#------------------------------------------------------------------------------ #$Date: 2026-05-07 23:59:50 +0100 (Thu, 07 May 2026) $ #$Revision: 305896 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721006.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_7721006 loop_ _publ_author_name 'Amrutha, P. R.' 'KUNDU, GARGI' 'GANESH, VEMURI LAKSHMI' 'Gonnade, Rajesh G.' 'Gopakumar, Gopinadhanpillai' 'Sen, Sakya Singha' _publ_section_title ; Reactions of saturated NHC•boranes with electron deficient alkyne and alkene. Borirane formation, their reactivities, and coupling of tetracyanoethylene ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT00852F _journal_year 2026 _chemical_formula_moiety 'C34 H49 B N2 O4' _chemical_formula_sum 'C34 H49 B N2 O4' _chemical_formula_weight 560.56 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.2979(8) _cell_length_b 17.8752(8) _cell_length_c 19.8239(8) _cell_measurement_reflns_used 232105 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26 _cell_measurement_theta_min 2.5 _cell_volume 6484.0(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 0.998 _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 0.1149 _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 331220 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 2.500 _diffrn_source 'micro-focus sealed tube' _diffrn_source_type 'Incoatech I\mS HB' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.1512 _exptl_absorpt_correction_T_min 0.0971 _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 1.148 _exptl_crystal_description plate _exptl_crystal_F_000 2432 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.503 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.076 _refine_ls_extinction_coef 0.0041(4) _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 1.091 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 393 _refine_ls_number_reflns 6362 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0425 _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^)+(0.0447P)^2^+4.3315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1040 _refine_ls_wR_factor_ref 0.1207 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5293 _reflns_number_total 6362 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00852f2.cif _cod_data_source_block mo_BM_001_0ma_a _cod_database_code 7721006 _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 0.996 _shelx_estimated_absorpt_t_min 0.985 _olex2_refinement_description ; 1. Others Fixed Sof: C3(0.5) H3A(0.5) H3B(0.5) C3A(0.5) H3C(0.5) H3D(0.5) 2.a Ternary CH refined with riding coordinates: C7(H7), C14(H14), C23(H23), C26(H26), C29(H29), C30(H30) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C3A(H3C,H3D), C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C12(H12), C19(H19), C20(H20), C21(H21) 2.d Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B, H28C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C) ; _shelx_res_file ; TITL mo_BM_001_0ma_a.res in Pbca mo_BM_001_0ma_a.res created by SHELXL-2018/3 at 08:16:43 on 02-Sep-2025 REM Old TITL mo_BM_001_0ma in Pbca REM SHELXT solution in Pbca: R1 0.181, Rweak 0.006, Alpha 0.021 REM 0.342 for 649 systematic absences, Orientation as input REM Formula found by SHELXT: C35 B N3 O3 CELL 0.71073 18.2979 17.8752 19.8239 90.000 90.000 90.000 ZERR 8.000 