# Supplementary Information (SI) for ChemComm.
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2403177'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 H9 N O), C30 H22 N10'
_chemical_formula_sum            'C38 H40 N12 O2'
_chemical_formula_weight         696.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.9056(6)
_cell_length_b                   10.0760(6)
_cell_length_c                   10.9491(5)
_cell_angle_alpha                107.517(5)
_cell_angle_beta                 91.562(4)
_cell_angle_gamma                116.601(6)
_cell_volume                     914.85(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4941
_cell_measurement_temperature    143
_cell_measurement_theta_max      31.2420
_cell_measurement_theta_min      2.4990
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.335
_diffrn_reflns_theta_min         2.532
_diffrn_ambient_temperature      143
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   0.50    1.01    --   12.67 -31.00 -74.00  168
  2  ω    -52.00  -8.00   0.50    1.01    --  -11.26 -57.00-180.00   88
  3  ω     53.00  85.00   0.50    1.01    --   12.67 179.00-180.00   64
  4  ω    -84.00 -44.00   0.50    1.01    --  -11.26 179.00 120.00   80
  5  ω    -11.00  73.00   0.50    1.01    --   12.67  31.00  84.00  168
  6  ω    -15.00  80.00   0.50    1.01    --   12.67  77.00 120.00  190
  7  ω     16.00  50.00   0.50    1.01    --   12.67 -99.00   0.00   68
  8  ω     -9.00  52.00   0.50    1.01    --   12.67 -99.00 -60.00  122
  9  ω    -74.00 -48.00   0.50    1.01    --  -11.26-179.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3284
_reflns_number_total             4973
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.057
_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)+(0.0563P)²+0.0751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O21)=Sof(C22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(N24)=Sof(C26)=
 Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=1-FVAR(1)
 Sof(O27)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(N30)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(H32C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C28)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C17(H17A,H17B,
 H17C), C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C23(H23A,H23B,H23C), C26(H26A,
 H26B,H26C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O27 O 0.3018(17) 0.1451(15) 0.2821(13) 0.0362(17) Uani 0.687(6) 1 d . . P A 1
N4 N 0.19939(13) 0.37190(14) 0.51909(11) 0.0237(3) Uani 1 1 d . . . . .
N11 N 0.55012(13) 0.55621(13) 0.39777(10) 0.0217(3) Uani 1 1 d . . . . .
N7 N 0.29775(13) 0.46247(13) 0.30488(10) 0.0232(3) Uani 1 1 d . . . . .
N1 N -0.18400(16) 0.26060(17) 0.44482(14) 0.0402(4) Uani 1 1 d . . . . .
N10 N -0.05031(16) 0.33187(18) 0.11822(13) 0.0426(4) Uani 1 1 d . . . . .
C12 C 0.60351(15) 0.62518(16) 0.29746(12) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.09980(16) 0.35420(16) 0.42027(13) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.61240(16) 0.77130(16) 0.31345(12) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.39530(16) 0.48311(16) 0.40097(12) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.14766(16) 0.39336(16) 0.31332(13) 0.0238(3) Uani 1 1 d . . . . .
C2 C -0.05855(17) 0.29841(17) 0.43420(13) 0.0272(3) Uani 1 1 d . . . . .
C5 C 0.34415(16) 0.43067(15) 0.50767(12) 0.0210(3) Uani 1 1 d . . . . .
C15 C 0.67298(17) 0.83962(17) 0.22064(13) 0.0269(3) Uani 1 1 d . . . . .
H15 H 0.682261 0.940298 0.229760 0.032 Uiso 1 1 calc R U . . .
C14 C 0.55681(18) 0.85256(18) 0.42290(13) 0.0284(3) Uani 1 1 d . . . . .
H14A H 0.444664 0.805092 0.401424 0.043 Uiso 1 1 calc R U . . .
H14B H 0.603788 0.965547 0.435245 0.043 Uiso 1 1 calc R U . . .
H14C H 0.585743 0.840027 0.503389 0.043 Uiso 1 1 calc R U . . .
C9 C 0.03844(17) 0.36097(17) 0.20458(14) 0.0279(3) Uani 1 1 d . . . . .
C19 C 0.64336(16) 0.54291(17) 0.19100(13) 0.0258(3) Uani 1 1 d . . . . .
C16 C 0.71999(17) 0.76537(19) 0.11567(13) 0.0287(3) Uani 1 1 d . . . . .
C18 C 0.70152(18) 0.61617(19) 0.10106(13) 0.0300(3) Uani 1 1 d . . . . .
H18 H 0.729427 0.562492 0.027428 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6257(2) 0.38211(18) 0.17418(16) 0.0366(4) Uani 1 1 d . . . . .
H20A H 0.710839 0.393583 0.231585 0.055 Uiso 1 1 calc R U . . .
H20B H 0.626620 0.329232 0.083279 0.055 Uiso 1 1 calc R U . . .
H20C H 0.527960 0.318562 0.196692 0.055 Uiso 1 1 calc R U . . .
C29 C 0.3625(9) -0.0507(8) 0.1485(7) 0.043(2) Uani 0.687(6) 1 d . . P A 1
H29A H 0.296482 -0.122813 0.063214 0.064 Uiso 0.687(6) 1 calc R U P A 1
H29B H 0.401844 -0.106183 0.186182 0.064 Uiso 0.687(6) 1 calc R U P A 1
H29C H 0.448942 0.040960 0.137902 0.064 Uiso 0.687(6) 1 calc R U P A 1
N30 N 0.1489(3) -0.1073(3) 0.26710(19) 0.0307(7) Uani 0.687(6) 1 d . . P A 1
C17 C 0.7947(2) 0.8473(2) 0.02235(16) 0.0442(5) Uani 1 1 d . . . . .
H17A H 0.786635 0.944583 0.040829 0.066 Uiso 1 1 calc R U . . .
H17B H 0.742725 0.776702 -0.067394 0.066 Uiso 1 1 calc R U . . .
H17C H 0.903389 0.873789 0.032997 0.066 Uiso 1 1 calc R U . . .
