Borane promoted aryl transfer reaction for the synthesis of α-aryl functionalised β-hydroxy and β-keto esters
Kaehler, Tanja; Lorenz, Jonas; Ould, Darren; Engl, Dorothea; Santi, Micol; Gierlichs, Lukas; Wirth, Thomas; Melen, Rebecca; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00643J

data_7158680
_publ_section_title
;
 Borane promoted aryl transfer reaction for the synthesis of \a-aryl
 functionalised \b-hydroxy and \b-keto esters
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00643J
_journal_year                    2022
_chemical_formula_moiety         'C23 H10 B F11 O3'
_chemical_formula_sum            'C23 H10 B F11 O3'
_chemical_formula_weight         554.12
_chemical_name_systematic
4-ethoxy-6-(4-fluorophenyl)-2,2-bis(perfluorophenyl)-2<i>H</i>-1,3\l^3^,2\l^4^-dioxaborinine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.148(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1068(3)
_cell_length_b                   13.2125(4)
_cell_length_c                   18.2143(7)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.5820
_cell_measurement_theta_min      4.0770
_cell_volume                     2188.30(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'XSHELL and Shellxle'
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELLXS
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.900
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       rod
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0620P)^2^+0.2963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3145
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           rm2146b_auto
_cod_original_cell_volume        2188.32(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158680
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.515
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              69416
_publcif_funding_html
;
;