# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_793_auto_sq
_database_code_depnum_ccdc_archive 'CCDC 2389889'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2024-10-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N5 O'
_chemical_formula_sum            'C17 H15 N5 O'
_chemical_formula_weight         305.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H15N5O
_chemical_oxdiff_usercomment     223k
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                   7.2189(3)
_cell_length_b                   25.5663(11)
_cell_length_c                   9.9465(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.788(4)
_cell_angle_gamma                90
_cell_volume                     1834.82(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    272.7(8)
_cell_measurement_theta_max      70.3150
_cell_measurement_theta_min      3.4220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21086
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.612
_diffrn_reflns_theta_min         3.457
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      272.7(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -59.00   0.50    3.19    --    0.00  37.00  30.00   54
  2  ω    -30.00  -3.00   0.50    3.19    --    0.00  37.00  30.00   54
  3  ω     31.00  57.00   0.50    3.19    --    0.00  37.00  30.00   52
  4  ω    -22.00  94.00   0.50   12.78    --    5.00  18.00  30.00  232
  5  ω   -153.00 -87.00   0.50   12.78    --  -94.70  28.00  60.00  132
  6  ω   -183.00-157.00   0.50   12.78    --  -94.70  46.00  90.00   52
  7  ω   -183.00 -30.00   0.50   12.78    --  -94.70  18.00-120.00  306
  8  ω   -165.00 -96.00   0.50   12.78    --  -94.70  18.00  30.00  138
  9  ω   -179.00 -63.00   0.50   12.78    --  -94.70  46.00 120.00  232
 10  ω    -71.00  -5.00   0.50   12.78    --  -94.70  46.00  90.00  132
 11  ω   -127.00 -80.00   0.50   12.78    --  -94.70  46.00  90.00   94
 12  ω   -112.00 -83.00   0.50   12.78    --  -94.70  53.00  52.34   58
 13  ω   -167.00-137.00   0.50   12.78    --  -94.70  53.00  52.34   60
 14  ω    -47.00  -6.00   0.50    3.19    --    0.00  37.00-180.00   82
 15  ω    -62.00 -35.00   0.50    3.19    --    0.00  46.00  60.00   54
 16  ω     57.00  89.00   0.50    3.19    --    0.00  37.00-180.00   64
 17  ω      4.00  51.00   0.50    3.19    --    0.00  37.00-180.00   94
 18  ω   -138.00 -93.00   0.50   12.78    --  -94.70  46.00   0.00   90
 19  ω    -49.00  -6.00   0.50   12.78    --  -94.70  46.00   0.00   86
 20  ω   -168.00-102.00   0.50   12.78    --  -94.70  55.00 160.04  132
 21  ω    -61.00  -5.00   0.50   12.78    --  -94.70  50.00 112.55  112
 22  ω    -96.00 -53.00   0.50   12.78    --  -94.70  54.00  70.88   86
 23  ω    -30.00  -5.00   0.50   12.78    --  -94.70  52.00 178.75   50
 24  ω    -60.00  -5.00   0.50   12.78    --  -94.70  49.00 133.05  110
 25  ω    -74.00  -5.00   0.50   12.78    --  -94.70  54.00  25.59  138
 26  ω    -36.00 -11.00   0.50   12.78    --  -94.70  55.00 136.70   50
 27  ω    -52.00 -11.00   0.50   12.78    --  -94.70  46.00 -30.00   82
 28  ω    -35.00  -6.00   0.50   12.78    --  -94.70  52.00 169.41   58
 29  ω   -150.00-124.00   0.50   12.78    --  -94.70  52.00 178.75   52
 30  ω    -56.00  -6.00   0.50   12.78    --  -94.70  55.00 160.04  100
 31  ω    -54.00  -6.00   0.50   12.78    --  -94.70  46.00-180.00   96
 32  ω    -75.00 -40.00   0.50   12.78    --  -94.70  55.00  82.77   70
 33  ω   -166.00-122.00   0.50   12.78    --  -94.70  55.00  82.77   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0792253000
_diffrn_orient_matrix_UB_12      -0.0559611000
_diffrn_orient_matrix_UB_13      0.0032580000
_diffrn_orient_matrix_UB_21      -0.0093313000
_diffrn_orient_matrix_UB_22      -0.0016773000
_diffrn_orient_matrix_UB_23      -0.1548508000
_diffrn_orient_matrix_UB_31      0.1981187000
_diffrn_orient_matrix_UB_32      0.0222659000
_diffrn_orient_matrix_UB_33      -0.0035369000
_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         0.920
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5005
_reflns_number_total             7079
_reflns_odcompleteness_completeness 99.97
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7079
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1484
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C44(H44), C35(H35), C45(H45), C11(H11), C10(H10), C31(H31),
 C8(H8), C33(H33), C18(H18), C25(H25), C41(H41), C32(H32), C43(H43), C42(H42),
 C22(H22), C20(H20), C21(H21), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N23(H23A,H23B), N46(H46A,H46B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O13 O 1.7223(4) 0.66057(12) 0.4547(3) 0.0767(8) Uani 1 1 d . . . . .
