#------------------------------------------------------------------------------
#$Date: 2026-04-05 14:29:24 +0200 (Sun 05 de Apr de 2026) $
#$Revision: 305452 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/60/1576098.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_1576098
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_issue                   3
_journal_name_full               'Materials horizons'
_journal_page_first              1412
_journal_page_last               1420
_journal_paper_doi               10.1039/d5mh01519g
_journal_volume                  13
_journal_year                    2026
_chemical_formula_moiety         'C3 H4 N2 O S'
_chemical_formula_sum            'C3 H4 N2 O S'
_chemical_formula_weight         116.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 99.493(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6533(5)
_cell_length_b                   11.5377(10)
_cell_length_c                   7.4907(8)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      7.12
_cell_volume                     481.90(8)
_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      295.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6115
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         7.117
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.891
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.6807.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0384
_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)+(0.0635P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                823
_reflns_number_total             883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5mh01519g2.cif
_cod_data_source_block           t_a
_cod_depositor_comments
'Adding full bibliography for 1576098--1576100.cif.'
_cod_database_code               1576098
_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   0.441
_shelx_estimated_absorpt_t_min   0.441
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2)
;
_shelx_res_file
;
TITL t_a.res in P2(1)/c
    t_a.res
    created by SHELXL-2019/1 at 10:43:45 on 25-Sep-2025
REM Old TITL t in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.188, Rweak 0.004, Alpha 0.019
REM <I/s> 0.566 for 50 systematic absences, Orientation as input
REM Formula found by SHELXT: C4 N O S
CELL 1.54178 5.6533 11.5377 7.4907 90 99.493 90
ZERR 4 0.0005 0.001 0.0008 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 12 16 8 4 4
EQIV $1 1-X,-0.5+Y,1.5-Z
EQIV $2 -X,1-Y,1-Z
EQIV $3 1-X,1-Y,1-Z

L.S. 10
PLAN  5
SIZE 0.2 0.2 0.2
TEMP 21.85
CONF
HTAB N1 O1_$1
HTAB N2 O1_$2
HTAB C3 O1_$3
BOND
htab
LIST 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\t_a.hkl">
REM </olex2.extras>

WGHT    0.063500    0.178500
FVAR       1.67034
S1    5    0.080273    0.138672    0.569746    11.00000    0.05216    0.03729 =
         0.06596   -0.00063   -0.01159   -0.00888
C1    1    0.236769    0.257734    0.629496    11.00000    0.03442    0.03648 =
         0.04227   -0.00054   -0.00456    0.00217
O1    4    0.300740    0.555488    0.622169    11.00000    0.03826    0.03273 =
         0.06400   -0.00069   -0.01012    0.00026
N1    3    0.450767    0.268048    0.733084    11.00000    0.03573    0.03517 =
         0.05865    0.00372   -0.01274    0.00405
AFIX  43
H1    2    0.535928    0.209893    0.777435    11.00000   -1.20000
AFIX   0
N2    3    0.162815    0.368857    0.577552    11.00000    0.03060    0.03423 =
         0.04967   -0.00010   -0.01199    0.00059
AFIX  43
H2    2    0.029835    0.384040    0.507748    11.00000   -1.20000
AFIX   0
C2    1    0.322100    0.451200    0.648314    11.00000    0.03095    0.03670 =
         0.04492   -0.00149   -0.00333   -0.00001
C3    1    0.524924    0.387160    0.763178    11.00000    0.03301    0.03927 =
         0.05233    0.00180   -0.01024   -0.00027
AFIX  23
H3A   2    0.676636    0.401733    0.722803    11.00000   -1.20000
H3B   2    0.538502    0.408218    0.889826    11.00000   -1.20000
AFIX   0
HKLF 4




REM  t_a.res in P2(1)/c
REM wR2 = 0.1086, GooF = S = 1.085, Restrained GooF = 1.085 for all data
REM R1 = 0.0384 for 823 Fo > 4sig(Fo) and 0.0401 for all 883 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0635      0.1784

REM Instructions for potential hydrogen bonds
HTAB N1 O1_$1
HTAB N2 O1_$2
HTAB C3 O1_$3

