#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:10:59 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306440 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721008.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_7721008 loop_ _publ_author_name 'Amrutha, P. R.' 'Kundu, Gargi' 'Ganesh, Vemuri Lakshmi' 'Gonnade, Rajesh G.' 'Gopakumar, Gopinadhanpillai' 'Sen, Sakya S.' _publ_section_title ; Reactions of saturated NHC·boranes with electron-deficient alkynes and alkenes. Borirane formation, their reactivities, and coupling of tetracyanoethylene. ; _journal_issue 21 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 8356 _journal_page_last 8365 _journal_paper_doi 10.1039/d6dt00852f _journal_volume 55 _journal_year 2026 _chemical_formula_moiety 'C33 H47 B N2 O4' _chemical_formula_sum 'C33 H47 B N2 O4' _chemical_formula_weight 546.53 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2025-09-02 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2025-10-07 deposited with the CCDC. 2026-05-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.683(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.7284(18) _cell_length_b 9.7573(10) _cell_length_c 18.4994(16) _cell_measurement_reflns_used 103189 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.471 _cell_measurement_theta_min 2.204 _cell_volume 3016.2(5) _computing_cell_refinement 'SAINT (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2016)' _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, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Photon II CPAD Area Detector' _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 122470 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.035 _diffrn_reflns_theta_min 2.633 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.6690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.204 _exptl_crystal_description plate _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.537 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack -0.2(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 374 _refine_ls_number_reflns 9605 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0434 _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^)+(0.0670P)^2^+1.3147P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1119 _refine_ls_wR_factor_ref 0.1161 _reflns_Friedel_coverage 0.996 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 8866 _reflns_number_total 9605 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00852f2.cif _cod_data_source_block mo_APR_21223_a _cod_depositor_comments 'Adding full bibliography for 7721003--7721010.cif.' _cod_database_code 7721008 _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 0.992 _shelx_estimated_absorpt_t_min 0.985 _olex2_refinement_description ; 1. Twinned data refinement Scales: 1.18125 -0.18125 2.a Ternary CH refined with riding coordinates: C11(H11), C14(H14), C23(H23), C26(H26), C29(H29) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C30(H30A,H30B) 2.c Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21) 2.d Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B, H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A, H28B,H28C), C33(H33A,H33B,H33C) ; _shelx_res_file ; TITL mo_APR_21223_a.res in Cc mo_APR_21223_a.res