Isothiourea catalysed enantioselective generation of point and axially chiral iminothia- and iminoselenazinanones
Nimmo, Alastair J.; Goodfellow, Alister S.; Guntley, Jacob T.; McKay, Aidan P.; Cordes, David B.; Bühl, Michael; Smith, Andrew D.; Chemical Science 16 (2025) 10494–10502; doi:10.1039/D5SC02435H

data_1575030
_publ_section_title
;
 Isothiourea catalysed enantioselective generation of point and axially
 chiral iminothia- and iminoselenazinanones
;
_journal_issue                   23
_journal_name_full               'Chemical Science'
_journal_page_first              10494
_journal_page_last               10502
_journal_paper_doi               10.1039/D5SC02435H
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 F3 N2 O3 S2'
_chemical_formula_sum            'C21 H21 F3 N2 O3 S2'
_chemical_formula_weight         470.52
_chemical_name_systematic
(R,Z)-N-(3-(2-isopropylphenyl)-4-oxo-6-(trifluoromethyl)-1,3-thiazinan-2-ylidene)-4-methylbenzenesulfonamide
_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             2024-08-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-17 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.07483(6)
_cell_length_b                   15.56758(15)
_cell_length_c                   17.59729(15)
_cell_measurement_reflns_used    25525
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.1030
_cell_measurement_theta_min      3.7570
_cell_volume                     2212.08(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 42.94a (release 21-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.109a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -89.00  89.00   0.50    0.50    --    0.00  28.00 -60.00  356
  2  \w    -84.00  94.00   0.50    0.50    --    5.00  18.00 120.00  356
  3  \w   -185.00  -8.00   0.50    4.00    --  -96.50  37.00-150.00  354
  4  \w   -185.00  -8.00   0.50    4.00    --  -96.50   0.00  90.00  354
  5  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 -90.00  354
  6  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00  90.00  354
  7  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-150.00  354
  8  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 120.00  354
  9  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-180.00  354
 10  \w   -185.00  -8.00   0.50    4.00    --  -96.50   0.00  90.00  354
 11  \w   -185.00  -8.00   0.50    4.00    --  -96.50   9.00 -60.00  354
 12  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00 150.00  354
 13  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00-120.00  354
 14  \w   -185.00  -8.00   0.50    4.00    --  -96.50  46.00  60.00  354
;
_diffrn_measurement_device       'AFC11: Quarter \c 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0845322000
_diffrn_orient_matrix_UB_12      -0.0276044000
_diffrn_orient_matrix_UB_13      0.0746085000
_diffrn_orient_matrix_UB_21      0.1158957000
_diffrn_orient_matrix_UB_22      -0.0784095000
_diffrn_orient_matrix_UB_23      0.0050171000
_diffrn_orient_matrix_UB_31      0.1257238000
_diffrn_orient_matrix_UB_32      0.0537066000
_diffrn_orient_matrix_UB_33      0.0455487000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43774
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.584
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.109a (Rigaku Oxford Diffraction, 2024)
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    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane into ethyl acetate'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0708P)^2^+0.5635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4432
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02435h2.cif
_cod_data_source_block           65
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1575030
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.352
_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:
 C20(H20), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C17(H17), C18(H18), C12(H12), C8(H8), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              65632