# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
# 
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data_202105134
_database_code_depnum_ccdc_archive 'CCDC 2163815'
loop_
_audit_author_name
_audit_author_address
'Xiang Zhao'
;Huaqiao University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N2'
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2335(11)
_cell_length_b                   10.0272(9)
_cell_length_c                   10.7951(9)
_cell_angle_alpha                88.861(7)
_cell_angle_beta                 77.287(9)
_cell_angle_gamma                65.410(10)
_cell_volume                     883.65(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5130
_cell_measurement_theta_min      4.1990
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6224
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         4.212
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  38.00   1.00    1.00    --  -33.50   0.00-180.00  143
  2  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -60.00   53
  3  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00  60.00   81
  4  ω    -34.00  59.00   1.00    1.00    --   36.47 -37.00 -60.00   93
  5  ω     14.00 107.00   1.00    1.00    --   36.47  37.00  30.00   93
  6  ω     24.00  97.00   1.00    1.00    --   36.47-134.00 -34.00   73
  7  ω    -34.00  59.00   1.00    1.00    --   36.47 -37.00 150.00   93
  8  ω     18.00 105.00   1.00    1.00    --   36.47  57.00  90.00   87
  9  ω     18.00 105.00   1.00    1.00    --   36.47  57.00-180.00   87
 10  ω    151.00 177.00   1.00    3.00    --  108.00  30.00  60.00   26
 11  ω     82.00 108.00   1.00    3.00    --  108.00  30.00  60.00   26
 12  ω     40.00  66.00   1.00    3.00    --  108.00-111.00 150.00   26
 13  ω     56.00 109.00   1.00    3.00    --  108.00 -94.00   0.00   53
 14  ω     50.00 122.00   1.00    3.00    --  108.00 -30.00 120.00   72
 15  ω     39.00 148.00   1.00    3.00    --  108.00 -15.00 -30.00  109
 16  ω     91.00 173.00   1.00    3.00    --  108.00  45.00 -30.00   82
 17  ω     38.00 109.00   1.00    3.00    --  108.00 -94.00 -90.00   71
 18  ω     40.00 124.00   1.00    3.00    --  108.00 -45.00-120.00   84
 19  ω     42.00 121.00   1.00    3.00    --  108.00 -61.00   0.00   79
 20  ω     58.00 128.00   1.00    3.00    --  108.00 -61.00 120.00   70
 21  ω    145.00 173.00   1.00    3.00    --  108.00  61.00 150.00   28
 22  ω     83.00 112.00   1.00    3.00    --  108.00-111.00 150.00   29
 23  ω     90.00 120.00   1.00    3.00    --  108.00  61.00 150.00   30
 24  ω     88.00 135.00   1.00    3.00    --  108.00 -77.00  30.00   47
 25  ω     66.00 105.00   1.00    3.00    --  108.00-111.00-120.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0420055000
_diffrn_orient_matrix_UB_12      -0.0136382000
_diffrn_orient_matrix_UB_13      -0.1467662000
_diffrn_orient_matrix_UB_21      -0.1213327000
_diffrn_orient_matrix_UB_22      -0.0691153000
_diffrn_orient_matrix_UB_23      0.0015165000
_diffrn_orient_matrix_UB_31      -0.1382486000
_diffrn_orient_matrix_UB_32      0.1541838000
_diffrn_orient_matrix_UB_33      0.0007416000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             3147
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0086(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0495
_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)+(0.0703P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1483
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
N1 N 0.3551(2) 0.27723(18) 0.59329(15) 0.0506(4) Uani 1 1 d . . . . .
N2 N 0.30175(19) 0.25561(16) 0.49078(14) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.2859(3) -0.0466(2) 0.6725(2) 0.0548(5) Uani 1 1 d . . . . .
H1 H 0.2520 -0.1093 0.6370 0.066 Uiso 1 1 calc R . . . .
C2 C 0.3247(3) -0.0685(2) 0.7881(2) 0.0626(6) Uani 1 1 d . . . . .
