#------------------------------------------------------------------------------
#$Date: 2021-10-01 01:18:43 +0300 (Fri, 01 Oct 2021) $
#$Revision: 269407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564785.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1564785
loop_
_publ_author_name
'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.'
_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       'φ and ω 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/[σ²(Fo²)+(0.0874P)²+0.5107P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4202(4) 0.57024(6) 0.49434(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.6913(4) 0.63015(6) 0.59701(11) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.5905(4) 0.67613(6) 0.55408(11) 0.0277(4) Uani 1 1 d . . . . .
C4 C 0.6509(5) 0.68563(7) 0.46447(12) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.7549 0.6622 0.4289 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5559(6) 0.72991(7) 0.42880(13) 0.0385(5) Uani 1 1 d . . . . .
C6 C 0.4016(6) 0.76524(7) 0.47689(15) 0.0425(5) Uani 1 1 d . . . . .
H6 H 0.3339 0.7949 0.4495 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3486(6) 0.75601(7) 0.56615(15) 0.0429(5) Uani 1 1 d . . . . .
H7 H 0.2454 0.7798 0.6013 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4460(5) 0.71214(7) 0.60469(13) 0.0347(5) Uani 1 1 d . . . . .
H8 H 0.4136 0.7066 0.6665 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8765(5) 0.62509(7) 0.67285(11) 0.0300(4) Uani 1 1 d . . . . .
H9 H 0.9479 0.6511 0.7104 0.036 Uiso 1 1 calc R U . . .
C10 C 0.9432(4) 0.57514(7) 0.68591(11) 0.0268(4) Uani 1 1 d . . . . .
H10 H 1.0689 0.5616 0.7330 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7924(4) 0.54923(6) 0.61766(10) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.7772(4) 0.49812(6) 0.59861(10) 0.0194(3) Uani 1 1 d . . . . .
C13 C 0.5915(4) 0.48247(6) 0.52712(10) 0.0186(3) Uani 1 1 d . . . . .
C14 C 0.9661(4) 0.46573(6) 0.66150(11) 0.0221(4) Uani 1 1 d . . . . .
H14A H 1.1335 0.4856 0.6906 0.027 Uiso 1 1 calc R U . . .
H14B H 1.0670 0.4397 0.6263 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7716(4) 0.44184(6) 0.73402(11) 0.0230(4) Uani 1 1 d . . . . .
H15A H 0.6803 0.4676 0.7719 0.028 Uiso 1 1 calc R U . . .
H15B H 0.5978 0.4231 0.7055 0.028 Uiso 1 1 calc R U . . .
C16 C 0.9699(4) 0.40757(7) 0.79241(12) 0.0278(4) Uani 1 1 d . . . . .
H16A H 1.1533 0.4260 0.8160 0.033 Uiso 1 1 calc R U . . .
H16B H 1.0485 0.3808 0.7543 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8019(5) 0.38484(7) 0.87129(12) 0.0312(4) Uani 1 1 d . . . . .
H17A H 0.6059 0.3695 0.8487 0.037 Uiso 1 1 calc R U . . .
H17B H 0.9350 0.3586 0.8976 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7239(5) 0.42124(8) 0.94458(11) 0.0322(4) Uani 1 1 d . . . . .
H18A H 0.9145 0.4401 0.9608 0.039 Uiso 1 1 calc R U . . .
H18B H 0.5665 0.4447 0.9205 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5989(5) 0.39785(9) 1.02884(13) 0.0459(6) Uani 1 1 d . . . . .
H19A H 0.4098 0.3786 1.0127 0.055 Uiso 1 1 calc R U . . .
H19B H 0.7575 0.3749 1.0537 0.055 Uiso 1 1 calc R U . . .
C20 C 0.5178(6) 0.43480(11) 1.10038(14) 0.0550(7) Uani 1 1 d . . . . .
H20A H 0.7021 0.4548 1.1154 0.082 Uiso 1 1 calc R U . . .
H20B H 0.4503 0.4175 1.1540 0.082 Uiso 1 1 calc R U . . .
H20C H 0.3487 0.4560 1.0780 0.082 Uiso 1 1 calc R U . . .
N1 N 0.6358(3) 0.58332(5) 0.56325(8) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.6223(6) 0.74005(7) 0.33468(13) 0.0593(6) Uani 1 1 d . . . . .
O1 O 0.2631(3) 0.60189(4) 0.45800(8) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.5436(7) 0.77949(7) 0.30415(14) 0.0954(9) Uani 1 1 d . . . . .
O3 O 0.7543(6) 0.70916(7) 0.29105(11) 0.0830(8) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0065 0.0035 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0115 0.0064 'Calculated using XDISP in WinGX (Farrugia, 1999)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 119.39(15) . . ?
O1 C1 C13 125.57(15) . 3_666 ?
N1 C1 C13 115.04(14) . 3_666 ?
C9 C2 N1 107.22(15) . . ?
C9 C2 C3 127.08(16) . . ?
N1 C2 C3 125.51(15) . . ?
C4 C3 C8 119.02(17) . . ?
C4 C3 C2 121.21(16) . . ?
C8 C3 C2 119.68(16) . . ?
C5 C4 C3 118.31(18) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 123.49(19) . . ?
C4 C5 N2 118.24(18) . . ?
C6 C5 N2 118.27(18) . . ?
C7 C6 C5 117.87(19) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 120.17(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.07(17) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C2 C9 C10 108.85(16) . . ?
C2 C9 H9 125.6 . . ?
C10 C9 H9 125.6 . . ?
C11 C10 C9 107.67(16) . . ?
C11 C10 H10 126.2 . . ?
C9 C10 H10 126.2 . . ?
C10 C11 N1 107.21(15) . . ?
C10 C11 C12 131.62(16) . . ?
N1 C11 C12 121.17(14) . . ?
C13 C12 C11 118.63(15) . . ?
C13 C12 C14 126.02(15) . . ?
C11 C12 C14 115.34(14) . . ?
C12 C13 C13 120.89(19) . 3_666 ?
C12 C13 C1 119.00(14) . 3_666 ?
C13 C13 C1 120.11(18) 3_666 3_666 ?
C12 C14 C15 113.41(14) . . ?
C12 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C12 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 111.19(14) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 115.11(15) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 113.96(16) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 114.19(18) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 113.3(2) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 N1 C11 109.03(13) . . ?
C2 N1 C1 126.80(14) . . ?
C11 N1 C1 123.49(14) . . ?
O2 N2 O3 122.88(19) . . ?
O2 N2 C5 117.94(19) . . ?
O3 N2 C5 119.18(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.214(2) . ?
C1 N1 1.411(2) . ?
C1 C13 1.474(2) 3_666 ?
C2 C9 1.373(3) . ?
C2 N1 1.392(2) . ?
C2 C3 1.469(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.394(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 N2 1.467(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 N1 1.396(2) . ?
C11 C12 1.425(2) . ?
C12 C13 1.383(2) . ?
C12 C14 1.510(2) . ?
C13 C13 1.467(3) 3_666 ?
C13 C1 1.474(2) 3_666 ?
C14 C15 1.529(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.516(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 O2 1.213(2) . ?
N2 O3 1.214(3) . ?
