# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_230307lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2247902'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N3 O2'
_chemical_formula_sum            'C19 H25 N3 O2'
_chemical_formula_weight         327.42
_chemical_absolute_configuration ?
_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   10.83365(16)
_cell_length_b                   14.19083(19)
_cell_length_c                   11.90925(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.2955(13)
_cell_angle_gamma                90
_cell_volume                     1816.09(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10562
_cell_measurement_temperature    103(6)
_cell_measurement_theta_max      74.4700
_cell_measurement_theta_min      4.8480
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
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    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13765
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         4.871
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_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    -76.00 -36.00   0.50    0.22    --  -77.70 125.00-150.00   80
  2  ω    -87.00 -62.00   0.50    0.22    --  -74.55 106.00-174.00   50
  3  ω    -90.00 -65.00   0.50    0.22    --  -77.70 106.00-174.00   50
  4  ω    -80.00 -25.00   0.50    0.22    --  -64.95 106.00-174.00  110
  5  ω   -118.00 -77.00   0.50    0.22    --  -74.55-125.00 -60.00   82
  6  ω   -100.00 -75.00   0.50    0.22    --  -74.55-125.00 -90.00   50
  7  ω   -115.00 -74.00   0.50    0.22    --  -77.70-125.00  90.00   82
  8  ω   -113.00 -82.00   0.50    0.22    --  -77.70-125.00 150.00   62
  9  ω   -118.00 -64.00   0.50    0.22    --  -74.55 -15.00  90.00  108
 10  ω     35.00  98.00   0.50    0.22    --   61.89   0.00-120.00  126
 11  ω     78.00 103.00   0.50    0.22    --   74.76-125.00-180.00   50
 12  ω     74.00  99.00   0.50    0.22    --   74.76-125.00-150.00   50
 13  ω     28.00  70.00   0.50    0.22    --   61.89 -95.00 -90.00   84
 14  ω     40.00  78.00   0.50    0.22    --   74.76-106.00  86.00   76
 15  ω     33.00  98.00   0.50    0.22    --   74.76-125.00 150.00  130
 16  ω     39.00  76.00   0.50    0.22    --   73.73 -95.00 150.00   74
 17  ω     35.00  70.00   0.50    0.22    --   61.89 -95.00 120.00   70
 18  ω     25.00  60.00   0.50    0.22    --   61.89-106.00  86.00   70
 19  ω     24.00  65.00   0.50    0.22    --   61.89 -95.00   0.00   82
 20  ω     43.00  70.00   0.50    0.22    --   74.76 -95.00 -60.00   54
 21  ω     32.00  63.00   0.50    0.22    --   61.89 -95.00-180.00   62
 22  ω     58.00 107.00   0.50    0.22    --   61.89  15.00  60.00   98
 23  ω     42.00  68.00   0.50    0.22    --   74.76   0.00  90.00   52
 24  ω     23.00  49.00   0.50    0.22    --   61.89-125.00  90.00   52
 25  ω     43.00  69.00   0.50    0.22    --   70.61 -95.00  30.00   52
 26  ω     37.00  62.00   0.50    0.22    --   74.76 -95.00-150.00   50
 27  ω     89.00 119.00   0.50    0.22    --   80.10 125.00 -90.00   60
 28  ω     79.00 104.00   0.50    0.22    --   80.10 125.00  90.00   50
 29  ω     47.00  85.00   0.50    0.22    --   61.89   0.00 150.00   76
 30  ω     30.00  88.00   0.50    0.22    --   61.89   0.00  30.00  116
 31  ω     24.00  49.00   0.50    0.22    --   61.89 -95.00 150.00   50
 32  ω     68.00  93.00   0.50    0.22    --   62.00  72.00 139.01   50
 33  ω     35.00  79.00   0.50    0.22    --   70.61 -95.00 -30.00   88
 34  ω     42.00  68.00   0.50    0.22    --   70.61  15.00 -90.00   52
 35  ω     76.00 113.00   0.50    0.22    --   70.61  15.00 -90.00   74
 36  ω    -61.00 -31.00   0.50    0.22    --  -74.55 125.00 120.00   60
 37  ω     81.00 120.00   0.50    0.22    --   74.76  15.00 -60.00   78
 38  ω     78.00 103.00   0.50    0.22    --   74.76-125.00 -30.00   50
