# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_041559_hl683_100k_a
_database_code_depnum_ccdc_archive 'CCDC 2337615'
loop_
_audit_author_name
_audit_author_address
'Lin Huang'
;Tianjin University
China
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2024-03-21 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 N4 O4'
_chemical_formula_sum            'C26 H16 N4 O4'
_chemical_formula_weight         448.43
_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'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6003(3)
_cell_length_b                   7.7459(2)
_cell_length_c                   22.1452(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.835(2)
_cell_angle_gamma                90
_cell_volume                     1989.63(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3524
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.2240
_cell_measurement_theta_min      3.9920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10166
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.607
_diffrn_reflns_theta_min         3.993
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -42.00   0.50    0.05    --  -36.74 110.00-111.00   58
  2  ω      8.00  73.00   0.50    0.05    --   36.74-110.00 153.00  130
  3  ω   -156.00-131.00   0.50    0.20    -- -100.00-110.00 153.00   50
  4  ω    -88.00 -24.00   0.50    0.20    -- -100.00 110.00-111.00  128
  5  ω    105.00 130.00   0.50    0.20    --  109.62 110.00-111.00   50
  6  ω     30.00 102.00   0.50    0.20    --  109.62-110.00 153.00  144
  7  ω     54.00  79.00   0.50    0.05    --   36.74  57.00-120.00   50
  8  ω      8.00 103.00   0.50    0.05    --   36.74  57.00 -90.00  190
  9  ω    -26.00   0.00   0.50    0.05    --   36.74 -77.00  90.00   52
 10  ω      8.00 112.00   0.50    0.05    --   36.74  57.00  90.00  208
 11  ω     20.00  48.00   0.50    0.05    --   36.74  57.00-120.00   56
 12  ω   -154.00-113.00   0.50    0.20    -- -100.00 179.00 -90.00   82
 13  ω   -154.00 -93.00   0.50    0.20    -- -100.00 -61.00 150.00  122
 14  ω    -89.00 -37.00   0.50    0.20    -- -100.00 111.00 -30.00  104
 15  ω   -176.00 -62.00   0.50    0.20    -- -100.00 -77.00-180.00  228
 16  ω   -176.00 -88.00   0.50    0.20    -- -100.00 -94.00 -90.00  176
 17  ω    -72.00 -47.00   0.50    0.20    -- -100.00 179.00 -90.00   50
 18  ω    142.00 168.00   0.50    0.20    --  109.62  61.00-120.00   52
 19  ω     82.00 168.00   0.50    0.20    --  109.62 111.00   0.00  172
 20  ω    111.00 137.00   0.50    0.20    --  109.62  61.00-120.00   52
 21  ω     83.00 109.00   0.50    0.20    --  109.62 -94.00-180.00   52
 22  ω     52.00  77.00   0.50    0.20    --  109.62 -94.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027517000
_diffrn_orient_matrix_UB_12      -0.1815680000
_diffrn_orient_matrix_UB_13      0.0283799000
_diffrn_orient_matrix_UB_21      -0.0724402000
_diffrn_orient_matrix_UB_22      -0.0700202000
_diffrn_orient_matrix_UB_23      -0.0534451000
_diffrn_orient_matrix_UB_31      0.1113108000
_diffrn_orient_matrix_UB_32      -0.0411329000
_diffrn_orient_matrix_UB_33      -0.0343042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2947
_reflns_number_total             3742
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.045
_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)+(0.0690P)²+0.2585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C21(H21), C20(H20)
1.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C25(H25A,H25B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C13(H13), C24(H24), C12(H12), C23(H23), C19(H19), C10(H10),
 C16(H16), C17(H17)
;
_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
O3 O -0.16025(14) 0.1382(2) 0.52555(7) 0.0290(4) Uani 1 1 d . . . . .
O1 O 0.85495(12) 0.2707(2) 0.15133(8) 0.0314(4) Uani 1 1 d . . . . .
O4 O -0.24398(12) 0.2962(2) 0.45676(8) 0.0300(4) Uani 1 1 d . . . . .
O2 O 0.74265(13) 0.4167(2) 0.09118(7) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.27648(14) 0.4728(2) 0.40346(8) 0.0186(4) Uani 1 1 d . . . . .
