#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:25:16 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243507 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556153.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_1556153
loop_
_publ_author_name
'Takase, Masayoshi'
'Inabe, Ayumi'
'Sugawara, Yuki'
'Fujita, Wataru'
'Nishinaga, Tohru'
'Nomura, Kotohiro'
_publ_section_title
;
 Donor-acceptor segregated paracyclophanes composed of naphthobipyrrole
 and stacked fluoroarenes.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3202
_journal_page_last               3205
_journal_paper_doi               10.1021/ol400882q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C40 H20 F8 N4'
_chemical_formula_weight         708.60
_chemical_name_common            4a
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 129.736(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.8969(19)
_cell_length_b                   25.977(2)
_cell_length_c                   14.1722(13)
_cell_measurement_temperature    173(2)
_cell_volume                     5916.1(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1217
_diffrn_reflns_av_sigmaI/netI    0.1492
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12642
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1645
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1975
_reflns_number_total             4242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400882q_si_002.cif
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               1556153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1A N 0.2879(3) 0.12736(18) 0.0656(4) 0.0381(12) Uani 1 1 d .
N2A N 0.5306(3) 0.16317(17) 0.0114(4) 0.0363(12) Uani 1 1 d .
C1A C 0.0713(4) 0.1671(2) 0.1928(6) 0.0465(17) Uani 1 1 d .
H1A H 0.0129 0.1648 0.1475 0.056 Uiso 1 1 calc R
C2A C 0.1060(3) 0.1526(2) 0.1411(6) 0.0469(17) Uani 1 1 d .
H2A H 0.0706 0.1404 0.0590 0.056 Uiso 1 1 calc R
C3A C 0.1912(3) 0.1553(2) 0.2042(6) 0.0395(15) Uani 1 1 d .
C4A C 0.2677(3) 0.1618(2) 0.1175(5) 0.0361(15) Uani 1 1 d .
H4A H 0.2833 0.1970 0.1344 0.043 Uiso 1 1 calc R
C5A C 0.2214(3) 0.1366(2) 0.1404(5) 0.0389(15) Uani 1 1 d .
C6A C 0.2093(3) 0.0858(2) 0.0947(5) 0.0384(15) Uani 1 1 d .
H6A H 0.1774 0.0598 0.0947 0.046 Uiso 1 1 calc R
C7A C 0.2509(3) 0.0804(2) 0.0507(5) 0.0426(16) Uani 1 1 d .
H7A H 0.2539 0.0500 0.0163 0.051 Uiso 1 1 calc R
C8A C 0.3455(3) 0.1360(2) 0.0462(5) 0.0354(15) Uani 1 1 d .
C9A C 0.4052(3) 0.0997(2) 0.0777(5) 0.0366(15) Uani 1 1 d .
C10A C 0.4602(3) 0.1074(2) 0.0584(5) 0.0364(15) Uani 1 1 d .
C11A C 0.4648(3) 0.1535(2) 0.0135(5) 0.0357(15) Uani 1 1 d .
C12A C 0.4066(3) 0.1898(2) -0.0162(5) 0.0369(15) Uani 1 1 d .
C13A C 0.3479(3) 0.1817(2) -0.0035(5) 0.0369(15) Uani 1 1 d .
C14A C 0.5283(4) 0.1933(2) -0.0707(5) 0.0453(16) Uani 1 1 d .
H14A H 0.4800 0.2074 -0.1449 0.054 Uiso 1 1 calc R
C15A C 0.6089(3) 0.1990(2) -0.0254(5) 0.0424(16) Uani 1 1 d .
H15A H 0.6258 0.2171 -0.0644 0.051 Uiso 1 1 calc R
C16A C 0.6630(3) 0.1732(2) 0.0902(5) 0.0383(15) Uani 1 1 d .
C17A C 0.6123(3) 0.1511(2) 0.1083(6) 0.0453(16) Uani 1 1 d .
H17A H 0.6305 0.1305 0.1770 0.054 Uiso 1 1 calc R
C18A C 0.7554(3) 0.1722(2) 0.1712(6) 0.0420(16) Uani 1 1 d .
