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_1557401
_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         'C14 H10 B Br3'
_chemical_formula_sum            'C14 H10 B Br3'
_chemical_formula_weight         428.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 100.580(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2781(3)
_cell_length_b                   5.93600(10)
_cell_length_c                   18.4485(4)
_cell_measurement_reflns_used    14704
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      31.9930
_cell_measurement_theta_min      3.7660
_cell_volume                     1429.37(5)
_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_temperature      170.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_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      8.00  95.00   1.00   30.00    --   26.59  57.00  60.00   87
  2  \w    -16.00  70.00   1.00   30.00    --   26.59-105.00 155.00   86
  3  \w    -20.00  67.00   1.00   30.00    --   26.59 -99.00 -60.00   87
  4  \w    -42.00  45.00   1.00   30.00    --   26.59 -57.00-180.00   87
  5  \w    -20.00  67.00   1.00   30.00    --   26.59 -99.00  60.00   87
  6  \w    -46.00  64.00   1.00   30.00    --   26.59 -19.00-120.00  110
  7  \w    -93.00  -6.00   1.00   30.00    --  -24.72 -57.00 -90.00   87
  8  \w    -93.00  -6.00   1.00   30.00    --  -24.72 -57.00  90.00   87
  9  \w    -93.00  -6.00   1.00   30.00    --  -24.72 -57.00-180.00   87
 10  \w    -42.00  45.00   1.00   30.00    --   26.59 -57.00  60.00   87
 11  \w      8.00  95.00   1.00   30.00    --   26.59  57.00 -30.00   87
 12  \w    -95.00  -2.00   1.00   30.00    --  -24.72 -37.00 -90.00   93
 13  \w    -93.00  -6.00   1.00   30.00    --  -24.72 -57.00 150.00   87
 14  \w     39.00  85.00   1.00   30.00    --   26.59 178.00 120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0339801000
_diffrn_orient_matrix_UB_12      0.0119060000
_diffrn_orient_matrix_UB_13      0.0342431000
_diffrn_orient_matrix_UB_21      -0.0405765000
_diffrn_orient_matrix_UB_22      0.0436545000
_diffrn_orient_matrix_UB_23      0.0160108000
_diffrn_orient_matrix_UB_31      -0.0123374000
_diffrn_orient_matrix_UB_32      -0.1106072000
_diffrn_orient_matrix_UB_33      0.0100204000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41168
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.444
_exptl_absorpt_correction_T_max  0.427
_exptl_absorpt_correction_T_min  0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.633
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0318P)^2^+0.2430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3527
_reflns_number_total             4355
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19002_reint_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_database_code               1557401
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H10 B Br3'
_chemical_oxdiff_usercomment     '@ 170 K KY124'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I)
;
_shelx_res_checksum              34008
_olex2_submission_original_sample_id KY124
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.703