# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2253546'
loop_
_audit_author_name
_audit_author_address
'he heng'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N4 O2'
_chemical_formula_weight         398.45

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8519(9)
_cell_length_b                   9.9144(11)
_cell_length_c                   12.8442(14)
_cell_angle_alpha                108.2800(10)
_cell_angle_beta                 93.0630(10)
_cell_angle_gamma                108.3660(10)
_cell_volume                     1001.21(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3880
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.41

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5053
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3473
_reflns_number_gt                3002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.2239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3473
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C24 C 0.3350(3) 0.0922(2) -0.43766(17) 0.0759(6) Uani 1 1 d . . . . .
H24A H 0.301616 -0.013347 -0.482177 0.114 Uiso 1 1 calc R U . . .
H24B H 0.342036 0.150928 -0.485304 0.114 Uiso 1 1 calc R U . . .
H24C H 0.438816 0.123036 -0.393151 0.114 Uiso 1 1 calc R U . . .
C23 C 0.2136(2) 0.1175(2) -0.36283(15) 0.0624(5) Uani 1 1 d . . . . .
H23A H 0.205346 0.055775 -0.316426 0.075 Uiso 1 1 calc R U . . .
H23B H 0.108649 0.083643 -0.408500 0.075 Uiso 1 1 calc R U . . .
C22 C 0.2553(2) 0.2817(2) -0.28855(15) 0.0572(4) Uani 1 1 d . . . . .
H22A H 0.264678 0.343886 -0.334691 0.069 Uiso 1 1 calc R U . . .
H22B H 0.167898 0.290489 -0.247501 0.069 Uiso 1 1 calc R U . . .
N4 N 0.34598(14) 0.18933(14) -0.07862(10) 0.0431(3) Uani 1 1 d . . . . .
C13 C 0.74850(17) 0.31330(18) 0.23628(12) 0.0436(4) Uani 1 1 d . . . . .
H13A H 0.835061 0.372022 0.213229 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6770(2) 0.3454(2) 0.42600(14) 0.0566(4) Uani 1 1 d . . . . .
H15A H 0.583727 0.360251 0.403542 0.068 Uiso 1 1 calc R U . . .
O2 O 1.00852(14) 0.25740(14) 0.30672(10) 0.0554(3) Uani 1 1 d . . . . .
C7 C 0.2006(2) -0.03320(19) 0.04536(15) 0.0524(4) Uani 1 1 d . . . . .
H7A H 0.125976 -0.055103 -0.016762 0.063 Uiso 1 1 calc R U . . .
N2 N 0.54037(16) 0.44752(16) -0.21515(11) 0.0483(3) Uani 1 1 d . . . . .
O1 O 0.82191(12) 0.45488(14) 0.07422(9) 0.0516(3) Uani 1 1 d . . . . .
C4 C 0.44240(17) 0.29595(17) -0.11767(12) 0.0406(3) Uani 1 1 d . . . . .
C5 C 0.41791(16) 0.18072(16) 0.00787(12) 0.0400(3) Uani 1 1 d . . . . .
N3 N 0.57797(14) 0.26904(14) 0.06304(10) 0.0392(3) Uani 1 1 d . . . . .
C12 C 0.61009(17) 0.23949(17) 0.16342(12) 0.0395(3) Uani 1 1 d . . . . .
C14 C 0.77635(18) 0.31019(17) 0.34907(12) 0.0436(4) Uani 1 1 d . . . . .
C11 C 0.46309(18) 0.11739(17) 0.16313(12) 0.0416(3) Uani 1 1 d . . . . .
C6 C 0.35003(17) 0.08219(17) 0.06956(12) 0.0419(3) Uani 1 1 d . . . . .
N1 N 0.65746(15) 0.47339(15) -0.13116(10) 0.0443(3) Uani 1 1 d . . . . .
C2 C 0.60191(17) 0.38444(17) -0.07035(12) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.68298(17) 0.37848(17) 0.02741(12) 0.0398(3) Uani 1 1 d . . . . .
C3 C 0.40940(19) 0.34067(18) -0.20786(12) 0.0452(4) Uani 1 1 d . . . . .
C16 C 0.7159(3) 0.3587(2) 0.53619(15) 0.0684(6) Uani 1 1 d . . . . .
H16A H 0.648149 0.380909 0.586743 0.082 Uiso 1 1 calc R U . . .
C17 C 0.8545(3) 0.3388(2) 0.56969(15) 0.0676(6) Uani 1 1 d . . . . .
H17A H 0.881102 0.349090 0.643501 0.081 Uiso 1 1 calc R U . . .
C20 C 1.1502(2) 0.2295(3) 0.3368(2) 0.0721(6) Uani 1 1 d . . . . .
H20A H 1.203190 0.208340 0.273437 0.108 Uiso 1 1 calc R U . . .
H20B H 1.221940 0.317343 0.395751 0.108 Uiso 1 1 calc R U . . .
H20C H 1.120866 0.144159 0.361355 0.108 Uiso 1 1 calc R U . . .
C19 C 0.91635(19) 0.28981(17) 0.38603(13) 0.0445(4) Uani 1 1 d . . . . .
C8 C 0.1666(2) -0.1142(2) 0.11644(15) 0.0587(5) Uani 1 1 d . . . . .
H8A H 0.066813 -0.190861 0.102881 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2800(2) -0.08242(19) 0.20816(15) 0.0569(4) Uani 1 1 d . . . . .
