#------------------------------------------------------------------------------ #$Date: 2024-09-06 02:56:54 +0300 (Fri, 06 Sep 2024) $ #$Revision: 294490 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572076.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_1572076 loop_ _publ_author_name 'Wieprecht, Nele' 'Krummenacher, Ivo' 'Wüst, Leonie' 'Michel, Maximilian' 'Fuchs, Sonja' 'Nees, Samuel' 'Härterich, Marcel' 'Braunschweig, Holger' _publ_section_title ; The forgotten borole: synthesis, properties and reactivity of a 1-boraindene. ; _journal_issue 31 _journal_name_full 'Chemical science' _journal_page_first 12496 _journal_page_last 12501 _journal_paper_doi 10.1039/d4sc03817g _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C30 H27 B O' _chemical_formula_sum 'C30 H27 B O' _chemical_formula_weight 414.32 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2024-04-10 _audit_creation_method 'CIF-fill 1.4u (K.Radacki, 2005-23)' _audit_update_record ; 2024-06-05 deposited with the CCDC. 2024-07-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.511(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.9933(2) _cell_length_b 12.0387(2) _cell_length_c 17.7494(3) _cell_measurement_reflns_used 10233 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 74.3090 _cell_measurement_theta_min 4.2370 _cell_volume 2252.18(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector HPA _diffrn_detector_area_resol_mean 10.0 _diffrn_detector_type 'HyPix Arc150' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): -------------------------------------------------------------------------- 1 \w -118.00 -86.00 0.50 0.39 -- -69.77 -15.00 -60.00 64 2 \w -72.00 -34.00 0.50 0.39 -- -69.77 -15.00 -60.00 76 3 \w -71.00 -41.00 0.50 0.39 -- -76.38 -15.00 -30.00 60 4 \w -127.00 -77.00 0.50 0.39 -- -76.38 -15.00 -30.00 100 5 \w -108.00 -65.00 0.50 0.39 -- -60.28 -15.00 90.00 86 6 \w -108.00 -51.00 0.50 0.39 -- -76.38 -15.00-120.00 114 7 \w -125.00 -43.00 0.50 0.39 -- -76.38 -15.00-180.00 164 8 \w -74.00 -48.00 0.50 0.39 -- -76.38 112.00-180.00 52 9 \w -97.00 -33.00 0.50 0.39 -- -79.50 116.00-156.28 128 10 \w -97.00 -48.00 0.50 0.39 -- -79.50 116.00 31.76 98 11 \w -97.00 -37.00 0.50 0.39 -- -79.50 115.00 132.32 120 12 \w -60.00 -31.00 0.50 0.39 -- -76.38 112.00 90.00 58 13 \w -55.00 -26.00 0.50 0.39 -- -60.28 126.00 30.00 58 14 \w 48.00 126.00 0.50 0.39 -- 84.40 15.00 120.00 156 15 \w 48.00 103.00 0.50 0.39 -- 84.40 15.00 -90.00 110 16 \w 65.00 135.00 0.50 0.39 -- 84.40 15.00-180.00 140 17 \w 25.00 51.00 0.50 0.39 -- 71.40-126.00-150.00 52 18 \w 20.00 54.00 0.50 0.39 -- 58.64-126.00 0.00 68 19 \w 31.00 56.00 0.50 0.39 -- 71.40 -95.00 60.00 50 20 \w 30.00 56.00 0.50 0.39 -- 71.40 -95.00 120.00 52 21 \w 32.00 93.00 0.50 0.39 -- 76.43-112.00 30.00 122 22 \w 48.00 93.00 0.50 0.39 -- 76.43-112.00 -30.00 90 23 \w 66.00 92.00 0.50 0.39 -- 84.40 -95.00 60.00 52 24 \w 25.00 52.00 0.50 0.39 -- 58.64 -95.00 0.00 54 25 \w 16.00 55.00 0.50 0.39 -- 58.64 -95.00 -60.00 78 26 \w 16.00 56.00 0.50 0.39 -- 58.64 -95.00-150.00 80 27 \w 65.00 92.00 0.50 0.39 -- 84.40 -95.00-180.00 54 28 \w 66.00 92.00 0.50 0.39 -- 84.40 -95.00 -60.00 52 29 \w 50.00 92.00 0.50 0.39 -- 84.40 -95.00 -90.00 84 30 \w 42.00 74.00 0.50 0.39 -- 84.40 -95.00 -30.00 64 31 \w 67.00 92.00 0.50 0.39 -- 84.40 -95.00-120.00 50 32 \w 63.00 88.00 0.50 0.39 -- 84.40 -95.00-150.00 50 33 \w 51.00 92.00 0.50 0.39 -- 84.40 -95.00 0.00 82 34 \w 42.00 92.00 0.50 0.39 -- 84.40 -95.00 30.00 100 35 \w 46.00 92.00 0.50 0.39 -- 84.40 -95.00 120.00 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku XtaLAB Synergy-R' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type ; CrysAlisPro convention (1999,Acta A55,543-557) ; _diffrn_orient_matrix_UB_11 -0.1315611000 _diffrn_orient_matrix_UB_12 -0.0158334000 _diffrn_orient_matrix_UB_13 -0.0593324000 _diffrn_orient_matrix_UB_21 0.0011947000 _diffrn_orient_matrix_UB_22 -0.1232576000 _diffrn_orient_matrix_UB_23 0.0236733000 _diffrn_orient_matrix_UB_31 -0.0635432000 _diffrn_orient_matrix_UB_32 0.0309284000 _diffrn_orient_matrix_UB_33 0.0641081000 _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_xray_symbol K-L~2,3~ _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 26463 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.946 _diffrn_reflns_theta_min 4.260 _diffrn_source 'rotating-anode X-ray tube' _diffrn_source_type 'PhotonJet-R X-ray Source' _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.19585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.222 _exptl_crystal_description plate _exptl_crystal_F_000 880 _exptl_crystal_preparation ; For data collection the crystal was immersed in a film of perfluoropolyether oil, mounted on a polyimide loop and transferred to stream of cold nitrogen (Oxford Cryostream 800). ; _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.216 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 4516 _refine_ls_number_restraints 220 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0431 _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^)+(0.0704P)^2^+0.4380P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1117 _refine_ls_wR_factor_ref 0.1189 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3658 _reflns_number_total 4516 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc03817g2.cif _cod_data_source_block 1-THF _cod_depositor_comments 'Adding full bibliography for 1572071--1572079.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1572076 _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 0.850 _shelx_estimated_absorpt_t_max 0.948 _shelx_res_file ; TITL NeWi011_NeWi_a.res in P2(1)/n NeWi011_NeWi_a.res created by SHELXL-2018/3 at 10:57:08 on 10-Apr-2024 REM Old TITL NeWi011_NeWi in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.154, Rweak 0.119, Alpha 0.023, Orientation as input REM Formula found by SHELXT: C31 B CELL 1.54184 10.9933 12.0387 17.7494 90.000 106.511 90.000 ZERR 4.000 0.0002 0.0002 0.0003 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H B O UNIT 120 108 4 4 TEMP -173 SIZE 0.10 0.28 0.31 L.S. 10 BOND $H LIST 4 acta conf FMAP 2 PLAN 20 WGHT 0.070400 0.438000 FVAR 0.49431 0.15899 RESI 1 MAIN B1 3 0.248652 0.703389 0.682461 11.00000 0.01876 0.01966 = 0.01772 0.00038 0.00303 -0.00002 C2 1 0.372658 0.767419 0.670025 11.00000 0.01571 0.01979 = 0.01859 0.00233 0.00269 0.00107 C3 1 0.456235 0.787404 0.741605 11.00000 0.01533 0.01906 = 0.01951 0.00190 0.00251 0.00211 C4 1 0.411629 0.740858 0.806436 11.00000 0.01756 0.01863 = 0.01883 0.00059 0.00316 0.00212 C5 1 0.468150 0.749096 0.887250 11.00000 0.02166 0.02397 = 0.01929 -0.00149 0.00253 0.00036 AFIX 43 H5 2 0.545027 0.789236 0.907062 11.00000 -1.20000 AFIX 0 C6 1 0.410344 0.697625 0.938645 11.00000 0.02871 0.02630 = 0.01530 0.00018 0.00437 0.00344 AFIX 43 H6 2 0.449336 0.701029 0.993708 11.00000 -1.20000 AFIX 0 C7 1 0.296454 0.641612 0.909827 11.00000 0.02778 0.02309 = 0.02259 0.00268 0.01055 0.00257 AFIX 43 H7 2 0.258087 0.606053 0.945073 11.00000 -1.20000 AFIX 0 C8 1 0.237886 0.637408 0.828741 11.00000 0.01915 0.02218 = 0.02404 -0.00010 0.00574 -0.00015 AFIX 43 H8 2 0.157908 0.601844 0.809437 11.00000 -1.20000 AFIX 0 C9 1 0.295415 0.684593 0.776399 11.00000 0.01795 0.01940 = 0.01832 0.00038 0.00335 0.00236 C10 1 0.110941 0.760604 0.656724 11.00000 0.01748 0.02138 = 0.01448 0.00022 0.00222 0.00023 C11 1 0.001370 0.697759 0.652697 11.00000 0.02066 0.02157 = 0.02229 0.00279 0.00449 0.00018 AFIX 43 H11 2 0.008526 0.619392 0.658583 11.00000 -1.20000 AFIX 0 C12 1 -0.116773 0.746894 0.640385 11.00000 0.01792 0.02764 = 0.02349 0.00164 0.00496 -0.00102 AFIX 43 H12 2 -0.189024 0.702025 0.637554 11.00000 -1.20000 AFIX 0 C13 1 -0.130020 0.861231 0.632180 11.00000 0.02111 0.02744 = 0.02152 -0.00080 0.00440 0.00596 AFIX 43 H13 2 -0.210840 0.894968 0.624104 11.00000 -1.20000 AFIX 0 C14 1 -0.023824 0.925762 0.635907 11.00000 0.02670 0.02149 = 0.02252 -0.00264 0.00409 0.00219 AFIX 43 H14 2 -0.031718 1.004119 0.630245 