#------------------------------------------------------------------------------
#$Date: 2025-01-05 17:37:27 +0200 (Sun, 05 Jan 2025) $
#$Revision: 297065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160327.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_7160327
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         'C16 H19 N O5'
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 99.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5277(3)
_cell_length_b                   13.5344(5)
_cell_length_c                   17.0980(6)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4672
_cell_measurement_theta_min      2.8438
_cell_volume                     1491.60(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.928
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_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            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0370
_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)+(0.0298P)²+0.7760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3146
_reflns_number_total             3430
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01501k2.cif
_cod_data_source_block           dbt5
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160327
_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   0.946
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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 0.77164(17) 0.48804(8) 0.36227(7) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.75054(18) 0.50603(8) 0.28038(7) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.90689(19) 0.47101(9) 0.23956(7) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.895069 0.482861 0.184268 0.024 Uiso 1 1 calc R U . . .
C4 C 1.0769(2) 0.41996(9) 0.27753(8) 0.0234(3) Uani 1 1 d . . . . .
H4 H 1.182238 0.398474 0.248951 0.028 Uiso 1 1 calc R U . . .
C5 C 1.0924(2) 0.40024(9) 0.35815(8) 0.0238(3) Uani 1 1 d . . . . .
H5 H 1.207284 0.363796 0.384582 0.029 Uiso 1 1 calc R U . . .
C6 C 0.94121(19) 0.43356(9) 0.39978(7) 0.0206(2) Uani 1 1 d . . . . .
H6 H 0.952517 0.419265 0.454698 0.025 Uiso 1 1 calc R U . . .
C7 C 0.56739(18) 0.55254(8) 0.23374(7) 0.0167(2) Uani 1 1 d . . . . .
O1 O 0.53063(15) 0.51873(7) 0.15915(5) 0.0233(2) Uani 1 1 d . . . . .
H1 H 0.411(3) 0.5531(13) 0.1359(10) 0.035 Uiso 1 1 d . U . . .
C8 C 0.44461(18) 0.62254(8) 0.26053(6) 0.0157(2) Uani 1 1 d . . . . .
C9 C 0.50505(17) 0.66834(8) 0.34085(6) 0.0145(2) Uani 1 1 d . . . . .
H9 H 0.408088 0.723999 0.346977 0.017 Uiso 1 1 calc R U . . .
O2 O 0.71018(12) 0.70604(6) 0.34640(4) 0.01599(17) Uani 1 1 d . . . . .
C10 C 0.49351(17) 0.59227(8) 0.40572(6) 0.0155(2) Uani 1 1 d . . . . .
N1 N 0.62315(15) 0.51387(7) 0.41011(6) 0.0167(2) Uani 1 1 d . . . . .
H1N H 0.625(2) 0.4780(12) 0.4534(9) 0.026(4) Uiso 1 1 d . . . . .
O3 O 0.37260(13) 0.60291(6) 0.45361(5) 0.02074(19) Uani 1 1 d . . . . .
C11 C 0.25882(18) 0.65500(8) 0.20786(7) 0.0171(2) Uani 1 1 d . . . . .
O4 O 0.21443(14) 0.62894(7) 0.13827(5) 0.0244(2) Uani 1 1 d . . . . .
O5 O 0.13639(12) 0.71513(6) 0.24158(5) 0.01881(18) Uani 1 1 d . . . . .
C12 C -0.05383(18) 0.74567(10) 0.19178(7) 0.0220(3) Uani 1 1 d . . . . .
H12A H -0.020118 0.783828 0.146788 0.033 Uiso 1 1 calc R U . . .
H12B H -0.135523 0.786682 0.222666 0.033 Uiso 1 1 calc R U . . .
H12C H -0.134397 0.687132 0.172231 0.033 Uiso 1 1 calc R U . . .
C13 C 0.77176(18) 0.76251(9) 0.41699(7) 0.0184(2) Uani 1 1 d . . . . .
H13A H 0.753954 0.722802 0.464080 0.022 Uiso 1 1 calc R U . . .
H13B H 0.684690 0.822504 0.416208 0.022 Uiso 1 1 calc R U . . .
C14 C 0.99591(18) 0.79105(9) 0.42082(7) 0.0179(2) Uani 1 1 d . . . . .
H14A H 1.013227 0.827449 0.372065 0.022 Uiso 1 1 calc R U . . .
H14B H 1.081956 0.730550 0.423314 0.022 Uiso 1 1 calc R U . . .
C15 C 1.07064(19) 0.85535(9) 0.49271(7) 0.0211(2) Uani 1 1 d . . . . .
H15A H 1.061005 0.817254 0.541430 0.025 Uiso 1 1 calc R U . . .
H15B H 0.978364 0.913508 0.491920 0.025 Uiso 1 1 calc R U . . .
C16 C 1.2931(2) 0.89057(11) 0.49518(8) 0.0282(3) Uani 1 1 d . . . . .
H16A H 1.386560 0.833471 0.500195 0.042 Uiso 1 1 calc R U . . .
H16B H 1.331166 0.934563 0.540680 0.042 Uiso 1 1 calc R U . . .
H16C H 1.304714 0.926361 0.446246 0.042 Uiso 1 1 calc R U . . .
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'
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
C6 C1 C2 119.59(10) . . ?