N1 N 0.46661(13) 0.4939(2) 0.33266(8) 0.0173(4) Uani 1 1 d . . . . .
N4 N -0.15627(15) 0.2406(2) 0.48294(8) 0.0231(4) Uani 1 1 d . . . . .
N3 N 0.76729(14) 0.3583(2) 0.14176(8) 0.0215(4) Uani 1 1 d . . . . .
C7 C 0.18182(16) 0.6235(2) 0.32238(9) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.51575(16) 0.5205(2) 0.22601(9) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.39952(16) 0.5900(2) 0.21427(9) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.22074(16) 0.6448(2) 0.26350(9) 0.0162(4) Uani 1 1 d . . . . .
C22 C 0.54242(16) 0.4644(2) 0.28652(9) 0.0163(4) Uani 1 1 d . . . . .
C5 C 0.34177(16) 0.6433(2) 0.26386(9) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.59080(16) 0.4854(2) 0.17996(9) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.573554 0.522774 0.140951 0.021 Uiso 1 1 calc R . . . .
C9 C 0.00122(16) 0.5308(3) 0.28206(10) 0.0192(4) Uani 1 1 d . . . . .
H9 H -0.074573 0.496912 0.288352 0.023 Uiso 1 1 calc R . . . .
C1 C 0.69193(16) 0.3947(3) 0.19135(9) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.15392(16) 0.6059(2) 0.21227(9) 0.0169(4) Uani 1 1 d . . . . .
C8 C 0.07744(17) 0.5494(2) 0.33294(9) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.17016(17) 0.4189(2) 0.42425(9) 0.0178(4) Uani 1 1 d . . . . .
C13 C 0.33495(17) 0.5697(2) 0.15927(9) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.373663 0.547588 0.123614 0.021 Uiso 1 1 calc R . . . .
C14 C 0.06611(17) 0.4629(2) 0.39143(9) 0.0184(4) Uani 1 1 d . . . . .
C24 C 0.71920(16) 0.3357(3) 0.24937(10) 0.0195(4) Uani 1 1 d . . . . .
H24 H 0.786281 0.272606 0.256327 0.023 Uiso 1 1 calc R . . . .
C21 C 0.38958(16) 0.6428(2) 0.32723(9) 0.0172(4) Uani 1 1 d . . . . .
H21 H 0.431498 0.750097 0.335710 0.021 Uiso 1 1 calc R . . . .
C12 C 0.21592(17) 0.5822(2) 0.15805(9) 0.0183(4) Uani 1 1 d . . . . .
H12 H 0.176136 0.574994 0.121374 0.022 Uiso 1 1 calc R . . . .
C18 C -0.04436(17) 0.2982(3) 0.46256(9) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.27942(16) 0.6297(2) 0.36727(9) 0.0173(4) Uani 1 1 d . . . . .
H20 H 0.272836 0.731816 0.393125 0.021 Uiso 1 1 calc R . . . .
C23 C 0.64612(16) 0.3716(3) 0.29637(9) 0.0185(4) Uani 1 1 d . . . . .
H23 H 0.665321 0.334236 0.335141 0.022 Uiso 1 1 calc R . . . .
C19 C -0.03911(17) 0.4031(3) 0.41187(9) 0.0200(4) Uani 1 1 d . . . . .
H19 H -0.106692 0.433570 0.391435 0.024 Uiso 1 1 calc R . . . .
C10 C 0.03665(16) 0.5614(2) 0.22420(10) 0.0184(4) Uani 1 1 d . . . . .
H10 H -0.016177 0.553263 0.192336 0.022 Uiso 1 1 calc R . . . .
C16 C 0.16085(17) 0.3118(3) 0.47556(9) 0.0202(4) Uani 1 1 d . . . . .
H16 H 0.227055 0.281021 0.497160 0.024 Uiso 1 1 calc R . . . .
C17 C 0.05446(18) 0.2520(3) 0.49424(9) 0.0221(4) Uani 1 1 d . . . . .
H17 H 0.049629 0.180918 0.527964 0.026 Uiso 1 1 calc R . . . .
