Dipyrrolonaphthyridinediones - structurally unique cross-conjugated dyes.
Grzybowski, Marek; Deperasińska, Irena; Chotkowski, Maciej; Banasiewicz, Marzena; Makarewicz, Artur; Kozankiewicz, Bolesław; Gryko, Daniel T.; Chemical communications (Cambridge, England) 52 (2016) 5108–5111; doi:10.1039/c6cc01017b

data_7118818
_publ_section_title
;
 Dipyrrolonaphthyridinediones - structurally unique cross-conjugated dyes.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5108
_journal_page_last               5111
_journal_paper_doi               10.1039/c6cc01017b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
 dipyrrolo[1,2-b:1 ,2 -g][2,6]naphthyridine-5,11-dione
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-02-02 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3920(10)
_cell_length_b                   24.3920(10)
_cell_length_c                   4.8236(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.62
_cell_volume                     2869.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7619
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         3.624
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichloroethane/methanol'
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0547P)^2^+0.3487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                886
_reflns_number_total             1156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01017b2.cif
_cod_data_source_block           MGG492_0ma
_cod_depositor_comments          'Adding full bibliography for 7118818.cif.'
_cod_original_cell_volume        2869.9(3)
_cod_database_code               7118818
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2014-3
_shelx_res_checksum              25106
_shelx_hkl_checksum              18565