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_1557397
_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         'C36 H36 B Br'
_chemical_formula_sum            'C36 H36 B Br'
_chemical_formula_weight         559.37
_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             2019-10-25
_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                80.254(4)
_cell_angle_beta                 85.195(5)
_cell_angle_gamma                68.593(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4803(5)
_cell_length_b                   9.1672(5)
_cell_length_c                   19.9099(11)
_cell_measurement_reflns_used    7180
_cell_measurement_temperature    150.03(13)
_cell_measurement_theta_max      75.6340
_cell_measurement_theta_min      2.2090
_cell_volume                     1419.82(15)
_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(13)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.957
_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    -44.00  11.00   1.00    1.00    --   44.80  60.00 150.00   55
  2  \w    -44.00  97.00   1.00    1.00    --   44.80  60.00  60.00  141
  3  \w    102.00 134.00   1.00    1.00    --   44.80  60.00  60.00   32
  4  \w    -45.00  24.00   1.00    1.00    --   44.80  60.00-120.00   69
  5  \w     34.00 113.00   1.00    1.00    --   44.80  60.00 150.00   79
  6  \w     65.00 100.00   1.00    1.00    --   44.80  20.00   0.00   35
  7  \w     75.00 134.00   1.00    1.00    --   44.80  60.00-120.00   59
  8  \w    -43.00  21.00   1.00    1.00    --   44.80  20.00   0.00   64
  9  \w    155.00 195.00   1.00    5.00    --  108.20  50.00 -30.00   40
 10  \w    106.00 196.00   1.00    5.00    --  108.20  50.00  60.00   90
 11  \w    109.00 145.00   1.00    5.00    --  108.20  50.00 -30.00   36
 12  \w     34.00  92.00   1.00    5.00    --  108.20  50.00 -90.00   58
 13  \w    103.00 129.00   1.00    5.00    --  108.20  50.00 -90.00   26
 14  \w    119.00 168.00   1.00    5.00    --  108.20  20.00-180.00   49
 15  \w     24.00  51.00   1.00    5.00    --  108.20  50.00 150.00   27
 16  \w    130.00 187.00   1.00    5.00    --  108.20  50.00   0.00   57
 17  \w    121.00 161.00   1.00    5.00    --  108.20  50.00 120.00   40
 18  \w    104.00 197.00   1.00    5.00    --  108.20  50.00 150.00   93
 19  \w     19.00  73.00   1.00    5.00    --  108.20  50.00 120.00   54
 20  \w     93.00 122.00   1.00    5.00    --  108.20  50.00   0.00   29
 21  \w     97.00 155.00   1.00    5.00    --  108.20  50.00-180.00   58
 22  \w     22.00 197.00   1.00    5.00    --  108.20  10.00-180.00  175
 23  \w    145.00 193.00   1.00    5.00    --  108.20  50.00-120.00   48
 24  \w     40.00  66.00   1.00    5.00    --  108.20  50.00-180.00   26
 25  \w     47.00 197.00   1.00    5.00    --  108.20  50.00 -60.00  150
 26  \w     20.00 142.00   1.00    5.00    --  108.20  40.00   0.00  122
 27  \w     73.00 196.00   1.00    5.00    --  108.20  50.00  90.00  123
 28  \w    103.00 138.00   1.00    5.00    --  108.20  50.00-150.00   35
 29  \w     55.00  81.00   1.00    5.00    --  108.20  50.00-120.00   26
 30  \w     65.00  90.00   1.00    5.00    --  108.20  50.00 150.00   25
 31  \w    148.00 173.00   1.00    5.00    --  108.20  20.00  30.00   25
 32  \w    145.00 172.00   1.00    5.00    --  108.20  50.00-150.00   27
 33  \w     45.00 119.00   1.00    5.00    --  108.20  20.00  30.00   74
;
_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      0.1297834000
_diffrn_orient_matrix_UB_12      -0.0456112000
_diffrn_orient_matrix_UB_13      0.0566798000
_diffrn_orient_matrix_UB_21      -0.1226480000
_diffrn_orient_matrix_UB_22      -0.0526605000
_diffrn_orient_matrix_UB_23      0.0510622000
_diffrn_orient_matrix_UB_31      0.0786557000
_diffrn_orient_matrix_UB_32      -0.1687520000
_diffrn_orient_matrix_UB_33      -0.0185499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9463
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.276
_diffrn_reflns_theta_min         2.252
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    2.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78770
_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_colour_primary    orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.073
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         9463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0686P)^2^+0.5967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7835
_reflns_number_total             9463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           lmji12
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_original_cell_volume        1419.82(14)
_cod_database_code               1557397
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.860
_diffrn_oxdiff_ac4_digest_frames
;
015fab16c3fe43f2f5759bb23481cd7cf500032b991
;
_reflns_odcompleteness_completeness 96.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6082(10)
 0.3918(10)
2. 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
3.a Ternary CH refined with riding coordinates:
 C31(H31), C28(H28), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C34(H34a,H34b), C35(H35a,H35b)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C18(H18), C17(H17), C13(H13), C6(H6), C12(H12), C15(H15)
3.d Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c), C32(H32a,H32b,H32c), C29(H29a,H29b,H29c), C26(H26a,H26b,
 H26c), C33(H33a,H33b,H33c), C30(H30a,H30b,H30c), C36(H36a,H36b,H36c)
;
_shelx_res_checksum              32055
_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 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.801