N15 N 0.6958(4) 0.61721(13) 0.8627(4) 0.0625(8) Uani 1 1 d . . . . .
N29 N 0.6385(4) 0.42731(12) 0.6320(4) 0.0592(8) Uani 1 1 d . . . . .
N38 N 0.1738(4) 0.38662(13) 0.3980(4) 0.0640(9) Uani 1 1 d . . . . .
N2 N 1.1379(4) 0.57677(12) 0.6302(4) 0.0568(8) Uani 1 1 d . . . . .
N27 N 0.3366(4) 0.44431(12) 0.5322(4) 0.0608(8) Uani 1 1 d . . . . .
N4 N 0.8448(4) 0.56012(12) 0.7275(3) 0.0584(8) Uani 1 1 d . . . . .
N16 N 0.7159(4) 0.65450(14) 0.9398(4) 0.0662(9) Uani 1 1 d . . . . .
N39 N 0.1939(5) 0.35068(13) 0.3144(4) 0.0676(9) Uani 1 1 d . . . . .
N23 N 0.9839(4) 0.49879(13) 0.5983(4) 0.0790(11) Uani 1 1 d . . . . .
H23A H 0.889810 0.478834 0.609967 0.095 Uiso 1 1 calc R U . . .
H23B H 1.073812 0.488192 0.550633 0.095 Uiso 1 1 calc R U . . .
N46 N 0.4875(4) 0.50579(13) 0.6618(4) 0.0788(12) Uani 1 1 d . . . . .
H46A H 0.393868 0.526097 0.648037 0.095 Uiso 1 1 calc R U . . .
H46B H 0.580818 0.516242 0.710527 0.095 Uiso 1 1 calc R U . . .
C1 C 1.1399(4) 0.62496(13) 0.6845(4) 0.0508(8) Uani 1 1 d . . . . .
C5 C 0.8538(4) 0.60733(14) 0.7832(4) 0.0529(9) Uani 1 1 d . . . . .
O36 O 1.2363(4) 0.34266(15) 0.8043(4) 0.0903(10) Uani 1 1 d . . . . .
C28 C 0.4880(5) 0.45755(14) 0.6070(5) 0.0590(10) Uani 1 1 d . . . . .
C9 C 1.5878(5) 0.67244(16) 0.5436(4) 0.0583(9) Uani 1 1 d . . . . .
C7 C 1.3031(5) 0.65809(13) 0.6589(4) 0.0510(8) Uani 1 1 d . . . . .
C12 C 1.3359(5) 0.70419(14) 0.7308(4) 0.0576(9) Uani 1 1 d . . . . .
H12 H 1.251553 0.715309 0.793606 0.069 Uiso 1 1 calc R U . . .
C40 C 0.0338(6) 0.34121(16) 0.2296(4) 0.0642(10) Uani 1 1 d . . . . .
C30 C 0.7964(5) 0.34489(14) 0.6070(4) 0.0559(9) Uani 1 1 d . . . . .
C3 C 0.9902(5) 0.54644(14) 0.6546(4) 0.0595(10) Uani 1 1 d . . . . .
C26 C 0.3390(5) 0.39681(14) 0.4785(4) 0.0560(9) Uani 1 1 d . . . . .
C17 C 0.5595(5) 0.66457(18) 1.0217(4) 0.0646(10) Uani 1 1 d . . . . .
C24 C 0.6325(5) 0.37892(14) 0.5792(4) 0.0550(9) Uani 1 1 d . . . . .
C6 C 0.9951(5) 0.64200(14) 0.7626(4) 0.0566(9) Uani 1 1 d . . . . .
H6 H 0.994184 0.675471 0.799213 0.068 Uiso 1 1 calc R U . . .
C44 C -0.2769(7) 0.3549(2) 0.1518(6) 0.0915(16) Uani 1 1 d . . . . .
H44 H -0.391311 0.371198 0.159357 0.110 Uiso 1 1 calc R U . . .
C35 C 0.9362(5) 0.36102(16) 0.6976(4) 0.0603(10) Uani 1 1 d . . . . .
H35 H 0.924947 0.392492 0.743502 0.072 Uiso 1 1 calc R U . . .
