#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/14/2211482.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_2211482
loop_
_publ_author_name
'Fan, Shuang'
'Liang, Ying'
'He, Hong-Wu'
_publ_section_title
6-(4-Fluorophenyl)-5-morpholino-3-phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one
_journal_coeditor_code           JH2037
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5731
_journal_page_last               o5733
_journal_paper_doi               10.1107/S160053680604904X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H17 F N4 O2 S2'
_chemical_formula_moiety         'C21 H17 F N4 O2 S2'
_chemical_formula_sum            'C21 H17 F N4 O2 S2'
_chemical_formula_weight         440.51
_chemical_name_systematic
;
6-(4-Fluorophenyl)-5-morpholino-3-phenyl-2-thioxo-2,3-
dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one
;
_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                 110.077(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1915(15)
_cell_length_b                   16.982(2)
_cell_length_c                   11.4220(14)
_cell_measurement_reflns_used    5993
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.20
_cell_volume                     2038.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23710
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9431
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0471
_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)+(0.0603P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                3524
_reflns_number_total             4869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2037.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2038.9(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               2211482
_cod_database_fobs_code          2211482
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
F F1 0.13894(12) 0.96514(8) 1.05469(12) 0.0816(4) Uani d . 1
N N1 0.73216(13) 0.94794(7) 0.64430(13) 0.0405(3) Uani d . 1
N N2 0.58009(13) 0.87122(7) 0.69555(12) 0.0404(3) Uani d . 1
N N3 0.41599(13) 0.94226(7) 0.73812(12) 0.0385(3) Uani d . 1
N N4 0.42695(13) 0.80333(8) 0.74593(13) 0.0433(3) Uani d . 1
O O1 0.39464(12) 1.07714(7) 0.70896(12) 0.0517(3) Uani d . 1
O O2 0.33350(16) 0.67440(8) 0.58172(14) 0.0763(5) Uani d . 1
S S1 0.88022(5) 1.04957(3) 0.57273(5) 0.05263(16) Uani d . 1
S S2 0.63984(4) 1.08721(2) 0.62038(4) 0.04533(14) Uani d . 1
C C1 0.97112(18) 0.75349(11) 0.67840(19) 0.0568(5) Uani d . 1
H H1 1.0239 0.7100 0.6862 0.068 Uiso calc R 1
C C2 0.9022(2) 0.78168(13) 0.5632(2) 0.0674(6) Uani d . 1
H H2 0.9079 0.7570 0.4926 0.081 Uiso calc R 1
C C3 0.96254(18) 0.78903(12) 0.78181(19) 0.0600(5) Uani d . 1
H H3 1.0094 0.7696 0.8603 0.072 Uiso calc R 1
C C4 0.88454(18) 0.85406(11) 0.77155(16) 0.0542(5) Uani d . 1
H H4 0.8790 0.8786 0.8423 0.065 Uiso calc R 1
C C5 0.8240(2) 0.84650(12) 0.55009(18) 0.0592(5) Uani d . 1
H H5 0.7779 0.8660 0.4715 0.071 Uiso calc R 1
C C6 0.81590(15) 0.88133(9) 0.65503(15) 0.0399(4) Uani d . 1
C C7 0.75823(16) 1.02266(10) 0.61237(14) 0.0416(4) Uani d . 1
C C8 0.62065(16) 0.94162(9) 0.67114(14) 0.0379(4) Uani d . 1
C C9 0.55838(16) 1.01128(9) 0.66270(14) 0.0401(4) Uani d . 1
C C10 0.45107(16) 1.01699(9) 0.70055(14) 0.0404(4) Uani d . 1
C C11 0.47569(15) 0.87289(9) 0.72399(14) 0.0375(4) Uani d . 1
C C12 0.50187(18) 0.73181(10) 0.75193(17) 0.0515(5) Uani d . 1
H H12A 0.4884 0.6956 0.8119 0.062 Uiso calc R 1
H H12B 0.5916 0.7451 0.7799 0.062 Uiso calc R 1
C C13 0.4649(2) 0.69273(12) 0.6268(2) 0.0694(6) Uani d . 1
H H13A 0.4843 0.7275 0.5684 0.083 Uiso calc R 1
H H13B 0.5139 0.6448 0.6335 0.083 Uiso calc R 1
C C14 0.29005(16) 0.78536(11) 0.69473(17) 0.0497(4) Uani d . 1
H H14A 0.2415 0.8339 0.6820 0.060 Uiso calc R 1
H H14B 0.2664 0.7530 0.7533 0.060 Uiso calc R 1
C C15 0.2599(2) 0.74248(12) 0.57277(18) 0.0650(6) Uani d . 1
H H15A 0.1707 0.7280 0.5429 0.078 Uiso calc R 1
H H15B 0.2740 0.7777 0.5119 0.078 Uiso calc R 1
C C16 0.33926(15) 0.94589(9) 0.81808(15) 0.0391(4) Uani d . 1
C C17 0.39358(17) 0.92238(10) 0.94054(16) 0.0451(4) Uani d . 1
H H17 0.4764 0.9032 0.9693 0.054 Uiso calc R 1
C C18 0.21729(16) 0.97583(10) 0.77485(17) 0.0462(4) Uani d . 1
H H18 0.1811 0.9914 0.6921 0.055 Uiso calc R 1
C C19 0.32543(19) 0.92729(11) 1.02016(17) 0.0527(5) Uani d . 1
H H19 0.3598 0.9099 1.1022 0.063 Uiso calc R 1
C C20 0.14918(17) 0.98258(11) 0.85474(18) 0.0517(5) Uani d . 1
H H20 0.0671 1.0030 0.8273 0.062 Uiso calc R 1
C C21 0.20557(19) 0.95844(11) 0.97515(18) 0.0531(5) 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C7 N1 C8 114.68(14) ?
