Highly emissive water-soluble tetraazaperopyrenes as fluorescent markers
Lena Hahn; Simin Oz; Hubert Wadepohl; Lutz H. Gade; Chem.Commun. 50 (2014) 4941–; doi:10.1039/C4CC01254B

data_7112613
_publ_section_title
;
 Highly emissive water-soluble tetraazaperopyrenes as fluorescent markers
;
_journal_name_full               Chem.Commun.
_journal_page_first              4941
_journal_paper_doi               10.1039/C4CC01254B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C48 H20 F14 N8, 3(C4 H8 O)'
_chemical_formula_sum            'C60 H44 F14 N8 O3'
_chemical_formula_weight         1191.03
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_lh5
_audit_creation_date             2014-02-12
_audit_update_record             'Wed Feb 12 16:11:49 CET 2014'
_cell_angle_alpha                90
_cell_angle_beta                 108.873(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.096(10)
_cell_length_b                   11.551(5)
_cell_length_c                   22.445(10)
_cell_measurement_reflns_used    8099
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.39
_cell_volume                     5175(4)
_computing_cell_refinement
;
SAINT 8.x (Bruker AXS, 1997-2012). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT 8.x (Bruker AXS, 1997-2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al., 2004)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            61657
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.659
_diffrn_reflns_theta_min         1.918
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             2440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         7908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0660P)^2^+8.4620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5881
_reflns_number_total             7908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01254b2.cif
_cod_data_source_block           ga_lh5
_cod_original_cell_volume        5176(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7112613
_audit_block_refno               1860
_audit_block_usercomment         LH353
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C51(H51A,
 H51B), C52(H52A,H52B)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35)
;
_shelx_res_checksum              58285