data_benzotriazole@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, C6 H5 N3'
_chemical_formula_sum              'C65 H48 N16'
_chemical_formula_weight           1053.19
_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                     26.659(2)
_cell_length_b                     26.659(2)
_cell_length_c                     7.4645(8)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       5304.9(10)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1689
_cell_measurement_temperature      173.00
_cell_measurement_theta_max        56.126
_cell_measurement_theta_min        3.316
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.652
_exptl_absorpt_correction_T_max    0.7516
_exptl_absorpt_correction_T_min    0.4902
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.0742 after correction.
The Ratio of minimum to maximum transmission is 0.6522.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.319
_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    0.0784
_diffrn_reflns_av_unetI/netI       0.0512
_diffrn_reflns_Laue_measured_fraction_full  0.986
_diffrn_reflns_Laue_measured_fraction_max  0.986
_diffrn_reflns_limit_h_max         25
_diffrn_reflns_limit_h_min         -20
_diffrn_reflns_limit_k_max         25
_diffrn_reflns_limit_k_min         -19
_diffrn_reflns_limit_l_max         6
_diffrn_reflns_limit_l_min         -7
_diffrn_reflns_number              7601
_diffrn_reflns_point_group_measured_fraction_full  0.986
_diffrn_reflns_point_group_measured_fraction_max  0.986
_diffrn_reflns_theta_full          47.790
_diffrn_reflns_theta_max           47.790
_diffrn_reflns_theta_min           6.157
_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                     ?
_diffrn_source_current             1.0
_diffrn_source_power               0.05
_diffrn_source_voltage             50.0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  907
_reflns_number_total               1220
_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         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_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           0.264
_refine_diff_density_min           -0.246
_refine_diff_density_rms           0.060
_refine_ls_extinction_coef         0.0028(18)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       176
_refine_ls_number_reflns           1220
_refine_ls_number_restraints       99
_refine_ls_R_factor_all            0.1765
_refine_ls_R_factor_gt             0.1510
_refine_ls_restrained_S_all        1.134
_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+30.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.3837
_refine_ls_wR_factor_ref           0.4085
_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
 C12-C13 = C17-C12 = C17-C16 = C15-C16 = C15-C14 = C13-C14
 1.39 with sigma of 0.001
 C17-C14 = C15-C12 = C16-C13
 2.78 with sigma of 0.001
3. Restrained planarity
 N2, N3, N4, C12, C13, C14, C15, C16, C17
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N4 \\sim N2 \\sim N3 \\sim C12 \\sim C17 \\sim C13 \\sim C16 \\sim C14 \\sim
C15: within 2A with sigma of 0.03 and sigma for terminal atoms of 0.03 within 2A
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: N2(0.25) H2(0.25) N3(0.25) N4(0.25) C12(0.25) C17(0.25) C13(0.25)
 H13(0.25) C14(0.25) H14(0.25) C15(0.25) H15(0.25) C16(0.25) H16(0.25)
6.a :
 N2(N3,N4,C12,C17)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), N2(H2), C13(H13),
 C14(H14), C15(H15), C16(H16)
;
_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
 N1 N 0.6677(3) 0.7396(4) 0.6426(13) 0.137(4) Uani 1 1 d . . . . .
 C1 C 0.500000 0.750000 1.125000 0.051(4) Uani 1 4 d S T P . .
 C2 C 0.5456(3) 0.7465(3) 1.0010(8) 0.058(2) Uani 1 1 d . . . . .
 C3 C 0.5516(3) 0.7833(3) 0.8688(9) 0.076(3) Uani 1 1 d . . . . .
 H3 H 0.528085 0.809961 0.860743 0.091 Uiso 1 1 calc R U . . .
 C4 C 0.5910(4) 0.7814(4) 0.7505(11) 0.095(3) Uani 1 1 d . . . . .
 H4 H 0.594161 0.806770 0.661841 0.114 Uiso 1 1 calc R U . . .
 C5 C 0.6258(3) 0.7439(5) 0.7572(12) 0.099(3) Uani 1 1 d . . . . .
 C6 C 0.6202(3) 0.7079(4) 0.8838(13) 0.102(3) Uani 1 1 d . . . . .
 H6 H 0.643765 0.681225 0.890597 0.122 Uiso 1 1 calc R U . . .
 C7 C 0.5806(3) 0.7094(3) 1.0029(10) 0.082(3) Uani 1 1 d . . . . .
 H7 H 0.577675 0.683440 1.089656 0.098 Uiso 1 1 calc R U . . .
 C8 C 0.6676(5) 0.7612(7) 0.497(2) 0.171(6) Uani 1 1 d . U . . .
 H8 H 0.639265 0.781117 0.466903 0.206 Uiso 1 1 calc R U . . .
