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_1575890
_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_formula_moiety         'C34 H40 P2, 3(C H4 O), 2(Cl)'
_chemical_formula_sum            'C37 H52 Cl2 O3 P2'
_chemical_formula_weight         677.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-14 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.6810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8117(2)
_cell_length_b                   11.70200(10)
_cell_length_c                   17.50060(10)
_cell_measurement_reflns_used    52632
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.7290
_cell_measurement_theta_min      4.5080
_cell_volume                     3656.50(6)
_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 0.993
_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    -64.00 -10.00   1.00    2.00    --    0.00 -57.00  90.00   54
  2  \w    -20.00  69.00   1.00    2.00    --    0.00  57.00-120.00   89
  3  \w    -21.00   5.00   1.00    2.00    --    0.00  57.00 -60.00   26
  4  \w     12.00  39.00   1.00    2.00    --    0.00  57.00 -60.00   27
  5  \w     -3.00  22.00   1.00    2.00    --    0.00 -57.00  90.00   25
  6  \w    -29.00  68.00   1.00    2.00    --    0.00  77.00 120.00   97
  7  \w    -29.00  -4.00   1.00    2.00    --   16.00 106.00 -49.15   25
  8  \w    -31.00   1.00   1.00    2.00    --   20.00 118.00-118.57   32
  9  \w    -42.00 -16.00   1.00    8.00    --   28.00 145.00 -27.67   26
 10  \w     -9.00  16.00   1.00    8.00    --   36.00 103.00-105.47   25
 11  \w      5.00  30.00   1.00    8.00    --   44.00  90.00 135.42   25
 12  \w      6.00  31.00   1.00    8.00    --   44.00  89.00-144.32   25
 13  \w      6.00  31.00   1.00    8.00    --   44.00  88.00 -76.49   25
 14  \w      6.00  31.00   1.00    8.00    --   44.00  88.00  75.49   25
 15  \w     14.00  39.00   1.00    8.00    --   48.00  82.00-150.45   25
 16  \w     16.00  41.00   1.00    8.00    --   48.00  81.00  14.81   25
 17  \w     18.00  43.00   1.00    8.00    --   52.00  81.00 115.62   25
 18  \w     18.00  43.00   1.00    8.00    --   52.00  82.00-113.89   25
 19  \w     18.00  43.00   1.00    8.00    --   52.00  82.00 140.54   25
 20  \w     18.00  43.00   1.00    8.00    --   52.00  82.00 -20.88   25
 21  \w     19.00  44.00   1.00    8.00    --   52.00  80.00-130.85   25
 22  \w     19.00  44.00   1.00    8.00    --   52.00  80.00  97.74   25
 23  \w    -53.00 -23.00   1.00    8.00    --  -53.50 -77.00 150.00   30
 24  \w    -50.00 -24.00   1.00    8.00    --  -53.50 -77.00-120.00   26
 25  \w    -84.00  17.00   1.00    8.00    --  -53.50  77.00 120.00  101
 26  \w    -58.00 -22.00   1.00    8.00    --  -53.50 -77.00   0.00   36
 27  \w    -92.00  -3.00   1.00    8.00    --  -53.50 125.00 -60.00   89
 28  \w     23.00  49.00   1.00    8.00    --   54.61  77.00 -30.00   26
 29  \w     23.00  49.00   1.00    8.00    --   54.61  77.00  60.00   26
 30  \w     23.00  89.00   1.00    8.00    --   54.61-125.00-120.00   66
 31  \w     25.00  51.00   1.00    8.00    --   56.00  76.00 172.93   26
 32  \w     28.00  54.00   1.00    8.00    --   60.00  77.00 179.67   26
 33  \w     96.00 129.00   1.00    8.00    --   60.00  77.00 -13.54   33
 34  \w     76.00 103.00   1.00    8.00    --   60.00  77.00 -60.25   27
