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_1557399
_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 H78 B2 Br2'
_chemical_formula_sum            'C62 H78 B2 Br2'
_chemical_formula_weight         1004.68
_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             2019-05-08
_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                93.579(3)
_cell_angle_beta                 100.145(3)
_cell_angle_gamma                90.470(3)
_cell_formula_units_Z            1
_cell_length_a                   9.4752(4)
_cell_length_b                   9.8107(4)
_cell_length_c                   15.1088(6)
_cell_measurement_reflns_used    8973
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      75.9150
_cell_measurement_theta_min      2.9580
_cell_volume                     1379.57(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (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 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.954
_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     67.00 132.00   1.00    1.00    --   45.10  40.00-107.00   65
  2  \w    -43.00  -3.00   1.00    1.00    --   45.10  40.00-107.00   40
  3  \w     77.00 134.00   1.00    1.00    --   45.10  60.00   0.00   57
  4  \w    -44.00  -8.00   1.00    1.00    --   45.10  60.00   0.00   36
  5  \w    -44.00  43.00   1.00    1.00    --   45.10  60.00-180.00   87
  6  \w    -30.00 133.00   1.00    1.00    --   45.10  60.00 120.00  163
  7  \w     46.00 134.00   1.00    1.00    --   45.10  60.00-180.00   88
  8  \w    111.00 142.00   1.00    2.00    --  108.20  50.00-180.00   31
  9  \w     42.00  71.00   1.00    2.00    --  108.20  50.00-180.00   29
 10  \w     42.00  79.00   1.00    2.00    --  108.20  50.00   0.00   37
 11  \w     26.00  55.00   1.00    2.00    --  108.20  50.00  60.00   29
 12  \w     23.00  49.00   1.00    2.00    --  108.20  50.00-120.00   26
 13  \w     79.00 105.00   1.00    2.00    --  108.20  50.00  60.00   26
 14  \w    134.00 197.00   1.00    2.00    --  108.20  50.00  60.00   63
 15  \w     28.00  75.00   1.00    2.00    --  108.20  50.00 -60.00   47
 16  \w    101.00 133.00   1.00    2.00    --  108.20  50.00 -60.00   32
 17  \w    138.00 181.00   1.00    2.00    --  108.20  50.00   0.00   43
 18  \w     89.00 183.00   1.00    2.00    --  108.20  50.00  30.00   94
 19  \w     27.00  81.00   1.00    2.00    --  108.20  50.00  30.00   54
 20  \w    140.00 166.00   1.00    2.00    --  108.20  50.00 -30.00   26
 21  \w     67.00  93.00   1.00    2.00    --  108.20  50.00 150.00   26
 22  \w     72.00 163.00   1.00    2.00    --  108.20  50.00-120.00   91
 23  \w    169.00 195.00   1.00    2.00    --  108.20  50.00-120.00   26
 24  \w     19.00 193.00   1.00    2.00    --  108.20  10.00-150.00  174
 25  \w     40.00  66.00   1.00    2.00    --  108.20  50.00  90.00   26
 26  \w     73.00 195.00   1.00    2.00    --  108.20  50.00  90.00  122
 27  \w    142.00 168.00   1.00    2.00    --  108.20  50.00 -60.00   26
 28  \w    148.00 176.00   1.00    2.00    --  108.20  50.00-180.00   28
 29  \w     26.00  52.00   1.00    2.00    --  108.20  50.00-150.00   26
 30  \w    132.00 168.00   1.00    2.00    --  108.20  50.00-150.00   36
 31  \w     81.00 183.00   1.00    2.00    --  108.20  50.00 -90.00  102
 32  \w     21.00 139.00   1.00    2.00    --  108.20  40.00 -30.00  118
 33  \w     82.00 107.00   1.00    2.00    --  108.20  50.00   0.00   25
 34  \w    144.00 169.00   1.00    2.00    --  108.20  50.00 150.00   25
 35  \w    109.00 197.00   1.00    2.00    --  108.20  50.00 120.00   88
 36  \w     38.00  78.00   1.00    2.00    --  108.20  40.00-107.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0707400000
_diffrn_orient_matrix_UB_12      -0.0842836000
_diffrn_orient_matrix_UB_13      0.0635989000
_diffrn_orient_matrix_UB_21      0.0920718000
_diffrn_orient_matrix_UB_22      -0.1231098000
_diffrn_orient_matrix_UB_23      -0.0197887000
_diffrn_orient_matrix_UB_31      0.1175180000
_diffrn_orient_matrix_UB_32      0.0500400000
_diffrn_orient_matrix_UB_33      0.0796152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18796
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.420
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    2.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0254P)^2^+0.9372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4870
_reflns_number_total             5521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           lmji13
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_database_code               1557399
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_ac4_digest_frames
;
015d56c373958fd557b095d281d2e6323000031dd92
;
_reflns_odcompleteness_completeness 96.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C3(H3), C19(H19), C21(H21)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C24(H24A,H24B,H24C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              40109
_olex2_submission_original_sample_id lmji13
_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 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.827