#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:10:59 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306440 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721007.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_7721007 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 'C32 H45 B N2 O4' _chemical_formula_sum 'C32 H45 B N2 O4' _chemical_formula_weight 532.51 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/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 91.399(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.2071(6) _cell_length_b 10.1666(6) _cell_length_c 32.2381(17) _cell_measurement_reflns_used 92644 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 32.235 _cell_measurement_theta_min 2.40 _cell_volume 3016.7(3) _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 0.1152 _diffrn_reflns_av_unetI/netI 0.0368 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 149855 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.526 _diffrn_reflns_theta_min 2.369 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.1497 _exptl_absorpt_correction_T_min 0.1167 _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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.172 _exptl_crystal_description Plate _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.325 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef 0.0086(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 365 _refine_ls_number_reflns 6931 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0482 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+2.0886P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1083 _refine_ls_wR_factor_ref 0.1233 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5231 _reflns_number_total 6931 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00852f2.cif _cod_data_source_block mo_apr_240725_a _cod_depositor_comments 'Adding full bibliography for 7721003--7721010.cif.' _cod_database_code 7721007 _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.a Ternary CH refined with riding coordinates: C10(H10), C13(H13), C22(H22), C25(H25), C29(H29) 1.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C30(H30A,H30B), C2(H2A,H2B) 1.c Aromatic/amide H refined with riding coordinates: C18(H18), C19(H19), C20(H20), C7(H7), C8(H8), C9(H9) 1.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B, H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A, H27B,H27C), C33(H33A,H33B,H33C) ; _shelx_res_file ; TITL mo_apr_240725_a.res in P2(1)/c mo_apr_240725_a.res created by SHELXL-2018/3 at 19:40:56 on 02-Sep-2025 REM Old TITL mo_apr_240725 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.159, Rweak 0.009, Alpha 0.029 REM 0.681 for 369 systematic absences, Orientation as input REM Formula found by SHELXT: C33 N2 O4 CELL 0.71073 9.2071 10.1666 32.2381 90.000 91.399 90.000 ZERR 4.000 0.0006 0.0006 0.0017 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H B N O UNIT 128 180 4 8 16 TEMP -173.150 L.S. 10 BOND OMIT 0 1 1 OMIT 1 2 1 OMIT -1 1 6 OMIT -2 2 7 LIST 4 FMAP 2 PLAN 10 ACTA CONF SIZE 0.20 0.12 0.1 WGHT 0.037300 2.088600 EXTI 0.008586 FVAR 0.37415 O1 5 0.532657 0.461105 0.382594 11.00000 0.02261 0.02768 = 0.02091 0.00199 0.00383 0.00420 O2 5 0.711378 0.371479 0.346402 11.00000 0.02897 0.03716 = 0.03518 -0.00364 0.00508 0.00979 O3 5 0.760624 0.740060 0.381537 11.00000 0.02126 0.03248 = 0.03582 -0.00075 -0.00528 0.00000 O4 5 0.587204 0.894432 0.376451 11.00000 0.02675 0.02503 = 0.03226 -0.00258 -0.00460 -0.00033 N1 4 0.192656 0.589990 0.416394 11.00000 0.01853 0.02544 = 0.01633 -0.00151 0.00233 -0.00097 N2 4 0.197035 0.542421 0.350913 11.00000 0.01782 0.03307 = 0.01765 -0.00431 0.00211 -0.00071 C1 1 0.038269 0.563283 0.405618 11.00000 0.01696 0.03794 = 0.02194 -0.00136 0.00219 -0.00002 AFIX 23 H1A 2 -0.024729 0.636932 0.414128 11.00000 -1.20000 H1B 2 0.004706 0.481136 0.418804 11.00000 -1.20000 AFIX 0 C10 1 0.182576 0.746486 0.287586 11.00000 0.02481 0.03158 = 0.02955 -0.00083 -0.00158 0.00186 AFIX 13 H10 2 0.181937 0.760347 0.318290 11.00000 -1.20000 AFIX 0 C11 1 0.276254 0.853582 0.268574 11.00000 0.04154 0.03078 = 0.03482 0.00302 -0.00314 -0.00066 AFIX 137 H11A 2 0.376717 0.844411 0.278917 11.00000 -1.50000 H11B 2 0.238872 0.940204 0.276310 11.00000 -1.50000 H11C 2 0.273304 0.844876 0.238290 11.00000 -1.50000 AFIX 0 C12 1 0.026422 0.763188 0.270355 11.00000 0.03133 0.04807 = 0.05347 0.00549 -0.00518 0.00739 AFIX 137 H12A 2 -0.034406 0.691659 0.280590 11.00000 -1.50000 H12B 2 0.026668 0.760780 0.239967 11.00000 -1.50000 H12C 2 -0.012494 0.847767 0.279528 11.00000 -1.50000 AFIX 0 C13 1 0.288571 0.273920 0.335337 11.00000 0.03510 0.03178 = 0.02696 0.00307 0.00102 0.00286 AFIX 13 H13 2 0.301617 0.317963 0.362912 11.00000 -1.20000 AFIX 0 C14 1 0.142577 0.202991 0.335148 11.00000 0.04063 0.05140 = 0.06261 0.03009 0.00334 -0.00436 AFIX 137 H14A 2 0.064555 0.267163 0.338882 11.00000 -1.50000 H14B 2 0.141899 0.138838 0.357831 11.00000 -1.50000 H14C 2 0.127476 0.157399 0.308608 11.00000 -1.50000 AFIX 0 C15 1 0.410266 0.173759 0.331351 11.00000 0.04120 0.02771 = 0.04620 0.00211 -0.00280 0.00300 AFIX 137 H15A 2 0.504136 0.219248 0.331955 11.00000 -1.50000 H15B 2 0.397955 0.126196 0.305060 11.00000 -1.50000 H15C 2 0.407075 0.111331 0.354474 11.00000 -1.50000 AFIX 0 C16 1 0.226544 0.622971 0.459093 11.00000 0.01770 0.02515 = 0.01600 -0.00204 0.00391 0.00036 C17 1 0.231024 0.754901 0.470741 11.00000 0.02081 0.02405 = 0.02135 -0.00124 0.00353 -0.00046 C18 1 0.239240 0.783176 0.513219 11.00000 0.02490 0.02341 = 0.02540 -0.00637 0.00367 -0.00117 AFIX 43 H18 2 0.240827 0.872281 0.522094 11.00000 -1.20000 AFIX 0 C19 1 0.245090 0.683902 0.542500 11.00000 0.02244 0.03066 = 0.01879 -0.00455 0.00318 -0.00066 AFIX 43 H19 2 0.248915 0.705089 0.571207 11.00000 -1.20000 AFIX 0 C20 1 0.245380 0.553456 0.530011 11.00000 0.02013 0.02605 = 0.01850 0.00100 0.00255 -0.00042 AFIX 43 H20 2 0.252871 0.485886 0.550305 11.00000 -1.20000 AFIX 0 C21 1 0.234833 0.519878 0.488079 11.00000 0.01554 0.02260 = 0.02046 -0.00083 0.00269 -0.00003 C22 1 0.241948 0.376928 0.474821 11.00000 0.02233 0.02205 = 0.02169 -0.00145 0.00204 -0.00002 AFIX 13 H22 2 0.202361 0.370748 0.445724 11.00000 -1.20000 AFIX 0 C23 1 0.400671 0.332939 0.474772 11.00000 0.02332 0.02462 = 0.03940 -0.00371 0.00537 0.00081 AFIX 137 H23A 2 0.406097 0.241748 0.465081 11.00000 -1.50000 H23B 2 0.442338 0.338996 0.502972 11.00000 -1.50000 H23C 2 0.455357 0.389868 0.456233 11.00000 -1.50000 AFIX 0 C24 1 0.151789 0.286493 0.501877 11.00000 0.02843 0.02593 = 0.03871 -0.00206 0.01058 -0.00241 AFIX 137 H24A 2 0.150084 0.197835 0.489942 11.00000 -1.50000 H24B 2 0.052343 0.320374 0.503122 11.00000 -1.50000 H24C 2 0.195063 0.283215 0.529934 11.00000 -1.50000 AFIX 0 C25 1 0.227332 0.865978 0.439188 11.00000 0.03714 0.02467 = 0.02548 0.00202 0.00542 -0.00294 AFIX 13 H25 2 0.246033 0.827204 0.411315 11.00000 -1.20000 AFIX 0 C26 1 0.345699 0.966323 0.448656 11.00000 0.04564 0.02718 = 0.03934 0.00010 0.00907 -0.00898 AFIX 137 H26A 2 0.347493 1.031742 0.426348 11.00000 -1.50000 H26B 2 0.439975 0.921756 0.450741 11.00000 -1.50000 H26C 2 0.326028 1.010238 0.474991 11.00000 -1.50000 AFIX 0 C27 1 0.077496 0.932023 0.437077 11.00000 0.04092 0.04009 = 0.05363 0.02312 0.00110 0.00206 AFIX 137 H27A 2 0.078967 1.004957 0.417216 11.00000 -1.50000 H27B 2 0.053724 0.965726 0.464571 11.00000 -1.50000 H27C 2 0.004091 0.867570 0.428097 11.00000 -1.50000 AFIX 0 C29 1 0.528917 0.683168 0.350724 11.00000 0.01879 0.02608 = 0.01949 0.00004 0.00037 -0.00052 AFIX 13 H29 2 0.453386 0.732788 0.334314 11.00000 -1.20000 AFIX 0 C30 1 0.606047 0.579878 0.324469 11.00000 0.02024 0.03257 = 0.01951 -0.00058 0.00237 -0.00269 AFIX 23 H30A 2 0.546717 0.558273 0.299363 11.00000 -1.20000 H30B 2 0.701594 0.613197 0.315730 11.00000 -1.20000 AFIX 0 C31 1 0.625199 0.460110 0.351580 11.00000 0.01984 0.03179 = 0.02153 -0.00329 0.00111 0.00087 C32 1 0.638379 0.771883 0.370768 11.00000 0.02203 0.02795 = 0.01896 0.00315 0.00114 -0.00129 C33 1 0.688162 0.984721 0.396119 11.00000 0.03548 0.03028 = 0.04926 -0.00704 -0.00901 -0.00469 AFIX 137 H33A 2 0.640614 1.069941 0.399974 11.00000 -1.50000 H33B 2 0.772714 0.996000 0.378579 11.00000 -1.50000 H33C 2 0.719763 0.949576 0.423169 11.00000 -1.50000 AFIX 0 B1 3 0.456985 0.591631 0.387951 11.00000 0.01938 0.02531 = 0.01765 -0.00121 0.00106 0.00125 H1 2 0.482902 0.633568 0.418869 11.00000 -1.50000 C2 1 0.039430 0.550009 0.358997 11.00000 0.01973 0.05837 = 0.02481 -0.00968 0.00298 -0.00305 AFIX 23 H2A 2 -0.011770 0.469311 0.349601 11.00000 -1.20000 H2B 2 -0.005676 0.627352 0.345182 11.00000 -1.20000 AFIX 0 C3 1 0.279096 0.572387 0.384371 11.00000 0.02157 0.01818 = 0.01640 0.00018 0.00158 0.00103 C4 1 0.290139 0.380755 0.302138 11.00000 0.02153 0.02763 = 0.02277 -0.00226 0.00061 -0.00133 C5 1 0.245715 0.510416 0.310095 11.00000 0.01712 0.03074 = 0.01691 -0.00403 0.00061 -0.00058 C6 1 0.237785 0.608253 0.279317 11.00000 0.01784 0.02846 = 0.02175 -0.00269 -0.00108 -0.00342 C7 1 0.279920 0.573454 0.239538 11.00000 0.02642 0.03677 = 0.01890 0.00093 0.00015 -0.00420 