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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/10/4121096.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_4121096
loop_
_publ_author_name
'Yue-Biao Zhang'
'Jie Su'
'Hiroyasu Furukawa'
'Yifeng Yun'
'Felipe Gándara'
'Adam Duong'
'Xiaodong Zou'
'Omar M. Yaghi'
_publ_section_title
;
 Single-Crystal Structure of a Covalent Organic Framework
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16336
_journal_page_last               16339
_journal_paper_doi               10.1021/ja409033p
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C78 H58 Cl2 N4'
_chemical_formula_sum            'C78 H58 Cl2 N4'
_chemical_formula_weight         1122.18
_chemical_name_common            'Molecular Analogue of COF-320'
_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                   28.7128(12)
_cell_length_b                   28.7128(12)
_cell_length_c                   7.4609(4)
_cell_measurement_reflns_used    7530
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      61.13
_cell_measurement_theta_min      3.08
_cell_volume                     6151.0(5)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Gobel mirrors'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18875
_diffrn_reflns_theta_full        61.72
_diffrn_reflns_theta_max         61.72
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    1.315
_exptl_absorpt_correction_T_max  0.8581
_exptl_absorpt_correction_T_min  0.7346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0474
_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)+(0.0576P)²+6.5607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                1736
_reflns_number_total             2344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja409033p_si_004.cif
_cod_data_source_block           Molecular_Analogue_Of_COF-320
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4121096
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0000 0.2500 0.1250 0.0320(10) Uani 1 4 d S . .
C2 C -0.02221(7) 0.28653(7) -0.0006(3) 0.0318(5) Uani 1 1 d U . .
C3 C -0.01445(7) 0.33423(7) 0.0114(3) 0.0354(5) Uani 1 1 d U . .
H3 H 0.0027 0.3463 0.1099 0.043 Uiso 1 1 calc R . .
C4 C -0.03137(7) 0.36456(8) -0.1179(3) 0.0367(5) Uani 1 1 d U . .
H4 H -0.0258 0.3970 -0.1065 0.044 Uiso 1 1 calc R . .
C5 C -0.05644(7) 0.34793(7) -0.2639(3) 0.0343(5) Uani 1 1 d U . .
C6 C -0.06676(7) 0.30076(7) -0.2708(3) 0.0351(5) Uani 1 1 d U . .
H6 H -0.0858 0.2890 -0.3646 0.042 Uiso 1 1 calc R . .
C7 C -0.04969(7) 0.27084(7) -0.1431(3) 0.0341(5) Uani 1 1 d U . .
H7 H -0.0567 0.2386 -0.1518 0.041 Uiso 1 1 calc R . .
C8 C -0.04469(8) 0.40538(8) -0.4743(3) 0.0404(6) Uani 1 1 d . . .
H8 H -0.0147 0.4088 -0.4226 0.048 Uiso 1 1 calc R . .
C9 C -0.05705(8) 0.43455(8) -0.6275(3) 0.0389(6) Uani 1 1 d U . .
C10 C -0.02655(8) 0.46876(8) -0.6845(3) 0.0422(6) Uani 1 1 d U . .
H10 H 0.0025 0.4726 -0.6254 0.051 Uiso 1 1 calc R . .
C11 C -0.03804(8) 0.49745(8) -0.8268(3) 0.0430(6) Uani 1 1 d U . .
H11 H -0.0175 0.5219 -0.8602 0.052 Uiso 1 1 calc R . .
C12 C -0.07929(8) 0.49096(8) -0.9217(3) 0.0402(6) Uani 1 1 d U . .
C13 C -0.10922(9) 0.45575(8) -0.8658(3) 0.0475(6) Uani 1 1 d U . .
H13 H -0.1374 0.4505 -0.9295 0.057 Uiso 1 1 calc R . .
C14 C -0.09870(8) 0.42831(8) -0.7190(3) 0.0454(6) Uani 1 1 d U . .
H14 H -0.1201 0.4051 -0.6806 0.054 Uiso 1 1 calc R . .
C15 C -0.09003(8) 0.51993(8) -1.0814(3) 0.0424(6) Uani 1 1 d U . .
C16 C -0.08139(8) 0.56743(8) -1.0807(3) 0.0468(6) Uani 1 1 d U . .
H16 H -0.0692 0.5817 -0.9759 0.056 Uiso 1 1 calc R . .
C17 C -0.09032(9) 0.59428(9) -1.2308(3) 0.0506(7) Uani 1 1 d U . .
H17 H -0.0848 0.6269 -1.2277 0.061 Uiso 1 1 calc R . .
C18 C -0.10718(9) 0.57390(9) -1.3848(4) 0.0526(7) Uani 1 1 d U . .
