#------------------------------------------------------------------------------ #$Date: 2024-06-01 01:14:32 +0300 (Sat, 01 Jun 2024) $ #$Revision: 292134 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571740.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_1571740 loop_ _publ_author_name 'Zhu, Mengjie' 'Wang, Puzhao' 'Wu, Zhengqiu' 'Zhong, Yangfa' 'Su, Laiman' 'Xin, Yuquan' 'Spokoyny, Alex' 'Zou, Chao' 'mu, xin' _publ_section_title ; A Pd-Catalyzed Route to Carborane-Fused Boron Heterocycles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02214A _journal_year 2024 _chemical_formula_moiety 'C14 H22 B10 N2 O4' _chemical_formula_sum 'C14 H22 B10 N2 O4' _chemical_formula_weight 390.43 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2023-03-24 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-01-04 deposited with the CCDC. 2024-05-28 downloaded from the CCDC. ; _cell_angle_alpha 104.407(2) _cell_angle_beta 96.511(2) _cell_angle_gamma 91.171(2) _cell_formula_units_Z 2 _cell_length_a 7.6015(3) _cell_length_b 10.8533(4) _cell_length_c 12.8730(5) _cell_measurement_reflns_used 6531 _cell_measurement_temperature 213.00 _cell_measurement_theta_max 54.931 _cell_measurement_theta_min 3.664 _cell_volume 1020.70(7) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 213.00 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0351 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14131 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.985 _diffrn_reflns_theta_min 3.663 _diffrn_source_current 2.86 _diffrn_source_power 0.1995708 _diffrn_source_voltage 69.78 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.6348 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1130 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.8455. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.270 _exptl_crystal_description block _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.183 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3851 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0513 _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^)+(0.0864P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1430 _refine_ls_wR_factor_ref 0.1565 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2934 _reflns_number_total 3851 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02214a2.cif _cod_data_source_block mj23176_0m _cod_database_code 1571740 _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_max 0.980 _shelx_estimated_absorpt_t_min 0.972 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11) 2.b Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C14(H14A,H14B,H14C) 2.c Boron cage BH refined with riding coordinates: C1(H1), B2(H2), B3(H3A), B4(H4A), B5(H5A), B6(H6), C7(H7), B8(H8), B11(H11A), B12(H12) ; _shelx_res_file ; TITL mj23176_0m_a.res in P-1 mj23176_0m.res created by SHELXL-2018/3 at 08:36:05 on 24-Mar-2023 REM Old TITL mj23176_0m in P-1 REM SHELXT solution in P-1: R1 0.223, Rweak 0.011, Alpha 0.059 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C14 C7 N4 O2 CELL 1.34139 7.6015 10.8533 12.873 104.407 96.511 91.171 ZERR 2 0.0003 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H B N O DISP B 0.007 0.0029 26.6 DISP C 0.0137 0.0067 57.1 DISP H 0 0 0.6 DISP N 0.0241 0.0134 109.9 DISP O 0.0389 0.0241 193.4 UNIT 28 44 20 4 8 L.S. 8 PLAN 5 SIZE 0.05 0.07 0.07 TEMP -60.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.086400 0.166700 FVAR 2.05282 O1 5 0.547953 0.045935 0.744398 11.00000 0.10910 0.08636 = 0.05115 -0.00566 0.01466 -0.04665 O2 5 0.494483 0.130107 0.912079 11.00000 0.10033 0.10235 = 0.06175 -0.00543 0.03159 -0.04333 O3 5 0.853994 0.651864 0.682566 11.00000 0.09127 0.05941 = 0.06726 0.00089 0.03890 -0.00758 O4 5 0.787852 0.782004 0.833764 11.00000 0.09601 0.05966 = 0.06669 -0.01088 0.03094 -0.02193 N1 4 0.841387 0.245755 0.786008 11.00000 0.04845 0.05715 = 0.04598 0.00851 0.00208 -0.00709 N2 4 0.585809 0.464081 0.716925 11.00000 0.04497 0.04965 = 0.05481 -0.00239 0.01476 0.00001 C1 1 0.916626 0.296061 0.488512 11.00000 0.06291 0.04895 = 0.05343 0.00621 0.02342 0.00558 AFIX 153 H1 2 1.031883 0.326268 0.453344 11.00000 -1.20000 AFIX 0 B2 3 0.721315 0.262346 0.408748 11.00000 0.08183 0.05607 = 0.04307 0.00521 0.01172 0.01023 AFIX 153 H2 2 0.697818 0.266035 0.322909 11.00000 -1.20000 AFIX 0 C3 1 0.987663 0.314216 0.846212 11.00000 0.05629 0.08986 = 0.06269 0.01646 -0.00815 -0.02104 AFIX 43 H3 2 1.077359 0.351912 0.817947 11.00000 -1.20000 AFIX 0 C4 1 0.984780 0.319929 0.952450 11.00000 0.07954 0.09506 = 0.05889 0.01456 -0.01789 -0.02143 AFIX 43 H4 2 1.070676 0.361042 1.009680 11.00000 -1.20000 AFIX 0 C5 1 0.831614 0.253851 0.960706 11.00000 0.08240 0.06630 = 0.04616 0.00898 0.00120 -0.00734 AFIX 43 H5 2 0.794386 0.242338 1.024989 