# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2421489'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-03-20 downloaded from the CCDC.
;
_audit_creation_date             2024-12-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2 O2'
_chemical_formula_sum            'C23 H16 N2 O2'
_chemical_formula_weight         352.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1641(2)
_cell_length_b                   11.1647(2)
_cell_length_c                   19.4105(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.089(2)
_cell_angle_gamma                90
_cell_volume                     1741.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4333
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.1690
_cell_measurement_theta_min      4.5680
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.139a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.457
_diffrn_reflns_theta_min         4.587
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  32.00   1.00    1.23    --  -35.62  78.00-174.00   89
  2  ω    -20.00  63.00   1.00    1.23    --   35.62 -78.00  60.00   83
  3  ω     71.00 128.00   1.00    4.92    --  106.81 -78.00  60.00   57
  4  ω    104.00 170.00   1.00    4.92    --  106.81  78.00-174.00   66
  5  ω    -96.00 -68.00   1.00    1.23    --  -35.62-178.00 -90.00   28
  6  ω    -67.00 -39.00   1.00    1.23    --  -35.62-178.00 -90.00   28
  7  ω    -13.00  18.00   1.00    1.23    --   35.62 -77.00-180.00   31
  8  ω    -12.00  61.00   1.00    1.23    --   35.62 -77.00 -30.00   73
  9  ω    -29.00  16.00   1.00    1.23    --   35.62 -38.00 120.00   45
 10  ω    118.00 174.00   1.00    4.92    --  106.81 111.00  60.00   56
 11  ω     38.00  65.00   1.00    4.92    --  106.81 -94.00-150.00   27
 12  ω     42.00 128.00   1.00    4.92    --  106.81 -30.00  60.00   86
 13  ω     43.00  99.00   1.00    4.92    --  106.81-111.00 120.00   56
 14  ω    118.00 171.00   1.00    4.92    --  106.81  77.00 150.00   53
 15  ω    145.00 173.00   1.00    4.92    --  106.81 111.00 150.00   28
 16  ω     62.00 102.00   1.00    4.92    --  106.81-111.00   0.00   40
 17  ω    109.00 174.00   1.00    4.92    --  106.81  77.00 120.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1141626000
_diffrn_orient_matrix_UB_12      -0.0632821000
_diffrn_orient_matrix_UB_13      0.0439019000
_diffrn_orient_matrix_UB_21      -0.1331015000
_diffrn_orient_matrix_UB_22      0.0974804000
_diffrn_orient_matrix_UB_23      -0.0206001000
_diffrn_orient_matrix_UB_31      -0.0772971000
_diffrn_orient_matrix_UB_32      -0.0744271000
_diffrn_orient_matrix_UB_33      -0.0643947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2977
_reflns_number_total             3310
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.5038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.23556(14) 0.47422(9) 0.50854(5) 0.0317(2) Uani 1 1 d . . . . .
O2 O 0.24193(11) 0.36562(8) 0.28386(4) 0.0237(2) Uani 1 1 d . . . . .
N1 N 0.25115(13) 0.42264(9) 0.39680(5) 0.0185(2) Uani 1 1 d . . . . .
N2 N 0.27565(13) 0.12478(9) 0.31637(5) 0.0202(2) Uani 1 1 d . . . . .
C1 C 0.24740(15) 0.39516(12) 0.46721(6) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.25252(15) 0.26687(11) 0.48610(6) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.21415(18) 0.23553(13) 0.55119(7) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.190130 0.296050 0.582361 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2113(2) 0.11650(14) 0.57003(7) 0.0327(3) Uani 1 1 d . . . . .
H4 H 0.183919 0.094659 0.613941 0.039 Uiso 1 1 calc R U . . .
C5 C 0.24867(19) 0.02856(13) 0.52436(8) 0.0323(3) Uani 1 1 d . . . . .
H5 H 0.247329 -0.053410 0.537376 0.039 Uiso 1 1 calc R U . . .
C6 C 0.28784(17) 0.05970(12) 0.46004(7) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.314172 -0.000935 0.429423 0.032 Uiso 1 1 calc R U . . .
C7 C 0.28876(15) 0.17928(11) 0.44017(6) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.33449(15) 0.21508(11) 0.37075(6) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.26658(14) 0.33858(11) 0.34509(6) 0.0176(2) Uani 1 1 d . . . . .
