#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224335.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_2224335
loop_
_publ_author_name
'Liang, Ying'
'He, Hong-Wu'
'Yang, Zi-Wen'
_publ_section_title
6-(4-Fluorophenethyl)-7-imino-3-phenyl-2,3,6,7-tetrahydro-1,3-thiazolo[4,5-d]pyrimidine-2-thione
_journal_coeditor_code           JH2113
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3098
_journal_paper_doi               10.1107/S1600536809047576
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H15 F N4 S2'
_chemical_formula_moiety         'C19 H15 F N4 S2'
_chemical_formula_sum            'C19 H15 F N4 S2'
_chemical_formula_weight         382.47
_chemical_name_systematic
;
6-(4-Fluorophenethyl)-7-imino-3-phenyl-2,3,6,7-tetrahydro-\
1,3-thiazolo[4,5-d]pyrimidine-2-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6449(13)
_cell_length_b                   12.3780(19)
_cell_length_c                   16.546(3)
_cell_measurement_reflns_used    5242
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.46
_cell_volume                     1769.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13207
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9385
_exptl_absorpt_correction_T_min  0.9098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0451
_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)+(0.0630P)²+0.3948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                3442
_reflns_number_total             4047
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2113.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224335
_cod_database_fobs_code          2224335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4958(2) 1.34258(14) 0.58804(13) 0.0535(5) Uani d . 1 . .
C C2 0.4537(2) 1.33892(14) 0.50835(13) 0.0542(5) Uani d . 1 . .
H H2 0.4863 1.3917 0.4726 0.065 Uiso calc R 1 . .
C C3 0.3607(2) 1.25414(15) 0.48189(11) 0.0502(4) Uani d . 1 . .
H H3 0.3306 1.2503 0.4276 0.060 Uiso calc R 1 . .
C C4 0.31153(19) 1.17484(13) 0.53462(11) 0.0429(4) Uani d . 1 . .
C C5 0.3617(2) 1.18055(15) 0.61453(11) 0.0504(4) Uani d . 1 . .
H H5 0.3335 1.1265 0.6503 0.060 Uiso calc R 1 . .
C C6 0.4530(2) 1.26536(16) 0.64208(12) 0.0572(5) Uani d . 1 . .
H H6 0.4846 1.2697 0.6961 0.069 Uiso calc R 1 . .
C C7 0.2083(2) 1.08369(14) 0.50454(11) 0.0482(4) Uani d . 1 . .
H H7A 0.1203 1.1133 0.4745 0.058 Uiso calc R 1 . .
H H7B 0.1696 1.0439 0.5503 0.058 Uiso calc R 1 . .
C C8 0.29661(19) 1.00780(14) 0.45073(12) 0.0467(4) Uani d . 1 . .
H H8A 0.3450 1.0496 0.4087 0.056 Uiso calc R 1 . .
H H8B 0.3782 0.9732 0.4827 0.056 Uiso calc R 1 . .
C C9 0.10871(19) 0.95138(14) 0.34270(10) 0.0422(4) Uani d . 1 . .
C C10 0.03504(19) 0.85689(13) 0.30865(10) 0.0411(4) Uani d . 1 . .
C C11 0.04789(18) 0.75959(13) 0.34560(9) 0.0379(3) Uani d . 1 . .
C C12 0.1989(2) 0.82329(14) 0.44484(11) 0.0458(4) Uani d . 1 . .
H H12 0.2567 0.8135 0.4925 0.055 Uiso calc R 1 . .
C C13 -0.0990(2) 0.70793(14) 0.23294(10) 0.0445(4) Uani d . 1 . .
C C14 -0.02508(18) 0.56612(13) 0.33171(10) 0.0402(4) Uani d . 1 . .
C C15 0.0719(3) 0.49373(17) 0.29640(13) 0.0621(5) Uani d . 1 . .
H H15 0.1341 0.5146 0.2541 0.075 Uiso calc R 1 . .
C C16 0.0753(3) 0.38912(19) 0.32496(16) 0.0780(7) Uani d . 1 . .
H H16 0.1398 0.3386 0.3014 0.094 Uiso calc R 1 . .
C C17 -0.0147(3) 0.35897(17) 0.38718(18) 0.0776(8) Uani d . 1 . .
H H17 -0.0116 0.2881 0.4058 0.093 Uiso calc R 1 . .