11.00000 -1.20000 AFIX 0 C15 1 0.094382 0.875519 0.647961 11.00000 0.01976 0.02173 = 0.01907 -0.00212 0.00332 -0.00229 AFIX 43 H15 2 0.166095 0.920854 0.650302 11.00000 -1.20000 AFIX 0 C16 1 0.401216 0.796244 0.595669 11.00000 0.01822 0.01901 = 0.01783 -0.00078 0.00294 -0.00322 C17 1 0.314640 0.853353 0.534351 11.00000 0.01978 0.02210 = 0.01916 -0.00109 0.00277 -0.00016 AFIX 43 H17 2 0.233685 0.872851 0.539563 11.00000 -1.20000 AFIX 0 C18 1 0.345613 0.881681 0.466334 11.00000 0.02900 0.02241 = 0.01856 0.00171 0.00203 -0.00080 AFIX 43 H18 2 0.286809 0.922224 0.426164 11.00000 -1.20000 AFIX 0 C19 1 0.462237 0.851120 0.456531 11.00000 0.02895 0.02756 = 0.01879 0.00048 0.00729 -0.00489 AFIX 43 H19 2 0.483201 0.870672 0.409884 11.00000 -1.20000 AFIX 0 C20 1 0.547555 0.791955 0.515325 11.00000 0.02108 0.02667 = 0.02301 -0.00370 0.00686 -0.00398 AFIX 43 H20 2 0.626706 0.769635 0.508608 11.00000 -1.20000 AFIX 0 C21 1 0.517653 0.765265 0.583927 11.00000 0.01828 0.02294 = 0.01918 0.00060 0.00258 -0.00090 AFIX 43 H21 2 0.577272 0.725108 0.623908 11.00000 -1.20000 AFIX 0 C22 1 0.576055 0.852895 0.758856 11.00000 0.01753 0.02158 = 0.01668 -0.00137 0.00424 -0.00024 C23 1 0.577842 0.957761 0.725231 11.00000 0.01930 0.02201 = 0.02025 -0.00025 0.00450 0.00177 AFIX 43 H23 2 0.503330 0.985079 0.688375 11.00000 -1.20000 AFIX 0 C24 1 0.686920 1.022581 0.744908 11.00000 0.02544 0.02078 = 0.02623 -0.00275 0.00931 -0.00340 AFIX 43 H24 2 0.686101 1.094054 0.722084 11.00000 -1.20000 AFIX 0 C25 1 0.796974 0.983238 0.797768 11.00000 0.02024 0.03014 = 0.03032 -0.00744 0.00621 -0.00741 AFIX 43 H25 2 0.871380 1.027764 0.811503 11.00000 -1.20000 AFIX 0 C26 1 0.797780 0.878654 0.830420 11.00000 0.01862 0.03250 = 0.02789 -0.00055 -0.00032 -0.00028 AFIX 43 H26 2 0.873402 0.850814 0.865903 11.00000 -1.20000 AFIX 0 C27 1 0.688245 0.814278 0.811427 11.00000 0.01960 0.02454 = 0.02326 0.00107 0.00118 0.00061 AFIX 43 H27 2 0.689682 0.742938 0.834542 11.00000 -1.20000 AFIX 0 RESI 0 RESI 2 THF RESI 0 SAME_THF O1 > C4 SIMU 0.008 O1_2 > C4_12 RIGU 0.004 O1_2 > C4_12 RESI 2 THF PART 1 21.0 O1 4 0.230947 0.585423 0.639826 21.00000 0.02452 0.02314 = 0.02016 -0.00025 -0.00074 0.00367 C1 1 0.337851 0.507105 0.671765 21.00000 0.02486 0.02509 = 0.02575 -0.00269 0.00382 0.00782 AFIX 23 H1A 2 0.327385 0.466874 0.718171 21.00000 -1.20000 H1B 2 0.420245 0.546585 0.686611 21.00000 -1.20000 AFIX 0 C2 1 0.328598 0.428935 0.603974 21.00000 0.02663 0.02671 = 0.02952 -0.00215 0.00793 0.00148 AFIX 23 H2A 2 0.265771 0.369359 0.602208 21.00000 -1.20000 H2B 2 0.411832 0.395112 0.606717 21.00000 -1.20000 AFIX 0 C3 1 0.284814 0.507159 0.533615 21.00000 0.03605 0.03488 = 0.02691 -0.00607 0.00325 -0.00175 AFIX 23 H3A 2 0.355329 0.554879 0.528418 21.00000 -1.20000 H3B 2 0.250382 0.465067 0.484220 21.00000 -1.20000 AFIX 0 C4 1 0.182041 0.575612 0.553429 21.00000 0.02901 0.02640 = 0.02023 0.00089 -0.00003 -0.00278 AFIX 23 H4A 2 0.173048 0.649394 0.527801 21.00000 -1.20000 H4B 2 0.099215 0.536865 0.537702 21.00000 -1.20000 AFIX 0 PART 0 RESI 0 RESI 12 THF PART 2 -21.0 O1 4 0.230339 0.584251 0.638334 -21.00000 0.01870 0.01968 = 0.01653 0.00088 0.00066 0.00317 C1 1 0.181379 0.582999 0.551689 -21.00000 0.03104 0.02381 = 0.01601 -0.00166 -0.00150 -0.00026 AFIX 23 H1A 2 0.216399 0.645770 0.528426 -21.00000 -1.20000 H1B 2 0.087606 0.587661 0.534681 -21.00000 -1.20000 AFIX 0 C2 1 0.225964 0.473033 0.527913 -21.00000 0.02733 0.02869 = 0.02706 -0.00890 0.00124 -0.00084 AFIX 23 H2A 2 0.234967 0.476265 0.474021 -21.00000 -1.20000 H2B 2 0.167141 0.412080 0.531039 -21.00000 -1.20000 AFIX 0 C3 1 0.354301 0.458837 0.588937 -21.00000 0.03196 0.03942 = 0.03330 -0.01117 0.00351 0.00933 AFIX 23 H3A 2 0.382317 0.380363 0.592740 -21.00000 -1.20000 H3B 2 0.419888 0.505826 0.576432 -21.00000 -1.20000 AFIX 0 C4 1 0.327187 0.496775 0.664022 -21.00000 0.02318 0.02229 = 0.02738 0.00041 -0.00270 0.00724 AFIX 23 H4A 2 0.294481 0.434624 0.689197 -21.00000 -1.20000 H4B 2 0.404762 0.526727 0.701683 -21.00000 -1.20000 RESI 0 PART 0 AFIX 0 HKLF 4 REM NeWi011_NeWi_a.res in P2(1)/n REM wR2 = 0.118873, GooF = S = 1.04445, Restrained GooF = 1.02692 for all data REM R1 = 0.043126 for 3658 Fo > 4sig(Fo) and 0.055464 for all 4516 data REM 335 parameters refined using 220 restraints END WGHT 0.0703 0.4373 REM Highest difference peak 0.216, deepest hole -0.263, 1-sigma level 0.049 Q1 1 0.3105 0.7355 0.6706 11.00000 0.05 0.22 Q2 1 0.2767 0.6788 0.7327 11.00000 0.05 0.20 Q3 1 0.3953 0.8030 0.7019 11.00000 0.05 0.16 Q4 1 0.1762 0.7295 0.6671 11.00000 0.05 0.16 Q5 1 0.5125 0.8111 0.7530 11.00000 0.05 0.15 Q6 1 -0.0110 0.5816 0.6345 11.00000 0.05 0.15 Q7 1 0.2006 0.5852 0.9351 11.00000 0.05 0.14 Q8 1 0.6335 0.8237 0.7762 11.00000 0.05 0.14 Q9 1 0.1578 0.3964 0.6392 11.00000 0.05 0.14 Q10 1 0.1605 0.6866 0.9283 11.00000 0.05 0.14 Q11 1 0.7410 0.8247 0.5135 11.00000 0.05 0.14 Q12 1 0.3591 0.8180 0.5640 11.00000 0.05 0.13 Q13 1 0.2831 0.6346 0.5215 11.00000 0.05 0.13 Q14 1 0.0587 0.5170 0.5985 11.00000 0.05 0.13 Q15 1 0.3855 1.0166 0.4955 11.00000 0.05 0.13 Q16 1 0.3867 0.5294 0.7263 11.00000 0.05 0.13 Q17 1 0.3414 0.3387 0.6125 11.00000 0.05 0.13 Q18 1 0.2639 0.3602 0.7390 11.00000 0.05 0.13 Q19 1 0.6604 0.6159 0.6271 11.00000 0.05 0.13 Q20 1 0.2483 0.3000 0.5298 11.00000 0.05 0.13 ; _shelx_res_checksum 24230 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 B1_1 B 0.24865(15) 0.70339(13) 0.68246(9) 0.0192(3) Uani 1 1 d . . . . . C2_1 C 0.37266(12) 0.76742(11) 0.67003(8) 0.0185(3) Uani 1 1 d . . . . . C3_1 C 0.45624(12) 0.78740(11) 0.74160(8) 0.0185(3) Uani 1 1 d . . . . . C4_1 C 0.41163(13) 0.74086(11) 0.80644(8) 0.0188(3) Uani 1 1 d . . . . . C5_1 C 0.46815(13) 0.74910(12) 0.88725(8) 0.0223(3) Uani 1 1 d . . . . . H5_1 H 0.545027 0.789236 0.907062 0.027 Uiso 1 1 calc R U . . . C6_1 C 0.41034(14) 0.69763(12) 0.93864(8) 0.0238(3) Uani 1 1 d . . . . . H6_1 H 0.449336 0.701029 0.993708 0.029 Uiso 1 1 calc R U . . . C7_1 C 0.29645(14) 0.64161(12) 0.90983(8) 0.0238(3) Uani 1 1 d . . . . . H7_1 H 0.258087 0.606053 0.945073 0.029 Uiso 1 1 calc R U . . . C8_1 C 0.23789(13) 0.63741(12) 0.82874(8) 0.0219(3) Uani 1 1 d . . . . . H8_1 H 0.157908 0.601844 0.809437 0.026 Uiso 1 1 calc R U . . . C9_1 C 0.29542(12) 0.68459(11) 0.77640(8) 0.0189(3) Uani 1 1 d . . . . . C10_1 C 0.11094(12) 0.76060(11) 0.65672(7) 0.0183(3) Uani 1 1 d . . . . . C11_1 C 0.00137(13) 0.69776(12) 0.65270(8) 0.0218(3) Uani 1 1 d . . . . . H11_1 H 0.008526 0.619392 0.658583 0.026 Uiso 1 1 calc R U . . . C12_1 C -0.11677(13) 0.74689(12) 0.64039(8) 0.0232(3) Uani 1 1 d . . . . . H12_1 H -0.189024 0.702025 0.637554 0.028 Uiso 1 1 calc R U . . . C13_1 C -0.13002(14) 0.86123(12) 0.63218(8) 0.0237(3) Uani 1 1 d . . . . . H13_1 H -0.210840 0.894968 0.624104 0.028 Uiso 1 1 calc R U . . . C14_1 C -0.02382(14) 0.92576(12) 0.63591(8) 0.0242(3) Uani 1 1 d . . . . . H14_1 H -0.031718 1.004119 0.630245 0.029 Uiso 1 1 calc R U . . . C15_1 C 0.09438(13) 0.87552(12) 0.64796(8) 0.0206(3) Uani 1 1 d . . . . . H15_1 H 0.166095 0.920854 0.650302 0.025 Uiso 1 1 calc R U . . . C16_1 C 0.40122(13) 0.79624(11) 0.59567(8) 0.0188(3) Uani 1 1 d . . . . . C17_1 C 0.31464(13) 0.85335(11) 0.53435(8) 0.0209(3) Uani 1 1 d . . . . . H17_1 H 0.233685 0.872851 0.539563 0.025 Uiso 1 1 calc R U . . . C18_1 C 0.34561(14) 0.88168(12) 0.46633(8) 0.0243(3) Uani 1 1 d . . . . . H18_1 H 0.286809 0.922224 0.426164 0.029 Uiso 1 1 calc R U . . . C19_1 C 0.46224(14) 0.85112(12) 0.45653(8) 0.0250(3) Uani 1 1 d . . . . . H19_1 H 0.483201 0.870672 0.409884 0.030 Uiso 1 1 calc R U . . . C20_1 C 0.54756(14) 0.79195(12) 0.51533(8) 0.0235(3) Uani 1 1 d . . . . . H20_1 H 0.626706 0.769635 0.508608 0.028 Uiso 1 1 calc R U . . . C21_1 C 0.51765(13) 0.76527(12) 0.58393(8) 0.0207(3) Uani 1 1 d . . . . . H21_1 H 0.577272 0.725108 0.623908 0.025 Uiso 1 1 calc R U . . . C22_1 C 0.57605(12) 0.85289(11) 0.75886(7) 0.0187(3) Uani 1 1 d . . . . . C23_1 C 0.57784(13) 0.95776(12) 0.72523(8) 0.0207(3) Uani 1 1 d . . . . . H23_1 H 