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_1575886
_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, 2(Cl)'
_chemical_formula_sum            'C34 H40 Cl2 P2'
_chemical_formula_weight         581.50
_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'
_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                 104.4060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.24390(10)
_cell_length_b                   18.9138(2)
_cell_length_c                   11.37540(10)
_cell_measurement_reflns_used    24187
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.6500
_cell_measurement_theta_min      4.6460
_cell_volume                     1509.53(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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    -21.00  69.00   1.00    3.00    --    0.00  57.00-150.00   90
  2  \w    -26.00  72.00   1.00    3.00    --    0.00  38.00 120.00   98
  3  \w    -38.00  11.00   1.00    3.00    --   10.00 110.00-112.33   49
  4  \w    -31.00  15.00   1.00    3.00    --   14.00 105.00 144.84   46
  5  \w    -38.00  -5.00   1.00    3.00    --   22.00 129.00  70.23   33
  6  \w      2.00  45.00   1.00    9.00    --   34.00  81.00 -98.14   43
  7  \w     -2.00  24.00   1.00    9.00    --   38.00  96.00 -16.74   26
  8  \w      6.00  33.00   1.00    9.00    --   42.00  88.00  -2.18   27
  9  \w      5.00  33.00   1.00    9.00    --   42.00  89.00 116.81   28
 10  \w     14.00  45.00   1.00    9.00    --   46.00  81.00  30.14   31
 11  \w     13.00  40.00   1.00    9.00    --   46.00  83.00-126.04   27
 12  \w     13.00  45.00   1.00    9.00    --   46.00  82.00 -58.30   32
 13  \w     17.00  45.00   1.00    9.00    --   50.00  82.00  97.10   28
 14  \w     21.00 120.00   1.00    9.00    --   50.00  75.00 -26.77   99
 15  \w     18.00  45.00   1.00    9.00    --   50.00  81.00-114.69   27
 16  \w     24.00 124.00   1.00    9.00    --   54.00  77.00 120.00  100
 17  \w     24.00 124.00   1.00    9.00    --   54.00  77.00 150.00  100
 18  \w     24.00 124.00   1.00    9.00    --   54.00  77.00   0.00  100
 19  \w     24.00 124.00   1.00    9.00    --   54.00  77.00-180.00  100
 20  \w     24.00 124.00   1.00    9.00    --   54.00  77.00  51.27  100
 21  \w    -15.00  75.00   1.00    9.00    --   54.00 -57.00   0.00   90
 22  \w    -15.00  75.00   1.00    9.00    --   54.00 -57.00 -90.00   90
 23  \w     23.00 111.00   1.00    9.00    --   54.00-125.00-150.00   88
 24  \w     24.00 124.00   1.00    9.00    --   54.00  77.00 -60.00  100
 25  \w     23.00 111.00   1.00    9.00    --   54.00-125.00 -90.00   88
 26  \w     29.00 128.00   1.00    9.00    --   58.00  75.00 -97.63   99
 27  \w     33.00 126.00   1.00    9.00    --   58.00  69.00 -46.88   93
 28  \w     32.00 127.00   1.00    9.00    --   58.00  70.00 152.47   95
 29  \w     29.00  65.00   1.00    9.00    --   58.00  76.00  31.34   36
 30  \w     30.00  67.00   1.00    9.00    --   58.00  74.00-146.08   37
 31  \w     32.00  57.00   1.00    9.00    --   58.00  74.00 -79.41   25
 32  \w     30.00  55.00   1.00    9.00    --   58.00  76.00  70.68   25
 33  \w     37.00  80.00   1.00    9.00    --   62.00  73.00 -35.06   43
 34  \w     42.00  69.00   1.00    9.00    --   62.00  70.00 113.64   27
 35  \w     39.00  66.00   1.00    9.00    --   62.00  73.00 177.22   27
 36  \w     46.00  76.00   1.00    9.00    --   62.00  62.00  35.01   30
 37  \w     36.00  62.00   1.00    9.00    --   62.00  70.00-115.22   26
 38  \w     42.00  77.00   1.00    9.00    --   62.00  63.00 -50.34   35
 39  \w     32.00  61.00   1.00    9.00    --   62.00  77.00  69.08   29
 40  \w     41.00  68.00   1.00    9.00    --   62.00  66.00  -3.11   27
 41  \w     36.00  63.00   1.00    9.00    --   62.00  73.00 166.36   27
 42  \w     44.00  72.00   1.00    9.00    --   66.00  65.00 119.46   28
 43  \w     40.00  66.00   1.00    9.00    --   66.00  71.00  44.84   26
 44  \w     49.00  75.00   1.00    9.00    --   70.00  70.00 120.15   26
 45  \w     42.00  69.00   1.00    9.00    --   70.00  73.00 -57.71   27
 46  \w     42.00 139.00   1.00    9.00    --   70.00  74.00-106.71   97
 47  \w     90.00 120.00   1.00    9.00    --   74.00  63.00 -17.44   30
 48  \w     53.00  87.00   1.00    9.00    --   74.00  63.00 -17.44   34
 49  \w     53.00 130.00   1.00    9.00    --   74.00  51.00  34.42   77
 50  \w     54.00  81.00   1.00    9.00    --   74.00  69.00 147.46   27
 51  \w     55.00 121.00   1.00    9.00    --   74.00  59.00  75.32   66
 52  \w     46.00 104.00   1.00    9.00    --   74.00  75.00 131.12   58
 53  \w     53.00 101.00   1.00    9.00    --   78.00  69.00 169.60   48
 54  \w     51.00  78.00   1.00    9.00    --   78.00  71.00-154.43   27
 55  \w     48.00  74.00   1.00    9.00    --   78.00  77.00  78.74   26
 56  \w     50.00  76.00   1.00    9.00    --   78.00  73.00  25.46   26
 57  \w     53.00  86.00   1.00   21.00    --   82.00  75.00 -49.18   33
