#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222034
loop_
_publ_author_name
'Khan, Mahmood-ul-Hassan'
'Hameed, Shahid'
'Tahir, M. Nawaz'
'Bokhari, Tanveer Hussain'
'Khan, Islam Ullah'
_publ_section_title
6-(1-Adamantyl)-3-(2-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole
_journal_coeditor_code           HB2984
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1437
_journal_paper_doi               10.1107/S1600536809019692
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H19 F N4 S'
_chemical_formula_moiety         'C19 H19 F N4 S'
_chemical_formula_sum            'C19 H19 F N4 S'
_chemical_formula_weight         354.44
_chemical_name_systematic
;
6-(1-Adamantyl)-3-(2-fluorophenyl)-1,2,4-
triazolo[3,4-b][1,3,4]thiadiazole
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2684(9)
_cell_length_b                   12.4293(9)
_cell_length_c                   20.2231(15)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      2.46
_cell_volume                     3335.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22695
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+1.3259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                3116
_reflns_number_total             4486
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2984.cif
_cod_data_source_block           I
_cod_database_code               2222034
_cod_database_fobs_code          2222034
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.25232(4) -0.15058(4) 0.23126(2) 0.0517(2) Uani . . 1.000
F F1 0.35571(14) -0.27396(11) 0.52074(7) 0.0839(6) Uani . . 1.000
N N1 0.20243(13) -0.22822(13) 0.41446(9) 0.0543(6) Uani . . 1.000
N N2 0.17459(14) -0.24778(14) 0.34844(9) 0.0591(6) Uani . . 1.000
N N3 0.29443(10) -0.12526(11) 0.35182(7) 0.0360(4) Uani . . 1.000
N N4 0.36117(10) -0.05549(11) 0.32199(7) 0.0343(4) Uani . . 1.000
C C1 0.32252(13) -0.10525(14) 0.47314(9) 0.0392(5) Uani . . 1.000
C C2 0.36251(16) -0.16551(17) 0.52410(10) 0.0517(6) Uani . . 1.000
C C3 0.41073(19) -0.1200(2) 0.57717(10) 0.0639(8) Uani . . 1.000
C C4 0.41784(17) -0.0094(2) 0.58048(10) 0.0611(8) Uani . . 1.000
C C5 0.37749(16) 0.05301(18) 0.53119(10) 0.0549(7) Uani . . 1.000
C C6 0.33120(14) 0.00584(15) 0.47758(9) 0.0463(6) Uani . . 1.000
C C7 0.27374(13) -0.15494(14) 0.41576(9) 0.0403(5) Uani . . 1.000
C C8 0.23167(13) -0.18403(14) 0.31343(10) 0.0437(5) Uani . . 1.000
C C9 0.34740(12) -0.06062(13) 0.25887(8) 0.0348(5) Uani . . 1.000
C C10 0.40431(12) 0.00535(13) 0.20943(8) 0.0337(4) Uani . . 1.000
C C11 0.48759(15) 0.07039(18) 0.24376(9) 0.0504(6) Uani . . 1.000