H9A H 0.255604 -0.139821 0.254063 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4281(2) 0.03254(18) 0.23245(14) 0.0492(4) Uani 1 1 d . . . . .
H10A H 0.502948 0.052808 0.294006 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8182(2) 0.5833(2) -0.11783(15) 0.0546(4) Uani 1 1 d . . . . .
H21A H 0.820623 0.628778 -0.173875 0.082 Uiso 1 1 calc R U . . .
H21B H 0.844064 0.660430 -0.045514 0.082 Uiso 1 1 calc R U . . .
H21C H 0.895728 0.533007 -0.125316 0.082 Uiso 1 1 calc R U . . .
C18 C 0.9547(2) 0.30380(19) 0.49567(14) 0.0577(5) Uani 1 1 d . . . . .
H18A H 1.047958 0.289590 0.519160 0.069 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
C24 C23 1.507(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 C22 1.518(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C3 1.498(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 C5 1.2904(19) . ?
N4 C4 1.381(2) . ?
C13 C12 1.340(2) . ?
C13 C14 1.468(2) . ?
C13 H13A 0.9300 . ?
C15 C14 1.393(2) . ?
C15 C16 1.393(3) . ?
C15 H15A 0.9300 . ?
O2 C19 1.362(2) . ?
O2 C20 1.425(2) . ?
C7 C8 1.381(3) . ?
C7 C6 1.391(2) . ?
C7 H7A 0.9300 . ?
N2 C3 1.332(2) . ?
N2 N1 1.3576(18) . ?
O1 C1 1.2231(18) . ?
C4 C2 1.388(2) . ?
C4 C3 1.411(2) . ?
C5 N3 1.4135(18) . ?
C5 C6 1.452(2) . ?
N3 C1 1.404(2) . ?
N3 C12 1.4420(19) . ?
C12 C11 1.471(2) . ?
C14 C19 1.399(2) . ?
C11 C10 1.390(2) . ?
C11 C6 1.399(2) . ?
N1 C2 1.353(2) . ?
N1 C21 1.456(2) . ?
C2 C1 1.439(2) . ?
C16 C17 1.371(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 C18 1.384(2) . ?
C8 C9 1.392(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 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
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24 C23 C22 113.72(16) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C3 C22 C23 112.84(14) . . ?
C3 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C3 C22 H22B 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C5 N4 C4 113.43(12) . . ?
C12 C13 C14 126.12(14) . . ?
C12 C13 H13A 116.9 . . ?
C14 C13 H13A 116.9 . . ?
C14 C15 C16 120.77(18) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C19 O2 C20 118.24(14) . . ?
C8 C7 C6 117.93(16) . . ?
C8 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
C3 N2 N1 106.71(13) . . ?
N4 C4 C2 123.87(13) . . ?
N4 C4 C3 130.95(13) . . ?
C2 C4 C3 105.18(14) . . ?
N4 C5 N3 126.41(14) . . ?
N4 C5 C6 127.12(13) . . ?
N3 C5 C6 106.45(12) . . ?
C1 N3 C5 123.17(12) . . ?
C1 N3 C12 126.10(12) . . ?
C5 N3 C12 110.53(12) . . ?
C13 C12 N3 123.97(14) . . ?
C13 C12 C11 131.08(14) . . ?
N3 C12 C11 104.95(12) . . ?
C15 C14 C19 118.02(15) . . ?
C15 C14 C13 121.68(15) . . ?
C19 C14 C13 119.83(14) . . ?
C10 C11 C6 119.52(14) . . ?
C10 C11 C12 131.49(14) . . ?
C6 C11 C12 108.83(13) . . ?
C7 C6 C11 121.75(15) . . ?
C7 C6 C5 129.22(14) . . ?
C11 C6 C5 109.01(13) . . ?
C2 N1 N2 110.90(12) . . ?
C2 N1 C21 128.90(13) . . ?
N2 N1 C21 120.19(13) . . ?
N1 C2 C4 107.19(13) . . ?
N1 C2 C1 129.37(13) . . ?
C4 C2 C1 123.42(14) . . ?
O1 C1 N3 123.65(13) . . ?
O1 C1 C2 126.68(14) . . ?
N3 C1 C2 109.67(12) . . ?
N2 C3 C4 110.01(13) . . ?
N2 C3 C22 121.77(15) . . ?
C4 C3 C22 128.21(15) . . ?
C17 C16 C15 119.64(18) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.90(16) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C19 C18 124.21(15) . . ?
O2 C19 C14 114.82(13) . . ?
C18 C19 C14 120.97(16) . . ?
C7 C8 C9 120.66(16) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C10 C9 C8 121.41(17) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C11 118.70(16) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 C19 119.69(18) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?

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
C24 C23 C22 C3 -63.3(2) . . . . ?
C5 N4 C4 C2 0.9(2) . . . . ?
C5 N4 C4 C3 -179.17(15) . . . . ?
C4 N4 C5 N3 1.0(2) . . . . ?
C4 N4 C5 C6 179.12(13) . . . . ?
N4 C5 N3 C1 -1.6(2) . . . . ?
C6 C5 N3 C1 179.98(12) . . . . ?
N4 C5 N3 C12 173.51(13) . . . . ?
C6 C5 N3 C12 -4.95(15) . . . . ?
C14 C13 C12 N3 167.01(14) . . . . ?
C14 C13 C12 C11 -13.2(3) . . . . ?
C1 N3 C12 C13 -1.0(2) . . . . ?