C45 C -0.1334(6) 0.36651(19) 0.2424(5) 0.0776(12) Uani 1 1 d . . . . .
H45 H -0.149346 0.390855 0.310583 0.093 Uiso 1 1 calc R U . . .
C11 C 1.4926(5) 0.73326(15) 0.7092(4) 0.0626(10) Uani 1 1 d . . . . .
H11 H 1.513497 0.763723 0.758434 0.075 Uiso 1 1 calc R U . . .
C10 C 1.6181(5) 0.71824(15) 0.6167(5) 0.0639(10) Uani 1 1 d . . . . .
H10 H 1.722925 0.738431 0.602789 0.077 Uiso 1 1 calc R U . . .
C31 C 0.8135(5) 0.29746(15) 0.5418(5) 0.0633(10) Uani 1 1 d . . . . .
H31 H 0.720198 0.286173 0.482064 0.076 Uiso 1 1 calc R U . . .
C8 C 1.4305(5) 0.64266(15) 0.5635(4) 0.0576(9) Uani 1 1 d . . . . .
H8 H 1.409742 0.612396 0.513440 0.069 Uiso 1 1 calc R U . . .
C33 C 1.1054(6) 0.28285(18) 0.6517(5) 0.0704(11) Uani 1 1 d . . . . .
H33 H 1.209711 0.262030 0.666290 0.085 Uiso 1 1 calc R U . . .
C18 C 0.3992(6) 0.63446(19) 1.0168(5) 0.0734(11) Uani 1 1 d . . . . .
H18 H 0.388778 0.606006 0.958756 0.088 Uiso 1 1 calc R U . . .
C25 C 0.4822(5) 0.36215(14) 0.5001(5) 0.0611(10) Uani 1 1 d . . . . .
H25 H 0.478558 0.328732 0.463112 0.073 Uiso 1 1 calc R U . . .
C34 C 1.0920(5) 0.33009(18) 0.7191(4) 0.0658(10) Uani 1 1 d . . . . .
C41 C 0.0546(7) 0.3049(2) 0.1294(5) 0.0839(13) Uani 1 1 d . . . . .
H41 H 0.166362 0.287127 0.122962 0.101 Uiso 1 1 calc R U . . .
C32 C 0.9696(5) 0.26658(17) 0.5653(5) 0.0677(11) Uani 1 1 d . . . . .
H32 H 0.980512 0.234658 0.521396 0.081 Uiso 1 1 calc R U . . .
C43 C -0.2501(9) 0.3193(3) 0.0503(6) 0.0969(18) Uani 1 1 d . . . . .
H43 H -0.346176 0.312109 -0.011483 0.116 Uiso 1 1 calc R U . . .
C42 C -0.0866(8) 0.2947(2) 0.0396(5) 0.0928(16) Uani 1 1 d . . . . .
H42 H -0.070048 0.270738 -0.029260 0.111 Uiso 1 1 calc R U . . .
C22 C 0.5772(7) 0.7069(2) 1.1084(5) 0.0806(13) Uani 1 1 d . . . . .
H22 H 0.684772 0.726899 1.110881 0.097 Uiso 1 1 calc R U . . .
C20 C 0.2742(8) 0.6897(3) 1.1858(6) 0.0984(18) Uani 1 1 d . . . . .
H20 H 0.177671 0.698632 1.241264 0.118 Uiso 1 1 calc R U . . .
C14 C 1.7055(8) 0.6129(2) 0.3821(6) 0.0854(14) Uani 1 1 d . . . . .
H14A H 1.812650 0.608199 0.328550 0.128 Uiso 1 1 calc R U . . .
H14B H 1.596385 0.614078 0.324496 0.128 Uiso 1 1 calc R U . . .
H14C H 1.696247 0.584348 0.444034 0.128 Uiso 1 1 calc R U . . .
C21 C 0.4334(8) 0.7188(2) 1.1908(5) 0.0920(16) Uani 1 1 d . . . . .
H21 H 0.444650 0.746743 1.250282 0.110 Uiso 1 1 calc R U . . .
C19 C 0.2539(7) 0.6474(2) 1.0999(6) 0.0926(16) Uani 1 1 d . . . . .
H19 H 0.145109 0.627928 1.097609 0.111 Uiso 1 1 calc R U . . .
C37 C 1.2309(8) 0.3916(2) 0.8726(6) 0.0991(17) Uani 1 1 d . . . . .
H37A H 1.214407 0.419297 0.808147 0.149 Uiso 1 1 calc R U . . .
H37B H 1.345054 0.396775 0.922945 0.149 Uiso 1 1 calc R U . . .
