Regioselective Synthesis of Chromones via Cyclocarbonylative Sonogashira Coupling Catalyzed by Highly Active Bridged-Bis(N-Heterocyclic Carbene)Palladium(II) Complexes.
Mansour, Waseem; Fettouhi, Mohammed; El Ali, Bassam; ACS omega 5 (2020) 32515–32529; doi:10.1021/acsomega.0c04706

data_4518295
_publ_section_title
;
 Regioselective Synthesis of Chromones via Cyclocarbonylative Sonogashira
 Coupling Catalyzed by Highly Active Bridged-Bis(N-Heterocyclic
 Carbene)Palladium(II) Complexes.
;
_journal_issue                   50
_journal_name_full               'ACS omega'
_journal_page_first              32515
_journal_page_last               32529
_journal_paper_doi               10.1021/acsomega.0c04706
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C23 H28 Br2 N4 Pd, C3 H7 N O'
_chemical_formula_sum            'C26 H35 Br2 N5 O Pd'
_chemical_formula_weight         699.81
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2158(6)
_cell_length_b                   18.1879(7)
_cell_length_c                   9.2992(4)
_cell_measurement_reflns_used    9730
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.245
_cell_measurement_theta_min      2.46
_cell_volume                     2742.63(19)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS D8 Quest diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            76298
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_min         2.512
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.619
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.549
_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_colour            colorless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.039
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+3.9596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2954
_reflns_number_total             3528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c04706_si_001.cif
_cod_data_source_block           new
_cod_depositor_comments
'Adding full bibliography for 4518294--4518295.cif.'
_cod_database_code               4518295
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.490
_shelx_estimated_absorpt_t_max   0.714
_shelx_res_checksum              24874
_shelx_hkl_checksum              97803