#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:29:55 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252919 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157495.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_7157495 loop_ _publ_author_name 'Zou, Chun-Xin' 'Hou, Zi-Lin' 'Bai, Ming' 'Guo, Rui' 'Lin, Bin' 'Wang, Xiao-Bo' 'Huang, Xiao-Xiao' 'Song, Shao-Jiang' _publ_section_title ; Highly modified steroids from Inonotus obliquus. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3908 _journal_page_last 3916 _journal_paper_doi 10.1039/d0ob00474j _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_sum 'C22 H32 O4' _chemical_formula_weight 360.47 _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' _atom_sites_solution_hydrogens geom _audit_update_record ; 2020-01-03 deposited with the CCDC. 2020-05-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 113.567(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 12.5521(12) _cell_length_b 6.6052(6) _cell_length_c 12.9824(12) _cell_measurement_reflns_used 9904 _cell_measurement_temperature 210.(2) _cell_measurement_theta_max 57.1258 _cell_measurement_theta_min 3.2311 _cell_volume 986.58(16) _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 946)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 210.(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON II' _diffrn_radiation_monochromator 'Helios Multi-layer Optic' _diffrn_radiation_type ' Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13515 _diffrn_reflns_theta_full 57.13 _diffrn_reflns_theta_max 57.13 _diffrn_reflns_theta_min 3.23 _diffrn_source MetalJet _diffrn_source_type 'Liquid Metal source' _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.176 _refine_diff_density_min -0.132 _refine_ls_abs_structure_details ; Flack x determined using 1696 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 4004 _refine_ls_number_restraints 256 _refine_ls_restrained_S_all 0.931 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0303 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.1073 _reflns_number_gt 3886 _reflns_number_total 4004 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00474j2.cif _cod_data_source_block SYYK_HSB8 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7157495.cif. ; _cod_database_code 7157495 _shelx_res_file ; TITL SYYK_HSB8_0m_a.res in P2(1) SYYK_HSB8_0m.res created by SHELXL-2018/3 at 23:44:27 on 30-Jul-2019 CELL 1.34139 12.5521 6.6052 12.9824 90.000 113.567 90.000 ZERR 2.00 0.0012 0.0006 0.0012 