#------------------------------------------------------------------------------ #$Date: 2021-01-04 05:17:54 +0200 (Mon, 04 Jan 2021) $ #$Revision: 260432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559805.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_1559805 loop_ _publ_author_name 'Chi, Lu-Ping' 'Li, Xiao-Ming' 'Wan, Yu-Peng' 'Li, Xin' 'Wang, Bin-Gui' _publ_section_title ; Ophiobolin Sesterterpenoids and Farnesylated Phthalide Derivatives from the Deep Sea Cold-Seep-Derived Fungus Aspergillus insuetus SD-512. ; _journal_issue 12 _journal_name_full 'Journal of natural products' _journal_page_first 3652 _journal_page_last 3660 _journal_paper_doi 10.1021/acs.jnatprod.0c00860 _journal_volume 83 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_sum 'C25 H38 O2' _chemical_formula_weight 370.55 _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_creation_method SHELXL-2018/3 _cell_angle_alpha 90 _cell_angle_beta 105.919(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.5452(14) _cell_length_b 6.0471(7) _cell_length_c 16.751(2) _cell_measurement_reflns_used 637 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 63.8110 _cell_measurement_theta_min 4.1640 _cell_volume 1124.6(2) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.1281 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_unetI/netI 0.1050 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3645 _diffrn_reflns_point_group_measured_fraction_full 0.694 _diffrn_reflns_point_group_measured_fraction_max 0.694 _diffrn_reflns_theta_full 66.007 _diffrn_reflns_theta_max 66.007 _diffrn_reflns_theta_min 2.743 _exptl_absorpt_coefficient_mu 0.512 _exptl_absorpt_correction_T_max 0.9506 _exptl_absorpt_correction_T_min 0.8615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.094 _exptl_crystal_description needle _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.231 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details ; Flack x determined using 262 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.2(4) _refine_ls_extinction_coef 0.0071(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 251 _refine_ls_number_reflns 2716 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.1050 _refine_ls_R_factor_gt 0.0562 _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^)+(0.0002P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.0773 _reflns_Friedel_coverage 0.263 _reflns_Friedel_fraction_full 0.323 _reflns_Friedel_fraction_max 0.323 _reflns_number_gt 1488 _reflns_number_total 2716 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file np0c00860_si_002.cif _cod_data_source_block 190729a _cod_depositor_comments 'Adding full bibliography for 1559804--1559806.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1559805 _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 0.861 _shelx_estimated_absorpt_t_max 0.951 _shelx_res_file ; TITL 190729a in P21 190729a.res created by SHELXL-2018/3 at 11:45:53 on 07-Oct-2020 CELL 1.54178 11.5452 6.0471 16.751 90 105.919 90 ZERR 2 0.0014 0.0007 0.002 0 0.003 0 LATT -1 SYMM -x,1/2+y,-z SFAC C H O UNIT 50 76 4 OMIT -1.00 132.10 OMIT -10 1 3 OMIT 2 2 11 OMIT -9 2 1 OMIT -1 -1 2 OMIT -10 3 12 OMIT 7 0 7 OMIT 1 0 0 OMIT 0 2 12 OMIT -5 1 2 OMIT -11 3 12 OMIT -5 0 2 L.S. 8 ACTA BOND $h FMAP 2 PLAN 25 conf htab dfix 2.16 0.01 h5 h9 size 0.30 0.14 0.10 WGHT 0.000241 EXTI 0.007067 FVAR 0.45276 O1 3 0.866442 1.044475 0.356255 11.00000 0.06405 0.05340 = 0.12240 0.02209 0.01702 -0.01405 O2 3 0.934284 0.489226 0.325649 11.00000 0.05537 0.07267 = 0.08786 0.01429 0.02136 0.00282 AFIX 147 H2 2 0.910394 0.363539 0.330455 11.00000 -1.50000 AFIX 0 C1 1 0.831233 0.893254 0.391571 11.00000 0.05063 0.04886 = 0.09414 0.00025 0.01555 -0.00115 C2 1 0.871627 0.830575 0.477888 11.00000 0.07099 0.07132 = 0.06333 -0.01416 0.00959 -0.00348 AFIX 43 H2A 2 0.932471 0.902691 0.517289 11.00000 -1.20000 AFIX 0 C3 1 0.811143 0.657002 0.494157 11.00000 0.04521 0.06269 = 0.04645 -0.00576 0.00887 0.00262 C4 1 0.715708 0.577626 0.417827 11.00000 0.04882 0.04394 = 0.04772 -0.00609 0.01420 -0.00570 AFIX 13 H4 2 0.737045 0.429033 0.403279 