#------------------------------------------------------------------------------ #$Date: 2018-04-20 18:02:28 +0300 (Fri, 20 Apr 2018) $ #$Revision: 207424 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/05/7230513.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_7230513 loop_ _publ_author_name 'Lu, Ni-Hong' 'Zhang, Zi-Wei' 'Guo, Rui-Wei' 'Yang, Li-Xia' 'Song, Ya-Xian' 'Ye, Jin-Shan' 'Shi, Yan-Kun' _publ_section_title ; Yunnanterpene G, a spiro-triterpene from the roots of Cimicifuga foetida, downregulates the expression of CD147 and MMPs in PMA differentiated THP-1 cells ; _journal_issue 27 _journal_name_full 'RSC Advances' _journal_page_first 15036 _journal_paper_doi 10.1039/C8RA01895B _journal_volume 8 _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety 'C30 H44 O6, H2 O' _chemical_formula_sum 'C30 H46 O7' _chemical_formula_weight 518.67 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-12-22 deposited with the CCDC. 2018-04-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.545(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.1629(2) _cell_length_b 18.1237(6) _cell_length_c 12.4853(4) _cell_measurement_reflns_used 5779 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 69.19 _cell_measurement_theta_min 4.88 _cell_volume 1361.25(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_unetI/netI 0.0536 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11631 _diffrn_reflns_point_group_measured_fraction_full 0.890 _diffrn_reflns_point_group_measured_fraction_max 0.868 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 69.594 _diffrn_reflns_theta_min 4.880 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.265 _exptl_crystal_description prism _exptl_crystal_F_000 564 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.020 _exptl_transmission_factor_max 0.7532 _exptl_transmission_factor_min 0.5076 _refine_diff_density_max 0.207 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 1674 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.07(11) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 343 _refine_ls_number_reflns 4459 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0456 _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^)+(0.0841P)^2^+0.0487P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1209 _reflns_Friedel_coverage 0.732 _reflns_Friedel_fraction_full 0.786 _reflns_Friedel_fraction_max 0.759 _reflns_number_gt 4262 _reflns_number_total 4459 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ra01895b2.cif _cod_data_source_block cu_kys35_0m _cod_database_code 7230513 _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_estimated_absorpt_t_min 0.763 _shelx_estimated_absorpt_t_max 0.986 _shelx_res_file ; a.res created by SHELXL-2014/7 TITL a in P2(1) CELL 1.54178 6.1629 18.1237 12.4853 90.000 102.545 90.000 ZERR 2.00 0.0002 0.0006 0.0004 0.000 0.002 0.000 LATT -1 SYMM -x, y+1/2, -z SFAC C H O UNIT 60 92 14 L.S. 10 ACTA BOND $H FMAP 2 PLAN -4 HTAB O12 O1S_$2 HTAB O24 O16 HTAB O25 O12_$1 HTAB O1S O3 HTAB O1S O25_$3 HTAB O12 O1S_$2 HTAB O24 O16 HTAB O25 O12_$1 HTAB O1S O3 HTAB O1S O25_$3 HTAB O1S O3 HTAB O1S O25_$3 EQIV $3 x, y-1, z HTAB O12 O1S_$2 EQIV $2 -x, y+1/2, -z+2 HTAB O24 O16 HTAB O25 O12_$1 EQIV $1 -x+1, y+1/2, -z+2 HTAB CONF