C32 C 0.0595(9) -0.0524(9) 0.3557(6) 0.0400(19) Uani 0.687(6) 1 d . . P A 1
H32A H -0.031974 -0.144325 0.360331 0.060 Uiso 0.687(6) 1 calc R U P A 1
H32B H 0.028001 0.011490 0.322394 0.060 Uiso 0.687(6) 1 calc R U P A 1
H32C H 0.123329 0.011870 0.442996 0.060 Uiso 0.687(6) 1 calc R U P A 1
C31 C 0.1117(6) -0.2722(6) 0.2239(4) 0.0354(9) Uani 0.687(6) 1 d . . P A 1
H31A H 0.180350 -0.285874 0.279202 0.053 Uiso 0.687(6) 1 calc R U P A 1
H31B H 0.124489 -0.305910 0.133165 0.053 Uiso 0.687(6) 1 calc R U P A 1
H31C H 0.004829 -0.336718 0.229942 0.053 Uiso 0.687(6) 1 calc R U P A 1
C28 C 0.2696(4) 0.0055(3) 0.2390(2) 0.0266(7) Uani 0.687(6) 1 d . . P A 1
O21 O 0.275(4) 0.145(3) 0.290(3) 0.040(5) Uani 0.313(6) 1 d . . P A 2
C22 C 0.2003(9) -0.0012(10) 0.2787(6) 0.0386(18) Uani 0.313(6) 1 d . . P A 2
C23 C 0.0744(19) -0.0597(19) 0.3536(15) 0.045(4) Uani 0.313(6) 1 d . . P A 2
H23A H 0.051992 0.026116 0.398622 0.068 Uiso 0.313(6) 1 calc R U P A 2
H23B H 0.107479 -0.094266 0.417761 0.068 Uiso 0.313(6) 1 calc R U P A 2
H23C H -0.018414 -0.148973 0.293084 0.068 Uiso 0.313(6) 1 calc R U P A 2
N24 N 0.2422(7) -0.1045(7) 0.2130(5) 0.0432(19) Uani 0.313(6) 1 d . . P A 2
C26 C 0.157(2) -0.2778(16) 0.1949(12) 0.068(5) Uani 0.313(6) 1 d . . P A 2
H26A H 0.127145 -0.289940 0.277086 0.103 Uiso 0.313(6) 1 calc R U P A 2
H26B H 0.223500 -0.325600 0.168681 0.103 Uiso 0.313(6) 1 calc R U P A 2
H26C H 0.064562 -0.330848 0.127045 0.103 Uiso 0.313(6) 1 calc R U P A 2
C25 C 0.376(2) -0.047(2) 0.1540(14) 0.047(5) Uani 0.313(6) 1 d . . P A 2
H25A H 0.456256 0.054279 0.215495 0.070 Uiso 0.313(6) 1 calc R U P A 2
H25B H 0.347399 -0.031926 0.074595 0.070 Uiso 0.313(6) 1 calc R U P A 2
H25C H 0.413497 -0.124307 0.131760 0.070 Uiso 0.313(6) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O27 C28 1.223(13) . ?
N4 C3 1.3579(18) . ?
N4 C5 1.3101(17) . ?
N11 C12 1.4598(16) . ?
N11 C6 1.3793(17) . ?
N11 C5 1.3859(17) 2_666 ?
N7 C6 1.3103(17) . ?
N7 C8 1.3501(18) . ?
N1 C2 1.1460(19) . ?
N10 C9 1.1444(19) . ?
C12 C13 1.3906(19) . ?
C12 C19 1.3921(19) . ?
C3 C8 1.3758(19) . ?
C3 C2 1.440(2) . ?
C13 C15 1.3968(19) . ?
C13 C14 1.5029(19) . ?
C6 C5 1.4370(18) . ?
C8 C9 1.440(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C19 C18 1.3908(19) . ?
C19 C20 1.501(2) . ?
C16 C18 1.388(2) . ?
C16 C17 1.508(2) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 C28 1.526(8) . ?
N30 C32 1.482(8) . ?
N30 C31 1.445(6) . ?
N30 C28 1.353(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O21 C22 1.28(3) . ?
C22 C23 1.504(18) . ?
C22 N24 1.314(11) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N24 C26 1.505(15) . ?
N24 C25 1.444(17) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C5 N4 C3 116.14(11) . . ?
C6 N11 C12 120.01(11) . . ?
C6 N11 C5 120.17(10) . 2_666 ?
C5 N11 C12 119.79(11) 2_666 . ?
C6 N7 C8 116.51(11) . . ?
C13 C12 N11 117.95(12) . . ?
C13 C12 C19 123.06(12) . . ?
C19 C12 N11 118.98(12) . . ?
N4 C3 C8 121.97(13) . . ?
N4 C3 C2 117.14(11) . . ?
C8 C3 C2 120.84(12) . . ?
C12 C13 C15 116.92(13) . . ?
C12 C13 C14 122.50(12) . . ?
C15 C13 C14 120.56(13) . . ?
N11 C6 C5 120.00(12) . . ?
N7 C6 N11 118.51(11) . . ?
N7 C6 C5 121.49(12) . . ?
N7 C8 C3 121.93(12) . . ?
N7 C8 C9 117.08(12) . . ?
C3 C8 C9 120.99(13) . . ?
N1 C2 C3 176.71(16) . . ?
N4 C5 N11 118.69(11) . 2_666 ?
N4 C5 C6 121.63(12) . . ?
N11 C5 C6 119.68(12) 2_666 . ?
C13 C15 H15 118.9 . . ?
C16 C15 C13 122.17(14) . . ?
C16 C15 H15 118.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N10 C9 C8 178.46(16) . . ?
C12 C19 C20 121.50(12) . . ?
C18 C19 C12 117.33(13) . . ?
C18 C19 C20 121.17(13) . . ?
C15 C16 C18 118.43(13) . . ?
C15 C16 C17 120.76(15) . . ?
C18 C16 C17 120.78(14) . . ?
C19 C18 H18 119.0 . . ?
C16 C18 C19 121.96(13) . . ?
C16 C18 H18 119.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
C31 N30 C32 119.6(4) . . ?
C28 N30 C32 116.5(4) . . ?
C28 N30 C31 123.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N30 C32 H32A 109.5 . . ?
N30 C32 H32B 109.5 . . ?
N30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N30 C31 H31A 109.5 . . ?
N30 C31 H31B 109.5 . . ?
N30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O27 C28 C29 121.4(8) . . ?
O27 C28 N30 122.0(8) . . ?
N30 C28 C29 116.6(4) . . ?
O21 C22 C23 122.2(17) . . ?
O21 C22 N24 121.2(17) . . ?
N24 C22 C23 116.1(10) . . ?
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 . . ?
C22 N24 C26 123.4(8) . . ?
C22 N24 C25 117.4(9) . . ?
C25 N24 C26 119.2(8) . . ?
N24 C26 H26A 109.5 . . ?
N24 C26 H26B 109.5 . . ?
N24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N24 C25 H25A 109.5 . . ?
N24 C25 H25B 109.5 . . ?
N24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
N4 C3 C8 N7 -5.0(2) . . . . ?
N4 C3 C8 C9 174.61(13) . . . . ?
N11 C12 C13 C15 176.05(12) . . . . ?
N11 C12 C13 C14 -5.35(19) . . . . ?
N11 C12 C19 C18 -176.63(12) . . . . ?
N11 C12 C19 C20 2.9(2) . . . . ?
N11 C6 C5 N4 174.69(12) . . . . ?
N11 C6 C5 N11 -4.5(2) . . . 2_666 ?
N7 C6 C5 N4 -5.7(2) . . . . ?
N7 C6 C5 N11 175.10(12) . . . 2_666 ?
C12 N11 C6 N7 7.17(18) . . . . ?
C12 N11 C6 C5 -173.19(12) . . . . ?
C12 C13 C15 C16 1.1(2) . . . . ?
C12 C19 C18 C16 0.1(2) . . . . ?
