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_7240094
_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         'C14 H21 N3 S'
_chemical_formula_sum            'C14 H21 N3 S'
_chemical_formula_weight         263.40
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-22
_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                90
_cell_angle_beta                 114.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8339(2)
_cell_length_b                   15.8974(2)
_cell_length_c                   9.4749(2)
_cell_measurement_reflns_used    12263
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.1
_cell_measurement_theta_min      5.1
_cell_volume                     1348.26(5)
_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    -26.00  25.00   0.50    0.50    --  -54.56  19.00  60.00  102
  2  \w   -127.00 -33.00   0.50    0.50    --  -54.56 -77.00 120.00  188
  3  \w   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 150.00   96
  4  \w   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00   0.00   96
  5  \w   -130.00 -82.00   0.50    0.50    --  -54.56 -99.00 -60.00   96
  6  \w   -163.00 -78.00   0.50    2.00    --  -86.25-111.00-150.00  170
  7  \w     98.00 178.00   0.50    2.00    --  107.75 113.00  69.65  160
  8  \w    153.00 178.00   0.50    2.00    --  107.75  45.00  30.00   50
  9  \w    127.00 177.00   0.50    2.00    --  107.75 111.00 -60.00  100
 10  \w    129.00 178.00   0.50    2.00    --  107.75 111.00 -90.00   98
 11  \w    117.00 143.00   0.50    2.00    --  107.75  45.00 -90.00   52
 12  \w    107.00 176.00   0.50    2.00    --  107.75  61.00 -90.00  138
 13  \w     98.00 178.00   0.50    2.00    --  107.75  15.00   0.00  160
 14  \w    100.00 178.00   0.50    2.00    --  107.75  61.00   0.00  156
 15  \w     99.00 134.00   0.50    2.00    --  107.75  15.00  90.00   70
 16  \w    104.00 129.00   0.50    2.00    --  107.75  45.00 150.00   50
 17  \w    131.00 168.00   0.50    2.00    --  107.75  45.00 150.00   74
 18  \w    100.00 126.00   0.50    2.00    --  107.75  45.00  30.00   52
 19  \w     88.00 178.00   0.50    2.00    --  107.75  73.00 -48.67  180
 20  \w     78.00 110.00   0.50    2.00    --  107.75 -78.00  84.85   64
 21  \w     82.00 111.00   0.50    2.00    --  107.75-111.00 120.00   58
 22  \w     54.00  81.00   0.50    2.00    --  107.75 -77.00 120.00   54
 23  \w     53.00  90.00   0.50    2.00    --  107.75-111.00  90.00   74
 24  \w     38.00  67.00   0.50    2.00    --  107.75 -78.00  84.85   58
 25  \w     32.00  58.00   0.50    2.00    --  107.75-111.00 120.00   52
 26  \w     40.00  66.00   0.50    2.00    --  107.75 -61.00 -30.00   52
 27  \w     53.00  79.00   0.50    2.00    --  107.75 -94.00 -60.00   52
 28  \w     85.00 111.00   0.50    2.00    --  107.75-111.00 -90.00   52
 29  \w     78.00 103.00   0.50    2.00    --  107.75 -94.00 -30.00   50
 30  \w     41.00  71.00   0.50    2.00    --  107.75 -61.00-120.00   60
 31  \w     58.00 104.00   0.50    2.00    --  107.75 -77.00-150.00   92
 32  \w     75.00 103.00   0.50    2.00    --  107.75 -94.00-180.00   56
 33  \w     66.00  97.00   0.50    2.00    --  107.75 -77.00-180.00   62
 34  \w     41.00  75.00   0.50    2.00    --  107.75-111.00 -90.00   68
 35  \w     35.00  61.00   0.50    2.00    --  107.75 -55.00-118.00   52
 36  \w     88.00 138.00   0.50    2.00    --  107.75  73.00 179.37  100
;
_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      0.1538168000
_diffrn_orient_matrix_UB_12      0.0433428000
_diffrn_orient_matrix_UB_13      0.0604804000
_diffrn_orient_matrix_UB_21      0.0473689000
_diffrn_orient_matrix_UB_22      -0.0470466000
_diffrn_orient_matrix_UB_23      0.1552494000
_diffrn_orient_matrix_UB_31      0.0609542000
_diffrn_orient_matrix_UB_32      -0.0728009000
_diffrn_orient_matrix_UB_33      -0.0644067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15881
_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         79.304
_diffrn_reflns_theta_min         5.566
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.795
_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    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0422P)^2^+0.4756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2798
_reflns_number_total             2920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00733a2.cif
_cod_data_source_block           emam4
_cod_depositor_comments
'Adding full bibliography for 7240094--7240096.cif.'
_cod_database_code               7240094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              15296