created by SHELXL-2018/3 at 08:53:02 on 02-Sep-2025 REM Old TITL mo_APR_21223 in Cc REM SHELXT solution in Cc: R1 0.100, Rweak 0.025, Alpha 0.001 REM 1.566 for 188 systematic absences, Orientation as input REM Flack x = -0.041 ( 0.249 ) from 2869 Parsons' quotients REM Formula found by SHELXT: C34 N2 O4 CELL 0.71073 16.7284 9.7573 18.4994 90.000 92.683 90.000 ZERR 4.000 0.0018 0.0010 0.0016 0.000 0.003 0.000 LATT -7 SYMM X, -Y, 1/2+Z SFAC C H B N O UNIT 132 188 4 8 16 CONF ACTA SIZE 0.2 0.12 0.1 LIST 4 OMIT 2 0 0 OMIT 1 1 0 OMIT -1 1 0 TEMP -173.150 TWIN L.S. 30 BOND FMAP 2 PLAN 20 WGHT 0.067000 1.314700 BASF -0.18125 FVAR 0.49735 O1 5 0.416017 0.561480 0.515103 11.00000 0.01938 0.01839 = 0.02106 0.00156 0.00375 -0.00292 O2 5 0.388590 0.394558 0.592952 11.00000 0.04054 0.02590 = 0.02585 0.00480 0.00707 -0.01069 O3 5 0.560399 0.324231 0.442900 11.00000 0.04144 0.02220 = 0.07003 -0.02149 0.02966 -0.01367 O4 5 0.659116 0.475030 0.429336 11.00000 0.02488 0.02268 = 0.02870 -0.00471 0.00735 -0.00190 N1 4 0.513989 0.865560 0.431486 11.00000 0.01693 0.01002 = 0.01276 0.00054 0.00294 0.00074 N2 4 0.472977 0.857737 0.548155 11.00000 0.01754 0.01336 = 0.01253 0.00105 0.00317 0.00197 C1 1 0.492761 0.790271 0.488305 11.00000 0.01420 0.01225 = 0.01306 0.00072 0.00124 0.00063 C2 1 0.472526 1.009253 0.552308 11.00000 0.02530 0.01303 = 0.01864 -0.00256 0.00502 0.00138 AFIX 23 H2A 2 0.526638 1.042818 0.567304 11.00000 -1.20000 H2B 2 0.434874 1.039502 0.588828 11.00000 -1.20000 AFIX 0 C3 1 0.447415 1.067921 0.479377 11.00000 0.02192 0.01246 = 0.02143 0.00121 0.00350 0.00394 AFIX 23 H3A 2 0.448017 1.169322 0.481179 11.00000 -1.20000 H3B 2 0.392622 1.037323 0.464651 11.00000 -1.20000 AFIX 0 C4 1 0.506598 1.016525 0.426354 11.00000 0.02862 0.01030 = 0.01911 0.00110 0.00658 0.00070 AFIX 23 H4A 2 0.488361 1.042564 0.376553 11.00000 -1.20000 H4B 2 0.559474 1.059374 0.437075 11.00000 -1.20000 AFIX 0 C5 1 0.547856 0.803218 0.368834 11.00000 0.01647 0.01215 = 0.01169 0.00092 0.00404 -0.00068 C6 1 0.496458 0.769083 0.309052 11.00000 0.01432 0.01438 = 0.01475 0.00158 0.00276 -0.00173 C7 1 0.529685 0.706078 0.249992 11.00000 0.02100 0.02230 = 0.01421 -0.00160 0.00323 -0.00518 AFIX 43 H7 2 0.496111 0.679064 0.209656 11.00000 -1.20000 AFIX 0 C8 1 0.611553 0.682380 0.249557 11.00000 0.02182 0.02399 = 0.01782 -0.00428 0.00757 -0.00144 AFIX 43 H8 2 0.633374 0.636865 0.209587 11.00000 -1.20000 AFIX 0 C9 1 0.661757 0.724913 0.307312 11.00000 0.01555 0.02029 = 0.02003 -0.00059 0.00553 -0.00044 AFIX 43 H9 2 0.717842 0.711226 0.305373 11.00000 -1.20000 AFIX 0 C10 1 0.631178 0.787451 0.368174 11.00000 0.01533 0.01438 = 0.01537 0.00184 0.00255 -0.00177 C11 1 0.407302 0.798792 0.307136 11.00000 0.01562 0.02050 = 0.01608 0.00373 0.00234 -0.00099 AFIX 13 H11 2 0.393550 0.835744 0.355420 11.00000 -1.20000 AFIX 0 C12 1 0.357221 0.669419 0.291856 11.00000 0.01768 0.02448 = 0.02862 0.00278 -0.00046 -0.00658 AFIX 137 H12A 2 0.372971 0.598220 0.327072 11.00000 -1.50000 H12B 2 0.366322 0.636452 0.242881 11.00000 -1.50000 H12C 2 0.300375 0.690933 0.295852 11.00000 -1.50000 AFIX 0 C13 1 0.385836 0.907217 0.249678 11.00000 0.02107 0.03063 = 0.03377 0.01353 0.00021 0.00094 AFIX 137 H13A 2 0.420651 0.987222 0.257210 11.00000 -1.50000 H13B 2 0.329886 0.934892 