H37C H 1.129477 0.391741 0.932828 0.149 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
O13 C9 1.368(5) . ?
O13 C14 1.419(6) . ?
N15 N16 1.229(4) . ?
N15 C5 1.431(5) . ?
N29 C28 1.350(4) . ?
N29 C24 1.344(5) . ?
N38 N39 1.250(5) . ?
N38 C26 1.439(5) . ?
N2 C1 1.345(5) . ?
N2 C3 1.346(5) . ?
N27 C28 1.346(5) . ?
N27 C26 1.327(5) . ?
N4 C5 1.329(5) . ?
N4 C3 1.340(5) . ?
N16 C17 1.436(5) . ?
N39 C40 1.430(5) . ?
N23 C3 1.341(5) . ?
N46 C28 1.348(5) . ?
C1 C7 1.479(5) . ?
C1 C6 1.392(5) . ?
C5 C6 1.372(5) . ?
O36 C34 1.360(5) . ?
O36 C37 1.425(7) . ?
C9 C10 1.392(6) . ?
C9 C8 1.386(5) . ?
C7 C12 1.395(5) . ?
C7 C8 1.399(5) . ?
C12 C11 1.376(5) . ?
C40 C45 1.379(6) . ?
C40 C41 1.373(6) . ?
C30 C24 1.487(5) . ?
C30 C35 1.395(5) . ?
C30 C31 1.382(5) . ?
C26 C25 1.373(5) . ?
C17 C18 1.390(6) . ?
C17 C22 1.386(6) . ?
C24 C25 1.389(5) . ?
C44 C45 1.384(7) . ?
C44 C43 1.379(8) . ?
C35 C34 1.386(5) . ?
C11 C10 1.366(6) . ?
C31 C32 1.390(5) . ?
C33 C34 1.386(6) . ?
C33 C32 1.349(6) . ?
C18 C19 1.396(6) . ?
C41 C42 1.359(7) . ?
C43 C42 1.344(9) . ?
C22 C21 1.377(7) . ?
C20 C21 1.368(9) . ?
C20 C19 1.384(8) . ?

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
C9 O13 C14 117.9(3) . . ?
N16 N15 C5 113.6(3) . . ?
C24 N29 C28 116.1(3) . . ?
N39 N38 C26 113.0(3) . . ?
C1 N2 C3 117.0(3) . . ?
C26 N27 C28 115.6(3) . . ?
C5 N4 C3 115.7(3) . . ?
N15 N16 C17 114.4(3) . . ?
N38 N39 C40 114.1(3) . . ?
N2 C1 C7 117.0(3) . . ?
N2 C1 C6 120.8(3) . . ?
C6 C1 C7 122.2(3) . . ?
N4 C5 N15 111.2(3) . . ?
N4 C5 C6 123.5(3) . . ?
C6 C5 N15 125.3(3) . . ?
C34 O36 C37 118.2(4) . . ?
N27 C28 N29 126.3(3) . . ?
N27 C28 N46 116.2(3) . . ?
N46 C28 N29 117.5(3) . . ?
O13 C9 C10 114.9(3) . . ?
O13 C9 C8 124.9(4) . . ?
C8 C9 C10 120.2(4) . . ?
C12 C7 C1 121.2(3) . . ?
C12 C7 C8 118.8(3) . . ?
C8 C7 C1 120.0(3) . . ?
C11 C12 C7 120.2(4) . . ?
C45 C40 N39 124.0(4) . . ?
C41 C40 N39 116.0(4) . . ?
C41 C40 C45 120.0(4) . . ?
C35 C30 C24 120.2(3) . . ?
C31 C30 C24 120.6(3) . . ?
C31 C30 C35 119.3(3) . . ?
N4 C3 N2 125.8(3) . . ?
N4 C3 N23 116.5(3) . . ?
N23 C3 N2 117.7(3) . . ?
N27 C26 N38 111.6(3) . . ?
N27 C26 C25 123.1(3) . . ?
C25 C26 N38 125.2(3) . . ?
C18 C17 N16 123.3(4) . . ?
C22 C17 N16 115.7(4) . . ?
C22 C17 C18 120.9(4) . . ?
N29 C24 C30 116.8(3) . . ?
N29 C24 C25 121.4(3) . . ?
C25 C24 C30 121.8(3) . . ?
C5 C6 C1 117.1(3) . . ?
C43 C44 C45 120.0(6) . . ?
C34 C35 C30 119.9(4) . . ?
C40 C45 C44 118.6(5) . . ?
C10 C11 C12 121.3(4) . . ?
C11 C10 C9 119.5(3) . . ?
