Inter- and intra-molecular C-H borylation for the formation of PAHs containing triarylborane and indole units.
Escande, A.; Crossley, D. L.; Cid, J.; Cade, I. A.; Vitorica-Yrezabal, I; Ingleson, M. J.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 17160–17167; doi:10.1039/c6dt03526d

data_7040769
_publ_section_title
;
 Inter- and intra-molecular C-H borylation for the formation of PAHs
 containing triarylborane and indole units.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17160
_journal_page_last               17167
_journal_paper_doi               10.1039/c6dt03526d
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C33 H32 B N'
_chemical_formula_sum            'C33 H32 B N'
_chemical_formula_weight         453.40
_chemical_properties_physical    ', Moisture-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-07-18 deposited with the CCDC.
2016-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.198(12)
_cell_angle_beta                 93.594(10)
_cell_angle_gamma                92.798(11)
_cell_formula_units_Z            2
_cell_length_a                   7.8135(10)
_cell_length_b                   12.3648(19)
_cell_length_c                   12.4862(16)
_cell_measurement_reflns_used    2572
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6120
_cell_measurement_theta_min      2.0690
_cell_volume                     1182.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0730820000
_diffrn_orient_matrix_UB_12      -0.0008843000
_diffrn_orient_matrix_UB_13      0.0335991000
_diffrn_orient_matrix_UB_21      0.0413559000
_diffrn_orient_matrix_UB_22      -0.0253337000
_diffrn_orient_matrix_UB_23      -0.0439357000
_diffrn_orient_matrix_UB_31      0.0279486000
_diffrn_orient_matrix_UB_32      0.0507380000
_diffrn_orient_matrix_UB_33      -0.0099618000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_unetI/netI     0.1452
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9631
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.514
_diffrn_reflns_theta_min         1.610
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0760
_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^)+(0.0556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2270
_reflns_number_total             4194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt03526d2.cif
_cod_data_source_block           ae450_crystal2
_cod_depositor_comments          'Adding full bibliography for 7040769.cif.'
_cod_database_code               7040769
_shelxl_version_number           2014/6
_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 Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00D), C00H(H00E,H00F), C00I(H00H,H00I), C00K(H00K,H00L), C00S(H00U,
 H00V), C00U(H00X,H00Y), C00W(H00,H)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00G(H00G), C00J(H00J), C00N(H00P), C00O(H00Q),
 C00P(H00R), C00Q(H00S), C00R(H00T), C00T(H00W), C00V(H00Z), C00X(H0AA)
2.c Idealised Me refined as rotating group:
 C00L(H00M,H00N,H00O), C00Y(H1AA,HA,HB)
;
_shelx_res_checksum              2672
_olex2_submission_special_instructions 'No special instructions were received'