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_7132256
_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         'C H2 Cl2, B C24 F20, C36 H44 B'
_chemical_formula_sum            'C61 H46 B2 Cl2 F20'
_chemical_formula_weight         1251.566
_chemical_name_systematic        C61H46B2Cl2F20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2023-08-23
_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                71.230(1)
_cell_angle_beta                 82.932(1)
_cell_angle_gamma                79.863(1)
_cell_formula_units_Z            2
_cell_length_a                   12.4793(1)
_cell_length_b                   14.1126(2)
_cell_length_c                   16.1478(2)
_cell_measurement_reflns_used    21127
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.4340
_cell_measurement_theta_min      2.9030
_cell_volume                     2643.86(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_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 0.9993
_diffrn_measured_fraction_theta_max 0.9639
_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     32.00  79.00   0.50    0.97    --  102.75 -77.00 120.00   94
  2  \w     43.00  68.00   0.50    0.97    --  102.75 -61.00  30.00   50
  3  \w    -23.00  68.00   0.50    0.24    --   47.66 -77.00 -30.00  182
  4  \w     39.00  64.00   0.50    0.97    --  102.75 -77.00-180.00   50
  5  \w     68.00 105.00   0.50    0.97    --  102.75 -77.00-180.00   74
  6  \w     18.00  90.00   0.50    0.24    --   47.66-125.00 -60.00  144
  7  \w     77.00 107.00   0.50    0.97    --  102.75-105.00-114.79   60
  8  \w     37.00 107.00   0.50    0.97    --  102.75-102.00  20.48  140
  9  \w     46.00  87.00   0.50    0.97    --  102.75 -94.00 -30.00   82
 10  \w     46.00  96.00   0.50    0.97    --  102.75 -94.00  30.00  100
 11  \w     41.00 107.00   0.50    0.97    --  102.75-125.00 120.00  132
 12  \w     66.00 102.00   0.50    0.97    --  102.75-101.00 124.00   72
 13  \w    -11.00  50.00   0.50    0.24    --   47.66-101.00 124.00  122
 14  \w     33.00 100.00   0.50    0.97    --  102.75 -94.00 -60.00  134
 15  \w     36.00  94.00   0.50    0.97    --  102.75 -94.00 -90.00  116
 16  \w    122.00 175.00   0.50    0.97    --  102.75  30.00-150.00  106
 17  \w     98.00 167.00   0.50    0.97    --  102.75 101.00-132.00  138
 18  \w     37.00 111.00   0.50    0.24    --   47.66  57.00 -90.00  148
 19  \w     94.00 174.00   0.50    0.97    --  102.75  45.00 150.00  160
 20  \w    -10.00  26.00   0.50    0.24    --  -47.66  19.00  30.00   72
 21  \w    -26.00   2.00   0.50    0.24    --  -47.66  19.00 150.00   56
 22  \w   -111.00 -83.00   0.50    0.97    -- -102.75 125.00 150.00   56
 23  \w      0.00  26.00   0.50    0.24    --  -47.66  19.00 -30.00   52
 24  \w    -48.00  17.00   0.50    0.24    --  -47.66 101.00-132.00  130
 25  \w    -97.00 -72.00   0.50    0.97    -- -102.75 101.00-132.00   50
 26  \w    -68.00 -35.00   0.50    0.97    -- -102.75 125.00 150.00   66
 27  \w    -59.00 -32.00   0.50    0.97    -- -102.75  61.00 -30.00   54
 28  \w    -60.00 -32.00   0.50    0.97    -- -102.75  61.00   0.00   56
 29  \w    -64.00 -31.00   0.50    0.97    -- -102.75  61.00-120.00   66
 30  \w    -65.00 -40.00   0.50    0.97    -- -102.75  61.00-150.00   50
 31  \w    -62.00 -36.00   0.50    0.97    -- -102.75  61.00-180.00   52
 32  \w   -172.00 -74.00   0.50    0.97    -- -102.75   0.00-120.00  196
 33  \w   -175.00-107.00   0.50    0.97    -- -102.75 -30.00 -30.00  136
 34  \w   -173.00 -93.00   0.50    0.97    -- -102.75 -45.00  30.00  160
 35  \w   -162.00-136.00   0.50    0.97    -- -102.75-101.00 124.00   52
 36  \w   -132.00-106.00   0.50    0.97    -- -102.75-101.00 124.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       '\w scans'
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9639
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34697
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9639
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.71
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_exptl_absorpt_coefficient_mu    2.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (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    1.572
_exptl_crystal_description       prism
_exptl_crystal_F_000             1278.799
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.5089
_refine_diff_density_min         -0.5978
_refine_diff_density_rms         0.0510
_refine_ls_d_res_high            0.7921
_refine_ls_d_res_low             15.2502
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    86
_refine_ls_number_parameters     785
_refine_ls_number_reflns         10736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0419
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+1.3045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9584
_reflns_number_total             10736
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc04830f2.cif
_cod_data_source_block           BoroceniumB(C6F5)4_autored
_cod_database_code               7132256
_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(H34a)=Sof(H34b)=Sof(H31a)=Sof(H31b)=Sof(C32B)=Sof(H32c)=Sof(H32d)=
 Sof(C33B)=Sof(H33c)=Sof(H33d)=1-FVAR(1)
 Sof(H34c)=Sof(H34d)=Sof(H31c)=Sof(H31d)=Sof(C33A)=Sof(H33a)=Sof(H33b)=
 Sof(C32A)=Sof(H32a)=Sof(H32b)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C22(H22a,H22b), C16(H16a,H16b), C15(H15a,H15b), C23(H23a,
 H23b), C27(H27a,H27b), C19(H19a,H19b), C26(H26a,H26b), C35(H35a,H35b),
 C30(H30a,H30b), C24(H24a,H24b), C25(H25a,H25b), C34(H34c,H34d), C34(H34a,H34b),
  C18(H18a,H18b), C17(H17a,H17b), C31(H31c,H31d), C31(H31a,H31b), C33A(H33a,
 H33b), C32A(H32a,H32b), C62(H62a,H62b), C32B(H32c,H32d), C33B(H33c,H33d)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C2(H2), C10(H10), C8(H8), C9(H9), C3(H3), C4(H4)
;
_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
;