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_1564785
_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         'C40 H42 N4 O6'
_chemical_formula_sum            'C40 H42 N4 O6'
_chemical_formula_weight         674.77
_chemical_name_systematic
6,12-Diheptyl-3,9-bis(3-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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-07-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.466(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.2829(4)
_cell_length_b                   27.290(2)
_cell_length_c                   14.9334(13)
_cell_measurement_reflns_used    26557
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.296
_cell_measurement_theta_min      2.073
_cell_volume                     1744.8(3)
_computing_cell_refinement       'SAINT V8.38A Bruker, Madison WI'
_computing_data_collection       'Bruker APEX3 Bruker, Madison WI'
_computing_data_reduction        'SAINT V8.38A Bruker, Madison WI'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 with PHOTON-II CPAD detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26557
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_min         2.073
_diffrn_source                   'Advanced Light Source, station 12.2.1'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             716
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0580
_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^)+(0.0874P)^2^+0.5107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2966
_reflns_number_total             4022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03670j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1744.9(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1564785
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              43174