# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_N-acetyl-2-(1H-1_2_3-triazol-1-yl)-L-tryptophan_methyl_ester
_database_code_depnum_ccdc_archive 'CCDC 2298364'
loop_
_audit_author_name
_audit_author_address
'Yuki Wada'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_audit_creation_date             2023-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
y.wada@chem.titech.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N5 O3'
_chemical_formula_sum            'C16 H17 N5 O3'
_chemical_formula_weight         327.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.78319(6)
_cell_length_b                   10.61767(7)
_cell_length_c                   9.51916(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.9580(8)
_cell_angle_gamma                90
_cell_volume                     804.830(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24799
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      75.5420
_cell_measurement_theta_min      5.1020
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26347
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.621
_diffrn_reflns_theta_min         5.125
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -30.00   0.50    0.06    -- -102.00  61.00-180.00   88
  2  ω    -74.00 -30.00   0.50    0.06    -- -102.00  61.00 -30.00   88
  3  ω   -124.00 -30.00   0.50    0.06    -- -102.00  77.00  60.00  188
  4  ω     -6.00  26.00   0.50    0.06    --  -48.44  19.00  30.00   64
  5  ω     27.00 121.00   0.50    0.06    --   48.44  77.00   0.00  188
  6  ω     27.00 121.00   0.50    0.06    --   48.44  77.00  30.00  188
  7  ω     27.00 121.00   0.50    0.06    --   48.44  77.00 -60.00  188
  8  ω     27.00 121.00   0.50    0.06    --   48.44  77.00 -30.00  188
  9  ω     39.00 121.00   0.50    0.06    --   48.44  37.00  30.00  164
 10  ω     39.00 123.00   0.50    0.06    --   48.44  19.00 -30.00  168
 11  ω     38.00 123.00   0.50    0.06    --   48.44  13.00-101.00  170
 12  ω     81.00 174.00   0.50    0.06    --  102.75  77.00-120.00  186
 13  ω     81.00 174.00   0.50    0.06    --  102.75  77.00 -90.00  186
 14  ω     81.00 174.00   0.50    0.06    --  102.75  77.00 -60.00  186
 15  ω    115.00 141.00   0.50    0.06    --  102.75  77.00   0.00   52
 16  ω     81.00 106.00   0.50    0.06    --  102.75  77.00   0.00   50
 17  ω     81.00 165.00   0.50    0.06    --  102.75  77.00  30.00  168
 18  ω     88.00 174.00   0.50    0.06    --  102.75  61.00 -30.00  172
 19  ω     90.00 117.00   0.50    0.06    --  102.75  61.00 -90.00   54
 20  ω     92.00 174.00   0.50    0.06    --  102.75  45.00 -30.00  164
 21  ω     92.00 170.00   0.50    0.06    --  102.75  13.00-101.00  156
 22  ω     31.00  79.00   0.50    0.06    --  102.75 -61.00 -60.00   96
 23  ω     31.00 106.00   0.50    0.06    --  102.75 -94.00 -90.00  150
 24  ω     32.00  76.00   0.50    0.06    --  102.75 -61.00-150.00   88
 25  ω     31.00 106.00   0.50    0.06    --  102.75 -94.00-150.00  150
 26  ω     19.00  93.00   0.50    0.06    --   48.44-125.00-120.00  148
 27  ω     32.00 103.00   0.50    0.06    --  102.75 -94.00-180.00  142
 28  ω     31.00 106.00   0.50    0.06    --  102.75 -94.00 -60.00  150
 29  ω     34.00 111.00   0.50    0.06    --  102.75-125.00   0.00  154
 30  ω     31.00 106.00   0.50    0.06    --  102.75 -94.00  90.00  150
 31  ω   -121.00 -37.00   0.50    0.06    --  -48.44 -13.00  86.00  168
 32  ω   -121.00 -37.00   0.50    0.06    --  -48.44 -37.00  30.00  168
 33  ω   -119.00 -34.00   0.50    0.06    --  -48.44 -57.00   0.00  170
 34  ω   -118.00 -32.00   0.50    0.06    -- -102.00 134.00 -55.95  172
