Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid.
Panda, Subhankar; Pradhan, Nirmalya; Manna, Debasis; ACS combinatorial science 20 (2018) 573–578; doi:10.1021/acscombsci.8b00071

data_4515830
_publ_section_title
;
 Ring-Opening of Indoles: An Unconventional Route for the Transformation
 of Indoles to 1 H-Pyrazoles Using Lewis Acid.
;
_journal_issue                   10
_journal_name_full               'ACS combinatorial science'
_journal_page_first              573
_journal_page_last               578
_journal_paper_doi               10.1021/acscombsci.8b00071
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C23 H16 N4 O'
_chemical_formula_sum            'C23 H16 N4 O'
_chemical_formula_weight         364.40
_space_group_crystal_system      monoclinic
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_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 107.132(8)
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_cell_length_b                   9.9810(6)
_cell_length_c                   16.3134(14)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      3.39
_cell_volume                     1949.4(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.175
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.382
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       Needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1314
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_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1802
_reflns_number_total             3444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co8b00071_si_002.cif
_cod_data_source_block           exp_4814
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515830
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              26069
_shelx_hkl_checksum              59909