Hydroarylation of alkynes <i>via</i> dual <i>ortho</i>-C-H functionalization of diaryl amines on a dicopper(I,I) platform.
Pal, Nilay Kumar; Patra, Moumita; Pandey, Prabhakar K.; Bera, Jitendra K.; Chemical communications (Cambridge, England) 59 (2023) 8079–8082; doi:10.1039/d3cc01251d

data_7131733
_publ_section_title
;
 Hydroarylation of alkynes <i>via</i> dual <i>ortho</i>-C-H
 functionalization of diaryl amines on a dicopper(I,I) platform.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8079
_journal_page_last               8082
_journal_paper_doi               10.1039/d3cc01251d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 Br N'
_chemical_formula_sum            'C21 H17 Br N'
_chemical_formula_weight         363.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-03 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0166(4)
_cell_length_b                   13.4004(6)
_cell_length_c                   15.2143(7)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.68
_cell_volume                     1634.41(13)
_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      296.15
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.025
_exptl_absorpt_coefficient_mu    2.514
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0215
_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^)+(0.0269P)^2^+1.0790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1952
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01251d2.cif
_cod_data_source_block           dihydroacridine_3_13
_cod_depositor_comments
'Adding full bibliography for 7131731--7131733.cif.'
_cod_database_code               7131733
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H20 of C20
 At 1.2 times of:
  H18 of C18, H19 of C19, H12 of C12, H11 of C11, H9 of C9, H10 of C10
2. Others
 Fixed Sof: H20(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C12(H12), C11(H11), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              26947
_shelx_hkl_checksum              27929
_olex2_submission_special_instructions 'No special instructions were received'