#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228452.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_2228452
loop_
_publ_author_name
'Khan, Mahmood-ul-Hassan'
'Hameed, Shahid'
'Akhtar, Tashfeen'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 6-(Adamantan-1-yl)-3-(3-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole
;
_journal_coeditor_code           KP2286
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3215
_journal_page_last               o3216
_journal_paper_doi               10.1107/S1600536810046428
_journal_volume                  66
_journal_year                    2010
_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-(Adamantan-1-yl)-3-(3-fluorophenyl)-1,2,4-
triazolo[3,4-b][1,3,4]thiadiazole
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.379(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6385(16)
_cell_length_b                   6.6555(5)
_cell_length_c                   11.6634(16)
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      3.05
_cell_volume                     802.2(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2006)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publcif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ and 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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6164
_diffrn_reflns_theta_full        26.14
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         3.36
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1708
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                1223
_reflns_number_total             1708
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2286.cif
_cod_data_source_block           I
_cod_original_cell_volume        802.25(17)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2228452
_cod_database_fobs_code          2228452
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,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 0.42509(5) 0.75000 0.98501(5) 0.0307(2) Uani . . 1.000
F F1A -0.2195(2) 0.75000 1.1429(2) 0.0500(6) Uani . . 0.900
N N1 0.17319(15) 0.75000 0.85412(15) 0.0251(5) Uani . . 1.000
N N2 0.20898(15) 0.75000 0.98446(16) 0.0243(5) Uani . . 1.000
N N3 0.35605(17) 0.75000 1.18934(17) 0.0325(6) Uani . . 1.000
N N4 0.23242(17) 0.75000 1.18047(16) 0.0311(6) Uani . . 1.000
C C1 0.27709(18) 0.75000 0.84027(19) 0.0249(6) Uani . . 1.000
C C2 0.33636(19) 0.75000 1.06956(19) 0.0268(6) Uani . . 1.000
C C3 0.14499(19) 0.75000 1.05806(19) 0.0257(6) Uani . . 1.000
C C4 0.00535(19) 0.75000 1.0101(2) 0.0248(6) Uani . . 1.000
C C5 -0.0419(2) 0.75000 1.1000(2) 0.0318(7) Uani . . 1.000
C C6 -0.1732(2) 0.75000 1.0556(2) 0.0342(7) Uani . . 1.000
C C7 -0.2599(2) 0.75000 0.9272(2) 0.0378(8) Uani . . 1.000
C C8 -0.2117(2) 0.75000 0.8390(2) 0.0367(8) Uani . . 1.000
C C9 -0.08020(19) 0.75000 0.8790(2) 0.0299(7) Uani . . 1.000
C C10 0.27522(18) 0.75000 0.71113(18) 0.0254(6) Uani . . 1.000
C C11 0.34448(16) 0.9374(3) 0.69694(15) 0.0362(5) Uani . . 1.000
C C12 0.34071(17) 0.9366(3) 0.56371(15) 0.0413(6) Uani . . 1.000
C C13 0.20148(17) 0.9360(3) 0.45854(15) 0.0428(6) Uani . . 1.000
