#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/65/1516595.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_1516595 loop_ _publ_author_name 'Yurchenko, Anton N.' 'Smetanina, Olga F.' 'Kalinovsky, Anatoly I.' 'Pushilin, Michael A.' 'Glazunov, Valeriy P.' 'Khudyakova, Yuliya V.' 'Kirichuk, Natalya N.' 'Ermakova, Svetlana P.' 'Dyshlovoy, Sergey A.' 'Yurchenko, Ekaterina A.' 'Afiyatullov, Shamil Sh' _publ_section_title ; Oxirapentyns F-K from the Marine-Sediment-Derived Fungus Isaria felina KMM 4639. ; _journal_issue 6 _journal_name_full 'Journal of natural products' _journal_page_first 1321 _journal_page_last 1328 _journal_paper_doi 10.1021/np500014m _journal_volume 77 _journal_year 2014 _chemical_absolute_configuration unk _chemical_formula_moiety 'C18 H26 O8' _chemical_formula_sum 'C18 H26 O8' _chemical_formula_weight 370.39 _chemical_name_systematic ;1-((3S,4aR,5S,6S,7R,8S)-4a,5,6,7,8-pentahydroxy-2,2-dimethyl-7- (3-methylbut-3-en-1-yn-1-yl)octahydro-2H-chromen-3-yl)ethanone ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.5390(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.9116(2) _cell_length_b 7.09400(10) _cell_length_c 26.0972(5) _cell_measurement_reflns_used 9954 _cell_measurement_temperature 140(2) _cell_measurement_theta_max 32.10 _cell_measurement_theta_min 2.49 _cell_volume 1829.21(6) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 140(2) _diffrn_detector_area_resol_mean 83.33 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 41996 _diffrn_reflns_theta_full 32.14 _diffrn_reflns_theta_max 32.14 _diffrn_reflns_theta_min 2.06 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_correction_T_min 0.9625 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'sadabs-2012/1 (Sheldrick, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.436 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 6809 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0317 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.2369P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.0906 _reflns_number_gt 6029 _reflns_number_total 6809 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL tb2013_02_0m in P2(1) CELL 0.71073 9.9116 7.0940 26.0972 90.000 94.539 90.000 ZERR 4.00 0.0002 0.0001 0.0005 0.000 0.001 0.000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H O UNIT 72 104 32 MERG 3 L.S. 4 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.182 0.292 0.364 TEMP -133.000 WGHT 0.0543 0.2369 FVAR 0.22857 O1 3 0.128139 0.719161 0.397965 11.00000 0.01549 0.01450 = 0.01105 0.00109 -0.00380 0.00232 O2 3 -0.140472 0.549433 0.362905 11.00000 0.01623 0.02414 = 0.01887 -0.00444 -0.00741 0.00388 O3 3 -0.239284 0.588267 0.282995 11.00000 0.03798 0.05179 = 0.02761 -0.00534 -0.02007 0.00934 O4 3 -0.006994 0.457764 0.459888 11.00000 0.01054 0.01942 = 0.01566 -0.00028 0.00203 0.00138 AFIX 147 H4 2 -0.045882 0.553501 0.446803 11.00000 -1.50000 AFIX 0 O5 3 0.272674 0.153687 0.431252 11.00000 0.01488 0.01559 = 0.01694 -0.00203 0.00139 0.00353 AFIX 147 H5 2 0.347226 0.209161 0.436951 11.00000 -1.50000 AFIX 0 O6 3 0.136501 0.339880 0.547437 11.00000 0.01646 0.02504 = 0.01277 0.00245 0.00378 -0.00108 AFIX 147 H6 2 0.067417 0.387370 0.531749 11.00000 -1.50000 AFIX 0 O7 3 0.436716 0.429024 0.476436 11.00000 0.00924 0.02133 = 0.01433 0.00269 -0.00025 0.00337 AFIX 147 H7 2 0.501116 0.385099 0.495663 