#------------------------------------------------------------------------------ #$Date: 2020-05-28 06:49:47 +0300 (Thu, 28 May 2020) $ #$Revision: 252429 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157518.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_7157518 loop_ _publ_author_name 'Zhang, Chuyi' 'Wang, Qian' 'Tian, Song' 'Zhang, Jianwei' 'Li, Jiaoyi' 'Zhou, Ling' 'Lu, Jian' _publ_section_title ; Palladium-Catalyzed Regioselective Synthesis of B(4,5)- or B(4)-Substituted o-Carboranes Containing \a,\b-Unsaturated Carbonyls ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00698J _journal_year 2020 _chemical_formula_moiety 'C22 H44 B10 O4' _chemical_formula_sum 'C22 H44 B10 O4' _chemical_formula_weight 480.67 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014 _audit_update_record ; 2020-01-09 deposited with the CCDC. 2020-05-26 downloaded from the CCDC. ; _cell_angle_alpha 87.493(9) _cell_angle_beta 84.584(8) _cell_angle_gamma 66.838(7) _cell_formula_units_Z 2 _cell_length_a 10.486(5) _cell_length_b 11.704(6) _cell_length_c 13.581(7) _cell_measurement_reflns_used 1886 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.37 _cell_measurement_theta_min 2.43 _cell_volume 1525.5(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.860 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0491 _diffrn_reflns_Laue_measured_fraction_full 0.860 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6963 _diffrn_reflns_point_group_measured_fraction_full 0.860 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.024 _diffrn_reflns_theta_min 1.506 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_T_max 0.7450 _exptl_absorpt_correction_T_min 0.6468 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.046 _exptl_crystal_density_meas 0 _exptl_crystal_description Block _exptl_crystal_F_000 516 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.250 _refine_diff_density_max 0.410 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.093 _refine_ls_extinction_coef 0.033(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 378 _refine_ls_number_reflns 4756 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0835 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1942P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2398 _refine_ls_wR_factor_ref 0.2813 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3089 _reflns_number_total 4756 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00698j2.