 58  \w     60.00 119.00   1.00   21.00    --   82.00  65.00  41.46   59
 59  \w     71.00 153.00   1.00   21.00    --   86.00  65.00 -29.52   82
 60  \w     58.00 118.00   1.00   21.00    --   86.00  76.00-157.90   60
 61  \w     70.00 103.00   1.00   21.00    --   90.00  56.00 177.73   33
 62  \w     69.00 112.00   1.00   21.00    --   90.00  62.00 154.89   43
 63  \w     69.00  95.00   1.00   21.00    --   94.00  72.00 -50.78   26
 64  \w     64.00 163.00   1.00   21.00    --   94.00  77.00-103.70   99
 65  \w     79.00 115.00   1.00   21.00    --   98.00  58.00  65.97   36
 66  \w    117.00 165.00   1.00   21.00    --  108.00  64.00 150.00   48
 67  \w     86.00 112.00   1.00   21.00    --  108.00  64.00 150.00   26
 68  \w    114.00 177.00   1.00   21.00    --  108.00  77.00  30.00   63
 69  \w     81.00 107.00   1.00   21.00    --  108.00  77.00  30.00   26
 70  \w     86.00 175.00   1.00   21.00    --  108.00  64.00-180.00   89
 71  \w     36.00  79.00   1.00   21.00    --  108.00 -92.00 -60.00   43
 72  \w     96.00 123.00   1.00   21.00    --  108.00  50.00 120.00   27
 73  \w     87.00 175.00   1.00   21.00    --  108.00  64.00   0.00   88
 74  \w     78.00 105.00   1.00   21.00    --  108.00  77.00-150.00   27
 75  \w     41.00 131.00   1.00   21.00    --  108.00 -64.00  90.00   90
 76  \w    120.00 164.00   1.00   21.00    --  108.00  64.00  60.00   44
 77  \w     36.00 109.00   1.00   21.00    --  108.00 -92.00  30.00   73
 78  \w     86.00 114.00   1.00   21.00    --  108.00  64.00  60.00   28
 79  \w     86.00 119.00   1.00   21.00    --  108.00  64.00  30.00   33
 80  \w     41.00 108.00   1.00   21.00    --  108.00-111.00 -90.00   67
 81  \w     85.00 112.00   1.00   21.00    --  108.00  64.00 -90.00   27
 82  \w     45.00 105.00   1.00   21.00    --  108.00-111.00   0.00   60
 83  \w     86.00 112.00   1.00   21.00    --  108.00  63.00 -99.57   26
 84  \w     85.00 174.00   1.00   21.00    --  108.00  64.00  90.00   89
 85  \w     85.00 165.00   1.00   21.00    --  108.00  64.00 -30.00   80
 86  \w     85.00 172.00   1.00   21.00    --  108.00  64.00 -53.24   87
 87  \w     78.00 105.00   1.00   21.00    --  108.00  77.00 -60.00   27
 88  \w     81.00 113.00   1.00   21.00    --  108.00-111.00-180.00   32
 89  \w     85.00 114.00   1.00   21.00    --  108.00  64.00 120.00   29
 90  \w     79.00 104.00   1.00   21.00    --  108.00  77.00 150.00   25
 91  \w     80.00 106.00   1.00   21.00    --  108.00  77.00  60.00   26
 92  \w     79.00 104.00   1.00   21.00    --  108.00  77.00-180.00   25
 93  \w     80.00 107.00   1.00   21.00    --  108.00  77.00   0.00   27
 94  \w     85.00 169.00   1.00   21.00    --  108.00  77.00 -90.00   84
 95  \w     79.00 104.00   1.00   21.00    --  108.00  77.00  90.00   25
 96  \w     86.00 163.00   1.00   21.00    --  108.00  64.00-120.00   77
 97  \w     82.00 177.00   1.00   21.00    --  108.00  77.00 120.00   95
 98  \w     86.00 159.00   1.00   21.00    --  108.00  64.00-150.00   73
 99  \w     86.00 111.00   1.00   21.00    --  108.00  64.00 -60.00   25
100  \w    105.00 130.00   1.00   21.00    --  108.00 -50.00  30.00   25
101  \w     39.00  87.00   1.00   21.00    --  108.00 -50.00  30.00   48
102  \w     79.00 105.00   1.00   21.00    --  108.00  77.00 -30.00   26
103  \w     66.00  91.00   1.00   21.00    --  108.00 -92.00 120.00   25
;
_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      0.1670026000
_diffrn_orient_matrix_UB_12      0.0021950000
_diffrn_orient_matrix_UB_13      0.1143531000
_diffrn_orient_matrix_UB_21      -0.1362139000
_diffrn_orient_matrix_UB_22      -0.0216527000
_diffrn_orient_matrix_UB_23      0.0783336000
_diffrn_orient_matrix_UB_31      0.0422167000
_diffrn_orient_matrix_UB_32      -0.0784795000
_diffrn_orient_matrix_UB_33      -0.0184585000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35263
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.729
_diffrn_reflns_theta_min         4.645
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.090
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.781
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0525P)^2^+0.6604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2795
_reflns_number_total             2892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_4a_ba_jm83
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_database_code               1575886
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C34 H40 P2 Cl2'
_chemical_oxdiff_usercomment     'JM_Napt_Cl, irregualr, yellow'
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.689
_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 Ternary CH refined with riding coordinates:
 C12(H12), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C6(H6), C9(H9), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C16(H16A,H16B,
 H16C)
;
_shelx_res_checksum              44819
_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
;