 35  ω   -111.00 -33.00   0.50    0.06    -- -102.00 125.00 -30.00  156
 36  ω   -165.00 -91.00   0.50    0.06    -- -102.00 -13.00  86.00  148
 37  ω   -174.00 -80.00   0.50    0.06    -- -102.00 -77.00  67.32  188
 38  ω   -174.00 -80.00   0.50    0.06    -- -102.00 -77.00  30.00  188
 39  ω   -174.00 -81.00   0.50    0.06    -- -102.00 -76.00  93.13  186
 40  ω   -174.00 -80.00   0.50    0.06    -- -102.00 -77.00   0.00  188
 41  ω   -174.00 -82.00   0.50    0.06    -- -102.00 -73.00   8.29  184
 42  ω   -174.00 -81.00   0.50    0.06    -- -102.00 -74.00  18.42  186
 43  ω   -174.00 -83.00   0.50    0.06    -- -102.00 -69.00  31.12  182
 44  ω   -174.00 -85.00   0.50    0.06    -- -102.00 -64.00  63.62  178
 45  ω   -174.00 -80.00   0.50    0.06    -- -102.00 -77.00 -45.16  188
 46  ω   -174.00 -87.00   0.50    0.06    -- -102.00 -61.00 -60.00  174
 47  ω   -174.00 -80.00   0.50    0.06    -- -102.00 -77.00 -30.00  188
 48  ω   -174.00 -81.00   0.50    0.06    -- -102.00 -74.00 -19.18  186
 49  ω   -174.00 -88.00   0.50    0.06    -- -102.00 -57.00 -40.76  172
 50  ω   -174.00 -91.00   0.50    0.06    -- -102.00 -45.00 -30.00  166
 51  ω   -174.00 -87.00   0.50    0.06    -- -102.00 -59.00  33.43  174
 52  ω   -174.00 -87.00   0.50    0.06    -- -102.00 -61.00  30.00  174
 53  ω   -174.00 -87.00   0.50    0.06    -- -102.00 -59.00  53.62  174
 54  ω   -169.00 -91.00   0.50    0.06    -- -102.00 -15.00-120.00  156
;
_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      0.0027528000
_diffrn_orient_matrix_UB_12      0.0252874000
_diffrn_orient_matrix_UB_13      0.1604453000
_diffrn_orient_matrix_UB_21      0.1934365000
_diffrn_orient_matrix_UB_22      -0.0032698000
_diffrn_orient_matrix_UB_23      0.0736496000
_diffrn_orient_matrix_UB_31      0.0038912000
_diffrn_orient_matrix_UB_32      0.1427937000
_diffrn_orient_matrix_UB_33      -0.0266954000
_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         0.804
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                3159
_reflns_number_total             3170
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.051
_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)+(0.0422P)²+0.1230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0674
_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:
 C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), N7(H7), C9(H9), C10(H10), C11(H11), C12(H12), N21(H21)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
;
_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 0.83592(16) 0.47264(14) 0.16153(15) 0.0201(3) Uani 1 1 d . . . . .
N4 N 0.67517(17) 0.43449(16) 0.07834(16) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.65774(18) 0.40799(16) -0.06176(16) 0.0274(3) Uani 1 1 d . . . . .
C4 C 0.8071(2) 0.42758(18) -0.0686(2) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.828515 0.414419 -0.157348 0.031 Uiso 1 1 calc R U . . .
C5 C 0.9216(2) 0.46912(18) 0.07185(19) 0.0233(3) Uani 1 1 d . . . . .
H5 H 1.035791 0.490747 0.100474 0.028 Uiso 1 1 calc R U . . .
C6 C 0.89738(19) 0.50130(16) 0.32115(17) 0.0191(3) Uani 1 1 d . . . . .
N7 N 1.05430(16) 0.45774(14) 0.41672(15) 0.0213(3) Uani 1 1 d . . . . .
H7 H 1.119875 0.411629 0.388473 0.026 Uiso 1 1 calc R U . . .
C8 C 1.09087(19) 0.49887(16) 0.56431(18) 0.0201(3) Uani 1 1 d . . . . .
C9 C 1.2386(2) 0.48580(18) 0.7004(2) 0.0253(4) Uani 1 1 d . . . . .
H9 H 1.331639 0.439022 0.702208 0.030 Uiso 1 1 calc R U . . .
C10 C 1.2429(2) 0.54401(19) 0.83176(19) 0.0274(4) Uani 1 1 d . . . . .
H10 H 1.341239 0.537164 0.926028 0.033 Uiso 1 1 calc R U . . .
C11 C 1.1053(2) 0.61316(19) 0.8295(2) 0.0268(4) Uani 1 1 d . . . . .