C3 N4 C5 N11 -176.71(11) . . . 2_666 ?
C3 N4 C5 C6 4.06(19) . . . . ?
C13 C12 C19 C18 3.2(2) . . . . ?
C13 C12 C19 C20 -177.29(14) . . . . ?
C13 C15 C16 C18 2.0(2) . . . . ?
C13 C15 C16 C17 -175.85(15) . . . . ?
C6 N11 C12 C13 77.93(16) . . . . ?
C6 N11 C12 C19 -102.23(15) . . . . ?
C6 N7 C8 C3 3.4(2) . . . . ?
C6 N7 C8 C9 -176.23(12) . . . . ?
C8 N7 C6 N11 -178.69(12) . . . . ?
C8 N7 C6 C5 1.68(19) . . . . ?
C2 C3 C8 N7 172.42(13) . . . . ?
C2 C3 C8 C9 -8.0(2) . . . . ?
C5 N4 C3 C8 1.0(2) . . . . ?
C5 N4 C3 C2 -176.51(12) . . . . ?
C5 N11 C12 C13 -99.82(15) 2_666 . . . ?
C5 N11 C12 C19 80.02(16) 2_666 . . . ?
C5 N11 C6 N7 -175.09(12) 2_666 . . . ?
C5 N11 C6 C5 4.6(2) 2_666 . . . ?
C15 C16 C18 C19 -2.6(2) . . . . ?
C14 C13 C15 C16 -177.53(13) . . . . ?
C19 C12 C13 C15 -3.8(2) . . . . ?
C19 C12 C13 C14 174.82(13) . . . . ?
C20 C19 C18 C16 -179.40(14) . . . . ?
C17 C16 C18 C19 175.21(15) . . . . ?
C32 N30 C28 O27 -1.5(9) . . . . ?
C32 N30 C28 C29 179.6(5) . . . . ?
C31 N30 C28 O27 -176.7(8) . . . . ?
C31 N30 C28 C29 4.4(5) . . . . ?
O21 C22 N24 C26 -178.7(18) . . . . ?
O21 C22 N24 C25 0(2) . . . . ?
C23 C22 N24 C26 8.9(12) . . . . ?
C23 C22 N24 C25 -172.3(11) . . . . ?

_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
;
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2403178'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N10'
_chemical_formula_sum            'C22 H22 N10'
_chemical_formula_weight         426.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6557(5)
_cell_length_b                   14.4716(8)
_cell_length_c                   17.0096(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2130.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    143
_cell_measurement_theta_max      30.7410
_cell_measurement_theta_min      2.8390
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.425
_diffrn_reflns_theta_min         2.815
_diffrn_ambient_temperature      143.0
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  37.00   0.50    2.94    --   12.67 -29.00-127.00  156
  2  ω     -3.00  52.00   0.50    2.94    --   12.67 -99.00-180.00  110
  3  ω     18.00  44.00   0.50    2.94    --   12.67 -99.00   0.00   52
  4  ω      9.00  46.00   0.50    2.94    --  -11.26  57.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2026
_reflns_number_total             2981
_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 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
_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     166
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0520
_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)+(0.0560P)²+0.5806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Sof(H12A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(H14D)=Sof(H14E)=Sof(H14F)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=1-FVAR(1)
 Sof(H12)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(C17)=Sof(H17A)=Sof(H17B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C12(H12), C12(H12A)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16(H16D,H16E,H16F), C14(H14A,H14B,H14C), C14(H14D,H14E,
 H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N11 N 0.04090(15) 0.54575(8) 0.57094(6) 0.0274(3) Uani 1 1 d . . . . .
N4 N 0.18980(15) 0.37353(9) 0.43399(7) 0.0301(3) Uani 1 1 d . . . . .
N7 N 0.27837(15) 0.47233(8) 0.56797(7) 0.0302(3) Uani 1 1 d . . . . .
N1 N 0.50513(18) 0.22801(11) 0.41906(8) 0.0458(4) Uani 1 1 d . . . . .
C5 C 0.09867(17) 0.43625(10) 0.46514(8) 0.0266(3) Uani 1 1 d . . . . .
C6 C 0.14205(17) 0.48452(9) 0.53588(8) 0.0261(3) Uani 1 1 d . . . . .
N10 N 0.64972(19) 0.39325(12) 0.58962(9) 0.0501(4) Uani 1 1 d . . . . .
C8 C 0.37297(18) 0.40925(10) 0.53406(9) 0.0317(3) Uani 1 1 d . . . . .
C3 C 0.32775(18) 0.35878(10) 0.46972(8) 0.0309(3) Uani 1 1 d . . . . .
C2 C 0.42481(19) 0.28635(11) 0.43897(9) 0.0356(4) Uani 1 1 d . . . . .
C12 C 0.0828(2) 0.59128(10) 0.64770(8) 0.0354(4) Uani 1 1 d . . . . .
H12 H 0.186003 0.563934 0.660136 0.042 Uiso 0.622(5) 1 calc R U P A 1
H12A H -0.012001 0.629036 0.657672 0.042 Uiso 0.378(5) 1 calc R U P A 2
C9 C 0.5255(2) 0.39964(11) 0.56687(9) 0.0368(4) Uani 1 1 d . . . . .
C16 C 0.1984(2) 0.73553(12) 0.70623(11) 0.0480(5) Uani 1 1 d . . . . .
H16A H 0.219517 0.800789 0.695211 0.072 Uiso 0.622(5) 1 calc R U P A 1
H16B H 0.295863 0.703100 0.716061 0.072 Uiso 0.622(5) 1 calc R U P A 1
H16C H 0.131910 0.730653 0.752689 0.072 Uiso 0.622(5) 1 calc R U P A 1
H16D H 0.094297 0.761119 0.712624 0.072 Uiso 0.378(5) 1 calc R U P A 2
H16E H 0.270315 0.785246 0.692435 0.072 Uiso 0.378(5) 1 calc R U P A 2
H16F H 0.231291 0.706659 0.755578 0.072 Uiso 0.378(5) 1 calc R U P A 2
C14 C -0.0375(3) 0.45769(13) 0.72257(11) 0.0574(6) Uani 1 1 d . . . . .