C26 C 0.38577(17) 0.4485(3) 0.43559(10) 0.0251(5) Uani 1 1 d . . . . .
H26A H 0.379719 0.349395 0.462136 0.030 Uiso 1 1 calc R . . . .
H26B H 0.401437 0.549149 0.460451 0.030 Uiso 1 1 calc R . . . .
C25 C 0.48650(17) 0.4206(3) 0.39250(9) 0.0231(4) Uani 1 1 d . . . . .
H25A H 0.555435 0.472094 0.410072 0.028 Uiso 1 1 calc R . . . .
H25B H 0.500291 0.297673 0.388476 0.028 Uiso 1 1 calc R . . . .


_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
O3 N4 1.234(2) . ?
O1 N3 1.238(2) . ?
O4 N4 1.241(2) . ?
O2 N3 1.237(3) . ?
N2 C15 1.387(3) . ?
N2 C20 1.457(3) . ?
N2 C26 1.457(3) . ?
N1 C22 1.377(3) . ?
N1 C21 1.462(3) . ?
N1 C25 1.457(3) . ?
N4 C18 1.451(3) . ?
N3 C1 1.441(3) . ?
C7 C6 1.396(3) . ?
C7 C8 1.363(3) . ?
C7 C20 1.496(3) . ?
C3 C4 1.471(3) . ?
C3 C22 1.438(3) . ?
C3 C2 1.378(3) . ?
C4 C5 1.359(3) . ?
C4 C13 1.429(3) . ?
C6 C5 1.404(3) . ?
C6 C11 1.398(3) . ?
C22 C23 1.416(3) . ?
C5 C21 1.501(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.429(3) . ?
C9 C10 1.372(3) . ?
C1 C24 1.396(3) . ?
C11 C12 1.420(3) . ?
C11 C10 1.432(3) . ?
C8 C14 1.466(3) . ?
C15 C14 1.441(3) . ?
C15 C16 1.412(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.384(3) . ?
C14 C19 1.388(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.380(3) . ?
C21 H21 0.9800 . ?
C21 C20 1.569(3) . ?
C12 H12 0.9300 . ?
C18 C19 1.388(3) . ?
C18 C17 1.382(3) . ?
C20 H20 0.9800 . ?
C23 H23 0.9300 . ?
C19 H19 0.9300 . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C25 1.535(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 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
C15 N2 C20 117.50(16) . . ?
C15 N2 C26 124.80(17) . . ?
C20 N2 C26 110.44(16) . . ?
C22 N1 C21 117.77(16) . . ?
C22 N1 C25 121.05(16) . . ?
C25 N1 C21 118.07(16) . . ?
O3 N4 O4 122.74(17) . . ?
O3 N4 C18 118.63(18) . . ?
O4 N4 C18 118.63(17) . . ?
O1 N3 C1 118.85(18) . . ?
O2 N3 O1 122.23(18) . . ?
O2 N3 C1 118.92(16) . . ?
C6 C7 C20 111.40(17) . . ?
C8 C7 C6 120.67(18) . . ?
C8 C7 C20 124.38(18) . . ?
C22 C3 C4 117.34(18) . . ?
C2 C3 C4 121.93(18) . . ?
C2 C3 C22 120.02(17) . . ?
C5 C4 C3 115.45(18) . . ?
C5 C4 C13 117.63(17) . . ?
C13 C4 C3 125.29(18) . . ?
C7 C6 C5 109.31(17) . . ?
C7 C6 C11 123.35(18) . . ?
C11 C6 C5 123.07(18) . . ?
N1 C22 C3 120.68(17) . . ?
N1 C22 C23 121.36(18) . . ?
C23 C22 C3 117.90(18) . . ?
C4 C5 C6 120.17(18) . . ?
C4 C5 C21 125.07(17) . . ?
C6 C5 C21 111.17(17) . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.48(19) . . ?
C1 C2 H2 119.8 . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C10 C9 C8 121.90(18) . . ?
C2 C1 N3 118.75(18) . . ?
C2 C1 C24 120.86(19) . . ?
C24 C1 N3 120.37(17) . . ?
C6 C11 C12 115.62(17) . . ?
C6 C11 C10 114.79(18) . . ?
C12 C11 C10 128.25(19) . . ?
