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#$Date: 2025-10-28 16:27:46 +0200 (Tue, 28 Oct 2025) $
#$Revision: 303074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/60/1576099.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_1576099
loop_
_publ_author_name
'Chen, Xiang'
'Tao, Siyu'
'Chen, ruijia'
'Zhao, Zihao'
'Zhang, Qiang'
'Li, Anze'
'Yang, Guangxin'
'Liu, Wenbin'
'Yuan, Wang Zhang'
_publ_section_title
;
 Site-Selective Thionation and Doping Enabled Tunable Full-Color Emission
 in Nonconventional Luminophores
;
_journal_name_full               'Materials Horizons'
_journal_paper_doi               10.1039/D5MH01519G
_journal_year                    2025
_chemical_formula_moiety         'C3 H3 N O S2'
_chemical_formula_sum            'C3 H3 N O S2'
_chemical_formula_weight         133.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-09-25
_audit_creation_method
;
Olex2 1.5-ac6-018
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_audit_update_record
;
2025-09-25 deposited with the CCDC.	2025-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.849(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2223(6)
_cell_length_b                   7.5798(6)
_cell_length_c                   9.9313(8)
_cell_measurement_reflns_used    7170
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      6.90
_cell_volume                     530.06(7)
_computing_cell_refinement       ' APEX5 v2023.9--2 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-018 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL--2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9695
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.383
_diffrn_reflns_theta_min         6.904
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.066
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1040 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.7638.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         963
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0193P)²+0.3022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                933
_reflns_number_total             963
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5mh01519g2.cif
_cod_data_source_block           a_a
_cod_database_code               1576099
_shelx_shelxl_version_number     2019/1
_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_max   0.398
_shelx_estimated_absorpt_t_min   0.325
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 S2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_shelx_res_file
;
TITL A_a.res in P2(1)/n
    a_a.res
    created by SHELXL-2019/1 at 13:24:06 on 25-Sep-2025
REM Old TITL A in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.098, Rweak 0.002, Alpha 0.020
REM <I/s> 0.903 for 85 systematic absences, Orientation as input
REM Formula found by SHELXT: C3 N O S2
CELL 1.54178 7.2223 7.5798 9.9313 90 102.849 90
ZERR 4 0.0006 0.0006 0.0008 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 12 12 4 4 8
EQIV $1 1-X,1-Y,1-Z
EQIV $2 -1+X,+Y,+Z
DELU 0.001 0.001 S2 C1

L.S. 10
PLAN  1
SIZE 0.18 0.16 0.14
TEMP -100.15
CONF
HTAB N1 O1_$1
HTAB C3 S2_$2
LIST 4
BOND
MORE -1
BOND $H
htab
fmap 2
acta
OMIT 0 0 6
REM <olex2.extras>
REM <HklSrc "%.\\A_a.hkl">
REM </olex2.extras>

WGHT    0.019300    0.302200
FVAR       1.19508
S1    5    0.525222    0.965832    0.752832    11.00000    0.02479    0.02173 =
         0.02442   -0.00823    0.00781   -0.00217
S2    5    0.827518    0.961859    0.590132    11.00000    0.02101    0.02745 =
         0.02701   -0.00133    0.00688   -0.00714
O1    4    0.314238    0.528856    0.590351    11.00000    0.02615    0.02022 =
         0.02404   -0.00340    0.01147   -0.00532
N1    3    0.557963    0.719136    0.583277    11.00000    0.02080    0.01742 =
         0.01841   -0.00261    0.00915   -0.00143
AFIX  43
H1    2    0.603147    0.656688    0.523105    11.00000   -1.20000
AFIX   0
C1    1    0.641541    0.873911    0.634622    11.00000    0.01732    0.01879 =
         0.01570    0.00124    0.00149    0.00115
C2    1    0.401015    0.663967    0.628556    11.00000    0.01940    0.01777 =
         0.01554    0.00238    0.00535    0.00156
C3    1    0.349995    0.791898    0.730040    11.00000    0.02079    0.01913 =
         0.02105   -0.00170    0.00848    0.00042
AFIX  23
H3A   2    0.352139    0.732489    0.819149    11.00000   -1.20000
H3B   2    0.221295    0.840555    0.694019    11.00000   -1.20000
AFIX   0
HKLF 4