0.0008 0.0008 0.0008 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H B N O UNIT 272 392 8 16 32 OMIT -3.00 52.00 OMIT 0 0 2 OMIT 1 1 1 OMIT 0 2 0 OMIT 2 0 0 OMIT 0 4 2 OMIT 1 0 2 OMIT 4 0 0 OMIT 4 2 1 OMIT 2 3 1 OMIT 2 2 0 OMIT 1 2 3 OMIT 4 1 1 OMIT 6 0 2 OMIT 4 2 3 SIZE 0.2 0.13 0.05 CONF TEMP -173.150 L.S. 10 BOND LIST 6 FMAP 2 PLAN 5 ACTA WGHT 0.044700 4.331501 EXTI 0.004078 FVAR 0.28807 O1 5 0.534493 0.326373 0.148113 11.00000 0.04067 0.02961 = 0.02624 -0.00026 -0.00217 0.00447 O2 5 0.431035 0.392662 0.135254 11.00000 0.03175 0.05407 = 0.03126 0.00311 -0.01251 0.00333 O3 5 0.424238 0.292876 0.384902 11.00000 0.02845 0.02619 = 0.03025 0.00134 0.00867 -0.00060 O4 5 0.406964 0.415604 0.364793 11.00000 0.02459 0.02640 = 0.04134 -0.00301 0.00696 0.00451 N1 4 0.661518 0.297736 0.283953 11.00000 0.01571 0.01917 = 0.02821 0.00430 0.00275 0.00070 N2 4 0.686448 0.417173 0.247360 11.00000 0.01687 0.01900 = 0.02379 0.00262 0.00121 0.00107 C1 1 0.638077 0.367534 0.271648 11.00000 0.02007 0.01886 = 0.01577 -0.00039 -0.00127 -0.00075 C2 1 0.737477 0.273316 0.271995 11.00000 0.01917 0.02437 = 0.05386 0.00834 0.00812 0.00475 AFIX 23 H2A 2 0.750983 0.235034 0.305862 11.00000 -1.20000 H2B 2 0.740992 0.250109 0.226767 11.00000 -1.20000 AFIX 0 PART 1 C3 1 0.788427 0.335601 0.276164 10.50000 0.01460 0.03265 = 0.02795 0.00085 -0.00003 0.00291 AFIX 23 H3A 2 0.836747 0.319108 0.259325 10.50000 -1.20000 H3B 2 0.794265 0.350194 0.324037 10.50000 -1.20000 AFIX 0 PART 2 C3A 1 0.776799 0.322479 0.224252 10.50000 0.02016 0.02292 = 0.04430 0.00387 0.00975 0.00268 AFIX 23 H3C 2 0.829802 0.311800 0.227033 10.50000 -1.20000 H3D 2 0.760553 0.310983 0.177758 10.50000 -1.20000 AFIX 0 PART 0 C4 1 0.764806 0.400619 0.237558 11.00000 0.01787 0.02642 = 0.04875 0.00799 0.00887 0.00250 AFIX 23 H4A 2 0.774138 0.391533 0.189054 11.00000 -1.20000 H4B 2 0.794002 0.444640 0.251420 11.00000 -1.20000 AFIX 0 C5 1 0.666236 0.494183 0.234137 11.00000 0.01492 0.01844 = 0.02422 0.00188 0.00158 -0.00055 C6 1 0.666954 0.545690 0.287647 11.00000 0.01627 0.02275 = 0.02413 0.00037 0.00246 -0.00344 C7 1 0.689894 0.524428 0.358955 11.00000 0.02440 0.02683 = 0.02240 0.00015 -0.00047 -0.00419 AFIX 13 H7 2 0.687156 0.468717 0.362796 11.00000 -1.20000 AFIX 0 C8 1 0.639964 0.557834 0.413031 11.00000 0.03608 0.03700 = 0.02367 -0.00474 0.00160 -0.00344 AFIX 137 H8A 2 0.589058 0.544956 0.402971 11.00000 -1.50000 H8B 2 0.645475 0.612365 0.413493 11.00000 -1.50000 H8C 2 0.653375 0.537580 0.457270 11.00000 -1.50000 AFIX 0 C9 1 0.769627 0.547734 0.371284 11.00000 0.02857 0.05115 = 0.03046 0.00534 -0.00580 -0.00936 AFIX 137 H9A 2 0.800953 0.525415 0.336602 11.00000 -1.50000 H9B 2 0.785204 0.530286 0.415889 11.00000 -1.50000 H9C 2 0.773568 0.602362 0.369221 11.00000 -1.50000 AFIX 0 C10 1 0.648691 0.619498 0.273016 11.00000 0.01936 0.02040 = 0.02935 -0.00473 0.00244 -0.00285 AFIX 43 H10 2 0.647273 0.655212 0.308481 11.00000 -1.20000 AFIX 0 C11 1 0.632552 0.641976 0.207892 11.00000 0.02032 0.01828 = 0.03461 0.00151 0.00078 -0.00028 AFIX 43 H11 2 0.619389 0.692458 0.199124 11.00000 -1.20000 AFIX 0 C12 1 0.635599 0.590968 0.155693 11.00000 0.02138 0.02221 = 0.02608 0.00381 -0.00092 -0.00080 AFIX 43 H12 2 0.626104 0.607253 0.110926 11.00000 -1.20000 AFIX 0 C13 1 0.652348 0.516008 0.167421 11.00000 0.01754 0.02121 = 0.02334 0.00096 