data_benzimidazole@COF-300
_audit_creation_date               2025-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number       '2019/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C41 H28 N4, C7 H6 N2'
_chemical_formula_sum              'C69 H52 N12'
_chemical_formula_weight           1049.22
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'tetragonal'
_space_group_IT_number             88
_space_group_name_H-M_alt          'I 41/a'
_space_group_name_Hall             '-I 4ad'
loop_
  _space_group_symop_operation_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'

_cell_length_a                     27.031(5)
_cell_length_b                     27.031(5)
_cell_length_c                     7.394(2)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       5402(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      ?
_cell_measurement_temperature      173.00
_cell_measurement_theta_max        ?
_cell_measurement_theta_min        ?
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.616
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     ?
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.290
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         ?
_exptl_crystal_F_000               2200
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0572
_diffrn_reflns_av_unetI/netI       0.0337
_diffrn_reflns_Laue_measured_fraction_full  0.986
_diffrn_reflns_Laue_measured_fraction_max  0.986
_diffrn_reflns_limit_h_max         26
_diffrn_reflns_limit_h_min         -23
_diffrn_reflns_limit_k_max         27
_diffrn_reflns_limit_k_min         -27
_diffrn_reflns_limit_l_max         7
_diffrn_reflns_limit_l_min         -7
_diffrn_reflns_number              10614
_diffrn_reflns_point_group_measured_fraction_full  0.986
_diffrn_reflns_point_group_measured_fraction_max  0.986
_diffrn_reflns_theta_full          52.212
_diffrn_reflns_theta_max           52.212
_diffrn_reflns_theta_min           4.627
_diffrn_ambient_temperature        173.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.986
_diffrn_measured_fraction_theta_max  0.986
_diffrn_measurement_device_type    ?
_diffrn_measurement_method         ?
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1235
_reflns_number_total               1501
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.242
_refine_diff_density_min           -0.205
_refine_diff_density_rms           0.046
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       175
_refine_ls_number_reflns           1501
_refine_ls_number_restraints       261
_refine_ls_R_factor_all            0.1295
_refine_ls_R_factor_gt             0.1172
_refine_ls_restrained_S_all        0.982
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.2000P)²+11.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.3386
_refine_ls_wR_factor_ref           0.3523
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C16-C15 = C16-C17 = C12-C17 = C13-C12 = C13-C14 = C15-C14
 1.39 with sigma of 0.001
 C15-C12 = C16-C13 = C14-C17
 2.78 with sigma of 0.001
3. Restrained planarity
 C16, C15, C14, C13, C12, C17, N2, C18, N3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C16 \\sim C15 \\sim C17 \\sim C13 \\sim C14 \\sim C12 \\sim N2 \\sim N3 \\sim
C18: within 3.8A with sigma of 0.03 and sigma for terminal atoms of 0.03 within
3.8A
Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(N2) \\sim Ueq,
Uanis(N3) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
5. Others
 Fixed Sof: C16(0.25) H16(0.25) C15(0.25) H15(0.25) C14(0.25) H14(0.25)
 C13(0.25) H13(0.25) C12(0.25) C17(0.25) N2(0.25) H2(0.25) C18(0.25) H18(0.25)
 N3(0.25)
6.a :
 C12(C17,N2,C18,N3)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C4(H4), C6(H6), C8(H8), C11(H11), C10(H10), C16(H16),
 C15(H15), C14(H14), C13(H13), N2(H2), C18(H18)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C2 C 0.45439(15) 0.24649(15) 0.0014(5) 0.0598(13) Uani 1 1 d . . . . .
 C1 C 0.500000 0.250000 -0.125000 0.058(2) Uani 1 4 d S T P . .
 C3 C 0.44855(17) 0.28241(17) 0.1350(5) 0.0723(15) Uani 1 1 d . . . . .
 H3 H 0.472145 0.308330 0.144326 0.087 Uiso 1 1 calc R U . . .
 C7 C 0.42014(17) 0.20875(18) -0.0025(6) 0.0763(15) Uani 1 1 d . . . . .
 H7 H 0.423598 0.182980 -0.088931 0.092 Uiso 1 1 calc R U . . .
 C4 C 0.4095(2) 0.2811(2) 0.2531(6) 0.0875(17) Uani 1 1 d . . . . .
 H4 H 0.406259 0.306410 0.341578 0.105 Uiso 1 1 calc R U . . .
 N1 N 0.3319(2) 0.2409(2) 0.3579(8) 0.125(2) Uani 1 1 d . . . . .
 C6 C 0.38104(19) 0.2077(2) 0.1165(7) 0.0925(18) Uani 1 1 d . . . . .
 H6 H 0.357674 0.181494 0.109574 0.111 Uiso 1 1 calc R U . . .
 C5 C 0.37525(19) 0.2440(2) 0.2454(7) 0.0887(17) Uani 1 1 d . . . . .
 C8 C 0.3333(3) 0.2576(4) 0.5097(10) 0.138(3) Uani 1 1 d . . . . .
