π-Extended diphosphonium-bridged ladder stilbenes: water-soluble fluorophores with up to eight annulated rings.
Senn, Sebastian; Mörsdorf, Jean-Marc; Bertrams, Maria-Sophie; Kerzig, Christoph; Ballmann, Joachim; Chemical science 16 (2025) 20517–20526; doi:10.1039/d5sc03752b

data_1575881
_publ_section_title
;
 &#x3c0;-Extended diphosphonium-bridged ladder stilbenes: water-soluble
 fluorophores with up to eight annulated rings.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              20517
_journal_page_last               20526
_journal_paper_doi               10.1039/d5sc03752b
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H40 P2'
_chemical_formula_sum            'C34 H40 P2'
_chemical_formula_weight         510.60
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-03-14 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                105.871(2)
_cell_angle_beta                 90.048(2)
_cell_angle_gamma                100.228(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8371(2)
_cell_length_b                   11.6905(2)
_cell_length_c                   12.3737(3)
_cell_measurement_reflns_used    16060
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.9750
_cell_measurement_theta_min      3.7200
_cell_volume                     1481.90(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     19.00  64.00   1.00    2.00    --    0.00  77.00-180.00   45
  2  \w     18.00  71.00   1.00    2.00    --    0.00  77.00   0.00   53
  3  \w    -31.00  14.00   1.00    2.00    --    0.00  77.00   0.00   45
  4  \w    -31.00  17.00   1.00    2.00    --    0.00  77.00-180.00   48
  5  \w    -18.00  54.00   1.00    2.00    --    0.00  57.00 120.00   72
  6  \w    -32.00  -7.00   1.00    2.00    --   22.00 123.00 178.84   25
  7  \w    -23.00   2.00   1.00    2.00    --   26.00 115.00 -56.72   25
  8  \w      3.00  28.00   1.00    7.00    --   42.00  91.00  21.71   25
  9  \w      3.00  28.00   1.00    7.00    --   42.00  91.00-102.47   25
 10  \w      2.00  27.00   1.00    7.00    --   42.00  92.00 122.95   25
 11  \w     12.00  37.00   1.00    7.00    --   46.00  81.00-170.58   25
 12  \w     11.00  36.00   1.00    7.00    --   46.00  83.00  71.56   25
 13  \w     14.00  45.00   1.00    7.00    --   46.00  82.00 -49.60   31
 14  \w     70.00 121.00   1.00    7.00    --   50.00  76.00  86.23   51
 15  \w     16.00  41.00   1.00    7.00    --   50.00  82.00  17.57   25
 16  \w     16.00  41.00   1.00    7.00    --   50.00  82.00 -93.57   25
 17  \w     22.00  49.00   1.00    7.00    --   50.00  76.00  86.23   27
 18  \w     28.00  55.00   1.00    7.00    --   54.48  77.00-180.00   27
 19  \w     24.00  49.00   1.00    7.00    --   54.48  77.00 -30.00   25
 20  \w     24.00  85.00   1.00    7.00    --   54.48-125.00-120.00   61
 21  \w     24.00  72.00   1.00    7.00    --   54.48-125.00-180.00   48
 22  \w     27.00  54.00   1.00    7.00    --   54.48  77.00 -60.00   27
 23  \w     29.00  56.00   1.00    7.00    --   54.48  77.00 120.00   27
 24  \w     24.00  49.00   1.00    7.00    --   54.48  77.00 -90.00   25
 25  \w     23.00  50.00   1.00    7.00    --   54.48  77.00 150.00   27
 26  \w     29.00  56.00   1.00    7.00    --   54.48  77.00  30.00   27
