#------------------------------------------------------------------------------
#$Date: 2025-06-19 03:22:11 +0200 (Thu 19 de Jun de 2025) $
#$Revision: 300128 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/05/7250564.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_7250564
loop_
_publ_author_name
'Liu, Huimin'
'Zhuang, Zeyan'
'Hou, Yawen'
'Zhu, Yujiao'
'Xu, Ruofeng'
'Chen, Bin'
'Hu, Rong'
'Zhao, Zujin'
_publ_section_title
;
 Oxidation reduces spin-orbital coupling to achieve robust fluorescent
 emission in halogen substituted
 dithieno[3,2-b:2′,3′-d]thiophene
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP01121C
_journal_year                    2025
_chemical_formula_moiety         '0.286(C8 H4 O2 S3)'
_chemical_formula_sum            'C2.29 H1.14 O0.57 S0.86'
_chemical_formula_weight         65.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-01-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-08-21 deposited with the CCDC.	2025-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.31(3)
_cell_angle_gamma                90
_cell_formula_units_Z            14
_cell_length_a                   9.756(2)
_cell_length_b                   12.219(2)
_cell_length_c                   7.5175(15)
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_cell_volume                     875.5(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3495
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.015
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_min         3.335
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0334
_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)+(0.0512P)²+0.5716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                703
_reflns_number_total             773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp01121c2.cif
_cod_data_source_block           tref_CCDC2
_cod_database_code               7250564
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
;
_shelx_res_file
;
TITL tref in C2/c #15
    tref.res
    created by SHELXL-2018/3 at 09:30:23 on 10-Jan-2024
REM reset to C2/c #15
CELL 0.71073 9.7556 12.2185 7.5175 90 102.305 90
ZERR 14 0.002 0.0024 0.0015 0 0.03 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O S
UNIT 32 16 8 12

L.S. 4 0 0
PLAN  5
CONF
BOND $H
HTAB
MORE -1
fmap 2 53
ACTA
SHEL 999 0.84
OMIT 1 11 4
REM <olex2.extras>
REM <HklSrc "%.\\tref.hkl">
REM </olex2.extras>

WGHT    0.051200    0.571600
EXTI    0.008754
FVAR       0.19432
C1    1    0.424054    0.534021    0.227257    11.00000    0.02440    0.02561 =
         0.03267   -0.00019    0.00357    0.00164
C2    1    0.365906    0.430573    0.209563    11.00000    0.02125    0.02656 =
         0.03385   -0.00080    0.00107    0.00143
C3    1    0.217863    0.429423    0.162368    11.00000    0.02278    0.03238 =
         0.04326   -0.00172    0.00053   -0.00323
AFIX  43
H3    2    0.162797    0.366614    0.144262    11.00000   -1.20000
AFIX   0
C4    1    0.167235    0.534225    0.147159    11.00000    0.02041    0.04074 =
         0.04246   -0.00159    0.00075    0.00377
AFIX  43
H4    2    0.072048    0.550875    0.118278    11.00000   -1.20000
AFIX   0
O1    3    0.501362    0.268452    0.087363    11.00000    0.03663    0.03186 =
         0.05191   -0.01165    0.00185    0.00215
S1    4    0.296307    0.631743    0.186510    11.00000    0.02697    0.02809 =
         0.04798   -0.00120    0.00142    0.00560
S2    4    0.500000    0.330543    0.250000    10.50000    0.02160    0.02236 =
         0.03981    0.00000    0.00005    0.00000
HKLF 4




REM  tref in C2/c #15
REM wR2 = 0.0966, GooF = S = 1.090, Restrained GooF = 1.090 for all data
REM R1 = 0.0334 for 703 Fo > 4sig(Fo) and 0.0354 for all 773 data
REM 61 parameters refined using 0 restraints