H14A H -0.088247 0.433445 0.675381 0.086 Uiso 0.622(5) 1 calc R U P A 1
H14B H -0.102593 0.445700 0.768600 0.086 Uiso 0.622(5) 1 calc R U P A 1
H14C H 0.062676 0.427208 0.729467 0.086 Uiso 0.622(5) 1 calc R U P A 1
H14D H -0.027932 0.412570 0.679891 0.086 Uiso 0.378(5) 1 calc R U P A 2
H14E H -0.139959 0.486424 0.720558 0.086 Uiso 0.378(5) 1 calc R U P A 2
H14F H -0.024177 0.426405 0.773217 0.086 Uiso 0.378(5) 1 calc R U P A 2
C18 C 0.1188(5) 0.6930(2) 0.63723(17) 0.0368(8) Uani 0.622(5) 1 d . . P A 1
H18A H 0.185030 0.700557 0.590208 0.044 Uiso 0.622(5) 1 calc R U P A 1
H18B H 0.021183 0.726658 0.627453 0.044 Uiso 0.622(5) 1 calc R U P A 1
C17 C -0.0134(4) 0.56054(19) 0.71375(13) 0.0336(8) Uani 0.622(5) 1 d . . P A 1
H17A H -0.116093 0.590048 0.708537 0.040 Uiso 0.622(5) 1 calc R U P A 1
H17B H 0.033593 0.583951 0.762926 0.040 Uiso 0.622(5) 1 calc R U P A 1
C15 C 0.1971(8) 0.6625(4) 0.6402(3) 0.0370(13) Uani 0.378(5) 1 d . . P A 2
H15A H 0.180815 0.694491 0.589451 0.044 Uiso 0.378(5) 1 calc R U P A 2
H15B H 0.300219 0.632953 0.638161 0.044 Uiso 0.378(5) 1 calc R U P A 2
C13 C 0.0759(7) 0.5257(3) 0.7141(2) 0.0359(13) Uani 0.378(5) 1 d . . P A 2
H13A H 0.176489 0.493123 0.714857 0.043 Uiso 0.378(5) 1 calc R U P A 2
H13B H 0.072077 0.563633 0.762491 0.043 Uiso 0.378(5) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C5 1.3798(19) 5_566 ?
N11 C6 1.3810(18) . ?
N11 C12 1.5068(17) . ?
N4 C5 1.3140(19) . ?
N4 C3 1.357(2) . ?
N7 C6 1.3120(19) . ?
N7 C8 1.3551(19) . ?
N1 C2 1.145(2) . ?
C5 C6 1.4412(19) . ?
N10 C9 1.146(2) . ?
C8 C3 1.373(2) . ?
C8 C9 1.440(2) . ?
C3 C2 1.441(2) . ?
C12 H12 1.0000 . ?
C12 H12A 1.0000 . ?
C12 C18 1.515(3) . ?
C12 C17 1.467(3) . ?
C12 C15 1.434(5) . ?
C12 C13 1.476(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C16 C18 1.494(3) . ?
C16 C15 1.542(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C14 C17 1.510(3) . ?
C14 C13 1.398(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C5 N11 C6 118.96(11) 5_566 . ?
C5 N11 C12 120.89(12) 5_566 . ?
C6 N11 C12 120.15(12) . . ?
C5 N4 C3 117.16(12) . . ?
C6 N7 C8 117.19(12) . . ?
N11 C5 C6 120.53(12) 5_566 . ?
N4 C5 N11 118.47(12) . 5_566 ?
N4 C5 C6 121.00(13) . . ?
N11 C6 C5 120.42(13) . . ?
N7 C6 N11 118.48(12) . . ?
N7 C6 C5 121.10(13) . . ?
N7 C8 C3 121.70(14) . . ?
N7 C8 C9 117.00(13) . . ?
C3 C8 C9 121.26(14) . . ?
N4 C3 C8 121.62(14) . . ?
N4 C3 C2 117.70(13) . . ?
C8 C3 C2 120.66(14) . . ?
N1 C2 C3 175.87(17) . . ?
N11 C12 H12 103.0 . . ?
N11 C12 H12A 100.9 . . ?
N11 C12 C18 111.87(15) . . ?
C18 C12 H12 103.0 . . ?
C17 C12 N11 113.23(15) . . ?
C17 C12 H12 103.0 . . ?
C17 C12 C18 120.1(2) . . ?
C15 C12 N11 113.8(2) . . ?
C15 C12 H12A 100.9 . . ?
C15 C12 C13 123.9(3) . . ?
C13 C12 N11 111.8(2) . . ?
C13 C12 H12A 100.9 . . ?
N10 C9 C8 176.75(17) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C18 C16 H16A 109.5 . . ?
C18 C16 H16B 109.5 . . ?
C18 C16 H16C 109.5 . . ?
C15 C16 H16D 109.5 . . ?
C15 C16 H16E 109.5 . . ?
C15 C16 H16F 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C17 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
C17 C14 H14C 109.5 . . ?
C13 C14 H14D 109.5 . . ?
C13 C14 H14E 109.5 . . ?
C13 C14 H14F 109.5 . . ?
C12 C18 H18A 108.8 . . ?
C12 C18 H18B 108.8 . . ?
C16 C18 C12 113.8(2) . . ?
C16 C18 H18A 108.8 . . ?
C16 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C12 C17 C14 117.0(2) . . ?
C12 C17 H17A 108.1 . . ?
C12 C17 H17B 108.1 . . ?
C14 C17 H17A 108.1 . . ?
C14 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C12 C15 C16 115.6(3) . . ?
C12 C15 H15A 108.4 . . ?
C12 C15 H15B 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C12 C13 H13A 106.3 . . ?
C12 C13 H13B 106.3 . . ?
C14 C13 C12 124.0(4) . . ?
C14 C13 H13A 106.3 . . ?
C14 C13 H13B 106.3 . . ?
H13A C13 H13B 106.4 . . ?

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
N11 C5 C6 N11 3.6(2) 5_566 . . . ?
N11 C5 C6 N7 -175.66(13) 5_566 . . . ?
N11 C12 C18 C16 -165.4(2) . . . . ?
N11 C12 C17 C14 47.2(3) . . . . ?
N11 C12 C15 C16 156.7(3) . . . . ?
N11 C12 C13 C14 -39.2(6) . . . . ?
N4 C5 C6 N11 -175.65(12) . . . . ?
N4 C5 C6 N7 5.1(2) . . . . ?
N7 C8 C3 N4 4.1(2) . . . . ?
N7 C8 C3 C2 -174.42(13) . . . . ?
C5 N11 C6 N7 175.73(12) 5_566 . . . ?
C5 N11 C6 C5 -3.5(2) 5_566 . . . ?
C5 N11 C12 C18 -72.0(2) 5_566 . . . ?
C5 N11 C12 C17 67.5(2) 5_566 . . . ?
C5 N11 C12 C15 -106.4(4) 5_566 . . . ?
C5 N11 C12 C13 107.2(3) 5_566 . . . ?
C5 N4 C3 C8 -2.2(2) . . . . ?
C5 N4 C3 C2 176.37(13) . . . . ?
C6 N11 C12 C18 108.5(2) . . . . ?
C6 N11 C12 C17 -112.0(2) . . . . ?
C6 N11 C12 C15 74.0(4) . . . . ?
C6 N11 C12 C13 -72.3(3) . . . . ?
C6 N7 C8 C3 -1.2(2) . . . . ?
C6 N7 C8 C9 176.75(13) . . . . ?
C8 N7 C6 N11 177.54(12) . . . . ?
C8 N7 C6 C5 -3.2(2) . . . . ?
C3 N4 C5 N11 178.56(12) . . . 5_566 ?
C3 N4 C5 C6 -2.2(2) . . . . ?
C12 N11 C6 N7 -4.74(19) . . . . ?
C12 N11 C6 C5 176.00(12) . . . . ?
