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_7129827
_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      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             2021-09-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2022-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9830(2)
_cell_length_b                   13.0537(3)
_cell_length_c                   16.2653(3)
_cell_measurement_reflns_used    7620
_cell_measurement_temperature    298.07(14)
_cell_measurement_theta_max      77.3460
_cell_measurement_theta_min      4.5640
_cell_volume                     2544.26(9)
_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      air
_diffrn_ambient_temperature      298.07(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.965
_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     82.00 175.00   0.50    0.79    --  107.75  83.00  94.00  186
  2  \w    109.00 165.00   0.50    0.79    --  107.75  37.00   0.00  112
  3  \w    -22.00  11.00   0.50    0.20    --   47.57 -19.00 -90.00   66
  4  \w    -25.00   1.00   0.50    0.20    --   47.57 -19.00-150.00   52
  5  \w    -26.00  13.00   0.50    0.20    --   47.57 -19.00-120.00   78
  6  \w     -3.00  22.00   0.50    0.20    --   47.57 -19.00   0.00   50
  7  \w     38.00  63.00   0.50    0.79    --  107.75 -57.00  30.00   50
  8  \w     45.00  99.00   0.50    0.79    --  107.75 -77.00 120.00  108
  9  \w     35.00  63.00   0.50    0.79    --  107.75 -57.00 120.00   56
 10  \w     35.00  60.00   0.50    0.79    --  107.75 -57.00   0.00   50
 11  \w     36.00  99.00   0.50    0.79    --  107.75 -77.00-180.00  126
 12  \w     36.00 111.00   0.50    0.79    --  107.75-125.00  87.00  150
 13  \w     47.00  91.00   0.50    0.79    --  107.75 -99.00  90.00   88
 14  \w    -45.00  24.00   0.50    0.20    --  -47.57  39.00 -59.00  138
 15  \w    -16.00  16.00   0.50    0.20    --  -47.57  19.00 -90.00   64
 16  \w    -69.00 -32.00   0.50    0.79    -- -100.00  57.00 -60.00   74
 17  \w    -69.00 -44.00   0.50    0.79    -- -100.00  57.00 -30.00   50
 18  \w    -33.00 -27.00   0.50    0.79    -- -100.00  57.00  30.00   12
;
_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      -0.0925014000
_diffrn_orient_matrix_UB_12      -0.0700906000
_diffrn_orient_matrix_UB_13      -0.0342284000
_diffrn_orient_matrix_UB_21      -0.0632375000
_diffrn_orient_matrix_UB_22      0.0946877000
_diffrn_orient_matrix_UB_23      -0.0319608000
_diffrn_orient_matrix_UB_31      0.0629906000
_diffrn_orient_matrix_UB_32      -0.0077208000
_diffrn_orient_matrix_UB_33      -0.0823059000
_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  0.0393
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12576
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.584
_diffrn_reflns_theta_min         4.583
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43642
_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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                4304
_reflns_number_total             5047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00457g2.cif
_cod_data_source_block           yangkx_0910_auto
_cod_original_cell_volume        2544.27(8)
_cod_database_code               7129827
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 99.19
_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:
 C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31)
;
_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 2.343
_oxdiff_exptl_absorpt_empirical_full_min 0.610