#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227928.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_2227928
loop_
_publ_author_name
'Li, Gong-Chun'
'Ju, Zhi-Yu'
'Wang, Hong-Sheng'
'Niu, Yu-Jiao'
'Yang, Feng-Ling'
_publ_section_title
;
 6-Hydroxy-4-(pyridin-3-yl)-5-(2-thienylcarbonyl)-6-trifluoromethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one
;
_journal_coeditor_code           PV2334
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2852
_journal_paper_doi               10.1107/S1600536810041085
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H12 F3 N3 O3 S'
_chemical_formula_moiety         'C15 H12 F3 N3 O3 S'
_chemical_formula_sum            'C15 H12 F3 N3 O3 S'
_chemical_formula_weight         371.34
_chemical_name_systematic
;
6-Hydroxy-4-(pyridin-3-yl)-5-(2-thienylcarbonyl)-6-trifluoromethyl-
3,4,5,6-tetrahydropyrimidin-2(1H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.223(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.694(3)
_cell_length_b                   5.9710(8)
_cell_length_c                   17.6910(16)
_cell_measurement_reflns_used    5438
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.70
_cell_volume                     3123.6(6)
_computing_cell_refinement
'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_collection
'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15077
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrystalClear-SM Expert; Rigaku/MSC, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0355
_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)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2888
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2.0 σ(I)'
_cod_data_source_file            pv2334.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227928
_cod_database_fobs_code          2227928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S S1 0.026595(14) 0.12707(8) 0.92814(2) 0.03528(14) Uani d . 1 . .
F F1 0.10963(3) -0.11784(17) 0.62064(4) 0.0313(2) Uani d . 1 . .
F F2 0.06951(3) -0.11496(17) 0.71617(5) 0.0298(2) Uani d . 1 . .
F F3 0.09202(3) 0.19531(16) 0.67005(5) 0.0302(2) Uani d . 1 . .
O O1 0.15452(3) -0.25213(17) 0.75794(5) 0.0181(2) Uani d . 1 . .
O O2 0.25389(3) 0.21588(17) 0.70458(5) 0.0176(2) Uani d . 1 . .
O O3 0.10702(3) -0.12933(18) 0.89515(5) 0.0238(2) Uani d . 1 . .
N N1 0.18320(4) 0.0743(2) 0.70261(6) 0.0155(3) Uani d . 1 . .
N N2 0.21958(4) 0.2166(2) 0.81451(6) 0.0153(3) Uani d . 1 . .
N N3 0.19968(4) 0.2310(2) 1.07057(6) 0.0179(3) Uani d . 1 . .
C C1 0.14728(4) -0.0243(2) 0.74123(7) 0.0146(3) Uani d . 1 . .
C C2 0.22112(4) 0.1687(2) 0.74020(7) 0.0143(3) Uani d . 1 . .
C C3 0.18652(4) 0.1181(2) 0.86052(7) 0.0136(3) Uani d . 1 . .
H H3 0.1952 -0.0410 0.8719 0.016 Uiso calc R 1 . .
C C4 0.14098(4) 0.1215(2) 0.81197(7) 0.0141(3) Uani d . 1 . .
H H4 0.1345 0.2788 0.7949 0.017 Uiso calc R 1 . .
C C5 0.10424(5) -0.0160(3) 0.68637(7) 0.0211(3) Uani d . 1 . .
C C6 0.18514(4) 0.2436(2) 0.93467(7) 0.0144(3) Uani d . 1 . .
C C7 0.16718(4) 0.4565(3) 0.93907(7) 0.0178(3) Uani d . 1 . .
H H7 0.1565 0.5349 0.8943 0.021 Uiso calc R 1 . .
C C8 0.16500(5) 0.5540(3) 1.01013(7) 0.0208(3) Uani d . 1 . .
H H8 0.1524 0.6990 1.0148 0.025 Uiso calc R 1 . .
C C9 0.18153(5) 0.4355(3) 1.07377(7) 0.0201(3) Uani d . 1 . .
H H9 0.1799 0.5025 1.1222 0.024 Uiso calc R 1 . .
C C10 0.20114(4) 0.1383(2) 1.00190(7) 0.0153(3) Uani d . 1 . .
H H10 0.2138 -0.0072 0.9990 0.018 Uiso calc R 1 . .
C C11 0.10371(4) 0.0461(3) 0.85989(7) 0.0168(3) Uani d . 1 . .
C C12 0.06578(5) 0.1986(3) 0.86639(7) 0.0206(3) Uani d . 1 . .
C C13 0.05608(5) 0.4038(3) 0.83352(9) 0.0255(3) Uani d . 1 . .
H H13 0.0738 0.4723 0.7978 0.031 Uiso calc R 1 . .
