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_1575885
_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, 4(C H2 Cl2), 2(Cl)'
_chemical_formula_sum            'C38 H48 Cl10 P2'
_chemical_formula_weight         921.20
_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                 112.535(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0324(2)
_cell_length_b                   10.6843(2)
_cell_length_c                   15.1691(3)
_cell_measurement_reflns_used    16477
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.6080
_cell_measurement_theta_min      3.4930
_cell_volume                     2250.30(8)
_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 2018/2 (Sheldrick, 2018)'
_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 0.991
_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    -16.00  69.00   1.00    1.00    --    0.00  57.00 -90.00   85
  2  \w     24.00  55.00   1.00    1.00    --    0.00  57.00-180.00   31
  3  \w     10.00  71.00   1.00    1.00    --    0.00  77.00 -30.00   61
  4  \w    -32.00   8.00   1.00    1.00    --    0.00  77.00 -30.00   40
  5  \w    -19.00  15.00   1.00    1.00    --    0.00  57.00-180.00   34
  6  \w    -43.00 -10.00   1.00    1.00    --   10.00 124.00  20.33   33
  7  \w    -33.00   8.00   1.00    1.00    --   14.00 112.00 102.78   41
  8  \w    -40.00 -14.00   1.00    6.00    --   30.00 145.00  62.79   26
  9  \w    -18.00   7.00   1.00    6.00    --   30.00 113.00 -83.54   25
 10  \w      3.00  28.00   1.00    6.00    --   42.00  90.00  83.92   25
 11  \w      3.00  28.00   1.00    6.00    --   42.00  91.00 -98.09   25
 12  \w     11.00  36.00   1.00    6.00    --   46.00  84.00-139.46   25
 13  \w     11.00  36.00   1.00    6.00    --   46.00  84.00 -81.62   25
 14  \w     12.00  37.00   1.00    6.00    --   46.00  82.00 153.90   25
 15  \w     13.00  38.00   1.00    6.00    --   46.00  80.00  52.26   25
 16  \w     17.00  42.00   1.00    6.00    --   50.00  80.00  -5.67   25
 17  \w     16.00  45.00   1.00    6.00    --   50.00  82.00  64.55   29
 18  \w     69.00 125.00   1.00    6.00    --   54.47  77.00 150.00   56
 19  \w     23.00  49.00   1.00    6.00    --   54.47  77.00 150.00   26
 20  \w    -15.00  67.00   1.00    6.00    --   54.47 -57.00  30.00   82
 21  \w     -7.00  76.00   1.00    6.00    --   54.47 -57.00  90.00   83
 22  \w     24.00 111.00   1.00    6.00    --   54.47-125.00 -60.00   87
 23  \w     26.00  53.00   1.00    6.00    --   58.00  77.00 -46.25   27
 24  \w     26.00  53.00   1.00    6.00    --   58.00  77.00-137.59   27
 25  \w     86.00 129.00   1.00    6.00    --   58.00  77.00 -46.25   43
 26  \w     33.00  69.00   1.00    6.00    --   58.00  77.00 -85.63   36
 27  \w     32.00  59.00   1.00    6.00    --   62.00  74.00 100.76   27
 28  \w     74.00 133.00   1.00    6.00    --   62.00  76.00  39.22   59
 29  \w     31.00  69.00   1.00    6.00    --   62.00  76.00  39.22   38
 30  \w     31.00  57.00   1.00    6.00    --   62.00  75.00   3.35   26
 31  \w     32.00  57.00   1.00    6.00    --   62.00  75.00-175.33   25
 32  \w     39.00  64.00   1.00    6.00    --   70.00  77.00  70.36   25
 33  \w     39.00  68.00   1.00    6.00    --   70.00  76.00-113.69   29
 34  \w     41.00  66.00   1.00    6.00    --   70.00  74.00  54.63   25
 35  \w     87.00 114.00   1.00    6.00    --   70.00  77.00-178.55   27
 36  \w     38.00  65.00   1.00    6.00    --   70.00  77.00-178.55   27
 37  \w     78.00 115.00   1.00    6.00    --   70.00  76.00  10.25   37
 38  \w     39.00  71.00   1.00    6.00    --   70.00  76.00  10.25   32
 39  \w     40.00  66.00   1.00    6.00    --   70.00  74.00 -49.57   26
 40  \w    106.00 141.00   1.00    6.00    --   70.00  77.00  70.36   35
 41  \w     46.00  79.00   1.00    6.00    --   74.00  72.00 145.34   33
 42  \w     81.00 134.00   1.00    6.00    --   74.00  74.00 122.15   53
 43  \w     45.00  75.00   1.00    6.00    --   74.00  74.00 122.15   30
 44  \w     44.00  71.00   1.00    6.00    --   74.00  74.00 -27.69   27
 45  \w     42.00 103.00   1.00    6.00    --   74.00  77.00-155.66   61
 46  \w     51.00  76.00   1.00    6.00    --   78.00  70.00  46.08   25
 47  \w     47.00  87.00   1.00    6.00    --   78.00  77.00 -83.67   40
 48  \w     54.00  80.00   1.00    6.00    --   78.00  62.00  37.86   26
 49  \w     55.00  89.00   1.00    6.00    --   78.00  63.00 172.94   34