H18 H -0.1129 0.5923 -1.4883 0.063 Uiso 1 1 calc R . .
C19 C -0.11575(9) 0.52686(9) -1.3882(4) 0.0579(7) Uani 1 1 d U . .
H19 H -0.1275 0.5127 -1.4941 0.069 Uiso 1 1 calc R . .
C20 C -0.10725(9) 0.49989(9) -1.2370(3) 0.0520(7) Uani 1 1 d U . .
H20 H -0.1133 0.4674 -1.2403 0.062 Uiso 1 1 calc R . .
N1 N -0.07236(6) 0.37572(6) -0.4077(2) 0.0392(5) Uani 1 1 d . . .
C1S C -0.255(2) 0.496(3) -1.733(4) 0.44(6) Uani 0.25 1 d PDU A -1
H1SA H -0.2843 0.5099 -1.7760 0.528 Uiso 0.25 1 calc PR A -1
H1SB H -0.2524 0.4644 -1.7843 0.528 Uiso 0.25 1 calc PR A -1
Cl1 Cl -0.2570(7) 0.4917(6) -1.498(3) 0.330(10) Uani 0.25 1 d PDU A -1
Cl2 Cl -0.2079(3) 0.5299(3) -1.8105(19) 0.257(5) Uani 0.25 1 d PDU A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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
C2 C1 C2 111.60(8) 15 6_454
C2 C1 C2 105.29(15) 15 12_666
C2 C1 C2 111.60(8) 6_454 12_666
C2 C1 C2 111.60(8) 15 .
C2 C1 C2 105.29(15) 6_454 .
C2 C1 C2 111.60(8) 12_666 .
C3 C2 C7 117.16(19) . .
C3 C2 C1 124.33(16) . .
C7 C2 C1 118.39(16) . .
C4 C3 C2 121.2(2) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C3 C4 C5 120.7(2) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 118.3(2) . .
C6 C5 N1 117.01(19) . .
C4 C5 N1 124.65(19) . .
C7 C6 C5 120.6(2) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C2 121.8(2) . .
C6 C7 H7 119.1 . .
C2 C7 H7 119.1 . .
N1 C8 C9 122.7(2) . .
N1 C8 H8 118.6 . .
C9 C8 H8 118.6 . .
C10 C9 C14 119.1(2) . .
C10 C9 C8 119.6(2) . .
C14 C9 C8 121.3(2) . .
C9 C10 C11 120.5(2) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C10 C11 C12 120.9(2) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C13 C12 C11 118.1(2) . .
C13 C12 C15 121.3(2) . .
C11 C12 C15 120.6(2) . .
C14 C13 C12 121.1(2) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C13 C14 C9 120.3(2) . .
C13 C14 H14 119.9 . .
C9 C14 H14 119.9 . .
C16 C15 C20 118.4(2) . .
C16 C15 C12 120.7(2) . .
C20 C15 C12 120.9(2) . .
C17 C16 C15 120.8(2) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C18 C17 C16 120.2(2) . .
C18 C17 H17 119.9 . .
C16 C17 H17 119.9 . .
C19 C18 C17 119.8(2) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C18 C19 C20 120.1(2) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C15 C20 C19 120.7(2) . .
C15 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C8 N1 C5 118.37(19) . .
Cl1 C1S Cl2 113.3(17) . .
Cl1 C1S H1SA 108.9 . .
Cl2 C1S H1SA 108.9 . .
Cl1 C1S H1SB 108.9 . .
Cl2 C1S H1SB 108.9 . .
H1SA C1S H1SB 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.544(2) 15
C1 C2 1.544(2) 6_454
C1 C2 1.544(2) 12_666
C1 C2 1.544(2) .
C2 C3 1.390(3) .
C2 C7 1.398(3) .
C3 C4 1.387(3) .
C3 H3 0.9500 .
C4 C5 1.390(3) .
C4 H4 0.9500 .
C5 C6 1.388(3) .
C5 N1 1.413(3) .
C6 C7 1.373(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 N1 1.267(3) .
C8 C9 1.461(3) .
C8 H8 0.9500 .
C9 C10 1.383(3) .
C9 C14 1.389(3) .
C10 C11 1.384(3) .
C10 H10 0.9500 .
C11 C12 1.393(3) .
C11 H11 0.9500 .
C12 C13 1.391(3) .
C12 C15 1.486(3) .
C13 C14 1.382(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.386(3) .
C15 C20 1.387(3) .
C16 C17 1.383(3) .
C16 H16 0.9500 .
C17 C18 1.377(3) .
C17 H17 0.9500 .
C18 C19 1.373(4) .
C18 H18 0.9500 .
C19 C20 1.390(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C1S Cl1 1.76(2) .
C1S Cl2 1.76(2) .
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122778