11.00000 -1.50000 AFIX 0 O8 3 0.343043 0.795438 0.470351 11.00000 0.01769 0.01540 = 0.02444 0.00656 -0.01013 -0.00468 AFIX 147 H8 2 0.305115 0.876558 0.450675 11.00000 -1.50000 AFIX 0 O9 3 0.873083 1.091191 0.101828 11.00000 0.01186 0.00554 = 0.01268 -0.00021 -0.00373 -0.00070 O10 3 1.141013 0.920805 0.137073 11.00000 0.01153 0.01503 = 0.01719 0.00347 -0.00383 -0.00223 O11 3 1.242695 0.958516 0.216642 11.00000 0.02652 0.03673 = 0.02326 0.00218 -0.01144 -0.00780 O12 3 1.007448 0.827452 0.040455 11.00000 0.00838 0.01002 = 0.01671 0.00036 0.00242 -0.00129 AFIX 147 H12 2 1.045506 0.924708 0.052978 11.00000 -1.50000 AFIX 0 O13 3 0.727868 0.524164 0.069505 11.00000 0.01221 0.00694 = 0.01844 0.00243 0.00162 -0.00255 AFIX 147 H13 2 0.653651 0.580812 0.064214 11.00000 -1.50000 AFIX 0 O14 3 0.864274 0.708298 -0.046827 11.00000 0.01374 0.01584 = 0.01529 -0.00183 0.00412 0.00136 AFIX 147 H14 2 0.929059 0.769208 -0.032221 11.00000 -1.50000 AFIX 0 O15 3 0.563671 0.798745 0.023991 11.00000 0.00669 0.01294 = 0.01560 -0.00208 0.00023 -0.00348 AFIX 147 H15 2 0.501069 0.749314 0.004972 11.00000 -1.50000 AFIX 0 O16 3 0.657330 1.165826 0.029360 11.00000 0.01418 0.00586 = 0.02466 -0.00480 -0.00886 0.00522 AFIX 147 H16 2 0.697282 1.251583 0.046803 11.00000 -1.50000 AFIX 0 C1 1 0.083019 0.676232 0.345108 11.00000 0.02084 0.02004 = 0.00973 0.00065 -0.00277 0.00282 C2 1 -0.011317 0.503633 0.343196 11.00000 0.02041 0.01955 = 0.01187 -0.00351 -0.00454 0.00439 AFIX 13 H2 2 -0.027518 0.460572 0.306742 11.00000 -1.20000 AFIX 0 C3 1 0.046521 0.340187 0.375904 11.00000 0.01852 0.01634 = 0.01258 -0.00340 -0.00441 0.00071 AFIX 23 H3A 2 0.120293 0.280026 0.358335 11.00000 -1.20000 H3B 2 -0.025185 0.244763 0.379154 11.00000 -1.20000 AFIX 0 C4 1 0.101470 0.403035 0.429541 11.00000 0.01001 0.01401 = 0.01111 -0.00104 -0.00018 0.00077 C5 1 0.173780 0.242015 0.459888 11.00000 0.01198 0.01332 = 0.01286 0.00071 0.00040 0.00019 AFIX 13 H5A 2 0.104105 0.144928 0.466507 11.00000 -1.20000 AFIX 0 C6 1 0.237173 0.310340 0.512487 11.00000 0.01330 0.01543 = 0.01075 0.00182 0.00045 -0.00002 AFIX 13 H6A 2 0.296598 0.206174 0.526936 11.00000 -1.20000 AFIX 0 C7 1 0.329893 0.485130 0.506820 11.00000 0.01088 0.01537 = 0.01104 0.00068 -0.00110 -0.00010 C8 1 0.252415 0.644078 0.476714 11.00000 0.01064 0.01284 = 0.01269 0.00051 -0.00278 -0.00012 AFIX 13 H8A 2 0.175560 0.688243 0.496256 11.00000 -1.20000 AFIX 0 C9 1 0.198184 0.568464 0.424499 11.00000 0.01047 0.01323 = 0.01121 0.00033 -0.00144 0.00008 AFIX 13 H9 2 0.275539 0.527409 0.404778 11.00000 -1.20000 AFIX 0 C10 1 0.202487 0.637634 0.312920 11.00000 0.03204 0.03136 = 0.01620 0.00523 0.00769 0.00584 AFIX 137 H10A 2 0.272115 0.734197 0.320134 11.00000 -1.50000 H10B 2 0.171388 0.640839 0.276338 11.00000 -1.50000 H10C 2 0.240492 0.513138 0.321669 11.00000 -1.50000 AFIX 0 C11 1 0.009886 0.854730 0.326181 11.00000 0.03152 0.02066 = 0.01840 0.00262 -0.00857 0.00501 AFIX 137 H11A 2 -0.058580 0.888138 0.349731 11.00000 -1.50000 H11B 2 -0.034123 0.833071 0.291725 11.00000 -1.50000 H11C 2 0.075268 0.957923 0.324901 11.00000 -1.50000 AFIX 0 C12 1 -0.247170 0.581748 0.328648 11.00000 0.02323 0.02406 = 0.03217 -0.00797 -0.01630 0.00577 C13 1 -0.373531 0.607678 0.355864 11.00000 0.01955 0.03594 = 0.05169 -0.01483 -0.00905 0.00671 AFIX 137 H13A 2 -0.364747 0.720706 0.377461 11.00000 -1.50000 H13B 2 -0.387266 