data_2-Methylimidazole@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, C4 H6 N2'
_chemical_formula_sum              'C45 H34 N6'
_chemical_formula_weight           658.78
_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                     27.2075(11)
_cell_length_b                     27.2075(11)
_cell_length_c                     7.3528(5)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       5442.9(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      5354
_cell_measurement_temperature      293.00
_cell_measurement_theta_max        62.428
_cell_measurement_theta_min        4.597
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.375
_exptl_absorpt_correction_T_max    0.7464
_exptl_absorpt_correction_T_min    0.5977
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1217 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.8008.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      0.804
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         ?
_exptl_crystal_F_000               1384
_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    0.0571
_diffrn_reflns_av_unetI/netI       0.0389
_diffrn_reflns_Laue_measured_fraction_full  0.937
_diffrn_reflns_Laue_measured_fraction_max  0.937
_diffrn_reflns_limit_h_max         31
_diffrn_reflns_limit_h_min         -22
_diffrn_reflns_limit_k_max         31
_diffrn_reflns_limit_k_min         -26
_diffrn_reflns_limit_l_max         7
_diffrn_reflns_limit_l_min         -7
_diffrn_reflns_number              13809
_diffrn_reflns_point_group_measured_fraction_full  0.937
_diffrn_reflns_point_group_measured_fraction_max  0.937
_diffrn_reflns_theta_full          63.828
_diffrn_reflns_theta_max           63.828
_diffrn_reflns_theta_min           6.235
_diffrn_ambient_temperature        293.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.937
_diffrn_measured_fraction_theta_max  0.937
_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                  1524
_reflns_number_total               2110
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.506
_refine_diff_density_min           -0.296
_refine_diff_density_rms           0.086
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       148
_refine_ls_number_reflns           2110
_refine_ls_number_restraints       82
_refine_ls_R_factor_all            0.1826
_refine_ls_R_factor_gt             0.1518
_refine_ls_restrained_S_all        1.002
_refine_ls_shift/su_max            0.000
_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            0.3825
_refine_ls_wR_factor_ref           0.4121
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-C12 = N3-C12 = C14-N3 = C14-N2 = C13-N2
 1.345 with sigma of 0.001
 C14-C15
 1.5 with sigma of 0.01
 N2-C15 \\sim N3-C15
 with sigma of 0.02
3. Restrained planarity
 C12, N3, C14, N2, C13, C15
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C14 \\sim C12 \\sim N3 \\sim C13 \\sim N2 \\sim C15: within 2A with sigma of
0.02 and sigma for terminal atoms of 0.03 within 2A
Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: C12(0.25) H12(0.25) N3(0.25) C14(0.25) N2(0.25) H2(0.25) C13(0.25)
 H13(0.25) C15(0.25) H15A(0.25) H15B(0.25) H15C(0.25)
6.a Riding coordinates:
 C15(H15A,H15B,H15C)
6.b :
 C12(N3,C14,N2,C13)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), N2(H2),
 C13(H13)
;
_atom_sites_solution_hydrogens     mixed
_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 0.66781(19) 0.2402(2) 0.3559(7) 0.0841(18) Uani 1 1 d . . . . .
 C1 C 0.500000 0.250000 -0.125000 0.0339(18) Uani 1 4 d S T P . .
 C2 C 0.54529(15) 0.24616(15) 0.0032(5) 0.0375(11) Uani 1 1 d . . . . .
 C3 C 0.55174(18) 0.28175(18) 0.1353(6) 0.0513(14) Uani 1 1 d . . . . .
 H3 H 0.528887 0.307034 0.144758 0.062 Uiso 1 1 calc R U . . .
 C4 C 0.5913(2) 0.2808(2) 0.2539(7) 0.0623(16) Uani 1 1 d . . . . .
 H4 H 0.595069 0.305614 0.339809 0.075 Uiso 1 1 calc R U . . .
 C5 C 0.62510(18) 0.2432(2) 0.2447(7) 0.0599(15) Uani 1 1 d . . . . .
 C6 C 0.61841(19) 0.2070(2) 0.1165(7) 0.0627(16) Uani 1 1 d . . . . .
 H6 H 0.640802 0.181290 0.108798 0.075 Uiso 1 1 calc R U . . .