 27  \w     24.00  51.00   1.00    7.00    --   54.48  77.00  60.00   27
 28  \w      1.00  97.00   1.00    7.00    --   54.48 -99.00 -30.00   96
 29  \w     29.00  56.00   1.00    7.00    --   58.00  77.00 160.06   27
 30  \w     27.00  52.00   1.00    7.00    --   58.00  77.00   0.59   25
 31  \w     35.00  62.00   1.00    7.00    --   58.00  73.00 -92.92   27
 32  \w    102.00 129.00   1.00    7.00    --   58.00  77.00   0.59   27
 33  \w     95.00 122.00   1.00    7.00    --   58.00  77.00-138.88   27
 34  \w     26.00  52.00   1.00    7.00    --   58.00  77.00-138.88   26
 35  \w     28.00  55.00   1.00    7.00    --   58.00  74.00 -18.88   27
 36  \w     89.00 131.00   1.00    7.00    --   62.00  77.00 -65.25   42
 37  \w     30.00  62.00   1.00    7.00    --   62.00  77.00 -65.25   32
 38  \w     31.00  58.00   1.00    7.00    --   62.00  77.00  67.66   27
 39  \w     31.00  58.00   1.00    7.00    --   62.00  75.00 106.37   27
 40  \w     30.00  58.00   1.00    7.00    --   62.00  77.00  33.95   28
 41  \w     34.00  67.00   1.00    7.00    --   62.00  71.00 -97.78   33
 42  \w     35.00  66.00   1.00    7.00    --   66.00  76.00 -36.71   31
 43  \w     36.00  61.00   1.00    7.00    --   66.00  75.00  41.59   25
 44  \w     38.00  65.00   1.00    7.00    --   66.00  73.00 -72.82   27
 45  \w     39.00 103.00   1.00    7.00    --   66.00  72.00  16.99   64
 46  \w     40.00  65.00   1.00    7.00    --   66.00  75.00 -24.55   25
 47  \w     47.00 130.00   1.00    7.00    --   70.00  64.00 179.14   83
 48  \w     41.00  71.00   1.00    7.00    --   70.00  76.00-129.17   30
 49  \w     39.00  66.00   1.00    7.00    --   70.00  75.00-158.14   27
 50  \w     41.00  68.00   1.00    7.00    --   70.00  77.00  45.11   27
 51  \w     39.00  66.00   1.00    7.00    --   70.00  77.00 121.44   27
 52  \w    111.00 136.00   1.00    7.00    --   70.00  76.00-129.17   25
 53  \w     43.00  70.00   1.00    7.00    --   70.00  71.00   7.75   27
 54  \w     98.00 136.00   1.00    7.00    --   74.00  70.00-109.82   38
 55  \w     53.00  89.00   1.00    7.00    --   74.00  70.00-109.82   36
 56  \w     93.00 139.00   1.00    7.00    --   74.00  66.00 -73.30   46
 57  \w     55.00  85.00   1.00    7.00    --   74.00  66.00 -73.30   30
 58  \w     83.00 145.00   1.00    7.00    --   74.00  75.00  17.98   62
 59  \w     46.00  78.00   1.00    7.00    --   74.00  75.00  17.98   32
 60  \w     51.00  85.00   1.00    7.00    --   74.00  64.00 -79.01   34
 61  \w     48.00  77.00   1.00    7.00    --   78.00  77.00 137.10   29
 62  \w     57.00  84.00   1.00    7.00    --   78.00  73.00 116.89   27
 63  \w     55.00  81.00   1.00    7.00    --   78.00  62.00  45.25   26
 64  \w     53.00  80.00   1.00    7.00    --   78.00  72.00  77.91   27
 65  \w     51.00  78.00   1.00    7.00    --   78.00  70.00 110.12   27
 66  \w     75.00 102.00   1.00   16.00    --   82.00  68.00 102.61   27
 67  \w     61.00  88.00   1.00   16.00    --   82.00  55.00-171.56   27
 68  \w    124.00 152.00   1.00   16.00    --   82.00  77.00  49.83   28
 69  \w     50.00  76.00   1.00   16.00    --   82.00  77.00  49.83   26
 70  \w     51.00  77.00   1.00   16.00    --   82.00  75.00 -69.65   26
 71  \w     64.00 131.00   1.00   16.00    --   86.00  55.00 -68.16   67