0.497320 0.377433 11.00000 -1.50000 H13C 2 -0.451176 0.621956 0.330489 11.00000 -1.50000 AFIX 0 C14 1 0.380726 0.548399 0.558581 11.00000 0.01405 0.01755 = 0.01463 0.00181 -0.00217 -0.00040 C15 1 0.418644 0.580505 0.602614 11.00000 0.01931 0.02024 = 0.01441 0.00123 -0.00144 -0.00293 C16 1 0.455387 0.609231 0.656533 11.00000 0.02781 0.02472 = 0.01144 0.00045 -0.00072 -0.00645 C17 1 0.585737 0.621972 0.674975 11.00000 0.02775 0.06024 = 0.01302 0.00370 -0.00589 -0.01062 AFIX 93 H17A 2 0.655746 0.611995 0.652275 11.00000 -1.20000 H17B 2 0.607756 0.640944 0.710694 11.00000 -1.20000 AFIX 0 C18 1 0.341338 0.615158 0.690279 11.00000 0.03251 0.04298 = 0.02307 -0.00645 0.00943 -0.00871 AFIX 137 H18A 2 0.372843 0.669415 0.723635 11.00000 -1.50000 H18B 2 0.307923 0.486981 0.695284 11.00000 -1.50000 H18C 2 0.268110 0.692984 0.674151 11.00000 -1.50000 AFIX 0 C19 1 0.918149 1.049845 0.154774 11.00000 0.01551 0.01084 = 0.01252 -0.00134 -0.00304 -0.00025 C20 1 1.012396 0.876342 0.157088 11.00000 0.01323 0.01003 = 0.01405 0.00259 -0.00326 -0.00058 AFIX 13 H20 2 1.028807 0.834376 0.193631 11.00000 -1.20000 AFIX 0 C21 1 0.953749 0.712428 0.124746 11.00000 0.01240 0.00722 = 0.01555 0.00283 -0.00239 -0.00004 AFIX 23 H21A 2 0.879627 0.653697 0.142435 11.00000 -1.20000 H21B 2 1.024960 0.616096 0.121743 11.00000 -1.20000 AFIX 0 C22 1 0.899203 0.774061 0.070932 11.00000 0.00752 0.00502 = 0.01350 0.00091 0.00000 0.00013 C23 1 0.826555 0.612136 0.040808 11.00000 0.00968 0.00463 = 0.01430 -0.00002 0.00056 0.00014 AFIX 13 H23 2 0.896271 0.514923 0.034341 11.00000 -1.20000 AFIX 0 C24 1 0.763629 0.679159 -0.011797 11.00000 0.01076 0.00650 = 0.01353 -0.00132 0.00050 0.00072 AFIX 13 H24 2 0.704220 0.574767 -0.026118 11.00000 -1.20000 AFIX 0 C25 1 0.670613 0.854870 -0.006438 11.00000 0.00787 0.00611 = 0.01294 -0.00068 -0.00102 0.00013 C26 1 0.748079 1.014101 0.023361 11.00000 0.00821 0.00428 = 0.01394 0.00008 -0.00262 0.00109 AFIX 13 H26 2 0.824924 1.057670 0.003726 11.00000 -1.20000 AFIX 0 C27 1 0.802430 0.939781 0.075734 11.00000 0.00682 0.00464 = 0.01350 -0.00018 -0.00086 0.00007 AFIX 13 H27 2 0.725213 0.899551 0.095640 11.00000 -1.20000 AFIX 0 C28 1 0.798562 1.012648 0.186953 11.00000 0.02343 0.02437 = 0.01601 -0.00085 0.00485 0.00388 AFIX 137 H28A 2 0.728574 1.108269 0.179158 11.00000 -1.50000 H28B 2 0.829288 1.018480 0.223546 11.00000 -1.50000 H28C 2 0.761168 0.887351 0.178782 11.00000 -1.50000 AFIX 0 C29 1 0.992047 1.228298 0.173388 11.00000 0.02700 0.01153 = 0.02203 -0.00443 -0.01059 0.00069 AFIX 137 H29A 2 1.060826 1.260288 0.149834 11.00000 -1.50000 H29B 2 1.035748 1.207279 0.207924 11.00000 -1.50000 H29C 2 0.927126 1.332174 0.174385 11.00000 -1.50000 AFIX 0 C30 1 1.249403 0.951523 0.170866 11.00000 0.01558 0.01307 = 0.02616 0.00445 -0.00823 -0.00254 C31 1 1.375170 0.974159 0.143239 11.00000 0.01470 0.02545 = 0.04012 0.00888 -0.00293 -0.00539 AFIX 137 H31A 2 1.370844 1.093137 0.124097 11.00000 -1.50000 H31B 2 1.382658 0.868950 0.119294 11.00000 -1.50000 H31C 2 1.454326 0.975206 0.168245 11.00000 -1.50000 AFIX 0 C32 1 0.620110 0.916395 -0.058405 11.00000 0.01177 0.00798 = 0.01637 -0.00117 -0.00177 -0.00022 C33 1 0.582484 0.946503 -0.102470 11.00000 0.01545 0.01049 = 0.01716 -0.00120 -0.00207 0.00079 C34 1 0.546408 0.977011 -0.156343 11.00000 0.02083 0.01568 = 0.01457 0.00078 -0.00137 0.00334 C35 1 0.416634 0.991804 -0.174722 