SIZE 0.020 0.120 0.400 HTAB O1S O25_$3 HTAB O1S O3 HTAB O25 O12_$1 HTAB O24 O16 HTAB O12 O1S_$2 TEMP -173.000 WGHT 0.084100 0.048700 FVAR 0.18899 O1S 3 -0.012605 0.075841 0.816896 11.00000 0.03005 0.02827 = 0.03223 0.00441 0.01777 0.00282 AFIX 3 H1SA 2 0.105207 0.048289 0.823352 11.00000 -1.50000 H1SB 2 -0.010306 0.104746 0.762799 11.00000 -1.50000 AFIX 0 O3 3 0.112601 0.178943 0.659069 11.00000 0.02996 0.02169 = 0.02882 -0.00148 0.01024 -0.00161 O16 3 0.364725 0.768946 0.727632 11.00000 0.03140 0.02062 = 0.02464 -0.00191 0.01793 -0.00142 O23 3 0.573903 0.853372 0.838357 11.00000 0.02646 0.02300 = 0.02506 0.00260 0.00837 0.00010 O25 3 0.368264 0.992513 0.839205 11.00000 0.02662 0.02247 = 0.02388 -0.00525 0.01274 -0.00035 AFIX 147 H25 2 0.473773 1.016465 0.877596 11.00000 -1.50000 AFIX 0 O24 3 0.277156 0.879750 0.595516 11.00000 0.04512 0.02420 = 0.01884 -0.00110 0.01276 -0.00223 AFIX 147 H24 2 0.330686 0.837110 0.595769 11.00000 -1.50000 AFIX 0 O12 3 0.284298 0.572560 1.036886 11.00000 0.02570 0.02551 = 0.01663 -0.00060 0.01172 0.00067 AFIX 147 H12 2 0.189911 0.578075 1.075696 11.00000 -1.50000 AFIX 0 C3 1 0.244458 0.226502 0.697684 11.00000 0.02283 0.02052 = 0.02444 -0.00091 0.00872 0.00479 C2 1 0.303154 0.241840 0.819017 11.00000 0.02995 0.02245 = 0.02446 0.00110 0.01251 -0.00251 AFIX 23 H2A 2 0.465167 0.235803 0.847202 11.00000 -1.20000 H2B 2 0.225041 0.206592 0.858107 11.00000 -1.20000 AFIX 0 C1 1 0.233574 0.321287 0.839148 11.00000 0.02639 0.01979 = 0.02272 -0.00118 0.01250 -0.00246 AFIX 23 H1A 2 0.069330 0.324685 0.820920 11.00000 -1.20000 H1B 2 0.285249 0.333351 0.917905 11.00000 -1.20000 AFIX 0 C10 1 0.328062 0.377102 0.771327 11.00000 0.02468 0.02081 = 0.02063 0.00038 0.01110 -0.00011 C9 1 0.307027 0.458743 0.799994 11.00000 0.02641 0.01789 = 0.01897 -0.00096 0.01197 -0.00295 C8 1 0.268464 0.511705 0.705516 11.00000 0.02189 0.02059 = 0.02094 -0.00051 0.01029 -0.00297 C14 1 0.169031 0.584898 0.725321 11.00000 0.02326 0.02188 = 0.01578 -0.00156 0.00865 -0.00110 C15 1 0.226013 0.650514 0.658712 11.00000 0.02524 0.02192 = 0.01744 0.00002 0.00961 0.00113 AFIX 23 H15A 2 0.383708 0.648702 0.653096 11.00000 -1.20000 H15B 2 0.130624 0.650779 0.583872 11.00000 -1.20000 AFIX 0 C16 1 0.181259 0.718481 0.723458 11.00000 0.02441 0.02287 = 0.01875 0.00344 0.00941 0.00092 AFIX 13 H16 2 0.039269 0.742481 0.685416 11.00000 -1.20000 AFIX 0 C23 1 0.350950 0.835698 0.786358 11.00000 0.02685 0.02030 = 0.02139 -0.00045 0.01247 0.00140 C24 1 0.269050 0.900389 0.704667 11.00000 0.02980 0.02161 = 0.01842 -0.00115 0.01062 -0.00042 AFIX 13 H24A 2 0.115622 0.916162 0.708852 11.00000 -1.20000 AFIX 0 C25 1 0.437570 0.961858 0.745433 11.00000 0.02687 0.02086 = 0.02273 -0.00193 0.01234 -0.00045 C27 1 0.454870 1.020983 0.662190 11.00000 0.03454 0.02009 = 0.03095 0.00112 0.01581 -0.00036 AFIX 137 H27A 2 0.311991 1.046564 0.640331 11.00000 -1.50000 H27B 2 0.493359 0.998228 0.597570 11.00000 -1.50000 H27C 2 0.570467 1.056464 0.694736 11.00000 -1.50000 AFIX 0 C19 1 0.532222 0.419744 0.825498 11.00000 0.02697 0.02032 = 0.02281 -0.00084 0.00872 -0.00100 AFIX 23 H19A 2 0.640247 0.432644 0.780268 11.00000 -1.20000 H19B 2 0.599095 0.408571 0.903281 11.00000 -1.20000 AFIX 0 C11 1 0.195824 0.476653 0.895484 11.00000 0.02865 0.02284 = 0.01910 -0.00096 0.01331 -0.00223 AFIX 23 H11A 2 0.281428 0.451657 0.961842 11.00000 -1.20000 H11B 2 0.045367 0.454527 0.878787 11.00000 -1.20000 AFIX 0 C12 1 0.171695 0.559584 0.924480 11.00000 0.02073 0.02365 = 0.01646 -0.00013 0.00902 0.00145 AFIX 13 H12A 2 0.010043 0.569975 0.918148 11.00000 -1.20000 AFIX 0 C13 1 0.257211 0.612154 0.846726 11.00000 0.02136 0.02191 = 0.01577 -0.00125 0.01039 0.00052 C7 1 0.306976 0.492804 0.608406 11.00000 0.03365 0.02075 = 0.02218 0.00213 0.01575 -0.00099 AFIX 43 H7 2 0.291112 0.529517 0.552937 11.00000 -1.20000 AFIX 0 C6 1 0.374487 0.416175 0.581720 11.00000 0.03782 0.02322 = 0.02349 0.00038 0.01683 0.00003 AFIX 23 H6A 2 0.538685 0.412665 0.597817 11.00000 -1.20000 H6B 2 0.318570 0.406361 0.502523 11.00000 -1.20000 AFIX 0 C5 1 0.281062 0.358129 0.649048 11.00000 0.02517 0.02160 = 0.02035 -0.00093 0.01025 0.00032 AFIX 13 H5 2 0.115826 0.359862 0.622955 11.00000 -1.20000 AFIX 0 C4 1 0.352401 0.277801 0.626436 11.00000 0.02620 0.02347 = 0.01953 -0.00206 0.01030 -0.00111 C30 1 0.605339 0.266751 0.656932 11.00000 0.02977 0.02416 = 0.02872 -0.00073 0.01536 0.00054 AFIX 137 H30A 2 0.639586 0.214055 0.654496 11.00000 -1.50000 H30B 2 0.663733 0.285691 0.731116 11.00000 -1.50000 H30C 2 0.674149 0.293455 0.604650 11.00000 -1.50000 AFIX 0 C29 1 0.263856 0.257702 0.506082 11.00000 0.03515 0.02541 = 0.02121 -0.00377 0.01108 -0.00215 AFIX 137 H29A 2 0.291654 0.205303 0.495057 11.00000 -1.50000 H29B 2 0.339449 0.287610 0.459876 11.00000 -1.50000 H29C 2 0.103642 0.267296 0.486079 11.00000 -1.50000 AFIX 0 C17 1 0.161004 0.691697 0.839070 11.00000 0.02217 0.02012 = 0.01893 0.00006 0.01028 0.00128 AFIX 13 H17 2 -0.001556 0.686632 0.836675 11.00000 -1.20000 AFIX 0 C20 1 0.249637 0.749836 0.927011 11.00000 0.02382 0.02128 = 0.01750 0.00017 0.01028 -0.00030 AFIX 13 H20 2 0.412096 0.741758 0.956688 11.00000 -1.20000 AFIX 0 C22 1 0.212769 0.825602 0.871930 11.00000 0.02505 0.02123 = 0.02167 -0.00021 0.01198 0.00166 AFIX 23 H22A 2 0.053486 0.831297 0.836714 11.00000 -1.20000 H22B 2 0.252012 0.864511 0.928480 11.00000 -1.20000 AFIX 0 C26 1 0.645234 0.915632 0.785212 11.00000 0.02571 0.02219 = 0.02617 -0.00131 0.01366 -0.00104 AFIX 23 H26A 2 0.709082 0.899788 0.722688 11.00000 -1.20000 H26B 2 0.758912 0.944077 0.837179 11.00000 -1.20000 AFIX 0 C21 1 0.125994 0.747254 1.020819 11.00000 0.02978 0.02224 = 0.02089 -0.00023 0.01522 0.00156 AFIX 137 H21A 2 0.178509 0.787410 1.072526 11.00000 -1.50000 H21B 2 0.154191 0.699805 1.058947 11.00000 -1.50000 H21C 2 -0.033891 0.752894 0.991054 11.00000 -1.50000 AFIX 0 C28 1 -0.087089 0.574184 0.695220 11.00000 0.02530 0.02621 = 0.01988 -0.00243 0.00893 -0.00086 AFIX 137 H28A 2 -0.133707 0.561303 0.617373 11.00000 -1.50000 H28B 2 -0.160230 0.620070 0.709340 11.00000 -1.50000 H28C 2 -0.128920 0.534418 0.739956 11.00000 -1.50000 AFIX 0 C18 1 0.513806 0.614367 0.876633 11.00000 0.02379 0.01981 = 0.02096 0.00002 0.01143 -0.00026 AFIX 137 H18A 2 0.564234 0.627057 0.954368 11.00000 -1.50000 H18B 2 0.567266 0.651573 0.831563 11.00000 -1.50000 H18C 2 0.572737 0.565877 0.862944 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM a in P2(1) REM R1 = 0.0456 for 4262 Fo > 4sig(Fo) and 0.0472 for all 4459 data REM 343 parameters refined using 1 restraints END