#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/35/2213563.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_2213563
loop_
_publ_author_name
'Hartung, Jens'
'Gross, Andreas'
'Bergsträsser, Uwe'
_publ_section_title
;
 5-(4-Chlorophenyl)-3-hydroxy-4-methylthiazole-2(3H)-thione: an
 instance of bifurcated hydrogen bonding
;
_journal_coeditor_code           SJ2277
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2743
_journal_page_last               o2745
_journal_paper_doi               10.1107/S1600536807018016
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 Cl N O S2'
_chemical_formula_moiety         'C10 H8 Cl N O S2'
_chemical_formula_sum            'C10 H8 Cl N O S2'
_chemical_formula_weight         257.74
_chemical_name_systematic
;
5-(4-Chlorophenyl)-3-hydroxy-4-methylthiazole-2(3H)-thione:
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.843(2)
_cell_length_b                   14.707(3)
_cell_length_c                   15.312(3)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      1.90
_cell_volume                     2214.7(8)
_computing_cell_refinement       'CELL in IPDS Software'
_computing_data_collection       'EXPOSE in IPDS Software (Stoe & Cie, 1998)'
_computing_data_reduction        'INTEGRATE in IPDS Software'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1994)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25254
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         50
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0299
_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)+(0.0492P)²+0.4154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                3008
_reflns_number_total             3499
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2277.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213563
_cod_database_fobs_code          2213563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C2' 0.9308(2) 0.60197(14) 0.40065(12) 0.0445(5) Uani d . 1
C C2 0.45265(19) 0.67331(13) 0.25501(12) 0.0419(4) Uani d . 1
C C4' 0.92944(19) 0.63026(13) 0.55209(12) 0.0425(4) Uani d . 1
C C4 0.44585(19) 0.63862(14) 0.10445(12) 0.0428(4) Uani d . 1
C C5' 0.7990(2) 0.60281(13) 0.53784(12) 0.0423(4) Uani d . 1
C C5 0.58170(19) 0.65126(13) 0.11789(12) 0.0399(4) Uani d . 1
C C6' 1.0020(2) 0.66381(17) 0.63306(13) 0.0570(6) Uani d . 1
H H17'A 0.9368 0.6839 0.6738 0.085 Uiso calc R 1
H H17'B 1.0602 0.7136 0.6188 0.085 Uiso calc R 1
H H17'C 1.0557 0.6155 0.6587 0.085 Uiso calc R 1
C C6 0.3645(2) 0.61025(19) 0.02501(14) 0.0645(6) Uani d . 1
H H17A 0.3122 0.6610 0.0029 0.097 Uiso calc R 1
H H17B 0.3043 0.5617 0.0397 0.097 Uiso calc R 1
H H17C 0.4244 0.5897 -0.0188 0.097 Uiso calc R 1
C C51 0.69215(19) 0.64507(13) 0.05669(12) 0.0399(4) Uani d . 1
C C51' 0.6866(2) 0.59617(13) 0.59779(12) 0.0420(4) Uani d . 1
C C52 0.8189(2) 0.61156(15) 0.08553(12) 0.0475(5) Uani d . 1
H H18 0.8311 0.5915 0.1429 0.057 Uiso calc R 1
C C52' 0.5542(2) 0.61610(14) 0.56718(13) 0.0488(5) Uani d . 1