0.00124 -0.00037 C14 1 0.657140 0.461809 0.108501 11.00000 0.02982 0.02193 = 0.02155 -0.00023 0.00011 0.00245 AFIX 13 H14 2 0.655594 0.409726 0.126859 11.00000 -1.20000 AFIX 0 C15 1 0.729748 0.471915 0.070482 11.00000 0.03663 0.04046 = 0.02702 -0.00187 0.00724 0.00509 AFIX 137 H15A 2 0.732882 0.435071 0.033989 11.00000 -1.50000 H15B 2 0.770607 0.464643 0.101764 11.00000 -1.50000 H15C 2 0.732018 0.522470 0.051471 11.00000 -1.50000 AFIX 0 C16 1 0.593673 0.471011 0.059034 11.00000 0.03894 0.02729 = 0.02632 -0.00154 -0.00641 -0.00016 AFIX 137 H16A 2 0.594868 0.430354 0.025888 11.00000 -1.50000 H16B 2 0.598142 0.519150 0.035739 11.00000 -1.50000 H16C 2 0.547325 0.469426 0.083767 11.00000 -1.50000 AFIX 0 C17 1 0.619431 0.241961 0.320537 11.00000 0.01544 0.02007 = 0.02810 0.00637 0.00123 0.00137 C18 1 0.614233 0.248024 0.390926 11.00000 0.01941 0.02238 = 0.02786 0.00438 -0.00151 0.00132 C19 1 0.577853 0.190852 0.425242 11.00000 0.02488 0.02858 = 0.02553 0.00706 -0.00077 0.00071 AFIX 43 H19 2 0.572688 0.193785 0.472853 11.00000 -1.20000 AFIX 0 C20 1 0.549318 0.130271 0.391293 11.00000 0.02325 0.02580 = 0.03258 0.00999 0.00024 -0.00168 AFIX 43 H20 2 0.524512 0.092162 0.415613 11.00000 -1.20000 AFIX 0 C21 1 0.556557 0.124576 0.322015 11.00000 0.02096 0.02054 = 0.03265 0.00365 -0.00161 -0.00026 AFIX 43 H21 2 0.536934 0.082289 0.299331 11.00000 -1.20000 AFIX 0 C22 1 0.592228 0.179974 0.284951 11.00000 0.01725 0.02093 = 0.02766 0.00398 0.00057 0.00314 C23 1 0.600747 0.170453 0.208886 11.00000 0.02200 0.02200 = 0.02681 0.00236 0.00178 -0.00100 AFIX 13 H23 2 0.620098 0.218357 0.189918 11.00000 -1.20000 AFIX 0 C24 1 0.527636 0.153455 0.174590 11.00000 0.02443 0.03402 = 0.02936 0.00258 -0.00066 -0.00224 AFIX 137 H24A 2 0.534312 0.152990 0.125542 11.00000 -1.50000 H24B 2 0.491942 0.192036 0.186762 11.00000 -1.50000 H24C 2 0.509857 0.104460 0.189515 11.00000 -1.50000 AFIX 0 C25 1 0.655065 0.107855 0.191844 11.00000 0.02673 0.02775 = 0.03625 -0.00269 0.00242 0.00258 AFIX 137 H25A 2 0.662709 0.106121 0.142940 11.00000 -1.50000 H25B 2 0.635450 0.059795 0.207275 11.00000 -1.50000 H25C 2 0.701731 0.117665 0.214433 11.00000 -1.50000 AFIX 0 C26 1 0.648129 0.311485 0.431290 11.00000 0.02990 0.02841 = 0.02663 0.00363 -0.00303 -0.00442 AFIX 13 H26 2 0.669603 0.347952 0.398571 11.00000 -1.20000 AFIX 0 C27 1 0.591970 0.353272 0.473998 11.00000 0.04539 0.04064 = 0.03024 -0.00773 -0.00090 -0.00232 AFIX 137 H27A 2 0.616103 0.394218 0.498174 11.00000 -1.50000 H27B 2 0.569992 0.318717 0.506579 11.00000 -1.50000 H27C 2 0.553766 0.373703 0.444657 11.00000 -1.50000 AFIX 0 C28 1 0.710508 0.282091 0.476053 11.00000 0.04001 0.04264 = 0.05587 0.00495 -0.02161 -0.00740 AFIX 137 H28A 2 0.734214 0.324188 0.498949 11.00000 -1.50000 H28B 2 0.746406 0.255874 0.447999 11.00000 -1.50000 H28C 2 0.690643 0.247487 0.509728 11.00000 -1.50000 AFIX 0 C29 1 0.491377 0.403707 0.238684 11.00000 0.02061 0.02273 = 0.02718 0.00340 -0.00119 0.00220 AFIX 13 H29 2 0.458615 0.447959 0.244842 11.00000 -1.20000 AFIX 0 C30 1 0.487425 0.344024 0.294628 11.00000 0.01821 0.01964 = 0.02417 -0.00041 -0.00013 0.00099 AFIX 13 H30 2 0.494545 0.290876 0.280321 11.00000 -1.20000 AFIX 0 C31 1 0.435947 0.357058 0.349599 11.00000 0.01678 0.02284 = 0.02881 -0.00045 -0.00209 -0.00173 C32 1 0.378936 0.300339 0.443401 11.00000 0.04386 0.04414 = 