#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:39:43 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160113.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_7160113
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         'C15 H12 Br0 Cl N O'
_chemical_formula_sum            'C15 H12 Br0 Cl N O'
_chemical_formula_weight         257.71
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.4024(11)
_cell_length_b                   8.0914(4)
_cell_length_c                   16.3490(8)
_cell_measurement_reflns_used    5566
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.869
_cell_measurement_theta_min      2.353
_cell_volume                     2699.0(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi scan & omega scan'
_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  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19163
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9234
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                3401
_reflns_number_total             4314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00954a2.cif
_cod_data_source_block           d24546
_cod_depositor_comments
'Adding full bibliography for 7160113--7160115.cif.'
_cod_database_code               7160113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.58996(14) 0.1700(4) 0.56694(19) 0.0316(7) Uani 1 1 d . . .
C2 C 0.60281(15) 0.0542(4) 0.63226(19) 0.0290(7) Uani 1 1 d . . .
C3 C 0.55187(18) 0.0306(4) 0.6966(2) 0.0341(8) Uani 1 1 d . . .
C4 C 0.53263(17) -0.1299(5) 0.7165(3) 0.0469(10) Uani 1 1 d . . .
H4 H 0.5527 -0.2218 0.6904 0.056 Uiso 1 1 calc R . .
C5 C 0.4838(2) -0.1548(5) 0.7747(3) 0.0598(12) Uani 1 1 d . . .
H5 H 0.4693 -0.2638 0.7866 0.072 Uiso 1 1 calc R . .
C6 C 0.4563(2) -0.0219(7) 0.8152(3) 0.0667(14) Uani 1 1 d . . .
H6 H 0.4229 -0.0396 0.8547 0.080 Uiso 1 1 calc R . .
C7 C 0.4769(2) 0.1345(6) 0.7984(2) 0.0578(11) Uani 1 1 d . . .
H7 H 0.4589 0.2251 0.8278 0.069 Uiso 1 1 calc R . .
C8 C 0.52403(18) 0.1626(5) 0.7389(2) 0.0440(9) Uani 1 1 d . . .
H8 H 0.5374 0.2725 0.7269 0.053 Uiso 1 1 calc R . .
C9 C 0.53037(14) 0.2412(3) 0.5538(2) 0.0319(7) Uani 1 1 d . . .
H9 H 0.4965 0.2111 0.5907 0.038 Uiso 1 1 calc R . .
C10 C 0.45226(13) 0.4254(3) 0.4897(2) 0.0340(7) Uani 1 1 d . . .
C11 C 0.41090(17) 0.4390(4) 0.5553(2) 0.0481(9) Uani 1 1 d . . .
H11 H 0.4239 0.3956 0.6068 0.058 Uiso 1 1 calc R . .
C12 C 0.3505(2) 0.5149(4) 0.5478(4) 0.0587(14) Uani 1 1 d . . .
H12 H 0.3220 0.5228 0.5936 0.070 Uiso 1 1 calc R . .
C13 C 0.33188(17) 0.5805(4) 0.4716(3) 0.0544(11) Uani 1 1 d . . .
H13 H 0.2906 0.6332 0.4654 0.065 Uiso 1 1 calc R . .
C14 C 0.37339(18) 0.5678(4) 0.4071(3) 0.0560(10) Uani 1 1 d . . .
H14 H 0.3608 0.6122 0.3557 0.067 Uiso 1 1 calc R . .
C15 C 0.4338(2) 0.4914(4) 0.4148(3) 0.0441(10) Uani 1 1 d . . .
H15 H 0.4624 0.4841 0.3691 0.053 Uiso 1 1 calc R . .
C16 C 0.66133(14) 0.6658(3) 0.42879(18) 0.0300(7) Uani 1 1 d . . .
C17 C 0.64846(15) 0.5485(4) 0.36510(19) 0.0294(7) Uani 1 1 d . . .
C18 C 0.70077(19) 0.5173(3) 0.3021(2) 0.0318(8) Uani 1 1 d . . .
C19 C 0.71561(16) 0.3541(4) 0.2825(2) 0.0388(9) Uani 1 1 d . . .
H19 H 0.6922 0.2669 0.3082 0.047 Uiso 1 1 calc R . .
C20 C 0.76396(19) 0.3173(5) 0.2263(3) 0.0518(11) Uani 1 1 d . . .
H20 H 0.7741 0.2054 0.2139 0.062 Uiso 1 1 calc R . .
C21 C 0.7974(2) 0.4432(6) 0.1883(3) 0.0551(11) Uani 1 1 d . . .
H21 H 0.8310 0.4181 0.1501 0.066 Uiso 1 1 calc R . .
C22 C 0.78242(17) 0.6069(5) 0.2055(2) 0.0487(9) Uani 1 1 d . . .
H22 H 0.8052 0.6940 0.1790 0.058 Uiso 1 1 calc R . .
C23 C 0.73407(17) 0.6412(4) 0.2616(2) 0.0380(8) Uani 1 1 d . . .
H23 H 0.7233 0.7532 0.2728 0.046 Uiso 1 1 calc R . .
C24 C 0.72152(14) 0.7337(3) 0.44435(19) 0.0303(7) Uani 1 1 d . . .