 H8 H 0.362978 0.272730 0.551092 0.165 Uiso 1 1 calc R U . . .
 C9 C 0.2902(2) 0.2551(4) 0.6325(9) 0.146(3) Uani 1 1 d . . . . .
 C11 C 0.2968(3) 0.2634(5) 0.8124(10) 0.185(5) Uani 1 1 d . . . . .
 H11 H 0.328503 0.272153 0.857783 0.222 Uiso 1 1 calc R U . . .
 C10 C 0.2429(3) 0.2412(5) 0.5714(10) 0.193(5) Uani 1 1 d . . . . .
 H10 H 0.238178 0.234673 0.446341 0.232 Uiso 1 1 calc R U . . .
 C16 C 0.3668(6) 0.4099(8) 0.178(2) 0.334(13) Uani 0.25 1 d D U P . .
 H16 H 0.395112 0.417574 0.249014 0.400 Uiso 0.25 1 calc R U P . .
 C15 C 0.3682(6) 0.4127(7) -0.010(2) 0.329(14) Uani 0.25 1 d D U P . .
 H15 H 0.398092 0.422469 -0.066772 0.395 Uiso 0.25 1 calc R U P . .
 C14 C 0.3274(7) 0.4017(9) -0.117(2) 0.334(14) Uani 0.25 1 d D U P . .
 H14 H 0.329066 0.403846 -0.245243 0.401 Uiso 0.25 1 calc R U P . .
 C13 C 0.2841(7) 0.3876(10) -0.030(2) 0.336(13) Uani 0.25 1 d D U P . .
 H13 H 0.255796 0.380062 -0.100816 0.404 Uiso 0.25 1 calc R U P . .
 C12 C 0.2806(7) 0.3841(8) 0.157(2) 0.335(14) Uani 0.25 1 d DG U P . .
 C17 C 0.3225(7) 0.3955(7) 0.258(2) 0.333(13) Uani 0.25 1 d DG U P . .
 N2 N 0.3110(11) 0.3897(12) 0.440(2) 0.337(13) Uani 0.25 1 d G U P . .
 H2 H 0.331165 0.394688 0.531258 0.404 Uiso 0.25 1 calc R U P . .
 C18 C 0.2619(11) 0.3748(12) 0.452(3) 0.337(14) Uani 0.25 1 d G U P . .
 H18 H 0.244295 0.368053 0.560245 0.404 Uiso 0.25 1 calc R U P . .
 N3 N 0.2431(7) 0.3713(11) 0.277(3) 0.333(13) Uani 0.25 1 d G U P . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 C2 C1 1.550(4) . ?
 C2 C3 1.394(6) . ?
 C2 C7 1.378(6) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.369(6) . ?
 C7 H7 0.9500 . ?
 C7 C6 1.375(6) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.368(8) . ?
 N1 C5 1.440(7) . ?
 N1 C8 1.211(9) . ?
 C6 H6 0.9500 . ?
 C6 C5 1.377(8) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.478(9) . ?
 C9 C11 1.361(10) . ?
 C9 C10 1.408(11) . ?
 C11 H11 0.9500 . ?
 C11 C10 1.381(10) 13_556 ?
 C10 H10 0.9500 . ?
 C16 H16 0.9500 . ?
 C16 C15 1.3902(11) . ?
 C16 C17 1.3902(11) . ?
 C15 H15 0.9500 . ?
 C15 C14 1.3902(11) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.3903(11) . ?
 C13 H13 0.9500 . ?
 C13 C12 1.3903(11) . ?
 C12 C17 1.3902(11) . ?
 C12 N3 1.3905(11) . ?
 C17 N2 1.3905(11) . ?
 N2 H2 0.8800 . ?
 N2 C18 1.3895(11) . ?
 C18 H18 0.9500 . ?
 C18 N3 1.3902(11) . ?

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
  _geom_angle_publ_flag
 C3 C2 C1 118.3(3) . . ?
 C7 C2 C1 124.6(3) . . ?
 C7 C2 C3 117.0(4) . . ?
 C2 C1 C2 111.32(14) 6_554 16_655 ?
 C2 C1 C2 111.32(14) 16_655 . ?
 C2 C1 C2 105.8(3) 6_554 . ?
 C2 C1 C2 105.8(3) 16_655 11_665 ?
 C2 C1 C2 111.32(14) 6_554 11_665 ?
 C2 C1 C2 111.32(14) 11_665 . ?
 C2 C3 H3 119.3 . . ?
 C4 C3 C2 121.4(4) . . ?
 C4 C3 H3 119.3 . . ?
 C2 C7 H7 119.4 . . ?
 C6 C7 C2 121.2(5) . . ?
 C6 C7 H7 119.4 . . ?
 C3 C4 H4 119.5 . . ?
 C5 C4 C3 120.9(5) . . ?
 C5 C4 H4 119.5 . . ?
 C8 N1 C5 119.2(7) . . ?
 C7 C6 H6 119.5 . . ?