0.503330 0.985079 0.688375 0.025 Uiso 1 1 calc R U . . . C24_1 C 0.68692(13) 1.02258(12) 0.74491(8) 0.0237(3) Uani 1 1 d . . . . . H24_1 H 0.686101 1.094054 0.722084 0.028 Uiso 1 1 calc R U . . . C25_1 C 0.79697(14) 0.98324(13) 0.79777(9) 0.0271(3) Uani 1 1 d . . . . . H25_1 H 0.871380 1.027764 0.811503 0.033 Uiso 1 1 calc R U . . . C26_1 C 0.79778(14) 0.87865(13) 0.83042(9) 0.0278(3) Uani 1 1 d . . . . . H26_1 H 0.873402 0.850814 0.865903 0.033 Uiso 1 1 calc R U . . . C27_1 C 0.68824(13) 0.81428(12) 0.81143(8) 0.0235(3) Uani 1 1 d . . . . . H27_1 H 0.689682 0.742938 0.834542 0.028 Uiso 1 1 calc R U . . . O1_2 O 0.231(6) 0.585(5) 0.640(2) 0.024(2) Uani 0.159(5) 1 d D U P A 1 C1_2 C 0.338(3) 0.507(3) 0.6718(14) 0.026(2) Uani 0.159(5) 1 d D U P A 1 H1A_2 H 0.327385 0.466874 0.718171 0.031 Uiso 0.159(5) 1 calc R U P A 1 H1B_2 H 0.420245 0.546585 0.686611 0.031 Uiso 0.159(5) 1 calc R U P A 1 C2_2 C 0.3286(13) 0.4289(11) 0.6040(7) 0.0276(19) Uani 0.159(5) 1 d D U P A 1 H2A_2 H 0.265771 0.369359 0.602208 0.033 Uiso 0.159(5) 1 calc R U P A 1 H2B_2 H 0.411832 0.395112 0.606717 0.033 Uiso 0.159(5) 1 calc R U P A 1 C3_2 C 0.2848(14) 0.5072(10) 0.5336(6) 0.0338(18) Uani 0.159(5) 1 d D U P A 1 H3A_2 H 0.355329 0.554879 0.528418 0.041 Uiso 0.159(5) 1 calc R U P A 1 H3B_2 H 0.250382 0.465067 0.484220 0.041 Uiso 0.159(5) 1 calc R U P A 1 C4_2 C 0.182(3) 0.576(4) 0.553(2) 0.027(2) Uani 0.159(5) 1 d D U P A 1 H4A_2 H 0.173048 0.649394 0.527801 0.032 Uiso 0.159(5) 1 calc R U P A 1 H4B_2 H 0.099215 0.536865 0.537702 0.032 Uiso 0.159(5) 1 calc R U P A 1 O1_12 O 0.2303(10) 0.5843(9) 0.6383(4) 0.0192(4) Uani 0.841(5) 1 d D U P A 2 C1_12 C 0.1814(7) 0.5830(6) 0.5517(4) 0.0253(7) Uani 0.841(5) 1 d D U P A 2 H1A_12 H 0.216399 0.645770 0.528426 0.030 Uiso 0.841(5) 1 calc R U P A 2 H1B_12 H 0.087606 0.587661 0.534681 0.030 Uiso 0.841(5) 1 calc R U P A 2 C2_12 C 0.2260(2) 0.47303(18) 0.52791(11) 0.0290(5) Uani 0.841(5) 1 d D U P A 2 H2A_12 H 0.234967 0.476265 0.474021 0.035 Uiso 0.841(5) 1 calc R U P A 2 H2B_12 H 0.167141 0.412080 0.531039 0.035 Uiso 0.841(5) 1 calc R U P A 2 C3_12 C 0.3543(2) 0.4588(3) 0.58894(16) 0.0361(6) Uani 0.841(5) 1 d D U P A 2 H3A_12 H 0.382317 0.380363 0.592740 0.043 Uiso 0.841(5) 1 calc R U P A 2 H3B_12 H 0.419888 0.505826 0.576432 0.043 Uiso 0.841(5) 1 calc R U P A 2 C4_12 C 0.3272(6) 0.4968(5) 0.6640(3) 0.0263(7) Uani 0.841(5) 1 d D U P A 2 H4A_12 H 0.294481 0.434624 0.689197 0.032 Uiso 0.841(5) 1 calc R U P A 2 H4B_12 H 0.404762 0.526727 0.701683 0.032 Uiso 0.841(5) 1 calc R U P A 2 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 B1_1 0.0188(7) 0.0197(7) 0.0177(7) 0.0004(6) 0.0030(6) 0.0000(6) C2_1 0.0157(6) 0.0198(7) 0.0186(6) 0.0023(5) 0.0027(5) 0.0011(5) C3_1 0.0153(6) 0.0191(6) 0.0195(6) 0.0019(5) 0.0025(5) 0.0021(5) C4_1 0.0176(7) 0.0186(6) 0.0188(7) 0.0006(5) 0.0032(5) 0.0021(5) C5_1 0.0217(7) 0.0240(7) 0.0193(7) -0.0015(5) 0.0025(6) 0.0004(6) C6_1 0.0287(8) 0.0263(7) 0.0153(6) 0.0002(5) 0.0044(6) 0.0034(6) C7_1 0.0278(8) 0.0231(7) 0.0226(7) 0.0027(6) 0.0106(6) 0.0026(6) C8_1 0.0192(7) 0.0222(7) 0.0240(7) -0.0001(5) 0.0057(6) -0.0001(5) C9_1 0.0179(7) 0.0194(6) 0.0183(6) 0.0004(5) 0.0034(5) 0.0024(5) C10_1 0.0175(7) 0.0214(7) 0.0145(6) 0.0002(5) 0.0022(5) 0.0002(5) C11_1 0.0207(7) 0.0216(7) 0.0223(7) 0.0028(5) 0.0045(6) 0.0002(5) C12_1 0.0179(7) 0.0276(7) 0.0235(7) 0.0016(6) 0.0050(6) -0.0010(6) C13_1 0.0211(7) 0.0274(7) 0.0215(7) -0.0008(6) 0.0044(5) 0.0060(6) C14_1 0.0267(7) 0.0215(7) 0.0225(7) -0.0026(5) 0.0041(6) 0.0022(6) C15_1 0.0198(7) 0.0217(7) 0.0191(6) -0.0021(5) 0.0033(5) -0.0023(5) C16_1 0.0182(7) 0.0190(6) 0.0178(6) -0.0008(5) 0.0029(5) -0.0032(5) C17_1 0.0198(7) 0.0221(7) 0.0192(6) -0.0011(5) 0.0028(5) -0.0002(5) C18_1 0.0290(8) 0.0224(7) 0.0186(6) 0.0017(5) 0.0020(6) -0.0008(6) C19_1 0.0290(8) 0.0276(8) 0.0188(6) 0.0005(6) 0.0073(6) -0.0049(6) C20_1 0.0211(7) 0.0267(7) 0.0230(7) -0.0037(6) 0.0069(6) -0.0040(6) C21_1 0.0183(7) 0.0229(7) 0.0192(7) 0.0006(5) 0.0026(5) -0.0009(5) C22_1 