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_4130637
_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 O5'
_chemical_formula_sum            'C19 H27 B2 F3 O5'
_chemical_formula_weight         414.02
_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     direct
_audit_creation_date             2016-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                104.079(3)
_cell_angle_beta                 98.934(3)
_cell_angle_gamma                114.197(4)
_cell_formula_units_Z            4
_cell_length_a                   13.1779(5)
_cell_length_b                   13.6565(6)
_cell_length_c                   14.0817(5)
_cell_measurement_reflns_used    8409
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.1070
_cell_measurement_theta_min      1.7640
_cell_volume                     2146.96(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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    -68.00  55.00   0.50   45.00    --  -35.00  70.00 270.00  246
  2  \w    -68.00  37.00   0.50   45.00    --  -35.00  70.00  90.00  210
  3  \w   -125.00 -80.00   0.50   45.00    --  -35.00   0.00   0.00   90
  4  \w    -69.00 -34.00   0.50   45.00    --  -35.00   0.00  90.00   70
  5  \w    -50.00 -20.00   0.50   45.00    --  -35.00  70.00 180.00   60
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0318803000
_diffrn_orient_matrix_UB_12      -0.0276088000
_diffrn_orient_matrix_UB_13      -0.0185808000
_diffrn_orient_matrix_UB_21      -0.0336784000
_diffrn_orient_matrix_UB_22      -0.0158071000
_diffrn_orient_matrix_UB_23      -0.0508051000
_diffrn_orient_matrix_UB_31      0.0405834000
_diffrn_orient_matrix_UB_32      0.0515341000
_diffrn_orient_matrix_UB_33      -0.0038296000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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       -17
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.811
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              '(Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         7765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0300P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5844
_reflns_number_total             7765
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 176.7269\% 
 around [-0.69 0.72 -0.05] (reciprocal) or [-0.71 0.70 -0.00] (direct)
;
_cod_data_source_file            ja6b05436_si_003.cif
_cod_data_source_block           cd144_twin1_hklf4
_cod_original_cell_volume        2146.96(16)
_cod_database_code               4130637
_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), C21(H21), C5(H5), C24(H24), C6(H6), C23(H23)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C36(H36A,H36B,
 H36C), C29(H29A,H29B,H29C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,
 H9B,H9C), C28(H28A,H28B,H28C), C17(H17A,H17B,H17C), C30(H30A,H30B,H30C),
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C31(H31A,H31B,H31C), C18(H18A,H18B,
 H18C), C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.802
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2