Catalytic asymmetric Michael/cyclization of 3 isothiocyanato thiobutyrolactone: an approach to the construction of a library of bispiro[pyrazolone-thiobutyrolactone] skeletons
Liu, Ren-Ming; Zhang, Min; Han, Xiao-Xue; Liu, Xiong-Li; Pan, Bo-Wen; Tian, You-Ping; Peng, Li-Jun; Yuan, Weicheng; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00773H

data_7158724
_publ_section_title
;
 Catalytic asymmetric Michael/cyclization of 3 isothiocyanato
 thiobutyrolactone: an approach to the construction of a library of
 bispiro[pyrazolone-thiobutyrolactone] skeletons
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00773H
_journal_year                    2022
_chemical_formula_moiety         'C22 H17 Cl2 N3 O2 S2'
_chemical_formula_sum            'C22 H17 Cl2 N3 O2 S2'
_chemical_formula_weight         490.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-04-04
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-04 deposited with the CCDC.	2022-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.790(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0271(6)
_cell_length_b                   10.9083(6)
_cell_length_c                   11.1404(8)
_cell_measurement_reflns_used    2584
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.2310
_cell_measurement_theta_min      2.6660
_cell_volume                     1055.60(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.852
_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    -59.00  37.00   1.00    1.00    --   11.90 -57.00 -60.00   96
  2  \w    -48.00  32.00   1.00    1.00    --   11.90 -57.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0345180000
_diffrn_orient_matrix_UB_12      -0.0281259000
_diffrn_orient_matrix_UB_13      -0.0431057000
_diffrn_orient_matrix_UB_21      -0.0470884000
_diffrn_orient_matrix_UB_22      0.0357605000
_diffrn_orient_matrix_UB_23      -0.0488508000
_diffrn_orient_matrix_UB_31      0.0570952000
_diffrn_orient_matrix_UB_32      0.0464564000
_diffrn_orient_matrix_UB_33      0.0115226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5127
_diffrn_reflns_point_group_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.665
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0290P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.459
_reflns_number_gt                3533
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00773h2.cif
_cod_data_source_block           153
_cod_database_code               7158724
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C17(H17), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              13128
_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 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.730