Benzotetramisole catalyzed kinetic resolution of 2H-azirines.
Peng, Qiupeng; Guo, Donghui; Zhang, Bei; Liu, Lala; Wang, Jian; Chemical communications (Cambridge, England) 56 (2020) 12427–12430; doi:10.1039/d0cc05379a

data_7127204
_publ_section_title
;
 Benzotetramisole catalyzed kinetic resolution of 2H-azirines.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12427
_journal_page_last               12430
_journal_paper_doi               10.1039/d0cc05379a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H8 Cl F N2 O4'
_chemical_formula_sum            'C15 H8 Cl F N2 O4'
_chemical_formula_weight         334.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-29
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.614(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.32650(10)
_cell_length_b                   13.4831(2)
_cell_length_c                   12.3293(3)
_cell_measurement_reflns_used    5923
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.6720
_cell_measurement_theta_min      4.8560
_cell_volume                     717.79(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -92.00  -4.00   1.00    1.00    --  -40.81 125.00  30.00   88
  2  \w    -48.00  29.00   1.00    1.00    --  -40.81  38.00-150.00   77
  3  \w    -64.00  33.00   1.00    1.00    --  -40.81  38.00 -60.00   97
  4  \w   -106.00 -67.00   1.00    1.00    --  -40.81 -77.00-150.00   39
  5  \w   -108.00 -81.00   1.00    1.00    --  -40.81 -57.00 -60.00   27
  6  \w   -106.00 -55.00   1.00    1.00    --  -40.81-152.00-132.00   51
  7  \w    -40.00 -13.00   1.00    1.00    --  -40.81 -57.00 -60.00   27
  8  \w      8.00  85.00   1.00    1.00    --   40.81  77.00 150.00   77
  9  \w     11.00  94.00   1.00    1.00    --   40.81  77.00-120.00   83
 10  \w     14.00  75.00   1.00    1.00    --   40.81  57.00  90.00   61
 11  \w      8.00  87.00   1.00    1.00    --   40.81  77.00 -30.00   79
 12  \w     75.00 102.00   1.00    1.00    --  107.77  77.00  60.00   27
 13  \w     33.00 140.00   1.00    1.00    --  107.77 -77.00-180.00  107
 14  \w     79.00 108.00   1.00    1.00    --  107.77  61.00-150.00   29
 15  \w    136.00 164.00   1.00    1.00    --  107.77  77.00  30.00   28
 16  \w     75.00 102.00   1.00    1.00    --  107.77  77.00 -30.00   27
 17  \w     76.00 101.00   1.00    1.00    --  107.77  77.00  30.00   25
 18  \w     42.00 110.00   1.00    1.00    --  107.77 -95.00  90.00   68
 19  \w     75.00 123.00   1.00    1.00    --  107.77  77.00 150.00   48
 20  \w    129.00 177.00   1.00    1.00    --  107.77  77.00 -90.00   48
 21  \w     75.00 101.00   1.00    1.00    --  107.77  77.00 -60.00   26
 22  \w    133.00 159.00   1.00    1.00    --  107.77  77.00 150.00   26
 23  \w     81.00 161.00   1.00    1.00    --  107.77  61.00 -30.00   80
 24  \w     75.00 101.00   1.00    1.00    --  107.77  77.00   0.00   26
 25  \w     77.00 103.00   1.00    1.00    --  107.77  77.00-120.00   26
 26  \w    115.00 170.00   1.00    1.00    --  107.77  77.00-120.00   55
 27  \w     75.00 101.00   1.00    1.00    --  107.77  77.00 -90.00   26
 28  \w     75.00 101.00   1.00    1.00    --  107.77  77.00-180.00   26
 29  \w     75.00 149.00   1.00    1.00    --  107.77  77.00-150.00   74
 30  \w     79.00 110.00   1.00    1.00    --  107.77  61.00 -90.00   31
 31  \w     75.00 102.00   1.00    1.00    --  107.77  77.00  90.00   27
 32  \w     79.00 105.00   1.00    1.00    --  107.77  61.00  30.00   26
 33  \w     80.00 177.00   1.00    1.00    --  107.77  61.00   0.00   97
 34  \w    144.00 169.00   1.00    1.00    --  107.77  61.00 -60.00   25
 35  \w     84.00 122.00   1.00    1.00    --  107.77  61.00 -60.00   38
 36  \w     88.00 115.00   1.00    1.00    --  107.77-125.00  60.00   27
 37  \w     81.00 170.00   1.00    1.00    --  107.77  61.00  60.00   89
 38  \w     79.00 106.00   1.00    1.00    --  107.77  61.00 120.00   27
 39  \w     79.00 168.00   1.00    1.00    --  107.77  61.00  90.00   89
 40  \w     75.00 177.00   1.00    1.00    --  107.77  77.00 120.00  102
 41  \w     78.00 118.00   1.00    1.00    --  107.77-125.00 -60.00   40
 42  \w     79.00 106.00   1.00    1.00    --  107.77  61.00-120.00   27
 43  \w     40.00 134.00   1.00    1.00    --  107.77 -61.00 -60.00   94
 44  \w     81.00 164.00   1.00    1.00    --  107.77  61.00-180.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0394337000
_diffrn_orient_matrix_UB_12      -0.0411807000
_diffrn_orient_matrix_UB_13      -0.1166036000
_diffrn_orient_matrix_UB_21      -0.0248849000
_diffrn_orient_matrix_UB_22      -0.1059349000
_diffrn_orient_matrix_UB_23      0.0455624000
_diffrn_orient_matrix_UB_31      -0.3536281000
_diffrn_orient_matrix_UB_32      0.0120156000
_diffrn_orient_matrix_UB_33      0.0017828000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.921
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0489P)^2^+0.2497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2794
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05379a2.cif
_cod_data_source_block           20191128pengqiupeng
_cod_depositor_comments          'Adding full bibliography for 7127204.cif.'
_cod_database_code               7127204
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N)
;
_shelx_res_checksum              54834
_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.693