0.03756 0.00514 0.01810 0.00152 AFIX 137 H32A 2 0.372444 0.251236 0.464556 11.00000 -1.50000 H32B 2 0.331178 0.320344 0.430161 11.00000 -1.50000 H32C 2 0.402176 0.334548 0.475530 11.00000 -1.50000 AFIX 0 C33 1 0.490894 0.370138 0.171272 11.00000 0.02569 0.02652 = 0.02718 0.00633 -0.00499 -0.00262 C34 1 0.421507 0.355067 0.071587 11.00000 0.05048 0.06518 = 0.03250 0.00148 -0.01917 -0.00968 AFIX 137 H34A 2 0.375606 0.371388 0.050797 11.00000 -1.50000 H34B 2 0.420019 0.300881 0.078984 11.00000 -1.50000 H34C 2 0.462415 0.367356 0.041664 11.00000 -1.50000 AFIX 0 B1 3 0.557834 0.397553 0.290714 11.00000 0.01856 0.01909 = 0.02290 -0.00015 0.00035 0.00038 H1 2 0.560516 0.442551 0.329001 11.00000 -1.50000 HKLF 4 REM mo_BM_001_0ma_a.res in Pbca REM wR2 = 0.120689, GooF = S = 1.09103, Restrained GooF = 1.09103 for all data REM R1 = 0.042528 for 5293 Fo > 4sig(Fo) and 0.058444 for all 6362 data REM 393 parameters refined using 0 restraints END WGHT 0.0447 4.3315 REM Highest difference peak 0.503, deepest hole -0.476, 1-sigma level 0.076 Q1 1 0.7878 0.4392 0.2088 11.00000 0.05 0.50 Q2 1 0.7906 0.4056 0.2867 11.00000 0.05 0.49 Q3 1 0.7378 0.2163 0.2657 11.00000 0.05 0.41 Q4 1 0.7662 0.2861 0.3233 11.00000 0.05 0.29 Q5 1 0.6558 0.6224 0.1790 11.00000 0.05 0.25 ; _shelx_res_checksum 52523 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 0.53449(7) 0.32637(6) 0.14811(6) 0.0322(3) Uani 1 1 d . . . . . O2 O 0.43104(7) 0.39266(8) 0.13525(6) 0.0390(3) Uani 1 1 d . . . . . O3 O 0.42424(6) 0.29288(6) 0.38490(6) 0.0283(3) Uani 1 1 d . . . . . O4 O 0.40696(6) 0.41560(6) 0.36479(6) 0.0308(3) Uani 1 1 d . . . . . N1 N 0.66152(6) 0.29774(7) 0.28395(6) 0.0210(3) Uani 1 1 d . . . . . N2 N 0.68645(6) 0.41717(7) 0.24736(6) 0.0199(3) Uani 1 1 d . . . . . C1 C 0.63808(8) 0.36753(8) 0.27165(7) 0.0182(3) Uani 1 1 d . . . . . C2 C 0.73748(8) 0.27332(9) 0.27199(10) 0.0325(4) Uani 1 1 d . . . . . H2A H 0.750983 0.235034 0.305862 0.039 Uiso 1 1 calc R U . A 1 H2B H 0.740992 0.250109 0.226767 0.039 Uiso 1 1 calc R U . A 1 C3 C 0.78843(16) 0.33560(18) 0.27616(17) 0.0251(6) Uani 0.5 1 d . . P B 1 H3A H 0.836747 0.319108 0.259325 0.030 Uiso 0.5 1 calc R U P B 1 H3B H 0.794265 0.350194 0.324037 0.030 Uiso 0.5 1 calc R U P B 1 C3A C 0.77680(17) 0.32248(17) 0.22425(19) 0.0291(7) Uani 0.5 1 d . . P B 2 H3C H 0.829802 0.311800 0.227033 0.035 Uiso 0.5 1 calc R U P B 2 H3D H 0.760553 0.310983 0.177758 0.035 Uiso 0.5 1 calc R U P B 2 C4 C 0.76481(8) 0.40062(9) 0.23756(10) 0.0310(4) Uani 1 1 d . . . . . H4A H 0.774138 0.391533 0.189054 0.037 Uiso 1 1 calc R U . B 1 H4B H 0.794002 0.444640 0.251420 0.037 Uiso 1 1 calc R U . B 1 C5 C 0.66624(7) 0.49418(8) 0.23414(7) 0.0192(3) Uani 1 1 d . . . . . C6 C 0.66695(8) 0.54569(8) 0.28765(7) 0.0210(3) Uani 1 1 d . . . . . C7 C 0.68989(8) 0.52443(9) 0.35895(7) 0.0245(3) Uani 1 1 d . . . . . H7 H 0.687156 0.468717 0.362796 0.029 Uiso 1 1 calc R U . . . C8 C 0.63996(10) 0.55783(10) 0.41303(8) 0.0323(4) Uani 1 1 d . . . . . H8A H 0.589058 0.544956 0.402971 0.048 Uiso 1 1 calc R U . . . H8B H 0.645475 0.612365 0.413493 0.048 Uiso 1 1 calc R U . . . H8C H 0.653375 0.537580 0.457270 0.048 Uiso 1 1 calc R U . . . C9 C 0.76963(9) 0.54773(11) 0.37128(9) 0.0367(4) Uani 1 1 d . . . . . H9A H 0.800953 0.525415 0.336602 0.055 Uiso 1 1 calc R U . . . H9B H 0.785204 0.530286 0.415889 