AFIX 43 H7 2 0.276236 0.637112 0.217966 11.00000 -1.20000 AFIX 0 C8 1 0.327082 0.447082 0.231141 11.00000 0.03100 0.04110 = 0.01949 -0.00774 0.00458 -0.00341 AFIX 43 H8 2 0.356343 0.425348 0.203930 11.00000 -1.20000 AFIX 0 C9 1 0.332111 0.352420 0.261767 11.00000 0.02941 0.02972 = 0.02810 -0.00840 0.00312 -0.00055 AFIX 43 H9 2 0.364720 0.266349 0.255292 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM mo_apr_240725_a.res in P2(1)/c REM wR2 = 0.123343, GooF = S = 1.06592, Restrained GooF = 1.06592 for all data REM R1 = 0.048232 for 5231 Fo > 4sig(Fo) and 0.073264 for all 6931 data REM 365 parameters refined using 0 restraints END WGHT 0.0373 2.0885 REM Highest difference peak 0.325, deepest hole -0.307, 1-sigma level 0.054 Q1 1 0.2436 0.5623 0.2943 11.00000 0.05 0.33 Q2 1 0.0439 0.4642 0.3693 11.00000 0.05 0.31 Q3 1 0.2508 0.5741 0.4759 11.00000 0.05 0.31 Q4 1 0.2309 0.8045 0.4555 11.00000 0.05 0.30 Q5 1 0.2422 0.4443 0.4818 11.00000 0.05 0.29 Q6 1 0.2183 0.6136 0.4402 11.00000 0.05 0.28 Q7 1 0.2530 0.5262 0.5063 11.00000 0.05 0.28 Q8 1 0.2399 0.6926 0.4638 11.00000 0.05 0.28 Q9 1 0.2210 0.6745 0.2862 11.00000 0.05 0.26 Q10 1 0.2392 0.7660 0.4914 11.00000 0.05 0.25 ; _shelx_res_checksum 1455 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.53266(12) 0.46111(12) 0.38259(3) 0.0237(3) Uani 1 1 d . . . . . O2 O 0.71138(14) 0.37148(13) 0.34640(4) 0.0337(3) Uani 1 1 d . . . . . O3 O 0.76062(13) 0.74006(13) 0.38154(4) 0.0300(3) Uani 1 1 d . . . . . O4 O 0.58720(13) 0.89443(12) 0.37645(4) 0.0281(3) Uani 1 1 d . . . . . N1 N 0.19266(14) 0.58999(14) 0.41639(4) 0.0201(3) Uani 1 1 d . . . . . N2 N 0.19704(14) 0.54242(15) 0.35091(4) 0.0228(3) Uani 1 1 d . . . . . C1 C 0.03827(17) 0.56328(19) 0.40562(5) 0.0256(4) Uani 1 1 d . . . . . H1A H -0.024729 0.636932 0.414128 0.031 Uiso 1 1 calc R U . . . H1B H 0.004706 0.481136 0.418804 0.031 Uiso 1 1 calc R U . . . C10 C 0.18258(19) 0.74649(18) 0.28759(6) 0.0287(4) Uani 1 1 d . . . . . H10 H 0.181937 0.760347 0.318290 0.034 Uiso 1 1 calc R U . . . C11 C 0.2763(2) 0.85358(19) 0.26857(6) 0.0358(4) Uani 1 1 d . . . . . H11A H 0.376717 0.844411 0.278917 0.054 Uiso 1 1 calc R U . . . H11B H 0.238872 0.940204 0.276310 0.054 Uiso 1 1 calc R U . . . H11C H 0.273304 0.844876 0.238290 0.054 Uiso 1 1 calc R U . . . C12 C 0.0264(2) 0.7632(2) 0.27035(7) 0.0444(5) Uani 1 1 d . . . . . H12A H -0.034406 0.691659 0.280590 0.067 Uiso 1 1 calc R U . . . H12B H 0.026668 0.760780 0.239967 0.067 Uiso 1 1 calc R U . . . H12C H -0.012494 0.847767 0.279528 0.067 Uiso 1 1 calc R U . . . C13 C 0.2886(2) 0.27392(19) 0.33534(6) 0.0313(4) Uani 1 1 d . . . . . H13 H 0.301617 0.317963 0.362912 0.038 Uiso 1 1 calc R U . . . C14 C 0.1426(2) 0.2030(2) 0.33515(8) 0.0515(6) Uani 1 1 d . . . . . H14A H 0.064555 0.267163 0.338882 0.077 Uiso 1 1 calc R U . . . H14B H 0.141899 0.138838 0.357831 0.077 Uiso 1 1 calc R U . . . H14C H 0.127476 0.157399 0.308608 0.077 Uiso 1 1 calc R U . . . C15 C 0.4103(2) 0.1738(2) 0.33135(7) 0.0384(5) Uani 1 1 d . . . . . H15A H 0.504136 