C19A C 0.7922(4) 0.1875(2) 0.1235(6) 0.0488(17) Uani 1 1 d .
H19A H 0.7580 0.2006 0.0421 0.059 Uiso 1 1 calc R
C20A C 0.8772(4) 0.1848(2) 0.1887(6) 0.0493(17) Uani 1 1 d .
H20A H 0.9000 0.1953 0.1512 0.059 Uiso 1 1 calc R
F1A F 0.2931(2) 0.21875(12) -0.0350(3) 0.0574(10) Uani 1 1 d .
F2A F 0.4074(2) 0.23628(12) -0.0573(3) 0.0558(10) Uani 1 1 d .
F3A F 0.40893(18) 0.05483(12) 0.1281(3) 0.0533(10) Uani 1 1 d .
F4A F 0.51298(18) 0.06871(12) 0.0873(3) 0.0530(10) Uani 1 1 d .
N1B N 0.8460(3) 1.02606(16) 0.2008(4) 0.0356(12) Uani 1 1 d .
N2B N 0.8828(3) 0.83303(18) 0.2871(4) 0.0386(12) Uani 1 1 d .
C1B C 1.0723(3) 1.0361(2) 0.3671(5) 0.0348(15) Uani 1 1 d .
C2B C 0.9968(3) 1.03730(19) 0.3428(5) 0.0327(14) Uani 1 1 d .
C3B C 0.9217(3) 1.03425(19) 0.2238(5) 0.0303(14) Uani 1 1 d .
C4B C 0.7688(3) 1.0452(2) 0.1016(5) 0.0407(16) Uani 1 1 d .
H4B H 0.7585 1.0704 0.0448 0.049 Uiso 1 1 calc R
C5B C 0.7107(3) 1.0211(2) 0.1009(5) 0.0421(16) Uani 1 1 d .
H5B H 0.6524 1.0270 0.0431 0.051 Uiso 1 1 calc R
C6B C 0.7510(3) 0.9852(2) 0.2011(5) 0.0360(15) Uani 1 1 d .
C7B C 0.8346(3) 0.9898(2) 0.2627(5) 0.0348(14) Uani 1 1 d .
H7B H 0.8775 0.9715 0.3349 0.042 Uiso 1 1 calc R
C8B C 0.7063(3) 0.9546(2) 0.2310(5) 0.0348(15) Uani 1 1 d .
C9B C 0.6401(3) 0.9788(2) 0.2120(5) 0.0433(16) Uani 1 1 d .
H9B H 0.6276 1.0132 0.1826 0.052 Uiso 1 1 calc R
C10B C 0.5909(3) 0.9552(2) 0.2337(6) 0.0499(18) Uani 1 1 d .
H10B H 0.5452 0.9732 0.2175 0.060 Uiso 1 1 calc R
C11B C 0.6085(3) 0.9056(2) 0.2788(5) 0.0434(16) Uani 1 1 d .
H11B H 0.5771 0.8894 0.2975 0.052 Uiso 1 1 calc R
C12B C 0.6734(3) 0.8804(2) 0.2958(5) 0.0423(16) Uani 1 1 d .
H12B H 0.6850 0.8460 0.3247 0.051 Uiso 1 1 calc R
C13B C 0.7231(3) 0.9030(2) 0.2727(5) 0.0358(15) Uani 1 1 d .
C14B C 0.8254(3) 0.8725(2) 0.2432(5) 0.0356(15) Uani 1 1 d .
H14B H 0.8132 0.8977 0.1852 0.043 Uiso 1 1 calc R
C15B C 0.7893(3) 0.8697(2) 0.2956(5) 0.0343(14) Uani 1 1 d .
C16B C 0.8255(4) 0.8263(2) 0.3754(6) 0.0553(19) Uani 1 1 d .
H16B H 0.8123 0.8140 0.4243 0.066 Uiso 1 1 calc R
C17B C 0.8827(4) 0.8056(2) 0.3688(6) 0.0576(19) Uani 1 1 d .