0.253566 11.00000 -1.50000 H13C 2 0.393225 0.868965 0.201465 11.00000 -1.50000 AFIX 0 C14 1 0.688454 0.846503 0.426761 11.00000 0.01670 0.01937 = 0.01802 0.00156 0.00033 -0.00400 AFIX 13 H14 2 0.656797 0.870565 0.469504 11.00000 -1.20000 AFIX 0 C15 1 0.725004 0.978941 0.397816 11.00000 0.02897 0.02109 = 0.02741 0.00111 0.00166 -0.00993 AFIX 137 H15A 2 0.759675 1.020929 0.435823 11.00000 -1.50000 H15B 2 0.682068 1.042904 0.383190 11.00000 -1.50000 H15C 2 0.756581 0.957456 0.355974 11.00000 -1.50000 AFIX 0 C16 1 0.756406 0.750410 0.452354 11.00000 0.02118 0.02733 = 0.03685 0.00280 -0.00980 -0.00303 AFIX 137 H16A 2 0.789431 0.795466 0.490517 11.00000 -1.50000 H16B 2 0.789471 0.728454 0.411562 11.00000 -1.50000 H16C 2 0.733802 0.665814 0.471361 11.00000 -1.50000 AFIX 0 C17 1 0.457930 0.790576 0.616172 11.00000 0.01843 0.01495 = 0.01220 0.00040 0.00386 0.00263 C18 1 0.378759 0.755287 0.631344 11.00000 0.01874 0.01880 = 0.01541 -0.00153 0.00458 0.00183 C19 1 0.365946 0.699838 0.699417 11.00000 0.02485 0.02384 = 0.01890 0.00044 0.00853 -0.00037 AFIX 43 H19 2 0.313401 0.673149 0.710842 11.00000 -1.20000 AFIX 0 C20 1 0.428300 0.682917 0.750677 11.00000 0.03448 0.02580 = 0.01551 0.00336 0.00639 0.00252 AFIX 43 H20 2 0.418308 0.644438 0.796555 11.00000 -1.20000 AFIX 0 C21 1 0.505014 0.722032 0.735040 11.00000 0.02891 0.02738 = 0.01441 0.00191 0.00103 0.00589 AFIX 43 H21 2 0.547200 0.711134 0.770768 11.00000 -1.20000 AFIX 0 C22 1 0.521753 0.777360 0.667623 11.00000 0.02025 0.02073 = 0.01446 -0.00125 0.00207 0.00457 C23 1 0.606363 0.826344 0.654719 11.00000 0.01805 0.02535 = 0.01812 -0.00141 -0.00089 0.00282 AFIX 13 H23 2 0.607964 0.857170 0.603254 11.00000 -1.20000 AFIX 0 C24 1 0.669508 0.715053 0.667286 11.00000 0.01901 0.03358 = 0.02582 -0.00578 -0.00362 0.00600 AFIX 137 H24A 2 0.721324 0.748720 0.652149 11.00000 -1.50000 H24B 2 0.654100 0.633553 0.638979 11.00000 -1.50000 H24C 2 0.673675 0.691374 0.718806 11.00000 -1.50000 AFIX 0 C25 1 0.626852 0.949402 0.703507 11.00000 0.03286 0.02992 = 0.03272 -0.01109 -0.00019 -0.00372 AFIX 137 H25A 2 0.681889 0.978812 0.696128 11.00000 -1.50000 H25B 2 0.621798 0.923255 0.754237 11.00000 -1.50000 H25C 2 0.589981 1.024895 0.691379 11.00000 -1.50000 AFIX 0 C26 1 0.308795 0.782132 0.578021 11.00000 0.01763 0.02579 = 0.01858 -0.00247 0.00330 0.00079 AFIX 13 H26 2 0.329839 0.787486 0.528387 11.00000 -1.20000 AFIX 0 C27 1 0.244679 0.669537 0.577896 11.00000 0.02141 0.03388 = 0.03321 -0.00803 0.00505 -0.00575 AFIX 137 H27A 2 0.207593 0.681337 0.535763 11.00000 -1.50000 H27B 2 0.215116 0.675895 0.622273 11.00000 -1.50000 H27C 2 0.270402 0.579508 0.575571 11.00000 -1.50000 AFIX 0 C28 1 0.269830 0.920298 0.594911 11.00000 0.02170 0.03163 = 0.03088 -0.00211 -0.00182 0.00716 AFIX 137 H28A 2 0.223153 0.934853 0.561794 11.00000 -1.50000 H28B 2 0.308587 0.994234 0.588806 11.00000 -1.50000 H28C 2 0.252887 0.919965 0.644909 11.00000 -1.50000 AFIX 0 C29 1 0.563490 0.531963 0.513231 11.00000 0.01967 0.01318 = 0.02238 -0.00003 0.00161 0.00040 AFIX 13 H29 2 0.607787 0.593933 0.531002 11.00000 -1.20000 AFIX 0 C30 1 0.526156 0.456274 0.575531 11.00000 0.02786 0.01742 = 0.02204 0.00527 -0.00035 0.00177 AFIX 23 H30A 2 0.543726 0.359380 0.576725 11.00000 -1.20000 H30B 2 0.542522 0.499572 0.622309 11.00000 -1.20000 AFIX 0 C31 1 0.436410 0.464719 0.562583 11.00000 0.02843 0.01545 = 0.01771 -0.00055 0.00083 -0.00249 C32 1 0.591410 0.431694 0.458617 11.00000 0.02181 0.01495 = 0.03247 0.00033 0.00531 0.00183 C33 1 0.692717 0.386372 0.376837 11.00000 0.03105 0.03445 = 0.03658 -0.01377 0.01405 -0.00333 AFIX 137 H33A 2 0.741646 0.427713 0.359477 11.00000 -1.50000 H33B 2 0.653962 0.373389 0.336031 11.00000 -1.50000 H33C 2 0.705495 0.297458 0.399146 11.00000 -1.50000 AFIX 0 B1 3 0.486071 0.620461 0.477375 11.00000 0.01732 0.01388 = 0.01770 0.00061 0.00123 -0.00142 H1 2 0.477824 0.602184 0.421109 11.00000 -1.50000 HKLF 4 REM mo_APR_21223_a.res in Cc REM wR2 = 0.116118, GooF = S = 1.04131, Restrained GooF = 1.04120 for all data REM R1 = 0.043394 for 8866 Fo > 4sig(Fo) and 0.049214 for all 9605 data REM 374 parameters refined using 2 restraints END WGHT 0.0670 1.3147 REM Highest difference peak 0.537, deepest hole -0.262, 1-sigma level 0.047 Q1 1 0.6270 0.4599 0.3835 11.00000 0.05 0.54 Q2 1 0.3833 0.6191 0.4439 11.00000 0.05 0.53 Q3 1 0.5037 0.5583 0.5636 11.00000 0.05 0.47 Q4 1 0.5058 0.5286 0.4315 11.00000 0.05 0.47 Q5 1 0.5385 0.6292 0.4987 11.00000 0.05 0.41 Q6 1 0.4322 0.4629 0.4659 11.00000 0.05 0.35 Q7 1 0.5633 0.4078 0.4257 11.00000 0.05 0.33 Q8 1 0.4163 0.7756 0.6224 11.00000 0.05 0.30 Q9 1 0.4879 0.8036 0.6462 11.00000 0.05 0.28 Q10 1 0.6348 0.6908 0.2827 11.00000 0.05 0.27 Q11 1 0.5725 0.6866 0.2572 11.00000 0.05 0.27 Q12 1 0.5903 0.8044 0.3680 11.00000 0.05 0.26 Q13 1 0.4269 0.3880 0.5808 11.00000 0.05 0.26 Q14 1 0.5629 0.8009 0.6648 11.00000 0.05 0.25 Q15 1 0.5227 0.7844 0.3388 11.00000 0.05 0.25 Q16 1 0.3979 0.6967 0.7271 11.00000 0.05 0.25 Q17 1 0.4834 0.8334 0.5153 11.00000 0.05 0.24 Q18 1 0.6714 0.3052 0.3799 11.00000 0.05 0.23 Q19 1 0.6421 0.7437 0.3395 11.00000 0.05 0.23 Q20 1 0.5118 0.7380 0.2847 11.00000 0.05 0.23 ; _shelx_res_checksum 86172 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, 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 O1 O 0.41602(9) 0.56148(15) 0.51510(8) 0.0195(3) Uani 1 1 d . . . . . O2 O 0.38859(11) 0.39456(18) 0.59295(9) 0.0306(4) Uani 1 1 d . . . . . O3 O 0.56040(12) 0.32423(19) 0.44290(13) 0.0437(5) Uani 1 1 d . . . . . O4 O 0.65912(10) 0.47503(16) 0.42934(9) 0.0252(3) Uani 1 1 d . . . . . N1 N 0.51399(9) 0.86556(15) 0.43149(8) 0.0132(3) Uani 1 1 d . . . . . N2 N 0.47298(10) 0.85774(16) 0.54816(8) 0.0144(3) Uani 1 1 d . . . . . C1 C 0.49276(11) 0.79027(17) 0.48830(10) 0.0132(3) Uani 1 1 d . . . . . C2 C 0.47253(13) 1.00925(19) 0.55231(11) 0.0189(3) Uani 1 1 d . . . . . H2A H 0.526638 1.042818 0.567304 0.023 Uiso 1 1 calc R U . . . H2B H 0.434874 1.039502 0.588828 0.023 Uiso 1 1 calc R U . . . C3 C 0.44741(12) 1.06792(19) 0.47938(11) 0.0185(3) Uani 1 1 d . . . . . H3A H 0.448017 1.169322 0.481179 0.022 Uiso 1 1 calc R U . . . H3B H 0.392622 1.037323 0.464651 0.022 Uiso 1 1 calc R U . . . C4 C 0.50660(13) 1.01653(18) 0.42635(11) 0.0192(4) Uani 1 1 d . . . . . H4A H 0.488361 1.042564 0.376553 0.023 Uiso 1 1 calc R U . . . H4B H 0.559474 1.059374 0.437075 0.023 Uiso 1 1 calc R U . . . C5 C 0.54786(11) 0.80322(18) 0.36883(9) 0.0133(3) Uani 1 1 d . . . . . C6 C 0.49646(11) 0.76908(19) 0.30905(10) 0.0144(3) Uani 1 1 d . . . . . C7 C 0.52969(12) 0.7061(2) 0.24999(10) 