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 1525.4(13) _cod_database_code 7157518 _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 0.975 _shelx_estimated_absorpt_t_max 0.985 _shelxl_version_number 2014-3 _shelx_res_file ; TITL 1 in P-1 CELL 0.71073 10.4856 11.7038 13.5809 87.493 84.584 66.838 ZERR 2.00 0.0050 0.0059 0.0065 0.009 0.008 0.007 LATT 1 SFAC C H B O UNIT 44 88 20 8 OMIT 7 -2 1 OMIT 1 3 1 OMIT 2 6 1 OMIT -1 2 3 OMIT 2 5 3 OMIT -1 -6 10 L.S. 4 ACTA BOND FMAP 2 PLAN 20 SIZE 0.25 0.30 0.40 TEMP 23.000 WGHT 0.194200 EXTI 0.032764 FVAR 0.27292 MOLE 1 B1 3 0.505978 0.736192 0.385384 11.00000 0.07641 0.09782 = 0.04862 -0.00111 0.00349 -0.02012 B2 3 0.411706 0.885944 0.334232 11.00000 0.06271 0.08955 = 0.04752 -0.01030 0.00663 -0.00381 B3 3 0.429411 0.749622 0.272545 11.00000 0.05990 0.08473 = 0.05260 0.00206 0.00521 -0.02177 B4 3 0.445407 0.877272 0.204268 11.00000 0.04504 0.06182 = 0.04958 -0.00848 0.00087 -0.00688 B5 3 0.562649 0.720727 0.173864 11.00000 0.04999 0.05449 = 0.05135 -0.00218 -0.00498 -0.01153 B6 3 0.720857 0.692503 0.228751 11.00000 0.05533 0.06063 = 0.05071 -0.01101 -0.00622 -0.00645 B7 3 0.685639 0.703002 0.357161 11.00000 0.07035 0.08058 = 0.04852 -0.00491 -0.01023 -0.01080 B8 3 0.568400 0.854347 0.387986 11.00000 0.07920 0.08913 = 0.04377 -0.01863 -0.00244 -0.01140 B9 3 0.531292 0.942383 0.276591 11.00000 0.06092 0.06678 = 0.06268 -0.02189 -0.00120 -0.00748 B10 3 0.599007 0.635777 0.286071 11.00000 0.07256 0.06943 = 0.05378 -0.00118 -0.00770 -0.01496 C1 1 0.351315 0.962383 0.126091 11.00000 0.05261 0.06239 = 0.05564 -0.00230 -0.00219 -0.01074 C2 1 0.221078 1.032873 0.143257 11.00000 0.04828 0.06560 = 0.05622 0.00240 -0.00324 -0.00897 AFIX 43 H2 2 0.179454 1.033366 0.206903 11.00000 -1.20000 AFIX 0 C3 1 0.134766 1.112625 0.067435 11.00000 0.04297 0.05616 = 0.06162 -0.00549 -0.00082 -0.01286 C4 1 -0.103487 1.264743 0.046620 11.00000 0.05057 0.07209 = 0.07470 0.00391 -0.01243 -0.00622 C5 1 -0.122083 1.206377 -0.044101 11.00000 0.09180 0.11449 = 0.14757 -0.01426 -0.05784 -0.01932 AFIX 33 H5A 2 -0.191606 1.267626 -0.080914 11.00000 -1.50000 H5B 2 -0.035480 1.174382 -0.084448 11.00000 -1.50000 H5C 2 -0.151073 1.139741 -0.025050 11.00000 -1.50000 AFIX 0 C6 1 -0.061423 1.370271 0.020032 11.00000 0.10896 0.05496 = 0.19932 0.01592 -0.05814 -0.01253 AFIX 33 H6A 2 -0.130697 1.430980 -0.017305 11.00000 -1.50000 H6B 2 -0.052756 1.407573 0.079260 11.00000 -1.50000 H6C 2 0.026348 1.340409 -0.019029 11.00000 -1.50000 AFIX 0 C7 1 -0.230394 1.304510 0.118873 11.00000 0.06627 0.17611 = 0.13475 0.03156 0.01169 0.03401 AFIX 33 H7A 2 -0.307453 1.366181 0.088538 11.00000 -1.50000 H7B 2 -0.252313 1.233910 0.137851 11.00000 -1.50000 H7C 2 -0.212519 1.338856 0.176406 11.00000 -1.50000 AFIX 0 C8 1 0.570531 0.664789 0.070289 11.00000 0.04757 0.05375 = 0.05659 -0.00128 -0.00676 -0.01362 AFIX 43 H23 2 0.533453 0.604763 0.067940 11.00000 -1.20000 AFIX 0 C9 1 0.623576 0.693026 -0.013663 11.00000 0.06238 0.06273 = 0.05773 -0.00839 -0.00015 -0.02485 C10 1 0.635346 0.626911 -0.106507 11.00000 0.05663 0.05776 = 0.05119 -0.00674 -0.00572 -0.01849 C11 1 0.723630 0.620682 -0.280152 11.00000 0.09393 0.07868 = 0.04319 -0.01543 0.00546 -0.02948 C12 1 0.831386 0.489225 -0.275173 11.00000 0.10730 0.11175 = 