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_7132175
_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         'C18 H18 I N O2 S'
_chemical_formula_sum            'C18 H18 I N O2 S'
_chemical_formula_weight         439.29
_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             2022-04-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-07-22 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1858(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.96313(11)
_cell_length_b                   6.06546(8)
_cell_length_c                   32.0458(3)
_cell_measurement_reflns_used    9044
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.2750
_cell_measurement_theta_min      2.7510
_cell_volume                     1741.81(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.927
_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    -24.00  37.00   0.50    0.05    --   47.57 -37.00-120.00  122
  2  \w    108.00 170.00   0.50    0.05    --  107.75 105.00  90.00  124
  3  \w    -27.00  23.00   0.50    0.05    --   47.57 -19.00   0.00  100
  4  \w    -24.00   1.00   0.50    0.05    --   47.57 -19.00 -30.00   50
  5  \w    -27.00  20.00   0.50    0.05    --   47.57 -19.00 -60.00   94
  6  \w      0.00  26.00   0.50    0.05    --   47.57-105.00 -10.00   52
  7  \w     69.00 100.00   0.50    0.05    --  107.75-105.00 -10.00   62
  8  \w   -101.00 -70.00   0.50    0.05    -- -100.00  77.00  90.00   62
  9  \w    -52.00 -27.00   0.50    0.05    -- -100.00  77.00  90.00   50
 10  \w    -68.00 -28.00   0.50    0.05    -- -100.00  57.00  60.00   80
 11  \w    -66.00 -27.00   0.50    0.05    -- -100.00  57.00  90.00   78
 12  \w    -69.00 -43.00   0.50    0.05    -- -100.00  57.00  30.00   52
 13  \w    -68.00 -29.00   0.50    0.05    -- -100.00  57.00 -60.00   78
 14  \w    -69.00 -27.00   0.50    0.05    -- -100.00  57.00 -90.00   84
 15  \w   -121.00 -87.00   0.50    0.05    -- -100.00 -37.00-180.00   68
 16  \w   -107.00 -56.00   0.50    0.05    -- -100.00 105.00  90.00  102
 17  \w    -78.00  -6.00   0.50    0.05    --  -47.57 105.00  90.00  144
 18  \w   -159.00-134.00   0.50    0.05    -- -100.00 -37.00-180.00   50
 19  \w   -156.00 -95.00   0.50    0.05    -- -100.00-105.00 -10.00  122
 20  \w     36.00  61.00   0.50    0.05    --  107.75 -57.00 150.00   50
 21  \w     46.00  71.00   0.50    0.05    --  107.75 -77.00  30.00   50
 22  \w     38.00  63.00   0.50    0.05    --  107.75 -57.00  30.00   50
 23  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 120.00   50
 24  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00   0.00   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      -0.1003301000
_diffrn_orient_matrix_UB_12      -0.1878579000
_diffrn_orient_matrix_UB_13      0.0154933000
_diffrn_orient_matrix_UB_21      0.1350224000
_diffrn_orient_matrix_UB_22      -0.1572929000
_diffrn_orient_matrix_UB_23      0.0008244000
_diffrn_orient_matrix_UB_31      0.0355400000
_diffrn_orient_matrix_UB_32      0.0668216000
_diffrn_orient_matrix_UB_33      0.0455133000
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10301
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.474
_diffrn_reflns_theta_min         2.758
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32469
_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    1.675
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.118
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0896P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3296
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04580c2.cif
_cod_data_source_block           wangsht_0412-4_auto
_cod_database_code               7132175
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.407
_shelx_estimated_absorpt_t_min   0.256
_reflns_odcompleteness_completeness 99.24
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              23324
_shelx_hkl_checksum              30418
_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 3.116
_oxdiff_exptl_absorpt_empirical_full_min 0.414