11.00000 -1.20000 AFIX 0 C5 1 0.728463 0.742221 0.349873 11.00000 0.04691 0.03689 = 0.05795 0.00247 0.01999 -0.00318 AFIX 13 H5 2 0.655825 0.834234 0.337378 11.00000 -1.20000 AFIX 0 C6 1 0.728519 0.630120 0.269080 11.00000 0.04509 0.05161 = 0.05350 0.00790 0.01949 0.00388 C7 1 0.633129 0.555439 0.212616 11.00000 0.06242 0.05790 = 0.05240 0.00000 0.02728 0.01251 AFIX 43 H7 2 0.651963 0.481141 0.169197 11.00000 -1.20000 AFIX 0 C8 1 0.499897 0.565915 0.204096 11.00000 0.05837 0.05272 = 0.04398 -0.00119 0.01627 0.00671 AFIX 23 H8A 2 0.467723 0.419657 0.187489 11.00000 -1.20000 H8B 2 0.465142 0.664003 0.157919 11.00000 -1.20000 AFIX 0 C9 1 0.449881 0.638854 0.276455 11.00000 0.05446 0.03514 = 0.04103 0.00323 0.01628 0.00481 AFIX 13 H9 2 0.484186 0.784944 0.294093 11.00000 -1.20000 AFIX 0 C10 1 0.487662 0.483463 0.355439 11.00000 0.04290 0.04195 = 0.04986 -0.00125 0.01058 -0.00341 C11 1 0.588331 0.572338 0.428573 11.00000 0.04801 0.04683 = 0.04624 0.00267 0.01670 -0.00283 AFIX 23 H11A 2 0.567065 0.721634 0.440358 11.00000 -1.20000 H11B 2 0.590088 0.482982 0.476981 11.00000 -1.20000 AFIX 0 C12 1 0.369954 0.469976 0.382097 11.00000 0.05491 0.06962 = 0.04987 0.00508 0.01966 -0.01351 AFIX 23 H12A 2 0.366812 0.333582 0.411908 11.00000 -1.20000 H12B 2 0.363791 0.593845 0.417496 11.00000 -1.20000 AFIX 0 C13 1 0.269433 0.477199 0.301654 11.00000 0.05277 0.07931 = 0.05017 0.00701 0.00820 -0.01002 AFIX 23 H13A 2 0.263478 0.338728 0.271566 11.00000 -1.20000 H13B 2 0.192452 0.509906 0.311810 11.00000 -1.20000 AFIX 0 C14 1 0.309948 0.664274 0.255110 11.00000 0.04322 0.05164 = 0.04960 -0.00229 0.01192 0.00526 AFIX 13 H14 2 0.296062 0.800277 0.282939 11.00000 -1.20000 AFIX 0 C15 1 0.241990 0.695322 0.163741 11.00000 0.03771 0.06963 = 0.05089 -0.00030 0.00649 0.00340 AFIX 13 H15 2 0.270737 0.584916 0.130820 11.00000 -1.20000 AFIX 0 C16 1 0.265457 0.928329 0.133522 11.00000 0.09106 0.06114 = 0.05528 -0.00266 0.01449 0.01655 AFIX 23 H16A 2 0.225304 1.035672 0.159745 11.00000 -1.20000 H16B 2 0.351230 0.957717 0.152704 11.00000 -1.20000 AFIX 0 C17 1 0.224130 0.966570 0.039001 11.00000 0.11049 0.08009 = 0.05578 0.01527 0.01536 0.01778 AFIX 23 H17A 2 0.139770 0.927459 0.017802 11.00000 -1.20000 H17B 2 0.232936 1.121653 0.027069 11.00000 -1.20000 AFIX 0 C18 1 0.297757 0.829150 -0.002729 11.00000 0.07084 0.08709 = 0.05805 0.01357 0.01362 0.00208 AFIX 43 H18 2 0.379637 0.861322 0.011230 11.00000 -1.20000 AFIX 0 C19 1 0.261604 0.668106 -0.056807 11.00000 0.10281 0.07413 = 0.06693 0.00912 0.02010 -0.00311 C20 1 0.351257 0.543415 -0.091954 11.00000 0.21952 0.10107 = 0.10317 -0.00497 0.06246 0.02374 AFIX 137 H20A 2 0.431646 0.589082 -0.063576 11.00000 -1.50000 H20B 2 0.335495 0.575172 -0.150105 11.00000 -1.50000 H20C 2 0.343125 0.387416 -0.084329 11.00000 -1.50000 AFIX 0 C21 1 0.133102 0.592441 -0.089004 11.00000 0.16255 0.13539 = 0.10166 -0.00502 -0.01109 -0.05934 AFIX 137 H21A 2 0.085850 0.655049 -0.055596 11.00000 -1.50000 H21B 2 0.129950 0.434029 -0.086477 11.00000 -1.50000 H21C 2 0.101491 0.639951 -0.145490 11.00000 -1.50000 AFIX 0 C22 1 0.833258 0.534286 0.574229 11.00000 0.06268 0.10324 = 0.05032 0.00159 0.00793 0.00190 AFIX 137 H22A 2 0.897786 0.603646 0.615208 11.00000 -1.50000 H22B 2 0.854678 0.384095 0.566312 11.00000 -1.50000 H22C 2 0.761538 0.536175 0.592676 11.00000 -1.50000 AFIX 0 C23 1 0.852677 0.596038 0.256570 11.00000 0.05716 0.08305 = 0.07236 0.02221 0.02730 0.01237 AFIX 23 H23A 2 0.845177 0.507481 0.207127 11.00000 -1.20000 H23B 2 0.885679 0.738510 0.247661 11.00000 -1.20000 AFIX 0 C24 1 0.519411 0.245089 0.335099 11.00000 0.08257 0.04145 = 0.06765 -0.00185 0.01253 -0.00376 AFIX 137 H24A 2 0.537577 0.157241 0.384726 11.00000 -1.50000 H24B 2 0.588180 0.248570 0.313380 11.00000 -1.50000 H24C 2 0.452165 0.181643 0.294579 11.00000 -1.50000 AFIX 0 C25 1 0.107423 0.659922 0.151715 11.00000 0.05337 0.15192 = 0.08072 0.01381 0.00874 -0.01151 AFIX 137 H25A 2 0.064509 0.691896 0.095206 11.00000 -1.50000 H25B 2 0.079898 0.756521 0.188172 11.00000 -1.50000 H25C 2 0.093200 0.509077 0.164201 11.00000 -1.50000 AFIX 0 HKLF 4 REM 190729a in P21 REM