Intramolecular C–N bond activation by a transient boryl anion
Nahon, Emily E.; Nelmes, Gareth Roland; Brothers, Penelope Jane; Hicks, Jamie; Chemical Communications  (2023) –; doi:10.1039/D3CC05182J

data_7132333
_publ_section_title
;
 Intramolecular C--N bond activation by a transient boryl anion
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC05182J
_journal_year                    2023
_chemical_formula_moiety         'C44 H58 B F N2 O'
_chemical_formula_sum            'C44 H58 B F N2 O'
_chemical_formula_weight         660.73
_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             2023-10-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-17 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                89.601(9)
_cell_angle_beta                 88.022(8)
_cell_angle_gamma                61.747(10)
_cell_formula_units_Z            2
_cell_length_a                   11.5584(9)
_cell_length_b                   12.1098(15)
_cell_length_c                   15.8128(18)
_cell_measurement_reflns_used    5357
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.8920
_cell_measurement_theta_min      4.9540
_cell_volume                     1948.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.947
_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     28.00  89.00   1.00    1.50    --   36.03-125.00-150.00   61
  2  \w     18.00 100.00   1.00    1.50    --   36.03  38.00 150.00   82
  3  \w     20.00  91.00   1.00    1.50    --   36.03  57.00-150.00   71
  4  \w     17.00 105.00   1.00    1.50    --   36.03  38.00   0.00   88
  5  \w     17.00 105.00   1.00    1.50    --   36.03  38.00  90.00   88
  6  \w      0.00  53.00   1.00    1.50    --   36.03 -57.00-150.00   53
  7  \w     33.00  89.00   1.00    1.50    --   36.03-125.00  30.00   56
  8  \w     40.00 109.00   1.00    6.00    --  109.68-111.00  30.00   69
  9  \w     60.00 109.00   1.00    6.00    --  109.68-111.00 120.00   49
 10  \w     92.00 175.00   1.00    6.00    --  109.68  61.00 -30.00   83
 11  \w     44.00 124.00   1.00    6.00    --  109.68 -45.00 -90.00   80
 12  \w     41.00  82.00   1.00    6.00    --  109.68 -45.00  90.00   41
 13  \w    100.00 126.00   1.00    6.00    --  109.68 -45.00  90.00   26
 14  \w     43.00 126.00   1.00    6.00    --  109.68 -45.00-180.00   83
 15  \w     56.00 106.00   1.00    6.00    --  109.68 -95.00-180.00   50
 16  \w     41.00 123.00   1.00    6.00    --  109.68 -45.00   0.00   82
 17  \w     40.00 178.00   1.00    6.00    --  109.68   0.00 -60.00  138
 18  \w     54.00 115.00   1.00    6.00    --  109.68 -77.00-120.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11769
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.886
_diffrn_reflns_theta_min         4.145
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (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    1.126
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7485
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0394P)^2^+0.5307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6556
_reflns_number_total             7485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05182j2.cif
_cod_data_source_block           3-f
_cod_database_code               7132333
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C18 = C17-C19 = C17-C20 = C17-C18A = C17-C19A = C17-C20A
 1.53 with sigma of 0.008
 C18-C19 = C19-C20 = C20-C18 = C18A-C19A = C19A-C20A = C20A-C18A
 2.5 with sigma of 0.008
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C20 \\sim C18A \\sim C19A \\sim C20A: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C27(H27), C39(H39), C42(H42)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C9(H9), C12(H12), C11(H11), C23(H23), C25(H25),
 C37(H37), C24(H24), C35(H35), C36(H36)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C14(H14A,H14B,
 H14C), C29(H29A,H29B,H29C), C16(H16A,H16B,H16C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C28(H28A,H28B,H28C), C43(H43A,H43B,H43C), C20(H20A,H20B,H20C),
 C44(H44A,H44B,H44C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C18A(H18D,H18E,
 H18F), C19A(H19D,H19E,H19F), C20A(H20D,H20E,H20F)
;
_shelx_res_checksum              28353
_shelx_hkl_checksum              30261
_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
;