#------------------------------------------------------------------------------ #$Date: 2024-12-06 22:40:09 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296703 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160164.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_7160164 loop_ _publ_author_name 'Havlíková, Tereza' 'Nallappan, Sundaravelu' 'Císařová, Ivana' 'Rycek, Lukas' _publ_section_title ; Synthesis and structural confirmation of selaginpulvilin X. ; _journal_issue 45 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8843 _journal_page_last 8846 _journal_paper_doi 10.1039/d4ob01529k _journal_volume 22 _journal_year 2024 _chemical_compound_source 'synthesized by the authors' _chemical_formula_moiety 'C29 H22 O4' _chemical_formula_sum 'C29 H22 O4' _chemical_formula_weight 434.46 _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 mixed _atom_sites_solution_primary direct _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2024-08-07 deposited with the CCDC. 2024-10-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.343(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4717(5) _cell_length_b 12.7788(7) _cell_length_c 18.5575(10) _cell_measurement_reflns_used 9886 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 68.3069 _cell_measurement_theta_min 4.8448 _cell_volume 2209.6(2) _computing_cell_refinement 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_data_collection 'Bruker Instrument Service v8.5.1.2 Release' _computing_data_reduction 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'Helios Cu multilayer optic' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0158 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 31736 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.301 _diffrn_reflns_theta_min 4.845 _diffrn_source 'I\mS micro-focus sealed tube' _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). "Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination" J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_description prism _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.126 _exptl_crystal_size_min 0.082 _refine_diff_density_max 0.220 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 4039 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0317 _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^)+(0.0368P)^2^+0.8408P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.0808 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3844 _reflns_number_total 4039 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01529k2.cif _cod_data_source_block cu_th119_rycek _cod_depositor_comments 'Adding full bibliography for 7160164.