# 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. 
# 
#######################################################################

data_caiyh_200720
_database_code_depnum_ccdc_archive 'CCDC 2109208'
loop_
_audit_author_name
_audit_author_address
'Huaanzi Hu'
;Changzhou University
China
;
_audit_update_record             
;
2021-09-11 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_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         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   11.7433(5)
_cell_length_b                   11.7433(5)
_cell_length_c                   14.1086(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1945.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3720
_cell_measurement_temperature    304.05(16)
_cell_measurement_theta_max      67.9860
_cell_measurement_theta_min      3.6840
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (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    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17779
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.899
_diffrn_reflns_theta_min         3.764
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.05(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  72.00   0.50    1.00    --   46.12-132.00 -64.00   60
  2  ω   -175.00 -83.00   0.50    2.00    -- -100.00 -17.00 -20.00  184
  3  ω     33.00 104.00   0.50    2.00    --  105.44-108.00-169.00  142
  4  ω   -109.00 -76.00   0.50    1.00    --  -46.12-125.00   0.00   66
  5  ω     38.00 108.00   0.50    1.00    --   46.12  57.00-120.00  140
  6  ω     41.00  83.00   0.50    2.00    --  105.44 -94.00 120.00   84
  7  ω     33.00  76.00   0.50    2.00    --  105.44 -94.00  30.00   86
  8  ω     89.00 114.00   0.50    2.00    --  107.00-133.00 -64.00   50
  9  ω    -49.00 -23.00   0.50    1.00    --  -46.37 -77.00 -90.00   52
 10  ω    -50.00 -24.00   0.50    1.00    --  -46.37 -77.00-150.00   52
 11  ω     31.00  61.00   0.50    1.00    --   46.37  57.00-150.00   60
 12  ω     83.00 113.00   0.50    1.00    --   46.37 133.00   4.00   60
 13  ω     32.00  76.00   0.50    1.00    --   46.37  19.00 -90.00   88
 14  ω   -107.00 -79.00   0.50    2.00    -- -100.00 -70.00-136.53   56
 15  ω    -99.00 -74.00   0.50    2.00    -- -100.00 -82.00-100.88   50
 16  ω   -109.00 -82.00   0.50    2.00    -- -100.00 -62.00 -96.66   54
 17  ω   -101.00 -75.00   0.50    2.00    -- -100.00 -80.00 -67.45   52
 18  ω   -104.00 -78.00   0.50    2.00    -- -100.00 -77.00 -90.00   52
 19  ω   -106.00 -81.00   0.50    2.00    -- -100.00 -64.00-125.93   50
 20  ω   -167.00-141.00   0.50    2.00    -- -100.00 -70.00-136.53   52
 21  ω   -140.00-114.00   0.50    2.00    -- -100.00 -82.00-100.88   52
 22  ω   -106.00 -80.00   0.50    2.00    -- -100.00 -70.00 -88.07   52
 23  ω   -157.00-131.00   0.50    2.00    -- -100.00 -77.00-120.00   52
 24  ω   -113.00 -80.00   0.50    2.00    -- -100.00 -70.00-106.38   66
 25  ω   -102.00 -76.00   0.50    2.00    -- -100.00 -77.00-120.00   52
 26  ω   -134.00 -84.00   0.50    2.00    -- -100.00 -54.00 -84.78  100
 27  ω   -172.00-146.00   0.50    2.00    -- -100.00 -80.00 -67.45   52
 28  ω   -106.00 -80.00   0.50    2.00    -- -100.00 -76.00-137.45   52
 29  ω   -105.00 -79.00   0.50    2.00    -- -100.00 -70.00-110.82   52
 30  ω     83.00 109.00   0.50    2.00    --  107.00  77.00-150.00   52
 31  ω     41.00 105.00   0.50    2.00    --  107.00 -94.00  90.00  128
 32  ω     92.00 117.00   0.50    2.00    --  107.00-125.00-180.00   50
 33  ω     37.00  62.00   0.50    2.00    --  107.00-125.00-180.00   50
 34  ω     89.00 177.00   0.50    2.00    --  107.00  15.00-120.00  176
 35  ω     23.00 118.00   0.50    1.00    --   46.37  77.00 -30.00  190
 36  ω     30.00 118.00   0.50    1.00    --   46.37  57.00  90.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1136230000
_diffrn_orient_matrix_UB_12      -0.0643682000
_diffrn_orient_matrix_UB_13      0.0104445000
_diffrn_orient_matrix_UB_21      -0.0657374000
_diffrn_orient_matrix_UB_22      -0.1106730000
_diffrn_orient_matrix_UB_23      0.0214524000
_diffrn_orient_matrix_UB_31      -0.0019914000
_diffrn_orient_matrix_UB_32      -0.0285492000
_diffrn_orient_matrix_UB_33      -0.1064812000
_diffrn_oxdiff_digest_frames     
;
019fe6862e2cc66f4991e39ecc426003e5007627299
;
_diffrn_oxdiff_digest_hkl        
;
0150fb2b048dfe1587d85e501403b7ff2aea8a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                2883
_reflns_number_total             3816
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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         0.276
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0013(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.072
_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)+(0.1041P)²+0.2839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.2010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N13(H13), C8(H8), C7(H7), C18(H18), C19(H19), C6(H6), C5(H5), C16(H16),
 C17(H17), C0AA(H0AA)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C25(H25A,H25B,H25C)
;
_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
O22 O 0.4824(3) 0.2649(3) 0.5083(3) 0.0684(10) Uani 1 1 d . . . . .