H H18' 0.5390 0.6340 0.5094 0.059 Uiso calc R 1
C C53' 0.4455(2) 0.60974(15) 0.62104(14) 0.0516(5) Uani d . 1
H H23' 0.3581 0.6235 0.5997 0.062 Uiso calc R 1
C C53 0.9262(2) 0.60763(16) 0.03086(13) 0.0528(5) Uani d . 1
H H23 1.0099 0.5851 0.0512 0.063 Uiso calc R 1
C C54' 0.4675(2) 0.58286(13) 0.70652(13) 0.0462(5) Uani d . 1
C C54 0.9086(2) 0.63740(14) -0.05454(13) 0.0476(5) Uani d . 1
C C55' 0.5972(2) 0.56279(14) 0.73884(13) 0.0489(5) Uani d . 1
H H10' 0.6112 0.5449 0.7968 0.059 Uiso calc R 1
C C55 0.7851(2) 0.67061(15) -0.08499(12) 0.0491(5) Uani d . 1
H H10 0.7739 0.6903 -0.1426 0.059 Uiso calc R 1
C C56 0.6773(2) 0.67478(14) -0.02975(12) 0.0476(5) Uani d . 1
H H9 0.5940 0.6977 -0.0505 0.057 Uiso calc R 1
C C56' 0.7063(2) 0.56930(14) 0.68487(13) 0.0467(5) Uani d . 1
H H9' 0.7934 0.5557 0.7068 0.056 Uiso calc R 1
N N3 0.37983(15) 0.65263(11) 0.18184(10) 0.0433(4) Uani d . 1
N N3' 0.99787(15) 0.62739(12) 0.47443(10) 0.0449(4) Uani d . 1
Cl Cl1 1.04344(6) 0.63260(5) -0.12435(4) 0.0741(2) Uani d . 1
Cl Cl1' 0.33059(6) 0.57221(4) 0.77373(4) 0.06810(19) Uani d . 1
O O1' 1.13351(14) 0.65224(12) 0.47449(10) 0.0622(4) Uani d . 1
H H1' 1.1591(10) 0.64975(16) 0.4267(18) 0.093 Uiso calc R 1
O O1 0.24051(14) 0.64225(12) 0.18253(10) 0.0624(4) Uani d . 1
H H1 0.2138(10) 0.6523(4) 0.2336(18) 0.094 Uiso calc R 1
S S1' 0.76744(5) 0.57572(4) 0.42756(3) 0.04812(15) Uani d . 1
S S1 0.62032(5) 0.67879(4) 0.22697(3) 0.04540(15) Uani d . 1
S S2' 0.99656(5) 0.59761(5) 0.30185(3) 0.05829(17) Uani d . 1
S S2 0.38791(5) 0.68903(4) 0.35287(3) 0.05618(17) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
N3' C2' S2' 125.40(15)
N3' C2' S1' 107.11(14)
S2' C2' S1' 127.49(12)
N3 C2 S2 124.86(15)
N3 C2 S1 106.69(13)
S2 C2 S1 128.45(12)
C5' C4' N3' 110.00(17)
C5' C4' C6' 130.67(18)
N3' C4' C6' 119.29(17)
C5 C4 N3 110.02(17)
C5 C4 C6 131.02(19)
N3 C4 C6 118.91(17)
C4' C5' C51' 130.69(18)
C4' C5' S1' 110.67(15)
C51' C5' S1' 118.60(14)
C4 C5 C51 130.23(17)
C4 C5 S1 110.59(14)
C51 C5 S1 119.18(13)
C4' C6' H17'A 109.5
C4' C6' H17'B 109.5
H17'A C6' H17'B 109.5
C4' C6' H17'C 109.5
H17'A C6' H17'C 109.5
H17'B C6' H17'C 109.5
C4 C6 H17A 109.5
C4 C6 H17B 109.5
H17A C6 H17B 109.5
C4 C6 H17C 109.5
H17A C6 H17C 109.5
H17B C6 H17C 109.5
C56 C51 C52 117.90(18)
C56 C51 C5 122.32(17)
C52 C51 C5 119.74(17)
C56' C51' C52' 118.07(19)
C56' C51' C5' 122.44(18)
C52' C51' C5' 119.49(18)
C53 C52 C51 121.38(18)
C53 C52 H18 119.3
C51 C52 H18 119.3
C53' C52' C51' 121.34(19)
C53' C52' H18' 119.3
C51' C52' H18' 119.3
C54' C53' C52' 119.47(19)
C54' C53' H23' 120.3
C52' C53' H23' 120.3
C52 C53 C54 119.51(19)
C52 C53 H23 120.2
C54 C53 H23 120.2
C53' C54' C55' 120.63(19)
C53' C54' Cl1' 119.59(16)
C55' C54' Cl1' 119.78(16)
C55 C54 C53 120.57(19)
C55 C54 Cl1 119.52(15)
C53 C54 Cl1 119.92(16)
C54' C55' C56' 119.92(19)
C54' C55' H10' 120.0
C56' C55' H10' 120.0
C54 C55 C56 119.84(18)
C54 C55 H10 120.1
C56 C55 H10 120.1
C55 C56 C51 120.81(18)
C55 C56 H9 119.6
C51 C56 H9 119.6
