#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:00:13 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301809 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/12/2311218.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_2311218
loop_
_publ_author_name
'Fathima, Nikhath'
'Nagarajaiah, H.'
'Begum, Noor Shahina'
_publ_section_title
;
 Methyl
 4-(4-hy-droxy-phen-yl)-6-methyl-2-sulfanyl-idene-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.
;
_journal_coeditor_code           LH5689
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Structure reports online'
_journal_page_first              o306
_journal_paper_doi               10.1107/S1600536814002888
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H14 N2 O3 S'
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_name_systematic
'Methyl 4-(4-hydroxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                88.337(3)
_cell_angle_beta                 84.870(3)
_cell_angle_gamma                89.937(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3016(12)
_cell_length_b                   7.6855(13)
_cell_length_c                   11.4706(19)
_cell_measurement_reflns_used    2703
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.78
_cell_volume                     640.84(18)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEX CCD detector'
_diffrn_measurement_method       '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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3897
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.648
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0666
_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)+(0.0743P)²+1.6810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.2238
_reflns_number_gt                2084
_reflns_number_total             2703
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5689sup1.cif
_cod_data_source_block           I
_cod_database_code               2311218
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
_atom_site_symmetry_multiplicity
C C1 0.3658(6) 0.2646(6) -0.0479(4) 0.0338(9) Uani d . 1 1
H H1A 0.4523 0.3220 -0.1042 0.051 Uiso calc R 1 1
H H1B 0.2455 0.3127 -0.0541 0.051 Uiso calc R 1 1
H H1C 0.3637 0.1424 -0.0627 0.051 Uiso calc R 1 1
C C2 0.7615(6) 0.2492(5) 0.0356(4) 0.0304(9) Uani d . 1 1
C C3 0.9034(6) 0.1552(8) -0.1446(4) 0.0438(12) Uani d . 1 1
H H3A 0.9746 0.2601 -0.1569 0.066 Uiso calc R 1 1
H H3B 0.8711 0.1151 -0.2186 0.066 Uiso calc R 1 1
H H3C 0.9744 0.0675 -0.1079 0.066 Uiso calc R 1 1
C C4 0.6180(5) 0.2981(5) 0.2393(4) 0.0278(8) Uani d . 1 1
H H4 0.7320 0.3627 0.2462 0.033 Uiso calc R 1 1
C C5 0.5918(5) 0.2811(5) 0.1099(4) 0.0270(8) Uani d . 1 1
C C6 0.4216(5) 0.2909(5) 0.0729(4) 0.0299(9) Uani d . 1 1
C C7 0.2938(6) 0.3954(5) 0.2612(4) 0.0294(9) Uani d . 1 1
C C8 0.6324(5) 0.1204(5) 0.3004(3) 0.0259(8) Uani d . 1 1
C C9 0.4829(6) 0.0075(5) 0.3100(4) 0.0331(10) Uani d . 1 1
H H9 0.3732 0.0437 0.2818 0.040 Uiso calc R 1 1
C C10 0.4930(5) -0.1559(5) 0.3601(4) 0.0331(10) Uani d . 1 1
H H10 0.3905 -0.2284 0.3665 0.040 Uiso calc R 1 1
C C11 0.6558(5) -0.2129(5) 0.4010(3) 0.0280(8) Uani d . 1 1
C C12 0.8074(6) -0.1033(6) 0.3943(4) 0.0365(10) Uani d . 1 1
H H12 0.9166 -0.1396 0.4232 0.044 Uiso calc R 1 1