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7160164 _shelx_shelxl_version_number 2019/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.862 _shelx_estimated_absorpt_t_max 0.945 _shelx_res_file ; TITL cu_th119_rycek_a.res in P2(1)/n cu_th119_rycek.res created by SHELXL-2019/3 at 14:37:34 on 07-Aug-2024 REM Old TITL cu_th119_rycek in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.097, Rweak 0.002, Alpha 0.019 REM 0.757 for 204 systematic absences, Orientation as input REM Formula found by SHELXT: C29 O4 CELL 1.54178 9.4717 12.7788 18.5575 90.000 100.343 90.000 ZERR 4.000 0.0005 0.0007 0.0010 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H O UNIT 116 88 16 TEMP -153.150 SIZE 0.082 0.126 0.22 L.S. 10 BOND $H LIST 4 ACTA FMAP 2 PLAN -20 WGHT 0.036800 0.840800 FVAR 0.72728 O1 3 0.383389 0.521319 0.664159 11.00000 0.02683 0.02262 = 0.02263 0.00216 0.00066 0.00472 O2 3 0.696857 1.145735 0.769403 11.00000 0.03138 0.02541 = 0.02460 -0.00392 0.00701 -0.00789 O3 3 0.004154 0.135910 0.614891 11.00000 0.03133 0.02129 = 0.03184 0.00528 0.00545 -0.00584 O4 3 -0.033895 0.876522 0.738928 11.00000 0.02362 0.02589 = 0.02685 -0.00978 0.00437 0.00145 AFIX 3 H4 2 0.020515 0.910200 0.776813 11.00000 -1.50000 AFIX 0 C1 1 0.325621 0.562020 0.393816 11.00000 0.02008 0.03046 = 0.01893 0.00020 0.00639 0.00096 AFIX 43 H1 2 0.332974 0.556898 0.343553 11.00000 -1.20000 AFIX 0 C2 1 0.274792 0.477726 0.428788 11.00000 0.01974 0.02275 = 0.02149 -0.00356 0.00499 -0.00005 AFIX 43 H2 2 0.247282 0.415353 0.402078 11.00000 -1.20000 AFIX 0 C3 1 0.263477 0.483304 0.502887 11.00000 0.01431 0.01960 = 0.02069 -0.00043 0.00370 0.00185 C4 1 0.303031 0.575942 0.541756 11.00000 0.01450 0.01931 = 0.01950 0.00014 0.00295 0.00235 C5 1 0.353735 0.661983 0.505983 11.00000 0.01513 0.02016 = 0.02221 0.00116 0.00209 0.00057 C6 1 0.365585 0.653409 0.431884 11.00000 0.01781 0.02538 = 0.02333 0.00447 0.00526 -0.00097 AFIX 43 H6 2 0.401213 0.710647 0.407815 11.00000 -1.20000 AFIX 0 C7 1 0.401135 0.756127 0.544982 11.00000 0.02019 0.02192 = 0.02286 0.00390 0.00490 -0.00121 C8 1 0.446484 0.834201 0.577558 11.00000 0.02235 0.02176 = 0.02539 0.00336 0.00412 -0.00122 C9 1 0.504379 0.920789 0.622240 11.00000 0.02150 0.01817 = 0.02513 0.00173 0.00199 0.00022 C10 1 0.462015 0.938281 0.690043 11.00000 0.02196 0.02196 = 0.03151 0.00244 0.00888 -0.00267 AFIX 43 H10 2 0.388023 0.896698 0.703768 11.00000 -1.20000 AFIX 0 C11 1 0.526453 1.014945 0.736802 11.00000 0.02679 0.02422 = 0.02543 -0.00021 0.01042 -0.00042 AFIX 43 H11 2 0.496150 1.026304 0.782274 11.00000 -1.20000 AFIX 0 C12 1 0.636099 1.076021 0.717654 11.00000 0.02173 0.01723 = 0.02279 0.00075 0.00182 0.00129 C13 1 0.676387 1.062431 0.649700 11.00000 0.02474 0.02279 = 0.02619 0.00107 0.00737 -0.00586 AFIX 43 H13 2 0.748553 1.105508 0.635631 11.00000 -1.20000 AFIX 0 C14 1 0.610126 0.985323 0.602651 11.00000 0.02955 0.02551 = 0.02321 -0.00074 0.00826 -0.00439 AFIX 43 H14 2 0.637380 0.976366 0.556206 11.00000 -1.20000 AFIX 0 C15 1 0.202818 0.391598 0.536009 11.00000 0.01745 0.02006 = 0.01663 -0.00185 0.00086 -0.00180 C16 1 0.251765 0.290960 0.525529 11.00000 0.01990 0.02250 = 0.02007 -0.00321 0.00382 0.00013 AFIX 43 H16 2 0.329399 0.281959 0.500043 11.00000 -1.20000 AFIX 0 C17 1 0.189607 0.203215 0.551521 11.00000 0.02627 0.01815 = 0.02254 -0.00276 0.00087 0.00112 AFIX 43 H17 2 0.225454 0.135244 0.544513 11.00000 -1.20000 AFIX 0 C18 1 0.074833 0.216059 0.587745 11.00000 0.02167 0.02101 = 0.01907 0.00224 -0.00094 -0.00467 C19 