C C14 0.1337(2) 0.75000 0.4720(2) 0.0382(8) Uani . . 1.000
C C15 0.1355(2) 0.75000 0.6040(2) 0.0368(7) Uani . . 1.000
C C16 0.4093(2) 0.75000 0.5501(2) 0.0441(9) Uani . . 1.000
F F1B -0.2859(18) 0.75000 0.7166(11) 0.052(5) Uani . . 0.100
H H7 -0.3504(11) 0.75000 0.902(2) 0.0450 Uiso . . 1.000
H H8A -0.276(4) 0.75000 0.7516(18) 0.0440 Uiso . . 0.900
H H9 -0.04830 0.75000 0.81730 0.0360 Uiso calc . 1.000
H H11A 0.30140 1.05980 0.70660 0.0440 Uiso calc R 1.000
H H11B 0.43540 0.93830 0.76530 0.0440 Uiso calc R 1.000
H H12 0.38550 1.05930 0.55460 0.0490 Uiso calc R 1.000
H H5 0.01550 0.75000 1.19000 0.0380 Uiso calc . 1.000
H H13B 0.19930 0.93710 0.37270 0.0510 Uiso calc R 1.000
H H14 0.04200 0.75000 0.40260 0.0460 Uiso calc . 1.000
H H15A 0.08990 0.87050 0.61220 0.0440 Uiso calc . 0.500
H H15B 0.08990 0.62950 0.61220 0.0440 Uiso calc . 0.500
H H16A 0.40810 0.75000 0.46460 0.0530 Uiso calc . 1.000
H H16B 0.50060 0.75000 0.61760 0.0530 Uiso calc . 1.000
H H13A 0.15650 1.05780 0.46590 0.0510 Uiso calc R 1.000
H H6B -0.21(3) 0.75000 1.11(2) 0.0410 Uiso . . 0.100
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'
F F 0.0171 0.0103 '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'
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
C1 S1 C2 . . . 88.25(11) no
N2 N1 C1 . . . 108.20(17) no
N1 N2 C2 . . . 118.84(18) no
N1 N2 C3 . . . 135.60(19) no
C2 N2 C3 . . . 105.56(17) no
N4 N3 C2 . . . 104.65(18) no
N3 N4 C3 . . . 109.67(18) no
S1 C1 N1 . . . 115.88(15) no
S1 C1 C10 . . . 121.10(17) no
N1 C1 C10 . . . 123.02(19) no
S1 C2 N2 . . . 108.83(15) no
S1 C2 N3 . . . 138.93(19) no
N2 C2 N3 . . . 112.2(2) no
N2 C3 N4 . . . 107.9(2) no
N2 C3 C4 . . . 126.26(18) no
N4 C3 C4 . . . 125.9(2) no
C3 C4 C5 . . . 117.99(19) no
C3 C4 C9 . . . 122.1(2) no
C5 C4 C9 . . . 119.9(2) no
C4 C5 C6 . . . 118.3(2) no
F1A C6 C5 . . . 118.5(2) no
F1A C6 C7 . . . 118.4(2) no
C5 C6 C7 . . . 123.2(2) no
C6 C7 C8 . . . 117.9(2) no
C7 C8 C9 . . . 121.1(2) no
F1B C8 C7 . . . 122.2(10) no
F1B C8 C9 . . . 116.8(10) no
C4 C9 C8 . . . 119.6(2) no
C1 C10 C11 . . . 110.08(11) no
C1 C10 C15 . . . 109.90(19) no
C1 C10 C11 . . 4_565 110.08(11) no
C11 C10 C15 . . . 109.02(11) no
C11 C10 C11 . . 4_565 108.71(18) no
C11 C10 C15 4_565 . . 109.02(11) no
C10 C11 C12 . . . 109.55(15) no
C11 C12 C13 . . . 109.96(17) no
C11 C12 C16 . . . 109.64(15) no
C13 C12 C16 . . . 109.24(16) no
C12 C13 C14 . . . 109.39(16) no
C13 C14 C15 . . . 109.73(12) no
C13 C14 C13 . . 4_565 109.66(19) no
C13 C14 C15 4_565 . . 109.73(12) no
C10 C15 C14 . . . 109.9(2) no
C12 C16 C12 . . 4_565 109.20(19) no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
C5 C6 H6B . . . 122.00 no
C7 C6 H6B . . . 115.00 no
C6 C7 H7 . . . 119.4(13) no
C8 C7 H7 . . . 122.7(13) no
C7 C8 H8A . . . 114(3) no
C9 C8 H8A . . . 125(3) no
C4 C9 H9 . . . 120.00 no
C8 C9 H9 . . . 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
C16 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
C13 C14 H14 4_565 . . 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
C12 C16 H16A . . . 110.00 no
C12 C16 H16B . . . 110.00 no