0.0175(7) 0.0216(7) 0.0167(6) -0.0014(5) 0.0042(5) -0.0002(5) C23_1 0.0193(7) 0.0220(7) 0.0202(6) -0.0003(5) 0.0045(5) 0.0018(5) C24_1 0.0254(7) 0.0208(7) 0.0262(7) -0.0028(6) 0.0093(6) -0.0034(6) C25_1 0.0202(7) 0.0301(8) 0.0303(8) -0.0074(6) 0.0062(6) -0.0074(6) C26_1 0.0186(7) 0.0325(8) 0.0279(7) -0.0006(6) -0.0003(6) -0.0003(6) C27_1 0.0196(7) 0.0245(7) 0.0233(7) 0.0011(6) 0.0012(6) 0.0006(6) O1_2 0.025(4) 0.023(4) 0.020(3) 0.000(3) -0.001(3) 0.004(3) C1_2 0.025(3) 0.025(3) 0.026(3) -0.003(3) 0.004(3) 0.008(3) C2_2 0.027(3) 0.027(3) 0.030(3) -0.002(3) 0.008(3) 0.001(3) C3_2 0.036(3) 0.035(3) 0.027(3) -0.006(3) 0.003(3) -0.002(3) C4_2 0.029(3) 0.026(4) 0.020(3) 0.001(3) 0.000(3) -0.003(3) O1_12 0.0187(8) 0.0197(8) 0.0165(8) 0.0009(7) 0.0007(7) 0.0032(7) C1_12 0.0310(11) 0.0238(15) 0.0160(10) -0.0017(10) -0.0015(9) -0.0003(9) C2_12 0.0273(12) 0.0287(10) 0.0271(9) -0.0089(7) 0.0012(8) -0.0008(9) C3_12 0.0320(12) 0.0394(14) 0.0333(12) -0.0112(10) 0.0035(9) 0.0093(10) C4_12 0.0232(15) 0.0223(14) 0.0274(13) 0.0004(10) -0.0027(11) 0.0072(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.1193 0 0 1 0.1407 2 -1 -2 0.0525 -2 1 2 0.0558 1 0 2 0.1483 -1 0 -2 0.1277 1 0 0 0.0980 -1 0 0 0.0857 0 1 1 0.1264 0 -1 -1 0.1597 0 -2 1 0.1293 -2 1 1 0.0396 2 -1 -1 0.0739 1 0 -1 0.0395 -2 -1 2 0.0577 1 1 2 0.1218 -1 0 2 0.0787 0 -1 2 0.1337 -1 -1 2 0.0902 1 0 -2 0.0743 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 O1_2 B1_1 C10_1 105.6(19) . . ? O1_2 B1_1 C9_1 109.0(17) . . ? C10_1 B1_1 C9_1 110.57(11) . . ? C10_1 B1_1 O1_12 105.3(3) . . ? C9_1 B1_1 O1_12 109.6(3) . . ? O1_2 B1_1 C2_1 110(3) . . ? C10_1 B1_1 C2_1 120.93(11) . . ? C9_1 B1_1 C2_1 99.93(11) . . ? O1_12 B1_1 C2_1 110.3(4) . . ? C3_1 C2_1 C16_1 122.15(12) . . ? C3_1 C2_1 B1_1 108.96(11) . . ? C16_1 C2_1 B1_1 128.79(12) . . ? C2_1 C3_1 C4_1 111.91(12) . . ? C2_1 C3_1 C22_1 127.45(12) . . ? C4_1 C3_1 C22_1 120.55(12) . . ? C5_1 C4_1 C9_1 120.92(12) . . ? C5_1 C4_1 C3_1 128.46(13) . . ? C9_1 C4_1 C3_1 110.61(11) . . ? C4_1 C5_1 C6_1 119.19(13) . . ? C4_1 C5_1 H5_1 120.4 . . ? C6_1 C5_1 H5_1 120.4 . . ? C7_1 C6_1 C5_1 120.40(13) . . ? C7_1 C6_1 H6_1 119.8 . . ? C5_1 C6_1 H6_1 119.8 . . ? C6_1 C7_1 C8_1 120.01(13) . . ? C6_1 C7_1 H7_1 120.0 . . ? C8_1 C7_1 H7_1 120.0 . . ? C9_1 C8_1 C7_1 120.67(13) . . ? C9_1 C8_1 H8_1 119.7 . . ? C7_1 C8_1 H8_1 119.7 . . ? C8_1 C9_1 C4_1 118.73(12) . . ? C8_1 C9_1 B1_1 132.66(13) . . ? C4_1 C9_1 B1_1 108.14(11) . . ? C15_1 C10_1 C11_1 116.35(12) . . ? C15_1 C10_1 B1_1 122.55(12) . . ? C11_1 C10_1 B1_1 120.52(12) . . ? C12_1 C11_1 C10_1 121.91(13) . . ? C12_1 C11_1 H11_1 119.0 . . ? C10_1 C11_1 H11_1 119.0 . . ? C11_1 C12_1 C13_1 120.36(13) . . ? C11_1 C12_1 H12_1 119.8 . . ? C13_1 C12_1 H12_1 119.8 . . ? C12_1 C13_1 C14_1 119.24(13) . . ? C12_1 C13_1 H13_1 120.4 . . ? C14_1 C13_1 H13_1 120.4 . . ? C13_1 C14_1 C15_1 119.95(13) . . ? C13_1 C14_1 H14_1 120.0 . . ? C15_1 C14_1 H14_1 120.0 . . ? C14_1 C15_1 C10_1 122.19(13) . . ? C14_1 C15_1 H15_1 118.9 . . ? C10_1 C15_1 H15_1 118.9 . . ? C21_1 C16_1 C17_1 117.40(12) . . ? C21_1 C16_1 C2_1 120.17(12) . . ? C17_1 C16_1 C2_1 122.42(12) . . ? C18_1 C17_1 C16_1 120.98(13) . . ? C18_1 C17_1 H17_1 119.5 . . ? C16_1 C17_1 H17_1 119.5 . . ? C17_1 C18_1 C19_1 120.45(13) . . ? C17_1 C18_1 H18_1 119.8 . . ? C19_1 C18_1 H18_1 119.8 . . ? C20_1 C19_1 C18_1 119.49(13) . . ? C20_1 C19_1 H19_1 120.3 . . ? C18_1 C19_1 H19_1 120.3 . . ? C19_1 C20_1 C21_1 120.13(13) . . ? C19_1 C20_1 H20_1 119.9 . . ? C21_1 C20_1 H20_1 119.9 . . ? C20_1 C21_1 C16_1 121.50(13) . . ? C20_1 C21_1 H21_1 119.3 . . ? C16_1 C21_1 H21_1 119.3 . . ? C27_1 C22_1 C23_1 117.92(13) . . ? C27_1 C22_1 C3_1 121.46(12) . . ? C23_1 C22_1 C3_1 120.56(12) . . ? C24_1 C23_1 C22_1 121.02(13) . . ? C24_1 C23_1 H23_1 119.5 . . ? C22_1 C23_1 H23_1 119.5 . . ? C25_1 C24_1 C23_1 120.19(13) . . ? C25_1 C24_1 H24_1 119.9 . . ? C23_1 C24_1 H24_1 119.9 . . ? C26_1 C25_1 C24_1 119.62(14) . . ? C26_1 C25_1 H25_1 120.2 . . ? C24_1 C25_1 