#------------------------------------------------------------------------------ #$Date: 2024-05-01 03:35:29 +0300 (Wed, 01 May 2024) $ #$Revision: 291429 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159926.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_7159926 loop_ _publ_author_name 'Li, Xiao-Dong' 'Li, Xiao-Ming' 'Wang, Bin-Gui' 'Li, Xin' _publ_section_title ; Antimicrobial sesterterpenoids with a unique 5/8/6/5 tetracyclic carbon-ring-system and diepoxide polyketides from a deep sea-sediment-sourced fungus Chaetomium globosum SD-347 ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00449C _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C25 H42 O3' _chemical_formula_sum 'C25 H42 O3' _chemical_formula_weight 390.58 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-12-10 deposited with the CCDC. 2024-04-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.005 _cell_length_b 10.685 _cell_length_c 26.893 _cell_measurement_reflns_used 9924 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.05 _cell_measurement_theta_min 5.29 _cell_volume 2300.250 _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker d8 venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_unetI/netI 0.0200 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 28454 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.440 _diffrn_reflns_theta_min 5.287 _exptl_absorpt_coefficient_mu 0.554 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.128 _exptl_crystal_description block _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.120 _exptl_transmission_factor_max 0.7531 _exptl_transmission_factor_min 0.6904 _refine_diff_density_max 1.061 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.078 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.1(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 4221 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0867 _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^)+(0.1836P)^2^+1.0625P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2500 _refine_ls_wR_factor_ref 0.2563 _reflns_Friedel_coverage 0.738 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 3972 _reflns_number_total 4221 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00449c2.cif _cod_data_source_block a_a _cod_original_cell_volume 2300.3 _cod_database_code 7159926 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.907 _shelx_estimated_absorpt_t_max 0.936 _shelx_res_file ; TITL a_a P 21 21 21 R = New: P212121 a_a.res created by SHELXL-2018/3 at 13:40:31 on 08-Nov-2019 CELL 1.54178 8.0050 10.6850 26.8930 90.000 90.000 90.000 ZERR 4 0.0000 0.0000 0.0000 0.000 0.000 0.000 LATT -1 SYMM 0.50000 - X , - Y , 0.50000 + Z SYMM 0.50000 + X , 0.50000 - Y , - Z SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H O UNIT 100 168 12 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 100 FMAP 2 PLAN -20 ACTA size 0.18 0.15 0.12 conf omit 0 0 4 delu 0.002 c4 c24 delu 0.002 c22 c25 BOND $H CONF TWIN WGHT 0.183600 1.062500 BASF 0.08887 FVAR 1.18092 O1 3 0.338189 -0.283032 0.567572 11.00000 0.03046 0.04450 = 0.03798 0.00841 0.00031 -0.00080 O2 3 0.581476 -0.351495 0.532927 11.00000 0.03034 0.06151 = 0.05464 0.01582 0.00529 0.00187 AFIX 3 H2 2 0.548876 -0.304895 0.508158 11.00000 -1.50000 AFIX 0 O3 3 -0.045296 -0.305923 0.543264 11.00000 0.02916 0.05147 = 0.04647 0.00630 -0.00309 0.00643 AFIX 3 H1 2 -0.147396 -0.305523 0.541024 11.00000 -1.50000 AFIX 0 C1 1 0.044258 -0.419231 0.554465 11.00000 0.02472 0.04311 = 0.04259 0.00683 -0.00093 0.00004 C2 1 -0.075847 -0.530809 0.549067 11.00000 0.04357 0.05836 = 0.06024 0.00041 -0.00011 -0.01551 AFIX 23 H2A 2 -0.033596 -0.603943 0.566344 11.00000 -1.20000 H2B 2 -0.185917 -0.510529 0.561818 11.00000 -1.20000 AFIX 0 C3 1 -0.080274 -0.551638 0.494411 11.00000 0.19795 0.26958 = 0.10090 -0.10003 0.07153 -0.18575 AFIX 23 H3A 2 -0.114818 -0.636805 0.487324 11.00000 -1.20000 H3B 2 -0.159835 -0.495010 0.479117 11.00000 -1.20000 AFIX 0 C4 1 0.084387 -0.529572 0.474567 11.00000 0.05490 0.08623 = 0.05521 -0.02179 -0.00260 0.00214 AFIX 13 H4 2 0.082732 -0.496174 0.440632 11.00000 -1.20000 AFIX 0 C5 1 0.174229 -0.442109 0.512047 11.00000 0.03299 0.04526 = 0.04000 0.00434 -0.00058 0.00318 AFIX 13 H5 2 0.193212 -0.361856 0.495335 11.00000 -1.20000 AFIX 0 C6 1 0.343328 -0.489447 0.530467 11.00000 0.03538 0.04863 = 0.04776 0.00276 0.00240 0.00864 AFIX 23 H6A 2 0.409568 -0.515383 0.502076 11.00000 -1.20000 H6B 2 0.325630 -0.562397 0.551279 11.00000 -1.20000 AFIX 0 C7 1 0.441705 -0.391375 0.560130 11.00000 0.02933 0.04571 = 0.04643 0.01094 0.00117 0.00330 C8 1 0.499645 -0.427419 0.613641 11.00000 0.03279 0.05905 = 0.04864 0.01360 -0.00537 0.00213 AFIX 13 H8 2 0.613915 -0.395538 0.616886 11.00000 -1.20000 AFIX 0 C9 1 0.391094 -0.346094 0.648836 11.00000 0.03551 0.06171 = 0.04117 0.00864 -0.00470 0.00034 AFIX 13 H9 2 0.344501 -0.398224 0.675418 11.00000 -1.20000 AFIX 0 C10 1 0.249088 -0.301362 0.613717 11.00000 0.03008 0.04892 = 0.03426 0.00564 -0.00033 -0.00104 C11 1 0.117575 -0.408836 0.607469 11.00000 0.03047 0.04547 = 0.03748 0.00756 -0.00148 0.00210 AFIX 13 H11 2 0.178591 -0.487030 0.613202 11.00000 -1.20000 AFIX 0 C12 1 0.169525 -0.172780 0.625663 11.00000 0.04007 0.04989 = 0.03965 -0.00435 -0.00590 -0.00008 AFIX 23 H12A 2 0.115061 -0.140455 0.596113 11.00000 -1.20000 H12B 2 0.085149 -0.183271 0.651213 11.00000 -1.20000 AFIX 0 C13 1 0.299536 -0.079351 0.643377 11.00000 0.04780 0.05697 = 0.04188 -0.00008 -0.00207 -0.00656 AFIX 13 H13 2 0.381952 -0.075008 0.616486 11.00000 -1.20000 AFIX 0 C14 1 0.397344 -0.129432 0.689073 11.00000 0.05782 0.07118 = 0.04335 -0.00446 -0.01393 -0.01314 C15 1 0.496972 -0.239767 0.671469 11.00000 0.04660 0.08630 = 0.05165 0.00092 -0.02146 -0.00436 AFIX 23 H15A 2 0.559930 -0.273009 0.699314 11.00000 -1.20000 H15B 2 0.576596 -0.211411 0.646725 11.00000 -1.20000 AFIX 0 C16 1 0.497241 -0.012528 0.702262 11.00000 0.07937 0.10184 = 0.07925 -0.02708 -0.02798 -0.02780 AFIX 23 H16A 2 0.590977 -0.001998 0.679790 11.00000 -1.20000 H16B 2 0.538958 -0.017273 0.736073 11.00000 -1.20000 AFIX 0 C17 1 0.371442 0.096223 0.696619 11.00000 0.10408 0.07941 = 0.08849 -0.02212 -0.02521 -0.01781 AFIX 23 H17A 2 0.310250 0.108591 0.727361 11.00000 -1.20000 H17B 2 0.429492 0.173230 0.688478 11.00000 -1.20000 AFIX 0 C18 1 0.250969 0.059649 0.654287 11.00000 0.07251 0.05778 = 0.05474 -0.00556 0.00209 -0.01514 AFIX 13 H18 2 0.287096 0.107603 0.625145 11.00000 -1.20000 AFIX 0 C19 1 -0.018110 -0.404228 0.647084 11.00000 0.04354 0.06556 = 0.04523 0.00706 0.00809 -0.00661 AFIX 137 H19A 2 -0.095942 -0.338771 0.639264 11.00000 -1.50000 H19B 2 0.031714 -0.387999 0.678908 11.00000 -1.50000 H19C 2 -0.075672 -0.483009 0.648064 11.00000 -1.50000 AFIX 0 C20 1 0.508663 -0.567462 0.626739 11.00000 0.04829 0.06702 = 0.07235 0.02884 -0.00221 0.01431 AFIX 137 H20A 2 0.397623 -0.600018 0.630550 11.00000 -1.50000 H20B 2 0.569162 -0.577984 0.657276 11.00000 -1.50000 H20C 2 0.564828 -0.611742 0.600561 11.00000 -1.50000 AFIX 0 C21 1 0.283337 -0.166555 0.733618 11.00000 0.08529 0.09736 = 0.03928 0.00104 -0.00714 0.00137 AFIX 137 H21A 2 0.208649 -0.232102 0.723528 11.00000 -1.50000 H21B 2 0.219780 -0.095060 0.744081 11.00000 -1.50000 H21C 2 0.351304 -0.195388 0.760706 11.00000 -1.50000 AFIX 0 C22 1 0.068698 0.094205 0.662577 11.00000 0.09164 0.05772 = 0.08742 -0.00841 -0.00238 0.00886 AFIX 13 H22 2 0.006423 0.074976 0.632148 11.00000 -1.20000 AFIX 0 C23 1 0.054822 0.236949 0.672606 11.00000 0.18210 0.06583 = 0.25382 -0.01280 0.07421 0.02999 AFIX 137 H23A 2 0.091882 0.282272 0.643826 11.00000 -1.50000 H23B 2 0.123348 0.258721 0.700595 11.00000 -1.50000 H23C 2 -0.059341 0.258100 0.679598 11.00000 -1.50000 AFIX 0 C24 1 0.149647 -0.674956 0.477376 11.00000 0.13069 0.10315 = 0.34994 -0.09781 -0.07933 0.04089 AFIX 137 H24A 2 0.090344 -0.724464 0.453381 11.00000 -1.50000 H24B 2 0.129657 -0.707618 0.510094 11.00000 -1.50000 H24C 2 0.267127 -0.677854 0.470297 11.00000 -1.50000 AFIX 0 C25 1 -0.020473 0.040569 0.704415 11.00000 0.14607 0.15182 = 0.17350 0.03037 0.06664 0.01637 AFIX 137 H25A 2 -0.095453 0.101804 0.717988 11.00000 -1.50000 H25B 2 0.058020 0.015380 0.729480 11.00000 -1.50000 H25C 2 -0.083002 -0.030975 0.693469 11.00000 -1.50000 AFIX 0 HKLF 4 REM a_a P 21 21 21 R = New: P212121 REM wR2 = 0.256257, GooF = S = 1.06568, Restrained GooF = 1.06723 for all data REM R1 = 0.086730 for 3972 Fo > 4sig(Fo) and 0.089997 for all 4221 data REM 260 parameters refined using 2 restraints END WGHT 0.1866 0.9641 REM Highest difference peak 1.061, deepest hole -0.577, 1-sigma level 0.078 Q1 1 0.1919 -0.5724 0.4327 11.00000 0.05 1.06 Q2 1 -0.0464 0.0831 0.6192 11.00000 