#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/32/2213221.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_2213221
loop_
_publ_author_name
'Ismail, Nur Liyana'
'Othman, Eliyanti'
'Yamin, Bohari M.'
_publ_section_title
;
 A new triclinic polymorph of
 4,5,6-trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione
;
_journal_coeditor_code           CI2337
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2442
_journal_page_last               o2443
_journal_paper_doi               10.1107/S1600536807016844
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H16 N2 S'
_chemical_formula_moiety         'C13 H16 N2 S'
_chemical_formula_sum            'C13 H16 N2 S'
_chemical_formula_weight         232.34
_chemical_name_systematic
;
4,5,6-trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                108.598(4)
_cell_angle_beta                 103.053(4)
_cell_angle_gamma                107.937(4)
_cell_formula_units_Z            2
_cell_length_a                   8.486(2)
_cell_length_b                   8.649(2)
_cell_length_c                   10.336(3)
_cell_measurement_reflns_used    4053
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.2
_cell_volume                     638.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6568
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.20
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.20
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.048
_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)+(0.0349P)²+0.2733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.120
_reflns_number_gt                2186
_reflns_number_total             2620
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2337.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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        638.4(3)
_cod_database_code               2213221
_cod_database_fobs_code          2213221
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 0.29366(8) 0.54872(7) 0.85797(7) 0.0515(2) Uani d . 1
N N1 0.0232(2) 0.2275(2) 0.7380(2) 0.0451(4) Uani d . 1
N N2 0.2934(2) 0.2490(2) 0.8659(2) 0.0480(5) Uani d . 1
H H2A 0.4062 0.3115 0.9056 0.058 Uiso calc R 1
C C1 -0.1197(3) 0.3419(3) 0.5804(3) 0.0516(6) Uani d . 1
H H1A -0.0605 0.3103 0.5178 0.062 Uiso calc R 1
C C2 -0.2358(4) 0.4194(4) 0.5489(3) 0.0624(7) Uani d . 1
H H2B -0.2549 0.4394 0.4646 0.075 Uiso calc R 1
C C3 -0.3221(3) 0.4665(3) 0.6412(3) 0.0629(7) Uani d . 1
H H3A -0.3999 0.5182 0.6197 0.075 Uiso calc R 1
C C4 -0.2941(4) 0.4375(4) 0.7655(3) 0.0646(7) Uani d . 1
H H4A -0.3527 0.4702 0.8284 0.078 Uiso calc R 1
C C5 -0.1793(3) 0.3600(3) 0.7981(3) 0.0550(6) Uani d . 1
H H5A -0.1605 0.3403 0.8826 0.066 Uiso calc R 1
C C6 -0.0931(3) 0.3122(3) 0.7046(2) 0.0431(5) Uani d . 1
C C7 -0.0494(3) 0.0390(3) 0.6953(3) 0.0484(5) Uani d . 1
C C8 0.0472(3) -0.0355(3) 0.7484(3) 0.0511(6) Uani d . 1
H H8A -0.0026 -0.1593 0.7152 0.061 Uiso calc R 1
C C9 0.2316(3) 0.0666(3) 0.8585(3) 0.0455(5) Uani d . 1
C C10 0.1983(3) 0.3295(3) 0.8196(2) 0.0399(5) Uani d . 1
C C11 -0.2357(4) -0.0662(3) 0.5862(3) 0.0761(9) Uani d . 1
H H11A -0.2706 -0.1907 0.5656 0.114 Uiso calc R 1
H H11B -0.2412 -0.0508 0.4975 0.114 Uiso calc R 1
H H11D -0.3145 -0.0245 0.6256 0.114 Uiso calc R 1
C C12 0.2357(4) 0.0768(4) 1.0090(3) 0.0656(7) Uani d . 1
H H12A 0.1557 0.1270 1.0368 0.098 Uiso calc R 1
H H12D 0.3540 0.1510 1.0790 0.098 Uiso calc R 1
H H12B 0.2001 -0.0413 1.0061 0.098 Uiso calc R 1
C C13 0.3578(3) -0.0129(3) 0.8118(3) 0.0615(7) Uani d . 1
H H13D 0.3537 -0.0184 0.7168 0.092 Uiso calc R 1
H H13A 0.3227 -0.1313 0.8082 0.092 Uiso calc R 1
H H13B 0.4765 0.0610 0.8811 0.092 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0424(3) 0.0372(3) 0.0661(4) 0.0116(2) 0.0064(3) 0.0246(3)