H2 H 0.3141 -0.1458 0.8323 0.075 Uiso 1 1 calc R . . . .
C3 C 0.3800(3) 0.0217(2) 0.8425(2) 0.0611(6) Uani 1 1 d . . . . .
H3 H 0.4074 0.0017 0.9208 0.073 Uiso 1 1 calc R . . . .
C4 C 0.3945(3) 0.1378(2) 0.78320(19) 0.0570(5) Uani 1 1 d . . . . .
H4 H 0.4313 0.1972 0.8200 0.068 Uiso 1 1 calc R . . . .
C5 C 0.3521(2) 0.1659(2) 0.66407(18) 0.0469(5) Uani 1 1 d . . . . .
C6 C 0.2983(2) 0.0736(2) 0.60758(17) 0.0447(4) Uani 1 1 d . . . . .
C7 C 0.2682(2) 0.13446(19) 0.49235(17) 0.0426(4) Uani 1 1 d . . . . .
C8 C 0.2197(2) 0.0986(2) 0.38551(18) 0.0445(4) Uani 1 1 d . . . . .
C9 C 0.1911(3) -0.0272(2) 0.3767(2) 0.0579(6) Uani 1 1 d . . . . .
H9 H 0.2017 -0.0886 0.4430 0.069 Uiso 1 1 calc R . . . .
C10 C 0.1481(3) -0.0612(3) 0.2726(2) 0.0711(7) Uani 1 1 d . . . . .
H10 H 0.1302 -0.1454 0.2681 0.085 Uiso 1 1 calc R . . . .
C11 C 0.1311(3) 0.0309(3) 0.1730(2) 0.0709(7) Uani 1 1 d . . . . .
H11 H 0.1017 0.0079 0.1021 0.085 Uiso 1 1 calc R . . . .
C12 C 0.1575(3) 0.1551(3) 0.1791(2) 0.0578(5) Uani 1 1 d . . . . .
H12 H 0.1445 0.2159 0.1124 0.069 Uiso 1 1 calc R . . . .
C13 C 0.2038(2) 0.1921(2) 0.28439(18) 0.0448(4) Uani 1 1 d . . . . .
C14 C 0.2358(2) 0.3210(2) 0.29237(18) 0.0454(5) Uani 1 1 d . . . . .
C15 C 0.2848(2) 0.3515(2) 0.39360(17) 0.0451(5) Uani 1 1 d . . . . .
C16 C 0.3197(3) 0.4800(2) 0.41303(19) 0.0522(5) Uani 1 1 d . . . . .
C17 C 0.4537(3) 0.4864(3) 0.3472(2) 0.0671(6) Uani 1 1 d . . . . .
H17A H 0.5283 0.4098 0.2874 0.081 Uiso 1 1 calc R . . . .
H17B H 0.4743 0.5677 0.3603 0.081 Uiso 1 1 calc R . . . .
C18 C 0.1931(4) 0.6003(3) 0.5103(3) 0.0796(8) Uani 1 1 d . . . . .
H18A H 0.0934 0.6453 0.4816 0.119 Uiso 1 1 calc GR . . . .
H18B H 0.2325 0.6731 0.5215 0.119 Uiso 1 1 calc GR . . . .
H18C H 0.1726 0.5595 0.5900 0.119 Uiso 1 1 calc GR . . . .
C19 C 0.2140(3) 0.4227(2) 0.18755(19) 0.0485(5) Uani 1 1 d . . . . .
C20 C 0.0740(3) 0.5519(3) 0.1995(2) 0.0711(7) Uani 1 1 d . . . . .
H20 H -0.0089 0.5759 0.2734 0.085 Uiso 1 1 calc R . . . .
C21 C 0.0554(3) 0.6463(3) 0.1028(3) 0.0831(8) Uani 1 1 d . . . . .
H21 H -0.0393 0.7332 0.1125 0.100 Uiso 1 1 calc R . . . .