11.00000 -1.20000 AFIX 0 C6 1 0.743808 0.208201 0.859044 11.00000 0.06098 0.04934 = 0.04273 0.00518 0.00687 -0.00441 C2 1 0.589120 0.121322 0.829416 11.00000 0.07407 0.05666 = 0.04435 0.00563 0.01144 -0.01171 C8 1 0.340869 0.042733 0.893024 11.00000 0.11175 0.13423 = 0.08989 0.01358 0.03288 -0.06069 AFIX 137 H8A 2 0.252603 0.064137 0.840621 11.00000 -1.50000 H8B 2 0.291336 0.049157 0.960267 11.00000 -1.50000 H8C 2 0.375770 -0.043623 0.865418 11.00000 -1.50000 AFIX 0 C9 1 0.448276 0.423683 0.762417 11.00000 0.05995 0.06425 = 0.09140 -0.01350 0.03689 -0.01239 AFIX 43 H9 2 0.387899 0.343461 0.737015 11.00000 -1.20000 AFIX 0 C10 1 0.410923 0.514957 0.849017 11.00000 0.07236 0.07482 = 0.08925 -0.01673 0.04553 -0.01414 AFIX 43 H10 2 0.322022 0.509473 0.893053 11.00000 -1.20000 AFIX 0 C11 1 0.528677 0.617784 0.860228 11.00000 0.06484 0.06506 = 0.05850 -0.01024 0.02249 -0.00440 AFIX 43 H11 2 0.534328 0.694996 0.913774 11.00000 -1.20000 AFIX 0 C12 1 0.635806 0.587211 0.779399 11.00000 0.04734 0.04926 = 0.04313 0.00055 0.00722 0.00110 C13 1 0.768548 0.671271 0.757470 11.00000 0.05441 0.04841 = 0.04165 0.00374 0.00643 0.00381 C14 1 0.912305 0.874898 0.818814 11.00000 0.09729 0.05813 = 0.09120 -0.00056 0.02824 -0.02150 AFIX 137 H14A 2 0.869065 0.903827 0.755537 11.00000 -1.50000 H14B 2 1.025711 0.837149 0.808821 11.00000 -1.50000 H14C 2 0.926508 0.946693 0.881950 11.00000 -1.50000 AFIX 0 B3 3 0.844546 0.141117 0.446825 11.00000 0.06465 0.04897 = 0.05153 0.00201 0.01933 0.00705 AFIX 153 H3A 2 0.901354 0.066574 0.385861 11.00000 -1.20000 AFIX 0 B4 3 0.956451 0.203272 0.577053 11.00000 0.04714 0.04977 = 0.05640 0.00663 0.01586 0.00705 AFIX 153 H4A 2 1.088465 0.170879 0.602111 11.00000 -1.20000 AFIX 0 B5 3 0.901200 0.365686 0.620395 11.00000 0.04662 0.04597 = 0.04868 0.00278 0.01527 -0.00134 AFIX 153 H5A 2 0.997527 0.438815 0.674067 11.00000 -1.20000 AFIX 0 B6 3 0.754622 0.402623 0.514630 11.00000 0.06852 0.04936 = 0.04972 0.00729 0.01642 0.01109 AFIX 153 H6 2 0.754750 0.498551 0.498714 11.00000 -1.20000 AFIX 0 C7 1 0.628250 0.153516 0.461724 11.00000 0.05758 0.05172 = 0.04314 -0.00353 0.00531 0.00340 AFIX 153 H7 2 0.533490 0.080277 0.406794 11.00000 -1.20000 AFIX 0 B8 3 0.761052 0.106121 0.558773 11.00000 0.04986 0.04673 = 0.04905 0.00267 0.01064 0.00349 AFIX 153 H8 2 0.760504 0.008566 0.571308 11.00000 -1.20000 AFIX 0 B9 3 0.796458 0.244966 0.669145 11.00000 0.04169 0.04548 = 0.04503 0.00294 0.00777 -0.00208 B10 3 0.670294 0.372484 0.630555 11.00000 0.04318 0.04497 = 0.04585 0.00071 0.00984 0.00156 B11 3 0.559513 0.305958 0.497380 11.00000 0.05869 0.05376 = 0.05016 0.00229 0.00195 0.01122 AFIX 153 H11A 2 0.427893 0.337278 0.470272 11.00000 -1.20000 AFIX 0 B12 3 0.584837 0.209600 0.590600 11.00000 0.04466 0.05069 = 0.04372 -0.00261 0.00712 0.00018 AFIX 153 H12 2 0.468444 0.178665 0.624361 11.00000 -1.20000 AFIX 0 HKLF 4 REM mj23176_0m_a.res in P-1 REM wR2 = 0.1565, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0513 for 2934 Fo > 4sig(Fo) and 0.0678 for all 3851 data REM 273 parameters refined using 0 restraints END WGHT 0.0851 0.1705 REM Highest difference peak 0.183, deepest hole -0.174, 1-sigma level 0.036 Q1 1 0.8128 0.4858 0.4819 11.00000 0.05 0.18 Q2 1 0.7094 0.1940 0.6232 11.00000 0.05 0.18 Q3 1 0.6914 0.7835 0.7764 11.00000 0.05 0.16 Q4 1 0.6890 0.2318 0.6361 11.00000 0.05 0.16 Q5 1 0.5897 0.3094 0.5808 11.00000 0.05 0.15 ; _shelx_res_checksum 72522 _olex2_submission_special_instructions 'No special instructions were received' 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 O1 O 0.5480(2) 0.04594(16) 0.74440(11) 0.0867(5) Uani 1 1 d . . . . . O2 O 0.4945(2) 0.13011(17) 0.91208(12) 0.0918(6) Uani 1 1 d . . . . . O3 O 0.8540(2) 0.65186(13) 0.68257(12) 0.0732(4) Uani 1 1 d . . . . . O4 O 0.7879(2) 0.78200(14) 0.83376(12) 0.0776(5) Uani 1 1 d . . . . . N1 N 0.84139(19) 0.24575(14) 0.78601(11) 0.0518(4) Uani 1 1 d . . . . . N2 N 0.58581(18) 0.46408(14) 0.71693(12) 0.0519(4) Uani 1 1 d . . . . . C1 C 0.9166(3) 0.29606(17) 0.48851(15) 0.0550(5) Uani 1 1 d . . . . . H1 H 1.031883 0.326268 0.453344 0.066 Uiso 1 1 calc R U . . . B2 B 0.7213(3) 0.2623(2) 0.40875(18) 0.0612(6) Uani 1 1 d . . . . . H2 H 0.697818 0.266035 0.322909 0.073 Uiso 1 1 calc R U . . . C3 C 0.9877(3) 0.3142(2) 0.84621(17) 0.0717(6) Uani 1 1 d . . . . . H3 H 1.077359 0.351912 0.817947 0.086 Uiso 1 1 calc R U . . . C4 C 0.9848(3) 0.3199(3) 0.95245(18) 0.0812(7) Uani 1 1 d . . . . . H4 H 1.070676 0.361042 1.009680 0.097 Uiso 1 1 calc R U . . . C5 C 0.8316(3) 0.2539(2) 0.96071(16) 0.0666(5) Uani 1 1 d . . . . . H5 H 0.794386 0.242338 1.024989 0.080 Uiso 1 1 calc R U . . . C6 C 0.7438(2) 0.20820(17) 0.85904(14) 0.0522(4) Uani 1 1 d . . . . . C2 C 0.5891(3) 0.12132(19) 0.82942(15) 0.0595(5) Uani 1 1 d . . . . . C8 