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_1557406
_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         '0.5(C58 H54 B2 Br2), 0.5[C6H14], 0.5[C6H14]'
_chemical_formula_sum            'C64 H68 B2 Br2'
_chemical_formula_weight         1018.62
_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             2019-10-24
_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                91.36(3)
_cell_angle_beta                 92.15(3)
_cell_angle_gamma                116.43(3)
_cell_formula_units_Z            2
_cell_length_a                   13.450(3)
_cell_length_b                   14.624(3)
_cell_length_c                   15.214(3)
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.68
_cell_volume                     2675.1(12)
_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_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            82876
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.398
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.189
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_T_max  0.4296
_exptl_absorpt_correction_T_min  0.3779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.8797.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.124
_refine_diff_density_max         1.027
_refine_diff_density_min         -1.158
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         10942
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0790P)^2^+6.4076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7912
_reflns_number_total             10942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19004
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_original_cell_volume        2675.1(11)
_cod_database_code               1557406
_shelx_shelxl_version_number     2018/3
_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
 C32, C33, C34, C35, C36, C37
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 C57
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C38A, C40A, C39A, C41A, C38B, C40B, C39B, C41B
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3. Uiso/Uaniso restraints and constraints
C38A \\sim C40A \\sim C39A \\sim C41A \\sim C38B \\sim C40B \\sim C39B \\sim
C41B: within 2A with sigma of 0.012 and sigma for terminal atoms of 0.024
C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37: within 2A with sigma of
0.012 and sigma for terminal atoms of 0.024
C57: within 2A with sigma of 0.016 and sigma for terminal atoms of 0.032
4. Others
 Sof(C38B)=Sof(C40B)=Sof(H40D)=Sof(H40E)=Sof(H40F)=Sof(C39B)=Sof(H39D)=
 Sof(H39E)=Sof(H39F)=Sof(C41B)=Sof(H41D)=Sof(H41E)=Sof(H41F)=1-FVAR(1)
 Sof(C38A)=Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(C39A)=Sof(H39A)=
 Sof(H39B)=Sof(H39C)=Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(H41C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C15(H15), C14(H14), C25(H25), C23(H23), C33(H33), C34(H34),
 C36(H36), C37(H37), C44(H44), C43(H43), C52(H52), C54(H54), C49(H49), C12(H12),
  C11(H11), C4(H4), C5(H5)
5.b Fitted hexagon refined as free rotating group:
 C32(C33,C34,C35,C36,C37)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C57(H57A,H57B,
 H57C), C58(H58A,H58B,H58C), C56(H56A,H56B,H56C), C9(H9A,H9B,H9C), C8(H8A,H8B,
 H8C), C10(H10A,H10B,H10C), C40A(H40A,H40B,H40C), C39A(H39A,H39B,H39C),
 C41A(H41A,H41B,H41C), C40B(H40D,H40E,H40F), C39B(H39D,H39E,H39F), C41B(H41D,
 H41E,H41F)
;
_shelx_res_checksum              66014
_shelx_fab_checksum              37674
_olex2_submission_special_instructions 'No special instructions were received'