C10 C 0.22470(15) 0.54721(11) 0.37626(6) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.06970(16) 0.58392(12) 0.34257(7) 0.0240(3) Uani 1 1 d . . . . .
H11 H -0.018786 0.527908 0.332227 0.029 Uiso 1 1 calc R U . . .
C12 C 0.04434(17) 0.70355(13) 0.32394(7) 0.0272(3) Uani 1 1 d . . . . .
H12 H -0.061399 0.729465 0.300147 0.033 Uiso 1 1 calc R U . . .
C13 C 0.17316(19) 0.78483(12) 0.34005(7) 0.0294(3) Uani 1 1 d . . . . .
H13 H 0.155063 0.866898 0.328180 0.035 Uiso 1 1 calc R U . . .
C14 C 0.32887(19) 0.74692(13) 0.37352(7) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.417300 0.802917 0.384138 0.035 Uiso 1 1 calc R U . . .
C15 C 0.35549(17) 0.62698(12) 0.39152(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H 0.462035 0.600300 0.413971 0.029 Uiso 1 1 calc R U . . .
C16 C 0.52232(15) 0.22283(11) 0.37335(6) 0.0184(2) Uani 1 1 d . . . . .
C17 C 0.64325(16) 0.29065(11) 0.41423(6) 0.0209(3) Uani 1 1 d . . . . .
H17 H 0.616801 0.343357 0.449113 0.025 Uiso 1 1 calc R U . . .
C18 C 0.80632(16) 0.27857(12) 0.40220(7) 0.0246(3) Uani 1 1 d . . . . .
H18 H 0.892511 0.324223 0.429338 0.030 Uiso 1 1 calc R U . . .
C19 C 0.84483(16) 0.20112(13) 0.35132(7) 0.0254(3) Uani 1 1 d . . . . .
H19 H 0.956813 0.194510 0.344387 0.030 Uiso 1 1 calc R U . . .
C20 C 0.72158(16) 0.13292(12) 0.31027(6) 0.0230(3) Uani 1 1 d . . . . .
H20 H 0.747439 0.079953 0.275394 0.028 Uiso 1 1 calc R U . . .
C21 C 0.55949(16) 0.14535(11) 0.32229(6) 0.0194(3) Uani 1 1 d . . . . .
C22 C 0.40199(16) 0.08834(11) 0.29038(6) 0.0202(3) Uani 1 1 d . . . . .
C23 C 0.38779(17) -0.00418(13) 0.23405(7) 0.0276(3) Uani 1 1 d . . . . .
H23A H 0.278206 -0.042392 0.228533 0.041 Uiso 1 1 calc R U . . .
H23B H 0.474651 -0.064792 0.246762 0.041 Uiso 1 1 calc R U . . .
H23C H 0.401214 0.033958 0.189907 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2081(16) . ?
O2 C9 1.2084(15) . ?
N1 C1 1.4062(15) . ?
N1 C9 1.3958(15) . ?
N1 C10 1.4525(15) . ?
N2 C8 1.4777(15) . ?
N2 C22 1.2908(16) . ?
C1 C2 1.4774(17) . ?
C2 C3 1.3984(18) . ?
C2 C7 1.3896(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3863(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3900(18) . ?
C7 C8 1.5137(16) . ?
C8 C9 1.5362(16) . ?
C8 C16 1.5279(16) . ?
C10 C11 1.3809(18) . ?
C10 C15 1.3821(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3898(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3913(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3796(17) . ?
C16 C21 1.3885(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3980(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3894(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3952(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3904(17) . ?
C21 C22 1.4708(17) . ?
C22 C23 1.4937(17) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 N1 C10 116.62(10) . . ?
C9 N1 C1 124.91(10) . . ?
C9 N1 C10 118.31(10) . . ?
C22 N2 C8 108.19(10) . . ?
O1 C1 N1 120.26(12) . . ?
O1 C1 C2 123.07(11) . . ?
N1 C1 C2 116.63(11) . . ?
C3 C2 C1 117.76(11) . . ?
C7 C2 C1 121.53(11) . . ?
C7 C2 C3 120.67(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.82(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.66(13) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.50(13) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.27(13) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 119.06(11) . . ?
C2 C7 C8 119.92(11) . . ?
C6 C7 C8 120.98(11) . . ?
N2 C8 C7 110.84(10) . . ?
N2 C8 C9 109.09(9) . . ?
N2 C8 C16 105.13(9) . . ?