0.08305 -0.03208 0.00557 -0.00570 AFIX 33 H12A 2 0.853148 0.453454 -0.339999 11.00000 -1.50000 H12B 2 0.914182 0.490176 -0.251155 11.00000 -1.50000 H12C 2 0.795245 0.440580 -0.231203 11.00000 -1.50000 AFIX 0 C13 1 0.593990 0.627810 -0.321733 11.00000 0.13476 0.16141 = 0.06583 -0.01098 -0.03551 -0.03965 AFIX 33 H13A 2 0.616589 0.592888 -0.386869 11.00000 -1.50000 H13B 2 0.551544 0.582021 -0.279880 11.00000 -1.50000 H13C 2 0.530406 0.713109 -0.325210 11.00000 -1.50000 AFIX 0 C14 1 0.783988 0.705992 -0.335166 11.00000 0.21798 0.13756 = 0.07279 -0.02151 0.04388 -0.09263 AFIX 33 H14A 2 0.809452 0.680520 -0.402909 11.00000 -1.50000 H14B 2 0.715785 0.789820 -0.332466 11.00000 -1.50000 H14C 2 0.864950 0.701658 -0.304959 11.00000 -1.50000 AFIX 0 C15 1 0.816882 0.863734 0.286839 11.00000 0.07607 0.10427 = 0.08460 -0.02440 -0.01557 -0.03524 C16 1 0.800690 0.970181 0.352294 11.00000 0.13450 0.13253 = 0.11812 -0.03461 -0.00509 -0.07289 AFIX 23 H16A 2 0.714687 1.039260 0.339485 11.00000 -1.20000 H16B 2 0.791327 0.944779 0.420628 11.00000 -1.20000 AFIX 0 C17 1 0.912797 1.014122 0.340930 11.00000 0.18362 0.16426 = 0.08850 -0.01206 -0.01733 -0.11736 AFIX 23 H17A 2 0.925746 1.037208 0.272390 11.00000 -1.20000 H17B 2 0.998584 0.947624 0.357927 11.00000 -1.20000 AFIX 0 C18 1 0.880967 1.128418 0.408282 11.00000 0.40848 0.23506 = 0.14297 0.02203 -0.05916 -0.25866 AFIX 23 H18A 2 0.786954 1.145156 0.436569 11.00000 -1.20000 H18B 2 0.939510 1.092306 0.461988 11.00000 -1.20000 AFIX 0 C19 1 0.882214 1.218614 0.401169 11.00000 0.78430 0.19689 = 0.10988 -0.03147 0.05987 -0.26289 AFIX 23 H19A 2 0.818662 1.258130 0.350846 11.00000 -1.20000 H19B 2 0.974225 1.203856 0.369693 11.00000 -1.20000 AFIX 0 C20 1 0.856650 1.317996 0.469826 11.00000 0.29356 0.12147 = 0.14193 -0.04711 0.00245 -0.06282 AFIX 33 H20A 2 0.868014 1.386886 0.434823 11.00000 -1.50000 H20B 2 0.763441 1.344077 0.500510 11.00000 -1.50000 H20C 2 0.921545 1.288916 0.519664 11.00000 -1.50000 AFIX 0 C21 1 0.693000 0.826516 0.290286 11.00000 0.05930 0.07166 = 0.05321 -0.01707 -0.00995 -0.01151 C22 1 0.620990 0.835569 0.186468 11.00000 0.04743 0.05853 = 0.04477 -0.01020 -0.00209 -0.01142 H1 2 0.460206 0.709768 0.448834 11.00000 0.09716 H3 2 0.530700 1.034546 0.268550 11.00000 0.05344 H4 2 0.666782 0.868695 0.129386 11.00000 0.05151 H5 2 0.328961 0.726109 0.265250 11.00000 0.08347 H6 2 0.306876 0.951054 0.365505 11.00000 0.08746 H7 2 0.591840 0.888720 0.451941 11.00000 0.10255 H8 2 0.773128 0.654978 0.402609 11.00000 0.09813 H9 2 0.834170 0.893618 0.222574 11.00000 0.12033 H10 2 0.912120 0.784222 0.290021 11.00000 0.12705 H11 2 0.393914 0.962908 0.050419 11.00000 0.10031 H12 2 0.673858 0.754824 -0.015124 11.00000 0.06739 H24 2 0.821086 0.644999 0.191246 11.00000 0.06379 H25 2 0.628156 0.528331 0.285576 11.00000 0.08898 O1 4 0.176233 1.123619 -0.015958 11.00000 0.05618 0.08523 = 0.06279 