Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes.
Sodre, Elaine R.; Guido, Bruna C.; de Souza, Paulo E. N.; Machado, Daniel F. S.; Carvalho-Silva, Valter H; Chaker, Juliano A.; Gatto, Claudia C.; Correa, Jose R.; Fernandes, Talita de A; Neto, Brenno A. D.; The Journal of organic chemistry 85 (2020) 12614–12634; doi:10.1021/acs.joc.0c01805

data_4038756
_publ_section_title
;
 Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and
 Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell
 Imaging Probes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12614
_journal_page_last               12634
_journal_paper_doi               10.1021/acs.joc.0c01805
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C22 H12 N2 S'
_chemical_formula_sum            'C22 H12 N2 S'
_chemical_formula_weight         336.40
_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     iterative
_audit_creation_date             2020-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.826(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0548(17)
_cell_length_b                   10.6734(15)
_cell_length_c                   13.4266(19)
_cell_measurement_reflns_used    3738
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.45
_cell_volume                     1711.5(4)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0746
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_min         1.705
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1017 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0134(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0507P)^2^+0.5354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2077
_reflns_number_total             3145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01805_si_003.cif
_cod_data_source_block           ban_ers_3_0m
_cod_depositor_comments
'Adding full bibliography for 4038755--4038756.cif.'
_cod_database_code               4038756
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.916
_shelx_res_checksum              74053
_shelx_hkl_checksum              66904