 35  \w     30.00  55.00   1.00    8.00    --   60.00  75.00-122.08   25
 36  \w     29.00  54.00   1.00    8.00    --   60.00  77.00-100.01   25
 37  \w     28.00  55.00   1.00    8.00    --   60.00  77.00 -30.60   27
 38  \w     31.00  57.00   1.00    8.00    --   60.00  76.00 -48.58   26
 39  \w     30.00  56.00   1.00    8.00    --   60.00  77.00 -60.25   26
 40  \w     33.00  59.00   1.00    8.00    --   60.00  76.00-114.40   26
 41  \w     34.00  60.00   1.00    8.00    --   60.00  76.00-139.26   26
 42  \w     31.00  64.00   1.00    8.00    --   60.00  77.00 -13.54   33
 43  \w     28.00  62.00   1.00    8.00    --   60.00  77.00  30.03   34
 44  \w     29.00  55.00   1.00    8.00    --   60.00  77.00  21.24   26
 45  \w     32.00  58.00   1.00    8.00    --   60.00  76.00 103.05   26
 46  \w     34.00  60.00   1.00    8.00    --   64.00  75.00 106.14   26
 47  \w     35.00  61.00   1.00    8.00    --   64.00  72.00 145.92   26
 48  \w     86.00 119.00   1.00    8.00    --   64.00  70.00  73.88   33
 49  \w     82.00 109.00   1.00    8.00    --   64.00  75.00 106.14   27
 50  \w     37.00  80.00   1.00    8.00    --   64.00  70.00  73.88   43
 51  \w     37.00  74.00   1.00    8.00    --   64.00  68.00  96.64   37
 52  \w     36.00  67.00   1.00    8.00    --   64.00  72.00 123.35   31
 53  \w     34.00  60.00   1.00    8.00    --   64.00  77.00 126.10   26
 54  \w     33.00  58.00   1.00    8.00    --   64.00  77.00 -82.33   25
 55  \w     36.00  63.00   1.00    8.00    --   64.00  76.00-164.33   27
 56  \w     37.00  73.00   1.00    8.00    --   68.00  75.00  40.15   36
 57  \w     40.00  66.00   1.00    8.00    --   68.00  70.00-171.11   26
 58  \w     47.00  73.00   1.00    8.00    --   68.00  73.00 162.85   26
 59  \w     72.00 101.00   1.00    8.00    --   68.00  76.00-142.57   29
 60  \w     40.00  68.00   1.00    8.00    --   68.00  76.00-142.57   28
 61  \w     43.00 109.00   1.00    8.00    --   68.00  70.00 150.69   66
 62  \w     71.00  98.00   1.00    8.00    --   68.00  74.00 -37.94   27
 63  \w     38.00  65.00   1.00    8.00    --   68.00  74.00 -37.94   27
 64  \w     43.00  96.00   1.00    8.00    --   68.00  69.00 -47.77   53
 65  \w     40.00  73.00   1.00    8.00    --   68.00  75.00   5.15   33
 66  \w     37.00  66.00   1.00    8.00    --   68.00  77.00 -87.90   29
 67  \w     45.00  71.00   1.00    8.00    --   72.00  70.00 136.34   26
 68  \w     47.00  72.00   1.00    8.00    --   72.00  67.00 126.91   25
 69  \w     42.00 142.00   1.00    8.00    --   72.00  77.00 -38.41  100
 70  \w     48.00  76.00   1.00    8.00    --   72.00  70.00 -12.87   28
 71  \w     44.00 100.00   1.00    8.00    --   72.00  70.00  39.25   56
 72  \w     45.00  71.00   1.00    8.00    --   72.00  74.00 147.59   26
 73  \w     41.00  68.00   1.00    8.00    --   72.00  75.00  -2.71   27
 74  \w     54.00  83.00   1.00    8.00    --   72.00  54.00 106.11   29
 75  \w     46.00 147.00   1.00    8.00    --   76.00  75.00  55.88  101
 76  \w     46.00  72.00   1.00    8.00    --   76.00  74.00 101.64   26
 77  \w     53.00 112.00   1.00    8.00    --   76.00  67.00 152.76   59
 78  \w     51.00  77.00   1.00    8.00    --   76.00  69.00 -65.53   26
 79  \w     45.00  82.00   1.00    8.00    --   76.00  75.00-131.20   37
 80  \w     52.00  94.00   1.00    8.00    --   76.00  66.00 -97.86   42
