Copper nanoparticle-catalyzed synthesis of N-arylated indoles, carbazoles, and N-alkylated indoles
Pandey, Ankit; Kaur, Bhupinder; Dwivedi, Khilesh C.; Balakrishna, Maravanji S.; New Journal of Chemistry 49 (2025) 17936–17950; doi:10.1039/D5NJ02820E

data_7064008
_publ_section_title
;
 Copper nanoparticle-catalyzed synthesis of N-arylated indoles,
 carbazoles, and N-alkylated indoles
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17936
_journal_page_last               17950
_journal_paper_doi               10.1039/D5NJ02820E
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C28 H26 N O2 P'
_chemical_formula_sum            'C28 H26 N O2 P'
_chemical_formula_weight         439.47
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-02-17 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.001(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9961(16)
_cell_length_b                   16.8436(16)
_cell_length_c                   9.6647(9)
_cell_measurement_reflns_used    9788
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.49
_cell_volume                     2358.0(4)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0776
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            153066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.854
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1609 before and 0.0824 after correction. The Ratio of minimum to maximum transmission is 0.6560. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0289P)^2^+1.6280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3691
_reflns_number_total             4157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02820e2.cif
_cod_data_source_block           Compound_L3
_cod_depositor_comments
'Adding full bibliography for 7064007--7064013.cif.'
_cod_database_code               7064008
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C2(H2), C5(H5), C4(H4), C19(H19), C3(H3), C21(H21), C15(H15),
 C10(H10), C25(H25), C12(H12), C17(H17), C16(H16), C11(H11), C24(H24), C18(H18),
  C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C27(H27a,H27b,H27c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              9756
_olex2_submission_special_instructions 'No special instructions were received'