C C18 -0.1101(3) 0.4326(2) 0.42259(16) 0.0739(7) Uani d . 1 . .
H H18 -0.1711 0.4117 0.4653 0.089 Uiso calc R 1 . .
C C19 -0.1156(2) 0.53768(16) 0.39494(12) 0.0554(5) Uani d . 1 . .
H H19 -0.1796 0.5882 0.4188 0.066 Uiso calc R 1 . .
N N1 0.19862(15) 0.92398(11) 0.41267(8) 0.0411(3) Uani d . 1 . .
N N2 0.12708(17) 0.73932(11) 0.41615(9) 0.0459(3) Uani d . 1 . .
N N3 0.1072(2) 1.04959(13) 0.31970(11) 0.0605(4) Uani d . 1 . .
H H3A 0.052(3) 1.0564(19) 0.2764(15) 0.073 Uiso d . 1 . .
N N4 -0.02702(16) 0.67676(11) 0.30352(8) 0.0397(3) Uani d . 1 . .
F F1 0.58230(17) 1.42773(10) 0.61527(9) 0.0823(4) Uani d . 1 . .
S S1 -0.07386(6) 0.84673(4) 0.21932(3) 0.05356(16) Uani d . 1 . .
S S2 -0.19713(7) 0.63041(4) 0.16868(3) 0.06299(18) Uani d . 1 . .
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_3
_geom_angle
_geom_angle_publ_flag
C2 C1 F1 . . 118.50(18) ?
C2 C1 C6 . . 122.77(17) ?
F1 C1 C6 . . 118.72(18) ?
C1 C2 C3 . . 118.01(18) ?
C1 C2 H2 . . 121.0 ?
C3 C2 H2 . . 121.0 ?
C2 C3 C4 . . 121.47(17) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 118.15(16) ?
C5 C4 C7 . . 121.30(16) ?
C3 C4 C7 . . 120.54(16) ?
C4 C5 C6 . . 121.04(18) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C1 C6 C5 . . 118.50(18) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
C4 C7 C8 . . 110.67(14) ?
C4 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
N1 C8 C7 . . 113.30(14) ?
N1 C8 H8A . . 108.9 ?
C7 C8 H8A . . 108.9 ?
N1 C8 H8B . . 108.9 ?
C7 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
N3 C9 N1 . . 118.24(15) ?
N3 C9 C10 . . 131.12(16) ?
N1 C9 C10 . . 110.63(14) ?
C11 C10 C9 . . 121.06(15) ?
C11 C10 S1 . . 110.87(12) ?
C9 C10 S1 . . 128.06(12) ?
C10 C11 N2 . . 125.78(15) ?
C10 C11 N4 . . 113.49(14) ?
N2 C11 N4 . . 120.72(14) ?
N2 C12 N1 . . 126.76(15) ?
N2 C12 H12 . . 116.6 ?
N1 C12 H12 . . 116.6 ?
N4 C13 S2 . . 127.02(13) ?
N4 C13 S1 . . 109.46(12) ?
S2 C13 S1 . . 123.52(10) ?
C15 C14 C19 . . 121.81(18) ?
C15 C14 N4 . . 118.95(17) ?
C19 C14 N4 . . 119.19(15) ?
C14 C15 C16 . . 118.4(2) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C17 C16 C15 . . 120.7(2) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 120.3(2) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C17 C18 C19 . . 120.1(2) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C14 C19 C18 . . 118.7(2) ?
C14 C19 H19 . . 120.6 ?
C18 C19 H19 . . 120.6 ?
C12 N1 C9 . . 122.40(13) ?
C12 N1 C8 . . 119.05(14) ?
C9 N1 C8 . . 118.54(14) ?
C12 N2 C11 . . 113.08(14) ?
C9 N3 H3A . . 110.2(16) ?
C13 N4 C11 . . 114.58(13) ?
C13 N4 C14 . . 123.01(13) ?
C11 N4 C14 . . 122.39(12) ?
C10 S1 C13 . . 91.60(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.359(3) ?
C1 F1 . 1.362(2) ?
C1 C6 . 1.367(3) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(2) ?
C4 C7 . 1.515(2) ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.515(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.470(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N3 . 1.274(2) ?
C9 N1 . 1.418(2) ?
C9 C10 . 1.439(2) ?
C10 C11 . 1.354(2) ?