H11 H 1.112728 0.652212 0.921922 0.032 Uiso 1 1 calc R U . . .
C12 C 0.9593(2) 0.62533(17) 0.69486(19) 0.0219(3) Uani 1 1 d . . . . .
H12 H 0.866636 0.671811 0.694283 0.026 Uiso 1 1 calc R U . . .
C13 C 0.95117(19) 0.56759(16) 0.55947(17) 0.0186(3) Uani 1 1 d . . . . .
C14 C 0.82655(18) 0.56880(15) 0.40114(17) 0.0182(3) Uani 1 1 d . . . . .
C15 C 0.65819(18) 0.63241(16) 0.34681(18) 0.0192(3) Uani 1 1 d . . . . .
H15A H 0.617189 0.653060 0.235404 0.023 Uiso 1 1 calc R U . . .
H15B H 0.671092 0.712357 0.404254 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2342(2) 0.74986(18) 0.4607(2) 0.0262(4) Uani 1 1 d . . . . .
H16A H 0.129062 0.709499 0.390739 0.039 Uiso 1 1 calc R U . . .
H16B H 0.243830 0.832352 0.419028 0.039 Uiso 1 1 calc R U . . .
H16C H 0.234390 0.760696 0.563045 0.039 Uiso 1 1 calc R U . . .
O17 O 0.37494(13) 0.67148(12) 0.47452(13) 0.0233(3) Uani 1 1 d . . . . .
O18 O 0.25548(14) 0.64229(13) 0.21641(13) 0.0248(3) Uani 1 1 d . . . . .
C19 C 0.36872(18) 0.62506(16) 0.34184(18) 0.0186(3) Uani 1 1 d . . . . .
C20 C 0.52698(18) 0.54914(16) 0.37074(17) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.575917 0.516888 0.479605 0.022 Uiso 1 1 calc R U . . .
N21 N 0.48664(16) 0.44356(13) 0.26493(16) 0.0206(3) Uani 1 1 d . . . . .
H21 H 0.534490 0.438228 0.200448 0.025 Uiso 1 1 calc R U . . .
O22 O 0.30918(15) 0.35729(12) 0.35201(15) 0.0259(3) Uani 1 1 d . . . . .
C23 C 0.37875(19) 0.35401(16) 0.26253(19) 0.0220(3) Uani 1 1 d . . . . .
C24 C 0.3484(2) 0.2501(2) 0.1470(2) 0.0328(4) Uani 1 1 d . . . . .
H24A H 0.387365 0.170070 0.201803 0.049 Uiso 1 1 calc R U . . .
H24B H 0.410017 0.267850 0.084094 0.049 Uiso 1 1 calc R U . . .
H24C H 0.228039 0.244460 0.079647 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N4 1.3569(19) . ?
N1 C5 1.356(2) . ?
N1 C6 1.414(2) . ?
N4 N3 1.307(2) . ?
N3 C4 1.357(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(2) . ?
C5 H5 0.9500 . ?
C6 N7 1.372(2) . ?
C6 C14 1.371(2) . ?
N7 H7 0.8800 . ?
N7 C8 1.374(2) . ?
C8 C9 1.401(2) . ?
C8 C13 1.411(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.406(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.402(2) . ?
C13 C14 1.441(2) . ?
C14 C15 1.505(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C20 1.544(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O17 1.450(2) . ?
O17 C19 1.3352(19) . ?
O18 C19 1.2026(19) . ?
C19 C20 1.528(2) . ?
C20 H20 1.0000 . ?
C20 N21 1.448(2) . ?
N21 H21 0.8800 . ?
N21 C23 1.336(2) . ?
O22 C23 1.241(2) . ?
C23 C24 1.500(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N1 C6 121.51(13) . . ?
C5 N1 N4 109.97(13) . . ?
C5 N1 C6 128.37(14) . . ?
N3 N4 N1 107.74(13) . . ?
N4 N3 C4 108.46(14) . . ?
N3 C4 H4 125.4 . . ?
N3 C4 C5 109.30(14) . . ?
C5 C4 H4 125.4 . . ?
N1 C5 C4 104.52(14) . . ?
N1 C5 H5 127.7 . . ?
C4 C5 H5 127.7 . . ?
N7 C6 N1 117.45(14) . . ?
C14 C6 N1 130.70(14) . . ?
C14 C6 N7 111.85(13) . . ?