0.219248 0.331955 0.058 Uiso 1 1 calc R U . . . H15B H 0.397955 0.126196 0.305060 0.058 Uiso 1 1 calc R U . . . H15C H 0.407075 0.111331 0.354474 0.058 Uiso 1 1 calc R U . . . C16 C 0.22654(17) 0.62297(16) 0.45909(5) 0.0196(3) Uani 1 1 d . . . . . C17 C 0.23102(17) 0.75490(16) 0.47074(5) 0.0220(3) Uani 1 1 d . . . . . C18 C 0.23924(18) 0.78318(17) 0.51322(5) 0.0245(4) Uani 1 1 d . . . . . H18 H 0.240827 0.872281 0.522094 0.029 Uiso 1 1 calc R U . . . C19 C 0.24509(18) 0.68390(17) 0.54250(5) 0.0239(4) Uani 1 1 d . . . . . H19 H 0.248915 0.705089 0.571207 0.029 Uiso 1 1 calc R U . . . C20 C 0.24538(17) 0.55346(17) 0.53001(5) 0.0215(3) Uani 1 1 d . . . . . H20 H 0.252871 0.485886 0.550305 0.026 Uiso 1 1 calc R U . . . C21 C 0.23483(16) 0.51988(16) 0.48808(5) 0.0195(3) Uani 1 1 d . . . . . C22 C 0.24195(17) 0.37693(16) 0.47482(5) 0.0220(3) Uani 1 1 d . . . . . H22 H 0.202361 0.370748 0.445724 0.026 Uiso 1 1 calc R U . . . C23 C 0.40067(19) 0.33294(18) 0.47477(6) 0.0290(4) Uani 1 1 d . . . . . H23A H 0.406097 0.241748 0.465081 0.044 Uiso 1 1 calc R U . . . H23B H 0.442338 0.338996 0.502972 0.044 Uiso 1 1 calc R U . . . H23C H 0.455357 0.389868 0.456233 0.044 Uiso 1 1 calc R U . . . C24 C 0.1518(2) 0.28649(18) 0.50188(6) 0.0309(4) Uani 1 1 d . . . . . H24A H 0.150084 0.197835 0.489942 0.046 Uiso 1 1 calc R U . . . H24B H 0.052343 0.320374 0.503122 0.046 Uiso 1 1 calc R U . . . H24C H 0.195063 0.283215 0.529934 0.046 Uiso 1 1 calc R U . . . C25 C 0.2273(2) 0.86598(18) 0.43919(5) 0.0290(4) Uani 1 1 d . . . . . H25 H 0.246033 0.827204 0.411315 0.035 Uiso 1 1 calc R U . . . C26 C 0.3457(2) 0.96632(19) 0.44866(6) 0.0373(5) Uani 1 1 d . . . . . H26A H 0.347493 1.031742 0.426348 0.056 Uiso 1 1 calc R U . . . H26B H 0.439975 0.921756 0.450741 0.056 Uiso 1 1 calc R U . . . H26C H 0.326028 1.010238 0.474991 0.056 Uiso 1 1 calc R U . . . C27 C 0.0775(2) 0.9320(2) 0.43708(7) 0.0449(5) Uani 1 1 d . . . . . H27A H 0.078967 1.004957 0.417216 0.067 Uiso 1 1 calc R U . . . H27B H 0.053724 0.965726 0.464571 0.067 Uiso 1 1 calc R U . . . H27C H 0.004091 0.867570 0.428097 0.067 Uiso 1 1 calc R U . . . C29 C 0.52892(17) 0.68317(17) 0.35072(5) 0.0215(3) Uani 1 1 d . . . . . H29 H 0.453386 0.732788 0.334314 0.026 Uiso 1 1 calc R U . . . C30 C 0.60605(18) 0.57988(17) 0.32447(5) 0.0241(4) Uani 1 1 d . . . . . H30A H 0.546717 0.558273 0.299363 0.029 Uiso 1 1 calc R U . . . H30B H 0.701594 0.613197 0.315730 0.029 Uiso 1 1 calc R U . . . C31 C 0.62520(18) 0.46011(18) 0.35158(5) 0.0244(4) Uani 1 1 d . . . . . C32 C 0.63838(18) 0.77188(17) 0.37077(5) 0.0230(3) Uani 1 1 d . . . . . C33 C 0.6882(2) 0.9847(2) 0.39612(7) 0.0385(5) Uani 1 1 d . . . . . H33A H 0.640614 1.069941 0.399974 0.058 Uiso 1 1 calc R U . . . H33B H 0.772714 0.996000 0.378579 0.058 Uiso 1 1 calc R U . . . H33C H 0.719763 0.949576 0.423169 0.058 Uiso 1 1 calc R U . . . B1 B 0.4570(2) 0.59163(19) 0.38795(5) 0.0208(4) Uani 1 1 d . . . . . H1 H 0.483(2) 0.6336(19) 0.4189(6) 0.031 Uiso 1 1 d . U . . . C2 C 0.03943(19) 0.5500(2) 0.35900(5) 