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_1557405
_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         'C62 H56 B2 Br2, 1[C6H14]'
_chemical_formula_sum            'C62 H56 B2 Br2'
_chemical_formula_weight         982.50
_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
_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                82.02(3)
_cell_angle_beta                 73.02(3)
_cell_angle_gamma                71.06(3)
_cell_formula_units_Z            1
_cell_length_a                   9.836(2)
_cell_length_b                   10.894(2)
_cell_length_c                   14.514(3)
_cell_measurement_reflns_used    3372
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      26.6560
_cell_measurement_theta_min      3.6050
_cell_volume                     1405.2(6)
_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    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -46.00   3.00   1.00   30.00    --   -9.35  91.00-122.00   49
  2  \w    -24.00  27.00   1.00   30.00    --   -9.35 -91.00 123.00   51
  3  \w    -24.00  47.00   1.00   30.00    --   10.52 -91.00 123.00   71
  4  \w    -41.00  21.00   1.00   30.00    --   -9.35  77.00 -60.00   62
  5  \w    -41.00  21.00   1.00   30.00    --   -9.35  77.00  90.00   62
  6  \w    -41.00  21.00   1.00   30.00    --   -9.35  77.00   0.00   62
  7  \w    -41.00  21.00   1.00   30.00    --   -9.35  77.00  30.00   62
  8  \w    -41.00  21.00   1.00   30.00    --   -9.35  77.00 150.00   62
  9  \w     14.00  56.00   1.00   30.00    --   10.52  57.00 -90.00   42
 10  \w    -59.00  36.00   1.00   30.00    --   10.52 -57.00-150.00   95
;
_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      0.0066641000
_diffrn_orient_matrix_UB_12      -0.0171834000
_diffrn_orient_matrix_UB_13      -0.0468534000
_diffrn_orient_matrix_UB_21      -0.0690689000
_diffrn_orient_matrix_UB_22      0.0476142000
_diffrn_orient_matrix_UB_23      -0.0003373000
_diffrn_orient_matrix_UB_31      0.0378462000
_diffrn_orient_matrix_UB_32      0.0467686000
_diffrn_orient_matrix_UB_33      -0.0205437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22003
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  0.76096
_exptl_absorpt_correction_T_min  0.75364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       blade
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and DCM  by solvent layering'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0453P)^2^+2.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3711
_reflns_number_total             5328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19008_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_original_cell_volume        1405.1(6)
_cod_database_code               1557405
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C70 H68 Br2 '
_chemical_oxdiff_usercomment     '@ 120 K'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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. Rigid bond restraints
 C29A, C31A, C29B, C31B
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3. Uiso/Uaniso restraints and constraints
C29A \\sim C31A \\sim C29B \\sim C31B: within 2A with sigma of 0.012 and sigma
for terminal atoms of 0.024
4. Others
 Sof(C29B)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(C31B)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=1-FVAR(1)
 Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C31A)=Sof(H31A)=Sof(H31B)=
 Sof(H31C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3AA(H3AA), C10(H10), C5(H5), C11(H11), C26(H26), C23(H23), C27(H27),
 C24(H24), C17(H17), C15(H15)
5.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C29A(H29A,H29B,H29C), C31A(H31A,
 H31B,H31C), C29B(H29D,H29E,H29F), C31B(H31D,H31E,H31F), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              51119
_shelx_fab_checksum              11163
_olex2_submission_original_sample_id KY170
_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 1.109
_oxdiff_exptl_absorpt_empirical_full_min 0.821