wR2 = 0.0773, GooF = S = 0.967, Restrained GooF = 1.052 for all data REM R1 = 0.0562 for 1488 Fo > 4sig(Fo) and 0.1050 for all 2716 data REM 251 parameters refined using 2 restraints END WGHT 0.0114 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 x, y-1, z HTAB O2 O1_$1 HTAB C23 O1 REM Highest difference peak 0.231, deepest hole -0.145, 1-sigma level 0.036 Q1 1 0.7000 0.7233 0.3412 11.00000 0.05 0.23 Q2 1 0.4800 0.6650 0.2854 11.00000 0.05 0.19 Q3 1 0.5975 0.7192 0.4291 11.00000 0.05 0.15 Q4 1 0.5060 0.3684 0.3522 11.00000 0.05 0.15 Q5 1 0.4677 0.5266 0.2872 11.00000 0.05 0.15 Q6 1 0.7655 0.6225 0.2672 11.00000 0.05 0.14 Q7 1 0.2492 0.7578 0.1738 11.00000 0.05 0.13 Q8 1 0.3195 0.7737 0.2535 11.00000 0.05 0.13 Q9 1 0.4564 0.5185 0.1531 11.00000 0.05 0.13 Q10 1 0.0697 0.5951 0.1754 11.00000 0.05 0.13 Q11 1 0.2966 0.6463 -0.0725 11.00000 0.05 0.12 Q12 1 0.7941 0.4931 0.3501 11.00000 0.05 0.12 Q13 1 0.8800 0.2403 0.4671 11.00000 0.05 0.12 Q14 1 0.2236 0.4973 -0.1557 11.00000 0.05 0.12 Q15 1 0.7397 0.4506 0.1580 11.00000 0.05 0.12 Q16 1 0.5744 0.3999 0.4932 11.00000 0.05 0.11 Q17 1 0.3039 0.4861 0.3179 11.00000 0.05 0.11 Q18 1 0.8957 0.5605 0.4483 11.00000 0.05 0.11 Q19 1 0.4652 0.0946 0.3960 11.00000 0.05 0.11 Q20 1 0.8074 1.0485 0.2858 11.00000 0.05 0.11 Q21 1 0.0762 1.0008 0.1230 11.00000 0.05 0.11 Q22 1 0.6397 0.6917 0.2076 11.00000 0.05 0.11 Q23 1 0.3371 0.2550 0.1829 11.00000 0.05 0.11 Q24 1 0.8149 0.6212 0.5373 11.00000 0.05 0.11 Q25 1 0.3964 0.9848 0.1333 11.00000 0.05 0.11 ; _shelx_res_checksum 2824 _shelx_hkl_file ; 0 -4 0 1.82 1.03 0 -4 1 15.35 2.95 0 -4 2 10.38 2.42 0 -4 3 45.59 5.26 0 -4 4 52.42 5.84 0 -4 5 20.66 3.80 0 -4 6 66.28 7.04 0 -4 7 22.89 4.26 0 -4 8 16.34 3.71 0 -4 9 44.58 6.26 0 -4 10 14.70 3.59 0 -3 2 54.55 4.78 0 -3 3 26.48 3.41 0 -3 4 41.00 4.42 0 -3 5 73.50 6.22 0 -3 6 18.34 3.26 0 -3 7 13.58 2.95 0 -3 8 52.26 6.07 0 -3 9 13.76 3.32 0 -3 10 22.28 4.28 0 -3 11 11.30 3.15 0 -3 12 10.04 2.99 0 -2 0 971.23 14.82 0 -2 -1 25.22 1.90 0 -2 -1 24.51 2.37 0 -2 2 158.34 6.48 0 -2 -2 156.01 5.56 0 -2 -2 154.29 6.31 0 -2 3 76.51 4.75 0 -2 -3 74.68 4.35 0 -2 3 82.69 3.36 0 -2 4 145.24 6.99 0 -2 -4 149.02 6.78 0 -2 5 43.64 4.13 0 -2 6 171.30 8.73 0 -2 7 1.69 1.00 0 -2 8 17.41 3.22 0 -2 9 25.07 4.05 0 -2 10 14.99 3.34 0 -2 11 10.08 2.92 0 -2 12 24.58 4.55 0 -2 13 23.83 4.73 0 -1 0 0.91 0.34 0 -1 0 1.30 0.27 0 -1 -1 1000.00 9.74 0 -1 -2 355.00 7.06 0 -1 2 355.76 4.43 0 -1 -3 957.06 13.47 0 -1 4 333.92 8.97 0 -1 -4 331.53 8.87 0 -1 -5 19.46 2.39 0 -1 5 20.25 2.45 0 -1 -6 73.17 4.40 0 -1 6 74.66 5.14 0 -1 -7 8.02 1.51 0 -1 7 9.21 2.00 0 -1 8 39.69 4.38 0 -1 9 43.89 4.97 0 -1 10 8.71 2.46 0 -1 11 1.37 0.88 0 -1 12 2.75 1.41 0 -1 13 0.85 1.05 0 -1 -13 2.54 1.99 0 -1 13 -1.25 1.08 0 -1 -14 7.19 3.26 0 -1 14 4.72 2.06 0 -1 -15 7.02 3.24 0 -1 -16 1.31 1.73 0 -1 -17 -1.01 1.19 0 -1 -18 6.53 2.53 0 -1 -19 0.92 0.88 0 0 1 204.77 3.02 0 0 2 114.84 3.19 0 0 3 252.72 5.78 0 0 -4 98.17 2.93 0 0 -5 0.10 0.19 0 0 -5 -0.02 0.20 0 0 5 -0.17 0.36 0 0 6 14.25 2.14 0 0 -6 14.64 2.03 0 0 -6 15.61 1.42 0 0 7 3.31 1.14 0 0 8 3.41 1.27 0 0 9 13.30 2.64 0 0 10 2.77 1.30 0 0 11 -1.00 0.90 0 0 12 22.25 4.05 0 0 12 25.01 4.34 0 0 -13 19.28 5.54 0 0 13 20.42 4.06 0 0 14 24.38 4.58 0 0 -14 38.68 7.78 0 0 -15 0.46 0.99 0 0 -16 0.75 1.23 0 0 -17 2.53 1.90 0 0 -18 1.25 1.27 0 0 -19 11.88 3.17 0 1 -1 992.06 10.36 0 1 -2 353.44 3.46 0 1 4 335.94 8.61 0 1 4 335.54 9.07 0 1 5 18.44 2.25 0 1 5 20.41 2.48 0 1 6 67.78 4.86 0 1 7 7.93 1.79 0 1 8 42.57 4.53 0 1 9 48.45 5.17 0 1 10 10.44 2.55 0 1 11 0.68 0.44 0 1 12 4.04 1.82 0 1 13 1.70 1.19 0 1 -13 -1.61 1.60 0 1 -14 6.60 3.22 0 1 14 5.30 2.08 0 1 -15 4.92 2.97 0 1 -16 -0.49 1.03 0 1 -17 1.23 1.36 0 1 -18 6.93 2.82 0 1 -19 0.70 0.85 0 2 0 980.41 14.86 0 2 1 25.05 2.37 0 2 -1 25.43 2.46 0 2 -1 25.47 2.35 0 2 -2 158.38 5.95 0 2 2 153.38 6.10 0 2 3 76.32 4.46 0 2 3 81.31 4.64 0 2 -3 75.97 4.32 0 2 4 143.58 6.75 0 2 4 148.27 6.62 0 2 5 49.14 4.02 0 2 -12 8.55 3.42 0 2 -13 31.41 6.69 0 2 -14 10.42 3.99 0 2 -15 2.58 1.98 0 2 -16 0.86 0.83 0 2 -16 1.11 1.52 0 2 -17 5.02 2.54 0 2 -17 2.69 1.28 0 2 -18 1.18 