Design, synthesis, and time-gated cell imaging of carbon-bridged triangulenium dyes with long fluorescence lifetime and red emission.
Rosenberg, M.; Rostgaard, K. R.; Liao, Z.; Madsen, A Ø; Martinez, K. L.; Vosch, T.; Laursen, B. W.; Chemical science 9 (2018) 3122–3130; doi:10.1039/c8sc00089a

data_1548990
_publ_section_title
;
 Design, synthesis, and time-gated cell imaging of carbon-bridged
 triangulenium dyes with long fluorescence lifetime and red emission.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3122
_journal_page_last               3130
_journal_paper_doi               10.1039/c8sc00089a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'F6 P, C22 H15 O2'
_chemical_formula_sum            'C22 H15 F6 O2 P'
_chemical_formula_weight         456.31
_chemical_name_systematic
'12,12-dimethylbenzo[8,1]isochromeno[3,4,5,6-klmn]xanthenium hexafluorophosphate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-06-21 deposited with the CCDC.
2018-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                74.017(2)
_cell_angle_beta                 89.013(2)
_cell_angle_gamma                64.503(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4805(5)
_cell_length_b                   8.5013(4)
_cell_length_c                   14.7698(8)
_cell_measurement_reflns_used    6546
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.37
_cell_measurement_theta_min      2.68
_cell_volume                     917.65(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23324
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.68
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014) was used for absorption correction. wR2(int) was 0.1279 before and 0.0503 after correction. The Ratio of minimum to maximum transmission is 0.9297. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'recrystallized from ethanol/acetonitrile'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                3775
_reflns_number_total             5562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc00089a2.cif
_cod_data_source_block           mo_d8v960_0mcopy
_cod_depositor_comments
'Adding full bibliography for 1548989--1548992.cif.'
_cod_database_code               1548990
_olex2_refinement_description
;
;
_olex2_exptl_crystal_mounting_method 'On kapton loop'
_olex2_submission_original_sample_id D8V960
_olex2_submission_special_instructions 'No special instructions were received'