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_1575884
_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'
_chemical_formula_sum            'C34 H40 P2'
_chemical_formula_weight         510.60
_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                 104.0550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.67190(10)
_cell_length_b                   11.97920(10)
_cell_length_c                   11.09950(10)
_cell_measurement_reflns_used    12318
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.6920
_cell_measurement_theta_min      5.1520
_cell_volume                     1376.49(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     40.00  70.00   1.00    2.00    --    0.00  38.00-120.00   30
  2  \w    -27.00  27.00   1.00    2.00    --    0.00  38.00-120.00   54
  3  \w     11.00  71.00   1.00    2.00    --    0.00  77.00 150.00   60
  4  \w    -18.00  16.00   1.00    2.00    --    0.00 -57.00  30.00   34
  5  \w    -30.00   9.00   1.00    2.00    --    0.00  77.00 150.00   39
  6  \w    -66.00 -41.00   1.00    2.00    --    0.00 -57.00  30.00   25
  7  \w    -37.00   0.00   1.00    2.00    --   10.00 109.00  47.64   37
  8  \w    -32.00  -5.00   1.00    2.00    --   22.00 123.00 169.41   27
  9  \w      1.00  28.00   1.00    5.00    --   38.00  88.00 -37.22   27
 10  \w     15.00  41.00   1.00    5.00    --   46.00  78.00-112.41   26
 11  \w     10.00  35.00   1.00    5.00    --   46.00  85.00  39.69   25
 12  \w     11.00  36.00   1.00    5.00    --   46.00  84.00  90.88   25
 13  \w     11.00  36.00   1.00    5.00    --   46.00  84.00-173.27   25
 14  \w     12.00  37.00   1.00    5.00    --   46.00  81.00 -59.35   25
 15  \w     17.00  42.00   1.00    5.00    --   50.00  80.00 -35.16   25
 16  \w     18.00  43.00   1.00    5.00    --   50.00  79.00 143.66   25
 17  \w      1.00  96.00   1.00    5.00    --   54.47 -99.00 120.00   95
 18  \w     24.00 101.00   1.00    5.00    --   54.47-125.00 -30.00   77
 19  \w     25.00  51.00   1.00    5.00    --   54.47  77.00  90.00   26
 20  \w     24.00  50.00   1.00    5.00    --   54.47  77.00  30.00   26
 21  \w     77.00 113.00   1.00    5.00    --   54.47  77.00-120.00   36
 22  \w     24.00  50.00   1.00    5.00    --   54.47  77.00-120.00   26
 23  \w    -14.00  74.00   1.00    5.00    --   54.47 -57.00 -30.00   88
 24  \w     77.00 125.00   1.00    5.00    --   54.47  77.00  90.00   48
 25  \w     31.00  57.00   1.00    5.00    --   62.00  75.00 166.45   26
 26  \w     77.00 132.00   1.00    5.00    --   62.00  75.00 -36.61   55
 27  \w     31.00  73.00   1.00    5.00    --   62.00  75.00 -36.61   42
 28  \w     32.00  60.00   1.00    5.00    --   62.00  75.00-103.43   28
 29  \w     30.00  56.00   1.00    5.00    --   62.00  77.00-165.95   26
 30  \w     38.00  68.00   1.00    5.00    --   66.00  76.00 108.79   30
 31  \w     40.00  68.00   1.00    5.00    --   66.00  69.00  78.22   28
 32  \w    115.00 140.00   1.00    5.00    --   70.00  72.00 -12.32   25
 33  \w     41.00  73.00   1.00    5.00    --   70.00  72.00 -12.32   32
 34  \w     41.00  77.00   1.00    5.00    --   70.00  73.00-161.37   36
 35  \w     43.00  70.00   1.00    5.00    --   70.00  71.00   7.19   27
 36  \w     43.00 101.00   1.00    5.00    --   70.00  72.00 -87.32   58
 37  \w     46.00 144.00   1.00    5.00    --   74.00  73.00  25.88   98
 38  \w    108.00 134.00   1.00    5.00    --   74.00  77.00  84.12   26
 39  \w     42.00  75.00   1.00    5.00    --   74.00  77.00  84.12   33
 40  \w     52.00  78.00   1.00    5.00    --   78.00  68.00 147.18   26
 41  \w     52.00  83.00   1.00    5.00    --   78.00  67.00-102.53   31
 42  \w     47.00  77.00   1.00    5.00    --   78.00  76.00 111.19   30
 43  \w     50.00 133.00   1.00   10.00    --   82.00  77.00-142.71   83
 44  \w     66.00  92.00   1.00   10.00    --   86.00  53.00   6.24   26
 45  \w     58.00 119.00   1.00   10.00    --   86.00  70.00-168.78   61
