Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes.
Mfuh, Adelphe M.; Nguyen, Vu T.; Chhetri, Bhuwan; Burch, Jessica E.; Doyle, John D.; Nesterov, Vladimir N.; Arman, Hadi D.; Larionov, Oleg V.; Journal of the American Chemical Society 138 (2016) 8408–8411; doi:10.1021/jacs.6b05436

data_4130636
_publ_section_title
;
 Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective,
 Photoinduced Dual C-H/C-X Borylation of Haloarenes.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8408
_journal_page_last               8411
_journal_paper_doi               10.1021/jacs.6b05436
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C19 H27 B2 F3 O4'
_chemical_formula_sum            'C19 H27 B2 F3 O4'
_chemical_formula_weight         398.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.279(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9964(6)
_cell_length_b                   14.6674(5)
_cell_length_c                   12.8154(6)
_cell_measurement_reflns_used    7451
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2740
_cell_measurement_theta_min      3.6830
_cell_volume                     2065.34(16)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6876
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.111
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0100P)^2^+4.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6312
_reflns_number_total             6876
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05436_si_002.cif
_cod_data_source_block           cd1444_twin1_hklf4
_cod_database_code               4130636
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6004(14) 0.3996(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C5(H5)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C12(H12A,H12B,
 H12C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'