.82(19) . . ? O1 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? O1 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C30 C35 C34 119.9(3) . . ? C30 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C12 C13 C14 59.82(14) . . ? C12 C13 H13A 117.8 . . ? C14 C13 H13A 117.8 . . ? C12 C13 H13B 117.8 . . ? C14 C13 H13B 117.8 . . ? H13A C13 H13B 114.9 . . ? C20 C21 C22 122.0(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C8 C7 C6 128.0(3) . . ? C8 C7 H7 116.0 . . ? C6 C7 H7 116.0 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C24 C25 C20 119.9(3) . . ? C24 C25 H25 120.0 . . ? C20 C25 H25 120.0 . . ? C3 C4 C5 120.9(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C7 C8 C9 124.8(3) . . ? C7 C8 H8 117.6 . . ? C9 C8 H8 117.6 . . ? C32 C31 C30 120.7(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C2 C1 C6 121.6(2) . . ? C2 C1 H1 119.2 . . ? C6 C1 H1 119.2 . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C33 C32 C31 119.9(3) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C33 C34 C35 120.2(3) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C23 C24 C25 121.6(3) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C23 C22 C21 119.8(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C34 C33 C32 120.3(3) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C24 C23 C22 119.5(3) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C28 C27 C26 119.34(18) . . ? C28 C27 C11 123.03(19) . . ? C26 C27 C11 117.62(16) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 O5 C29 1.432(2) . ? O5 O4 1.475(2) . ? O4 C26 1.428(2) . ? O3 C12 1.411(2) . ? O3 N1 1.447(2) . ? O1 C10 1.339(3) . ? O1 C9 1.461(3) . ? O2 C10 1.204(2) . ? C10 C11 1.505(3) . ? C11 C27 1.524(3) . ? C11 C12 1.525(3) . ? C11 H11 0.9800 . ? C29 C28 1.492(3) . ? C29 C30 1.512(3) . ? C29 H29 0.9800 . ? C19 C20 1.518(3) . ? C19 C26 1.568(3) . ? C19 C17 1.571(3) . ? C19 H19 0.9800 . ? N1 C15 1.274(3) . ? C12 C13 1.484(3) . ? C12 C14 1.489(3) . ? C26 C27 1.513(3) . ? C26 H26 0.9800 . ? C28 C27 1.323(3) . ? C28 H28 0.9300 . ? C30 C35 1.376(3) . ? C30 C31 1.379(3) . ? C15 C16 1.502(3) . ? C15 C17 1.518(3) . ? C17 C18 1.533(3) . ? C17 H17 0.9800 . ? C20 C21 1.378(3) . ? C20 C25 1.397(3) . ? C6 C1 1.391(3) . ? C6 C5 1.393(3) . ? C6 C7 1.463(3) . ? C14 C13 1.503(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C9 C8 1.500(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C35 C34 1.390(4) . ? C35 H35 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C21 C22 1.388(4) . ? C21 H21 0.9300 . ? C7 C8 1.300(3) . ? C7 H7 0.9300 . ? C5 C4 1.368(3) . ? C5 H5 0.9300 . ? C25 C24 1.384(4) . ? C25 H25 0.9300 . ? C4 C3 1.365(4) . ? C4 H4 0.9300 . ? C8 H8 0.9300 . ? C31 C32 1.376(4) . ? C31 H31 0.9300 . ? C1 C2 1.373(3) . ? C1 H1 0.9300 . ? C2 C3 1.364(4) . ? C2 H2 0.9300 . ? C32 C33 1.366(4) . ? C32 H32 0.9300 . ? C34 C33 1.361(4) . ? C34 H34 0.9300 . ? C3 H3 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C24 C23 1.358(4) . ? C24 H24 0.9300 . ? C22 C23 1.359(4) . ? C22 H22 0.9300 . ? C33 H33 0.9300 . ? C23 H23 