Polysubstitution of dipyrrolonaphthyridinediones as a potent strategy towards strongly emitting fluorophores
Skonieczny, Kamil; Kielesiński, Łukasz; Grzybowski, Marek; Gryko, Daniel T.; Chemical Communications 61 (2025) 10178–10181; doi:10.1039/D5CC01880C

data_7134652
_publ_section_title
;
 Polysubstitution of dipyrrolonaphthyridinediones as a potent strategy
 towards strongly emitting fluorophores
;
_journal_issue                   55
_journal_name_full               'Chemical Communications'
_journal_page_first              10178
_journal_page_last               10181
_journal_paper_doi               10.1039/D5CC01880C
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H34 I2 N2 O2'
_chemical_formula_sum            'C28 H34 I2 N2 O2'
_chemical_formula_weight         684.37
_chemical_name_systematic        LKI1087-10
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-20
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-03-25 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.217(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.5672(7)
_cell_length_b                   4.64730(10)
_cell_length_c                   18.6492(4)
_cell_measurement_reflns_used    10977
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      34.2770
_cell_measurement_theta_min      2.6340
_cell_volume                     2683.62(10)
_computing_cell_refinement       'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 44.85a 64-bit (release 11-12-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_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    -49.00 -23.00   0.50  200.00    --   -2.00 -38.00  73.36   52
  2  \w     19.00  45.00   0.50  200.00    --   -2.00  41.00-157.80   52
  3  \w    -49.00 -23.00   0.50  200.00    --   -2.00 -37.00  47.69   52
  4  \w     19.00  45.00   0.50  200.00    --   -2.00  41.00 -65.83   52
  5  \w    -49.00 -23.00   0.50  200.00    --   -2.00 -37.00-140.23   52
  6  \w    -49.00 -23.00   0.50  200.00    --   -2.00 -38.00 -23.25   52
  7  \w    -49.00 -23.00   0.50  200.00    --   -2.00 -36.00   3.24   52
  8  \w    -36.00  -9.00   0.50  200.00    --    2.00 -72.00  45.28   54
  9  \w    -49.00 -23.00   0.50  200.00    --   -2.00 -39.00 -77.30   52
 10  \w    -43.00 -17.00   0.50  200.00    --   -2.04 -64.00-142.80   52
 11  \w    -42.00 -16.00   0.50  200.00    --   -2.04 -67.00  -9.77   52
 12  \w     19.00  45.00   0.50  200.00    --   -2.04  40.00 152.13   52
 13  \w    -40.00 -14.00   0.50  200.00    --   -2.04 -70.00 178.37   52
 14  \w    -43.00 -17.00   0.50  200.00    --    3.76 -42.00 -43.18   52
 15  \w     25.00  51.00   0.50  200.00    --    3.76  41.00 151.22   52
 16  \w     25.00  51.00   0.50  200.00    --    3.76  36.00 -95.74   52
 17  \w     25.00  51.00   0.50  200.00    --    3.76  41.00-139.25   52
 18  \w    -43.00 -17.00   0.50  200.00    --    3.76 -42.00 -87.42   52
 19  \w    -45.00 -20.00   0.50  200.00    --    2.00 -36.00 113.33   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131411000
_diffrn_orient_matrix_UB_12      -0.0150589000
_diffrn_orient_matrix_UB_13      -0.0265967000
_diffrn_orient_matrix_UB_21      -0.0156431000
_diffrn_orient_matrix_UB_22      0.0748706000
_diffrn_orient_matrix_UB_23      -0.0257238000
_diffrn_orient_matrix_UB_31      0.0103647000
_diffrn_orient_matrix_UB_32      0.1321761000
_diffrn_orient_matrix_UB_33      0.0115583000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            40165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.779
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95272
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.85a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       needle
_exptl_crystal_F_000             1352
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.018
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5043
_reflns_number_total             6814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01880c3.cif
_cod_data_source_block           lki1087_mo_auto
_cod_depositor_comments
'Adding full bibliography for 7134652--7134653.cif.'
_cod_database_code               7134652
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H34N2 O2I2'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.616
_diffrn_oxdiff_digest_od_ed
;

;
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              7563
_olex2_exptl_crystal_mounting_method loop
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.860