Visible-light triggered Cu-catalyzed C–H bond activation to afford isocoumarin and isoquinolinone scaffolds at room temperature
Sau, Subham; Das, Krishna Mohan; Thakur, Arunabha; Chemical Communications 61 (2025) 8851–8854; doi:10.1039/D5CC01651G

data_7134538
_publ_section_title
;
 Visible-light triggered Cu-catalyzed C--H bond activation to afford
 isocoumarin and isoquinolinone scaffolds at room temperature
;
_journal_issue                   49
_journal_name_full               'Chemical Communications'
_journal_page_first              8851
_journal_page_last               8854
_journal_paper_doi               10.1039/D5CC01651G
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C2 H6 O S, C19 H11 N5 O3'
_chemical_formula_sum            'C21 H17 N5 O4 S'
_chemical_formula_weight         435.46
_chemical_name_systematic        Photon
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-20 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                94.493(3)
_cell_angle_beta                 102.417(2)
_cell_angle_gamma                97.971(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5805(6)
_cell_length_b                   8.7953(7)
_cell_length_c                   15.9373(12)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.35
_cell_volume                     1021.26(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            42990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_min         3.331
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1478 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.9092.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.573
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.573
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.1231
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3678
_refine_ls_wR_factor_ref         0.4441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             4498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01651g2.cif
_cod_data_source_block           at_ss_27_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134537--7134538.cif.'
_cod_database_code               7134538
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C19(H19), C27(H27), C20(H20), C21(H21), C25(H25), C26(H26)
1.b X=CH2 refined with riding coordinates:
 N14(H14A,H14B)
1.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              84569
_shelx_hkl_checksum              90062
_olex2_submission_special_instructions 'No special instructions were received'