Enantioselective synthesis of 1,2-disubstituted thiocyclobutanes via Michael addition
Robert, Emma G. L.; Waser, Jerome; Chemical Science 16 (2025) 12115–12121; doi:10.1039/D5SC01727K

data_1574707
_publ_section_title
;
 Enantioselective synthesis of 1,2-disubstituted thiocyclobutanes via
 Michael addition
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              12115
_journal_page_last               12121
_journal_paper_doi               10.1039/D5SC01727K
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H17 N O5 S'
_chemical_formula_sum            'C16 H17 N O5 S'
_chemical_formula_weight         335.36
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-09 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.01559(8)
_cell_length_b                   9.23324(15)
_cell_length_c                   32.6513(5)
_cell_measurement_reflns_used    5601
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.5480
_cell_measurement_theta_min      2.6960
_cell_volume                     1512.09(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (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, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_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     69.00 116.00   0.50    1.50    --   77.93 143.00-169.00   94
  2  \w     73.00 107.00   0.50    1.50    --   77.93   0.00-180.00   68
  3  \w     47.00 116.00   0.50    1.50    --   77.93  15.00  60.00  138
  4  \w     44.00  69.00   0.50    1.50    --   69.57-143.00 135.00   50
  5  \w     53.00  78.00   0.50    1.50    --   77.93-143.00 135.00   50
  6  \w     42.00  75.00   0.50    1.50    --   69.57 -95.00 120.00   66
  7  \w     34.00  76.00   0.50    1.50    --   69.57 -95.00 -30.00   84
  8  \w     49.00  84.00   0.50    1.50    --   77.93 -95.00 -60.00   70
  9  \w     50.00  78.00   0.50    1.50    --   69.57-127.00 -54.00   56
 10  \w     29.00  73.00   0.50    1.50    --   66.04 -95.00-150.00   88
 11  \w     54.00  86.00   0.50    1.50    --   77.93 -95.00-180.00   64
 12  \w     36.00  73.00   0.50    1.50    --   77.93-127.00 -54.00   74
 13  \w     60.00  85.00   0.50    1.50    --   77.93 -95.00 120.00   50
 14  \w    -95.00 -31.00   0.50    1.50    --  -69.34 125.00 150.00  128
 15  \w    -80.00 -55.00   0.50    1.50    --  -66.76 127.00  20.00   50
 16  \w    -92.00 -28.00   0.50    1.50    --  -66.76 125.00 -30.00  128
 17  \w    -61.00 -35.00   0.50    1.50    --  -66.76 143.00-169.00   52
 18  \w    -71.00 -32.00   0.50    1.50    --  -66.76   0.00 -90.00   78
 19  \w   -110.00 -84.00   0.50    1.50    --  -69.34 -15.00 -60.00   52
 20  \w    -58.00 -33.00   0.50    1.50    --  -69.34   0.00 -60.00   50
 21  \w    -63.00 -38.00   0.50    1.50    --  -69.34 -15.00 -60.00   50
 22  \w    -61.00 -33.00   0.50    1.50    --  -69.34   0.00 120.00   56
 23  \w   -100.00 -75.00   0.50    1.50    --  -69.34-143.00 135.00   50
 24  \w   -106.00 -72.00   0.50    1.50    --  -66.76-143.00 135.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0768175000
_diffrn_orient_matrix_UB_12      0.1593918000
_diffrn_orient_matrix_UB_13      -0.0074513000
_diffrn_orient_matrix_UB_21      -0.2120703000
_diffrn_orient_matrix_UB_22      -0.0484992000
_diffrn_orient_matrix_UB_23      -0.0312556000
_diffrn_orient_matrix_UB_31      -0.2083882000
_diffrn_orient_matrix_UB_32      -0.0093899000
_diffrn_orient_matrix_UB_33      0.0345569000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            11468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.638
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.146
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(12)
_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     209
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0502P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                2629
_reflns_number_total             2947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01727k2.cif
_cod_data_source_block           egr-07-242
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 

 Adding full bibliography for 1574706--1574707.cif.
;
_cod_database_code               1574707
_shelx_shelxl_version_number     2019/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C16 H17 N O5 S'
_chemical_oxdiff_usercomment     'TOLUENE, DCM, CDCl3'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.830
_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:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              35818
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.814