0.000 0.003 0.000 LATT -1 SYMM -x, y+1/2, -z SFAC C H O UNIT 44 64 8 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -63.190 ACTA L.S. 4 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF simu 0.01 0.2 2.0 delu WGHT 0.100000 FVAR 1.31253 0.59488 O1 3 0.497627 0.667585 -0.051046 11.00000 0.06628 0.04315 = 0.02733 0.00031 0.01753 -0.00008 part 1 O2 3 0.927708 0.351596 0.905829 21.00000 0.10159 0.10846 = 0.06016 0.04331 0.03752 0.04128 part 2 O2A 3 0.891660 0.312261 0.873847 -21.00000 0.13378 0.07202 = 0.11671 0.01989 0.09808 0.00024 part 0 O3 3 1.039584 0.361930 0.545640 11.00000 0.04685 0.05645 = 0.05684 -0.00857 0.02306 0.00539 O4 3 0.582615 0.528221 0.553396 11.00000 0.06160 0.04606 = 0.03327 0.00299 0.02170 0.00608 C1 1 0.806623 0.627900 0.852619 11.00000 0.14253 0.09166 = 0.11007 0.01915 0.09249 0.03843 AFIX 137 H14 2 0.778704 0.575890 0.907172 11.00000 -1.50000 H13 2 0.741274 0.650026 0.781510 11.00000 -1.50000 H1 2 0.847012 0.754898 0.879473 11.00000 -1.50000 AFIX 0 C2 1 0.886979 0.480322 0.836967 11.00000 0.04485 0.06319 = 0.04092 0.00064 0.01380 0.00050 C3 1 0.931948 0.528495 0.746992 11.00000 0.03026 0.04303 = 0.03137 0.00212 0.00291 0.00464 AFIX 13 H12 2 0.885125 0.642421 0.701808 11.00000 -1.20000 AFIX 0 C4 1 0.930514 0.359055 0.664298 11.00000 0.02853 0.03516 = 0.03568 0.00291 0.00422 0.00196 C5 1 0.812420 0.328541 0.565663 11.00000 0.03153 0.03592 = 0.03549 0.00151 0.00228 -0.00309 AFIX 23 H16 2 0.819261 0.216165 0.519393 11.00000 -1.20000 H17 2 0.755249 0.289185 0.595815 11.00000 -1.20000 AFIX 0 C6 1 0.766590 0.513653 0.490586 11.00000 0.03229 0.03900 = 0.03171 0.00585 0.00138 -0.00777 AFIX 23 H5 2 0.818824 0.544460 0.453246 11.00000 -1.20000 H4 2 0.766912 0.630229 0.537404 11.00000 -1.20000 AFIX 0 C7 1 0.643197 0.482756 0.401198 11.00000 0.02832 0.03019 = 0.02511 0.00087 0.00547 -0.00286 AFIX 13 H3 2 0.638735 0.342264 0.373203 11.00000 -1.20000 AFIX 0 C8 1 0.610352 0.626082 0.297313 11.00000 0.02579 0.03175 = 0.02433 -0.00041 0.00767 -0.00207 C9 1 0.482552 0.584242 0.216105 11.00000 0.02703 0.03011 = 0.02376 -0.00176 0.00549 -0.00176 AFIX 13 H23 2 0.477627 0.439596 0.194703 11.00000 -1.20000 AFIX 0 C10 1 0.445047 0.709056 0.106416 11.00000 0.03462 0.03530 = 0.02344 0.00004 0.00577 0.00147 AFIX 13 H22 2 0.447266 0.853323 0.127856 11.00000 -1.20000 AFIX 0 C11 1 0.320704 0.663847 0.024547 11.00000 0.03783 0.06158 = 0.02866 -0.00207 0.00163 0.00262 AFIX 137 H21 2 0.307219 0.721620 -0.048310 11.00000 -1.50000 H20 2 0.266727 0.722691 0.052651 11.00000 -1.50000 H2 2 0.309121 0.518490 0.017256 11.00000 -1.50000 AFIX 0 C12 1 0.529292 0.684939 0.050238 11.00000 0.04558 0.03342 = 0.02793 0.00179 0.01307 0.00183 C13 1 0.656273 0.693154 0.125742 11.00000 0.04333 0.05343 = 0.03552 0.00331 0.02119 -0.00034 AFIX 23 H32 2 0.678884 0.834699 0.144995 11.00000 -1.20000 H31 2 0.701244 0.640666 0.084844 11.00000 -1.20000 AFIX 0 C14 1 0.687128 0.571721 0.234204 11.00000 0.03089 0.04855 = 0.03136 0.00179 0.01289 0.00312 AFIX 23 H30 2 0.768654 0.596789 0.283483 11.00000 -1.20000 H29 2 0.678714 0.427028 0.216013 11.00000 -1.20000 AFIX 0 C15 1 0.972830 0.151023 0.719436 11.00000 0.04748 0.03899 = 0.05333 0.01032 0.00748 0.00580 AFIX 137 H6 2 0.916259 0.095482 0.745218 11.00000 -1.50000 H7 2 1.046896 0.166834 0.782845 11.00000 -1.50000 H8 2 0.981950 0.059912 0.664923 11.00000 -1.50000 AFIX 0 C16 1 1.024541 0.431311 0.624867 11.00000 0.02903 0.03645 = 0.04110 0.00158 0.00837 0.00682 C17 1 1.095836 0.597169 0.700944 11.00000 0.03128 0.04353 = 0.04852 -0.00054 0.00900 -0.00320 AFIX 23 H9 2 1.079074 0.727880 0.661984 11.00000 -1.20000 H10 2 1.179056 0.568609 0.726188 11.00000 -1.20000 AFIX 0 C18 1 1.060177 0.599156 0.799939 11.00000 0.03565 0.04733 = 0.03647 -0.00282 0.00148 -0.00117 AFIX 23 H11 2 1.066667 0.735458 0.831707 11.00000 -1.20000 H15 2 1.108000 0.505800 0.858997 11.00000 -1.20000 AFIX 0 C19 1 0.554436 0.501133 0.453773 11.00000 0.04083 0.03111 = 0.03105 0.00618 0.01463 0.00159 C20 1 0.429194 0.480080 0.374858 11.00000 0.03415 0.05329 = 0.04383 0.01325 0.01798 0.00100 AFIX 23 H25 2 0.379735 0.514220 0.414690 11.00000 -1.20000 H24 2 0.413587 0.339042 0.349907 11.00000 -1.20000 AFIX 0 C21 1 0.398709 0.616673 0.273121 11.00000 0.02710 0.04110 = 0.03293 0.00310 0.01050 0.00136 AFIX 23 H18 2 0.402006 0.758391 0.296551 11.00000 -1.20000 H19 2 0.319206 0.587930 0.219577 11.00000 -1.20000 AFIX 0 C22 1 0.629309 0.847920 0.337384 11.00000 0.03653 0.03231 = 0.02931 -0.00270 0.00955 -0.00760 AFIX 137 H27 2 0.710988 0.869790 0.383763 11.00000 -1.50000 H26 2 0.583680 0.876379 0.380882 11.00000 -1.50000 H28 2 0.605191 0.937212 0.272727 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM SYYK_HSB8_0m_a.res in P2(1) REM wR2 = 0.1073, GooF = S = 0.955, Restrained GooF = 0.931 for all data REM R1 = 0.0303 for 3886 Fo > 4sig(Fo) and 0.0311 for all 4004 data REM 249 parameters refined using 256 restraints END WGHT 0.0513 0.0626 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y+1/2, -z HTAB C10 O1_$1 EQIV $2 -x+2, y+1/2, -z+1 HTAB C17 O3_$2 