0.0343(4) Uani 1 1 d . . . . . H2A H -0.011770 0.469311 0.349601 0.041 Uiso 1 1 calc R U . . . H2B H -0.005676 0.627352 0.345182 0.041 Uiso 1 1 calc R U . . . C3 C 0.27910(17) 0.57239(15) 0.38437(4) 0.0187(3) Uani 1 1 d . . . . . C4 C 0.29014(18) 0.38075(17) 0.30214(5) 0.0240(3) Uani 1 1 d . . . . . C5 C 0.24571(17) 0.51042(17) 0.31009(5) 0.0216(3) Uani 1 1 d . . . . . C6 C 0.23779(17) 0.60825(17) 0.27932(5) 0.0227(3) Uani 1 1 d . . . . . C7 C 0.27992(19) 0.57345(19) 0.23954(5) 0.0274(4) Uani 1 1 d . . . . . H7 H 0.276236 0.637112 0.217966 0.033 Uiso 1 1 calc R U . . . C8 C 0.3271(2) 0.44708(19) 0.23114(5) 0.0305(4) Uani 1 1 d . . . . . H8 H 0.356343 0.425348 0.203930 0.037 Uiso 1 1 calc R U . . . C9 C 0.33211(19) 0.35242(19) 0.26177(5) 0.0290(4) Uani 1 1 d . . . . . H9 H 0.364720 0.266349 0.255292 0.035 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 0.0226(6) 0.0277(6) 0.0209(5) 0.0020(5) 0.0038(4) 0.0042(5) O2 0.0290(7) 0.0372(8) 0.0352(7) -0.0036(6) 0.0051(5) 0.0098(6) O3 0.0213(6) 0.0325(7) 0.0358(7) -0.0007(5) -0.0053(5) 0.0000(5) O4 0.0267(6) 0.0250(6) 0.0323(6) -0.0026(5) -0.0046(5) -0.0003(5) N1 0.0185(7) 0.0254(7) 0.0163(6) -0.0015(5) 0.0023(5) -0.0010(5) N2 0.0178(7) 0.0331(8) 0.0177(6) -0.0043(6) 0.0021(5) -0.0007(6) C1 0.0170(8) 0.0379(10) 0.0219(8) -0.0014(7) 0.0022(6) 0.0000(7) C10 0.0248(9) 0.0316(10) 0.0296(9) -0.0008(7) -0.0016(7) 0.0019(7) C11 0.0415(11) 0.0308(10) 0.0348(10) 0.0030(8) -0.0031(8) -0.0007(9) C12 0.0313(11) 0.0481(13) 0.0535(13) 0.0055(10) -0.0052(9) 0.0074(9) C13 0.0351(10) 0.0318(10) 0.0270(9) 0.0031(7) 0.0010(7) 0.0029(8) C14 0.0406(12) 0.0514(14) 0.0626(14) 0.0301(12) 0.0033(10) -0.0044(10) C15 0.0412(11) 0.0277(10) 0.0462(11) 0.0021(9) -0.0028(9) 0.0030(8) C16 0.0177(7) 0.0251(8) 0.0160(7) -0.0020(6) 0.0039(5) 0.0004(6) C17 0.0208(8) 0.0240(8) 0.0214(8) -0.0012(6) 0.0035(6) -0.0005(6) C18 0.0249(8) 0.0234(8) 0.0254(8) -0.0064(7) 0.0037(6) -0.0012(7) C19 0.0224(8) 0.0307(9) 0.0188(7) -0.0045(7) 0.0032(6) -0.0007(7) C20 0.0201(8) 0.0261(9) 0.0185(7) 0.0010(6) 0.0026(6) -0.0004(7) C21 0.0155(7) 0.0226(8) 0.0205(7) -0.0008(6) 0.0027(6) 0.0000(6) C22 0.0223(8) 0.0220(8) 0.0217(8) -0.0015(6) 0.0020(6) 0.0000(7) C23 0.0233(9) 0.0246(9) 0.0394(10) -0.0037(8) 0.0054(7) 0.0008(7) C24 0.0284(9) 0.0259(9) 0.0387(10) -0.0021(8) 0.0106(7) -0.0024(7) C25 0.0371(10) 0.0247(9) 0.0255(8) 0.0020(7) 0.0054(7) -0.0029(8) C26 0.0456(12) 0.0272(10) 0.0393(10) 0.0001(8) 0.0091(9) -0.0090(9) C27 0.0409(12) 0.0401(12) 0.0536(13) 0.0231(10) 0.0011(9) 0.0021(9) C29 0.0188(8) 0.0261(9) 0.0195(7) 0.0000(6) 0.0004(6) -0.0005(6) C30 0.0202(8) 0.0326(9) 0.0195(7) -0.0006(7) 0.0024(6) -0.0027(7) C31 0.0198(8) 0.0318(9) 0.0215(8) -0.0033(7) 0.0011(6) 0.0009(7) C32 0.0220(8) 0.0279(9) 0.0190(7) 0.0032(7) 0.0011(6) -0.0013(7) C33 0.0355(11) 0.0303(10) 0.0493(12) -0.0070(9) -0.0090(9) -0.0047(8) B1 0.0194(9) 0.0253(9) 0.0177(8) -0.0012(7) 0.0011(6) 0.0013(7) C2 0.0197(9) 0.0584(13) 0.0248(9) -0.0097(8) 0.0030(6) -0.0031(8) C3 0.0216(8) 0.0182(8) 0.0164(7) 