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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/51/2225154.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_2225154
loop_
_publ_author_name
'Saeed, Aamer'
'Bolte, Michael'
_publ_section_title
;
 1-(4-Chlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione
;
_journal_coeditor_code           ZQ2028
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o440
_journal_paper_doi               10.1107/S1600536810001777
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H15 Cl N2 S'
_chemical_formula_moiety         'C13 H15 Cl N2 S'
_chemical_formula_sum            'C13 H15 Cl N2 S'
_chemical_formula_weight         266.78
_chemical_name_systematic
;
1-(4-Chlorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.026(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.6710(18)
_cell_length_b                   10.8343(10)
_cell_length_c                   14.8619(13)
_cell_measurement_reflns_used    6686
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      3.4
_cell_volume                     2691.9(4)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Stoe IPDS II two-circle diffractometer'
_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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7624
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         3.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0349
_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)+(0.0634P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2134
_reflns_number_total             2512
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2028.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2225154
_cod_database_fobs_code          2225154
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 0.57142(2) 0.69991(4) 0.42770(3) 0.02504(14) Uani d . 1 . .
Cl Cl1 0.68751(3) 0.59306(4) 0.93548(3) 0.03636(15) Uani d . 1 . .
N N1 0.47205(7) 0.78438(12) 0.47357(11) 0.0219(3) Uani d . 1 . .
H H1 0.4318(11) 0.7666(19) 0.2421(18) 0.027(5) Uiso d . 1 . .
C C2 0.48383(9) 0.75825(14) 0.39373(13) 0.0202(3) Uani d . 1 . .
N N3 0.42364(8) 0.78513(13) 0.28874(12) 0.0239(3) Uani d . 1 . .
C C4 0.33943(9) 0.80299(15) 0.24811(13) 0.0240(4) Uani d . 1 . .
C C5 0.34219(9) 0.86623(15) 0.34036(14) 0.0251(3) Uani d . 1 . .
H H5 0.2983 0.9165 0.3221 0.030 Uiso calc R 1 . .
C C6 0.40392(9) 0.85420(15) 0.44661(14) 0.0238(3) Uani d . 1 . .
C C7 0.29744(11) 0.67811(18) 0.21978(17) 0.0364(4) Uani d . 1 . .
H H7A 0.3015 0.6356 0.1651 0.055 Uiso calc R 1 . .
H H7B 0.2410 0.6907 0.1886 0.055 Uiso calc R 1 . .
H H7C 0.3229 0.6280 0.2874 0.055 Uiso calc R 1 . .
C C8 0.29878(10) 0.88397(18) 0.14363(15) 0.0348(4) Uani d . 1 . .
H H9A 0.3273 0.9627 0.1621 0.052 Uiso calc R 1 . .
H H9B 0.2432 0.8993 0.1157 0.052 Uiso calc R 1 . .
H H9C 0.2999 0.8416 0.0863 0.052 Uiso calc R 1 . .
C C9 0.40992(11) 0.91451(18) 0.54228(15) 0.0342(4) Uani d . 1 . .
H H8A 0.3607 0.9608 0.5143 0.051 Uiso calc R 1 . .
H H8B 0.4557 0.9710 0.5804 0.051 Uiso calc R 1 . .
H H8C 0.4173 0.8511 0.5946 0.051 Uiso calc R 1 . .
C C11 0.52708(9) 0.73685(15) 0.58519(12) 0.0209(3) Uani d . 1 . .
C C12 0.51342(9) 0.62101(15) 0.60981(13) 0.0236(3) Uani d . 1 . .
H H12 0.4698 0.5727 0.5531 0.028 Uiso calc R 1 . .
C C13 0.56377(9) 0.57500(15) 0.71809(14) 0.0251(3) Uani d . 1 . .
H H13 0.5550 0.4955 0.7359 0.030 Uiso calc R 1 . .
C C14 0.62664(9) 0.64743(15) 0.79878(13) 0.0237(3) Uani d . 1 . .
C C15 0.64175(9) 0.76243(16) 0.77479(14) 0.0271(4) Uani d . 1 . .
H H15 0.6859 0.8099 0.8313 0.033 Uiso calc R 1 . .
C C16 0.59136(10) 0.80791(15) 0.66666(14) 0.0260(4) Uani d . 1 . .
H H16 0.6009 0.8869 0.6488 0.031 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . . 120.78(13) ?
C2 N1 C11 . . 119.87(12) ?
C6 N1 C11 . . 119.30(13) ?
N3 C2 N1 . . 116.59(13) ?
N3 C2 S1 . . 121.92(13) ?
N1 C2 S1 . . 121.46(11) ?
C2 N3 C4 . . 124.65(15) ?
C2 N3 H1 . . 114.6(14) ?
C4 N3 H1 . . 117.4(13) ?