0.76 0 2 -18 2.70 1.58 0 2 -19 2.15 1.19 0 3 0 -0.28 0.54 0 3 1 21.57 2.84 0 3 2 57.90 4.67 0 3 3 27.62 3.34 0 3 4 41.59 4.22 0 3 5 71.25 5.64 0 3 6 20.94 3.21 0 3 7 15.64 2.92 0 3 8 52.63 5.53 0 3 9 14.62 3.01 0 3 -11 12.15 3.13 0 3 -12 12.89 3.31 0 3 -13 1.66 1.19 0 3 -14 6.93 2.74 0 3 -15 1.48 1.05 0 3 -16 5.28 1.80 0 3 -17 1.18 0.74 0 4 1 13.27 2.73 0 4 2 9.63 2.33 0 4 3 43.19 4.88 0 4 4 52.11 5.39 0 4 -8 14.47 3.80 0 4 -8 20.46 4.22 0 4 -8 16.91 3.82 0 4 -9 47.96 6.54 0 4 -9 47.45 6.53 0 4 -9 50.36 6.68 0 4 -10 12.17 3.25 0 4 -10 13.64 3.50 0 4 -10 9.39 2.82 0 4 -11 3.24 1.69 0 4 -11 1.25 1.06 0 4 -12 1.62 1.25 0 4 -12 2.24 1.32 0 4 -13 0.72 0.81 0 4 -13 0.16 0.47 0 4 -14 6.12 1.90 0 4 -14 4.08 1.63 0 4 -15 2.47 1.21 0 4 -15 2.59 1.20 0 4 -16 1.35 0.76 0 5 0 -0.32 0.58 0 5 0 0.23 0.77 0 5 1 14.68 4.21 0 5 1 10.19 3.04 0 5 -1 16.46 4.45 0 5 -1 10.06 3.02 0 5 -2 14.37 3.50 0 5 2 26.57 5.70 0 5 -2 20.56 4.99 0 5 2 17.51 3.85 0 5 -3 2.58 1.48 0 5 3 3.97 1.58 0 5 -3 5.04 2.54 0 5 3 3.38 2.08 0 5 -4 11.58 3.13 0 5 4 14.13 3.48 0 5 4 14.31 4.27 0 5 -5 29.33 4.97 0 5 -5 20.66 4.24 0 5 5 25.79 5.74 0 5 -6 8.14 2.69 0 5 -6 9.21 2.83 0 5 6 14.23 4.31 0 5 7 1.71 1.53 0 5 -7 1.25 1.07 0 5 -7 0.50 0.71 0 5 -8 0.83 0.88 0 5 -8 1.36 0.73 0 5 -9 4.89 2.00 0 5 -9 3.85 1.79 0 5 -10 11.28 2.90 0 5 -10 10.95 2.86 0 5 -11 0.14 0.36 0 5 -11 0.20 0.39 0 5 -12 0.67 0.69 0 5 -13 4.46 1.51 0 6 0 -0.83 0.91 0 6 0 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0.53 -10 0 4 6.54 3.31 -10 0 4 4.97 2.29 10 0 -4 4.68 2.01 -10 0 3 11.87 4.24 10 0 -3 8.65 2.71 -10 0 2 6.16 3.01 10 0 -2 10.56 2.96 -10 0 1 2.90 2.08 10 0 -1 2.33 1.43 -10 0 0 -0.01 0.75 10 0 0 -1.26 1.11 -10 0 -1 2.88 2.06 -10 0 -2 1.93 1.72 -10 0 -3 -0.51 1.06 -10 0 -4 0.17 0.68 -10 0 -5 4.26 2.42 -10 0 -6 -0.33 0.87 -10 0 -7 -1.70 1.41 -10 0 -8 -0.60 0.83 -10 0 -9 -0.69 0.80 -10 1 7 1.96 1.32 -10 1 6 0.45 0.69 -10 1 4 2.08 1.73 -10 1 3 1.92 1.78 -10 1 2 2.50 2.53 -10 1 1 0.36 0.92 -10 1 0 6.46 3.14 -10 1 -1 1.73 1.65 -10 1 -2 1.43 1.53 -10 1 -3 3.89 2.44 -10 1 -4 5.37 2.78 -10 1 -5 2.69 1.99 -10 1 -6 0.08 1.53 -10 1 -7 0.17 0.59 -10 1 -8 0.19 0.81 -10 1 -9 2.63 1.44 10 2 -5 11.62 3.36 -10 2 4 2.94 2.14 10 2 -4 2.36 1.51 -10 2 3 26.22 6.38 10 2 -3 16.99 3.92 -10 2 2 3.06 2.53 10 2 -2 12.28 3.50 -10 2 1 3.58 2.33 -10 2 0 -1.86 1.67 -10 2 -1 10.45 3.87 -10 2 -2 4.03 2.41 -10 2 -3 1.75 1.62 -10 2 -4 -1.14 1.31 -10 2 -5 0.96 1.64 -10 2 -6 -0.01 0.92 -10 2 -7 0.49 0.97 -10 2 -8 -0.47 0.73 -10 2 -9 0.54 0.70 -10 3 12 0.46 0.57 10 3 -10 -0.40 0.59 10 3 -9 5.86 2.31 10 3 -8 4.01 1.86 10 3 -7 2.31 1.45 10 3 -6 0.85 0.93 10 3 -5 4.00 1.98 10 3 -4 2.29 1.48 10 3 -3 0.91 0.95 -10 3 2 -4.24 2.36 10 3 -2 -0.27 0.62 -10 3 1 0.53 1.03 10 3 -1 0.68 0.86 -10 3 0 5.83 2.75 10 3 0 2.20 1.45 -10 3 -1 0.65 1.06 10 3 1 1.54 1.18 -10 3 -2 -3.59 2.09 -10 3 -3 3.87 2.07 -10 3 -4 3.17 1.83 -10 3 -5 0.38 0.74 -10 3 -6 -1.16 1.00 -10 3 -7 -0.02 0.44 10 3 7 -1.07 0.77 -10 4 12 0.66 0.61 10 4 -12 0.93 0.60 -10 4 11 -1.06 0.81 10 4 -11 1.52 0.89 -10 4 10 0.44 0.61 10 4 -10 1.30 0.91 10 4 -9 1.79 1.14 10 4 -8 2.57 1.34 10 4 -7 3.55 1.62 10 4 -6 -0.35 0.58 10 4 -5 0.88 0.86 10 4 -4 1.41 1.05 10 4 -3 1.17 1.00 10 4 -2 0.95 0.91 10 4 -1 -0.70 0.75 10 4 0 -0.60 0.74 10 4 1 0.89 0.81 10 4 2 1.26 0.94 10 4 3 0.30 0.76 10 4 4 1.43 0.84 10 4 5 0.27 0.39 -10 5 8 -0.46 0.55 10 5 -8 0.68 0.57 -10 5 7 0.04 0.49 10 5 -7 0.66 0.59 -10 5 6 0.53 0.75 10 5 -6 0.51 0.56 -10 5 5 -0.48 0.51 10 5 -5 1.10 0.81 -10 5 4 -1.70 0.90 10 5 -4 0.77 0.76 -10 5 3 0.86 0.61 10 5 -3 0.13 0.34 10 5 -2 1.33 0.83 10 5 -1 -0.63 0.59 10 5 0 0.58 0.53 -11 -3 13 0.57 0.57 -11 -3 12 3.04 1.38 -11 -3 11 -0.12 0.39 -11 -3 10 -0.48 0.65 -11 -3 9 -0.65 0.78 -11 -3 8 1.59 1.17 -11 -3 7 2.56 1.45 -11 -3 6 0.33 0.59 -11 -3 5 0.50 0.71 -11 -3 4 2.69 1.53 -11 -3 3 2.18 1.37 -11 -3 2 0.16 0.46 -11 -3 1 0.56 0.73 -11 -3 0 2.88 1.50 -11 -3 -1 -0.23 0.45 -11 -3 -2 0.67 0.70 -11 -3 -3 0.85 0.73 -11 -3 -4 -0.76 0.62 -11 -2 15 0.05 0.63 -11 -2 14 1.35 0.99 -11 -2 13 10.83 2.84 -11 -2 12 0.38 0.63 -11 -2 11 1.03 1.02 -11 -2 10 1.01 1.05 -11 -2 9 -0.92 1.01 -11 -2 8 2.87 