C C12 0.54359(15) 0.13979(18) 0.19241(10) 0.0543(7) Uani . . 1.000
C C13 0.47109(16) 0.21626(17) 0.15982(11) 0.0581(7) Uani . . 1.000
C C14 0.38813(17) 0.15387(18) 0.12638(12) 0.0626(8) Uani . . 1.000
C C15 0.33138(15) 0.08502(16) 0.17677(11) 0.0527(6) Uani . . 1.000
C C16 0.4512(2) -0.06639(17) 0.15637(11) 0.0657(8) Uani . . 1.000
C C17 0.5082(3) 0.0039(2) 0.10590(12) 0.0802(9) Uani . . 1.000
C C18 0.59042(18) 0.0674(2) 0.14102(13) 0.0730(9) Uani . . 1.000
C C19 0.4329(3) 0.0822(2) 0.07399(11) 0.0855(10) Uani . . 1.000
H H3 0.43812 -0.16293 0.61028 0.0767 Uiso . . 1.000
H H4 0.45004 0.02286 0.61619 0.0733 Uiso . . 1.000
H H5 0.38143 0.12757 0.53400 0.0658 Uiso . . 1.000
H H6 0.30545 0.04888 0.44397 0.0555 Uiso . . 1.000
H H11A 0.45818 0.11629 0.27742 0.0604 Uiso . . 1.000
H H11B 0.53468 0.02185 0.26512 0.0604 Uiso . . 1.000
H H12 0.59673 0.18097 0.21460 0.0651 Uiso . . 1.000
H H13A 0.44245 0.26409 0.19273 0.0697 Uiso . . 1.000
H H13B 0.50652 0.25966 0.12744 0.0697 Uiso . . 1.000
H H14 0.34099 0.20433 0.10564 0.0751 Uiso . . 1.000
H H15A 0.30145 0.13091 0.21022 0.0633 Uiso . . 1.000
H H15B 0.27764 0.04595 0.15483 0.0633 Uiso . . 1.000
H H16A 0.49735 -0.11705 0.17670 0.0789 Uiso . . 1.000
H H16B 0.39877 -0.10692 0.13405 0.0789 Uiso . . 1.000
H H17 0.53836 -0.04191 0.07176 0.0963 Uiso . . 1.000
H H18A 0.62742 0.11032 0.10915 0.0876 Uiso . . 1.000
H H18B 0.63734 0.01826 0.16203 0.0876 Uiso . . 1.000
H H19A 0.37972 0.04208 0.05216 0.1027 Uiso . . 1.000
H H19B 0.46694 0.12570 0.04103 0.1027 Uiso . . 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C9 . . . 87.82(8) no
N2 N1 C7 . . . 109.15(16) no
N1 N2 C8 . . . 104.93(16) no
N4 N3 C7 . . . 135.23(14) no
N4 N3 C8 . . . 118.95(14) no
C7 N3 C8 . . . 105.81(14) no
N3 N4 C9 . . . 108.10(13) no
C2 C1 C6 . . . 117.36(17) no
C2 C1 C7 . . . 122.17(17) no
C6 C1 C7 . . . 120.47(16) no
F1 C2 C1 . . . 118.53(18) no
F1 C2 C3 . . . 118.78(19) no
C1 C2 C3 . . . 122.7(2) no
C2 C3 C4 . . . 118.7(2) no
C3 C4 C5 . . . 120.1(2) no
C4 C5 C6 . . . 120.4(2) no
C1 C6 C5 . . . 120.75(18) no
N1 C7 N3 . . . 108.16(16) no
N1 C7 C1 . . . 128.78(17) no
N3 C7 C1 . . . 122.99(15) no
S1 C8 N2 . . . 139.20(16) no
S1 C8 N3 . . . 108.85(13) no
N2 C8 N3 . . . 111.95(18) no
S1 C9 N4 . . . 116.26(12) no
S1 C9 C10 . . . 119.54(12) no
N4 C9 C10 . . . 124.18(15) no
C9 C10 C11 . . . 110.45(14) no
C9 C10 C15 . . . 108.84(14) no
C9 C10 C16 . . . 110.78(14) no
C11 C10 C15 . . . 107.99(15) no
C11 C10 C16 . . . 109.38(16) no
C15 C10 C16 . . . 109.35(15) no
C10 C11 C12 . . . 109.70(15) no
C11 C12 C13 . . . 109.91(17) no
C11 C12 C18 . . . 109.21(18) no
C13 C12 C18 . . . 109.78(18) no
