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

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

data_exp_11734
_database_code_depnum_ccdc_archive 'CCDC 2192315'
loop_
_audit_author_name
_audit_author_address
CuiBo
;Huaqiao University
China
;
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2024-01-22 downloaded from the CCDC.
;
_audit_creation_date             2022-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 O'
_chemical_formula_sum            'C23 H17 N3 O'
_chemical_formula_weight         351.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8882(10)
_cell_length_b                   9.6114(14)
_cell_length_c                   17.595(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.512(10)
_cell_angle_gamma                90
_cell_volume                     1821.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5600
_cell_measurement_theta_min      4.2200
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45050
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.17
_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  0.0427
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7901
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.499
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  46.00   1.00    7.50    --  -16.28  57.00 -30.00   77
  2  ω     12.00  82.00   1.00    7.50    --   15.49  38.00-120.00   70
  3  ω     42.00  67.00   1.00    7.50    --   15.49 178.00   0.00   25
  4  ω    -25.00  23.00   1.00    7.50    --  -16.28 -99.00 120.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0535324000
_diffrn_orient_matrix_UB_12      0.0378255000
_diffrn_orient_matrix_UB_13      -0.0160491000
_diffrn_orient_matrix_UB_21      -0.0018641000
_diffrn_orient_matrix_UB_22      -0.0375551000
_diffrn_orient_matrix_UB_23      -0.0348746000
_diffrn_orient_matrix_UB_31      -0.0383320000
_diffrn_orient_matrix_UB_32      -0.0510083000
_diffrn_orient_matrix_UB_33      0.0137396000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1743
_reflns_number_total             3708
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.141
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.055
_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)+(0.0521P)²+0.2417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1885
_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. Restrained distances
 C10A-C7A
 2.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7A) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C8) = Uanis(C8A)
Uanis(N1) = Uanis(N1A)
Uanis(C7) = Uanis(C7A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C6) = Uanis(C6A)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C15) = Uanis(C15A)
Uanis(O1) = Uanis(O1A)
Uanis(N2) = Uanis(N2A)
Uanis(N3) = Uanis(N3A)
4. Others
 Sof(O1A)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(C6A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=
 Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(H1A)=Sof(C7A)=
 Sof(C8A)=Sof(C9A)=Sof(C14A)=Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=
 Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(C15A)=Sof(C16A)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(N2)=Sof(N3)=Sof(C6)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C7)=Sof(C8)=Sof(C9)=
 Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14)=Sof(C15)=Sof(C16)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C1(H1), C2(H2), C3(H3),
 C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C5A(H5A), C4A(H4A),
 C3A(H3A), C2A(H2A), C1A(H1A), C14A(H14A), C13A(H13A), C12A(H12A), C11A(H11A)
5.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C9(C10,C11,C12,C13,C14), C6A(C5A,C4A,C3A,C2A,C1A),
 C9A(C14A,C13A,C12A,C11A,C10A)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F)
;
_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
C18 C 0.6471(3) 0.0460(3) 0.33293(17) 0.0520(8) Uani 1 1 d . . . . .
C19 C 0.7335(3) 0.0316(4) 0.2836(2) 0.0687(10) Uani 1 1 d . . . . .
H19 H 0.808403 0.079608 0.292762 0.082 Uiso 1 1 calc R . . . .
C20 C 0.7081(4) -0.0547(4) 0.2205(2) 0.0790(11) Uani 1 1 d . . . . .
H20 H 0.766183 -0.064652 0.187097 0.095 Uiso 1 1 calc R . . . .
C21 C 0.5992(4) -0.1250(4) 0.2069(2) 0.0857(12) Uani 1 1 d . . . . .
H21 H 0.583379 -0.183953 0.164712 0.103 Uiso 1 1 calc R . . . .
C22 C 0.5124(4) -0.1095(4) 0.2551(3) 0.0876(12) Uani 1 1 d . . . . .
H22 H 0.437357 -0.157027 0.245182 0.105 Uiso 1 1 calc R . . . .
C23 C 0.5359(3) -0.0237(4) 0.3183(2) 0.0671(10) Uani 1 1 d . . . . .
H23 H 0.476673 -0.012962 0.350932 0.081 Uiso 1 1 calc R . . . .
