Pd-catalyzed <i>ortho</i>-/<i>meta</i>-C-H-annulation of biphenyl amines with enynes through non-rollover cyclometallation.
Suri Babu, Undamatla; Naveen Kumar, Muniganti; Mahesh, Shivunapuram; Nanubolu, Jagadeesh Babu; Sridhar Reddy, Maddi; Organic & biomolecular chemistry 23 (2025) 292–296; doi:10.1039/d4ob01689k

data_7160219
_publ_section_title
;
 Pd-catalyzed <i>ortho</i>-/<i>meta</i>-C-H-annulation of biphenyl amines
 with enynes through non-rollover cyclometallation.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              292
_journal_page_last               296
_journal_paper_doi               10.1039/d4ob01689k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C33 H24 F4 N2 O2'
_chemical_formula_sum            'C33 H24 F4 N2 O2'
_chemical_formula_weight         556.54
_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   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-06-30 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.697(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.940(5)
_cell_length_b                   16.898(8)
_cell_length_c                   14.590(8)
_cell_measurement_reflns_used    5990
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.978
_cell_measurement_theta_min      2.271
_cell_volume                     2609(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.996
_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       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41526
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.415
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         5950
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0549P)^2^+0.4826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2929
_reflns_number_total             5950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01689k2.cif
_cod_data_source_block           KB1371_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160219.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160219
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              77238