C C13 0.7924(6) 0.0628(6) 0.3433(4) 0.0335(9) Uani d . 1 1
H H13 0.8938 0.1367 0.3381 0.040 Uiso calc R 1 1
N N1 0.2744(5) 0.3334(5) 0.1523(3) 0.0313(8) Uani d . 1 1
H H1 0.1650 0.3200 0.1318 0.038 Uiso calc R 1 1
N N2 0.4641(4) 0.3976(4) 0.2940(3) 0.0265(7) Uani d . 1 1
H H2 0.4851 0.4620 0.3514 0.032 Uiso calc R 1 1
O O1 0.9147(4) 0.2737(5) 0.0673(3) 0.0431(8) Uani d . 1 1
O O2 0.7382(4) 0.1894(4) -0.0701(3) 0.0372(8) Uani d . 1 1
O O3 0.6613(4) -0.3807(4) 0.4445(3) 0.0308(7) Uani d . 1 1
H H3 0.7489 -0.3919 0.4840 0.046 Uiso calc R 1 1
S S1 0.10843(14) 0.46706(14) 0.34469(10) 0.0335(3) Uani d . 1 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 C1 H1A 109.5
C6 C1 H1B 109.5
H1A C1 H1B 109.5
C6 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 O2 121.7(4)
O1 C2 C5 123.1(4)
O2 C2 C5 115.2(3)
O2 C3 H3A 109.5
O2 C3 H3B 109.5
H3A C3 H3B 109.5
O2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N2 C4 C5 108.7(3)
N2 C4 C8 110.9(3)
C5 C4 C8 111.5(3)
N2 C4 H4 108.6
C5 C4 H4 108.6
C8 C4 H4 108.6
C6 C5 C2 125.5(4)
C6 C5 C4 120.0(4)
C2 C5 C4 114.5(3)
C5 C6 N1 119.0(4)
C5 C6 C1 128.1(4)
N1 C6 C1 112.8(3)
N2 C7 N1 116.2(4)
N2 C7 S1 123.7(3)
N1 C7 S1 120.2(3)
C13 C8 C9 117.7(4)
C13 C8 C4 122.3(3)
C9 C8 C4 120.0(4)
C10 C9 C8 121.7(4)
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 C11 120.0(4)
C9 C10 H10 120.0
C11 C10 H10 120.0
O3 C11 C10 117.5(4)
O3 C11 C12 122.3(4)
C10 C11 C12 120.1(4)
C11 C12 C13 118.5(4)
C11 C12 H12 120.7
C13 C12 H12 120.7
C8 C13 C12 122.0(4)
C8 C13 H13 119.0
C12 C13 H13 119.0
C7 N1 C6 123.7(3)
C7 N1 H1 118.1
C6 N1 H1 118.1
C7 N2 C4 124.6(3)
C7 N2 H2 117.7
C4 N2 H2 117.7
C2 O2 C3 116.3(3)
C11 O3 H3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.498(6)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 O1 1.223(5)
C2 O2 1.334(5)
C2 C5 1.465(6)
C3 O2 1.443(5)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 N2 1.463(5)
C4 C5 1.523(6)
C4 C8 1.525(6)
C4 H4 0.9800
C5 C6 1.350(5)
C6 N1 1.390(5)
C7 N2 1.331(5)
C7 N1 1.370(5)
C7 S1 1.688(4)
C8 C13 1.376(6)
C8 C9 1.390(5)
C9 C10 1.370(6)
C9 H9 0.9300
C10 C11 1.382(6)
C10 H10 0.9300
C11 O3 1.371(5)
C11 C12 1.387(6)
C12 C13 1.398(6)
C12 H12 0.9300
C13 H13 0.9300
N1 H1 0.8600
N2 H2 0.8600
O3 H3 0.8200
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
N1 H1 O1 1_455 0.860 2.060 2.923(5) 174
N2 H2 O3 1_565 0.860 2.140 2.929(4) 152
O3 H3 S1 2_656 0.820 2.360 3.122(3) 155
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
O1 C2 C5 C6 165.7(4)
O2 C2 C5 C6 -14.8(6)
O1 C2 C5 C4 -16.3(6)
O2 C2 C5 C4 163.2(3)
N2 C4 C5 C6 -25.1(5)
C8 C4 C5 C6 97.4(4)
N2 C4 C5 C2 156.8(3)
C8 C4 C5 C2 -80.7(4)
C2 C5 C6 N1 -175.8(4)
C4 C5 C6 N1 6.3(6)
C2 C5 C6 C1 2.8(7)
C4 C5 C6 C1 -175.1(4)
N2 C4 C8 C13 -126.2(4)
C5 C4 C8 C13 112.5(4)
N2 C4 C8 C9 56.5(5)
C5 C4 C8 C9 -64.8(5)
C13 C8 C9 C10 -0.1(7)
C4 C8 C9 C10 177.3(4)
C8 C9 C10 C11 -1.0(7)
C9 C10 C11 O3 -176.6(4)
C9 C10 C11 C12 1.8(7)
O3 C11 C12 C13 176.8(4)
C10 C11 C12 C13 -1.5(7)
C9 C8 C13 C12 0.4(7)
C4 C8 C13 C12 -177.0(4)
C11 C12 C13 C8 0.4(7)
N2 C7 N1 C6 -6.5(6)
S1 C7 N1 C6 172.3(3)
C5 C6 N1 C7 11.6(6)
C1 C6 N1 C7 -167.2(4)
N1 C7 N2 C4 -17.7(6)
S1 C7 N2 C4 163.6(3)
C5 C4 N2 C7 32.0(5)
C8 C4 N2 C7 -90.9(5)
O1 C2 O2 C3 0.1(6)
C5 C2 O2 C3 -179.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 749507