C30 C31 C32 120.2(4) . . ?
C9 C8 C7 120.1(4) . . ?
C32 C33 C34 121.1(4) . . ?
C17 C18 C19 119.2(5) . . ?
C26 C25 C24 117.4(3) . . ?
O36 C34 C35 124.3(4) . . ?
O36 C34 C33 116.3(4) . . ?
C35 C34 C33 119.4(4) . . ?
C42 C41 C40 120.6(5) . . ?
C33 C32 C31 120.1(4) . . ?
C42 C43 C44 120.7(5) . . ?
C43 C42 C41 120.1(6) . . ?
C21 C22 C17 119.1(5) . . ?
C21 C20 C19 121.3(5) . . ?
C20 C21 C22 120.5(5) . . ?
C20 C19 C18 119.0(5) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.595 0.003 -0.135 201.0 43.9 ?
2 -0.792 0.503 0.135 201.0 44.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_special_details  ?
_platon_squeeze_void_probe_radius 1.20
_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 1.891
_oxdiff_exptl_absorpt_empirical_full_min 0.407
####################################################################### 
# 
# 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_798_auto
_database_code_depnum_ccdc_archive 'CCDC 2389890'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-10-10 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N5 O3, C4 H8 O2'
_chemical_formula_sum            'C22 H23 N5 O5'
_chemical_formula_weight         437.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H17N5O2
_chemical_oxdiff_usercomment     '223 K'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.37273(19)
_cell_length_b                   9.0040(3)
_cell_length_c                   16.1224(4)
_cell_angle_alpha                96.732(2)
_cell_angle_beta                 95.788(2)
_cell_angle_gamma                94.114(2)
_cell_volume                     1053.68(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    222.9(3)
_cell_measurement_theta_max      72.0230
_cell_measurement_theta_min      4.9400
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20019
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.637
_diffrn_reflns_theta_min         2.777
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      222.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    0.88    --    0.00  28.00 150.00  356
  2  ω    -89.00  89.00   0.50    0.88    --    0.00  46.00 -90.00  356
  3  ω    -84.00  94.00   0.50    3.51    --    5.00  18.00 -30.00  356
  4  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00-126.04  358
  5  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00-178.12  358
  6  ω   -184.00  -5.00   0.50    3.51    --  -94.70  42.00  19.51  358
  7  ω   -184.00  -5.00   0.50    3.51    --  -94.70   9.00-180.00  358
  8  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 110.09  358
  9  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 -31.17  358
 10  ω   -184.00  -5.00   0.50    3.51    --  -94.70  53.00-107.55  358
 11  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 161.16  358
 12  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00  32.29  358
 13  ω   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 -67.24  358
 14  ω    -89.00  89.00   0.50    0.88    --    0.00   9.00-150.00  356
 15  ω    -89.00  89.00   0.50    0.88    --    0.00  46.00   0.00  356
 16  ω   -184.00-101.00   0.50    3.51    --  -94.70  53.00  80.39  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471902000
_diffrn_orient_matrix_UB_12      -0.0673993000
_diffrn_orient_matrix_UB_13      -0.0926584000
_diffrn_orient_matrix_UB_21      0.0660161000
_diffrn_orient_matrix_UB_22      0.1506271000
_diffrn_orient_matrix_UB_23      -0.0280053000
_diffrn_orient_matrix_UB_31      0.1945330000
_diffrn_orient_matrix_UB_32      -0.0516222000
_diffrn_orient_matrix_UB_33      -0.0014045000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3216
_reflns_number_total             4049
_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 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.063
_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)+(0.0717P)²+0.2170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1328
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C2(H2), C13(H13), C8(H8), C19(H19), C9(H9), C21(H21), C20(H20)
2.c X=CH2 refined with riding coordinates:
 N26(H26A,H26B)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
;
_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
O4 O 0.72102(17) 0.73960(13) 0.76467(6) 0.0507(3) Uani 1 1 d . . . . .
O6 O 0.82898(18) 0.96965(12) 0.73067(7) 0.0528(3) Uani 1 1 d . . . . .
O24 O 0.73995(18) -0.06132(15) -0.01091(7) 0.0603(4) Uani 1 1 d . . . . .
O27 O 0.74193(18) 1.33280(14) 0.76086(7) 0.0582(3) Uani 1 1 d . . . . .
N15 N 0.62189(17) 0.12900(14) 0.43985(7) 0.0386(3) Uani 1 1 d . . . . .
N17 N 0.63652(17) 0.02888(14) 0.29586(7) 0.0394(3) Uani 1 1 d . . . . .
