Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
Al-Wahaibi, Lamya H.; Blacque, Olivier; Al-Shaalan, Nora H.; Tiekink, Edward R. T.; El-Emam, Ali A.; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 159–161; doi:10.1515/ncrs-2022-0511

data_8107381
_publ_section_title
;
 Crystal structure of
 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile,
 C20H22N4OS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              159
_journal_page_last               161
_journal_paper_doi               10.1515/ncrs-2022-0511
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C20 H22 N4 O S'
_chemical_formula_sum            'C20 H22 N4 O S'
_chemical_formula_weight         366.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                114.083(5)
_cell_angle_beta                 104.326(4)
_cell_angle_gamma                90.369(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8528(3)
_cell_length_b                   11.3498(5)
_cell_length_c                   13.3896(9)
_cell_measurement_reflns_used    5077
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.4
_cell_measurement_theta_min      15.7
_cell_volume                     914.38(9)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'OLEX2 [4]'
_computing_publication_material  'OLEX2 [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -26.00  28.00   0.50    0.70    --  -51.56  19.00-120.00  108
  2  \w    -35.00 -10.00   0.50    0.70    --  -86.25  30.00  30.00   50
  3  \w    -73.00  21.00   0.50    0.70    --  -51.56  77.00  30.00  188
  4  \w     30.00 124.00   0.50    0.70    --   51.56  77.00  60.00  188
  5  \w    105.00 178.00   0.50    0.70    --  107.75  45.00 150.00  146
  6  \w     99.00 134.00   0.50    0.70    --  107.75  15.00  90.00   70
  7  \w     99.00 159.00   0.50    0.70    --  107.75  30.00  90.00  120
  8  \w    103.00 141.00   0.50    0.70    --  107.75  30.00 -30.00   76
  9  \w     98.00 150.00   0.50    0.70    --  107.75  15.00 -30.00  104
 10  \w     97.00 129.00   0.50    0.70    --  107.75  45.00-120.00   64
 11  \w    147.00 174.00   0.50    0.70    --  107.75  45.00-120.00   54
 12  \w    144.00 178.00   0.50    0.70    --  107.75  30.00-180.00   68
 13  \w    117.00 171.00   0.50    0.70    --  107.75  15.00-150.00  108
 14  \w     99.00 138.00   0.50    0.70    --  107.75  30.00-180.00   78
 15  \w     99.00 137.00   0.50    0.70    --  107.75 111.00-120.00   76
 16  \w     38.00  64.00   0.50    0.70    --  107.75 -61.00  60.00   52
 17  \w     36.00  95.00   0.50    0.70    --  107.75 -94.00   0.00  118
 18  \w     66.00 112.00   0.50    0.70    --  107.75-111.00 -60.00   92
 19  \w     96.00 129.00   0.50    0.70    --  107.75-140.00 -54.44   66
 20  \w     96.00 133.00   0.50    0.70    --  107.75-146.00  28.53   74
 21  \w     79.00 112.00   0.50    0.70    --  107.75-111.00 150.00   66
 22  \w     48.00  73.00   0.50    0.70    --  107.75-146.00  28.53   50
 23  \w     51.00 111.00   0.50    0.70    --  107.75-111.00   0.00  120
 24  \w     85.00 123.00   0.50    0.70    --  107.75-133.00 -89.68   76
 25  \w     59.00 112.00   0.50    0.70    --  107.75-111.00-120.00  106
 26  \w     52.00  78.00   0.50    0.70    --  107.75-133.00 -89.68   52
 27  \w     44.00  91.00   0.50    0.70    --  107.75-140.00 -54.44   94
 28  \w     41.00 112.00   0.50    0.70    --  107.75-111.00  60.00  142
 29  \w     46.00  79.00   0.50    0.70    --  107.75 -94.00 -60.00   66
 30  \w     48.00  78.00   0.50    0.70    --  107.75 -77.00   0.00   60
 31  \w     35.00 101.00   0.50    0.70    --  107.75 -77.00  60.00  132
 32  \w     35.00 101.00   0.50    0.70    --  107.75 -94.00 150.00  132
 33  \w     38.00  72.00   0.50    0.70    --  107.75 -77.00  90.00   68
 34  \w     34.00 108.00   0.50    0.70    --  107.75 -94.00  60.00  148
 35  \w     39.00  68.00   0.50    0.70    --  107.75 -61.00  90.00   58
 36  \w     37.00  63.00   0.50    0.70    --  107.75 -61.00 150.00   52
 37  \w     35.00  97.00   0.50    0.70    --  107.75 -77.00 150.00  124
 38  \w     36.00  63.00   0.50    0.70    --  107.75-111.00 150.00   54
 39  \w     30.00  98.00   0.50    0.70    --   51.56-125.00   0.00  136
 40  \w     42.00  77.00   0.50    0.70    --  107.75 -94.00 -90.00   70
 41  \w     39.00  70.00   0.50    0.70    --  107.75 -61.00 -90.00   62
 42  \w     39.00  65.00   0.50    0.70    --  107.75 -61.00 -30.00   52
 43  \w     31.00  61.00   0.50    0.70    --  107.75-111.00 -60.00   60
 44  \w     41.00  71.00   0.50    0.70    --  107.75 -61.00-180.00   60
 45  \w     50.00  77.00   0.50    0.70    --  107.75 -77.00-180.00   54
 46  \w   -128.00 -42.00   0.50    0.70    --  -51.56 -38.00 150.00  172
 47  \w   -127.00 -82.00   0.50    0.70    --  -51.56 -99.00 -30.00   90
 48  \w   -124.00 -30.00   0.50    0.70    --  -51.56 -77.00 -90.00  188
 49  \w   -126.00 -70.00   0.50    0.70    --  -51.56-125.00 150.00  112
 50  \w   -164.00 -77.00   0.50    0.70    --  -86.25 -30.00  30.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2019886000
_diffrn_orient_matrix_UB_12      -0.0261885000
_diffrn_orient_matrix_UB_13      0.0644911000
_diffrn_orient_matrix_UB_21      0.0339863000
_diffrn_orient_matrix_UB_22      -0.0945853000
_diffrn_orient_matrix_UB_23      -0.1139314000
_diffrn_orient_matrix_UB_31      0.1126498000
_diffrn_orient_matrix_UB_32      0.1131303000
_diffrn_orient_matrix_UB_33      -0.0069377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.553
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         24423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0844
_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^)+(0.1623P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2217
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                19275
_reflns_number_total             24423
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9916\% 
 around [0.00 -0.00 1.00] (reciprocal) or [0.40 0.40 0.82] (direct)
;
_cod_data_source_file            suppl_j_ncrs-2022-0511_suppl.cif
_cod_data_source_block           emam11_tw
_cod_database_code               8107381
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2
 0.87 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B),
 C19(H19A,H19B), C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              39025
_shelx_hkl_checksum              85824
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.832
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2