REM Highest difference peak  0.392,  deepest hole -0.213,  1-sigma level  0.054
Q1    1   0.1717  0.1398  0.4594  11.00000  0.05    0.39
Q2    1  -0.0074  0.1395  0.6761  11.00000  0.05    0.34
Q3    1   0.2406  0.5428  0.7135  11.00000  0.05    0.28
Q4    1   0.0985  0.0577  0.5657  11.00000  0.05    0.21
Q5    1   0.3544  0.5062  0.5605  11.00000  0.05    0.18
;
_shelx_res_checksum              29692
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.08027(10) 0.13867(4) 0.56975(8) 0.0542(3) Uani 1 1 d . . . . .
C1 C 0.2368(3) 0.25773(16) 0.6295(3) 0.0389(5) Uani 1 1 d . . . . .
O1 O 0.3007(2) 0.55549(11) 0.6222(2) 0.0471(4) Uani 1 1 d . . . . .
N1 N 0.4508(3) 0.26805(15) 0.7331(3) 0.0455(5) Uani 1 1 d . . . . .
H1 H 0.535928 0.209893 0.777435 0.055 Uiso 1 1 calc R U . . .
N2 N 0.1628(3) 0.36886(13) 0.5776(2) 0.0403(4) Uani 1 1 d . . . . .
H2 H 0.029835 0.384040 0.507748 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3221(3) 0.45120(16) 0.6483(3) 0.0386(5) Uani 1 1 d . . . . .
C3 C 0.5249(3) 0.38716(17) 0.7632(3) 0.0435(5) Uani 1 1 d . . . . .
H3A H 0.676636 0.401733 0.722803 0.052 Uiso 1 1 calc R U . . .
H3B H 0.538502 0.408218 0.889826 0.052 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 0.0522(4) 0.0373(4) 0.0660(4) -0.0006(2) -0.0116(3) -0.0089(2)
C1 0.0344(9) 0.0365(11) 0.0423(10) -0.0005(7) -0.0046(7) 0.0022(7)
O1 0.0383(7) 0.0327(8) 0.0640(9) -0.0007(6) -0.0101(6) 0.0003(6)
N1 0.0357(8) 0.0352(9) 0.0587(10) 0.0037(7) -0.0127(7) 0.0040(7)
N2 0.0306(8) 0.0342(9) 0.0497(10) -0.0001(6) -0.0120(7) 0.0006(6)
C2 0.0310(9) 0.0367(10) 0.0449(10) -0.0015(8) -0.0033(8) 0.0000(8)
C3 0.0330(10) 0.0393(11) 0.0523(12) 0.0018(8) -0.0102(8) -0.0003(8)
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
N1 C1 S1 128.76(15) . . ?
N1 C1 N2 106.53(16) . . ?
N2 C1 S1 124.71(14) . . ?
C1 N1 H1 123.6 . . ?
C1 N1 C3 112.89(15) . . ?
C3 N1 H1 123.6 . . ?
C1 N2 H2 123.6 . . ?
C2 N2 C1 112.89(15) . . ?
C2 N2 H2 123.6 . . ?
O1 C2 N2 125.86(18) . . ?
O1 C2 C3 128.28(18) . . ?
N2 C2 C3 105.86(16) . . ?
N1 C3 C2 101.73(15) . . ?
N1 C3 H3A 111.4 . . ?
N1 C3 H3B 111.4 . . ?
C2 C3 H3A 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
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 1.6551(19) . ?
C1 N1 1.330(3) . ?
C1 N2 1.384(2) . ?
O1 C2 1.222(2) . ?
N1 H1 0.8600 . ?
N1 C3 1.444(3) . ?
N2 H2 0.8600 . ?
N2 C2 1.355(2) . ?
C2 C3 1.508(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
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 0.86 2.09 2.943(2) 172.1 2_646 yes
N2 H2 O1 0.86 2.08 2.928(2) 168.7 3_566 yes
C3 H3A O1 0.97 2.65 3.268(3) 121.5 3_666 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
S1 C1 N1 C3 -176.89(15) . . . . ?
S1 C1 N2 C2 178.63(15) . . . . ?
C1 N1 C3 C2 -3.4(2) . . . . ?
C1 N2 C2 O1 179.27(19) . . . . ?
C1 N2 C2 C3 -0.8(2) . . . . ?
O1 C2 C3 N1 -177.7(2) . . . . ?
N1 C1 N2 C2 -1.3(2) . . . . ?
N2 C1 N1 C3 3.0(2) . . . . ?
N2 C2 C3 N1 2.4(2) . . . . ?