O1 O 0.8858(5) 0.1221(5) 0.4303(3) 0.0670(14) Uani 0.610(2) 1 d . . P A 1
N1 N 0.8838(6) 0.3548(6) 0.6119(4) 0.0527(14) Uani 0.610(2) 1 d . . P A 1
N2 N 0.6763(17) 0.123(2) 0.4071(6) 0.046(2) Uani 0.610(2) 1 d . . P A 1
N3 N 0.5811(14) 0.171(3) 0.4427(9) 0.047(2) Uani 0.610(2) 1 d . . P A 1
C6 C 0.8113(5) 0.4818(4) 0.4964(3) 0.0431(15) Uani 0.610(2) 1 d . . P A 1
C1 C 0.7423(4) 0.4803(4) 0.4233(4) 0.0556(16) Uani 0.610(2) 1 d G . P A 1
H1 H 0.701062 0.399623 0.404774 0.067 Uiso 0.610(2) 1 calc R . P A 1
C2 C 0.7349(4) 0.5992(6) 0.3779(2) 0.0675(18) Uani 0.610(2) 1 d G . P A 1
H2 H 0.688700 0.598153 0.329025 0.081 Uiso 0.610(2) 1 calc R . P A 1
C3 C 0.7965(5) 0.7197(4) 0.4056(3) 0.0601(16) Uani 0.610(2) 1 d G . P A 1
H3 H 0.791517 0.799286 0.375249 0.072 Uiso 0.610(2) 1 calc R . P A 1
C4 C 0.8655(5) 0.7213(4) 0.4787(3) 0.0568(18) Uani 0.610(2) 1 d G . P A 1
H4 H 0.906696 0.801892 0.497223 0.068 Uiso 0.610(2) 1 calc R . P A 1
C5 C 0.8729(4) 0.6023(6) 0.5241(2) 0.0618(15) Uani 0.610(2) 1 d G . P A 1
H5 H 0.919060 0.603364 0.572974 0.074 Uiso 0.610(2) 1 calc R . P A 1
C7 C 0.8208(7) 0.3576(6) 0.5445(4) 0.0443(15) Uani 0.610(2) 1 d . U P A 1
C8 C 0.7536(4) 0.2199(5) 0.5204(3) 0.0439(11) Uani 0.610(2) 1 d . . P A 1
C9 C 0.7978(4) 0.1366(6) 0.59120(18) 0.0430(14) Uani 0.610(2) 1 d . . P A 1
C10 C 0.8748(4) 0.2186(3) 0.6431(3) 0.0523(16) Uani 0.610(2) 1 d G . P A 1
C11 C 0.9280(4) 0.1636(5) 0.7134(3) 0.0662(18) Uani 0.610(2) 1 d G . P A 1
H11 H 0.979509 0.218444 0.748134 0.079 Uiso 0.610(2) 1 calc R . P A 1
C12 C 0.9043(5) 0.0265(5) 0.7317(2) 0.071(2) Uani 0.610(2) 1 d G . P A 1
H12 H 0.939886 -0.010399 0.778723 0.085 Uiso 0.610(2) 1 calc R . P A 1
C13 C 0.8273(5) -0.0556(3) 0.6798(3) 0.0737(18) Uani 0.610(2) 1 d G . P A 1
H13 H 0.811420 -0.147315 0.692051 0.088 Uiso 0.610(2) 1 calc R . P A 1
C14 C 0.7741(4) -0.0005(5) 0.6095(3) 0.0558(16) Uani 0.610(2) 1 d G . P A 1
H14 H 0.722577 -0.055389 0.574788 0.067 Uiso 0.610(2) 1 calc R . P A 1
C15 C 0.7849(7) 0.1504(6) 0.4469(4) 0.0470(14) Uani 0.610(2) 1 d . . P A 1
C16 C 0.6147(10) 0.2269(10) 0.5035(5) 0.0477(17) Uani 0.610(2) 1 d . . P A 1
C17 C 0.539(4) 0.308(4) 0.549(3) 0.088(2) Uani 0.610(2) 1 d . . P A 1
H17A H 0.542037 0.404666 0.535068 0.132 Uiso 0.610(2) 1 calc GR . P A 1
H17B H 0.570814 0.297758 0.602649 0.132 Uiso 0.610(2) 1 calc GR . P A 1
H17C H 0.454803 0.276084 0.539512 0.132 Uiso 0.610(2) 1 calc GR . P A 1
O1A O 0.8830(8) 0.1938(8) 0.4010(5) 0.0670(14) Uani 0.390(2) 1 d . . P A 2
