Benzyne-benzyne-RNC or CO triple sequential insertion into the Pd-C bond: synthesis of ten-membered N-heterocycles through stable ten- and eleven-membered palladacycles
Maria-Jose Oliva-Madrid; Isabel Saura-Llamas; Delia Bautista; Jose Vicente; Chem.Commun. 49 (2013) 7997–; doi:10.1039/c3cc43049a

data_7109697
_publ_section_title
;
 Benzyne-benzyne-RNC or CO triple sequential insertion into the Pd-C bond:
 synthesis of ten-membered N-heterocycles through stable ten- and
 eleven-membered palladacycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              7997
_journal_paper_doi               10.1039/c3cc43049a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C33 H33 Cl2 F3 N2 O5 S'
_chemical_formula_weight         697.57
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0215(8)
_cell_length_b                   12.1750(5)
_cell_length_c                   15.8959(7)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.39
_cell_volume                     3294.2(3)
_computing_cell_refinement       'SAINT V8.1????C (Bruker AXS Inc., 2011)'
_computing_data_collection       'APEX2 201?.? (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.1????C (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'high brilliance microfocus sealed tube'
_diffrn_radiation_type           'high brilliance microfocus sealed tube MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            84946
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9010
_exptl_absorpt_correction_T_min  0.8521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment
'The NH hydrogens free, ordered methyl groups rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         8153
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+2.1920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                7244
_reflns_number_total             8153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43049a.txt
_cod_data_source_block           jof882c_sp
_cod_original_sg_symbol_H-M      'P na2(1)'
_cod_database_code               7109697