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_7064009
_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         'C56 H52 Br2 Cu2 N2 O4 P2, 2(C2 H3 N)'
_chemical_formula_sum            'C60 H58 Br2 Cu2 N4 O4 P2'
_chemical_formula_weight         1247.94
_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   geom
_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                73.938(2)
_cell_angle_beta                 74.5220(10)
_cell_angle_gamma                78.104(2)
_cell_formula_units_Z            1
_cell_length_a                   9.3433(4)
_cell_length_b                   11.4881(5)
_cell_length_c                   14.2465(6)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.45
_cell_volume                     1401.66(11)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0640
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            70887
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         2.113
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4846
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.6499.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+0.6810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6260
_reflns_number_total             7004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02820e2.cif
_cod_data_source_block           Compound_8
_cod_depositor_comments
'Adding full bibliography for 7064007--7064013.cif.'
_cod_database_code               7064009
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.309
_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), C19(H19), C15(H15), C2(H2), C9(H9), C25(H25), C5(H5), C21(H21),
 C4(H4), C17(H17), C10(H10), C12(H12), C3(H3), C16(H16), C18(H18), C11(H11),
 C24(H24), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              71609
_olex2_submission_special_instructions 'No special instructions were received'