#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/18/2211841.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_2211841
loop_
_publ_author_name
'Hong Jiang'
'Chen-Xia Yu'
'Shu-Jiang Tu'
'Xiang-Shan Wang'
'Chang-sheng Yao'
_publ_section_title
3-[(6-Chloropyridin-3-yl)methyl]-2-thioxo-2,3,5,6-tetrahydropyrimidin-4(1H)-one
_journal_coeditor_code           HG2131
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o298
_journal_page_last               o299
_journal_paper_doi               10.1107/S1600536806049439
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H10 Cl N3 O S'
_chemical_formula_moiety         'C10 H10 Cl N3 O S'
_chemical_formula_sum            'C10 H10 Cl N3 O S'
_chemical_formula_weight         255.72
_chemical_name_systematic
3-[(6-Chloropyridin-3-yl)methyl]-2-thioxo-2,3,5,6-tetrahydropyrimidin-4(1H)-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.562(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.131(3)
_cell_length_b                   5.7977(14)
_cell_length_c                   20.957(5)
_cell_measurement_reflns_used    1449
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.96
_cell_measurement_theta_min      2.45
_cell_volume                     1206.0(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6496
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_correction_T_min  0.8952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SABABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.240
_refine_ls_extinction_coef       0.0031(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0489
_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)+(0.0614P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                1277
_reflns_number_total             2470
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2131.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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        1205.9(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211841
_cod_database_fobs_code          2211841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.98460(10) 0.3609(2) 0.09604(4) 0.0982(5) Uani d . 1 . .
Cl Cl1 0.36045(11) 0.4397(2) 0.24228(5) 0.1150(5) Uani d . 1 . .
O O1 0.6241(3) -0.2187(5) 0.03536(12) 0.1079(10) Uani d . 1 . .
N N1 0.8558(3) 0.2570(5) -0.02128(13) 0.0744(9) Uani d . 1 . .
H H1A 0.901(3) 0.360(6) -0.0349(17) 0.089 Uiso d . 1 . .
N N2 0.7897(2) 0.0472(4) 0.06012(11) 0.0587(7) Uani d . 1 . .
C C1 0.8710(3) 0.2151(5) 0.04145(15) 0.0598(8) Uani d . 1 A .
C C2 0.7853(12) 0.116(3) -0.0759(7) 0.078(4) Uani d PD 0.453(14) A 1
H H2A 0.8385 -0.0180 -0.0825 0.094 Uiso calc PR 0.453(14) A 1
H H2B 0.7658 0.2050 -0.1159 0.094 Uiso calc PR 0.453(14) A 1
C C3 0.6566(11) 0.045(3) -0.0549(6) 0.081(4) Uani d PDU 0.453(14) A 1
H H3A 0.6069 -0.0631 -0.0862 0.097 Uiso calc PR 0.453(14) A 1
H H3B 0.6003 0.1789 -0.0531 0.097 Uiso calc PR 0.453(14) A 1
C C2' 0.7328(13) 0.1882(16) -0.0652(5) 0.078(3) Uani d PD 0.547(14) A 2
H H2'A 0.7433 0.2039 -0.1099 0.093 Uiso calc PR 0.547(14) A 2
H H2'B 0.6589 0.2862 -0.0588 0.093 Uiso calc PR 0.547(14) A 2
C C3' 0.7029(13) -0.0599(16) -0.0513(5) 0.075(3) Uani d PD 0.547(14) A 2
H H3'A 0.6186 -0.1076 -0.0789 0.090 Uiso calc PR 0.547(14) A 2
H H3'B 0.7741 -0.1594 -0.0601 0.090 Uiso calc PR 0.547(14) A 2
C C4 0.6937(4) -0.0760(6) 0.01649(17) 0.0783(10) Uani d . 1 A .
C C5 0.7974(3) -0.0065(5) 0.12936(14) 0.0655(9) Uani d . 1 A .
H H5A 0.8839 0.0446 0.1541 0.079 Uiso calc R 1 . .
H H5B 0.7924 -0.1723 0.1345 0.079 Uiso calc R 1 . .
C C6 0.6877(3) 0.1047(5) 0.15670(12) 0.0530(7) Uani d . 1 . .
C C7 0.6365(3) 0.3181(5) 0.13526(14) 0.0583(8) Uani d . 1 A .
H H7 0.6695 0.3936 0.1025 0.070 Uiso calc R 1 B 1
C C8 0.4871(3) 0.3105(6) 0.21018(16) 0.0674(9) Uani d . 1 . .
C C9 0.5360(4) 0.0967(6) 0.23275(15) 0.0886(13) Uani d P 0.46(3) A 1
H H9 0.5022 0.0210 0.2652 0.106 Uiso calc PR 0.46(3) A 1
N N3 0.5369(3) 0.4208(5) 0.16196(16) 0.0787(12) Uani d P 0.46(3) A 1
N N3' 0.5360(4) 0.0967(6) 0.23275(15) 0.0886(13) Uani d P 0.54(3) A 2
C C9' 0.5369(3) 0.4208(5) 0.16196(16) 0.0787(12) Uani d P 0.54(3) A 2
H H9' 0.5035 0.5648 0.1473 0.094 Uiso calc PR 0.54(3) A 2
C C10 0.6369(4) -0.0019(5) 0.20568(14) 0.0653(9) Uani d . 1 A .