 39  ω     31.00  57.00   0.50    0.22    --   74.76-125.00 -30.00   52
 40  ω   -105.00 -75.00   0.50    0.22    --  -77.70 125.00-150.00   60
 41  ω   -108.00 -74.00   0.50    0.22    --  -77.70-125.00  30.00   68
 42  ω   -106.00 -74.00   0.50    0.22    --  -77.70-125.00   0.00   64
 43  ω    -73.00 -47.00   0.50    0.22    --  -77.70 125.00   0.00   52
 44  ω   -105.00 -79.00   0.50    0.22    --  -77.70 125.00   0.00   52
 45  ω     88.00 121.00   0.50    0.22    --   80.10 125.00 150.00   66
 46  ω     84.00 109.00   0.50    0.22    --   80.10-125.00 120.00   50
 47  ω     37.00  62.00   0.50    0.22    --   80.10-125.00-120.00   50
 48  ω     98.00 124.00   0.50    0.22    --   80.10 125.00-120.00   52
 49  ω     40.00  66.00   0.50    0.22    --   80.10-125.00 120.00   52
 50  ω     44.00  69.00   0.50    0.22    --   80.10-125.00  60.00   50
 51  ω     84.00 109.00   0.50    0.22    --   80.10-125.00-180.00   50
 52  ω     44.00  70.00   0.50    0.22    --   80.10-125.00-180.00   52
 53  ω     98.00 124.00   0.50    0.22    --   80.10 125.00-150.00   52
 54  ω     87.00 112.00   0.50    0.22    --   80.10 125.00 -60.00   50
 55  ω     84.00 109.00   0.50    0.22    --   80.10-125.00-120.00   50
 56  ω     78.00 107.00   0.50    0.22    --   80.10-125.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1007120000
_diffrn_orient_matrix_UB_12      0.0770954000
_diffrn_orient_matrix_UB_13      0.0183612000
_diffrn_orient_matrix_UB_21      0.0988951000
_diffrn_orient_matrix_UB_22      -0.0716752000
_diffrn_orient_matrix_UB_23      -0.0268666000
_diffrn_orient_matrix_UB_31      -0.0250851000
_diffrn_orient_matrix_UB_32      0.0265599000
_diffrn_orient_matrix_UB_33      -0.1262705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.686
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                2674
_reflns_number_total             2734
_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 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_extinction_coef       0.0017(2)
_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   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0259
_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)+(0.0426P)²+0.3553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0690
_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:
 C14(H14A,H14B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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
C2 C 0.52479(16) 0.32356(12) 0.47098(16) 0.0204(4) Uani 1 1 d . . . . .
C3 C 0.53494(16) 0.39586(12) 0.37746(16) 0.0199(4) Uani 1 1 d . . . . .
C4 C 0.61998(17) 0.47037(13) 0.39018(18) 0.0257(4) Uani 1 1 d . . . . .
H4 H 0.666524 0.481792 0.461993 0.031 Uiso 1 1 calc R U . . .
C5 C 0.63722(18) 0.52779(14) 0.2993(2) 0.0304(5) Uani 1 1 d . . . . .
H5 H 0.695948 0.577762 0.309121 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5694(2) 0.51266(14) 0.19464(19) 0.0322(5) Uani 1 1 d . . . . .
H6 H 0.582414 0.551776 0.132494 0.039 Uiso 1 1 calc R U . . .
C7 C 0.48215(18) 0.44052(14) 0.17980(18) 0.0274(4) Uani 1 1 d . . . . .
H7 H 0.434308 0.430694 0.108226 0.033 Uiso 1 1 calc R U . . .
C8 C 0.46589(16) 0.38292(12) 0.27118(17) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.21965(16) 0.22881(13) 0.19287(17) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.23741(16) 0.21107(12) 0.31026(16) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.189493 0.171182 0.351995 0.024 Uiso 1 1 calc R U . . .
C13 C 0.34005(16) 0.26459(12) 0.35126(16) 0.0181(4) Uani 1 1 d . . . . .
C14 C 0.61940(17) 0.24186(13) 0.45755(17) 0.0249(4) Uani 1 1 d . . . . .
H14A H 0.626208 0.201292 0.525690 0.030 Uiso 1 1 calc R U . . .
H14B H 0.587253 0.202657 0.391492 0.030 Uiso 1 1 calc R U . . .
C15 C 0.74677(18) 0.27821(13) 0.44166(18) 0.0274(4) Uani 1 1 d . . . . .
C17 C 0.8784(2) 0.31849(19) 0.3050(2) 0.0447(6) Uani 1 1 d . . . . .
