#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:04:55 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/54/1555458.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_1555458
loop_
_publ_author_name
'Tasior, Mariusz'
'Chotkowski, Maciej'
'Gryko, Daniel T.'
_publ_section_title
;
 Extension of Pyrrolopyrrole π-System: Approach to Constructing
 Hexacyclic Nitrogen-Containing Aromatic Systems.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6106
_journal_page_last               6109
_journal_paper_doi               10.1021/acs.orglett.5b03129
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C56 H40 F6 N6'
_chemical_formula_sum            'C56 H40 F6 N6'
_chemical_formula_weight         910.94
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 94.823(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.398(2)
_cell_length_b                   11.831(3)
_cell_length_c                   25.874(7)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.55
_cell_measurement_theta_min      3.43
_cell_volume                     2256.6(10)
_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 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32435
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.550
_diffrn_reflns_theta_min         3.428
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  0.8830
_exptl_absorpt_correction_T_min  0.8090
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0639
_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/[σ²(Fo²)+(0.0795P)²+1.5688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2980
_reflns_number_total             4116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b03129_si_002.cif
_cod_data_source_block           MT843_0m
_cod_original_cell_volume        2256.6(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555458
_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.
;
_shelx_estimated_absorpt_t_min   0.809
_shelx_estimated_absorpt_t_max   0.883
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 1.4062(3) 0.1168(2) 0.60886(10) 0.1166(10) Uani 1 1 d . . .
F2 F 1.5574(3) 0.22708(19) 0.56832(11) 0.1048(9) Uani 1 1 d . . .
F3' F 1.4056(6) 0.0728(3) 0.53692(19) 0.0667(11) Uani 0.5 1 d . . P
N1 N 0.6740(3) 0.50512(17) 0.54999(7) 0.0395(5) Uani 1 1 d . . .
N2 N 0.8517(3) 0.24916(18) 0.45722(8) 0.0459(5) Uani 1 1 d . . .
N3 N 0.3546(6) 0.1224(4) 0.20677(12) 0.1144(14) Uani 1 1 d . . .
C1 C 0.7066(3) 0.3106(2) 0.44377(9) 0.0405(6) Uani 1 1 d . . .
C2 C 0.6471(3) 0.3982(2) 0.47559(9) 0.0380(6) Uani 1 1 d . . .
C3 C 0.7574(3) 0.4246(2) 0.52169(9) 0.0385(6) Uani 1 1 d . . .
C4 C 0.9259(3) 0.3689(2) 0.53396(9) 0.0404(6) Uani 1 1 d . . .
C5 C 1.0612(4) 0.3967(2) 0.57414(10) 0.0470(6) Uani 1 1 d . . .
H5 H 1.0450 0.4591 0.5951 0.056 Uiso 1 1 calc R U .
C6 C 1.2147(4) 0.3330(2) 0.58240(11) 0.0498(7) Uani 1 1 d . . .
H6 H 1.3021 0.3524 0.6088 0.060 Uiso 1 1 calc R U .
C7 C 1.2412(4) 0.2391(2) 0.55156(10) 0.0463(6) Uani 1 1 d . . .
C8 C 1.4058(4) 0.1685(3) 0.56383(12) 0.0575(8) Uani 1 1 d . . .
C9 C 1.1171(4) 0.2115(2) 0.51142(10) 0.0474(6) Uani 1 1 d . . .
H9 H 1.1369 0.1492 0.4907 0.057 Uiso 1 1 calc R U .
C10 C 0.9594(3) 0.2772(2) 0.50130(10) 0.0420(6) Uani 1 1 d . . .
C11 C 0.6170(3) 0.2770(2) 0.39223(9) 0.0414(6) Uani 1 1 d . . .
C12 C 0.5664(4) 0.1655(2) 0.38469(11) 0.0570(8) Uani 1 1 d . . .
H12 H 0.5781 0.1154 0.4125 0.068 Uiso 1 1 calc R U .
C13 C 0.4989(5) 0.1276(3) 0.33658(12) 0.0645(9) Uani 1 1 d . . .
H13 H 0.4638 0.0525 0.3321 0.077 Uiso 1 1 calc R U .
C14 C 0.4835(4) 0.2009(3) 0.29517(11) 0.0564(8) Uani 1 1 d . . .
C15 C 0.4121(5) 0.1592(3) 0.24540(13) 0.0764(11) Uani 1 1 d . . .