EQIV $3 -x+1, y-1/2, -z+1 HTAB C20 O4_$3 REM Highest difference peak 0.176, deepest hole -0.132, 1-sigma level 0.027 Q1 1 0.4662 0.6451 0.1604 11.00000 0.05 0.18 Q2 1 0.5502 0.6068 0.2626 11.00000 0.05 0.15 Q3 1 0.5847 0.6624 0.0814 11.00000 0.05 0.14 Q4 1 0.7004 0.5072 0.4407 11.00000 0.05 0.14 Q5 1 0.6277 0.5473 0.3536 11.00000 0.05 0.13 ; _shelx_res_checksum 64266 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.49763(13) 0.6676(2) -0.05105(10) 0.0460(3) Uani d U . . 1.0 . . O O2 0.9277(11) 0.352(3) 0.9058(8) 0.088(3) Uani d U P . 0.59(4) A 1 O O2A 0.892(2) 0.312(2) 0.874(2) 0.092(5) Uani d U P . 0.41(4) A 2 O O3 1.03958(11) 0.3619(2) 0.54564(12) 0.0526(3) Uani d U . . 1.0 . . O O4 0.58261(12) 0.5282(2) 0.55340(10) 0.0461(3) Uani d U . . 1.0 . . C C1 0.8066(4) 0.6279(7) 0.8526(3) 0.1014(12) Uani d U . . 1.0 . . H H14 0.778704 0.57589 0.907172 0.152 Uiso calc U . R 1.0 . . H H13 0.741274 0.650026 0.78151 0.152 Uiso calc U . R 1.0 . . H H1 0.847012 0.754898 0.879473 0.152 Uiso calc U . R 1.0 . . C C2 0.88698(16) 0.4803(4) 0.83697(17) 0.0507(5) Uani d U . . 1.0 . . C C3 0.93195(13) 0.5285(3) 0.74699(13) 0.0379(4) Uani d U . . 1.0 . . H H12 0.885125 0.642421 0.701808 0.045 Uiso calc U . R 1.0 . . C C4 0.93051(12) 0.3591(3) 0.66430(13) 0.0359(3) Uani d U . . 1.0 . . C C5 0.81242(13) 0.3285(3) 0.56566(14) 0.0378(3) Uani d U . . 1.0 . . H H16 0.819261 0.216165 0.519393 0.045 Uiso calc U . R 1.0 . . H H17 0.755249 0.289185 0.595815 0.045 Uiso calc U . R 1.0 . . C C6 0.76659(13) 0.5137(3) 0.49059(13) 0.0380(4) Uani d U . . 1.0 . . H H5 0.818824 0.54446 0.453246 0.046 Uiso calc U . R 1.0 . . H H4 0.766912 0.630229 0.537404 0.046 Uiso calc U . R 1.0 . . C C7 0.64320(12) 0.4828(2) 0.40120(12) 0.0295(3) Uani d U . . 1.0 . . H H3 0.638735 0.342264 0.373203 0.035 Uiso calc U . R 1.0 . . C C8 0.61035(12) 0.6261(2) 0.29731(12) 0.0280(3) Uani d U . . 1.0 . . C C9 0.48255(11) 0.5842(2) 0.21610(12) 0.0284(3) Uani d U . . 1.0 . . H H23 0.477627 0.439596 0.194703 0.034 Uiso calc U . R 1.0 . . C C10 0.44505(12) 0.7091(3) 0.10642(11) 0.0330(3) Uani d U . . 1.0 . . H H22 0.447266 0.853323 0.127856 0.04 Uiso calc U . R 1.0 . . C C11 0.32070(15) 0.6638(4) 0.02455(13) 0.0464(4) Uani d U . . 1.0 . . H H21 0.307219 0.72162 -0.04831 0.07 Uiso calc U . R 1.0 . . H H20 0.266727 0.722691 0.052651 0.07 Uiso calc U . R 1.0 . . H H2 0.309121 0.51849 0.017256 0.07 Uiso calc U . R 1.0 . . C C12 0.52929(14) 0.6849(3) 0.05024(12) 0.0362(3) Uani d U . . 1.0 . . C C13 0.65627(15) 0.6932(3) 0.12574(13) 0.0424(4) Uani d U . . 