N11 N 0.71042(18) 0.37373(14) 0.49400(8) 0.0409(3) Uani 1 1 d . . . . .
N10 N 0.75729(18) 0.50162(14) 0.47590(8) 0.0414(3) Uani 1 1 d . . . . .
N26 N 0.5164(2) -0.11394(15) 0.38981(8) 0.0492(4) Uani 1 1 d . . . . .
H26A H 0.495815 -0.188741 0.349776 0.059 Uiso 1 1 calc R U . . .
H26B H 0.487031 -0.124804 0.439802 0.059 Uiso 1 1 calc R U . . .
O29 O 0.9977(2) 1.30199(19) 0.84071(9) 0.0773(4) Uani 1 1 d . . . . .
C12 C 0.7099(2) 0.16276(17) 0.28113(9) 0.0371(3) Uani 1 1 d . . . . .
C3 C 0.7557(2) 0.72558(17) 0.68221(9) 0.0386(3) Uani 1 1 d . . . . .
C18 C 0.7577(2) 0.17312(17) 0.19405(9) 0.0391(3) Uani 1 1 d . . . . .
C14 C 0.6906(2) 0.26055(17) 0.42228(9) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.7750(2) 0.61869(17) 0.54354(9) 0.0391(3) Uani 1 1 d . . . . .
C16 C 0.5935(2) 0.01787(16) 0.37449(9) 0.0382(3) Uani 1 1 d . . . . .
C7 C 0.8190(2) 0.86417(17) 0.66221(9) 0.0403(3) Uani 1 1 d . . . . .
C23 C 0.7258(2) 0.04654(18) 0.13389(9) 0.0412(4) Uani 1 1 d . . . . .
H23 H 0.675085 -0.044339 0.148478 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7315(2) 0.59947(17) 0.62508(9) 0.0404(3) Uani 1 1 d . . . . .
H2 H 0.688614 0.505807 0.639146 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7382(2) 0.28462(17) 0.34341(9) 0.0398(3) Uani 1 1 d . . . . .
H13 H 0.787283 0.378928 0.332806 0.048 Uiso 1 1 calc R U . . .
C22 C 0.7688(2) 0.0548(2) 0.05261(9) 0.0456(4) Uani 1 1 d . . . . .
C8 C 0.8603(2) 0.88472(18) 0.58297(10) 0.0470(4) Uani 1 1 d . . . . .
H8 H 0.902272 0.979146 0.569616 0.056 Uiso 1 1 calc R U . . .
C19 C 0.8340(2) 0.30633(19) 0.17152(10) 0.0485(4) Uani 1 1 d . . . . .
H19 H 0.856465 0.392132 0.211525 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8363(2) 0.75767(18) 0.52351(9) 0.0451(4) Uani 1 1 d . . . . .
H9 H 0.862522 0.766459 0.468337 0.054 Uiso 1 1 calc R U . . .
C5 C 0.7704(2) 0.89318(19) 0.79763(9) 0.0461(4) Uani 1 1 d . . . . .
H5A H 0.869409 0.900228 0.843627 0.055 Uiso 1 1 calc R U . . .
H5B H 0.665068 0.938626 0.819430 0.055 Uiso 1 1 calc R U . . .
C21 C 0.8459(2) 0.1883(2) 0.03078(10) 0.0512(4) Uani 1 1 d . . . . .
H21 H 0.876419 0.193338 -0.024088 0.061 Uiso 1 1 calc R U . . .
C28 C 0.9179(3) 1.30403(19) 0.77243(11) 0.0521(4) Uani 1 1 d . . . . .
C20 C 0.8770(2) 0.3129(2) 0.08998(11) 0.0532(4) Uani 1 1 d . . . . .
H20 H 0.928019 0.403545 0.075155 0.064 Uiso 1 1 calc R U . . .
C25 C 0.6687(3) -0.2027(2) 0.00758(12) 0.0634(5) Uani 1 1 d . . . . .
H25A H 0.659400 -0.275307 -0.042440 0.095 Uiso 1 1 calc R U . . .
H25B H 0.548344 -0.193761 0.026099 0.095 Uiso 1 1 calc R U . . .
H25C H 0.749553 -0.235881 0.051729 0.095 Uiso 1 1 calc R U . . .
C32 C 0.9975(3) 1.2790(2) 0.69147(12) 0.0623(5) Uani 1 1 d . . . . .
H32A H 0.899882 1.251314 0.646062 0.094 Uiso 1 1 calc R U . . .
H32B H 1.078451 1.198901 0.693385 0.094 Uiso 1 1 calc R U . . .
H32C H 1.066014 1.370395 0.682065 0.094 Uiso 1 1 calc R U . . .