C22 C 0.1757(4) 0.6122(3) -0.0067(3) 0.0769(8) Uani 1 1 d . . . . .
H22 H 0.1635 0.6755 -0.0717 0.092 Uiso 1 1 calc R . . . .
C23 C 0.3139(4) 0.4840(3) -0.0194(2) 0.0763(7) Uani 1 1 d . . . . .
H23 H 0.3958 0.4599 -0.0939 0.092 Uiso 1 1 calc R . . . .
C24 C 0.3340(3) 0.3898(3) 0.0767(2) 0.0662(6) Uani 1 1 d . . . . .
H24 H 0.4293 0.3034 0.0666 0.079 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
N1 N2 1.361(2) . ?
N1 C5 1.346(2) . ?
N2 C7 1.372(2) . ?
N2 C15 1.399(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.362(3) . ?
C1 C6 1.415(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.415(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.406(2) . ?
C7 C8 1.428(3) . ?
C8 C9 1.401(3) . ?
C8 C13 1.417(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.364(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.406(3) . ?
C13 C14 1.448(3) . ?
C14 C15 1.356(3) . ?
C14 C19 1.498(3) . ?
C15 C16 1.481(3) . ?
C16 C17 1.311(3) . ?
C16 C18 1.504(3) . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.381(3) . ?
C19 C24 1.377(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(3) . ?
C24 H24 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
C5 N1 N2 103.04(16) . . ?
N1 N2 C7 114.50(15) . . ?
N1 N2 C15 121.04(16) . . ?
C7 N2 C15 124.46(16) . . ?
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.5(2) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.0(2) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 126.51(19) . . ?
N1 C5 C6 112.87(17) . . ?
C4 C5 C6 120.62(19) . . ?
C1 C6 C5 119.20(18) . . ?
C7 C6 C1 136.28(19) . . ?
C7 C6 C5 104.51(16) . . ?
N2 C7 C6 105.06(16) . . ?
N2 C7 C8 118.46(17) . . ?
C6 C7 C8 136.45(18) . . ?
C9 C8 C7 122.06(18) . . ?
C9 C8 C13 119.41(18) . . ?
C13 C8 C7 118.52(18) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C14 119.51(18) . . ?
C12 C13 C8 118.06(19) . . ?
C12 C13 C14 122.43(19) . . ?
C13 C14 C19 119.64(17) . . ?
C15 C14 C13 121.04(17) . . ?
C15 C14 C19 119.32(18) . . ?
N2 C15 C16 116.02(17) . . ?
C14 C15 N2 117.95(18) . . ?
C14 C15 C16 126.02(17) . . ?
C15 C16 C18 116.29(19) . . ?
C17 C16 C15 120.8(2) . . ?
C17 C16 C18 122.9(2) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C14 121.08(19) . . ?
C24 C19 C14 120.70(18) . . ?
C24 C19 C20 118.2(2) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.1(2) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 120.6(2) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?

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 N2 C7 C6 1.6(2) . . . . ?
N1 N2 C7 C8 -176.79(16) . . . . ?
N1 N2 C15 C14 178.03(17) . . . . ?
N1 N2 C15 C16 -3.1(3) . . . . ?
N1 C5 C6 C1 -178.80(18) . . . . ?
N1 C5 C6 C7 0.6(2) . . . . ?
N2 N1 C5 C4 -179.08(19) . . . . ?
N2 N1 C5 C6 0.3(2) . . . . ?
N2 C7 C8 C9 176.78(18) . . . . ?
N2 C7 C8 C13 -1.8(3) . . . . ?
N2 C15 C16 C17 107.1(2) . . . . ?
N2 C15 C16 C18 -73.4(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C1 C6 C7 N2 178.0(2) . . . . ?
C1 C6 C7 C8 -4.0(4) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -178.5(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 N1 178.4(2) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.95(17) . . . . ?
C5 N1 N2 C7 -1.2(2) . . . . ?