1.0 . . H H32 0.678884 0.834699 0.144995 0.051 Uiso calc U . R 1.0 . . H H31 0.701244 0.640666 0.084844 0.051 Uiso calc U . R 1.0 . . C C14 0.68713(12) 0.5717(3) 0.23420(13) 0.0368(4) Uani d U . . 1.0 . . H H30 0.768654 0.596789 0.283483 0.044 Uiso calc U . R 1.0 . . H H29 0.678714 0.427028 0.216013 0.044 Uiso calc U . R 1.0 . . C C15 0.97283(17) 0.1510(3) 0.71944(18) 0.0506(4) Uani d U . . 1.0 . . H H6 0.916259 0.095482 0.745218 0.076 Uiso calc U . R 1.0 . . H H7 1.046896 0.166834 0.782845 0.076 Uiso calc U . R 1.0 . . H H8 0.98195 0.059912 0.664923 0.076 Uiso calc U . R 1.0 . . C C16 1.02454(12) 0.4313(3) 0.62487(14) 0.0373(3) Uani d U . . 1.0 . . C C17 1.09584(13) 0.5972(3) 0.70094(15) 0.0433(4) Uani d U . . 1.0 . . H H9 1.079074 0.72788 0.661984 0.052 Uiso calc U . R 1.0 . . H H10 1.179056 0.568609 0.726188 0.052 Uiso calc U . R 1.0 . . C C18 1.06018(14) 0.5992(3) 0.79994(14) 0.0439(4) Uani d U . . 1.0 . . H H11 1.066667 0.735458 0.831707 0.053 Uiso calc U . R 1.0 . . H H15 1.108 0.5058 0.858997 0.053 Uiso calc U . R 1.0 . . C C19 0.55444(13) 0.5011(3) 0.45377(13) 0.0342(3) Uani d U . . 1.0 . . C C20 0.42919(14) 0.4801(3) 0.37486(15) 0.0430(4) Uani d U . . 1.0 . . H H25 0.379735 0.51422 0.41469 0.052 Uiso calc U . R 1.0 . . H H24 0.413587 0.339042 0.349907 0.052 Uiso calc U . R 1.0 . . C C21 0.39871(12) 0.6167(3) 0.27312(12) 0.0342(3) Uani d U . . 1.0 . . H H18 0.402006 0.758391 0.296551 0.041 Uiso calc U . R 1.0 . . H H19 0.319206 0.58793 0.219577 0.041 Uiso calc U . R 1.0 . . C C22 0.62931(13) 0.8479(2) 0.33738(12) 0.0339(3) Uani d U . . 1.0 . . H H27 0.710988 0.86979 0.383763 0.051 Uiso calc U . R 1.0 . . H H26 0.58368 0.876379 0.380882 0.051 Uiso calc U . R 1.0 . . H H28 0.605191 0.937212 0.272727 0.051 Uiso calc U . R 1.0 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0663(8) 0.0431(7) 0.0273(6) -0.0001(6) 0.0175(5) 0.0003(5) O2 0.102(4) 0.108(7) 0.060(3) 0.041(4) 0.038(3) 0.043(4) O2A 0.134(9) 0.072(4) 0.117(10) 0.000(6) 0.098(8) 0.020(6) O3 0.0469(6) 0.0565(8) 0.0568(8) 0.0054(6) 0.0231(5) -0.0086(7) O4 0.0616(7) 0.0461(7) 0.0333(6) 0.0061(6) 0.0217(5) 0.0030(5) C1 0.143(3) 0.092(2) 0.110(2) 0.038(2) 0.092(3) 0.019(2) C2 0.0448(8) 0.0632(13) 0.0409(10) 0.0005(9) 0.0138(7) 0.0006(9) C3 0.0303(6) 0.0430(9) 0.0314(7) 0.0046(6) 0.0029(5) 0.0021(7) C4 0.0285(7) 0.0352(8) 0.0357(8) 0.0020(6) 0.0042(6) 0.0029(6) C5 0.0315(7) 0.0359(8) 0.0355(7) -0.0031(6) 0.0023(5) 0.0015(6) C6 0.0323(6) 0.0390(8) 0.0317(7) -0.0078(6) 0.0014(6) 0.0059(7) C7 