Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation.
Devaraj, Karthik; Ingner, Fredric J. L.; Sollert, Carina; Gates, Paul J.; Orthaber, Andreas; Pilarski, Lukasz T.; The Journal of organic chemistry 84 (2019) 5863–5871; doi:10.1021/acs.joc.9b00221

data_4034350
_publ_section_title
;
 Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H
 Silylation.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5863
_journal_page_last               5871
_journal_paper_doi               10.1021/acs.joc.9b00221
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C30 H22 F9 N O3 S Si'
_chemical_formula_sum            'C30 H22 F9 N O3 S Si'
_chemical_formula_weight         675.63
_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     dual
_audit_creation_date             2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                85.646(2)
_cell_angle_beta                 67.2200(10)
_cell_angle_gamma                85.535(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7186(3)
_cell_length_b                   11.7426(3)
_cell_length_c                   12.7090(3)
_cell_measurement_reflns_used    7106
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.40
_cell_volume                     1468.54(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.674
_diffrn_reflns_theta_min         1.740
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0787 before and 0.0494 after correction. The Ratio of minimum to maximum transmission is 0.9284. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         8990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0533P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5885
_reflns_number_total             8990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00221_si_002.cif
_cod_data_source_block           2_a
_cod_database_code               4034350
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.946
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9), C11(H11), C26(H26), C14(H14), C22(H22),
 C10(H10), C18(H18), C24(H24), C25(H25), C23(H23), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'