REM  A_a.res in P2(1)/n
REM wR2 = 0.0513, GooF = S = 1.084, Restrained GooF = 1.087 for all data
REM R1 = 0.0206 for 933 Fo > 4sig(Fo) and 0.0210 for all 963 data
REM 64 parameters refined using 1 restraints

END

WGHT      0.0193      0.3022

REM Instructions for potential hydrogen bonds
HTAB N1 O1_$1
HTAB C3 S2_$2

REM Highest difference peak  0.220,  deepest hole -0.234,  1-sigma level  0.049
Q1    1   0.4118  0.8618  0.7382  11.00000  0.05    0.22
;
_shelx_res_checksum              36918
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.52522(5) 0.96583(5) 0.75283(3) 0.02328(13) Uani 1 1 d . . . . .
S2 S 0.82752(5) 0.96186(5) 0.59013(4) 0.02492(13) Uani 1 1 d . U . . .
O1 O 0.31424(14) 0.52886(13) 0.59035(9) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.55796(15) 0.71914(15) 0.58328(11) 0.0181(2) Uani 1 1 d . . . . .
H1 H 0.603147 0.656688 0.523105 0.022 Uiso 1 1 calc R U . . .
C1 C 0.64154(17) 0.87391(18) 0.63462(13) 0.0176(3) Uani 1 1 d . U . . .
C2 C 0.40101(18) 0.66397(17) 0.62856(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.35000(18) 0.79190(18) 0.73004(13) 0.0197(3) Uani 1 1 d . . . . .
H3A H 0.352139 0.732489 0.819149 0.024 Uiso 1 1 calc R U . . .
H3B H 0.221295 0.840555 0.694019 0.024 Uiso 1 1 calc R U . . .
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
S1 0.0248(2) 0.0217(2) 0.0244(2) -0.00823(13) 0.00781(14) -0.00217(13)
S2 0.0210(2) 0.0275(2) 0.0270(2) -0.00133(14) 0.00688(15) -0.00714(13)
O1 0.0261(5) 0.0202(5) 0.0240(5) -0.0034(4) 0.0115(4) -0.0053(4)
N1 0.0208(5) 0.0174(5) 0.0184(5) -0.0026(4) 0.0091(4) -0.0014(4)
C1 0.0173(6) 0.0188(7) 0.0157(6) 0.0012(5) 0.0015(5) 0.0012(5)
C2 0.0194(6) 0.0178(7) 0.0155(6) 0.0024(5) 0.0054(5) 0.0016(5)
C3 0.0208(6) 0.0191(7) 0.0210(6) -0.0017(5) 0.0085(5) 0.0004(5)
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'
N N 0.0311 0.0180 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C3 93.05(6) . . ?
C1 N1 H1 121.1 . . ?
C1 N1 C2 117.88(11) . . ?
C2 N1 H1 121.1 . . ?
S2 C1 S1 124.48(8) . . ?
N1 C1 S1 110.95(9) . . ?
N1 C1 S2 124.57(10) . . ?
O1 C2 N1 124.01(12) . . ?
O1 C2 C3 124.50(11) . . ?
N1 C2 C3 111.49(11) . . ?
S1 C3 H3A 110.4 . . ?
S1 C3 H3B 110.4 . . ?
C2 C3 S1 106.60(9) . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
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 C1 1.7344(13) . ?
S1 C3 1.8065(14) . ?
S2 C1 1.6455(13) . ?
O1 C2 1.2165(16) . ?
N1 H1 0.8800 . ?
N1 C1 1.3652(17) . ?
N1 C2 1.3743(16) . ?
C2 C3 1.5023(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 1.98 2.8402(14) 167.1 3_666 yes
C3 H3B S2 0.99 2.95 3.9367(14) 176.1 1_455 yes
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
O1 C2 C3 S1 179.00(11) . . . . ?
N1 C2 C3 S1 -1.36(13) . . . . ?
C1 S1 C3 C2 1.64(10) . . . . ?
C1 N1 C2 O1 179.90(12) . . . . ?
C1 N1 C2 C3 0.26(16) . . . . ?
C2 N1 C1 S1 1.05(14) . . . . ?
C2 N1 C1 S2 -178.82(9) . . . . ?
C3 S1 C1 S2 178.30(9) . . . . ?
C3 S1 C1 N1 -1.58(10) . . . . ?
