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_7132328
_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         'C50 H64 K2 N2 O, C6 H6'
_chemical_formula_sum            'C56 H70 K2 N2 O'
_chemical_formula_weight         865.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 99.342(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2232(2)
_cell_length_b                   9.80740(10)
_cell_length_c                   28.2050(6)
_cell_measurement_reflns_used    8917
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.4700
_cell_measurement_theta_min      4.8800
_cell_volume                     4974.00(13)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_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     21.00  99.00   1.00    4.00    --   36.95  57.00  30.00   78
  2  \w    -26.00  58.00   1.00    4.00    --   36.95 -19.00  30.00   84
  3  \w     27.00  87.00   1.00    4.00    --   36.95-125.00 150.00   60
  4  \w     30.00 102.00   1.00    4.00    --   36.95  57.00-180.00   72
  5  \w     55.00 105.00   1.00   16.00    --  111.00 -92.00 120.00   50
  6  \w     44.00 122.00   1.00   16.00    --  111.00 -38.00  30.00   78
  7  \w    111.00 176.00   1.00   16.00    --  111.00  38.00 -30.00   65
  8  \w     48.00 108.00   1.00   16.00    --  111.00 -50.00 120.00   60
  9  \w    103.00 167.00   1.00   16.00    --  111.00  77.00  60.00   64
 10  \w     96.00 130.00   1.00   16.00    --  111.00 -38.00 -60.00   34
 11  \w     47.00  88.00   1.00   16.00    --  111.00 -38.00 -60.00   41
 12  \w    103.00 175.00   1.00   16.00    --  111.00  77.00-180.00   72
 13  \w     45.00 105.00   1.00   16.00    --  111.00 -92.00  60.00   60
;
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18657
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.736
_diffrn_reflns_theta_min         3.687
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82849
_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    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     552
_refine_ls_number_reflns         9738
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0748P)^2^+2.5139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8403
_reflns_number_total             9738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05182j2.cif
_cod_data_source_block           1
_cod_database_code               7132328
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.682
_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. Uiso/Uaniso restraints and constraints
C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C51: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
3.a Ternary CH refined with riding coordinates:
 C30(H30), C27(H27), C42(H42), C39(H39)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C6(H6), C5(H5), C25(H25), C23(H23), C3(H3), C13(H13),
 C24(H24), C35(H35), C36(H36), C37(H37), C49(H49), C50(H50), C46(H46), C45(H45),
  C48(H48), C47(H47), C55(H55), C54(H54), C53(H53), C52(H52), C51(H51), C56(H56)
3.c Fitted hexagon refined as free rotating group:
 C55(C54,C53,C52,C51,C56)
3.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C31(H31A,H31B,H31C), C28(H28A,H28B,H28C), C32(H32A,H32B,
 H32C), C40(H40A,H40B,H40C), C43(H43A,H43B,H43C), C41(H41A,H41B,H41C), C29(H29A,
 H29B,H29C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C),
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              96044
_shelx_hkl_checksum              3939
_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
;