0.055 Uiso 1 1 calc R U . . . H9C H 0.773568 0.602362 0.369221 0.055 Uiso 1 1 calc R U . . . C10 C 0.64869(8) 0.61950(8) 0.27302(8) 0.0230(3) Uani 1 1 d . . . . . H10 H 0.647273 0.655212 0.308481 0.028 Uiso 1 1 calc R U . . . C11 C 0.63255(8) 0.64198(8) 0.20789(8) 0.0244(3) Uani 1 1 d . . . . . H11 H 0.619389 0.692458 0.199124 0.029 Uiso 1 1 calc R U . . . C12 C 0.63560(8) 0.59097(8) 0.15569(8) 0.0232(3) Uani 1 1 d . . . . . H12 H 0.626104 0.607253 0.110926 0.028 Uiso 1 1 calc R U . . . C13 C 0.65235(8) 0.51601(8) 0.16742(7) 0.0207(3) Uani 1 1 d . . . . . C14 C 0.65714(9) 0.46181(9) 0.10850(8) 0.0244(3) Uani 1 1 d . . . . . H14 H 0.655594 0.409726 0.126859 0.029 Uiso 1 1 calc R U . . . C15 C 0.72975(10) 0.47191(10) 0.07048(9) 0.0347(4) Uani 1 1 d . . . . . H15A H 0.732882 0.435071 0.033989 0.052 Uiso 1 1 calc R U . . . H15B H 0.770607 0.464643 0.101764 0.052 Uiso 1 1 calc R U . . . H15C H 0.732018 0.522470 0.051471 0.052 Uiso 1 1 calc R U . . . C16 C 0.59367(10) 0.47101(9) 0.05903(8) 0.0309(4) Uani 1 1 d . . . . . H16A H 0.594868 0.430354 0.025888 0.046 Uiso 1 1 calc R U . . . H16B H 0.598142 0.519150 0.035739 0.046 Uiso 1 1 calc R U . . . H16C H 0.547325 0.469426 0.083767 0.046 Uiso 1 1 calc R U . . . C17 C 0.61943(8) 0.24196(8) 0.32054(8) 0.0212(3) Uani 1 1 d . . . . . C18 C 0.61423(8) 0.24802(8) 0.39093(8) 0.0232(3) Uani 1 1 d . . . . . C19 C 0.57785(8) 0.19085(9) 0.42524(8) 0.0263(3) Uani 1 1 d . . . . . H19 H 0.572688 0.193785 0.472853 0.032 Uiso 1 1 calc R U . . . C20 C 0.54932(8) 0.13027(9) 0.39129(8) 0.0272(3) Uani 1 1 d . . . . . H20 H 0.524512 0.092162 0.415613 0.033 Uiso 1 1 calc R U . . . C21 C 0.55656(8) 0.12458(9) 0.32202(8) 0.0247(3) Uani 1 1 d . . . . . H21 H 0.536934 0.082289 0.299331 0.030 Uiso 1 1 calc R U . . . C22 C 0.59223(8) 0.17997(8) 0.28495(8) 0.0219(3) Uani 1 1 d . . . . . C23 C 0.60075(8) 0.17045(8) 0.20889(8) 0.0236(3) Uani 1 1 d . . . . . H23 H 0.620098 0.218357 0.189918 0.028 Uiso 1 1 calc R U . . . C24 C 0.52764(9) 0.15346(10) 0.17459(8) 0.0293(4) Uani 1 1 d . . . . . H24A H 0.534312 0.152990 0.125542 0.044 Uiso 1 1 calc R U . . . H24B H 0.491942 0.192036 0.186762 0.044 Uiso 1 1 calc R U . . . H24C H 0.509857 0.104460 0.189515 0.044 Uiso 1 1 calc R U . . . C25 C 0.65507(9) 0.10786(9) 0.19184(9) 0.0302(4) Uani 1 1 d . . . . . H25A H 0.662709 0.106121 0.142940 0.045 Uiso 1 1 calc R U . . . H25B H 0.635450 0.059795 0.207275 0.045 Uiso 1 1 calc R U . . . H25C H 0.701731 0.117665 0.214433 0.045 Uiso 1 1 calc R U . . . C26 C 0.64813(9) 0.31149(9) 0.43129(8) 0.0283(4) Uani 1 1 d . . . . . H26 H 0.669603 0.347952 0.398571 0.034 Uiso 1 1 calc R U . . . C27 C 0.59197(11) 0.35327(11) 0.47400(9) 0.0388(4) Uani 1 1 d . . . . . H27A H 0.616103 0.394218 0.498174 0.058 Uiso 1 1 calc R U . . . H27B H 0.569992 0.318717 0.506579 0.058 Uiso 1 1 calc R U . . . H27C H 0.553766 0.373703 0.444657 0.058 Uiso 1 1 calc R U . . . C28 C 0.71051(11) 0.28209(11) 0.47605(11) 0.0462(5) Uani 1 1 d . . . . . H28A H 0.734214 0.324188 0.498949 0.069 Uiso 1 1 calc R U . . . H28B H 0.746406 0.255874 0.447999 0.069 Uiso 1 1 calc R U . . . H28C H 0.690643 0.247487 0.509728 0.069 Uiso 1 1 calc R U . . . C29 C 0.49138(8) 0.40371(8) 0.23868(8) 0.0235(3) Uani 1 1 d . . . . . H29 H 0.458615 0.447959 0.244842 0.028 Uiso 1 1 calc R U . . . C30 C 0.48742(8) 0.34402(8) 0.29463(7) 