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C29 O5 O4 C26 78.04(17) . . . . ? C9 O1 C10 O2 7.4(3) . . . . ? C9 O1 C10 C11 -170.81(17) . . . . ? O2 C10 C11 C27 -84.0(2) . . . . ? O1 C10 C11 C27 94.20(19) . . . . ? O2 C10 C11 C12 42.7(3) . . . . ? O1 C10 C11 C12 -139.18(18) . . . . ? O4 O5 C29 C28 -52.9(2) . . . . ? O4 O5 C29 C30 -174.07(14) . . . . ? C12 O3 N1 C15 132.81(19) . . . . ? N1 O3 C12 C13 148.15(17) . . . . ? N1 O3 C12 C14 81.3(2) . . . . ? N1 O3 C12 C11 -69.18(19) . . . . ? C10 C11 C12 O3 165.96(16) . . . . ? C27 C11 C12 O3 -68.2(2) . . . . ? C10 C11 C12 C13 -56.9(3) . . . . ? C27 C11 C12 C13 68.9(3) . . . . ? C10 C11 C12 C14 19.0(3) . . . . ? C27 C11 C12 C14 144.9(2) . . . . ? O5 O4 C26 C27 -55.57(19) . . . . ? O5 O4 C26 C19 72.60(19) . . . . ? C20 C19 C26 O4 -10.6(3) . . . . ? C17 C19 C26 O4 118.75(19) . . . . ? C20 C19 C26 C27 115.6(2) . . . . ? C17 C19 C26 C27 -115.1(2) . . . . ? O5 C29 C28 C27 13.8(3) . . . . ? C30 C29 C28 C27 129.5(2) . . . . ? O5 C29 C30 C35 -105.1(2) . . . . ? C28 C29 C30 C35 136.1(2) . . . . ? O5 C29 C30 C31 73.6(2) . . . . ? C28 C29 C30 C31 -45.2(3) . . . . ? O3 N1 C15 C16 177.15(18) . . . . ? O3 N1 C15 C17 -4.3(3) . . . . ? N1 C15 C17 C18 64.8(3) . . . . ? C16 C15 C17 C18 -116.7(2) . . . . ? N1 C15 C17 C19 -68.8(3) . . . . ? C16 C15 C17 C19 109.7(2) . . . . ? C20 C19 C17 C15 -140.83(19) . . . . ? C26 C19 C17 C15 87.9(2) . . . . ? C20 C19 C17 C18 87.9(2) . . . . ? C26 C19 C17 C18 -43.3(3) . . . . ? C26 C19 C20 C21 -116.2(2) . . . . ? C17 C19 C20 C21 111.5(2) . . . . ? C26 C19 C20 C25 63.9(3) . . . . ? C17 C19 C20 C25 -68.3(3) . . . . ? O3 C12 C14 C13 101.6(2) . . . . ? C11 C12 C14 C13 -112.9(2) . . . . ? C10 O1 C9 C8 79.4(3) . . . . ? C31 C30 C35 C34 0.0(4) . . . . ? C29 C30 C35 C34 178.7(2) . . . . ? O3 C12 C13 C14 -108.1(2) . . . . ? C11 C12 C13 C14 115.1(2) . . . . ? C25 C20 C21 C22 -0.7(4) . . . . ? C19 C20 C21 C22 179.5(2) . . . . ? C1 C6 C7 C8 177.9(3) . . . . ? C5 C6 C7 C8 -1.8(4) . . . . ? C1 C6 C5 C4 -1.4(4) . . . . ? C7 C6 C5 C4 178.3(2) . . . . ? C21 C20 C25 C24 -0.3(4) . . . . ? C19 C20 C25 C24 179.6(2) . . . . ? C6 C5 C4 C3 0.6(4) . . . . ? C6 C7 C8 C9 -179.0(2) . . . . ? O1 C9 C8 C7 -119.0(3) . . . . ? C35 C30 C31 C32 -0.3(4) . . . . ? C29 C30 C31 C32 -179.0(2) . . . . ? C5 C6 C1 C2 0.9(4) . . . . ? C7 C6 C1 C2 -178.8(2) . . . . ? C6 C1 C2 C3 0.4(4) . . . . ? C30 C31 C32 C33 0.1(4) . . . . ? C30 C35 C34 C33 0.5(4) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C5 C4 C3 C2 0.8(4) . . . . ? C20 C25 C24 C23 1.5(5) . . . . ? C20 C21 C22 C23 0.4(5) . . . . ? C35 C34 C33 C32 -0.7(5) . . . . ? C31 C32 C33 C34 0.4(4) . . . . ? C25 C24 C23 C22 -1.8(5) . . . . ? C21 C22 C23 C24 0.9(5) . . . . ? C29 C28 C27 C26 6.3(3) . . . . ? C29 C28 C27 C11 -172.63(18) . . . . ? O4 C26 C27 C28 15.2(3) . . . . ? C19 C26 C27 C28 -113.8(2) . . . . ? O4 C26 C27 C11 -165.76(17) . . . . ? C19 C26 C27 C11 65.2(2) . . . . ? C10 C11 C27 C28 -4.3(3) . . . . ? C12 C11 C27 C28 -131.9(2) . . . . ? C10 C11 C27 C26 176.70(18) . . . . ? C12 C11 C27 C26 49.1(2) . . . . ?