The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration: mechanistic and functionalisation studies
Yuan, K.; Kahan, R. J.; Si, C.; Williams, A.; Kirschner, S.; Uzelac, M.; Zysman-Colman, E.; Ingleson, M. J.; Chemical Science 11 (2020) 3258–3267; doi:10.1039/C9SC05404A

data_1557400
_publ_section_title
;
 The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration:
 mechanistic and functionalisation studies
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              3258
_journal_page_last               3267
_journal_paper_doi               10.1039/C9SC05404A
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C22 H26 B Br O2'
_chemical_formula_sum            'C22 H26 B Br O2'
_chemical_formula_weight         413.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-25 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7096(3)
_cell_length_b                   6.43840(10)
_cell_length_c                   15.5735(2)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.7340
_cell_measurement_theta_min      4.2530
_cell_volume                     2076.52(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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    -94.00 -35.00   1.00    1.00    --  -41.67 137.00  87.00   59
  2  \w    -75.00 -50.00   1.00    1.00    --  -41.67 132.00 -88.00   25
  3  \w     68.00  93.00   1.00    1.00    --   41.67-137.00  25.00   25
  4  \w     71.00  98.00   1.00    4.00    --  111.00-137.00  25.00   27
  5  \w     78.00 103.00   1.00    4.00    --  111.00-132.00-158.00   25
  6  \w    110.00 137.00   1.00    4.00    --  111.00 132.00 -88.00   27
  7  \w     96.00 136.00   1.00    4.00    --  111.00 137.00  87.00   40
  8  \w   -114.00 -19.00   1.00    1.00    --  -41.67 -38.00-180.00   95
  9  \w     27.00  64.00   1.00    1.00    --   41.67 -38.00 -60.00   37
 10  \w    -30.00  22.00   1.00    1.00    --   41.67 -38.00 -60.00   52
 11  \w     38.00 140.00   1.00    4.00    --  111.00 -77.00   0.00  102
 12  \w    108.00 134.00   1.00    4.00    --  111.00 -30.00   0.00   26
 13  \w     84.00 141.00   1.00    4.00    --  111.00  26.00  -4.93   57
 14  \w     39.00 102.00   1.00    4.00    --  111.00 -30.00   0.00   63
 15  \w    104.00 130.00   1.00    4.00    --  111.00 125.00-180.00   26
 16  \w    150.00 177.00   1.00    4.00    --  111.00 125.00-180.00   27
 17  \w     53.00  93.00   1.00    4.00    --  111.00-125.00  30.00   40
 18  \w     42.00  67.00   1.00    4.00    --  111.00 -45.00   0.00   25
 19  \w     82.00 134.00   1.00    4.00    --  111.00 -45.00   0.00   52
 20  \w     32.00  98.00   1.00    4.00    --  111.00 -94.00-180.00   66
 21  \w    152.00 178.00   1.00    4.00    --  111.00  26.00  -4.93   26
 22  \w     60.00 107.00   1.00    4.00    --  111.00 -94.00 -90.00   47
 23  \w    104.00 178.00   1.00    4.00    --  111.00  77.00 150.00   74
 24  \w    120.00 149.00   1.00    4.00    --  111.00  77.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0616858000
_diffrn_orient_matrix_UB_12      -0.0204803000
_diffrn_orient_matrix_UB_13      0.0546990000
_diffrn_orient_matrix_UB_21      0.0410389000
_diffrn_orient_matrix_UB_22      0.0078212000
_diffrn_orient_matrix_UB_23      0.0823861000
_diffrn_orient_matrix_UB_31      -0.0066560000
_diffrn_orient_matrix_UB_32      0.2383023000
_diffrn_orient_matrix_UB_33      0.0019401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12887
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.883
_diffrn_reflns_theta_min         4.270
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.782
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.275
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0907P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.807
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                3789
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19007_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_database_code               1557400
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H26 B Br O2'
_chemical_oxdiff_usercomment     '@ 120 K '
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.428
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C4(H4), C5(H5), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C9(H9A,H9B,H9C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              61534
_olex2_submission_original_sample_id KY-161
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.760