 C7 C 0.57873(17) 0.20846(18) -0.0015(6) 0.0516(13) Uani 1 1 d . . . . .
 H7 H 0.574679 0.183299 -0.085808 0.062 Uiso 1 1 calc R U . . .
 C8 C 0.6668(3) 0.2544(3) 0.5098(11) 0.097(2) Uani 1 1 d . . . . .
 H8 H 0.637348 0.266928 0.554008 0.116 Uiso 1 1 calc R U . . .
 C9 C 0.7099(2) 0.2535(3) 0.6354(9) 0.093(2) Uani 1 1 d . . . . .
 C10 C 0.7033(3) 0.2633(4) 0.8128(10) 0.105(3) Uani 1 1 d . . . . .
 H10 H 0.672569 0.272538 0.856688 0.126 Uiso 1 1 calc R U . . .
 C11 C 0.7436(3) 0.2594(4) 0.9297(10) 0.113(3) Uani 1 1 d . . . . .
 H11 H 0.739360 0.265458 1.053201 0.136 Uiso 1 1 calc R U . . .
 C12 C 0.7406(8) 0.3662(6) 0.357(5) 0.171(11) Uani 0.25 1 d DG U P . .
 H12 H 0.771494 0.352132 0.371700 0.206 Uiso 0.25 1 calc R U P . .
 N3 N 0.7184(8) 0.3761(6) 0.198(4) 0.191(10) Uani 0.25 1 d DG U P . .
 C14 C 0.6744(8) 0.3963(5) 0.234(4) 0.180(10) Uani 0.25 1 d DG U P . .
 N2 N 0.6694(10) 0.3990(7) 0.416(4) 0.184(10) Uani 0.25 1 d DG U P . .
 H2 H 0.644397 0.410555 0.473615 0.221 Uiso 0.25 1 calc R U P . .
 C13 C 0.7103(12) 0.3804(7) 0.492(4) 0.173(11) Uani 0.25 1 d DG U P . .
 H13 H 0.716589 0.377806 0.616080 0.208 Uiso 0.25 1 calc R U P . .
 C15 C 0.6377(10) 0.4128(7) 0.094(5) 0.145(11) Uani 0.25 1 d D U P . .
 H15A H 0.641499 0.447670 0.078862 0.218 Uiso 0.25 1 d R U P . .
 H15B H 0.605099 0.405890 0.137292 0.218 Uiso 0.25 1 d R U P . .
 H15C H 0.642739 0.396711 -0.020528 0.218 Uiso 0.25 1 d 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 1.423(7) . ?
 N1 C8 1.196(9) . ?
 C1 C2 1.555(4) . ?
 C1 C2 1.555(4) 6_554 ?
 C1 C2 1.555(4) 11_665 ?
 C1 C2 1.555(4) 16_655 ?
 C2 C3 1.383(6) . ?
 C2 C7 1.371(6) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.386(7) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.378(8) . ?
 C5 C6 1.374(8) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.386(7) . ?
 C7 H7 0.9300 . ?
 C8 H8 0.9300 . ?
 C8 C9 1.493(9) . ?
 C9 C10 1.344(10) . ?
 C9 C11 1.397(11) 13_656 ?
 C10 H10 0.9300 . ?
 C10 C11 1.397(9) . ?
 C11 H11 0.9300 . ?
 C12 H12 0.9300 . ?
 C12 N3 1.3451 . ?
 C12 C13 1.3455 . ?
 N3 C14 1.3447 . ?
 C14 N2 1.3451 . ?
 C14 C15 1.504(10) . ?
 N2 H2 0.8600 . ?
 N2 C13 1.3449 . ?
 C13 H13 0.9300 . ?
 C15 H15A 0.9602 . ?
 C15 H15B 0.9599 . ?
 C15 H15C 0.9599 . ?

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 120.5(6) . . ?
 C2 C1 C2 111.56(15) 11_665 6_554 ?
 C2 C1 C2 111.56(15) . 11_665 ?
 C2 C1 C2 105.4(3) . 6_554 ?
 C2 C1 C2 111.56(15) . 16_655 ?
 C2 C1 C2 105.4(3) 11_665 16_655 ?
 C2 C1 C2 111.56(15) 16_655 6_554 ?
 C3 C2 C1 118.6(3) . . ?
 C7 C2 C1 124.1(3) . . ?