C12 C13 C14 . . . 109.79(18) no
C13 C14 C15 . . . 110.41(19) no
C13 C14 C19 . . . 109.4(2) no
C15 C14 C19 . . . 109.39(19) no
C10 C15 C14 . . . 109.73(16) no
C10 C16 C17 . . . 109.51(17) no
C16 C17 C18 . . . 109.7(2) no
C16 C17 C19 . . . 108.5(3) no
C18 C17 C19 . . . 109.5(2) no
C12 C18 C17 . . . 109.6(2) no
C14 C19 C17 . . . 109.61(19) no
C2 C3 H3 . . . 121.00 no
C4 C3 H3 . . . 121.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C10 C11 H11A . . . 110.00 no
C10 C11 H11B . . . 110.00 no
C12 C11 H11A . . . 110.00 no
C12 C11 H11B . . . 110.00 no
H11A C11 H11B . . . 108.00 no
C11 C12 H12 . . . 109.00 no
C13 C12 H12 . . . 109.00 no
C18 C12 H12 . . . 109.00 no
C12 C13 H13A . . . 110.00 no
C12 C13 H13B . . . 110.00 no
C14 C13 H13A . . . 110.00 no
C14 C13 H13B . . . 110.00 no
H13A C13 H13B . . . 108.00 no
C13 C14 H14 . . . 109.00 no
C15 C14 H14 . . . 109.00 no
C19 C14 H14 . . . 109.00 no
C10 C15 H15A . . . 110.00 no
C10 C15 H15B . . . 110.00 no
C14 C15 H15A . . . 110.00 no
C14 C15 H15B . . . 110.00 no
H15A C15 H15B . . . 108.00 no
C10 C16 H16A . . . 110.00 no
C10 C16 H16B . . . 110.00 no
C17 C16 H16A . . . 110.00 no
C17 C16 H16B . . . 110.00 no
H16A C16 H16B . . . 108.00 no
C16 C17 H17 . . . 110.00 no
C18 C17 H17 . . . 110.00 no
C19 C17 H17 . . . 110.00 no
C12 C18 H18A . . . 110.00 no
C12 C18 H18B . . . 110.00 no
C17 C18 H18A . . . 110.00 no
C17 C18 H18B . . . 110.00 no
H18A C18 H18B . . . 108.00 no
C14 C19 H19A . . . 110.00 no
C14 C19 H19B . . . 110.00 no
C17 C19 H19A . . . 110.00 no
C17 C19 H19B . . . 110.00 no
H19A C19 H19B . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . . 1.735(2) no
S1 C9 . . 1.7758(17) no
F1 C2 . . 1.353(3) no
N1 N2 . . 1.407(3) no
N1 C7 . . 1.314(2) no
N2 C8 . . 1.305(3) no
N3 N4 . . 1.3784(19) no
N3 C7 . . 1.372(2) no
N3 C8 . . 1.353(2) no
N4 C9 . . 1.291(2) no
C1 C2 . . 1.380(3) no
C1 C6 . . 1.389(3) no
C1 C7 . . 1.465(3) no
C2 C3 . . 1.372(3) no
C3 C4 . . 1.380(4) no
C4 C5 . . 1.372(3) no
C5 C6 . . 1.377(3) no
C9 C10 . . 1.497(2) no
C10 C11 . . 1.535(3) no
C10 C15 . . 1.534(3) no
C10 C16 . . 1.528(3) no
C11 C12 . . 1.541(3) no
C12 C13 . . 1.504(3) no
C12 C18 . . 1.509(3) no
C13 C14 . . 1.507(3) no
C14 C15 . . 1.529(3) no
C14 C19 . . 1.506(4) no
C16 C17 . . 1.542(4) no
C17 C18 . . 1.522(4) no
C17 C19 . . 1.537(5) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12 H12 . . 0.9800 no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C14 H14 . . 0.9800 no
C15 H15A . . 0.9700 no
C15 H15B . . 0.9700 no
C16 H16A . . 0.9700 no
C16 H16B . . 0.9700 no
C17 H17 . . 0.9800 no
C18 H18A . . 0.9700 no
C18 H18B . . 0.9700 no
C19 H19A . . 0.9700 no