0.01030 0.00170 -0.01136 O2 4 0.003761 1.171091 0.104308 11.00000 0.04719 0.08296 = 0.06881 0.00679 -0.00057 0.00187 O3 4 0.602522 0.540560 -0.113433 11.00000 0.10175 0.09000 = 0.06400 -0.01511 0.00084 -0.05324 O4 4 0.691782 0.673764 -0.180045 11.00000 0.10089 0.07376 = 0.05041 -0.01629 0.00771 -0.04079 HKLF 4 REM 1 in P-1 REM R1 = 0.0835 for 3089 Fo > 4sig(Fo) and 0.1120 for all 4756 data REM 378 parameters refined using 0 restraints END WGHT 0.1944 0.0000 REM Highest difference peak 0.410, deepest hole -0.313, 1-sigma level 0.093 Q1 1 0.9614 1.1193 0.3654 11.00000 0.05 0.41 Q2 1 0.8949 0.8111 0.2311 11.00000 0.05 0.33 Q3 1 0.7544 0.5806 -0.4035 11.00000 0.05 0.33 Q4 1 0.9635 1.1853 0.3943 11.00000 0.05 0.32 Q5 1 1.0538 1.1015 0.3830 11.00000 0.05 0.31 Q6 1 -0.2394 1.2030 0.0928 11.00000 0.05 0.29 Q7 1 0.8198 1.2067 0.4116 11.00000 0.05 0.29 Q8 1 0.7701 0.6006 -0.3142 11.00000 0.05 0.27 Q9 1 0.5152 0.7741 -0.0033 11.00000 0.05 0.27 Q10 1 0.7715 0.5278 -0.3059 11.00000 0.05 0.27 Q11 1 0.7759 0.5615 -0.3019 11.00000 0.05 0.27 Q12 1 0.7445 0.4186 -0.2479 11.00000 0.05 0.26 Q13 1 0.9723 0.9357 0.3042 11.00000 0.05 0.25 Q14 1 0.8419 0.6179 -0.3807 11.00000 0.05 0.25 Q15 1 0.5772 0.7904 -0.0155 11.00000 0.05 0.25 Q16 1 0.7259 0.4781 -0.3751 11.00000 0.05 0.24 Q17 1 0.8275 0.7164 0.1834 11.00000 0.05 0.24 Q18 1 0.6423 0.6197 -0.3978 11.00000 0.05 0.24 Q19 1 0.4823 0.9092 0.3358 11.00000 0.05 0.24 Q20 1 0.9735 1.1928 0.3143 11.00000 0.05 0.24 ; _shelx_res_checksum 50932 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 B1 B 0.5060(5) 0.7362(5) 0.3854(3) 0.0792(12) Uani 1 1 d . . . . . B2 B 0.4117(4) 0.8859(4) 0.3342(3) 0.0751(12) Uani 1 1 d . . . . . B3 B 0.4294(4) 0.7496(4) 0.2725(3) 0.0685(10) Uani 1 1 d . . . . . B4 B 0.4454(3) 0.8773(3) 0.2043(2) 0.0566(9) Uani 1 1 d . . . . . B5 B 0.5626(3) 0.7207(3) 0.1739(2) 0.0546(8) Uani 1 1 d . . . . . B6 B 0.7209(4) 0.6925(3) 0.2288(3) 0.0602(9) Uani 1 1 d . . . . . B7 B 0.6856(4) 0.7030(4) 0.3572(3) 0.0718(11) Uani 1 1 d . . . . . B8 B 0.5684(5) 0.8543(4) 0.3880(3) 0.0770(12) Uani 1 1 d . . . . . B9 B 0.5313(4) 0.9424(4) 0.2766(3) 0.0685(10) Uani 1 1 d . . . . . B10 B 0.5990(4) 0.6358(4) 0.2861(3) 0.0691(10) Uani 1 1 d . . . . . C1 C 0.3513(3) 0.9624(3) 0.1261(2) 0.0606(8) Uani 1 1 d . . . . . C2 C 0.2211(3) 1.0329(3) 0.1433(2) 0.0610(8) Uani 1 1 d . . . . . H2 H 0.1795 1.0334 0.2069 0.073 Uiso 1 1 calc R U . . . C3 C 0.1348(3) 1.1126(3) 0.0674(2) 0.0557(8) Uani 1 1 d . . . . . C4 C -0.1035(3) 1.2647(3) 0.0466(3) 0.0710(9) Uani 1 1 d . . . . . C5 C -0.1221(5) 1.2064(5) -0.0441(4) 0.1208(17) Uani 1 1 d . . . . . H5A H -0.1916 1.2676 -0.0809 0.181 Uiso 1 1 calc R U . . . H5B H -0.0355 1.1744 -0.0844 0.181 Uiso 1 1 calc R U . . . H5C H -0.1511 1.1397 -0.0250 0.181 Uiso 1 1 calc R U . . . C6 C -0.0614(5) 1.3703(4) 0.0200(5) 0.1246(19) Uani 1 1 d . . . . . H6A H -0.1307 