# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nm01
_database_code_depnum_ccdc_archive 'CCDC 2210454'
loop_
_audit_author_name
_audit_author_address
'Gong Jianye'
;Inner Mongolia University
China
;
_audit_update_record             
;
2022-09-30 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-06-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N4 O2'
_chemical_formula_sum            'C26 H24 N4 O2'
_chemical_formula_weight         424.49
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.8659(13)
_cell_length_b                   11.4511(9)
_cell_length_c                   8.7949(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.531(6)
_cell_angle_gamma                90
_cell_volume                     2091.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3392
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.9270
_cell_measurement_theta_min      3.0150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9345
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  28.00   1.00    7.50    --  -11.59 -99.00 120.00   42
  2  ω    -29.00  78.00   1.00    7.50    --   11.74  19.00 -90.00  107
  3  ω     35.00  95.00   1.00    7.50    --   11.74 178.00 120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0303784000
_diffrn_orient_matrix_UB_12      -0.0276565000
_diffrn_orient_matrix_UB_13      0.0146031000
_diffrn_orient_matrix_UB_21      -0.0131529000
_diffrn_orient_matrix_UB_22      -0.0524450000
_diffrn_orient_matrix_UB_23      -0.0326529000
_diffrn_orient_matrix_UB_31      0.0083338000
_diffrn_orient_matrix_UB_32      0.0179614000
_diffrn_orient_matrix_UB_33      -0.0727358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2846
_reflns_number_total             3680
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.072
_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)+(0.0801P)²+1.4323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 O1, N3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim N3: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_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
O1 O 0.54677(10) 0.19266(19) 0.5526(2) 0.0387(6) Uani 1 1 d . U . . .
O2 O 0.74863(10) 0.4070(2) 0.4897(2) 0.0397(6) Uani 1 1 d . . . . .
N1 N 0.18206(10) 0.3638(2) 0.8778(3) 0.0260(6) Uani 1 1 d . . . . .
N2 N 0.46677(10) 0.2773(2) 0.6676(3) 0.0269(6) Uani 1 1 d . . . . .
N3 N 0.52599(11) 0.2839(2) 0.6232(3) 0.0304(6) Uani 1 1 d . U . . .
N4 N 0.62711(11) 0.3709(2) 0.6018(3) 0.0301(6) Uani 1 1 d . . . . .
C1 C 0.24798(12) 0.3564(2) 0.8535(3) 0.0225(6) Uani 1 1 d . . . . .
C2 C 0.29143(13) 0.4378(3) 0.9213(3) 0.0251(6) Uani 1 1 d . . . . .
H2 H 0.277299 0.492481 0.988677 0.030 Uiso 1 1 calc R U . . .
C3 C 0.35490(13) 0.4387(3) 0.8904(3) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.382958 0.493505 0.938058 0.030 Uiso 1 1 calc R U . . .
C4 C 0.37779(12) 0.3587(2) 0.7887(3) 0.0224(6) Uani 1 1 d . . . . .
C5 C 0.33478(12) 0.2745(2) 0.7259(3) 0.0227(6) Uani 1 1 d . . . . .
H5 H 0.349338 0.217986 0.661458 0.027 Uiso 1 1 calc R U . . .
C6 C 0.27110(13) 0.2727(3) 0.7569(3) 0.0239(6) Uani 1 1 d . . . . .
H6 H 0.243503 0.215553 0.713180 0.029 Uiso 1 1 calc R U . . .
C7 C 0.44412(12) 0.3681(2) 0.7437(3) 0.0227(6) Uani 1 1 d . . . . .
C8 C 0.48106(12) 0.4680(3) 0.7723(3) 0.0257(7) Uani 1 1 d . . . . .
H8 H 0.465683 0.530607 0.825509 0.031 Uiso 1 1 calc R U . . .
C9 C 0.54019(13) 0.4719(3) 0.7203(3) 0.0263(7) Uani 1 1 d . . . . .