O23 O 0.2450(3) 0.2416(4) 0.6569(3) 0.0750(11) Uani 1 1 d . . . . .
N3 N 0.2296(4) 0.1371(4) 0.5206(3) 0.0675(11) Uani 1 1 d . . . . .
O21 O 0.5341(3) 0.5224(4) 0.6154(4) 0.0962(16) Uani 1 1 d . . . . .
C11 C 0.4620(4) 0.3623(4) 0.5298(3) 0.0549(11) Uani 1 1 d . . . . .
C1 C 0.2498(4) 0.3346(4) 0.5007(3) 0.0552(11) Uani 1 1 d . . . . .
N13 N 0.6617(4) 0.4054(4) 0.5473(4) 0.0719(13) Uani 1 1 d . . . . .
H13 H 0.670672 0.345858 0.512630 0.086 Uiso 1 1 calc R . . . .
C2 C 0.2424(4) 0.2355(4) 0.5700(4) 0.0593(12) Uani 1 1 d . . . . .
C12 C 0.5579(4) 0.4382(5) 0.5674(4) 0.0632(13) Uani 1 1 d . . . . .
C10 C 0.3471(4) 0.4136(4) 0.5269(3) 0.0559(11) Uani 1 1 d . . . . .
H10A H 0.348361 0.475883 0.481695 0.067 Uiso 1 1 calc R . . . .
H10B H 0.331039 0.445989 0.588676 0.067 Uiso 1 1 calc R . . . .
C9 C 0.2601(4) 0.2718(4) 0.4073(4) 0.0565(11) Uani 1 1 d . . . . .
C24 C 0.1364(4) 0.4000(5) 0.5080(5) 0.0699(14) Uani 1 1 d . . . . .
H24A H 0.074224 0.348247 0.498198 0.105 Uiso 1 1 calc GR . . . .
H24B H 0.134281 0.458555 0.460547 0.105 Uiso 1 1 calc GR . . . .
H24C H 0.130161 0.433787 0.569678 0.105 Uiso 1 1 calc GR . . . .
C15 C 0.8376(5) 0.3898(7) 0.6425(4) 0.0810(19) Uani 1 1 d . . . . .
C4 C 0.2445(4) 0.1572(5) 0.4236(4) 0.0636(13) Uani 1 1 d . . . . .
C14 C 0.7631(5) 0.4650(6) 0.5810(5) 0.0816(19) Uani 1 1 d . . . . .
H14 H 0.737647 0.529196 0.620021 0.098 Uiso 1 1 calc R . . . .
C8 C 0.2785(5) 0.3122(6) 0.3171(4) 0.0714(14) Uani 1 1 d . . . . .
H8 H 0.288969 0.389522 0.305764 0.086 Uiso 1 1 calc R . . . .
C7 C 0.2811(5) 0.2323(8) 0.2423(4) 0.088(2) Uani 1 1 d . . . . .
H7 H 0.294845 0.257349 0.180818 0.105 Uiso 1 1 calc R . . . .
C18 C 0.9861(9) 0.2573(16) 0.7513(7) 0.141(4) Uani 1 1 d . . . . .
H18 H 1.035016 0.212841 0.787629 0.169 Uiso 1 1 calc R . . . .
C19 C 0.8367(8) 0.2746(9) 0.6383(7) 0.112(3) Uani 1 1 d . . . . .
H19 H 0.785521 0.238427 0.597957 0.135 Uiso 1 1 calc R . . . .
C6 C 0.2641(6) 0.1206(8) 0.2584(5) 0.093(2) Uani 1 1 d . . . . .
H6 H 0.264517 0.070144 0.207561 0.112 Uiso 1 1 calc R . . . .
C20 C 0.8286(6) 0.5139(7) 0.4962(6) 0.105(2) Uani 1 1 d . . . . .