1.4310 -0.0173 0.187 Uiso 1 1 calc R U . . . H6B H -0.0528 1.4076 0.0793 0.187 Uiso 1 1 calc R U . . . H6C H 0.0263 1.3404 -0.0190 0.187 Uiso 1 1 calc R U . . . C7 C -0.2304(5) 1.3045(6) 0.1189(4) 0.153(3) Uani 1 1 d . . . . . H7A H -0.3075 1.3662 0.0885 0.230 Uiso 1 1 calc R U . . . H7B H -0.2523 1.2339 0.1379 0.230 Uiso 1 1 calc R U . . . H7C H -0.2125 1.3389 0.1764 0.230 Uiso 1 1 calc R U . . . C8 C 0.5705(3) 0.6648(3) 0.0703(2) 0.0544(7) Uani 1 1 d . . . . . H23 H 0.5335 0.6048 0.0679 0.065 Uiso 1 1 calc R U . . . C9 C 0.6236(3) 0.6930(3) -0.0137(2) 0.0609(8) Uani 1 1 d . . . . . C10 C 0.6353(3) 0.6269(3) -0.1065(2) 0.0561(7) Uani 1 1 d . . . . . C11 C 0.7236(4) 0.6207(3) -0.2802(2) 0.0736(10) Uani 1 1 d . . . . . C12 C 0.8314(5) 0.4892(4) -0.2752(3) 0.1122(16) Uani 1 1 d . . . . . H12A H 0.8531 0.4535 -0.3400 0.168 Uiso 1 1 calc R U . . . H12B H 0.9142 0.4902 -0.2512 0.168 Uiso 1 1 calc R U . . . H12C H 0.7952 0.4406 -0.2312 0.168 Uiso 1 1 calc R U . . . C13 C 0.5940(5) 0.6278(5) -0.3217(3) 0.1242(19) Uani 1 1 d . . . . . H13A H 0.6166 0.5929 -0.3869 0.186 Uiso 1 1 calc R U . . . H13B H 0.5515 0.5820 -0.2799 0.186 Uiso 1 1 calc R U . . . H13C H 0.5304 0.7131 -0.3252 0.186 Uiso 1 1 calc R U . . . C14 C 0.7840(7) 0.7060(5) -0.3352(3) 0.139(2) Uani 1 1 d . . . . . H14A H 0.8095 0.6805 -0.4029 0.208 Uiso 1 1 calc R U . . . H14B H 0.7158 0.7898 -0.3325 0.208 Uiso 1 1 calc R U . . . H14C H 0.8650 0.7017 -0.3050 0.208 Uiso 1 1 calc R U . . . C15 C 0.8169(4) 0.8637(5) 0.2868(4) 0.0870(12) Uani 1 1 d . . . . . C16 C 0.8007(6) 0.9702(5) 0.3523(4) 0.1213(17) Uani 1 1 d . . . . . H16A H 0.7147 1.0393 0.3395 0.146 Uiso 1 1 calc R U . . . H16B H 0.7913 0.9448 0.4206 0.146 Uiso 1 1 calc R U . . . C17 C 0.9128(7) 1.0141(6) 0.3409(3) 0.1293(19) Uani 1 1 d . . . . . H17A H 0.9257 1.0372 0.2724 0.155 Uiso 1 1 calc R U . . . H17B H 0.9986 0.9476 0.3579 0.155 Uiso 1 1 calc R U . . . C18 C 0.8810(13) 1.1284(10) 0.4083(6) 0.219(5) Uani 1 1 d . . . . . H18A H 0.7870 1.1452 0.4366 0.263 Uiso 1 1 calc R U . . . H18B H 0.9395 1.0923 0.4620 0.263 Uiso 1 1 calc R U . . . C19 C 0.882(2) 1.2186(9) 0.4012(6) 0.347(11) Uani 1 1 d . . . . . H19A H 0.8187 1.2581 0.3508 0.417 Uiso 1 1 calc R U . . . H19B H 0.9742 1.2039 0.3697 0.417 Uiso 1 1 calc R U . . . C20 C 0.8566(10) 1.3180(6) 0.4698(5) 0.191(4) Uani 1 1 d . . . . . H20A H 0.8680 1.3869 0.4348 0.287 Uiso 1 1 calc R U . . . H20B H 0.7634 1.3441 0.5005 0.287 Uiso 1 1 calc R U . . . H20C H 0.9215 1.2889 0.5197 0.287 Uiso 1 1 calc R U . . . C21 C 0.6930(3) 0.8265(3) 0.2903(2) 0.0649(9) Uani 1 1 d . . . . . C22 C 0.6210(3) 0.8356(3) 0.1865(2) 0.0530(7) Uani 1 1 d . . . . . H1 H 0.460(4) 0.710(4) 0.449(3) 0.097(11) Uiso 1 1 d . . . . . H3 H 0.531(3) 1.035(3) 0.269(2) 0.053(7) Uiso 1 1 d . . . . . H4 H 0.667(3) 0.869(3) 0.129(2) 0.052(7) Uiso 1 1 d . . . . . H5 H 0.329(4) 0.726(3) 0.265(2) 