C30 C 0.6543(3) 1.3677(3) 0.83605(14) 0.0819(7) Uani 1 1 d . . . . .
H30A H 0.724129 1.451782 0.872332 0.098 Uiso 1 1 calc R U . . .
H30B H 0.649081 1.280654 0.867260 0.098 Uiso 1 1 calc R U . . .
C31 C 0.4713(3) 1.4068(3) 0.81192(18) 0.0937(8) Uani 1 1 d . . . . .
H31A H 0.477131 1.487736 0.777238 0.141 Uiso 1 1 calc R U . . .
H31B H 0.414267 1.439013 0.861898 0.141 Uiso 1 1 calc R U . . .
H31C H 0.399656 1.320047 0.780434 0.141 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
O4 C3 1.3722(17) . ?
O4 C5 1.429(2) . ?
O6 C7 1.3614(18) . ?
O6 C5 1.4325(19) . ?
O24 C22 1.3637(19) . ?
O24 C25 1.418(2) . ?
O27 C28 1.340(2) . ?
O27 C30 1.443(2) . ?
N15 C14 1.3271(19) . ?
N15 C16 1.3542(18) . ?
N17 C12 1.3422(19) . ?
N17 C16 1.3503(18) . ?
N11 N10 1.2540(18) . ?
N11 C14 1.4372(18) . ?
N10 C1 1.4140(18) . ?
N26 H26A 0.8700 . ?
N26 H26B 0.8700 . ?
N26 C16 1.3389(19) . ?
O29 C28 1.197(2) . ?
C12 C18 1.4934(19) . ?
C12 C13 1.386(2) . ?
C3 C7 1.386(2) . ?
C3 C2 1.365(2) . ?
C18 C23 1.397(2) . ?
C18 C19 1.390(2) . ?
C14 C13 1.390(2) . ?
C1 C2 1.411(2) . ?
C1 C9 1.385(2) . ?
C7 C8 1.373(2) . ?
C23 H23 0.9400 . ?
C23 C22 1.388(2) . ?
C2 H2 0.9400 . ?
C13 H13 0.9400 . ?
C22 C21 1.391(2) . ?
C8 H8 0.9400 . ?
C8 C9 1.392(2) . ?
C19 H19 0.9400 . ?
C19 C20 1.390(2) . ?
C9 H9 0.9400 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C21 H21 0.9400 . ?
C21 C20 1.375(2) . ?
C28 C32 1.484(2) . ?
C20 H20 0.9400 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 C31 1.446(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?

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 O4 C5 106.34(12) . . ?
C7 O6 C5 106.32(12) . . ?
C22 O24 C25 118.22(13) . . ?
C28 O27 C30 116.11(15) . . ?
C14 N15 C16 115.64(12) . . ?
C12 N17 C16 116.88(12) . . ?
N10 N11 C14 112.58(12) . . ?
N11 N10 C1 115.32(13) . . ?
H26A N26 H26B 120.0 . . ?
C16 N26 H26A 120.0 . . ?
C16 N26 H26B 120.0 . . ?
N17 C12 C18 116.31(13) . . ?
N17 C12 C13 121.61(13) . . ?
C13 C12 C18 122.07(13) . . ?
O4 C3 C7 109.43(13) . . ?
C2 C3 O4 127.91(14) . . ?
C2 C3 C7 122.65(14) . . ?
C23 C18 C12 119.49(14) . . ?
C19 C18 C12 121.34(14) . . ?
C19 C18 C23 119.17(14) . . ?
N15 C14 N11 112.26(12) . . ?
N15 C14 C13 123.43(13) . . ?
C13 C14 N11 124.31(14) . . ?
C2 C1 N10 123.90(14) . . ?
C9 C1 N10 114.58(13) . . ?
C9 C1 C2 121.52(14) . . ?
N17 C16 N15 125.62(13) . . ?
N26 C16 N15 116.71(13) . . ?
N26 C16 N17 117.67(13) . . ?
O6 C7 C3 110.16(13) . . ?
O6 C7 C8 127.58(14) . . ?
C8 C7 C3 122.25(14) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.10(15) . . ?
C22 C23 H23 119.9 . . ?
C3 C2 C1 115.70(14) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C12 C13 C14 116.75(14) . . ?
C12 C13 H13 121.6 . . ?
C14 C13 H13 121.6 . . ?
O24 C22 C23 124.60(15) . . ?
O24 C22 C21 115.09(14) . . ?
C23 C22 C21 120.31(15) . . ?
C7 C8 H8 121.9 . . ?
C7 C8 C9 116.16(14) . . ?
