#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/62/7056234.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7056234
loop_
_publ_author_name
'Delgado Espinosa, Zuly'
'Saeed, Aamer'
'Mahmood, Shamsul'
'Echeverría, Gustavo A.'
'Piro, Oscar E.'
'Erben, Mauricio Federico Federico'
_publ_section_title
;
 The Effect of Chalcogen Substitution on the Structure and Spectroscopy of
 4,7-Dimethyl-2H-chromen-2-one/thione Analogues
;
_journal_issue                   13
_journal_name_full               'New J. Chem.'
_journal_page_first              5770
_journal_page_last               5783
_journal_paper_doi               10.1039/C7NJ01311F
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C11 H10 O S'
_chemical_formula_weight         190.25
_chemical_name_systematic        4,7-Dimethyl-2H-chromen-2-thione
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-25 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.219(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0492(8)
_cell_length_b                   6.9453(6)
_cell_length_c                   13.528(1)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      71.1460
_cell_measurement_theta_min      4.5520
_cell_volume                     991.61(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3025
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.342
_diffrn_reflns_theta_min         4.558
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1049
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0889P)²+0.2361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                837
_reflns_number_total             1049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01311f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-07-22
;
_cod_original_cell_volume        991.6(1)
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               7056234
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.477
_shelx_estimated_absorpt_t_max   0.847
_shelx_res_file
;

    shelx.res created by SHELXL-2014/7

TITL Tiono in I2/m
CELL  1.54184  11.0492   6.9453  13.5275   90.000  107.219   90.000
ZERR     4.00   0.0008   0.0006   0.0010    0.000    0.008    0.000
LATT   2
SYMM  - X,   Y, - Z
SFAC  C    H    O    S
UNIT  44 40 4 4
MERG   2
SIZE   0.068 0.105 0.344
TEMP   24
REM    Crystal shape/color: needle/yellow
EQIV   $1 x, -y, z
DFIX   1.56 0.01 H10B H10B_$1
DFIX   0.96 0.01 C2 H2 C5 H5 C6 H6 C8 H8 C10 H10A C10 H10B C11 H11A C11 H11B
HTAB
FMAP   2
PLAN  -5
ACTA
L.S.   8
WGHT    0.088900    0.236100
FVAR       4.52726
C1    1    0.792491    0.000000    0.053770    10.50000    0.05114    0.08110 =
         0.06978    0.00000    0.02197    0.00000
C2    1    0.913587    0.000000    0.130665    10.50000    0.05094    0.07677 =
         0.07874    0.00000    0.01902    0.00000
C3    1    0.927617    0.000000    0.232436    10.50000    0.05489    0.06584 =
         0.07422    0.00000    0.00967    0.00000
C4    1    0.815696    0.000000    0.266793    10.50000    0.06055    0.05730 =
         0.06450    0.00000    0.00980    0.00000
C5    1    0.813942    0.000000    0.369872    10.50000    0.07504    0.08290 =
         0.05959    0.00000    0.00672    0.00000
C6    1    0.702465    0.000000    0.394805    10.50000    0.09498    0.08669 =
         0.05995    0.00000    0.02469    0.00000
C7    1    0.585768    0.000000    0.317478    10.50000    0.07757    0.07410 =
         0.06614    0.00000    0.03002    0.00000
C8    1    0.584767    0.000000    0.215383    10.50000    0.06114    0.07009 =
         0.06565    0.00000    0.02098    0.00000
C9    1    0.698278    0.000000    0.191849    10.50000    0.05699    0.05836 =
         0.05952    0.00000    0.01717    0.00000
C10   1    0.463584    0.000000    0.345766    10.50000    0.09539    0.11869 =
         0.08145    0.00000    0.04846    0.00000
C11   1    1.056859    0.000000    0.310568    10.50000    0.05823    0.10853 =
         0.08782    0.00000    0.00243    0.00000
O     3    0.688434    0.000000    0.087873    10.50000    0.04989    0.08688 =
         0.05904    0.00000    0.01745    0.00000
S1    4    0.769599    0.000000   -0.071203    10.50000    0.06251    0.17619 =
         0.06702    0.00000    0.02499    0.00000
H2    2    0.982357    0.000000    0.100834    10.50000    0.08435
H5    2    0.892338    0.000000    0.424389    10.50000    0.10392
H6    2    0.703999    0.000000    0.465991    10.50000    0.09138
H8    2    0.508834    0.000000    0.157919    10.50000    0.07525
H10A  2    0.388931    0.000000    0.287716    10.50000    0.19158
H10B  2    0.458303    0.111994    0.386048    11.00000    0.14672
H11A  2    1.119450    0.000000    0.274052    10.50000    0.12779
H11B  2    1.068273    0.110740    0.354472    11.00000    0.11574
HKLF    4

REM  Tiono in I2/m
REM R1 =  0.0495 for     837 Fo > 4sig(Fo)  and  0.0596 for all    1049 data
REM    105 parameters refined using      9 restraints

END

WGHT      0.0782      0.2709

REM Instructions for potential hydrogen bonds
EQIV $2 -x+2, -y, -z
HTAB C2 S1_$2
EQIV $3 -x+1, -y, -z
HTAB C8 S1_$3

