Deep-Red Aggregation-Induced Emission Luminogen Based on Dithiofuvalene-Fused Benzothiadiazole for Lipid Droplet-Specific Imaging
Yu, Ying; Xing, Hao; Park, Hojeong; Zhang, Ruoyao; Peng, Chen; Sung, Herman H.-Y.; Williams, Ian D.; Ma, Chao; Wong, Kam Sing; Li, Shijie; Xiong, Qingping; Li, Min-Hui; Zhao, Zheng; Tang, Ben Zhong; ACS Materials Letters 4 (2021) 159–164; doi:10.1021/acsmaterialslett.1c00570

data_4519264
_publ_section_title
;
 Deep-Red Aggregation-Induced Emission Luminogen Based on
 Dithiofuvalene-Fused Benzothiadiazole for Lipid Droplet-Specific Imaging
;
_journal_issue                   1
_journal_name_full               'ACS Materials Letters'
_journal_page_first              159
_journal_page_last               164
_journal_paper_doi               10.1021/acsmaterialslett.1c00570
_journal_volume                  4
_journal_year                    2021
_chemical_formula_moiety         'C14 N6 S5, C6 H5 Cl'
_chemical_formula_sum            'C20 H5 Cl N6 S5'
_chemical_formula_weight         525.05
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.644(5)
_cell_angle_beta                 75.956(5)
_cell_angle_gamma                77.935(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3216(5)
_cell_length_b                   10.4441(6)
_cell_length_c                   14.9898(9)
_cell_measurement_reflns_used    4418
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7850
_cell_measurement_theta_min      4.3510
_cell_volume                     1077.30(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     38.00 117.00   1.00    5.00    --  106.99-125.00  30.00   79
  2  \w   -117.00 -29.00   1.00    2.00    --  -40.57 -37.00  90.00   88
  3  \w   -119.00 -18.00   1.00    2.00    --  -40.57 -77.00-150.00  101
  4  \w      2.00  83.00   1.00    2.00    --   40.57 -99.00 -30.00   81
  5  \w     60.00 115.00   1.00    5.00    --  106.99-125.00-120.00   55
  6  \w     40.00 132.00   1.00    5.00    --  106.99 -30.00 -30.00   92
  7  \w     80.00 176.00   1.00    5.00    --  106.99  45.00 150.00   96
  8  \w     41.00 123.00   1.00    5.00    --  106.99 -61.00-150.00   82
  9  \w     38.00 136.00   1.00    5.00    --  106.99 -30.00 120.00   98
 10  \w     86.00 137.00   1.00    5.00    --  106.99  45.00 -60.00   51
 11  \w     35.00 138.00   1.00    5.00    --  106.99 -77.00  30.00  103
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0816698000
_diffrn_orient_matrix_UB_12      -0.0410876000
_diffrn_orient_matrix_UB_13      -0.0740222000
_diffrn_orient_matrix_UB_21      -0.0967776000
_diffrn_orient_matrix_UB_22      -0.1017597000
_diffrn_orient_matrix_UB_23      0.0740812000
_diffrn_orient_matrix_UB_31      -0.1801797000
_diffrn_orient_matrix_UB_32      0.1055338000
_diffrn_orient_matrix_UB_33      0.0216276000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6177
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.857
_diffrn_reflns_theta_min         4.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    6.299
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0346P)^2^+0.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4000
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tz1c00570_si_002.cif
_cod_data_source_block           yyu3cult
_cod_original_cell_volume        1077.31(12)
_cod_database_code               4519264
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.744
_shelx_estimated_absorpt_t_min   0.366
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              33444
_shelx_hkl_checksum              57336
_olex2_date_sample_data_collection 2018-10-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.797