N1A N 0.8813(11) 0.4150(10) 0.5874(7) 0.0527(14) Uani 0.390(2) 1 d . . P A 2
N2A N 0.665(3) 0.145(3) 0.3858(11) 0.046(2) Uani 0.390(2) 1 d . . P A 2
N3A N 0.556(2) 0.179(5) 0.4259(17) 0.047(2) Uani 0.390(2) 1 d . . P A 2
C6A C 0.8400(8) 0.1766(7) 0.6133(5) 0.0431(15) Uani 0.390(2) 1 d . . P A 2
C5A C 0.8951(7) 0.1845(7) 0.6897(5) 0.0618(15) Uani 0.390(2) 1 d G . P A 2
H5A H 0.929083 0.268081 0.709463 0.074 Uiso 0.390(2) 1 calc R . P A 2
C4A C 0.8993(7) 0.0676(10) 0.7365(3) 0.0568(18) Uani 0.390(2) 1 d G . P A 2
H4A H 0.936171 0.072913 0.787580 0.068 Uiso 0.390(2) 1 calc R . P A 2
C3A C 0.8485(8) -0.0573(7) 0.7069(4) 0.0601(16) Uani 0.390(2) 1 d G . P A 2
H3A H 0.851328 -0.135508 0.738245 0.072 Uiso 0.390(2) 1 calc R . P A 2
C2A C 0.7934(7) -0.0652(7) 0.6306(5) 0.0675(18) Uani 0.390(2) 1 d G . P A 2
H2A H 0.759396 -0.148763 0.610793 0.081 Uiso 0.390(2) 1 calc R . P A 2
C1A C 0.7892(6) 0.0517(11) 0.5838(3) 0.0556(16) Uani 0.390(2) 1 d G . P A 2
H1A H 0.752307 0.046403 0.532676 0.067 Uiso 0.390(2) 1 calc R . P A 2
C7A C 0.8278(12) 0.2964(10) 0.5629(7) 0.0443(15) Uani 0.390(2) 1 d D U P A 2
C8A C 0.7497(7) 0.3060(8) 0.4842(4) 0.0439(11) Uani 0.390(2) 1 d . . P A 2
C9A C 0.7732(7) 0.4558(5) 0.4661(6) 0.0430(14) Uani 0.390(2) 1 d . . P A 2
C14A C 0.7340(7) 0.5349(10) 0.4009(4) 0.0558(16) Uani 0.390(2) 1 d G . P A 2
H14A H 0.683050 0.495393 0.359411 0.067 Uiso 0.390(2) 1 calc R . P A 2
C13A C 0.7709(10) 0.6729(10) 0.3977(4) 0.0737(18) Uani 0.390(2) 1 d G . P A 2
H13A H 0.744649 0.725820 0.354070 0.088 Uiso 0.390(2) 1 calc R . P A 2
C12A C 0.8470(10) 0.7319(5) 0.4597(6) 0.071(2) Uani 0.390(2) 1 d G . P A 2
H12A H 0.871721 0.824287 0.457605 0.085 Uiso 0.390(2) 1 calc R . P A 2
C11A C 0.8863(7) 0.6529(9) 0.5250(4) 0.0662(18) Uani 0.390(2) 1 d G . P A 2
H11A H 0.937195 0.692327 0.566483 0.079 Uiso 0.390(2) 1 calc R . P A 2
C10A C 0.8494(7) 0.5148(9) 0.5282(4) 0.0523(16) Uani 0.390(2) 1 d DG . P A 2
C15A C 0.7842(11) 0.2101(11) 0.4204(6) 0.0470(14) Uani 0.390(2) 1 d . . P A 2
C16A C 0.6147(18) 0.2721(17) 0.4815(10) 0.0477(17) Uani 0.390(2) 1 d . . P A 2
C17A C 0.530(6) 0.310(7) 0.546(4) 0.088(2) Uani 0.390(2) 1 d . . P A 2
H17D H 0.446269 0.325738 0.521831 0.132 Uiso 0.390(2) 1 calc GR . P A 2
H17E H 0.561668 0.392896 0.572460 0.132 Uiso 0.390(2) 1 calc GR . P A 2
H17F H 0.532091 0.234701 0.581718 0.132 Uiso 0.390(2) 1 calc GR . P A 2


_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
C18 C19 1.378(4) . ?
