Crystal structure of 5-(adamantan-1-yl)-3-[(4-trifluoromethylanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C20H22F3N3OS
Al-Wahaibi, Lamya H.; Ghabbour, Hazem A.; Al-Omary, Fatmah A. M.; Tiekink, Edward R. T.; El-Emam, Ali A.; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 587–591; doi:10.1515/ncrs-2022-0144

data_8107160
_publ_section_title
;
 Crystal structure of
 5-(adamantan-1-yl)-3-[(4-trifluoromethylanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione,
 C20H22F3N3OS
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              587
_journal_page_last               591
_journal_paper_doi               10.1515/ncrs-2022-0144
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration nd
_chemical_formula_moiety         'C20 H22 F3 N3 O S'
_chemical_formula_sum            'C20 H22 F3 N3 O S'
_chemical_formula_weight         409.46
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                76.870(3)
_cell_angle_beta                 88.004(4)
_cell_angle_gamma                87.275(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9678(8)
_cell_length_b                   10.7614(14)
_cell_length_c                   13.0503(14)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.67
_cell_measurement_theta_min      2.79
_cell_volume                     951.60(19)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0506
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21069
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.786
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.429
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 2824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0629
_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^)+(0.1014P)^2^+0.9090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                6248
_reflns_number_total             6660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0144_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8107160
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              93360
_shelx_hkl_checksum              35921