C7 C8 C9 113.23(10) . . ?
C7 C8 C16 112.84(10) . . ?
C16 C8 C9 105.25(9) . . ?
O2 C9 N1 121.25(11) . . ?
O2 C9 C8 122.11(11) . . ?
N1 C9 C8 116.31(10) . . ?
C11 C10 N1 119.60(11) . . ?
C11 C10 C15 121.31(12) . . ?
C15 C10 N1 119.08(11) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.40(12) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.94(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.23(13) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.06(13) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 119.05(12) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C8 131.54(11) . . ?
C17 C16 C21 121.91(12) . . ?
C21 C16 C8 106.54(10) . . ?
C16 C17 H17 121.4 . . ?
C16 C17 C18 117.22(12) . . ?
C18 C17 H17 121.4 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.30(12) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.02(12) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.52(12) . . ?
C21 C20 H20 121.2 . . ?
C16 C21 C20 121.03(12) . . ?
C16 C21 C22 106.62(11) . . ?
C20 C21 C22 132.35(12) . . ?
N2 C22 C21 113.48(11) . . ?
N2 C22 C23 122.63(12) . . ?
C21 C22 C23 123.89(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C1 C2 C3 10.95(19) . . . . ?
O1 C1 C2 C7 -171.12(13) . . . . ?
N1 C1 C2 C3 -166.87(12) . . . . ?
N1 C1 C2 C7 11.06(17) . . . . ?
N1 C10 C11 C12 179.06(11) . . . . ?
N1 C10 C15 C14 -178.28(11) . . . . ?
N2 C8 C9 O2 -31.39(15) . . . . ?
N2 C8 C9 N1 155.10(10) . . . . ?
N2 C8 C16 C17 -179.33(12) . . . . ?
N2 C8 C16 C21 1.94(12) . . . . ?
C1 N1 C9 O2 167.78(11) . . . . ?
C1 N1 C9 C8 -18.65(16) . . . . ?
C1 N1 C10 C11 -99.59(13) . . . . ?
C1 N1 C10 C15 79.83(14) . . . . ?
C1 C2 C3 C4 177.60(13) . . . . ?
C1 C2 C7 C6 -178.43(11) . . . . ?
C1 C2 C7 C8 3.76(18) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C2 C7 C8 N2 -147.33(11) . . . . ?
C2 C7 C8 C9 -24.35(16) . . . . ?
C2 C7 C8 C16 95.07(13) . . . . ?
C3 C2 C7 C6 -0.57(19) . . . . ?
C3 C2 C7 C8 -178.37(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C2 1.0(2) . . . . ?
C5 C6 C7 C8 178.80(12) . . . . ?
C6 C7 C8 N2 34.91(16) . . . . ?
C6 C7 C8 C9 157.88(11) . . . . ?
C6 C7 C8 C16 -82.70(14) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C8 C9 O2 -155.33(11) . . . . ?
C7 C8 C9 N1 31.17(14) . . . . ?
C7 C8 C16 C17 -58.42(17) . . . . ?
C7 C8 C16 C21 122.85(11) . . . . ?
C8 N2 C22 C21 0.46(14) . . . . ?
C8 N2 C22 C23 179.63(11) . . . . ?
C8 C16 C17 C18 -178.46(12) . . . . ?
C8 C16 C21 C20 178.91(11) . . . . ?
C8 C16 C21 C22 -1.67(13) . . . . ?
C9 N1 C1 O1 179.15(12) . . . . ?
C9 N1 C1 C2 -2.96(17) . . . . ?
C9 N1 C10 C11 76.05(15) . . . . ?
C9 N1 C10 C15 -104.54(13) . . . . ?
C9 C8 C16 C17 65.52(16) . . . . ?
C9 C8 C16 C21 -113.21(10) . . . . ?
C10 N1 C1 O1 -5.53(17) . . . . ?
C10 N1 C1 C2 172.35(11) . . . . ?
C10 N1 C9 O2 -7.46(17) . . . . ?
C10 N1 C9 C8 166.10(10) . . . . ?
C10 C11 C12 C13 -0.90(19) . . . . ?
C11 C10 C15 C14 1.13(19) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C10 -0.7(2) . . . . ?
C15 C10 C11 C12 -0.34(19) . . . . ?
C16 C8 C9 O2 80.98(13) . . . . ?
C16 C8 C9 N1 -92.52(12) . . . . ?
C16 C17 C18 C19 -0.22(19) . . . . ?
