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_7158679
_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         'C19 H16 F6 O3'
_chemical_formula_sum            'C19 H16 F6 O3'
_chemical_formula_weight         406.32
_chemical_name_systematic
'Ethyl (2R)-3-hydroxy-2-methyl-3-(4-(trifluoromethyl)phenyl)-2-(3,4,5-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   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                101.608(3)
_cell_angle_beta                 91.454(2)
_cell_angle_gamma                100.640(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1188(2)
_cell_length_b                   10.3636(3)
_cell_length_c                   12.8288(4)
_cell_measurement_reflns_used    13803
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3320
_cell_measurement_theta_min      4.4010
_cell_volume                     909.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_molecular_graphics    'XSHELL and Shelxle'
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ShelXS
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.087
_diffrn_reflns_theta_min         3.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
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    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.188
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0088(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.5367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2996
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00643j2.cif
_cod_data_source_block           rm1831h
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct' was changed
to 'direct' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7158679
_shelx_estimated_absorpt_t_min   0.551
_shelx_estimated_absorpt_t_max   0.801
_shelx_res_checksum              78433