C C14 0.01670(5) 0.5012(3) 0.85897(10) 0.0372(4) Uani d . 1 . .
H H14 0.0049 0.6425 0.8423 0.045 Uiso calc R 1 . .
C C15 -0.00227(5) 0.3696(3) 0.90984(10) 0.0404(5) Uani d . 1 . .
H H15 -0.0289 0.4088 0.9328 0.048 Uiso calc R 1 . .
H H1 0.1888(5) 0.007(3) 0.6611(9) 0.024(4) Uiso d . 1 . .
H H2 0.2439(5) 0.260(3) 0.8390(9) 0.020(4) Uiso d . 1 . .
H H5 0.1814(6) -0.273(3) 0.7674(10) 0.031(5) Uiso 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 S1 C12 . . 91.49(9) ?
C1 O1 H5 . . 108.7(13) ?
C2 N1 C1 . . 123.09(10) ?
C2 N1 H1 . . 112.9(10) ?
C1 N1 H1 . . 114.8(11) ?
C2 N2 C3 . . 122.91(11) ?
C2 N2 H2 . . 117.3(11) ?
C3 N2 H2 . . 115.1(11) ?
C9 N3 C10 . . 117.51(11) ?
O1 C1 N1 . . 112.90(10) ?
O1 C1 C5 . . 105.49(11) ?
N1 C1 C5 . . 107.24(10) ?
O1 C1 C4 . . 113.67(10) ?
N1 C1 C4 . . 107.58(11) ?
C5 C1 C4 . . 109.76(11) ?
O2 C2 N2 . . 123.02(12) ?
O2 C2 N1 . . 119.57(11) ?
N2 C2 N1 . . 117.31(12) ?
N2 C3 C6 . . 110.93(11) ?
N2 C3 C4 . . 106.64(10) ?
C6 C3 C4 . . 112.73(11) ?
N2 C3 H3 . . 108.8 ?
C6 C3 H3 . . 108.8 ?
C4 C3 H3 . . 108.8 ?
C11 C4 C3 . . 109.42(10) ?
C11 C4 C1 . . 115.54(11) ?
C3 C4 C1 . . 106.24(10) ?
C11 C4 H4 . . 108.5 ?
C3 C4 H4 . . 108.5 ?
C1 C4 H4 . . 108.5 ?
F1 C5 F3 . . 107.07(11) ?
F1 C5 F2 . . 107.45(12) ?
F3 C5 F2 . . 107.35(11) ?
F1 C5 C1 . . 112.19(11) ?
F3 C5 C1 . . 111.18(12) ?
F2 C5 C1 . . 111.36(11) ?
C7 C6 C10 . . 118.08(12) ?
C7 C6 C3 . . 122.98(11) ?
C10 C6 C3 . . 118.90(12) ?
C6 C7 C8 . . 119.02(12) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C9 C8 C7 . . 118.65(14) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
N3 C9 C8 . . 123.19(12) ?
N3 C9 H9 . . 118.4 ?
C8 C9 H9 . . 118.4 ?
N3 C10 C6 . . 123.54(13) ?
N3 C10 H10 . . 118.2 ?
C6 C10 H10 . . 118.2 ?
O3 C11 C12 . . 121.48(13) ?
O3 C11 C4 . . 120.69(12) ?
C12 C11 C4 . . 117.68(13) ?
C13 C12 C11 . . 130.93(13) ?
C13 C12 S1 . . 111.21(11) ?
C11 C12 S1 . . 117.77(11) ?
C12 C13 C14 . . 112.26(16) ?
C12 C13 H13 . . 123.9 ?
C14 C13 H13 . . 123.9 ?
C15 C14 C13 . . 112.22(17) ?
C15 C14 H14 . . 123.9 ?
C13 C14 H14 . . 123.9 ?
C14 C15 S1 . . 112.82(13) ?
C14 C15 H15 . . 123.6 ?
S1 C15 H15 . . 123.6 ?
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
S1 C15 . 1.699(2) ?
S1 C12 . 1.7208(15) ?
F1 C5 . 1.3347(15) ?
F2 C5 . 1.3379(16) ?
F3 C5 . 1.3370(18) ?
O1 C1 . 1.4047(17) ?
O1 H5 . 0.81(2) ?
O2 C2 . 1.2390(16) ?
O3 C11 . 1.2187(17) ?
N1 C2 . 1.3753(17) ?
N1 C1 . 1.4435(17) ?
N1 H1 . 0.87(2) ?
N2 C2 . 1.3501(16) ?
N2 C3 . 1.4553(16) ?
N2 H2 . 0.85(2) ?
N3 C9 . 1.3379(19) ?
N3 C10 . 1.3393(16) ?
