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_4027627
_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         'C31 H23 N'
_chemical_formula_sum            'C31 H23 N'
_chemical_formula_weight         409.50
_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                 100.187(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0637(6)
_cell_length_b                   9.4505(3)
_cell_length_c                   14.8945(5)
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4214
_cell_measurement_theta_min      2.7517
_cell_volume                     2225.49(13)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8679
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0124(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0467P)^2^+0.3842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2986
_reflns_number_total             4074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300339a_si_006.cif
_cod_data_source_block           101015_lzl_3815c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027627