0.083(10) Uiso 1 1 d . . . . . H6 H 0.307(4) 0.951(3) 0.366(3) 0.087(11) Uiso 1 1 d . . . . . H7 H 0.592(4) 0.889(4) 0.452(3) 0.103(12) Uiso 1 1 d . . . . . H8 H 0.773(4) 0.655(4) 0.403(3) 0.098(12) Uiso 1 1 d . . . . . H9 H 0.834(5) 0.894(5) 0.223(4) 0.120(17) Uiso 1 1 d . . . . . H10 H 0.912(5) 0.784(5) 0.290(3) 0.127(16) Uiso 1 1 d . . . . . H11 H 0.394(4) 0.963(4) 0.050(3) 0.100(12) Uiso 1 1 d . . . . . H12 H 0.674(3) 0.755(3) -0.015(2) 0.067(9) Uiso 1 1 d . . . . . H24 H 0.821(3) 0.645(3) 0.191(2) 0.064(8) Uiso 1 1 d . . . . . H25 H 0.628(4) 0.528(4) 0.286(3) 0.089(11) Uiso 1 1 d . . . . . O1 O 0.1762(2) 1.1236(2) -0.01596(17) 0.0739(7) Uani 1 1 d . . . . . O2 O 0.0038(2) 1.1711(2) 0.10431(16) 0.0754(7) Uani 1 1 d . . . . . O3 O 0.6025(3) 0.5406(2) -0.11343(16) 0.0804(8) Uani 1 1 d . . . . . O4 O 0.6918(3) 0.6738(2) -0.18004(15) 0.0734(7) Uani 1 1 d . . . . . 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 0.076(3) 0.098(3) 0.049(2) -0.001(2) 0.0035(19) -0.020(2) B2 0.063(2) 0.090(3) 0.048(2) -0.0103(19) 0.0066(17) -0.004(2) B3 0.060(2) 0.085(3) 0.053(2) 0.0021(18) 0.0052(16) -0.022(2) B4 0.0450(17) 0.062(2) 0.0496(19) -0.0085(16) 0.0009(14) -0.0069(15) B5 0.0500(18) 0.0545(19) 0.0513(19) -0.0022(15) -0.0050(14) -0.0115(15) B6 0.055(2) 0.061(2) 0.0507(19) -0.0110(16) -0.0062(15) -0.0065(16) B7 0.070(2) 0.081(3) 0.049(2) -0.0049(18) -0.0102(17) -0.011(2) B8 0.079(3) 0.089(3) 0.044(2) -0.0186(19) -0.0024(18) -0.011(2) B9 0.061(2) 0.067(2) 0.063(2) -0.0219(19) -0.0012(17) -0.0075(19) B10 0.073(2) 0.069(2) 0.054(2) -0.0012(18) -0.0077(17) -0.015(2) C1 0.0526(17) 0.0624(19) 0.0556(18) -0.0023(14) -0.0022(14) -0.0107(15) C2 0.0483(16) 0.0656(19) 0.0562(18) 0.0024(15) -0.0032(13) -0.0090(15) C3 0.0430(15) 0.0562(17) 0.062(2) -0.0055(14) -0.0008(13) -0.0129(13) C4 0.0506(17) 0.072(2) 0.075(2) 0.0039(17) -0.0124(15) -0.0062(16) C5 0.092(3) 0.114(4) 0.148(4) -0.014(3) -0.058(3) -0.019(3) C6 0.109(3) 0.055(2) 0.199(6) 0.016(3) -0.058(4) -0.013(2) C7 0.066(3) 0.176(6) 0.135(4) 0.032(4) 0.012(3) 0.034(3) C8 0.0476(15) 0.0538(17) 0.0566(17) -0.0013(13) -0.0068(13) -0.0136(13) C9 0.0624(18) 0.0627(19) 0.0577(19) -0.0084(15) -0.0001(14) -0.0249(16) C10 0.0566(17) 0.0578(18) 0.0512(17) -0.0067(14) -0.0057(13) -0.0185(15) C11 0.094(2) 0.079(2) 0.0432(17) -0.0154(16) 0.0055(16) -0.0295(19) C12 0.107(3) 0.112(3) 0.083(3) -0.032(3) 0.006(2) -0.006(3) C13 0.135(4) 0.161(5) 0.066(3) -0.011(3) -0.036(3) -0.040(4) C14 0.218(6) 0.138(4) 0.073(3) -0.022(3) 0.044(3) -0.093(5) C15 0.076(3) 0.104(3) 0.085(3) -0.024(2) -0.016(2) -0.035(2) C16 0.134(4) 0.133(4) 0.118(4) -0.035(3) -0.005(3) -0.073(4) C17 0.184(5) 0.164(5) 0.088(3) -0.012(3) -0.017(3) -0.117(5) C18 0.408(14) 0.235(9) 0.143(6) 0.022(6) -0.059(7) -0.259(11) C19 0.78(3) 0.197(9) 0.110(6) -0.031(6) 0.060(10) -0.263(16) C20 0.294(10) 0.121(5) 0.142(5) -0.047(4) 