0.0283(6) 0.0302(7) 0.0251(6) -0.0029(5) 0.0055(5) 0.0009(5) C8 0.0258(6) 0.0318(7) 0.0243(6) -0.0021(5) 0.0077(5) -0.0004(5) C9 0.0270(6) 0.0301(7) 0.0238(6) -0.0018(5) 0.0055(5) -0.0018(5) C10 0.0346(6) 0.0353(8) 0.0234(7) 0.0015(6) 0.0058(5) 0.0000(6) C11 0.0378(8) 0.0616(11) 0.0287(7) 0.0026(8) 0.0016(6) -0.0021(8) C12 0.0456(8) 0.0334(8) 0.0279(7) 0.0018(7) 0.0131(6) 0.0018(6) C13 0.0433(8) 0.0534(10) 0.0355(8) -0.0003(8) 0.0212(7) 0.0033(8) C14 0.0309(6) 0.0486(9) 0.0314(7) 0.0031(6) 0.0129(6) 0.0018(7) C15 0.0475(9) 0.0390(9) 0.0533(11) 0.0058(7) 0.0075(8) 0.0103(8) C16 0.0290(6) 0.0364(7) 0.0411(8) 0.0068(6) 0.0084(6) 0.0016(7) C17 0.0313(7) 0.0435(9) 0.0485(9) -0.0032(7) 0.0090(6) -0.0005(8) C18 0.0356(7) 0.0473(9) 0.0365(8) -0.0012(7) 0.0015(6) -0.0028(7) C19 0.0408(7) 0.0311(7) 0.0311(7) 0.0016(6) 0.0146(6) 0.0062(6) C20 0.0341(7) 0.0533(10) 0.0438(9) 0.0010(7) 0.0180(7) 0.0133(8) C21 0.0271(6) 0.0411(8) 0.0329(7) 0.0014(6) 0.0105(5) 0.0031(6) C22 0.0365(7) 0.0323(7) 0.0293(7) -0.0076(6) 0.0096(5) -0.0027(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0389 0.0241 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 H14 . . 109.5 ? C2 C1 H13 . . 109.5 ? H14 C1 H13 . . 109.5 ? C2 C1 H1 . . 109.5 ? H14 C1 H1 . . 109.5 ? H13 C1 H1 . . 109.5 ? O2 C2 C1 . . 118.7(6) ? O2A C2 C1 . . 118.9(7) ? O2 C2 C3 . . 123.1(5) ? O2A C2 C3 . . 121.7(7) ? C1 C2 C3 . . 116.9(2) ? C2 C3 C4 . . 118.50(16) ? C2 C3 C18 . . 111.19(14) ? C4 C3 C18 . . 104.36(13) ? C2 C3 H12 . . 107.4 ? C4 C3 H12 . . 107.4 ? C18 C3 H12 . . 107.4 ? C5 C4 C16 . . 112.11(13) ? C5 C4 C15 . . 107.97(14) ? C16 C4 C15 . . 105.26(14) ? C5 C4 C3 . . 114.41(13) ? C16 C4 C3 . . 102.07(13) ? C15 C4 C3 . . 114.61(14) ? C6 C5 C4 . . 114.78(13) ? C6 C5 H16 . . 108.6 ? C4 C5 H16 . . 108.6 ? C6 C5 H17 . . 108.6 ? C4 C5 H17 . . 108.6 ? H16 C5 H17 . . 107.5 ? C5 C6 C7 . . 112.69(13) ? C5 C6 H5 . . 109.1 ? C7 C6 H5 . . 109.1 ? C5 C6 H4 . . 109.1 ? C7 C6 H4 . . 109.1 ? H5 C6 H4 . . 107.8 ? C19 C7 C6 . . 110.37(12) ? C19 C7 C8 . . 110.49(12) ? C6 C7 C8 . . 114.26(11) ? C19 C7 H3 . . 107.1 ? C6 C7 H3 . . 107.1 ? C8 C7 H3 . . 107.1 ? C14 C8 C22 . . 110.92(12) ? C14 C8 C9 . . 107.13(11) ? C22 C8 C9 . . 112.13(12) ? C14 C8 C7 . . 108.27(12) ? C22 C8 C7 . . 109.44(11) ? C9 C8 C7 . . 108.84(11) ? C21 C9 C10 . . 110.91(11) ? C21 C9 C8 . . 111.83(11) ? C10 C9 C8 . . 112.45(11) ? C21 C9 H23 . . 107.1 ? C10 C9 H23 . . 107.1 ? C8 C9 H23 . . 107.1 ? C12 C10 C11 . . 111.15(12) ? C12 C10 C9 . . 111.92(12) ? C11 C10 C9 . . 