A Brønsted acid-catalyzed thioacid addition to in situ generated aldimine for the synthesis of isoindolinones with N,S-acetal framework
Sadhu, Milon Mohan; Khajuria, Chhavi; Singh, Vinod K.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01532C

data_7158954
_publ_section_title
;
 A Br\/onsted acid-catalyzed thioacid addition to in situ generated
 aldimine for the synthesis of isoindolinones with N,S-acetal framework
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01532C
_journal_year                    2022
_chemical_formula_moiety         'C17 H15 N O3 S'
_chemical_formula_sum            'C17 H15 N O3 S'
_chemical_formula_weight         313.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-08-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-22 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.498(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1813(4)
_cell_length_b                   17.3871(7)
_cell_length_c                   8.5577(4)
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      3.12
_cell_volume                     1473.07(11)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30371
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         2.343
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1296 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9117.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0386P)^2^+0.6065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             3733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01532c2.cif
_cod_data_source_block           f1_a
_cod_depositor_comments
;

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H30 N2 O6 S2'
_cod_original_formula_weight         626.72
_cod_original_formula_moiety         '2(C17 H15 N O3 S)'
_cod_original_formula_units_Z            2
_cod_database_code               7158954
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00K(H00A,H00F,H00K), C00M(H00M,H00N,H00O)
;
_shelx_res_checksum              18437
_olex2_submission_special_instructions 'No special instructions were received'