H25_1 120.2 . . ? C25_1 C26_1 C27_1 120.21(14) . . ? C25_1 C26_1 H26_1 119.9 . . ? C27_1 C26_1 H26_1 119.9 . . ? C26_1 C27_1 C22_1 121.03(14) . . ? C26_1 C27_1 H27_1 119.5 . . ? C22_1 C27_1 H27_1 119.5 . . ? C4_2 O1_2 C1_2 111.1(16) . . ? C4_2 O1_2 B1_1 122(4) . . ? C1_2 O1_2 B1_1 114(4) . . ? O1_2 C1_2 C2_2 103.0(16) . . ? O1_2 C1_2 H1A_2 111.2 . . ? C2_2 C1_2 H1A_2 111.2 . . ? O1_2 C1_2 H1B_2 111.2 . . ? C2_2 C1_2 H1B_2 111.2 . . ? H1A_2 C1_2 H1B_2 109.1 . . ? C1_2 C2_2 C3_2 101.6(15) . . ? C1_2 C2_2 H2A_2 111.4 . . ? C3_2 C2_2 H2A_2 111.4 . . ? C1_2 C2_2 H2B_2 111.4 . . ? C3_2 C2_2 H2B_2 111.4 . . ? H2A_2 C2_2 H2B_2 109.3 . . ? C4_2 C3_2 C2_2 103.1(15) . . ? C4_2 C3_2 H3A_2 111.1 . . ? C2_2 C3_2 H3A_2 111.1 . . ? C4_2 C3_2 H3B_2 111.1 . . ? C2_2 C3_2 H3B_2 111.1 . . ? H3A_2 C3_2 H3B_2 109.1 . . ? O1_2 C4_2 C3_2 102.0(17) . . ? O1_2 C4_2 H4A_2 111.4 . . ? C3_2 C4_2 H4A_2 111.4 . . ? O1_2 C4_2 H4B_2 111.4 . . ? C3_2 C4_2 H4B_2 111.4 . . ? H4A_2 C4_2 H4B_2 109.2 . . ? C4_12 O1_12 C1_12 109.4(3) . . ? C4_12 O1_12 B1_1 120.2(6) . . ? C1_12 O1_12 B1_1 118.1(7) . . ? O1_12 C1_12 C2_12 104.4(4) . . ? O1_12 C1_12 H1A_12 110.9 . . ? C2_12 C1_12 H1A_12 110.9 . . ? O1_12 C1_12 H1B_12 110.9 . . ? C2_12 C1_12 H1B_12 110.9 . . ? H1A_12 C1_12 H1B_12 108.9 . . ? C1_12 C2_12 C3_12 102.0(3) . . ? C1_12 C2_12 H2A_12 111.4 . . ? C3_12 C2_12 H2A_12 111.4 . . ? C1_12 C2_12 H2B_12 111.4 . . ? C3_12 C2_12 H2B_12 111.4 . . ? H2A_12 C2_12 H2B_12 109.2 . . ? C4_12 C3_12 C2_12 102.5(3) . . ? C4_12 C3_12 H3A_12 111.3 . . ? C2_12 C3_12 H3A_12 111.3 . . ? C4_12 C3_12 H3B_12 111.3 . . ? C2_12 C3_12 H3B_12 111.3 . . ? H3A_12 C3_12 H3B_12 109.2 . . ? O1_12 C4_12 C3_12 104.4(3) . . ? O1_12 C4_12 H4A_12 110.9 . . ? C3_12 C4_12 H4A_12 110.9 . . ? O1_12 C4_12 H4B_12 110.9 . . ? C3_12 C4_12 H4B_12 110.9 . . ? H4A_12 C4_12 H4B_12 108.9 . . ? 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 B1_1 O1_2 1.59(5) . ? B1_1 C10_1 1.607(2) . ? B1_1 C9_1 1.6150(19) . ? B1_1 O1_12 1.619(9) . ? B1_1 C2_1 1.635(2) . ? C2_1 C3_1 1.3611(18) . ? C2_1 C16_1 1.4820(18) . ? C3_1 C4_1 1.4830(18) . ? C3_1 C22_1 1.4904(18) . ? C4_1 C5_1 1.3953(19) . ? C4_1 C9_1 1.4100(19) . ? C5_1 C6_1 1.3962(19) . ? C5_1 H5_1 0.9500 . ? C6_1 C7_1 1.386(2) . ? C6_1 H6_1 0.9500 . ? C7_1 C8_1 1.401(2) . ? C7_1 H7_1 0.9500 . ? C8_1 C9_1 1.3856(19) . ? C8_1 H8_1 0.9500 . ? C10_1 C15_1 1.3982(19) . ? C10_1 C11_1 1.4069(19) . ? C11_1 C12_1 1.3868(19) . ? C11_1 H11_1 0.9500 . ? C12_1 C13_1 1.387(2) . ? C12_1 H12_1 0.9500 . ? C13_1 C14_1 1.388(2) . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.3936(19) . ? C14_1 H14_1 0.9500 . ? C15_1 H15_1 0.9500 . ? C16_1 C21_1 1.4045(19) . ? C16_1 C17_1 1.4051(19) . ? C17_1 C18_1 1.3869(19) . ? C17_1 H17_1 0.9500 . ? C18_1 C19_1 1.391(2) . ? C18_1 H18_1 0.9500 . ? C19_1 C20_1 1.386(2) . ? C19_1 H19_1 0.9500 . ? C20_1 C21_1 1.3862(19) . ? C20_1 H20_1 0.9500 . ? C21_1 H21_1 0.9500 . ? C22_1 C27_1 1.3978(19) . ? C22_1 C23_1 1.3989(19) . ? C23_1 C24_1 1.3895(19) . ? C23_1 H23_1 0.9500 . ? C24_1 C25_1 1.387(2) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.385(2) . ? C25_1 H25_1 0.9500 . ? C26_1 C27_1 1.391(2) . ? C26_1 H26_1 0.9500 . ? C27_1 H27_1 0.9500 . ? O1_2 C4_2 1.48(2) . ? O1_2 C1_2 1.49(2) . ? C1_2 C2_2 1.508(18) . ? C1_2 H1A_2 0.9900 . ? C1_2 H1B_2 0.9900 . ? C2_2 C3_2 1.529(13) . ? C2_2 H2A_2 0.9900 . ? C2_2 H2B_2 0.9900 . ? C3_2 C4_2 1.518(19) . ? C3_2 H3A_2 0.9900 . ? C3_2 H3B_2 0.9900 . ? C4_2 H4A_2 0.9900 . ? C4_2 H4B_2 0.9900 . ? O1_12 C4_12 1.475(4) . ? O1_12 C1_12 1.478(4) . ? C1_12 C2_12 1.513(6) . ? C1_12 H1A_12 0.9900 . ? C1_12 H1B_12 0.9900 . ? C2_12 C3_12 1.525(3) . ? C2_12 H2A_12 0.9900 . ? C2_12 H2B_12 0.9900 . ? C3_12 C4_12 1.516(5) . ? C3_12 H3A_12 0.9900 . ? C3_12 H3B_12 0.9900 . ? C4_12 H4A_12 0.9900 . ? C4_12 H4B_12 0.9900 . ? 