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_7064007
_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         'C27 H24 N O2 P'
_chemical_formula_sum            'C27 H24 N O2 P'
_chemical_formula_weight         425.44
_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                87.939(3)
_cell_angle_beta                 80.976(3)
_cell_angle_gamma                67.318(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6288(8)
_cell_length_b                   10.9399(10)
_cell_length_c                   11.7383(9)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.42
_cell_volume                     1126.33(17)
_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  0.0618
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            52855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.757
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5599
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1361 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.7508. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.039
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0339P)^2^+0.7246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3635
_reflns_number_total             3973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02820e2.cif
_cod_data_source_block           compound_L2
_cod_depositor_comments
'Adding full bibliography for 7064007--7064013.cif.'
_cod_database_code               7064007
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.911
_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 Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C25(H25), C9(H9), C15(H15), C5(H5), C3(H3), C23(H23),
 C21(H21), C4(H4), C24(H24), C10(H10), C19(H19), C12(H12), C16(H16), C11(H11),
 C22(H22), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              43703
_olex2_submission_special_instructions 'No special instructions were received'