0.05 1.04 Q3 1 0.0114 -0.6267 0.5064 11.00000 0.05 0.52 Q4 1 0.6690 -0.6576 0.5668 11.00000 0.05 0.26 Q5 1 0.2659 -0.4585 0.5215 11.00000 0.05 0.22 Q6 1 0.4277 -0.3839 0.5073 11.00000 0.05 0.21 Q7 1 0.6650 -0.1020 0.6756 11.00000 0.05 0.21 Q8 1 0.3912 -0.4417 0.5536 11.00000 0.05 0.20 Q9 1 0.2903 -0.6728 0.6499 11.00000 0.05 0.20 Q10 1 0.0895 0.2047 0.6997 11.00000 0.05 0.20 Q11 1 0.4270 0.1990 0.6696 11.00000 0.05 0.20 Q12 1 0.1048 -0.4457 0.5316 11.00000 0.05 0.19 Q13 1 0.1580 0.0857 0.6843 11.00000 0.05 0.19 Q14 1 0.3413 0.1401 0.7054 11.00000 0.05 0.19 Q15 1 0.3381 -0.1180 0.6636 11.00000 0.05 0.18 Q16 1 0.3176 0.4863 0.1934 11.00000 0.05 0.18 Q17 1 0.3529 -0.6145 0.5456 11.00000 0.05 0.18 Q18 1 0.4382 -0.0402 0.6064 11.00000 0.05 0.18 Q19 1 0.1669 -0.3313 0.4346 11.00000 0.05 0.17 Q20 1 -0.0174 -0.4379 0.4608 11.00000 0.05 0.17 ; _shelx_res_checksum 28756 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3382(3) -0.2830(3) 0.56757(10) 0.0376(7) Uani 1 1 d . . . . . O2 O 0.5815(4) -0.3515(3) 0.53293(13) 0.0488(8) Uani 1 1 d . . . . . H2 H 0.548876 -0.304895 0.508158 0.073 Uiso 1 1 d R U . . . O3 O -0.0453(4) -0.3059(3) 0.54326(11) 0.0424(7) Uani 1 1 d . . . . . H1 H -0.147396 -0.305523 0.541024 0.064 Uiso 1 1 d R U . . . C1 C 0.0443(5) -0.4192(4) 0.55446(16) 0.0368(9) Uani 1 1 d . . . . . C2 C -0.0758(7) -0.5308(5) 0.5491(2) 0.0541(12) Uani 1 1 d . . . . . H2A H -0.033596 -0.603943 0.566344 0.065 Uiso 1 1 calc R U . . . H2B H -0.185917 -0.510529 0.561818 0.065 Uiso 1 1 calc R U . . . C3 C -0.0803(18) -0.5516(16) 0.4944(4) 0.189(8) Uani 1 1 d . . . . . H3A H -0.114818 -0.636805 0.487324 0.227 Uiso 1 1 calc R U . . . H3B H -0.159835 -0.495010 0.479117 0.227 Uiso 1 1 calc R U . . . C4 C 0.0844(7) -0.5296(7) 0.4746(2) 0.0654(15) Uani 1 1 d . U . . . H4 H 0.082732 -0.496174 0.440632 0.079 Uiso 1 1 calc R U . . . C5 C 0.1742(5) -0.4421(4) 0.51205(16) 0.0394(9) Uani 1 1 d . . . . . H5 H 0.193212 -0.361856 0.495335 0.047 Uiso 1 1 calc R U . . . C6 C 0.3433(5) -0.4894(4) 0.53047(18) 0.0439(10) Uani 1 1 d . . . . . H6A H 0.409568 -0.515383 0.502076 0.053 Uiso 1 1 calc R U . . . H6B H 0.325630 -0.562397 0.551279 0.053 Uiso 1 1 calc R U . . . C7 C 0.4417(5) -0.3914(4) 0.56013(17) 0.0405(10) Uani 1 1 d . . . . . C8 C 0.4996(6) -0.4274(5) 0.61364(18) 0.0468(11) Uani 1 1 d . . . . . H8 H 0.613915 -0.395538 0.616886 0.056 Uiso 1 1 calc R U . . . C9 C 0.3911(6) -0.3461(5) 0.64884(17) 0.0461(11) Uani 1 1 d . . . . . H9 H 0.344501 -0.398224 0.675418 0.055 Uiso 1 1 calc R U . . . C10 C 0.2491(5) -0.3014(4) 0.61372(14) 0.0378(9) Uani 1 1 d . . . . . C11 C 0.1176(5) -0.4088(4) 0.60747(15) 0.0378(9) Uani 1 1 d . . . . . H11 H 0.178591 -0.487030 0.613202 0.045 Uiso 1 1 calc R U . . . C12 C 0.1695(6) -0.1728(4) 0.62566(17) 0.0432(10) Uani 1 1 d . . . . . H12A H 0.115061 -0.140455 0.596113 0.052 Uiso 1 1 calc R U . . . H12B H 0.085149 -0.183271 0.651213 0.052 Uiso 1 1 calc R U . . . C13 C 0.2995(7) -0.0794(5) 0.64338(18) 0.0489(11) Uani 1 1 d . . . . . H13 H 0.381952 -0.075008 0.616486 0.059 Uiso 1 1 calc R U . . . C14 C 0.3973(8) -0.1294(6) 0.68907(19) 0.0575(13) Uani 1 1 d . . . . . C15 C 0.4970(7) -0.2398(6) 0.6715(2) 0.0615(14) Uani 1 1 d . . . . . H15A H 0.559930 -0.273009 0.699314 0.074 Uiso 1 1 calc R U . . . H15B H 0.576596 -0.211411 0.646725 0.074 Uiso 1 1 calc R U . . . C16 C 0.4972(10) -0.0125(8) 0.7023(3) 0.087(2) Uani 1 1 d . . . . . H16A H 0.590977 -0.001998 0.679790 0.104 Uiso 1 1 calc R U . . . H16B H 0.538958 -0.017273 0.736073 0.104 Uiso 1 1 calc R U . . . C17 C 0.3714(12) 0.0962(8) 0.6966(3) 0.091(2) Uani 1 1 d . . . . . H17A H 0.310250 0.108591 0.727361 0.109 Uiso 1 1 calc R U . . . H17B H 0.429492 0.173230 0.688478 0.109 Uiso 1 1 calc R U . . . C18 C 0.2510(8) 0.0596(5) 0.6543(2) 0.0617(14) Uani 1 1 d . . . . . H18 H 0.287096 0.107603 0.625145 0.074 Uiso 1 1 calc R U . . . C19 C -0.0181(6) -0.4042(5) 0.64708(19) 0.0514(12) Uani 1 1 d . . . . . H19A H -0.095942 -0.338771 0.639264 0.077 Uiso 1 1 calc R U . . . H19B H 0.031714 -0.387999 0.678908 0.077 Uiso 1 1 calc R U . . . H19C H -0.075672 -0.483009 0.648064 0.077 Uiso 1 1 calc R U . . . C20 C 0.5087(7) -0.5675(6) 0.6267(2) 0.0626(15) Uani 1 1 d . . . . . H20A H 0.397623 -0.600018 0.630550 0.094 Uiso 1 1 calc R U . . . H20B H 0.569162 -0.577984 0.657276 0.094 Uiso 1 1 calc R U . . . H20C H 0.564828 -0.611742 0.600561 0.094 Uiso 1 1 calc R U . . . C21 C 0.2833(10) -0.1666(8) 0.7336(2) 0.0740(18) Uani 1 1 d . . . . . H21A H 0.208649 -0.232102 0.723528 0.111 Uiso 1 1 calc R U . . . H21B H 0.219780 -0.095060 0.744081 0.111 Uiso 1 1 calc R U . . . H21C H 0.351304 -0.195388 0.760706 0.111 Uiso 1 1 calc R U . . . C22 C 0.0687(11) 0.0942(6) 0.6626(3) 0.0789(18) Uani 1 1 d . U . . . H22 H 0.006423 0.074976 0.632148 0.095 Uiso 1 1 calc R U . . . C23 C 0.055(2) 0.2369(10) 0.6726(6) 0.167(7) Uani 1 1 d . . . . . H23A H 0.091882 0.282272 0.643826 0.251 Uiso 1 1 calc R U . . . H23B H 0.123348 0.258721 0.700595 0.251 Uiso 1 1 calc R U . . . H23C H -0.059341 0.258100 0.679598 0.251 Uiso 1 1 calc R U . . . C24 C 0.1496(18) -0.6750(12) 0.4774(9) 0.195(8) Uani 1 1 d . U . . . H24A H 0.090344 -0.724464 0.453381 0.292 Uiso 1 1 calc R U . . . H24B H 0.129657 -0.707618 0.510094 0.292 Uiso 1 1 calc R U . . . H24C H 0.267127 -0.677854 0.470297 0.292 Uiso 1 1 calc R U . . . C25 C -0.0205(18) 0.0406(15) 0.7044(6) 0.157(6) Uani 1 1 d . U . . . H25A H -0.095453 0.101804 0.717988 0.236 Uiso 1 1 calc R U . . . H25B H 0.058020 0.015380 0.729480 0.236 Uiso 1 1 calc R U . . . H25C H -0.083002 -0.030975 0.693469 0.236 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 0.0305(13) 0.0445(15) 0.0380(14) 0.0084(12) 0.0003(11) -0.0008(12) O2 0.0303(14) 0.0615(19) 0.0546(19) 0.0158(15) 0.0053(13) 0.0019(14) O3 0.0292(14) 0.0515(17) 