REM Highest difference peak  0.142,  deepest hole -0.230,  1-sigma level  0.059
Q1    1   0.3970  0.1549  0.2896  11.00000  0.05    0.14
Q2    1   0.6168  0.2526  0.0235  11.00000  0.05    0.13
Q3    1   0.4171  0.2406  0.3123  11.00000  0.05    0.13
Q4    1   0.8592  0.0000  0.0938  10.50000  0.05    0.13
Q5    1   0.4880  0.1632  0.1700  11.00000  0.05    0.12
;
_shelx_res_checksum              8704
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.7925(2) 0.0000 0.0538(2) 0.0665(7) Uani 1 2 d S T P
C2 C 0.9136(2) 0.0000 0.1307(2) 0.0689(7) Uani 1 2 d DS T P
C3 C 0.9276(2) 0.0000 0.2324(2) 0.0670(7) Uani 1 2 d S T P
C4 C 0.8157(2) 0.0000 0.2668(2) 0.0627(6) Uani 1 2 d S T P
C5 C 0.8139(3) 0.0000 0.3699(2) 0.0754(8) Uani 1 2 d DS T P
C6 C 0.7025(3) 0.0000 0.3948(2) 0.0802(9) Uani 1 2 d DS T P
C7 C 0.5858(3) 0.0000 0.3175(2) 0.0707(7) Uani 1 2 d S T P
C8 C 0.5848(3) 0.0000 0.2154(2) 0.0651(7) Uani 1 2 d DS T P
C9 C 0.6983(2) 0.0000 0.1918(2) 0.0583(6) Uani 1 2 d S T P
C10 C 0.4636(4) 0.0000 0.3458(3) 0.0937(11) Uani 1 2 d DS T P
C11 C 1.0569(3) 0.0000 0.3106(3) 0.0890(10) Uani 1 2 d DS T P
O O 0.68843(16) 0.0000 0.08787(14) 0.0650(5) Uani 1 2 d S T P
S1 S 0.76960(7) 0.0000 -0.07120(6) 0.1006(5) Uani 1 2 d S T P
H2 H 0.982(2) 0.0000 0.101(3) 0.084(10) Uiso 1 2 d DS . P
H5 H 0.892(2) 0.0000 0.424(2) 0.104(12) Uiso 1 2 d DS . P
H6 H 0.704(4) 0.0000 0.4660(12) 0.091(11) Uiso 1 2 d DS . P
H8 H 0.5088(19) 0.0000 0.1579(17) 0.075(9) Uiso 1 2 d DS . P
H10A H 0.389(4) 0.0000 0.288(4) 0.19(3) Uiso 1 2 d DS . P
H10B H 0.458(4) 0.1120(7) 0.3860(17) 0.147(13) Uiso 1 1 d D . .
H11A H 1.119(4) 0.0000 0.274(3) 0.128(16) Uiso 1 2 d DS . P
H11B H 1.068(3) 0.111(3) 0.3545(19) 0.116(10) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0511(12) 0.0811(17) 0.0698(16) 0.000 0.0220(11) 0.000
C2 0.0509(13) 0.0768(17) 0.0787(18) 0.000 0.0190(12) 0.000
C3 0.0549(13) 0.0658(15) 0.0742(17) 0.000 0.0097(12) 0.000
C4 0.0605(14) 0.0573(13) 0.0645(15) 0.000 0.0098(12) 0.000
C5 0.0750(18) 0.0829(19) 0.0596(16) 0.000 0.0067(13) 0.000
C6 0.095(2) 0.087(2) 0.0600(16) 0.000 0.0247(16) 0.000
C7 0.0776(17) 0.0741(16) 0.0661(16) 0.000 0.0300(13) 0.000
C8 0.0611(14) 0.0701(16) 0.0656(15) 0.000 0.0210(12) 0.000
C9 0.0570(13) 0.0584(13) 0.0595(14) 0.000 0.0172(11) 0.000
C10 0.095(2) 0.119(3) 0.081(2) 0.000 0.048(2) 0.000
C11 0.0582(16) 0.109(3) 0.088(2) 0.000 0.0024(15) 0.000
O 0.0499(9) 0.0869(13) 0.0590(10) 0.000 0.0174(8) 0.000
S1 0.0625(5) 0.1762(11) 0.0670(5) 0.000 0.0250(4) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O C1 C2 117.1(3)
O C1 S1 117.6(2)
C2 C1 S1 125.3(2)
C3 C2 C1 123.1(3)
C2 C3 C4 118.8(2)
C2 C3 C11 121.3(3)
C4 C3 C11 119.9(3)
C9 C4 C5 116.2(3)
C9 C4 C3 117.9(3)
C5 C4 C3 125.9(2)
C6 C5 C4 121.6(3)
C5 C6 C7 120.8(3)
C8 C7 C6 118.8(3)
C8 C7 C10 120.8(3)
C6 C7 C10 120.4(3)
C7 C8 C9 119.5(3)
O C9 C8 115.6(2)
O C9 C4 121.3(2)
C8 C9 C4 123.1(3)
C1 O C9 121.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O 1.360(3)
C1 C2 1.431(4)
C1 S1 1.634(3)
C2 C3 1.339(4)
C3 C4 1.444(4)
C3 C11 1.504(4)
C4 C9 1.390(4)
C4 C5 1.400(4)
C5 C6 1.370(5)
C6 C7 1.399(5)
C7 C8 1.378(4)
C7 C10 1.508(5)
C8 C9 1.382(4)
C9 O 1.378(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13899044