0.0002(6) 0.0016(6) 0.0010(6) C4 0.0215(8) 0.0276(9) 0.0228(8) -0.0023(7) 0.0006(6) -0.0013(7) C5 0.0171(8) 0.0307(9) 0.0169(7) -0.0040(6) 0.0006(6) -0.0006(7) C6 0.0178(8) 0.0285(9) 0.0217(8) -0.0027(7) -0.0011(6) -0.0034(7) C7 0.0264(9) 0.0368(10) 0.0189(8) 0.0009(7) 0.0001(6) -0.0042(8) C8 0.0310(10) 0.0411(11) 0.0195(8) -0.0077(7) 0.0046(7) -0.0034(8) C9 0.0294(9) 0.0297(9) 0.0281(9) -0.0084(7) 0.0031(7) -0.0006(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 113.49(13) . . ? C32 O4 C33 115.15(14) . . ? C16 N1 C1 116.77(12) . . ? C3 N1 C1 112.48(12) . . ? C3 N1 C16 130.66(13) . . ? C3 N2 C2 112.50(13) . . ? C3 N2 C5 127.40(13) . . ? C5 N2 C2 120.06(13) . . ? N1 C1 C2 102.71(12) . . ? C11 C10 C12 107.97(16) . . ? C6 C10 C11 113.22(15) . . ? C6 C10 C12 110.63(16) . . ? C15 C13 C14 109.51(17) . . ? C15 C13 C4 113.43(15) . . ? C4 C13 C14 110.94(15) . . ? C17 C16 N1 119.01(14) . . ? C17 C16 C21 122.56(14) . . ? C21 C16 N1 117.90(14) . . ? C16 C17 C18 117.52(15) . . ? C16 C17 C25 122.34(14) . . ? C18 C17 C25 120.14(15) . . ? C19 C18 C17 121.24(16) . . ? C18 C19 C20 120.04(15) . . ? C19 C20 C21 121.00(15) . . ? C16 C21 C22 121.96(14) . . ? C20 C21 C16 117.59(15) . . ? C20 C21 C22 120.33(14) . . ? C21 C22 C23 109.18(13) . . ? C21 C22 C24 112.84(13) . . ? C24 C22 C23 110.96(14) . . ? C17 C25 C27 111.12(15) . . ? C26 C25 C17 111.13(15) . . ? C26 C25 C27 110.80(16) . . ? C30 C29 B1 102.26(13) . . ? C32 C29 C30 109.68(13) . . ? C32 C29 B1 107.59(12) . . ? C31 C30 C29 106.40(13) . . ? O1 C31 C30 111.23(14) . . ? O2 C31 O1 122.80(16) . . ? O2 C31 C30 125.97(15) . . ? O3 C32 O4 122.21(15) . . ? O3 C32 C29 125.18(16) . . ? O4 C32 C29 112.61(14) . . ? O1 B1 C29 102.44(12) . . ? O1 B1 C3 110.33(13) . . ? C3 B1 C29 115.24(13) . . ? N2 C2 C1 102.15(13) . . ? N1 C3 N2 108.64(13) . . ? N1 C3 B1 122.75(13) . . ? N2 C3 B1 128.58(13) . . ? C5 C4 C13 122.14(15) . . ? C9 C4 C13 120.97(16) . . ? C9 C4 C5 116.86(16) . . ? C4 C5 N2 118.54(14) . . ? C6 C5 N2 118.29(15) . . ? C6 C5 C4 123.03(14) . . ? C5 C6 C10 122.84(14) . . ? C7 C6 C10 119.84(15) . . ? C7 C6 C5 117.31(16) . . ? C8 C7 C6 120.71(16) . . ? C9 C8 C7 120.85(16) . . ? C8 C9 C4 121.21(17) . . ? 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 1.3294(19) . ? O1 B1 1.511(2) . ? O2 C31 1.215(2) . ? O3 C32 1.214(2) . ? O4 C32 1.346(2) . ? O4 C33 1.442(2) . ? N1 C1 1.480(2) . ? N1 C16 1.4435(19) . ? N1 C3 1.3309(19) . ? N2 C2 1.483(2) . ? N2 C3 1.337(2) . ? N2 C5 1.4378(19) . ? C1 C2 1.509(2) . ? C10 C11 1.527(3) . ? C10 C12 1.538(3) . ? C10 C6 1.520(2) . ? C13 C14 1.525(3) . ? C13 C15 1.522(3) . ? C13 C4 1.525(2) . ? C16 C17 1.393(2) . ? C16 C21 1.405(2) . ? C17 C18 1.399(2) . ? C17 C25 1.520(2) . ? C18 C19 1.382(2) . ? C19 C20 1.386(2) . ? C20 C21 1.395(2) . ? C21 C22 1.517(2) . ? C22 C23 1.528(2) . ? C22 C24 1.527(2) . ? C25 C26 1.518(3) . ? C25 C27 1.534(3) . ? C29 C30 1.534(2) . ? C29 C32 1.488(2) . ? C29 B1 1.668(2) . ? C30 C31 1.507(2) . ? B1 C3 1.651(2) . ? C4 C5 1.406(2) . ? C4 C9 1.397(2) . ? C5 C6 1.406(2) . ? C6 C7 