 72  \w    105.00 153.00   1.00   16.00    --   86.00  66.00-172.54   48
 73  \w     60.00  91.00   1.00   16.00    --   86.00  66.00-172.54   31
 74  \w    117.00 144.00   1.00   16.00    --   86.00  77.00-132.53   27
 75  \w     54.00  94.00   1.00   16.00    --   86.00  77.00-132.53   40
 76  \w     80.00 156.00   1.00   16.00    --   86.00  76.00 130.16   76
 77  \w     65.00  94.00   1.00   16.00    --   86.00  61.00-153.21   29
 78  \w     55.00 144.00   1.00   16.00    --   86.00  77.00 -43.59   89
 79  \w     66.00  93.00   1.00   16.00    --   90.00  62.00-141.74   27
 80  \w     62.00  90.00   1.00   16.00    --   90.00  70.00 124.76   28
 81  \w     65.00  90.00   1.00   16.00    --   90.00  41.00  29.99   25
 82  \w    128.00 164.00   1.00   16.00    --   94.00  55.00-156.12   36
 83  \w     72.00  98.00   1.00   16.00    --   94.00  55.00-156.12   26
 84  \w     72.00  98.00   1.00   16.00    --   98.00  66.00  66.67   26
 85  \w     80.00 160.00   1.00   16.00    --  102.00  54.00 103.43   80
 86  \w     37.00  76.00   1.00   16.00    --  108.96 -92.00  30.00   39
 87  \w     36.00 109.00   1.00   16.00    --  108.96 -92.00-120.00   73
 88  \w     81.00 108.00   1.00   16.00    --  108.96  71.00 -67.03   27
 89  \w     82.00 116.00   1.00   16.00    --  108.96  38.00  60.00   34
 90  \w     85.00 165.00   1.00   16.00    --  108.96  64.00 150.00   80
 91  \w     85.00 113.00   1.00   16.00    --  108.96  64.00  90.00   28
 92  \w     88.00 169.00   1.00   16.00    --  108.96  64.00  60.00   81
 93  \w     84.00 172.00   1.00   16.00    --  108.96  64.00 -90.00   88
 94  \w     88.00 172.00   1.00   16.00    --  108.96  64.00-180.00   84
 95  \w     80.00 115.00   1.00   16.00    --  108.96  77.00   0.00   35
 96  \w     41.00 132.00   1.00   16.00    --  108.96 -64.00  30.00   91
 97  \w     85.00 161.00   1.00   16.00    --  108.96  64.00 120.00   76
 98  \w     65.00 111.00   1.00   16.00    --  108.96-111.00   0.00   46
 99  \w     85.00 112.00   1.00   16.00    --  108.96  64.00 -30.00   27
100  \w    136.00 176.00   1.00   16.00    --  108.96  64.00-150.00   40
101  \w     86.00 134.00   1.00   16.00    --  108.96  64.00-150.00   48
102  \w    119.00 144.00   1.00   16.00    --  108.96  77.00  90.00   25
103  \w     78.00 105.00   1.00   16.00    --  108.96  77.00  90.00   27
104  \w     77.00 103.00   1.00   16.00    --  108.96  77.00 150.00   26
105  \w     82.00 109.00   1.00   16.00    --  108.96  77.00-180.00   27
106  \w    117.00 158.00   1.00   16.00    --  108.96  77.00   0.00   41
107  \w     78.00 166.00   1.00   16.00    --  108.96  77.00 -60.00   88
108  \w     77.00 104.00   1.00   16.00    --  108.96  77.00-120.00   27
109  \w     85.00 112.00   1.00   16.00    --  108.96  64.00   0.00   27
110  \w     78.00 103.00   1.00   16.00    --  108.96  77.00 120.00   25
111  \w     77.00 103.00   1.00   16.00    --  108.96  77.00  60.00   26
112  \w    113.00 170.00   1.00   16.00    --  108.96  77.00  30.00   57
113  \w     77.00 104.00   1.00   16.00    --  108.96  77.00  30.00   27
114  \w     47.00 109.00   1.00   16.00    --  108.96-111.00-150.00   62
115  \w     77.00 104.00   1.00   16.00    --  108.96  77.00-150.00   27