C5 N3 C12 C13 -175.84(13) . . . . ?
C1 N3 C12 C11 179.22(12) . . . . ?
C5 N3 C12 C11 4.33(15) . . . . ?
C16 C15 C14 C19 -0.5(2) . . . . ?
C16 C15 C14 C13 -172.64(15) . . . . ?
C12 C13 C14 C15 -53.8(2) . . . . ?
C12 C13 C14 C19 134.13(16) . . . . ?
C13 C12 C11 C10 -6.5(3) . . . . ?
N3 C12 C11 C10 173.29(15) . . . . ?
C13 C12 C11 C6 178.20(15) . . . . ?
N3 C12 C11 C6 -1.99(15) . . . . ?
C8 C7 C6 C11 -0.5(2) . . . . ?
C8 C7 C6 C5 177.99(15) . . . . ?
C10 C11 C6 C7 1.9(2) . . . . ?
C12 C11 C6 C7 177.83(13) . . . . ?
C10 C11 C6 C5 -176.90(13) . . . . ?
C12 C11 C6 C5 -0.96(16) . . . . ?
N4 C5 C6 C7 6.5(3) . . . . ?
N3 C5 C6 C7 -175.07(14) . . . . ?
N4 C5 C6 C11 -174.84(14) . . . . ?
N3 C5 C6 C11 3.60(16) . . . . ?
C3 N2 N1 C2 -0.25(17) . . . . ?
C3 N2 N1 C21 178.72(13) . . . . ?
N2 N1 C2 C4 0.64(17) . . . . ?
C21 N1 C2 C4 -178.22(14) . . . . ?
N2 N1 C2 C1 -177.77(14) . . . . ?
C21 N1 C2 C1 3.4(3) . . . . ?
N4 C4 C2 N1 179.23(12) . . . . ?
C3 C4 C2 N1 -0.74(16) . . . . ?
N4 C4 C2 C1 -2.2(2) . . . . ?
C3 C4 C2 C1 177.78(13) . . . . ?
C5 N3 C1 O1 -179.60(13) . . . . ?
C12 N3 C1 O1 6.1(2) . . . . ?
C5 N3 C1 C2 0.19(18) . . . . ?
C12 N3 C1 C2 -174.10(12) . . . . ?
N1 C2 C1 O1 -0.5(3) . . . . ?
C4 C2 C1 O1 -178.68(14) . . . . ?
N1 C2 C1 N3 179.71(13) . . . . ?
C4 C2 C1 N3 1.54(19) . . . . ?
N1 N2 C3 C4 -0.24(17) . . . . ?
N1 N2 C3 C22 -179.40(14) . . . . ?
N4 C4 C3 N2 -179.36(14) . . . . ?
C2 C4 C3 N2 0.61(17) . . . . ?
N4 C4 C3 C22 -0.3(3) . . . . ?
C2 C4 C3 C22 179.71(15) . . . . ?
C23 C22 C3 N2 112.45(18) . . . . ?
C23 C22 C3 C4 -66.5(2) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C20 O2 C19 C18 2.8(2) . . . . ?
C20 O2 C19 C14 -177.74(15) . . . . ?
C15 C14 C19 O2 -179.27(13) . . . . ?
C13 C14 C19 O2 -7.0(2) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C13 C14 C19 C18 172.49(14) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C6 C11 C10 C9 -1.6(2) . . . . ?
C12 C11 C10 C9 -176.43(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
O2 C19 C18 C17 179.15(15) . . . . ?
C14 C19 C18 C17 -0.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes
C13 H13A O1 0.93 2.20 2.8509(19) 126.4 . yes
C21 H21A O2 0.96 2.62 3.466(2) 146.7 2_765 yes
C21 H21C O1 0.96 2.51 3.363(2) 148.7 2_765 yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2255363'
loop_
_audit_author_name
_audit_author_address
'he heng'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2023-04-11 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 N2 O'
_chemical_formula_weight         374.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   11.023(4)
_cell_length_b                   14.004(6)
_cell_length_c                   13.233(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.61
_cell_angle_gamma                90
_cell_volume                     1856.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2385
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.69

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4758
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         22.766
_diffrn_reflns_theta_full        22.766
_diffrn_measured_fraction_theta_max 0.710
_diffrn_measured_fraction_theta_full 0.710
_diffrn_reflns_Laue_measured_fraction_max 0.710
_diffrn_reflns_Laue_measured_fraction_full 0.710
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_point_group_measured_fraction_full 0.710
_reflns_number_total             1784
_reflns_number_gt                1120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0014P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1784
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C26 C 0.3277(4) 0.3406(3) 0.5676(2) 0.1015(13) Uani 1 1 d . . . . .
H26A H 0.303024 0.324363 0.627037 0.152 Uiso 1 1 calc R U . . .
H26B H 0.289337 0.295154 0.508393 0.152 Uiso 1 1 calc R U . . .
H26C H 0.423079 0.339523 0.594446 0.152 Uiso 1 1 calc R U . . .
O1 O 0.2797(2) 0.43322(17) 0.52767(17) 0.0804(7) Uani 1 1 d . . . . .
C23 C 0.2467(3) 0.5554(2) 0.4014(3) 0.0701(9) Uani 1 1 d . . . . .
H23A H 0.194890 0.585394 0.432320 0.084 Uiso 1 1 calc R U . . .
C24 C 0.2643(4) 0.5976(2) 0.3158(3) 0.0771(10) Uani 1 1 d . . . . .
