#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:31:23 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240095.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240095
loop_
_publ_author_name
'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'
_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       'ω 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/[σ²(Fo²)+(0.0985P)²+1.4753P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.774
_shelx_estimated_absorpt_t_max   0.962
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8302(7) -0.0933(4) 0.3319(4) 0.0425(9) Uani 1 1 d . . . . .
C2 C 0.6639(6) -0.0246(4) 0.3725(4) 0.0423(9) Uani 1 1 d . . . . .
H2 H 0.540827 -0.072330 0.365541 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6775(6) 0.1183(4) 0.4250(3) 0.0348(8) Uani 1 1 d . . . . .
H3 H 0.562372 0.168180 0.452651 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8579(5) 0.1864(3) 0.4365(3) 0.0299(7) Uani 1 1 d . . . . .
C5 C 1.0255(6) 0.1123(4) 0.3932(3) 0.0372(8) Uani 1 1 d . . . . .
H5 H 1.149519 0.158965 0.399964 0.045 Uiso 1 1 calc R U . . .
C6 C 1.0119(7) -0.0286(4) 0.3406(4) 0.0442(9) Uani 1 1 d . . . . .
H6 H 1.125515 -0.079671 0.311216 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7644(5) 0.4250(3) 0.5615(3) 0.0289(7) Uani 1 1 d . . . . .
C8 C 0.5616(5) 0.5764(3) 0.7165(3) 0.0271(7) Uani 1 1 d . . . . .
C9 C 0.4269(5) 0.6451(3) 0.8181(3) 0.0262(6) Uani 1 1 d . . . . .
C10 C 0.2175(5) 0.5712(3) 0.7795(3) 0.0303(7) Uani 1 1 d . . . . .
H10A H 0.159190 0.572279 0.701521 0.036 Uiso 1 1 calc R U . . .
H10B H 0.228344 0.474865 0.762957 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0810(5) 0.6416(4) 0.8839(4) 0.0353(8) Uani 1 1 d . . . . .
H11 H -0.054527 0.593268 0.857900 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1702(5) 0.6379(4) 1.0040(4) 0.0360(8) Uani 1 1 d . . . . .
H12A H 0.081459 0.682054 1.071368 0.043 Uiso 1 1 calc R U . . .
H12B H 0.181594 0.542050 0.988871 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3770(5) 0.7129(4) 1.0443(3) 0.0338(7) Uani 1 1 d . . . . .
H13 H 0.434949 0.710825 1.122738 0.041 Uiso 1 1 calc R U . . .
C14 C 0.5137(5) 0.6424(4) 0.9401(3) 0.0304(7) Uani 1 1 d . . . . .
H14A H 0.526802 0.546723 0.925089 0.036 Uiso 1 1 calc R U . . .
H14B H 0.648352 0.689560 0.966364 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0641(5) 0.7899(4) 0.9076(4) 0.0399(8) Uani 1 1 d . . . . .
H15A H -0.025505 0.836010 0.974036 0.048 Uiso 1 1 calc R U . . .
H15B H 0.006256 0.792541 0.830246 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2714(5) 0.8639(3) 0.9479(4) 0.0355(8) Uani 1 1 d . . . . .
H16 H 0.259316 0.960801 0.963662 0.043 Uiso 1 1 calc R U . . .
C17 C 0.4080(5) 0.7943(3) 0.8436(3) 0.0306(7) Uani 1 1 d . . . . .
H17A H 0.541692 0.842887 0.868998 0.037 Uiso 1 1 calc R U . . .
H17B H 0.351845 0.797946 0.766375 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3604(6) 0.8612(4) 1.0677(3) 0.0375(8) Uani 1 1 d . . . . .
H18A H 0.274058 0.908337 1.135857 0.045 Uiso 1 1 calc R U . . .
H18B H 0.494324 0.909347 1.093718 0.045 Uiso 1 1 calc R U . . .
F1 F 0.8171(5) -0.2327(2) 0.2803(3) 0.0692(9) Uani 1 1 d . . . . .
N1 N 0.8818(4) 0.3287(3) 0.4849(3) 0.0322(6) Uani 1 1 d . . . . .
H1 H 0.994(6) 0.364(4) 0.466(4) 0.031(10) Uiso 1 1 d . . . . .
N2 N 0.7814(4) 0.5499(3) 0.5773(3) 0.0301(6) Uani 1 1 d . . . . .
N3 N 0.6645(4) 0.6371(3) 0.6669(3) 0.0301(6) Uani 1 1 d . . . . .
S1 S 0.59776(13) 0.40117(8) 0.65452(8) 0.0323(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 F1 118.7(4) . . ?
C2 C1 C6 122.8(4) . . ?
F1 C1 C6 118.5(4) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 N1 123.3(3) . . ?
C5 C4 N1 117.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 N1 120.5(3) . . ?
N2 C7 S1 113.6(2) . . ?
N1 C7 S1 125.7(3) . . ?
N3 C8 C9 125.2(3) . . ?
N3 C8 S1 113.0(2) . . ?
C9 C8 S1 121.8(2) . . ?
C8 C9 C17 110.0(3) . . ?
C8 C9 C10 110.4(3) . . ?
C17 C9 C10 109.1(3) . . ?
C8 C9 C14 110.1(3) . . ?