11.00000 0.02367 0.05101 = 0.01564 -0.00186 -0.00497 0.00985 AFIX 93 H35A 2 0.346516 0.982155 -0.152061 11.00000 -1.20000 H35B 2 0.394807 1.011933 -0.210405 11.00000 -1.20000 AFIX 0 C36 1 0.661236 0.982660 -0.190411 11.00000 0.02630 0.02940 = 0.02313 0.00429 0.00680 0.00249 AFIX 137 H36A 2 0.629554 1.036237 -0.223832 11.00000 -1.50000 H36B 2 0.694835 0.854478 -0.195253 11.00000 -1.50000 H36C 2 0.734380 1.060958 -0.174419 11.00000 -1.50000 HKLF 4 REM tb2013_02_0m in P2(1) REM R1 = 0.0317 for 6029 Fo > 4sig(Fo) and 0.0362 for all 6809 data REM 487 parameters refined using 1 restraints END WGHT 0.0543 0.2369 REM Highest difference peak 0.436, deepest hole -0.178, 1-sigma level 0.046 Q1 1 0.7771 0.9778 0.0493 11.00000 0.05 0.44 Q2 1 0.0755 0.3679 0.4013 11.00000 0.05 0.40 Q3 1 0.2043 0.2690 0.4873 11.00000 0.05 0.39 Q4 1 0.2262 0.6039 0.4501 11.00000 0.05 0.39 Q5 1 0.6538 0.8827 -0.0313 11.00000 0.05 0.38 Q6 1 0.5603 0.9566 -0.1307 11.00000 0.05 0.36 Q7 1 0.9280 0.7524 0.0984 11.00000 0.05 0.36 Q8 1 0.7967 0.6416 0.0143 11.00000 0.05 0.36 Q9 1 0.4400 0.5916 0.6315 11.00000 0.05 0.35 Q10 1 0.8536 0.8513 0.0741 11.00000 0.05 0.35 Q11 1 0.7191 0.7692 -0.0092 11.00000 0.05 0.35 Q12 1 0.8945 1.0724 0.1299 11.00000 0.05 0.35 Q13 1 0.0375 0.5898 0.3424 11.00000 0.05 0.34 Q14 1 0.1414 0.3174 0.4423 11.00000 0.05 0.34 Q15 1 0.1532 0.4917 0.4263 11.00000 0.05 0.33 Q16 1 0.2853 0.4042 0.5091 11.00000 0.05 0.32 Q17 1 0.3463 0.5142 0.5319 11.00000 0.05 0.32 Q18 1 0.1074 0.6920 0.3701 11.00000 0.05 0.31 Q19 1 0.8637 0.6916 0.0563 11.00000 0.05 0.30 Q20 1 0.2962 0.5613 0.4891 11.00000 0.05 0.29 ; _cod_data_source_file np500014m_si_002.cif _cod_data_source_block tb2013_02_0m _cod_depositor_comments 'Adding full bibliography for 1516595.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1516595 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.12814(9) 0.71916(13) 0.39797(3) 0.01396(16) Uani 1 1 d . O2 O -0.14047(9) 0.54944(16) 0.36291(4) 0.02023(19) Uani 1 1 d . O3 O -0.23928(13) 0.5883(2) 0.28299(5) 0.0404(3) Uani 1 1 d . O4 O -0.00700(8) 0.45777(14) 0.45989(3) 0.01517(17) Uani 1 1 d . H4 H -0.0460 0.5533 0.4468 0.023 Uiso 1 1 calc R O5 O 0.27267(9) 0.15368(13) 0.43125(3) 0.01583(17) Uani 1 1 d . H5 H 0.3472 0.2093 0.4369 0.024 Uiso 1 1 calc R O6 O 0.13650(9) 0.33986(15) 0.54744(3) 0.01797(18) Uani 1 1 d . H6 H 0.0674 0.3875 0.5318 0.027 Uiso 1 1 calc R O7 O 0.43672(8) 0.42902(14) 0.47644(3) 0.01505(17) Uani 1 1 d . H7 H 0.5011 0.3851 0.4957 0.023 Uiso 1 1 calc R O8 O 0.34304(10) 0.79544(14) 0.47035(4) 0.0198(2) Uani 1 1 d . H8 H 0.3052 0.8765 0.4506 0.030 Uiso 1 1 calc R O9 O 0.87308(8) 1.09119(11) 0.10183(3) 0.01028(15) Uani 1 1 d . O10 O 1.14101(9) 0.92081(13) 0.13707(3) 0.01485(17) Uani 1 1 d . O11 O 1.24269(11) 0.95852(19) 0.21664(4) 0.0296(2) Uani 1 1 d . O12 O 1.00745(8) 0.82746(12) 0.04045(3) 0.01162(15) Uani 1 1 d . H12 H 1.0455 0.9247 0.0530 0.017 Uiso 1 1 calc R O13 O 0.72787(9) 0.52416(12) 0.06950(3) 0.01251(16) Uani 1 1 d . H13 H 0.6537 0.5810 0.0643 0.019 Uiso 1 1 calc R O14 O 0.86428(9) 0.70829(13) -0.04683(3) 0.01480(17) Uani 1 1 d . H14 H 0.9291 0.7692 -0.0322 0.022 Uiso 1 1 calc R O15 O 0.56368(8) 0.79874(12) 0.02399(3) 0.01178(15) Uani 1 1 d . H15 H 0.5011 0.7493 0.0050 0.018 Uiso 1 1 calc R O16 O 0.65733(9) 1.16582(12) 0.02936(4) 0.01545(17) Uani 1 1 d . H16 H 0.6973 1.2517 0.0468 0.023 Uiso 