#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500080.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_4500080
loop_
_publ_author_name
'Eric Demers'
'Thierry Maris'
'Janie Cabana'
'Jean-Hugues Fournier'
'James D. Wuest'
_publ_section_title
;
 Weakly Bonded Molecular Networks Built from Tetranitro and
 Tetracyanospirobifluorenes
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              1237
_journal_page_last               1245
_journal_paper_doi               10.1021/cg049590t
_journal_volume                  5
_journal_year                    2005
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C53 H28 N4'
_chemical_formula_sum            'C53 H28 N4'
_chemical_formula_weight         720.79
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2114(9)
_cell_length_b                   13.2114(9)
_cell_length_c                   21.539(3)
_cell_measurement_reflns_used    3467
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      67.24
_cell_measurement_theta_min      3.92
_cell_volume                     3759.4(6)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart 2000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11979
_diffrn_reflns_theta_full        70.04
_diffrn_reflns_theta_max         70.04
_diffrn_reflns_theta_min         3.93
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.8900
_exptl_absorpt_correction_T_min  0.8700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0629
_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)+(0.0780P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1186
_reflns_number_total             1780
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            deposit.cif
_cod_data_source_block           jiw655
_cod_original_sg_symbol_H-M      I41/a
_cod_database_code               4500080
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
C1 C 0.5000 0.7500 0.1250 0.0456(8) Uani 1 4 d S
C2 C 0.45307(11) 0.67386(11) 0.08043(8) 0.0458(4) Uani 1 1 d .
C3 C 0.47004(12) 0.70268(12) 0.01847(8) 0.0493(5) Uani 1 1 d .
C4 C 0.43262(14) 0.64372(14) -0.02925(8) 0.0562(5) Uani 1 1 d .
H4 H 0.4436 0.6618 -0.0709 0.067 Uiso 1 1 calc .
C5 C 0.37836(14) 0.55707(14) -0.01423(9) 0.0596(5) Uani 1 1 d .
H5 H 0.3522 0.5169 -0.0465 0.072 Uiso 1 1 calc .
C6 C 0.36124(13) 0.52747(13) 0.04714(9) 0.0546(5) Uani 1 1 d .
C7 C 0.40046(11) 0.58750(12) 0.09485(8) 0.0508(5) Uani 1 1 d .
H7 H 0.3909 0.5688 0.1365 0.061 Uiso 1 1 calc .
C8 C 0.30548(13) 0.43268(14) 0.06306(9) 0.0599(5) Uani 1 1 d .
C9 C 0.33519(15) 0.37394(14) 0.11257(10) 0.0672(6) Uani 1 1 d .
H9 H 0.3907 0.3944 0.1368 0.081 Uiso 1 1 calc .
C10 C 0.28431(16) 0.28416(16) 0.12763(12) 0.0745(6) Uani 1 1 d .
C11 C 0.20469(17) 0.25203(17) 0.09163(13) 0.0831(7) Uani 1 1 d .
H11 H 0.1713 0.1913 0.1014 0.100 Uiso 1 1 calc .
C12 C 0.17411(18) 0.30736(19) 0.04218(13) 0.0908(8) Uani 1 1 d .
H12 H 0.1192 0.2855 0.0179 0.109 Uiso 1 1 calc .
C13 C 0.22575(17) 0.39934(17) 0.02694(11) 0.0816(7) Uani 1 1 d .
H13 H 0.2053 0.4372 -0.0078 0.098 Uiso 1 1 calc .
C14 C 0.3217(2) 0.2241(2) 0.17863(15) 0.0954(8) Uani 1 1 d .
N14 N 0.3564(2) 0.1768(2) 0.21940(15) 0.1464(12) 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 0.0181 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'
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
_geom_angle_publ_flag
C2 C1 C2 15_565 6_564 113.43(6) y
C2 C1 C2 15_565 . 113.43(6) y
C2 C1 C2 6_564 . 101.82(12) y
C2 C1 C2 15_565 12_766 101.82(12) y
C2 C1 C2 6_564 12_766 113.42(6) y
C2 C1 C2 . 12_766 113.43(6) y
C7 C2 C3 . . 121.41(15) y
C7 C2 C1 . . 127.82(14) y
C3 C2 C1 . . 110.77(12) y
C4 C3 C2 . . 119.77(16) y
C4 C3 C3 . 6_564 131.92(11) y
C2 C3 C3 . 6_564 108.31(9) y
C3 C4 C5 . . 118.44(17) y
C3 C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C4 C5 C6 . . 122.32(17) y
C4 C5 H5 . . 118.8 ?