C6 C1 N1 115.61(10) . . ?
C2 C1 N1 124.57(10) . . ?
C1 C2 C3 118.11(11) . . ?
C1 C2 C7 123.89(10) . . ?
C3 C2 C7 117.83(10) . . ?
C4 C3 C2 121.88(11) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.30(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.11(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.95(11) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 C8 121.97(11) . . ?
O1 C7 C2 112.21(10) . . ?
C8 C7 C2 125.82(10) . . ?
C7 O1 H1 104.2(10) . . ?
C7 C8 C11 118.45(10) . . ?
C7 C8 C9 120.64(10) . . ?
C11 C8 C9 120.85(10) . . ?
O2 C9 C8 108.53(9) . . ?
O2 C9 C10 110.37(9) . . ?
C8 C9 C10 110.53(9) . . ?
O2 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C9 O2 C13 112.57(8) . . ?
O3 C10 N1 121.06(10) . . ?
O3 C10 C9 121.01(10) . . ?
N1 C10 C9 117.92(10) . . ?
C10 N1 C1 130.18(10) . . ?
C10 N1 H1N 113.8(10) . . ?
C1 N1 H1N 115.5(10) . . ?
O4 C11 O5 121.81(11) . . ?
O4 C11 C8 123.78(11) . . ?
O5 C11 C8 114.41(10) . . ?
C11 O5 C12 115.85(9) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 108.37(9) . . ?
O2 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O2 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 C15 111.54(9) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 112.57(10) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 1.3986(17) . ?
C1 C2 1.4063(16) . ?
C1 N1 1.4076(14) . ?
C2 C3 1.4066(16) . ?
C2 C7 1.4698(16) . ?
C3 C4 1.3793(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3920(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3807(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.3405(14) . ?
C7 C8 1.3660(16) . ?
O1 H1 0.942(18) . ?
C8 C11 1.4593(16) . ?
C8 C9 1.5015(15) . ?
C9 O2 1.4220(13) . ?
C9 C10 1.5239(15) . ?
C9 H9 1.0000 . ?
O2 C13 1.4315(13) . ?
C10 O3 1.2323(14) . ?
C10 N1 1.3519(15) . ?
N1 H1N 0.883(16) . ?
C11 O4 1.2310(14) . ?
C11 O5 1.3338(14) . ?
O5 C12 1.4503(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5047(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5222(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5226(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 O4 0.942(18) 1.648(18) 2.5258(13) 153.4(16) . yes
N1 H1N O3 0.883(16) 1.929(16) 2.8121(13) 178.6(15) 3_666 yes
C14 H14B O3 0.99 2.56 3.5225(14) 165 1_655 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 -2.25(16) . . . . ?
N1 C1 C2 C3 -176.51(11) . . . . ?
C6 C1 C2 C7 172.89(11) . . . . ?
N1 C1 C2 C7 -1.37(18) . . . . ?
C1 C2 C3 C4 0.28(17) . . . . ?
C7 C2 C3 C4 -175.16(11) . . . . ?
C2 C3 C4 C5 1.59(19) . . . . ?
C3 C4 C5 C6 -1.46(19) . . . . ?
C4 C5 C6 C1 -0.53(19) . . . . ?
C2 C1 C6 C5 2.41(18) . . . . ?
N1 C1 C6 C5 177.17(11) . . . . ?
C1 C2 C7 O1 -148.04(11) . . . . ?
C3 C2 C7 O1 27.11(15) . . . . ?
C1 C2 C7 C8 32.17(18) . . . . ?
C3 C2 C7 C8 -152.68(11) . . . . ?
O1 C7 C8 C11 5.08(17) . . . . ?
C2 C7 C8 C11 -175.15(10) . . . . ?
O1 C7 C8 C9 -172.08(10) . . . . ?
C2 C7 C8 C9 7.69(17) . . . . ?
C7 C8 C9 O2 53.35(13) . . . . ?
C11 C8 C9 O2 -123.75(11) . . . . ?
C7 C8 C9 C10 -67.82(13) . . . . ?
C11 C8 C9 C10 115.09(11) . . . . ?
C8 C9 O2 C13 172.37(9) . . . . ?
C10 C9 O2 C13 -66.37(11) . . . . ?
O2 C9 C10 O3 122.32(11) . . . . ?
C8 C9 C10 O3 -117.61(12) . . . . ?
O2 C9 C10 N1 -56.30(13) . . . . ?
C8 C9 C10 N1 63.77(13) . . . . ?
O3 C10 N1 C1 -179.84(11) . . . . ?
C9 C10 N1 C1 -1.22(18) . . . . ?
C6 C1 N1 C10 151.16(12) . . . . ?
C2 C1 N1 C10 -34.37(19) . . . . ?
C7 C8 C11 O4 -6.07(17) . . . . ?
C9 C8 C11 O4 171.09(11) . . . . ?
C7 C8 C11 O5 173.00(10) . . . . ?
C9 C8 C11 O5 -9.84(15) . . . . ?
O4 C11 O5 C12 1.46(16) . . . . ?
C8 C11 O5 C12 -177.63(9) . . . . ?
C9 O2 C13 C14 174.96(9) . . . . ?
O2 C13 C14 C15 177.52(9) . . . . ?
C13 C14 C15 C16 -176.41(10) . . . . ?