0.0191(4) Uani 1 1 d . . . . . H7 H 0.496111 0.679064 0.209656 0.023 Uiso 1 1 calc R U . . . C8 C 0.61155(12) 0.6824(2) 0.24956(11) 0.0210(4) Uani 1 1 d . . . . . H8 H 0.633374 0.636865 0.209587 0.025 Uiso 1 1 calc R U . . . C9 C 0.66176(12) 0.7249(2) 0.30731(11) 0.0185(3) Uani 1 1 d . . . . . H9 H 0.717842 0.711226 0.305373 0.022 Uiso 1 1 calc R U . . . C10 C 0.63118(11) 0.78745(19) 0.36817(10) 0.0150(3) Uani 1 1 d . . . . . C11 C 0.40730(11) 0.7988(2) 0.30714(10) 0.0174(3) Uani 1 1 d . . . . . H11 H 0.393550 0.835744 0.355420 0.021 Uiso 1 1 calc R U . . . C12 C 0.35722(13) 0.6694(2) 0.29186(13) 0.0236(4) Uani 1 1 d . . . . . H12A H 0.372971 0.598220 0.327072 0.035 Uiso 1 1 calc R U . . . H12B H 0.366322 0.636452 0.242881 0.035 Uiso 1 1 calc R U . . . H12C H 0.300375 0.690933 0.295852 0.035 Uiso 1 1 calc R U . . . C13 C 0.38584(14) 0.9072(3) 0.24968(14) 0.0285(5) Uani 1 1 d . . . . . H13A H 0.420651 0.987222 0.257210 0.043 Uiso 1 1 calc R U . . . H13B H 0.329886 0.934892 0.253566 0.043 Uiso 1 1 calc R U . . . H13C H 0.393225 0.868965 0.201465 0.043 Uiso 1 1 calc R U . . . C14 C 0.68845(12) 0.8465(2) 0.42676(11) 0.0180(3) Uani 1 1 d . . . . . H14 H 0.656797 0.870565 0.469504 0.022 Uiso 1 1 calc R U . . . C15 C 0.72500(14) 0.9789(2) 0.39782(13) 0.0258(4) Uani 1 1 d . . . . . H15A H 0.759675 1.020929 0.435823 0.039 Uiso 1 1 calc R U . . . H15B H 0.682068 1.042904 0.383190 0.039 Uiso 1 1 calc R U . . . H15C H 0.756581 0.957456 0.355974 0.039 Uiso 1 1 calc R U . . . C16 C 0.75641(14) 0.7504(2) 0.45235(14) 0.0288(5) Uani 1 1 d . . . . . H16A H 0.789431 0.795466 0.490517 0.043 Uiso 1 1 calc R U . . . H16B H 0.789471 0.728454 0.411562 0.043 Uiso 1 1 calc R U . . . H16C H 0.733802 0.665814 0.471361 0.043 Uiso 1 1 calc R U . . . C17 C 0.45793(11) 0.79058(19) 0.61617(10) 0.0151(3) Uani 1 1 d . . . . . C18 C 0.37876(12) 0.7553(2) 0.63134(10) 0.0175(3) Uani 1 1 d . . . . . C19 C 0.36595(13) 0.6998(2) 0.69942(11) 0.0223(4) Uani 1 1 d . . . . . H19 H 0.313401 0.673149 0.710842 0.027 Uiso 1 1 calc R U . . . C20 C 0.42830(14) 0.6829(2) 0.75068(11) 0.0251(4) Uani 1 1 d . . . . . H20 H 0.418308 0.644438 0.796555 0.030 Uiso 1 1 calc R U . . . C21 C 0.50501(14) 0.7220(2) 0.73504(11) 0.0236(4) Uani 1 1 d . . . . . H21 H 0.547200 0.711134 0.770768 0.028 Uiso 1 1 calc R U . . . C22 C 0.52175(12) 0.7774(2) 0.66762(10) 0.0184(4) Uani 1 1 d . . . . . C23 C 0.60636(12) 0.8263(2) 0.65472(11) 0.0206(4) Uani 1 1 d . . . . . H23 H 0.607964 0.857170 0.603254 0.025 Uiso 1 1 calc R U . . . C24 C 0.66951(13) 0.7151(2) 0.66729(13) 0.0263(4) Uani 1 1 d . . . . . H24A H 0.721324 0.748720 0.652149 0.039 Uiso 1 1 calc R U . . . H24B H 0.654100 0.633553 0.638979 0.039 Uiso 1 1 calc R U . . . H24C H 0.673675 0.691374 0.718806 0.039 Uiso 1 1 calc R U . . . C25 C 0.62685(16) 0.9494(3) 0.70351(14) 0.0319(5) Uani 1 1 d . . . . . H25A H 0.681889 0.978812 0.696128 0.048 Uiso 1 1 calc R U . . . H25B H 0.621798 0.923255 0.754237 0.048 Uiso 1 1 calc R U . . . H25C H 0.589981 1.024895 0.691379 0.048 Uiso 1 1 calc R U . . . C26 C 0.30880(12) 0.7821(2) 0.57802(11) 0.0206(4) Uani 1 1 d . . . . . H26 H 0.329839 0.787486 0.528387 0.025 Uiso 1 1 calc R U . . . C27 C 0.24468(14) 0.6695(3) 0.57790(14) 0.0294(5) Uani 1 1 d . . . . . H27A H 0.207593 0.681337 0.535763 