#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025221.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_4025221
loop_
_publ_author_name
'Changsik Song'
'Timothy M. Swager'
_publ_section_title
;
 Reactive Conducting Thiepin Polymers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              999
_journal_page_last               1005
_journal_paper_doi               10.1021/jo902079j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C16 H12 O2 S3'
_chemical_formula_weight         332.44
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.712(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7243(6)
_cell_length_b                   7.8174(3)
_cell_length_c                   14.3030(6)
_cell_measurement_reflns_used    8512
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.97
_cell_volume                     1422.62(11)
_computing_cell_refinement       'SAINT 5 (Bruker-AXS, 2003)'
_computing_data_collection       'SMART 5 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT 5 (Bruker-AXS, 2003)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28151
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.9030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0337
_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)+(0.0535P)²+0.5784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                3458
_reflns_number_total             3840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902079j_si_002.cif
_cod_data_source_block           05158
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z 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               4025221
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63881(2) 0.02943(4) 0.96772(2) 0.01671(9) Uani 1 1 d . . .
O1 O 1.07999(7) -0.03771(15) 1.29992(7) 0.0233(2) Uani 1 1 d . . .
C1 C 0.97322(10) -0.04761(17) 1.29050(9) 0.0166(2) Uani 1 1 d . . .
O2 O 0.98385(7) -0.15991(13) 1.44197(6) 0.0201(2) Uani 1 1 d . . .
S2 S 0.62258(3) -0.25723(4) 1.10850(2) 0.01646(9) Uani 1 1 d . . .
C2 C 0.91554(10) 0.00002(17) 1.21236(9) 0.0156(2) Uani 1 1 d . . .
H2 H 0.9509 0.0491 1.1608 0.019 Uiso 1 1 calc R . .
S3 S 0.45087(2) -0.22423(4) 1.25169(2) 0.01711(9) Uani 1 1 d . . .
C3 C 0.80542(10) -0.02224(15) 1.20698(8) 0.0138(2) Uani 1 1 d . . .
C4 C 0.75261(9) 0.03032(16) 1.11885(8) 0.0138(2) Uani 1 1 d . . .
C5 C 0.78151(10) 0.17864(17) 1.06601(9) 0.0158(2) Uani 1 1 d . . .
H5 H 0.8328 0.2591 1.0865 0.019 Uiso 1 1 calc R . .
C6 C 0.72771(10) 0.19227(17) 0.98322(9) 0.0169(2) Uani 1 1 d . . .
H6 H 0.7383 0.2816 0.9393 0.020 Uiso 1 1 calc R . .
C7 C 0.67563(10) -0.06153(16) 1.07292(8) 0.0146(2) Uani 1 1 d . . .
C8 C 0.57953(10) -0.19434(16) 1.21911(9) 0.0146(2) Uani 1 1 d . . .
C9 C 0.47647(10) -0.14746(16) 1.36139(9) 0.0166(2) Uani 1 1 d . . .
H9 H 0.4257 -0.1401 1.4093 0.020 Uiso 1 1 calc R . .
C10 C 0.57874(10) -0.09805(16) 1.37180(8) 0.0152(2) Uani 1 1 d . . .
H10 H 0.6067 -0.0506 1.4280 0.018 Uiso 1 1 calc R . .
C11 C 0.63981(9) -0.12486(15) 1.28969(8) 0.0136(2) Uani 1 1 d . . .
C12 C 0.75356(9) -0.08972(15) 1.28510(8) 0.0140(2) Uani 1 1 d . . .
C13 C 0.81293(10) -0.12880(16) 1.36624(9) 0.0159(2) Uani 1 1 d . . .
H13 H 0.7776 -0.1680 1.4203 0.019 Uiso 1 1 calc R . .
C14 C 0.92061(10) -0.11172(17) 1.36930(9) 0.0165(2) Uani 1 1 d . . .
C15 C 1.14089(11) -0.0474(2) 1.21746(10) 0.0224(3) Uani 1 1 d . . .
H15A H 1.1242 -0.1536 1.1840 0.034 Uiso 1 1 calc R . .
H15B H 1.2158 -0.0461 1.2344 0.034 Uiso 1 1 calc R . .
H15C H 1.1247 0.0507 1.1772 0.034 Uiso 1 1 calc R . .
C16 C 0.93371(12) -0.2308(2) 1.52196(10) 0.0238(3) Uani 1 1 d . . .
H16A H 0.8841 -0.1474 1.5472 0.036 Uiso 1 1 calc R . .
H16B H 0.9869 -0.2588 1.5697 0.036 Uiso 1 1 calc R . .
H16C H 0.8958 -0.3350 1.5038 0.036 Uiso 1 1 calc R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C7 91.24(6) . . ?
C1 O1 C15 117.85(11) . . ?
O1 C1 C2 125.64(12) . . ?
O1 C1 C14 115.01(11) . . ?
C2 C1 C14 119.34(12) . . ?
C14 O2 C16 116.98(10) . . ?
C7 S2 C8 98.24(6) . . ?
C1 C2 C3 121.85(12) . . ?
C9 S3 C8 91.71(6) . . ?
C12 C3 C2 118.51(11) . . ?
C12 C3 C4 124.62(11) . . ?
C2 C3 C4 116.86(11) . . ?
C7 C4 C5 110.86(11) . . ?
C7 C4 C3 125.13(11) . . ?
C5 C4 C3 123.83(11) . . ?
C6 C5 C4 113.03(12) . . ?
C5 C6 S1 112.15(10) . . ?
C4 C7 S1 112.69(9) . . ?
C4 C7 S2 126.34(10) . . ?
S1 C7 S2 120.85(7) . . ?
C11 C8 S3 112.26(9) . . ?
C11 C8 S2 126.69(10) . . ?
S3 C8 S2 121.00(7) . . ?
C10 C9 S3 111.76(9) . . ?
C9 C10 C11 113.33(11) . . ?
C8 C11 C10 110.93(11) . . ?
C8 C11 C12 125.48(11) . . ?
C10 C11 C12 123.51(11) . . ?
C3 C12 C13 118.87(11) . . ?
C3 C12 C11 125.11(11) . . ?
C13 C12 C11 116.02(11) . . ?
C14 C13 C12 121.86(11) . . ?
O2 C14 C13 125.22(11) . . ?
O2 C14 C1 115.28(11) . . ?
C13 C14 C1 119.42(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7155(14) . ?
S1 C7 1.7239(13) . ?
O1 C1 1.3658(15) . ?
O1 C15 1.4212(16) . ?
C1 C2 1.3806(18) . ?
C1 C14 1.4101(17) . ?
O2 C14 1.3598(15) . ?
O2 C16 1.4288(16) . ?
S2 C7 1.7503(13) . ?
S2 C8 1.7510(13) . ?
C2 C3 1.4130(17) . ?
S3 C9 1.7075(13) . ?
S3 C8 1.7236(13) . ?
C3 C12 1.4073(16) . ?
C3 C4 1.4792(17) . ?
C4 C7 1.3750(17) . ?
C4 C5 1.4344(17) . ?
C5 C6 1.3646(18) . ?
C8 C11 1.3723(17) . ?
C9 C10 1.3637(18) . ?
C10 C11 1.4315(16) . ?
C11 C12 1.4755(17) . ?
C12 C13 1.4104(17) . ?
C13 C14 1.3767(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659142
2 PubChem 45112366
