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_1548991
_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, C23 H18 N O'
_chemical_formula_sum            'C23 H18 F6 N O P'
_chemical_formula_weight         469.36
_chemical_name_systematic
;
'8,12,12-trimethyl-8,12-dihydro-3a2H-benzo[8,1]isochromeno[3,4,5,6-klmn]
acridinium 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             2016-06-14
_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                87.939(5)
_cell_angle_beta                 85.555(8)
_cell_angle_gamma                62.365(8)
_cell_formula_units_Z            8
_cell_length_a                   14.162(3)
_cell_length_b                   15.264(4)
_cell_length_c                   20.039(5)
_cell_measurement_reflns_used    7470
_cell_measurement_temperature    122.4
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.54
_cell_volume                     3826.1(16)
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      122.4
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'four-circle kappa-geometry 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  0.0817
_diffrn_reflns_av_unetI/netI     0.1189
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22235
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.52
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4563
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1931
_exptl_crystal_preparation       'Crystallized from CH2Cl2'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.205
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       0.0065(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         10648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.056
_refine_ls_R_factor_all          0.2891
_refine_ls_R_factor_gt           0.2362
_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^)+(0.1508P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5448
_refine_ls_wR_factor_ref         0.5657
_reflns_number_gt                6585
_reflns_number_total             10648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc00089a2.cif
_cod_data_source_block           mo_d8v1061m_0ma
_cod_depositor_comments
;

2019-01-24
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 1548989--1548992.cif.
;
_cod_original_cell_volume        3826.0(16)
_cod_original_formula_moiety     '4(F6 P), 4(C23 H18 N O)'
_cod_original_formula_sum        'C92 H72 F24 N4 O4 P4 '
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1877.46
_cod_database_code               1548991
_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:
 C1(H1), C4DA(H4DA), C3DA(H3DA), C6CA(H6CA), C9CA(H9CA), C1DA(H1DA), C9(H9),
 C0BA(H0BA), C4BA(H4BA), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C4(H4), C7CA(H7CA), C9BA(H9BA), C7AA(H7AA), C1AA(H1AA), C2AA(H2AA), C3AA(H3AA),
  C5CA(H5CA), C6AA(H6AA), C8AA(H8AA), C3BA(H3BA), C30(H30), C32(H32), C33(H33),
 C43(H43), C44(H44), C47(H47), C54(H54), C55(H55), C56(H56), C58(H58), C59(H59)
2.b Idealised Me refined as rotating group:
 C1CA(H1CA,H1CB,H1CC), C0CA(H0CA,H0CB,H0CC), C7BA(H7BA,H7BB,H7BC), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C5DA(H5DA,H5DB,H5DC)
;
_olex2_exptl_crystal_mounting_method 'Kapton loop'
_olex2_submission_original_sample_id D8V1061
_olex2_submission_special_instructions 'No special instructions were received'