0.0465(16) 0.0063(13) -0.0031(12) 0.0064(12) C1 0.0247(17) 0.043(2) 0.043(2) 0.0068(17) -0.0009(16) 0.0000(16) C2 0.044(2) 0.058(3) 0.060(3) 0.000(2) 0.000(2) -0.016(2) C3 0.198(11) 0.270(16) 0.101(7) -0.100(9) 0.072(8) -0.186(12) C4 0.055(3) 0.086(4) 0.055(3) -0.022(3) -0.003(3) 0.002(3) C5 0.0330(19) 0.045(2) 0.040(2) 0.0043(17) -0.0006(17) 0.0032(17) C6 0.035(2) 0.049(2) 0.048(2) 0.0028(18) 0.0024(18) 0.0086(19) C7 0.0293(19) 0.046(2) 0.046(2) 0.0109(19) 0.0012(17) 0.0033(16) C8 0.033(2) 0.059(3) 0.049(2) 0.014(2) -0.0054(18) 0.0021(19) C9 0.036(2) 0.062(3) 0.041(2) 0.009(2) -0.0047(18) 0.000(2) C10 0.0301(18) 0.049(2) 0.0343(19) 0.0056(17) -0.0003(15) -0.0010(16) C11 0.0305(19) 0.045(2) 0.037(2) 0.0076(17) -0.0015(16) 0.0021(17) C12 0.040(2) 0.050(2) 0.040(2) -0.0044(17) -0.0059(18) -0.0001(19) C13 0.048(3) 0.057(3) 0.042(2) 0.000(2) -0.002(2) -0.007(2) C14 0.058(3) 0.071(3) 0.043(2) -0.004(2) -0.014(2) -0.013(3) C15 0.047(3) 0.086(4) 0.052(3) 0.001(3) -0.021(2) -0.004(3) C16 0.079(4) 0.102(5) 0.079(4) -0.027(4) -0.028(4) -0.028(4) C17 0.104(6) 0.079(5) 0.088(5) -0.022(4) -0.025(5) -0.018(4) C18 0.073(4) 0.058(3) 0.055(3) -0.006(2) 0.002(3) -0.015(3) C19 0.044(2) 0.066(3) 0.045(2) 0.007(2) 0.008(2) -0.007(2) C20 0.048(3) 0.067(3) 0.072(3) 0.029(3) -0.002(3) 0.014(2) C21 0.085(4) 0.097(5) 0.039(3) 0.001(3) -0.007(3) 0.001(4) C22 0.092(5) 0.058(3) 0.087(4) -0.008(3) -0.002(4) 0.009(3) C23 0.182(13) 0.066(5) 0.254(17) -0.013(7) 0.074(13) 0.030(7) C24 0.131(9) 0.103(6) 0.35(2) -0.098(10) -0.079(13) 0.041(7) C25 0.146(10) 0.152(12) 0.174(13) 0.030(9) 0.067(10) 0.016(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C7 O1 C10 107.2(3) . . ? C7 O2 H2 109.5 . . ? C1 O3 H1 121.1 . . ? O3 C1 C2 108.7(3) . . ? O3 C1 C11 108.8(3) . . ? C2 C1 C11 112.3(4) . . ? O3 C1 C5 108.1(3) . . ? C2 C1 C5 103.1(4) . . ? C11 C1 C5 115.6(3) . . ? C3 C2 C1 103.0(5) . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2B 111.2 . . ? C1 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C4 C3 C2 108.6(8) . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.3 . . ? C3 C4 C24 96.8(11) . . ? C3 C4 C5 106.4(5) . . ? C24 C4 C5 113.1(7) . . ? C3 C4 H4 113.1 . . ? C24 C4 H4 113.1 . . ? C5 C4 H4 113.1 . . ? C6 C5 C4 115.0(4) . . ? C6 C5 C1 113.9(3) . . ? C4 C5 C1 105.1(4) . . ? C6 C5 H5 107.5 . . ? C4 C5 H5 107.5 . . ? C1 C5 H5 107.5 . . ? C5 C6 C7 113.4(4) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? O2 C7 O1 106.7(3) . . ? O2 C7 C6 110.2(4) . . ? O1 C7 C6 109.1(3) . . ? O2 C7 C8 108.6(3) . . ? O1 C7 C8 104.0(4) . . ? C6 C7 C8 117.6(4) . . ? C20 C8 C9 115.6(4) . . ? C20 C8 C7 117.7(5) . . ? C9 C8 C7 105.0(4) . . ? C20 C8 H8 105.9 . . ? C9 C8 H8 105.9 . . ? C7 C8 H8 105.9 . . ? C15 C9 C8 110.2(4) . . ? C15 C9 C10 114.5(4) . . ? C8 C9 C10 102.2(4) . . ? C15 C9 H9 109.9 . . ? C8 C9 H9 109.9 . . ? C10 C9 H9 109.9 . . ? O1 C10 C12 105.1(3) . . ? O1 