#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/86/2018636.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018636
loop_
_publ_author_name
'Fouad, Farid'
'Bunge, Scott D.'
'Ellman, Brett D.'
'Twieg, Robert J.'
_publ_section_title
;
 Tetranaphthyleno[5,6-bcd:11,12-b'c'd':17,18-b''c''d'':23,24-b'''c'''d''']tetrafuran
;
_journal_coeditor_code           FN3112
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o465
_journal_page_last               o467
_journal_paper_doi               10.1107/S0108270112040681
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C40 H16 O4'
_chemical_formula_moiety         'C40 H16 O4'
_chemical_formula_sum            'C40 H16 O4'
_chemical_formula_weight         560.53
_chemical_name_systematic
;
Tetranaphthyleno[5,6-bcd:11,12-b'c'd':17,18-
b''c''d'':23,24-
b'''c'''d''']tetrafuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.746(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.592(3)
_cell_length_b                   4.3936(8)
_cell_length_c                   17.713(3)
_cell_measurement_reflns_used    1241
_cell_measurement_temperature    187(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.66
_cell_volume                     1192.1(4)
_computing_cell_refinement       'SAINT (Bruker 2007)'
_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_data_reduction        'SAINT (Bruker 2007)'
_computing_molecular_graphics
;
XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      187(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8923
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0415
_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)+(0.0461P)²+0.6737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                1466
_reflns_number_total             2117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3112.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2018636
_cod_database_fobs_code          2018636
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 -0.10332(9) 0.4901(4) 0.18331(8) 0.0250(4) Uani d . 1 1
O O2 0.17712(9) 1.0623(3) 0.09905(8) 0.0250(4) Uani d . 1 1
C C1 -0.13080(14) 0.3288(5) 0.11529(12) 0.0233(5) Uani d . 1 1
C C2 -0.07813(14) 0.3909(5) 0.06309(12) 0.0223(5) Uani d . 1 1
C C3 -0.01310(14) 0.5995(5) 0.09933(12) 0.0221(5) Uani d . 1 1
C C4 -0.03077(14) 0.6531(5) 0.17136(13) 0.0230(5) Uani d . 1 1
C C5 0.01945(14) 0.8499(5) 0.22650(13) 0.0235(5) Uani d . 1 1
C C6 0.00122(15) 0.9075(5) 0.30021(13) 0.0279(6) Uani d . 1 1
H H6 -0.0477 0.8139 0.3155 0.034 Uiso calc R 1 1
C C7 0.05408(15) 1.0987(6) 0.35000(13) 0.0307(6) Uani d . 1 1
H H7 0.0410 1.1371 0.3994 0.037 Uiso calc R 1 1
C C8 0.12686(15) 1.2374(6) 0.32898(14) 0.0315(6) Uani d . 1 1
H H8 0.1630 1.3665 0.3645 0.038 Uiso calc R 1 1
C C9 0.14660(15) 1.1888(5) 0.25737(13) 0.0279(6) Uani d . 1 1
H H9 0.1958 1.2861 0.2434 0.033 Uiso calc R 1 1
C C10 0.09373(14) 0.9942(5) 0.20465(12) 0.0226(5) Uani d . 1 1
C C11 0.10960(14) 0.9358(5) 0.12968(13) 0.0233(5) Uani d . 1 1
C C12 0.05925(14) 0.7457(5) 0.07765(12) 0.0217(5) Uani d . 1 1
