[4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives.
Cao, Dongdong; Ying, Anguo; Mo, Hanjie; Chen, Dingben; Chen, Gang; Wang, Zhiming; Yang, Jianguo; The Journal of organic chemistry 83 (2018) 12568–12574; doi:10.1021/acs.joc.8b01876

data_4035419
_publ_section_title
;
 [4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles:
 Entry to Substituted Carbazol-4-amine Derivatives.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12568
_journal_page_last               12574
_journal_paper_doi               10.1021/acs.joc.8b01876
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C26 H19 N3 O2 S'
_chemical_formula_weight         437.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.739(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.05130(10)
_cell_length_b                   22.4128(5)
_cell_length_c                   15.8276(3)
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.6570
_cell_measurement_theta_min      8.5550
_cell_volume                     2121.72(7)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.908
_diffrn_reflns_theta_min         3.445
_exptl_absorpt_coefficient_mu    1.592
_exptl_crystal_colour            coloeless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0477
_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
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.6684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3577
_reflns_number_total             4022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01876_si_002.cif
_cod_data_source_block           C:\Users\win7\Desktop\2685\OLEX2_~1\exp_2685
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035419
_shelxl_version_number           2013-4
_shelx_res_checksum              58456