C9 C8 C3 N4 -173.75(14) . . . . ?
C9 C8 C3 C2 7.7(2) . . . . ?
C18 C12 C17 C14 -177.0(2) . . . . ?
C17 C12 C18 C16 58.2(4) . . . . ?
C15 C12 C13 C14 178.4(4) . . . . ?
C13 C12 C15 C16 -61.5(7) . . . . ?

_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
;
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2404808'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2024-11-23 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-11-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 N16 O2 S2 Zn'
_chemical_formula_sum            'C28 H20 N16 O2 S2 Zn'
_chemical_formula_weight         742.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H Zn'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3572(5)
_cell_length_b                   13.3654(5)
_cell_length_c                   11.4576(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.790(6)
_cell_angle_gamma                90
_cell_volume                     1412.05(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    143
_cell_measurement_theta_max      30.0640
_cell_measurement_theta_min      2.6030
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8653
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.405
_diffrn_reflns_theta_min         2.604
_diffrn_ambient_temperature      143
_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 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  89.00   0.50    2.00    --   21.12  49.00 157.00  148
  2  ω    -61.00  49.00   0.50    2.00    --   21.12 -49.00  10.00  220
  3  ω    -14.00  34.00   0.50    2.00    --  -19.87 -99.00-120.00   96
  4  ω    -69.00 -44.00   0.50    2.00    --  -19.87 179.00-180.00   50
  5  ω   -113.00 -88.00   0.50    2.00    --  -19.87 179.00-180.00   50
  6  ω     84.00 109.00   0.50    2.00    --   21.12-179.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0625606000
_diffrn_orient_matrix_UB_12      -0.0029918000
_diffrn_orient_matrix_UB_13      0.0445503000
_diffrn_orient_matrix_UB_21      0.0332730000
_diffrn_orient_matrix_UB_22      -0.0321732000
_diffrn_orient_matrix_UB_23      -0.0366859000
_diffrn_orient_matrix_UB_31      0.0299052000
_diffrn_orient_matrix_UB_32      0.0420831000
_diffrn_orient_matrix_UB_33      -0.0248834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             3630
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.259
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.074
_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)+(0.0796P)²+1.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C15(H15), C5(H5)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), 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
Zn20 Zn 0.500000 0.500000 0.500000 0.0257(2) Uani 1 2 d S . P A .
S22 S 0.77241(11) 0.48454(7) 0.70928(9) 0.0267(2) Uani 1 1 d . . . A 1
O21 O 0.6157(3) 0.51701(18) 0.6983(2) 0.0287(6) Uani 1 1 d . . . . .
N19 N 0.6502(3) 0.58934(18) 0.4479(2) 0.0176(6) Uani 1 1 d . . . . .
N1 N 0.1836(3) 0.53601(19) 0.6037(2) 0.0185(6) Uani 1 1 d . . . . .
N006 N 0.3812(3) 0.61904(18) 0.5316(2) 0.0171(6) Uani 1 1 d . . . . .
N16 N 0.9744(3) 0.65310(19) 0.3367(3) 0.0201(6) Uani 1 1 d . . . . .
N10 N 0.5400(3) 0.74889(18) 0.4782(3) 0.0184(6) Uani 1 1 d . . . . .
N7 N 0.3087(3) 0.88056(19) 0.5550(3) 0.0210(6) Uani 1 1 d . . . . .
N4 N 0.0937(3) 0.75534(19) 0.6326(3) 0.0204(6) Uani 1 1 d . . . . .
N13 N 0.8129(3) 0.82480(19) 0.3916(3) 0.0198(6) Uani 1 1 d . . . . .
C18 C 0.7721(4) 0.5580(2) 0.4088(3) 0.0168(7) Uani 1 1 d . . . . .
C17 C 0.8525(4) 0.6471(2) 0.3812(3) 0.0181(7) Uani 1 1 d . . . . .
C2 C 0.2555(4) 0.6160(2) 0.5761(3) 0.0170(7) Uani 1 1 d . . . . .
C9 C 0.4221(4) 0.7154(2) 0.5164(3) 0.0153(6) Uani 1 1 d . . . . .
C11 C 0.6433(4) 0.6918(2) 0.4481(3) 0.0177(7) Uani 1 1 d . . . . .
C12 C 0.7726(4) 0.7304(2) 0.4069(3) 0.0171(7) Uani 1 1 d . . . . .
C3 C 0.2080(4) 0.7199(2) 0.5903(3) 0.0176(7) Uani 1 1 d . . . . .
C8 C 0.3126(4) 0.7809(2) 0.5532(3) 0.0174(7) Uani 1 1 d . . . . .
C6 C 0.1940(4) 0.9162(2) 0.5973(3) 0.0219(7) Uani 1 1 d . . . . .
H6 H 0.182881 0.986711 0.601523 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9364(4) 0.8311(2) 0.3478(3) 0.0212(7) Uani 1 1 d . . . . .
H14 H 0.972937 0.895557 0.334159 0.025 Uiso 1 1 calc R U . . .
C15 C 1.0147(4) 0.7468(2) 0.3209(3) 0.0213(7) Uani 1 1 d . . . . .
H15 H 1.101202 0.757452 0.289722 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0888(4) 0.8550(2) 0.6358(3) 0.0234(8) Uani 1 1 d . . . . .
H5 H 0.010937 0.886026 0.665376 0.028 Uiso 1 1 calc R U . . .
C25 C 0.8822(5) 0.5907(3) 0.7477(4) 0.0403(11) Uani 1 1 d . . . . .
H25A H 0.866544 0.638902 0.682363 0.060 Uiso 1 1 calc R U . A 1
H25B H 0.984383 0.570525 0.763171 0.060 Uiso 1 1 calc R U . A 1
H25C H 0.856727 0.621580 0.818978 0.060 Uiso 1 1 calc R U . A 1
C24 C 0.8123(5) 0.4215(3) 0.8492(4) 0.0359(10) Uani 1 1 d . . . . .
H24A H 0.766805 0.457429 0.907826 0.054 Uiso 1 1 calc R U . A 1
H24B H 0.917568 0.419514 0.875551 0.054 Uiso 1 1 calc R U . A 1
H24C H 0.774420 0.353030 0.840763 0.054 Uiso 1 1 calc R U . A 1


_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
Zn20 O21 2.355(3) 3_666 ?
Zn20 O21 2.355(3) . ?
Zn20 N19 2.010(3) . ?
Zn20 N19 2.010(3) 3_666 ?
Zn20 N006 2.009(3) 3_666 ?
Zn20 N006 2.009(3) . ?
S22 O21 1.514(3) . ?
S22 C25 1.763(4) . ?
S22 C24 1.794(4) . ?
N19 C18 1.360(4) . ?
N19 C11 1.370(4) . ?
N1 C18 1.339(4) 3_666 ?
N1 C2 1.330(4) . ?
N006 C2 1.360(4) . ?
N006 C9 1.363(4) . ?
N16 C17 1.329(4) . ?
N16 C15 1.329(4) . ?
N10 C9 1.332(4) . ?
