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_7129826
_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_absolute_configuration ad
_chemical_formula_moiety         'C33 H27 N O2 S'
_chemical_formula_sum            'C33 H27 N O2 S'
_chemical_formula_weight         501.61
_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             2021-08-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-10-27 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                   12.0118(2)
_cell_length_b                   12.7811(2)
_cell_length_c                   16.9520(3)
_cell_measurement_reflns_used    5319
_cell_measurement_temperature    302.76(10)
_cell_measurement_theta_max      74.5700
_cell_measurement_theta_min      4.3160
_cell_volume                     2602.54(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.76(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 0.955
_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    -23.00  27.00   0.50    0.30    --   46.57 -26.00-131.00  100
  2  \w     32.00  61.00   0.50    1.00    --  104.25 -61.00  30.00   58
  3  \w     83.00 110.00   0.50    1.00    --  104.25-125.00 120.00   54
  4  \w     34.00  78.00   0.50    1.00    --  104.25-125.00 120.00   88
  5  \w    -38.00  21.00   0.50    0.30    --  -46.57  37.00  90.00  118
  6  \w   -106.00 -43.00   0.50    1.00    -- -102.00 113.00-124.00  126
  7  \w    -55.00 -29.00   0.50    1.00    -- -102.00  61.00 -60.00   52
  8  \w    -68.00 -43.00   0.50    1.00    -- -102.00  61.00  90.00   50
  9  \w   -167.00 -95.00   0.50    1.00    -- -102.00 -26.00-131.00  144
 10  \w   -107.00 -77.00   0.50    0.30    --  -46.57-125.00 -90.00   60
 11  \w   -175.00 -94.00   0.50    1.00    -- -102.00-103.00  44.00  162
 12  \w   -115.00 -78.00   0.50    0.30    --  -46.57-125.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282518000
_diffrn_orient_matrix_UB_12      -0.0115801000
_diffrn_orient_matrix_UB_13      -0.0882204000
_diffrn_orient_matrix_UB_21      0.0328503000
_diffrn_orient_matrix_UB_22      0.1150352000
_diffrn_orient_matrix_UB_23      -0.0139023000
_diffrn_orient_matrix_UB_31      0.1206921000
_diffrn_orient_matrix_UB_32      -0.0340734000
_diffrn_orient_matrix_UB_33      -0.0168936000
_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  0.0322
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9855
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.994
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.343
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (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    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(12)
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0510P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.592
_reflns_Friedel_fraction_full    0.811
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                4158
_reflns_number_total             4657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00457g2.cif
_cod_data_source_block           yangyq_0826-1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' 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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7129826
_shelx_shelxl_version_number     2018/1
_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:
 C7(H11), C12(H17), C16(H24)
2.b Secondary CH2 refined with riding coordinates:
 C25(H35,H36)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H20), C21(H32), C33(H45), C22(H34), C15(H23), C1(H28), C29(H42), C30(H44),
  C19(H31), C26(H38), C39(H48), C49(H54), C40(H50), C27(H41), C52(H58),
 C59(H62), C63(H65), C60(H64), C53(H61)
2.d Idealised Me refined as rotating group:
 C51(H55,H56,H57)
;
_shelx_res_checksum              50574
_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 7.420
_oxdiff_exptl_absorpt_empirical_full_min 0.563