Regioselective conjugate addition of isoxazol-5-ones to ethenesulfonyl fluoride
Zhu, Dongyu; Chen, Yuan; Zhang, Xue-jing; Yan, Ming; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00737A

data_7158708
_publ_section_title
;
 Regioselective conjugate addition of isoxazol-5-ones to ethenesulfonyl
 fluoride
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00737A
_journal_year                    2022
_chemical_formula_moiety         'C18 H16 F N O4 S'
_chemical_formula_sum            'C18 H16 F N O4 S'
_chemical_formula_weight         361.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-12 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.857(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6101(6)
_cell_length_b                   13.2345(4)
_cell_length_c                   10.6349(5)
_cell_measurement_reflns_used    5492
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2640
_cell_measurement_theta_min      3.7150
_cell_volume                     1658.54(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    123.00 178.00   0.50    0.50    --  105.51  81.00 -94.00  110
  2  \w     89.00 135.00   0.50    0.50    --  105.51  61.00   0.00   92
  3  \w    -23.00  28.00   0.50    0.10    --   45.81 -19.00  60.00  102
  4  \w    -20.00  49.00   0.50    0.10    --   45.81 -81.00 143.00  138
  5  \w     37.00  63.00   0.50    0.50    --  105.51 -81.00 143.00   52
  6  \w     84.00 109.00   0.50    0.50    --  105.51 -81.00 143.00   50
  7  \w     41.00  66.00   0.50    0.50    --  105.51 -94.00  30.00   50
  8  \w     57.00 105.00   0.50    0.50    --  105.51 -94.00 -30.00   96
  9  \w     41.00  66.00   0.50    0.50    --  105.51 -61.00 -90.00   50
 10  \w     44.00  69.00   0.50    0.50    --  105.51 -61.00-180.00   50
 11  \w     32.00  67.00   0.50    0.50    --  105.51 -61.00 -60.00   70
 12  \w     40.00  73.00   0.50    0.50    --  105.51 -61.00  60.00   66
 13  \w     35.00  70.00   0.50    0.50    --  105.51 -61.00 150.00   70
 14  \w    -59.00 -34.00   0.50    0.50    -- -100.00  61.00 120.00   50
 15  \w    -69.00 -37.00   0.50    0.50    -- -100.00  61.00  90.00   64
 16  \w    -53.00 -27.00   0.50    0.50    -- -100.00  61.00 -30.00   52
 17  \w    -54.00 -28.00   0.50    0.50    -- -100.00  61.00-120.00   52
 18  \w   -173.00 -81.00   0.50    0.50    -- -100.00 -15.00-180.00  184
 19  \w   -100.00 -74.00   0.50    0.10    --  -45.81-125.00-150.00   52
 20  \w   -113.00 -74.00   0.50    0.10    --  -45.81-125.00 -60.00   78
 21  \w   -151.00 -98.00   0.50    0.50    -- -100.00 -81.00 143.00  106
 22  \w    -72.00  16.00   0.50    0.10    --  -45.81  81.00 -94.00  176
 23  \w   -124.00 -27.00   0.50    0.50    -- -100.00  81.00 -94.00  194
;
_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      0.0529065000
_diffrn_orient_matrix_UB_12      0.0920725000
_diffrn_orient_matrix_UB_13      -0.0439198000
_diffrn_orient_matrix_UB_21      -0.1195804000
_diffrn_orient_matrix_UB_22      0.0412657000
_diffrn_orient_matrix_UB_23      -0.0793241000
_diffrn_orient_matrix_UB_31      0.0005352000
_diffrn_orient_matrix_UB_32      0.0580971000
_diffrn_orient_matrix_UB_33      0.1257151000
_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  0.0658
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9675
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.025
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0804P)^2^+0.2799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00737a2.cif
_cod_data_source_block           zhudy_210928_auto
_cod_database_code               7158708
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOSF
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.629
_reflns_odcompleteness_completeness 98.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C12(H12A,H12B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C14(H14), C6(H6), C2(H2), C16(H16), C5(H5), C15(H15),
 C3(H3), C4(H4)
;
_shelx_res_checksum              35599
_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 2.228
_oxdiff_exptl_absorpt_empirical_full_min 0.362