WGHT 0.0848 0.0386 REM Instructions for potential hydrogen bonds HTAB O1S O25_$3 HTAB O1S O3 HTAB O25 O12_$1 HTAB O24 O16 HTAB O12 O1S_$2 REM Highest difference peak 0.207, deepest hole -0.277, 1-sigma level 0.057 Q1 1 0.3571 0.9320 0.7189 11.00000 0.05 0.21 Q2 1 0.1886 0.6534 0.8493 11.00000 0.05 0.20 Q3 1 0.1878 0.6168 0.6824 11.00000 0.05 0.20 Q4 1 0.3228 0.3176 0.6361 11.00000 0.05 0.19 ; _shelx_res_checksum 23466 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 O1S O -0.0126(3) 0.07584(12) 0.81690(17) 0.0285(5) Uani 1 1 d . . H1SA H 0.1052 0.0483 0.8234 0.043 Uiso 1 1 d R U H1SB H -0.0103 0.1047 0.7628 0.043 Uiso 1 1 d R U O3 O 0.1126(3) 0.17894(11) 0.65907(17) 0.0262(5) Uani 1 1 d . . O16 O 0.3647(3) 0.76895(11) 0.72763(16) 0.0238(4) Uani 1 1 d . . O23 O 0.5739(3) 0.85337(12) 0.83836(16) 0.0244(4) Uani 1 1 d . . O25 O 0.3683(3) 0.99251(11) 0.83921(16) 0.0232(4) Uani 1 1 d . . H25 H 0.4738 1.0165 0.8776 0.035 Uiso 1 1 calc R U O24 O 0.2772(4) 0.87975(12) 0.59552(16) 0.0285(5) Uani 1 1 d . . H24 H 0.3307 0.8371 0.5958 0.043 Uiso 1 1 calc R U O12 O 0.2843(3) 0.57256(12) 1.03689(15) 0.0215(4) Uani 1 1 d . . H12 H 0.1899 0.5781 1.0757 0.032 Uiso 1 1 calc R U C3 C 0.2445(5) 0.22650(16) 0.6977(2) 0.0221(6) Uani 1 1 d . . C2 C 0.3032(5) 0.24184(16) 0.8190(2) 0.0246(6) Uani 1 1 d . . H2A H 0.4652 0.2358 0.8472 0.030 Uiso 1 1 calc R U H2B H 0.2250 0.2066 0.8581 0.030 Uiso 1 1 calc R U C1 C 0.2336(5) 0.32129(16) 0.8391(2) 0.0219(6) Uani 1 1 d . . H1A H 0.0693 0.3247 0.8209 0.026 Uiso 1 1 calc R U H1B H 0.2852 0.3334 0.9179 0.026 Uiso 1 1 calc R U C10 C 0.3281(5) 0.37710(16) 0.7713(2) 0.0211(6) Uani 1 1 d . . C9 C 0.3070(5) 0.45874(15) 0.8000(2) 0.0200(6) Uani 1 1 d . . C8 C 0.2685(5) 0.51170(15) 0.7055(2) 0.0203(6) Uani 1 1 d . . C14 C 0.1690(4) 0.58490(15) 0.7253(2) 0.0196(6) Uani 1 1 d . . C15 C 0.2260(5) 0.65051(16) 0.6587(2) 0.0208(5) Uani 1 1 d . . H15A H 0.3837 0.6487 0.6531 0.025 Uiso 1 1 calc R U H15B H 0.1306 0.6508 0.5839 0.025 Uiso 1 1 calc R U C16 C 0.1813(5) 0.71848(16) 0.7235(2) 0.0213(6) Uani 1 1 d . . H16 H 0.0393 0.7425 0.6854 0.026 Uiso 1 1 calc R U C23 C 0.3509(5) 0.83570(16) 0.7864(2) 0.0217(6) Uani 1 1 d . . C24 C 0.2691(5) 0.90039(16) 0.7047(2) 0.0225(6) Uani 1 1 d . . H24A H 0.1156 0.9162 0.7089 0.027 Uiso 1 1 calc R U C25 C 0.4376(5) 0.96186(16) 0.7454(2) 0.0224(6) Uani 1 1 d . . C27 C 0.4549(5) 1.02098(17) 0.6622(3) 0.0272(6) Uani 1 1 d . . H27A H 0.3120 1.0466 0.6403 0.041 Uiso 1 1 calc R U H27B H 0.4934 0.9982 0.5976 0.041 Uiso 1 1 calc R U H27C H 0.5705 1.0565 0.6947 0.041 Uiso 1 1 calc R U C19 C 0.5322(5) 0.41974(16) 0.8255(2) 0.0229(6) Uani 1 1 d . . H19A H 0.6402 0.4326 0.7803 0.027 Uiso 1 1 calc R U H19B H 0.5991 0.4086 0.9033 0.027 Uiso 1 1 calc R U C11 C 0.1958(5) 0.47665(15) 0.8955(2) 0.0223(6) Uani 1 1 d . . H11A H 0.2814 0.4517 0.9618 0.027 Uiso 1 1 calc R U H11B H 0.0454 0.4545 0.8788 0.027 Uiso 1 1 calc R U C12 C 0.1717(4) 0.55958(16) 0.9245(2) 0.0195(5) Uani 1 1 d . . H12A H 0.0100 0.5700 0.9181 0.023 Uiso 1 1 calc R U C13 C 0.2572(4) 0.61215(15) 0.8467(2) 0.0187(5) Uani 1 1 d . . C7 C 0.3070(5) 0.49280(17) 0.6084(2) 0.0241(6) Uani 1 1 d . . H7 H 0.2911 0.5295 0.5529 0.029 Uiso 1 1 calc R U C6 C 0.3745(5) 0.41618(17) 0.5817(2) 0.0266(6) Uani 1 1 d . . H6A