1.394(2) . ? C7 C8 1.385(3) . ? C8 C9 1.379(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 O1 B1 C3 N1 112.75(16) . . . . ? O1 B1 C3 N2 -69.6(2) . . . . ? N1 C1 C2 N2 11.66(19) . . . . ? N1 C16 C17 C18 169.27(14) . . . . ? N1 C16 C17 C25 -10.8(2) . . . . ? N1 C16 C21 C20 -170.40(13) . . . . ? N1 C16 C21 C22 13.5(2) . . . . ? N2 C5 C6 C10 1.1(2) . . . . ? N2 C5 C6 C7 -177.41(14) . . . . ? C1 N1 C16 C17 -93.19(18) . . . . ? C1 N1 C16 C21 78.65(19) . . . . ? C1 N1 C3 N2 3.50(19) . . . . ? C1 N1 C3 B1 -178.40(15) . . . . ? C10 C6 C7 C8 -178.38(16) . . . . ? C11 C10 C6 C5 135.86(17) . . . . ? C11 C10 C6 C7 -45.7(2) . . . . ? C12 C10 C6 C5 -102.79(19) . . . . ? C12 C10 C6 C7 75.7(2) . . . . ? C13 C4 C5 N2 -0.2(2) . . . . ? C13 C4 C5 C6 -175.95(15) . . . . ? C13 C4 C9 C8 176.85(17) . . . . ? C14 C13 C4 C5 89.5(2) . . . . ? C14 C13 C4 C9 -88.5(2) . . . . ? C15 C13 C4 C5 -146.72(17) . . . . ? C15 C13 C4 C9 35.3(2) . . . . ? C16 N1 C1 C2 173.11(15) . . . . ? C16 N1 C3 N2 179.74(15) . . . . ? C16 N1 C3 B1 -2.2(3) . . . . ? C16 C17 C18 C19 1.0(2) . . . . ? C16 C17 C25 C26 -131.73(17) . . . . ? C16 C17 C25 C27 104.4(2) . . . . ? C16 C21 C22 C23 95.74(18) . . . . ? C16 C21 C22 C24 -140.38(16) . . . . ? C17 C16 C21 C20 1.1(2) . . . . ? C17 C16 C21 C22 -175.02(15) . . . . ? C17 C18 C19 C20 1.1(3) . . . . ? C18 C17 C25 C26 48.2(2) . . . . ? C18 C17 C25 C27 -75.6(2) . . . . ? C18 C19 C20 C21 -2.2(2) . . . . ? C19 C20 C21 C16 1.1(2) . . . . ? C19 C20 C21 C22 177.31(15) . . . . ? C20 C21 C22 C23 -80.31(18) . . . . ? C20 C21 C22 C24 43.6(2) . . . . ? C21 C16 C17 C18 -2.2(2) . . . . ? C21 C16 C17 C25 177.81(15) . . . . ? C25 C17 C18 C19 -178.95(15) . . . . ? C29 C30 C31 O1 20.73(18) . . . . ? C29 C30 C31 O2 -160.20(17) . . . . ? C29 B1 C3 N1 -131.86(16) . . . . ? C29 B1 C3 N2 45.8(2) . . . . ? C30 C29 C32 O3 -31.4(2) . . . . ? C30 C29 C32 O4 149.32(13) . . . . ? C30 C29 B1 O1 12.61(15) . . . . ? C30 C29 B1 C3 -107.22(15) . . . . ? C31 O1 B1 C29 -0.77(16) . . . . ? C31 O1 B1 C3 122.42(14) . . . . ? C32 C29 C30 C31 94.72(15) . . . . ? C32 C29 B1 O1 -102.88(14) . . . . ? C32 C29 B1 C3 137.29(14) . . . . ? C33 O4 C32 O3 0.1(2) . . . . ? C33 O4 C32 C29 179.48(14) . . . . ? B1 O1 C31 O2 168.70(16) . . . . ? B1 O1 C31 C30 -12.20(18) . . . . ? B1 C29 C30 C31 -19.24(16) . . . . ? B1 C29 C32 O3 79.13(19) . . . . ? B1 C29 C32 O4 -100.20(15) . . . . ? C2 N2 C3 N1 5.1(2) . . . . ? C2 N2 C3 B1 -172.87(17) . . . . ? C2 N2 C5 C4 -99.99(19) . . . . ? C2 N2 C5 C6 76.0(2) . . . . ? C3 N1 C1 C2 -10.1(2) . . . . ? C3 N1 C16 C17 90.7(2) . . . . ? C3 N1 C16 C21 -97.4(2) . . . . ? C3 N2 C2 C1 -11.0(2) . . . . ? C3 N2 C5 C4 82.5(2) . . . . ? C3 N2 C5 C6 -101.5(2) . . . . ? C4 C5 C6 C10 176.88(15) . . . . ? C4 C5 C6 C7 -1.6(2) . . . . ? C5 N2 C2 C1 171.21(15) . . . . ? C5 N2 C3 N1 -177.31(15) . . . . ? C5 N2 C3 B1 4.7(3) . . . . ? C5 C4 C9 C8 -1.3(3) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C9 0.7(3) . . . . ? C7 C8 C9 C4 -0.1(3) . . . . ? C9 C4 C5 N2 177.94(14) . . . . ? C9 C4 C5 C6 2.2(2) . . . . ?