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_1548989
_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, C21 H15 N2 O'
_chemical_formula_sum            'C21 H15 F6 N2 O P'
_chemical_formula_weight         456.32
_chemical_name_systematic
'4,8-dimethyl-4,8-diaza-12-oxatriangulenium hexafluorophosphate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-03
_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                90.00
_cell_angle_beta                 96.101(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.861(3)
_cell_length_b                   10.695(4)
_cell_length_c                   23.818(10)
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      3.44
_cell_volume                     1737.8(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f 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  0.0000
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1546
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1594 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.7661.
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    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method CH3CN/2-propanol
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2257
_refine_ls_wR_factor_ref         0.2350
_reflns_number_gt                944
_reflns_number_total             1546
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc00089a2.cif
_cod_data_source_block           mo_d8v1234_0ma
_cod_depositor_comments
'Adding full bibliography for 1548989--1548992.cif.'
_cod_database_code               1548989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C12(H12), C0AA(H0AA), C21(H21)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_exptl_crystal_mounting_method 'on kapton loop'
_olex2_submission_original_sample_id D8V1234
_olex2_submission_special_instructions 'No special instructions were received'