H 0.5387 0.4127 0.5978 0.032 Uiso 1 1 calc R U H6B H 0.3186 0.4064 0.5025 0.032 Uiso 1 1 calc R U C5 C 0.2811(5) 0.35813(16) 0.6490(2) 0.0216(6) Uani 1 1 d . . H5 H 0.1158 0.3599 0.6230 0.026 Uiso 1 1 calc R U C4 C 0.3524(5) 0.27780(16) 0.6264(2) 0.0223(6) Uani 1 1 d . . C30 C 0.6053(5) 0.26675(17) 0.6569(2) 0.0262(6) Uani 1 1 d . . H30A H 0.6396 0.2141 0.6545 0.039 Uiso 1 1 calc R U H30B H 0.6637 0.2857 0.7311 0.039 Uiso 1 1 calc R U H30C H 0.6741 0.2935 0.6047 0.039 Uiso 1 1 calc R U C29 C 0.2639(5) 0.25770(17) 0.5061(2) 0.0265(6) Uani 1 1 d . . H29A H 0.2917 0.2053 0.4951 0.040 Uiso 1 1 calc R U H29B H 0.3394 0.2876 0.4599 0.040 Uiso 1 1 calc R U H29C H 0.1036 0.2673 0.4861 0.040 Uiso 1 1 calc R U C17 C 0.1610(4) 0.69170(15) 0.8391(2) 0.0195(5) Uani 1 1 d . . H17 H -0.0016 0.6866 0.8367 0.023 Uiso 1 1 calc R U C20 C 0.2496(4) 0.74984(15) 0.9270(2) 0.0200(6) Uani 1 1 d . . H20 H 0.4121 0.7418 0.9567 0.024 Uiso 1 1 calc R U C22 C 0.2128(5) 0.82560(16) 0.8719(2) 0.0216(6) Uani 1 1 d . . H22A H 0.0535 0.8313 0.8367 0.026 Uiso 1 1 calc R U H22B H 0.2520 0.8645 0.9285 0.026 Uiso 1 1 calc R U C26 C 0.6452(5) 0.91563(16) 0.7852(2) 0.0235(6) Uani 1 1 d . . H26A H 0.7091 0.8998 0.7227 0.028 Uiso 1 1 calc R U H26B H 0.7589 0.9441 0.8372 0.028 Uiso 1 1 calc R U C21 C 0.1260(5) 0.74725(16) 1.0208(2) 0.0228(6) Uani 1 1 d . . H21A H 0.1785 0.7874 1.0725 0.034 Uiso 1 1 calc R U H21B H 0.1542 0.6998 1.0589 0.034 Uiso 1 1 calc R U H21C H -0.0339 0.7529 0.9911 0.034 Uiso 1 1 calc R U C28 C -0.0871(5) 0.57418(17) 0.6952(2) 0.0232(6) Uani 1 1 d . . H28A H -0.1337 0.5613 0.6174 0.035 Uiso 1 1 calc R U H28B H -0.1602 0.6201 0.7093 0.035 Uiso 1 1 calc R U H28C H -0.1289 0.5344 0.7400 0.035 Uiso 1 1 calc R U C18 C 0.5138(4) 0.61437(15) 0.8766(2) 0.0205(6) Uani 1 1 d . . H18A H 0.5642 0.6271 0.9544 0.031 Uiso 1 1 calc R U H18B H 0.5673 0.6516 0.8316 0.031 Uiso 1 1 calc R U H18C H 0.5727 0.5659 0.8629 0.031 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 O1S 0.0301(10) 0.0283(11) 0.0322(11) 0.0044(9) 0.0178(8) 0.0028(9) O3 0.0300(11) 0.0217(10) 0.0288(10) -0.0015(9) 0.0102(8) -0.0016(8) O16 0.0314(11) 0.0206(10) 0.0246(10) -0.0019(8) 0.0179(8) -0.0014(8) O23 0.0265(10) 0.0230(10) 0.0251(10) 0.0026(8) 0.0084(8) 0.0001(8) O25 0.0266(10) 0.0225(10) 0.0239(9) -0.0052(8) 0.0127(8) -0.0003(8) O24 0.0451(13) 0.0242(10) 0.0188(9) -0.0011(8) 0.0128(8) -0.0022(9) O12 0.0257(9) 0.0255(10) 0.0166(9) -0.0006(8) 0.0117(7) 0.0007(8) C3 0.0228(13) 0.0205(13) 0.0244(14) -0.0009(11) 0.0087(10) 0.0048(11) C2 0.0299(14) 0.0225(15) 0.0245(14) 0.0011(11) 0.0125(11) -0.0025(11) C1 0.0264(14) 0.0198(13) 0.0227(13) -0.0012(11) 0.0125(11) -0.0025(11) C10 0.0247(14) 0.0208(14) 0.0206(13) 0.0004(11) 0.0111(10) -0.0001(11) C9 0.0264(14) 0.0179(13) 0.0190(13) -0.0010(11) 0.0120(11) -0.0030(11) C8 0.0219(13) 0.0206(13) 0.0209(13) -0.0005(11) 0.0103(10) -0.0030(10) C14 0.0233(13) 0.0219(14) 0.0158(12) -0.0016(11) 0.0087(10) -0.0011(11) C15 0.0252(13) 0.0219(13) 0.0174(12) 0.0000(11) 0.0096(10) 0.0011(11) C16 0.0244(13) 0.0229(13) 0.0188(12) 0.0034(11) 0.0094(10) 0.0009(11) C23 0.0268(14) 0.0203(14) 0.0214(13) -0.0004(11) 0.0125(10) 0.0014(11) C24 0.0298(14) 0.0216(14) 0.0184(13) -0.0011(11) 0.0106(11) -0.0004(11) C25 0.0269(14) 0.0209(13) 