#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:39:43 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160114.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160114
loop_
_publ_author_name
'Suresh, Sundaram'
'Palla, Sowndarya'
'Chung, Dai-Ru'
'Chien, Hung-Sheng'
'Du, Bo-Xun'
'Shinde, Jivan'
'Kavala, Veerababurao'
'Yao, Ching-Fa'
_publ_section_title
;
 Catalyst-free reactions of anilines with β-chloroenones: synthesis
 of α-chloroenaminones and 1,4-benzodiazepines.
;
_journal_issue                   45
_journal_name_full               'Organic & 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/[σ²(Fo²)+(0.0869P)²+20.4408P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48789(9) 0.3563(2) 0.5165(3) 0.0345(6) Uani 1 1 d . . .
C2 C 0.46542(9) 0.4304(2) 0.5522(3) 0.0335(6) Uani 1 1 d . . .
H2 H 0.4739 0.4503 0.6382 0.040 Uiso 1 1 calc R . .
C3 C 0.43009(9) 0.4758(2) 0.4602(3) 0.0309(6) Uani 1 1 d . . .
H3 H 0.4144 0.5271 0.4837 0.037 Uiso 1 1 calc R . .
C4 C 0.41754(9) 0.4470(2) 0.3343(3) 0.0298(6) Uani 1 1 d . . .
C5 C 0.44181(10) 0.3739(2) 0.3009(3) 0.0368(7) Uani 1 1 d . . .
H5 H 0.4341 0.3551 0.2148 0.044 Uiso 1 1 calc R . .
C6 C 0.47713(10) 0.3282(2) 0.3919(3) 0.0381(7) Uani 1 1 d . . .
H6 H 0.4936 0.2783 0.3686 0.046 Uiso 1 1 calc R . .
C7 C 0.37793(9) 0.4892(2) 0.2333(3) 0.0313(6) Uani 1 1 d . . .
C8 C 0.34966(9) 0.5629(2) 0.2709(3) 0.0317(6) Uani 1 1 d . . .
H8A H 0.3666 0.6247 0.3006 0.038 Uiso 1 1 calc R . .
H8B H 0.3421 0.5353 0.3421 0.038 Uiso 1 1 calc R . .
C9 C 0.30709(9) 0.5875(2) 0.1610(3) 0.0344(6) Uani 1 1 d . . .
H9 H 0.2936 0.5224 0.1254 0.041 Uiso 1 1 calc R . .
C10 C 0.27417(9) 0.6389(2) 0.2072(3) 0.0325(6) Uani 1 1 d . . .
C11 C 0.25105(9) 0.5765(2) 0.2648(3) 0.0388(7) Uani 1 1 d . . .
C12 C 0.21735(10) 0.6170(2) 0.3158(3) 0.0366(7) Uani 1 1 d . . .
C13 C 0.22612(12) 0.6153(3) 0.4451(3) 0.0570(10) Uani 1 1 d . . .
H13 H 0.2545 0.5959 0.5001 0.068 Uiso 1 1 calc R . .
C14 C 0.19451(14) 0.6411(3) 0.4956(3) 0.0599(10) Uani 1 1 d . . .
H14 H 0.2009 0.6394 0.5845 0.072 Uiso 1 1 calc R . .
C15 C 0.15369(12) 0.6693(2) 0.4156(3) 0.0443(8) Uani 1 1 d . . .
C16 C 0.14397(11) 0.6732(3) 0.2871(3) 0.0461(8) Uani 1 1 d . . .
H16 H 0.1157 0.6936 0.2329 0.055 Uiso 1 1 calc R . .
C17 C 0.17595(10) 0.6470(3) 0.2376(3) 0.0422(7) Uani 1 1 d . . .
H17 H 0.1694 0.6497 0.1487 0.051 Uiso 1 1 calc R . .
C18 C 0.26600(9) 0.7392(2) 0.1986(3) 0.0335(6) Uani 1 1 d . . .
H18 H 0.2420 0.7592 0.2229 0.040 Uiso 1 1 calc R . .
C19 C 0.32490(10) 0.8124(2) 0.1325(3) 0.0344(6) Uani 1 1 d . . .
C20 C 0.34871(11) 0.8997(2) 0.1501(3) 0.0463(8) Uani 1 1 d . . .
