#------------------------------------------------------------------------------
#$Date: 2023-09-05 21:10:31 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286046 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/95/1569578.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_1569578
loop_
_publ_author_name
'Ortiz-Rodríguez, Luis A'
'Fang, Ye-Guang'
'Niogret, Germain'
'Hadidi, Kaivin'
'Hoehn, Sean J.'
'Folkwein, Heather J.'
'Jockusch, Steffen'
'Tor, Yitzhak'
'Cui, Ganglong'
'Levi, Liraz'
'Crespo-Hernández, Carlos E'
_publ_section_title
;
 Thieno[3,4-d]pyrimidin-4(3H)-thione: an effective,
 oxygenation independent, heavy-atom-free photosensitizer for cancer
 cells.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              8831
_journal_page_last               8841
_journal_paper_doi               10.1039/d3sc02592f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C6 H4 N2 S2'
_chemical_formula_sum            'C6 H4 N2 S2'
_chemical_formula_weight         168.23
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2021-06-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.375(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.523(5)
_cell_length_b                   9.208(4)
_cell_length_c                   7.108(3)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.410
_cell_measurement_theta_min      2.967
_cell_volume                     677.5(5)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.349
_diffrn_reflns_theta_min         1.967
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0719 before and 0.0330 after correction. The Ratio of minimum to maximum transmission is 0.8657. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0258
_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)+(0.0367P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1247
_reflns_number_total             1385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02592f2.cif
_cod_data_source_block           tor_this_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569577--1569578.cif.
;
_cod_original_cell_volume        677.4(5)
_cod_database_code               1569578
_shelx_shelxl_version_number     2016/6
_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   0.966
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5)
;
_shelx_res_file
;
TITL TOR_thIS_0m_a.res in P2(1)/c
    tor_this_0m_a.res
    created by SHELXL-2016/6 at 15:26:05 on 28-May-2019
REM Old TITL Integration of TOR_thIS
REM SHELXT solution in P2(1)/c
REM R1 0.096, Rweak 0.002, Alpha 0.018, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: C6 N2 S2
CELL 0.71073 10.5232 9.2076 7.1076 90 100.375 90
ZERR 4 0.0047 0.0037 0.0031 0 0.015 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 24 16 8 8

L.S. 10
PLAN  20
SIZE 0.05 0.08 0.22
TEMP -173.15
BOND $H
LIST 6
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\TOR_thIS_0m_a.hkl">
REM </olex2.extras>

WGHT    0.036700    0.356400
FVAR       0.49162
S2    4    0.065484    0.858847    0.402373    11.00000    0.01781    0.02011 =
         0.01910   -0.00064   -0.00101    0.00634
S1    4    0.241293    0.364231    0.507760    11.00000    0.01892    0.01378 =
         0.03636   -0.00221   -0.00294   -0.00167
N1    3    0.421683    0.550038    0.672983    11.00000    0.01416    0.01328 =
         0.02149    0.00042    0.00113    0.00215
AFIX  43
H1    2    0.468961    0.472829    0.709757    11.00000   -1.20000
AFIX   0
N2    3    0.418254    0.807773    0.680748    11.00000    0.01568    0.01523 =
         0.01993   -0.00202    0.00164   -0.00006
C3    1    0.230456    0.663327    0.521166    11.00000    0.01483    0.01543 =
         0.01415   -0.00117    0.00401    0.00071
C6    1    0.292397    0.799508    0.577307    11.00000    0.01634    0.01619 =
         0.01356   -0.00038    0.00373    0.00008
C1    1    0.474339    0.683469    0.722418    11.00000    0.01298    0.01889 =
         0.01832   -0.00223    0.00131   -0.00077
AFIX  43
H1A   2    0.559817    0.685315    0.793814    11.00000   -1.20000
AFIX   0
C2    1    0.299490    0.528835    0.569407    11.00000    0.01561    0.01654 =
         0.01576   -0.00021    0.00438    0.00027
C4    1    0.105843    0.680322    0.424331    11.00000    0.01736    0.01763 =
         0.01675   -0.00246    0.00315    0.00108
AFIX  43
H4    2    0.049910    0.602636    0.376229    11.00000   -1.20000
AFIX   0
C5    1    0.213105    0.916282    0.520575    11.00000    0.02001    0.01640 =
         0.01967   -0.00115    0.00260    0.00174
AFIX  43
H5    2    0.236993    1.015049    0.543799    11.00000   -1.20000
AFIX   0
HKLF 4




REM  TOR_thIS_0m_a.res in P2(1)/c
REM R1 =  0.0258 for    1247 Fo > 4sig(Fo)  and  0.0296 for all    1385 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0367      0.3561

