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_7132325
_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         'C20 H24 Br2 O'
_chemical_formula_sum            'C20 H24 Br2 O'
_chemical_formula_weight         440.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 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                 91.5310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.75690(10)
_cell_length_b                   16.9749(2)
_cell_length_c                   12.7839(2)
_cell_measurement_reflns_used    5305
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.4870
_cell_measurement_theta_min      5.2130
_cell_volume                     1899.62(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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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     23.00 104.00   1.00    1.00    --   36.95  57.00-120.00   81
  2  \w     -9.00  47.00   1.00    1.00    --   36.95 -57.00   0.00   56
  3  \w     10.00  76.00   1.00    1.00    --   36.95 -99.00 -60.00   66
  4  \w     28.00  90.00   1.00    1.00    --   36.95-125.00-180.00   62
  5  \w     47.00  92.00   1.00    2.00    --  111.00 -64.00  30.00   45
  6  \w     91.00 137.00   1.00    2.00    --  111.00  64.00-180.00   46
  7  \w    107.00 161.00   1.00    2.00    --  111.00  77.00  90.00   54
  8  \w    152.00 178.00   1.00    2.00    --  111.00  64.00-180.00   26
  9  \w     81.00 134.00   1.00    2.00    --  111.00 -77.00  60.00   53
 10  \w     44.00 128.00   1.00    2.00    --  111.00 -25.00   0.00   84
 11  \w     99.00 124.00   1.00    2.00    --  111.00 -64.00  30.00   25
 12  \w     91.00 171.00   1.00    2.00    --  111.00  64.00 150.00   80
 13  \w     91.00 153.00   1.00    2.00    --  111.00  64.00-120.00   62
 14  \w    -83.00 -53.00   1.00    1.00    --  -36.95 125.00 -90.00   30
 15  \w    -42.00 -13.00   1.00    1.00    --  -36.95 125.00 -90.00   29
 16  \w    -53.00  30.00   1.00    1.00    --  -36.95  57.00 120.00   83
 17  \w     74.00 105.00   1.00    1.00    --   36.95  38.00   0.00   31
 18  \w     19.00  70.00   1.00    1.00    --   36.95  38.00   0.00   51
 19  \w    -30.00  42.00   1.00    1.00    --   36.95 -57.00-150.00   72
 20  \w     81.00 125.00   1.00    2.00    --  111.00  12.00 -90.00   44
 21  \w     59.00 122.00   1.00    2.00    --  111.00 -38.00  60.00   63
 22  \w     81.00 109.00   1.00    2.00    --  111.00-111.00 -90.00   28
 23  \w     42.00  68.00   1.00    2.00    --  111.00-111.00 -90.00   26
 24  \w    102.00 128.00   1.00    2.00    --  111.00 -38.00 -90.00   26
 25  \w     47.00  82.00   1.00    2.00    --  111.00 -38.00 -90.00   35
 26  \w     61.00 108.00   1.00    2.00    --  111.00-111.00-150.00   47
 27  \w     48.00 109.00   1.00    2.00    --  111.00-111.00  30.00   61
 28  \w     78.00 166.00   1.00    2.00    --  111.00  12.00 -30.00   88
 29  \w     47.00 109.00   1.00    2.00    --  111.00   0.00-180.00   62
;
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6801
_diffrn_reflns_point_group_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.737
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.842
_diffrn_reflns_theta_min         5.211
_exptl_absorpt_coefficient_mu    5.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91818
_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    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0212
_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^)+(0.0322P)^2^+0.7009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0557
_reflns_Friedel_coverage         0.482
_reflns_Friedel_fraction_full    0.494
_reflns_Friedel_fraction_max     0.480
_reflns_number_gt                2791
_reflns_number_total             2821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05182j2.cif
_cod_data_source_block           bromoether
_cod_database_code               7132325
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.737
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C12(H12), C4(H4), C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C10(H10A,H10B,
 H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              52717
_shelx_hkl_checksum              49009
_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
;