0.0207(3) Uani 1 1 d . . . . . H30 H 0.494545 0.290876 0.280321 0.025 Uiso 1 1 calc R U . . . C31 C 0.43595(8) 0.35706(8) 0.34960(8) 0.0228(3) Uani 1 1 d . . . . . C32 C 0.37894(11) 0.30034(11) 0.44340(10) 0.0419(5) Uani 1 1 d . . . . . H32A H 0.372444 0.251236 0.464556 0.063 Uiso 1 1 calc R U . . . H32B H 0.331178 0.320344 0.430161 0.063 Uiso 1 1 calc R U . . . H32C H 0.402176 0.334548 0.475530 0.063 Uiso 1 1 calc R U . . . C33 C 0.49089(9) 0.37014(9) 0.17127(8) 0.0265(3) Uani 1 1 d . . . . . C34 C 0.42151(12) 0.35507(13) 0.07159(10) 0.0494(5) Uani 1 1 d . . . . . H34A H 0.375606 0.371388 0.050797 0.074 Uiso 1 1 calc R U . . . H34B H 0.420019 0.300881 0.078984 0.074 Uiso 1 1 calc R U . . . H34C H 0.462415 0.367356 0.041664 0.074 Uiso 1 1 calc R U . . . B1 B 0.55783(9) 0.39755(9) 0.29071(9) 0.0202(3) Uani 1 1 d . . . . . H1 H 0.5605(10) 0.4426(10) 0.3290(9) 0.030 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 0.0407(7) 0.0296(6) 0.0262(6) -0.0003(5) -0.0022(5) 0.0045(5) O2 0.0318(7) 0.0541(8) 0.0313(6) 0.0031(6) -0.0125(5) 0.0033(6) O3 0.0284(6) 0.0262(6) 0.0302(6) 0.0013(5) 0.0087(5) -0.0006(5) O4 0.0246(6) 0.0264(6) 0.0413(7) -0.0030(5) 0.0070(5) 0.0045(5) N1 0.0157(6) 0.0192(6) 0.0282(7) 0.0043(5) 0.0028(5) 0.0007(5) N2 0.0169(6) 0.0190(6) 0.0238(6) 0.0026(5) 0.0012(5) 0.0011(5) C1 0.0201(7) 0.0189(7) 0.0158(6) -0.0004(5) -0.0013(5) -0.0008(5) C2 0.0192(8) 0.0244(8) 0.0539(11) 0.0083(8) 0.0081(7) 0.0047(6) C3 0.0146(14) 0.0326(17) 0.0280(17) 0.0009(14) 0.0000(12) 0.0029(12) C3A 0.0202(15) 0.0229(16) 0.044(2) 0.0039(14) 0.0097(14) 0.0027(12) C4 0.0179(8) 0.0264(8) 0.0488(10) 0.0080(7) 0.0089(7) 0.0025(6) C5 0.0149(7) 0.0184(7) 0.0242(7) 0.0019(6) 0.0016(5) -0.0006(5) C6 0.0163(7) 0.0228(7) 0.0241(8) 0.0004(6) 0.0025(6) -0.0034(6) C7 0.0244(8) 0.0268(8) 0.0224(7) 0.0002(6) -0.0005(6) -0.0042(6) C8 0.0361(9) 0.0370(9) 0.0237(8) -0.0047(7) 0.0016(7) -0.0034(7) C9 0.0286(9) 0.0512(11) 0.0305(9) 0.0053(8) -0.0058(7) -0.0094(8) C10 0.0194(7) 0.0204(7) 0.0293(8) -0.0047(6) 0.0024(6) -0.0028(6) C11 0.0203(7) 0.0183(7) 0.0346(8) 0.0015(6) 0.0008(6) -0.0003(6) C12 0.0214(7) 0.0222(7) 0.0261(8) 0.0038(6) -0.0009(6) -0.0008(6) C13 0.0175(7) 0.0212(7) 0.0233(7) 0.0010(6) 0.0012(6) -0.0004(6) C14 0.0298(8) 0.0219(7) 0.0216(7) -0.0002(6) 0.0001(6) 0.0024(6) C15 0.0366(10) 0.0405(10) 0.0270(8) -0.0019(7) 0.0072(7) 0.0051(8) C16 0.0389(9) 0.0273(8) 0.0263(8) -0.0015(7) -0.0064(7) -0.0002(7) C17 0.0154(7) 0.0201(7) 0.0281(8) 0.0064(6) 0.0012(6) 0.0014(6) C18 0.0194(7) 0.0224(7) 0.0279(8) 0.0044(6) -0.0015(6) 0.0013(6) C19 0.0249(8) 0.0286(8) 0.0255(8) 0.0071(6) -0.0008(6) 0.0007(6) C20 0.0232(8) 0.0258(8) 0.0326(8) 0.0100(7) 0.0002(6) -0.0017(6) C21 0.0210(7) 0.0205(7) 0.0326(8) 0.0037(6) -0.0016(6) -0.0003(6) C22 0.0172(7) 0.0209(7) 0.0277(8) 0.0040(6) 0.0006(6) 0.0031(6) C23 0.0220(7) 0.0220(7) 0.0268(8) 0.0024(6) 0.0018(6) -0.0010(6) C24 0.0244(8) 0.0340(9) 0.0294(8) 0.0026(7) -0.0007(6) -0.0022(7) C25 0.0267(8) 0.0278(8) 0.0363(9) -0.0027(7) 0.0024(7) 0.0026(7) C26 0.0299(8) 0.0284(8) 0.0266(8) 0.0036(7) -0.0030(7) -0.0044(7) C27 0.0454(11) 0.0406(10) 0.0302(9) -0.0077(8) -0.0009(8) -0.0023(8) C28 0.0400(11) 0.0426(11) 0.0559(12) 0.0050(9) -0.0216(9) -0.0074(9) C29 0.0206(7) 0.0227(7) 0.0272(8) 0.0034(6) -0.0012(6) 0.0022(6) C30 0.0182(7) 0.0196(7) 