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_7159303
_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         'C10 H9 Br Cl N O2'
_chemical_formula_sum            'C10 H9 Br Cl N O2'
_chemical_formula_weight         290.54
_chemical_name_systematic        4b-pCl
_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     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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.47910(10)
_cell_length_b                   14.1480(4)
_cell_length_c                   27.7407(8)
_cell_measurement_reflns_used    7744
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5200
_cell_measurement_theta_min      3.1710
_cell_volume                     2150.41(10)
_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 0.981
_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    103.00 128.00   0.50    0.06    --  107.00  15.00-150.00   50
  2  \w     99.00 129.00   0.50    0.06    --  107.00  15.00 -90.00   60
  3  \w     99.00 128.00   0.50    0.06    --  107.00  15.00 -60.00   58
  4  \w    -11.00  30.00   0.50    0.05    --  -44.46  38.00 -30.00   82
  5  \w    -12.00  31.00   0.50    0.05    --  -44.46  38.00-150.00   86
  6  \w    -73.00 -33.00   0.50    0.06    -- -104.00  77.00 -30.00   80
  7  \w    -93.00 -67.00   0.50    0.06    -- -104.00 116.00  55.00   52
  8  \w    -57.00 -31.00   0.50    0.06    -- -104.00 116.00  55.00   52
  9  \w    -71.00 -26.00   0.50    0.05    --  -44.46 100.00 -29.00   90
 10  \w   -123.00 -40.00   0.50    0.05    --  -44.46 -26.00  44.00  166
 11  \w   -159.00 -95.00   0.50    0.06    -- -104.00 -26.00  44.00  128
 12  \w   -132.00 -97.00   0.50    0.06    -- -104.00 -15.00 -60.00   70
 13  \w   -128.00-100.00   0.50    0.06    -- -104.00 -15.00 -90.00   56
 14  \w   -123.00 -97.00   0.50    0.06    -- -104.00 -15.00-120.00   52
 15  \w     34.00  62.00   0.50    0.06    --  107.00 -77.00-180.00   56
 16  \w     42.00  68.00   0.50    0.06    --  107.00 -77.00 -90.00   52
 17  \w     41.00  67.00   0.50    0.06    --  107.00 -77.00 -60.00   52
 18  \w     33.00  88.00   0.50    0.06    --  107.00 -95.00   0.00  110
 19  \w     60.00  91.00   0.50    0.06    --  107.00-125.00 -30.00   62
 20  \w     34.00  61.00   0.50    0.06    --  107.00-100.00-133.00   54
 21  \w     69.00  94.00   0.50    0.06    --  107.00-100.00-133.00   50
;
_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      0.0566111000
_diffrn_orient_matrix_UB_12      -0.1055552000
_diffrn_orient_matrix_UB_13      0.0078108000
_diffrn_orient_matrix_UB_21      -0.0782546000
_diffrn_orient_matrix_UB_22      -0.0211244000
_diffrn_orient_matrix_UB_23      -0.0522399000
_diffrn_orient_matrix_UB_31      0.2638784000
_diffrn_orient_matrix_UB_32      0.0164226000
_diffrn_orient_matrix_UB_33      -0.0172484000
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.614
_diffrn_reflns_theta_min         3.186
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70665
_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    1.795
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate-Hexane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0420P)^2^+0.2980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4135
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00555k2.cif
_cod_data_source_block           sample3_auto
_cod_depositor_comments
;
Adding full bibliography for 7159303--7159304.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H18 Br2 Cl2 N2 O4'
_cod_original_formula_weight         581.08
_cod_original_formula_moiety         '2(C10 H9 Br Cl N O2)'
_cod_original_formula_units_Z            4
_cod_database_code               7159303
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H9BrClNO2
_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), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), N2(H2), C15(H15), C16(H16), C18(H18),
 C19(H19)
;
_shelx_res_checksum              17369
_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 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.733