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_1575243
_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         'C35 H24 N4 O7, C2 H3 N'
_chemical_formula_sum            'C37 H27 N5 O7'
_chemical_formula_weight         653.63
_chemical_name_systematic        PM-26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-10-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-05 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0923(14)
_cell_length_b                   11.9690(14)
_cell_length_c                   21.896(3)
_cell_measurement_reflns_used    9280
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.39
_cell_volume                     3169.1(7)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68865
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.041
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_min         2.394
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.0155(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         5580
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0313P)^2^+0.9553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4923
_reflns_number_total             5580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02963e2.cif
_cod_data_source_block           tp_pm_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1575243--1575244.cif.'
_cod_original_cell_volume        3169.0(6)
_cod_database_code               1575243
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B), C00Y(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00F(H00F), C00H(H00H), C00Q(H00Q), C00T(H00T), C00V(H00V),
 C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C017(H017), C018(H018), C019(H019), C01A(H01A), C01C(H01C),
 C01D(H01D)
2.d Idealised Me refined as rotating group:
 C01B(H01B,H01E,H01F)
;
_shelx_res_checksum              25818
_shelx_hkl_checksum              60489
_olex2_submission_special_instructions 'No special instructions were received'