A combined crystallographic and theoretical investigation of noncovalent interactions in 1,3,4-oxadiazole-2-thione-N-Mannich derivatives: in vitro bioactivity and molecular docking
Al-Wahaibi, Lamya H.; Alagappan, Kowsalya; Gomila, Rosa M.; Blacque, Olivier; Frontera, Antonio; Percino, M. Judith; El-Emam, Ali A.; Thamotharan, Subbiah; RSC Advances 13 (2023) 34064–34077; doi:10.1039/D3RA07169C

data_7247760
_publ_section_title
;
 A combined crystallographic and theoretical investigation of noncovalent
 interactions in 1,3,4-oxadiazole-2-thione-N-Mannich derivatives: in vitro
 bioactivity and molecular docking
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              34064
_journal_page_last               34077
_journal_paper_doi               10.1039/D3RA07169C
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H11 Cl F3 N3 O S'
_chemical_formula_sum            'C16 H11 Cl F3 N3 O S'
_chemical_formula_weight         385.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-10-18 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7906(2)
_cell_length_b                   13.1169(6)
_cell_length_c                   25.4767(12)
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      75.9680
_cell_measurement_theta_min      3.4900
_cell_volume                     1600.90(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -72.00  37.90   0.70   10.00    --  -38.50  19.00 -30.00  157
  2  \w     27.00  97.00   0.70   10.00    --   43.36-125.00 -90.00  100
  3  \w     27.00  97.00   0.70   10.00    --   43.36-125.00 120.00  100
  4  \w    103.00 176.50   0.70   40.00    --  111.00  77.00 120.00  105
  5  \w     71.00 176.70   0.70   40.00    --  111.00  15.00-180.00  151
  6  \w     38.00 108.00   0.70   40.00    --  111.00-111.00-150.00  100
  7  \w    103.00 176.50   0.70   40.00    --  111.00  77.00  90.00  105
  8  \w    103.00 176.50   0.70   40.00    --  111.00  77.00   0.00  105
  9  \w    103.00 176.50   0.70   40.00    --  111.00  77.00-180.00  105
 10  \w    103.00 176.50   0.70   40.00    --  111.00  77.00 150.00  105
 11  \w     40.00 139.40   0.70   40.00    --  111.00 -77.00 150.00  142
 12  \w     38.00 108.00   0.70   40.00    --  111.00-111.00-120.00  100
 13  \w     40.00 139.40   0.70   40.00    --  111.00 -77.00   0.00  142
 14  \w     18.00 110.40   0.70   10.00    --   43.36  57.00  30.00  132
 15  \w     18.00 110.40   0.70   10.00    --   43.36  57.00 -60.00  132
 16  \w     18.00 110.40   0.70   10.00    --   43.36  57.00-180.00  132
 17  \w     89.00 176.50   0.70   40.00    --  111.00  45.00-120.00  125
 18  \w     85.00 176.70   0.70   40.00    --  111.00  61.00  60.00  131
 19  \w     90.00 176.80   0.70   40.00    --  111.00  30.00 -60.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1859274000
_diffrn_orient_matrix_UB_12      -0.0560956000
_diffrn_orient_matrix_UB_13      0.0401005000
_diffrn_orient_matrix_UB_21      0.2097463000
_diffrn_orient_matrix_UB_22      0.0257213000
_diffrn_orient_matrix_UB_23      0.0438694000
_diffrn_orient_matrix_UB_31      -0.1581054000
_diffrn_orient_matrix_UB_32      0.0999747000
_diffrn_orient_matrix_UB_33      0.0111605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.399
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.741
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0545P)^2^+0.2988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2874
_reflns_number_total             3244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra07169c2.cif
_cod_data_source_block           emam-51
_cod_database_code               7247760
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.432
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
;
_shelx_res_checksum              51798