C10 C9 101.7(3) . . ? C12 C10 C9 116.6(4) . . ? O1 C10 C11 109.8(3) . . ? C12 C10 C11 113.3(3) . . ? C9 C10 C11 109.4(4) . . ? C19 C11 C1 112.1(3) . . ? C19 C11 C10 112.4(4) . . ? C1 C11 C10 114.0(3) . . ? C19 C11 H11 105.8 . . ? C1 C11 H11 105.8 . . ? C10 C11 H11 105.8 . . ? C13 C12 C10 111.5(4) . . ? C13 C12 H12A 109.3 . . ? C10 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C10 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 111.6(4) . . ? C12 C13 C18 120.9(5) . . ? C14 C13 C18 107.7(4) . . ? C12 C13 H13 105.1 . . ? C14 C13 H13 105.1 . . ? C18 C13 H13 105.1 . . ? C15 C14 C16 116.0(5) . . ? C15 C14 C13 106.8(4) . . ? C16 C14 C13 99.6(5) . . ? C15 C14 C21 110.7(5) . . ? C16 C14 C21 109.7(5) . . ? C13 C14 C21 113.7(5) . . ? C14 C15 C9 114.3(4) . . ? C14 C15 H15A 108.7 . . ? C9 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C9 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C14 C16 C17 104.6(5) . . ? C14 C16 H16A 110.8 . . ? C17 C16 H16A 110.8 . . ? C14 C16 H16B 110.8 . . ? C17 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C18 C17 C16 106.8(6) . . ? C18 C17 H17A 110.4 . . ? C16 C17 H17A 110.4 . . ? C18 C17 H17B 110.4 . . ? C16 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? C22 C18 C17 115.5(6) . . ? C22 C18 C13 119.8(5) . . ? C17 C18 C13 102.9(5) . . ? C22 C18 H18 105.9 . . ? C17 C18 H18 105.9 . . ? C13 C18 H18 105.9 . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C8 C20 H20A 109.5 . . ? C8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C25 C22 C18 119.3(8) . . ? C25 C22 C23 102.6(10) . . ? C18 C22 C23 109.4(9) . . ? C25 C22 H22 108.3 . . ? C18 C22 H22 108.3 . . ? C23 C22 H22 108.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C4 C24 H24A 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C7 1.438(5) . ? O1 C10 1.445(5) . ? O2 C7 1.403(5) . ? O2 H2 0.8716 . ? O3 C1 1.439(5) . ? O3 H1 0.8195 . ? C1 C2 1.538(6) . ? C1 C11 1.546(6) . ? C1 C5 1.563(6) . ? C2 C3 1.487(11) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.441(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C24 1.641(13) . ? C4 C5 1.551(7) . ? C4 H4 0.9800 . ? C5 C6 1.528(6) . ? C5 H5 0.9800 . ? C6 C7 1.534(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.560(6) . ? C8 C20 1.539(7) . ? C8 C9 1.551(7) . ? C8 H8 0.9800 . ? C9 C15 1.543(8) . ? C9 C10 1.553(6) . ? C9 H9 0.9800 . ? C10 C12 1.548(6) . ? C10 C11 1.567(6) . ? C11 C19 1.522(6) . ? C11 H11 0.9800 . ? C12 C13 1.519(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.552(7) . ? C13 C18 1.563(8) . ? C13 H13 0.9800 . ? C14 C15 1.500(9) . ? C14 C16 1.525(9) . ? C14 C21 1.557(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.545(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.542(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C22 1.521(11) . ? C18 H18 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C25 1.451(14) . ? C22 