 46  \w    113.00 151.00   1.00   10.00    --   86.00  53.00   6.24   38
 47  \w     61.00  87.00   1.00   10.00    --   86.00  73.00 166.22   26
 48  \w     67.00  92.00   1.00   10.00    --   90.00  47.00 -21.04   25
 49  \w     58.00 154.00   1.00   10.00    --   90.00  77.00 -82.44   96
 50  \w     63.00 101.00   1.00   10.00    --   90.00  68.00 145.54   38
 51  \w     72.00 103.00   1.00   10.00    --   94.00  59.00 -98.55   31
 52  \w    123.00 172.00   1.00   10.00    --  102.00  68.00 -33.03   49
 53  \w     75.00 101.00   1.00   10.00    --  102.00  68.00 -33.03   26
 54  \w     41.00  70.00   1.00   10.00    --  108.94-111.00 -90.00   29
 55  \w     77.00 162.00   1.00   10.00    --  108.94  77.00-180.00   85
 56  \w     77.00 147.00   1.00   10.00    --  108.94  77.00  30.00   70
 57  \w     77.00 164.00   1.00   10.00    --  108.94  77.00-120.00   87
 58  \w    107.00 165.00   1.00   10.00    --  108.94  77.00 120.00   58
 59  \w     77.00 103.00   1.00   10.00    --  108.94  77.00 120.00   26
 60  \w     77.00 177.00   1.00   10.00    --  108.94  77.00 -90.00  100
 61  \w    121.00 156.00   1.00   10.00    --  108.94  77.00  60.00   35
 62  \w     79.00 113.00   1.00   10.00    --  108.94  77.00  60.00   34
 63  \w     40.00 110.00   1.00   10.00    --  108.94-111.00  90.00   70
 64  \w     77.00 157.00   1.00   10.00    --  108.94  77.00   0.00   80
 65  \w    135.00 175.00   1.00   10.00    --  108.94 111.00 120.00   40
 66  \w     85.00 172.00   1.00   10.00    --  108.94  64.00-150.00   87
 67  \w     41.00  98.00   1.00   10.00    --  108.94 -92.00-180.00   57
 68  \w    136.00 178.00   1.00   10.00    --  108.94 111.00 150.00   42
 69  \w     77.00 178.00   1.00   10.00    --  108.94  77.00  90.00  101
 70  \w    100.00 174.00   1.00   10.00    --  108.94 111.00  30.00   74
 71  \w     36.00  99.00   1.00   10.00    --  108.94 -92.00 120.00   63
 72  \w     39.00 109.00   1.00   10.00    --  108.94-111.00 -30.00   70
 73  \w     77.00 160.00   1.00   10.00    --  108.94  77.00 -60.00   83
 74  \w     84.00 109.00   1.00   10.00    --  108.94  64.00 150.00   25
 75  \w    153.00 178.00   1.00   10.00    --  108.94  77.00 -21.97   25
 76  \w     77.00 103.00   1.00   10.00    --  108.94  77.00 -30.00   26
 77  \w     77.00 111.00   1.00   10.00    --  108.94  77.00 -21.97   34
 78  \w     84.00 110.00   1.00   10.00    --  108.94  64.00  60.00   26
 79  \w     78.00 104.00   1.00   10.00    --  108.94  77.00-150.00   26
 80  \w     79.00 160.00   1.00   10.00    --  108.94  77.00 150.00   81
 81  \w     80.00 109.00   1.00   10.00    --  108.94-111.00 -90.00   29
;
_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      0.1319928000
_diffrn_orient_matrix_UB_12      0.0153354000
_diffrn_orient_matrix_UB_13      0.0927297000
_diffrn_orient_matrix_UB_21      -0.0322192000
_diffrn_orient_matrix_UB_22      -0.0959858000
_diffrn_orient_matrix_UB_23      0.0798282000
_diffrn_orient_matrix_UB_31      0.0605967000
_diffrn_orient_matrix_UB_32      -0.0842468000
_diffrn_orient_matrix_UB_33      -0.0741903000
_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  0.0745
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.891
_diffrn_reflns_theta_min         5.158
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       irregular
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0614P)^2^+0.7106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2465
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_4bdiylide_ba_ss10
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575884
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C34H40P2
_chemical_oxdiff_usercomment     ss232
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.704
_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), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10)
2.c 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              71917
_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
;