Synthesis of 3-sulfonylisoindolin-1-ones from olefinic amides and sodium sulfinates <i>via</i> electrooxidative tandem cyclization.
Wang, Xuecheng; Zhao, Ziyue; Guo, Jiajie; Wang, Jijin; Zhao, Jincan; Organic & biomolecular chemistry 22 (2024) 5897–5901; doi:10.1039/d4ob00980k

data_7160015
_publ_section_title
;
 Synthesis of 3-sulfonylisoindolin-1-ones from olefinic amides and sodium
 sulfinates <i>via</i> electrooxidative tandem cyclization.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5897
_journal_page_last               5901
_journal_paper_doi               10.1039/d4ob00980k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H24 F3 N O3 S, C H Cl3'
_chemical_formula_sum            'C31 H25 Cl3 F3 N O3 S'
_chemical_formula_weight         654.93
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2024-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.020(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.756(7)
_cell_length_b                   13.906(7)
_cell_length_c                   15.357(8)
_cell_measurement_reflns_used    6488
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      21.902
_cell_measurement_theta_min      2.316
_cell_volume                     3120(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      299.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42473
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.111
_diffrn_reflns_theta_min         1.984
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         7344
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0949
_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^)+(0.1235P)^2^+3.5366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2367
_refine_ls_wR_factor_ref         0.2895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3791
_reflns_number_total             7344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00980k2.cif
_cod_data_source_block           3ta
_cod_depositor_comments          'Adding full bibliography for 7160015.cif.'
_cod_database_code               7160015
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.808
_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. Restrained distances
 Cl1B-Cl3B
 3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1B) = Uanis(Cl1A) = Uanis(Cl3A) = Uanis(Cl3B) = Uanis(Cl2A) =
Uanis(Cl2B)
4. Others
 Sof(F2B)=Sof(F3B)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(H31A)=Sof(Cl3B)=Sof(Cl2B)=Sof(Cl1B)=1-FVAR(2)
 Sof(Cl1A)=Sof(Cl3A)=Sof(Cl2A)=Sof(H31)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C31(H31A), C31(H31)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C13(H13), C16(H16), C26(H26), C25(H25), C4(H4), C18(H18), C29(H29),
 C14(H14), C19(H19), C15(H15), C6(H6), C21(H21), C3(H3), C28(H28), C7(H7)
5.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              74271
_olex2_submission_special_instructions 'No special instructions were received'