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_7064011
_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         'C54 H48 Br2 Cu2 N2 O4 P2'
_chemical_formula_sum            'C54 H48 Br2 Cu2 N2 O4 P2'
_chemical_formula_weight         1137.78
_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
_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                110.624(6)
_cell_angle_beta                 109.704(9)
_cell_angle_gamma                92.648(7)
_cell_formula_units_Z            1
_cell_length_a                   11.1119(19)
_cell_length_b                   11.501(2)
_cell_length_c                   11.673(2)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.66
_cell_volume                     1291.2(4)
_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      150.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            74286
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         1.926
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3560
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1400 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.4774.
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    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6435
_refine_ls_number_restraints     159
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0320P)^2^+0.9266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5943
_reflns_number_total             6435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02820e2.cif
_cod_data_source_block           Compound_5
_cod_depositor_comments
'Adding full bibliography for 7064007--7064013.cif.'
_cod_database_code               7064011
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.304
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N007-H007 = N1-H007
 1.05 with sigma of 0.02
 O2-C13 \\sim O0-C33
 with sigma of 0.02
 O2-C00R \\sim O0-C26
 with sigma of 0.02
 N007-C7 \\sim N1-C7
 with sigma of 0.02
 N007-C8 \\sim N1-C29
 with sigma of 0.02
 C13-C12 \\sim C33-C28
 with sigma of 0.02
 C13-C8 \\sim C33-C29
 with sigma of 0.02
 C12-C11 \\sim C28-C32
 with sigma of 0.02
 C00R-C27 \\sim C26-C00Y
 with sigma of 0.02
 C8-C9 \\sim C29-C30
 with sigma of 0.02
 C11-C10 \\sim C32-C31
 with sigma of 0.02
 C9-C10 \\sim C30-C31
 with sigma of 0.02
 O2-C12 \\sim O0-C28
 with sigma of 0.04
 O2-C8 \\sim O0-C29
 with sigma of 0.04
 O2-C27 \\sim O0-C00Y
 with sigma of 0.04
 N007-C13 \\sim N1-C33
 with sigma of 0.04
 N007-C9 \\sim N1-C30
 with sigma of 0.04
 C13-C00R \\sim C33-C26
 with sigma of 0.04
 C13-C11 \\sim C33-C32
 with sigma of 0.04
 C13-C9 \\sim C33-C30
 with sigma of 0.04
 C7-C8 \\sim C7-C29
 with sigma of 0.04
 C12-C8 \\sim C28-C29
 with sigma of 0.04
 C12-C10 \\sim C28-C31
 with sigma of 0.04
 C8-C10 \\sim C29-C31
 with sigma of 0.04
 C11-C9 \\sim C32-C30
 with sigma of 0.04
 Br1-Cu1 \\sim Br-Cu1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(N007) = Uanis(C13) = Uanis(C12) = Uanis(C00R) = Uanis(C8) =
Uanis(C11) = Uanis(C9) = Uanis(C10) = Uanis(C27) = Uanis(N1) = Uanis(C29) =
Uanis(C30) = Uanis(C31) = Uanis(C32) = Uanis(C28) = Uanis(C33) = Uanis(O0) =
Uanis(C26) = Uanis(C00Y)
Uanis(Br1) = Uanis(Br)
4. Rigid body (RIGU) restrains
 O2, N007, C13, C12, C00R, C8, C11, C9, C10, C27, N1, C29, C30, C31, C32, C28,
 C33, O0, C26, C00Y
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Br1, Br
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N1)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=
 Sof(C28)=Sof(H28)=Sof(C33)=Sof(O0)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C00Y)=
 Sof(H00C)=Sof(H00D)=Sof(H00E)=1-FVAR(1)
 Sof(O2)=Sof(N007)=Sof(C13)=Sof(C12)=Sof(H12)=Sof(C00R)=Sof(H00A)=Sof(H00B)=
 Sof(C8)=Sof(C11)=Sof(H11)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(H27C)=FVAR(1)
 Sof(Br)=1-FVAR(2)
 Sof(Br1)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C26(H26A,H26B)
6.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C2(H2), C21(H21), C25(H25), C15(H15), C22(H22), C17(H17),
 C23(H23), C4(H4), C16(H16), C24(H24), C12(H12), C5(H5), C18(H18), C11(H11),
 C9(H9), C10(H10), C30(H30), C31(H31), C32(H32), C28(H28)
6.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C00Y(H00C,H00D,H00E)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 19 electrons were 
found in a volume of 99A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[CH3CN] per formula unit 
which account for 22 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              69438
_shelx_fab_checksum              51130
_olex2_submission_special_instructions 'No special instructions were received'