C7 N1 C6 123.51(14) ?
C8 N1 C6 121.76(13) ?
C11 N2 C8 115.11(14) ?
C11 N3 C10 121.47(14) ?
C11 N3 C16 121.31(13) ?
C10 N3 C16 115.54(13) ?
C11 N4 C12 118.01(14) ?
C11 N4 C14 122.37(14) ?
C12 N4 C14 110.36(14) ?
C15 O2 C13 110.83(15) ?
C9 S2 C7 91.64(8) yes
C3 C1 C2 119.84(18) ?
C3 C1 H1 120.1 ?
C2 C1 H1 120.1 ?
C1 C2 C5 120.79(19) ?
C1 C2 H2 119.6 ?
C5 C2 H2 119.6 ?
C1 C3 C4 120.68(18) ?
C1 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
C6 C4 C3 118.57(17) ?
C6 C4 H4 120.7 ?
C3 C4 H4 120.7 ?
C6 C5 C2 118.66(18) ?
C6 C5 H5 120.7 ?
C2 C5 H5 120.7 ?
C5 C6 C4 121.45(16) ?
C5 C6 N1 120.00(15) ?
C4 C6 N1 118.54(15) ?
N1 C7 S1 126.86(13) yes
N1 C7 S2 109.31(12) yes
S1 C7 S2 123.84(10) yes
N2 C8 C9 126.05(16) ?
N2 C8 N1 120.58(14) ?
C9 C8 N1 113.27(14) yes
C8 C9 C10 120.47(15) ?
C8 C9 S2 111.08(13) yes
C10 C9 S2 127.99(13) ?
O1 C10 C9 126.74(16) ?
O1 C10 N3 120.88(16) ?
C9 C10 N3 112.27(14) ?
N2 C11 N4 118.22(14) ?
N2 C11 N3 123.33(15) ?
N4 C11 N3 118.38(15) ?
N4 C12 C13 110.87(15) ?
N4 C12 H12A 109.5 ?
C13 C12 H12A 109.5 ?
N4 C12 H12B 109.5 ?
C13 C12 H12B 109.5 ?
H12A C12 H12B 108.1 ?
O2 C13 C12 110.92(17) ?
O2 C13 H13A 109.5 ?
C12 C13 H13A 109.5 ?
O2 C13 H13B 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 108.0 ?
N4 C14 C15 109.88(15) ?
N4 C14 H14A 109.7 ?
C15 C14 H14A 109.7 ?
N4 C14 H14B 109.7 ?
C15 C14 H14B 109.7 ?
H14A C14 H14B 108.2 ?
O2 C15 C14 113.10(16) ?
O2 C15 H15A 109.0 ?
C14 C15 H15A 109.0 ?
O2 C15 H15B 109.0 ?
C14 C15 H15B 109.0 ?
H15A C15 H15B 107.8 ?
C17 C16 C18 120.48(17) ?
C17 C16 N3 118.36(15) ?
C18 C16 N3 121.07(15) ?
C19 C17 C16 120.11(17) ?
C19 C17 H17 119.9 ?
C16 C17 H17 119.9 ?
C16 C18 C20 119.82(17) ?
C16 C18 H18 120.1 ?
C20 C18 H18 120.1 ?
C21 C19 C17 118.02(17) ?
C21 C19 H19 121.0 ?
C17 C19 H19 121.0 ?
C21 C20 C18 118.18(17) ?
C21 C20 H20 120.9 ?
C18 C20 H20 120.9 ?
F1 C21 C20 118.48(18) ?
F1 C21 C19 118.16(18) ?
C20 C21 C19 123.35(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C21 1.364(2) ?
N1 C7 1.379(2) yes
N1 C8 1.388(2) yes
N1 C6 1.447(2) yes
N2 C11 1.316(2) yes
N2 C8 1.3417(19) ?
N3 C11 1.3908(19) yes
N3 C10 1.437(2) ?