C 0.3409(4) 0.0427(3) 0.8930(2) 0.1139(11) Uani 1 1 d . . . . . H8A H 0.252603 0.064137 0.840621 0.171 Uiso 1 1 calc R U . . . H8B H 0.291336 0.049157 0.960267 0.171 Uiso 1 1 calc R U . . . H8C H 0.375770 -0.043623 0.865418 0.171 Uiso 1 1 calc R U . . . C9 C 0.4483(3) 0.4237(2) 0.76242(19) 0.0758(7) Uani 1 1 d . . . . . H9 H 0.387899 0.343461 0.737015 0.091 Uiso 1 1 calc R U . . . C10 C 0.4109(3) 0.5150(2) 0.8490(2) 0.0829(8) Uani 1 1 d . . . . . H10 H 0.322022 0.509473 0.893053 0.100 Uiso 1 1 calc R U . . . C11 C 0.5287(3) 0.6178(2) 0.86023(16) 0.0663(6) Uani 1 1 d . . . . . H11 H 0.534328 0.694996 0.913774 0.080 Uiso 1 1 calc R U . . . C12 C 0.6358(2) 0.58721(17) 0.77940(13) 0.0485(4) Uani 1 1 d . . . . . C13 C 0.7685(2) 0.67127(17) 0.75747(13) 0.0495(4) Uani 1 1 d . . . . . C14 C 0.9123(3) 0.8749(2) 0.8188(2) 0.0847(7) Uani 1 1 d . . . . . H14A H 0.869065 0.903827 0.755537 0.127 Uiso 1 1 calc R U . . . H14B H 1.025711 0.837149 0.808821 0.127 Uiso 1 1 calc R U . . . H14C H 0.926508 0.946693 0.881950 0.127 Uiso 1 1 calc R U . . . B3 B 0.8445(3) 0.1411(2) 0.44683(17) 0.0559(5) Uani 1 1 d . . . . . H3A H 0.901354 0.066574 0.385861 0.067 Uiso 1 1 calc R U . . . B4 B 0.9565(3) 0.2033(2) 0.57705(17) 0.0515(5) Uani 1 1 d . . . . . H4A H 1.088465 0.170879 0.602111 0.062 Uiso 1 1 calc R U . . . B5 B 0.9012(3) 0.36569(19) 0.62040(16) 0.0480(5) Uani 1 1 d . . . . . H5A H 0.997527 0.438815 0.674067 0.058 Uiso 1 1 calc R U . . . B6 B 0.7546(3) 0.4026(2) 0.51463(17) 0.0560(5) Uani 1 1 d . . . . . H6 H 0.754750 0.498551 0.498714 0.067 Uiso 1 1 calc R U . . . C7 C 0.6283(2) 0.15352(17) 0.46172(14) 0.0536(5) Uani 1 1 d . . . . . H7 H 0.533490 0.080277 0.406794 0.064 Uiso 1 1 calc R U . . . B8 B 0.7611(3) 0.1061(2) 0.55877(16) 0.0499(5) Uani 1 1 d . . . . . H8 H 0.760504 0.008566 0.571308 0.060 Uiso 1 1 calc R U . . . B9 B 0.7965(2) 0.24497(19) 0.66914(15) 0.0454(4) Uani 1 1 d . . . . . B10 B 0.6703(2) 0.37248(18) 0.63055(16) 0.0463(5) Uani 1 1 d . . . . . B11 B 0.5595(3) 0.3060(2) 0.49738(17) 0.0564(5) Uani 1 1 d . . . . . H11A H 0.427893 0.337278 0.470272 0.068 Uiso 1 1 calc R U . . . B12 B 0.5848(3) 0.20960(19) 0.59060(16) 0.0488(5) Uani 1 1 d . . . . . H12 H 0.468444 0.178665 0.624361 0.059 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1091(12) 0.0864(11) 0.0512(8) -0.0057(8) 0.0147(8) -0.0467(9) O2 0.1003(12) 0.1024(13) 0.0617(9) -0.0054(8) 0.0316(8) -0.0433(10) O3 0.0913(10) 0.0594(8) 0.0673(9) 0.0009(7) 0.0389(8) -0.0076(7) O4 0.0960(11) 0.0597(9) 0.0667(9) -0.0109(7) 0.0309(8) -0.0219(8) N1 0.0485(8) 0.0571(9) 0.0460(8) 0.0085(7) 0.0021(6) -0.0071(7) N2 0.0450(8) 0.0497(8) 0.0548(9) -0.0024(7) 0.0148(6) 0.0000(6) C1 0.0629(11) 0.0489(10) 0.0534(10) 0.0062(8) 0.0234(8) 0.0056(8) B2 0.0818(15) 0.0561(13) 0.0431(11) 0.0052(9) 0.0117(10) 0.0102(11) C3 0.0563(11) 0.0899(16) 0.0627(13) 0.0165(11) -0.0081(9) -0.0210(11) C4 0.0795(15) 0.0951(17) 0.0589(13) 0.0146(12) -0.0179(11) -0.0214(13) C5 0.0824(14) 0.0663(13) 0.0462(11) 0.0090(9) 0.0012(10) -0.0073(11) C6 0.0610(11) 0.0493(10) 0.0427(9) 0.0052(7) 0.0069(8) -0.0044(8) C2 0.0741(13) 0.0567(11) 0.0443(10) 0.0056(8) 0.0114(9) -0.0117(9) C8 0.112(2) 0.134(3) 0.0899(19) 0.0136(18) 0.0329(17) -0.061(2) C9 0.0599(12) 0.0643(13) 0.0914(16) -0.0135(11) 0.0369(11) -0.0124(10) C10 0.0724(14) 0.0748(14) 0.0892(16) -0.0167(12) 0.0455(12) -0.0141(11) C11 0.0648(12) 0.0651(12) 0.0585(12) -0.0102(10) 0.0225(9) -0.0044(10) C12 0.0473(9) 0.0493(9) 0.0431(9) 0.0005(7) 0.0072(7) 0.0011(7) C13 0.0544(10) 0.0484(10) 0.0417(9) 0.0037(7) 0.0064(7) 0.0038(8) C14 0.0973(17) 0.0581(13) 0.0912(17) -0.0006(12) 0.0282(14) -0.0215(12) B3 0.0647(13) 0.0490(11) 0.0515(12) 0.0020(9) 0.0193(10) 0.0070(10) B4 0.0471(10) 0.0498(11) 0.0564(12) 0.0066(9) 0.0159(9) 0.0071(9) B5 0.0466(10) 0.0460(11) 0.0487(11) 0.0028(8) 0.0153(8) -0.0013(8) B6 0.0685(13) 0.0494(12) 0.0497(12) 0.0073(9) 0.0164(10) 0.0111(10) C7 0.0576(10) 0.0517(10) 0.0431(9) -0.0035(8) 0.0053(8) 0.0034(8) B8 0.0499(10) 0.0467(11) 0.0490(11) 0.0027(8) 0.0106(8) 0.0035(8) B9 0.0417(9) 0.0455(10) 0.0450(10) 0.0029(8) 0.0078(8) -0.0021(8) B10 0.0432(10) 0.0450(10) 0.0459(10) 0.0007(8) 0.0098(8) 0.0016(8) B11 0.0587(12) 0.0538(12) 0.0502(11) 0.0023(9) 0.0020(9) 0.0112(10) B12 0.0447(10) 0.0507(11) 0.0437(10) -0.0026(8) 0.0071(8) 0.0002(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 '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 C2 O2 C8 116.22(17) . . ? C13 O4 C14 116.07(16) . . ? C3 N1 C6 106.06(15) . . ? C3 N1 B9 120.62(16) . . ? C6 N1 B9 132.09(15) . . ? C9 N2 C12 105.68(14) . . ? C9 N2 B10 120.64(15) . . ? C12 N2 B10 132.75(14) . . ? B2 C1 H1 117.8 . . ? B2 C1 B3 63.04(13) . . ? B2 C1 B4 114.81(15) . . ? B2 C1 B5 114.92(14) . . ? B2 C1 B6 62.62(12) . . ? B3 C1 H1 117.8 . . ? B3 C1 