C5 N1 N2 C15 179.05(16) . . . . ?
C5 C6 C7 N2 -1.3(2) . . . . ?
C5 C6 C7 C8 176.7(2) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C6 C7 C8 C13 -179.5(2) . . . . ?
C7 N2 C15 C14 -1.7(3) . . . . ?
C7 N2 C15 C16 177.15(17) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C7 C8 C13 C12 179.40(17) . . . . ?
C7 C8 C13 C14 -0.5(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C13 C14 C15 1.7(3) . . . . ?
C8 C13 C14 C19 -178.06(17) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C8 C13 C14 -179.03(18) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C11 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 -178.12(18) . . . . ?
C12 C13 C14 C19 2.1(3) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C13 C14 C15 N2 -0.7(3) . . . . ?
C13 C14 C15 C16 -179.43(18) . . . . ?
C13 C14 C19 C20 99.6(3) . . . . ?
C13 C14 C19 C24 -80.8(3) . . . . ?
C14 C15 C16 C17 -74.1(3) . . . . ?
C14 C15 C16 C18 105.4(2) . . . . ?
C14 C19 C20 C21 179.3(2) . . . . ?
C14 C19 C24 C23 -179.7(2) . . . . ?
C15 N2 C7 C6 -178.65(16) . . . . ?
C15 N2 C7 C8 3.0(3) . . . . ?
C15 C14 C19 C20 -80.2(3) . . . . ?
C15 C14 C19 C24 99.4(3) . . . . ?
C19 C14 C15 N2 179.09(16) . . . . ?
C19 C14 C15 C16 0.4(3) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C20 C19 C24 C23 0.0(4) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 -0.5(5) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C24 C19 C20 C21 -0.4(4) . . . . ?

_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 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.906
####################################################################### 
# 
# 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_20210127
_database_code_depnum_ccdc_archive 'CCDC 2163816'
loop_
_audit_author_name
_audit_author_address
'xiang zhao'
;Huaqiao University
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-23 downloaded from the CCDC.
;
_audit_creation_date             2021-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 N2'
_chemical_formula_sum            'C24 H20 N2'
_chemical_formula_weight         336.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.5537(10)
_cell_length_b                   8.6676(3)
_cell_length_c                   20.5338(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3658.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0120
_cell_measurement_theta_min      4.2850
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9387
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.302
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -17.00   1.00    1.75    --  -33.50 -77.00-180.00   85
  2  ω    -26.00  10.00   1.00    1.75    --   36.47 -57.00-180.00   36
  3  ω     26.00  53.00   1.00    1.75    --   36.47 -57.00-180.00   27
  4  ω     80.00 106.00   1.00    1.75    --   36.47 178.00-150.00   26
  5  ω     11.00  65.00   1.00    1.75    --   36.47  77.00   0.00   54
  6  ω    124.00 173.00   1.00    6.50    --  108.00 111.00-150.00   49
  7  ω     88.00 176.00   1.00    6.50    --  108.00  61.00 -30.00   88
  8  ω     77.00 120.00   1.00    6.50    --  108.00 -61.00-150.00   43
  9  ω     67.00  97.00   1.00    6.50    --  108.00 -94.00 -30.00   30
 10  ω     48.00 109.00   1.00    6.50    --  108.00 -94.00-150.00   61
 11  ω   -108.00 -74.00   1.00    2.00    --  -33.50 178.00  60.00   34
 12  ω     46.00  73.00   1.00    2.00    --   36.47  57.00   0.00   27
 13  ω     38.00  64.00   1.00    2.00    --   36.47 -77.00   0.00   26
 14  ω     39.00  67.00   1.00    6.50    --  108.00 -45.00 -60.00   28
 15  ω     90.00 119.00   1.00    6.50    --  108.00 -45.00 -60.00   29
 16  ω     78.00 104.00   1.00    6.50    --  108.00 -30.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0569911000
_diffrn_orient_matrix_UB_12      0.0284703000
_diffrn_orient_matrix_UB_13      0.0472252000
_diffrn_orient_matrix_UB_21      0.0463232000
_diffrn_orient_matrix_UB_22      0.0854494000
_diffrn_orient_matrix_UB_23      0.0466928000
_diffrn_orient_matrix_UB_31      -0.0151696000
_diffrn_orient_matrix_UB_32      0.1532379000
_diffrn_orient_matrix_UB_33      -0.0348112000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2473
_reflns_number_total             3273
_reflns_odcompleteness_completeness 99.79
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.00115(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.035
_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)+(0.0590P)²+0.2341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1216
_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 Ternary CH refined with riding coordinates:
 C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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
N1 N 0.55604(6) 0.42861(14) 0.38279(6) 0.0452(3) Uani 1 1 d . . . . .