C16 C21 C22 N2 0.84(14) . . . . ?
C16 C21 C22 C23 -178.32(12) . . . . ?
C17 C16 C21 C20 0.03(18) . . . . ?
C17 C16 C21 C22 179.45(11) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 -0.08(19) . . . . ?
C19 C20 C21 C16 -0.04(18) . . . . ?
C19 C20 C21 C22 -179.29(13) . . . . ?
C20 C21 C22 N2 -179.84(13) . . . . ?
C20 C21 C22 C23 1.0(2) . . . . ?
C21 C16 C17 C18 0.10(18) . . . . ?
C22 N2 C8 C7 -123.67(11) . . . . ?
C22 N2 C8 C9 111.00(11) . . . . ?
C22 N2 C8 C16 -1.45(13) . . . . ?

_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_4j
_database_code_depnum_ccdc_archive 'CCDC 2421586'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-03-20 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   8.9460(2)
_cell_length_b                   14.0474(3)
_cell_length_c                   11.9068(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.636(2)
_cell_angle_gamma                90
_cell_volume                     1454.13(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3476
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0880
_cell_measurement_theta_min      5.5920
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6325
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.445
_diffrn_reflns_theta_min         4.952
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -13.00   1.00    1.00    --  -35.37 136.00 118.00   79
  2  ω    -92.00 -58.00   1.00    1.00    --  -35.37 133.00 -60.00   34
  3  ω     88.00 114.00   1.00    1.92    --  106.81-133.00-127.00   26
  4  ω    109.00 134.00   1.00    1.92    --  106.81 136.00 118.00   25
  5  ω    110.00 135.00   1.00    1.92    --  106.81 133.00 -60.00   25
  6  ω     55.00 106.00   1.00    1.92    --  106.81-136.00  53.00   51
  7  ω    -30.00  -4.00   1.00    1.00    --   35.37 -57.00-180.00   26
  8  ω     17.00 101.00   1.00    1.00    --   35.37  38.00 -30.00   84
  9  ω     10.00  35.00   1.00    1.00    --   35.37 -77.00 -60.00   25
 10  ω    -19.00  43.00   1.00    1.00    --   35.37 -77.00-120.00   62
 11  ω     33.00 100.00   1.00    1.00    --   35.37  57.00   0.00   67
 12  ω     38.00  90.00   1.00    1.92    --  106.81 -95.00-150.00   52
 13  ω     74.00 108.00   1.00    1.92    --  106.81-111.00 -60.00   34
 14  ω     49.00 124.00   1.00    1.92    --  106.81 -61.00-150.00   75
 15  ω     60.00  85.00   1.00    1.92    --  106.81-111.00 -30.00   25
 16  ω     85.00 143.00   1.00    1.92    --  106.81  30.00 120.00   58
 17  ω     90.00 166.00   1.00    1.92    --  106.81  61.00 -30.00   76
 18  ω    125.00 150.00   1.00    1.92    --  106.81 111.00-180.00   25
 19  ω    114.00 172.00   1.00    1.92    --  106.81  77.00   0.00   58
 20  ω    103.00 161.00   1.00    1.92    --  106.81  77.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1257484000
_diffrn_orient_matrix_UB_12      0.0081824000
_diffrn_orient_matrix_UB_13      -0.1128299000
_diffrn_orient_matrix_UB_21      0.0059639000
_diffrn_orient_matrix_UB_22      0.1094069000
_diffrn_orient_matrix_UB_23      0.0104368000
_diffrn_orient_matrix_UB_31      0.1245225000
_diffrn_orient_matrix_UB_32      0.0032471000
_diffrn_orient_matrix_UB_33      -0.0698617000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2393
_reflns_number_total             2757
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.061
_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)+(0.0556P)²+0.3096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.64732(13) 0.41963(9) 0.46012(11) 0.0550(3) Uani 1 1 d . . . . .
N1 N 0.48594(14) 0.19194(9) 0.67598(11) 0.0424(3) Uani 1 1 d . . . . .
N2 N 0.49721(14) 0.31048(9) 0.52675(11) 0.0401(3) Uani 1 1 d . . . . .
C1 C 0.3592(2) 0.05418(12) 0.73887(17) 0.0579(5) Uani 1 1 d . . . . .
H1A H 0.296327 0.013649 0.681850 0.087 Uiso 1 1 calc R U . . .