C7 C8 C9 116.61(19) . . ?
C7 C8 C14 115.82(18) . . ?
C9 C8 C14 126.02(18) . . ?
N2 C15 C14 120.26(18) . . ?
N2 C15 C16 121.51(18) . . ?
C16 C15 C14 118.13(18) . . ?
C4 C13 H13 119.4 . . ?
C12 C13 C4 121.28(19) . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C8 117.94(17) . . ?
C19 C14 C8 122.11(18) . . ?
C19 C14 C15 119.41(19) . . ?
C1 C24 H24 120.2 . . ?
C23 C24 C1 119.66(18) . . ?
C23 C24 H24 120.2 . . ?
N1 C21 C5 107.24(16) . . ?
N1 C21 H21 110.6 . . ?
N1 C21 C20 113.85(15) . . ?
C5 C21 H21 110.6 . . ?
C5 C21 C20 103.62(15) . . ?
C20 C21 H21 110.6 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.65(18) . . ?
C13 C12 H12 119.7 . . ?
C19 C18 N4 118.79(19) . . ?
C17 C18 N4 120.10(19) . . ?
C17 C18 C19 121.09(19) . . ?
N2 C20 C7 108.37(16) . . ?
N2 C20 C21 112.98(16) . . ?
N2 C20 H20 110.4 . . ?
C7 C20 C21 103.95(16) . . ?
C7 C20 H20 110.4 . . ?
C21 C20 H20 110.4 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.05(19) . . ?
C24 C23 H23 119.5 . . ?
C14 C19 C18 120.56(19) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C9 C10 C11 120.82(18) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N2 C26 H26A 109.1 . . ?
N2 C26 H26B 109.1 . . ?
N2 C26 C25 112.30(17) . . ?
H26A C26 H26B 107.9 . . ?
C25 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
N1 C25 C26 113.51(16) . . ?
N1 C25 H25A 108.9 . . ?
N1 C25 H25B 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.000 76.1 22.5 ?
2 0.500 0.000 0.500 76.1 22.5 ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.893
_oxdiff_exptl_absorpt_empirical_full_min 0.578
####################################################################### 
# 
# 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_041890_100k_a
_database_code_depnum_ccdc_archive 'CCDC 2337616'
loop_
_audit_author_name
_audit_author_address
'Lin Huang'
;Tianjin University
China
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2024-03-21 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 N4 O4'
_chemical_formula_sum            'C26 H18 N4 O4'
_chemical_formula_weight         450.44
_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'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.30850(10)
_cell_length_b                   9.13480(10)
_cell_length_c                   21.6558(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.3680(10)
_cell_angle_gamma                90
_cell_volume                     2026.66(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.0940
_cell_measurement_theta_min      4.0990
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24851
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.691
_diffrn_reflns_theta_min         4.108
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00   0.00   0.50    0.05    --   36.99   7.00 -89.00   86
  2  ω     12.00  37.00   0.50    0.05    --   36.99  -7.00  94.00   50
  3  ω     37.00 118.00   0.50    0.05    --   36.99   7.00 -89.00  162
  4  ω   -114.00 -89.00   0.50    0.05    -- -100.00  -7.00  94.00   50
  5  ω     23.00  49.00   0.50    0.05    --  109.62   7.00 -89.00   52
  6  ω     71.00 133.00   0.50    0.05    --  109.62   7.00 -89.00  124
  7  ω   -103.00  -7.00   0.50    0.05    --  -36.99 -57.00 -30.00  192
  8  ω    -83.00 -49.00   0.50    0.05    --  -36.99-179.00-120.00   68