 C7 C6 C5 121.0(5) . . ?
 C5 C6 H6 119.5 . . ?
 C4 C5 N1 124.8(5) . . ?
 C4 C5 C6 118.3(4) . . ?
 C6 C5 N1 116.8(5) . . ?
 N1 C8 H8 119.1 . . ?
 N1 C8 C9 121.8(8) . . ?
 C9 C8 H8 119.1 . . ?
 C11 C9 C8 119.3(7) . . ?
 C11 C9 C10 118.4(6) . . ?
 C10 C9 C8 122.1(7) . . ?
 C9 C11 H11 120.3 . . ?
 C9 C11 C10 119.5(9) . 13_556 ?
 C10 C11 H11 120.3 13_556 . ?
 C9 C10 H10 119.0 . . ?
 C11 C10 C9 122.1(8) 13_556 . ?
 C11 C10 H10 119.0 13_556 . ?
 C15 C16 H16 121.3 . . ?
 C17 C16 H16 121.3 . . ?
 C17 C16 C15 117.4(13) . . ?
 C16 C15 H15 118.7 . . ?
 C16 C15 C14 122.6(13) . . ?
 C14 C15 H15 118.7 . . ?
 C15 C14 H14 121.3 . . ?
 C15 C14 C13 117.4(13) . . ?
 C13 C14 H14 121.3 . . ?
 C14 C13 H13 118.7 . . ?
 C12 C13 C14 122.6(13) . . ?
 C12 C13 H13 118.7 . . ?
 C13 C12 N3 134.5(13) . . ?
 C17 C12 C13 117.4(13) . . ?
 C17 C12 N3 108.0 . . ?
 C16 C17 C12 122.6(13) . . ?
 C16 C17 N2 129.5(13) . . ?
 C12 C17 N2 107.9 . . ?
 C17 N2 H2 126.0 . . ?
 C18 N2 C17 108.0 . . ?
 C18 N2 H2 126.0 . . ?
 N2 C18 H18 126.0 . . ?
 N2 C18 N3 108.0 . . ?
 N3 C18 H18 126.0 . . ?
 C18 N3 C12 108.0 . . ?

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_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 C2 C3 C4 C5 1.0(7) . . . . ?
 C2 C7 C6 C5 -1.0(8) . . . . ?
 C1 C2 C3 C4 -179.0(4) . . . . ?
 C1 C2 C7 C6 178.8(4) . . . . ?
 C3 C2 C1 C2 174.1(3) . . . 16_655 ?
 C3 C2 C1 C2 53.0(3) . . . 6_554 ?
 C3 C2 C1 C2 -68.1(2) . . . 11_665 ?
 C3 C2 C7 C6 2.2(7) . . . . ?
 C3 C4 C5 N1 -176.8(5) . . . . ?
 C3 C4 C5 C6 0.3(8) . . . . ?
 C7 C2 C1 C2 -2.4(4) . . . 16_655 ?
 C7 C2 C1 C2 -123.5(4) . . . 6_554 ?
 C7 C2 C1 C2 115.4(5) . . . 11_665 ?
 C7 C2 C3 C4 -2.2(6) . . . . ?
 C7 C6 C5 C4 -0.3(8) . . . . ?
 C7 C6 C5 N1 177.1(5) . . . . ?
 N1 C8 C9 C11 164.5(10) . . . . ?
 N1 C8 C9 C10 -11.2(15) . . . . ?
 C5 N1 C8 C9 -179.3(7) . . . . ?
 C8 N1 C5 C4 -31.4(10) . . . . ?
 C8 N1 C5 C6 151.4(7) . . . . ?
 C8 C9 C11 C10 -177.1(10) . . . 13_556 ?
 C8 C9 C10 C11 177.0(10) . . . 13_556 ?
 C11 C9 C10 C11 1.3(19) . . . 13_556 ?
 C10 C9 C11 C10 -1.3(19) . . . 13_556 ?
 C16 C15 C14 C13 0.1(3) . . . . ?
 C16 C17 N2 C18 180.0(5) . . . . ?
 C15 C16 C17 C12 0.0(4) . . . . ?
 C15 C16 C17 N2 -180.0(3) . . . . ?
 C15 C14 C13 C12 -0.2(7) . . . . ?
 C14 C13 C12 C17 0.2(7) . . . . ?
 C14 C13 C12 N3 179.9(4) . . . . ?
 C13 C12 C17 C16 -0.2(6) . . . . ?
 C13 C12 C17 N2 179.9(5) . . . . ?
 C13 C12 N3 C18 -179.8(7) . . . . ?
 C12 C17 N2 C18 0.0 . . . . ?
 C17 C16 C15 C14 0.0(2) . . . . ?
 C17 C12 N3 C18 -0.1 . . . . ?
 C17 N2 C18 N3 0.0 . . . . ?
 N2 C18 N3 C12 0.1 . . . . ?
 N3 C12 C17 C16 -179.9(5) . . . . ?
 N3 C12 C17 N2 0.1 . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
