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_1575889
_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)'
_chemical_formula_sum            'C33 H50 Cl2 O3 P2'
_chemical_formula_weight         627.57
_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                 100.276(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.56569(18)
_cell_length_b                   21.6248(5)
_cell_length_c                   21.1554(5)
_cell_measurement_reflns_used    11724
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.9120
_cell_measurement_theta_min      4.0890
_cell_volume                     3405.64(14)
_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  (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 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    176.00 217.00   1.00    5.00   2.02   0.00 -40.00    --    41
  2  \w    -22.00  69.00   1.00    5.00    --    0.00  57.00-180.00   91
  3  \w    -16.00  35.00   1.00    5.00    --    0.00 -84.00 -77.00   51
  4  \f    127.00 166.00   1.00    5.00   2.02   0.00 -40.00    --    39
  5  \w     32.00 123.00   1.00   30.00    --   54.00  57.00-120.00   91
  6  \w     32.00 123.00   1.00   30.00    --   54.00  57.00 -60.00   91
  7  \w     23.00 112.00   1.00   30.00    --   54.00-125.00  30.00   89
  8  \w    -17.00  86.00   1.00   30.00    --   54.00 -77.00 150.00  103
  9  \w    -19.00  81.00   1.00   30.00    --   54.00 -38.00 -30.00  100
 10  \w     27.00 127.00   1.00   30.00    --   54.00  38.00-180.00  100
 11  \w    -15.00  76.00   1.00   30.00    --   54.00 -57.00  90.00   91
 12  \w     40.00 133.00   1.00   60.00    --  108.00 -64.00 -90.00   93
 13  \w     35.00 109.00   1.00   60.00    --  108.00 -92.00-150.00   74
 14  \w     35.00 135.00   1.00   60.00    --  108.00 -38.00-120.00  100
 15  \w     35.00 109.00   1.00   60.00    --  108.00 -92.00-120.00   74
 16  \w     83.00 176.00   1.00   60.00    --  108.00  64.00  90.00   93
 17  \w     35.00 135.00   1.00   60.00    --  108.00 -38.00-180.00  100
 18  \w     35.00 112.00   1.00   60.00    --  108.00-111.00   0.00   77
 19  \w     35.00 109.00   1.00   60.00    --  108.00 -92.00  60.00   74
 20  \w     98.00 178.00   1.00   60.00    --  108.00  84.00  42.00   80
 21  \w     83.00 176.00   1.00   60.00    --  108.00  64.00-150.00   93
 22  \w     85.00 178.00   1.00   60.00    --  108.00  50.00-180.00   93
 23  \w     81.00 178.00   1.00   60.00    --  108.00  38.00 150.00   97
 24  \w     35.00 112.00   1.00   60.00    --  108.00-111.00-180.00   77
 25  \w     37.00 131.00   1.00   60.00    --  108.00 -50.00  60.00   94
 26  \w    -73.00  27.00   1.00    5.00    --    0.00 -38.00   0.00  100
 27  \w    -73.00  27.00   1.00    5.00    --    0.00 -38.00 -90.00  100
 28  \w     27.00 127.00   1.00   30.00    --   54.00  38.00  60.00  100
 29  \w     22.00  80.00   1.00   30.00    --   54.00  77.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0845349000
_diffrn_orient_matrix_UB_12      0.0340121000
_diffrn_orient_matrix_UB_13      0.0620812000
_diffrn_orient_matrix_UB_21      0.1864711000
_diffrn_orient_matrix_UB_22      -0.0056119000
_diffrn_orient_matrix_UB_23      -0.0191107000
_diffrn_orient_matrix_UB_31      -0.0293572000
_diffrn_orient_matrix_UB_32      0.0623400000
_diffrn_orient_matrix_UB_33      -0.0355542000
_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  0.0806
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.433
_diffrn_reflns_theta_min         2.947
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.503
_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            'fluorescent intense yellow'
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6441
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0846
_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^)+(0.1243P)^2^+5.8025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2241
_refine_ls_wR_factor_ref         0.2375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5287
_reflns_number_total             6441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03752b3.cif
_cod_data_source_block           cmpd_4aPh_ba_jm79
_cod_depositor_comments
'Adding full bibliography for 1575881--1575890.cif.'
_cod_original_cell_volume        3405.63(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575889
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C33H50Cl2O3P2
_chemical_oxdiff_usercomment     JM_1_2_Cl
_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
2. Restrained distances
 P1-C19A \\sim P1-C19B
 with sigma of 0.02
 O2-C32 \\sim O3-C33 \\sim C31-O1
 with sigma of 0.02
 H3A-H33C \\sim H1-H31A \\sim H2A-H32C
 with sigma of 0.02
 C19A-C21A \\sim C19B-C21B
 with sigma of 0.02
 C19A-C20A \\sim C19B-C21B
 with sigma of 0.02
 P1-C21A \\sim P1-C21B
 with sigma of 0.02
 P1-C20A \\sim P1-C21B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C20A) = Uanis(C19A) = Uanis(C21A) = Uanis(C19B) = Uanis(C21B) =
Uanis(C20B)
4. Rigid body (RIGU) restrains
 C33, O3, C32, O2, O1, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C21B)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C19B)=Sof(H19B)=Sof(C20B)=
 Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C19A)=Sof(H19A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C20A)=
 Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C25(H25), C28(H28), C22(H22), C19A(H19A), C19B(H19B)
6.b Me refined as rotating group:
 C33(H33A,H33B,H33C), C31(H31A,H31B,H31C)
6.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C13(H13), C2(H2), C18(H18), C14(H14), C16(H16), C15(H15),
 C4(H4), C3(H3)
6.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C29(H29A,H29B,
 H29C), C23(H23A,H23B,H23C), C32(H32A,H32B,H32C), C24(H24A,H24B,H24C),
 C21A(H21A,H21B,H21C), C20A(H20A,H20B,H20C), C21B(H21D,H21E,H21F), C20B(H20D,
 H20E,H20F)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A), O2(H2A)
;
_shelx_res_checksum              91845
_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
;