C17 C9 C14 108.7(3) . . ?
C10 C9 C14 108.5(3) . . ?
C11 C10 C9 110.1(3) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C15 C11 C10 109.0(3) . . ?
C15 C11 C12 109.6(3) . . ?
C10 C11 C12 109.5(3) . . ?
C15 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
C13 C12 C11 109.5(3) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C18 C13 C12 110.0(3) . . ?
C18 C13 C14 109.0(3) . . ?
C12 C13 C14 109.3(3) . . ?
C18 C13 H13 109.5 . . ?
C12 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C13 C14 C9 110.3(3) . . ?
C13 C14 H14A 109.6 . . ?
C9 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C9 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C11 C15 C16 109.5(3) . . ?
C11 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C11 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C18 C16 C15 110.0(3) . . ?
C18 C16 C17 109.7(3) . . ?
C15 C16 C17 109.6(3) . . ?
C18 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
C16 C17 C9 109.6(3) . . ?
C16 C17 H17A 109.7 . . ?
C9 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C9 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C16 C18 C13 109.3(3) . . ?
C16 C18 H18A 109.8 . . ?
C13 C18 H18A 109.8 . . ?
C16 C18 H18B 109.8 . . ?
C13 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C7 N1 C4 128.2(3) . . ?
C7 N1 H1 114(2) . . ?
C4 N1 H1 117(2) . . ?
C7 N2 N3 113.0(3) . . ?
C8 N3 N2 113.2(3) . . ?
C7 S1 C8 87.14(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.357(6) . ?
C1 F1 1.368(4) . ?
C1 C6 1.375(6) . ?
C2 C3 1.402(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(5) . ?
C4 N1 1.404(4) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.299(4) . ?
C7 N1 1.363(4) . ?
C7 S1 1.738(3) . ?
C8 N3 1.298(4) . ?
C8 C9 1.500(4) . ?
C8 S1 1.754(3) . ?
C9 C17 1.535(4) . ?
C9 C10 1.542(4) . ?
C9 C14 1.545(5) . ?
C10 C11 1.533(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.530(5) . ?
C11 C12 1.533(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.530(5) . ?
C13 C14 1.531(5) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.525(5) . ?
C16 C17 1.530(5) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 H1 0.93(4) . ?
N2 N3 1.388(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2 0.93(4) 1.99(4) 2.920(4) 175(4) 2_766 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C2 C3 C4 N1 178.2(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
N1 C4 C5 C6 -177.9(3) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
F1 C1 C6 C5 -179.7(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
N3 C8 C9 C17 7.0(5) . . . . ?
S1 C8 C9 C17 -174.2(2) . . . . ?
N3 C8 C9 C10 127.5(3) . . . . ?
S1 C8 C9 C10 -53.7(4) . . . . ?
N3 C8 C9 C14 -112.7(4) . . . . ?
S1 C8 C9 C14 66.1(3) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C17 C9 C10 C11 -59.2(4) . . . . ?
C14 C9 C10 C11 59.0(4) . . . . ?
C9 C10 C11 C15 59.8(4) . . . . ?
C9 C10 C11 C12 -60.1(4) . . . . ?
C15 C11 C12 C13 -59.3(4) . . . . ?
C10 C11 C12 C13 60.3(4) . . . . ?
C11 C12 C13 C18 59.4(4) . . . . ?
C11 C12 C13 C14 -60.3(4) . . . . ?
C18 C13 C14 C9 -60.0(4) . . . . ?
C12 C13 C14 C9 60.3(4) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C17 C9 C14 C13 59.3(3) . . . . ?
C10 C9 C14 C13 -59.2(3) . . . . ?
C10 C11 C15 C16 -60.3(4) . . . . ?
C12 C11 C15 C16 59.5(4) . . . . ?
C11 C15 C16 C18 -59.9(4) . . . . ?
C11 C15 C16 C17 60.8(4) . . . . ?
C18 C16 C17 C9 60.7(4) . . . . ?
C15 C16 C17 C9 -60.2(4) . . . . ?
C8 C9 C17 C16 -179.7(3) . . . . ?
C10 C9 C17 C16 59.0(4) . . . . ?
C14 C9 C17 C16 -59.1(3) . . . . ?
C15 C16 C18 C13 59.7(4) . . . . ?
C17 C16 C18 C13 -61.0(4) . . . . ?
C12 C13 C18 C16 -59.5(4) . . . . ?
C14 C13 C18 C16 60.4(4) . . . . ?
N2 C7 N1 C4 -165.6(3) . . . . ?
S1 C7 N1 C4 19.7(5) . . . . ?
C3 C4 N1 C7 22.3(6) . . . . ?
C5 C4 N1 C7 -160.8(3) . . . . ?
N1 C7 N2 N3 -174.3(3) . . . . ?
S1 C7 N2 N3 1.0(4) . . . . ?
C9 C8 N3 N2 178.2(3) . . . . ?
S1 C8 N3 N2 -0.7(4) . . . . ?
C7 N2 N3 C8 -0.2(4) . . . . ?
N2 C7 S1 C8 -1.1(3) . . . . ?
N1 C7 S1 C8 173.9(3) . . . . ?
N3 C8 S1 C7 1.0(3) . . . . ?
C9 C8 S1 C7 -177.9(3) . . . . ?