C16 C 0.5356(4) 0.3132(3) 0.30210(10) 0.0552(7) Uani 1 1 d . . .
H16 H 0.5260 0.3629 0.2742 0.066 Uiso 1 1 calc R U .
C17 C 0.6015(4) 0.3506(2) 0.35050(10) 0.0477(6) Uani 1 1 d . . .
H17 H 0.6357 0.4257 0.3552 0.057 Uiso 1 1 calc R U .
C18 C 0.5083(3) 0.5318(2) 0.52233(9) 0.0374(5) Uani 1 1 d . . .
C19 C 0.7384(3) 0.5377(2) 0.60173(9) 0.0393(6) Uani 1 1 d . . .
C20 C 0.7344(4) 0.4609(2) 0.64158(10) 0.0482(7) Uani 1 1 d . . .
H20 H 0.6785 0.3911 0.6358 0.058 Uiso 1 1 calc R U .
C21 C 0.8143(4) 0.4882(3) 0.69064(11) 0.0557(7) Uani 1 1 d . . .
H21 H 0.8115 0.4358 0.7173 0.067 Uiso 1 1 calc R U .
C22 C 0.8981(4) 0.5916(3) 0.70060(11) 0.0532(7) Uani 1 1 d . . .
C23 C 0.8974(4) 0.6675(2) 0.65996(11) 0.0521(7) Uani 1 1 d . . .
H23 H 0.9510 0.7380 0.6657 0.062 Uiso 1 1 calc R U .
C24 C 0.8192(4) 0.6415(2) 0.61099(10) 0.0449(6) Uani 1 1 d . . .
H24 H 0.8212 0.6941 0.5843 0.054 Uiso 1 1 calc R U .
C25 C 0.9882(6) 0.6262(3) 0.75323(13) 0.0783(10) Uani 1 1 d . . .
H25A H 1.1142 0.6431 0.7488 0.094 Uiso 1 1 calc R U .
H25B H 0.9321 0.6961 0.7632 0.094 Uiso 1 1 calc R U .
C26 C 0.9845(6) 0.5465(4) 0.79724(12) 0.0793(11) Uani 1 1 d . . .
H26A H 1.0449 0.4770 0.7886 0.095 Uiso 1 1 calc R U .
H26B H 0.8594 0.5282 0.8022 0.095 Uiso 1 1 calc R U .
C27 C 1.0759(6) 0.5931(4) 0.84799(13) 0.0823(11) Uani 1 1 d . . .
H27A H 1.1996 0.6143 0.8426 0.099 Uiso 1 1 calc R U .
H27B H 1.0124 0.6608 0.8574 0.099 Uiso 1 1 calc R U .
C28 C 1.0788(7) 0.5108(4) 0.89189(15) 0.1018(14) Uani 1 1 d . . .
H28A H 0.9566 0.4909 0.8981 0.153 Uiso 1 1 calc R U .
H28B H 1.1378 0.5446 0.9226 0.153 Uiso 1 1 calc R U .
H28C H 1.1436 0.4441 0.8832 0.153 Uiso 1 1 calc R U .
F3" F 1.4574(9) 0.1135(6) 0.5220(3) 0.107(2) Uiso 0.5 1 d . . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C3 N1 C18 107.20(19) . .
C3 N1 C19 123.5(2) . .
C18 N1 C19 128.5(2) . .
C1 N2 C10 119.2(2) . .
N2 C1 C2 122.4(2) . .
N2 C1 C11 112.3(2) . .
C2 C1 C11 125.3(2) . .
C1 C2 C18 137.7(2) . 3_666
C1 C2 C3 117.6(2) . .
C18 C2 C3 104.4(2) 3_666 .
N1 C3 C2 110.3(2) . .
N1 C3 C4 128.7(2) . .
C2 C3 C4 121.1(2) . .
C10 C4 C5 117.9(2) . .
C10 C4 C3 114.7(2) . .
C5 C4 C3 127.4(2) . .
C6 C5 C4 120.9(3) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 120.4(3) . .
C5 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C9 C7 C6 120.5(2) . .
C9 C7 C8 120.9(3) . .
C6 C7 C8 118.5(2) . .
F1 C8 F2 103.2(3) . .
F1 C8 F3' 93.9(3) . .
F2 C8 F3' 117.3(3) . .
