Synthesis of pyrroloindolines and furoindolines via cascade dearomatization of indole derivatives with carbenium ion
Chuan Liu; Qin Yin; Li-Xin Dai; Shu-Li You; Chem.Commun. 51 (2015) 5971–; doi:10.1039/C5cc00780A

data_7116855
_publ_section_title
;
 Synthesis of pyrroloindolines and furoindolines via cascade
 dearomatization of indole derivatives with carbenium ion
;
_journal_name_full               Chem.Commun.
_journal_page_first              5971
_journal_paper_doi               10.1039/C5cc00780A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C25 H24 N2 O2 S3'
_chemical_formula_sum            'C25 H24 N2 O2 S3'
_chemical_formula_weight         480.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-29 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.461(2)
_cell_length_b                   12.938(3)
_cell_length_c                   15.619(3)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.68
_cell_measurement_theta_min      3.42
_cell_volume                     2311.8(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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16134
_diffrn_reflns_theta_full        65.99
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         4.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.137
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0059(4)
_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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0646P)^2^+1.1327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                3839
_reflns_number_total             3959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00780a2.cif
_cod_data_source_block           190
_cod_original_cell_volume        2311.7(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7116855