#------------------------------------------------------------------------------
#$Date: 2025-01-05 17:37:27 +0200 (Sun, 05 Jan 2025) $
#$Revision: 297065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160329.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_7160329
loop_
_publ_author_name
'Caletková, Oľga'
'Pinčeková, Lucia'
'Nováčiková, Jana'
'Gyepes, Róbert'
'Olejníková, Petra'
'Pôbiš, Peter'
'Kanďárová, Helena'
'Berkeš, Dušan'
_publ_section_title
;
 A novel 1-benzoazepine-derived Michael acceptor and its hetero-adducts
 active against MRSA.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9394
_journal_page_last               9402
_journal_paper_doi               10.1039/d4ob01501k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 Cl N2 O4, C2 H3 N'
_chemical_formula_sum            'C20 H18 Cl N3 O4'
_chemical_formula_weight         399.82
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.933(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6021(9)
_cell_length_b                   24.331(2)
_cell_length_c                   7.7431(7)
_cell_measurement_reflns_used    1947
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.1974
_cell_measurement_theta_min      3.6333
_cell_volume                     1865.6(3)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16741
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.357
_diffrn_reflns_theta_min         3.633
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0478
_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/[σ²(Fo²)+(0.0531P)²+0.1043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2275
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01501k2.cif
_cod_data_source_block           dbt7
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1865.5(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160329
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.855
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7120(3) 0.37353(11) 0.9704(4) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.6467(3) 0.41890(11) 0.8636(4) 0.0199(6) Uani 1 1 d . . . . .
C3 C 0.6525(3) 0.46966(11) 0.9499(4) 0.0244(6) Uani 1 1 d . . . . .
H3 H 0.607727 0.500344 0.878121 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7215(3) 0.47635(11) 1.1367(4) 0.0255(6) Uani 1 1 d . . . . .
H4 H 0.724046 0.511189 1.193215 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7871(3) 0.43160(12) 1.2411(4) 0.0271(6) Uani 1 1 d . . . . .
H5 H 0.836306 0.436008 1.369555 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7815(3) 0.38081(11) 1.1602(4) 0.0245(6) Uani 1 1 d . . . . .
H6 H 0.825317 0.350344 1.234052 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5653(3) 0.41543(11) 0.6658(4) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.4614(2) 0.45095(8) 0.6169(3) 0.0261(5) Uani 1 1 d . . . . .
H1 H 0.416(3) 0.4488(14) 0.494(5) 0.039 Uiso 1 1 d . U . . .
C8 C 0.5900(3) 0.38113(11) 0.5418(4) 0.0200(6) Uani 1 1 d . . . . .
C9 C 0.7107(3) 0.34337(11) 0.5961(4) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.708891 0.323229 0.482668 0.023 Uiso 1 1 calc R U . . .
N2 N 0.8381(2) 0.37349(9) 0.6680(3) 0.0212(5) Uani 1 1 d . . . . .
H2N H 0.828(3) 0.4109(15) 0.663(4) 0.036(9) Uiso 1 1 d . . . . .
C10 C 0.7000(3) 0.30081(11) 0.7357(4) 0.0202(6) Uani 1 1 d . . . . .
N1 N 0.7031(2) 0.31909(9) 0.9029(3) 0.0207(5) Uani 1 1 d . . . . .
H1N H 0.702(3) 0.2954(13) 0.981(4) 0.027(8) Uiso 1 1 d . . . . .
O2 O 0.68946(19) 0.25146(7) 0.6991(3) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.4943(3) 0.38123(11) 0.3510(4) 0.0214(6) Uani 1 1 d . . . . .
O3 O 0.39847(19) 0.41350(8) 0.2933(3) 0.0260(4) Uani 1 1 d . . . . .
O4 O 0.51711(19) 0.34333(8) 0.2430(2) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.4257(3) 0.34403(13) 0.0526(4) 0.0290(7) Uani 1 1 d . . . . .
H12A H 0.333858 0.335997 0.047424 0.043 Uiso 1 1 calc R U . . .
H12B H 0.453707 0.316183 -0.017834 0.043 Uiso 1 1 calc R U . . .
H12C H 0.427665 0.380402 -0.000791 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9531(3) 0.35316(11) 0.6424(3) 0.0213(6) Uani 1 1 d . . . . .
C14 C 1.0566(3) 0.38961(12) 0.6459(4) 0.0238(6) Uani 1 1 d . . . . .
H14 H 1.047658 0.427661 0.666590 0.029 Uiso 1 1 calc R U . . .
C15 C 1.1718(3) 0.37070(12) 0.6196(4) 0.0244(6) Uani 1 1 d . . . . .
H15 H 1.241823 0.395564 0.623515 0.029 Uiso 1 1 calc R U . . .
C16 C 1.1839(3) 0.31569(13) 0.5879(4) 0.0288(7) Uani 1 1 d . . . . .
Cl1 Cl 1.32885(8) 0.29241(3) 0.55195(13) 0.0451(3) Uani 1 1 d . . . . .
C17 C 1.0843(3) 0.27862(12) 0.5850(4) 0.0305(7) Uani 1 1 d . . . . .
H17 H 1.094437 0.240688 0.563937 0.037 Uiso 1 1 calc R U . . .
C18 C 0.9697(3) 0.29718(12) 0.6131(4) 0.0259(6) Uani 1 1 d . . . . .
H18 H 0.901606 0.271733 0.612547 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0866(3) 0.41175(15) 0.1138(4) 0.0418(8) Uani 1 1 d . . . . .
H19A H 0.150049 0.409580 0.047948 0.063 Uiso 1 1 calc R U . . .