  9  ω   -125.00 -46.00   0.50    0.05    --  -36.99-179.00-150.00  158
 10  ω    -25.00   0.00   0.50    0.05    --  -36.99 -77.00-180.00   50
 11  ω   -125.00 -50.00   0.50    0.05    --  -36.99 179.00 150.00  150
 12  ω    -46.00 -20.00   0.50    0.05    --  -36.99 -77.00 120.00   52
 13  ω    -51.00 -25.00   0.50    0.05    --  -36.99 -77.00  90.00   52
 14  ω   -116.00   0.00   0.50    0.05    --  -36.99 -77.00 -30.00  232
 15  ω    -88.00   2.00   0.50    0.05    --  -36.99 -37.00 -30.00  180
 16  ω      3.00  30.00   0.50    0.05    --   36.99  77.00 -30.00   54
 17  ω      1.00  27.00   0.50    0.05    --   36.99  93.00  84.78   52
 18  ω    -84.00 -59.00   0.50    0.05    -- -100.00 -83.00 -41.58   50
 19  ω    -92.00 -65.00   0.50    0.05    -- -100.00 -68.00 -79.50   54
 20  ω    -93.00 -68.00   0.50    0.05    -- -100.00 -61.00  60.00   50
 21  ω   -164.00-138.00   0.50    0.05    -- -100.00 -83.00 -41.58   52
 22  ω    -88.00 -63.00   0.50    0.05    -- -100.00 -74.00  63.56   50
 23  ω   -163.00-138.00   0.50    0.05    -- -100.00 -68.00 -79.50   50
 24  ω   -138.00 -21.00   0.50    0.05    -- -100.00  77.00 120.00  234
 25  ω   -175.00 -70.00   0.50    0.05    -- -100.00 -63.00 -67.45  210
 26  ω   -177.00 -63.00   0.50    0.05    -- -100.00 -73.00  39.06  228
 27  ω    -85.00 -60.00   0.50    0.05    -- -100.00 -81.00  -4.17   50
 28  ω    -99.00 -59.00   0.50    0.05    -- -100.00 -82.00  56.08   80
 29  ω   -172.00-142.00   0.50    0.05    -- -100.00 -71.00  20.00   60
 30  ω    -90.00 -64.00   0.50    0.05    -- -100.00 -73.00 -42.32   52
 31  ω   -177.00-152.00   0.50    0.05    -- -100.00 -77.00 -60.00   50
 32  ω    -87.00 -62.00   0.50    0.05    -- -100.00 -77.00 -60.00   50
 33  ω    -87.00 -62.00   0.50    0.05    -- -100.00 -77.00  30.00   50
 34  ω    -86.00 -60.00   0.50    0.05    -- -100.00 -81.00  -6.68   52
 35  ω    -87.00 -62.00   0.50    0.05    -- -100.00 -80.00  42.43   50
 36  ω    -92.00 -66.00   0.50    0.05    -- -100.00 -66.00  59.99   52
 37  ω    -89.00 -64.00   0.50    0.05    -- -100.00 -48.00  54.54   50
 38  ω    -87.00 -62.00   0.50    0.05    -- -100.00 -78.00   0.44   50
 39  ω    -85.00 -59.00   0.50    0.05    -- -100.00 -82.00 -25.82   52
 40  ω    -89.00 -64.00   0.50    0.05    -- -100.00 -77.00  90.00   50
 41  ω    -85.00 -60.00   0.50    0.05    -- -100.00 -81.00 -16.93   50
 42  ω    -86.00 -61.00   0.50    0.05    -- -100.00 -81.00  28.18   50
 43  ω   -169.00 -67.00   0.50    0.05    -- -100.00 -62.00  -9.13  204
 44  ω    -90.00 -65.00   0.50    0.05    -- -100.00 -68.00  -7.33   50
 45  ω    -89.00 -63.00   0.50    0.05    -- -100.00 -77.00  60.00   52
 46  ω    -86.00 -61.00   0.50    0.05    -- -100.00 -79.00  17.08   50
 47  ω   -175.00-149.00   0.50    0.05    -- -100.00 -79.00  17.08   52
 48  ω   -174.00-149.00   0.50    0.05    -- -100.00 -81.00 -16.93   50
 49  ω   -118.00 -93.00   0.50    0.05    -- -100.00   7.00 -89.00   50
 50  ω    -91.00 -66.00   0.50    0.05    -- -100.00 -68.00 -54.56   50
 51  ω   -173.00 -65.00   0.50    0.05    -- -100.00 -44.00  34.66  216
 52  ω   -148.00 -65.00   0.50    0.05    -- -100.00 -45.00 -61.99  166
 53  ω    -89.00 -64.00   0.50    0.05    -- -100.00 -72.00 -84.48   50
