Organocatalytic inverse-electron-demand Diels–Alder reaction between 5-alkenyl thiazolones and β,γ-unsaturated carbonyl compounds
Yang, Kai-Xuan; Ji, Dong-Sheng; Zheng, Haixue; Gu, Yucheng; Xu, Peng-Fei; Chemical Communications  (2022) –; doi:10.1039/D2CC00457G

data_7129825
_publ_section_title
;
 Organocatalytic inverse-electron-demand Diels--Alder reaction between
 5-alkenyl thiazolones and \b,\g-unsaturated carbonyl compounds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00457G
_journal_year                    2022
_chemical_formula_moiety         'C32 H25 N O2 S'
_chemical_formula_sum            'C32 H25 N O2 S'
_chemical_formula_weight         487.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.4821(10)
_cell_angle_beta                 90.1949(8)
_cell_angle_gamma                109.3327(13)
_cell_formula_units_Z            4
_cell_length_a                   9.37881(10)
_cell_length_b                   10.99282(19)
_cell_length_c                   26.0777(2)
_cell_measurement_reflns_used    51471
_cell_measurement_temperature    280.0(2)
_cell_measurement_theta_max      77.3330
_cell_measurement_theta_min      3.3860
_cell_volume                     2523.63(6)
_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      air
_diffrn_ambient_temperature      280.0(2)
_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 0.942
_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     33.00  68.00   0.50    0.05    --   56.00  78.00-165.14   70
  2  \w     45.00  79.00   0.50    0.05    --   68.00  78.00-142.74   68
  3  \w     29.00  54.00   0.50    0.05    --   52.00  78.00 -98.17   50
  4  \w     41.00  66.00   0.50    0.05    --   64.00  77.00 -42.00   50
  5  \w     30.00  59.00   0.50    0.05    --   52.00  76.00-119.54   58
  6  \w     42.00  68.00   0.50    0.05    --   64.00  77.00  24.32   52
  7  \w     34.00  89.00   0.50    0.05    --   56.00  76.00   6.99  110
  8  \w     42.00  71.00   0.50    0.05    --   64.00  75.00  54.54   58
  9  \w     82.00 108.00   0.50    0.05    --   64.00  72.00  20.22   52
 10  \w     45.00  73.00   0.50    0.05    --   68.00  78.00  71.06   56
 11  \w     46.00  72.00   0.50    0.05    --   68.00  75.00  96.42   52
 12  \w     33.00  58.00   0.50    0.05    --   56.00  77.00 120.93   50
 13  \w     41.00  66.00   0.50    0.05    --   64.00  77.00 161.84   50
 14  \w     43.00  68.00   0.50    0.05    --   64.00  72.00  20.22   50
 15  \w    102.00 131.00   0.50    0.05    --   60.00  71.00 -52.33   58
 16  \w     43.00  73.00   0.50    0.05    --   60.00  71.00 -52.33   60
 17  \w     -3.00  51.00   0.50    0.05    --   12.00  58.00 -59.28  108
 18  \w     73.00  98.00   0.50    0.05    --  107.75 -99.00-120.00   50
 19  \w     30.00  92.00   0.50    0.05    --   47.57-122.00-110.00  124
 20  \w     45.00 102.00   0.50    0.05    --   47.57-150.00  87.00  114
 21  \w     56.00 110.00   0.50    0.05    --  107.75-122.00-110.00  108
 22  \w     51.00 129.00   0.50    0.05    --  107.75-150.00  87.00  156
 23  \w     39.00 112.00   0.50    0.05    --  107.75-125.00 120.00  146
 24  \w     38.00 112.00   0.50    0.05    --  107.75-125.00  90.00  148
 25  \w     81.00 106.00   0.50    0.05    --  107.75 -99.00  90.00   50
 26  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00  90.00   50
 27  \w    102.00 135.00   0.50    0.05    --  107.75 122.00 -29.00   66
 28  \w     88.00 113.00   0.50    0.05    --  107.75 150.00 132.00   50
 29  \w     42.00 102.00   0.50    0.05    --  107.75 -77.00-120.00  120
 30  \w     36.00  62.00   0.50    0.05    --  107.75 -57.00 -60.00   52
 31  \w     35.00  72.00   0.50    0.05    --  107.75 -77.00  90.00   74
 32  \w    -25.00  24.00   0.50    0.05    --    4.00  91.00  60.67   98
 33  \w     -2.00  23.00   0.50    0.05    --   28.00  93.00  -4.65   50
 34  \w      4.00  33.00   0.50    0.05    --   28.00  92.00 130.21   58
