Catalyst-free reactions of anilines with β-chloroenones: synthesis of α-chloroenaminones and 1,4-benzodiazepines.
Suresh, Sundaram; Palla, Sowndarya; Chung, Dai-Ru; Chien, Hung-Sheng; Du, Bo-Xun; Shinde, Jivan; Kavala, Veerababurao; Yao, Ching-Fa; Organic & biomolecular chemistry 22 (2024) 8857–8868; doi:10.1039/d4ob00954a

data_7160114
_publ_section_title
;
 Catalyst-free reactions of anilines with &#x3b2;-chloroenones: synthesis
 of &#x3b1;-chloroenaminones and 1,4-benzodiazepines.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8857
_journal_page_last               8868
_journal_paper_doi               10.1039/d4ob00954a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C24 H18 Br2 N2 O2'
_chemical_formula_sum            'C24 H18 Br2 N2 O2'
_chemical_formula_weight         526.22
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-06-04 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.33
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.4571(15)
_cell_length_b                   13.4666(5)
_cell_length_c                   11.2783(5)
_cell_measurement_reflns_used    6561
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.68
_cell_volume                     4622.5(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23074
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_T_max  0.9015
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.546
_refine_diff_density_min         -1.033
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.685
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.685
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+20.4408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                3449
_reflns_number_total             4072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00954a2.cif
_cod_data_source_block           d25025
_cod_depositor_comments
'Adding full bibliography for 7160113--7160115.cif.'
_cod_original_cell_volume        4622.4(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160114