Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes.
Guin, Avishek; Deswal, Shiksha; Harariya, Mahesh Singh; Biju, Akkattu T.; Chemical science 15 (2024) 12473–12479; doi:10.1039/d4sc02194k

data_1572044
_publ_section_title
;
 Lewis acid-catalyzed diastereoselective formal ene reaction of
 thioindolinones/thiolactams with bicyclobutanes.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              12473
_journal_page_last               12479
_journal_paper_doi               10.1039/d4sc02194k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.478
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_block_doi                 10.5517/ccdc.csd.cc2jd83b
_audit_creation_date             2024-02-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-02-26 deposited with the CCDC.	2024-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                84.098(2)
_cell_angle_beta                 80.590(2)
_cell_angle_gamma                65.900(1)
_cell_formula_units_Z            2
_cell_length_a                   8.8830(5)
_cell_length_b                   10.7359(6)
_cell_length_c                   10.9008(6)
_cell_measurement_reflns_used    8988
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.59
_cell_measurement_theta_min      2.53
_cell_volume                     935.44(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9940
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26876
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9940
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.62
_diffrn_reflns_theta_min         1.90
_diffrn_source_current           75.0
_diffrn_source_power             3.375
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0504 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.9436.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             408.437
_refine_diff_density_max         0.4532
_refine_diff_density_min         -0.4963
_refine_diff_density_rms         0.0666
_refine_ls_d_res_high            0.6777
_refine_ls_d_res_low             10.7455
_refine_ls_goodness_of_fit_ref   1.0445
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0445
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.0063
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.2624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                5072
_reflns_number_total             6247
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4sc02194k2.cif
_cod_data_source_block           Ag_AC_SO2_120K_0m_a
_cod_depositor_comments          'Adding full bibliography for 1572044.cif.'
_cod_database_code               1572044
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b)
1.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'