 54  ω   -135.00 -64.00   0.50    0.05    -- -100.00 -71.00  20.00  142
 55  ω     27.00 110.00   0.50    0.05    --  109.62-111.00  90.00  166
 56  ω     45.00  85.00   0.50    0.05    --  109.62 -94.00   0.00   80
 57  ω     37.00  65.00   0.50    0.05    --  109.62 -94.00-150.00   56
 58  ω     77.00 103.00   0.50    0.05    --  109.62 -94.00 -60.00   52
 59  ω     99.00 124.00   0.50    0.05    --  109.62  -7.00  94.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0197303000
_diffrn_orient_matrix_UB_12      -0.0162616000
_diffrn_orient_matrix_UB_13      -0.0712224000
_diffrn_orient_matrix_UB_21      0.1490717000
_diffrn_orient_matrix_UB_22      -0.0010018000
_diffrn_orient_matrix_UB_23      -0.0014784000
_diffrn_orient_matrix_UB_31      0.0010482000
_diffrn_orient_matrix_UB_32      -0.1678750000
_diffrn_orient_matrix_UB_33      0.0068990000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3507
_reflns_number_total             3817
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.042
_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)+(0.0596P)²+0.7378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1041
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B)
1.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C5(H5), C22(H22), C26(H26), C3(H3A), C12(H12), C18(H18),
 C25(H25), C13(H13), C16(H16), C14(H14), C23(H23), C17(H17)
;
_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 -0.18956(10) 0.00399(10) 0.39468(4) 0.0272(2) Uani 1 1 d . . . . .
O2 O -0.30816(10) -0.06972(11) 0.46489(5) 0.0288(2) Uani 1 1 d . . . . .
O3 O 0.78468(9) 0.40763(11) 0.83554(4) 0.0294(2) Uani 1 1 d . . . . .
O4 O 0.84483(10) 0.26814(14) 0.76321(5) 0.0390(3) Uani 1 1 d . . . . .
N2 N 0.06934(10) 0.37895(11) 0.61205(5) 0.0185(2) Uani 1 1 d . . . . .
N1 N -0.22008(10) 0.00590(12) 0.44849(5) 0.0215(2) Uani 1 1 d . . . . .
N3 N 0.23980(11) 0.21745(12) 0.70071(5) 0.0226(2) Uani 1 1 d . . . . .
H3 H 0.229681 0.151481 0.672255 0.027 Uiso 1 1 calc R . . . .
N4 N 0.75914(11) 0.32636(13) 0.79031(5) 0.0249(3) Uani 1 1 d . . . . .
C2 C -0.11211(12) 0.19536(14) 0.59719(6) 0.0198(3) Uani 1 1 d . . . . .
H2 H -0.132802 0.199454 0.637878 0.024 Uiso 1 1 calc R . . . .
C6 C 0.02188(12) 0.27767(13) 0.51569(5) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.21652(12) 0.44606(13) 0.47432(6) 0.0192(3) Uani 1 1 d . . . . .
C1 C -0.01200(12) 0.28086(13) 0.57808(5) 0.0182(3) Uani 1 1 d . . . . .
C21 C 0.36467(12) 0.24901(14) 0.72339(5) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.12751(12) 0.37768(13) 0.51403(5) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.15325(12) 0.43527(13) 0.57295(6) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.29281(12) 0.54558(14) 0.51379(6) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.25881(12) 0.54299(14) 0.57578(6) 0.0192(3) Uani 1 1 d . . . . .
C4 C -0.14684(12) 0.10252(14) 0.49285(6) 0.0193(3) Uani 1 1 d . . . . .
C5 C -0.04863(12) 0.18666(13) 0.47250(6) 0.0193(3) Uani 1 1 d . . . . .
H5 H -0.030219 0.182726 0.431452 0.023 Uiso 1 1 calc R . . . .
C22 C 0.46660(13) 0.17627(14) 0.69718(6) 0.0214(3) Uani 1 1 d . . . . .
H22 H 0.446509 0.110736 0.664656 0.026 Uiso 1 1 calc R . . . .
C15 C 0.38926(12) 0.63552(14) 0.49444(6) 0.0216(3) Uani 1 1 d . . . . .