1.71 -11 -2 7 6.83 2.79 -11 -2 6 0.74 1.03 -11 -2 5 3.61 1.92 -11 -2 4 6.13 2.48 -11 -2 3 5.28 2.30 -11 -2 2 4.31 2.28 -11 -1 16 1.24 0.86 -11 -1 15 1.51 1.01 -11 -1 14 -0.30 0.61 -11 -1 13 0.36 0.63 -11 -1 12 0.93 1.01 -11 -1 11 2.51 1.73 -11 -1 10 -0.55 0.82 -11 -1 9 0.33 0.97 -11 -1 8 1.52 1.31 -11 -1 7 1.27 1.22 -11 -1 6 1.17 1.20 -11 -1 5 2.79 2.00 -11 -1 4 3.78 2.21 -11 -1 3 1.78 1.58 -11 0 16 -1.80 0.94 -11 0 15 2.95 1.36 -11 0 14 3.06 1.65 -11 0 13 -0.35 0.63 -11 0 12 2.29 1.44 -11 0 11 1.59 1.24 -11 0 10 4.74 2.12 -11 0 9 2.45 1.56 -11 0 8 1.28 1.20 -11 0 7 -0.66 0.88 -11 0 6 -0.28 0.61 -11 0 5 1.09 1.13 -11 0 4 3.12 1.84 -11 0 3 -1.10 1.40 -11 0 3 0.56 0.87 -11 0 2 1.46 1.50 -11 0 1 -0.24 0.80 -11 0 0 4.40 2.46 -11 0 -1 4.11 2.61 -11 0 -2 1.26 1.35 -11 0 -3 2.16 1.86 -11 0 -4 7.31 3.03 -11 0 -5 0.71 0.93 -11 0 -6 2.23 1.46 -11 0 -7 2.10 1.25 -11 1 3 1.98 2.12 -11 1 2 -0.55 1.12 -11 1 1 5.73 2.87 -11 1 0 1.16 1.41 -11 1 -1 4.57 2.57 -11 1 -2 2.39 1.87 -11 1 -3 0.93 1.23 -11 1 -4 1.18 1.20 -11 1 -5 1.70 1.40 -11 1 -6 -0.42 0.70 -11 1 -7 0.56 0.73 -11 2 3 1.20 1.47 11 2 -3 1.37 1.42 -11 2 2 2.70 1.99 11 2 -2 2.24 1.37 -11 2 1 4.15 2.40 11 2 -1 1.52 1.11 -11 2 0 1.37 1.43 11 2 0 0.00 0.37 -11 2 -1 -0.29 0.76 -11 2 -2 0.36 1.22 -11 2 -3 2.49 2.20 -11 2 -4 1.38 1.23 -11 2 -5 3.55 1.92 -11 2 -6 0.78 0.84 -11 2 -7 -0.36 0.57 -11 3 12 -0.01 0.66 11 3 -8 -0.10 0.44 11 3 -7 -1.07 0.88 11 3 -6 1.09 0.93 11 3 -5 0.28 0.53 11 3 -4 -0.13 0.43 11 3 -3 0.98 0.89 11 3 -2 0.69 0.75 11 3 -1 -1.22 0.96 -11 3 0 0.55 0.89 11 3 0 1.25 0.97 -11 3 -1 0.42 0.97 11 3 1 -0.49 0.66 -11 3 -2 0.12 0.57 11 3 2 0.13 0.35 -11 3 -3 1.80 1.25 11 3 3 0.15 0.36 -11 3 -4 -1.12 0.91 11 3 4 -0.13 0.38 11 3 5 0.30 0.43 -11 4 10 -0.46 0.53 -11 4 9 0.02 0.24 11 4 -9 1.45 0.81 11 4 -8 0.92 0.71 11 4 -7 0.63 0.64 11 4 -6 0.22 0.44 11 4 -5 0.07 0.35 11 4 -4 0.93 0.77 11 4 -3 0.52 0.58 11 4 -2 0.03 0.27 11 4 -1 1.01 0.76 11 4 0 2.15 1.05 11 4 1 0.19 0.62 11 4 2 0.97 0.67 -12 -3 11 0.52 0.54 -12 -3 10 0.72 0.69 -12 -3 9 1.62 0.98 -12 -3 8 0.85 0.78 -12 -3 7 -0.07 0.31 -12 -3 6 -1.09 0.88 -12 -3 5 2.53 1.23 -12 -3 4 0.16 0.39 -12 -3 3 0.89 0.78 -12 -3 2 -1.38 0.92 -12 -3 1 3.00 1.32 -12 -3 0 1.45 0.87 -12 -3 -1 1.19 0.75 -12 -2 14 0.97 0.69 -12 -2 13 -0.44 0.58 -12 -2 12 0.75 0.74 -12 -2 11 1.11 0.92 -12 -2 10 -0.57 0.72 -12 -2 9 3.09 1.57 -12 -2 8 1.56 1.14 -12 -2 7 0.03 0.33 -12 -2 6 1.49 1.18 -12 -2 5 -0.12 0.51 -12 -2 4 3.67 1.77 -12 -2 3 0.62 0.79 -12 -2 2 1.20 1.04 -12 -2 1 0.84 0.84 -12 -2 0 0.16 0.44 -12 -2 -1 3.07 1.56 -12 -2 -2 3.64 1.53 -12 -2 -3 2.60 1.22 -12 -2 -4 -0.11 0.31 -12 -1 15 0.42 0.52 -12 -1 14 2.38 1.34 -12 -1 13 2.93 1.42 -12 -1 12 1.87 1.21 -12 -1 11 -0.22 0.54 -12 -1 10 -1.62 1.18 -12 -1 9 0.62 0.83 -12 -1 8 1.75 1.30 -12 -1 7 1.41 1.18 -12 -1 6 2.45 1.71 -12 -1 5 -0.93 1.02 -12 -1 4 0.03 0.44 -12 -1 3 6.25 2.38 -12 -1 2 1.95 1.37 -12 -1 1 0.36 0.65 -12 0 14 -0.21 0.45 -12 0 13 -0.50 0.61 -12 0 12 0.12 0.43 -12 0 11 -1.03 0.92 -12 0 10 0.50 0.69 -12 0 9 -0.04 0.38 -12 0 8 2.37 1.48 -12 0 7 1.33 1.12 -12 0 6 2.62 1.56 -12 0 5 -1.26 1.10 -12 0 4 -0.60 0.81 -12 0 3 2.29 1.49 -12 0 2 -0.21 0.98 -12 0 1 0.57 0.82 -12 0 0 -0.28 0.69 -12 0 -1 0.13 0.64 -12 0 -2 -0.54 0.83 -12 0 -3 0.13 0.59 -12 0 -4 3.23 1.60 -12 0 -5 4.41 1.61 -12 1 1 1.25 1.33 -12 1 0 5.37 2.73 -12 1 -1 1.64 1.41 -12 1 -2 1.69 1.37 -12 1 -3 -0.19 0.63 -12 1 -4 1.61 1.61 -12 1 -5 1.41 1.01 12 2 -1 -0.85 0.76 -12 2 0 -0.86 1.06 12 2 0 1.46 0.96 -12 2 -1 4.48 2.25 12 2 1 2.86 1.28 -12 2 -2 0.39 0.72 12 2 2 0.31 0.46 -12 2 -3 2.05 1.54 12 2 3 0.86 0.67 -12 2 -4 0.35 0.61 12 3 -5 1.40 0.89 12 3 -4 1.84 1.00 12 3 -3 1.21 0.82 12 3 -2 -0.93 0.72 12 3 -1 0.52 0.57 12 3 0 0.47 0.52 12 3 1 0.16 0.35 12 3 2 0.54 0.49 -13 -2 11 0.52 0.57 -13 -2 10 0.22 0.40 -13 -2 9 0.60 0.63 -13 -2 8 1.35 0.94 -13 -2 7 0.47 0.60 -13 -2 6 1.14 0.86 -13 -2 5 0.23 0.47 -13 -2 4 1.01 0.82 -13 -2 3 0.78 0.71 -13 -2 2 2.95 1.30 -13 -2 1 1.50 0.92 -13 -2 0 0.26 0.44 -13 -2 -1 2.56 1.04 -13 -1 12 0.55 0.58 -13 -1 11 -0.44 0.57 -13 -1 10 0.03 0.31 -13 -1 9 -0.09 0.38 -13 -1 8 0.40 0.62 -13 -1 7 1.63 1.22 -13 -1 6 1.38 1.03 -13 -1 5 0.75 0.81 -13 -1 4 -0.29 0.54 -13 -1 3 1.46 1.03 -13 -1 2 4.62 1.79 -13 -1 1 0.33 0.54 -13 -1 0 0.58 0.70 -13 -1 -1 0.30 0.40 -13 -1 -2 1.49 0.88 -13 0 11 0.63 0.63 -13 0 10 0.37 0.55 -13 0 9 1.88 1.09 -13 0 8 1.57 1.04 -13 0 7 3.75 1.59 -13 0 6 0.86 1.06 -13 0 5 0.38 0.62 -13 0 4 -0.21 0.50 -13 0 3 0.12 0.42 -13 0 2 0.59 0.71 -13 0 1 8.29 2.27 -13 0 0 -0.19 0.45 -13 0 -1 0.16 0.39 -13 0 -2 -0.26 0.40 -14 -1 7 2.91 1.15 -14 -1 6 1.80 0.91 -14 -1 5 0.91 0.66 -14 -1 4 2.81 1.11 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 28014 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8664(4) 1.0445(7) 0.3563(3) 0.0816(15) Uani 1 1 d . . . . . O2 O 0.9343(3) 0.4892(7) 0.3256(3) 0.0716(13) Uani 1 1 d . . . . . H2 H 0.910394 0.363539 0.330455 0.107 Uiso 1 1 calc R U . . . C1 C 0.8312(6) 0.8933(10) 0.3916(4) 0.065(2) Uani 1 1 d . . . . . C2 C 0.8716(6) 0.8306(11) 0.4779(4) 0.070(2) Uani 1 1 d . . . . . H2A H 0.932471 0.902691 0.517289 0.084 Uiso 1 1 calc R U . . . C3 C 0.8111(5) 0.6570(10) 0.4942(4) 0.0522(16) Uani 1 1 d . . . . . C4 C 0.7157(4) 0.5776(9) 0.4178(3) 0.0466(15) Uani 1 1 d . . . . . H4 H 0.737045 0.429033 0.403279 0.056 Uiso 1 1 calc R U . . . C5 C 0.7285(5) 0.7422(8) 0.3499(3) 0.0461(15) Uani 1 1 d . . . . . H5 H 0.655825 0.834234 0.337378 0.055 Uiso 1 1 calc DR U . . . C6 C 0.7285(5) 0.6301(10) 0.2691(3) 0.0489(15) Uani 1 1 d . . . . . C7 C 0.6331(5) 0.5554(10) 0.2126(3) 0.0553(16) Uani 1 1 d . . . . . H7 H 0.651963 0.481141 0.169197 0.066 Uiso 1 1 calc R U . . . C8 C 0.4999(4) 0.5659(9) 0.2041(3) 0.0512(16) Uani 1 1 d . . . . . H8A H 0.467723 0.419657 0.187489 0.061 Uiso 1 1 calc R U . . . H8B H 0.465142 0.664003 0.157919 0.061 Uiso 1 1 calc R U . . . C9 C 0.4499(4) 0.6389(9) 0.2765(3) 0.0429(14) Uani 1 1 d . . . . . H9 H 0.484186 0.784944 0.294093 0.051 Uiso 1 1 calc DR U . . . C10 C 0.4877(5) 0.4835(9) 0.3554(3) 0.0453(14) Uani 1 1 d . . . . . C11 C 0.5883(4) 0.5723(9) 0.4286(3) 0.0463(14) Uani 1 1 d . . . . . H11A H 0.567065 0.721634 0.440358 0.056 Uiso 1 1 calc R U . . . H11B H 0.590088 0.482982 0.476981 0.056 Uiso 1 1 calc R U . . . C12 C 0.3700(4) 0.4700(11) 0.3821(3) 0.0571(17) Uani 1 1 d . . . . . H12A H 0.366812 0.333582 0.411908 0.069 Uiso 1 1 calc R U . . . H12B H 0.363791 0.593845 0.417496 0.069 Uiso 1 1 calc R U . . . C13 C 0.2694(5) 0.4772(11) 0.3017(3) 0.0619(18) Uani 1 1 d . . . . . H13A H 0.263478 0.338728 0.271566 0.074 Uiso 1 1 calc R U . . . H13B H 0.192452 0.509906 0.311810 0.074 Uiso 1 1 calc R U . . . C14 C 0.3099(4) 0.6643(10) 0.2551(3) 0.0483(15) Uani 1 1 d . . . . . H14 H 0.296062 0.800277 0.282939 0.058 Uiso 1 1 calc R U . . . C15 C 0.2420(5) 0.6953(11) 0.1637(3) 0.0539(16) Uani 1 1 d . . . . . H15 H 0.270737 0.584916 0.130820 0.065 Uiso 1 1 calc R U . . . C16 C 0.2655(6) 0.9283(10) 0.1335(3) 0.070(2) Uani 1 1 d . . . . . H16A H 0.225304 1.035672 0.159745 0.084 Uiso 1 1 calc R U . . . H16B H 0.351230 0.957717 0.152704 0.084 Uiso 1 1 calc R U . . . C17 C 0.2241(6) 0.9666(12) 0.0390(3) 0.084(2) Uani 1 1 d . . . . . H17A H 0.139770 0.927459 0.017802 0.100 Uiso 1 1 calc R U . . . H17B H 0.232936 1.121653 0.027069 0.100 Uiso 1 1 calc R U . . . C18 C 0.2978(6) 0.8292(11) -0.0027(4) 0.073(2) Uani 1 1 d . . . . . H18 H 0.379637 0.861322 0.011230 0.087 Uiso 1 1 calc R U . . . C19 C 0.2616(8) 0.6681(13) -0.0568(4) 0.082(2) Uani 1 1 d . . . . . C20 C 0.3513(7) 0.5434(13) -0.0920(4) 0.138(4) Uani 1 1 d . . . . . H20A H 0.431646 0.589082 -0.063576 0.206 Uiso 1 1 calc R U . . . H20B H 0.335495 0.575172 -0.150105 0.206 Uiso 1 1 calc R U . . . H20C H 0.343125 0.387416 -0.084329 0.206 Uiso 1 1 calc R U . . . C21 C 0.1331(7) 0.5924(14) -0.0890(4) 0.143(4) Uani 1 1 d . . . . . H21A H 0.085850 0.655049 -0.055596 0.214 Uiso 1 1 calc R U . . . H21B H 0.129950 0.434029 -0.086477 0.214 Uiso 1 1 calc R U . . . H21C H 0.101491 0.639951 -0.145490 0.214 Uiso 1 1 calc R U . . . C22 C 0.8333(5) 0.5343(11) 0.5742(3) 0.074(2) Uani 1 1 d . . . . . H22A H 0.897786 0.603646 0.615208 0.110 Uiso 1 1 calc R U . . . H22B H 0.854678 0.384095 0.566312 0.110 Uiso 1 1 calc R U . . . H22C H 