H20A H 0.857724 0.452641 0.458205 0.157 Uiso 1 1 calc GR . . . .
H20B H 0.890705 0.559726 0.518607 0.157 Uiso 1 1 calc GR . . . .
H20C H 0.778338 0.559966 0.458617 0.157 Uiso 1 1 calc GR . . . .
C5 C 0.2458(6) 0.0788(6) 0.3501(5) 0.0845(18) Uani 1 1 d . . . . .
H5 H 0.235021 0.001549 0.361249 0.101 Uiso 1 1 calc R . . . .
C16 C 0.9146(7) 0.4409(10) 0.7027(6) 0.120(3) Uani 1 1 d . . . . .
H16 H 0.917420 0.519731 0.708103 0.144 Uiso 1 1 calc R . . . .
C17 C 0.9904(8) 0.3704(16) 0.7572(6) 0.143(5) Uani 1 1 d . . . . .
H17 H 1.043434 0.404458 0.797158 0.171 Uiso 1 1 calc R . . . .
C25 C 0.2153(9) 0.0270(6) 0.5640(7) 0.118(3) Uani 1 1 d . . . . .
H25A H 0.276348 -0.022226 0.544805 0.177 Uiso 1 1 calc GR . . . .
H25B H 0.143939 -0.005236 0.544385 0.177 Uiso 1 1 calc GR . . . .
H25C H 0.216004 0.035042 0.631704 0.177 Uiso 1 1 calc GR . . . .
C0AA C 0.9113(10) 0.2083(12) 0.6932(8) 0.145(4) Uani 1 1 d . . . . .
H0AA H 0.908447 0.129287 0.689009 0.174 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
O22 C11 1.207(6) . ?
O23 C2 1.229(6) . ?
N3 C2 1.358(7) . ?
N3 C4 1.399(8) . ?
N3 C25 1.441(8) . ?
O21 C12 1.231(6) . ?
C11 C12 1.531(7) . ?
C11 C10 1.479(7) . ?
C1 C2 1.523(7) . ?
C1 C10 1.517(7) . ?
C1 C9 1.515(7) . ?
C1 C24 1.540(7) . ?
N13 H13 0.8600 . ?
N13 C12 1.310(7) . ?
N13 C14 1.460(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 C4 1.377(8) . ?
C9 C8 1.376(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 C14 1.515(10) . ?
C15 C19 1.355(11) . ?
C15 C16 1.378(10) . ?
C4 C5 1.387(8) . ?
C14 H14 0.9800 . ?
C14 C20 1.535(11) . ?
C8 H8 0.9300 . ?
C8 C7 1.412(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.346(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.332(17) . ?
C18 C0AA 1.333(16) . ?
C19 H19 0.9300 . ?
C19 C0AA 1.405(13) . ?
C6 H6 0.9300 . ?
C6 C5 1.400(11) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.438(17) . ?
C17 H17 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C0AA H0AA 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
C2 N3 C4 110.1(4) . . ?
C2 N3 C25 124.0(6) . . ?
C4 N3 C25 125.5(5) . . ?
O22 C11 C12 119.5(4) . . ?
O22 C11 C10 124.1(4) . . ?
C10 C11 C12 116.3(4) . . ?
C2 C1 C24 106.7(4) . . ?
C10 C1 C2 110.7(4) . . ?
C10 C1 C24 109.3(4) . . ?
C9 C1 C2 101.0(4) . . ?
C9 C1 C10 116.7(4) . . ?
C9 C1 C24 111.7(4) . . ?
C12 N13 H13 118.4 . . ?
C12 N13 C14 123.2(5) . . ?
C14 N13 H13 118.4 . . ?
O23 C2 N3 124.3(5) . . ?
O23 C2 C1 126.5(5) . . ?
N3 C2 C1 109.1(5) . . ?
O21 C12 C11 119.4(4) . . ?
O21 C12 N13 124.5(5) . . ?
N13 C12 C11 116.0(4) . . ?
C11 C10 C1 116.4(4) . . ?
C11 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C1 C10 H10A 108.2 . . ?
C1 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
C4 C9 C1 108.7(4) . . ?
C8 C9 C1 130.4(5) . . ?
C8 C9 C4 120.9(5) . . ?
C1 C24 H24A 109.5 . . ?
C1 C24 H24B 109.5 . . ?
C1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C15 C14 123.5(6) . . ?
C19 C15 C16 117.8(8) . . ?
C16 C15 C14 118.6(8) . . ?
C9 C4 N3 110.2(4) . . ?
C9 C4 C5 121.4(6) . . ?
C5 C4 N3 128.4(6) . . ?
N13 C14 C15 112.2(6) . . ?