 C9 C 0.7095(5) 0.7578(7) 0.3645(17) 0.165(5) Uani 1 1 d . U . . .
 C10 C 0.7015(6) 0.7647(7) 0.193(2) 0.188(6) Uani 1 1 d . U . . .
 H10 H 0.668914 0.772772 0.150735 0.225 Uiso 1 1 calc R U . . .
 C11 C 0.7577(6) 0.7399(7) 0.4271(19) 0.192(6) Uani 1 1 d . U . . .
 H11 H 0.762048 0.731302 0.549667 0.231 Uiso 1 1 calc R U . . .
 N2 N 0.7549(7) 0.8481(9) 0.781(3) 0.264(18) Uani 0.25 1 d G U P . .
 H2 H 0.780538 0.832699 0.831268 0.317 Uiso 0.25 1 calc R U P . .
 N3 N 0.7461(9) 0.8526(11) 0.598(3) 0.270(19) Uani 0.25 1 d G U P . .
 N4 N 0.7018(9) 0.8795(11) 0.575(2) 0.256(18) Uani 0.25 1 d G U P . .
 C12 C 0.7160(6) 0.8720(7) 0.871(2) 0.259(17) Uani 0.25 1 d DG U P . .
 C17 C 0.6832(6) 0.8915(7) 0.744(3) 0.243(17) Uani 0.25 1 d DG U P . .
 C13 C 0.7040(7) 0.8802(10) 1.0503(19) 0.252(19) Uani 0.25 1 d D U P . .
 H13 H 0.725877 0.867341 1.139684 0.302 Uiso 0.25 1 calc R U P . .
 C14 C 0.6615(7) 0.9063(10) 1.104(2) 0.233(19) Uani 0.25 1 d D U P . .
 H14 H 0.654037 0.911378 1.227531 0.280 Uiso 0.25 1 calc R U P . .
 C15 C 0.6303(7) 0.9247(9) 0.970(2) 0.235(19) Uani 0.25 1 d D U P . .
 H15 H 0.601070 0.942688 1.003940 0.282 Uiso 0.25 1 calc R U P . .
 C16 C 0.6401(7) 0.9180(9) 0.789(2) 0.239(18) Uani 0.25 1 d D U P . .
 H16 H 0.618287 0.930918 0.699416 0.287 Uiso 0.25 1 calc R 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
 N1 C5 1.412(12) . ?
 N1 C8 1.230(16) . ?
 C1 C2 1.530(7) 6_564 ?
 C1 C2 1.530(7) . ?
 C1 C2 1.530(7) 12_768 ?
 C1 C2 1.530(7) 15_567 ?
 C2 C3 1.401(9) . ?
 C2 C7 1.361(10) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.374(11) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.362(13) . ?
 C5 C6 1.357(13) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.380(11) . ?
 C7 H7 0.9500 . ?
 C8 H8 0.9500 . ?
 C8 C9 1.495(18) . ?
 C9 C10 1.308(16) . ?
 C9 C11 1.449(19) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.416(17) 13_665 ?
 C11 H11 0.9500 . ?
 N2 H2 0.8800 . ?
 N2 N3 1.3916(11) . ?
 N2 C12 1.3917(11) . ?
 N3 N4 1.3911(11) . ?
 N4 C17 1.3913(11) . ?
 C12 C17 1.3903(10) . ?
 C12 C13 1.3903(11) . ?
 C17 C16 1.3903(11) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.3903(11) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.3903(11) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.3903(11) . ?
 C16 H16 0.9500 . ?

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
 C8 N1 C5 119.7(12) . . ?
 C2 C1 C2 105.5(5) 12_768 15_567 ?
 C2 C1 C2 111.5(2) . 12_768 ?
 C2 C1 C2 111.5(2) . 15_567 ?
 C2 C1 C2 105.5(5) . 6_564 ?
 C2 C1 C2 111.5(2) 12_768 6_564 ?
 C2 C1 C2 111.5(2) 6_564 15_567 ?
 C3 C2 C1 118.4(6) . . ?
 C7 C2 C1 125.6(6) . . ?
 C7 C2 C3 116.0(6) . . ?
 C2 C3 H3 119.5 . . ?
 C4 C3 C2 121.0(8) . . ?
 C4 C3 H3 119.5 . . ?
 C3 C4 H4 119.2 . . ?
 C5 C4 C3 121.6(8) . . ?
 C5 C4 H4 119.2 . . ?
 C4 C5 N1 125.1(11) . . ?
 C6 C5 N1 116.8(11) . . ?
 C6 C5 C4 118.0(7) . . ?
 C5 C6 H6 119.6 . . ?
 C5 C6 C7 120.8(9) . . ?
 C7 C6 H6 119.6 . . ?
 C2 C7 C6 122.6(8) . . ?