C C13 0.09723(14) 0.7503(5) 0.00995(12) 0.0222(5) Uani d . 1 1
C C14 0.16743(14) 0.9424(5) 0.02521(12) 0.0230(5) Uani d . 1 1
C C15 0.22335(14) 1.0122(5) -0.02711(12) 0.0230(5) Uani d . 1 1
C C16 0.20398(14) 0.8695(5) -0.10166(12) 0.0236(5) Uani d . 1 1
C C17 0.25848(15) 0.9325(5) -0.15476(13) 0.0280(6) Uani d . 1 1
H H17 0.2467 0.8399 -0.2041 0.034 Uiso calc R 1 1
C C18 0.32821(15) 1.1252(5) -0.13629(14) 0.0302(6) Uani d . 1 1
H H18 0.3642 1.1653 -0.1729 0.036 Uiso calc R 1 1
C C19 0.34703(15) 1.2639(6) -0.06371(14) 0.0311(6) Uani d . 1 1
H H19 0.3957 1.3966 -0.0515 0.037 Uiso calc R 1 1
C C20 0.29571(14) 1.2093(5) -0.01050(14) 0.0281(6) Uani d . 1 1
H H20 0.3090 1.3054 0.0383 0.034 Uiso calc R 1 1
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C4 O1 C1 . . 104.97(16)
C11 O2 C14 . . 104.99(17)
C2 C1 O1 . . 110.76(19)
C2 C1 C16 . 3_565 124.7(2)
O1 C1 C16 . 3_565 124.49(19)
C1 C2 C13 . 3_565 118.5(2)
C1 C2 C3 . . 106.77(19)
C13 C2 C3 3_565 . 134.7(2)
C4 C3 C12 . . 118.9(2)
C4 C3 C2 . . 106.19(19)
C12 C3 C2 . . 134.9(2)
C3 C4 O1 . . 111.29(19)
C3 C4 C5 . . 124.1(2)
O1 C4 C5 . . 124.61(19)
C6 C5 C4 . . 124.3(2)
C6 C5 C10 . . 118.8(2)
C4 C5 C10 . . 116.8(2)
C7 C6 C5 . . 120.2(2)
C7 C6 H6 . . 119.9
C5 C6 H6 . . 119.9
C6 C7 C8 . . 121.0(2)
C6 C7 H7 . . 119.5
C8 C7 H7 . . 119.5
C9 C8 C7 . . 120.6(2)
C9 C8 H8 . . 119.7
C7 C8 H8 . . 119.7
C8 C9 C10 . . 120.0(2)
C8 C9 H9 . . 120.0
C10 C9 H9 . . 120.0
C9 C10 C11 . . 123.1(2)
C9 C10 C5 . . 119.3(2)
C11 C10 C5 . . 117.55(19)
C12 C11 O2 . . 111.16(19)
C12 C11 C10 . . 124.0(2)
O2 C11 C10 . . 124.8(2)
C11 C12 C3 . . 118.6(2)
C11 C12 C13 . . 106.18(19)
C3 C12 C13 . . 135.2(2)
C14 C13 C2 . 3_565 118.4(2)
C14 C13 C12 . . 106.47(19)
C2 C13 C12 3_565 . 135.2(2)
C13 C14 O2 . . 111.20(18)
C13 C14 C15 . . 124.8(2)
O2 C14 C15 . . 124.0(2)
C20 C15 C14 . . 124.2(2)
C20 C15 C16 . . 118.8(2)
C14 C15 C16 . . 117.1(2)
C17 C16 C1 . 3_565 125.0(2)
C17 C16 C15 . . 118.5(2)
C1 C16 C15 3_565 . 116.54(19)
C18 C17 C16 . . 120.9(2)
C18 C17 H17 . . 119.6
C16 C17 H17 . . 119.6
C17 C18 C19 . . 120.6(2)
C17 C18 H18 . . 119.7
C19 C18 H18 . . 119.7
C20 C19 C18 . . 120.4(2)
C20 C19 H19 . . 119.8
C18 C19 H19 . . 119.8
C19 C20 C15 . . 120.9(2)
C19 C20 H20 . . 119.6
C15 C20 H20 . . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C4 . 1.388(3)
O1 C1 . 1.395(3)
O2 C11 . 1.387(3)
O2 C14 . 1.392(3)
C1 C2 . 1.374(3)
C1 C16 3_565 1.420(3)
C2 C13 3_565 1.416(3)
C2 C3 . 1.427(3)
C3 C4 . 1.375(3)
C3 C12 . 1.412(3)
C4 C5 . 1.425(3)
C5 C6 . 1.410(3)
C5 C10 . 1.435(3)
C6 C7 . 1.375(3)
C6 H6 . 0.9500
C7 C8 . 1.398(3)
C7 H7 . 0.9500
C8 C9 . 1.376(3)
C8 H8 . 0.9500
C9 C10 . 1.413(3)
C9 H9 . 0.9500
C10 C11 . 1.419(3)
C11 C12 . 1.376(3)
C12 C13 . 1.433(3)
C13 C14 . 1.369(3)
C13 C2 3_565 1.416(3)
C14 C15 . 1.419(3)
C15 C20 . 1.409(3)
C15 C16 . 1.442(3)
C16 C17 . 1.407(3)
C16 C1 3_565 1.420(3)
C17 C18 . 1.369(3)
C17 H17 . 0.9500
C18 C19 . 1.404(3)
C18 H18 . 0.9500
C19 C20 . 1.367(3)
C19 H19 . 0.9500
C20 H20 . 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86188287
