Thieno[3,4-<i>d</i>]pyrimidin-4(3<i>H</i>)-thione: an effective, oxygenation independent, heavy-atom-free photosensitizer for cancer cells.
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; Chemical science 14 (2023) 8831–8841; doi:10.1039/d3sc02592f

data_1569577
_publ_section_title
;
 Thieno[3,4-<i>d</i>]pyrimidin-4(3<i>H</i>)-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 O S'
_chemical_formula_sum            'C6 H4 N2 O S'
_chemical_formula_weight         152.17
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.809(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0765(12)
_cell_length_b                   3.7722(4)
_cell_length_c                   25.105(2)
_cell_measurement_reflns_used    1841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.20
_cell_volume                     1207.5(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7242
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         1.629
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1067 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8513. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0462
_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/[\s^2^(Fo^2^)+(0.0364P)^2^+0.7216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1804
_reflns_number_total             2454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02592f2.cif
_cod_data_source_block           tor_thinb
_cod_depositor_comments
'Adding full bibliography for 1569577--1569578.cif.'
_cod_database_code               1569577
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-H1 = N1'-H1'
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C1'(H1'A), C4'(H4'), C6'(H6')
;
_shelx_res_checksum              88490
_olex2_submission_special_instructions 'No special instructions were received'