1 1 calc R C1 C 0.08301(13) 0.6762(2) 0.34511(4) 0.0171(2) Uani 1 1 d . C2 C -0.01131(13) 0.50364(19) 0.34320(5) 0.0176(2) Uani 1 1 d . H2 H -0.0275 0.4606 0.3067 0.021 Uiso 1 1 calc R C3 C 0.04652(13) 0.34018(18) 0.37590(4) 0.0161(2) Uani 1 1 d . H3A H 0.1203 0.2800 0.3583 0.019 Uiso 1 1 calc R H3B H -0.0252 0.2448 0.3792 0.019 Uiso 1 1 calc R C4 C 0.10147(11) 0.40303(17) 0.42954(4) 0.01178(19) Uani 1 1 d . C5 C 0.17378(11) 0.24202(17) 0.45989(4) 0.0128(2) Uani 1 1 d . H5A H 0.1041 0.1449 0.4665 0.015 Uiso 1 1 calc R C6 C 0.23718(12) 0.31034(18) 0.51249(4) 0.0132(2) Uani 1 1 d . H6A H 0.2966 0.2062 0.5269 0.016 Uiso 1 1 calc R C7 C 0.32990(11) 0.48513(17) 0.50682(4) 0.0126(2) Uani 1 1 d . C8 C 0.25242(11) 0.64408(17) 0.47672(4) 0.0123(2) Uani 1 1 d . H8A H 0.1756 0.6882 0.4963 0.015 Uiso 1 1 calc R C9 C 0.19818(11) 0.56846(17) 0.42450(4) 0.01178(19) Uani 1 1 d . H9 H 0.2755 0.5274 0.4048 0.014 Uiso 1 1 calc R C10 C 0.20248(16) 0.6376(2) 0.31292(5) 0.0263(3) Uani 1 1 d . H10A H 0.2721 0.7341 0.3201 0.039 Uiso 1 1 calc R H10B H 0.1714 0.6409 0.2763 0.039 Uiso 1 1 calc R H10C H 0.2404 0.5131 0.3216 0.039 Uiso 1 1 calc R C11 C 0.00988(16) 0.8547(2) 0.32618(5) 0.0241(3) Uani 1 1 d . H11A H -0.0587 0.8881 0.3497 0.036 Uiso 1 1 calc R H11B H -0.0341 0.8331 0.2917 0.036 Uiso 1 1 calc R H11C H 0.0752 0.9579 0.3249 0.036 Uiso 1 1 calc R C12 C -0.24717(15) 0.5818(2) 0.32865(6) 0.0275(3) Uani 1 1 d . C13 C -0.37353(15) 0.6077(3) 0.35586(8) 0.0364(4) Uani 1 1 d . H13A H -0.3648 0.7207 0.3775 0.055 Uiso 1 1 calc R H13B H -0.3873 0.4973 0.3774 0.055 Uiso 1 1 calc R H13C H -0.4512 0.6220 0.3305 0.055 Uiso 1 1 calc R C14 C 0.38072(12) 0.54840(19) 0.55858(5) 0.0156(2) Uani 1 1 d . C15 C 0.41865(13) 0.5805(2) 0.60261(5) 0.0181(2) Uani 1 1 d . C16 C 0.45540(15) 0.6092(2) 0.65653(5) 0.0215(3) Uani 1 1 d . C17 C 0.58573(17) 0.6220(3) 0.67498(6) 0.0341(4) Uani 1 1 d . H17A H 0.6557 0.6120 0.6523 0.041 Uiso 1 1 calc R H17B H 0.6077 0.6409 0.7107 0.041 Uiso 1 1 calc R C18 C 0.34133(17) 0.6152(3) 0.69028(6) 0.0325(4) Uani 1 1 d . H18A H 0.3728 0.6694 0.7236 0.049 Uiso 1 1 calc R H18B H 0.3079 0.4870 0.6953 0.049 Uiso 1 1 calc R H18C H 0.2681 0.6930 0.6742 0.049 Uiso 1 1 calc R C19 C 0.91815(12) 1.04985(17) 0.15477(4) 0.0132(2) Uani 1 1 d . C20 C 1.01240(12) 0.87633(16) 0.15709(4) 0.0127(2) Uani 1 1 d . H20 H 1.0288 0.8344 0.1936 0.015 Uiso 1 1 calc R C21 C 0.95375(11) 0.71243(15) 0.12475(4) 0.01189(19) Uani 1 1 d . H21A H 0.8796 0.6537 0.1424 0.014 Uiso 1 1 calc R H21B H 1.0250 0.6161 0.1217 0.014 Uiso 1 1 calc R C22 C 0.89920(10) 0.77406(15) 0.07093(4) 0.00872(17) Uani 1 1 d . C23 C 0.82656(11) 0.61214(15) 0.04081(4) 0.00956(18) Uani 1 1 d . H23 H 0.8963 0.5149 0.0343 0.011 Uiso 1 1 calc R C24 C 0.76363(11) 0.67916(15) -0.01180(4) 0.01028(18) Uani 1 1 d . H24 H 0.7042 0.5748 -0.0261 0.012 Uiso 1 1 calc R C25 C 0.67062(10) 0.85488(15) -0.00643(4) 0.00906(18) Uani 1 1 d . C26 C 0.74808(11) 1.01410(14) 0.02336(4) 0.00900(18) Uani 1 1 d . H26 H 0.8249 1.0577 0.0037 0.011 Uiso 1 1 calc R C27 C 0.80243(10) 0.93978(14) 0.07573(4) 0.00841(17) Uani 1 1 d . H27 H 0.7252 0.8996 0.0956 0.010 Uiso 1 1 calc R C28 C 0.79856(14) 1.0126(2) 0.18695(5) 0.0211(2) Uani 1 1 d . H28A H 0.7286 1.1084 0.1792 0.032 Uiso 1 1 calc R H28B H 0.8293 1.0183 0.2235 0.032 Uiso 1 1 calc R H28C H 0.7611 0.8874 0.1787 0.032 Uiso 1 1 calc R C29 C 0.99205(15) 