1 0.024885 0.316266 0.599333 11.00000 0.01742 0.02492 = 0.01970 0.00092 0.00300 -0.00086 AFIX 43 H19 2 -0.052956 0.325070 0.624701 11.00000 -1.20000 AFIX 0 C20 1 0.088635 0.402746 0.573910 11.00000 0.01873 0.01900 = 0.01889 -0.00149 0.00174 0.00086 AFIX 43 H20 2 0.054420 0.470749 0.582294 11.00000 -1.20000 AFIX 0 C21 1 0.306209 0.581820 0.623485 11.00000 0.01661 0.01697 = 0.01976 0.00044 0.00157 -0.00339 C22 1 0.218022 0.660867 0.652891 11.00000 0.01950 0.01640 = 0.01756 0.00048 0.00451 -0.00296 C23 1 0.255798 0.692299 0.726213 11.00000 0.01940 0.02341 = 0.01797 0.00173 0.00257 -0.00119 AFIX 43 H23 2 0.338295 0.663082 0.756135 11.00000 -1.20000 AFIX 0 C24 1 0.174319 0.765343 0.755452 11.00000 0.02266 0.02512 = 0.01559 -0.00323 0.00408 -0.00373 AFIX 43 H24 2 0.202707 0.788127 0.804650 11.00000 -1.20000 AFIX 0 C25 1 0.050621 0.805292 0.712493 11.00000 0.02064 0.01794 = 0.02213 -0.00279 0.00734 -0.00277 C26 1 0.009453 0.772653 0.640041 11.00000 0.02024 0.01868 = 0.02183 -0.00048 0.00013 0.00050 AFIX 43 H26 2 -0.076817 0.798269 0.611323 11.00000 -1.20000 AFIX 0 C27 1 0.094470 0.702952 0.610125 11.00000 0.02285 0.01793 = 0.01637 -0.00141 0.00203 -0.00232 AFIX 43 H27 2 0.068740 0.683476 0.560082 11.00000 -1.20000 AFIX 0 C28 1 0.815928 1.205510 0.755648 11.00000 0.03310 0.03427 = 0.02985 -0.00370 0.00407 -0.01400 AFIX 137 H28A 2 0.852301 1.248967 0.798475 11.00000 -1.50000 H28B 2 0.785573 1.250494 0.712906 11.00000 -1.50000 H28C 2 0.891934 1.158244 0.746090 11.00000 -1.50000 AFIX 0 C29 1 0.059571 0.032721 0.610905 11.00000 0.05618 0.02005 = 0.03996 0.00256 0.01162 -0.00461 AFIX 137 H29A 2 0.001192 -0.016735 0.633300 11.00000 -1.50000 H29B 2 0.158979 0.030279 0.637179 11.00000 -1.50000 H29C 2 0.056625 0.013707 0.559496 11.00000 -1.50000 REM ##### AFIX 0 HKLF 4 REM cu_th119_rycek_a.res in P2(1)/n REM wR2 = 0.0808, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.0317 for 3844 Fo > 4sig(Fo) and 0.0330 for all 4039 data REM 300 parameters refined using 0 restraints END WGHT 0.0368 0.8408 REM Highest difference peak 0.220, deepest hole -0.188, 1-sigma level 0.037 Q1 1 0.2974 0.5812 0.5787 11.00000 0.05 0.22 Q2 1 0.3166 0.5182 0.5288 11.00000 0.05 0.19 Q3 1 0.3068 0.6227 0.5226 11.00000 0.05 0.17 Q4 1 0.0631 0.8141 0.6698 11.00000 0.05 0.16 Q5 1 0.2424 0.4349 0.5234 11.00000 0.05 0.16 Q6 1 0.2170 0.6641 0.6902 11.00000 0.05 0.16 Q7 1 0.1163 0.3939 0.5327 11.00000 0.05 0.15 Q8 1 0.2855 0.4805 0.4694 11.00000 0.05 0.15 Q9 1 0.2379 0.4933 0.4656 11.00000 0.05 0.15 Q10 1 0.1422 0.6597 0.6349 11.00000 0.05 0.15 Q11 1 0.5042 0.9213 0.6587 11.00000 0.05 0.15 Q12 1 0.1743 0.3974 0.5690 11.00000 0.05 0.15 Q13 1 0.2533 0.6237 0.6370 11.00000 0.05 0.15 Q14 1 0.1326 0.8065 0.7260 11.00000 0.05 0.15 Q15 1 0.0931 0.7646 0.7396 11.00000 0.05 0.14 Q16 1 0.2590 0.3453 0.5500 11.00000 0.05 0.14 Q17 1 0.3696 0.7802 0.5799 11.00000 0.05 0.14 Q18 1 0.2384 0.5441 0.5179 11.00000 0.05 0.14 Q19 1 0.5332 0.9636 0.6079 11.00000 0.05 0.14 Q20 1 0.1589 0.2138 0.5896 11.00000 0.05 0.14 ; _shelx_res_checksum 7518 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 