B4 62.19(12) . . ? B3 C1 B5 114.79(15) . . ? B3 C1 B6 115.35(15) . . ? B4 C1 H1 117.3 . . ? B4 C1 B6 116.08(14) . . ? B5 C1 H1 117.3 . . ? B5 C1 B4 63.32(11) . . ? B5 C1 B6 63.37(12) . . ? B6 C1 H1 116.9 . . ? C1 B2 H2 125.6 . . ? C1 B2 B3 58.69(12) . . ? C1 B2 B6 59.41(12) . . ? C1 B2 B11 104.82(14) . . ? B3 B2 H2 120.9 . . ? B6 B2 H2 121.4 . . ? B6 B2 B3 109.09(16) . . ? C7 B2 C1 100.85(16) . . ? C7 B2 H2 125.5 . . ? C7 B2 B3 58.27(12) . . ? C7 B2 B6 105.37(15) . . ? C7 B2 B11 59.50(12) . . ? B11 B2 H2 121.8 . . ? B11 B2 B3 108.63(16) . . ? B11 B2 B6 59.82(12) . . ? N1 C3 H3 124.8 . . ? C4 C3 N1 110.3(2) . . ? C4 C3 H3 124.8 . . ? C3 C4 H4 126.5 . . ? C3 C4 C5 107.07(18) . . ? C5 C4 H4 126.5 . . ? C4 C5 H5 126.0 . . ? C6 C5 C4 108.07(19) . . ? C6 C5 H5 126.0 . . ? N1 C6 C2 124.82(15) . . ? C5 C6 N1 108.45(17) . . ? C5 C6 C2 126.24(18) . . ? O1 C2 O2 121.61(18) . . ? O1 C2 C6 126.84(18) . . ? O2 C2 C6 111.50(16) . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9 124.6 . . ? C10 C9 N2 110.89(19) . . ? C10 C9 H9 124.6 . . ? C9 C10 H10 126.5 . . ? C9 C10 C11 106.94(18) . . ? C11 C10 H10 126.5 . . ? C10 C11 H11 126.0 . . ? C12 C11 C10 108.04(17) . . ? C12 C11 H11 126.0 . . ? N2 C12 C13 125.53(15) . . ? C11 C12 N2 108.45(16) . . ? C11 C12 C13 125.87(16) . . ? O3 C13 O4 121.25(17) . . ? O3 C13 C12 127.79(16) . . ? O4 C13 C12 110.96(15) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 B3 B2 58.27(13) . . ? C1 B3 H3A 125.6 . . ? C1 B3 B4 59.30(12) . . ? C1 B3 B8 105.40(14) . . ? B2 B3 H3A 121.1 . . ? B4 B3 B2 108.48(15) . . ? B4 B3 H3A 121.7 . . ? B4 B3 B8 60.21(12) . . ? C7 B3 C1 100.67(14) . . ? C7 B3 B2 58.45(13) . . ? C7 B3 H3A 125.7 . . ? C7 B3 B4 104.93(14) . . ? C7 B3 B8 59.29(12) . . ? B8 B3 B2 108.83(15) . . ? B8 B3 H3A 121.4 . . ? C1 B4 B3 58.52(12) . . ? C1 B4 H4A 125.1 . . ? C1 B4 B5 58.08(11) . . ? C1 B4 B8 104.64(15) . . ? C1 B4 B9 104.97(14) . . ? B3 B4 H4A 121.6 . . ? B3 B4 B5 107.45(15) . . ? B3 B4 B8 60.01(12) . . ? B3 B4 B9 108.59(14) . . ? B5 B4 H4A 121.7 . . ? B8 B4 H4A 122.1 . . ? B8 B4 B5 108.32(13) . . ? B8 B4 B9 60.57(11) . . ? B9 B4 H4A 121.7 . . ? B9 B4 B5 60.46(11) . . ? C1 B5 B4 58.61(11) . . ? C1 B5 H5A 125.0 . . ? C1 B5 B6 58.70(11) . . ? C1 B5 B9 104.74(14) . . ? C1 B5 B10 105.29(14) . . ? B4 B5 H5A 121.3 . . ? B4 B5 B6 108.34(14) . . ? B4 B5 B9 59.64(11) . . ? B6 B5 H5A 121.1 . . ? B6 B5 B9 109.38(14) . . ? B9 B5 H5A 121.6 . . ? B10 B5 B4 109.40(14) . . ? B10 B5 H5A 121.2 . . ? B10 B5 B6 60.18(12) . . ? B10 B5 B9 61.85(11) . . ? C1 B6 B2 57.97(12) . . ? C1 B6 B5 57.93(11) . . ? C1 B6 H6 125.5 . . ? C1 B6 B10 104.21(15) . . ? C1 B6 B11 103.93(15) . . ? B2 B6 B5 106.64(15) . . ? B2 B6 H6 121.8 . . ? B2 B6 B10 108.43(16) . . ? B5 B6 H6 122.5 . . ? B10 B6 B5 59.55(11) . . ? B10 B6 H6 122.0 . . ? B11 B6 B2 60.08(13) . . ? B11 B6 B5 107.23(15) . . ? B11 B6 H6 122.4 . . ? B11 B6 B10 60.58(12) . . ? B2 C7 H7 117.5 . . ? B2 C7 B8 115.59(15) . . ? B2 C7 B11 62.57(13) . . ? B2 C7 B12 114.68(14) . . ? B3 C7 B2 63.27(13) . . ? B3 C7 H7 117.5 . . ? B3 C7 B8 62.63(12) . . ? B3 C7 B11 115.28(15) . . ? B3 C7 B12 114.87(14) . . ? B8 C7 H7 116.8 . . ? B8 C7 B11 116.01(13) . . ? B11 C7 H7 117.2 . . ? B12 C7 H7 117.7 . . ? B12 C7 B8 63.39(11) . . ? B12 C7 B11 62.86(12) . . ? B3 B8 B4 59.78(12) . . ? B3 B8 H8 121.9 . . ? B3 B8 B9 108.13(15) . . ? B3 B8 B12 106.72(15) . . ? B4 B8 H8 122.8 . . ? B4 B8 B9 60.23(11) . . ? B4 B8 B12 107.03(14) . . ? C7 B8 B3 58.08(12) . . ? C7 B8 B4 103.68(15) . . ? C7 B8 H8 125.4 . . ? C7 B8 B9 104.39(14) . . ? C7 B8 B12 58.00(11) . . ? B9 B8 H8 122.0 . . ? B12 B8 H8 122.3 . . ? B12 B8 B9 59.83(10) . . ? N1 B9 B4 120.52(15) . . ? N1 B9 B5 118.11(14) . . ? N1 B9 B8 125.63(16) . . ? N1 B9 B10 120.67(14) . . ? N1 B9 B12 127.05(15) . . ? B4 B9 B5 59.90(11) . . ? B4 B9 B8 59.21(11) . . ? B4 B9 B10 106.99(14) . . ? B4 B9 B12 106.36(13) . . ? B5 B9 B10 58.56(11) . . ? B8 B9 B5 106.82(14) . . ? B8 B9 B10 107.94(13) . . ? B12 B9 B5 105.48(14) . . ? B12 B9 B8 59.99(10) . . ? B12 B9 B10 59.64(11) . . ? N2 B10 B5 125.62(14) . . ? N2 B10 B6 128.14(16) . . ? N2 B10 B9 118.04(15) . . ? N2 B10 B11 123.01(15) . . ? N2 B10 B12 117.70(14) . . ? B5 B10 B6 60.27(11) . . ? B5 B10 B9 59.59(11) . . ? B5 B10 B11 106.49(13) . . ? B5 B10 B12 105.50(13) . . ? B6 B10 B9 107.66(13) . . ? B6 B10 B11 58.93(12) . . ? B6 B10 B12 106.00(13) . . ? B11 B10 B9 106.57(13) . . ? B11 B10 B12 59.30(12) . . ? B12 B10 B9 58.65(11) . . ? B2 B11 B10 108.38(15) . . ? B2 B11 H11A 122.0 . . ? B2 B11 B12 106.84(15) . . ? B6 B11 B2 60.10(13) . . ? B6 B11 B10 60.50(11) . . ? B6 B11 H11A 122.1 . . ? B6 B11 B12 108.28(15) . . ? C7 B11 B2 57.93(12) . . ? C7 B11 B6 104.39(15) . . ? C7 B11 B10 104.95(14) . . ? C7 B11 H11A 125.3 . . ? C7 B11 B12 58.00(11) . . ? B10 B11 H11A 121.6 . . ? B12 