0.0242(7) -0.0004(6) -0.0001(6) 0.0010(6) C31 0.0168(7) 0.0228(7) 0.0288(8) -0.0004(6) -0.0021(6) -0.0017(6) C32 0.0439(11) 0.0441(11) 0.0376(10) 0.0051(8) 0.0181(8) 0.0015(9) C33 0.0257(8) 0.0265(8) 0.0272(8) 0.0063(6) -0.0050(6) -0.0026(6) C34 0.0505(12) 0.0652(14) 0.0325(10) 0.0015(9) -0.0192(9) -0.0097(10) B1 0.0186(8) 0.0191(8) 0.0229(8) -0.0001(6) 0.0003(6) 0.0004(6) 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 C33 O2 C34 114.64(15) . . ? C31 O3 C32 115.41(13) . . ? C1 N1 C2 123.15(12) . . ? C1 N1 C17 124.00(12) . . ? C17 N1 C2 112.10(11) . . ? C1 N2 C4 123.70(12) . . ? C1 N2 C5 121.63(12) . . ? C5 N2 C4 114.47(11) . . ? N1 C1 N2 117.97(13) . . ? N1 C1 B1 124.01(12) . . ? N2 C1 B1 117.75(12) . . ? N1 C2 C3A 112.66(17) . . ? C3 C2 N1 111.60(17) . . ? C2 C3 C4 113.0(2) . . ? C4 C3A C2 112.7(2) . . ? C3 C4 N2 112.25(16) . . ? C3A C4 N2 111.52(17) . . ? C6 C5 N2 118.92(13) . . ? C13 C5 N2 118.76(13) . . ? C13 C5 C6 122.12(13) . . ? C5 C6 C7 122.68(13) . . ? C10 C6 C5 117.50(14) . . ? C10 C6 C7 119.76(13) . . ? C6 C7 C8 112.86(13) . . ? C6 C7 C9 109.98(13) . . ? C8 C7 C9 110.47(14) . . ? C11 C10 C6 121.39(14) . . ? C12 C11 C10 119.93(14) . . ? C11 C12 C13 121.25(14) . . ? C5 C13 C14 122.48(13) . . ? C12 C13 C5 117.68(14) . . ? C12 C13 C14 119.81(13) . . ? C13 C14 C15 110.58(13) . . ? C13 C14 C16 112.36(13) . . ? C16 C14 C15 109.22(13) . . ? C18 C17 N1 118.63(13) . . ? C18 C17 C22 122.44(13) . . ? C22 C17 N1 118.57(13) . . ? C17 C18 C26 123.61(14) . . ? C19 C18 C17 117.41(14) . . ? C19 C18 C26 118.95(14) . . ? C20 C19 C18 121.19(15) . . ? C19 C20 C21 120.43(15) . . ? C20 C21 C22 121.02(15) . . ? C17 C22 C23 123.25(13) . . ? C21 C22 C17 117.46(14) . . ? C21 C22 C23 119.29(14) . . ? C22 C23 C24 111.83(13) . . ? C22 C23 C25 111.42(13) . . ? C24 C23 C25 108.88(13) . . ? C18 C26 C27 112.48(14) . . ? C18 C26 C28 110.57(14) . . ? C27 C26 C28 110.28(15) . . ? C30 C29 B1 61.54(10) . . ? C33 C29 C30 111.89(13) . . ? C33 C29 B1 124.41(13) . . ? C29 C30 B1 61.00(10) . . ? C31 C30 C29 117.22(13) . . ? C31 C30 B1 117.30(13) . . ? O3 C31 C30 110.56(13) . . ? O4 C31 O3 122.11(14) . . ? O4 C31 C30 127.32(14) . . ? O1 C33 O2 121.40(15) . . ? O1 C33 C29 127.44(14) . . ? O2 C33 C29 111.13(14) . . ? C29 B1 C1 124.46(13) . . ? C29 B1 C30 57.46(9) . . ? C30 B1 C1 123.01(13) . . ? 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 C33 1.208(2) . ? O2 C33 1.3681(19) . ? O2 C34 1.440(2) . ? O3 C31 1.3609(19) . ? O3 C32 1.432(2) . ? O4 C31 1.2113(19) . ? N1 C1 1.3417(18) . ? N1 C2 1.4760(19) . ? N1 C17 1.4536(18) . ? N2 C1 1.3426(18) . ? N2 C4 1.4768(19) . ? N2 C5 1.4493(18) . ? C1 B1 1.608(2) . ? C2 C3 1.454(4) . ? C2 C3A 1.478(4) . ? C3 C4 1.457(3) . ? C3A C4 1.438(4) . ? C5 C6 1.405(2) . ? C5 C13 1.402(2) . ? C6 C7 1.523(2) . ? C6 C10 1.392(2) . ? C7 C8 1.530(2) . ? C7 C9 1.537(2) . ? C10 C11 1.384(2) . ? C11 C12 1.380(2) . ? C12 C13 1.394(2) . ? C13 C14 1.520(2) . ? C14 C15 1.538(2) . ? C14 C16 1.529(2) . ? C17 C18 1.403(2) . ? C17 C22 1.405(2) . ? C18 C19 1.397(2) . ? C18 C26 1.520(2) . ? C19 C20 1.378(2) . ? C20 C21 1.383(2) . ? C21 C22 1.395(2) . ? C22 C23 1.525(2) . ? C23 C24 1.531(2) . ? C23 C25 1.534(2) . ? C26 C27 1.527(2) . ? C26 C28 1.538(2) . ? C29 C30 1.541(2) . ? C29 C33 1.465(2) . ? C29 B1 1.598(2) . ? C30 C31 1.459(2) . ? C30 B1 1.607(2) . ? 