Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC.
Zhang, Xue; Feng, Chengjie; Jiang, Tao; Li, Yifei; Pan, Ling; Xu, Xianxiu; Organic letters 17 (2015) 3576–3579; doi:10.1021/acs.orglett.5b01676

data_1555100
_publ_section_title
;
 Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and
 Spiro[indene-1,3'-pyrrole] Derivatives from Alkyne-Tethered
 Chalcones/Cinnamates and TosMIC.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3576
_journal_page_last               3579
_journal_paper_doi               10.1021/acs.orglett.5b01676
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H15 Cl I N O2'
_chemical_formula_sum            'C21 H15 Cl I N O2'
_chemical_formula_weight         475.69
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.380(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.057(3)
_cell_length_b                   13.631(3)
_cell_length_c                   13.716(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1937.8(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13514
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.08
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.7490
_exptl_absorpt_correction_T_min  0.6512
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2756
_reflns_number_total             4688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01676_si_002.cif
_cod_data_source_block           11
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1555100