F1 C8 F3" 120.5(4) . .
F2 C8 F3" 91.6(4) . .
F3' C8 F3" 32.3(3) . .
F1 C8 C7 113.0(3) . .
F2 C8 C7 113.5(3) . .
F3' C8 C7 113.7(3) . .
F3" C8 C7 112.5(4) . .
C7 C9 C10 120.2(2) . .
C7 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
N2 C10 C4 124.4(2) . .
N2 C10 C9 115.7(2) . .
C4 C10 C9 119.8(2) . .
C12 C11 C17 119.1(2) . .
C12 C11 C1 118.4(2) . .
C17 C11 C1 122.1(2) . .
C13 C12 C11 120.9(3) . .
C13 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
C12 C13 C14 119.9(3) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 C16 119.9(3) . .
C13 C14 C15 118.8(3) . .
C16 C14 C15 121.3(3) . .
N3 C15 C14 177.5(5) . .
C17 C16 C14 119.8(3) . .
C17 C16 H16 120.1 . .
C14 C16 H16 120.1 . .
C16 C17 C11 120.5(3) . .
C16 C17 H17 119.8 . .
C11 C17 H17 119.8 . .
C18 C18 N1 108.5(3) 3_666 .
C18 C18 C2 109.6(3) 3_666 3_666
N1 C18 C2 141.9(2) . 3_666
C20 C19 C24 119.6(2) . .
C20 C19 N1 119.6(2) . .
C24 C19 N1 120.5(2) . .
C19 C20 C21 119.7(3) . .
C19 C20 H20 120.1 . .
C21 C20 H20 120.1 . .
C22 C21 C20 121.5(3) . .
C22 C21 H21 119.2 . .
C20 C21 H21 119.2 . .
C23 C22 C21 117.3(3) . .
C23 C22 C25 118.7(3) . .
C21 C22 C25 124.0(3) . .
C24 C23 C22 121.8(3) . .
C24 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
C19 C24 C23 120.0(2) . .
C19 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C26 C25 C22 118.8(3) . .
C26 C25 H25A 107.6 . .
C22 C25 H25A 107.6 . .
C26 C25 H25B 107.6 . .
C22 C25 H25B 107.6 . .
H25A C25 H25B 107.0 . .
C25 C26 C27 113.3(3) . .
C25 C26 H26A 108.9 . .
C27 C26 H26A 108.9 . .
C25 C26 H26B 108.9 . .
C27 C26 H26B 108.9 . .
H26A C26 H26B 107.7 . .
C28 C27 C26 113.3(4) . .
C28 C27 H27A 108.9 . .
C26 C27 H27A 108.9 . .
C28 C27 H27B 108.9 . .
C26 C27 H27B 108.9 . .
H27A C27 H27B 107.7 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C8 1.316(4) .
F2 C8 1.315(4) .
F3' C8 1.329(5) .
N1 C3 1.379(3) .
N1 C18 1.403(3) .
N1 C19 1.436(3) .
N2 C1 1.319(3) .
N2 C10 1.376(3) .
N3 C15 1.139(4) .
C1 C2 1.416(3) .
C1 C11 1.493(3) .
C2 C18 1.421(3) 3_666
C2 C3 1.422(3) .
C3 C4 1.422(3) .
C4 C10 1.409(4) .
C4 C5 1.420(4) .
C5 C6 1.364(4) .
C5 H5 0.9300 .
C6 C7 1.391(4) .
C6 H6 0.9300 .
C7 C9 1.367(4) .
C7 C8 1.489(4) .
C8 F3" 1.346(7) .
C9 C10 1.408(4) .
C9 H9 0.9300 .
C11 C12 1.380(4) .
C11 C17 1.384(4) .
C12 C13 1.377(4) .
C12 H12 0.9300 .
C13 C14 1.376(4) .
C13 H13 0.9300 .
C14 C16 1.390(5) .
C14 C15 1.437(4) .
C16 C17 1.378(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C18 1.376(5) 3_666
C18 C2 1.421(3) 3_666
C19 C20 1.376(4) .
C19 C24 1.378(4) .
C20 C21 1.393(4) .
C20 H20 0.9300 .
C21 C22 1.386(4) .
C21 H21 0.9300 .
C22 C23 1.383(4) .
C22 C25 1.521(4) .
C23 C24 1.382(4) .
C23 H23 0.9300 .
