Direct annulation between glycine derivatives and thiiranes through photoredox/iron cooperative catalysis
Wang, Shutao; Gao, Yuan; Hu, Yansong; Zhou, Jintao; Chen, Zhidang; Liu, Zhao; Zhang, Yuan; Chemical Communications  (2023) –; doi:10.1039/D3CC04580C

data_7132176
_publ_section_title
;
 Direct annulation between glycine derivatives and thiiranes through
 photoredox/iron cooperative catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04580C
_journal_year                    2023
_chemical_formula_moiety         'C19 H21 N O4 S'
_chemical_formula_sum            'C19 H0.25 N O4 S'
_chemical_formula_weight         338.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-22 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.4142(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.61353(9)
_cell_length_b                   27.3767(4)
_cell_length_c                   10.14913(14)
_cell_measurement_reflns_used    8272
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3100
_cell_measurement_theta_min      3.2410
_cell_volume                     1779.72(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_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     66.00  92.00   0.50    0.05    --   47.57 143.00 -20.00   52
  2  \w    106.00 168.00   0.50    0.07    --  107.75  37.00 -90.00  124
  3  \w     64.00 113.00   0.50    0.07    --  107.75 143.00 -20.00   98
  4  \w    104.00 134.00   0.50    0.07    --  107.75 126.00 170.00   60
  5  \w    -68.00 -28.00   0.50    0.07    -- -100.00  57.00-150.00   80
  6  \w   -103.00 -78.00   0.50    0.07    -- -100.00 143.00 -20.00   50
  7  \w   -112.00 -66.00   0.50    0.07    -- -100.00 126.00 170.00   92
  8  \w    -92.00 -56.00   0.50    0.05    --  -47.57 126.00 170.00   72
  9  \w    -27.00  23.00   0.50    0.05    --   47.57 -19.00  60.00  100
 10  \w    -14.00  12.00   0.50    0.05    --   47.57 -19.00 150.00   52
 11  \w    -27.00  21.00   0.50    0.05    --   47.57 -19.00-150.00   96
 12  \w    -27.00  10.00   0.50    0.05    --   47.57 -19.00-180.00   74
 13  \w     56.00  81.00   0.50    0.07    --  107.75-143.00 -75.00   50
 14  \w     56.00  84.00   0.50    0.05    --   47.57-126.00  93.00   56
 15  \w     84.00 109.00   0.50    0.07    --  107.75-126.00  93.00   50
 16  \w     47.00  98.00   0.50    0.07    --  107.75 -99.00  90.00  102
 17  \w     35.00  94.00   0.50    0.07    --  107.75 -77.00 120.00  118
 18  \w     47.00  90.00   0.50    0.07    --  107.75 -77.00  90.00   86
 19  \w     36.00  61.00   0.50    0.07    --  107.75 -57.00  60.00   50
 20  \w     35.00  63.00   0.50    0.07    --  107.75 -57.00 -90.00   56
 21  \w     37.00  62.00   0.50    0.07    --  107.75 -57.00-120.00   50
 22  \w     36.00  61.00   0.50    0.07    --  107.75 -57.00-150.00   50
 23  \w   -175.00-150.00   0.50    0.07    -- -100.00 -19.00 -30.00   50
 24  \w   -145.00 -89.00   0.50    0.07    -- -100.00 -19.00 -30.00  112
 25  \w   -112.00 -87.00   0.50    0.07    -- -100.00 -37.00   0.00   50
 26  \w   -119.00 -94.00   0.50    0.05    --  -47.57-143.00 -75.00   50
 27  \w   -145.00-120.00   0.50    0.07    -- -100.00-143.00 -75.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0542441000
_diffrn_orient_matrix_UB_12      0.0376568000
_diffrn_orient_matrix_UB_13      0.1163092000
_diffrn_orient_matrix_UB_21      0.0678783000
_diffrn_orient_matrix_UB_22      -0.0417038000
_diffrn_orient_matrix_UB_23      0.1034906000
_diffrn_orient_matrix_UB_31      0.2242473000
_diffrn_orient_matrix_UB_32      0.0034884000
_diffrn_orient_matrix_UB_33      -0.0175995000
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11436
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.587
_diffrn_reflns_theta_min         3.229
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             677
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0588P)^2^+0.6972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3261
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04580c2.cif
_cod_data_source_block           wangshut_0427_auto
_cod_original_cell_volume        1779.73(4)
_cod_database_code               7132176
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H00B), C11(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C12(H00A,H00C), C13(H00K,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H00D), C16(H00E), C18(H00F), C19(H00G), C5(H00H), C3(H00J), C7(H00M),
 C15(H00N), C17(H00R)
2.d Idealised Me refined as rotating group:
 C2(H00O,H00P,H00Q), C9(H00S,H00T,H00U)
;
_shelx_res_checksum              34661
_shelx_hkl_checksum              74944
_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 2.575
_oxdiff_exptl_absorpt_empirical_full_min 0.474