0.044 Uiso 1 1 calc R U . . . H27B H 0.215116 0.675895 0.622273 0.044 Uiso 1 1 calc R U . . . H27C H 0.270402 0.579508 0.575571 0.044 Uiso 1 1 calc R U . . . C28 C 0.26983(14) 0.9203(3) 0.59491(13) 0.0282(4) Uani 1 1 d . . . . . H28A H 0.223153 0.934853 0.561794 0.042 Uiso 1 1 calc R U . . . H28B H 0.308587 0.994234 0.588806 0.042 Uiso 1 1 calc R U . . . H28C H 0.252887 0.919965 0.644909 0.042 Uiso 1 1 calc R U . . . C29 C 0.56349(12) 0.53196(19) 0.51323(11) 0.0184(3) Uani 1 1 d . . . . . H29 H 0.607787 0.593933 0.531002 0.022 Uiso 1 1 calc R U . . . C30 C 0.52616(14) 0.4563(2) 0.57553(12) 0.0225(4) Uani 1 1 d . . . . . H30A H 0.543726 0.359380 0.576725 0.027 Uiso 1 1 calc R U . . . H30B H 0.542522 0.499572 0.622309 0.027 Uiso 1 1 calc R U . . . C31 C 0.43641(13) 0.4647(2) 0.56258(11) 0.0205(4) Uani 1 1 d . . . . . C32 C 0.59141(13) 0.4317(2) 0.45862(13) 0.0229(4) Uani 1 1 d . . . . . C33 C 0.69272(15) 0.3864(3) 0.37684(15) 0.0336(5) Uani 1 1 d . . . . . H33A H 0.741646 0.427713 0.359477 0.050 Uiso 1 1 calc R U . . . H33B H 0.653962 0.373389 0.336031 0.050 Uiso 1 1 calc R U . . . H33C H 0.705495 0.297458 0.399146 0.050 Uiso 1 1 calc R U . . . B1 B 0.48607(13) 0.6205(2) 0.47738(11) 0.0163(4) Uani 1 1 d . . . . . H1 H 0.4778(18) 0.602(3) 0.4211(16) 0.024 Uiso 1 1 d . 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 0.0194(7) 0.0184(6) 0.0211(6) 0.0016(5) 0.0038(5) -0.0029(5) O2 0.0405(10) 0.0259(8) 0.0258(8) 0.0048(6) 0.0071(7) -0.0107(7) O3 0.0414(10) 0.0222(8) 0.0700(14) -0.0215(9) 0.0297(10) -0.0137(7) O4 0.0249(8) 0.0227(7) 0.0287(8) -0.0047(6) 0.0073(6) -0.0019(6) N1 0.0169(7) 0.0100(6) 0.0128(6) 0.0005(5) 0.0029(5) 0.0007(5) N2 0.0175(7) 0.0134(6) 0.0125(6) 0.0011(5) 0.0032(5) 0.0020(5) C1 0.0142(7) 0.0123(7) 0.0131(7) 0.0007(6) 0.0012(6) 0.0006(6) C2 0.0253(9) 0.0130(8) 0.0186(8) -0.0026(6) 0.0050(7) 0.0014(7) C3 0.0219(9) 0.0125(7) 0.0214(9) 0.0012(7) 0.0035(7) 0.0039(6) C4 0.0286(10) 0.0103(7) 0.0191(8) 0.0011(6) 0.0066(7) 0.0007(7) C5 0.0165(8) 0.0122(7) 0.0117(7) 0.0009(6) 0.0040(6) -0.0007(6) C6 0.0143(8) 0.0144(7) 0.0148(7) 0.0016(6) 0.0028(6) -0.0017(6) C7 0.0210(9) 0.0223(9) 0.0142(8) -0.0016(6) 0.0032(7) -0.0052(7) C8 0.0218(9) 0.0240(9) 0.0178(8) -0.0043(7) 0.0076(7) -0.0014(7) C9 0.0155(8) 0.0203(9) 0.0200(8) -0.0006(7) 0.0055(6) -0.0004(7) C10 0.0153(8) 0.0144(7) 0.0154(8) 0.0018(6) 0.0026(6) -0.0018(6) C11 0.0156(8) 0.0205(8) 0.0161(8) 0.0037(6) 0.0023(6) -0.0010(6) C12 0.0177(9) 0.0245(10) 0.0286(10) 0.0028(8) -0.0005(7) -0.0066(7) C13 0.0211(10) 0.0306(11) 0.0338(11) 0.0135(9) 0.0002(8) 0.0009(8) C14 0.0167(8) 0.0194(8) 0.0180(8) 0.0016(7) 0.0003(6) -0.0040(7) C15 0.0290(11) 0.0211(9) 0.0274(10) 0.0011(8) 0.0017(8) -0.0099(8) C16 0.0212(10) 0.0273(10) 0.0368(12) 0.0028(9) -0.0098(8) -0.0030(8) C17 0.0184(8) 0.0150(8) 0.0122(7) 0.0004(6) 0.0039(6) 0.0026(6) C18 0.0187(8) 0.0188(8) 0.0154(8) -0.0015(7) 0.0046(6) 0.0018(7) C19 0.0248(10) 0.0238(9) 0.0189(9) 0.0004(7) 0.0085(7) -0.0004(7) C20 0.0345(11) 0.0258(10) 0.0155(8) 0.0034(7) 0.0064(8) 0.0025(8) C21 0.0289(10) 0.0274(10) 0.0144(8) 0.0019(8) 0.0010(7) 0.0059(8) C22 0.0202(9) 0.0207(8) 0.0145(8) -0.0012(6) 0.0021(7) 0.0046(7) C23 0.0180(9) 0.0253(9) 0.0181(8) -0.0014(7) -0.0009(6) 0.0028(7) C24 0.0190(9) 0.0336(11) 