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_1557398
_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         'C22 H26 B Br O2'
_chemical_formula_sum            'C22 H26 B Br O2'
_chemical_formula_weight         413.15
_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                 97.511(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4265(4)
_cell_length_b                   15.8695(10)
_cell_length_c                   20.6170(11)
_cell_measurement_reflns_used    4753
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      27.2530
_cell_measurement_theta_min      4.0710
_cell_volume                     2084.6(2)
_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 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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      7.00  59.00   1.00   15.00    --   10.52-127.00  99.00   52
  2  \w     22.00  47.00   1.00   15.00    --   10.52-143.00 -70.00   25
  3  \w    -15.00  31.00   1.00   15.00    --   -9.35 -99.00  30.00   46
  4  \w     -5.00  21.00   1.00   15.00    --   10.52 -99.00 150.00   26
  5  \w    -23.00  89.00   1.00   15.00    --   10.52  19.00 -30.00  112
  6  \w    -28.00  33.00   1.00   15.00    --   10.52 -77.00 -30.00   61
;
_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      0.0235783000
_diffrn_orient_matrix_UB_12      -0.0326918000
_diffrn_orient_matrix_UB_13      0.0232641000
_diffrn_orient_matrix_UB_21      0.0165193000
_diffrn_orient_matrix_UB_22      0.0303731000
_diffrn_orient_matrix_UB_23      0.0253839000
_diffrn_orient_matrix_UB_31      -0.1075645000
_diffrn_orient_matrix_UB_32      -0.0025045000
_diffrn_orient_matrix_UB_33      0.0042851000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18476
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        27.483
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.984
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0133P)^2^+2.7772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3693
_reflns_number_total             4679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19006_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_database_code               1557398
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H26 B Br O2'
_chemical_oxdiff_usercomment     '@ 120 K KY161'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C1A, C2A, C19A, C20A, C21A, C22A, C1B, C2B, C19B, C20B, C21B, C22B
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C1B \\sim C2B
\\sim C19B \\sim C20B \\sim C21B \\sim C22B: within 2A with sigma of 0.012 and
sigma for terminal atoms of 0.024
4. Others
 Sof(C1B)=Sof(C2B)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20B)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22B)=
 Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22A)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C8(H8), C7(H7), C9(H9), C14(H14), C13(H13), C11(H11)
5.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C19A(H19A,H19B,H19C), C20A(H20A,
 H20B,H20C), C21A(H21A,H21B,H21C), C22A(H22A,H22B,H22C), C19B(H19D,H19E,H19F),
 C20B(H20D,H20E,H20F), C21B(H21D,H21E,H21F), C22B(H22D,H22E,H22F)
;
_shelx_res_checksum              35982
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.779