B11 B10 60.63(11) . . ? B12 B11 H11A 121.8 . . ? C7 B12 B8 58.61(11) . . ? C7 B12 B9 105.14(13) . . ? C7 B12 B10 105.40(15) . . ? C7 B12 B11 59.15(11) . . ? C7 B12 H12 124.8 . . ? B8 B12 B10 109.74(14) . . ? B8 B12 H12 120.9 . . ? B9 B12 B8 60.19(11) . . ? B9 B12 B10 61.71(11) . . ? B9 B12 H12 121.4 . . ? B10 B12 H12 121.3 . . ? B11 B12 B8 108.97(14) . . ? B11 B12 B9 109.63(15) . . ? B11 B12 B10 60.07(12) . . ? B11 B12 H12 120.8 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.196(2) . ? O2 C2 1.336(2) . ? O2 C8 1.448(3) . ? O3 C13 1.201(2) . ? O4 C13 1.343(2) . ? O4 C14 1.431(3) . ? N1 C3 1.369(2) . ? N1 C6 1.392(2) . ? N1 B9 1.502(2) . ? N2 C9 1.370(2) . ? N2 C12 1.397(2) . ? N2 B10 1.508(2) . ? C1 H1 1.1100 . ? C1 B2 1.684(3) . ? C1 B3 1.692(3) . ? C1 B4 1.706(3) . ? C1 B5 1.696(3) . ? C1 B6 1.710(3) . ? B2 H2 1.1100 . ? B2 B3 1.765(3) . ? B2 B6 1.764(3) . ? B2 C7 1.684(3) . ? B2 B11 1.764(3) . ? C3 H3 0.9400 . ? C3 C4 1.356(3) . ? C4 H4 0.9400 . ? C4 C5 1.383(3) . ? C5 H5 0.9400 . ? C5 C6 1.367(3) . ? C6 C2 1.446(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 H9 0.9400 . ? C9 C10 1.356(3) . ? C10 H10 0.9400 . ? C10 C11 1.385(3) . ? C11 H11 0.9400 . ? C11 C12 1.374(2) . ? C12 C13 1.444(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? B3 H3A 1.1100 . ? B3 B4 1.755(3) . ? B3 C7 1.681(3) . ? B3 B8 1.759(3) . ? B4 H4A 1.1100 . ? B4 B5 1.786(3) . ? B4 B8 1.763(3) . ? B4 B9 1.781(3) . ? B5 H5A 1.1100 . ? B5 B6 1.789(3) . ? B5 B9 1.796(3) . ? B5 B10 1.776(3) . ? B6 H6 1.1100 . ? B6 B10 1.788(3) . ? B6 B11 1.759(3) . ? C7 H7 1.1100 . ? C7 B8 1.703(3) . ? C7 B11 1.713(3) . ? C7 B12 1.692(2) . ? B8 H8 1.1100 . ? B8 B9 1.787(3) . ? B8 B12 1.783(3) . ? B9 B10 1.836(3) . ? B9 B12 1.780(3) . ? B10 B11 1.789(3) . ? B10 B12 1.799(3) . ? B11 H11A 1.1100 . ? B11 B12 1.775(3) . ? B12 H12 1.1100 . ? 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 N1 C3 C4 C5 -0.4(3) . . . . ? N1 C6 C2 O1 20.2(3) . . . . ? N1 C6 C2 O2 -162.36(19) . . . . ? N1 B9 B10 N2 -10.7(2) . . . . ? N1 B9 B10 B5 106.23(17) . . . . ? N1 B9 B10 B6 144.00(15) . . . . ? N1 B9 B10 B11 -154.06(15) . . . . ? N1 B9 B10 B12 -117.67(17) . . . . ? N1 B9 B12 C7 -153.03(17) . . . . ? N1 B9 B12 B8 -114.0(2) . . . . ? N1 B9 B12 B10 107.37(19) . . . . ? N1 B9 B12 B11 144.85(17) . . . . ? N2 C9 C10 C11 -0.2(3) . . . . ? N2 C12 C13 O3 1.8(3) . . . . ? N2 C12 C13 O4 -178.86(17) . . . . ? N2 B10 B11 B2 155.59(17) . . . . ? N2 B10 B11 B6 117.93(19) . . . . ? N2 B10 B11 C7 -143.77(17) . . . . ? N2 B10 B11 B12 -105.01(19) . . . . ? N2 B10 B12 C7 153.26(15) . . . . ? N2 B10 B12 B8 -145.11(16) . . . . ? N2 B10 B12 B9 -107.57(17) . . . . ? N2 B10 B12 B11 113.82(18) . . . . ? C1 B2 B3 B4 32.90(14) . . . . ? C1 B2 B3 C7 129.43(14) . . . . ? C1 B2 B3 B8 96.84(15) . . . . ? C1 B2 B6 B5 -32.80(14) . . . . ? C1 B2 B6 B10 -95.55(16) . . . . ? C1 B2 B6 B11 -133.44(16) . . . . ? C1 B2 C7 B3 -42.22(13) . . . . ? C1 B2 C7 B8 -6.49(18) . . . . ? C1 B2 C7 B11 100.92(14) . . . . ? C1 B2 C7 B12 64.45(18) . . . . ? C1 B2 B11 B6 40.28(15) . . . . ? C1 B2 B11 C7 -94.02(16) . . . . ? C1 B2 B11 B10 2.4(2) . . . . ? C1 B2 B11 B12 -61.49(19) . . . . ? C1 B3 B4 B5 32.60(13) . . . . ? C1 B3 B4 B8 134.08(14) . . . . ? C1 B3 B4 B9 96.52(15) . . . . ? C1 B3 C7 B2 41.96(13) . . . . ? C1 B3 C7 B8 -101.67(15) . . . . ? C1 B3 C7 B11 5.9(2) . . . . ? C1 B3 C7 B12 -64.41(19) . . . . ? C1 B3 B8 B4 -39.84(13) . . . . ? C1 B3 B8 C7 93.43(15) . . . . ? C1 B3 B8 B9 -2.54(19) . . . . ? C1 B3 B8 B12 60.47(17) . . . . ? C1 B4 B5 B6 32.49(14) . . . . ? C1 B4 B5 B9 134.66(15) . . . . ? C1 B4 B5 B10 96.47(16) . . . . ? C1 B4 B8 B3 39.28(12) . . . . ? C1 B4 B8 C7 -0.22(16) . . . . ? C1 B4 B8 B9 -99.15(14) . . . . ? C1 B4 B8 B12 -60.50(16) . . . . ? C1 B4 B9 N1 -145.56(16) . . . . ? C1 B4 B9 B5 -38.68(13) . . . . ? C1 B4 B9 B8 98.60(15) . . . . ? C1 B4 B9 B10 -2.51(17) . . . . ? C1 B4 B9 B12 60.03(17) . . . . ? C1 B5 B6 B2 32.81(14) . . . . ? C1 B5 B6 B10 134.77(15) . . . . ? C1 B5 B6 B11 95.92(15) . . . . ? C1 B5 B9 N1 149.74(15) . . . . ? C1 B5 B9 B4 38.89(13) . . . . ? C1 B5 B9 B8 1.38(18) . . . . ? C1 B5 B9 B10 -99.70(15) . . . . ? C1 B5 B9 B12 -61.32(16) . . . . ? C1 B5 B10 N2 -156.73(17) . . . . ? C1 B5 B10 B6 -38.97(13) . . . . ? C1 B5 B10 B9 98.79(14) . . . . ? C1 B5 B10 B11 -1.06(18) . . . . ? C1 B5 B10 B12 60.88(17) . . . . ? C1 B6 B10 N2 152.21(17) . . . . ? C1 B6 B10 B5 38.36(13) . . . . ? C1 B6 B10 B9 0.89(18) . . . . ? C1 B6 B10 B11 -98.18(15) . . . . ? C1 B6 B10 B12 -60.64(17) . . . . ? C1 B6 B11 B2 -39.36(14) . . . . ? C1 B6 B11 C7 -0.60(18) . . . . ? C1 B6 B11 B10 98.65(15) . . . . ? C1 B6 B11 B12 59.96(17) . . . . ? B2 C1 B3 B4 -143.19(15) . . . . ? B2 C1 B3 C7 -42.06(14) . . . . ? B2 C1 B3 B8 -102.90(16) . . . . ? B2 C1 B4 B3 36.04(14) . . . . ? B2 