 C7 C2 C3 117.2(4) . . ?
 C2 C3 H3 119.1 . . ?
 C2 C3 C4 121.9(4) . . ?
 C4 C3 H3 119.1 . . ?
 C3 C4 H4 120.0 . . ?
 C5 C4 C3 120.1(5) . . ?
 C5 C4 H4 120.0 . . ?
 C4 C5 N1 124.0(5) . . ?
 C6 C5 N1 117.5(5) . . ?
 C6 C5 C4 118.5(4) . . ?
 C5 C6 H6 119.6 . . ?
 C5 C6 C7 120.9(5) . . ?
 C7 C6 H6 119.6 . . ?
 C2 C7 C6 121.5(5) . . ?
 C2 C7 H7 119.3 . . ?
 C6 C7 H7 119.3 . . ?
 N1 C8 H8 117.9 . . ?
 N1 C8 C9 124.2(7) . . ?
 C9 C8 H8 117.9 . . ?
 C10 C9 C8 119.4(7) . . ?
 C10 C9 C11 120.3(6) . 13_656 ?
 C11 C9 C8 120.2(7) 13_656 . ?
 C9 C10 H10 120.8 . . ?
 C9 C10 C11 118.4(8) . . ?
 C11 C10 H10 120.8 . . ?
 C9 C11 C10 121.2(7) 13_656 . ?
 C9 C11 H11 119.4 13_656 . ?
 C10 C11 H11 119.4 . . ?
 N3 C12 H12 126.0 . . ?
 N3 C12 C13 108.0 . . ?
 C13 C12 H12 126.0 . . ?
 C14 N3 C12 108.0 . . ?
 N3 C14 N2 108.0 . . ?
 N3 C14 C15 125.2(9) . . ?
 N2 C14 C15 126.8(9) . . ?
 C14 N2 H2 126.0 . . ?
 C13 N2 C14 108.0 . . ?
 C13 N2 H2 126.0 . . ?
 C12 C13 H13 126.0 . . ?
 N2 C13 C12 108.0 . . ?
 N2 C13 H13 126.0 . . ?
 C14 C15 H15A 107.6 . . ?
 C14 C15 H15B 109.1 . . ?
 C14 C15 H15C 111.7 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?

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 -177.5(5) . . . . ?
 N1 C8 C9 C10 -170.0(9) . . . . ?
 N1 C8 C9 C11 7.6(13) . . . 13_656 ?
 C1 C2 C3 C4 -179.8(4) . . . . ?
 C1 C2 C7 C6 -180.0(4) . . . . ?
 C2 C1 C2 C3 -175.1(4) 11_665 . . . ?
 C2 C1 C2 C3 67.4(3) 16_655 . . . ?
 C2 C1 C2 C3 -53.8(3) 6_554 . . . ?
 C2 C1 C2 C7 -115.1(5) 16_655 . . . ?
 C2 C1 C2 C7 123.7(4) 6_554 . . . ?
 C2 C1 C2 C7 2.5(4) 11_665 . . . ?
 C2 C3 C4 C5 -1.3(8) . . . . ?
 C3 C2 C7 C6 -2.4(7) . . . . ?
 C3 C4 C5 N1 177.4(5) . . . . ?
 C3 C4 C5 C6 -0.1(8) . . . . ?
 C4 C5 C6 C7 0.3(8) . . . . ?
 C5 N1 C8 C9 -179.1(7) . . . . ?
 C5 C6 C7 C2 1.1(8) . . . . ?
 C7 C2 C3 C4 2.5(7) . . . . ?
 C8 N1 C5 C4 35.0(10) . . . . ?
 C8 N1 C5 C6 -147.3(7) . . . . ?
 C8 C9 C10 C11 176.3(8) . . . . ?
 C9 C10 C11 C9 1.3(15) . . . 13_656 ?
 C11 C9 C10 C11 -1.3(15) 13_656 . . . ?
 C12 N3 C14 N2 0.0 . . . . ?
 C12 N3 C14 C15 180.0 . . . . ?
 N3 C12 C13 N2 0.0 . . . . ?
 N3 C14 N2 C13 0.0 . . . . ?
 C14 N2 C13 C12 0.0 . . . . ?
 C13 C12 N3 C14 0.0 . . . . ?
 C15 C14 N2 C13 180.0 . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