C19 H19B . . 0.9700 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15A S1 7_555 0.97 2.84 3.640(2) 140 yes
C12 H12 Cg1 4_655 0.98 2.90 3.713(2) 140 yes
C18 H18B Cg1 6_555 0.97 2.83 3.787(3) 170 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 S1 C8 N2 . . . . -179.0(2) no
C9 S1 C8 N3 . . . . 1.05(13) no
C8 S1 C9 N4 . . . . -0.64(14) no
C8 S1 C9 C10 . . . . -179.31(14) no
C7 N1 N2 C8 . . . . -0.1(2) no
N2 N1 C7 N3 . . . . -0.2(2) no
N2 N1 C7 C1 . . . . 176.70(17) no
N1 N2 C8 S1 . . . . -179.67(17) no
N1 N2 C8 N3 . . . . 0.3(2) no
C7 N3 N4 C9 . . . . 179.60(18) no
C8 N3 N4 C9 . . . . 0.9(2) no
N4 N3 C7 N1 . . . . -178.48(16) no
N4 N3 C7 C1 . . . . 4.4(3) no
C8 N3 C7 N1 . . . . 0.33(19) no
C8 N3 C7 C1 . . . . -176.77(16) no
N4 N3 C8 S1 . . . . -1.38(18) no
N4 N3 C8 N2 . . . . 178.67(15) no
C7 N3 C8 S1 . . . . 179.58(12) no
C7 N3 C8 N2 . . . . -0.4(2) no
N3 N4 C9 S1 . . . . 0.02(17) no
N3 N4 C9 C10 . . . . 178.62(14) no
C6 C1 C2 F1 . . . . -179.52(18) no
C6 C1 C2 C3 . . . . -1.0(3) no
C7 C1 C2 F1 . . . . -0.3(3) no
C7 C1 C2 C3 . . . . 178.2(2) no
C2 C1 C6 C5 . . . . -0.4(3) no
C7 C1 C6 C5 . . . . -179.61(18) no
C2 C1 C7 N1 . . . . 50.7(3) no
C2 C1 C7 N3 . . . . -132.83(19) no
C6 C1 C7 N1 . . . . -130.1(2) no
C6 C1 C7 N3 . . . . 46.3(3) no
F1 C2 C3 C4 . . . . 179.9(2) no
C1 C2 C3 C4 . . . . 1.3(3) no
C2 C3 C4 C5 . . . . -0.3(3) no
C3 C4 C5 C6 . . . . -1.1(3) no
C4 C5 C6 C1 . . . . 1.5(3) no
S1 C9 C10 C11 . . . . -175.71(12) no
S1 C9 C10 C15 . . . . 65.90(17) no
S1 C9 C10 C16 . . . . -54.36(19) no
N4 C9 C10 C11 . . . . 5.7(2) no
N4 C9 C10 C15 . . . . -112.66(18) no
N4 C9 C10 C16 . . . . 127.08(18) no
C9 C10 C11 C12 . . . . -178.63(15) no
C15 C10 C11 C12 . . . . -59.7(2) no
C16 C10 C11 C12 . . . . 59.2(2) no
C9 C10 C15 C14 . . . . 179.60(16) no
C11 C10 C15 C14 . . . . 59.7(2) no
C16 C10 C15 C14 . . . . -59.3(2) no
C9 C10 C16 C17 . . . . 179.4(2) no
C11 C10 C16 C17 . . . . -58.6(2) no
C15 C10 C16 C17 . . . . 59.5(2) no
C10 C11 C12 C13 . . . . 60.2(2) no
C10 C11 C12 C18 . . . . -60.3(2) no
C11 C12 C13 C14 . . . . -59.2(2) no
C18 C12 C13 C14 . . . . 61.0(2) no
C11 C12 C18 C17 . . . . 61.0(2) no
C13 C12 C18 C17 . . . . -59.6(2) no
C12 C13 C14 C15 . . . . 59.4(2) no
C12 C13 C14 C19 . . . . -61.0(2) no
C13 C14 C15 C10 . . . . -60.1(2) no
C19 C14 C15 C10 . . . . 60.3(2) no
C13 C14 C19 C17 . . . . 59.7(3) no
C15 C14 C19 C17 . . . . -61.4(3) no
C10 C16 C17 C18 . . . . 59.5(3) no
C10 C16 C17 C19 . . . . -60.1(2) no
C16 C17 C18 C12 . . . . -60.8(3) no
C19 C17 C18 C12 . . . . 58.2(3) no
C16 C17 C19 C14 . . . . 61.2(3) no
C18 C17 C19 C14 . . . . -58.5(3) no