 C2 C7 H7 118.7 . . ?
 C6 C7 H7 118.7 . . ?
 N1 C8 H8 118.2 . . ?
 N1 C8 C9 123.7(14) . . ?
 C9 C8 H8 118.2 . . ?
 C10 C9 C8 121.0(14) . . ?
 C10 C9 C11 120.5(13) . . ?
 C11 C9 C8 118.0(12) . . ?
 C9 C10 H10 120.6 . . ?
 C9 C10 C11 118.9(15) . 13_665 ?
 C11 C10 H10 120.6 13_665 . ?
 C9 C11 H11 119.9 . . ?
 C10 C11 C9 120.3(14) 13_665 . ?
 C10 C11 H11 119.9 13_665 . ?
 N3 N2 H2 126.0 . . ?
 N3 N2 C12 108.0 . . ?
 C12 N2 H2 126.0 . . ?
 N4 N3 N2 108.0 . . ?
 N3 N4 C17 108.0 . . ?
 C17 C12 N2 108.0 . . ?
 C17 C12 C13 117.0(12) . . ?
 C13 C12 N2 135.0(12) . . ?
 C12 C17 N4 108.1 . . ?
 C12 C17 C16 123.0(12) . . ?
 C16 C17 N4 128.9(12) . . ?
 C12 C13 H13 118.5 . . ?
 C14 C13 C12 123.0(12) . . ?
 C14 C13 H13 118.5 . . ?
 C13 C14 H14 121.5 . . ?
 C13 C14 C15 117.0(12) . . ?
 C15 C14 H14 121.5 . . ?
 C14 C15 H15 118.5 . . ?
 C14 C15 C16 123.0(12) . . ?
 C16 C15 H15 118.5 . . ?
 C17 C16 H16 121.5 . . ?
 C15 C16 C17 117.0(12) . . ?
 C15 C16 H16 121.5 . . ?

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
 N1 C5 C6 C7 179.3(8) . . . . ?
 N1 C8 C9 C10 154.5(18) . . . . ?
 N1 C8 C9 C11 -17(2) . . . . ?
 C1 C2 C3 C4 -178.3(6) . . . . ?
 C1 C2 C7 C6 178.3(7) . . . . ?
 C2 C1 C2 C3 53.5(5) 6_564 . . . ?
 C2 C1 C2 C3 -67.7(4) 12_768 . . . ?
 C2 C1 C2 C3 174.6(6) 15_567 . . . ?
 C2 C1 C2 C7 -2.9(7) 15_567 . . . ?
 C2 C1 C2 C7 114.7(8) 12_768 . . . ?
 C2 C1 C2 C7 -124.1(7) 6_564 . . . ?
 C2 C3 C4 C5 -0.2(13) . . . . ?
 C3 C2 C7 C6 0.7(11) . . . . ?
 C3 C4 C5 N1 -179.1(8) . . . . ?
 C3 C4 C5 C6 0.7(14) . . . . ?
 C4 C5 C6 C7 -0.5(14) . . . . ?
 C5 N1 C8 C9 -178.3(12) . . . . ?
 C5 C6 C7 C2 -0.2(14) . . . . ?
 C7 C2 C3 C4 -0.5(10) . . . . ?
 C8 N1 C5 C4 -21.3(18) . . . . ?
 C8 N1 C5 C6 158.9(13) . . . . ?
 C8 C9 C10 C11 -178.6(16) . . . 13_665 ?
 C8 C9 C11 C10 179.0(16) . . . 13_665 ?
 C10 C9 C11 C10 7(3) . . . 13_665 ?
 C11 C9 C10 C11 -7(3) . . . 13_665 ?
 N2 N3 N4 C17 -0.1 . . . . ?
 N2 C12 C17 N4 0.0 . . . . ?
 N2 C12 C17 C16 -179.9(3) . . . . ?
 N2 C12 C13 C14 179.9(4) . . . . ?
 N3 N2 C12 C17 -0.1 . . . . ?
 N3 N2 C12 C13 -179.8(3) . . . . ?
 N3 N4 C17 C12 0.0 . . . . ?
 N3 N4 C17 C16 179.9(3) . . . . ?
 N4 C17 C16 C15 -179.9(3) . . . . ?
 C12 N2 N3 N4 0.1 . . . . ?
 C12 C17 C16 C15 0.0(6) . . . . ?
 C12 C13 C14 C15 -0.1(8) . . . . ?
 C17 C12 C13 C14 0.1(6) . . . . ?
 C13 C12 C17 N4 179.8(3) . . . . ?
 C13 C12 C17 C16 -0.1(4) . . . . ?
 C13 C14 C15 C16 0.0(9) . . . . ?
 C14 C15 C16 C17 0.0(8) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
