Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core
Sadowski, Bartłomiej; Kaliszewska, Marzena; Poronik, Yevgen M.; Czichy, Małgorzata; Janasik, Patryk; Banasiewicz, Marzena; Mierzwa, Dominik; Gadomski, Wojciech; Lohrey, Trevor D.; Clark, John A.; Łapkowski, Mieczysław; Kozankiewicz, Bolesław; Vullev, Valentine I.; Sobolewski, Andrzej L.; Piatkowski, Piotr; Gryko, Daniel T.; Chemical Science  (2021) –; doi:10.1039/D1SC03670J

data_1564784
_publ_section_title
;
 Potent strategy towards strongly emissive nitroaromatics through a weakly
 electron-deficient core
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03670J
_journal_year                    2021
_chemical_formula_moiety         'C42 H46 N4 O6'
_chemical_formula_sum            'C42 H46 N4 O6'
_chemical_formula_weight         702.83
_chemical_name_systematic
6,12-Diheptyl-3,9-bis(2-methyl-4-nitrophenyl)-5H,11H-dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.544(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8094(2)
_cell_length_b                   12.3555(4)
_cell_length_c                   31.0929(10)
_cell_measurement_reflns_used    2335
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.67
_cell_measurement_theta_min      2.85
_cell_volume                     1844.09(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0849
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            36814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.675
_diffrn_reflns_theta_min         2.848
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9270
_exptl_absorpt_correction_T_min  0.8670
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             748
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1593P)^2^+1.2976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2335
_reflns_number_total             3383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03670j2.cif
_cod_data_source_block           BS591_B_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1564784
_shelx_estimated_absorpt_t_min   0.867
_shelx_estimated_absorpt_t_max   0.927
_shelxl_version_number           2014-3
_shelx_res_checksum              70123