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_1557402
_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         'C44 H42 B2 Br2 O2'
_chemical_formula_sum            'C44 H42 B2 Br2 O2'
_chemical_formula_weight         784.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-25
_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            8
_cell_length_a                   42.071(3)
_cell_length_b                   29.3977(10)
_cell_length_c                   6.6541(2)
_cell_measurement_reflns_used    6228
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      67.2960
_cell_measurement_theta_min      4.6040
_cell_volume                     8229.7(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -112.00 -15.00   1.00   15.00    --  -41.67 -57.00-166.00   97
  2  \w    -68.00  28.00   1.00   15.00    --  -41.67  57.00 -24.00   96
  3  \w    -28.00  68.00   1.00   15.00    --   41.67 -57.00-166.00   96
  4  \w     15.00 112.00   1.00   15.00    --   41.67  57.00 -24.00   97
  5  \w     82.00 178.00   1.00   25.00    --  108.85  57.00 -24.00   96
  6  \w     39.00 135.00   1.00   25.00    --  108.85 -57.00-166.00   96
  7  \w     61.00 128.00   1.00   15.00    --   41.67 178.00 -90.00   67
  8  \w     61.00 128.00   1.00   15.00    --   41.67 178.00  30.00   67
  9  \w     61.00 128.00   1.00   15.00    --   41.67 178.00-180.00   67
 10  \w     85.00 178.00   1.00   25.00    --  108.85  30.00 -60.00   93
 11  \w     35.00 140.00   1.00   25.00    --  108.85 -77.00  90.00  105
 12  \w     85.00 178.00   1.00   25.00    --  108.85  45.00-120.00   93
 13  \w     37.00 113.00   1.00   25.00    --  108.85-125.00-150.00   76
 14  \w     37.00 113.00   1.00   25.00    --  108.85-125.00  90.00   76
 15  \w   -112.00 -15.00   1.00   15.00    --  -41.67 -57.00  90.00   97
;
_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      -0.0805889000
_diffrn_orient_matrix_UB_12      -0.0342232000
_diffrn_orient_matrix_UB_13      -0.0034994000
_diffrn_orient_matrix_UB_21      -0.1544264000
_diffrn_orient_matrix_UB_22      0.0108663000
_diffrn_orient_matrix_UB_23      -0.0358114000
_diffrn_orient_matrix_UB_31      0.1525007000
_diffrn_orient_matrix_UB_32      -0.0071186000
_diffrn_orient_matrix_UB_33      -0.0381105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            41818
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        50.433
_diffrn_reflns_theta_max         50.433
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       needle
_exptl_crystal_F_000             3216
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.027
_refine_diff_density_max         1.324
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0907
_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^)+(0.0894P)^2^+159.7395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2404
_refine_ls_wR_factor_ref         0.2580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3155
_reflns_number_total             4320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19003_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_original_cell_volume        8229.7(6)
_cod_database_code               1557402
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H42 B2 Br2 O2'
_chemical_oxdiff_usercomment     '@ 120 K KY123'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C37(H37), C27(H27), C6(H6), C17(H17), C2(H2A), C36(H36), C30(H30),
 C11(H11), C40(H40), C29(H29), C39(H39), C26(H26)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C44(H44A,H44B,H44C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C),
 C42(H42A,H42B,H42C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C), C43(H43A,H43B,H43C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_shelx_res_checksum              13007
_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 1.626
_oxdiff_exptl_absorpt_empirical_full_min 0.597