C10 S1 . 1.7356(16) ?
C11 N2 . 1.361(2) ?
C11 N4 . 1.390(2) ?
C12 N2 . 1.294(2) ?
C12 N1 . 1.355(2) ?
C12 H12 . 0.9300 ?
C13 N4 . 1.364(2) ?
C13 S2 . 1.6501(17) ?
C13 S1 . 1.7472(18) ?
C14 C15 . 1.369(3) ?
C14 C19 . 1.369(3) ?
C14 N4 . 1.447(2) ?
C15 C16 . 1.378(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.359(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.371(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.379(3) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
N3 H3A . 0.86(2) ?
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
C15 H15 N3 2_545 0.93 2.61 3.486(3) 156.4
C19 H19 Cg3 3_665 0.93 2.74 3.637(2) 161
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
F1 C1 C2 C3 . . . . -177.55(17) ?
C6 C1 C2 C3 . . . . 1.4(3) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C2 C3 C4 C5 . . . . -1.9(3) ?
C2 C3 C4 C7 . . . . 179.23(16) ?
C3 C4 C5 C6 . . . . 2.7(3) ?
C7 C4 C5 C6 . . . . -178.48(17) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
F1 C1 C6 C5 . . . . 178.28(18) ?
C4 C5 C6 C1 . . . . -1.4(3) ?
C5 C4 C7 C8 . . . . -109.01(19) ?
C3 C4 C7 C8 . . . . 69.8(2) ?
C4 C7 C8 N1 . . . . -173.93(15) ?
N3 C9 C10 C11 . . . . -177.3(2) ?
N1 C9 C10 C11 . . . . 4.0(2) ?
N3 C9 C10 S1 . . . . 4.0(3) ?
N1 C9 C10 S1 . . . . -174.59(13) ?
C9 C10 C11 N2 . . . . 0.3(3) ?
S1 C10 C11 N2 . . . . 179.18(14) ?
C9 C10 C11 N4 . . . . -178.47(15) ?
S1 C10 C11 N4 . . . . 0.37(19) ?
C19 C14 C15 C16 . . . . 1.2(3) ?
N4 C14 C15 C16 . . . . 178.58(18) ?
C14 C15 C16 C17 . . . . -0.5(4) ?
C15 C16 C17 C18 . . . . -0.2(4) ?
C16 C17 C18 C19 . . . . 0.3(4) ?
C15 C14 C19 C18 . . . . -1.1(3) ?
N4 C14 C19 C18 . . . . -178.46(17) ?
C17 C18 C19 C14 . . . . 0.3(3) ?
N2 C12 N1 C9 . . . . 3.5(3) ?
N2 C12 N1 C8 . . . . -175.59(17) ?
N3 C9 N1 C12 . . . . 175.35(18) ?
C10 C9 N1 C12 . . . . -5.8(2) ?
N3 C9 N1 C8 . . . . -5.6(2) ?
C10 C9 N1 C8 . . . . 173.26(14) ?
C7 C8 N1 C12 . . . . -100.26(19) ?
C7 C8 N1 C9 . . . . 80.6(2) ?
N1 C12 N2 C11 . . . . 1.3(3) ?
C10 C11 N2 C12 . . . . -3.2(3) ?
N4 C11 N2 C12 . . . . 175.53(15) ?
S2 C13 N4 C11 . . . . 179.73(13) ?
S1 C13 N4 C11 . . . . -0.73(19) ?
S2 C13 N4 C14 . . . . 1.2(3) ?
S1 C13 N4 C14 . . . . -179.28(13) ?
C10 C11 N4 C13 . . . . 0.2(2) ?
N2 C11 N4 C13 . . . . -178.63(15) ?
C10 C11 N4 C14 . . . . 178.81(15) ?
N2 C11 N4 C14 . . . . -0.1(2) ?
C15 C14 N4 C13 . . . . 76.3(2) ?
C19 C14 N4 C13 . . . . -106.2(2) ?
C15 C14 N4 C11 . . . . -102.1(2) ?
C19 C14 N4 C11 . . . . 75.4(2) ?
C11 C10 S1 C13 . . . . -0.66(14) ?
C9 C10 S1 C13 . . . . 178.08(17) ?
N4 C13 S1 C10 . . . . 0.78(14) ?
S2 C13 S1 C10 . . . . -179.66(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655954