C55' C56' C51' 120.57(19)
C55' C56' H9' 119.7
C51' C56' H9' 119.7
C2 N3 O1 121.09(16)
C2 N3 C4 119.58(16)
O1 N3 C4 119.30(15)
C2' N3' O1' 121.12(16)
C2' N3' C4' 119.40(16)
O1' N3' C4' 119.48(15)
N3' O1' H1' 109.5
N3 O1 H1 109.5
C2' S1' C5' 92.81(9)
C2 S1 C5 93.10(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2' N3' 1.338(2)
C2' S2' 1.671(2)
C2' S1' 1.720(2)
C2 N3 1.340(2)
C2 S2 1.668(2)
C2 S1 1.724(2)
C4' C5' 1.355(3)
C4' N3' 1.391(2)
C4' C6' 1.489(3)
C4 C5 1.357(3)
C4 N3 1.390(2)
C4 C6 1.488(3)
C5' C51' 1.470(3)
C5' S1' 1.7505(19)
C5 C51 1.467(3)
C5 S1 1.7453(19)
C6' H17'A 0.9600
C6' H17'B 0.9600
C6' H17'C 0.9600
C6 H17A 0.9600
C6 H17B 0.9600
C6 H17C 0.9600
C51 C56 1.396(3)
C51 C52 1.396(3)
C51' C56' 1.397(3)
C51' C52' 1.398(3)
C52 C53 1.375(3)
C52 H18 0.9300
C52' C53' 1.380(3)
C52' H18' 0.9300
C53' C54' 1.376(3)
C53' H23' 0.9300
C53 C54 1.383(3)
C53 H23 0.9300
C54' C55' 1.382(3)
C54' Cl1' 1.736(2)
C54 C55 1.373(3)
C54 Cl1 1.739(2)
C55' C56' 1.384(3)
C55' H10' 0.9300
C55 C56 1.385(3)
C55 H10 0.9300
C56 H9 0.9300
C56' H9' 0.9300
N3 O1 1.380(2)
N3' O1' 1.384(2)
O1' H1' 0.7841
O1 H1 0.8476
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
O1' H1' S2 1_655 0.78 2.63 3.2266(18) 134.8
O1 H1 S2' 1_455 0.85 2.55 3.1452(18) 128.3
C52 H18 S2' . 0.93 2.87 3.688(2) 146.8
C52' H18' S2 . 0.93 2.88 3.763(2) 158.1
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
N3' C4' C5' C51' -178.31(19)
C6' C4' C5' C51' -0.7(4)
N3' C4' C5' S1' -0.6(2)
C6' C4' C5' S1' 176.96(19)
N3 C4 C5 C51 -179.38(18)
C6 C4 C5 C51 3.3(4)
N3 C4 C5 S1 0.7(2)
C6 C4 C5 S1 -176.7(2)
C4 C5 C51 C56 37.7(3)
S1 C5 C51 C56 -142.38(17)
C4 C5 C51 C52 -144.7(2)
S1 C5 C51 C52 35.2(2)
C4' C5' C51' C56' -36.8(3)
S1' C5' C51' C56' 145.69(17)
C4' C5' C51' C52' 144.1(2)
S1' C5' C51' C52' -33.4(2)
C56 C51 C52 C53 -0.1(3)
C5 C51 C52 C53 -177.8(2)
C56' C51' C52' C53' 0.1(3)
C5' C51' C52' C53' 179.27(19)
C51' C52' C53' C54' -0.3(3)
C51 C52 C53 C54 0.0(3)
C52' C53' C54' C55' 0.4(3)
C52' C53' C54' Cl1' -178.50(16)
C52 C53 C54 C55 -0.1(3)
C52 C53 C54 Cl1 -179.91(18)
C53' C54' C55' C56' -0.3(3)
Cl1' C54' C55' C56' 178.60(16)
C53 C54 C55 C56 0.3(3)
Cl1 C54 C55 C56 -179.89(17)
C54 C55 C56 C51 -0.4(3)
C52 C51 C56 C55 0.3(3)
C5 C51 C56 C55 177.91(19)
C54' C55' C56' C51' 0.1(3)
C52' C51' C56' C55' 0.0(3)
C5' C51' C56' C55' -179.14(19)
S2 C2 N3 O1 -0.2(3)
S1 C2 N3 O1 179.32(15)
S2 C2 N3 C4 -178.18(15)
S1 C2 N3 C4 1.3(2)
C5 C4 N3 C2 -1.4(3)
C6 C4 N3 C2 176.36(19)
C5 C4 N3 O1 -179.40(17)
C6 C4 N3 O1 -1.7(3)
S2' C2' N3' O1' -0.7(3)
S1' C2' N3' O1' 179.45(14)
S2' C2' N3' C4' 178.25(16)
S1' C2' N3' C4' -1.6(2)
C5' C4' N3' C2' 1.5(3)
C6' C4' N3' C2' -176.40(19)
C5' C4' N3' O1' -179.53(17)
C6' C4' N3' O1' 2.6(3)
N3' C2' S1' C5' 0.94(16)
S2' C2' S1' C5' -178.88(16)
C4' C5' S1' C2' -0.20(17)
C51' C5' S1' C2' 177.83(16)
N3 C2 S1 C5 -0.70(15)
S2 C2 S1 C5 178.77(15)
C4 C5 S1 C2 0.01(16)
C51 C5 S1 C2 -179.95(16)
H1 O1 N3 C2 1.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24737570
