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_1575888
_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         'C30 H38 P2, 3(C H4 O), 2(Cl), H2 O'
_chemical_formula_sum            'C33 H52 Cl2 O4 P2'
_chemical_formula_weight         645.58
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-14 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.842(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8799(3)
_cell_length_b                   10.1289(4)
_cell_length_c                   43.307(2)
_cell_measurement_reflns_used    7463
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      68.6400
_cell_measurement_theta_min      4.0790
_cell_volume                     3454.7(2)
_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 0.999
_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    -22.00  69.00   1.00    5.00    --    0.00  57.00 -90.00   91
  2  \w    -27.00  73.00   1.00    5.00    --    0.00  38.00-150.00  100
  3  \w    -16.00  35.00   1.00    5.00    --    0.00 -84.00  71.00   51
  4  \w    -25.00  17.00   1.00    5.00    --   20.00 103.00 -38.91   42
  5  \w    -30.00   1.00   1.00    5.00    --   24.00 121.00 129.16   31
  6  \w    -14.00  12.00   1.00   10.00    --   32.00 108.00 -80.15   26
  7  \w    -15.00  11.00   1.00   10.00    --   32.00 109.00-162.24   26
  8  \w     -8.00  18.00   1.00   10.00    --   36.00 102.00-144.94   26
  9  \w      6.00  33.00   1.00   10.00    --   44.00  89.00  75.36   27
 10  \w      6.00  33.00   1.00   10.00    --   44.00  88.00 -24.36   27
 11  \w     15.00  45.00   1.00   10.00    --   48.00  80.00-169.28   30
 12  \w     14.00  45.00   1.00   10.00    --   48.00  81.00 -20.48   31
 13  \w     13.00  40.00   1.00   10.00    --   48.00  83.00-118.00   27
 14  \w     18.00  45.00   1.00   10.00    --   52.00  82.00 -93.75   27
 15  \w     18.00  45.00   1.00   10.00    --   52.00  82.00 113.33   27
 16  \w    -93.00  -2.00   1.00   10.00    --  -53.50 125.00  60.00   91
 17  \w      1.00  97.00   1.00   10.00    --   54.75 -99.00-180.00   96
 18  \w     23.00 111.00   1.00   10.00    --   54.75-125.00  30.00   88
 19  \w     25.00 127.00   1.00   10.00    --   56.00  76.00-107.55  102
 20  \w     28.00 131.00   1.00   10.00    --   60.00  77.00  26.99  103
 21  \w     28.00 131.00   1.00   10.00    --   60.00  77.00-170.81  103
 22  \w     29.00 131.00   1.00   10.00    --   60.00  75.00  73.23  102
 23  \w     29.00 131.00   1.00   10.00    --   60.00  76.00   0.10  102
 24  \w     28.00 131.00   1.00   10.00    --   60.00  77.00 -58.64  103
 25  \w     33.00 135.00   1.00   10.00    --   64.00  75.00 -95.13  102
 26  \w     33.00 135.00   1.00   10.00    --   64.00  75.00 142.91  102
 27  \w     40.00 138.00   1.00   10.00    --   68.00  70.00 106.63   98
 28  \w     36.00 139.00   1.00   10.00    --   68.00  77.00 -32.85  103
 29  \w     40.00  81.00   1.00   10.00    --   68.00  70.00-136.17   41
 30  \w     43.00  69.00   1.00   10.00    --   72.00  72.00 109.91   26
 31  \w     41.00  67.00   1.00   10.00    --   72.00  77.00-176.27   26
 32  \w     40.00 143.00   1.00   10.00    --   72.00  77.00  57.02  103
 33  \w     48.00 116.00   1.00   10.00    --   76.00  70.00-114.15   68
 34  \w     46.00 143.00   1.00   10.00    --   76.00  74.00  -9.89   97
 35  \w     59.00  84.00   1.00   10.00    --   80.00  64.00  58.49   25
 36  \w     52.00  78.00   1.00   10.00    --   80.00  70.00  34.10   26
 37  \w     58.00  85.00   1.00   25.00    --   84.00  71.00 157.51   27
 38  \w     57.00  83.00   1.00   25.00    --   84.00  69.00 122.72   26
 39  \w     53.00  83.00   1.00   25.00    --   84.00  75.00 -82.29   30
 40  \w    120.00 151.00   1.00   25.00    --   84.00  75.00   8.87   31
 41  \w     53.00 122.00   1.00   25.00    --   84.00  76.00 -66.42   69
 42  \w     53.00  86.00   1.00   25.00    --   84.00  75.00   8.87   33
 43  \w    102.00 157.00   1.00   25.00    --   88.00  74.00 176.31   55
 44  \w     60.00  87.00   1.00   25.00    --   88.00  74.00 176.31   27
 45  \w    120.00 156.00   1.00   25.00    --   88.00  68.00-157.49   36
 46  \w     61.00  87.00   1.00   25.00    --   88.00  68.00-157.49   26
 47  \w     59.00  85.00   1.00   25.00    --   88.00  73.00 124.33   26
 48  \w     63.00  92.00   1.00   25.00    --   88.00  64.00-127.52   29
 49  \w    136.00 162.00   1.00   25.00    --   92.00  73.00  57.11   26