N2 N 0.61989(7) 0.41143(15) 0.39800(7) 0.0507(3) Uani 1 1 d . . . . .
C1 C 0.62729(9) 0.75565(19) 0.29879(8) 0.0536(4) Uani 1 1 d . . . . .
H1 H 0.5988 0.8187 0.2757 0.064 Uiso 1 1 calc R . . . .
C2 C 0.69218(9) 0.7869(2) 0.30031(9) 0.0589(5) Uani 1 1 d . . . . .
H2 H 0.7079 0.8714 0.2773 0.071 Uiso 1 1 calc R . . . .
C3 C 0.73623(9) 0.6947(2) 0.33577(9) 0.0584(4) Uani 1 1 d . . . . .
H3 H 0.7801 0.7207 0.3362 0.070 Uiso 1 1 calc R . . . .
C4 C 0.71574(8) 0.5682(2) 0.36944(9) 0.0546(4) Uani 1 1 d . . . . .
H4 H 0.7450 0.5078 0.3928 0.065 Uiso 1 1 calc R . . . .
C5 C 0.64867(8) 0.53164(17) 0.36788(8) 0.0466(4) Uani 1 1 d . . . . .
C6 C 0.60402(8) 0.62513(17) 0.33307(7) 0.0453(4) Uani 1 1 d . . . . .
C7 C 0.54305(8) 0.55554(17) 0.34361(7) 0.0443(4) Uani 1 1 d . . . . .
C8 C 0.47726(8) 0.58830(17) 0.32615(7) 0.0457(4) Uani 1 1 d . . . . .
C9 C 0.46010(9) 0.7159(2) 0.28754(9) 0.0575(4) Uani 1 1 d . . . . .
H9 H 0.4925 0.7797 0.2709 0.069 Uiso 1 1 calc R . . . .
C10 C 0.39624(10) 0.7472(2) 0.27419(9) 0.0641(5) Uani 1 1 d . . . . .
H10 H 0.3855 0.8316 0.2484 0.077 Uiso 1 1 calc R . . . .
C11 C 0.34740(9) 0.6532(2) 0.29906(9) 0.0617(5) Uani 1 1 d . . . . .
H11 H 0.3040 0.6764 0.2907 0.074 Uiso 1 1 calc R . . . .
C12 C 0.36298(9) 0.5262(2) 0.33589(8) 0.0533(4) Uani 1 1 d . . . . .
H12 H 0.3299 0.4632 0.3517 0.064 Uiso 1 1 calc R . . . .
C13 C 0.42801(8) 0.49003(18) 0.35008(7) 0.0447(4) Uani 1 1 d . . . . .
C14 C 0.44546(8) 0.35655(17) 0.38904(7) 0.0453(4) Uani 1 1 d . . . . .
C15 C 0.50836(8) 0.32629(17) 0.40513(8) 0.0459(4) Uani 1 1 d . . . . .
C16 C 0.39173(8) 0.25273(17) 0.41151(8) 0.0481(4) Uani 1 1 d . . . . .
C17 C 0.37226(10) 0.1283(2) 0.37429(10) 0.0653(5) Uani 1 1 d . . . . .