C1 C5 . 1.5337(18) ?
C1 C4 . 1.5495(17) ?
C3 C6 . 1.5145(17) ?
C3 C4 . 1.5345(17) ?
C3 H3 . 1.0000 ?
C4 C11 . 1.5222(17) ?
C4 H4 . 1.0000 ?
C6 C7 . 1.383(2) ?
C6 C10 . 1.3902(17) ?
C7 C8 . 1.3922(18) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3813(19) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.461(2) ?
C12 C13 . 1.375(2) ?
C13 C14 . 1.416(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.355(3) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
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
O1 H5 O2 4_546 0.81(2) 1.94(2) 2.7466(14) 173(2) yes
N2 H2 N3 7_557 0.85(2) 2.21(2) 3.0153(15) 159(2) yes
N1 H1 N3 6 0.87(2) 2.19(2) 3.0378(16) 167(2) yes
C3 H3 O1 . 1.00 2.58 2.961(2) 102 ?
C3 H3 O2 4_546 1.00 2.57 3.255(2) 126 yes
C7 H7 O3 1_565 0.95 2.49 3.108(2) 123 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
C2 N1 C1 O1 . . . . -88.51(15) ?
C2 N1 C1 C5 . . . . 155.73(13) ?
C2 N1 C1 C4 . . . . 37.72(17) ?
C3 N2 C2 O2 . . . . -165.46(13) ?
C3 N2 C2 N1 . . . . 18.18(19) ?
C1 N1 C2 O2 . . . . 167.89(12) ?
C1 N1 C2 N2 . . . . -15.6(2) ?
C2 N2 C3 C6 . . . . -165.76(12) ?
C2 N2 C3 C4 . . . . -42.66(17) ?
N2 C3 C4 C11 . . . . -173.34(11) ?
C6 C3 C4 C11 . . . . -51.37(15) ?
N2 C3 C4 C1 . . . . 61.28(13) ?
C6 C3 C4 C1 . . . . -176.75(11) ?
O1 C1 C4 C11 . . . . -55.20(14) ?
N1 C1 C4 C11 . . . . 179.03(10) ?
C5 C1 C4 C11 . . . . 62.66(15) ?
O1 C1 C4 C3 . . . . 66.33(13) ?
N1 C1 C4 C3 . . . . -59.43(13) ?
C5 C1 C4 C3 . . . . -175.80(11) ?
O1 C1 C5 F1 . . . . -64.29(14) ?
N1 C1 C5 F1 . . . . 56.29(16) ?
C4 C1 C5 F1 . . . . 172.87(12) ?
O1 C1 C5 F3 . . . . 175.84(10) ?
N1 C1 C5 F3 . . . . -63.58(14) ?
C4 C1 C5 F3 . . . . 53.01(15) ?
O1 C1 C5 F2 . . . . 56.18(14) ?
N1 C1 C5 F2 . . . . 176.76(11) ?
C4 C1 C5 F2 . . . . -66.65(15) ?
N2 C3 C6 C7 . . . . 71.30(16) ?
C4 C3 C6 C7 . . . . -48.22(17) ?
N2 C3 C6 C10 . . . . -111.02(13) ?
C4 C3 C6 C10 . . . . 129.46(13) ?
C10 C6 C7 C8 . . . . -1.32(19) ?
C3 C6 C7 C8 . . . . 176.37(12) ?
C6 C7 C8 C9 . . . . 1.0(2) ?
C10 N3 C9 C8 . . . . -0.8(2) ?
C7 C8 C9 N3 . . . . 0.1(2) ?
C9 N3 C10 C6 . . . . 0.38(19) ?
C7 C6 C10 N3 . . . . 0.7(2) ?
C3 C6 C10 N3 . . . . -177.13(12) ?
C3 C4 C11 O3 . . . . -52.53(17) ?
C1 C4 C11 O3 . . . . 67.28(16) ?
C3 C4 C11 C12 . . . . 123.10(12) ?
C1 C4 C11 C12 . . . . -117.09(13) ?
O3 C11 C12 C13 . . . . 178.48(14) ?
C4 C11 C12 C13 . . . . 2.9(2) ?
O3 C11 C12 S1 . . . . 2.12(18) ?
C4 C11 C12 S1 . . . . -173.47(9) ?
C15 S1 C12 C13 . . . . 0.00(12) ?
C15 S1 C12 C11 . . . . 177.05(11) ?
C11 C12 C13 C14 . . . . -176.56(14) ?
S1 C12 C13 C14 . . . . -0.02(16) ?
C12 C13 C14 C15 . . . . 0.03(19) ?
C13 C14 C15 S1 . . . . -0.04(18) ?
C12 S1 C15 C14 . . . . 0.02(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 560942