0.0227(13) -0.0019(11) 0.0123(11) -0.0004(12) C27 0.0345(16) 0.0201(13) 0.0309(15) 0.0011(12) 0.0158(13) -0.0004(12) C19 0.0270(14) 0.0203(13) 0.0228(13) -0.0008(11) 0.0087(11) -0.0010(11) C11 0.0287(14) 0.0228(15) 0.0191(12) -0.0010(11) 0.0133(11) -0.0022(11) C12 0.0207(12) 0.0236(14) 0.0165(12) -0.0001(11) 0.0090(10) 0.0015(11) C13 0.0214(13) 0.0219(13) 0.0158(12) -0.0012(11) 0.0104(10) 0.0005(10) C7 0.0336(15) 0.0208(13) 0.0222(13) 0.0021(11) 0.0158(11) -0.0010(11) C6 0.0378(16) 0.0232(14) 0.0235(14) 0.0004(12) 0.0168(12) 0.0000(12) C5 0.0252(13) 0.0216(14) 0.0204(13) -0.0009(11) 0.0103(10) 0.0003(11) C4 0.0262(14) 0.0235(14) 0.0195(13) -0.0021(10) 0.0103(11) -0.0011(11) C30 0.0298(15) 0.0242(14) 0.0287(14) -0.0007(12) 0.0154(12) 0.0005(12) C29 0.0352(15) 0.0254(14) 0.0212(13) -0.0038(12) 0.0111(11) -0.0022(12) C17 0.0222(12) 0.0201(13) 0.0189(13) 0.0001(11) 0.0103(10) 0.0013(11) C20 0.0238(13) 0.0213(13) 0.0175(12) 0.0002(11) 0.0103(10) -0.0003(11) C22 0.0251(14) 0.0212(13) 0.0217(13) -0.0002(10) 0.0120(11) 0.0017(10) C26 0.0257(14) 0.0222(14) 0.0262(13) -0.0013(11) 0.0137(11) -0.0010(11) C21 0.0298(14) 0.0222(13) 0.0209(13) -0.0002(11) 0.0152(11) 0.0016(11) C28 0.0253(13) 0.0262(14) 0.0199(12) -0.0024(11) 0.0089(10) -0.0009(11) C18 0.0238(14) 0.0198(13) 0.0210(13) 0.0000(11) 0.0114(10) -0.0003(11) 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 H1SA O1S H1SB 105.5 C23 O16 C16 114.9(2) C23 O23 C26 109.3(2) C25 O25 H25 109.5 C24 O24 H24 109.5 C12 O12 H12 109.5 O3 C3 C2 121.7(3) O3 C3 C4 122.6(2) C2 C3 C4 115.6(2) C3 C2 C1 108.8(2) C3 C2 H2A 109.9 C1 C2 H2A 109.9 C3 C2 H2B 109.9 C1 C2 H2B 109.9 H2A C2 H2B 108.3 C10 C1 C2 112.3(2) C10 C1 H1A 109.1 C2 C1 H1A 109.1 C10 C1 H1B 109.1 C2 C1 H1B 109.1 H1A C1 H1B 107.9 C19 C10 C1 118.5(2) C19 C10 C5 121.5(2) C1 C10 C5 113.3(2) C19 C10 C9 60.34(18) C1 C10 C9 116.8(2) C5 C10 C9 116.2(2) C8 C9 C19 116.2(2) C8 C9 C11 117.1(2) C19 C9 C11 118.4(2) C8 C9 C10 116.2(2) C19 C9 C10 58.91(18) C11 C9 C10 117.4(2) C7 C8 C9 121.5(3) C7 C8 C14 122.5(3) C9 C8 C14 115.8(2) C8 C14 C15 116.4(2) C8 C14 C28 106.2(2) C15 C14 C28 107.8(2) C8 C14 C13 111.5(2) C15 C14 C13 101.9(2) C28 C14 C13 113.1(2) C16 C15 C14 104.4(2) C16 C15 H15A 110.9 C14 C15 H15A 110.9 C16 C15 H15B 110.9 C14 C15 H15B 110.9 H15A C15 H15B 108.9 O16 C16 C15 107.4(2) O16 C16 C17 112.6(2) C15 C16 C17 107.4(2) O16 C16 H16 109.8 C15 C16 H16 109.8 C17 C16 H16 109.8 O23 C23 O16 105.4(2) O23 C23 C22 109.9(2) O16 C23 C22 111.4(2) O23 C23 C24 105.8(2) O16 C23 C24 110.3(2) C22 C23 C24 113.5(2) O24 C24 C25 110.3(2) O24 C24 C23 110.7(2) C25 C24 C23 103.2(2) O24 C24 H24A 110.8 C25 C24 H24A 110.8 C23 C24 H24A 110.8 O25 C25 C27 111.3(2) O25 C25 C26 108.9(2) C27 C25 C26 115.8(2) O25 C25 C24 104.5(2) C27 C25 C24 115.5(2) C26 C25 C24 99.8(2) C25 C27 H27A 109.5 C25 C27 H27B 109.5 H27A C27 H27B 109.5 C25 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C10 C19 C9 60.75(19) C10 C19 H19A 117.7 C9 C19 H19A 117.7 C10 C19 H19B 117.7 C9 C19 H19B 117.7 H19A C19 H19B 114.8 C9 C11 C12 117.7(2) C9 C11 H11A 107.9 C12 C11 H11A 107.9 C9 C11 H11B 107.9 C12 C11 H11B 107.9 H11A C11 H11B 107.2 O12 C12 C13 110.8(2) O12 C12 C11 109.4(2) C13 C12 C11 112.9(2) O12 C12 H12A 107.8 C13 C12 H12A 107.8 C11 C12 H12A 107.8 C12 C13 C18 109.7(2) C12 C13 