 35  \w     75.00 100.00   0.50    0.05    --   47.57 150.00 132.00   50
 36  \w    -10.00  16.00   0.50    0.05    --   20.00  95.00 148.18   52
 37  \w    -96.00 -71.00   0.50    0.05    --  -47.57 150.00 132.00   50
 38  \w   -128.00 -90.00   0.50    0.05    -- -100.00 150.00 132.00   76
 39  \w    -98.00 -63.00   0.50    0.05    -- -100.00 122.00 -29.00   70
 40  \w   -109.00 -37.00   0.50    0.05    -- -100.00 125.00 -60.00  144
 41  \w    -57.00 -32.00   0.50    0.05    --  -47.57 122.00 -29.00   50
 42  \w    -66.00 -28.00   0.50    0.05    -- -100.00  57.00 -60.00   76
 43  \w    -69.00 -35.00   0.50    0.05    -- -100.00  57.00   0.00   68
 44  \w   -109.00 -27.00   0.50    0.05    -- -100.00  77.00-120.00  164
 45  \w    -92.00 -28.00   0.50    0.05    -- -100.00  77.00-180.00  128
 46  \w    -51.00 -25.00   0.50    0.05    --  -47.57 -77.00 -30.00   52
 47  \w    -59.00 -33.00   0.50    0.05    --  -56.00 -78.00-120.05   52
 48  \w   -117.00 -91.00   0.50    0.05    --  -56.00 -78.00-120.05   52
 49  \w   -124.00 -99.00   0.50    0.05    --  -88.00 -78.00-119.50   50
 50  \w    -95.00 -65.00   0.50    0.05    --  -88.00 -78.00-119.50   60
 51  \w   -101.00 -75.00   0.50    0.05    --  -47.57 -77.00 -30.00   52
 52  \w   -169.00-143.00   0.50    0.05    --  -96.00 -78.00 161.47   52
 53  \w   -157.00-131.00   0.50    0.05    --  -92.00 -77.00 123.65   52
 54  \w   -130.00 -69.00   0.50    0.05    --  -92.00 -77.00 123.65  122
 55  \w   -107.00 -73.00   0.50    0.05    --  -96.00 -78.00 161.47   68
 56  \w    -56.00 -28.00   0.50    0.05    --  -47.57 -77.00 120.00   56
 57  \w   -156.00 -69.00   0.50    0.05    --  -92.00 -76.00  87.27  174
 58  \w   -165.00 -80.00   0.50    0.05    -- -100.00 -77.00  30.00  170
 59  \w   -107.00 -70.00   0.50    0.05    --  -92.00 -75.00  39.41   74
 60  \w    -90.00 -65.00   0.50    0.05    --  -88.00 -76.00 -50.55   50
 61  \w    -81.00 -49.00   0.50    0.05    --  -72.00 -76.00 -68.35   64
 62  \w    -86.00 -61.00   0.50    0.05    --  -84.00 -76.00 -95.35   50
 63  \w   -121.00 -71.00   0.50    0.05    --  -92.00 -75.00 -90.99  100
 64  \w   -169.00 -77.00   0.50    0.05    -- -100.00 -77.00 -60.00  184
 65  \w    -92.00 -66.00   0.50    0.05    --  -88.00 -74.00  90.64   52
 66  \w    -80.00 -54.00   0.50    0.05    --  -76.00 -74.00  69.78   52
 67  \w    -83.00 -58.00   0.50    0.05    --  -80.00 -74.00 158.63   50
 68  \w    -95.00 -66.00   0.50    0.05    --  -88.00 -75.00 159.37   58
 69  \w   -158.00-108.00   0.50    0.05    --  -88.00 -75.00 159.37  100
 70  \w   -164.00 -70.00   0.50    0.05    --  -92.00 -74.00 130.15  188
 71  \w    -82.00 -55.00   0.50    0.05    --  -76.00 -73.00 165.75   54
 72  \w    -80.00 -55.00   0.50    0.05    --  -76.00 -73.00 118.78   50
 73  \w    -99.00 -67.00   0.50    0.05    --  -88.00 -72.00  48.18   64
 74  \w    -84.00 -59.00   0.50    0.05    --  -80.00 -73.00 -28.83   50
 75  \w    -96.00 -63.00   0.50    0.05    --  -84.00 -72.00 -38.35   66
 76  \w    -85.00 -59.00   0.50    0.05    --  -80.00 -73.00 -68.27   52
 77  \w    -85.00 -59.00   0.50    0.05    --  -80.00 -73.00-112.07   52
 78  \w    -87.00 -61.00   0.50    0.05    --  -80.00 -73.00-174.87   52
 79  \w    -82.00 -47.00   0.50    0.05    --  -68.00 -72.00-171.52   70
 80  \w    -74.00 -48.00   0.50    0.05    --  -68.00 -71.00-160.65   52
 81  \w    -81.00 -55.00   0.50    0.05    --  -76.00 -72.00-132.38   52
 82  \w    -79.00 -48.00   0.50    0.05    --  -68.00 -69.00 -48.53   62
 83  \w   -101.00 -76.00   0.50    0.05    --  -96.00 -69.00-101.23   50
 84  \w   -142.00-116.00   0.50    0.05    --  -96.00 -69.00-101.23   52
 85  \w    -95.00 -65.00   0.50    0.05    --  -84.00 -72.00  22.55   60
 86  \w    -74.00 -48.00   0.50    0.05    --  -68.00 -69.00  66.25   52
 87  \w    -86.00 -60.00   0.50    0.05    --  -80.00 -71.00  87.37   52
 88  \w    -85.00 -58.00   0.50    0.05    --  -76.00 -66.00 121.03   54