0.0258(10) -0.0058(8) -0.0036(7) 0.0060(8) C25 0.0329(12) 0.0299(11) 0.0327(12) -0.0111(9) -0.0002(9) -0.0037(9) C26 0.0176(8) 0.0258(10) 0.0186(8) -0.0025(7) 0.0033(7) 0.0008(7) C27 0.0214(10) 0.0339(12) 0.0332(11) -0.0080(9) 0.0050(8) -0.0057(8) C28 0.0217(10) 0.0316(11) 0.0309(11) -0.0021(9) -0.0018(8) 0.0072(8) C29 0.0197(9) 0.0132(8) 0.0224(9) 0.0000(7) 0.0016(7) 0.0004(6) C30 0.0279(10) 0.0174(8) 0.0220(9) 0.0053(7) -0.0004(7) 0.0018(7) C31 0.0284(10) 0.0155(8) 0.0177(8) -0.0006(7) 0.0008(7) -0.0025(7) C32 0.0218(9) 0.0150(8) 0.0325(10) 0.0003(7) 0.0053(8) 0.0018(7) C33 0.0311(12) 0.0344(12) 0.0366(13) -0.0138(10) 0.0141(10) -0.0033(10) B1 0.0173(9) 0.0139(8) 0.0177(9) 0.0006(7) 0.0012(7) -0.0014(7) 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' N N 0.0061 0.0033 '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 C31 O1 B1 113.47(16) . . ? C32 O4 C33 116.53(18) . . ? C1 N1 C4 124.72(15) . . ? C1 N1 C5 121.62(14) . . ? C5 N1 C4 113.66(14) . . ? C1 N2 C2 122.30(15) . . ? C1 N2 C17 123.58(15) . . ? C17 N2 C2 113.86(14) . . ? N1 C1 B1 117.76(15) . . ? N2 C1 N1 117.47(15) . . ? N2 C1 B1 124.59(15) . . ? N2 C2 C3 109.56(15) . . ? C2 C3 C4 106.94(16) . . ? N1 C4 C3 110.10(15) . . ? C6 C5 N1 118.72(16) . . ? C10 C5 N1 118.64(16) . . ? C10 C5 C6 122.51(16) . . ? C5 C6 C11 122.42(16) . . ? C7 C6 C5 117.98(17) . . ? C7 C6 C11 119.60(17) . . ? C8 C7 C6 120.53(18) . . ? C7 C8 C9 120.38(18) . . ? C8 C9 C10 121.21(17) . . ? C5 C10 C14 122.93(17) . . ? C9 C10 C5 117.12(17) . . ? C9 C10 C14 119.71(17) . . ? C6 C11 C12 112.00(16) . . ? C6 C11 C13 110.27(16) . . ? C13 C11 C12 109.42(18) . . ? C10 C14 C15 108.48(16) . . ? C10 C14 C16 114.89(17) . . ? C16 C14 C15 108.72(17) . . ? C18 C17 N2 119.07(17) . . ? C22 C17 N2 118.20(17) . . ? C22 C17 C18 122.34(17) . . ? C17 C18 C26 122.12(17) . . ? C19 C18 C17 117.36(18) . . ? C19 C18 C26 120.45(18) . . ? C20 C19 C18 121.4(2) . . ? C21 C20 C19 120.01(19) . . ? C20 C21 C22 121.3(2) . . ? C17 C22 C23 123.24(17) . . ? C21 C22 C17 117.55(18) . . ? C21 C22 C23 119.14(17) . . ? C22 C23 C24 113.25(18) . . ? C22 C23 C25 109.73(17) . . ? C24 C23 C25 109.52(18) . . ? C18 C26 C27 113.26(19) . . ? C18 C26 C28 109.94(17) . . ? C27 C26 C28 108.98(18) . . ? C30 C29 B1 102.31(15) . . ? C32 C29 C30 110.18(16) . . ? C32 C29 B1 109.33(17) . . ? C31 C30 C29 107.00(16) . . ? O1 C31 C30 111.55(17) . . ? O2 C31 O1 123.8(2) . . ? O2 C31 C30 124.6(2) . . ? O3 C32 O4 122.6(2) . . ? O3 C32 C29 126.1(2) . . ? O4 C32 C29 111.18(18) . . ? O1 B1 C1 111.82(15) . . ? O1 B1 C29 102.97(15) . . ? C29 B1 C1 114.74(15) . . ? 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 C31 1.323(2) . ? O1 B1 1.506(3) . ? O2 C31 1.211(3) . ? O3 C32 1.200(3) . ? O4 C32 1.346(3) . ? O4 C33 1.435(3) . ? N1 C1 1.344(2) . ? N1 C4 1.481(2) . ? N1 C5 1.448(2) . ? N2 C1 1.343(2) . ? N2 C2 1.480(2) . ? N2 C17 1.451(2) . ? C1 B1 1.672(3) . ? C2 C3 1.507(3) . ? C3 C4 1.512(3) . ? C5 C6 1.409(2) . ? C5 C10 1.403(3) . ? C6 C7 1.392(3) . ? C6 C11 1.518(3) . ? C7 C8 1.389(3) . ? C8 C9 1.391(3) . ? C9 C10 1.398(3) . ? C10 C14 1.526(3) . ? C11 C12 1.534(3) . ? C11 C13 1.530(3) . ? C14 C15 1.537(3) . ? C14 C16 1.531(3) . ? C17 C18 1.409(3) . ? C17 C22 1.403(3) . ? C18 C19 1.396(3) . ? C18 C26 1.518(3) . ? C19 C20 1.386(3) . ? C20 C21 1.382(3) . ? C21 C22 1.399(3) . ? C22 C23 1.523(3) . ? C23 C24 1.525(3) . ? C23 C25 1.531(3) . ? C26 C27 1.535(3) . ? C26 C28 1.536(3) . ? C29 C30 1.527(3) . ? C29 C32 1.497(3) . ? C29 B1 1.668(3) . ? C30 C31 1.511(3) . ? 