0.002(6) -0.063(6) C21 0.0593(18) 0.072(2) 0.0532(17) -0.0171(15) -0.0100(14) -0.0115(16) C22 0.0474(15) 0.0585(17) 0.0448(16) -0.0102(13) -0.0021(12) -0.0114(13) O1 0.0562(13) 0.0852(17) 0.0628(14) 0.0103(12) 0.0017(10) -0.0114(11) O2 0.0472(12) 0.0830(16) 0.0688(14) 0.0068(12) -0.0006(10) 0.0019(11) O3 0.1017(18) 0.0900(18) 0.0640(14) -0.0151(12) 0.0008(12) -0.0532(16) O4 0.1009(17) 0.0738(15) 0.0504(13) -0.0163(11) 0.0077(11) -0.0408(14) 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' B B 0.0013 0.0007 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag B8 B1 B3 107.8(3) . . ? B8 B1 B10 108.2(3) . . ? B3 B1 B10 60.1(2) . . ? B8 B1 B7 59.7(3) . . ? B3 B1 B7 107.9(3) . . ? B10 B1 B7 60.3(2) . . ? B8 B1 B2 59.6(3) . . ? B3 B1 B2 59.7(2) . . ? B10 B1 B2 107.7(3) . . ? B7 B1 B2 107.1(3) . . ? B9 B2 B8 61.0(3) . . ? B9 B2 B4 60.5(2) . . ? B8 B2 B4 109.0(3) . . ? B9 B2 B3 108.6(3) . . ? B8 B2 B3 107.4(3) . . ? B4 B2 B3 60.4(2) . . ? B9 B2 B1 108.3(3) . . ? B8 B2 B1 59.1(3) . . ? B4 B2 B1 108.3(3) . . ? B3 B2 B1 59.6(2) . . ? B1 B3 B2 60.6(3) . . ? B1 B3 B10 60.0(2) . . ? B2 B3 B10 108.3(3) . . ? B1 B3 B4 108.5(3) . . ? B2 B3 B4 59.7(2) . . ? B10 B3 B4 108.3(3) . . ? B1 B3 B5 108.2(3) . . ? B2 B3 B5 108.3(3) . . ? B10 B3 B5 59.7(2) . . ? B4 B3 B5 60.68(19) . . ? C1 B4 C22 119.0(3) . . ? C1 B4 B2 127.1(3) . . ? C22 B4 B2 103.6(2) . . ? C1 B4 B9 117.9(3) . . ? C22 B4 B9 59.09(19) . . ? B2 B4 B9 59.1(2) . . ? C1 B4 B3 129.2(3) . . ? C22 B4 B3 103.2(2) . . ? B2 B4 B3 59.9(2) . . ? B9 B4 B3 107.2(3) . . ? C1 B4 B5 120.6(2) . . ? C22 B4 B5 58.05(18) . . ? B2 B4 B5 107.8(3) . . ? B9 B4 B5 108.1(2) . . ? B3 B4 B5 59.7(2) . . ? C8 B5 C22 120.6(2) . . ? C8 B5 B10 125.8(3) . . ? C22 B5 B10 103.5(2) . . ? C8 B5 B3 128.1(3) . . ? C22 B5 B3 103.2(2) . . ? B10 B5 B3 59.9(2) . . ? C8 B5 B6 118.9(2) . . ? C22 B5 B6 58.12(19) . . ? B10 B5 B6 59.4(2) . . ? B3 B5 B6 106.9(2) . . ? C8 B5 B4 121.5(2) . . ? C22 B5 B4 58.19(18) . . ? B10 B5 B4 107.6(2) . . ? B3 B5 B4 59.6(2) . . ? B6 B5 B4 107.2(2) . . ? C22 B6 C21 57.45(18) . . ? C22 B6 B7 104.3(2) . . ? C21 B6 B7 58.6(2) . . ? C22 B6 B10 104.0(3) . . ? C21 B6 B10 105.7(3) . . ? B7 B6 B10 60.9(2) . . ? C22 B6 B5 58.39(18) . . ? C21 B6 B5 105.7(2) . . ? B7 B6 B5 108.7(3) . . ? B10 B6 B5 59.8(2) . . ? C21 B7 B6 59.8(2) . . ? C21 B7 B8 59.6(2) . . ? B6 B7 B8 109.1(3) . . ? C21 B7 B1 105.8(3) . . ? B6 B7 B1 108.3(3) . . ? B8 B7 B1 59.5(3) . . ? C21 B7 B10 105.9(3) . . ? B6 B7 B10 60.0(2) . . ? B8 B7 B10 107.6(3) . . ? B1 B7 B10 59.8(2) . . ? C21 B8 B1 106.0(3) . . ? C21 B8 B7 58.5(2) . . ? B1 B8 B7 60.8(3) . . ? C21 B8 B2 105.2(2) . . ? B1 B8 B2 61.2(3) . . ? B7 B8 B2 109.2(3) . . ? C21 B8 B9 59.1(2) . . ? B1 B8 B9 108.5(3) . . ? B7 B8 B9 108.0(3) . . ? B2 B8 B9 59.1(2) . . ? C22 B9 C21 57.01(17) . . ? C22 B9 B2 104.2(3) . . ? C21 B9 B2 105.5(3) . . ? C22 B9 B4 58.58(18) . . ? C21 B9 B4 