 81  \w     45.00  71.00   1.00    8.00    --   76.00  77.00 -96.15   26
 82  \w     51.00 150.00   1.00    8.00    --   80.00  72.00 163.97   99
 83  \w     60.00  86.00   1.00    8.00    --   80.00  62.00 105.85   26
 84  \w     51.00  86.00   1.00    8.00    --   80.00  73.00 -56.21   35
 85  \w     58.00 149.00   1.00    8.00    --   80.00  57.00   5.49   91
 86  \w     49.00  75.00   1.00    8.00    --   80.00  75.00-173.71   26
 87  \w     53.00  78.00   1.00   14.00    --   84.00  77.00-130.43   25
 88  \w     55.00  82.00   1.00   14.00    --   84.00  76.00-140.55   27
 89  \w     53.00  99.00   1.00   14.00    --   84.00  76.00 122.09   46
 90  \w     53.00 152.00   1.00   14.00    --   84.00  76.00 -56.40   99
 91  \w    126.00 152.00   1.00   14.00    --   84.00  77.00  25.56   26
 92  \w     52.00  78.00   1.00   14.00    --   84.00  77.00  25.56   26
 93  \w     53.00  79.00   1.00   14.00    --   84.00  77.00 161.95   26
 94  \w     55.00  81.00   1.00   14.00    --   84.00  74.00-109.86   26
 95  \w     57.00  83.00   1.00   14.00    --   88.00  76.00  -9.30   26
 96  \w     67.00  97.00   1.00   14.00    --   88.00  55.00 -18.02   30
 97  \w     61.00 134.00   1.00   14.00    --   88.00  73.00-137.11   73
 98  \w     60.00  89.00   1.00   14.00    --   88.00  71.00 -88.02   29
 99  \w     66.00  92.00   1.00   14.00    --   92.00  73.00 -89.12   26
100  \w     63.00  91.00   1.00   14.00    --   92.00  72.00-179.55   28
101  \w    126.00 155.00   1.00   14.00    --   92.00  75.00  69.32   29
102  \w     61.00  87.00   1.00   14.00    --   92.00  75.00  69.32   26
103  \w     70.00  95.00   1.00   14.00    --   92.00  64.00  13.65   25
104  \w     67.00  99.00   1.00   14.00    --   92.00  67.00  20.27   32
105  \w    121.00 165.00   1.00   14.00    --   96.00  72.00  36.78   44
106  \w     67.00  94.00   1.00   14.00    --   96.00  72.00  36.78   27
107  \w     66.00 108.00   1.00   14.00    --   96.00  76.00-164.03   42
108  \w     75.00 106.00   1.00   14.00    --   96.00  55.00 -23.41   31
109  \w     73.00 130.00   1.00   14.00    --   96.00  46.00 -85.15   57
110  \w     68.00  94.00   1.00   14.00    --  100.00  77.00  75.02   26
111  \w     77.00 171.00   1.00   14.00    --  100.00  50.00 122.42   94
112  \w     74.00 101.00   1.00   14.00    --  100.00  66.00 -74.91   27
113  \w     69.00 115.00   1.00   14.00    --  100.00  75.00-139.72   46
114  \w     73.00  98.00   1.00   14.00    --  100.00  70.00 159.29   25
115  \w     79.00 104.00   1.00   14.00    --  100.00  66.00 -38.28   25
116  \w     73.00 171.00   1.00   14.00    --  104.00  75.00 140.22   98
117  \w    123.00 148.00   1.00   14.00    --  104.00  72.00 122.79   25
118  \w     75.00 101.00   1.00   14.00    --  104.00  72.00 122.79   26
119  \w    121.00 148.00   1.00   14.00    --  109.22  64.00-120.00   27
120  \w     85.00 111.00   1.00   14.00    --  109.22  64.00-120.00   26
121  \w     85.00 176.00   1.00   14.00    --  109.22  64.00-180.00   91
122  \w     85.00 127.00   1.00   14.00    --  109.22  64.00 -30.00   42
123  \w     78.00 104.00   1.00   14.00    --  109.22  77.00 -90.00   26
124  \w     43.00 109.00   1.00   14.00    --  109.22 -92.00  90.00   66
125  \w     80.00 178.00   1.00   14.00    --  109.22  77.00 150.00   98
126  \w     86.00 112.00   1.00   14.00    --  109.22  64.00   0.00   26
