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_7134653
_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 Br2 N2 O2'
_chemical_formula_sum            'C28 H34 Br2 N2 O2'
_chemical_formula_weight         590.39
_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             2025-03-19
_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                74.174(13)
_cell_angle_beta                 89.890(8)
_cell_angle_gamma                76.786(12)
_cell_formula_units_Z            1
_cell_length_a                   4.5767(4)
_cell_length_b                   9.1416(19)
_cell_length_c                   16.1020(16)
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      72.2210
_cell_measurement_theta_min      5.1790
_cell_volume                     629.67(16)
_computing_cell_refinement       'CrysAlisPro 1.171.44.85a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.44.85a (Rigaku OD, 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      100.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.689
_diffrn_measured_fraction_theta_max 0.651
_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      6.00 115.00   1.00    1.00  52.94  75.62 -60.00    --   109
  2  \f    127.00 234.00   1.00    1.00  89.48  74.69   0.00    --   107
  3  \f    127.00 234.00   1.00    1.00  37.25  74.69 -20.00    --   107
  4  \f    246.00 356.00   1.00    1.00  52.00  74.69 -60.00    --   110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.3079497000
_diffrn_orient_matrix_UB_12      -0.0049966000
_diffrn_orient_matrix_UB_13      0.0379800000
_diffrn_orient_matrix_UB_21      -0.1525736000
_diffrn_orient_matrix_UB_22      0.0578331000
_diffrn_orient_matrix_UB_23      -0.0920858000
_diffrn_orient_matrix_UB_31      0.0440775000
_diffrn_orient_matrix_UB_32      -0.1707013000
_diffrn_orient_matrix_UB_33      -0.0028718000
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.689
_diffrn_reflns_Laue_measured_fraction_max 0.651
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2173
_diffrn_reflns_point_group_measured_fraction_full 0.689
_diffrn_reflns_point_group_measured_fraction_max 0.651
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         2.858
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56257
_exptl_absorpt_correction_type   multi-scan
_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.

The crystal selected for X-ray experiment was small needle 
with dimensions 0.028 mm x 0.034 mm x 0.167 mm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       needle
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.028
_refine_diff_density_max         2.544
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       0.0046(19)
_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   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0999
_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^)+(0.1305P)^2^+12.7192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2790
_refine_ls_wR_factor_ref         0.2828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1462
_reflns_number_total             1681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01880c3.cif
_cod_data_source_block           wit_ksk0401r5di-10_auto
_cod_depositor_comments
'Adding full bibliography for 7134652--7134653.cif.'
_cod_database_code               7134653
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c18h28n2o6LiCl
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.534
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              85010
_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.693