N10 C11 1.323(4) . ?
N7 C8 1.333(4) . ?
N7 C6 1.339(4) . ?
N4 C3 1.335(4) . ?
N4 C5 1.333(4) . ?
N13 C12 1.337(4) . ?
N13 C14 1.339(5) . ?
C18 C17 1.472(4) . ?
C17 C12 1.400(4) . ?
C2 C3 1.475(4) . ?
C9 C8 1.463(4) . ?
C11 C12 1.465(5) . ?
C3 C8 1.394(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.407(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.405(5) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
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
O21 Zn20 O21 180.0 . 3_666 ?
N19 Zn20 O21 90.05(10) . 3_666 ?
N19 Zn20 O21 90.05(11) 3_666 . ?
N19 Zn20 O21 89.95(11) 3_666 3_666 ?
N19 Zn20 O21 89.95(11) . . ?
N19 Zn20 N19 180.00(11) 3_666 . ?
N006 Zn20 O21 85.83(10) . . ?
N006 Zn20 O21 94.17(10) . 3_666 ?
N006 Zn20 O21 94.17(10) 3_666 . ?
N006 Zn20 O21 85.83(10) 3_666 3_666 ?
N006 Zn20 N19 91.10(10) . . ?
N006 Zn20 N19 88.90(10) 3_666 . ?
N006 Zn20 N19 88.90(10) . 3_666 ?
N006 Zn20 N19 91.10(10) 3_666 3_666 ?
N006 Zn20 N006 180.00(14) 3_666 . ?
O21 S22 C25 107.78(19) . . ?
O21 S22 C24 105.11(18) . . ?
C25 S22 C24 97.5(2) . . ?
S22 O21 Zn20 109.42(14) . . ?
C18 N19 Zn20 125.6(2) . . ?
C18 N19 C11 110.5(3) . . ?
C11 N19 Zn20 123.9(2) . . ?
C2 N1 C18 123.5(3) . 3_666 ?
C2 N006 Zn20 125.78(19) . . ?
C2 N006 C9 110.8(2) . . ?
C9 N006 Zn20 123.3(2) . . ?
C15 N16 C17 113.0(3) . . ?
C11 N10 C9 125.1(3) . . ?
C8 N7 C6 112.8(3) . . ?
C5 N4 C3 113.4(3) . . ?
C12 N13 C14 112.9(3) . . ?
N19 C18 C17 108.0(3) . . ?
N1 C18 N19 128.1(3) 3_666 . ?
N1 C18 C17 123.9(3) 3_666 . ?
N16 C17 C18 129.4(3) . . ?
N16 C17 C12 123.9(3) . . ?
C12 C17 C18 106.7(3) . . ?
N1 C2 N006 128.1(3) . . ?
N1 C2 C3 123.9(3) . . ?
N006 C2 C3 108.0(3) . . ?
N006 C9 C8 107.7(3) . . ?
N10 C9 N006 128.7(3) . . ?
N10 C9 C8 123.6(3) . . ?
N19 C11 C12 108.1(3) . . ?
N10 C11 N19 127.8(3) . . ?
N10 C11 C12 124.1(3) . . ?
N13 C12 C17 123.4(3) . . ?
N13 C12 C11 129.9(3) . . ?
C17 C12 C11 106.7(3) . . ?
N4 C3 C2 130.4(3) . . ?
N4 C3 C8 123.4(3) . . ?
C8 C3 C2 106.1(3) . . ?
N7 C8 C9 128.7(3) . . ?
N7 C8 C3 123.9(3) . . ?
C3 C8 C9 107.5(2) . . ?
N7 C6 H6 118.2 . . ?
N7 C6 C5 123.6(3) . . ?
C5 C6 H6 118.2 . . ?
N13 C14 H14 118.4 . . ?
N13 C14 C15 123.2(3) . . ?
C15 C14 H14 118.4 . . ?
N16 C15 C14 123.7(3) . . ?
N16 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
N4 C5 C6 122.9(3) . . ?
N4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
S22 C25 H25A 109.5 . . ?
S22 C25 H25B 109.5 . . ?
S22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
S22 C24 H24A 109.5 . . ?
S22 C24 H24B 109.5 . . ?
S22 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
Zn20 N19 C18 N1 0.4(5) . . . 3_666 ?
Zn20 N19 C18 C17 -179.4(2) . . . . ?
Zn20 N19 C11 N10 -1.8(5) . . . . ?
Zn20 N19 C11 C12 178.9(2) . . . . ?
Zn20 N006 C2 N1 -2.4(5) . . . . ?
Zn20 N006 C2 C3 177.5(2) . . . . ?
Zn20 N006 C9 N10 1.1(5) . . . . ?
Zn20 N006 C9 C8 -177.4(2) . . . . ?
N19 C18 C17 N16 -177.4(3) . . . . ?
N19 C18 C17 C12 0.5(4) . . . . ?
N19 C11 C12 N13 179.5(3) . . . . ?
N19 C11 C12 C17 1.0(4) . . . . ?
N1 C18 C17 N16 2.8(6) 3_666 . . . ?
N1 C18 C17 C12 -179.4(3) 3_666 . . . ?
N1 C2 C3 N4 1.5(6) . . . . ?
N1 C2 C3 C8 179.3(3) . . . . ?
N006 C2 C3 N4 -178.4(3) . . . . ?
N006 C2 C3 C8 -0.6(4) . . . . ?
N006 C9 C8 N7 179.0(3) . . . . ?
N006 C9 C8 C3 0.2(4) . . . . ?
N16 C17 C12 N13 -1.6(6) . . . . ?
N16 C17 C12 C11 177.1(3) . . . . ?
N10 C9 C8 N7 0.5(6) . . . . ?
N10 C9 C8 C3 -178.4(3) . . . . ?
N10 C11 C12 N13 0.1(6) . . . . ?
N10 C11 C12 C17 -178.4(3) . . . . ?
N7 C6 C5 N4 -0.6(6) . . . . ?
N4 C3 C8 N7 -0.7(6) . . . . ?
N4 C3 C8 C9 178.3(3) . . . . ?
N13 C14 C15 N16 -0.3(6) . . . . ?
C18 N19 C11 N10 178.7(3) . . . . ?
C18 N19 C11 C12 -0.7(4) . . . . ?
C18 N1 C2 N006 0.3(6) 3_666 . . . ?
C18 N1 C2 C3 -179.6(3) 3_666 . . . ?
C18 C17 C12 N13 -179.5(3) . . . . ?
C18 C17 C12 C11 -0.8(4) . . . . ?
C17 N16 C15 C14 -0.3(5) . . . . ?
C2 N006 C9 N10 177.9(3) . . . . ?
C2 N006 C9 C8 -0.5(4) . . . . ?
C2 C3 C8 N7 -178.7(3) . . . . ?
C2 C3 C8 C9 0.2(4) . . . . ?
C9 N006 C2 N1 -179.2(3) . . . . ?
C9 N006 C2 C3 0.7(4) . . . . ?
C9 N10 C11 N19 1.0(6) . . . . ?