C6 N7 H7 126.1 . . ?
C6 N7 C8 107.87(13) . . ?
C8 N7 H7 126.1 . . ?
N7 C8 C9 129.77(15) . . ?
N7 C8 C13 107.82(13) . . ?
C9 C8 C13 122.33(15) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 116.97(16) . . ?
C10 C9 H9 121.5 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.65(15) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.17(16) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.57(15) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C14 107.75(13) . . ?
C12 C13 C8 119.32(13) . . ?
C12 C13 C14 132.78(15) . . ?
C6 C14 C13 104.69(13) . . ?
C6 C14 C15 130.84(14) . . ?
C13 C14 C15 124.47(14) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C20 112.25(13) . . ?
H15A C15 H15B 107.9 . . ?
C20 C15 H15A 109.2 . . ?
C20 C15 H15B 109.2 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C16 H16A 109.5 . . ?
O17 C16 H16B 109.5 . . ?
O17 C16 H16C 109.5 . . ?
C19 O17 C16 115.67(13) . . ?
O17 C19 C20 110.69(12) . . ?
O18 C19 O17 124.73(14) . . ?
O18 C19 C20 124.57(14) . . ?
C15 C20 H20 109.1 . . ?
C19 C20 C15 110.51(13) . . ?
C19 C20 H20 109.1 . . ?
N21 C20 C15 108.64(12) . . ?
N21 C20 C19 110.26(12) . . ?
N21 C20 H20 109.1 . . ?
C20 N21 H21 119.1 . . ?
C23 N21 C20 121.79(13) . . ?
C23 N21 H21 119.1 . . ?
N21 C23 C24 116.19(15) . . ?
O22 C23 N21 121.31(16) . . ?
O22 C23 C24 122.50(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 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 N4 N3 C4 0.7(2) . . . . ?
N1 C6 N7 C8 178.27(14) . . . . ?
N1 C6 C14 C13 -178.67(16) . . . . ?
N1 C6 C14 C15 1.7(3) . . . . ?
N4 N1 C5 C4 0.0(2) . . . . ?
N4 N1 C6 N7 136.86(16) . . . . ?
N4 N1 C6 C14 -44.0(3) . . . . ?
N4 N3 C4 C5 -0.7(2) . . . . ?
N3 C4 C5 N1 0.4(2) . . . . ?
C5 N1 N4 N3 -0.4(2) . . . . ?
C5 N1 C6 N7 -38.2(2) . . . . ?
C5 N1 C6 C14 140.95(19) . . . . ?
C6 N1 N4 N3 -176.31(16) . . . . ?
C6 N1 C5 C4 175.54(17) . . . . ?
C6 N7 C8 C9 -175.73(18) . . . . ?
C6 N7 C8 C13 1.09(18) . . . . ?
C6 C14 C15 C20 96.3(2) . . . . ?
N7 C6 C14 C13 0.50(19) . . . . ?
N7 C6 C14 C15 -179.17(16) . . . . ?
N7 C8 C9 C10 176.18(17) . . . . ?
N7 C8 C13 C12 -177.01(15) . . . . ?
N7 C8 C13 C14 -0.79(18) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C8 C13 C14 C6 0.19(18) . . . . ?
C8 C13 C14 C15 179.89(15) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C9 C8 C13 C14 176.32(16) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
C11 C12 C13 C14 -174.90(18) . . . . ?
C12 C13 C14 C6 175.69(18) . . . . ?
C12 C13 C14 C15 -4.6(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C13 C14 C15 C20 -83.31(19) . . . . ?
C14 C6 N7 C8 -1.02(19) . . . . ?
C14 C15 C20 C19 169.82(13) . . . . ?
C14 C15 C20 N21 -69.10(16) . . . . ?
C15 C20 N21 C23 178.44(14) . . . . ?
C16 O17 C19 O18 -1.3(2) . . . . ?
C16 O17 C19 C20 177.55(13) . . . . ?
O17 C19 C20 C15 -94.53(15) . . . . ?
O17 C19 C20 N21 145.35(13) . . . . ?
O18 C19 C20 C15 84.32(19) . . . . ?
O18 C19 C20 N21 -35.8(2) . . . . ?
C19 C20 N21 C23 -60.32(19) . . . . ?
C20 N21 C23 O22 -0.5(2) . . . . ?
C20 N21 C23 C24 179.96(15) . . . . ?

_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 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.791
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and hexane.'
