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_7132257
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                103.9700(10)
_cell_angle_beta                 97.9440(10)
_cell_angle_gamma                107.094(2)
_cell_formula_units_Z            4
_cell_length_a                   12.2748(2)
_cell_length_b                   15.6480(2)
_cell_length_c                   16.1985(2)
_cell_measurement_reflns_used    21075
_cell_measurement_temperature    93
_cell_measurement_theta_max      74.6260
_cell_measurement_theta_min      2.8680
_cell_volume                     2811.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.968
_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     88.00 118.00   0.50    0.21    --  104.88  30.00 120.00   60
  2  \w    132.00 157.00   0.50    0.21    --  104.88  30.00 120.00   50
  3  \w     84.00 176.00   0.50    0.21    --  104.88  45.00  30.00  184
  4  \w     89.00 140.00   0.50    0.21    --  104.88  95.00 -43.00  102
  5  \w     29.00  54.00   0.50    0.21    --  104.88 -45.00  90.00   50
  6  \w     41.00  66.00   0.50    0.21    --  104.88 -61.00 150.00   50
  7  \w     31.00 106.00   0.50    0.21    --  104.88 -77.00  60.00  150
  8  \w     31.00 106.00   0.50    0.21    --  104.88 -77.00 -90.00  150
  9  \w     70.00 106.00   0.50    0.21    --  104.88 -77.00-150.00   72
 10  \w     39.00  65.00   0.50    0.21    --  104.88 -77.00-150.00   52
 11  \w     30.00  55.00   0.50    0.21    --  104.88 -45.00-150.00   50
 12  \w     19.00  94.00   0.50    0.05    --   41.30-125.00-180.00  150
 13  \w     33.00  76.00   0.50    0.21    --  104.88-125.00-120.00   86
 14  \w     87.00 112.00   0.50    0.21    --  104.88-125.00   0.00   50
 15  \w     76.00 112.00   0.50    0.21    --  104.88-125.00  60.00   72
 16  \w     74.00 112.00   0.50    0.21    --  104.88-125.00  90.00   76
 17  \w     31.00  57.00   0.50    0.21    --  104.88-125.00  90.00   52
 18  \w     35.00  61.00   0.50    0.21    --  104.88-125.00  60.00   52
 19  \w     35.00  76.00   0.50    0.21    --  104.88 -94.00  60.00   82
 20  \w     36.00  77.00   0.50    0.21    --  104.88 -94.00   0.00   82
 21  \w     62.00 106.00   0.50    0.21    --  104.88 -94.00  90.00   88
 22  \w     75.00 103.00   0.50    0.21    --  104.88 -95.00-153.00   56
 23  \w     72.00 104.00   0.50    0.21    --  104.88 -94.00-180.00   64
 24  \w    -26.00  76.00   0.50    0.05    --   41.30 -95.00-153.00  204
 25  \w    -20.00   6.00   0.50    0.05    --  -41.30  19.00-150.00   52
 26  \w    -15.00  36.00   0.50    0.05    --  -41.30  37.00 120.00  102
 27  \w    -66.00  33.00   0.50    0.05    --  -41.30  77.00  60.00  198
 28  \w    -39.00  35.00   0.50    0.05    --  -41.30  37.00  30.00  148
 29  \w      4.00  31.00   0.50    0.05    --  -41.30  37.00 -30.00   54
 30  \w    -39.00 -13.00   0.50    0.05    --  -41.30  37.00 -30.00   52
 31  \w    -52.00   1.00   0.50    0.05    --  -41.30  95.00 -43.00  106
 32  \w   -102.00 -47.00   0.50    0.21    -- -104.00 125.00 120.00  110
 33  \w    -66.00 -41.00   0.50    0.21    -- -104.00  61.00  30.00   50
 34  \w    -66.00 -41.00   0.50    0.21    -- -104.00  61.00 -30.00   50