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 C29 -99.09(18) . . . . ? N1 C1 B1 C30 -28.5(2) . . . . ? N1 C2 C3 C4 -47.8(3) . . . . ? N1 C2 C3A C4 44.3(3) . . . . ? N1 C17 C18 C19 -175.59(13) . . . . ? N1 C17 C18 C26 2.2(2) . . . . ? N1 C17 C22 C21 175.50(13) . . . . ? N1 C17 C22 C23 -3.7(2) . . . . ? N2 C1 B1 C29 86.95(18) . . . . ? N2 C1 B1 C30 157.55(14) . . . . ? N2 C5 C6 C7 1.5(2) . . . . ? N2 C5 C6 C10 178.74(12) . . . . ? N2 C5 C13 C12 -177.72(13) . . . . ? N2 C5 C13 C14 0.5(2) . . . . ? C1 N1 C2 C3 26.3(3) . . . . ? C1 N1 C2 C3A -20.4(3) . . . . ? C1 N1 C17 C18 -75.63(18) . . . . ? C1 N1 C17 C22 111.05(16) . . . . ? C1 N2 C4 C3 -18.5(3) . . . . ? C1 N2 C4 C3A 28.7(3) . . . . ? C1 N2 C5 C6 83.45(17) . . . . ? C1 N2 C5 C13 -101.62(16) . . . . ? C2 N1 C1 N2 -0.1(2) . . . . ? C2 N1 C1 B1 -174.01(14) . . . . ? C2 N1 C17 C18 94.67(16) . . . . ? C2 N1 C17 C22 -78.65(17) . . . . ? C2 C3 C4 N2 44.3(3) . . . . ? C2 C3A C4 N2 -47.6(3) . . . . ? C4 N2 C1 N1 -4.0(2) . . . . ? C4 N2 C1 B1 170.30(14) . . . . ? C4 N2 C5 C6 -91.53(16) . . . . ? C4 N2 C5 C13 83.40(17) . . . . ? C5 N2 C1 N1 -178.54(13) . . . . ? C5 N2 C1 B1 -4.2(2) . . . . ? C5 N2 C4 C3 156.31(19) . . . . ? C5 N2 C4 C3A -156.5(2) . . . . ? C5 C6 C7 C8 -137.27(15) . . . . ? C5 C6 C7 C9 98.88(17) . . . . ? C5 C6 C10 C11 -1.9(2) . . . . ? C5 C13 C14 C15 -100.92(16) . . . . ? C5 C13 C14 C16 136.76(15) . . . . ? C6 C5 C13 C12 -3.0(2) . . . . ? C6 C5 C13 C14 175.23(13) . . . . ? C6 C10 C11 C12 -1.1(2) . . . . ? C7 C6 C10 C11 175.42(13) . . . . ? C10 C6 C7 C8 45.55(19) . . . . ? C10 C6 C7 C9 -78.30(18) . . . . ? C10 C11 C12 C13 2.2(2) . . . . ? C11 C12 C13 C5 -0.2(2) . . . . ? C11 C12 C13 C14 -178.43(14) . . . . ? C12 C13 C14 C15 77.24(18) . . . . ? C12 C13 C14 C16 -45.09(19) . . . . ? C13 C5 C6 C7 -173.26(13) . . . . ? C13 C5 C6 C10 4.0(2) . . . . ? C17 N1 C1 N2 169.18(13) . . . . ? C17 N1 C1 B1 -4.8(2) . . . . ? C17 N1 C2 C3 -144.09(19) . . . . ? C17 N1 C2 C3A 169.2(2) . . . . ? C17 C18 C19 C20 1.1(2) . . . . ? C17 C18 C26 C27 123.38(16) . . . . ? C17 C18 C26 C28 -112.83(17) . . . . ? C17 C22 C23 C24 -128.69(15) . . . . ? C17 C22 C23 C25 109.20(16) . . . . ? C18 C17 C22 C21 2.4(2) . . . . ? C18 C17 C22 C23 -176.80(14) . . . . ? C18 C19 C20 C21 0.4(2) . . . . ? C19 C18 C26 C27 -58.87(19) . . . . ? C19 C18 C26 C28 64.91(19) . . . . ? C19 C20 C21 C22 -0.5(2) . . . . ? C20 C21 C22 C17 -0.9(2) . . . . ? C20 C21 C22 C23 178.39(14) . . . . ? C21 C22 C23 C24 52.07(18) . . . . ? C21 C22 C23 C25 -70.03(17) . . . . ? C22 C17 C18 C19 -2.5(2) . . . . ? C22 C17 C18 C26 175.23(14) . . . . ? C26 C18 C19 C20 -176.80(14) . . . . ? C29 C30 C31 O3 164.11(12) . . . . ? C29 C30 C31 O4 -17.1(2) . . . . ? C29 C30 B1 C1 -112.70(16) . . . . ? C30 C29 C33 O1 -59.8(2) . . . . ? C30 C29 C33 O2 118.09(14) . . . . ? C30 C29 B1 C1 110.23(16) . . . . ? C31 C30 B1 C1 139.69(14) . . . . ? C31 C30 B1 C29 -107.60(15) . . . . ? C32 O3 C31 O4 -3.6(2) . . . . ? C32 O3 C31 C30 175.31(14) . . . . ? C33 C29 C30 C31 -133.91(14) . . . . ? C33 C29 C30 B1 118.36(14) . . . . ? C33 C29 B1 C1 12.0(2) . . . . ? C33 C29 B1 C30 -98.20(16) . . . . ? C34 O2 C33 O1 5.4(2) . . . . ? C34 O2 C33 C29 -172.63(15) . . . . ? B1 C29 C30 C31 107.73(15) . . . . ? B1 C29 C33 O1 9.9(3) . . . . ? B1 C29 C33 O2 -172.23(14) . . . . ? B1 C30 C31 O3 -126.26(14) . . . . ? B1 C30 C31 O4 52.6(2) . . . . ?