H24A H 0.224021 0.656062 0.288209 0.093 Uiso 1 1 calc R U . . .
C25 C 0.3413(3) 0.5541(2) 0.2701(2) 0.0707(10) Uani 1 1 d . . . . .
H25A H 0.354439 0.583617 0.212497 0.085 Uiso 1 1 calc R U . . .
C9 C 0.7801(3) 0.4247(2) 0.2860(2) 0.0613(9) Uani 1 1 d . . . . .
H9A H 0.734793 0.454210 0.323148 0.074 Uiso 1 1 calc R U . . .
C8 C 0.9199(4) 0.4191(2) 0.3358(2) 0.0725(10) Uani 1 1 d . . . . .
H8A H 0.966551 0.445512 0.405897 0.087 Uiso 1 1 calc R U . . .
C7 C 0.9883(3) 0.3762(2) 0.2843(3) 0.0729(9) Uani 1 1 d . . . . .
H7A H 1.080633 0.370838 0.320729 0.087 Uiso 1 1 calc R U . . .
N2 N 0.5738(3) 0.32908(16) -0.04429(18) 0.0597(7) Uani 1 1 d . . . . .
C22 C 0.3055(3) 0.4684(2) 0.4427(2) 0.0606(8) Uani 1 1 d . . . . .
C21 C 0.3821(3) 0.4236(2) 0.3973(2) 0.0543(8) Uani 1 1 d . . . . .
H21A H 0.422116 0.365113 0.425104 0.065 Uiso 1 1 calc R U . . .
C20 C 0.3992(3) 0.4666(2) 0.3094(2) 0.0554(8) Uani 1 1 d . . . . .
N1 N 0.5700(3) 0.38661(15) 0.12411(17) 0.0513(6) Uani 1 1 d . . . . .
C10 C 0.7110(3) 0.38668(18) 0.1827(2) 0.0484(7) Uani 1 1 d . . . . .
C2 C 0.7123(3) 0.3159(2) 0.0135(2) 0.0554(8) Uani 1 1 d . . . . .
C3 C 0.7816(4) 0.2765(2) -0.0421(3) 0.0716(10) Uani 1 1 d . . . . .
H3A H 0.736573 0.255923 -0.115180 0.086 Uiso 1 1 calc R U . . .
C1 C 0.5131(3) 0.36335(19) 0.0119(2) 0.0520(8) Uani 1 1 d . . . . .
C15 C 0.1165(3) 0.4230(2) -0.0663(3) 0.0705(9) Uani 1 1 d . . . . .
H15A H 0.028326 0.436244 -0.079918 0.085 Uiso 1 1 calc R U . . .
C19 C 0.4880(3) 0.42367(19) 0.2651(2) 0.0563(8) Uani 1 1 d . . . . .
H19A H 0.566798 0.397820 0.317498 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4710(3) 0.41680(19) 0.1606(2) 0.0489(7) Uani 1 1 d . . . . .
C11 C 0.7794(3) 0.34659(18) 0.1237(2) 0.0528(8) Uani 1 1 d . . . . .
C4 C 0.9197(4) 0.2678(2) 0.0123(3) 0.0822(11) Uani 1 1 d . . . . .
H4A H 0.966347 0.240030 -0.024731 0.099 Uiso 1 1 calc R U . . .
C6 C 0.9217(3) 0.3396(2) 0.1766(3) 0.0613(8) Uani 1 1 d . . . . .
C18 C 0.3724(3) 0.3847(2) -0.0285(2) 0.0537(8) Uani 1 1 d . . . . .
C13 C 0.3458(3) 0.41789(19) 0.0579(2) 0.0538(7) Uani 1 1 d . . . . .
C14 C 0.2142(3) 0.4382(2) 0.0393(3) 0.0671(9) Uani 1 1 d . . . . .
H14A H 0.193190 0.461208 0.095970 0.081 Uiso 1 1 calc R U . . .
C16 C 0.1432(4) 0.3895(2) -0.1512(3) 0.0777(10) Uani 1 1 d . . . . .
H16A H 0.074197 0.380766 -0.221222 0.093 Uiso 1 1 calc R U . . .
C17 C 0.2734(4) 0.3683(2) -0.1337(2) 0.0693(10) Uani 1 1 d . . . . .
H17A H 0.293363 0.344090 -0.190371 0.083 Uiso 1 1 calc R U . . .
C5 C 0.9874(4) 0.2987(2) 0.1175(3) 0.0771(10) Uani 1 1 d . . . . .
H5A H 1.079765 0.292643 0.151275 0.092 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
C26 O1 1.417(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O1 C22 1.362(3) . ?
C23 C24 1.361(4) . ?
C23 C22 1.382(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.374(4) . ?
C24 H24A 0.9300 . ?
C25 C20 1.379(4) . ?
C25 H25A 0.9300 . ?
C9 C10 1.366(4) . ?
C9 C8 1.404(4) . ?
C9 H9A 0.9300 . ?
C8 C7 1.349(4) . ?
C8 H8A 0.9300 . ?
C7 C6 1.401(4) . ?
C7 H7A 0.9300 . ?
N2 C1 1.283(3) . ?
N2 C2 1.405(3) . ?
C22 C21 1.375(4) . ?
C21 C20 1.391(3) . ?
C21 H21A 0.9300 . ?
C20 C19 1.463(4) . ?
N1 C1 1.389(3) . ?
N1 C10 1.419(3) . ?