N3 C4 C5 . . 106.41(13) ?
N3 C4 C7 . . 109.73(13) ?
C5 C4 C7 . . 111.46(15) ?
N3 C4 C8 . . 107.47(14) ?
C5 C4 C8 . . 111.52(14) ?
C7 C4 C8 . . 110.09(14) ?
C6 C5 C4 . . 122.23(14) ?
C6 C5 H5 . . 118.9 ?
C4 C5 H5 . . 118.9 ?
C5 C6 N1 . . 118.87(15) ?
C5 C6 C9 . . 124.65(15) ?
N1 C6 C9 . . 116.40(13) ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H9A . . 109.5 ?
C4 C8 H9B . . 109.5 ?
H9A C8 H9B . . 109.5 ?
C4 C8 H9C . . 109.5 ?
H9A C8 H9C . . 109.5 ?
H9B C8 H9C . . 109.5 ?
C6 C9 H8A . . 109.5 ?
C6 C9 H8B . . 109.5 ?
H8A C9 H8B . . 109.5 ?
C6 C9 H8C . . 109.5 ?
H8A C9 H8C . . 109.5 ?
H8B C9 H8C . . 109.5 ?
C12 C11 C16 . . 120.79(14) ?
C12 C11 N1 . . 118.79(13) ?
C16 C11 N1 . . 120.40(14) ?
C11 C12 C13 . . 119.95(14) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C14 C13 C12 . . 118.71(15) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.88(14) ?
C15 C14 Cl1 . . 119.14(12) ?
C13 C14 Cl1 . . 118.97(13) ?
C14 C15 C16 . . 119.19(14) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C11 C16 C15 . . 119.47(15) ?
C11 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
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 C2 . 1.6904(15) ?
Cl1 C14 . 1.7465(16) ?
N1 C2 . 1.374(2) ?
N1 C6 . 1.4327(19) ?
N1 C11 . 1.4462(19) ?
C2 N3 . 1.336(2) ?
N3 C4 . 1.482(2) ?
N3 H1 . 0.83(2) ?
C4 C5 . 1.504(2) ?
C4 C7 . 1.527(2) ?
C4 C8 . 1.534(2) ?
C5 C6 . 1.330(2) ?
C5 H5 . 0.9500 ?
C6 C9 . 1.502(2) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H9A . 0.9800 ?
C8 H9B . 0.9800 ?
C8 H9C . 0.9800 ?
C9 H8A . 0.9800 ?
C9 H8B . 0.9800 ?
C9 H8C . 0.9800 ?
C11 C12 . 1.382(2) ?
C11 C16 . 1.390(2) ?
C12 C13 . 1.397(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.382(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.381(2) ?
C15 C16 . 1.393(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 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
N3 H1 S1 2_655 0.83(2) 2.59(2) 3.4054(16) 169.1(17)
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
C6 N1 C2 N3 . . . . -9.4(2) ?
C11 N1 C2 N3 . . . . 168.04(14) ?
C6 N1 C2 S1 . . . . 168.43(11) ?
C11 N1 C2 S1 . . . . -14.1(2) ?
N1 C2 N3 C4 . . . . -19.9(2) ?
S1 C2 N3 C4 . . . . 162.28(12) ?
C2 N3 C4 C5 . . . . 36.3(2) ?
C2 N3 C4 C7 . . . . -84.4(2) ?
C2 N3 C4 C8 . . . . 155.86(16) ?
N3 C4 C5 C6 . . . . -26.8(2) ?
C7 C4 C5 C6 . . . . 92.80(19) ?
C8 C4 C5 C6 . . . . -143.71(17) ?
C4 C5 C6 N1 . . . . 3.6(2) ?
C4 C5 C6 C9 . . . . -179.71(16) ?
C2 N1 C6 C5 . . . . 17.2(2) ?
C11 N1 C6 C5 . . . . -160.24(15) ?
C2 N1 C6 C9 . . . . -159.70(15) ?
C11 N1 C6 C9 . . . . 22.8(2) ?
C2 N1 C11 C12 . . . . -87.68(19) ?
C6 N1 C11 C12 . . . . 89.81(18) ?
C2 N1 C11 C16 . . . . 93.85(19) ?
C6 N1 C11 C16 . . . . -88.66(19) ?
C16 C11 C12 C13 . . . . 1.1(2) ?
N1 C11 C12 C13 . . . . -177.39(14) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C12 C13 C14 C15 . . . . -1.2(3) ?
C12 C13 C14 Cl1 . . . . 177.54(13) ?
C13 C14 C15 C16 . . . . 1.2(3) ?
Cl1 C14 C15 C16 . . . . -177.54(13) ?
C12 C11 C16 C15 . . . . -1.1(3) ?
N1 C11 C16 C15 . . . . 177.36(15) ?
C14 C15 C16 C11 . . . . -0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 598093