C9 N10 C11 C12 -179.7(3) . . . . ?
C11 N19 C18 N1 180.0(3) . . . 3_666 ?
C11 N19 C18 C17 0.1(4) . . . . ?
C11 N10 C9 N006 -0.7(6) . . . . ?
C11 N10 C9 C8 177.6(3) . . . . ?
C12 N13 C14 C15 0.0(5) . . . . ?
C3 N4 C5 C6 0.4(5) . . . . ?
C8 N7 C6 C5 0.1(5) . . . . ?
C6 N7 C8 C9 -178.2(3) . . . . ?
C6 N7 C8 C3 0.5(5) . . . . ?
C14 N13 C12 C17 0.9(5) . . . . ?
C14 N13 C12 C11 -177.5(3) . . . . ?
C15 N16 C17 C18 178.6(3) . . . . ?
C15 N16 C17 C12 1.1(5) . . . . ?
C5 N4 C3 C2 177.7(3) . . . . ?
C5 N4 C3 C8 0.1(5) . . . . ?
C25 S22 O21 Zn20 114.32(19) . . . . ?
C24 S22 O21 Zn20 -142.45(17) . . . . ?

_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 1.481
_oxdiff_exptl_absorpt_empirical_full_min 0.746
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2403179'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H42 N10'
_chemical_formula_sum            'C40 H42 N10'
_chemical_formula_weight         662.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.1684(8)
_cell_length_b                   9.2231(4)
_cell_length_c                   12.1013(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.561(5)
_cell_angle_gamma                90
_cell_volume                     1816.52(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4816
_cell_measurement_temperature    143
_cell_measurement_theta_max      31.2280
_cell_measurement_theta_min      2.8440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20618
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.286
_diffrn_reflns_theta_min         2.503
_diffrn_ambient_temperature      143.0
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  84.00   0.50  190.00    --   12.51  77.00 -60.00  198
  2  ω     16.00  42.00   0.50  190.00    --   12.51  57.00 -90.00   52
  3  ω     39.00  81.00   0.50  190.00    --   12.51 179.00-150.00   84
  4  ω     40.00  91.00   0.50  190.00    --   12.51 179.00  30.00  102
  5  ω     39.00  72.00   0.50  190.00    --   12.51 179.00  60.00   66
  6  ω    -56.00 -31.00   0.50  190.00    --  -11.11 109.00-149.00   50
  7  ω      7.00  57.00   0.50  190.00    --   12.51-109.00 114.00  100
  8  ω      3.00  52.00   0.50  190.00    --   12.51 -99.00-150.00   98
  9  ω    -74.00 -49.00   0.50  190.00    --  -11.11 179.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2952
_reflns_number_total             5050
_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 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.034
_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)+(0.0726P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1529
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C20(H20)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C19(H19A,H19B,
 H19C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N4 N 0.41656(8) 0.24849(16) 0.43086(12) 0.0228(3) Uani 1 1 d . . . . .
N22 N 0.42518(8) 0.70959(16) 0.58573(12) 0.0243(3) Uani 1 1 d . . . . .
N6 N 0.41804(8) 0.48483(15) 0.49819(12) 0.0218(3) Uani 1 1 d . . . . .
N1 N 0.38931(10) -0.1086(2) 0.33819(15) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.45509(9) 0.14498(19) 0.38840(14) 0.0224(4) Uani 1 1 d . . . . .
C23 C 0.46797(10) 0.83222(19) 0.62233(15) 0.0245(4) Uani 1 1 d . . . . .
N25 N 0.40263(10) 1.0370(2) 0.70981(17) 0.0472(5) Uani 1 1 d . . . . .
C2 C 0.41597(11) 0.0061(2) 0.35909(15) 0.0274(4) Uani 1 1 d . . . . .
C5 C 0.45633(9) 0.37113(18) 0.46180(14) 0.0203(4) Uani 1 1 d . . . . .
C15 C 0.19772(9) 0.58438(18) 0.37613(14) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.21233(9) 0.39799(18) 0.52639(14) 0.0205(4) Uani 1 1 d . . . . .
C21 C 0.46103(9) 0.61028(19) 0.54112(14) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.29670(9) 0.39358(19) 0.54390(14) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.331160 0.329681 0.599999 0.026 Uiso 1 1 calc R U . . .
C16 C 0.14280(10) 0.69185(19) 0.28933(15) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.16523(9) 0.49497(18) 0.44382(15) 0.0218(4) Uani 1 1 d . . . . .
H14 H 0.108018 0.500672 0.432929 0.026 Uiso 1 1 calc R U . . .
C24 C 0.42999(11) 0.9438(2) 0.67136(17) 0.0314(4) Uani 1 1 d . . . . .
C20 C 0.28193(9) 0.57654(18) 0.39491(14) 0.0215(4) Uani 1 1 d . . . . .
H20 H 0.306529 0.634935 0.350460 0.026 Uiso 1 1 calc R U . . .
C7 C 0.32939(9) 0.48328(19) 0.47862(14) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.17438(10) 0.29280(19) 0.59244(16) 0.0246(4) Uani 1 1 d . . . . .
C18 C 0.18316(12) 0.7465(2) 0.20151(17) 0.0352(5) Uani 1 1 d . . . . .
H18A H 0.233005 0.800986 0.242520 0.053 Uiso 1 1 calc R U . . .
H18B H 0.144804 0.809890 0.144628 0.053 Uiso 1 1 calc R U . . .
H18C H 0.197577 0.663808 0.161042 0.053 Uiso 1 1 calc R U . . .
C11 C 0.22445(12) 0.2870(2) 0.72185(17) 0.0381(5) Uani 1 1 d . . . . .
H11A H 0.279575 0.249754 0.730751 0.057 Uiso 1 1 calc R U . . .
H11B H 0.197122 0.222867 0.762590 0.057 Uiso 1 1 calc R U . . .
H11C H 0.228750 0.384670 0.755155 0.057 Uiso 1 1 calc R U . . .
C13 C 0.08575(11) 0.3335(2) 0.58268(18) 0.0326(4) Uani 1 1 d . . . . .
H13A H 0.084487 0.432835 0.610889 0.049 Uiso 1 1 calc R U . . .
H13B H 0.065183 0.266631 0.629889 0.049 Uiso 1 1 calc R U . . .
H13C H 0.051005 0.327173 0.501029 0.049 Uiso 1 1 calc R U . . .
C19 C 0.06024(11) 0.6222(2) 0.22201(17) 0.0375(5) Uani 1 1 d . . . . .
H19A H 0.069824 0.536889 0.179781 0.056 Uiso 1 1 calc R U . . .
H19B H 0.026427 0.692376 0.166398 0.056 Uiso 1 1 calc R U . . .
H19C H 0.031708 0.592718 0.276806 0.056 Uiso 1 1 calc R U . . .
C12 C 0.17347(13) 0.1424(2) 0.5378(2) 0.0394(5) Uani 1 1 d . . . . .
H12A H 0.142126 0.146681 0.454603 0.059 Uiso 1 1 calc R U . . .
