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_7134537
_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         '0.174(C14 H8 N2 O3), 0.043(H4 O2)'
_chemical_formula_sum            'C2.43 H1.57 N0.35 O0.61'
_chemical_formula_weight         45.43
_chemical_name_systematic        Photon
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-27 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.816(2)
_cell_angle_gamma                90
_cell_formula_units_Z            46
_cell_length_a                   19.1986(12)
_cell_length_b                   7.3351(5)
_cell_length_c                   16.7240(10)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.45
_cell_volume                     2343.0(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.0656
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            50286
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         2.133
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1585 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.8790.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0582
_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^)+(0.1058P)^2^+1.5316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.2107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1837
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01651g2.cif
_cod_data_source_block           at_ss18_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134537--7134538.cif.'
_cod_database_code               7134537
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H00C(0.5) H00E(0.5)
3.a Free rotating group:
 O004(H00C,H00E)
3.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
3.c X=CH2 refined with riding coordinates:
 N005(H00A,H00B)
;
_shelx_res_checksum              18244
_shelx_hkl_checksum              55975
_olex2_submission_special_instructions 'No special instructions were received'