Catalytic asymmetric CO<sub>2</sub> utilization reaction for the enantioselective synthesis of chiral 2-oxazolidinones.
Nishiyori, Ryuichi; Mori, Taiki; Shirakawa, Seiji; Organic & biomolecular chemistry 21 (2023) 4002–4006; doi:10.1039/d3ob00555k

data_7159304
_publ_section_title
;
 Catalytic asymmetric CO<sub>2</sub> utilization reaction for the
 enantioselective synthesis of chiral 2-oxazolidinones.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4002
_journal_page_last               4006
_journal_paper_doi               10.1039/d3ob00555k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C11 H9 Br F3 N O3'
_chemical_formula_sum            'C11 H9 Br F3 N O3'
_chemical_formula_weight         340.10
_chemical_name_systematic        4d-OCF3
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-06
_audit_creation_method
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_audit_update_record
;
2023-02-25 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6831(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3801(2)
_cell_length_b                   5.46613(14)
_cell_length_c                   18.0363(4)
_cell_measurement_reflns_used    4847
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6090
_cell_measurement_theta_min      2.4880
_cell_volume                     1218.02(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     94.00 119.00   0.50    0.09    --  107.00  61.00-150.00   50
  2  \w     95.00 121.00   0.50    0.09    --  107.00  61.00-180.00   52
  3  \w    129.00 174.00   0.50    0.09    --  107.00  61.00-150.00   90
  4  \w    148.00 175.00   0.50    0.09    --  107.00  45.00 -30.00   54
  5  \w    -60.00 -35.00   0.50    0.05    --  -44.46 -52.00 136.47   50
  6  \w    -94.00 -42.00   0.50    0.05    --  -44.46 -52.00 125.27  104
  7  \w    -96.00 -70.00   0.50    0.05    --  -44.46 -52.00 136.47   52
  8  \w    -62.00 -36.00   0.50    0.05    --  -44.46 -48.00 152.10   52
  9  \w   -115.00 -81.00   0.50    0.05    --  -44.46 -47.00 162.02   68
 10  \w    -63.00 -38.00   0.50    0.05    --  -44.46 -47.00 162.02   50
 11  \w    -58.00 -33.00   0.50    0.05    --  -44.46 -52.00  56.99   50
 12  \w    -76.00 -36.00   0.50    0.05    --  -44.46 -38.00  60.00   80
 13  \w   -115.00 -89.00   0.50    0.05    --  -44.46 -38.00  60.00   52
 14  \w    -68.00 -36.00   0.50    0.05    --  -44.46 -38.00-150.00   64
 15  \w    -79.00 -34.00   0.50    0.05    --  -44.46 -51.00-165.99   90
 16  \w   -108.00 -82.00   0.50    0.05    --  -44.46 -51.00-165.99   52
 17  \w   -115.00 -90.00   0.50    0.09    -- -104.00 -62.00-107.23   50
 18  \w   -116.00 -91.00   0.50    0.09    -- -104.00 -61.00-120.00   50
 19  \w   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00-180.00   50
 20  \w   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00-150.00   50
 21  \w   -174.00-136.00   0.50    0.09    -- -104.00 -61.00-180.00   76
 22  \w   -175.00-139.00   0.50    0.09    -- -104.00 -61.00-150.00   72
 23  \w   -168.00-142.00   0.50    0.09    -- -104.00 -62.00-107.23   52
 24  \w   -171.00-145.00   0.50    0.09    -- -104.00 -59.00-125.54   52
 25  \w   -126.00 -93.00   0.50    0.09    -- -104.00 -59.00-125.54   66
 26  \w   -116.00 -91.00   0.50    0.09    -- -104.00 -59.00-134.31   50
 27  \w   -117.00 -92.00   0.50    0.09    -- -104.00 -58.00-172.85   50
 28  \w   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00 120.00   50
 29  \w   -115.00 -90.00   0.50    0.09    -- -104.00 -61.00 150.00   50
 30  \w   -124.00 -91.00   0.50    0.09    -- -104.00 -58.00 161.27   66
 31  \w   -118.00 -93.00   0.50    0.09    -- -104.00 -58.00 168.14   50
 32  \w   -118.00 -93.00   0.50    0.09    -- -104.00 -57.00 179.39   50
 33  \w   -175.00-149.00   0.50    0.09    -- -104.00 -58.00 161.27   52
 34  \w   -172.00-146.00   0.50    0.09    -- -104.00 -58.00 168.14   52
 35  \w   -168.00-141.00   0.50    0.09    -- -104.00 -49.00 117.13   54
 36  \w   -121.00 -93.00   0.50    0.09    -- -104.00 -49.00 117.13   56
 37  \w   -119.00 -94.00   0.50    0.09    -- -104.00 -46.00-101.41   50
 38  \w   -122.00 -96.00   0.50    0.09    -- -104.00 -46.00-111.79   52
 39  \w   -131.00-105.00   0.50    0.09    -- -104.00 -45.00-150.00   52
 40  \w   -118.00 -93.00   0.50    0.09    -- -104.00 -45.00-180.00   50
 41  \w   -171.00-145.00   0.50    0.09    -- -104.00 -46.00-101.41   52
 42  \w   -121.00 -96.00   0.50    0.09    -- -104.00 -43.00-175.24   50
 43  \w   -118.00 -93.00   0.50    0.09    -- -104.00 -45.00 120.00   50
 44  \w   -122.00 -96.00   0.50    0.09    -- -104.00 -43.00 176.36   52
 45  \w   -123.00 -97.00   0.50    0.09    -- -104.00 -43.00 167.51   52
 46  \w   -126.00 -97.00   0.50    0.09    -- -104.00 -30.00  90.00   58
 47  \w   -128.00-103.00   0.50    0.09    -- -104.00 -15.00-120.00   50
 48  \w   -120.00 -95.00   0.50    0.09    -- -104.00 -30.00-180.00   50
 49  \w    -27.00   2.00   0.50    0.05    --   44.46 -38.00  30.00   58
 50  \w     36.00  99.00   0.50    0.09    --  107.00-125.00 -90.00  126
 51  \w     35.00  83.00   0.50    0.09    --  107.00 -95.00-150.00   96
 52  \w     34.00  59.00   0.50    0.09    --  107.00 -95.00-180.00   50
 53  \w     68.00  93.00   0.50    0.09    --  107.00 -95.00-180.00   50
 54  \w      3.00  74.00   0.50    0.05    --   44.46 -99.00 -60.00  142
 55  \w     57.00  84.00   0.50    0.09    --  107.00 -95.00 150.00   54
 56  \w     35.00  74.00   0.50    0.09    --  107.00 -95.00 120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1233760000
_diffrn_orient_matrix_UB_12      -0.0350339000
_diffrn_orient_matrix_UB_13      0.0004956000
_diffrn_orient_matrix_UB_21      0.0092721000
_diffrn_orient_matrix_UB_22      -0.0091618000
_diffrn_orient_matrix_UB_23      0.0854904000
_diffrn_orient_matrix_UB_31      -0.0153191000
_diffrn_orient_matrix_UB_32      0.2797031000
_diffrn_orient_matrix_UB_33      0.0029076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6540
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.110
_diffrn_reflns_theta_min         2.455
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.855
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane-Hexane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0338P)^2^+0.6125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                2137
_reflns_number_total             2195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00555k2.cif
_cod_data_source_block           sample2_auto
_cod_depositor_comments
'Adding full bibliography for 7159303--7159304.cif.'
_cod_original_cell_volume        1218.01(4)
_cod_database_code               7159304
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H9BrF3NO3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9)
;
_shelx_res_checksum              85967
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.741