H12B H 0.147759 0.072534 0.576468 0.059 Uiso 1 1 calc R U . . .
H12C H 0.229953 0.111980 0.547524 0.059 Uiso 1 1 calc R U . . .
C17 C 0.12748(14) 0.8213(2) 0.35950(19) 0.0440(5) Uani 1 1 d . . . . .
H17A H 0.101384 0.787259 0.415934 0.066 Uiso 1 1 calc R U . . .
H17B H 0.091348 0.891233 0.306394 0.066 Uiso 1 1 calc R U . . .
H17C H 0.179940 0.867937 0.400960 0.066 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
N4 C3 1.353(2) . ?
N4 C5 1.313(2) . ?
N22 C23 1.345(2) . ?
N22 C21 1.312(2) . ?
N6 C5 1.382(2) . ?
N6 C21 1.382(2) . ?
N6 C7 1.4641(19) . ?
N1 C2 1.148(2) . ?
C3 C23 1.384(2) 3_666 ?
C3 C2 1.438(2) . ?
C23 C24 1.443(3) . ?
N25 C24 1.147(2) . ?
C5 C21 1.441(2) 3_666 ?
C15 C16 1.531(2) . ?
C15 C14 1.397(2) . ?
C15 C20 1.392(2) . ?
C9 C8 1.396(2) . ?
C9 C14 1.392(2) . ?
C9 C10 1.529(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(2) . ?
C16 C18 1.527(3) . ?
C16 C19 1.533(3) . ?
C16 C17 1.535(3) . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C20 C7 1.380(2) . ?
C10 C11 1.529(3) . ?
C10 C13 1.535(2) . ?
C10 C12 1.534(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C5 N4 C3 116.34(13) . . ?
C21 N22 C23 116.37(14) . . ?
C5 N6 C7 121.10(13) . . ?
C21 N6 C5 120.26(13) . . ?
C21 N6 C7 118.19(13) . . ?
N4 C3 C23 121.68(15) . 3_666 ?
N4 C3 C2 118.44(14) . . ?
C23 C3 C2 119.81(15) 3_666 . ?
N22 C23 C3 122.32(15) . 3_666 ?
N22 C23 C24 117.65(14) . . ?
C3 C23 C24 120.00(16) 3_666 . ?
N1 C2 C3 175.90(19) . . ?
N4 C5 N6 119.19(13) . . ?
N4 C5 C21 121.50(15) . 3_666 ?
N6 C5 C21 119.31(14) . 3_666 ?
C14 C15 C16 120.71(14) . . ?
C20 C15 C16 121.76(15) . . ?
C20 C15 C14 117.46(15) . . ?
C8 C9 C10 119.77(15) . . ?
C14 C9 C8 117.73(14) . . ?
C14 C9 C10 122.43(14) . . ?
N22 C21 N6 118.35(13) . . ?
N22 C21 C5 121.45(15) . 3_666 ?
N6 C21 C5 120.19(14) . 3_666 ?
C9 C8 H8 120.4 . . ?
C7 C8 C9 119.13(15) . . ?
C7 C8 H8 120.4 . . ?
C15 C16 C19 110.88(15) . . ?
C15 C16 C17 107.48(15) . . ?
C18 C16 C15 111.99(13) . . ?
C18 C16 C19 108.43(15) . . ?
C18 C16 C17 108.88(16) . . ?
C19 C16 C17 109.13(15) . . ?
C15 C14 H14 118.3 . . ?
C9 C14 C15 123.42(14) . . ?
C9 C14 H14 118.3 . . ?
N25 C24 C23 176.7(2) . . ?
C15 C20 H20 120.3 . . ?
C7 C20 C15 119.48(15) . . ?
C7 C20 H20 120.3 . . ?
C8 C7 N6 120.29(14) . . ?
C20 C7 N6 116.95(14) . . ?
C20 C7 C8 122.75(14) . . ?
C9 C10 C13 112.43(14) . . ?
C9 C10 C12 107.22(14) . . ?
C11 C10 C9 111.32(14) . . ?
C11 C10 C13 107.93(15) . . ?
C11 C10 C12 109.57(16) . . ?
C12 C10 C13 108.31(15) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C3 N4 C5 N6 175.52(14) . . . . ?
C3 N4 C5 C21 -4.6(2) . . . 3_666 ?
C23 N22 C21 N6 -177.51(15) . . . . ?
C23 N22 C21 C5 3.6(2) . . . 3_666 ?
C5 N4 C3 C23 -0.3(2) . . . 3_666 ?
C5 N4 C3 C2 176.76(15) . . . . ?
C5 N6 C21 N22 -173.15(15) . . . . ?
C5 N6 C21 C5 5.8(3) . . . 3_666 ?
C5 N6 C7 C8 73.4(2) . . . . ?
C5 N6 C7 C20 -107.89(18) . . . . ?
C15 C20 C7 N6 -177.20(14) . . . . ?
C15 C20 C7 C8 1.5(3) . . . . ?
C9 C8 C7 N6 177.72(15) . . . . ?
C9 C8 C7 C20 -0.9(3) . . . . ?
C21 N22 C23 C3 1.4(2) . . . 3_666 ?
C21 N22 C23 C24 179.74(16) . . . . ?
C21 N6 C5 N4 174.15(15) . . . . ?
C21 N6 C5 C21 -5.7(2) . . . 3_666 ?
C21 N6 C7 C8 -114.39(18) . . . . ?
C21 N6 C7 C20 64.3(2) . . . . ?
C8 C9 C14 C15 1.8(2) . . . . ?
C8 C9 C10 C11 46.7(2) . . . . ?
C8 C9 C10 C13 167.90(16) . . . . ?
C8 C9 C10 C12 -73.2(2) . . . . ?
C16 C15 C14 C9 -178.21(16) . . . . ?
C16 C15 C20 C7 176.53(16) . . . . ?
C14 C15 C16 C18 -163.81(16) . . . . ?
C14 C15 C16 C19 -42.6(2) . . . . ?
C14 C15 C16 C17 76.6(2) . . . . ?
C14 C15 C20 C7 -0.4(2) . . . . ?
C14 C9 C8 C7 -0.7(2) . . . . ?
C14 C9 C10 C11 -136.62(17) . . . . ?
C14 C9 C10 C13 -15.4(2) . . . . ?
C14 C9 C10 C12 103.55(19) . . . . ?
C20 C15 C16 C18 19.3(2) . . . . ?
C20 C15 C16 C19 140.59(17) . . . . ?
C20 C15 C16 C17 -100.21(19) . . . . ?
C20 C15 C14 C9 -1.2(2) . . . . ?
C7 N6 C5 N4 -13.8(2) . . . . ?
C7 N6 C5 C21 166.35(14) . . . 3_666 ?
C7 N6 C21 N22 14.5(2) . . . . ?
C7 N6 C21 C5 -166.53(14) . . . 3_666 ?
C10 C9 C8 C7 176.20(15) . . . . ?
C10 C9 C14 C15 -175.01(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
;
