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_7157570
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 N2 O3 S, C2 H6 O'
_chemical_formula_sum            'C18 H22 N2 O4 S'
_chemical_formula_weight         362.43
_chemical_name_common            'febuxostat ethanol solvate'
_chemical_name_systematic
;
2-(3-cyano-4-isobutyloxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic 
acid ethanol solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.994(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7274(2)
_cell_length_b                   17.7820(5)
_cell_length_c                   10.7340(4)
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.6190
_cell_measurement_theta_min      2.2480
_cell_volume                     891.23(6)
_computing_cell_refinement
'CrysAlisPro (Rigaku Oxford Diffraction, 2015)'
_computing_data_collection
'CrysAlisPro (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction
'CrysAlisPro (Rigaku Oxford Diffraction, 2015)'
_computing_molecular_graphics
; 
XP/ShelXTL (Bruker-AXS, 1998) & Mercury (Macrae et al., 2008) 
;
_computing_publication_material
'PLATON (Spek, 2009) & publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3575
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6054
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.094
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro (Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack & Wagner, 2013).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0298
_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^)+(0.0439P)^2^+0.0696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.695
_reflns_Friedel_fraction_max     0.596
_reflns_number_gt                2917
_reflns_number_total             3070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00028k2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7157503--7157570.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157570
_publcif_datablock.id            {6678ffee-2fd8-4f1b-8a51-e4c39f09ceef}
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.929
_shelxl_version_number           2014/6
_shelx_res_checksum              55021
_publcif_funding_html
;
;