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_1575882
_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 Cl2 P2, 6(C1 H2 Cl2), 2(Cl)'
_chemical_formula_sum            'C40 H52 Cl16 P2'
_chemical_formula_weight         1161.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2023-05-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-07-08 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.394(2)
_cell_angle_beta                 79.220(2)
_cell_angle_gamma                89.6000(10)
_cell_formula_units_Z            2
_cell_length_a                   10.3156(2)
_cell_length_b                   11.7343(2)
_cell_length_c                   23.0477(5)
_cell_measurement_reflns_used    29517
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.6590
_cell_measurement_theta_min      3.7540
_cell_volume                     2731.66(9)
_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 2018/3 (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 0.982
_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    -69.00  22.00   1.00    2.00    --    0.00 -57.00 150.00   91
  2  \w    -22.00  69.00   1.00    2.00    --    0.00  57.00 -30.00   91
  3  \w    -22.00  69.00   1.00    2.00    --    0.00  57.00-180.00   91
  4  \w    -30.00  18.00   1.00    2.00    --   14.00 101.00-104.71   48
  5  \w    -29.00  10.00   1.00    2.00    --   18.00 111.00  67.78   39
  6  \w    -41.00 -13.00   1.00   15.00    --   30.00 147.00 -91.53   28
  7  \w     -2.00  28.00   1.00   15.00    --   38.00  92.00 -68.19   30
  8  \w      4.00  33.00   1.00   15.00    --   42.00  89.00  66.26   29
  9  \w     10.00  36.00   1.00   15.00    --   46.00  85.00 -91.38   26
 10  \w     10.00  36.00   1.00   15.00    --   46.00  85.00-154.70   26
 11  \w     12.00  45.00   1.00   15.00    --   46.00  82.00 127.21   33
 12  \w     16.00  45.00   1.00   15.00    --   50.00  82.00  47.98   29
 13  \w     16.00  45.00   1.00   15.00    --   50.00  82.00 156.18   29
 14  \w     17.00  45.00   1.00   15.00    --   50.00  80.00 -69.86   28
 15  \w     16.00  45.00   1.00   15.00    --   50.00  81.00   2.66   29
 16  \w     16.00  45.00   1.00   15.00    --   50.00  81.00  86.73   29
 17  \w      1.00  97.00   1.00   15.00    --   54.47 -99.00-180.00   96
 18  \w     23.00 111.00   1.00   15.00    --   54.47-125.00  30.00   88
 19  \w    -16.00  86.00   1.00   15.00    --   54.47 -77.00  30.00  102
 20  \w     23.00 125.00   1.00   15.00    --   54.47  77.00 -30.00  102
 21  \w     27.00 129.00   1.00   15.00    --   58.00  76.00-142.16  102
 22  \w     27.00 129.00   1.00   15.00    --   58.00  76.00  58.40  102
 23  \w     30.00 133.00   1.00   15.00    --   62.00  77.00-174.89  103
 24  \w     30.00 133.00   1.00   15.00    --   62.00  77.00 -41.52  103
 25  \w     30.00 133.00   1.00   15.00    --   62.00  77.00 123.35  103
 26  \w     31.00 133.00   1.00   15.00    --   62.00  75.00 -12.86  102
 27  \w     30.00 133.00   1.00   15.00    --   62.00  77.00  26.76  103
 28  \w     35.00 137.00   1.00   15.00    --   66.00  76.00 -88.37  102
 29  \w     35.00 137.00   1.00   15.00    --   66.00  75.00 159.76  102
 30  \w     39.00 141.00   1.00   15.00    --   70.00  75.00  85.18  102
 31  \w     38.00 141.00   1.00   15.00    --   70.00  77.00-126.71  103
 32  \w     42.00 140.00   1.00   15.00    --   70.00  70.00 -63.09   98
 33  \w     47.00 144.00   1.00   15.00    --   74.00  69.00  45.90   97
 34  \w     46.00 144.00   1.00   15.00    --   74.00  70.00-145.53   98
 35  \w     46.00 144.00   1.00   15.00    --   74.00  71.00   5.80   98
 36  \w     43.00 145.00   1.00   15.00    --   74.00  76.00 103.14  102
 37  \w     47.00 149.00   1.00   15.00    --   78.00  76.00 -46.80  102
 38  \w     47.00 149.00   1.00   15.00    --   78.00  75.00  46.70  102
 39  \w     50.00 148.00   1.00   15.00    --   78.00  70.00-178.90   98
 40  \w     47.00 149.00   1.00   15.00    --   78.00  75.00-129.15  102
 41  \w     50.00 116.00   1.00   35.00    --   82.00  77.00 109.81   66
 42  \w     50.00  86.00   1.00   35.00    --   82.00  77.00 130.55   36
 43  \w     58.00  95.00   1.00   35.00    --   86.00  73.00 -93.15   37
 44  \w     54.00  81.00   1.00   35.00    --   86.00  77.00 -41.71   27
 45  \w     55.00 144.00   1.00   35.00    --   86.00  76.00-115.35   89
 46  \w     55.00  97.00   1.00   35.00    --   86.00  75.00-174.90   42
 47  \w     63.00 125.00   1.00   35.00    --   90.00  69.00-135.56   62
 48  \w     64.00  93.00   1.00   35.00    --   94.00  74.00 -35.46   29
