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_1575883
_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                 109.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.6337(2)
_cell_length_b                   10.87690(10)
_cell_length_c                   14.8298(2)
_cell_measurement_reflns_used    11747
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.8290
_cell_measurement_theta_min      3.6650
_cell_volume                     2218.77(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.127a 64-bit (release 16-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_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 0.995
_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      6.00  41.00   1.00    3.00    --    0.00  77.00-150.00   35
  2  \w    -23.00  14.00   1.00    3.00    --    0.00 -57.00-180.00   37
  3  \w     46.00  71.00   1.00    3.00    --    0.00  77.00-150.00   25
  4  \w    -29.00  -2.00   1.00    3.00    --    0.00  77.00-150.00   27
  5  \w    -21.00  65.00   1.00    3.00    --    0.00  57.00 -30.00   86
  6  \w    -69.00 -26.00   1.00    3.00    --    0.00 -57.00-180.00   43
  7  \w    -40.00 -15.00   1.00    3.00    --   14.00 121.00  -7.11   25
  8  \w    -39.00  -3.00   1.00    3.00    --   18.00 126.00  87.38   36
  9  \w    -18.00   7.00   1.00    7.00    --   30.00 113.00  29.95   25
 10  \w      3.00  28.00   1.00    7.00    --   42.00  90.00-158.99   25
 11  \w     10.00  35.00   1.00    7.00    --   46.00  85.00  72.21   25
 12  \w     10.00  35.00   1.00    7.00    --   46.00  85.00 -56.82   25
 13  \w     11.00  36.00   1.00    7.00    --   46.00  83.00-143.76   25
 14  \w     11.00  36.00   1.00    7.00    --   46.00  84.00  -9.45   25
 15  \w     17.00  42.00   1.00    7.00    --   50.00  80.00 149.02   25
 16  \w      2.00  81.00   1.00    7.00    --   54.47 -99.00 150.00   79
 17  \w     25.00  88.00   1.00    7.00    --   54.47-125.00   0.00   63
 18  \w    -14.00  85.00   1.00    7.00    --   54.47 -77.00   0.00   99
 19  \w     -5.00  76.00   1.00    7.00    --   54.47 -57.00-180.00   81
 20  \w     26.00  52.00   1.00    7.00    --   58.00  77.00 -30.57   26
 21  \w     28.00  55.00   1.00    7.00    --   58.00  75.00-113.17   27
 22  \w     86.00 126.00   1.00    7.00    --   58.00  77.00 -30.57   40
 23  \w     96.00 129.00   1.00    7.00    --   58.00  75.00-113.17   33
 24  \w     26.00  52.00   1.00    7.00    --   58.00  77.00 108.96   26
 25  \w     92.00 128.00   1.00    7.00    --   58.00  77.00 108.96   36
 26  \w     33.00 122.00   1.00    7.00    --   62.00  72.00  38.65   89
 27  \w     31.00  74.00   1.00    7.00    --   62.00  77.00  -6.45   43
 28  \w     34.00  59.00   1.00    7.00    --   62.00  74.00 126.02   25
 29  \w     33.00  70.00   1.00    7.00    --   62.00  77.00 155.59   37
 30  \w     32.00 133.00   1.00    7.00    --   62.00  75.00-143.19  101
 31  \w     31.00 125.00   1.00    7.00    --   62.00  77.00-179.19   94
 32  \w     31.00 128.00   1.00    7.00    --   62.00  75.00 -69.07   97
 33  \w     71.00 130.00   1.00    7.00    --   62.00  74.00  82.52   59
 34  \w     32.00  65.00   1.00    7.00    --   62.00  74.00  82.52   33
 35  \w     77.00 104.00   1.00   17.00    --  108.94  77.00  60.00   27
 36  \w     84.00 168.00   1.00   17.00    --  108.94  64.00 120.00   84
 37  \w     85.00 165.00   1.00   17.00    --  108.94  64.00  60.00   80
 38  \w     84.00 110.00   1.00   17.00    --  108.94  64.00 -60.00   26
 39  \w     77.00 104.00   1.00   17.00    --  108.94  77.00-120.00   27
 40  \w     36.00 106.00   1.00   17.00    --  108.94 -92.00 150.00   70
 41  \w     85.00 166.00   1.00   17.00    --  108.94  64.00   0.00   81
 42  \w     77.00 177.00   1.00   17.00    --  108.94  77.00 150.00  100
 43  \w     36.00  94.00   1.00   17.00    --  108.94 -92.00 -60.00   58
 44  \w     36.00  74.00   1.00   17.00    --  108.94 -92.00-150.00   38
 45  \w     78.00 103.00   1.00   17.00    --  108.94  77.00   0.00   25
 46  \w     40.00 110.00   1.00   17.00    --  108.94-111.00 120.00   70
 47  \w     77.00 103.00   1.00   17.00    --  108.94  77.00-150.00   26
 48  \w     78.00 103.00   1.00   17.00    --  108.94  77.00  30.00   25
 49  \w     77.00 177.00   1.00   17.00    --  108.94  77.00 -60.00  100
 50  \w     77.00 103.00   1.00   17.00    --  108.94  77.00-180.00   26
 51  \w     84.00 175.00   1.00   17.00    --  108.94  64.00-150.00   91
 52  \w     38.00 105.00   1.00   17.00    --  108.94 -92.00   0.00   67
 53  \w     84.00 110.00   1.00   17.00    --  108.94  64.00 150.00   26
 54  \w     40.00 112.00   1.00   17.00    --  108.94-111.00 -90.00   72
 55  \w     77.00 103.00   1.00   17.00    --  108.94  77.00 120.00   26
 56  \w     77.00 103.00   1.00   17.00    --  108.94  77.00 -30.00   26
 57  \w     84.00 112.00   1.00   17.00    --  108.94  64.00  90.00   28
 58  \w     84.00 166.00   1.00   17.00    --  108.94  64.00 -90.00   82
 59  \w     84.00 164.00   1.00   17.00    --  108.94  64.00-180.00   80
 60  \w     78.00 103.00   1.00   17.00    --  108.94  77.00 -90.00   25
 61  \w    118.00 163.00   1.00   17.00    --  108.94  64.00 -30.00   45
 62  \w     80.00 174.00   1.00   17.00    --  108.94  77.00  90.00   94
 63  \w     84.00 110.00   1.00   17.00    --  108.94  64.00 -30.00   26
 64  \w     36.00  68.00   1.00   17.00    --  108.94 -92.00  60.00   32
 65  \w     84.00 174.00   1.00   17.00    --  108.94  64.00-120.00   90
 66  \w     84.00 174.00   1.00   17.00    --  108.94  64.00  30.00   90
;
_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      0.1050214000
_diffrn_orient_matrix_UB_12      -0.0151058000
_diffrn_orient_matrix_UB_13      0.0695871000
_diffrn_orient_matrix_UB_21      0.0324027000
_diffrn_orient_matrix_UB_22      0.1082641000
_diffrn_orient_matrix_UB_23      -0.0489311000
_diffrn_orient_matrix_UB_31      -0.0213334000
_diffrn_orient_matrix_UB_32      0.0901241000
_diffrn_orient_matrix_UB_33      0.0705403000
_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  0.0588
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_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            30956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.108
_diffrn_reflns_theta_min         3.664
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.635
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       irregular
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0626P)^2^+1.8038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3706
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_4b_ba_ss14
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575883
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C17H18PCl5
_chemical_oxdiff_usercomment     ss311
_shelx_estimated_absorpt_t_max   0.619
_shelx_estimated_absorpt_t_min   0.457
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9)
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              41551
_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
;