#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/71/2217109.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_2217109
loop_
_publ_author_name
'Bo Liu'
'Mingjie Zhang'
'Naijing Cui'
'Jie Zhu'
'Jin Cui'
_publ_section_title
;Ethyl
 4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
 monohydrate
;
_journal_coeditor_code           HK2363
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o261
_journal_page_last               o261
_journal_paper_doi               10.1107/S1600536807065737
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H16 N2 O3 S, H2 O'
_chemical_formula_moiety         'C14 H16 N2 O3 S, H2 O'
_chemical_formula_sum            'C14 H18 N2 O4 S'
_chemical_formula_weight         310.36
_chemical_name_systematic
;Ethyl
4-(4-hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.406(5)
_cell_angle_beta                 95.251(5)
_cell_angle_gamma                104.393(5)
_cell_formula_units_Z            2
_cell_length_a                   5.6702(17)
_cell_length_b                   11.212(3)
_cell_length_c                   12.343(4)
_cell_measurement_reflns_used    1137
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      3.32
_cell_volume                     756.5(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker SMART CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3958
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.1375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1741
_reflns_number_total             2655
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2363.cif
_cod_data_source_block           I
_cod_database_code               2217109
_cod_database_fobs_code          2217109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.30417(14) 0.38411(6) 0.11066(6) 0.0509(3) Uani d . 1
O O1 0.1221(4) 0.95058(17) 0.15444(17) 0.0588(6) Uani d . 1
O O2 -0.2131(3) 0.83224(15) 0.21777(15) 0.0464(5) Uani d . 1
O O3 0.1542(4) 0.70709(18) 0.67773(14) 0.0520(5) Uani d . 1
H H3 0.2977 0.7438 0.6934 0.078 Uiso calc R 1
O O4 0.6317(5) 0.8288(2) 0.72788(18) 0.0688(7) Uani d D 1
H H4A 0.700(6) 0.7722(19) 0.753(3) 0.088(13) Uiso d D 1
H H4B 0.681(6) 0.8966(17) 0.765(2) 0.096(14) Uiso d D 1
N N1 0.2842(4) 0.61232(19) 0.06966(18) 0.0417(6) Uani d D 1
H H1A 0.385(4) 0.602(2) 0.0205(16) 0.047(8) Uiso d D 1
N N2 0.0298(4) 0.51470(18) 0.19204(17) 0.0376(5) Uani d D 1
H H2A -0.020(5) 0.4483(17) 0.231(2) 0.061(9) Uiso d D 1
C C1 0.1972(5) 0.5103(2) 0.12598(19) 0.0343(6) Uani d . 1
C C2 -0.0549(5) 0.6237(2) 0.2218(2) 0.0351(6) Uani d . 1
H H2 -0.2327 0.6050 0.2044 0.042 Uiso calc R 1
C C3 0.0627(4) 0.7321(2) 0.1543(2) 0.0334(6) Uani d . 1
C C4 0.2179(5) 0.7224(2) 0.0817(2) 0.0378(6) Uani d . 1
C C5 0.3300(6) 0.8169(2) 0.0035(2) 0.0521(8) Uani d . 1
H H5A 0.2437 0.8805 -0.0010 0.078 Uiso calc R 1
H H5B 0.3197 0.7784 -0.0671 0.078 Uiso calc R 1
H H5C 0.4986 0.8521 0.0286 0.078 Uiso calc R 1
C C6 -0.0012(5) 0.8494(2) 0.1737(2) 0.0401(6) Uani d . 1
C C7 -0.2762(6) 0.9417(2) 0.2582(3) 0.0563(8) Uani d . 1
H H7A -0.4527 0.9281 0.2532 0.068 Uiso calc R 1
H H7B -0.2115 1.0112 0.2139 0.068 Uiso calc R 1
C C8 -0.1728(7) 0.9697(3) 0.3736(3) 0.0710(10) Uani d . 1
H H8A -0.2140 0.8963 0.4147 0.106 Uiso calc R 1
H H8B -0.2398 1.0318 0.4038 0.106 Uiso calc R 1
H H8C 0.0018 0.9990 0.3766 0.106 Uiso calc R 1
C C9 0.0011(4) 0.6489(2) 0.34304(19) 0.0319(6) Uani d . 1