C17 115.9(2) C18 C13 C17 110.4(2) C12 C13 C14 108.7(2) C18 C13 C14 111.2(2) C17 C13 C14 100.6(2) C8 C7 C6 123.4(3) C8 C7 H7 118.3 C6 C7 H7 118.3 C7 C6 C5 110.9(2) C7 C6 H6A 109.5 C5 C6 H6A 109.5 C7 C6 H6B 109.5 C5 C6 H6B 109.5 H6A C6 H6B 108.1 C10 C5 C6 112.4(2) C10 C5 C4 112.9(2) C6 C5 C4 112.7(2) C10 C5 H5 106.1 C6 C5 H5 106.1 C4 C5 H5 106.1 C29 C4 C3 108.6(2) C29 C4 C30 109.8(2) C3 C4 C30 108.8(2) C29 C4 C5 110.2(2) C3 C4 C5 106.6(2) C30 C4 C5 112.7(2) C4 C30 H30A 109.5 C4 C30 H30B 109.5 H30A C30 H30B 109.5 C4 C30 H30C 109.5 H30A C30 H30C 109.5 H30B C30 H30C 109.5 C4 C29 H29A 109.5 C4 C29 H29B 109.5 H29A C29 H29B 109.5 C4 C29 H29C 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 C20 C17 C16 111.2(2) C20 C17 C13 121.4(2) C16 C17 C13 103.9(2) C20 C17 H17 106.4 C16 C17 H17 106.4 C13 C17 H17 106.4 C21 C20 C22 108.7(2) C21 C20 C17 111.6(2) C22 C20 C17 107.4(2) C21 C20 H20 109.7 C22 C20 H20 109.7 C17 C20 H20 109.7 C23 C22 C20 112.0(2) C23 C22 H22A 109.2 C20 C22 H22A 109.2 C23 C22 H22B 109.2 C20 C22 H22B 109.2 H22A C22 H22B 107.9 O23 C26 C25 105.4(2) O23 C26 H26A 110.7 C25 C26 H26A 110.7 O23 C26 H26B 110.7 C25 C26 H26B 110.7 H26A C26 H26B 108.8 C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C14 C28 H28A 109.5 C14 C28 H28B 109.5 H28A C28 H28B 109.5 C14 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C13 C18 H18A 109.5 C13 C18 H18B 109.5 H18A C18 H18B 109.5 C13 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 O1S H1SA 0.8704 O1S H1SB 0.8573 O3 C3 1.211(4) O16 C23 1.427(3) O16 C16 1.446(3) O23 C23 1.423(4) O23 C26 1.426(4) O25 C25 1.442(3) O25 H25 0.8400 O24 C24 1.424(3) O24 H24 0.8400 O12 C12 1.443(3) O12 H12 0.8400 C3 C2 1.505(4) C3 C4 1.535(4) C2 C1 1.539(4) C2 H2A 0.9900 C2 H2B 0.9900 C1 C10 1.514(4) C1 H1A 0.9900 C1 H1B 0.9900 C10 C19 1.506(4) C10 C5 1.530(4) C10 C9 1.534(4) C9 C8 1.499(4) C9 C19 1.528(4) C9 C11 1.533(4) C8 C7 1.330(4) C8 C14 1.504(4) C14 C15 1.535(4) C14 C28 1.553(4) C14 C13 1.575(3) C15 C16 1.531(4) C15 H15A 0.9900 C15 H15B 0.9900 C16 C17 1.553(4) C16 H16 1.0000 C23 C22 1.515(4) C23 C24 1.564(4) C24 C25 1.533(4) C24 H24A 1.0000 C25 C27 1.513(4) C25 C26 1.520(4) C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C19 H19A 0.9900 C19 H19B 0.9900 C11 C12 1.561(4) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.533(4) C12 H12A 1.0000 C13 C18 1.544(4) C13 C17 1.554(4) C7 C6 1.508(4) C7 H7 0.9500 C6 C5 1.535(4) C6 H6A 0.9900 C6 H6B 0.9900 C5 C4 1.564(4) C5 H5 1.0000 C4 C29 1.527(4) C4 C30 1.535(4) C30 H30A 0.9800 C30 H30B 0.9800 C30 H30C 0.9800 C29 H29A 0.9800 C29 H29B 0.9800 C29 H29C 0.9800 C17 C20 1.534(4) C17 H17 1.0000 C20 C21 1.530(4) C20 C22 1.530(4) C20 H20 1.0000 C22 H22A 0.9900 C22 H22B 0.9900 C26 H26A 0.9900 C26 H26B 0.9900 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O1S 0.84 1.91 2.733(3) 168.0 2_557 O24 H24 O16 0.84 2.03 2.580(3) 122.3 . O25 H25 O12 0.84 1.92 2.765(3) 178.9 2_657 O1S H1SB O3 0.86 2.12 2.938(3) 159.9 . O1S H1SA O25 0.87 1.88 2.754(3) 177.4 1_545 O12 H12 O1S 0.84 1.91 2.733(3) 168.0 2_557 O24 H24 O16 0.84 2.03 2.580(3) 122.3 . O25 H25 O12 0.84 1.92 2.765(3) 178.9 2_657 O1S H1SB O3 0.86 2.12 2.938(3) 159.9 . O1S H1SA O25 0.87 1.88 2.754(3) 177.4 1_545 O1S H1SB O3 0.86 2.12 2.938(3) 159.9 . O1S H1SA O25 0.87 1.88 2.754(3) 177.4 