H17A H 0.881683 0.314210 0.223299 0.067 Uiso 1 1 calc R U . . .
H17B H 0.949305 0.284600 0.345519 0.067 Uiso 1 1 calc R U . . .
H17C H 0.881858 0.384818 0.328097 0.067 Uiso 1 1 calc R U . . .
C19 C 0.54731(16) 0.36469(13) 0.59043(16) 0.0227(4) Uani 1 1 d . . . . .
H19A H 0.632932 0.390320 0.603203 0.027 Uiso 1 1 calc R U . . .
H19B H 0.542028 0.313086 0.645563 0.027 Uiso 1 1 calc R U . . .
C20 C 0.45633(16) 0.44257(13) 0.61411(16) 0.0221(4) Uani 1 1 d . . . . .
H20A H 0.471174 0.498838 0.568547 0.026 Uiso 1 1 calc R U . . .
H20B H 0.370148 0.420842 0.590275 0.026 Uiso 1 1 calc R U . . .
C21 C 0.46968(18) 0.46964(14) 0.73831(17) 0.0254(4) Uani 1 1 d . . . . .
H21A H 0.551362 0.500556 0.758792 0.030 Uiso 1 1 calc R U . . .
H21B H 0.468622 0.411672 0.784424 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3675(2) 0.53563(14) 0.76756(19) 0.0327(5) Uani 1 1 d . . . . .
H22A H 0.375077 0.596771 0.728987 0.039 Uiso 1 1 calc R U . . .
H22B H 0.285449 0.508332 0.738848 0.039 Uiso 1 1 calc R U . . .
C23 C 0.3734(3) 0.5524(2) 0.8934(2) 0.0601(9) Uani 1 1 d . . . . .
H23A H 0.303606 0.592458 0.908244 0.090 Uiso 1 1 calc R U . . .
H23B H 0.452003 0.583595 0.921381 0.090 Uiso 1 1 calc R U . . .
H23C H 0.368408 0.491881 0.932329 0.090 Uiso 1 1 calc R U . . .
C24 C 0.12266(19) 0.18799(16) 0.10590(19) 0.0316(5) Uani 1 1 d . . . . .
H24A H 0.040549 0.211734 0.118368 0.047 Uiso 1 1 calc R U . . .
H24B H 0.123707 0.119129 0.112143 0.047 Uiso 1 1 calc R U . . .
H24C H 0.140150 0.206359 0.030178 0.047 Uiso 1 1 calc R U . . .
N1 N 0.39838(14) 0.28383(11) 0.45601(14) 0.0209(3) Uani 1 1 d . . . . .
N9 N 0.37851(14) 0.30935(10) 0.26065(13) 0.0188(3) Uani 1 1 d . . . . .
N10 N 0.30341(14) 0.28856(11) 0.16105(13) 0.0216(3) Uani 1 1 d . . . . .
O16 O 0.76364(13) 0.27691(10) 0.33168(13) 0.0315(3) Uani 1 1 d . . . . .
O18 O 0.82283(14) 0.30691(12) 0.51589(15) 0.0414(4) Uani 1 1 d . . . . .
H1 H 0.373(2) 0.2542(16) 0.518(2) 0.029(6) Uiso 1 1 d . . . . .


_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
C2 C3 1.529(3) . ?
C2 C14 1.569(2) . ?
C2 C19 1.528(3) . ?
C2 N1 1.471(2) . ?
C3 C4 1.398(2) . ?
C3 C8 1.398(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 N9 1.404(2) . ?
C11 C12 1.409(3) . ?
C11 C24 1.495(3) . ?
C11 N10 1.332(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 N1 1.353(2) . ?
C13 N9 1.362(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(3) . ?
C15 O16 1.345(3) . ?
C15 O18 1.201(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 O16 1.447(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.531(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.524(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.511(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 H1 0.92(3) . ?
N9 N10 1.382(2) . ?

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
C3 C2 C14 108.26(15) . . ?
C19 C2 C3 113.84(15) . . ?
C19 C2 C14 110.36(15) . . ?
N1 C2 C3 108.72(15) . . ?
N1 C2 C14 108.34(14) . . ?
N1 C2 C19 107.18(15) . . ?
C4 C3 C2 122.42(17) . . ?
C4 C3 C8 117.83(17) . . ?
C8 C3 C2 119.46(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.83(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(18) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.31(19) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.05(19) . . ?
C8 C7 H7 120.5 . . ?
C3 C8 N9 117.10(16) . . ?