H9 H 0.564935 0.539108 0.736396 0.032 Uiso 1 1 calc R U . . .
C10 C 0.56463(14) 0.3792(3) 0.6445(3) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.67103(14) 0.4630(3) 0.6617(4) 0.0362(8) Uani 1 1 d . . . . .
H11A H 0.666077 0.475983 0.768885 0.043 Uiso 1 1 calc R U . . .
H11B H 0.661046 0.535234 0.606909 0.043 Uiso 1 1 calc R U . . .
C12 C 0.73840(14) 0.4273(3) 0.6430(3) 0.0361(8) Uani 1 1 d . . . . .
H12A H 0.767532 0.488048 0.683915 0.043 Uiso 1 1 calc R U . . .
H12B H 0.748379 0.356700 0.701584 0.043 Uiso 1 1 calc R U . . .
C13 C 0.70463(16) 0.3191(3) 0.4266(4) 0.0437(9) Uani 1 1 d . . . . .
H13A H 0.714412 0.245534 0.478416 0.052 Uiso 1 1 calc R U . . .
H13B H 0.710411 0.308447 0.319364 0.052 Uiso 1 1 calc R U . . .
C14 C 0.63524(14) 0.3514(3) 0.4423(3) 0.0330(7) Uani 1 1 d . . . . .
H14A H 0.623970 0.421539 0.383985 0.040 Uiso 1 1 calc R U . . .
H14B H 0.607048 0.288833 0.402580 0.040 Uiso 1 1 calc R U . . .
C15 C 0.15546(12) 0.4754(3) 0.9106(3) 0.0239(6) Uani 1 1 d . . . . .
C16 C 0.16712(12) 0.5724(3) 0.8229(3) 0.0254(7) Uani 1 1 d . . . . .
H16 H 0.191585 0.565030 0.740457 0.030 Uiso 1 1 calc R U . . .
C17 C 0.14246(13) 0.6799(3) 0.8579(3) 0.0286(7) Uani 1 1 d . . . . .
H17 H 0.151696 0.745174 0.801078 0.034 Uiso 1 1 calc R U . . .
C18 C 0.10422(14) 0.6913(3) 0.9766(3) 0.0314(7) Uani 1 1 d . . . . .
H18 H 0.087540 0.763784 0.999520 0.038 Uiso 1 1 calc R U . . .
C19 C 0.09089(14) 0.5940(3) 1.0613(3) 0.0325(7) Uani 1 1 d . . . . .
H19 H 0.064279 0.600773 1.139747 0.039 Uiso 1 1 calc R U . . .
C20 C 0.11687(14) 0.4869(3) 1.0298(3) 0.0288(7) Uani 1 1 d . . . . .
H20 H 0.108524 0.422161 1.088710 0.035 Uiso 1 1 calc R U . . .
C21 C 0.14071(12) 0.2646(2) 0.8738(3) 0.0216(6) Uani 1 1 d . . . . .
C22 C 0.16064(13) 0.1605(3) 0.9413(3) 0.0237(6) Uani 1 1 d . . . . .
H22 H 0.202728 0.152386 0.985496 0.028 Uiso 1 1 calc R U . . .
C23 C 0.11781(14) 0.0675(3) 0.9435(3) 0.0283(7) Uani 1 1 d . . . . .
H23 H 0.131552 -0.002823 0.988574 0.034 Uiso 1 1 calc R U . . .
C24 C 0.05519(14) 0.0787(3) 0.8795(3) 0.0307(7) Uani 1 1 d . . . . .
H24 H 0.026515 0.016820 0.882995 0.037 Uiso 1 1 calc R U . . .
C25 C 0.03534(13) 0.1820(3) 0.8104(3) 0.0333(8) Uani 1 1 d . . . . .
H25 H -0.006788 0.189661 0.766361 0.040 Uiso 1 1 calc R U . . .