N1 C12 1.429(3) . ?
C10 C11 1.409(4) . ?
C2 C3 1.377(4) . ?
C2 C11 1.400(4) . ?
C3 C4 1.393(5) . ?
C3 H3A 0.9300 . ?
C1 C18 1.445(4) . ?
C15 C16 1.359(4) . ?
C15 C14 1.380(4) . ?
C15 H15A 0.9300 . ?
C19 C12 1.319(3) . ?
C19 H19A 0.9300 . ?
C12 C13 1.479(4) . ?
C11 C6 1.430(4) . ?
C4 C5 1.348(4) . ?
C4 H4A 0.9300 . ?
C6 C5 1.390(4) . ?
C18 C13 1.374(4) . ?
C18 C17 1.384(4) . ?
C13 C14 1.396(4) . ?
C14 H14A 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C5 H5A 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
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 O1 C26 117.7(2) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C24 C25 C20 120.1(3) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C1 N2 C2 116.4(2) . . ?
O1 C22 C21 125.0(3) . . ?
O1 C22 C23 114.9(3) . . ?
C21 C22 C23 120.1(3) . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C25 C20 C21 119.8(3) . . ?
C25 C20 C19 119.7(3) . . ?
C21 C20 C19 120.2(2) . . ?
C1 N1 C10 119.2(2) . . ?
C1 N1 C12 111.3(3) . . ?
C10 N1 C12 129.2(2) . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 N1 125.1(3) . . ?
C11 C10 N1 114.4(2) . . ?
C3 C2 C11 120.6(3) . . ?
C3 C2 N2 118.7(3) . . ?
C11 C2 N2 120.6(3) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
N2 C1 N1 126.5(3) . . ?
N2 C1 C18 127.0(3) . . ?
N1 C1 C18 106.5(3) . . ?
C16 C15 C14 122.9(3) . . ?
C16 C15 H15A 118.5 . . ?
C14 C15 H15A 118.5 . . ?
C12 C19 C20 128.6(3) . . ?
C12 C19 H19A 115.7 . . ?
C20 C19 H19A 115.7 . . ?
C19 C12 N1 125.5(3) . . ?
C19 C12 C13 129.3(3) . . ?
N1 C12 C13 104.1(2) . . ?
C2 C11 C10 121.9(3) . . ?
C2 C11 C6 119.0(3) . . ?
C10 C11 C6 119.1(2) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C5 C6 C7 123.2(3) . . ?
C5 C6 C11 118.4(3) . . ?
C7 C6 C11 118.4(3) . . ?
C13 C18 C17 122.7(3) . . ?
C13 C18 C1 109.3(3) . . ?
C17 C18 C1 127.8(3) . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 C12 108.7(3) . . ?
C14 C13 C12 131.9(3) . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 H14A 121.2 . . ?
C13 C14 H14A 121.2 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C18 117.5(3) . . ?
C16 C17 H17A 121.3 . . ?
C18 C17 H17A 121.3 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?

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
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C20 1.2(5) . . . . ?
C10 C9 C8 C7 -0.5(4) . . . . ?
C9 C8 C7 C6 3.0(5) . . . . ?
C26 O1 C22 C21 -4.5(4) . . . . ?
C26 O1 C22 C23 174.8(3) . . . . ?
C24 C23 C22 O1 -179.5(3) . . . . ?
C24 C23 C22 C21 -0.1(5) . . . . ?
O1 C22 C21 C20 179.1(3) . . . . ?
C23 C22 C21 C20 -0.3(4) . . . . ?
C24 C25 C20 C21 -1.5(5) . . . . ?
C24 C25 C20 C19 -176.1(3) . . . . ?
C22 C21 C20 C25 1.1(4) . . . . ?
C22 C21 C20 C19 175.6(2) . . . . ?
C8 C9 C10 C11 -3.5(4) . . . . ?
C8 C9 C10 N1 179.1(2) . . . . ?
C1 N1 C10 C9 167.1(2) . . . . ?
C12 N1 C10 C9 -6.0(4) . . . . ?
C1 N1 C10 C11 -10.4(3) . . . . ?
C12 N1 C10 C11 176.5(2) . . . . ?
C1 N2 C2 C3 178.0(3) . . . . ?
C1 N2 C2 C11 -5.2(4) . . . . ?
C11 C2 C3 C4 -0.3(4) . . . . ?
N2 C2 C3 C4 176.6(2) . . . . ?
C2 N2 C1 N1 -1.5(4) . . . . ?
C2 N2 C1 C18 179.0(2) . . . . ?
C10 N1 C1 N2 9.8(4) . . . . ?
C12 N1 C1 N2 -176.0(3) . . . . ?
C10 N1 C1 C18 -170.7(2) . . . . ?
C12 N1 C1 C18 3.6(3) . . . . ?
C25 C20 C19 C12 -44.9(4) . . . . ?
C21 C20 C19 C12 140.5(3) . . . . ?
C20 C19 C12 N1 170.3(3) . . . . ?
C20 C19 C12 C13 -23.7(5) . . . . ?
C1 N1 C12 C19 164.5(2) . . . . ?
C10 N1 C12 C19 -22.0(4) . . . . ?
C1 N1 C12 C13 -4.4(3) . . . . ?
C10 N1 C12 C13 169.1(2) . . . . ?
C3 C2 C11 C10 -179.7(2) . . . . ?
N2 C2 C11 C10 3.5(4) . . . . ?
