Electronic effect of substituents on anilines favors 1,4-addition to trans-β-nitrostyrenes: access to N-substituted 3-arylindoles and 3-arylindoles.
Gattu, Radhakrishna; Bhattacharjee, Suchandra; Mahato, Karuna; Khan, Abu T.; Organic & biomolecular chemistry 16 (2018) 3760–3770; doi:10.1039/c8ob00736e

data_7156230
_publ_section_title
;
 Electronic effect of substituents on anilines favors 1,4-addition to
 trans-\b-nitrostyrenes: access to N-substituted 3-arylindoles and
 3-arylindoles.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3760
_journal_page_last               3770
_journal_paper_doi               10.1039/c8ob00736e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C15 H12 Cl N'
_chemical_formula_weight         241.71
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-09-23 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.387(10)
_cell_angle_beta                 94.259(10)
_cell_angle_gamma                98.976(10)
_cell_formula_units_Z            4
_cell_length_a                   9.4630(12)
_cell_length_b                   9.9221(11)
_cell_length_c                   13.5665(16)
_cell_measurement_reflns_used    1256
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.0940
_cell_volume                     1221.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8345
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             504.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0733P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.2047
_reflns_number_gt                2125
_reflns_number_total             4285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob00736e2.cif
_cod_data_source_block           exp_3932
_cod_depositor_comments          'Adding full bibliography for 7156230.cif.'
_cod_database_code               7156230