C26 C 0.07804(13) 0.2752(3) 0.8060(3) 0.0269(7) Uani 1 1 d . . . . .
H26 H 0.064593 0.344477 0.757753 0.032 Uiso 1 1 calc R U . . .


_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
O1 N3 1.310(3) . ?
O2 C12 1.405(4) . ?
O2 C13 1.437(4) . ?
N1 C1 1.415(3) . ?
N1 C15 1.434(4) . ?
N1 C21 1.424(3) . ?
N2 N3 1.334(3) . ?
N2 C7 1.346(4) . ?
N3 C10 1.359(4) . ?
N4 C10 1.395(4) . ?
N4 C11 1.462(4) . ?
N4 C14 1.446(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.397(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.479(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.357(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.488(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.513(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.387(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(4) . ?
C21 C26 1.389(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(4) . ?
C26 H26 0.9300 . ?

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
C12 O2 C13 109.6(2) . . ?
C1 N1 C15 119.0(2) . . ?
C1 N1 C21 123.0(2) . . ?
C21 N1 C15 118.1(2) . . ?
N3 N2 C7 118.8(2) . . ?
O1 N3 N2 116.9(2) . . ?
O1 N3 C10 119.1(2) . . ?
N2 N3 C10 124.0(3) . . ?
C10 N4 C11 115.1(2) . . ?
C10 N4 C14 118.2(2) . . ?
C14 N4 C11 109.5(2) . . ?
C2 C1 N1 119.8(2) . . ?
C2 C1 C6 118.1(2) . . ?
C6 C1 N1 122.0(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 120.7(3) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
N2 C7 C4 117.3(2) . . ?
N2 C7 C8 120.7(2) . . ?
C8 C7 C4 121.9(2) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 H8 120.9 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.9(3) . . ?
C10 C9 H9 119.0 . . ?
N3 C10 N4 117.8(3) . . ?
N3 C10 C9 116.3(3) . . ?
C9 C10 N4 125.6(3) . . ?
N4 C11 H11A 109.8 . . ?
N4 C11 H11B 109.8 . . ?
N4 C11 C12 109.2(3) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
O2 C12 C11 112.6(3) . . ?
O2 C12 H12A 109.1 . . ?
O2 C12 H12B 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 H13A 109.2 . . ?
O2 C13 H13B 109.2 . . ?
O2 C13 C14 112.0(3) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
N4 C14 C13 109.2(2) . . ?
N4 C14 H14A 109.8 . . ?
N4 C14 H14B 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 N1 120.7(2) . . ?
C16 C15 C20 119.3(3) . . ?
C20 C15 N1 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C22 C21 N1 121.5(2) . . ?
C22 C21 C26 119.5(3) . . ?
C26 C21 N1 118.9(3) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.9(3) . . ?
C21 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?

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
O1 N3 C10 N4 -5.6(4) . . . . ?
O1 N3 C10 C9 -179.6(3) . . . . ?
O2 C13 C14 N4 -57.1(4) . . . . ?
N1 C1 C2 C3 -174.8(3) . . . . ?
N1 C1 C6 C5 174.5(2) . . . . ?
N1 C15 C16 C17 -178.5(2) . . . . ?
N1 C15 C20 C19 -179.6(3) . . . . ?
N1 C21 C22 C23 176.1(2) . . . . ?
N1 C21 C26 C25 -175.4(2) . . . . ?
N2 N3 C10 N4 175.6(2) . . . . ?
N2 N3 C10 C9 1.7(4) . . . . ?
N2 C7 C8 C9 0.5(4) . . . . ?
N3 N2 C7 C4 178.9(2) . . . . ?
N3 N2 C7 C8 1.6(4) . . . . ?
N4 C11 C12 O2 59.4(3) . . . . ?
C1 N1 C15 C16 47.5(4) . . . . ?
C1 N1 C15 C20 -133.4(3) . . . . ?
C1 N1 C21 C22 42.5(4) . . . . ?