C3 C2 C11 C6 2.2(4) . . . . ?
N2 C2 C11 C6 -174.6(2) . . . . ?
C9 C10 C11 C2 -173.4(2) . . . . ?
N1 C10 C11 C2 4.3(3) . . . . ?
C9 C10 C11 C6 4.8(4) . . . . ?
N1 C10 C11 C6 -177.6(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C8 C7 C6 C5 176.9(3) . . . . ?
C8 C7 C6 C11 -1.6(4) . . . . ?
C2 C11 C6 C5 -2.6(4) . . . . ?
C10 C11 C6 C5 179.2(2) . . . . ?
C2 C11 C6 C7 175.9(2) . . . . ?
C10 C11 C6 C7 -2.2(4) . . . . ?
N2 C1 C18 C13 178.4(3) . . . . ?
N1 C1 C18 C13 -1.2(3) . . . . ?
N2 C1 C18 C17 3.5(5) . . . . ?
N1 C1 C18 C17 -176.0(2) . . . . ?
C17 C18 C13 C14 -1.4(4) . . . . ?
C1 C18 C13 C14 -176.6(2) . . . . ?
C17 C18 C13 C12 173.6(2) . . . . ?
C1 C18 C13 C12 -1.5(3) . . . . ?
C19 C12 C13 C18 -164.7(3) . . . . ?
N1 C12 C13 C18 3.5(3) . . . . ?
C19 C12 C13 C14 9.4(5) . . . . ?
N1 C12 C13 C14 177.7(3) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C12 C13 C14 C15 -173.3(2) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C13 C18 C17 C16 1.9(4) . . . . ?
C1 C18 C17 C16 176.1(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C7 C6 C5 C4 -177.3(3) . . . . ?
C11 C6 C5 C4 1.1(4) . . . . ?

_refine_diff_density_max         0.087
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.021

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2253576'
loop_
_audit_author_name
_audit_author_address
'he heng'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N4 O'
_chemical_formula_weight         382.45

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.810(7)
_cell_length_b                   10.948(8)
_cell_length_c                   11.015(8)
_cell_angle_alpha                61.711(8)
_cell_angle_beta                 82.606(9)
_cell_angle_gamma                76.072(9)
_cell_volume                     1011.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2727
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5137
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3508
_reflns_number_gt                2872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.2598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C24 C 0.2865(3) 1.3681(3) 0.3731(3) 0.0912(8) Uani 1 1 d . . . . .
H24A H 0.337856 1.389993 0.426271 0.137 Uiso 1 1 calc R U . . .
H24B H 0.292673 1.434031 0.277249 0.137 Uiso 1 1 calc R U . . .
H24C H 0.189777 1.374848 0.402806 0.137 Uiso 1 1 calc R U . . .
C23 C 0.3483(2) 1.2187(2) 0.3936(3) 0.0684(6) Uani 1 1 d . . . . .
H23A H 0.446478 1.212005 0.365256 0.082 Uiso 1 1 calc R U . . .
H23B H 0.343565 1.152811 0.490834 0.082 Uiso 1 1 calc R U . . .
C22 C 0.2731(2) 1.1770(2) 0.3134(2) 0.0584(5) Uani 1 1 d . . . . .
H22A H 0.176816 1.176561 0.347251 0.070 Uiso 1 1 calc R U . . .
H22B H 0.270655 1.248039 0.217416 0.070 Uiso 1 1 calc R U . . .
N4 N 0.53297(15) 1.08472(15) 0.14019(15) 0.0477(4) Uani 1 1 d . . . . .
C13 C 0.83011(19) 0.70653(19) 0.05433(19) 0.0497(4) Uani 1 1 d . . . . .
H13A H 0.916188 0.708985 0.007560 0.060 Uiso 1 1 calc R U . . .
N3 N 0.29303(17) 0.91903(17) 0.41211(16) 0.0555(4) Uani 1 1 d . . . . .
C10 C 0.9249(2) 0.9907(2) -0.13504(19) 0.0543(5) Uani 1 1 d . . . . .
H10A H 0.981678 0.917257 -0.149524 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8611(2) 1.2359(2) -0.1873(2) 0.0612(5) Uani 1 1 d . . . . .
H8A H 0.877497 1.327452 -0.237372 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7535(2) 1.2115(2) -0.0909(2) 0.0562(5) Uani 1 1 d . . . . .
H7A H 0.696733 1.284951 -0.076450 0.067 Uiso 1 1 calc R U . . .
O1 O 0.62439(17) 0.64821(14) 0.29738(14) 0.0714(5) Uani 1 1 d . . . . .
C4 C 0.45188(18) 1.00060(18) 0.24349(18) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.62809(18) 1.01621(17) 0.08945(17) 0.0445(4) Uani 1 1 d . . . . .
N2 N 0.65253(15) 0.86909(14) 0.13035(14) 0.0437(3) Uani 1 1 d . . . . .
C12 C 0.77056(18) 0.83112(18) 0.05386(17) 0.0450(4) Uani 1 1 d . . . . .
N1 N 0.37620(17) 0.80944(16) 0.39562(16) 0.0526(4) Uani 1 1 d . . . . .
C2 C 0.47298(19) 0.85521(18) 0.29393(18) 0.0463(4) Uani 1 1 d . . . . .
C11 C 0.81809(19) 0.96364(19) -0.03609(18) 0.0473(4) Uani 1 1 d . . . . .