C6 C5 H5 . . 118.8 ?
C5 C6 C7 . . 118.48(17) y
C5 C6 C8 . . 122.15(17) y
C7 C6 C8 . . 119.34(18) y
C2 C7 C6 . . 119.56(17) y
C2 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C13 . . 118.30(19) y
C9 C8 C6 . . 120.69(17) y
C13 C8 C6 . . 121.0(2) y
C8 C9 C10 . . 121.32(19) y
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C11 C10 C9 . . 119.9(2) y
C11 C10 C14 . . 121.5(2) y
C9 C10 C14 . . 118.5(2) y
C12 C11 C10 . . 120.4(2) y
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 119.8(2) y
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C8 C13 C12 . . 120.3(2) y
C8 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
N14 C14 C10 . . 177.0(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 15_565 1.5224(15) y
C1 C2 6_564 1.5225(15) y
C1 C2 . 1.5225(15) y
C1 C2 12_766 1.5225(15) y
C2 C7 . 1.372(2) y
C2 C3 . 1.406(2) y
C3 C4 . 1.381(2) y
C3 C3 6_564 1.480(3) y
C4 C5 . 1.389(3) y
C4 H4 . 0.94 ?
C5 C6 . 1.397(3) y
C5 H5 . 0.94 ?
C6 C7 . 1.398(2) y
C6 C8 . 1.493(2) y
C7 H7 . 0.94 ?
C8 C9 . 1.376(3) y
C8 C13 . 1.382(3) y
C9 C10 . 1.401(3) y
C9 H9 . 0.94 ?
C10 C11 . 1.374(3) y
C10 C14 . 1.442(4) y
C11 C12 . 1.354(3) y
C11 H11 . 0.94 ?
C12 C13 . 1.432(3) y
C12 H12 . 0.94 ?
C13 H13 . 0.94 ?
C14 N14 . 1.171(4) y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C2 C7 15_565 . -58.13(18) y
C2 C1 C2 C7 6_564 . 179.63(18) y
C2 C1 C2 C7 12_766 . 57.40(19) y
C2 C1 C2 C3 15_565 . 121.85(8) y
C2 C1 C2 C3 6_564 . -0.39(8) y
C2 C1 C2 C3 12_766 . -122.62(8) y
C7 C2 C3 C4 . . 0.5(2) y
C1 C2 C3 C4 . . -179.48(12) y
C7 C2 C3 C3 . 6_564 -179.04(16) y
C1 C2 C3 C3 . 6_564 0.98(19) y
C2 C3 C4 C5 . . 0.3(2) y
C3 C3 C4 C5 6_564 . 179.7(2) y
C3 C4 C5 C6 . . -0.5(3) y
C4 C5 C6 C7 . . -0.1(3) y
C4 C5 C6 C8 . . -178.18(16) y
C3 C2 C7 C6 . . -1.1(2) y
C1 C2 C7 C6 . . 178.88(13) y
C5 C6 C7 C2 . . 0.9(2) y
C8 C6 C7 C2 . . 179.02(15) y
C5 C6 C8 C9 . . 141.96(18) y
C7 C6 C8 C9 . . -36.1(3) y
C5 C6 C8 C13 . . -35.1(3) y
C7 C6 C8 C13 . . 146.80(19) y
C13 C8 C9 C10 . . -2.1(3) y
C6 C8 C9 C10 . . -179.24(17) y
C8 C9 C10 C11 . . 1.7(3) y
C8 C9 C10 C14 . . 177.6(2) y
C9 C10 C11 C12 . . -1.0(4) y
C14 C10 C11 C12 . . -176.8(2) y
C10 C11 C12 C13 . . 0.7(4) y
C9 C8 C13 C12 . . 1.8(3) y
C6 C8 C13 C12 . . 178.92(19) y
C11 C12 C13 C8 . . -1.1(4) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101386603