H1B H 0.317134 0.057052 0.805877 0.087 Uiso 1 1 calc R U . . .
H1C H 0.461812 0.029031 0.760210 0.087 Uiso 1 1 calc R U . . .
C2 C 0.36297(18) 0.15173(10) 0.69022(13) 0.0407(3) Uani 1 1 d . . . . .
C3 C 0.22337(17) 0.21065(10) 0.65277(12) 0.0379(3) Uani 1 1 d . . . . .
C4 C 0.07003(19) 0.19371(12) 0.64858(15) 0.0483(4) Uani 1 1 d . . . . .
H4 H 0.038304 0.137146 0.676281 0.058 Uiso 1 1 calc R U . . .
C5 C -0.03465(18) 0.26390(14) 0.60170(15) 0.0532(4) Uani 1 1 d . . . . .
H5 H -0.138761 0.254091 0.596980 0.064 Uiso 1 1 calc R U . . .
C6 C 0.01312(19) 0.34864(13) 0.56162(15) 0.0502(4) Uani 1 1 d . . . . .
H6 H -0.059580 0.394589 0.530198 0.060 Uiso 1 1 calc R U . . .
C7 C 0.16766(18) 0.36610(11) 0.56758(13) 0.0423(4) Uani 1 1 d . . . . .
H7 H 0.200005 0.423186 0.541586 0.051 Uiso 1 1 calc R U . . .
C8 C 0.27101(16) 0.29569(10) 0.61343(12) 0.0359(3) Uani 1 1 d . . . . .
C9 C 0.44450(16) 0.29004(10) 0.63120(13) 0.0372(3) Uani 1 1 d . . . . .
C10 C 0.53209(16) 0.36345(10) 0.71446(13) 0.0394(3) Uani 1 1 d . . . . .
C11 C 0.5366(2) 0.37736(13) 0.83006(15) 0.0519(4) Uani 1 1 d . . . . .
H11 H 0.480327 0.338961 0.868706 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6283(2) 0.45097(15) 0.88646(16) 0.0624(5) Uani 1 1 d . . . . .
H12 H 0.634231 0.461680 0.964460 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7116(2) 0.50897(14) 0.82830(18) 0.0627(5) Uani 1 1 d . . . . .
H13 H 0.771621 0.558034 0.867764 0.075 Uiso 1 1 calc R U . . .
C14 C 0.70602(18) 0.49443(12) 0.71317(17) 0.0532(4) Uani 1 1 d . . . . .
H14 H 0.760765 0.533223 0.673791 0.064 Uiso 1 1 calc R U . . .
C15 C 0.61652(16) 0.42038(11) 0.65787(14) 0.0407(3) Uani 1 1 d . . . . .
C16 C 0.59268(16) 0.38694(11) 0.53697(14) 0.0401(3) Uani 1 1 d . . . . .
C17 C 0.44219(19) 0.25918(13) 0.41902(14) 0.0488(4) Uani 1 1 d . . . . .
H17A H 0.438403 0.302692 0.355153 0.059 Uiso 1 1 calc R U . . .
H17B H 0.338128 0.237453 0.414948 0.059 Uiso 1 1 calc R U . . .
C18 C 0.5394(3) 0.17513(16) 0.40481(18) 0.0760(6) Uani 1 1 d . . . . .
H18A H 0.497659 0.145442 0.331503 0.114 Uiso 1 1 calc R U . . .
H18B H 0.540131 0.130222 0.465718 0.114 Uiso 1 1 calc R U . . .
H18C H 0.642546 0.195919 0.408125 0.114 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.2239(18) . ?
N1 C2 1.2829(19) . ?
N1 C9 1.4926(18) . ?
N2 C9 1.4588(18) . ?
N2 C16 1.3597(19) . ?
N2 C17 1.452(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.491(2) . ?
C2 C3 1.477(2) . ?
C3 C4 1.381(2) . ?
C3 C8 1.3864(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C8 C9 1.5183(19) . ?
C9 C10 1.515(2) . ?
C10 C11 1.381(2) . ?
C10 C15 1.380(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(2) . ?
C15 C16 1.481(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.499(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 N1 C9 107.77(12) . . ?
C16 N2 C9 113.68(12) . . ?
C16 N2 C17 123.09(13) . . ?
C17 N2 C9 123.03(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 123.67(15) . . ?
N1 C2 C3 113.82(13) . . ?
C3 C2 C1 122.51(14) . . ?