C6 C 0.73229(18) 1.07340(18) -0.01568(18) 0.0466(4) Uani 1 1 d . . . . .
C1 C 0.5857(2) 0.77572(18) 0.24659(18) 0.0482(4) Uani 1 1 d . . . . .
C3 C 0.33838(19) 1.03507(19) 0.32159(19) 0.0500(4) Uani 1 1 d . . . . .
C14 C 0.79197(18) 0.56811(18) 0.11075(18) 0.0469(4) Uani 1 1 d . . . . .
C15 C 0.8937(2) 0.4457(2) 0.1738(2) 0.0613(5) Uani 1 1 d . . . . .
H15A H 0.983899 0.452815 0.183446 0.074 Uiso 1 1 calc R U . . .
C16 C 0.8631(2) 0.3140(2) 0.2223(2) 0.0679(6) Uani 1 1 d . . . . .
H16A H 0.931406 0.233019 0.267611 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7326(3) 0.3015(2) 0.2041(2) 0.0657(6) Uani 1 1 d . . . . .
H17A H 0.712407 0.212343 0.236022 0.079 Uiso 1 1 calc R U . . .
C18 C 0.6317(2) 0.4214(2) 0.1385(2) 0.0633(5) Uani 1 1 d . . . . .
H18A H 0.543508 0.413283 0.124510 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6602(2) 0.5539(2) 0.09309(19) 0.0544(5) Uani 1 1 d . . . . .
H19A H 0.590469 0.634290 0.050310 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9463(2) 1.1285(2) -0.2125(2) 0.0582(5) Uani 1 1 d . . . . .
C20 C 1.0588(3) 1.1600(3) -0.3237(3) 0.0800(7) Uani 1 1 d . . . . .
H20B H 1.059888 1.259223 -0.366969 0.120 Uiso 1 1 calc R U . . .
H20C H 1.148544 1.105975 -0.283570 0.120 Uiso 1 1 calc R U . . .
H20D H 1.039615 1.134752 -0.391240 0.120 Uiso 1 1 calc R U . . .
C21 C 0.3505(2) 0.6677(2) 0.4786(2) 0.0643(5) Uani 1 1 d . . . . .
H21B H 0.418039 0.602771 0.454539 0.096 Uiso 1 1 calc R U . . .
H21C H 0.358769 0.640610 0.574397 0.096 Uiso 1 1 calc R U . . .
H21D H 0.257559 0.665663 0.461983 0.096 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
C24 C23 1.517(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 C22 1.499(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C3 1.495(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 C5 1.293(2) . ?
N4 C4 1.379(2) . ?
C13 C12 1.346(3) . ?
C13 C14 1.464(3) . ?
C13 H13A 0.9300 . ?
N3 C3 1.328(3) . ?
N3 N1 1.355(2) . ?
C10 C11 1.386(3) . ?
C10 C9 1.391(3) . ?
C10 H10A 0.9300 . ?
C8 C7 1.375(3) . ?
C8 C9 1.392(3) . ?
C8 H8A 0.9300 . ?
C7 C6 1.391(3) . ?
C7 H7A 0.9300 . ?
O1 C1 1.211(2) . ?
C4 C2 1.385(3) . ?
C4 C3 1.408(3) . ?
C5 N2 1.417(2) . ?
C5 C6 1.447(3) . ?
N2 C1 1.407(2) . ?
N2 C12 1.440(2) . ?
C12 C11 1.466(3) . ?
N1 C2 1.353(2) . ?
N1 C21 1.446(3) . ?
C2 C1 1.439(3) . ?
C11 C6 1.387(3) . ?
C14 C19 1.387(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.375(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.369(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.373(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C9 C20 1.507(3) . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20D 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 H21D 0.9600 . ?

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
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 C24 112.48(19) . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C3 C22 C23 114.02(16) . . ?
C3 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C3 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C5 N4 C4 113.72(15) . . ?
C12 C13 C14 135.37(18) . . ?
C12 C13 H13A 112.3 . . ?
C14 C13 H13A 112.3 . . ?
C3 N3 N1 106.69(16) . . ?
C11 C10 C9 119.45(19) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C7 C8 C9 122.27(18) . . ?
C7 C8 H8A 118.9 . . ?
C9 C8 H8A 118.9 . . ?
C8 C7 C6 117.87(19) . . ?
C8 C7 H7A 121.1 . . ?
C6 C7 H7A 121.1 . . ?
C2 C4 N4 123.89(16) . . ?
C2 C4 C3 105.29(16) . . ?
N4 C4 C3 130.80(16) . . ?
N4 C5 N2 126.04(16) . . ?
N4 C5 C6 126.79(16) . . ?
N2 C5 C6 107.13(14) . . ?
C1 N2 C5 122.35(14) . . ?
C1 N2 C12 126.84(15) . . ?
C5 N2 C12 109.77(14) . . ?
C13 C12 N2 131.40(17) . . ?
C13 C12 C11 123.56(17) . . ?
N2 C12 C11 105.02(14) . . ?
N3 N1 C2 110.94(15) . . ?
N3 N1 C21 119.80(16) . . ?
C2 N1 C21 129.22(16) . . ?
N1 C2 C4 106.98(15) . . ?
N1 C2 C1 129.84(16) . . ?
C4 C2 C1 123.05(17) . . ?
C6 C11 C10 120.25(17) . . ?
C6 C11 C12 109.56(17) . . ?
C10 C11 C12 130.11(17) . . ?
C11 C6 C7 121.03(18) . . ?