127  \w     78.00 145.00   1.00   14.00    --  109.22  77.00  30.00   67
128  \w     80.00 176.00   1.00   14.00    --  109.22  77.00  90.00   96
129  \w     58.00  84.00   1.00   14.00    --  109.22 -38.00-120.00   26
130  \w     79.00 144.00   1.00   14.00    --  109.22  77.00   0.00   65
131  \w     80.00 178.00   1.00   14.00    --  109.22  77.00-150.00   98
132  \w     88.00 176.00   1.00   14.00    --  109.22  64.00 -60.00   88
133  \w     40.00 112.00   1.00   14.00    --  109.22-111.00  30.00   72
134  \w     78.00 104.00   1.00   14.00    --  109.22  77.00-120.00   26
135  \w    142.00 169.00   1.00   14.00    --  109.22 111.00 -90.00   27
136  \w     80.00 107.00   1.00   14.00    --  109.22  77.00-180.00   27
137  \w    117.00 177.00   1.00   14.00    --  109.22  77.00 -30.00   60
138  \w     79.00 104.00   1.00   14.00    --  109.22  77.00 -30.00   25
139  \w    112.00 158.00   1.00   14.00    --  109.22 111.00-120.00   46
140  \w     38.00  74.00   1.00   14.00    --  109.22 -92.00-120.00   36
141  \w     45.00  70.00   1.00   14.00    --  109.22 -92.00  60.00   25
142  \w     37.00  83.00   1.00   14.00    --  109.22 -92.00 -30.00   46
143  \w     46.00 111.00   1.00   14.00    --  109.22-111.00-150.00   65
144  \w     79.00 168.00   1.00   14.00    --  109.22  77.00  14.53   89
145  \w     87.00 113.00   1.00   14.00    --  109.22  64.00  90.00   26
146  \w     85.00 176.00   1.00   14.00    --  109.22  64.00 -90.00   91
147  \w     57.00  83.00   1.00   14.00    --  109.22 -92.00  30.00   26
148  \w     78.00 115.00   1.00   14.00    --  109.22  77.00 120.00   37
149  \w     86.00 177.00   1.00   14.00    --  109.22  64.00  60.00   91
150  \w     44.00 112.00   1.00   14.00    --  109.22-111.00 -60.00   68
151  \w     79.00 106.00   1.00   14.00    --  109.22  77.00 -60.00   27
152  \f    -60.00 210.00   1.00    0.20   0.00   0.00   0.00    --   270
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0818734000
_diffrn_orient_matrix_UB_12      0.0130391000
_diffrn_orient_matrix_UB_13      -0.0138104000
_diffrn_orient_matrix_UB_21      0.0272036000
_diffrn_orient_matrix_UB_22      0.0414881000
_diffrn_orient_matrix_UB_23      0.0921503000
_diffrn_orient_matrix_UB_31      -0.0006367000
_diffrn_orient_matrix_UB_32      0.1242073000
_diffrn_orient_matrix_UB_33      -0.0294890000
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            97563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.931
_diffrn_reflns_theta_min         4.518
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.732
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         7023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0513P)^2^+1.8166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6611
_reflns_number_total             7023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd4cPh_ba_ss2
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1575890
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C37H52Cl2O3P2
_chemical_oxdiff_usercomment     ss15
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.630
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26), C29(H29), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A), O3(H3A)
;
_shelx_res_checksum              79190
_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
;