Base-catalyzed diastereodivergent thia-Michael addition to chiral β-trifluoromethyl-α,β-unsaturated <i>N</i>-acylated oxazolidin-2-ones.
Racochote, Sasirome; Naweephattana, Phiphob; Surawatanawong, Panida; Kuhakarn, Chutima; Leowanawat, Pawaret; Reutrakul, Vichai; Soorukram, Darunee; Organic & biomolecular chemistry 21 (2023) 7180–7187; doi:10.1039/d3ob00999h

data_7159525
_publ_section_title
;
 Base-catalyzed diastereodivergent thia-Michael addition to chiral
 &#x3b2;-trifluoromethyl-&#x3b1;,&#x3b2;-unsaturated <i>N</i>-acylated
 oxazolidin-2-ones.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7180
_journal_page_last               7187
_journal_paper_doi               10.1039/d3ob00999h
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 F3 N O3 S'
_chemical_formula_sum            'C17 H20 F3 N O3 S'
_chemical_formula_weight         375.40
_chemical_name_systematic        II_SR_XRD_03_RT_2
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-10-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-19 deposited with the CCDC.	2023-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4848(3)
_cell_length_b                   11.8755(7)
_cell_length_c                   32.4602(19)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.61
_cell_volume                     2114.3(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'PHOTON 100 CMOS DETECTOR'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       '\k-Geometry Diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            19206
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.294
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'X-ray tube'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_target            Cu
_diffrn_source_type              'Micro focus tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.720
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5190
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.6892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.092(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0726
_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^)+(0.1764P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2141
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3356
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00999h2.cif
_cod_data_source_block           ii_sr_xrd_03_rt_2_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159524--7159525.cif.'
_cod_database_code               7159525
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.847
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              23695
_shelx_hkl_checksum              97392
_olex2_submission_original_sample_id II_SR_XRD_03_RT_2
_olex2_submission_special_instructions 'No special instructions were received'