1_545 O12 H12 O1S 0.84 1.91 2.733(3) 168.0 2_557 O24 H24 O16 0.84 2.03 2.580(3) 122.3 . O25 H25 O12 0.84 1.92 2.765(3) 178.9 2_657 O1S H1SA O25 0.87 1.88 2.754(3) 177.4 1_545 O1S H1SB O3 0.86 2.12 2.938(3) 159.9 . O25 H25 O12 0.84 1.92 2.765(3) 178.9 2_657 O24 H24 O16 0.84 2.03 2.580(3) 122.3 . O12 H12 O1S 0.84 1.91 2.733(3) 168.0 2_557 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 O3 C3 C2 C1 -117.8(3) C4 C3 C2 C1 58.9(3) C3 C2 C1 C10 -53.2(3) C2 C1 C10 C19 -99.7(3) C2 C1 C10 C5 51.9(3) C2 C1 C10 C9 -168.8(2) C19 C10 C9 C8 106.2(3) C1 C10 C9 C8 -144.8(3) C5 C10 C9 C8 -6.7(4) C1 C10 C9 C19 109.1(3) C5 C10 C9 C19 -112.9(3) C19 C10 C9 C11 -108.2(3) C1 C10 C9 C11 0.9(4) C5 C10 C9 C11 138.9(3) C19 C9 C8 C7 49.7(4) C11 C9 C8 C7 -162.5(3) C10 C9 C8 C7 -16.7(4) C19 C9 C8 C14 -134.4(3) C11 C9 C8 C14 13.4(4) C10 C9 C8 C14 159.1(2) C7 C8 C14 C15 -32.1(4) C9 C8 C14 C15 152.1(2) C7 C8 C14 C28 87.9(3) C9 C8 C14 C28 -87.9(3) C7 C8 C14 C13 -148.4(3) C9 C8 C14 C13 35.8(3) C8 C14 C15 C16 -159.5(2) C28 C14 C15 C16 81.4(3) C13 C14 C15 C16 -37.9(3) C23 O16 C16 C15 -179.5(2) C23 O16 C16 C17 -61.4(3) C14 C15 C16 O16 136.0(2) C14 C15 C16 C17 14.7(3) C26 O23 C23 O16 108.3(2) C26 O23 C23 C22 -131.5(2) C26 O23 C23 C24 -8.6(3) C16 O16 C23 O23 145.1(2) C16 O16 C23 C22 25.9(3) C16 O16 C23 C24 -101.2(3) O23 C23 C24 O24 100.8(3) O16 C23 C24 O24 -12.7(3) C22 C23 C24 O24 -138.6(3) O23 C23 C24 C25 -17.2(3) O16 C23 C24 C25 -130.7(2) C22 C23 C24 C25 103.4(3) O24 C24 C25 O25 163.2(2) C23 C24 C25 O25 -78.5(3) O24 C24 C25 C27 40.6(3) C23 C24 C25 C27 158.9(2) O24 C24 C25 C26 -84.2(3) C23 C24 C25 C26 34.1(3) C1 C10 C19 C9 -106.4(3) C5 C10 C19 C9 104.4(3) C8 C9 C19 C10 -106.1(3) C11 C9 C19 C10 106.6(3) C8 C9 C11 C12 -34.1(4) C19 C9 C11 C12 113.0(3) C10 C9 C11 C12 -179.4(2) C9 C11 C12 O12 -121.3(2) C9 C11 C12 C13 2.6(3) O12 C12 C13 C18 46.1(3) C11 C12 C13 C18 -77.1(3) O12 C12 C13 C17 -79.7(3) C11 C12 C13 C17 157.2(2) O12 C12 C13 C14 167.9(2) C11 C12 C13 C14 44.8(3) C8 C14 C13 C12 -66.4(3) C15 C14 C13 C12 168.7(2) C28 C14 C13 C12 53.3(3) C8 C14 C13 C18 54.6(3) C15 C14 C13 C18 -70.3(3) C28 C14 C13 C18 174.2(2) C8 C14 C13 C17 171.5(2) C15 C14 C13 C17 46.6(2) C28 C14 C13 C17 -68.9(3) C9 C8 C7 C6 4.9(4) C14 C8 C7 C6 -170.7(3) C8 C7 C6 C5 29.1(4) C19 C10 C5 C6 -30.4(4) C1 C10 C5 C6 178.9(2) C9 C10 C5 C6 39.4(3) C19 C10 C5 C4 98.4(3) C1 C10 C5 C4 -52.3(3) C9 C10 C5 C4 168.2(2) C7 C6 C5 C10 -49.5(3) C7 C6 C5 C4 -178.4(2) O3 C3 C4 C29 0.2(4) C2 C3 C4 C29 -176.4(2) O3 C3 C4 C30 -119.3(3) C2 C3 C4 C30 64.1(3) O3 C3 C4 C5 118.9(3) C2 C3 C4 C5 -57.8(3) C10 C5 C4 C29 169.8(2) C6 C5 C4 C29 -61.6(3) C10 C5 C4 C3 52.2(3) C6 C5 C4 C3 -179.2(2) C10 C5 C4 C30 -67.1(3) C6 C5 C4 C30 61.5(3) O16 C16 C17 C20 28.9(3) C15 C16 C17 C20 146.9(2) O16 C16 C17 C13 -103.4(3) C15 C16 C17 C13 14.6(3) C12 C13 C17 C20 79.8(3) C18 C13 C17 C20 -45.7(3) C14 C13 C17 C20 -163.2(2) C12 C13 C17 C16 -154.1(2) C18 C13 C17 C16 80.4(3) C14 C13 C17 C16 -37.2(2) C16 C17 C20 C21 148.8(2) C13 C17 C20 C21 -88.5(3) C16 C17 C20 C22 29.7(3) C13 C17 C20 C22 152.4(2) O23 C23 C22 C20 -79.1(3) O16 C23 C22 C20 37.4(3) C24 C23 C22 C20 162.7(2) C21 C20 C22 C23 173.6(2) C17 C20 C22 C23 -65.5(3) C23 O23 C26 C25 31.7(3) O25 C25 C26 O23 68.5(3) C27 C25 C26 O23 -165.3(2) C24 C25 C26 O23 -40.7(3)