H19B H -0.005977 0.413497 0.024062 0.063 Uiso 1 1 calc R U . . .
H19C H 0.096677 0.379139 0.191862 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1147(3) 0.46062(13) 0.2284(4) 0.0292(7) Uani 1 1 d . . . . .
N3 N 0.1392(3) 0.49858(12) 0.3203(4) 0.0423(7) 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C6 C1 C2 118.9(2) . . ?
C6 C1 N1 116.5(2) . . ?
C2 C1 N1 124.4(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 C7 117.4(2) . . ?
C1 C2 C7 123.5(2) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 122.6(2) . . ?
O1 C7 C2 112.0(2) . . ?
C8 C7 C2 125.4(2) . . ?
C7 O1 H1 110(2) . . ?
C7 C8 C11 118.1(2) . . ?
C7 C8 C9 122.2(2) . . ?
C11 C8 C9 119.7(2) . . ?
N2 C9 C8 112.2(2) . . ?
N2 C9 C10 111.2(2) . . ?
C8 C9 C10 109.9(2) . . ?
N2 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C13 N2 C9 120.3(2) . . ?
C13 N2 H2N 116(2) . . ?
C9 N2 H2N 114(2) . . ?
O2 C10 N1 120.6(2) . . ?
O2 C10 C9 121.5(2) . . ?
N1 C10 C9 118.0(2) . . ?
C10 N1 C1 129.3(2) . . ?
C10 N1 H1N 118(2) . . ?
C1 N1 H1N 113(2) . . ?
O3 C11 O4 121.8(2) . . ?
O3 C11 C8 123.4(2) . . ?
O4 C11 C8 114.8(2) . . ?
C11 O4 C12 115.4(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C18 122.3(2) . . ?
N2 C13 C14 119.4(2) . . ?
C18 C13 C14 118.3(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 Cl1 119.1(2) . . ?
C17 C16 Cl1 119.7(2) . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C19 178.7(3) . . ?
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 C6 1.400(4) . ?
C1 C2 1.405(4) . ?
C1 N1 1.415(3) . ?
C2 C3 1.395(4) . ?
C2 C7 1.467(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.344(3) . ?
C7 C8 1.366(4) . ?
O1 H1 0.90(3) . ?
C8 C11 1.463(4) . ?
C8 C9 1.508(4) . ?
C9 N2 1.461(3) . ?
C9 C10 1.530(4) . ?
C9 H9 1.0000 . ?
N2 C13 1.394(4) . ?
N2 H2N 0.92(3) . ?
C10 O2 1.230(3) . ?
C10 N1 1.359(3) . ?
N1 H1N 0.84(3) . ?
C11 O3 1.234(3) . ?
C11 O4 1.324(3) . ?
O4 C12 1.446(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.402(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 Cl1 1.751(3) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.450(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.138(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.90(3) 1.73(4) 2.522(3) 145(3) . yes
C9 H9 O4 1.00 2.26 2.771(3) 110 . yes
N2 H2N N3 0.92(3) 2.23(4) 3.121(4) 165(3) 3_666 yes
N1 H1N O2 0.84(3) 2.08(3) 2.909(3) 170(3) 4_566 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C3 173.8(2) . . . . ?
C6 C1 C2 C7 -176.7(3) . . . . ?
N1 C1 C2 C7 -2.6(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C7 C2 C3 C4 177.2(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
N1 C1 C6 C5 -175.2(3) . . . . ?
C3 C2 C7 O1 -29.7(3) . . . . ?
C1 C2 C7 O1 146.8(3) . . . . ?
C3 C2 C7 C8 149.6(3) . . . . ?
C1 C2 C7 C8 -33.9(4) . . . . ?
O1 C7 C8 C11 -3.7(4) . . . . ?
C2 C7 C8 C11 177.1(2) . . . . ?
O1 C7 C8 C9 177.0(2) . . . . ?
C2 C7 C8 C9 -2.3(4) . . . . ?
C7 C8 C9 N2 -59.9(3) . . . . ?
C11 C8 C9 N2 120.7(3) . . . . ?
C7 C8 C9 C10 64.3(3) . . . . ?
C11 C8 C9 C10 -115.1(3) . . . . ?
C8 C9 N2 C13 -148.8(2) . . . . ?
C10 C9 N2 C13 87.7(3) . . . . ?
N2 C9 C10 O2 -118.9(3) . . . . ?
C8 C9 C10 O2 116.2(3) . . . . ?
N2 C9 C10 N1 60.8(3) . . . . ?
C8 C9 C10 N1 -64.0(3) . . . . ?
O2 C10 N1 C1 -178.7(2) . . . . ?
C9 C10 N1 C1 1.5(4) . . . . ?
C6 C1 N1 C10 -147.4(3) . . . . ?
C2 C1 N1 C10 38.3(4) . . . . ?
C7 C8 C11 O3 5.7(4) . . . . ?
C9 C8 C11 O3 -174.9(2) . . . . ?
C7 C8 C11 O4 -173.7(2) . . . . ?
C9 C8 C11 O4 5.7(3) . . . . ?
O3 C11 O4 C12 2.4(4) . . . . ?
C8 C11 O4 C12 -178.2(2) . . . . ?
C9 N2 C13 C18 -24.2(4) . . . . ?
C9 N2 C13 C14 155.9(2) . . . . ?
N2 C13 C14 C15 -179.6(2) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C14 C15 C16 Cl1 179.2(2) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
Cl1 C16 C17 C18 -179.8(2) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
N2 C13 C18 C17 178.9(3) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?
