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_4034349
_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         'C15 H12 I2'
_chemical_formula_sum            'C15 H12 I2'
_chemical_formula_weight         446.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7664(5)
_cell_length_b                   7.0835(2)
_cell_length_c                   23.4964(8)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      2.1
_cell_volume                     2790.55(15)
_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      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20255
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         2.117
_exptl_absorpt_coefficient_mu    4.484
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.'
_exptl_crystal_colour            'dull whiteish'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.327
_refine_diff_density_min         -1.326
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0236P)^2^+4.7606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2960
_reflns_number_total             3506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00221_si_003.cif
_cod_data_source_block           1_a
_cod_database_code               4034349
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.615
_shelx_estimated_absorpt_t_min   0.483
_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), C10(H10), C11(H11), C9(H9)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'