C C10 0.2363(5) 0.7051(2) 0.3872(2) 0.0388(6) Uani d . 1
H H10 0.3597 0.7294 0.3413 0.047 Uiso calc R 1
C C11 0.2911(5) 0.7258(2) 0.4978(2) 0.0410(6) Uani d . 1
H H11 0.4501 0.7639 0.5259 0.049 Uiso calc R 1
C C12 0.1096(5) 0.6899(2) 0.5672(2) 0.0371(6) Uani d . 1
C C13 -0.1259(5) 0.6333(2) 0.5247(2) 0.0428(7) Uani d . 1
H H13 -0.2488 0.6088 0.5708 0.051 Uiso calc R 1
C C14 -0.1787(5) 0.6130(2) 0.4140(2) 0.0392(6) Uani d . 1
H H14 -0.3377 0.5747 0.3862 0.047 Uiso calc R 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'
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
C6 O2 C7 117.0(2)
C12 O3 H3 109.5
C1 N1 C4 124.1(2)
C1 N1 H1A 114.2(17)
C4 N1 H1A 121.6(17)
C1 N2 C2 127.1(2)
C1 N2 H2A 116.3(18)
C2 N2 H2A 115.7(18)
N2 C1 N1 117.3(2)
N2 C1 S1 122.54(19)
N1 C1 S1 120.1(2)
N2 C2 C9 108.85(18)
N2 C2 C3 109.3(2)
C9 C2 C3 113.4(2)
N2 C2 H2 108.4
C9 C2 H2 108.4
C3 C2 H2 108.4
C4 C3 C6 121.1(2)
C4 C3 C2 122.1(2)
C6 C3 C2 116.7(2)
C3 C4 N1 119.6(2)
C3 C4 C5 127.9(2)
N1 C4 C5 112.4(2)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O1 C6 O2 122.9(2)
O1 C6 C3 125.3(3)
O2 C6 C3 111.7(2)
O2 C7 C8 110.0(2)
O2 C7 H7A 109.7
C8 C7 H7A 109.7
O2 C7 H7B 109.7
C8 C7 H7B 109.7
H7A C7 H7B 108.2
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 117.9(2)
C10 C9 C2 120.7(2)
C14 C9 C2 121.4(2)
C11 C10 C9 121.3(2)
C11 C10 H10 119.3
C9 C10 H10 119.3
C10 C11 C12 120.0(2)
C10 C11 H11 120.0
C12 C11 H11 120.0
O3 C12 C13 118.0(2)
O3 C12 C11 122.5(2)
C13 C12 C11 119.5(2)
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C9 121.3(2)
C13 C14 H14 119.4
C9 C14 H14 119.4
H4A O4 H4B 112.8(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.688(2)
O1 C6 1.213(3)
O2 C6 1.335(3)
O2 C7 1.458(3)
O3 C12 1.368(3)
O3 H3 0.8200
O4 H4A 0.87(3)
O4 H4B 0.855(10)
N1 C1 1.353(3)
N1 C4 1.387(3)
N1 H1A 0.895(10)
N2 C1 1.316(3)
N2 C2 1.476(3)
N2 H2A 0.892(10)
C2 C9 1.510(3)
C2 C3 1.526(3)
C2 H2 0.9800
C3 C4 1.333(3)
C3 C6 1.472(3)
C4 C5 1.500(4)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C7 C8 1.489(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.385(3)
C9 C14 1.390(3)
C10 C11 1.377(3)
C10 H10 0.9300
C11 C12 1.384(4)
C11 H11 0.9300
C12 C13 1.381(4)
C13 C14 1.376(4)
C13 H13 0.9300
C14 H14 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
O4 H4B O1 2_676 0.855(10) 1.999(14) 2.835(3) 166(3)
O4 H4A S1 2_666 0.87(3) 2.44(2) 3.189(2) 145(3)
N2 H2A O3 2_566 0.892(10) 2.097(11) 2.988(3) 177(3)
N1 H1A S1 2_665 0.895(10) 2.479(11) 3.363(2) 170(2)
O3 H3 O4 . 0.82 1.90 2.724(3) 179.3
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
C2 N2 C1 N1 -7.7(4)
C2 N2 C1 S1 171.99(18)
C4 N1 C1 N2 3.7(4)
C4 N1 C1 S1 -176.06(19)
C1 N2 C2 C9 -118.3(3)
C1 N2 C2 C3 6.0(3)
N2 C2 C3 C4 -0.5(3)
C9 C2 C3 C4 121.1(3)
N2 C2 C3 C6 -179.8(2)
C9 C2 C3 C6 -58.2(3)
C6 C3 C4 N1 176.6(2)
C2 C3 C4 N1 -2.8(4)
C6 C3 C4 C5 -6.3(4)
C2 C3 C4 C5 174.4(2)
C1 N1 C4 C3 1.4(4)
C1 N1 C4 C5 -176.2(2)
C7 O2 C6 O1 -9.2(4)
C7 O2 C6 C3 169.7(2)
C4 C3 C6 O1 -22.8(4)
C2 C3 C6 O1 156.6(2)
C4 C3 C6 O2 158.4(2)
C2 C3 C6 O2 -22.3(3)
C6 O2 C7 C8 -88.3(3)
N2 C2 C9 C10 77.4(3)
C3 C2 C9 C10 -44.5(3)
N2 C2 C9 C14 -100.6(3)
C3 C2 C9 C14 137.5(2)
C14 C9 C10 C11 -0.4(4)
C2 C9 C10 C11 -178.4(2)
C9 C10 C11 C12 0.2(4)
C10 C11 C12 O3 179.4(2)
C10 C11 C12 C13 0.0(4)
O3 C12 C13 C14 -179.4(2)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C9 -0.2(4)
C10 C9 C14 C13 0.4(4)
C2 C9 C14 C13 178.4(2)
