Palladium complexes with an annellated mesoionic carbene (MIC) ligand: catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives.
Tyagi, Akshi; Reshi, Noor U Din; Daw, Prosenjit; Bera, Jitendra K.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 15238–15248; doi:10.1039/d0dt02918a

data_7705605
_publ_section_title
;
 Palladium complexes with an annellated mesoionic carbene (MIC) ligand:
 catalytic sequential Sonogashira coupling/cyclization reaction for
 one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone
 derivatives.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15238
_journal_page_last               15248
_journal_paper_doi               10.1039/d0dt02918a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C53 H43 N3 P2 Pd, 2(F6 P), 2(C H2 Cl2)'
_chemical_formula_sum            'C56 H49 Cl6 F12 N3 O P4 Pd'
_chemical_formula_weight         1450.96
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2020-07-06 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.944(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1613(12)
_cell_length_b                   14.5225(12)
_cell_length_c                   31.355(3)
_cell_measurement_reflns_used    16409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      1.89
_cell_volume                     5935.5(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            59486
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.386
_diffrn_reflns_theta_min         2.416
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2920
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     713
_refine_ls_number_reflns         14796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0452P)^2^+6.9930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10484
_reflns_number_total             14796
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt02918a2.cif
_cod_data_source_block           Pd2
_cod_depositor_comments
'Adding full bibliography for 7705604--7705605.cif.'
_cod_database_code               7705605
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.849
_shelx_estimated_absorpt_t_min   0.836
_exptl_absorpt_special_details   SADABS
_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.a Secondary CH2 refined with riding coordinates:
 C54(H54A,H54B), C56(H56A,H56B)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C49(H49), C6(H6), C43(H43), C29(H29), C37(H37), C23(H23), C28(H28),
 C9(H9), C44(H44), C1(H1), C35(H35), C27(H27), C45(H45), C26(H26), C2(H2),
 C25(H25), C50(H50), C19(H19), C38(H38), C3(H3), C51(H51), C46(H46), C17(H17),
 C15(H15), C47(H47), C14(H14), C22(H22), C20(H20), C13(H13), C41(H41), C31(H31),
  C21(H21), C34(H34), C32(H32), C40(H40), C16(H16), C39(H39), C53(H53), C52(H52)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              38003
_shelx_fab_checksum              55860
_olex2_submission_special_instructions 'No special instructions were received'