H17 H 0.3938 0.1061 0.3356 0.078 Uiso 1 1 calc R . . . .
C18 C 0.32087(11) 0.0366(2) 0.39430(12) 0.0774(6) Uani 1 1 d . . . . .
H18 H 0.3080 -0.0468 0.3689 0.093 Uiso 1 1 calc R . . . .
C19 C 0.28894(10) 0.0680(2) 0.45130(12) 0.0760(6) Uani 1 1 d . . . . .
H19 H 0.2545 0.0061 0.4647 0.091 Uiso 1 1 calc R . . . .
C20 C 0.30800(11) 0.1906(2) 0.48826(11) 0.0739(6) Uani 1 1 d . . . . .
H20 H 0.2862 0.2124 0.5269 0.089 Uiso 1 1 calc R . . . .
C21 C 0.35914(10) 0.2824(2) 0.46897(9) 0.0617(5) Uani 1 1 d . . . . .
H21 H 0.3719 0.3651 0.4949 0.074 Uiso 1 1 calc R . . . .
C22 C 0.52935(9) 0.19037(18) 0.44606(9) 0.0542(4) Uani 1 1 d . . . . .
H22 H 0.4894 0.1334 0.4561 0.065 Uiso 1 1 calc R . . . .
C23 C 0.55761(12) 0.2390(3) 0.51174(10) 0.0814(7) Uani 1 1 d . . . . .
H23A H 0.5291 0.3124 0.5320 0.122 Uiso 1 1 calc GR . . . .
H23B H 0.5996 0.2851 0.5052 0.122 Uiso 1 1 calc GR . . . .
H23C H 0.5619 0.1500 0.5393 0.122 Uiso 1 1 calc GR . . . .
C24 C 0.57288(11) 0.0773(2) 0.40952(13) 0.0807(7) Uani 1 1 d . . . . .
H24A H 0.6147 0.1237 0.4022 0.121 Uiso 1 1 calc GR . . . .
H24B H 0.5533 0.0520 0.3685 0.121 Uiso 1 1 calc GR . . . .
H24C H 0.5781 -0.0148 0.4349 0.121 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3571(18) . ?
N1 C7 1.3889(19) . ?
N1 C15 1.399(2) . ?
N2 C5 1.348(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(3) . ?
C1 C6 1.416(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.410(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.415(2) . ?
C5 C6 1.418(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.428(2) . ?
C8 C9 1.406(2) . ?
C8 C13 1.411(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.403(2) . ?
C13 C14 1.451(2) . ?
C14 C15 1.360(2) . ?
C14 C16 1.497(2) . ?
C15 C22 1.510(2) . ?
C16 C17 1.381(2) . ?
C16 C21 1.381(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9800 . ?
C22 C23 1.528(3) . ?
C22 C24 1.524(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
N2 N1 C7 113.96(13) . . ?
N2 N1 C15 122.16(13) . . ?
C7 N1 C15 123.88(14) . . ?
C5 N2 N1 103.52(13) . . ?
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.58(17) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 121.90(16) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.27(17) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.04(17) . . ?
C5 C4 H4 121.0 . . ?
N2 C5 C4 126.19(16) . . ?
N2 C5 C6 112.89(15) . . ?
C4 C5 C6 120.92(15) . . ?
C1 C6 C5 119.26(15) . . ?
C7 C6 C1 136.03(16) . . ?
C7 C6 C5 104.71(13) . . ?
N1 C7 C6 104.91(14) . . ?
N1 C7 C8 119.02(14) . . ?
C6 C7 C8 136.02(14) . . ?
C9 C8 C7 122.40(15) . . ?
C9 C8 C13 119.43(16) . . ?
C13 C8 C7 118.16(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.63(17) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.21(17) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.26(17) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.02(17) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C14 119.72(15) . . ?
C12 C13 C8 118.43(15) . . ?
C12 C13 C14 121.85(15) . . ?
C13 C14 C16 117.82(14) . . ?