C1 N1 C21 C26 -140.4(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C2 C3 C4 C5 -3.2(4) . . . . ?
C2 C3 C4 C7 173.5(2) . . . . ?
C3 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C7 N2 168.5(3) . . . . ?
C3 C4 C7 C8 -14.2(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C7 C8 C9 -176.6(3) . . . . ?
C5 C4 C7 N2 -14.9(4) . . . . ?
C5 C4 C7 C8 162.3(3) . . . . ?
C6 C1 C2 C3 2.2(4) . . . . ?
C7 N2 N3 O1 178.5(2) . . . . ?
C7 N2 N3 C10 -2.8(4) . . . . ?
C7 C4 C5 C6 -173.7(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 N3 0.6(4) . . . . ?
C8 C9 C10 N4 -172.8(3) . . . . ?
C10 N4 C11 C12 165.1(2) . . . . ?
C10 N4 C14 C13 -167.7(3) . . . . ?
C11 N4 C10 N3 -165.1(3) . . . . ?
C11 N4 C10 C9 8.2(4) . . . . ?
C11 N4 C14 C13 57.9(3) . . . . ?
C12 O2 C13 C14 55.9(4) . . . . ?
C13 O2 C12 C11 -57.3(4) . . . . ?
C14 N4 C10 N3 63.0(4) . . . . ?
C14 N4 C10 C9 -123.6(3) . . . . ?
C14 N4 C11 C12 -59.0(3) . . . . ?
C15 N1 C1 C2 27.2(4) . . . . ?
C15 N1 C1 C6 -149.6(3) . . . . ?
C15 N1 C21 C22 -136.4(3) . . . . ?
C15 N1 C21 C26 40.7(3) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C15 C20 C19 -0.5(4) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 1.6(5) . . . . ?
C18 C19 C20 C15 -1.5(5) . . . . ?
C20 C15 C16 C17 2.4(4) . . . . ?
C21 N1 C1 C2 -151.6(3) . . . . ?
C21 N1 C1 C6 31.5(4) . . . . ?
C21 N1 C15 C16 -133.6(3) . . . . ?
C21 N1 C15 C20 45.6(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C21 C26 C25 1.8(4) . . . . ?
C22 C23 C24 C25 1.3(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C26 C21 C22 C23 -1.0(4) . . . . ?

_olex2_date_sample_data_collection 2020-06-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02-0816
_database_code_depnum_ccdc_archive 'CCDC 2210455'
loop_
_audit_author_name
_audit_author_address
'Gong Jianye'
;Inner Mongolia University
China
;
_audit_update_record             
;
2022-09-30 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N4 O'
_chemical_formula_sum            'C26 H24 N4 O'
_chemical_formula_weight         408.49
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.2739(12)
_cell_length_b                   11.0135(8)
_cell_length_c                   8.6873(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.211(5)
_cell_angle_gamma                90
_cell_volume                     2027.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4117
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9110
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.084
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00   4.00   1.00    5.00    --  -11.27  93.00 162.00   54
  2  ω     15.00  82.00   1.00    5.00    --   11.90  37.00 -30.00   67
  3  ω     -9.00  65.00   1.00    5.00    --   11.90  37.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0090985000
_diffrn_orient_matrix_UB_12      0.0552750000
_diffrn_orient_matrix_UB_13      -0.0334925000
_diffrn_orient_matrix_UB_21      -0.0296823000
_diffrn_orient_matrix_UB_22      0.0257156000
_diffrn_orient_matrix_UB_23      0.0124805000
_diffrn_orient_matrix_UB_31      0.0124899000
_diffrn_orient_matrix_UB_32      0.0208049000
_diffrn_orient_matrix_UB_33      0.0738063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3048
_reflns_number_total             3580
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.050
_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)+(0.0475P)²+0.5763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
;
_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
O1 O 0.73255(5) 0.57530(11) -0.00479(12) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.17763(6) 0.62573(12) 0.36735(14) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.47199(6) 0.55926(13) 0.27149(14) 0.0207(3) Uani 1 1 d . . . . .