REM Highest difference peak  0.380,  deepest hole -0.170,  1-sigma level  0.060
Q1    1   0.2566  0.5939  0.5561  11.00000  0.05    0.38
Q2    1   0.0746  0.7578  0.4291  11.00000  0.05    0.36
Q3    1   0.2622  0.7233  0.5513  11.00000  0.05    0.35
Q4    1   0.2713  0.4482  0.5491  11.00000  0.05    0.30
Q5    1   0.1486  0.8878  0.4700  11.00000  0.05    0.29
Q6    1   0.2442  0.8544  0.5843  11.00000  0.05    0.27
Q7    1   0.2652  0.8572  0.5383  11.00000  0.05    0.26
Q8    1   0.3639  0.8044  0.6294  11.00000  0.05    0.26
Q9    1   0.1636  0.6607  0.5142  11.00000  0.05    0.24
Q10   1   0.4407  0.8769  0.7304  11.00000  0.05    0.24
Q11   1   0.4401  0.6212  0.6913  11.00000  0.05    0.24
Q12   1   0.4455  0.7596  0.6670  11.00000  0.05    0.24
Q13   1   0.0737  0.6456  0.4340  11.00000  0.05    0.22
Q14   1   0.3684  0.5437  0.6266  11.00000  0.05    0.22
Q15   1   0.4231  0.7709  0.7039  11.00000  0.05    0.21
Q16   1   0.1511  0.3961  0.4937  11.00000  0.05    0.21
Q17   1   0.2429  0.3345  0.6138  11.00000  0.05    0.17
Q18   1   0.2163  0.9541  0.5460  11.00000  0.05    0.17
Q19   1   0.3064  0.2996  0.5809  11.00000  0.05    0.16
Q20   1  -0.0185  0.8827  0.4076  11.00000  0.05    0.14
;
_shelx_res_checksum              51963
_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
S2 S 0.06548(4) 0.85885(4) 0.40237(5) 0.01954(13) Uani 1 1 d . . . . .
S1 S 0.24129(4) 0.36423(4) 0.50776(6) 0.02400(14) Uani 1 1 d . . . . .
N1 N 0.42168(11) 0.55004(14) 0.67298(17) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.468961 0.472829 0.709757 0.020 Uiso 1 1 calc R . . . .
N2 N 0.41825(11) 0.80777(14) 0.68075(18) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.23046(14) 0.66333(16) 0.5212(2) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.29240(14) 0.79951(16) 0.5773(2) 0.0152(3) Uani 1 1 d . . . . .
C1 C 0.47434(14) 0.68347(16) 0.7224(2) 0.0169(3) Uani 1 1 d . . . . .
H1A H 0.559817 0.685315 0.793814 0.020 Uiso 1 1 calc R . . . .
C2 C 0.29949(14) 0.52884(16) 0.5694(2) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.10584(14) 0.68032(16) 0.4243(2) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.049910 0.602636 0.376229 0.021 Uiso 1 1 calc R . . . .
C5 C 0.21310(15) 0.91628(17) 0.5206(2) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.236993 1.015049 0.543799 0.023 Uiso 1 1 calc R . . . .
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
S2 0.0178(2) 0.0201(2) 0.0191(2) -0.00064(14) -0.00101(15) 0.00634(14)
S1 0.0189(2) 0.0138(2) 0.0364(3) -0.00221(15) -0.00294(17) -0.00167(14)
N1 0.0142(6) 0.0133(6) 0.0215(7) 0.0004(5) 0.0011(5) 0.0021(4)
N2 0.0157(6) 0.0152(6) 0.0199(7) -0.0020(5) 0.0016(5) -0.0001(5)
C3 0.0148(7) 0.0154(7) 0.0141(7) -0.0012(5) 0.0040(6) 0.0007(5)
C6 0.0163(7) 0.0162(7) 0.0136(7) -0.0004(6) 0.0037(5) 0.0001(6)
C1 0.0130(7) 0.0189(7) 0.0183(7) -0.0022(6) 0.0013(6) -0.0008(6)
C2 0.0156(7) 0.0165(7) 0.0158(7) -0.0002(6) 0.0044(5) 0.0003(6)
C4 0.0174(7) 0.0176(7) 0.0167(7) -0.0025(6) 0.0031(6) 0.0011(6)
C5 0.0200(7) 0.0164(7) 0.0197(8) -0.0011(6) 0.0026(6) 0.0017(6)
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'
N N 0.0061 0.0033 '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
C4 S2 C5 93.68(8) . . ?
C1 N1 H1 117.9 . . ?
C1 N1 C2 124.16(12) . . ?
C2 N1 H1 117.9 . . ?
C1 N2 C6 114.93(13) . . ?
C6 C3 C2 119.90(13) . . ?
C4 C3 C6 112.56(13) . . ?
C4 C3 C2 127.53(14) . . ?
N2 C6 C3 122.27(13) . . ?
C5 C6 N2 125.40(14) . . ?
C5 C6 C3 112.32(14) . . ?
N1 C1 H1A 117.0 . . ?
N2 C1 N1 125.97(13) . . ?
N2 C1 H1A 117.0 . . ?
N1 C2 S1 122.31(11) . . ?
N1 C2 C3 112.75(13) . . ?
C3 C2 S1 124.93(12) . . ?
S2 C4 H4 124.6 . . ?
C3 C4 S2 110.87(11) . . ?
C3 C4 H4 124.6 . . ?
S2 C5 H5 124.7 . . ?
C6 C5 S2 110.57(12) . . ?
C6 C5 H5 124.7 . . ?
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
S2 C4 1.6979(16) . ?
S2 C5 1.7113(17) . ?
S1 C2 1.6636(16) . ?
N1 H1 0.8800 . ?
N1 C1 1.367(2) . ?
N1 C2 1.3757(19) . ?
N2 C6 1.3963(19) . ?
N2 C1 1.297(2) . ?
C3 C6 1.436(2) . ?
C3 C2 1.445(2) . ?
C3 C4 1.376(2) . ?
C6 C5 1.376(2) . ?
C1 H1A 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