C26 C 0.39755(13) 0.34736(14) 0.77273(6) 0.0222(3) Uani 1 1 d . . . . .
H26 H 0.331901 0.396730 0.790383 0.027 Uiso 1 1 calc R . . . .
C3 C -0.17969(12) 0.10444(14) 0.55405(6) 0.0202(3) Uani 1 1 d . . . . .
H3A H -0.246355 0.045008 0.565398 0.024 Uiso 1 1 calc R . . . .
C12 C 0.32518(12) 0.63354(14) 0.61925(6) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.306284 0.633266 0.660253 0.026 Uiso 1 1 calc R . . . .
C18 C 0.24022(13) 0.43759(14) 0.41332(6) 0.0223(3) Uani 1 1 d . . . . .
H18 H 0.192367 0.373914 0.386090 0.027 Uiso 1 1 calc R . . . .
C25 C 0.52625(13) 0.37097(14) 0.79504(6) 0.0223(3) Uani 1 1 d . . . . .
H25 H 0.547384 0.434892 0.828047 0.027 Uiso 1 1 calc R . . . .
C13 C 0.42283(13) 0.72708(15) 0.60023(6) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.467220 0.789030 0.629411 0.029 Uiso 1 1 calc R . . . .
C24 C 0.62430(12) 0.29888(14) 0.76801(6) 0.0211(3) Uani 1 1 d . . . . .
C20 C 0.12170(12) 0.28216(14) 0.71897(6) 0.0212(3) Uani 1 1 d . . . . .
H20A H 0.138307 0.315411 0.761651 0.025 Uiso 1 1 calc R . . . .
H20B H 0.054406 0.207601 0.717353 0.025 Uiso 1 1 calc R . . . .
C19 C 0.07106(13) 0.41121(14) 0.67805(5) 0.0206(3) Uani 1 1 d . . . . .
H19A H -0.016632 0.435534 0.686829 0.025 Uiso 1 1 calc R . . . .
H19B H 0.126112 0.495841 0.688278 0.025 Uiso 1 1 calc R . . . .
C16 C 0.41156(13) 0.62373(15) 0.43091(6) 0.0244(3) Uani 1 1 d . . . . .
H16 H 0.475228 0.681080 0.415525 0.029 Uiso 1 1 calc R . . . .
C14 C 0.45450(13) 0.72973(14) 0.54010(6) 0.0239(3) Uani 1 1 d . . . . .
H14 H 0.518748 0.793317 0.529314 0.029 Uiso 1 1 calc R . . . .
C23 C 0.59448(13) 0.20109(15) 0.71905(6) 0.0228(3) Uani 1 1 d . . . . .
H23 H 0.660891 0.153111 0.701405 0.027 Uiso 1 1 calc R . . . .
C17 C 0.33906(14) 0.52765(15) 0.39232(6) 0.0250(3) Uani 1 1 d . . . . .
H17 H 0.355189 0.521264 0.350996 0.030 Uiso 1 1 calc R . . . .


_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 N1 1.2404(14) . ?
O2 N1 1.2245(15) . ?
O3 N4 1.2339(15) . ?
O4 N4 1.2340(15) . ?
N2 C1 1.3821(16) . ?
N2 C11 1.3756(16) . ?
N2 C19 1.4576(15) . ?
N1 C4 1.4529(16) . ?
N3 H3 0.8600 . ?
N3 C21 1.3569(17) . ?
N3 C20 1.4473(17) . ?
N4 C24 1.4420(17) . ?
C2 H2 0.9300 . ?
C2 C1 1.3933(18) . ?
C2 C3 1.3797(18) . ?
C6 C1 1.4328(16) . ?
C6 C7 1.4248(18) . ?
C6 C5 1.3941(17) . ?
C8 C7 1.4653(17) . ?
C8 C9 1.4235(18) . ?
C8 C18 1.3719(17) . ?
C21 C22 1.4143(18) . ?
C21 C26 1.4082(18) . ?
C7 C11 1.3783(17) . ?
C11 C10 1.4633(18) . ?
C9 C10 1.4250(17) . ?
C9 C15 1.3898(18) . ?
C10 C12 1.3767(18) . ?