N3 N 0.53212(6) 0.55558(12) 0.23193(14) 0.0205(3) Uani 1 1 d . . . . .
N4 N 0.61689(5) 0.63841(12) 0.11679(13) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.15177(7) 0.51065(14) 0.40088(16) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.10993(7) 0.50137(15) 0.51471(17) 0.0206(4) Uani 1 1 d . . . . .
H2 H 0.099111 0.570156 0.568514 0.025 Uiso 1 1 calc R U . . .
C3 C 0.08453(7) 0.39005(15) 0.54759(17) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.055616 0.384775 0.621428 0.027 Uiso 1 1 calc R U . . .
C4 C 0.10153(7) 0.28660(15) 0.47227(17) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.084907 0.211622 0.496507 0.027 Uiso 1 1 calc R U . . .
C5 C 0.14374(7) 0.29545(15) 0.35977(17) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.155907 0.225830 0.309665 0.025 Uiso 1 1 calc R U . . .
C6 C 0.16780(7) 0.40710(15) 0.32179(16) 0.0188(4) Uani 1 1 d . . . . .
H6 H 0.194668 0.412862 0.243422 0.023 Uiso 1 1 calc R U . . .
C7 C 0.13808(7) 0.73006(14) 0.36579(16) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.15989(7) 0.83842(14) 0.43253(16) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.201544 0.844356 0.474722 0.022 Uiso 1 1 calc R U . . .
C9 C 0.12011(7) 0.93795(15) 0.43687(16) 0.0203(4) Uani 1 1 d . . . . .
H9 H 0.135275 1.010476 0.480716 0.024 Uiso 1 1 calc R U . . .
C10 C 0.05771(7) 0.92931(16) 0.37584(17) 0.0220(4) Uani 1 1 d . . . . .
H10 H 0.030647 0.995194 0.381120 0.026 Uiso 1 1 calc R U . . .
C11 C 0.03602(7) 0.82234(16) 0.30720(17) 0.0222(4) Uani 1 1 d . . . . .
H11 H -0.005714 0.816553 0.265579 0.027 Uiso 1 1 calc R U . . .
C12 C 0.07587(7) 0.72382(15) 0.29989(17) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.061131 0.652966 0.250779 0.024 Uiso 1 1 calc R U . . .
C13 C 0.24192(7) 0.63504(14) 0.33916(16) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.26203(7) 0.72343(14) 0.24026(16) 0.0171(3) Uani 1 1 d . . . . .
H14 H 0.233164 0.779355 0.195379 0.020 Uiso 1 1 calc R U . . .
C15 C 0.32433(7) 0.72913(14) 0.20793(16) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.336449 0.788170 0.140030 0.020 Uiso 1 1 calc R U . . .
C16 C 0.36952(7) 0.64861(14) 0.27448(16) 0.0162(3) Uani 1 1 d . . . . .
C17 C 0.34933(7) 0.56121(14) 0.37541(16) 0.0178(3) Uani 1 1 d . . . . .
H17 H 0.378375 0.506229 0.421676 0.021 Uiso 1 1 calc R U . . .
C18 C 0.28704(7) 0.55478(14) 0.40791(16) 0.0175(3) Uani 1 1 d . . . . .
H18 H 0.274945 0.496235 0.476504 0.021 Uiso 1 1 calc R U . . .
C19 C 0.43560(7) 0.65505(14) 0.23439(16) 0.0164(3) Uani 1 1 d . . . . .
C20 C 0.45944(7) 0.75679(15) 0.16046(17) 0.0205(4) Uani 1 1 d . . . . .
H20 H 0.434730 0.825778 0.141539 0.025 Uiso 1 1 calc R U . . .
