Design, synthesis, and exploration of antibacterial activity of 6<i>H</i>-1,2-oxazin-6-ones.
Alcántar-Zavala, Eleazar; Delgado-Vargas, Francisco; Marín-González, Fabricio; Angulo, Gabriela López; Aguirre-Madrigal, Hugo Enrique; Ochoa-Terán, Adrián; Rodríguez-Vega, Gibrán; Aguirre-Hernández, Gerardo; Montes-Avila, Julio; RSC advances 14 (2024) 23828–23839; doi:10.1039/d4ra04220d

data_7249166
_publ_section_title
;
 Design, synthesis, and exploration of antibacterial activity of
 6<i>H</i>-1,2-oxazin-6-ones.
;
_journal_issue                   33
_journal_name_full               'RSC advances'
_journal_page_first              23828
_journal_page_last               23839
_journal_paper_doi               10.1039/d4ra04220d
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C17 H12 Cl N O2'
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73
_chemical_name_systematic
3-(4-chlorophenyl)-5-(p-tolyl)-6H-1,2-oxazin-6-one
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-05-28
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-06-09 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.691(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.54533(13)
_cell_length_b                   29.5464(5)
_cell_length_c                   7.4552(2)
_cell_measurement_reflns_used    5942
_cell_measurement_temperature    294.1(4)
_cell_measurement_theta_max      70.5110
_cell_measurement_theta_min      3.0020
_cell_volume                     1411.86(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1970
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -44.00  42.00   1.00    2.84    --    0.00  77.00  30.00   86
  2  \w      6.00  51.00   1.00    2.84    --    0.00 -99.00-120.00   45
  3  \w   -155.00 -82.00   1.00   11.36    --  -54.67 -77.00-180.00   73
  4  \w   -149.00 -82.00   1.00   11.36    --  -54.67 -99.00 -90.00   67
  5  \w    -86.00  -6.00   1.00   11.36    --  -54.67 125.00 120.00   80
  6  \w    103.00 155.00   1.00   11.36    --   54.67  77.00-120.00   52
  7  \w    103.00 155.00   1.00   11.36    --   54.67  77.00   0.00   52
  8  \w     97.00 146.00   1.00   11.36    --   54.67 125.00  30.00   49
  9  \w     18.00 109.00   1.00   11.36    --  109.35-111.00  60.00   91
 10  \w     61.00 146.00   1.00   11.36    --  109.35 178.00 -90.00   85
 11  \w    103.00 178.00   1.00   11.36    --  109.35  77.00 -90.00   75
 12  \w    104.00 178.00   1.00   11.36    --  109.35 111.00  30.00   74
 13  \w    103.00 178.00   1.00   11.36    --  109.35  77.00 -60.00   75
 14  \w    104.00 178.00   1.00   11.36    --  109.35 111.00 150.00   74
 15  \w     61.00 146.00   1.00   11.36    --  109.35 178.00   0.00   85
 16  \w    104.00 178.00   1.00   11.36    --  109.35 111.00   0.00   74
 17  \w     65.00 178.00   1.00   11.36    --  109.35  64.00  60.00  113
 18  \w    -21.00  44.00   1.00    2.84    --    0.00 -77.00-180.00   65
 19  \w    -21.00  44.00   1.00    2.84    --    0.00 -77.00  60.00   65
 20  \w   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00-150.00  134
 21  \w   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00 120.00  134
 22  \w   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00  30.00  134
 23  \w     13.00 147.00   1.00   11.36    --   54.67  57.00  30.00  134
 24  \w     27.00 112.00   1.00   11.36    --   54.67-125.00  30.00   85
 25  \w      8.00 145.00   1.00   11.36    --   54.67  38.00 -30.00  137
 26  \w     68.00 178.00   1.00   11.36    --  109.35  50.00-180.00  110
 27  \w    104.00 178.00   1.00   11.36    --  109.35 111.00  90.00   74
 28  \w     65.00 178.00   1.00   11.36    --  109.35  64.00-120.00  113
 29  \w     68.00 178.00   1.00   11.36    --  109.35  50.00   0.00  110
 30  \w     65.00 178.00   1.00   11.36    --  109.35  64.00 120.00  113
 31  \w     65.00 178.00   1.00   11.36    --  109.35  64.00 -60.00  113
 32  \w     65.00  99.00   1.00   11.36    --  109.35  64.00  90.00   34
 33  \w     65.00 178.00   1.00   11.36    --  109.35  64.00-150.00  113
 34  \w     13.00 106.00   1.00   11.36    --  109.35 -92.00  90.00   93
 35  \w     65.00 178.00   1.00   11.36    --  109.35  64.00  30.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1284231000
_diffrn_orient_matrix_UB_12      0.0433272000
_diffrn_orient_matrix_UB_13      0.0089913000
_diffrn_orient_matrix_UB_21      0.2031406000
_diffrn_orient_matrix_UB_22      0.0274882000
_diffrn_orient_matrix_UB_23      0.0542996000
_diffrn_orient_matrix_UB_31      -0.0020233000
_diffrn_orient_matrix_UB_32      0.0092554000
_diffrn_orient_matrix_UB_33      -0.2037458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.770
_diffrn_reflns_theta_min         2.991
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0451
_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/[\s^2^(Fo^2^)+(0.0595P)^2^+0.3478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04220d2.cif
_cod_data_source_block           ea-20000
_cod_original_cell_volume        1411.85(5)
_cod_database_code               7249166
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHONCl
_diffrn_oxdiff_digest_frames
;
01ca637be32266ce0a4c8804dec1f64cda00031f571
;
_diffrn_oxdiff_digest_hkl
;
01df3ceeae55fd2ff27d6132b31034a6947767
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              77457
_olex2_date_sample_data_collection 2021-05-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.350
_oxdiff_exptl_absorpt_empirical_full_min 0.421