H17B H 0.9169 0.7766 0.4141 0.069 Uiso 1 1 calc R
C19B C 0.9413(3) 0.8310(2) 0.2692(5) 0.0387(15) Uani 1 1 d .
F1B F 1.14166(17) 1.03427(12) 0.4850(3) 0.0458(9) Uani 1 1 d .
F2B F 0.99779(18) 1.03953(12) 0.4383(3) 0.0470(9) Uani 1 1 d .
C18B C 0.9727(4) 0.8753(2) 0.2609(6) 0.0531(18) Uani 1 1 d .
C20B C 0.9712(3) 0.7862(2) 0.2576(5) 0.0338(14) Uani 1 1 d .
F3B F 0.9518(3) 0.92171(13) 0.2773(5) 0.1056(18) Uani 1 1 d .
F4B F 0.94259(19) 0.74066(11) 0.2633(3) 0.0542(10) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C4A N1A C7A 108.6(5) . .
C4A N1A C8A 126.0(5) . .
C7A N1A C8A 124.9(5) . .
C14A N2A C17A 108.8(5) . .
C14A N2A C11A 127.5(5) . .
C17A N2A C11A 122.6(5) . .
C20A C1A C2A 118.5(6) 2_655 .
C1A C2A C3A 122.5(6) . .
C2A C3A C18A 118.6(6) . 2_655
C2A C3A C5A 117.5(6) . .
C18A C3A C5A 123.8(5) 2_655 .
C5A C4A N1A 108.6(5) . .
C4A C5A C6A 106.4(6) . .
C4A C5A C3A 129.2(5) . .
C6A C5A C3A 124.3(5) . .
C7A C6A C5A 109.0(5) . .
C6A C7A N1A 107.2(5) . .
C9A C8A C13A 115.1(5) . .
C9A C8A N1A 122.1(5) . .
C13A C8A N1A 122.8(5) . .
F3A C9A C10A 117.8(5) . .
F3A C9A C8A 119.6(5) . .
C10A C9A C8A 122.6(5) . .
F4A C10A C9A 117.7(5) . .
F4A C10A C11A 120.0(5) . .
C9A C10A C11A 122.3(5) . .
C12A C11A C10A 115.2(5) . .
C12A C11A N2A 123.5(5) . .
C10A C11A N2A 121.0(5) . .
F2A C12A C13A 117.2(5) . .
F2A C12A C11A 119.6(5) . .
C13A C12A C11A 123.2(5) . .
F1A C13A C12A 119.8(5) . .
F1A C13A C8A 118.8(5) . .
C12A C13A C8A 121.4(5) . .
C15A C14A N2A 107.2(5) . .
C14A C15A C16A 108.7(5) . .
C17A C16A C15A 105.8(5) . .
C17A C16A C18A 128.8(6) . .
C15A C16A C18A 125.4(5) . .
C16A C17A N2A 109.4(5) . .
C19A C18A C3A 117.3(5) . 2_655
C19A C18A C16A 118.4(6) . .
C3A C18A C16A 124.3(5) 2_655 .
C18A C19A C20A 122.9(6) . .
C1A C20A C19A 120.1(6) 2_655 .
C4B N1B C7B 108.7(4) . .
C4B N1B C3B 125.9(5) . .
C7B N1B C3B 124.6(4) . .
C17B N2B C14B 107.3(5) . .
C17B N2B C19B 127.6(5) . .
C14B N2B C19B 123.5(5) . .
F1B C1B C3B 119.7(5) . 2_755
F1B C1B C2B 117.6(5) . .
C3B C1B C2B 122.7(5) 2_755 .
F2B C2B C3B 120.2(5) . .
F2B C2B C1B 118.1(5) . .
C3B C2B C1B 121.7(5) . .
C1B C3B C2B 115.3(5) 2_755 .
C1B C3B N1B 123.3(5) 2_755 .
C2B C3B N1B 121.3(5) . .