1.22830(19) 0.17338(5) 0.0208(3) Uani 1 1 d . H29A H 1.0608 1.2603 0.1498 0.031 Uiso 1 1 calc R H29B H 1.0358 1.2073 0.2079 0.031 Uiso 1 1 calc R H29C H 0.9271 1.3322 0.1744 0.031 Uiso 1 1 calc R C30 C 1.24939(13) 0.95153(19) 0.17086(5) 0.0188(2) Uani 1 1 d . C31 C 1.37517(13) 0.9742(2) 0.14324(6) 0.0270(3) Uani 1 1 d . H31A H 1.3709 1.0932 0.1241 0.041 Uiso 1 1 calc R H31B H 1.3826 0.8690 0.1193 0.041 Uiso 1 1 calc R H31C H 1.4543 0.9751 0.1682 0.041 Uiso 1 1 calc R C32 C 0.62011(11) 0.91640(16) -0.05840(4) 0.0122(2) Uani 1 1 d . C33 C 0.58248(12) 0.94651(17) -0.10247(5) 0.0145(2) Uani 1 1 d . C34 C 0.54640(13) 0.97701(19) -0.15634(5) 0.0172(2) Uani 1 1 d . C35 C 0.41663(15) 0.9918(3) -0.17472(5) 0.0304(3) Uani 1 1 d . H35A H 0.3465 0.9821 -0.1521 0.037 Uiso 1 1 calc R H35B H 0.3948 1.0119 -0.2104 0.037 Uiso 1 1 calc R C36 C 0.66123(15) 0.9827(2) -0.19041(6) 0.0260(3) Uani 1 1 d . H36A H 0.6295 1.0360 -0.2239 0.039 Uiso 1 1 calc R H36B H 0.6949 0.8545 -0.1952 0.039 Uiso 1 1 calc R H36C H 0.7343 1.0612 -0.1744 0.039 Uiso 1 1 calc R 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 0.0155(4) 0.0145(4) 0.0111(4) 0.0011(3) -0.0038(3) 0.0023(3) O2 0.0162(4) 0.0241(5) 0.0189(4) -0.0044(4) -0.0074(3) 0.0039(4) O3 0.0380(6) 0.0519(8) 0.0276(6) -0.0053(6) -0.0200(5) 0.0093(6) O4 0.0106(4) 0.0194(4) 0.0157(4) -0.0003(3) 0.0020(3) 0.0014(3) O5 0.0149(4) 0.0156(4) 0.0170(4) -0.0020(3) 0.0014(3) 0.0035(3) O6 0.0165(4) 0.0251(5) 0.0128(4) 0.0024(3) 0.0038(3) -0.0011(4) O7 0.0093(3) 0.0214(5) 0.0144(4) 0.0027(3) -0.0003(3) 0.0034(3) O8 0.0177(4) 0.0154(4) 0.0245(5) 0.0066(3) -0.0101(3) -0.0047(3) O9 0.0118(3) 0.0055(3) 0.0127(4) -0.0002(3) -0.0037(3) -0.0007(3) O10 0.0116(4) 0.0150(4) 0.0172(4) 0.0035(3) -0.0038(3) -0.0022(3) O11 0.0265(5) 0.0368(6) 0.0232(5) 0.0022(4) -0.0115(4) -0.0078(5) O12 0.0084(3) 0.0100(4) 0.0167(4) 0.0004(3) 0.0024(3) -0.0013(3) O13 0.0122(3) 0.0069(3) 0.0184(4) 0.0024(3) 0.0016(3) -0.0025(3) O14 0.0138(4) 0.0158(4) 0.0153(4) -0.0018(3) 0.0041(3) 0.0014(3) O15 0.0067(3) 0.0130(4) 0.0156(4) -0.0021(3) 0.0002(3) -0.0035(3) O16 0.0142(4) 0.0059(3) 0.0246(4) -0.0048(3) -0.0089(3) 0.0052(3) C1 0.0209(5) 0.0200(6) 0.0098(5) 0.0007(4) -0.0028(4) 0.0028(5) C2 0.0204(6) 0.0195(6) 0.0119(5) -0.0035(4) -0.0046(4) 0.0044(5) C3 0.0185(5) 0.0164(5) 0.0126(5) -0.0034(4) -0.0044(4) 0.0007(4) C4 0.0100(4) 0.0140(5) 0.0111(5) -0.0010(4) -0.0002(4) 0.0008(4) C5 0.0120(4) 0.0134(5) 0.0129(5) 0.0007(4) 0.0004(4) 0.0002(4) C6 0.0133(5) 0.0155(5) 0.0108(5) 0.0018(4) 0.0004(4) 0.0000(4) C7 0.0109(4) 0.0154(5) 0.0111(5) 0.0007(4) -0.0011(4) -0.0001(4) C8 0.0107(4) 0.0129(5) 0.0127(5) 0.0005(4) -0.0028(4) -0.0001(4) C9 0.0105(4) 0.0132(5) 0.0113(5) 0.0003(4) -0.0014(4) 0.0001(4) C10 0.0321(7) 0.0314(8) 0.0162(6) 0.0052(5) 0.0077(5) 0.0058(6) C11 0.0315(7) 0.0206(6) 0.0184(6) 0.0026(5) -0.0085(5) 0.0050(5) C12 0.0232(6) 0.0241(7) 0.0322(7) -0.0080(6) -0.0163(5) 0.0058(5) C13 0.0196(6) 0.0360(9) 0.0517(10) -0.0148(8) -0.0091(7) 0.0067(6) C14 0.0140(5) 0.0176(5) 0.0147(5) 0.0018(4) -0.0022(4) -0.0004(4) C15 0.0193(5) 0.0203(6) 0.0144(5) 0.0012(4) -0.0014(4) -0.0029(5) C16 0.0278(6) 0.0248(6) 0.0114(5) 0.0004(4) -0.0007(4) -0.0065(5) C17 0.0278(7) 0.0603(12) 0.0131(6) 0.0037(6) -0.0059(5) -0.0106(7) C18 0.0325(8) 0.0430(10) 0.0231(7) -0.0065(6) 0.0094(6) -0.0087(7) C19 0.0155(5) 0.0108(5) 