C24 H24 0.9300 .
C25 C26 1.481(5) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C27 1.529(4) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C27 C28 1.495(6) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C10 N2 C1 C2 -6.2(4) . .
C10 N2 C1 C11 173.6(2) . .
N2 C1 C2 C18 -169.1(3) . 3_666
C11 C1 C2 C18 11.1(5) . 3_666
N2 C1 C2 C3 4.7(4) . .
C11 C1 C2 C3 -175.1(2) . .
C18 N1 C3 C2 -0.1(3) . .
C19 N1 C3 C2 170.8(2) . .
C18 N1 C3 C4 -178.5(2) . .
C19 N1 C3 C4 -7.6(4) . .
C1 C2 C3 N1 -175.5(2) . .
C18 C2 C3 N1 0.2(3) 3_666 .
C1 C2 C3 C4 3.1(4) . .
C18 C2 C3 C4 178.8(2) 3_666 .
N1 C3 C4 C10 169.8(2) . .
C2 C3 C4 C10 -8.5(3) . .
N1 C3 C4 C5 -11.2(4) . .
C2 C3 C4 C5 170.5(2) . .
C10 C4 C5 C6 -3.2(4) . .
C3 C4 C5 C6 177.9(3) . .
C4 C5 C6 C7 -0.2(4) . .
C5 C6 C7 C9 2.3(4) . .
C5 C6 C7 C8 -176.7(3) . .
C9 C7 C8 F1 -113.4(3) . .
C6 C7 C8 F1 65.6(4) . .
C9 C7 C8 F2 129.6(3) . .
C6 C7 C8 F2 -51.4(4) . .
C9 C7 C8 F3' -7.9(5) . .
C6 C7 C8 F3' 171.1(4) . .
C9 C7 C8 F3" 27.2(5) . .
C6 C7 C8 F3" -153.8(4) . .
C6 C7 C9 C10 -0.9(4) . .
C8 C7 C9 C10 178.1(3) . .
C1 N2 C10 C4 -0.1(4) . .
C1 N2 C10 C9 -176.5(2) . .
C5 C4 C10 N2 -171.8(2) . .
C3 C4 C10 N2 7.3(4) . .
C5 C4 C10 C9 4.5(4) . .
C3 C4 C10 C9 -176.4(2) . .
C7 C9 C10 N2 174.1(2) . .
C7 C9 C10 C4 -2.6(4) . .
N2 C1 C11 C12 55.1(3) . .
C2 C1 C11 C12 -125.1(3) . .
N2 C1 C11 C17 -117.6(3) . .
C2 C1 C11 C17 62.2(4) . .
C17 C11 C12 C13 -0.9(5) . .
C1 C11 C12 C13 -173.9(3) . .
C11 C12 C13 C14 0.8(5) . .
C12 C13 C14 C16 -0.2(5) . .
C12 C13 C14 C15 -179.8(3) . .
C13 C14 C16 C17 -0.4(4) . .
C15 C14 C16 C17 179.2(3) . .
C14 C16 C17 C11 0.3(4) . .
C12 C11 C17 C16 0.3(4) . .
C1 C11 C17 C16 173.0(2) . .
C3 N1 C18 C18 -0.1(3) . 3_666
C19 N1 C18 C18 -170.4(3) . 3_666
C3 N1 C18 C2 -179.8(3) . 3_666
C19 N1 C18 C2 9.9(5) . 3_666
C3 N1 C19 C20 -66.2(3) . .
C18 N1 C19 C20 102.7(3) . .
C3 N1 C19 C24 107.9(3) . .
C18 N1 C19 C24 -83.2(3) . .
C24 C19 C20 C21 -1.0(4) . .
N1 C19 C20 C21 173.2(2) . .
C19 C20 C21 C22 0.2(4) . .
C20 C21 C22 C23 0.7(5) . .
C20 C21 C22 C25 -179.8(3) . .
C21 C22 C23 C24 -1.0(4) . .
C25 C22 C23 C24 179.5(3) . .
C20 C19 C24 C23 0.7(4) . .
N1 C19 C24 C23 -173.4(2) . .
C22 C23 C24 C19 0.3(4) . .
C23 C22 C25 C26 178.2(3) . .
C21 C22 C25 C26 -1.2(6) . .
C22 C25 C26 C27 -178.6(3) . .
C25 C26 C27 C28 -177.7(4) . .
