Skeletal rearrangement of a boron-containing annulenic molecule into a macrocycle bridged by an electronically stabilized boron cation
Murata, Yukihiro; Özen, Cihan; Maeda, Satoshi; Fukushima, Takanori; Shoji, Yoshiaki; Chemical Communications  (2023) –; doi:10.1039/D3CC04830F

data_7132258
_publ_section_title
;
 Skeletal rearrangement of a boron-containing annulenic molecule into a
 macrocycle bridged by an electronically stabilized boron cation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04830F
_journal_year                    2023
_chemical_formula_moiety         'C36 H45 B'
_chemical_formula_sum            'C36 H45 B'
_chemical_formula_weight         488.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-27 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6346(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.31009(11)
_cell_length_b                   9.47225(5)
_cell_length_c                   24.91264(13)
_cell_measurement_reflns_used    60496
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.6730
_cell_measurement_theta_min      2.4420
_cell_volume                     5451.93(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  26.00   0.50    1.62    --  -46.27  80.00-133.00  192
  2  \w    -25.00  70.00   0.50    1.62    --   46.27 -80.00 103.00  190
  3  \w   -175.00 -80.00   0.50    6.49    -- -102.00 -80.00 103.00  190
  4  \w     84.00 178.00   0.50    6.49    --  104.75  80.00-133.00  188
  5  \w     32.00 129.00   0.50    6.49    --  104.75 -80.00 103.00  194
  6  \w    -19.00  29.00   0.50    1.62    --  -46.27  19.00 120.00   96
  7  \w    -32.00  27.00   0.50    1.62    --  -46.27  37.00 -30.00  118
  8  \w    -19.00  29.00   0.50    1.62    --  -46.27  19.00-150.00   96
  9  \w    -32.00  27.00   0.50    1.62    --  -46.27  37.00-120.00  118
 10  \w    -60.00 -29.00   0.50    6.49    -- -102.00  61.00-150.00   62
 11  \w    -60.00 -29.00   0.50    6.49    -- -102.00  61.00-180.00   62
 12  \w    -90.00 -29.00   0.50    6.49    -- -102.00  77.00  60.00  122
 13  \w   -126.00 -29.00   0.50    6.49    -- -102.00  80.00-133.00  194
 14  \w    -60.00 -29.00   0.50    6.49    -- -102.00  61.00 -60.00   62
 15  \w    -60.00 -29.00   0.50    6.49    -- -102.00  61.00  60.00   62
 16  \w     33.00  62.00   0.50    6.49    --  104.75 -45.00-180.00   58
 17  \w     33.00  62.00   0.50    6.49    --  104.75 -45.00 -60.00   58
 18  \w     33.00  62.00   0.50    6.49    --  104.75 -45.00 150.00   58
 19  \w     32.00 106.00   0.50    6.49    --  104.75 -94.00 -30.00  148
 20  \w     33.00  62.00   0.50    6.49    --  104.75 -45.00  90.00   58
 21  \w     32.00  82.00   0.50    6.49    --  104.75 -61.00   0.00  100
 22  \w     92.00 177.00   0.50    6.49    --  104.75  45.00-180.00  170
 23  \w     33.00  62.00   0.50    6.49    --  104.75 -45.00-120.00   58
 24  \w     31.00 118.00   0.50    1.62    --   46.27  57.00   0.00  174
 25  \w     31.00 118.00   0.50    1.62    --   46.27  57.00 120.00  174
 26  \w     31.00 118.00   0.50    1.62    --   46.27  57.00  30.00  174
 27  \w     24.00 118.00   0.50    1.62    --   46.27  77.00 -90.00  188
 28  \w     24.00 118.00   0.50    1.62    --   46.27  77.00 150.00  188
 29  \w     24.00 118.00   0.50    1.62    --   46.27  77.00-150.00  188
 30  \w   -175.00-116.00   0.50    6.49    -- -102.00 -77.00-180.00  118
 31  \w   -175.00 -85.00   0.50    6.49    -- -102.00 -61.00  60.00  180
 32  \w   -175.00 -79.00   0.50    6.49    -- -102.00 -77.00-120.00  192
 33  \w   -175.00 -79.00   0.50    6.49    -- -102.00 -77.00 150.00  192
 34  \w   -174.00 -89.00   0.50    6.49    -- -102.00 -45.00  30.00  170
 35  \w   -175.00 -79.00   0.50    6.49    -- -102.00 -77.00 120.00  192
 36  \w     92.00 178.00   0.50    6.49    --  104.75  30.00 -30.00  172
 37  \w     92.00 177.00   0.50    6.49    --  104.75  45.00   0.00  170
 38  \w     32.00 112.00   0.50    6.49    --  104.75-125.00 -30.00  160
 39  \w     88.00 178.00   0.50    6.49    --  104.75  61.00 -90.00  180
 40  \w     91.00 178.00   0.50    6.49    --  104.75  15.00 150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0297811000
_diffrn_orient_matrix_UB_12      -0.1352226000
_diffrn_orient_matrix_UB_13      0.0166929000
_diffrn_orient_matrix_UB_21      -0.0538987000
_diffrn_orient_matrix_UB_22      0.0353465000
_diffrn_orient_matrix_UB_23      -0.0405315000
_diffrn_orient_matrix_UB_31      0.0255566000
_diffrn_orient_matrix_UB_32      -0.0831710000
_diffrn_orient_matrix_UB_33      -0.0444097000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            108653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.959
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       prism
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         11313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0458P)^2^+2.5293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10289
_reflns_number_total             11313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04830f2.cif
_cod_data_source_block           mrt0462_autored
_cod_database_code               7132258
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C36BH45
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H59C)=Sof(H59D)=Sof(C60B)=Sof(H60C)=Sof(H60D)=Sof(C61B)=Sof(H61C)=
 Sof(H61D)=Sof(H62C)=Sof(H62D)=1-FVAR(1)
 Sof(H59A)=Sof(H59B)=Sof(C60A)=Sof(H60A)=Sof(H60B)=Sof(C61A)=Sof(H61A)=
 Sof(H61B)=Sof(H62A)=Sof(H62B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C56(H56)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C30(H30A,H30B), C31(H31A,H31B),
  C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C50(H50A,
 H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B),
 C55(H55A,H55B), C58(H58A,H58B), C59(H59A,H59B), C59(H59C,H59D), C60A(H60A,
 H60B), C61A(H61A,H61B), C60B(H60C,H60D), C61B(H61C,H61D), C62(H62A,H62B),
 C62(H62C,H62D), C63(H63A,H63B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B),
  C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C39(H39), C40(H40), C41(H41), C42(H42), C45(H45), C46(H46), C47(H47), C48(H48)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.913