C4 C3 C2 132.55(14) . . ?
C4 C3 C8 121.19(14) . . ?
C8 C3 C2 106.23(12) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.63(15) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.08(15) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.17(16) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.45(15) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C9 107.06(12) . . ?
C7 C8 C3 121.47(14) . . ?
C7 C8 C9 131.46(13) . . ?
N1 C9 C8 104.93(11) . . ?
N1 C9 C10 110.38(12) . . ?
N2 C9 N1 112.53(11) . . ?
N2 C9 C8 113.34(12) . . ?
N2 C9 C10 101.70(11) . . ?
C10 C9 C8 114.19(11) . . ?
C11 C10 C9 129.61(14) . . ?
C15 C10 C9 109.47(13) . . ?
C15 C10 C11 120.93(15) . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.48(17) . . ?
C12 C11 H11 121.3 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.25(18) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.69(17) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 121.1 . . ?
C13 C14 C15 117.89(17) . . ?
C15 C14 H14 121.1 . . ?
C10 C15 C14 121.75(16) . . ?
C10 C15 C16 108.71(13) . . ?
C14 C15 C16 129.54(15) . . ?
O1 C16 N2 125.64(15) . . ?
O1 C16 C15 128.04(15) . . ?
N2 C16 C15 106.32(12) . . ?
N2 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
N2 C17 C18 113.93(15) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 177.00(16) . . . . ?
N1 C2 C3 C8 -0.83(18) . . . . ?
N1 C9 C10 C11 -57.0(2) . . . . ?
N1 C9 C10 C15 122.52(13) . . . . ?
N2 C9 C10 C11 -176.60(15) . . . . ?
N2 C9 C10 C15 2.89(15) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
C1 C2 C3 C8 179.75(15) . . . . ?
C2 N1 C9 N2 -128.03(14) . . . . ?
C2 N1 C9 C8 -4.35(15) . . . . ?
C2 N1 C9 C10 119.12(13) . . . . ?
C2 C3 C4 C5 -176.37(16) . . . . ?
C2 C3 C8 C7 177.43(13) . . . . ?
C2 C3 C8 C9 -2.03(15) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C3 C8 C9 N1 3.84(15) . . . . ?
C3 C8 C9 N2 127.00(13) . . . . ?
C3 C8 C9 C10 -117.15(13) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C4 C3 C8 C9 179.83(14) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C6 C7 C8 C3 -0.3(2) . . . . ?
C6 C7 C8 C9 179.02(15) . . . . ?
C7 C8 C9 N1 -175.55(15) . . . . ?
C7 C8 C9 N2 -52.4(2) . . . . ?
C7 C8 C9 C10 63.5(2) . . . . ?
C8 C3 C4 C5 1.2(2) . . . . ?
C8 C9 C10 C11 61.0(2) . . . . ?
C8 C9 C10 C15 -119.56(13) . . . . ?
C9 N1 C2 C1 -177.24(15) . . . . ?
C9 N1 C2 C3 3.34(17) . . . . ?
C9 N2 C16 O1 -177.43(14) . . . . ?
C9 N2 C16 C15 3.07(16) . . . . ?
C9 N2 C17 C18 -92.45(19) . . . . ?
C9 C10 C11 C12 179.80(15) . . . . ?
C9 C10 C15 C14 179.12(13) . . . . ?
C9 C10 C15 C16 -1.28(16) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C15 C16 O1 179.51(15) . . . . ?
C10 C15 C16 N2 -1.01(16) . . . . ?
C11 C10 C15 C14 -1.3(2) . . . . ?
C11 C10 C15 C16 178.26(14) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
C13 C14 C15 C16 -178.13(15) . . . . ?
C14 C15 C16 O1 -0.9(3) . . . . ?
C14 C15 C16 N2 178.55(15) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C16 N2 C9 N1 -121.79(13) . . . . ?
C16 N2 C9 C8 119.34(13) . . . . ?
C16 N2 C9 C10 -3.70(15) . . . . ?
C16 N2 C17 C18 93.1(2) . . . . ?
C17 N2 C9 N1 63.33(18) . . . . ?
C17 N2 C9 C8 -55.54(18) . . . . ?
C17 N2 C9 C10 -178.57(13) . . . . ?
C17 N2 C16 O1 -2.6(2) . . . . ?
C17 N2 C16 C15 177.95(13) . . . . ?

_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.680