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_2 B1_1 C2_1 C3_1 -120.2(16) . . . . ? C10_1 B1_1 C2_1 C3_1 115.88(14) . . . . ? C9_1 B1_1 C2_1 C3_1 -5.50(14) . . . . ? O1_12 B1_1 C2_1 C3_1 -120.8(3) . . . . ? O1_2 B1_1 C2_1 C16_1 56.3(16) . . . . ? C10_1 B1_1 C2_1 C16_1 -67.62(19) . . . . ? C9_1 B1_1 C2_1 C16_1 171.01(13) . . . . ? O1_12 B1_1 C2_1 C16_1 55.7(3) . . . . ? C16_1 C2_1 C3_1 C4_1 -174.12(12) . . . . ? B1_1 C2_1 C3_1 C4_1 2.66(15) . . . . ? C16_1 C2_1 C3_1 C22_1 9.4(2) . . . . ? B1_1 C2_1 C3_1 C22_1 -173.77(12) . . . . ? C2_1 C3_1 C4_1 C5_1 -176.74(13) . . . . ? C22_1 C3_1 C4_1 C5_1 0.0(2) . . . . ? C2_1 C3_1 C4_1 C9_1 1.92(16) . . . . ? C22_1 C3_1 C4_1 C9_1 178.63(11) . . . . ? C9_1 C4_1 C5_1 C6_1 2.1(2) . . . . ? C3_1 C4_1 C5_1 C6_1 -179.38(13) . . . . ? C4_1 C5_1 C6_1 C7_1 -1.7(2) . . . . ? C5_1 C6_1 C7_1 C8_1 -0.7(2) . . . . ? C6_1 C7_1 C8_1 C9_1 2.9(2) . . . . ? C7_1 C8_1 C9_1 C4_1 -2.5(2) . . . . ? C7_1 C8_1 C9_1 B1_1 -173.63(14) . . . . ? C5_1 C4_1 C9_1 C8_1 0.0(2) . . . . ? C3_1 C4_1 C9_1 C8_1 -178.73(12) . . . . ? C5_1 C4_1 C9_1 B1_1 173.17(12) . . . . ? C3_1 C4_1 C9_1 B1_1 -5.61(15) . . . . ? O1_2 B1_1 C9_1 C8_1 -66(3) . . . . ? C10_1 B1_1 C9_1 C8_1 49.8(2) . . . . ? O1_12 B1_1 C9_1 C8_1 -65.9(5) . . . . ? C2_1 B1_1 C9_1 C8_1 178.33(14) . . . . ? O1_2 B1_1 C9_1 C4_1 122(3) . . . . ? C10_1 B1_1 C9_1 C4_1 -121.99(12) . . . . ? O1_12 B1_1 C9_1 C4_1 122.3(4) . . . . ? C2_1 B1_1 C9_1 C4_1 6.54(13) . . . . ? O1_2 B1_1 C10_1 C15_1 -148(2) . . . . ? C9_1 B1_1 C10_1 C15_1 94.19(15) . . . . ? O1_12 B1_1 C10_1 C15_1 -147.5(4) . . . . ? C2_1 B1_1 C10_1 C15_1 -21.89(19) . . . . ? O1_2 B1_1 C10_1 C11_1 41(2) . . . . ? C9_1 B1_1 C10_1 C11_1 -76.77(15) . . . . ? O1_12 B1_1 C10_1 C11_1 41.5(4) . . . . ? C2_1 B1_1 C10_1 C11_1 167.15(12) . . . . ? C15_1 C10_1 C11_1 C12_1 0.3(2) . . . . ? B1_1 C10_1 C11_1 C12_1 171.76(12) . . . . ? C10_1 C11_1 C12_1 C13_1 -0.5(2) . . . . ? C11_1 C12_1 C13_1 C14_1 0.4(2) . . . . ? C12_1 C13_1 C14_1 C15_1 -0.2(2) . . . . ? C13_1 C14_1 C15_1 C10_1 -0.1(2) . . . . ? C11_1 C10_1 C15_1 C14_1 0.02(19) . . . . ? B1_1 C10_1 C15_1 C14_1 -171.29(12) . . . . ? C3_1 C2_1 C16_1 C21_1 48.61(19) . . . . ? B1_1 C2_1 C16_1 C21_1 -127.49(15) . . . . ? C3_1 C2_1 C16_1 C17_1 -132.21(15) . . . . ? B1_1 C2_1 C16_1 C17_1 51.7(2) . . . . ? C21_1 C16_1 C17_1 C18_1 -2.5(2) . . . . ? C2_1 C16_1 C17_1 C18_1 178.27(13) . . . . ? C16_1 C17_1 C18_1 C19_1 1.9(2) . . . . ? C17_1 C18_1 C19_1 C20_1 0.0(2) . . . . ? C18_1 C19_1 C20_1 C21_1 -1.2(2) . . . . ? C19_1 C20_1 C21_1 C16_1 0.4(2) . . . . ? C17_1 C16_1 C21_1 C20_1 1.4(2) . . . . ? C2_1 C16_1 C21_1 C20_1 -179.38(13) . . . . ? C2_1 C3_1 C22_1 C27_1 -135.19(15) . . . . ? C4_1 C3_1 C22_1 C27_1 48.65(18) . . . . ? C2_1 C3_1 C22_1 C23_1 47.7(2) . . . . ? C4_1 C3_1 C22_1 C23_1 -128.48(13) . . . . ? C27_1 C22_1 C23_1 C24_1 -1.49(19) . . . . ? C3_1 C22_1 C23_1 C24_1 175.74(12) . . . . ? C22_1 C23_1 C24_1 C25_1 0.9(2) . . . . ? C23_1 C24_1 C25_1 C26_1 0.4(2) . . . . ? C24_1 C25_1 C26_1 C27_1 -1.2(2) . . . . ? C25_1 C26_1 C27_1 C22_1 0.6(2) . . . . ? C23_1 C22_1 C27_1 C26_1 0.8(2) . . . . ? C3_1 C22_1 C27_1 C26_1 -176.45(13) . . . . ? C10_1 B1_1 O1_2 C4_2 58(5) . . . . ? C9_1 B1_1 O1_2 C4_2 177(4) . . . . ? C2_1 B1_1 O1_2 C4_2 -74(5) . . . . ? C10_1 B1_1 O1_2 C1_2 -165(4) . . . . ? C9_1 B1_1 O1_2 C1_2 -46(5) . . . . ? C2_1 B1_1 O1_2 C1_2 63(4) . . . . ? C4_2 O1_2 C1_2 C2_2 -14(6) . . . . ? B1_1 O1_2 C1_2 C2_2 -156(3) . . . . ? O1_2 C1_2 C2_2 C3_2 35(4) . . . . ? C1_2 C2_2 C3_2 C4_2 -44(3) . . . . ? C1_2 O1_2 C4_2 C3_2 -13(6) . . . . ? B1_1 O1_2 C4_2 C3_2 126(4) . . . . ? C2_2 C3_2 C4_2 O1_2 35(4) . . . . ? C10_1 B1_1 O1_12 C4_12 -163.7(7) . . . . ? C9_1 B1_1 O1_12 C4_12 -44.8(9) . . . . ? C2_1 B1_1 O1_12 C4_12 64.2(9) . . . . ? C10_1 B1_1 O1_12 C1_12 58.0(9) . . . . ? C9_1 B1_1 O1_12 C1_12 176.9(7) . . . . ? C2_1 B1_1 O1_12 C1_12 -74.0(8) . . . . ? C4_12 O1_12 C1_12 C2_12 14.7(11) . . . . ? B1_1 O1_12 C1_12 C2_12 157.2(7) . . . . ? O1_12 C1_12 C2_12 C3_12 -34.7(8) . . . . ? C1_12 C2_12 C3_12 C4_12 41.6(5) . . . . ? C1_12 O1_12 C4_12 C3_12 11.5(11) . . . . ? B1_1 O1_12 C4_12 C3_12 -130.0(7) . . . . ? C2_12 C3_12 C4_12 O1_12 -32.8(7) . . . . ?