116  \w     80.00 107.00   1.00   16.00    --  108.96  77.00 -90.00   27
117  \w     78.00 176.00   1.00   16.00    --  108.96  77.00 -30.00   98
118  \w     74.00 109.00   1.00   16.00    --  108.96-111.00  90.00   35
119  \w     85.00 174.00   1.00   16.00    --  108.96  64.00-120.00   89
120  \w     40.00 127.00   1.00   16.00    --  108.96 -50.00-120.00   87
121  \w     76.00 103.00   1.00   16.00    --  108.96 -92.00 120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0997575000
_diffrn_orient_matrix_UB_12      0.0654642000
_diffrn_orient_matrix_UB_13      0.0659003000
_diffrn_orient_matrix_UB_21      0.0901344000
_diffrn_orient_matrix_UB_22      0.1222478000
_diffrn_orient_matrix_UB_23      0.0186424000
_diffrn_orient_matrix_UB_31      -0.0533610000
_diffrn_orient_matrix_UB_32      0.0142606000
_diffrn_orient_matrix_UB_33      -0.1100419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31950
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.133
_diffrn_reflns_theta_min         3.719
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 4248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         10602
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0783P)^2^+0.0773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                9980
_reflns_number_total             10602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_3b_ba_ss9
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_database_code               1575881
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C34H40P2
_chemical_oxdiff_usercomment     ss228
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.758
_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
 P51-C73A \\sim P51-C73B
 with sigma of 0.02
 C73A-C75A \\sim C73B-C75B
 with sigma of 0.02
 C73A-C74A \\sim C73B-C74B
 with sigma of 0.02
 P51-C75A \\sim P51-C75B
 with sigma of 0.02
 P51-C74A \\sim P51-C74B
 with sigma of 0.02
 C75A-C74A \\sim C75B-C74B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C73A \\sim C73B \\sim C74B \\sim C74A \\sim C75A \\sim C75B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C73A) = Uanis(C73B)
4. Others
 Sof(C73B)=Sof(H73B)=Sof(C74B)=Sof(H74D)=Sof(H74E)=Sof(H74F)=Sof(C75B)=
 Sof(H75D)=Sof(H75E)=Sof(H75F)=1-FVAR(1)
 Sof(C73A)=Sof(H73A)=Sof(C75A)=Sof(H75A)=Sof(H75B)=Sof(H75C)=Sof(C74A)=
 Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C29(H29), C82(H82), C26(H26), C79(H79), C23(H23), C32(H32), C76(H76),
 C73A(H73A), C73B(H73B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C53(H53), C8(H8), C59(H59), C58(H58), C9(H9), C67(H67), C64(H64),
 C65(H65), C15(H15), C20(H20), C55(H55), C54(H54), C14(H14), C68(H68), C56(H56),
  C4(H4), C17(H17), C70(H70), C69(H69), C6(H6), C18(H18), C5(H5), C19(H19)
5.c Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C34(H34A,H34B,H34C), C27(H27A,H27B,H27C), C81(H81A,H81B,
 H81C), C30(H30A,H30B,H30C), C28(H28A,H28B,H28C), C24(H24A,H24B,H24C), C83(H83A,
 H83B,H83C), C78(H78A,H78B,H78C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C),
 C77(H77A,H77B,H77C), C80(H80A,H80B,H80C), C25(H25A,H25B,H25C), C75A(H75A,H75B,
 H75C), C74A(H74A,H74B,H74C), C74B(H74D,H74E,H74F), C75B(H75D,H75E,H75F)
;
_shelx_res_checksum              4103
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;