C5B C4B N1B 107.3(5) . .
C4B C5B C6B 109.5(5) . .
C7B C6B C5B 106.2(5) . .
C7B C6B C8B 130.1(5) . .
C5B C6B C8B 123.5(5) . .
C6B C7B N1B 108.4(5) . .
C9B C8B C13B 117.6(6) . .
C9B C8B C6B 115.8(5) . .
C13B C8B C6B 126.5(5) . .
C8B C9B C10B 123.2(6) . .
C11B C10B C9B 119.8(6) . .
C10B C11B C12B 117.7(6) . .
C11B C12B C13B 123.6(6) . .
C12B C13B C8B 118.0(5) . .
C12B C13B C15B 115.7(5) . .
C8B C13B C15B 126.3(5) . .
C15B C14B N2B 109.8(5) . .
C14B C15B C16B 106.2(5) . .
C14B C15B C13B 128.1(5) . .
C16B C15B C13B 125.7(5) . .
C17B C16B C15B 107.5(6) . .
N2B C17B C16B 109.2(6) . .
C18B C19B C20B 114.9(5) . .
C18B C19B N2B 120.5(5) . .
C20B C19B N2B 124.7(5) . .
C18B C18B F3B 116.6(3) 2_755 .
C18B C18B C19B 122.6(3) 2_755 .
F3B C18B C19B 120.7(5) . .
F4B C20B C20B 118.9(3) . 2_755
F4B C20B C19B 118.7(5) . .
C20B C20B C19B 122.4(3) 2_755 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1A C4A 1.385(6) .
N1A C7A 1.388(6) .
N1A C8A 1.414(7) .
N2A C14A 1.377(7) .
N2A C17A 1.380(6) .
N2A C11A 1.417(6) .
C1A C20A 1.371(8) 2_655
C1A C2A 1.373(8) .
C2A C3A 1.391(7) .
C3A C18A 1.426(8) 2_655
C3A C5A 1.478(8) .
C4A C5A 1.367(7) .
C5A C6A 1.421(7) .
C6A C7A 1.362(7) .
C8A C9A 1.390(7) .
C8A C13A 1.397(7) .
C9A F3A 1.344(6) .
C9A C10A 1.355(7) .
C10A F4A 1.346(6) .
C10A C11A 1.388(7) .
C11A C12A 1.375(7) .
C12A F2A 1.346(6) .
C12A C13A 1.364(7) .
C13A F1A 1.336(6) .
C14A C15A 1.373(7) .
C15A C16A 1.429(7) .
C16A C17A 1.366(7) .
C16A C18A 1.487(7) .
C18A C19A 1.369(7) .
C18A C3A 1.426(8) 2_655
C19A C20A 1.384(7) .
C20A C1A 1.371(8) 2_655
N1B C4B 1.388(6) .
N1B C7B 1.408(6) .
N1B C3B 1.412(6) .
N2B C17B 1.361(7) .
N2B C14B 1.387(6) .
N2B C19B 1.400(6) .
C1B F1B 1.341(6) .
C1B C3B 1.372(7) 2_755
C1B C2B 1.383(7) .
C2B F2B 1.343(6) .
C2B C3B 1.389(7) .
C3B C1B 1.373(7) 2_755
C4B C5B 1.362(7) .
C5B C6B 1.436(7) .
C6B C7B 1.370(7) .
C6B C8B 1.482(7) .
C8B C9B 1.380(7) .
C8B C13B 1.415(7) .
C9B C10B 1.391(8) .
C10B C11B 1.379(7) .
C11B C12B 1.382(7) .
C12B C13B 1.401(7) .
C13B C15B 1.481(7) .
C14B C15B 1.356(7) .
C15B C16B 1.425(7) .
C16B C17B 1.367(8) .
C19B C18B 1.366(7) .
C19B C20B 1.379(7) .
C18B C18B 1.358(11) 2_755
C18B F3B 1.353(6) .
C20B F4B 1.350(5) .
C20B C20B 1.352(10) 2_755
