Iodo-Sulphonylation of 1,6-Enynones: A Metal-Free Strategy to Synthesize N-Substituted Succinimides
Sivanantham, Mathiyazhagan; Jennifer G, Abigail; Varathan, E.; Ramasamy, Mohankumar; Senadi, Gopal Chandru; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01277D

data_7158892
_publ_section_title
;
 Iodo-Sulphonylation of 1,6-Enynones: A Metal-Free Strategy to Synthesize
 N-Substituted Succinimides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01277D
_journal_year                    2022
_chemical_formula_moiety         'C26 H22 I N O4 S'
_chemical_formula_sum            'C26 H22 I N O4 S'
_chemical_formula_weight         571.40
_chemical_name_common            Organic
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-17 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.6510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8903(6)
_cell_length_b                   15.0921(7)
_cell_length_c                   14.6135(7)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.9230
_cell_measurement_theta_min      3.1496
_cell_volume                     2402.1(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Quest XRD'
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39026
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.075
_diffrn_reflns_theta_min         2.306
_exptl_absorpt_coefficient_mu    1.453
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6020
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0277P)^2^+1.7031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5438
_reflns_number_total             6983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01277d2.cif
_cod_data_source_block           SRM_RMK_SM_232_21032022_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158892
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.644
_shelx_estimated_absorpt_t_max   0.716
_shelx_res_checksum              32344