112.77(13) ? C12 C10 H22 . . 106.9 ? C11 C10 H22 . . 106.9 ? C9 C10 H22 . . 106.9 ? C10 C11 H21 . . 109.5 ? C10 C11 H20 . . 109.5 ? H21 C11 H20 . . 109.5 ? C10 C11 H2 . . 109.5 ? H21 C11 H2 . . 109.5 ? H20 C11 H2 . . 109.5 ? O1 C12 C13 . . 120.76(15) ? O1 C12 C10 . . 122.74(15) ? C13 C12 C10 . . 116.44(12) ? C12 C13 C14 . . 113.20(13) ? C12 C13 H32 . . 108.9 ? C14 C13 H32 . . 108.9 ? C12 C13 H31 . . 108.9 ? C14 C13 H31 . . 108.9 ? H32 C13 H31 . . 107.8 ? C13 C14 C8 . . 112.73(13) ? C13 C14 H30 . . 109.0 ? C8 C14 H30 . . 109.0 ? C13 C14 H29 . . 109.0 ? C8 C14 H29 . . 109.0 ? H30 C14 H29 . . 107.8 ? C4 C15 H6 . . 109.5 ? C4 C15 H7 . . 109.5 ? H6 C15 H7 . . 109.5 ? C4 C15 H8 . . 109.5 ? H6 C15 H8 . . 109.5 ? H7 C15 H8 . . 109.5 ? O3 C16 C17 . . 125.45(16) ? O3 C16 C4 . . 124.59(17) ? C17 C16 C4 . . 109.95(14) ? C16 C17 C18 . . 105.18(14) ? C16 C17 H9 . . 110.7 ? C18 C17 H9 . . 110.7 ? C16 C17 H10 . . 110.7 ? C18 C17 H10 . . 110.7 ? H9 C17 H10 . . 108.8 ? C17 C18 C3 . . 103.14(13) ? C17 C18 H11 . . 111.1 ? C3 C18 H11 . . 111.1 ? C17 C18 H15 . . 111.1 ? C3 C18 H15 . . 111.1 ? H11 C18 H15 . . 109.1 ? O4 C19 C20 . . 121.48(14) ? O4 C19 C7 . . 122.41(14) ? C20 C19 C7 . . 116.10(13) ? C19 C20 C21 . . 111.72(13) ? C19 C20 H25 . . 109.3 ? C21 C20 H25 . . 109.3 ? C19 C20 H24 . . 109.3 ? C21 C20 H24 . . 109.3 ? H25 C20 H24 . . 107.9 ? C20 C21 C9 . . 110.88(12) ? C20 C21 H18 . . 109.5 ? C9 C21 H18 . . 109.5 ? C20 C21 H19 . . 109.5 ? C9 C21 H19 . . 109.5 ? H18 C21 H19 . . 108.1 ? C8 C22 H27 . . 109.5 ? C8 C22 H26 . . 109.5 ? H27 C22 H26 . . 109.5 ? C8 C22 H28 . . 109.5 ? H27 C22 H28 . . 109.5 ? H26 C22 H28 . . 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C12 . 1.2175(18) ? O2 C2 . 1.191(9) ? O2A C2 . 1.201(15) ? O3 C16 . 1.208(2) ? O4 C19 . 1.210(2) ? C1 C2 . 1.474(4) ? C1 H14 . 0.97 ? C1 H13 . 0.97 ? C1 H1 . 0.97 ? C2 C3 . 1.520(3) ? C3 C4 . 1.546(2) ? C3 C18 . 1.548(2) ? C3 H12 . 0.99 ? C4 C5 . 1.5362(19) ? C4 C16 . 1.538(2) ? C4 C15 . 1.542(2) ? C5 C6 . 1.526(2) ? C5 H16 . 0.98 ? C5 H17 . 0.98 ? C6 C7 . 1.5330(18) ? C6 H5 . 0.98 ? C6 H4 . 0.98 ? C7 C19 . 1.5264(19) ? C7 C8 . 1.5622(19) ? C7 H3 . 0.99 ? C8 C14 . 1.5363(19) ? C8 C22 . 1.541(2) ? C8 C9 . 1.5520(17) ? C9 C21 . 1.5246(19) ? C9 C10 . 1.547(2) ? C9 H23 . 0.99 ? C10 C12 . 1.514(2) ? C10 C11 . 1.526(2) ? C10 H22 . 0.99 ? C11 H21 . 0.97 ? C11 H20 . 0.97 ? C11 H2 . 0.97 ? C12 C13 . 1.502(2) ? C13 C14 . 1.530(2) ? C13 H32 . 0.98 ? C13 H31 . 0.98 ? C14 H30 . 0.98 ? C14 H29 . 0.98 ? C15 H6 . 0.97 ? C15 H7 . 0.97 ? C15 H8 . 