C21 C 0.51906(7) 0.75224(15) 0.11741(17) 0.0208(4) Uani 1 1 d . . . . .
H21 H 0.535900 0.816852 0.065793 0.025 Uiso 1 1 calc R U . . .
C22 C 0.55451(7) 0.64719(14) 0.15313(16) 0.0169(3) Uani 1 1 d . . . . .
C23 C 0.62970(7) 0.67360(16) -0.04063(17) 0.0219(4) Uani 1 1 d . . . . .
H23A H 0.609593 0.750822 -0.067006 0.026 Uiso 1 1 calc R U . . .
H23B H 0.612191 0.613248 -0.113740 0.026 Uiso 1 1 calc R U . . .
C24 C 0.69981(7) 0.68411(16) -0.05124(18) 0.0254(4) Uani 1 1 d . . . . .
H24A H 0.707537 0.703030 -0.156927 0.030 Uiso 1 1 calc R U . . .
H24B H 0.716222 0.750522 0.013862 0.030 Uiso 1 1 calc R U . . .
C25 C 0.72050(7) 0.54639(16) 0.14960(17) 0.0230(4) Uani 1 1 d . . . . .
H25A H 0.736022 0.611633 0.217806 0.028 Uiso 1 1 calc R U . . .
H25B H 0.743302 0.473051 0.181736 0.028 Uiso 1 1 calc R U . . .
C26 C 0.65112(7) 0.52772(15) 0.16476(18) 0.0214(4) Uani 1 1 d . . . . .
H26A H 0.635559 0.460247 0.100395 0.026 Uiso 1 1 calc R U . . .
H26B H 0.644540 0.508816 0.271166 0.026 Uiso 1 1 calc R U . . .


_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
O1 C24 1.426(2) . ?
O1 C25 1.4242(18) . ?
N1 C1 1.422(2) . ?
N1 C7 1.423(2) . ?
N1 C13 1.4148(18) . ?
N2 N3 1.3551(16) . ?
N2 C19 1.331(2) . ?
N3 C22 1.331(2) . ?
N4 C22 1.3951(18) . ?
N4 C23 1.4705(18) . ?
N4 C26 1.461(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(2) . ?
C7 C12 1.395(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(2) . ?
C16 C17 1.396(2) . ?
C16 C19 1.480(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.409(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.356(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.400(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.507(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.508(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C25 O1 C24 109.24(11) . . ?
C1 N1 C7 118.81(12) . . ?
C13 N1 C1 119.87(13) . . ?
C13 N1 C7 121.30(13) . . ?
C19 N2 N3 120.27(13) . . ?
C22 N3 N2 119.85(13) . . ?
C22 N4 C23 116.91(11) . . ?
C22 N4 C26 116.93(12) . . ?
C26 N4 C23 110.82(12) . . ?
C2 C1 N1 119.66(14) . . ?
C6 C1 N1 120.87(13) . . ?
C6 C1 C2 119.47(15) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.97(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.76(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.35(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.46(15) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.92(14) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 N1 121.01(13) . . ?
C8 C7 C12 118.84(14) . . ?
C12 C7 N1 120.13(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.60(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.02(15) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.62(15) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.50(14) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.36(15) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 N1 120.93(13) . . ?
C14 C13 C18 117.93(13) . . ?
C18 C13 N1 121.14(14) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.80(14) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.68(14) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 117.33(13) . . ?
C15 C16 C19 120.38(13) . . ?
C17 C16 C19 122.26(14) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.29(14) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.95(14) . . ?
C17 C18 H18 119.5 . . ?
N2 C19 C16 116.68(14) . . ?
N2 C19 C20 121.02(13) . . ?
C20 C19 C16 122.30(14) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.76(15) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 121.1 . . ?
C20 C21 C22 117.90(15) . . ?
C22 C21 H21 121.1 . . ?
N3 C22 N4 117.12(13) . . ?
N3 C22 C21 121.98(13) . . ?