 50  \w     63.00  90.00   1.00   25.00    --   92.00  73.00  57.11   27
 51  \w     63.00 124.00   1.00   25.00    --   92.00  73.00 128.96   61
 52  \w     74.00 101.00   1.00   25.00    --   92.00  56.00  36.28   27
 53  \w     73.00  99.00   1.00   25.00    --  100.00  69.00  85.09   26
 54  \w     78.00 175.00   1.00   25.00    --  109.50  77.00 -90.00   97
 55  \w     79.00 178.00   1.00   25.00    --  109.50  77.00  60.00   99
 56  \w     78.00 104.00   1.00   25.00    --  109.50  77.00 -30.00   26
 57  \w     78.00 166.00   1.00   25.00    --  109.50  77.00-150.00   88
 58  \w     78.00 174.00   1.00   25.00    --  109.50  77.00  90.00   96
 59  \w     78.00 158.00   1.00   25.00    --  109.50  77.00 -60.00   80
 60  \w     39.00  82.00   1.00   25.00    --  109.50 -50.00-180.00   43
 61  \w     85.00 177.00   1.00   25.00    --  109.50  64.00 -30.00   92
 62  \w     85.00 111.00   1.00   25.00    --  109.50  64.00-120.00   26
 63  \w     85.00 111.00   1.00   25.00    --  109.50  64.00-180.00   26
 64  \w     78.00 163.00   1.00   25.00    --  109.50  77.00 120.00   85
 65  \w     38.00  86.00   1.00   25.00    --  109.50 -92.00  90.00   48
 66  \w     40.00  82.00   1.00   25.00    --  109.50 -92.00 -90.00   42
 67  \w     37.00 107.00   1.00   25.00    --  109.50 -92.00-180.00   70
 68  \w     41.00  77.00   1.00   25.00    --  109.50 -92.00   0.00   36
 69  \w     38.00 100.00   1.00   25.00    --  109.50 -92.00  30.00   62
 70  \w     58.00 113.00   1.00   25.00    --  109.50-111.00 -30.00   55
 71  \w     78.00 161.00   1.00   25.00    --  109.50  77.00 150.00   83
 72  \w     83.00 109.00   1.00   25.00    --  109.50  68.00  -4.96   26
 73  \w     79.00 160.00   1.00   25.00    --  109.50  77.00  30.00   81
 74  \w     86.00 111.00   1.00   25.00    --  109.50  64.00 -60.00   25
 75  \w     62.00 112.00   1.00   25.00    --  109.50-111.00 150.00   50
 76  \w     79.00 149.00   1.00   25.00    --  109.50  77.00   0.00   70
 77  \w     78.00 177.00   1.00   25.00    --  109.50  77.00-120.00   99
 78  \w     78.00 169.00   1.00   25.00    --  109.50  77.00-180.00   91
;
_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      -0.1390292000
_diffrn_orient_matrix_UB_12      -0.0529494000
_diffrn_orient_matrix_UB_13      0.0209191000
_diffrn_orient_matrix_UB_21      -0.0383703000
_diffrn_orient_matrix_UB_22      -0.1119827000
_diffrn_orient_matrix_UB_23      -0.0232921000
_diffrn_orient_matrix_UB_31      0.1320859000
_diffrn_orient_matrix_UB_32      -0.0883756000
_diffrn_orient_matrix_UB_33      0.0169102000
_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  0.1410
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            62610
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.832
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.738
_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    1.241
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6168
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0660P)^2^+4.5129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4328
_reflns_number_total             6168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_4bPh_ba_ss5
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_cell_volume        3454.8(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575888
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C33H52Cl2O4P2
_chemical_oxdiff_usercomment     'ss183, irregular, yellow'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.693
_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, All O(H,H) groups
2. Restrained distances
 C33A-O4A \\sim C33B-O4B
 with sigma of 0.02
 O4A-C33A \\sim O4B-C33B \\sim C31-O1 \\sim C32-O2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O4A \\sim O4B \\sim C33B \\sim C33A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C33B) = Uanis(C33A)
4. Others
 Sof(O4B)=Sof(H4B)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(1)
 Sof(O4A)=Sof(H4A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
5.a Free rotating group:
 O3(H3A,H3B)
5.b Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C25(H25), C28(H28)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C33B(H33D,H33E,H33F), C33A(H33A,H33B,H33C), C32(H32A,H32B,H32C),
 C31(H31A,H31B,H31C)
5.e Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O4B(H4B), O2(H2A), O1(H1)
;
_shelx_res_checksum              24984
_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
;