C1 B4 B5 -106.69(16) . . . . ? B2 C1 B4 B8 -3.98(18) . . . . ? B2 C1 B4 B9 -66.85(17) . . . . ? B2 C1 B5 B4 106.52(17) . . . . ? B2 C1 B5 B6 -36.85(16) . . . . ? B2 C1 B5 B9 67.13(19) . . . . ? B2 C1 B5 B10 2.8(2) . . . . ? B2 C1 B6 B5 142.23(16) . . . . ? B2 C1 B6 B10 103.08(17) . . . . ? B2 C1 B6 B11 40.42(15) . . . . ? B2 B3 B4 C1 -32.50(14) . . . . ? B2 B3 B4 B5 0.1(2) . . . . ? B2 B3 B4 B8 101.58(16) . . . . ? B2 B3 B4 B9 64.02(19) . . . . ? B2 B3 C7 B8 -143.63(15) . . . . ? B2 B3 C7 B11 -36.08(15) . . . . ? B2 B3 C7 B12 -106.37(17) . . . . ? B2 B3 B8 B4 -101.00(16) . . . . ? B2 B3 B8 C7 32.27(14) . . . . ? B2 B3 B8 B9 -63.70(18) . . . . ? B2 B3 B8 B12 -0.69(19) . . . . ? B2 B6 B10 N2 -147.28(18) . . . . ? B2 B6 B10 B5 98.87(16) . . . . ? B2 B6 B10 B9 61.40(18) . . . . ? B2 B6 B10 B11 -37.67(15) . . . . ? B2 B6 B10 B12 -0.13(19) . . . . ? B2 B6 B11 C7 38.76(14) . . . . ? B2 B6 B11 B10 138.02(16) . . . . ? B2 B6 B11 B12 99.32(16) . . . . ? B2 C7 B8 B3 -35.96(14) . . . . ? B2 C7 B8 B4 4.40(18) . . . . ? B2 C7 B8 B9 66.67(17) . . . . ? B2 C7 B8 B12 106.13(16) . . . . ? B2 C7 B11 B6 -39.83(15) . . . . ? B2 C7 B11 B10 -102.59(16) . . . . ? B2 C7 B11 B12 -142.63(16) . . . . ? B2 C7 B12 B8 -107.55(17) . . . . ? B2 C7 B12 B9 -67.76(19) . . . . ? B2 C7 B12 B10 -3.5(2) . . . . ? B2 C7 B12 B11 36.36(16) . . . . ? B2 B11 B12 C7 -32.50(14) . . . . ? B2 B11 B12 B8 -0.38(19) . . . . ? B2 B11 B12 B9 63.80(17) . . . . ? B2 B11 B12 B10 101.99(16) . . . . ? C3 N1 C6 C5 -0.1(2) . . . . ? C3 N1 C6 C2 -172.44(19) . . . . ? C3 N1 B9 B4 53.8(2) . . . . ? C3 N1 B9 B5 -16.1(2) . . . . ? C3 N1 B9 B8 125.8(2) . . . . ? C3 N1 B9 B10 -84.3(2) . . . . ? C3 N1 B9 B12 -157.53(18) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 N1 -0.2(2) . . . . ? C4 C5 C6 C2 172.1(2) . . . . ? C5 C6 C2 O1 -150.8(2) . . . . ? C5 C6 C2 O2 26.6(3) . . . . ? C6 N1 C3 C4 0.3(3) . . . . ? C6 N1 B9 B4 -140.87(19) . . . . ? C6 N1 B9 B5 149.32(18) . . . . ? C6 N1 B9 B8 -68.8(3) . . . . ? C6 N1 B9 B10 81.1(2) . . . . ? C6 N1 B9 B12 7.9(3) . . . . ? C8 O2 C2 O1 0.5(4) . . . . ? C8 O2 C2 C6 -177.1(2) . . . . ? C9 N2 C12 C11 0.1(2) . . . . ? C9 N2 C12 C13 -175.62(19) . . . . ? C9 N2 B10 B5 -138.7(2) . . . . ? C9 N2 B10 B6 143.6(2) . . . . ? C9 N2 B10 B9 -67.6(2) . . . . ? C9 N2 B10 B11 69.4(3) . . . . ? C9 N2 B10 B12 -0.3(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 N2 -0.2(3) . . . . ? C10 C11 C12 C13 175.5(2) . . . . ? C11 C12 C13 O3 -173.2(2) . . . . ? C11 C12 C13 O4 6.2(3) . . . . ? C12 N2 C9 C10 0.1(3) . . . . ? C12 N2 B10 B5 28.6(3) . . . . ? C12 N2 B10 B6 -49.1(3) . . . . ? C12 N2 B10 B9 99.7(2) . . . . ? C12 N2 B10 B11 -123.3(2) . . . . ? C12 N2 B10 B12 166.97(18) . . . . ? C14 O4 C13 O3 1.3(3) . . . . ? C14 O4 C13 C12 -178.11(18) . . . . ? B3 C1 B2 B6 143.54(16) . . . . ? B3 C1 B2 C7 41.99(12) . . . . ? B3 C1 B2 B11 103.05(17) . . . . ? B3 C1 B4 B5 -142.73(15) . . . . ? B3 C1 B4 B8 -40.02(13) . . . . ? B3 C1 B4 B9 -102.89(15) . . . . ? B3 C1 B5 B4 36.16(15) . . . . ? B3 C1 B5 B6 -107.21(18) . . . . ? B3 C1 B5 B9 -3.2(2) . . . . ? B3 C1 B5 B10 -67.52(19) . . . . ? B3 C1 B6 B2 -35.88(16) . . . . ? B3 C1 B6 B5 106.35(17) . . . . ? B3 C1 B6 B10 67.20(19) . . . . ? B3 C1 B6 B11 4.5(2) . . . . ? B3 B2 B6 C1 32.50(15) . . . . ? B3 B2 B6 B5 -0.3(2) . . . . ? B3 B2 B6 B10 -63.1(2) . . . . ? B3 B2 B6 B11 -100.94(18) . . . . ? B3 B2 C7 B8 35.73(14) . . . . ? B3 B2 C7 B11 143.14(15) . . . . ? B3 B2 C7 B12 106.67(16) . . . . ? B3 B2 B11 B6 101.72(18) . . . . ? B3 B2 B11 C7 -32.58(14) . . . . ? B3 B2 B11 B10 63.9(2) . . . . ? B3 B2 B11 B12 -0.1(2) . . . . ? B3 B4 B5 C1 -32.78(14) . . . . ? B3 B4 B5 B6 -0.29(19) . . . . ? B3 B4 B5 B9 101.88(15) . . . . ? B3 B4 B5 B10 63.69(18) . . . . ? B3 B4 B8 C7 -39.50(12) . . . . ? B3 B4 B8 B9 -138.44(15) . . . . ? B3 B4 B8 B12 -99.78(16) . . . . ? B3 B4 B9 N1 153.16(16) . . . . ? B3 B4 B9 B5 -99.96(16) . . . . ? B3 B4 B9 B8 37.32(14) . . . . ? B3 B4 B9 B10 -63.80(17) . . . . ? B3 B4 B9 B12 -1.3(2) . . . . ? B3 C7 B8 B4 40.36(13) . . . . ? B3 C7 B8 B9 102.64(15) . . . . ? B3 C7 B8 B12 142.09(15) . . . . ? B3 C7 B11 B2 36.34(16) . . . . ? B3 C7 B11 B6 -3.5(2) . . . . ? B3 C7 B11 B10 -66.25(19) . . . . ? B3 C7 B11 B12 -106.29(17) . . . . ? B3 C7 B12 B8 -36.97(15) . . . . ? B3 C7 B12 B9 2.8(2) . . . . ? B3 C7 B12 B10 67.05(19) . . . . ? B3 C7 B12 B11 106.94(18) . . . . ? B3 B8 B9 N1 -144.57(16) . . . . ? B3 B8 B9 B4 -37.10(14) . . . . ? B3 B8 B9 B5 0.72(18) . . . . ? B3 B8 B9 B10 62.37(17) . . . . ? B3 B8 B9 B12 99.20(16) . . . . ? B3 B8 B12 C7 32.99(13) . . . . ? B3 B8 B12 B9 -101.61(16) . . . . ? B3 B8 B12 B10 -63.42(17) . . . . ? B3 B8 B12 B11 0.66(18) . . . . ? B4 C1 B2 B3 -35.72(14) . . . . ? B4 C1 B2 B6 107.82(16) . . . . ? B4 C1 B2 C7 6.27(18) . . . . ? B4 C1 B2 B11 67.33(18) . . . . ? B4 