H16A C16 H16B . . . 108.00 no
C12 C16 H16A 4_565 . . 110.00 no
C12 C16 H16B 4_565 . . 110.00 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 C1 . . 1.773(2) no
S1 C2 . . 1.725(2) no
F1A C6 . . 1.353(3) no
F1B C8 . . 1.285(12) no
N1 N2 . . 1.379(2) no
N1 C1 . . 1.292(3) no
N2 C3 . . 1.371(3) no
N2 C2 . . 1.353(3) no
N3 N4 . . 1.394(3) no
N3 C2 . . 1.308(3) no
N4 C3 . . 1.318(3) no
C1 C10 . . 1.496(3) no
C3 C4 . . 1.455(3) no
C4 C9 . . 1.389(3) no
C4 C5 . . 1.390(3) no
C5 C6 . . 1.370(4) no
C6 C7 . . 1.368(3) no
C7 C8 . . 1.380(3) no
C8 C9 . . 1.380(4) no
C10 C11 . . 1.535(2) no
C10 C11 . 4_565 1.535(2) no
C10 C15 . . 1.529(3) no
C11 C12 . . 1.534(2) no
C12 C13 . . 1.517(3) no
C12 C16 . . 1.524(3) no
C13 C14 . . 1.514(3) no
C14 C15 . . 1.530(3) no
C5 H5 . . 0.9500 no
C6 H6B . . 0.9(3) no
C7 H7 . . 0.955(17) no
C8 H8A . . 0.95(2) no
C9 H9 . . 0.9500 no
C11 H11A . . 0.9900 no
C11 H11B . . 0.9900 no
C12 H12 . . 1.0000 no
C13 H13A . . 0.9900 no
C13 H13B . . 0.9900 no
C14 H14 . . 1.0000 no
C15 H15A . . 0.9900 no
C15 H15B . . 0.9900 no
C16 H16A . . 0.9900 no
C16 H16B . . 0.9900 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
C11 H11A F1A 2_557 0.99 2.67 3.526(3) 145
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
C2 S1 C1 N1 . . . . 0.000(10) no
C2 S1 C1 C10 . . . . 180.000(10) no
C1 S1 C2 N2 . . . . 0.000(10) no
C1 S1 C2 N3 . . . . -180.000(10) no
C1 N1 N2 C2 . . . . 0.000(10) no
C1 N1 N2 C3 . . . . 180.000(10) no
N2 N1 C1 S1 . . . . 0.000(10) no
N2 N1 C1 C10 . . . . 180.000(10) no
N1 N2 C3 C4 . . . . 0.000(10) no
C3 N2 C2 N3 . . . . 0.000(10) no
N1 N2 C2 S1 . . . . 0.000(10) no
C3 N2 C2 S1 . . . . 180.000(10) no
N1 N2 C3 N4 . . . . -180.000(10) no
C2 N2 C3 C4 . . . . 180.000(10) no
C2 N2 C3 N4 . . . . 0.000(10) no
N1 N2 C2 N3 . . . . 180.000(10) no
N4 N3 C2 S1 . . . . 180.000(10) no
N4 N3 C2 N2 . . . . 0.000(10) no
C2 N3 N4 C3 . . . . 0.000(10) no
N3 N4 C3 C4 . . . . -180.000(10) no
N3 N4 C3 N2 . . . . 0.000(10) no
N1 C1 C10 C11 . . . . 120.09(13) no
N1 C1 C10 C15 . . . . 0.000(10) no
S1 C1 C10 C15 . . . . 180.000(10) no
S1 C1 C10 C11 . . . . -59.91(13) no
N2 C3 C4 C5 . . . . 180.000(10) no
N2 C3 C4 C9 . . . . 0.000(10) no
N4 C3 C4 C5 . . . . 0.000(10) no
N4 C3 C4 C9 . . . . 180.000(10) no
C3 C4 C5 C6 . . . . 180.000(10) no
C9 C4 C5 C6 . . . . 0.000(10) no
C3 C4 C9 C8 . . . . 180.000(10) no
C5 C4 C9 C8 . . . . 0.000(10) no
C4 C5 C6 F1A . . . . 180.000(10) no
C4 C5 C6 C7 . . . . 0.000(10) no
F1A C6 C7 C8 . . . . 180.000(10) no
C5 C6 C7 C8 . . . . 0.000(10) no
C6 C7 C8 C9 . . . . 0.000(10) no
C7 C8 C9 C4 . . . . 0.000(10) no
C1 C10 C11 C12 . . . . -179.45(16) no
C15 C10 C11 C12 . . . . -58.8(2) no
C11 C10 C11 C12 4_565 . . . 59.90(19) no
C1 C10 C15 C14 . . . . 180.000(10) no
C11 C10 C15 C14 . . . . 59.27(12) no
C10 C11 C12 C13 . . . . 59.6(2) no
C10 C11 C12 C16 . . . . -60.5(2) no
C11 C12 C13 C14 . . . . -60.1(2) no
C16 C12 C13 C14 . . . . 60.2(2) no
C11 C12 C16 C12 . . . 4_565 60.3(2) no
C13 C12 C16 C12 . . . 4_565 -60.27(19) no
C12 C13 C14 C15 . . . . 60.2(2) no
C12 C13 C14 C13 . . . 4_565 -60.4(2) no
C13 C14 C15 C10 . . . . -60.28(14) no