C18 C23 1.375(4) . ?
C18 N2 1.492(16) . ?
C18 N2A 1.32(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.355(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(5) . ?
C23 H23 0.9300 . ?
O1 C15 1.209(8) . ?
N1 C7 1.279(10) . ?
N1 C10 1.428(6) . ?
N2 N3 1.37(3) . ?
N2 C15 1.310(18) . ?
N3 C16 1.21(2) . ?
C6 C1 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.459(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C7 C8 1.542(9) . ?
C8 C9 1.499(6) . ?
C8 C15 1.538(8) . ?
C8 C16 1.498(12) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C14 1.3900 . ?
C14 H14 0.9300 . ?
C16 C17 1.46(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1A C15A 1.186(13) . ?
N1A C7A 1.323(17) . ?
N1A C10A 1.421(10) . ?
N2A N3A 1.50(4) . ?
N2A C15A 1.49(3) . ?
N3A C16A 1.41(4) . ?
C6A C5A 1.3900 . ?
C6A C1A 1.3900 . ?
C6A C7A 1.448(10) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A C3A 1.3900 . ?
C3A H3A 0.9300 . ?
C3A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C2A C1A 1.3900 . ?
C1A H1A 0.9300 . ?
C7A C8A 1.518(16) . ?
C8A C9A 1.505(9) . ?
C8A C15A 1.541(14) . ?
C8A C16A 1.50(2) . ?
C9A C14A 1.3900 . ?
C9A C10A 1.3900 . ?
C14A H14A 0.9300 . ?
C14A C13A 1.3900 . ?
C13A H13A 0.9300 . ?
C13A C12A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3900 . ?
C16A C17A 1.60(8) . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 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
C19 C18 N2 121.6(8) . . ?
C23 C18 C19 119.9(3) . . ?
C23 C18 N2 118.2(8) . . ?
N2A C18 C19 118.3(14) . . ?
N2A C18 C23 120.8(15) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(3) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.7(3) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C7 N1 C10 108.5(6) . . ?
N3 N2 C18 119.3(14) . . ?
C15 N2 C18 128.8(15) . . ?
C15 N2 N3 111.9(13) . . ?
C16 N3 N2 114.0(12) . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C7 120.7(6) . . ?
C5 C6 C7 119.3(6) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C7 C6 122.6(7) . . ?
N1 C7 C8 113.9(5) . . ?
C6 C7 C8 123.6(6) . . ?
C9 C8 C7 98.5(4) . . ?
C9 C8 C15 112.5(4) . . ?
C15 C8 C7 116.7(5) . . ?
C16 C8 C7 116.1(6) . . ?
C16 C8 C9 112.3(4) . . ?
C16 C8 C15 101.3(6) . . ?
C10 C9 C8 109.4(5) . . ?
C10 C9 C14 120.0 . . ?
C14 C9 C8 130.6(5) . . ?
C9 C10 N1 109.6(5) . . ?
C11 C10 N1 130.4(5) . . ?
C11 C10 C9 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14 120.0 . . ?
O1 C15 N2 127.4(10) . . ?
O1 C15 C8 128.6(6) . . ?
N2 C15 C8 104.0(9) . . ?
N3 C16 C8 108.7(12) . . ?
N3 C16 C17 127(2) . . ?
C17 C16 C8 123.3(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7A N1A C10A 107.2(10) . . ?
C18 N2A N3A 116(3) . . ?
C18 N2A C15A 128(2) . . ?
C15A N2A N3A 115(2) . . ?
C16A N3A N2A 99(2) . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A C7A 122.4(9) . . ?
C1A C6A C7A 117.6(9) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C6A C1A H1A 120.0 . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
N1A C7A C6A 119.4(12) . . ?
N1A C7A C8A 113.9(8) . . ?
C6A C7A C8A 126.6(10) . . ?
C7A C8A C15A 117.7(8) . . ?
C9A C8A C7A 99.2(7) . . ?
C9A C8A C15A 110.6(6) . . ?
C16A C8A C7A 115.5(9) . . ?