0.38339(8) 0.52132(6) 0.66416(4) 0.02450(18) Uani 1 1 d . . . . . O2 O 0.69686(9) 1.14574(6) 0.76940(4) 0.02688(19) Uani 1 1 d . . . . . O3 O 0.00415(9) 0.13591(6) 0.61489(5) 0.02818(19) Uani 1 1 d . . . . . O4 O -0.03390(8) 0.87652(6) 0.73893(4) 0.02548(19) Uani 1 1 d . . . . . H4 H 0.020515 0.910200 0.776813 0.038 Uiso 1 1 d R U . . . C1 C 0.32562(11) 0.56202(9) 0.39382(6) 0.0228(2) Uani 1 1 d . . . . . H1 H 0.332974 0.556898 0.343553 0.027 Uiso 1 1 calc R U . . . C2 C 0.27479(11) 0.47773(9) 0.42879(6) 0.0212(2) Uani 1 1 d . . . . . H2 H 0.247282 0.415353 0.402078 0.025 Uiso 1 1 calc R U . . . C3 C 0.26348(11) 0.48330(8) 0.50289(6) 0.0181(2) Uani 1 1 d . . . . . C4 C 0.30303(11) 0.57594(8) 0.54176(6) 0.0178(2) Uani 1 1 d . . . . . C5 C 0.35373(11) 0.66198(8) 0.50598(6) 0.0193(2) Uani 1 1 d . . . . . C6 C 0.36559(11) 0.65341(9) 0.43188(6) 0.0220(2) Uani 1 1 d . . . . . H6 H 0.401213 0.710647 0.407815 0.026 Uiso 1 1 calc R U . . . C7 C 0.40114(11) 0.75613(9) 0.54498(6) 0.0215(2) Uani 1 1 d . . . . . C8 C 0.44648(12) 0.83420(9) 0.57756(6) 0.0232(2) Uani 1 1 d . . . . . C9 C 0.50438(12) 0.92079(8) 0.62224(6) 0.0219(2) Uani 1 1 d . . . . . C10 C 0.46202(12) 0.93828(9) 0.69004(6) 0.0246(2) Uani 1 1 d . . . . . H10 H 0.388023 0.896698 0.703768 0.030 Uiso 1 1 calc R U . . . C11 C 0.52645(12) 1.01494(9) 0.73680(6) 0.0248(2) Uani 1 1 d . . . . . H11 H 0.496150 1.026304 0.782274 0.030 Uiso 1 1 calc R U . . . C12 C 0.63610(11) 1.07602(8) 0.71765(6) 0.0209(2) Uani 1 1 d . . . . . C13 C 0.67639(12) 1.06243(9) 0.64970(6) 0.0242(2) Uani 1 1 d . . . . . H13 H 0.748553 1.105508 0.635631 0.029 Uiso 1 1 calc R U . . . C14 C 0.61013(12) 0.98532(9) 0.60265(6) 0.0257(2) Uani 1 1 d . . . . . H14 H 0.637380 0.976366 0.556206 0.031 Uiso 1 1 calc R U . . . C15 C 0.20282(11) 0.39160(8) 0.53601(5) 0.0183(2) Uani 1 1 d . . . . . C16 C 0.25176(11) 0.29096(8) 0.52553(6) 0.0208(2) Uani 1 1 d . . . . . H16 H 0.329399 0.281959 0.500043 0.025 Uiso 1 1 calc R U . . . C17 C 0.18961(12) 0.20321(8) 0.55152(6) 0.0228(2) Uani 1 1 d . . . . . H17 H 0.225454 0.135244 0.544513 0.027 Uiso 1 1 calc R U . . . C18 C 0.07483(11) 0.21606(9) 0.58775(6) 0.0212(2) Uani 1 1 d . . . . . C19 C 0.02488(11) 0.31627(9) 0.59933(6) 0.0207(2) Uani 1 1 d . . . . . H19 H -0.052956 0.325070 0.624701 0.025 Uiso 1 1 calc R U . . . C20 C 0.08863(11) 0.40275(8) 0.57391(5) 0.0191(2) Uani 1 1 d . . . . . H20 H 0.054420 0.470749 0.582294 0.023 Uiso 1 1 calc R U . . . C21 C 0.30621(11) 0.58182(8) 0.62348(6) 0.0180(2) Uani 1 1 d . . . . . C22 C 0.21802(11) 0.66087(8) 0.65289(6) 0.0177(2) Uani 1 1 d . . . . . C23 C 0.25580(11) 0.69230(8) 0.72621(6) 0.0204(2) Uani 1 1 d . . . . . H23 H 0.338295 0.663082 0.756135 0.024 Uiso 1 1 calc R U . . . C24 C 0.17432(11) 0.76534(9) 0.75545(6) 0.0210(2) Uani 1 1 d . . . . . H24 H 0.202707 0.788127 0.804650 0.025 Uiso 1 1 calc R U . . . C25 C 0.05062(11) 0.80529(8) 0.71249(6) 0.0198(2) Uani 1 1 d . . . . . C26 C 0.00945(11) 0.77265(8) 0.64004(6) 0.0207(2) Uani 1 1 d . . . . . H26 H -0.076817 0.798269 0.611323 0.025 Uiso 1 1 calc R U . . . C27 