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_7240095
_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_sum            'C18 H20 F N3 S'
_chemical_formula_weight         329.43
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-15 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                116.607(6)
_cell_angle_beta                 94.587(8)
_cell_angle_gamma                90.941(6)
_cell_formula_units_Z            2
_cell_length_a                   6.7254(7)
_cell_length_b                   10.9787(5)
_cell_length_c                   11.9955(10)
_cell_measurement_reflns_used    7073
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      78.9280
_cell_measurement_theta_min      4.0800
_cell_volume                     788.01(12)
_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_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12473
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.499
_diffrn_reflns_theta_min         4.142
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.851
_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    1.388
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.083
_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     212
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0985P)^2^+1.4753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2735
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00733a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7240094--7240096.cif.'
_cod_database_code               7240095
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.774
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              16440