Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles
Sandeep N. Raikar; Helena C. Malinakova; Journal of Organic Chemistry 78 (2013) 3832–3846; doi:10.1021/jo400246d

data_4028155
_publ_section_title
;
 Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides
 in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of
 Heterocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3832
_journal_page_last               3846
_journal_paper_doi               10.1021/jo400246d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   23.8895(15)
_cell_length_b                   9.8805(6)
_cell_length_c                   30.8596(19)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.25
_cell_measurement_theta_min      2.86
_cell_volume                     7284.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Platinum 135 CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator
'Helios MX high-brilliance multilayer x-ray opt'
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            62045
_diffrn_reflns_theta_full        67.66
_diffrn_reflns_theta_max         67.66
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         6473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0392P)^2^+2.4761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                5712
_reflns_number_total             6473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400246d_si_002.cif
_cod_data_source_block           v63a
_cod_database_code               4028155