Quantitative assessment of the nature of noncovalent interactions in N-substituted-5-(adamantan-1-yl)-1,3,4-thiadiazole-2-amines: insights from crystallographic and QTAIM analysis
El-Emam, Ali A.; Saveeth Kumar, Elangovan; Janani, Krishnakumar; Al-Wahaibi, Lamya H.; Blacque, Olivier; El-Awady, Mohamed I.; Al-Shaalan, Nora H.; Percino, M. Judith; Thamotharan, Subbiah; RSC Advances 10 (2020) 9840–9853; doi:10.1039/D0RA00733A

data_7240096
_publ_section_title
;
 Quantitative assessment of the nature of noncovalent interactions in
 N-substituted-5-(adamantan-1-yl)-1,3,4-thiadiazole-2-amines: insights
 from crystallographic and QTAIM analysis
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              9840
_journal_page_last               9853
_journal_paper_doi               10.1039/D0RA00733A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H20 Br N3 S'
_chemical_formula_sum            'C18 H20 Br N3 S'
_chemical_formula_weight         390.34
_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
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                110.417(2)
_cell_angle_beta                 95.240(2)
_cell_angle_gamma                93.613(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7648(2)
_cell_length_b                   11.4551(2)
_cell_length_c                   11.4985(2)
_cell_measurement_reflns_used    12771
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.8960
_cell_measurement_theta_min      4.0940
_cell_volume                     827.26(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_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   -124.00 -38.00   0.50    0.25    --  -51.56 -57.00 120.00  172
  2  \w   -127.00 -82.00   0.50    0.25    --  -51.56 -99.00-180.00   90
  3  \w   -127.00 -82.00   0.50    0.25    --  -51.56 -99.00 120.00   90
  4  \w    -92.00  -9.00   0.50    0.25    --  -51.56 125.00-180.00  166
  5  \w    -27.00  26.00   0.50    0.25    --   51.56 -19.00 -60.00  106
  6  \w   -157.00 -71.00   0.50    0.25    --  -86.25 -61.00  60.00  172
  7  \w     35.00 105.00   0.50    0.25    --  107.75 -77.00 -90.00  140
  8  \w     99.00 178.00   0.50    0.25    --  107.75 111.00 150.00  158
  9  \w     93.00 178.00   0.50    0.25    --  107.75  61.00-120.00  170
 10  \w     31.00 112.00   0.50    0.25    --  107.75-111.00-150.00  162
 11  \w     86.00 178.00   0.50    0.25    --  107.75  77.00 -90.00  184
 12  \w     37.00  71.00   0.50    0.25    --  107.75 -61.00  30.00   68
 13  \w     31.00 112.00   0.50    0.25    --  107.75-111.00 120.00  162
 14  \w     31.00 112.00   0.50    0.25    --  107.75-111.00  90.00  162
 15  \w     37.00  71.00   0.50    0.25    --  107.75 -61.00 150.00   68
 16  \w     35.00 105.00   0.50    0.25    --  107.75 -77.00-150.00  140
 17  \w     37.00  71.00   0.50    0.25    --  107.75 -61.00  60.00   68
 18  \w     37.00  71.00   0.50    0.25    --  107.75 -61.00  90.00   68
 19  \w     30.00 124.00   0.50    0.25    --   51.56  77.00 -60.00  188
 20  \w     42.00 128.00   0.50    0.25    --   51.56  38.00-120.00  172
 21  \w   -120.00 -94.00   0.50    0.25    --  -54.56 -38.00  30.00   52
 22  \w    -76.00 -48.00   0.50    0.25    --  -54.56 -38.00  30.00   56
 23  \w    -37.00  -3.00   0.50    0.25    --  -54.56  38.00-180.00   68
 24  \w   -115.00 -82.00   0.50    0.25    --  -86.25-111.00 -30.00   66
 25  \w   -157.00-131.00   0.50    0.25    --  -86.25-111.00 -30.00   52
 26  \w     51.00  77.00   0.50    0.25    --  107.75 -77.00 150.00   52
 27  \w     37.00  63.00   0.50    0.25    --  107.75 -61.00-150.00   52
 28  \w     39.00  71.00   0.50    0.25    --  107.75 -61.00 -30.00   64
 29  \w     78.00 109.00   0.50    0.25    --  107.75-111.00  30.00   62
 30  \w     34.00  60.00   0.50    0.25    --  107.75-111.00  30.00   52
 31  \w    129.00 177.00   0.50    0.25    --  107.75  77.00 120.00   96
 32  \w     75.00 105.00   0.50    0.25    --  107.75 -94.00-150.00   60
 33  \w     75.00 108.00   0.50    0.25    --  107.75 -94.00 120.00   66
 34  \w    109.00 135.00   0.50    0.25    --  107.75  15.00-180.00   52
 35  \w     36.00  71.00   0.50    0.25    --  107.75 -94.00-150.00   70
 36  \w    137.00 163.00   0.50    0.25    --  107.75  15.00-180.00   52
 37  \w     86.00 117.00   0.50    0.25    --  107.75  77.00 120.00   62
 38  \w     32.00  68.00   0.50    0.25    --  107.75-111.00 -30.00   72
 39  \w     82.00 107.00   0.50    0.25    --  107.75-111.00 -30.00   50
 40  \w    121.00 172.00   0.50    0.25    --  107.75  15.00  60.00  102
 41  \w     87.00 113.00   0.50    0.25    --  107.75-112.00 -16.91   52
 42  \w    110.00 135.00   0.50    0.25    --  107.75 111.00 -60.00   50
 43  \w     31.00  81.00   0.50    0.25    --  107.75-112.00 -16.91  100
 44  \w   -127.00 -33.00   0.50    0.25    --  -54.56 -77.00-150.00  188
 45  \w   -127.00 -44.00   0.50    0.25    --  -54.56 -77.00 120.00  166
 46  \w   -127.00 -41.00   0.50    0.25    --  -54.56 -57.00   0.00  172
;
_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      -0.0363154000
_diffrn_orient_matrix_UB_12      0.1349992000
_diffrn_orient_matrix_UB_13      0.0123138000
_diffrn_orient_matrix_UB_21      0.2174866000
_diffrn_orient_matrix_UB_22      0.0247806000
_diffrn_orient_matrix_UB_23      -0.0218877000
_diffrn_orient_matrix_UB_31      -0.0650032000
_diffrn_orient_matrix_UB_32      -0.0443715000
_diffrn_orient_matrix_UB_33      -0.1418147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14178
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.133
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.574
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (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    1.567
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.3959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3269
_reflns_number_total             3385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00733a2.cif
_cod_data_source_block           emam06
_cod_depositor_comments
'Adding full bibliography for 7240094--7240096.cif.'
_cod_database_code               7240096
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.711
_shelx_estimated_absorpt_t_min   0.361
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,
 H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              79311