C7 C8 C3 121.68(16) . . ?
C7 C8 N9 121.22(17) . . ?
C12 C11 C24 127.82(17) . . ?
N10 C11 C12 112.58(16) . . ?
N10 C11 C24 119.59(18) . . ?
C11 C12 H12 127.6 . . ?
C13 C12 C11 104.74(16) . . ?
C13 C12 H12 127.6 . . ?
N1 C13 C12 134.17(17) . . ?
N1 C13 N9 118.84(15) . . ?
N9 C13 C12 106.82(16) . . ?
C2 C14 H14A 109.1 . . ?
C2 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C2 112.35(15) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
O16 C15 C14 110.93(17) . . ?
O18 C15 C14 125.3(2) . . ?
O18 C15 O16 123.78(19) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
C2 C19 H19A 108.6 . . ?
C2 C19 H19B 108.6 . . ?
C2 C19 C20 114.64(15) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 112.24(15) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C20 C21 C22 113.35(16) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 112.52(19) . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
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 . . ?
C11 C24 H24A 109.5 . . ?
C11 C24 H24B 109.5 . . ?
C11 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 N1 H1 116.5(16) . . ?
C13 N1 C2 120.52(16) . . ?
C13 N1 H1 119.6(16) . . ?
C13 N9 C8 123.13(16) . . ?
C13 N9 N10 111.98(14) . . ?
N10 N9 C8 123.50(15) . . ?
C11 N10 N9 103.87(15) . . ?
C15 O16 C17 115.78(17) . . ?

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
C2 C3 C4 C5 172.13(17) . . . . ?
C2 C3 C8 C7 -172.66(17) . . . . ?
C2 C3 C8 N9 7.7(2) . . . . ?
C2 C14 C15 O16 -99.64(19) . . . . ?
C2 C14 C15 O18 78.6(2) . . . . ?
C2 C19 C20 C21 170.81(15) . . . . ?
C3 C2 C14 C15 47.6(2) . . . . ?
C3 C2 C19 C20 60.4(2) . . . . ?
C3 C2 N1 C13 39.3(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C8 N9 C13 14.2(2) . . . . ?
C3 C8 N9 N10 179.72(15) . . . . ?
C4 C3 C8 C7 1.3(3) . . . . ?
C4 C3 C8 N9 -178.32(15) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C6 C7 C8 N9 179.69(18) . . . . ?
C7 C8 N9 C13 -165.40(16) . . . . ?
C7 C8 N9 N10 0.1(3) . . . . ?
C8 C3 C4 C5 -1.7(3) . . . . ?
C8 N9 N10 C11 -167.94(15) . . . . ?
C11 C12 C13 N1 174.34(18) . . . . ?
C11 C12 C13 N9 -0.59(18) . . . . ?
C12 C11 N10 N9 0.64(19) . . . . ?
C12 C13 N1 C2 163.90(18) . . . . ?
C12 C13 N9 C8 168.00(16) . . . . ?
C12 C13 N9 N10 1.04(19) . . . . ?
C13 N9 N10 C11 -1.04(18) . . . . ?
C14 C2 C3 C4 -88.0(2) . . . . ?
C14 C2 C3 C8 85.70(19) . . . . ?
C14 C2 C19 C20 -177.68(15) . . . . ?
C14 C2 N1 C13 -78.1(2) . . . . ?
C14 C15 O16 C17 174.47(17) . . . . ?
C19 C2 C3 C4 35.1(2) . . . . ?
C19 C2 C3 C8 -151.19(16) . . . . ?
C19 C2 C14 C15 -77.6(2) . . . . ?
C19 C2 N1 C13 162.79(15) . . . . ?
C19 C20 C21 C22 -171.01(16) . . . . ?
C20 C21 C22 C23 173.1(2) . . . . ?
C24 C11 C12 C13 178.91(18) . . . . ?
C24 C11 N10 N9 -178.41(16) . . . . ?
N1 C2 C3 C4 154.51(16) . . . . ?
N1 C2 C3 C8 -31.8(2) . . . . ?
N1 C2 C14 C15 165.37(16) . . . . ?
N1 C2 C19 C20 -59.91(19) . . . . ?
N1 C13 N9 C8 -7.8(2) . . . . ?
N1 C13 N9 N10 -174.81(15) . . . . ?
N9 C13 N1 C2 -21.6(2) . . . . ?
N10 C11 C12 C13 0.0(2) . . . . ?
O18 C15 O16 C17 -3.8(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 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.802