C16A C8A C9A 113.4(8) . . ?
C16A C8A C15A 101.0(10) . . ?
C14A C9A C8A 131.0(8) . . ?
C14A C9A C10A 120.0 . . ?
C10A C9A C8A 109.0(8) . . ?
C9A C14A H14A 120.0 . . ?
C13A C14A C9A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C9A C10A N1A 110.7(9) . . ?
C11A C10A N1A 129.3(9) . . ?
C11A C10A C9A 120.0 . . ?
O1A C15A N2A 127.0(17) . . ?
O1A C15A C8A 128.1(11) . . ?
N2A C15A C8A 104.8(15) . . ?
N3A C16A C8A 120(2) . . ?
N3A C16A C17A 113(3) . . ?
C8A C16A C17A 126(3) . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 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
C18 C19 C20 C21 0.0(6) . . . . ?
C18 N2 N3 C16 177.5(14) . . . . ?
C18 N2 C15 O1 2(2) . . . . ?
C18 N2 C15 C8 -175.0(12) . . . . ?
C18 N2A N3A C16A 173.4(17) . . . . ?
C18 N2A C15A O1A 8(3) . . . . ?
C18 N2A C15A C8A -174.1(17) . . . . ?
C19 C18 C23 C22 1.2(5) . . . . ?
C19 C18 N2 N3 160.6(14) . . . . ?
C19 C18 N2 C15 -21.7(17) . . . . ?
C19 C18 N2A N3A 166.4(16) . . . . ?
C19 C18 N2A C15A -25(2) . . . . ?
C19 C20 C21 C22 1.0(6) . . . . ?
C20 C21 C22 C23 -0.8(6) . . . . ?
C21 C22 C23 C18 -0.2(6) . . . . ?
C23 C18 C19 C20 -1.0(5) . . . . ?
C23 C18 N2 N3 -26.3(18) . . . . ?
C23 C18 N2 C15 151.5(12) . . . . ?
C23 C18 N2A N3A -2(2) . . . . ?
C23 C18 N2A C15A 166.4(14) . . . . ?
N1 C7 C8 C9 -1.4(7) . . . . ?
N1 C7 C8 C15 -122.0(6) . . . . ?
N1 C7 C8 C16 118.7(7) . . . . ?
N1 C10 C11 C12 179.2(5) . . . . ?
N2 C18 C19 C20 172.0(7) . . . . ?
N2 C18 C23 C22 -172.1(7) . . . . ?
N2 N3 C16 C8 -2(2) . . . . ?
N2 N3 C16 C17 169(2) . . . . ?
N3 N2 C15 O1 -179.6(13) . . . . ?
N3 N2 C15 C8 2.9(16) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C7 C8 C9 -179.7(5) . . . . ?
C6 C7 C8 C15 59.7(7) . . . . ?
C6 C7 C8 C16 -59.6(8) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 N1 179.7(5) . . . . ?
C1 C6 C7 C8 -2.1(7) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C6 C7 N1 0.1(8) . . . . ?
C5 C6 C7 C8 178.3(4) . . . . ?
C7 N1 C10 C9 -1.9(6) . . . . ?
C7 N1 C10 C11 178.8(4) . . . . ?
C7 C6 C1 C2 -179.6(4) . . . . ?
C7 C6 C5 C4 179.6(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C7 C8 C9 C14 -179.5(4) . . . . ?
C7 C8 C15 O1 51.8(8) . . . . ?
C7 C8 C15 N2 -130.8(9) . . . . ?
C7 C8 C16 N3 131.0(14) . . . . ?
C7 C8 C16 C17 -41(2) . . . . ?
C8 C9 C10 N1 1.0(4) . . . . ?
C8 C9 C10 C11 -179.7(4) . . . . ?
C8 C9 C14 C13 179.6(4) . . . . ?
C9 C8 C15 O1 -61.0(7) . . . . ?
C9 C8 C15 N2 116.4(8) . . . . ?
C9 C8 C16 N3 -116.7(13) . . . . ?
C9 C8 C16 C17 72(2) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 N1 C7 C6 -179.6(5) . . . . ?
C10 N1 C7 C8 2.1(8) . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C14 C9 C10 N1 -179.4(4) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C15 N2 N3 C16 -1(3) . . . . ?