105.7(2) . . ? B2 B9 B4 60.4(2) . . ? C22 B9 B8 103.4(3) . . ? C21 B9 B8 58.7(2) . . ? B2 B9 B8 59.9(3) . . ? B4 B9 B8 108.0(3) . . ? B6 B10 B5 60.8(2) . . ? B6 B10 B1 107.6(3) . . ? B5 B10 B1 108.6(3) . . ? B6 B10 B3 108.3(3) . . ? B5 B10 B3 60.4(2) . . ? B1 B10 B3 59.8(2) . . ? B6 B10 B7 59.1(2) . . ? B5 B10 B7 108.0(3) . . ? B1 B10 B7 59.9(2) . . ? B3 B10 B7 107.4(3) . . ? C2 C1 B4 125.0(3) . . ? C1 C2 C3 123.6(3) . . ? O1 C3 O2 124.2(3) . . ? O1 C3 C2 124.9(3) . . ? O2 C3 C2 110.9(3) . . ? O2 C4 C6 109.3(3) . . ? O2 C4 C5 110.1(3) . . ? C6 C4 C5 111.0(4) . . ? O2 C4 C7 102.5(3) . . ? C6 C4 C7 111.0(4) . . ? C5 C4 C7 112.5(4) . . ? C9 C8 B5 127.1(3) . . ? C8 C9 C10 122.5(3) . . ? O3 C10 O4 124.8(3) . . ? O3 C10 C9 124.9(3) . . ? O4 C10 C9 110.3(3) . . ? O4 C11 C13 110.6(3) . . ? O4 C11 C12 108.6(3) . . ? C13 C11 C12 112.8(4) . . ? O4 C11 C14 101.3(3) . . ? C13 C11 C14 111.6(4) . . ? C12 C11 C14 111.3(4) . . ? C16 C15 C21 116.2(4) . . ? C17 C16 C15 116.0(5) . . ? C16 C17 C18 111.3(6) . . ? C19 C18 C17 137.9(9) . . ? C18 C19 C20 134.2(10) . . ? C15 C21 C22 117.2(3) . . ? C15 C21 B7 122.7(3) . . ? C22 C21 B7 109.1(3) . . ? C15 C21 B8 124.6(3) . . ? C22 C21 B8 109.4(2) . . ? B7 C21 B8 61.8(2) . . ? C15 C21 B6 115.7(3) . . ? C22 C21 B6 60.63(19) . . ? B7 C21 B6 61.6(2) . . ? B8 C21 B6 112.3(3) . . ? C15 C21 B9 117.8(3) . . ? C22 C21 B9 61.14(19) . . ? B7 C21 B9 113.2(3) . . ? B8 C21 B9 62.2(2) . . ? B6 C21 B9 113.3(2) . . ? C21 C22 B6 61.92(19) . . ? C21 C22 B5 113.4(2) . . ? B6 C22 B5 63.5(2) . . ? C21 C22 B4 112.7(2) . . ? B6 C22 B4 116.1(3) . . ? B5 C22 B4 63.76(19) . . ? C21 C22 B9 61.9(2) . . ? B6 C22 B9 115.0(2) . . ? B5 C22 B9 115.5(2) . . ? B4 C22 B9 62.3(2) . . ? C3 O2 C4 122.4(2) . . ? C10 O4 C11 121.9(3) . . ? 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 B8 1.750(7) . ? B1 B3 1.769(6) . ? B1 B10 1.772(6) . ? B1 B7 1.774(6) . ? B1 B2 1.787(6) . ? B2 B9 1.744(6) . ? B2 B8 1.759(6) . ? B2 B4 1.766(5) . ? B2 B3 1.771(6) . ? B3 B10 1.774(6) . ? B3 B4 1.779(6) . ? B3 B5 1.782(5) . ? B4 C1 1.557(5) . ? B4 C22 1.705(4) . ? B4 B9 1.769(5) . ? B4 B5 1.799(5) . ? B5 C8 1.559(4) . ? B5 C22 1.702(5) . ? B5 B10 1.771(5) . ? B5 B6 1.788(5) . ? B6 C22 1.697(5) . ? B6 C21 1.718(5) . ? B6 B7 1.748(5) . ? B6 B10 1.765(6) . ? B7 C21 1.697(6) . ? B7 B8 1.755(6) . ? B7 B10 1.781(6) . ? B8 C21 1.717(5) . ? B8 B9 1.778(6) . ? B9 C22 1.714(4) . ? B9 C21 1.725(5) . ? C1 C2 1.292(4) . ? C2 C3 1.476(4) . ? C3 O1 1.194(3) . ? C3 O2 1.329(3) . ? C4 O2 1.484(4) . ? C4 C6 1.487(6) . ? C4 C5 1.499(6) . ? C4 C7 1.502(6) . ? C8 C9 1.308(4) . ? C9 C10 1.478(4) . ? C10 O3 1.199(4) . ? C10 O4 1.321(4) . ? C11 O4 1.473(4) . ? C11 C13 1.492(6) . ? C11 C12 1.512(6) . ? C11 C14 1.516(6) . ? C15 C16 1.508(6) . ? C15 C21 1.520(5) . ? C16 C17 1.451(7) . ? C17 C18 1.561(10) . ? C18 C19 1.061(9) . ? C19 C20 1.448(10) . ? C21 C22 1.641(4) . ?