C1 B3 B2 143.19(15) . . . . ? B4 C1 B3 C7 101.13(15) . . . . ? B4 C1 B3 B8 40.29(13) . . . . ? B4 C1 B5 B6 -143.37(15) . . . . ? B4 C1 B5 B9 -39.39(13) . . . . ? B4 C1 B5 B10 -103.68(15) . . . . ? B4 C1 B6 B2 -105.82(18) . . . . ? B4 C1 B6 B5 36.41(15) . . . . ? B4 C1 B6 B10 -2.7(2) . . . . ? B4 C1 B6 B11 -65.40(19) . . . . ? B4 B3 C7 B2 102.78(16) . . . . ? B4 B3 C7 B8 -40.85(14) . . . . ? B4 B3 C7 B11 66.71(19) . . . . ? B4 B3 C7 B12 -3.6(2) . . . . ? B4 B3 B8 C7 133.27(15) . . . . ? B4 B3 B8 B9 37.30(13) . . . . ? B4 B3 B8 B12 100.31(15) . . . . ? B4 B5 B6 C1 -32.45(13) . . . . ? B4 B5 B6 B2 0.4(2) . . . . ? B4 B5 B6 B10 102.32(15) . . . . ? B4 B5 B6 B11 63.47(17) . . . . ? B4 B5 B9 N1 110.85(17) . . . . ? B4 B5 B9 B8 -37.50(13) . . . . ? B4 B5 B9 B10 -138.59(14) . . . . ? B4 B5 B9 B12 -100.21(14) . . . . ? B4 B5 B10 N2 141.72(18) . . . . ? B4 B5 B10 B6 -100.53(16) . . . . ? B4 B5 B10 B9 37.23(13) . . . . ? B4 B5 B10 B11 -62.62(18) . . . . ? B4 B5 B10 B12 -0.68(19) . . . . ? B4 B8 B9 N1 -107.47(18) . . . . ? B4 B8 B9 B5 37.82(14) . . . . ? B4 B8 B9 B10 99.47(15) . . . . ? B4 B8 B9 B12 136.30(16) . . . . ? B4 B8 B12 C7 95.76(16) . . . . ? B4 B8 B12 B9 -38.84(14) . . . . ? B4 B8 B12 B10 -0.65(19) . . . . ? B4 B8 B12 B11 63.43(17) . . . . ? B4 B9 B10 N2 -153.66(15) . . . . ? B4 B9 B10 B5 -36.75(13) . . . . ? B4 B9 B10 B6 1.02(18) . . . . ? B4 B9 B10 B11 62.96(17) . . . . ? B4 B9 B10 B12 99.35(14) . . . . ? B4 B9 B12 C7 -0.82(19) . . . . ? B4 B9 B12 B8 38.21(14) . . . . ? B4 B9 B12 B10 -100.42(15) . . . . ? B4 B9 B12 B11 -62.94(17) . . . . ? B5 C1 B2 B3 -106.41(17) . . . . ? B5 C1 B2 B6 37.13(16) . . . . ? B5 C1 B2 C7 -64.42(18) . . . . ? B5 C1 B2 B11 -3.4(2) . . . . ? B5 C1 B3 B2 106.60(17) . . . . ? B5 C1 B3 B4 -36.59(15) . . . . ? B5 C1 B3 C7 64.54(19) . . . . ? B5 C1 B3 B8 3.7(2) . . . . ? B5 C1 B4 B3 142.73(15) . . . . ? B5 C1 B4 B8 102.71(14) . . . . ? B5 C1 B4 B9 39.83(13) . . . . ? B5 C1 B6 B2 -142.23(16) . . . . ? B5 C1 B6 B10 -39.15(13) . . . . ? B5 C1 B6 B11 -101.81(16) . . . . ? B5 B4 B8 B3 99.99(16) . . . . ? B5 B4 B8 C7 60.49(16) . . . . ? B5 B4 B8 B9 -38.44(14) . . . . ? B5 B4 B8 B12 0.22(19) . . . . ? B5 B4 B9 N1 -106.88(18) . . . . ? B5 B4 B9 B8 137.28(15) . . . . ? B5 B4 B9 B10 36.16(13) . . . . ? B5 B4 B9 B12 98.71(15) . . . . ? B5 B6 B10 N2 113.85(19) . . . . ? B5 B6 B10 B9 -37.47(13) . . . . ? B5 B6 B10 B11 -136.54(15) . . . . ? B5 B6 B10 B12 -99.00(14) . . . . ? B5 B6 B11 B2 -99.64(16) . . . . ? B5 B6 B11 C7 -60.87(17) . . . . ? B5 B6 B11 B10 38.38(12) . . . . ? B5 B6 B11 B12 -0.31(18) . . . . ? B5 B9 B10 N2 -116.91(17) . . . . ? B5 B9 B10 B6 37.77(13) . . . . ? B5 B9 B10 B11 99.71(15) . . . . ? B5 B9 B10 B12 136.10(14) . . . . ? B5 B9 B12 C7 61.73(16) . . . . ? B5 B9 B12 B8 100.76(14) . . . . ? B5 B9 B12 B10 -37.87(12) . . . . ? B5 B9 B12 B11 -0.39(17) . . . . ? B5 B10 B11 B2 -0.9(2) . . . . ? B5 B10 B11 B6 -38.53(14) . . . . ? B5 B10 B11 C7 59.77(18) . . . . ? B5 B10 B11 B12 98.54(15) . . . . ? B5 B10 B12 C7 -60.81(17) . . . . ? B5 B10 B12 B8 0.82(18) . . . . ? B5 B10 B12 B9 38.36(13) . . . . ? B5 B10 B12 B11 -100.25(15) . . . . ? B6 C1 B2 B3 -143.54(16) . . . . ? B6 C1 B2 C7 -101.55(15) . . . . ? B6 C1 B2 B11 -40.49(15) . . . . ? B6 C1 B3 B2 35.73(16) . . . . ? B6 C1 B3 B4 -107.47(16) . . . . ? B6 C1 B3 C7 -6.3(2) . . . . ? B6 C1 B3 B8 -67.18(19) . . . . ? B6 C1 B4 B3 106.30(17) . . . . ? B6 C1 B4 B5 -36.43(15) . . . . ? B6 C1 B4 B8 66.28(18) . . . . ? B6 C1 B4 B9 3.4(2) . . . . ? B6 C1 B5 B4 143.37(15) . . . . ? B6 C1 B5 B9 103.98(15) . . . . ? B6 C1 B5 B10 39.69(14) . . . . ? B6 B2 B3 C1 -32.77(15) . . . . ? B6 B2 B3 B4 0.1(2) . . . . ? B6 B2 B3 C7 96.65(17) . . . . ? B6 B2 B3 B8 64.1(2) . . . . ? B6 B2 C7 B3 -103.23(17) . . . . ? B6 B2 C7 B8 -67.50(19) . . . . ? B6 B2 C7 B11 39.91(14) . . . . ? B6 B2 C7 B12 3.4(2) . . . . ? B6 B2 B11 C7 -134.30(16) . . . . ? B6 B2 B11 B10 -37.84(15) . . . . ? B6 B2 B11 B12 -101.77(16) . . . . ? B6 B5 B9 N1 -148.75(14) . . . . ? B6 B5 B9 B4 100.41(15) . . . . ? B6 B5 B9 B8 62.90(16) . . . . ? B6 B5 B9 B10 -38.18(12) . . . . ? B6 B5 B9 B12 0.19(17) . . . . ? B6 B5 B10 N2 -117.8(2) . . . . ? B6 B5 B10 B9 137.76(14) . . . . ? B6 B5 B10 B11 37.91(14) . . . . ? B6 B5 B10 B12 99.85(15) . . . . ? B6 B10 B11 B2 37.67(15) . . . . ? B6 B10 B11 C7 98.30(16) . . . . ? B6 B10 B11 B12 137.07(14) . . . . ? B6 B10 B12 C7 2.07(17) . . . . ? B6 B10 B12 B8 63.70(17) . . . . ? B6 B10 B12 B9 101.23(14) . . . . ? B6 B10 B12 B11 -37.37(13) . . . . ? B6 B11 B12 C7 -95.86(15) . . . . ? B6 B11 B12 B8 -63.73(17) . . . . ? B6 B11 B12 B9 0.45(18) . . . . ? B6 B11 B12 B10 38.63(12) . . . . ? C7 B2 B3 C1 -129.43(14) . . . . ? C7 B2 B3 B4 -96.52(15) . . . . ? C7 B2 B3 B8 -32.59(14) . . . . ? C7 B2 B6 C1 93.68(16) . . . . ? C7 B2 B6 B5 