N3 C16 1.454(2) ?
N4 C11 1.360(2) yes
N4 C12 1.464(2) ?
N4 C14 1.472(2) ?
O1 C10 1.2220(19) ?
O2 C15 1.402(2) ?
O2 C13 1.415(3) ?
S1 C7 1.6438(18) yes
S2 C9 1.7407(17) ?
S2 C7 1.7461(18) yes
C1 C3 1.359(3) ?
C1 C2 1.363(3) ?
C1 H1 0.9300 ?
C2 C5 1.382(3) ?
C2 H2 0.9300 ?
C3 C4 1.388(3) ?
C3 H3 0.9300 ?
C4 C6 1.369(2) ?
C4 H4 0.9300 ?
C5 C6 1.367(2) ?
C5 H5 0.9300 ?
C8 C9 1.359(2) ?
C9 C10 1.412(2) ?
C12 C13 1.499(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C15 1.504(3) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.379(2) ?
C16 C18 1.379(2) ?
C17 C19 1.376(2) ?
C17 H17 0.9300 ?
C18 C20 1.380(2) ?
C18 H18 0.9300 ?
C19 C21 1.368(3) ?
C19 H19 0.9300 ?
C20 C21 1.365(3) ?
C20 H20 0.9300 ?
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
C1 H1 O1 2_646 0.93 2.57 3.399(2) 148.6 yes
C5 H5 O1 3_676 0.93 2.48 3.384(2) 162.8 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
C3 C1 C2 C5 0.4(3)
C2 C1 C3 C4 -0.2(3)
C1 C3 C4 C6 0.4(3)
C1 C2 C5 C6 -0.8(3)
C2 C5 C6 C4 1.0(3)
C2 C5 C6 N1 -178.27(19)
C3 C4 C6 C5 -0.8(3)
C3 C4 C6 N1 178.48(16)
C7 N1 C6 C5 -74.4(2)
C8 N1 C6 C5 108.4(2)
C7 N1 C6 C4 106.31(19)
C8 N1 C6 C4 -70.8(2)
C8 N1 C7 S1 -178.63(12)
C6 N1 C7 S1 4.0(2)
C8 N1 C7 S2 1.50(17)
C6 N1 C7 S2 -175.83(12)
C9 S2 C7 N1 -1.25(12)
C9 S2 C7 S1 178.87(11)
C11 N2 C8 C9 -6.2(2)
C11 N2 C8 N1 177.70(14)
C7 N1 C8 N2 175.62(14)
C6 N1 C8 N2 -7.0(2)
C7 N1 C8 C9 -1.0(2)
C6 N1 C8 C9 176.40(14)
N2 C8 C9 C10 10.8(3)
N1 C8 C9 C10 -172.84(14)
N2 C8 C9 S2 -176.41(13)
N1 C8 C9 S2 -0.04(18)
C7 S2 C9 C8 0.75(13)
C7 S2 C9 C10 172.88(15)
C8 C9 C10 O1 172.44(16)
S2 C9 C10 O1 1.0(3)
C8 C9 C10 N3 -3.7(2)
S2 C9 C10 N3 -175.22(11)
C11 N3 C10 O1 177.15(14)
C16 N3 C10 O1 -17.5(2)
C11 N3 C10 C9 -6.4(2)
C16 N3 C10 C9 158.98(14)
C8 N2 C11 N4 177.94(14)
C8 N2 C11 N3 -5.0(2)
C12 N4 C11 N2 7.5(2)
C14 N4 C11 N2 -135.99(16)
C12 N4 C11 N3 -169.71(14)
C14 N4 C11 N3 46.8(2)
C10 N3 C11 N2 11.5(2)
C16 N3 C11 N2 -153.05(15)
C10 N3 C11 N4 -171.44(14)
C16 N3 C11 N4 24.0(2)
C11 N4 C12 C13 -92.69(19)
C14 N4 C12 C13 54.9(2)
C15 O2 C13 C12 58.3(2)
N4 C12 C13 O2 -57.5(2)
C11 N4 C14 C15 93.20(19)
C12 N4 C14 C15 -52.72(19)
C13 O2 C15 C14 -57.8(2)
N4 C14 C15 O2 55.0(2)
C11 N3 C16 C17 54.5(2)
C10 N3 C16 C17 -110.91(16)
C11 N3 C16 C18 -128.78(17)
C10 N3 C16 C18 65.81(19)
C18 C16 C17 C19 1.2(3)
N3 C16 C17 C19 177.94(16)
C17 C16 C18 C20 0.2(3)
N3 C16 C18 C20 -176.44(15)
C16 C17 C19 C21 -2.3(3)
C16 C18 C20 C21 -0.5(3)
C18 C20 C21 F1 179.81(16)
C18 C20 C21 C19 -0.6(3)
C17 C19 C21 F1 -178.44(16)
C17 C19 C21 C20 2.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125903
