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_7112612
_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         'C52 H32 F14 N8, 4(C F3 O3 S)'
_chemical_formula_sum            'C56 H32 F26 N8 O12 S4'
_chemical_formula_weight         1631.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_lh7
_audit_creation_date
;
'Wed Dec 04 11:54:00 2013'
;
_audit_update_record             'Wed Dec  4 11:58:12 CET 2013'
_cell_angle_alpha                90
_cell_angle_beta                 99.183(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5849(6)
_cell_length_b                   9.8070(4)
_cell_length_c                   29.9716(13)
_cell_measurement_reflns_used    8995
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      69.8990
_cell_measurement_theta_min      4.2470
_cell_volume                     3071.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -16.00   17.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 33

  2 omega   30.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 35

  3 omega  -27.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -150.0000 88

  4 omega  -58.00  -27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 31

  5 omega  -69.00    5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 74

  6 omega  -17.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 29

  7 omega  -68.00   17.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 85

  8 omega   24.00  124.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 100

  9 omega   82.00  122.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 40

 10 omega   25.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 38

 11 omega   24.00   78.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 54

 12 omega   24.00   54.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 30

 13 omega  -15.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 80

 14 omega   24.00  101.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 77

 15 omega   25.00   58.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 33

 16 omega   83.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 26

 17 omega   79.00  117.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 38

 18 omega   83.00  111.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 28

 19 omega  -16.00   79.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  -60.0000 95

 20 omega   24.00   55.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 31

 21 omega  -11.00   54.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 65

 22 omega   63.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 41

 23 omega   24.00   50.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 26

 24 omega   24.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 35

 25 omega   24.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 38

 26 omega   24.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 27

 27 omega   24.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 35

 28 omega   60.00  123.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 63

 29 omega   24.00   64.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 40

 30 omega   77.00  122.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 45

 31 omega   64.00  111.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 47

 32 omega  117.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 60

 33 omega   78.00  104.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 34 omega   78.00  104.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 35 omega   85.00  132.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 47

 36 omega   85.00  110.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   60.0000 25

 37 omega  108.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 69

 38 omega   82.00  145.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 63

 39 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 25

 40 omega   82.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 34

 41 omega   36.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 80

 42 omega   83.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   69.0000  137.4524 26

 43 omega   85.00  175.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 90

 44 omega   85.00  163.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   90.0000 78

 45 omega  132.00  165.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 33

 46 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 25

 47 omega  115.00  175.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 60

 48 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 49 omega   48.00  137.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 89

 50 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 51 omega   86.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  120.0000 25

 52 omega   82.00  132.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 50

 53 omega   85.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 46

 54 omega   85.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 26

 55 omega  109.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 65

 56 omega  111.00  168.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 57

 57 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 25

 58 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 25

 59 omega   78.00  104.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 60 omega  123.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 54

 61 omega   78.00  105.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

 62 omega  112.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 66

 63 omega   86.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   90.0000 29

 64 omega   86.00  175.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 89

 65 omega  128.00  170.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 42

 66 omega   78.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 67 omega   82.00  108.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 26

 68 omega   85.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  150.0000 31

 69 omega   39.00  138.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 99

 70 omega   85.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 26

 71 omega   36.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 79

 72 omega   81.00  107.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000 -136.7234 26

 73 omega   87.00  113.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   52.0000    4.5224 26

 74 omega   86.00  112.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   46.0000   67.4578 26

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0162778000
_diffrn_orient_matrix_UB_12      -0.1555287000
_diffrn_orient_matrix_UB_13      0.0034589000
_diffrn_orient_matrix_UB_21      0.0579769000
_diffrn_orient_matrix_UB_22      0.0056638000
_diffrn_orient_matrix_UB_23      0.0505228000
_diffrn_orient_matrix_UB_31      -0.1345207000
_diffrn_orient_matrix_UB_32      0.0212179000
_diffrn_orient_matrix_UB_33      0.0122216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            44255
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.847
_diffrn_reflns_theta_min         4.256
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.795
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1636
_exptl_crystal_size_max          0.1959
_exptl_crystal_size_mid          0.1290
_exptl_crystal_size_min          0.0934
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         5881
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0596P)^2^+6.9083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4499
_reflns_number_total             5881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc01254b2.cif
_cod_data_source_block           ga_lh7
_cod_original_cell_volume        3071.3(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7112612
_audit_block_refno               1919
_audit_block_usercomment         'LH253, irregular, red'
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C56 H32 F26 N8 O12 S4'
_chemical_oxdiff_usercomment     'LH253, irregular, red'
_shelx_estimated_absorpt_t_max   0.767
_shelx_estimated_absorpt_t_min   0.767
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 S1-O11 \\sim S1-O12 \\sim S1-O13
 with sigma of 0.01
 O11-O12 \\sim O11-O13 \\sim O12-O13
 with sigma of 0.01
 C51-F11 \\sim C51-F12 \\sim C51-F13
 with sigma of 0.01
 F11-F12 \\sim F11-F13 \\sim F12-F13
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O11 \\sim O12 \\sim O13 \\sim O21A \\sim O22A \\sim O23A \\sim O21B \\sim O22B
\\sim O23B \\sim S1 \\sim S2A \\sim S2B \\sim C1 \\sim C2 \\sim C3 \\sim C4
\\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C21 \\sim C23
\\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C29 \\sim C30 \\sim C31 \\sim C32
\\sim C33 \\sim C34 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C51 \\sim
C52A \\sim C52B: within 0.5A with sigma of 0.02 and sigma for terminal atoms of
0.04
4. Same fragment restrains
{S1, O11, O12, O13, F11, F12, F13, C51}
as
{S2A, O21A, O22A, O23A, F21A, F22A, F23A, C52A}
{S1, O11, O12, O13, F11, F12, F13, C51}
as
{S2B, O21B, O22B, O23B, F21B, F22B, F23B, C52B}
5. Others
 Sof(S2B)=Sof(O21B)=Sof(O22B)=Sof(O23B)=Sof(F21B)=Sof(F22B)=Sof(F23B)=
 Sof(C52B)=1-FVAR(1)
 Sof(S2A)=Sof(O21A)=Sof(O22A)=Sof(O23A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=
 Sof(C52A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C27(H27), C29(H29), C30(H30), C31(H31), C34(H34), C36(H36),
 C37(H37), C38(H38)
6.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              21238
_cell_oxdiff_length_a            10.5892(6)
_cell_oxdiff_length_b            9.8080(4)
_cell_oxdiff_length_c            29.9583(9)
_cell_oxdiff_angle_alpha         90.051(3)
_cell_oxdiff_angle_beta          99.209(4)
_cell_oxdiff_angle_gamma         90.006(4)
_cell_oxdiff_volume              3071.3(2)
_cell_oxdiff_measurement_reflns_used 8995