 35  \w    -77.00 -52.00   0.50    0.21    -- -104.00  95.00 -43.00   50
 36  \w    -62.00 -30.00   0.50    0.21    -- -104.00  61.00-120.00   64
 37  \w   -109.00 -54.00   0.50    0.21    -- -104.00 -15.00-120.00  110
 38  \w   -159.00-115.00   0.50    0.21    -- -104.00 -15.00-120.00   88
 39  \w   -175.00-128.00   0.50    0.21    -- -104.00 -45.00  60.00   94
 40  \w   -159.00-131.00   0.50    0.21    -- -104.00 -30.00 150.00   56
 41  \w   -158.00 -82.00   0.50    0.21    -- -104.00 -45.00 120.00  152
 42  \w   -108.00 -82.00   0.50    0.21    -- -104.00 -45.00  60.00   52
 43  \w   -142.00 -86.00   0.50    0.21    -- -104.00 -94.00 -60.00  112
 44  \w   -173.00 -84.00   0.50    0.21    -- -104.00 -95.00-153.00  178
;
_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           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.481
_diffrn_reflns_theta_min         2.885
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         11136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0597P)^2^+0.8670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9896
_reflns_number_total             11136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04830f2.cif
_cod_data_source_block           04117_autored
_cod_original_cell_volume        2811.60(7)
_cod_database_code               7132257
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.872
_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(H01R)=Sof(H01S)=Sof(H2AA)=Sof(H2AB)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(H01T)=Sof(H01U)=Sof(C021)=Sof(H02E)=Sof(H02F)=Sof(C022)=Sof(H02G)=
 Sof(H02H)=Sof(H2BC)=Sof(H2BD)=FVAR(1)
 Sof(H01G)=Sof(H01H)=Sof(H02A)=Sof(H02B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=1-FVAR(2)
 Sof(H01I)=Sof(H01J)=Sof(C01W)=Sof(H01V)=Sof(H01W)=Sof(C01Z)=Sof(H01X)=
 Sof(H01Y)=Sof(H02C)=Sof(H02D)=FVAR(2)
 Sof(H00S)=Sof(H00T)=Sof(H7)=Sof(HI)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=1-FVAR(3)
 Sof(H00V)=Sof(H00W)=Sof(HG)=Sof(HH)=Sof(C01M)=Sof(H9)=Sof(HK)=Sof(C01T)=
 Sof(H14)=Sof(HM)=FVAR(3)
3.a Ternary CH refined with riding coordinates:
 C001(H001), C002(H002), C005(H005), C00B(H00B), C00C(H00X), C00G(H00),
 C00I(H1), C00L(H00L), C00R(H00R), C00Z(H00Z)
3.b Secondary CH2 refined with riding coordinates:
 C003(H00K,H00M), C006(H00N,H00O), C007(H00P,H00Q), C008(H00V,H00W), C008(H00S,
 H00T), C00N(H2,H), C00O(H00A,H00C), C00P(H3,HA), C00T(H00D,H00E), C00V(H4,HB),
 C00W(H00F,H00G), C00X(H00H,H00I), C010(H01A,H01B), C011(H01C,H01D), C015(H01E,
 H01F), C017(H01Z,HC), C018(H01,HD), C019(H01I,H01J), C019(H01G,H01H), C01A(H5,
 HE), C01C(H6,HF), C01F(HG,HH), C01F(H7,HI), C01J(H8,HJ), C01M(H9,HK), C01N(H10,
 HL), C01O(H01O,H01P), C01T(H14,HM), C01U(H01T,H01U), C01U(H01R,H01S),
 C01W(H01V,H01W), C01Z(H01X,H01Y), C020(H02C,H02D), C020(H02A,H02B), C021(H02E,
 H02F), C022(H02G,H02H), C2(H2BC,H2BD), C2(H2AA,H2AB), C1(H1A,H1B), C3(H3A,H3B),
  C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00U(H00U), C00Y(H00Y), C013(H013), C016(H016), C01B(H01K),
 C01D(H01L), C01E(H01M), C01I(H01N), C01P(H01Q), C01Q(H11), C01R(H12),
 C01S(H13), C01V(H15), C01X(H16), C01Y(H17)
;
_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
;