END

WGHT      0.0512      0.5714

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.380,  deepest hole -0.345,  1-sigma level  0.062
Q1    1   0.4239  0.3792  0.2247  11.00000  0.05    0.38
Q2    1   0.2299  0.5814  0.1627  11.00000  0.05    0.32
Q3    1   0.3743  0.5814  0.2112  11.00000  0.05    0.30
Q4    1   0.3929  0.4874  0.2716  11.00000  0.05    0.28
Q5    1   0.3961  0.4802  0.1736  11.00000  0.05    0.26
;
_shelx_res_checksum              24830
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4241(2) 0.53402(17) 0.2273(3) 0.0279(5) Uani 1 1 d . . . . .
C2 C 0.3659(2) 0.43057(17) 0.2096(3) 0.0279(5) Uani 1 1 d . . . . .
C3 C 0.2179(2) 0.42942(19) 0.1624(3) 0.0338(5) Uani 1 1 d . . . . .
H3 H 0.162797 0.366614 0.144262 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1672(2) 0.53422(18) 0.1472(3) 0.0354(6) Uani 1 1 d . . . . .
H4 H 0.072048 0.550875 0.118278 0.043 Uiso 1 1 calc R U . . .
O1 O 0.50136(17) 0.26845(12) 0.0874(2) 0.0413(5) Uani 1 1 d . . . . .
S1 S 0.29631(6) 0.63174(4) 0.18651(8) 0.0353(3) Uani 1 1 d . . . . .
S2 S 0.500000 0.33054(6) 0.250000 0.0289(3) Uani 1 2 d S T P . .
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 0.0244(11) 0.0256(11) 0.0327(11) -0.0002(9) 0.0036(8) 0.0016(8)
C2 0.0212(11) 0.0266(11) 0.0339(11) -0.0008(9) 0.0011(8) 0.0014(8)
C3 0.0228(11) 0.0324(11) 0.0433(13) -0.0017(10) 0.0005(9) -0.0032(9)
C4 0.0204(11) 0.0407(13) 0.0425(12) -0.0016(11) 0.0008(9) 0.0038(9)
O1 0.0366(10) 0.0319(8) 0.0519(10) -0.0116(8) 0.0018(7) 0.0022(7)
S1 0.0270(4) 0.0281(4) 0.0480(5) -0.0012(2) 0.0014(3) 0.0056(2)
S2 0.0216(4) 0.0224(5) 0.0398(5) 0.000 0.0000(3) 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 0.0033 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
C1 C1 S1 135.57(7) 2_655 . ?
C2 C1 C1 113.68(12) . 2_655 ?
C2 C1 S1 110.74(16) . . ?
C1 C2 C3 114.25(18) . . ?
C1 C2 S2 110.03(15) . . ?
C3 C2 S2 135.71(16) . . ?
C2 C3 H3 125.0 . . ?
C4 C3 C2 110.08(19) . . ?
C4 C3 H3 125.0 . . ?
C3 C4 H4 123.3 . . ?
C3 C4 S1 113.42(16) . . ?
S1 C4 H4 123.3 . . ?
C1 S1 C4 91.50(11) . . ?
C2 S2 C2 92.57(14) 2_655 . ?
O1 S2 C2 110.99(10) 2_655 2_655 ?
O1 S2 C2 111.68(10) 2_655 . ?
O1 S2 C2 110.99(10) . . ?
O1 S2 C2 111.68(10) . 2_655 ?
O1 S2 O1 116.48(14) . 2_655 ?
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
C1 C1 1.448(4) 2_655 ?
C1 C2 1.380(3) . ?
C1 S1 1.706(2) . ?
C2 C3 1.412(3) . ?
C2 S2 1.769(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 S1 1.713(2) . ?
O1 S2 1.4413(16) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 -179.0(2) 2_655 . . . ?
C1 C1 C2 S2 0.1(3) 2_655 . . . ?
C1 C1 S1 C4 179.2(3) 2_655 . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 S2 C2 -0.05(11) . . . 2_655 ?
C1 C2 S2 O1 113.75(17) . . . 2_655 ?
C1 C2 S2 O1 -114.46(16) . . . . ?
C2 C1 S1 C4 0.17(16) . . . . ?
C2 C3 C4 S1 0.7(3) . . . . ?
C3 C2 S2 C2 178.9(3) . . . 2_655 ?
C3 C2 S2 O1 64.5(3) . . . . ?
C3 C2 S2 O1 -67.3(3) . . . 2_655 ?
C3 C4 S1 C1 -0.53(17) . . . . ?
S1 C1 C2 C3 0.2(3) . . . . ?
S1 C1 C2 S2 179.40(9) . . . . ?
S2 C2 C3 C4 -179.51(17) . . . . ?