 49  \w     65.00  91.00   1.00   35.00    --   94.00  74.00  27.74   26
 50  \w     63.00  89.00   1.00   35.00    --   94.00  75.00  69.87   26
 51  \w     66.00 102.00   1.00   35.00    --   94.00  74.00  36.90   36
 52  \w     63.00 156.00   1.00   35.00    --   94.00  75.00   4.49   93
 53  \w    132.00 163.00   1.00   35.00    --   98.00  70.00  56.92   31
 54  \w     70.00  96.00   1.00   35.00    --   98.00  70.00  56.92   26
 55  \w     69.00  95.00   1.00   35.00    --   98.00  75.00 163.85   26
 56  \w     70.00  99.00   1.00   35.00    --  102.00  77.00 -88.68   29
 57  \w     39.00 111.00   1.00   35.00    --  108.94-111.00 -30.00   72
 58  \w     77.00 162.00   1.00   35.00    --  108.94  77.00  60.00   85
 59  \w     57.00  87.00   1.00   35.00    --  108.94 -92.00  60.00   30
 60  \w     77.00 130.00   1.00   35.00    --  108.94  77.00 120.00   53
 61  \w     36.00 109.00   1.00   35.00    --  108.94 -92.00-180.00   73
 62  \w     77.00 178.00   1.00   35.00    --  108.94  77.00-180.00  101
 63  \w    115.00 175.00   1.00   35.00    --  108.94 111.00 120.00   60
 64  \w     47.00 104.00   1.00   35.00    --  108.94 -92.00 120.00   57
 65  \w     37.00  68.00   1.00   35.00    --  108.94 -92.00-120.00   31
 66  \w     48.00 112.00   1.00   35.00    --  108.94-111.00  60.00   64
 67  \w     79.00 176.00   1.00   35.00    --  108.94  74.00-143.25   97
 68  \w     78.00 178.00   1.00   35.00    --  108.94  77.00  97.25  100
 69  \w     80.00 177.00   1.00   35.00    --  108.94  77.00 -90.00   97
 70  \w     85.00 170.00   1.00   35.00    --  108.94  64.00  30.00   85
 71  \w     42.00  89.00   1.00   35.00    --  108.94 -92.00 -90.00   47
 72  \w     77.00 157.00   1.00   35.00    --  108.94  77.00 -60.00   80
 73  \w     77.00 175.00   1.00   35.00    --  108.94  77.00 -30.00   98
 74  \w     85.00 134.00   1.00   35.00    --  108.94  64.00  90.00   49
 75  \w     78.00 169.00   1.00   35.00    --  108.94  77.00   0.00   91
 76  \w     77.00 169.00   1.00   35.00    --  108.94  77.00-120.00   92
 77  \w     84.00 172.00   1.00   35.00    --  108.94  64.00 150.00   88
;
_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      0.0060317000
_diffrn_orient_matrix_UB_12      0.1230530000
_diffrn_orient_matrix_UB_13      0.0182090000
_diffrn_orient_matrix_UB_21      0.1512760000
_diffrn_orient_matrix_UB_22      0.0004898000
_diffrn_orient_matrix_UB_23      -0.0193291000
_diffrn_orient_matrix_UB_31      -0.0138741000
_diffrn_orient_matrix_UB_32      0.0469786000
_diffrn_orient_matrix_UB_33      -0.0628874000
_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  0.0908
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            65423
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.036
_diffrn_reflns_theta_min         3.779
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.144
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.730
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.253
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.00062(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         10392
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0857P)^2^+3.3693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8884
_reflns_number_total             10392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           ba_ss4
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_database_code               1575882
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34H40Cl4P2 (CH2Cl2)6'
_chemical_oxdiff_usercomment     ss163
_shelx_estimated_absorpt_t_max   0.599
_shelx_estimated_absorpt_t_min   0.307
_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. Restrained distances
 Cl17-C57 \\sim Cl15-C56
 with sigma of 0.02
 Cl18-C57 \\sim Cl16-C56
 with sigma of 0.02
 Cl17-Cl18 \\sim Cl15-Cl16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl17) = Uanis(Cl15) = Uanis(Cl18) = Uanis(Cl16)
Uanis(C57) = Uanis(C56)
4. Others
 Sof(Cl15)=Sof(Cl16)=Sof(C56)=Sof(H56A)=Sof(H56B)=1-FVAR(1)
 Sof(Cl17)=Sof(Cl18)=Sof(C57)=Sof(H57A)=Sof(H57B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26), C29(H29), C32(H32)
5.b Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C57(H57A,H57B), C55(H55A,H55B), C54(H54A,H54B), C51(H51A,
 H51B), C53(H53A,H53B), C52(H52A,H52B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21)
5.d 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)
;
_shelx_res_checksum              14287
_olex2_date_sample_data_collection 2023-05-17
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.070
_oxdiff_exptl_absorpt_empirical_full_min 0.561