0.0125(5) -0.0014(4) -0.0030(4) -0.0002(4) C20 0.0132(5) 0.0100(5) 0.0140(5) 0.0026(4) -0.0033(4) -0.0006(4) C21 0.0124(4) 0.0072(4) 0.0155(5) 0.0028(4) -0.0024(4) 0.0000(4) C22 0.0075(4) 0.0050(4) 0.0135(5) 0.0009(3) 0.0000(3) 0.0001(3) C23 0.0097(4) 0.0046(4) 0.0143(5) 0.0000(3) 0.0006(3) 0.0001(3) C24 0.0108(4) 0.0065(4) 0.0135(5) -0.0013(3) 0.0005(3) 0.0007(4) C25 0.0079(4) 0.0061(4) 0.0129(4) -0.0007(3) -0.0010(3) 0.0002(3) C26 0.0082(4) 0.0043(4) 0.0140(5) 0.0001(3) -0.0026(3) 0.0011(3) C27 0.0069(4) 0.0046(4) 0.0135(4) -0.0002(3) -0.0009(3) 0.0001(3) C28 0.0234(6) 0.0244(6) 0.0160(5) -0.0009(5) 0.0049(4) 0.0039(5) C29 0.0270(6) 0.0115(5) 0.0220(6) -0.0044(4) -0.0106(5) 0.0007(5) C30 0.0156(5) 0.0131(5) 0.0261(6) 0.0045(4) -0.0082(4) -0.0026(4) C31 0.0147(5) 0.0254(7) 0.0401(8) 0.0089(6) -0.0029(5) -0.0054(5) C32 0.0118(4) 0.0080(4) 0.0163(5) -0.0012(4) -0.0018(4) -0.0002(4) C33 0.0155(5) 0.0105(5) 0.0171(5) -0.0012(4) -0.0021(4) 0.0008(4) C34 0.0208(5) 0.0157(5) 0.0146(5) 0.0008(4) -0.0014(4) 0.0033(4) C35 0.0237(7) 0.0510(10) 0.0156(6) -0.0019(6) -0.0050(5) 0.0099(7) C36 0.0263(7) 0.0294(7) 0.0231(6) 0.0043(5) 0.0068(5) 0.0025(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 '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 C9 O1 C1 114.02(9) C12 O2 C2 118.01(11) C4 O4 H4 109.5 C5 O5 H5 109.5 C6 O6 H6 109.5 C7 O7 H7 109.5 C8 O8 H8 109.5 C27 O9 C19 113.95(8) C30 O10 C20 118.40(10) C22 O12 H12 109.5 C23 O13 H13 109.5 C24 O14 H14 109.5 C25 O15 H15 109.5 C26 O16 H16 109.5 O1 C1 C11 103.73(10) O1 C1 C10 111.50(10) C11 C1 C10 109.89(12) O1 C1 C2 109.83(10) C11 C1 C2 112.26(11) C10 C1 C2 109.54(11) O2 C2 C3 105.93(11) O2 C2 C1 111.13(10) C3 C2 C1 112.73(10) O2 C2 H2 109.0 C3 C2 H2 109.0 C1 C2 H2 109.0 C2 C3 C4 112.45(10) C2 C3 H3A 109.1 C4 C3 H3A 109.1 C2 C3 H3B 109.1 C4 C3 H3B 109.1 H3A C3 H3B 107.8 O4 C4 C9 109.96(9) O4 C4 C3 110.83(9) C9 C4 C3 109.02(9) O4 C4 C5 104.81(9) C9 C4 C5 110.22(9) C3 C4 C5 111.94(10) O5 C5 C4 111.68(9) O5 C5 C6 110.89(9) C4 C5 C6 111.48(10) O5 C5 H5A 107.5 C4 C5 H5A 107.5 C6 C5 H5A 107.5 O6 C6 C5 111.14(9) O6 C6 C7 113.18(10) C5 C6 C7 111.57(9) O6 C6 H6A 106.8 C5 C6 H6A 106.8 C7 C6 H6A 106.8 O7 C7 C14 112.27(9) O7 C7 C8 106.36(9) C14 C7 C8 111.36(10) O7 C7 C6 107.44(10) C14 C7 C6 108.47(9) C8 C7 C6 110.88(9) O8 C8 C9 110.12(10) O8 C8 C7 108.57(9) C9 C8 C7 108.93(10) O8 C8 H8A 109.7 C9 C8 H8A 109.7 C7 C8 H8A 109.7 O1 C9 C8 107.14(9) O1 C9 C4 109.48(9) C8 C9 C4 111.91(9) O1 C9 H9 109.4 C8 C9 H9 109.4 C4 C9 H9 109.4 C1 C10 H10A 109.5 C1 C10 H10B 109.5 H10A C10 H10B 109.5 C1 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C1 C11 H11A 109.5 C1 C11 H11B 109.5 H11A C11 H11B 109.5 C1 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 O3 C12 O2 123.69(15) O3 C12 C13 125.99(14) O2 C12 C13 110.33(14) C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C15 C14 C7 172.79(14) C14 C15 C16 175.37(14) C17 C16 C15 121.37(13) C17 C16 C18 122.64(13) C15 C16 C18 115.93(12) C16 C17 H17A 120.0 C16 C17 H17B 120.0 H17A C17 H17B 120.0 C16 C18 H18A 109.5 C16 C18 H18B 109.5 H18A C18 H18B 109.5 C16 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 O9 C19 C29 103.90(10) O9 C19 C28 111.41(9) C29 C19 C28 110.04(11) O9 C19 C20 109.81(9) C29 C19 C20 112.10(10) C28 C19 C20 109.50(10) O10 C20 C21 105.90(9) O10 C20 C19 111.03(9) C21 C20 C19 112.55(9) O10 C20 H20 109.1 C21 C20 H20 109.1 C19 C20 H20 