 50  \w     48.00  79.00   1.00    6.00    --   78.00  74.00 -23.64   31
 51  \w     56.00  83.00   1.00   22.00    --   82.00  66.00  89.30   27
 52  \w     54.00  84.00   1.00   22.00    --   82.00  70.00 -60.94   30
 53  \w    108.00 155.00   1.00   22.00    --   86.00  74.00 113.73   47
 54  \w     56.00 103.00   1.00   22.00    --   86.00  74.00 113.73   47
 55  \w     56.00 118.00   1.00   22.00    --   86.00  75.00 -26.54   62
 56  \w     57.00  84.00   1.00   22.00    --   86.00  72.00  92.13   27
 57  \w     60.00 158.00   1.00   22.00    --   90.00  76.00 -15.00   98
 58  \w     59.00 120.00   1.00   22.00    --   90.00  76.00-123.36   61
 59  \w     64.00  91.00   1.00   22.00    --   94.00  74.00-141.00   27
 60  \w     97.00 160.00   1.00   22.00    --   94.00  74.00  93.92   63
 61  \w     65.00  92.00   1.00   22.00    --   94.00  74.00  93.92   27
 62  \w    133.00 164.00   1.00   22.00    --   94.00  73.00 122.73   31
 63  \w     65.00  92.00   1.00   22.00    --   94.00  73.00 122.73   27
 64  \w     65.00 124.00   1.00   22.00    --   94.00  74.00 -78.51   59
 65  \w     66.00  94.00   1.00   22.00    --   94.00  71.00 162.68   28
 66  \w     72.00 103.00   1.00   22.00    --   98.00  66.00  27.13   31
 67  \w     72.00 172.00   1.00   22.00    --  102.00  74.00 153.84  100
 68  \w     77.00 147.00   1.00   22.00    --  108.94  77.00   0.00   70
 69  \w     77.00 159.00   1.00   22.00    --  108.94  77.00-120.00   82
 70  \w     38.00 105.00   1.00   22.00    --  108.94 -92.00  30.00   67
 71  \w     78.00 158.00   1.00   22.00    --  108.94  77.00 -60.00   80
 72  \w    125.00 168.00   1.00   22.00    --  108.94 111.00   0.00   43
 73  \w     77.00 178.00   1.00   22.00    --  108.94  77.00 -90.00  101
 74  \w     77.00 178.00   1.00   22.00    --  108.94  77.00 -30.00  101
 75  \w     40.00 103.00   1.00   22.00    --  108.94 -92.00 -30.00   63
 76  \w     36.00 108.00   1.00   22.00    --  108.94 -92.00-180.00   72
 77  \w     37.00  76.00   1.00   22.00    --  108.94 -92.00  90.00   39
 78  \w     53.00 110.00   1.00   22.00    --  108.94-111.00 -60.00   57
 79  \w     80.00 178.00   1.00   22.00    --  108.94  72.00 118.46   98
 80  \w     84.00 110.00   1.00   22.00    --  108.94  64.00-120.00   26
 81  \w     84.00 168.00   1.00   22.00    --  108.94  64.00-150.00   84
 82  \w    111.00 177.00   1.00   22.00    --  108.94  77.00-180.00   66
 83  \w     77.00 103.00   1.00   22.00    --  108.94  77.00-180.00   26
 84  \w     78.00 163.00   1.00   22.00    --  108.94  77.00  90.00   85
 85  \w     77.00 170.00   1.00   22.00    --  108.94  77.00  60.00   93
 86  \w     40.00 111.00   1.00   22.00    --  108.94-111.00 150.00   71
 87  \w     84.00 116.00   1.00   22.00    --  108.94  64.00-180.00   32
 88  \w     77.00 172.00   1.00   22.00    --  108.94  77.00  30.00   95
;
_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      0.0958252000
_diffrn_orient_matrix_UB_12      -0.0204617000
_diffrn_orient_matrix_UB_13      0.0855312000
_diffrn_orient_matrix_UB_21      -0.0145557000
_diffrn_orient_matrix_UB_22      -0.1427651000
_diffrn_orient_matrix_UB_23      -0.0112206000
_diffrn_orient_matrix_UB_31      0.0539943000
_diffrn_orient_matrix_UB_32      -0.0021398000
_diffrn_orient_matrix_UB_33      -0.0681570000
_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  0.0853
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.922
_diffrn_reflns_theta_min         3.520
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.542
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.484
_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    1.360
_exptl_crystal_description       irregular
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0771P)^2^+1.2921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3815
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_iso_4b_ba_ss3
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_cell_volume        2250.30(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575885
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C38H48Cl10P2
_chemical_oxdiff_usercomment     ssGB01
_shelx_estimated_absorpt_t_max   0.736
_shelx_estimated_absorpt_t_min   0.386
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_shelx_res_checksum              9306
_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
;