0.97 ? C16 C17 . 1.507(3) ? C17 C18 . 1.521(3) ? C17 H9 . 0.98 ? C17 H10 . 0.98 ? C18 H11 . 0.98 ? C18 H15 . 0.98 ? C19 C20 . 1.501(2) ? C20 C21 . 1.517(2) ? C20 H25 . 0.98 ? C20 H24 . 0.98 ? C21 H18 . 0.98 ? C21 H19 . 0.98 ? C22 H27 . 0.97 ? C22 H26 . 0.97 ? C22 H28 . 0.97 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 C2 C3 C4 . . . . 59.5(11) ? O2A C2 C3 C4 . . . . 28.3(19) ? C1 C2 C3 C4 . . . . -133.6(3) ? O2 C2 C3 C18 . . . . -61.4(11) ? O2A C2 C3 C18 . . . . -92.5(19) ? C1 C2 C3 C18 . . . . 105.6(3) ? C2 C3 C4 C5 . . . . 81.72(19) ? C18 C3 C4 C5 . . . . -153.97(14) ? C2 C3 C4 C16 . . . . -156.96(14) ? C18 C3 C4 C16 . . . . -32.66(16) ? C2 C3 C4 C15 . . . . -43.8(2) ? C18 C3 C4 C15 . . . . 80.54(17) ? C16 C4 C5 C6 . . . . -55.6(2) ? C15 C4 C5 C6 . . . . -171.07(15) ? C3 C4 C5 C6 . . . . 60.03(19) ? C4 C5 C6 C7 . . . . -173.93(14) ? C5 C6 C7 C19 . . . . 76.63(18) ? C5 C6 C7 C8 . . . . -158.14(13) ? C19 C7 C8 C14 . . . . -168.92(13) ? C6 C7 C8 C14 . . . . 65.91(17) ? C19 C7 C8 C22 . . . . 70.06(14) ? C6 C7 C8 C22 . . . . -55.11(16) ? C19 C7 C8 C9 . . . . -52.80(15) ? C6 C7 C8 C9 . . . . -177.97(13) ? C14 C8 C9 C21 . . . . 175.36(12) ? C22 C8 C9 C21 . . . . -62.72(15) ? C7 C8 C9 C21 . . . . 58.51(16) ? C14 C8 C9 C10 . . . . -59.07(16) ? C22 C8 C9 C10 . . . . 62.84(15) ? C7 C8 C9 C10 . . . . -175.93(12) ? C21 C9 C10 C12 . . . . 178.06(12) ? C8 C9 C10 C12 . . . . 52.00(17) ? C21 C9 C10 C11 . . . . -55.74(17) ? C8 C9 C10 C11 . . . . 178.20(13) ? C11 C10 C12 O1 . . . . 12.0(2) ? C9 C10 C12 O1 . . . . 139.12(16) ? C11 C10 C12 C13 . . . . -170.76(16) ? C9 C10 C12 C13 . . . . -43.7(2) ? O1 C12 C13 C14 . . . . -139.05(17) ? C10 C12 C13 C14 . . . . 43.7(2) ? C12 C13 C14 C8 . . . . -51.8(2) ? C22 C8 C14 C13 . . . . -64.00(17) ? C9 C8 C14 C13 . . . . 58.68(17) ? C7 C8 C14 C13 . . . . 175.90(13) ? C5 C4 C16 O3 . . . . -44.3(2) ? C15 C4 C16 O3 . . . . 72.8(2) ? C3 C4 C16 O3 . . . . -167.17(17) ? C5 C4 C16 C17 . . . . 136.89(15) ? C15 C4 C16 C17 . . . . -105.98(16) ? C3 C4 C16 C17 . . . . 14.00(16) ? O3 C16 C17 C18 . . . . -168.41(17) ? C4 C16 C17 C18 . . . . 10.40(18) ? C16 C17 C18 C3 . . . . -30.53(18) ? C2 C3 C18 C17 . . . . 168.76(16) ? C4 C3 C18 C17 . . . . 39.89(17) ? C6 C7 C19 O4 . . . . -2.7(2) ? C8 C7 C19 O4 . . . . -130.07(17) ? C6 C7 C19 C20 . . . . 178.29(14) ? C8 C7 C19 C20 . . . . 50.95(19) ? O4 C19 C20 C21 . . . . 130.42(18) ? C7 C19 C20 C21 . . . . -50.6(2) ? C19 C20 C21 C9 . . . . 52.75(19) ? C10 C9 C21 C20 . . . . 174.89(13) ? C8 C9 C21 C20 . . . . -58.71(17) ?