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 C1 B1 O1 -140.97(16) . . . . ? N1 C1 B1 C29 102.25(19) . . . . ? N1 C5 C6 C7 -178.42(16) . . . . ? N1 C5 C6 C11 1.7(2) . . . . ? N1 C5 C10 C9 179.03(16) . . . . ? N1 C5 C10 C14 -6.7(3) . . . . ? N2 C1 B1 O1 34.1(2) . . . . ? N2 C1 B1 C29 -82.7(2) . . . . ? N2 C2 C3 C4 -58.8(2) . . . . ? N2 C17 C18 C19 -175.51(17) . . . . ? N2 C17 C18 C26 1.5(3) . . . . ? N2 C17 C22 C21 175.17(17) . . . . ? N2 C17 C22 C23 -1.8(3) . . . . ? C1 N1 C4 C3 -19.6(3) . . . . ? C1 N1 C5 C6 94.5(2) . . . . ? C1 N1 C5 C10 -89.6(2) . . . . ? C1 N2 C2 C3 33.8(2) . . . . ? C1 N2 C17 C18 -93.6(2) . . . . ? C1 N2 C17 C22 93.4(2) . . . . ? C2 N2 C1 N1 1.2(3) . . . . ? C2 N2 C1 B1 -173.87(17) . . . . ? C2 N2 C17 C18 92.2(2) . . . . ? C2 N2 C17 C22 -80.8(2) . . . . ? C2 C3 C4 N1 51.9(2) . . . . ? C4 N1 C1 N2 -8.8(3) . . . . ? C4 N1 C1 B1 166.62(17) . . . . ? C4 N1 C5 C6 -86.1(2) . . . . ? C4 N1 C5 C10 89.7(2) . . . . ? C5 N1 C1 N2 170.45(16) . . . . ? C5 N1 C1 B1 -14.1(2) . . . . ? C5 N1 C4 C3 161.10(16) . . . . ? C5 C6 C7 C8 -2.2(3) . . . . ? C5 C6 C11 C12 -124.78(19) . . . . ? C5 C6 C11 C13 113.1(2) . . . . ? C5 C10 C14 C15 -100.9(2) . . . . ? C5 C10 C14 C16 137.25(19) . . . . ? C6 C5 C10 C9 -5.3(3) . . . . ? C6 C5 C10 C14 169.02(17) . . . . ? C6 C7 C8 C9 -1.9(3) . . . . ? C7 C6 C11 C12 55.3(2) . . . . ? C7 C6 C11 C13 -66.8(2) . . . . ? C7 C8 C9 C10 2.5(3) . . . . ? C8 C9 C10 C5 1.0(3) . . . . ? C8 C9 C10 C14 -173.47(18) . . . . ? C9 C10 C14 C15 73.3(2) . . . . ? C9 C10 C14 C16 -48.6(2) . . . . ? C10 C5 C6 C7 5.9(3) . . . . ? C10 C5 C6 C11 -174.00(17) . . . . ? C11 C6 C7 C8 177.70(18) . . . . ? C17 N2 C1 N1 -172.56(16) . . . . ? C17 N2 C1 B1 12.4(3) . . . . ? C17 N2 C2 C3 -151.87(16) . . . . ? C17 C18 C19 C20 1.4(3) . . . . ? C17 C18 C26 C27 143.75(19) . . . . ? C17 C18 C26 C28 -94.1(2) . . . . ? C17 C22 C23 C24 -126.1(2) . . . . ? C17 C22 C23 C25 111.2(2) . . . . ? C18 C17 C22 C21 2.5(3) . . . . ? C18 C17 C22 C23 -174.49(17) . . . . ? C18 C19 C20 C21 0.4(3) . . . . ? C19 C18 C26 C27 -39.3(3) . . . . ? C19 C18 C26 C28 82.9(2) . . . . ? C19 C20 C21 C22 -0.8(3) . . . . ? C20 C21 C22 C17 -0.6(3) . . . . ? C20 C21 C22 C23 176.5(2) . . . . ? C21 C22 C23 C24 57.0(2) . . . . ? C21 C22 C23 C25 -65.7(2) . . . . ? C22 C17 C18 C19 -2.9(3) . . . . ? C22 C17 C18 C26 174.16(18) . . . . ? C26 C18 C19 C20 -175.7(2) . . . . ? C29 C30 C31 O1 -16.8(2) . . . . ? C29 C30 C31 O2 165.0(2) . . . . ? C30 C29 C32 O3 33.7(3) . . . . ? C30 C29 C32 O4 -144.50(18) . . . . ? C30 C29 B1 O1 -10.17(18) . . . . ? C30 C29 B1 C1 111.57(17) . . . . ? C31 O1 B1 C1 -123.09(17) . . . . ? C31 O1 B1 C29 0.6(2) . . . . ? C32 C29 C30 C31 -100.71(19) . . . . ? C32 C29 B1 O1 106.61(17) . . . . ? C32 C29 B1 C1 -131.64(17) . . . . ? C33 O4 C32 O3 0.8(4) . . . . ? C33 O4 C32 C29 179.03(19) . . . . ? B1 O1 C31 O2 -171.93(19) . . . . ? B1 O1 C31 C30 9.8(2) . . . . ? B1 C29 C30 C31 15.46(19) . . . . ? B1 C29 C32 O3 -78.0(3) . . . . ? B1 C29 C32 O4 103.8(2) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 1.18125 2 -0.18125