0.761538 0.536175 0.592676 0.110 Uiso 1 1 calc R U . . . C23 C 0.8527(5) 0.5960(11) 0.2566(3) 0.069(2) Uani 1 1 d . . . . . H23A H 0.845177 0.507481 0.207127 0.083 Uiso 1 1 calc R U . . . H23B H 0.885679 0.738510 0.247661 0.083 Uiso 1 1 calc R U . . . C24 C 0.5194(5) 0.2451(9) 0.3351(3) 0.0655(19) Uani 1 1 d . . . . . H24A H 0.537577 0.157241 0.384726 0.098 Uiso 1 1 calc R U . . . H24B H 0.588180 0.248570 0.313380 0.098 Uiso 1 1 calc R U . . . H24C H 0.452165 0.181643 0.294579 0.098 Uiso 1 1 calc R U . . . C25 C 0.1074(5) 0.6599(13) 0.1517(3) 0.097(3) Uani 1 1 d . . . . . H25A H 0.064509 0.691896 0.095206 0.146 Uiso 1 1 calc R U . . . H25B H 0.079898 0.756521 0.188172 0.146 Uiso 1 1 calc R U . . . H25C H 0.093200 0.509077 0.164201 0.146 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 0.064(3) 0.053(3) 0.122(4) 0.022(3) 0.017(3) -0.014(3) O2 0.055(3) 0.073(3) 0.088(3) 0.014(3) 0.021(2) 0.003(3) C1 0.051(5) 0.049(4) 0.094(6) 0.000(4) 0.016(4) -0.001(3) C2 0.071(5) 0.071(5) 0.063(5) -0.014(4) 0.010(4) -0.003(4) C3 0.045(4) 0.063(4) 0.046(4) -0.006(3) 0.009(3) 0.003(4) C4 0.049(4) 0.044(4) 0.048(4) -0.006(3) 0.014(3) -0.006(3) C5 0.047(4) 0.037(3) 0.058(4) 0.002(3) 0.020(3) -0.003(3) C6 0.045(4) 0.052(4) 0.054(4) 0.008(3) 0.019(3) 0.004(3) C7 0.062(4) 0.058(4) 0.052(4) 0.000(3) 0.027(3) 0.013(4) C8 0.058(4) 0.053(4) 0.044(3) -0.001(3) 0.016(3) 0.007(3) C9 0.054(4) 0.035(3) 0.041(3) 0.003(3) 0.016(3) 0.005(3) C10 0.043(3) 0.042(3) 0.050(4) -0.001(3) 0.011(3) -0.003(3) C11 0.048(3) 0.047(3) 0.046(3) 0.003(3) 0.017(3) -0.003(3) C12 0.055(4) 0.070(4) 0.050(4) 0.005(4) 0.020(3) -0.014(4) C13 0.053(4) 0.079(5) 0.050(4) 0.007(4) 0.008(3) -0.010(4) C14 0.043(4) 0.052(4) 0.050(4) -0.002(3) 0.012(3) 0.005(3) C15 0.038(3) 0.070(5) 0.051(4) 0.000(3) 0.006(3) 0.003(3) C16 0.091(6) 0.061(5) 0.055(4) -0.003(3) 0.014(4) 0.017(4) C17 0.110(6) 0.080(5) 0.056(4) 0.015(4) 0.015(4) 0.018(5) C18 0.071(5) 0.087(6) 0.058(5) 0.014(4) 0.014(4) 0.002(5) C19 0.103(7) 0.074(5) 0.067(5) 0.009(4) 0.020(5) -0.003(6) C20 0.220(11) 0.101(7) 0.103(7) -0.005(6) 0.062(7) 0.024(8) C21 0.163(9) 0.135(9) 0.102(7) -0.005(6) -0.011(6) -0.059(8) C22 0.063(4) 0.103(6) 0.050(4) 0.002(4) 0.008(3) 0.002(5) C23 0.057(4) 0.083(5) 0.072(5) 0.022(4) 0.027(4) 0.012(4) C24 0.083(5) 0.041(4) 0.068(4) -0.002(3) 0.013(4) -0.004(4) C25 0.053(4) 0.152(8) 0.081(5) 0.014(6) 0.009(4) -0.012(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 C23 O2 H2 109.5 . . ? O1 C1 C2 128.7(7) . . ? O1 C1 C5 123.7(7) . . ? C2 C1 C5 107.6(6) . . ? C3 C2 C1 111.7(6) . . ? C3 C2 H2A 124.2 . . ? C1 C2 H2A 124.2 . . ? C2 C3 C22 127.4(6) . . ? C2 C3 C4 112.2(6) . . ? C22 C3 C4 120.4(5) . . ? C3 C4 C11 114.0(4) . . ? C3 C4 C5 102.8(4) . . ? C11 C4 C5 112.8(4) . . ? C3 C4 H4 109.0 . . ? C11 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? C1 C5 C6 119.5(5) . . ? C1 C5 C4 105.7(5) . . ? C6 C5 C4 113.1(4) . . ? C1 C5 H5 105.9 . . ? C6 C5 H5 105.9 . . ? C4 C5 H5 105.9 . . ? C7 C6 C5 126.1(5) . . ? C7 C6 C23 119.3(5) . . ? C5 C6 C23 114.6(5) . . ? C6 C7 C8 133.1(5) . . ? C6 C7 H7 113.4 . . ? C8 C7 H7 113.4 . . ? C7 C8 C9 122.0(4) . . ? C7 C8 H8A 106.8 . . ? C9 C8 H8A 106.8 . . ? C7 C8 H8B 106.8 . . ? C9 C8 H8B 106.8 . . ? H8A C8 H8B 106.7 . . ? C8 C9 C14 115.7(4) . . ? C8 C9 C10 114.2(4) . . ? C14 C9 C10 106.3(4) . . ? C8 C9 H9 106.7 . . ? C14 C9 H9 106.7 . . ? C10 C9 H9 106.7 . . ? C11 C10 C12 108.7(4) . . ? C11 C10 C24 109.2(5) . . ? C12 C10 C24 107.1(5) . . ? C11 C10 C9 115.7(5) . . ? C12 C10 C9 102.1(4) . . ? C24 C10 C9 113.3(5) . . ? C4 C11 C10 117.1(4) . . ? C4 C11 H11A 108.0 . . ? C10 C11 H11A 108.0 . . ? C4 C11 H11B 108.0 . . ? C10 C11 H11B 108.0 . . ? H11A C11 H11B 107.3 . . ? C13 C12 C10 105.1(4) . . ? C13 C12 H12A 110.7 . . ? C10 C12 H12A 110.7 . . ? C13 C12 H12B 110.7 . . ? C10 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 102.1(5) . . ? C14 C13 H13A 111.4 . . ? C12 C13 H13A 111.4 . . ? C14 C13 H13B 111.4 . . ? C12 C13 H13B 111.4 . . ? H13A C13 H13B 109.2 . . ? C13 C14 C15 117.4(5) . . ? C13 C14 C9 104.7(4) . . ? C15 C14 C9 117.1(4) . . ? C13 C14 H14 105.5 . . ? C15 C14 H14 105.5 . . ? C9 C14 H14 105.5 . . ? C25 C15 C14 109.8(4) . . ? C25 C15 C16 110.4(6) . . ? C14 C15 C16 110.6(5) . . ? C25 C15 H15 108.7 . . ? C14 C15 H15 108.7 . . ? C16 C15 H15 108.7 . . ? C17 C16 C15 116.1(5) . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16B 108.3 . . ? C15 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C18 C17 C16 110.0(5) . . ? C18 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C19 C18 C17 128.3(8) . . ? C19 C18 H18 115.8 . . ? C17 C18 H18 115.8 . . ? C18 C19 C21 124.5(8) . . ? C18 C19 C20 120.7(8) . . ? C21 C19 C20 114.8(8) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C3 C22 H22A 109.5 . . ? C3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C23 C6 112.8(4) . . ? O2 C23 H23A 109.0 . . ? C6 C23 H23A 109.0 . . ? O2 C23 H23B 109.0 . . ? C6 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C10 C24 H24A 109.5 . . ? C10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C15 C25 H25A 109.5 . . ? C15 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C15 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 C1 1.218(7) . ? O2 C23 1.430(6) . ? O2 H2 0.8200 . ? C1 C2 1.443(8) . ? C1 C5 1.508(7) . ? C2 C3 1.330(8) . ? C2 H2A 0.9300 . ? C3 C22 1.492(7) . ? C3 C4 1.519(7) . ? C4 C11 1.530(6) . ? C4 C5 1.549(6) . ? C4 H4 0.9800 . ? C5 C6 1.514(6) . ? C5 H5 0.9800 . ? C6 C7 1.319(7) . ? C6 C23 1.519(6) . ? C7 C8 1.507(6) . ? C7 H7 0.9300 . ? C8 C9 1.543(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.564(6) . ? C9 C10 1.583(6) . ? C9 H9 0.9800 . ? C10 C11 1.536(6) . ? C10 C12 1.545(6) . ? C10 C24 1.548(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.519(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.519(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.528(6) . ? C14 H14 0.9800 . ? C15 C25 1.526(6) . ? C15 C16 1.546(7) . ? C15 H15 0.9800 . ? C16 C17 1.541(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.493(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.317(8) . ? C18 H18 0.9300 . ? C19 C21 1.504(9) . ? C19 C20 1.523(9) . ? 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 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? 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 O1 C1 C2 C3 179.4(6) . . . . ? C5 C1 C2 C3 2.4(8) . . . . ? C1 C2 C3 C22 175.0(5) . . . . ? C1 C2 C3 C4 -1.1(8) . . . . ? C2 C3 C4 C11 -123.2(6) . . . . ? C22 C3 C4 C11 60.5(7) . . . . ? C2 C3 C4 C5 -0.7(7) . . . . ? C22 C3 C4 C5 -177.0(5) . . . . ? O1 C1 C5 C6 51.3(9) . . . . ? C2 C1 C5 C6 -131.5(5) . . . . ? O1 C1 C5 C4 -179.9(6) . . . . ? C2 C1 C5 C4 -2.7(6) . . . . ? C3 C4 C5 C1 2.1(6) . . . . ? C11 C4 C5 C1 125.3(5) . . . . ? C3 C4 C5 C6 134.5(5) . . . . ? C11 C4 C5 C6 -102.2(5) . . . . ? C1 C5 C6 C7 -156.6(6) . . . . ? C4 C5 C6 C7 78.1(7) . . . . ? C1 C5 C6 C23 26.1(8) . . . . ? C4 C5 C6 C23 -99.2(6) . . . . ? C5 C6 C7 C8 4.8(11) . . . . ? C23 C6 C7 C8 -178.0(6) . . . . ? C6 C7 C8 C9 -12.5(10) . . . . ? C7 C8 C9 C14 174.0(5) . . . . ? C7 C8 C9 C10 -62.1(7) . . . . ? C8 C9 C10 C11 103.0(5) . . . . ? C14 C9 C10 C11 -128.2(5) . . . . ? C8 C9 C10 C12 -139.1(5) . . . . ? C14 C9 C10 C12 -10.3(5) . . . . ? C8 C9 C10 C24 -24.2(7) . . . . ? C14 C9 C10 C24 104.6(5) . . . . ? C3 C4 C11 C10 -177.2(5) . . . . ? C5 C4 C11 C10 66.0(6) . . . . ? C12 C10 C11 C4 174.3(5) . . . . ? C24 C10 C11 C4 57.7(6) . . . . ? C9 C10 C11 C4 -71.5(6) . . . . ? C11 C10 C12 C13 156.9(5) . . . . ? C24 C10 C12 C13 -85.3(6) . . . . ? C9 C10 C12 C13 34.1(6) . . . . ? C10 C12 C13 C14 -45.5(6) . . . . ? C12 C13 C14 C15 169.4(5) . . . . ? C12 C13 C14 C9 37.7(6) . . . . ? C8 C9 C14 C13 111.2(5) . . . . ? C10 C9 C14 C13 -16.8(6) . . . . ? C8 C9 C14 C15 -20.8(8) . . . . ? C10 C9 C14 C15 -148.7(5) . . . . ? C13 C14 C15 C25 40.1(8) . . . . ? C9 C14 C15 C25 166.0(5) . . . . ? C13 C14 C15 C16 162.2(5) . . . . ? C9 C14 C15 C16 -71.9(7) . . . . ? C25 C15 C16 C17 -70.2(7) . . . . ? C14 C15 C16 C17 168.0(5) . . . . ? C15 C16 C17 C18 -66.9(7) . . . . ? C16 C17 C18 C19 116.9(8) . . . . ? C17 C18 C19 C21 1.2(12) . . . . ? C17 C18 C19 C20 -179.1(6) . . . . ? C7 C6 C23 O2 -125.9(6) . . . . ? C5 C6 C23 O2 51.6(8) . . . . ?