Cascade C-H functionalization/annulation of arylamides: access to succinimide-tethered isoquinoline-1,3-diones.
Maharana, Prabhat Kumar; Muthuraja, Perumal; Kar, Subhradeep; Veerappan, Tamilthendral; Punniyamurthy, Tharmalingam; Chemical communications (Cambridge, England) 61 (2025) 13449–13452; doi:10.1039/d5cc02963e

data_1575244
_publ_section_title
;
 Cascade C-H functionalization/annulation of arylamides: access to
 succinimide-tethered isoquinoline-1,3-diones.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13449
_journal_page_last               13452
_journal_paper_doi               10.1039/d5cc02963e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C38 H27 N5 O7), 3[C2H6SO]'
_chemical_formula_sum            'C82 H72 N10 O17 S3'
_chemical_formula_weight         1565.67
_chemical_name_systematic        PKM-545
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-11-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-02-05 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                79.425(3)
_cell_angle_beta                 72.534(3)
_cell_angle_gamma                64.120(3)
_cell_formula_units_Z            2
_cell_length_a                   15.0035(15)
_cell_length_b                   15.2445(15)
_cell_length_c                   19.376(2)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.24
_cell_volume                     3796.3(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            76100
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_min         1.487
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1673 before and 0.0852 after correction.
The Ratio of minimum to maximum transmission is 0.7504.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             1636
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     911
_refine_ls_number_reflns         13757
_refine_ls_number_restraints     865
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+3.8922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9344
_reflns_number_total             13757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02963e2.cif
_cod_data_source_block           pkm_545_0m_a
_cod_depositor_comments
'Adding full bibliography for 1575243--1575244.cif.'
_cod_database_code               1575244
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.976
_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
 N8-H8
 0.9 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C22(H22), C60(H60)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C25(H25A,H25B), C52(H52A,H52B), C63(H63A,H63B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35),
  C36(H36), C37(H37), C41(H41), C42(H42), C43(H43), C44(H44), C55(H55),
 C56(H56), C57(H57), C58(H58), C59(H59), C66(H66), C67(H67), C68(H68), C69(H69),
  C71(H71), C72(H72), C73(H73), C74(H74), C75(H75)
4.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C76(H76A,H76B,H76C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'