8,8′-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one): a twisted photosensitizer with AIE properties
Broumidis, Emmanouil; Jones, Callum M. S.; Koyioni, Maria; Kourtellaris, Andreas; Lloyd, Gareth O.; Marques-Hueso, Jose; Koutentis, Panayiotis A.; Vilela, Filipe; RSC Advances 11 (2021) 29102–29107; doi:10.1039/D1RA06263H

data_7243454
_publ_section_title
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 8,8&#x2032;-(Benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(quinolin-4(1H)-one):
 a twisted photosensitizer with AIE properties
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_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              29102
_journal_page_last               29107
_journal_paper_doi               10.1039/D1RA06263H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H16 N4 O2 S, 2(C2 F3 O2), 2(C2 H F3 O2)'
_chemical_formula_sum            'C32 H18 F12 N4 O10 S'
_chemical_formula_weight         878.56
_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             2020-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-26 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.14670(10)
_cell_length_b                   21.3962(3)
_cell_length_c                   20.1733(3)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7190
_cell_measurement_theta_min      4.1110
_cell_volume                     3516.24(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71065
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.948
_diffrn_reflns_theta_min         1.902
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       plates
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         6738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0513
_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/[\s^2^(Fo^2^)+(0.0795P)^2^+2.3563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5767
_reflns_number_total             6738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06263h2.cif
_cod_data_source_block           mk_1
_cod_database_code               7243454
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.781
_oxdiff_exptl_absorpt_empirical_full_max 1.658
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: C1C(0.5) O9(0.5) H9(0.5) F10(0.5) O10(0.5) F11(0.5) F12(0.5)
 C31(0.5) F7(0.5) O7(0.5) F8(0.5) O8(0.5) F9(0.5) C29(0.5) C30(0.5) F7A(0.5)
 O7A(0.5) F8A(0.5) O8A(0.5) F9A(0.5) C29A(0.5) C30A(0.5) O9A(0.5) H9A(0.5)
 F10A(0.5) O10A(0.5) F11A(0.5) F12A(0.5) C31A(0.5) C32A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23)
3.b Tetrahedral OH refined with riding coordinates:
 O9(H9), O5(H5A), O9A(H9A)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2)

One half of the trifluoroacetate:trifluoroacetic acid pairs is disordered. 
Refinement without the disorder resulted in an R factor at least 3% higher. 
The rotation of the trifluoromethyl group alone only improved the refinement
 a little and resulted in poor geometric shape to the molecule. 
It was therefore decide to model the whole molecule as disorder. 
The refinement was stable and a free variable gave the disorder as
 approximately 50:50. The occupancy was then fixed to this exactly.
The majority of the minor CIFCHECK alerts are associated with this disorder.
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_shelx_res_checksum              11251
_olex2_submission_special_instructions 'No special instructions were received'