A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with difluorinated silyl enol ethers and acylpyridine N-oxides
Sanz-Marco, Amparo; Esperilla, Daniel; Montesinos-Magraner, Marc; Vila, Carlos; Muñoz, M. Carmen; Pedro, José R.; Blay, Gonzalo; Organic & Biomolecular Chemistry 21 (2023) 345–350; doi:10.1039/D2OB01763F

data_7159039
_publ_section_title
;
 A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with
 difluorinated silyl enol ethers and acylpyridine N-oxides
;
_journal_issue                   2
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              345
_journal_page_last               350
_journal_paper_doi               10.1039/D2OB01763F
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H11 F2 N O3 S'
_chemical_formula_weight         299.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1283(4)
_cell_length_b                   10.6899(6)
_cell_length_c                   15.0823(7)
_cell_measurement_reflns_used    7962
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      29.7157
_cell_measurement_theta_min      2.8467
_cell_volume                     1310.51(12)
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36330
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.535
_diffrn_reflns_theta_min         2.335
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.3074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2908
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01763f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159039.cif.'
_cod_database_code               7159039
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014-1
_shelx_res_checksum              88569