N4 C22 C21 120.74(14) . . ?
N4 C23 H23A 109.6 . . ?
N4 C23 H23B 109.6 . . ?
N4 C23 C24 110.19(12) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
O1 C24 C23 112.26(14) . . ?
O1 C24 H24A 109.2 . . ?
O1 C24 H24B 109.2 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
O1 C25 H25A 109.2 . . ?
O1 C25 H25B 109.2 . . ?
O1 C25 C26 111.96(12) . . ?
H25A C25 H25B 107.9 . . ?
C26 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
N4 C26 C25 109.14(13) . . ?
N4 C26 H26A 109.9 . . ?
N4 C26 H26B 109.9 . . ?
C25 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?

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
O1 C25 C26 N4 -59.08(17) . . . . ?
N1 C1 C2 C3 179.84(13) . . . . ?
N1 C1 C6 C5 177.85(13) . . . . ?
N1 C7 C8 C9 -176.96(13) . . . . ?
N1 C7 C12 C11 175.66(13) . . . . ?
N1 C13 C14 C15 -177.28(13) . . . . ?
N1 C13 C18 C17 177.47(13) . . . . ?
N2 N3 C22 N4 179.57(12) . . . . ?
N2 N3 C22 C21 4.2(2) . . . . ?
N2 C19 C20 C21 4.7(2) . . . . ?
N3 N2 C19 C16 176.76(12) . . . . ?
N3 N2 C19 C20 -3.2(2) . . . . ?
N4 C23 C24 O1 55.78(18) . . . . ?
C1 N1 C7 C8 137.43(14) . . . . ?
C1 N1 C7 C12 -40.99(19) . . . . ?
C1 N1 C13 C14 149.41(14) . . . . ?
C1 N1 C13 C18 -29.7(2) . . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C1 2.7(2) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 N1 C1 C2 -39.48(19) . . . . ?
C7 N1 C1 C6 140.67(14) . . . . ?
C7 N1 C13 C14 -31.8(2) . . . . ?
C7 N1 C13 C18 149.15(14) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C7 C12 C11 -2.8(2) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C7 1.9(2) . . . . ?
C12 C7 C8 C9 1.5(2) . . . . ?
C13 N1 C1 C2 139.36(14) . . . . ?
C13 N1 C1 C6 -40.49(19) . . . . ?
C13 N1 C7 C8 -41.39(19) . . . . ?
C13 N1 C7 C12 140.19(14) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C13 C18 C17 -1.6(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C14 C15 C16 C19 178.43(13) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C15 C16 C19 N2 -164.18(13) . . . . ?
C15 C16 C19 C20 15.7(2) . . . . ?
C16 C17 C18 C13 0.7(2) . . . . ?
C16 C19 C20 C21 -175.24(14) . . . . ?
C17 C16 C19 N2 14.0(2) . . . . ?
C17 C16 C19 C20 -166.08(14) . . . . ?
C18 C13 C14 C15 1.8(2) . . . . ?
C19 N2 N3 C22 -1.2(2) . . . . ?
C19 C16 C17 C18 -178.20(13) . . . . ?
C19 C20 C21 C22 -1.8(2) . . . . ?
C20 C21 C22 N3 -2.5(2) . . . . ?
C20 C21 C22 N4 -177.79(13) . . . . ?
C22 N4 C23 C24 168.23(14) . . . . ?
C22 N4 C26 C25 -167.00(12) . . . . ?
C23 N4 C22 N3 136.61(14) . . . . ?
C23 N4 C22 C21 -47.9(2) . . . . ?
C23 N4 C26 C25 55.57(16) . . . . ?
C24 O1 C25 C26 59.77(17) . . . . ?
C25 O1 C24 C23 -57.99(17) . . . . ?
C26 N4 C22 N3 1.77(19) . . . . ?
C26 N4 C22 C21 177.25(13) . . . . ?
C26 N4 C23 C24 -54.33(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.599