C23 1.553(12) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 O3 C1 C2 C3 79.7(9) . . . . ? C11 C1 C2 C3 -159.9(9) . . . . ? C5 C1 C2 C3 -34.8(9) . . . . ? C1 C2 C3 C4 37.3(14) . . . . ? C2 C3 C4 C24 93.1(13) . . . . ? C2 C3 C4 C5 -23.5(15) . . . . ? C3 C4 C5 C6 126.5(10) . . . . ? C24 C4 C5 C6 21.4(11) . . . . ? C3 C4 C5 C1 0.5(10) . . . . ? C24 C4 C5 C1 -104.6(10) . . . . ? O3 C1 C5 C6 139.6(4) . . . . ? C2 C1 C5 C6 -105.4(4) . . . . ? C11 C1 C5 C6 17.5(5) . . . . ? O3 C1 C5 C4 -93.7(4) . . . . ? C2 C1 C5 C4 21.3(5) . . . . ? C11 C1 C5 C4 144.2(4) . . . . ? C4 C5 C6 C7 170.0(4) . . . . ? C1 C5 C6 C7 -68.7(5) . . . . ? C10 O1 C7 O2 -150.7(3) . . . . ? C10 O1 C7 C6 90.3(4) . . . . ? C10 O1 C7 C8 -36.0(4) . . . . ? C5 C6 C7 O2 -110.4(4) . . . . ? C5 C6 C7 O1 6.5(5) . . . . ? C5 C6 C7 C8 124.5(4) . . . . ? O2 C7 C8 C20 -105.8(5) . . . . ? O1 C7 C8 C20 140.8(4) . . . . ? C6 C7 C8 C20 20.1(6) . . . . ? O2 C7 C8 C9 124.0(4) . . . . ? O1 C7 C8 C9 10.7(4) . . . . ? C6 C7 C8 C9 -110.0(4) . . . . ? C20 C8 C9 C15 122.2(5) . . . . ? C7 C8 C9 C15 -106.4(4) . . . . ? C20 C8 C9 C10 -115.6(5) . . . . ? C7 C8 C9 C10 15.8(5) . . . . ? C7 O1 C10 C12 168.4(3) . . . . ? C7 O1 C10 C9 46.4(4) . . . . ? C7 O1 C10 C11 -69.3(4) . . . . ? C15 C9 C10 O1 82.5(5) . . . . ? C8 C9 C10 O1 -36.7(4) . . . . ? C15 C9 C10 C12 -31.2(6) . . . . ? C8 C9 C10 C12 -150.4(4) . . . . ? C15 C9 C10 C11 -161.4(4) . . . . ? C8 C9 C10 C11 79.4(4) . . . . ? O3 C1 C11 C19 65.9(4) . . . . ? C2 C1 C11 C19 -54.5(5) . . . . ? C5 C1 C11 C19 -172.3(4) . . . . ? O3 C1 C11 C10 -63.2(4) . . . . ? C2 C1 C11 C10 176.4(4) . . . . ? C5 C1 C11 C10 58.6(5) . . . . ? O1 C10 C11 C19 -160.5(3) . . . . ? C12 C10 C11 C19 -43.3(5) . . . . ? C9 C10 C11 C19 88.7(4) . . . . ? O1 C10 C11 C1 -31.5(5) . . . . ? C12 C10 C11 C1 85.7(4) . . . . ? C9 C10 C11 C1 -142.3(3) . . . . ? O1 C10 C12 C13 -73.6(4) . . . . ? C9 C10 C12 C13 38.1(5) . . . . ? C11 C10 C12 C13 166.5(4) . . . . ? C10 C12 C13 C14 -56.0(5) . . . . ? C10 C12 C13 C18 175.9(4) . . . . ? C12 C13 C14 C15 66.3(6) . . . . ? C18 C13 C14 C15 -158.8(5) . . . . ? C12 C13 C14 C16 -172.7(5) . . . . ? C18 C13 C14 C16 -37.8(6) . . . . ? C12 C13 C14 C21 -56.1(6) . . . . ? C18 C13 C14 C21 78.7(6) . . . . ? C16 C14 C15 C9 -168.5(5) . . . . ? C13 C14 C15 C9 -58.6(6) . . . . ? C21 C14 C15 C9 65.6(6) . . . . ? C8 C9 C15 C14 157.2(4) . . . . ? C10 C9 C15 C14 42.6(6) . . . . ? C15 C14 C16 C17 156.3(6) . . . . ? C13 C14 C16 C17 42.2(7) . . . . ? C21 C14 C16 C17 -77.4(7) . . . . ? C14 C16 C17 C18 -32.7(8) . . . . ? C16 C17 C18 C22 140.7(7) . . . . ? C16 C17 C18 C13 8.3(8) . . . . ? C12 C13 C18 C22 18.5(8) . . . . ? C14 C13 C18 C22 -111.3(6) . . . . ? C12 C13 C18 C17 148.3(6) . . . . ? C14 C13 C18 C17 18.5(6) . . . . ? C17 C18 C22 C25 -61.5(11) . . . . ? C13 C18 C22 C25 62.4(11) . . . . ? C17 C18 C22 C23 56.1(11) . . . . ? C13 C18 C22 C23 180.0(8) . . . . ?