C4 C5 1.3816(18) . ?
C4 C3 1.4039(17) . ?
C5 H5 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.3693(19) . ?
C15 C16 1.4237(18) . ?
C15 C14 1.4223(19) . ?
C26 H26 0.9300 . ?
C26 C25 1.3776(19) . ?
C3 H3A 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.4160(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.4229(19) . ?
C25 H25 0.9300 . ?
C25 C24 1.3889(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3773(19) . ?
C24 C23 1.3944(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.5312(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.374(2) . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
C17 H17 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
C1 N2 C19 126.42(10) . . ?
C11 N2 C1 107.50(10) . . ?
C11 N2 C19 126.01(11) . . ?
O1 N1 C4 117.54(11) . . ?
O2 N1 O1 122.55(11) . . ?
O2 N1 C4 119.91(10) . . ?
C21 N3 H3 116.3 . . ?
C21 N3 C20 127.40(11) . . ?
C20 N3 H3 116.3 . . ?
O3 N4 C24 118.91(11) . . ?
O4 N4 O3 122.40(11) . . ?
O4 N4 C24 118.68(11) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C3 C2 C1 118.12(11) . . ?
C7 C6 C1 106.11(10) . . ?
C5 C6 C1 118.77(11) . . ?
C5 C6 C7 135.11(11) . . ?
C9 C8 C7 105.07(10) . . ?
C18 C8 C7 136.98(12) . . ?
C18 C8 C9 117.94(12) . . ?
N2 C1 C2 129.12(11) . . ?
N2 C1 C6 108.55(11) . . ?
C2 C1 C6 122.33(11) . . ?
N3 C21 C22 118.17(11) . . ?
N3 C21 C26 123.30(12) . . ?
C26 C21 C22 118.51(12) . . ?
C6 C7 C8 144.90(11) . . ?
C11 C7 C6 106.90(11) . . ?
C11 C7 C8 108.17(11) . . ?
N2 C11 C7 110.94(11) . . ?
N2 C11 C10 137.82(11) . . ?
C7 C11 C10 111.19(11) . . ?
C8 C9 C10 112.20(11) . . ?
C15 C9 C8 124.24(12) . . ?
C15 C9 C10 123.56(12) . . ?
C9 C10 C11 103.36(11) . . ?
C12 C10 C11 138.04(12) . . ?
C12 C10 C9 118.60(12) . . ?
C5 C4 N1 118.19(11) . . ?
C5 C4 C3 123.79(12) . . ?
C3 C4 N1 118.02(11) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 C6 117.63(11) . . ?
C4 C5 H5 121.2 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.85(12) . . ?
C23 C22 H22 119.6 . . ?
C9 C15 C16 116.37(12) . . ?
C9 C15 C14 116.55(12) . . ?
C14 C15 C16 127.08(12) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.48(12) . . ?
C25 C26 H26 119.8 . . ?
C2 C3 C4 119.36(12) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C10 C12 H12 120.7 . . ?
C10 C12 C13 118.63(12) . . ?
C13 C12 H12 120.7 . . ?
C8 C18 H18 120.5 . . ?
C8 C18 C17 119.04(12) . . ?
C17 C18 H18 120.5 . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24 119.71(12) . . ?
C24 C25 H25 120.1 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.43(12) . . ?
C14 C13 H13 118.8 . . ?
C25 C24 N4 119.73(12) . . ?
C25 C24 C23 120.98(12) . . ?
C23 C24 N4 119.29(12) . . ?
N3 C20 H20A 108.9 . . ?
N3 C20 H20B 108.9 . . ?
N3 C20 C19 113.55(10) . . ?
H20A C20 H20B 107.7 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
N2 C19 C20 112.22(10) . . ?
N2 C19 H19A 109.2 . . ?
N2 C19 H19B 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.05(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.22(12) . . ?
C13 C14 H14 119.9 . . ?
C22 C23 C24 119.45(12) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C18 C17 H17 118.8 . . ?
C16 C17 C18 122.36(12) . . ?
C16 C17 H17 118.8 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.955
_oxdiff_exptl_absorpt_empirical_full_min 0.415
_chemical_properties_physical    Air-sensitive