N13 C14 H14 107.6 . . ?
N13 C14 C20 109.5(6) . . ?
C15 C14 H14 107.6 . . ?
C15 C14 C20 112.0(5) . . ?
C20 C14 H14 107.6 . . ?
C9 C8 H8 121.1 . . ?
C9 C8 C7 117.7(6) . . ?
C7 C8 H8 121.1 . . ?
C8 C7 H7 119.4 . . ?
C6 C7 C8 121.2(6) . . ?
C6 C7 H7 119.4 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C0AA 119.6(12) . . ?
C0AA C18 H18 120.2 . . ?
C15 C19 H19 119.2 . . ?
C15 C19 C0AA 121.6(9) . . ?
C0AA C19 H19 119.2 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.3(6) . . ?
C5 C6 H6 119.3 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C5 C6 117.4(6) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.1(11) . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 121.1(9) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C0AA C19 120.7(13) . . ?
C18 C0AA H0AA 119.6 . . ?
C19 C0AA H0AA 119.6 . . ?

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
O22 C11 C12 O21 -157.9(6) . . . . ?
O22 C11 C12 N13 20.2(7) . . . . ?
O22 C11 C10 C1 3.8(7) . . . . ?
N3 C4 C5 C6 -179.0(6) . . . . ?
C1 C9 C4 N3 -2.6(5) . . . . ?
C1 C9 C4 C5 178.0(5) . . . . ?
C1 C9 C8 C7 -178.3(5) . . . . ?
C2 N3 C4 C9 -3.9(6) . . . . ?
C2 N3 C4 C5 175.4(5) . . . . ?
C2 C1 C10 C11 58.7(5) . . . . ?
C2 C1 C9 C4 7.2(5) . . . . ?
C2 C1 C9 C8 -174.4(5) . . . . ?
C12 C11 C10 C1 -173.1(4) . . . . ?
C12 N13 C14 C15 119.2(6) . . . . ?
C12 N13 C14 C20 -115.7(7) . . . . ?
C10 C11 C12 O21 19.2(7) . . . . ?
C10 C11 C12 N13 -162.7(5) . . . . ?
C10 C1 C2 O23 47.4(7) . . . . ?
C10 C1 C2 N3 -133.9(4) . . . . ?
C10 C1 C9 C4 127.3(5) . . . . ?
C10 C1 C9 C8 -54.4(7) . . . . ?
C9 C1 C2 O23 171.7(5) . . . . ?
C9 C1 C2 N3 -9.6(5) . . . . ?
C9 C1 C10 C11 -56.0(6) . . . . ?
C9 C4 C5 C6 0.2(8) . . . . ?
C9 C8 C7 C6 1.2(9) . . . . ?
C24 C1 C2 O23 -71.4(6) . . . . ?
C24 C1 C2 N3 107.3(5) . . . . ?
C24 C1 C10 C11 176.0(4) . . . . ?
C24 C1 C9 C4 -105.9(5) . . . . ?
C24 C1 C9 C8 72.4(6) . . . . ?
C15 C19 C0AA C18 -0.3(18) . . . . ?
C15 C16 C17 C18 -1.1(15) . . . . ?
C4 N3 C2 O23 -172.5(5) . . . . ?
C4 N3 C2 C1 8.7(6) . . . . ?
C4 C9 C8 C7 -0.1(8) . . . . ?
C14 N13 C12 O21 0.8(10) . . . . ?
C14 N13 C12 C11 -177.2(5) . . . . ?
C14 C15 C19 C0AA 176.8(9) . . . . ?
C14 C15 C16 C17 -176.3(7) . . . . ?
C8 C9 C4 N3 178.8(5) . . . . ?
C8 C9 C4 C5 -0.5(8) . . . . ?
C8 C7 C6 C5 -1.5(10) . . . . ?
C7 C6 C5 C4 0.8(10) . . . . ?
C19 C15 C14 N13 23.5(9) . . . . ?
C19 C15 C14 C20 -100.1(8) . . . . ?
C19 C15 C16 C17 0.5(12) . . . . ?
C16 C15 C14 N13 -159.8(6) . . . . ?
C16 C15 C14 C20 76.5(8) . . . . ?
C16 C15 C19 C0AA 0.1(14) . . . . ?
C17 C18 C0AA C19 -0.2(19) . . . . ?
C25 N3 C2 O23 1.3(9) . . . . ?
C25 N3 C2 C1 -177.5(6) . . . . ?
C25 N3 C4 C9 -177.6(6) . . . . ?
C25 N3 C4 C5 1.7(10) . . . . ?
C0AA C18 C17 C16 0.9(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.290
_oxdiff_exptl_absorpt_empirical_full_min 0.631
