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_7158682
_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         'C18 H16 F4 O3'
_chemical_formula_sum            'C18 H16 F4 O3'
_chemical_formula_weight         356.31
_chemical_name_systematic
ethyl(2S,3S)-3-(4-fluorophenyl)-3-hydroxy-2-methyl-2-(2,4,6-trifluorophenyl)propanoate
_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   mixed
_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                113.593(6)
_cell_angle_beta                 103.792(7)
_cell_angle_gamma                90.918(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0494(7)
_cell_length_b                   9.9716(7)
_cell_length_c                   11.4118(7)
_cell_measurement_reflns_used    2857
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.6970
_cell_measurement_theta_min      4.0870
_cell_volume                     808.79(12)
_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 shelxle'
_computing_publication_material  'XCIF and publCIF'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6366
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.250
_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    1.463
_exptl_crystal_description       Block
_exptl_crystal_F_000             368
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0353P)^2^+0.2122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2279
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           RM2205_auto
_cod_original_cell_volume        808.80(11)
_cod_database_code               7158682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              10425
_publcif_funding_html
;
;