C15 C8 C9 C10 123.8(4) . . . . ?
C15 C8 C9 C14 -55.8(5) . . . . ?
C15 C8 C16 N3 3.6(13) . . . . ?
C15 C8 C16 C17 -167.9(19) . . . . ?
C16 C8 C9 C10 -122.7(6) . . . . ?
C16 C8 C9 C14 57.7(7) . . . . ?
C16 C8 C15 O1 178.8(6) . . . . ?
C16 C8 C15 N2 -3.8(9) . . . . ?
N1A C7A C8A C9A 2.1(11) . . . . ?
N1A C7A C8A C15A 121.3(11) . . . . ?
N1A C7A C8A C16A -119.5(12) . . . . ?
N2A C18 C19 C20 -169.6(11) . . . . ?
N2A C18 C23 C22 169.5(11) . . . . ?
N2A N3A C16A C8A 0(3) . . . . ?
N2A N3A C16A C17A -170(3) . . . . ?
N3A N2A C15A O1A 176.4(19) . . . . ?
N3A N2A C15A C8A -5(2) . . . . ?
C6A C5A C4A C3A 0.0 . . . . ?
C6A C7A C8A C9A 177.3(10) . . . . ?
C6A C7A C8A C15A -63.5(13) . . . . ?
C6A C7A C8A C16A 55.7(14) . . . . ?
C5A C6A C1A C2A 0.0 . . . . ?
C5A C6A C7A N1A 6.9(14) . . . . ?
C5A C6A C7A C8A -168.1(8) . . . . ?
C5A C4A C3A C2A 0.0 . . . . ?
C4A C3A C2A C1A 0.0 . . . . ?
C3A C2A C1A C6A 0.0 . . . . ?
C1A C6A C5A C4A 0.0 . . . . ?
C1A C6A C7A N1A -176.0(9) . . . . ?
C1A C6A C7A C8A 9.1(13) . . . . ?
C7A N1A C10A C9A 0.6(11) . . . . ?
C7A N1A C10A C11A -177.4(8) . . . . ?
C7A C6A C5A C4A 177.1(8) . . . . ?
C7A C6A C1A C2A -177.2(8) . . . . ?
C7A C8A C9A C14A 177.2(7) . . . . ?
C7A C8A C9A C10A -1.6(7) . . . . ?
C7A C8A C15A O1A -50.6(13) . . . . ?
C7A C8A C15A N2A 131.3(12) . . . . ?
C7A C8A C16A N3A -131.2(18) . . . . ?
C7A C8A C16A C17A 37(3) . . . . ?
C8A C9A C14A C13A -178.7(8) . . . . ?
C8A C9A C10A N1A 0.8(8) . . . . ?
C8A C9A C10A C11A 179.0(6) . . . . ?
C9A C8A C15A O1A 62.4(12) . . . . ?
C9A C8A C15A N2A -115.7(11) . . . . ?
C9A C8A C16A N3A 115.2(19) . . . . ?
C9A C8A C16A C17A -77(3) . . . . ?
C9A C14A C13A C12A 0.0 . . . . ?
C14A C9A C10A N1A -178.2(8) . . . . ?
C14A C9A C10A C11A 0.0 . . . . ?
C14A C13A C12A C11A 0.0 . . . . ?
C13A C12A C11A C10A 0.0 . . . . ?
C12A C11A C10A N1A 177.8(9) . . . . ?
C12A C11A C10A C9A 0.0 . . . . ?
C10A N1A C7A C6A -177.3(9) . . . . ?
C10A N1A C7A C8A -1.8(13) . . . . ?
C10A C9A C14A C13A 0.0 . . . . ?
C15A N2A N3A C16A 3(3) . . . . ?
C15A C8A C9A C14A 52.8(9) . . . . ?
C15A C8A C9A C10A -126.0(7) . . . . ?
C15A C8A C16A N3A -3.1(19) . . . . ?
C15A C8A C16A C17A 165(3) . . . . ?
C16A C8A C9A C14A -59.8(11) . . . . ?
C16A C8A C9A C10A 121.4(9) . . . . ?
C16A C8A C15A O1A -177.2(10) . . . . ?
C16A C8A C15A N2A 4.7(12) . . . . ?

_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 1.850
_oxdiff_exptl_absorpt_empirical_full_min 0.707
