#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200618.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_2200618
loop_
_publ_author_name
'Munshi, Parthapratim'
'Guru Row, T. N.'
_publ_section_title
;
 2H-Chromene-2-thione
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1175
_journal_page_last               o1176
_journal_paper_doi               10.1107/S1600536801019067
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C9 H6 O S'
_chemical_formula_moiety         'C9 H6 O S'
_chemical_formula_structural     'C9 H6 O S'
_chemical_formula_sum            'C9 H6 O S'
_chemical_formula_weight         162.21
_chemical_melting_point          371
_chemical_name_common            2-thiocoumarin
_chemical_name_systematic
;
2H-chromene-2-thione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1260(10)
_cell_length_b                   17.779(3)
_cell_length_c                   10.268(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.29
_cell_measurement_theta_min      6.07
_cell_volume                     753.2(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius Turbo-CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .1229
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            815
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .357
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .04
_refine_diff_density_max         .199
_refine_diff_density_min         -.259
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .840
_refine_ls_R_factor_all          .1638
_refine_ls_R_factor_gt           .0541
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1169P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1855
_reflns_number_gt                375
_reflns_number_total             815
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6115.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2200618
_cod_database_fobs_code          2200618
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_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
_atom_site_type_symbol
S1 1.2593(9) -.08497(13) .6906(2) .0613(9) Uani d . 1 . . S
O1 .9875(18) .0385(3) .7619(5) .0467(17) Uani d . 1 . . O
C1 1.072(2) -.0063(5) .6592(7) .039(2) Uani d . 1 . . C
C9 .695(3) .1257(4) .6242(8) .045(3) Uani d . 1 . . C
C8 .803(3) .1030(4) .7458(8) .045(3) Uani d . 1 . . C
C2 .976(3) .0190(4) .5324(7) .048(3) Uani d . 1 . . C
H2 1.0401 -.0083 .4597 .057 Uiso calc R 1 . . H
C4 .513(3) .1906(4) .6149(10) .055(3) Uani d . 1 . . C
H4 .4342 .2066 .5347 .066 Uiso calc R 1 . . H
C7 .743(3) .1440(4) .8571(8) .050(2) Uani d . 1 . . C
H7 .8250 .1289 .9373 .060 Uiso calc R 1 . . H
C3 .795(3) .0807(4) .5158(7) .046(2) Uani d . 1 . . C
H3 .7339 .0948 .4321 .056 Uiso calc R 1 . . H
C6 .555(3) .2086(5) .8456(8) .059(3) Uani d . 1 . . C
H6 .5016 .2364 .9193 .070 Uiso calc R 1 . . H
C5 .449(3) .2312(5) .7258(10) .064(3) Uani d . 1 . . C
H5 .3294 .2754 .7191 .076 Uiso calc R 1 . . H
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 .0697(19) .0619(14) .0521(12) .014(2) -.002(2) .0013(12)
O1 .057(4) .051(3) .032(3) -.007(4) -.004(4) .003(3)
C1 .025(6) .053(5) .038(4) -.018(5) -.007(4) -.007(4)
C9 .049(8) .038(4) .048(5) -.014(6) -.004(6) .008(4)
C8 .043(7) .045(5) .046(4) -.004(6) .002(6) .000(4)
C2 .058(7) .049(5) .036(5) -.007(6) -.006(6) .000(4)
C4 .046(7) .055(6) .064(6) -.009(6) -.010(7) .014(5)
C7 .052(7) .046(4) .052(5) -.001(7) -.002(8) -.003(4)
C3 .045(7) .061(5) .034(4) -.006(7) -.010(6) .011(4)
C6 .059(8) .064(6) .053(6) -.007(7) .008(6) -.013(5)
C5 .063(8) .043(6) .085(8) -.006(6) .012(8) -.006(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 10 -1
1 3 1
2 4 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C8 122.0(6) no
O1 C1 C2 116.6(8) no
O1 C1 S1 117.9(6) no
C2 C1 S1 125.5(7) no
C8 C9 C4 118.7(9) no
C8 C9 C3 116.5(8) no
C4 C9 C3 124.8(9) no
O1 C8 C9 121.6(8) no
O1 C8 C7 115.9(8) no
C9 C8 C7 122.5(8) no
C3 C2 C1 121.9(8) no
C3 C2 H2 119.1 no
C1 C2 H2 119.1 no
C5 C4 C9 119.1(10) no
C5 C4 H4 120.5 no
C9 C4 H4 120.5 no
C8 C7 C6 117.8(8) no
C8 C7 H7 121.1 no
C6 C7 H7 121.1 no
C2 C3 C9 121.3(7) no
C2 C3 H3 119.3 no
C9 C3 H3 119.3 no
C5 C6 C7 119.8(9) no
C5 C6 H6 120.1 no
C7 C6 H6 120.1 no
C6 C5 C4 122.1(10) no
C6 C5 H5 119.0 no
C4 C5 H5 119.0 no
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 C1 . 1.630(9) no
O1 C1 . 1.367(10) no
O1 C8 . 1.388(10) no
C1 C2 . 1.434(10) no
C9 C8 . 1.385(12) no
C9 C4 . 1.382(12) no
C9 C3 . 1.431(11) no
C8 C7 . 1.378(11) no
C2 C3 . 1.337(12) no
C2 H2 . .930 no
C4 C5 . 1.373(13) no
C4 H4 . .930 no
C7 C6 . 1.391(14) no
C7 H7 . .930 no
C3 H3 . .930 no
C6 C5 . 1.366(13) no
C6 H6 . .930 no
C5 H5 . .930 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 18736
2 PubChem 19890