60.88(19) . . . . ? C7 B2 B6 B10 -1.9(2) . . . . ? C7 B2 B6 B11 -39.76(15) . . . . ? C7 B2 B11 B6 134.30(16) . . . . ? C7 B2 B11 B10 96.46(16) . . . . ? C7 B2 B11 B12 32.53(14) . . . . ? C7 B3 B4 C1 -93.70(15) . . . . ? C7 B3 B4 B5 -61.10(18) . . . . ? C7 B3 B4 B8 40.38(14) . . . . ? C7 B3 B4 B9 2.8(2) . . . . ? C7 B3 B8 B4 -133.27(15) . . . . ? C7 B3 B8 B9 -95.97(15) . . . . ? C7 B3 B8 B12 -32.96(13) . . . . ? C7 B8 B9 N1 154.79(16) . . . . ? C7 B8 B9 B4 -97.74(15) . . . . ? C7 B8 B9 B5 -59.91(16) . . . . ? C7 B8 B9 B10 1.74(17) . . . . ? C7 B8 B9 B12 38.56(13) . . . . ? C7 B8 B12 B9 -134.60(15) . . . . ? C7 B8 B12 B10 -96.41(16) . . . . ? C7 B8 B12 B11 -32.33(13) . . . . ? C7 B11 B12 B8 32.13(13) . . . . ? C7 B11 B12 B9 96.31(14) . . . . ? C7 B11 B12 B10 134.49(14) . . . . ? B8 B3 B4 C1 -134.08(14) . . . . ? B8 B3 B4 B5 -101.48(15) . . . . ? B8 B3 B4 B9 -37.56(14) . . . . ? B8 B3 C7 B2 143.63(15) . . . . ? B8 B3 C7 B11 107.56(16) . . . . ? B8 B3 C7 B12 37.26(15) . . . . ? B8 B4 B5 C1 -96.17(16) . . . . ? B8 B4 B5 B6 -63.68(18) . . . . ? B8 B4 B5 B9 38.49(14) . . . . ? B8 B4 B5 B10 0.3(2) . . . . ? B8 B4 B9 N1 115.84(19) . . . . ? B8 B4 B9 B5 -137.28(15) . . . . ? B8 B4 B9 B10 -101.12(14) . . . . ? B8 B4 B9 B12 -38.57(14) . . . . ? B8 C7 B11 B2 106.76(18) . . . . ? B8 C7 B11 B6 66.93(19) . . . . ? B8 C7 B11 B10 4.2(2) . . . . ? B8 C7 B11 B12 -35.88(15) . . . . ? B8 C7 B12 B9 39.79(14) . . . . ? B8 C7 B12 B10 104.02(15) . . . . ? B8 C7 B12 B11 143.91(15) . . . . ? B8 B9 B10 N2 143.97(15) . . . . ? B8 B9 B10 B5 -99.12(14) . . . . ? B8 B9 B10 B6 -61.35(17) . . . . ? B8 B9 B10 B11 0.59(18) . . . . ? B8 B9 B10 B12 36.98(13) . . . . ? B8 B9 B12 C7 -39.03(14) . . . . ? B8 B9 B12 B10 -138.63(14) . . . . ? B8 B9 B12 B11 -101.15(15) . . . . ? B9 N1 C3 C4 169.03(19) . . . . ? B9 N1 C6 C5 -167.00(19) . . . . ? B9 N1 C6 C2 20.6(3) . . . . ? B9 B4 B5 C1 -134.66(15) . . . . ? B9 B4 B5 B6 -102.17(15) . . . . ? B9 B4 B5 B10 -38.19(13) . . . . ? B9 B4 B8 B3 138.44(15) . . . . ? B9 B4 B8 C7 98.94(14) . . . . ? B9 B4 B8 B12 38.66(13) . . . . ? B9 B5 B6 C1 -95.84(15) . . . . ? B9 B5 B6 B2 -63.03(18) . . . . ? B9 B5 B6 B10 38.92(13) . . . . ? B9 B5 B6 B11 0.07(18) . . . . ? B9 B5 B10 N2 104.5(2) . . . . ? B9 B5 B10 B6 -137.76(14) . . . . ? B9 B5 B10 B11 -99.85(15) . . . . ? B9 B5 B10 B12 -37.92(13) . . . . ? B9 B8 B12 C7 134.60(15) . . . . ? B9 B8 B12 B10 38.19(13) . . . . ? B9 B8 B12 B11 102.27(16) . . . . ? B9 B10 B11 B2 -63.30(18) . . . . ? B9 B10 B11 B6 -100.97(14) . . . . ? B9 B10 B11 C7 -2.66(18) . . . . ? B9 B10 B11 B12 36.10(12) . . . . ? B9 B10 B12 C7 -99.17(14) . . . . ? B9 B10 B12 B8 -37.53(13) . . . . ? B9 B10 B12 B11 -138.60(14) . . . . ? B10 N2 C9 C10 170.4(2) . . . . ? B10 N2 C12 C11 -168.6(2) . . . . ? B10 N2 C12 C13 15.7(3) . . . . ? B10 B5 B6 C1 -134.77(15) . . . . ? B10 B5 B6 B2 -101.95(17) . . . . ? B10 B5 B6 B11 -38.85(13) . . . . ? B10 B5 B9 N1 -110.56(16) . . . . ? B10 B5 B9 B4 138.59(14) . . . . ? B10 B5 B9 B8 101.09(14) . . . . ? B10 B5 B9 B12 38.38(12) . . . . ? B10 B6 B11 B2 -138.02(16) . . . . ? B10 B6 B11 C7 -99.25(15) . . . . ? B10 B6 B11 B12 -38.69(13) . . . . ? B10 B9 B12 C7 99.61(15) . . . . ? B10 B9 B12 B8 138.63(14) . . . . ? B10 B9 B12 B11 37.48(12) . . . . ? B10 B11 B12 C7 -134.49(14) . . . . ? B10 B11 B12 B8 -102.37(14) . . . . ? B10 B11 B12 B9 -38.19(12) . . . . ? B11 B2 B3 C1 -96.37(16) . . . . ? B11 B2 B3 B4 -63.5(2) . . . . ? B11 B2 B3 C7 33.06(14) . . . . ? B11 B2 B3 B8 0.5(2) . . . . ? B11 B2 B6 C1 133.44(16) . . . . ? B11 B2 B6 B5 100.64(16) . . . . ? B11 B2 B6 B10 37.89(14) . . . . ? B11 B2 C7 B3 -143.14(15) . . . . ? B11 B2 C7 B8 -107.41(15) . . . . ? B11 B2 C7 B12 -36.47(15) . . . . ? B11 B6 B10 N2 -109.6(2) . . . . ? B11 B6 B10 B5 136.54(15) . . . . ? B11 B6 B10 B9 99.07(14) . . . . ? B11 B6 B10 B12 37.54(13) . . . . ? B11 C7 B8 B3 -106.41(18) . . . . ? B11 C7 B8 B4 -66.05(18) . . . . ? B11 C7 B8 B9 -3.8(2) . . . . ? B11 C7 B8 B12 35.68(15) . . . . ? B11 C7 B12 B8 -143.91(15) . . . . ? B11 C7 B12 B9 -104.12(16) . . . . ? B11 C7 B12 B10 -39.89(13) . . . . ? B11 B10 B12 C7 39.44(13) . . . . ? B11 B10 B12 B8 101.07(15) . . . . ? B11 B10 B12 B9 138.60(14) . . . . ? B12 C7 B8 B3 -142.09(15) . . . . ? B12 C7 B8 B4 -101.73(14) . . . . ? B12 C7 B8 B9 -39.46(13) . . . . ? B12 C7 B11 B2 142.63(16) . . . . ? B12 C7 B11 B6 102.80(15) . . . . ? B12 C7 B11 B10 40.05(13) . . . . ? B12 B8 B9 N1 116.23(19) . . . . ? B12 B8 B9 B4 -136.30(16) . . . . ? B12 B8 B9 B5 -98.48(15) . . . . ? B12 B8 B9 B10 -36.83(13) . . . . ? B12 B9 B10 N2 106.99(17) . . . . ? B12 B9 B10 B5 -136.10(14) . . . . ? B12 B9 B10 B6 -98.33(15) . . . . ? B12 B9 B10 B11 -36.39(13) . . . . ? B12 B10 B11 B2 -99.40(16) . . . . ? B12 B10 B11 B6 -137.07(14) . . . . ? B12 B10 B11 C7 -38.76(13) . . . . ?