3-Alkenylation or 3-Alkylation of Indole with Propargylic Alcohols: Construction of 3,4-Dihydrocyclopenta[b]indole and 1,4-Dihydrocyclopenta[b]indole in the Presence of Different Catalysts
Li Zhang; Yuanxun Zhu; Guangwei Yin; Ping Lu; Yanguang Wang; Journal of Organic Chemistry 77 (2012) 9510–9520; doi:10.1021/jo300339a

data_4027624
_publ_section_title
;
 3-Alkenylation or 3-Alkylation of Indole with Propargylic Alcohols:
 Construction of 3,4-Dihydrocyclopenta[b]indole and
 1,4-Dihydrocyclopenta[b]indole in the Presence of Different Catalysts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9510
_journal_page_last               9520
_journal_paper_doi               10.1021/jo300339a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C37 H27 N'
_chemical_formula_sum            'C37 H27 N'
_chemical_formula_weight         485.60
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.609(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.6833(10)
_cell_length_b                   8.4181(4)
_cell_length_c                   18.4664(9)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3941
_cell_measurement_theta_min      2.9048
_cell_volume                     2692.7(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15095
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0546P)^2^+0.4724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                3288
_reflns_number_total             4923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300339a_si_003.cif
_cod_data_source_block           111111_lzl_85b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027624