Radical cascade cyclization of amino acid-tethered 1,6-enynones with sulfonyl hydrazides for N-terminal modification: synthesis of functionalized succinimide derivatives
Sivanantham, Mathiyazhagan; Jacob Stanley, Jenis; Muthu, Kesavan; Velmathi, Sivan; Senadi, Gopal Chandru; Ramasamy, Mohankumar; RSC Advances 15 (2025) 27486–27492; doi:10.1039/D5RA04754D

data_7250766
_publ_section_title
;
 Radical cascade cyclization of amino acid-tethered 1,6-enynones with
 sulfonyl hydrazides for N-terminal modification: synthesis of
 functionalized succinimide derivatives
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              27486
_journal_page_last               27492
_journal_paper_doi               10.1039/D5RA04754D
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C23 H22 I N O6 S'
_chemical_formula_sum            'C23 H22 I N O6 S'
_chemical_formula_weight         567.37
_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             2024-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-09 deposited with the CCDC.	2025-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.350(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0223(8)
_cell_length_b                   29.704(3)
_cell_length_c                   10.4353(11)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.46
_cell_volume                     2373.5(4)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            39644
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.157
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0700
_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^)+12.0771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3850
_reflns_number_total             5875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04754d2.cif
_cod_data_source_block           rmksmp2_413_060524_0m_a
_cod_database_code               7250766
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.779
_shelx_estimated_absorpt_t_min   0.684
_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. Uiso/Uaniso restraints and constraints
C15 \\sim C14: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
3. Others
 Sof(I1B)=1-FVAR(1)
 Sof(I1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
4.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              76192
_olex2_submission_special_instructions 'No special instructions were received'