C15 C14 C13 121.50(15) . . ?
C15 C14 C16 120.68(14) . . ?
N1 C15 C22 118.49(14) . . ?
C14 C15 N1 117.64(14) . . ?
C14 C15 C22 123.87(15) . . ?
C17 C16 C14 120.82(15) . . ?
C21 C16 C14 120.61(15) . . ?
C21 C16 C17 118.53(17) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.36(19) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.54(19) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.7(2) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.56(18) . . ?
C20 C21 H21 119.7 . . ?
C15 C22 H22 105.7 . . ?
C15 C22 C23 112.63(15) . . ?
C15 C22 C24 113.28(15) . . ?
C23 C22 H22 105.7 . . ?
C24 C22 H22 105.7 . . ?
C24 C22 C23 112.86(18) . . ?
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 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 N2 C5 C4 178.84(16) . . . . ?
N1 N2 C5 C6 -0.46(18) . . . . ?
N1 C7 C8 C9 178.97(14) . . . . ?
N1 C7 C8 C13 0.5(2) . . . . ?
N1 C15 C22 C23 65.6(2) . . . . ?
N1 C15 C22 C24 -64.0(2) . . . . ?
N2 N1 C7 C6 -0.05(17) . . . . ?
N2 N1 C7 C8 -177.99(14) . . . . ?
N2 N1 C15 C14 177.78(14) . . . . ?
N2 N1 C15 C22 -1.6(2) . . . . ?
N2 C5 C6 C1 -179.83(14) . . . . ?
N2 C5 C6 C7 0.44(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C7 N1 -179.88(17) . . . . ?
C1 C6 C7 C8 -2.5(3) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C1 C6 C7 179.79(18) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 N2 179.86(16) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -178.90(15) . . . . ?
C5 C6 C7 N1 -0.22(16) . . . . ?
C5 C6 C7 C8 177.19(18) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C6 C7 C8 C13 -176.68(17) . . . . ?
C7 N1 N2 C5 0.31(17) . . . . ?
C7 N1 C15 C14 -2.2(2) . . . . ?
C7 N1 C15 C22 178.44(14) . . . . ?
C7 C8 C9 C10 -177.15(17) . . . . ?
C7 C8 C13 C12 176.75(14) . . . . ?
C7 C8 C13 C14 -2.5(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C8 C13 C14 C15 2.3(2) . . . . ?
C8 C13 C14 C16 -178.02(14) . . . . ?
C9 C8 C13 C12 -1.8(2) . . . . ?
C9 C8 C13 C14 178.95(14) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C11 C12 C13 C14 179.85(16) . . . . ?
C12 C13 C14 C15 -176.88(15) . . . . ?
C12 C13 C14 C16 2.8(2) . . . . ?
C13 C8 C9 C10 1.3(3) . . . . ?
C13 C14 C15 N1 0.0(2) . . . . ?
C13 C14 C15 C22 179.33(14) . . . . ?
C13 C14 C16 C17 90.5(2) . . . . ?
C13 C14 C16 C21 -87.4(2) . . . . ?
C14 C15 C22 C23 -113.7(2) . . . . ?
C14 C15 C22 C24 116.66(19) . . . . ?
C14 C16 C17 C18 -177.49(18) . . . . ?
C14 C16 C21 C20 177.31(18) . . . . ?
C15 N1 N2 C5 -179.66(14) . . . . ?
C15 N1 C7 C6 179.92(13) . . . . ?
C15 N1 C7 C8 2.0(2) . . . . ?
C15 C14 C16 C17 -89.8(2) . . . . ?
C15 C14 C16 C21 92.3(2) . . . . ?
C16 C14 C15 N1 -179.64(13) . . . . ?
C16 C14 C15 C22 -0.3(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C16 C21 C20 -0.6(3) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
C21 C16 C17 C18 0.4(3) . . . . ?

_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 1.133
_oxdiff_exptl_absorpt_empirical_full_min 0.923