 89  \w    -87.00 -50.00   0.50    0.05    --  -68.00 -66.00  78.07   74
 90  \w   -145.00 -80.00   0.50    0.05    -- -100.00 -70.00  74.98  130
 91  \w   -157.00-132.00   0.50    0.05    --  -84.00 -65.00  -5.83   50
 92  \w   -155.00-129.00   0.50    0.05    --  -88.00 -66.00 -48.32   52
 93  \w   -173.00 -82.00   0.50    0.05    -- -100.00 -65.00 -25.86  182
 94  \w    -92.00 -66.00   0.50    0.05    --  -84.00 -65.00  -5.83   52
 95  \w    -80.00 -54.00   0.50    0.05    --  -72.00 -65.00   8.21   52
 96  \w   -100.00 -70.00   0.50    0.05    --  -88.00 -66.00 -48.32   60
 97  \w    -78.00 -52.00   0.50    0.05    --  -68.00 -65.00-108.27   52
 98  \w   -159.00 -70.00   0.50    0.05    --  -88.00 -64.00 -84.85  178
 99  \w   -152.00 -71.00   0.50    0.05    --  -88.00 -64.00-120.27  162
100  \w   -173.00-146.00   0.50    0.05    -- -100.00 -64.00  -0.11   54
101  \w   -170.00 -83.00   0.50    0.05    -- -100.00 -64.00   5.18  174
102  \w   -158.00 -78.00   0.50    0.05    --  -96.00 -64.00 169.90  160
103  \w   -143.00 -76.00   0.50    0.05    --  -92.00 -63.00 178.28  134
104  \w   -139.00 -86.00   0.50    0.05    -- -100.00 -64.00  -0.11  106
105  \w   -163.00 -75.00   0.50    0.05    --  -92.00 -61.00-153.49  176
106  \w   -153.00-119.00   0.50    0.05    --  -80.00 -62.00-167.73   68
107  \w   -101.00 -72.00   0.50    0.05    --  -88.00 -60.00-178.84   58
108  \w    -97.00 -63.00   0.50    0.05    --  -80.00 -62.00-167.73   68
109  \w   -119.00 -66.00   0.50    0.05    --  -47.57-150.00  87.00  106
110  \w    -40.00 -15.00   0.50    0.05    --  -40.00 -82.00 136.43   50
111  \w    -41.00 -16.00   0.50    0.05    --  -44.00 -90.00  63.06   50
112  \w    -40.00 -15.00   0.50    0.05    --  -44.00 -90.00 -83.71   50
113  \w   -138.00 -93.00   0.50    0.05    -- -100.00-122.00-110.00   90
114  \w   -122.00 -81.00   0.50    0.05    -- -100.00-150.00  87.00   82
;
_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      -0.0114590000
_diffrn_orient_matrix_UB_12      -0.1393866000
_diffrn_orient_matrix_UB_13      -0.0202071000
_diffrn_orient_matrix_UB_21      0.0207554000
_diffrn_orient_matrix_UB_22      -0.0297213000
_diffrn_orient_matrix_UB_23      0.0555445000
_diffrn_orient_matrix_UB_31      -0.1725758000
_diffrn_orient_matrix_UB_32      -0.0444894000
_diffrn_orient_matrix_UB_33      0.0057864000
_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  0.0955
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            82431
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.537
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49781
_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    1.283
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         10097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0578
_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^)+(0.1195P)^2^+0.2960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8699
_reflns_number_total             10097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00457g2.cif
_cod_data_source_block           yangkaixuan_0913-2_auto
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C64 H50 N2 O4 S2'
_cod_original_formula_weight         975.18
_cod_original_formula_moiety         '2(C32 H25 N O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7129825
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_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 Ternary CH refined with riding coordinates:
 C42(H42), C43(H43), C44(H44), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52), C53(H53), C55(H55), C56(H56), C57(H57), C58(H58),
  C60(H60), C61(H61), C62(H62), C63(H63), C64(H64), C2(H2), C3(H3), C4(H4),
 C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32)
;
_shelx_res_checksum              85829
_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 3.296
_oxdiff_exptl_absorpt_empirical_full_min 0.334