C9 C8 H8 121.9 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.17(16) . . ?
C20 C19 H19 119.9 . . ?
C1 C9 C8 121.71(14) . . ?
C1 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
O4 C5 O6 107.72(11) . . ?
O4 C5 H5A 110.2 . . ?
O4 C5 H5B 110.2 . . ?
O6 C5 H5A 110.2 . . ?
O6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C22 C21 H21 120.2 . . ?
C20 C21 C22 119.58(15) . . ?
C20 C21 H21 120.2 . . ?
O27 C28 C32 111.62(16) . . ?
O29 C28 O27 122.60(17) . . ?
O29 C28 C32 125.77(19) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.67(16) . . ?
C21 C20 H20 119.7 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C28 C32 H32A 109.5 . . ?
C28 C32 H32B 109.5 . . ?
C28 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O27 C30 H30A 110.0 . . ?
O27 C30 H30B 110.0 . . ?
O27 C30 C31 108.5(2) . . ?
H30A C30 H30B 108.4 . . ?
C31 C30 H30A 110.0 . . ?
C31 C30 H30B 110.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
O4 C3 C7 O6 0.76(18) . . . . ?
O4 C3 C7 C8 -178.22(15) . . . . ?
O4 C3 C2 C1 178.59(14) . . . . ?
O6 C7 C8 C9 -179.30(15) . . . . ?
O24 C22 C21 C20 178.71(15) . . . . ?
N15 C14 C13 C12 0.4(2) . . . . ?
N17 C12 C18 C23 -0.4(2) . . . . ?
N17 C12 C18 C19 179.82(14) . . . . ?
N17 C12 C13 C14 1.3(2) . . . . ?
N11 N10 C1 C2 -4.4(2) . . . . ?
N11 N10 C1 C9 176.67(13) . . . . ?
N11 C14 C13 C12 -179.98(13) . . . . ?
N10 N11 C14 N15 -173.12(12) . . . . ?
N10 N11 C14 C13 7.2(2) . . . . ?
N10 C1 C2 C3 -179.46(14) . . . . ?
N10 C1 C9 C8 179.72(15) . . . . ?
C12 N17 C16 N15 -1.6(2) . . . . ?
C12 N17 C16 N26 178.56(13) . . . . ?
C12 C18 C23 C22 179.72(14) . . . . ?
C12 C18 C19 C20 -179.94(15) . . . . ?
C3 O4 C5 O6 2.03(17) . . . . ?
C3 C7 C8 C9 -0.5(3) . . . . ?
C18 C12 C13 C14 -179.14(13) . . . . ?
C18 C23 C22 O24 -178.74(14) . . . . ?
C18 C23 C22 C21 0.8(2) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C14 N15 C16 N17 3.2(2) . . . . ?
C14 N15 C16 N26 -177.02(13) . . . . ?
C14 N11 N10 C1 178.56(12) . . . . ?
C16 N15 C14 N11 177.88(12) . . . . ?
C16 N15 C14 C13 -2.4(2) . . . . ?
C16 N17 C12 C18 179.70(13) . . . . ?
C16 N17 C12 C13 -0.7(2) . . . . ?
C7 O6 C5 O4 -1.58(17) . . . . ?
C7 C3 C2 C1 -0.1(2) . . . . ?
C7 C8 C9 C1 -0.2(3) . . . . ?
C23 C18 C19 C20 0.2(2) . . . . ?
C23 C22 C21 C20 -0.8(3) . . . . ?
C2 C3 C7 O6 179.65(14) . . . . ?
C2 C3 C7 C8 0.7(3) . . . . ?
C2 C1 C9 C8 0.8(3) . . . . ?
C13 C12 C18 C23 -179.93(14) . . . . ?
C13 C12 C18 C19 0.2(2) . . . . ?
C22 C21 C20 C19 0.6(3) . . . . ?
C19 C18 C23 C22 -0.5(2) . . . . ?
C9 C1 C2 C3 -0.6(2) . . . . ?
C5 O4 C3 C7 -1.72(17) . . . . ?
C5 O4 C3 C2 179.47(16) . . . . ?
C5 O6 C7 C3 0.54(18) . . . . ?
C5 O6 C7 C8 179.45(16) . . . . ?
C28 O27 C30 C31 175.54(19) . . . . ?
C25 O24 C22 C23 -3.0(3) . . . . ?
C25 O24 C22 C21 177.47(15) . . . . ?
C30 O27 C28 O29 2.4(3) . . . . ?
C30 O27 C28 C32 -176.47(18) . . . . ?

_olex2_exptl_crystal_mounting_method Cryoloop
_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 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.930