H24 H 0.7563 0.7020 0.4091 0.036 Uiso 1 1 calc R . .
C25 C 0.79849(13) 0.9164(3) 0.51275(19) 0.0325(7) Uani 1 1 d . . .
C26 C 0.84233(17) 0.9297(4) 0.4489(2) 0.0456(8) Uani 1 1 d . . .
H26 H 0.8315 0.8885 0.3962 0.055 Uiso 1 1 calc R . .
C27 C 0.9024(2) 1.0041(4) 0.4631(4) 0.0541(13) Uani 1 1 d . . .
H27 H 0.9331 1.0107 0.4195 0.065 Uiso 1 1 calc R . .
C28 C 0.91856(17) 1.0668(4) 0.5357(3) 0.0584(12) Uani 1 1 d . . .
H28 H 0.9599 1.1183 0.5434 0.070 Uiso 1 1 calc R . .
C29 C 0.87455(17) 1.0561(4) 0.5996(3) 0.0535(10) Uani 1 1 d . . .
H29 H 0.8852 1.1021 0.6514 0.064 Uiso 1 1 calc R . .
C30 C 0.81536(19) 0.9789(4) 0.5881(3) 0.0441(10) Uani 1 1 d . . .
H30 H 0.7858 0.9684 0.6327 0.053 Uiso 1 1 calc R . .
N1 N 0.51416(11) 0.3474(3) 0.49560(17) 0.0322(6) Uani 1 1 d . . .
H1 H 0.5438 0.3710 0.4582 0.039 Uiso 1 1 calc R . .
N2 N 0.73633(10) 0.8401(3) 0.50405(16) 0.0318(6) Uani 1 1 d . . .
H2 H 0.7057 0.8641 0.5401 0.038 Uiso 1 1 calc R . .
O1 O 0.65453(12) -0.0270(3) 0.63598(16) 0.0382(6) Uani 1 1 d . . .
O2 O 0.59590(12) 0.4721(3) 0.36015(16) 0.0380(6) Uani 1 1 d . . .
Cl1 Cl 0.65391(3) 0.20934(9) 0.49958(5) 0.0401(2) Uani 1 1 d . . .
Cl2 Cl 0.59645(3) 0.71364(10) 0.49455(5) 0.0409(2) 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'
Cl Cl 0.1484 0.1585 '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
C9 C1 C2 123.6(3) . . ?
C9 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 116.8(2) . . ?
O1 C2 C1 122.2(3) . . ?
O1 C2 C3 119.3(3) . . ?
C1 C2 C3 118.5(3) . . ?
C8 C3 C4 118.9(4) . . ?
C8 C3 C2 122.5(3) . . ?
C4 C3 C2 118.7(3) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
N1 C9 C1 127.7(3) . . ?
N1 C9 H9 116.2 . . ?
C1 C9 H9 116.2 . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 N1 122.2(3) . . ?
C15 C10 N1 118.3(3) . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.3(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C24 C16 C17 124.4(3) . . ?
C24 C16 Cl2 118.4(2) . . ?
C17 C16 Cl2 117.0(2) . . ?
O2 C17 C16 122.4(3) . . ?
O2 C17 C18 119.0(3) . . ?
C16 C17 C18 118.6(3) . . ?
C23 C18 C19 118.2(4) . . ?
C23 C18 C17 123.8(3) . . ?
C19 C18 C17 118.1(3) . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.1(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C18 121.7(3) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
N2 C24 C16 126.7(3) . . ?
N2 C24 H24 116.7 . . ?
C16 C24 H24 116.7 . . ?
C30 C25 C26 119.2(3) . . ?
C30 C25 N2 118.3(3) . . ?
C26 C25 N2 122.6(3) . . ?
C25 C26 C27 118.8(4) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 122.3(4) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C29 119.3(4) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C30 C29 C28 119.8(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C25 C30 C29 120.6(4) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C9 N1 C10 124.1(3) . . ?
C9 N1 H1 117.9 . . ?
C10 N1 H1 117.9 . . ?
C24 N2 C25 123.8(3) . . ?
C24 N2 H2 118.1 . . ?
C25 N2 H2 118.1 . . ?
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 C9 1.363(4) . ?
C1 C2 1.445(4) . ?
C1 Cl1 1.737(3) . ?
C2 O1 1.245(4) . ?
C2 C3 1.491(5) . ?
C3 C8 1.394(5) . ?
C3 C4 1.395(5) . ?
C4 C5 1.392(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.361(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.324(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(5) . ?
C10 C15 1.388(5) . ?
C10 N1 1.415(3) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.407(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.356(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C24 1.369(4) . ?
C16 C17 1.433(4) . ?
C16 Cl2 1.749(3) . ?
C17 O2 1.240(3) . ?
C17 C18 1.505(5) . ?
C18 C23 1.380(5) . ?
C18 C19 1.392(4) . ?
C19 C20 1.381(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 N2 1.336(4) . ?
C24 H24 0.9500 . ?
C25 C30 1.375(5) . ?
C25 C26 1.378(4) . ?
C25 N2 1.418(3) . ?
C26 C27 1.385(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.332(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.373(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