H20 H 0.3388 0.9563 0.1830 0.056 Uiso 1 1 calc R . .
C21 C 0.38671(12) 0.9063(3) 0.1207(4) 0.0520(9) Uani 1 1 d . . .
H21 H 0.4024 0.9671 0.1317 0.062 Uiso 1 1 calc R . .
C22 C 0.40152(12) 0.8237(3) 0.0756(3) 0.0507(9) Uani 1 1 d . . .
H22 H 0.4278 0.8270 0.0564 0.061 Uiso 1 1 calc R . .
C23 C 0.37812(11) 0.7364(3) 0.0584(3) 0.0436(8) Uani 1 1 d . . .
H23 H 0.3888 0.6797 0.0279 0.052 Uiso 1 1 calc R . .
C24 C 0.33917(10) 0.7287(2) 0.0844(3) 0.0351(7) Uani 1 1 d . . .
Br1 Br 0.534928(10) 0.29111(2) 0.64261(3) 0.04358(13) Uani 1 1 d . . .
Br2 Br 0.109812(17) 0.69982(3) 0.48635(4) 0.06671(16) Uani 1 1 d . . .
N1 N 0.31398(8) 0.64140(18) 0.0564(2) 0.0383(6) Uani 1 1 d . . .
H1 H 0.3292 0.6021 0.0204 0.046 Uiso 1 1 d R . .
N2 N 0.28610(8) 0.81303(18) 0.1619(2) 0.0365(6) Uani 1 1 d . . .
H2A H 0.2732 0.8713 0.1550 0.044 Uiso 1 1 calc R . .
O1 O 0.36867(7) 0.46119(17) 0.12426(19) 0.0447(5) Uani 1 1 d . . .
O2 O 0.25873(8) 0.48558(16) 0.2803(3) 0.0530(6) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.7(3) . . ?
C2 C1 Br1 119.1(2) . . ?
C6 C1 Br1 119.2(2) . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 118.6(3) . . ?
C3 C4 C7 122.6(2) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 C4 119.6(3) . . ?
O1 C7 C8 121.7(3) . . ?
C4 C7 C8 118.7(2) . . ?
C7 C8 C9 112.3(2) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 112.0(2) . . ?
N1 C9 C8 114.2(2) . . ?
C10 C9 C8 111.5(2) . . ?
N1 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
C18 C10 C11 119.5(3) . . ?
C18 C10 C9 124.7(3) . . ?
C11 C10 C9 115.8(2) . . ?
O2 C11 C10 122.1(3) . . ?
O2 C11 C12 116.0(3) . . ?
C10 C11 C12 121.9(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 119.0(3) . . ?
C17 C12 C11 122.4(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 Br2 120.2(3) . . ?
C14 C15 Br2 118.4(3) . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.9(3) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N2 C18 C10 130.7(3) . . ?
N2 C18 H18 114.6 . . ?
C10 C18 H18 114.6 . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 N2 117.5(3) . . ?
C24 C19 N2 122.7(3) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 122.0(3) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C19 C24 N1 121.1(3) . . ?
C19 C24 C23 117.9(3) . . ?
N1 C24 C23 120.9(3) . . ?
C24 N1 C9 118.2(2) . . ?
C24 N1 H1 103.0 . . ?
C9 N1 H1 109.2 . . ?
C18 N2 C19 130.0(2) . . ?
C18 N2 H2A 115.0 . . ?
C19 N2 H2A 115.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(4) . ?
C1 C6 1.379(4) . ?
C1 Br1 1.902(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 C7 1.502(4) . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.220(3) . ?
C7 C8 1.509(4) . ?
C8 C9 1.538(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.467(4) . ?
C9 C10 1.510(4) . ?
C9 H9 1.0000 . ?
C10 C18 1.373(4) . ?
C10 C11 1.425(4) . ?
C11 O2 1.249(4) . ?
C11 C12 1.504(4) . ?
C12 C13 1.385(5) . ?
C12 C17 1.387(4) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(5) . ?
C15 Br2 1.904(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N2 1.332(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 C24 1.398(4) . ?
C19 N2 1.410(4) . ?
C20 C21 1.387(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(4) . ?
C23 H23 0.9500 . ?
C24 N1 1.404(4) . ?
N1 H1 0.9092 . ?
N2 H2A 0.8800 . ?
