Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex.
Zhao, Jia-Hui; Zhou, Zhao-Zhao; Zhang, Yue; Su, Xuan; Chen, Xi-Meng; Liang, Yong-Min; Organic & biomolecular chemistry 18 (2020) 4390–4394; doi:10.1039/d0ob00028k

data_7157503
_publ_section_title
;
 Visible-light-mediated borylation of aryl and alkyl halides with a
 palladium complex.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4390
_journal_page_last               4394
_journal_paper_doi               10.1039/d0ob00028k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C14 H18 B N O2'
_chemical_formula_sum            'C14 H18 B N O2'
_chemical_formula_weight         243.10
_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     direct
_audit_creation_date             2019-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3720(3)
_cell_length_b                   12.8487(4)
_cell_length_c                   21.0007(8)
_cell_measurement_reflns_used    2329
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7650
_cell_measurement_theta_min      8.0750
_cell_volume                     2798.69(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -41.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  120.0000 51

  2 omega  -28.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000    0.0000 36

  3 omega  -58.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000    0.0000 28

  4 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -120.0000 26

  5 omega   21.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 47

  6 omega  -17.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -120.0000 26

  7 omega  -13.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 30

  8 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 26

  9 omega   48.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 34

 10 omega   36.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 46

 11 omega   48.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 56

 12 omega  100.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 36

 13 omega  102.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 63

 14 omega   48.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 36

 15 omega   54.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 47

 16 omega  142.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0098954000
_diffrn_orient_matrix_UB_12      0.0411805000
_diffrn_orient_matrix_UB_13      -0.0687388000
_diffrn_orient_matrix_UB_21      0.1129913000
_diffrn_orient_matrix_UB_22      0.0708417000
_diffrn_orient_matrix_UB_23      0.0198248000
_diffrn_orient_matrix_UB_31      0.0959472000
_diffrn_orient_matrix_UB_32      -0.0874632000
_diffrn_orient_matrix_UB_33      -0.0162916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6308
_diffrn_reflns_point_group_measured_fraction_full 0.976
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_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         4.210
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
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_exptl_absorpt_correction_T_min  0.60606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0770P)^2^+0.3437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1963
_reflns_number_total             2414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00028k2.cif
_cod_data_source_block           zhaojh_1022
_cod_depositor_comments
;Adding full bibliography for 7157503.cif.

 Adding full bibliography for 7157503--7157570.cif.
;
_cod_original_cell_volume        2798.70(15)
_cod_database_code               7157503
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 96.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C10(0.6) C11(0.6) H11A(0.6) H11B(0.6) H11C(0.6) C12(0.6) H12A(0.6)
 H12B(0.6) H12C(0.6) C13(0.6) H13A(0.6) H13B(0.6) H13C(0.6) C14(0.6) H14A(0.6)
 H14B(0.6) H14C(0.6) C10'(0.4) C11'(0.4) H11D(0.4) H11E(0.4) H11F(0.4)
 C12'(0.4) H12D(0.4) H12E(0.4) H12F(0.4) C13'(0.4) H13D(0.4) H13E(0.4)
 H13F(0.4) C14'(0.4) H14D(0.4) H14E(0.4) H14F(0.4)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F), C13'(H13D,H13E,H13F),
 C14'(H14D,H14E,H14F)
;
_shelx_res_checksum              22617
_olex2_date_sample_data_collection 2019-10-23
_olex2_submission_special_instructions 'No special instructions were received'