C11 C6 C5 108.51(16) . . ?
C7 C6 C5 130.46(17) . . ?
O1 C1 N2 122.62(17) . . ?
O1 C1 C2 127.51(17) . . ?
N2 C1 C2 109.84(16) . . ?
N3 C3 C4 110.09(16) . . ?
N3 C3 C22 121.53(18) . . ?
C4 C3 C22 128.38(18) . . ?
C19 C14 C15 118.05(18) . . ?
C19 C14 C13 122.27(16) . . ?
C15 C14 C13 119.43(17) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C14 120.53(18) . . ?
C18 C19 H19A 119.7 . . ?
C14 C19 H19A 119.7 . . ?
C10 C9 C8 119.09(19) . . ?
C10 C9 C20 119.9(2) . . ?
C8 C9 C20 121.0(2) . . ?
C9 C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C20 H20D 109.5 . . ?
H20B C20 H20D 109.5 . . ?
H20C C20 H20D 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C21 H21D 109.5 . . ?
H21B C21 H21D 109.5 . . ?
H21C C21 H21D 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
C24 C23 C22 C3 175.2(2) . . . . ?
C9 C8 C7 C6 1.0(3) . . . . ?
C5 N4 C4 C2 2.9(2) . . . . ?
C5 N4 C4 C3 -178.94(17) . . . . ?
C4 N4 C5 N2 0.3(2) . . . . ?
C4 N4 C5 C6 -177.44(15) . . . . ?
N4 C5 N2 C1 -8.8(3) . . . . ?
C6 C5 N2 C1 169.28(14) . . . . ?
N4 C5 N2 C12 -177.85(15) . . . . ?
C6 C5 N2 C12 0.23(17) . . . . ?
C14 C13 C12 N2 11.7(3) . . . . ?
C14 C13 C12 C11 -166.51(19) . . . . ?
C1 N2 C12 C13 13.5(3) . . . . ?
C5 N2 C12 C13 -178.09(18) . . . . ?
C1 N2 C12 C11 -168.06(15) . . . . ?
C5 N2 C12 C11 0.38(17) . . . . ?
C3 N3 N1 C2 -0.8(2) . . . . ?
C3 N3 N1 C21 -178.61(16) . . . . ?
N3 N1 C2 C4 0.5(2) . . . . ?
C21 N1 C2 C4 178.00(18) . . . . ?
N3 N1 C2 C1 176.54(17) . . . . ?
C21 N1 C2 C1 -6.0(3) . . . . ?
N4 C4 C2 N1 178.60(15) . . . . ?
C3 C4 C2 N1 0.02(19) . . . . ?
N4 C4 C2 C1 2.2(3) . . . . ?
C3 C4 C2 C1 -176.35(16) . . . . ?
C9 C10 C11 C6 0.8(3) . . . . ?
C9 C10 C11 C12 177.17(17) . . . . ?
C13 C12 C11 C6 177.74(16) . . . . ?
N2 C12 C11 C6 -0.88(18) . . . . ?
C13 C12 C11 C10 1.0(3) . . . . ?
N2 C12 C11 C10 -177.57(17) . . . . ?
C10 C11 C6 C7 -1.7(3) . . . . ?
C12 C11 C6 C7 -178.76(15) . . . . ?
C10 C11 C6 C5 178.11(15) . . . . ?
C12 C11 C6 C5 1.04(19) . . . . ?
C8 C7 C6 C11 0.8(3) . . . . ?
C8 C7 C6 C5 -178.95(18) . . . . ?
N4 C5 C6 C11 177.27(16) . . . . ?
N2 C5 C6 C11 -0.79(18) . . . . ?
N4 C5 C6 C7 -3.0(3) . . . . ?
N2 C5 C6 C7 178.99(17) . . . . ?
C5 N2 C1 O1 -165.73(17) . . . . ?
C12 N2 C1 O1 1.4(3) . . . . ?
C5 N2 C1 C2 12.3(2) . . . . ?
C12 N2 C1 C2 179.37(14) . . . . ?
N1 C2 C1 O1 -7.0(3) . . . . ?
C4 C2 C1 O1 168.49(19) . . . . ?
N1 C2 C1 N2 175.13(17) . . . . ?
C4 C2 C1 N2 -9.4(2) . . . . ?
N1 N3 C3 C4 0.8(2) . . . . ?
N1 N3 C3 C22 -178.17(16) . . . . ?
C2 C4 C3 N3 -0.5(2) . . . . ?
N4 C4 C3 N3 -178.98(17) . . . . ?
C2 C4 C3 C22 178.37(17) . . . . ?
N4 C4 C3 C22 -0.1(3) . . . . ?
C23 C22 C3 N3 95.6(2) . . . . ?
C23 C22 C3 C4 -83.2(3) . . . . ?
C12 C13 C14 C19 48.1(3) . . . . ?
C12 C13 C14 C15 -137.7(2) . . . . ?
C19 C14 C15 C16 -2.5(3) . . . . ?
C13 C14 C15 C16 -177.00(19) . . . . ?
C14 C15 C16 C17 2.6(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C18 C19 C14 1.2(3) . . . . ?
C15 C14 C19 C18 0.6(3) . . . . ?
C13 C14 C19 C18 174.93(17) . . . . ?
C11 C10 C9 C8 0.9(3) . . . . ?
C11 C10 C9 C20 -177.91(18) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C7 C8 C9 C20 177.0(2) . . . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038