H H10 0.6715 -0.1445 0.2210 0.078 Uiso calc R 1 C 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2' 119.8(5)
C1 N1 C2 128.1(6)
C2' N1 C2 29.6(4)
C1 N1 H1A 121(2)
C2' N1 H1A 116(2)
C2 N1 H1A 110(2)
C1 N2 C4 123.6(3)
C1 N2 C5 120.8(2)
C4 N2 C5 115.6(3)
N1 C1 N2 117.2(3)
N1 C1 S1 121.0(2)
N2 C1 S1 121.9(2)
N1 C2 C3 103.7(10)
N1 C2 H2A 111.0
C3 C2 H2A 111.0
N1 C2 H2B 111.0
C3 C2 H2B 111.0
H2A C2 H2B 109.0
C2 C3 C4 109.3(10)
C2 C3 H3A 109.8
C4 C3 H3A 109.8
C2 C3 H3B 109.8
C4 C3 H3B 109.8
H3A C3 H3B 108.3
N1 C2' C3' 108.7(8)
N1 C2' H2'A 109.9
C3' C2' H2'A 109.9
N1 C2' H2'B 109.9
C3' C2' H2'B 109.9
H2'A C2' H2'B 108.3
C4 C3' C2' 107.8(8)
C4 C3' H3'A 110.1
C2' C3' H3'A 110.1
C4 C3' H3'B 110.1
C2' C3' H3'B 110.1
H3'A C3' H3'B 108.5
O1 C4 N2 121.0(3)
O1 C4 C3' 121.6(4)
N2 C4 C3' 116.0(5)
O1 C4 C3 123.7(5)
N2 C4 C3 112.7(6)
C3' C4 C3 27.9(5)
N2 C5 C6 113.0(2)
N2 C5 H5A 109.0
C6 C5 H5A 109.0
N2 C5 H5B 109.0
C6 C5 H5B 109.0
H5A C5 H5B 107.8
C7 C6 C10 118.1(3)
C7 C6 C5 121.4(3)
C10 C6 C5 120.5(3)
C6 C7 N3 120.7(3)
C6 C7 H7 119.7
N3 C7 H7 119.7
N3 C8 C9 120.7(3)
N3 C8 Cl1 119.5(3)
C9 C8 Cl1 119.8(3)
C8 C9 C10 118.2(3)
C8 C9 H9 120.9
C10 C9 H9 120.9
C8 N3 C7 120.1(3)
C6 C10 C9 122.3(3)
C6 C10 H10 118.9
C9 C10 H10 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.679(3)
Cl1 C8 1.734(4)
O1 C4 1.204(4)
N1 C1 1.315(4)
N1 C2' 1.449(11)
N1 C2 1.472(14)
N1 H1A 0.83(3)
N2 C1 1.381(4)
N2 C4 1.391(4)
N2 C5 1.471(4)
C2 C3 1.515(9)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.626(14)
C3 H3A 0.9700
C3 H3B 0.9700
C2' C3' 1.510(8)
C2' H2'A 0.9700
C2' H2'B 0.9700
C3' C4 1.445(11)
C3' H3'A 0.9700
C3' H3'B 0.9700
C5 C6 1.495(4)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.381(4)
C6 C10 1.383(4)
C7 N3 1.383(4)
C7 H7 0.9300
C8 N3 1.374(4)
C8 C9 1.382(5)
C9 C10 1.388(5)
C9 H9 0.9300
C10 H10 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
N1 H1A S1 3_765 0.83(3) 2.49(3) 3.315(3) 169(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' N1 C1 N2 19.7(7)
C2 N1 C1 N2 -14.8(9)
C2' N1 C1 S1 -160.2(6)
C2 N1 C1 S1 165.3(7)
C4 N2 C1 N1 -0.5(5)
C5 N2 C1 N1 -178.4(3)
C4 N2 C1 S1 179.4(2)
C5 N2 C1 S1 1.6(4)
C1 N1 C2 C3 43.7(17)
C2' N1 C2 C3 -40.5(12)
N1 C2 C3 C4 -53.7(17)
C1 N1 C2' C3' -49.0(13)
C2 N1 C2' C3' 66.6(16)
N1 C2' C3' C4 57.3(15)
C1 N2 C4 O1 -179.0(3)
C5 N2 C4 O1 -1.0(5)
C1 N2 C4 C3' 14.0(7)
C5 N2 C4 C3' -168.1(6)
C1 N2 C4 C3 -16.5(7)
C5 N2 C4 C3 161.5(6)
C2' C3' C4 O1 151.2(8)
C2' C3' C4 N2 -41.8(13)
C2' C3' C4 C3 48.0(11)
C2 C3 C4 O1 -152.1(11)
C2 C3 C4 N2 45.9(15)
C2 C3 C4 C3' -57.1(13)
C1 N2 C5 C6 99.9(3)
C4 N2 C5 C6 -78.1(3)
N2 C5 C6 C7 -33.4(4)
N2 C5 C6 C10 148.3(3)
C10 C6 C7 N3 -0.3(4)
C5 C6 C7 N3 -178.7(3)
N3 C8 C9 C10 0.4(4)
Cl1 C8 C9 C10 179.7(2)
C9 C8 N3 C7 0.2(5)
Cl1 C8 N3 C7 -179.1(2)
C6 C7 N3 C8 -0.3(4)
C7 C6 C10 C9 1.0(4)
C5 C6 C10 C9 179.4(3)
C8 C9 C10 C6 -1.0(4)
