Synthesis of Tetrasubstituted Cyclopentadienes via Palladium-Catalyzed Reaction of (Z)-2-En-4-yn Acetates and N-Methyl Indoles
Mei-Jin Zhong; Xiang-Chuan Wang; Hai-Tao Zhu; Jie Hu; Lei Liu; Xue-Yuan Liu; Yong-Min Liang; Journal of Organic Chemistry 77 (2012) 10955–10961; doi:10.1021/jo3021055

data_4027769
_publ_section_title
;
 Synthesis of Tetrasubstituted Cyclopentadienes via Palladium-Catalyzed
 Reaction of (Z)-2-En-4-yn Acetates and N-Methyl Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10955
_journal_page_last               10961
_journal_paper_doi               10.1021/jo3021055
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration none
_chemical_formula_sum            'C33 H27 N'
_chemical_formula_weight         437.56
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 113.506(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.845(5)
_cell_length_b                   9.451(5)
_cell_length_c                   12.818(6)
_cell_measurement_reflns_used    980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.11
_cell_measurement_theta_min      2.77
_cell_volume                     1204.8(10)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.1143
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5366
_diffrn_reflns_theta_full        24.54
_diffrn_reflns_theta_max         24.54
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0215P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                1772
_reflns_number_total             3220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3021055_si_001.cif
_cod_data_source_block           p21
_cod_database_code               4027769