N1 0.0364(9) 0.0377(9) 0.0534(11) 0.0133(8) 0.0058(8) 0.0187(8)
N2 0.0331(9) 0.0382(9) 0.0670(12) 0.0133(8) 0.0071(8) 0.0240(9)
C1 0.0507(13) 0.0553(14) 0.0482(13) 0.0225(11) 0.0148(11) 0.0223(11)
C2 0.0631(16) 0.0633(16) 0.0568(15) 0.0268(13) 0.0054(13) 0.0309(13)
C3 0.0477(14) 0.0582(16) 0.0787(19) 0.0275(13) 0.0083(13) 0.0281(14)
C4 0.0572(15) 0.0717(18) 0.0761(18) 0.0354(14) 0.0300(14) 0.0317(15)
C5 0.0527(14) 0.0631(15) 0.0557(14) 0.0276(12) 0.0194(12) 0.0290(12)
C6 0.0349(11) 0.0396(11) 0.0487(12) 0.0139(9) 0.0069(9) 0.0181(9)
C7 0.0391(12) 0.0371(11) 0.0548(13) 0.0086(9) 0.0066(10) 0.0163(10)
C8 0.0486(13) 0.0335(11) 0.0582(14) 0.0105(10) 0.0076(11) 0.0175(10)
C9 0.0428(12) 0.0356(11) 0.0561(13) 0.0169(9) 0.0107(10) 0.0209(10)
C10 0.0377(11) 0.0364(10) 0.0423(11) 0.0134(9) 0.0105(9) 0.0169(9)
C11 0.0513(15) 0.0472(14) 0.093(2) 0.0040(12) -0.0094(14) 0.0247(14)
C12 0.0584(16) 0.0682(17) 0.0664(17) 0.0163(13) 0.0176(13) 0.0362(14)
C13 0.0600(15) 0.0519(14) 0.0731(17) 0.0324(13) 0.0163(13) 0.0232(13)
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'
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
C10 N1 C7 120.54(17)
C10 N1 C6 119.75(17)
C7 N1 C6 119.51(17)
C10 N2 C9 128.55(18)
C10 N2 H2A 115.7
C9 N2 H2A 115.7
C6 C1 C2 119.4(2)
C6 C1 H1A 120.3
C2 C1 H1A 120.3
C3 C2 C1 120.3(2)
C3 C2 H2B 119.9
C1 C2 H2B 119.9
C2 C3 C4 120.0(2)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C3 C4 C5 120.4(3)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C6 C5 C4 119.4(2)
C6 C5 H5A 120.3
C4 C5 H5A 120.3
C1 C6 C5 120.5(2)
C1 C6 N1 120.6(2)
C5 C6 N1 118.9(2)
C8 C7 N1 120.2(2)
C8 C7 C11 123.1(2)
N1 C7 C11 116.67(19)
C7 C8 C9 124.0(2)
C7 C8 H8A 118.0
C9 C8 H8A 118.0
N2 C9 C8 107.01(17)
N2 C9 C12 108.89(19)
C8 C9 C12 111.2(2)
N2 C9 C13 107.40(19)
C8 C9 C13 111.7(2)
C12 C9 C13 110.5(2)
N2 C10 N1 117.32(18)
N2 C10 S1 120.68(16)
N1 C10 S1 121.99(15)
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11D 109.5
H11A C11 H11D 109.5
H11B C11 H11D 109.5
C9 C12 H12A 109.5
C9 C12 H12D 109.5
H12A C12 H12D 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
H12D C12 H12B 109.5
C9 C13 H13D 109.5
C9 C13 H13A 109.5
H13D C13 H13A 109.5
C9 C13 H13B 109.5
H13D C13 H13B 109.5
H13A C13 H13B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 1.684(2) yes
N1 C10 1.360(3) yes
N1 C7 1.425(3) yes
N1 C6 1.444(3) yes
N2 C10 1.322(3) yes
N2 C9 1.472(3) yes
N2 H2A 0.86 ?
C1 C6 1.371(3) ?
C1 C2 1.389(3) ?
C1 H1A 0.93 ?
C2 C3 1.365(4) ?
C2 H2B 0.93 ?
C3 C4 1.368(4) ?
C3 H3A 0.93 ?
C4 C5 1.382(3) ?
C4 H4A 0.93 ?
C5 C6 1.375(3) ?
C5 H5A 0.93 ?
C7 C8 1.317(3) ?
C7 C11 1.501(3) ?
C8 C9 1.492(3) ?
C8 H8A 0.93 ?
C9 C12 1.522(3) ?
C9 C13 1.526(3) ?
C11 H11A 0.96 ?
C11 H11B 0.96 ?
C11 H11D 0.96 ?
C12 H12A 0.96 ?
C12 H12D 0.96 ?
C12 H12B 0.96 ?
C13 H13D 0.96 ?
C13 H13A 0.96 ?
C13 H13B 0.96 ?
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
N2 H2A S1 2_667 0.86 2.71 3.465(2) 148 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
C6 C1 C2 C3 0.3(4)
C1 C2 C3 C4 0.1(4)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 0.1(4)
C2 C1 C6 C5 -0.5(3)
C2 C1 C6 N1 178.3(2)
C4 C5 C6 C1 0.3(4)
C4 C5 C6 N1 -178.5(2)
C10 N1 C6 C1 90.4(3)
C7 N1 C6 C1 -94.7(3)
C10 N1 C6 C5 -90.7(3)
C7 N1 C6 C5 84.2(3)
C10 N1 C7 C8 7.9(4)
C6 N1 C7 C8 -166.9(2)
C10 N1 C7 C11 -170.6(2)
C6 N1 C7 C11 14.6(3)
N1 C7 C8 C9 2.5(4)
C11 C7 C8 C9 -179.1(3)
C10 N2 C9 C8 17.3(3)
C10 N2 C9 C12 -103.1(3)
C10 N2 C9 C13 137.3(2)
C7 C8 C9 N2 -13.2(3)
C7 C8 C9 C12 105.6(3)
C7 C8 C9 C13 -130.5(3)
C9 N2 C10 N1 -9.1(3)
C9 N2 C10 S1 172.22(18)
C7 N1 C10 N2 -4.9(3)
C6 N1 C10 N2 169.9(2)
C7 N1 C10 S1 173.71(17)
C6 N1 C10 S1 -11.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 672116