C 0.09447(11) 0.70295(8) 0.61013(6) 0.0192(2) Uani 1 1 d . . . . . H27 H 0.068740 0.683476 0.560082 0.023 Uiso 1 1 calc R U . . . C28 C 0.81593(14) 1.20551(10) 0.75565(7) 0.0326(3) Uani 1 1 d . . . . . H28A H 0.852301 1.248967 0.798475 0.049 Uiso 1 1 calc R U . . . H28B H 0.785573 1.250494 0.712906 0.049 Uiso 1 1 calc R U . . . H28C H 0.891934 1.158244 0.746090 0.049 Uiso 1 1 calc R U . . . C29 C 0.05957(17) 0.03272(10) 0.61090(8) 0.0384(3) Uani 1 1 d . . . . . H29A H 0.001192 -0.016735 0.633300 0.058 Uiso 1 1 calc R U . . . H29B H 0.158979 0.030279 0.637179 0.058 Uiso 1 1 calc R U . . . H29C H 0.056625 0.013707 0.559496 0.058 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 0.0268(4) 0.0226(4) 0.0226(4) 0.0022(3) 0.0007(3) 0.0047(3) O2 0.0314(4) 0.0254(4) 0.0246(4) -0.0039(3) 0.0070(3) -0.0079(3) O3 0.0313(4) 0.0213(4) 0.0318(4) 0.0053(3) 0.0055(3) -0.0058(3) O4 0.0236(4) 0.0259(4) 0.0269(4) -0.0098(3) 0.0044(3) 0.0015(3) C1 0.0201(5) 0.0305(6) 0.0189(5) 0.0002(4) 0.0064(4) 0.0010(4) C2 0.0197(5) 0.0227(5) 0.0215(5) -0.0036(4) 0.0050(4) -0.0001(4) C3 0.0143(5) 0.0196(5) 0.0207(5) -0.0004(4) 0.0037(4) 0.0019(4) C4 0.0145(5) 0.0193(5) 0.0195(5) 0.0001(4) 0.0030(4) 0.0024(4) C5 0.0151(5) 0.0202(5) 0.0222(5) 0.0012(4) 0.0021(4) 0.0006(4) C6 0.0178(5) 0.0254(6) 0.0233(5) 0.0045(4) 0.0053(4) -0.0010(4) C7 0.0202(5) 0.0219(5) 0.0229(5) 0.0039(4) 0.0049(4) -0.0012(4) C8 0.0224(5) 0.0218(6) 0.0254(6) 0.0034(5) 0.0041(4) -0.0012(4) C9 0.0215(5) 0.0182(5) 0.0251(5) 0.0017(4) 0.0020(4) 0.0002(4) C10 0.0220(5) 0.0220(5) 0.0315(6) 0.0024(5) 0.0089(4) -0.0027(4) C11 0.0268(6) 0.0242(6) 0.0254(5) -0.0002(4) 0.0104(4) -0.0004(5) C12 0.0217(5) 0.0172(5) 0.0228(5) 0.0007(4) 0.0018(4) 0.0013(4) C13 0.0247(6) 0.0228(5) 0.0262(6) 0.0011(4) 0.0074(4) -0.0059(4) C14 0.0296(6) 0.0255(6) 0.0232(5) -0.0007(4) 0.0083(5) -0.0044(5) C15 0.0175(5) 0.0201(5) 0.0166(5) -0.0019(4) 0.0009(4) -0.0018(4) C16 0.0199(5) 0.0225(5) 0.0201(5) -0.0032(4) 0.0038(4) 0.0001(4) C17 0.0263(6) 0.0181(5) 0.0225(5) -0.0028(4) 0.0009(4) 0.0011(4) C18 0.0217(5) 0.0210(5) 0.0191(5) 0.0022(4) -0.0009(4) -0.0047(4) C19 0.0174(5) 0.0249(6) 0.0197(5) 0.0009(4) 0.0030(4) -0.0009(4) C20 0.0187(5) 0.0190(5) 0.0189(5) -0.0015(4) 0.0017(4) 0.0009(4) C21 0.0166(5) 0.0170(5) 0.0198(5) 0.0004(4) 0.0016(4) -0.0034(4) C22 0.0195(5) 0.0164(5) 0.0176(5) 0.0005(4) 0.0045(4) -0.0030(4) C23 0.0194(5) 0.0234(5) 0.0180(5) 0.0017(4) 0.0026(4) -0.0012(4) C24 0.0227(5) 0.0251(6) 0.0156(5) -0.0032(4) 0.0041(4) -0.0037(4) C25 0.0206(5) 0.0179(5) 0.0221(5) -0.0028(4) 0.0073(4) -0.0028(4) C26 0.0202(5) 0.0187(5) 0.0218(5) -0.0005(4) 0.0001(4) 0.0005(4) C27 0.0228(5) 0.0179(5) 0.0164(5) -0.0014(4) 0.0020(4) -0.0023(4) C28 0.0331(6) 0.0343(7) 0.0298(6) -0.0037(5) 0.0041(5) -0.0140(5) C29 0.0562(9) 0.0201(6) 0.0400(7) 0.0026(5) 0.0116(6) -0.0046(6) 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' 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 C12 O2 C28 118.28(9) . . ? C18 O3 C29 117.65(9) . . ? C25 O4 H4 108.0 . . ? C6 C1 C2 120.20(10) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C2 