109.1 C20 C21 C22 112.47(9) C20 C21 H21A 109.1 C22 C21 H21A 109.1 C20 C21 H21B 109.1 C22 C21 H21B 109.1 H21A C21 H21B 107.8 O12 C22 C21 111.04(8) O12 C22 C27 110.10(8) C21 C22 C27 108.86(9) O12 C22 C23 104.71(8) C21 C22 C23 111.92(9) C27 C22 C23 110.17(8) O13 C23 C24 111.01(8) O13 C23 C22 111.85(9) C24 C23 C22 111.46(9) O13 C23 H23 107.4 C24 C23 H23 107.4 C22 C23 H23 107.4 O14 C24 C23 111.32(9) O14 C24 C25 113.00(9) C23 C24 C25 111.54(9) O14 C24 H24 106.9 C23 C24 H24 106.9 C25 C24 H24 106.9 O15 C25 C32 112.37(9) O15 C25 C26 106.58(9) C32 C25 C26 111.51(9) O15 C25 C24 107.21(8) C32 C25 C24 108.27(9) C26 C25 C24 110.84(8) O16 C26 C27 110.23(9) O16 C26 C25 108.46(8) C27 C26 C25 109.01(8) O16 C26 H26 109.7 C27 C26 H26 109.7 C25 C26 H26 109.7 O9 C27 C26 107.06(8) O9 C27 C22 109.32(8) C26 C27 C22 111.86(9) O9 C27 H27 109.5 C26 C27 H27 109.5 C22 C27 H27 109.5 C19 C28 H28A 109.5 C19 C28 H28B 109.5 H28A C28 H28B 109.5 C19 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C19 C29 H29A 109.5 C19 C29 H29B 109.5 H29A C29 H29B 109.5 C19 C29 H29C 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 O11 C30 O10 123.43(13) O11 C30 C31 125.97(12) O10 C30 C31 110.61(12) C30 C31 H31A 109.5 C30 C31 H31B 109.5 H31A C31 H31B 109.5 C30 C31 H31C 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 C33 C32 C25 172.65(12) C32 C33 C34 175.88(13) C35 C34 C33 121.22(12) C35 C34 C36 122.52(12) C33 C34 C36 116.21(11) C34 C35 H35A 120.0 C34 C35 H35B 120.0 H35A C35 H35B 120.0 C34 C36 H36A 109.5 C34 C36 H36B 109.5 H36A C36 H36B 109.5 C34 C36 H36C 109.5 H36A C36 H36C 109.5 H36B C36 H36C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.4242(14) O1 C1 1.4484(14) O2 C12 1.3493(15) O2 C2 1.4537(16) O3 C12 1.201(2) O4 C4 1.4384(14) O4 H4 0.8400 O5 C5 1.4240(14) O5 H5 0.8400 O6 C6 1.4197(14) O6 H6 0.8400 O7 C7 1.4286(14) O7 H7 0.8400 O8 C8 1.4181(15) O8 H8 0.8400 O9 C27 1.4256(13) O9 C19 1.4481(13) O10 C30 1.3525(14) O10 C20 1.4501(14) O11 C30 1.2027(18) O12 C22 1.4360(13) O12 H12 0.8400 O13 C23 1.4224(13) O13 H13 0.8400 O14 C24 1.4206(13) O14 H14 0.8400 O15 C25 1.4303(13) O15 H15 0.8400 O16 C26 1.4193(13) O16 H16 0.8400 C1 C11 1.5219(19) C1 C10 1.5298(19) C1 C2 1.539(2) C2 C3 1.5245(18) C2 H2 1.0000 C3 C4 1.5278(16) C3 H3A 0.9900 C3 H3B 0.9900 C4 C9 1.5275(16) C4 C5 1.5348(16) C5 C6 1.5419(16) C5 H5A 1.0000 C6 C7 1.5573(17) C6 H6A 1.0000 C7 C14 1.4739(16) C7 C8 1.5437(16) C8 C9 1.5224(15) C8 H8A 1.0000 C9 H9 1.0000 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 C13 1.499(2) C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 C15 1.2021(17) C15 C16 1.4399(17) C16 C17 1.345(2) C16 C18 1.488(2) C17 H17A 0.9500 C17 H17B 0.9500 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 C29 1.5227(17) C19 C28 1.5289(18) C19 C20 1.5435(16) C20 C21 1.5247(16) C20 H20 1.0000 C21 C22 1.5283(15) C21 H21A 0.9900 C21 H21B 0.9900 C22 C27 1.5287(14) C22 C23 1.5383(15) C23 C24 1.5376(15) C23 H23 1.0000 C24 C25 1.5632(15) C24 H24 1.0000 C25 C32 1.4741(15) C25 C26 1.5413(15) C26 C27 1.5230(14) C26 H26 1.0000 C27 H27 1.0000 C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 C29 H29A 0.9800 C29 H29B 0.9800 C29 H29C 0.9800 C30 C31 1.497(2) C31 H31A 0.9800 C31 H31B 0.9800 C31 H31C 0.9800 C32 C33 1.1998(16) C33 C34 1.4394(16) C34 C35 1.3408(18) C34 C36 1.4991(19) C35 H35A 0.9500 C35 H35B 0.9500 C36 H36A 0.9800 C36 H36B 0.9800 C36 H36C 0.9800