C3 120.93(10) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 119.20(10) . . ? C2 C3 C15 118.01(9) . . ? C4 C3 C15 122.73(9) . . ? C3 C4 C5 119.84(9) . . ? C3 C4 C21 120.86(9) . . ? C5 C4 C21 119.02(9) . . ? C6 C5 C4 119.56(10) . . ? C6 C5 C7 119.14(10) . . ? C4 C5 C7 121.20(9) . . ? C1 C6 C5 120.26(10) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C5 177.40(11) . . ? C7 C8 C9 174.56(12) . . ? C14 C9 C10 118.23(10) . . ? C14 C9 C8 121.62(10) . . ? C10 C9 C8 120.02(10) . . ? C11 C10 C9 120.79(10) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.24(10) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O2 C12 C13 124.84(10) . . ? O2 C12 C11 115.26(10) . . ? C13 C12 C11 119.90(10) . . ? C14 C13 C12 119.42(10) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C9 121.33(10) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? C16 C15 C20 118.10(10) . . ? C16 C15 C3 120.49(9) . . ? C20 C15 C3 121.25(9) . . ? C17 C16 C15 121.55(10) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 119.32(10) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? O3 C18 C17 124.60(10) . . ? O3 C18 C19 115.37(10) . . ? C17 C18 C19 120.03(10) . . ? C20 C19 C18 120.01(10) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 120.97(10) . . ? C19 C20 H20 119.5 . . ? C15 C20 H20 119.5 . . ? O1 C21 C22 121.21(9) . . ? O1 C21 C4 119.21(9) . . ? C22 C21 C4 119.58(9) . . ? C27 C22 C23 118.84(10) . . ? C27 C22 C21 121.65(9) . . ? C23 C22 C21 119.47(9) . . ? C24 C23 C22 120.73(10) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.68(10) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? O4 C25 C24 121.92(9) . . ? O4 C25 C26 117.83(10) . . ? C24 C25 C26 120.25(10) . . ? C27 C26 C25 119.85(10) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C22 120.56(9) . . ? C26 C27 H27 119.7 . . ? C22 C27 H27 119.7 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O3 C29 H29A 109.5 . . ? O3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 C21 1.2263(13) . ? O2 C12 1.3596(13) . ? O2 C28 1.4226(14) . ? O3 C18 1.3682(13) . ? O3 C29 1.4261(15) . ? O4 C25 1.3605(13) . ? O4 H4 0.9028 . ? C1 C6 1.3821(16) . ? C1 C2 1.3876(16) . ? C1 H1 0.9500 . ? C2 C3 1.4001(15) . ? C2 H2 0.9500 . ? C3 C4 1.4018(14) . ? C3 C15 1.4860(14) . ? C4 C5 1.4124(15) . ? C4 C21 1.5134(14) . ? C5 C6 1.4039(15) . ? C5 C7 1.4339(15) . ? C6 H6 0.9500 . ? C7 C8 1.2050(16) . ? C8 C9 1.4315(16) . ? C9 C14 1.3951(16) . ? C9 C10 1.4055(16) . ? C10 C11 1.3766(16) . ? C10 H10 0.9500 . ? C11 C12 1.3952(16) . ? C11 H11 0.9500 . ? C12 C13 1.3924(16) . ? C13 C14 1.3894(16) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.3925(15) . ? C15 C20 1.3992(15) . ? C16 C17 1.3923(16) . ? C16 H16 0.9500 . ? C17 C18 1.3867(16) . ? C17 H17 0.9500 . ? C18 C19 1.3951(16) . ? C19 C20 1.3823(15) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.4763(14) . ? C22 C27 1.3982(15) . ? C22 C23 1.4021(15) . ? C23 C24 1.3826(15) . ? C23 H23 0.9500 . ? C24 C25 1.3905(15) . ? C24 H24 0.9500 . ? C25 C26 1.3948(15) . ? C26 C27 1.3822(15) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ?