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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160807_MeV_-180
_database_code_depnum_ccdc_archive 'CCDC 2268733'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H5 N4, 0.5(C12 H14 N2)'
_chemical_formula_sum            'C21 H12 N5'
_chemical_formula_weight         334.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3110(4)
_cell_length_b                   19.5847(4)
_cell_length_c                   11.1122(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.012(3)
_cell_angle_gamma                90
_cell_volume                     3375.78(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    93
_cell_measurement_reflns_used    15886
_cell_measurement_theta_min      2.6230
_cell_measurement_theta_max      31.1550

_exptl_crystal_description       block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.736
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            27672
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3873
_reflns_number_gt                3417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+1.6845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3873
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.32873(6) 0.27822(5) 0.39192(9) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.36044(6) 0.28354(5) 0.52357(9) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.3748(8) 0.3261(7) 0.5691(12) 0.023 Uiso 1 1 d . U . . .
C3 C 0.36801(6) 0.21855(5) 0.57950(9) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.33317(7) 0.09731(6) 0.47683(11) 0.0259(2) Uani 1 1 d . . . . .
H4 H 0.349845 0.072723 0.554320 0.031 Uiso 1 1 calc R U . . .
C5 C 0.30082(8) 0.06297(6) 0.36020(12) 0.0308(3) Uani 1 1 d . . . . .
H5 H 0.295492 0.014651 0.358883 0.037 Uiso 1 1 calc R U . . .
C6 C 0.27679(7) 0.09900(6) 0.24781(11) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.255037 0.074976 0.170152 0.035 Uiso 1 1 calc R U . . .
C7 C 0.28391(7) 0.17056(6) 0.24608(10) 0.0240(2) Uani 1 1 d . . . . .
H7 H 0.267522 0.195014 0.168447 0.029 Uiso 1 1 calc R U . . .
C8 C 0.31542(6) 0.20435(5) 0.36048(10) 0.0194(2) Uani 1 1 d . . . . .
C9 C 0.34002(6) 0.16754(5) 0.47569(10) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.31275(6) 0.33322(5) 0.30725(9) 0.0194(2) Uani 1 1 d . . . . .
C11 C 0.27435(7) 0.32791(5) 0.17400(10) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.24323(7) 0.32620(5) 0.06578(9) 0.0312(2) Uani 1 1 d . . . . .
C12 C 0.33275(7) 0.40065(5) 0.35561(9) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.35169(7) 0.45446(5) 0.39726(9) 0.0285(2) Uani 1 1 d . . . . .
C13 C 0.39493(6) 0.20582(5) 0.70895(10) 0.0194(2) Uani 1 1 d . . . . .
C14 C 0.40368(7) 0.14030(5) 0.76734(10) 0.0227(2) Uani 1 1 d . . . . .
N3 N 0.41217(7) 0.08899(5) 0.82078(10) 0.0315(2) Uani 1 1 d . . . . .
C15 C 0.41442(6) 0.26228(5) 0.79417(9) 0.0197(2) Uani 1 1 d . . . . .
N4 N 0.42925(6) 0.30849(5) 0.86159(8) 0.0248(2) Uani 1 1 d . . . . .
N5 N 0.500000 0.51707(6) 0.750000 0.0279(3) Uani 1 2 d S T P . .
C16 C 0.54151(7) 0.55096(6) 0.85687(10) 0.0244(2) Uani 1 1 d . . . . .
H16 H 0.570798 0.526153 0.931203 0.029 Uiso 1 1 calc R U . . .
C17 C 0.54189(7) 0.62110(5) 0.85939(9) 0.0203(2) Uani 1 1 d . . . . .
H17 H 0.570688 0.644505 0.935647 0.024 Uiso 1 1 calc R U . . .
C18 C 0.500000 0.65818(7) 0.750000 0.0166(3) Uani 1 2 d S T P . .
C19 C 0.500000 0.73413(7) 0.750000 0.0177(3) Uani 1 2 d S T P . .
C20 C 0.54488(8) 0.77105(6) 0.85724(10) 0.0276(3) Uani 1 1 d . . . . .
H20 H 0.576572 0.747635 0.932024 0.033 Uiso 1 1 calc R U . . .
C21 C 0.54351(8) 0.84132(6) 0.85538(11) 0.0309(3) Uani 1 1 d . . . . .
H21 H 0.573684 0.865985 0.929452 0.037 Uiso 1 1 calc R U . . .
N6 N 0.500000 0.87550(6) 0.750000 0.0255(3) Uani 1 2 d S T P . .
C22 C 0.500000 0.44168(9) 0.750000 0.0634(8) Uani 1 2 d S T P . .
H22 H 0.467251 0.425005 0.665683 0.095 Uiso 0.5 1 calc R U P . .
H22A H 0.559463 0.425005 0.772125 0.095 Uiso 0.5 1 calc R U P . .
H22B H 0.473286 0.425005 0.812192 0.095 Uiso 0.5 1 calc R U P . .
C23 C 0.500000 0.95124(8) 0.750000 0.0382(4) Uani 1 2 d S T P . .
H23 H 0.465538 0.967922 0.666540 0.057 Uiso 0.5 1 calc R U P . .
H23A H 0.475156 0.967923 0.814294 0.057 Uiso 0.5 1 calc R U P . .
H23B H 0.559306 0.967923 0.769166 0.057 Uiso 0.5 1 calc R U P . .


_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
C1 C2 1.3965(14) . ?
C1 C10 1.4007(14) . ?
C1 C8 1.4885(14) . ?
C2 C3 1.4051(14) . ?
C2 H2 0.966(13) . ?
C3 C13 1.3905(14) . ?
C3 C9 1.4872(14) . ?
C4 C9 1.3802(15) . ?
C4 C5 1.4099(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3815(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4069(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3836(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4149(15) . ?
C10 C11 1.4220(14) . ?
C10 C12 1.4250(14) . ?
C11 N1 1.1522(15) . ?
C12 N2 1.1541(14) . ?
C13 C14 1.4250(14) . ?
C13 C15 1.4264(14) . ?
C14 N3 1.1537(14) . ?
C15 N4 1.1518(14) . ?
N5 C16 1.3460(13) . ?
N5 C16 1.3461(12) 2_656 ?
N5 C22 1.476(2) . ?
C16 C17 1.3741(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3994(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.4875(19) . ?
C19 C20 1.3926(13) . ?
C19 C20 1.3926(13) 2_656 ?
C20 C21 1.3764(16) . ?
C20 H20 0.9500 . ?
C21 N6 1.3450(14) . ?
C21 H21 0.9500 . ?
N6 C23 1.4834(19) . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22 0.9801 2_656 ?
C22 H22A 0.9800 2_656 ?
C22 H22B 0.9800 2_656 ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23 0.9800 2_656 ?
C23 H23A 0.9800 2_656 ?
C23 H23B 0.9800 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 125.32(9) . . ?
C2 C1 C8 107.35(9) . . ?
C10 C1 C8 127.34(9) . . ?
C1 C2 C3 110.44(9) . . ?
C1 C2 H2 124.3(8) . . ?
C3 C2 H2 125.2(8) . . ?
C13 C3 C2 125.20(9) . . ?
C13 C3 C9 127.23(9) . . ?
C2 C3 C9 107.54(9) . . ?
C9 C4 C5 118.38(11) . . ?
C9 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 120.55(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.30(10) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 118.21(11) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C9 120.56(10) . . ?
C7 C8 C1 131.79(10) . . ?
C9 C8 C1 107.63(9) . . ?
C4 C9 C8 121.00(10) . . ?
C4 C9 C3 131.95(10) . . ?
C8 C9 C3 107.02(9) . . ?
C1 C10 C11 125.02(9) . . ?
C1 C10 C12 119.08(9) . . ?
C11 C10 C12 115.86(9) . . ?
N1 C11 C10 177.47(12) . . ?
N2 C12 C10 177.65(12) . . ?
C3 C13 C14 125.99(9) . . ?
C3 C13 C15 118.82(9) . . ?
C14 C13 C15 115.18(9) . . ?
N3 C14 C13 176.35(12) . . ?
N4 C15 C13 178.93(12) . . ?
C16 N5 C16 120.92(13) . 2_656 ?
C16 N5 C22 119.54(7) . . ?
C16 N5 C22 119.54(7) 2_656 . ?
N5 C16 C17 120.59(10) . . ?
N5 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.21(10) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C17 117.48(13) . 2_656 ?
C17 C18 C19 121.26(6) . . ?
C17 C18 C19 121.26(6) 2_656 . ?
C20 C19 C20 117.43(14) . 2_656 ?
C20 C19 C18 121.28(7) . . ?
C20 C19 C18 121.28(7) 2_656 . ?
C21 C20 C19 120.30(11) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N6 C21 C20 120.82(11) . . ?
N6 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 N6 C21 120.31(14) . 2_656 ?
C21 N6 C23 119.85(7) . . ?
C21 N6 C23 119.84(7) 2_656 . ?
N5 C22 H22 109.5 . . ?
N5 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22 109.473(1) . 2_656 ?
H22 C22 H22 141.1 . 2_656 ?
H22A C22 H22 56.2 . 2_656 ?
H22B C22 H22 56.3 . 2_656 ?
N5 C22 H22A 109.473(1) . 2_656 ?
H22 C22 H22A 56.3 . 2_656 ?
H22A C22 H22A 141.1 . 2_656 ?
H22B C22 H22A 56.3 . 2_656 ?
H22 C22 H22A 109.5 2_656 2_656 ?
N5 C22 H22B 109.474(2) . 2_656 ?
H22 C22 H22B 56.2 . 2_656 ?
H22A C22 H22B 56.3 . 2_656 ?
H22B C22 H22B 141.1 . 2_656 ?
H22 C22 H22B 109.5 2_656 2_656 ?
H22A C22 H22B 109.5 2_656 2_656 ?
N6 C23 H23 109.5 . . ?
N6 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
N6 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N6 C23 H23 109.475(2) . 2_656 ?
H23 C23 H23 141.1 . 2_656 ?
H23A C23 H23 56.3 . 2_656 ?
H23B C23 H23 56.2 . 2_656 ?
N6 C23 H23A 109.475(2) . 2_656 ?
H23 C23 H23A 56.2 . 2_656 ?
H23A C23 H23A 141.1 . 2_656 ?
H23B C23 H23A 56.3 . 2_656 ?
H23 C23 H23A 109.5 2_656 2_656 ?
N6 C23 H23B 109.475(1) . 2_656 ?
H23 C23 H23B 56.3 . 2_656 ?
H23A C23 H23B 56.3 . 2_656 ?
H23B C23 H23B 141.1 . 2_656 ?
H23 C23 H23B 109.5 2_656 2_656 ?
H23A C23 H23B 109.5 2_656 2_656 ?

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
C10 C1 C2 C3 179.42(9) . . . . ?
C8 C1 C2 C3 -0.42(11) . . . . ?
C1 C2 C3 C13 -177.79(9) . . . . ?
C1 C2 C3 C9 0.75(11) . . . . ?
C9 C4 C5 C6 0.10(17) . . . . ?
C4 C5 C6 C7 0.11(18) . . . . ?
C5 C6 C7 C8 -0.29(17) . . . . ?
C6 C7 C8 C9 0.26(15) . . . . ?
C6 C7 C8 C1 -178.20(10) . . . . ?
C2 C1 C8 C7 178.52(10) . . . . ?
C10 C1 C8 C7 -1.32(18) . . . . ?
C2 C1 C8 C9 -0.09(11) . . . . ?
C10 C1 C8 C9 -179.93(10) . . . . ?
C5 C4 C9 C8 -0.12(16) . . . . ?
C5 C4 C9 C3 177.57(10) . . . . ?
C7 C8 C9 C4 -0.06(15) . . . . ?
C1 C8 C9 C4 178.74(9) . . . . ?
C7 C8 C9 C3 -178.27(9) . . . . ?
C1 C8 C9 C3 0.52(10) . . . . ?
C13 C3 C9 C4 -0.22(18) . . . . ?
C2 C3 C9 C4 -178.72(11) . . . . ?
C13 C3 C9 C8 177.72(10) . . . . ?
C2 C3 C9 C8 -0.78(11) . . . . ?
C2 C1 C10 C11 -174.95(10) . . . . ?
C8 C1 C10 C11 4.86(17) . . . . ?
C2 C1 C10 C12 2.53(15) . . . . ?
C8 C1 C10 C12 -177.65(9) . . . . ?
C2 C3 C13 C14 -179.43(10) . . . . ?
C9 C3 C13 C14 2.32(17) . . . . ?
C2 C3 C13 C15 1.98(15) . . . . ?
C9 C3 C13 C15 -176.27(9) . . . . ?
C16 N5 C16 C17 0.45(7) 2_656 . . . ?
C22 N5 C16 C17 -179.54(7) . . . . ?
N5 C16 C17 C18 -0.91(15) . . . . ?
C16 C17 C18 C17 0.45(7) . . . 2_656 ?
C16 C17 C18 C19 -179.56(7) . . . . ?
C17 C18 C19 C20 2.89(8) . . . . ?
C17 C18 C19 C20 -177.11(8) 2_656 . . . ?
C17 C18 C19 C20 -177.11(8) . . . 2_656 ?
C17 C18 C19 C20 2.89(8) 2_656 . . 2_656 ?
C20 C19 C20 C21 0.43(9) 2_656 . . . ?
C18 C19 C20 C21 -179.56(9) . . . . ?
C19 C20 C21 N6 -0.89(17) . . . . ?
C20 C21 N6 C21 0.45(9) . . . 2_656 ?
C20 C21 N6 C23 -179.55(9) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_20190318_PrV_-123
_database_code_depnum_ccdc_archive 'CCDC 2268735'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H5 N4), C16 H22 N2'
_chemical_formula_sum            'C46 H32 N10'
_chemical_formula_weight         724.81

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6480(3)
_cell_length_b                   11.3059(4)
_cell_length_c                   21.0344(7)
_cell_angle_alpha                74.729(3)
_cell_angle_beta                 82.132(3)
_cell_angle_gamma                70.001(3)
_cell_volume                     1861.86(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    4542
_cell_measurement_theta_min      2.0090
_cell_measurement_theta_max      25.6380

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Dark Blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.23777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.636
_oxdiff_exptl_absorpt_empirical_full_max 2.439
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            21752
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.510
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6796
_reflns_number_gt                3794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+0.7957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6796
_refine_ls_number_parameters     510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2319
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3609(4) 0.9397(3) 0.08743(16) 0.0490(9) Uani 1 1 d . . . . .
N2 N 0.0775(4) 0.6271(3) 0.04785(17) 0.0591(10) Uani 1 1 d . . . . .
N3 N -0.5083(4) 0.9468(3) 0.35155(16) 0.0495(9) Uani 1 1 d . . . . .
N4 N -0.1598(4) 0.6387(3) 0.48636(17) 0.0545(9) Uani 1 1 d . . . . .
N5 N 0.4805(4) 0.5983(3) 0.38756(18) 0.0488(9) Uani 1 1 d . . . . .
N6 N 0.6226(4) 0.5808(3) 0.18300(18) 0.0522(9) Uani 1 1 d . . . . .
N7 N -0.1265(4) 0.9775(3) 0.42068(17) 0.0489(9) Uani 1 1 d . . . . .
N8 N -0.3628(4) 1.1982(4) 0.23163(18) 0.0607(10) Uani 1 1 d . . . . .
N9 N 0.8998(4) 0.2874(3) 0.42615(15) 0.0393(8) Uani 1 1 d . . . . .
N10 N 1.2387(4) 0.2297(3) 0.10841(14) 0.0385(7) Uani 1 1 d . . . . .
C1 C -0.2033(5) 0.7782(4) 0.24512(18) 0.0370(9) Uani 1 1 d . . . . .
H1 H -0.308(5) 0.849(3) 0.2358(17) 0.044 Uiso 1 1 d . U . . .
C2 C -0.0907(4) 0.7174(3) 0.20015(17) 0.0332(8) Uani 1 1 d . . . . .
C3 C 0.0439(4) 0.6134(3) 0.23837(17) 0.0337(8) Uani 1 1 d . . . . .
C4 C 0.1887(4) 0.5278(3) 0.21892(19) 0.0396(9) Uani 1 1 d . . . . .
H4 H 0.216205 0.528001 0.173596 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2932(4) 0.4411(3) 0.2676(2) 0.0414(9) Uani 1 1 d . . . . .
H5 H 0.393853 0.382242 0.255106 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2533(5) 0.4392(4) 0.33341(19) 0.0421(9) Uani 1 1 d . . . . .
H6 H 0.325315 0.377489 0.365583 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1084(4) 0.5268(3) 0.35377(18) 0.0377(9) Uani 1 1 d . . . . .
H7 H 0.082646 0.526853 0.399139 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0042(4) 0.6130(3) 0.30595(17) 0.0336(8) Uani 1 1 d . . . . .
C9 C -0.1539(4) 0.7192(3) 0.30995(17) 0.0326(8) Uani 1 1 d . . . . .
C10 C -0.1070(4) 0.7499(3) 0.13241(18) 0.0372(9) Uani 1 1 d . . . . .
C11 C -0.2462(5) 0.8543(4) 0.10639(18) 0.0400(9) Uani 1 1 d . . . . .
C12 C -0.0020(5) 0.6812(4) 0.08648(19) 0.0415(9) Uani 1 1 d . . . . .
C13 C -0.2401(4) 0.7528(3) 0.36713(17) 0.0349(8) Uani 1 1 d . . . . .
C14 C -0.3907(5) 0.8597(4) 0.35983(18) 0.0384(9) Uani 1 1 d . . . . .
C15 C -0.1925(4) 0.6886(4) 0.43220(19) 0.0383(9) Uani 1 1 d . . . . .
C16 C 0.1584(4) 0.8597(3) 0.29518(18) 0.0382(9) Uani 1 1 d . . . . .
H16 H 0.169267 0.835508 0.341563 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2746(4) 0.8034(3) 0.24942(18) 0.0357(9) Uani 1 1 d . . . . .
C18 C 0.2139(4) 0.8722(3) 0.18295(18) 0.0344(8) Uani 1 1 d . . . . .
C19 C 0.2807(5) 0.8605(4) 0.12057(19) 0.0418(9) Uani 1 1 d . . . . .
H19 H 0.384306 0.797557 0.114884 0.050 Uiso 1 1 calc R U . . .
C20 C 0.1935(5) 0.9427(4) 0.06602(19) 0.0449(10) Uani 1 1 d . . . . .
H20 H 0.237917 0.935876 0.022759 0.054 Uiso 1 1 calc R U . . .
C21 C 0.0433(5) 1.0336(4) 0.07451(18) 0.0435(10) Uani 1 1 d . . . . .
H21 H -0.014266 1.088673 0.036736 0.052 Uiso 1 1 calc R U . . .
C22 C -0.0267(4) 1.0469(3) 0.13712(18) 0.0378(9) Uani 1 1 d . . . . .
H22 H -0.130436 1.110026 0.142328 0.045 Uiso 1 1 calc R U . . .
C23 C 0.0593(4) 0.9658(3) 0.19131(17) 0.0327(8) Uani 1 1 d . . . . .
C24 C 0.0241(4) 0.9566(3) 0.26317(17) 0.0334(8) Uani 1 1 d . . . . .
C25 C 0.4173(4) 0.6997(3) 0.26462(18) 0.0379(9) Uani 1 1 d . . . . .
C26 C 0.4539(4) 0.6432(4) 0.3319(2) 0.0413(9) Uani 1 1 d . . . . .
C27 C 0.5286(5) 0.6362(4) 0.2182(2) 0.0429(9) Uani 1 1 d . . . . .
C28 C -0.1167(4) 1.0287(3) 0.29443(17) 0.0353(8) Uani 1 1 d . . . . .
C29 C -0.1275(4) 1.0028(3) 0.3644(2) 0.0369(9) Uani 1 1 d . . . . .
C30 C -0.2523(5) 1.1213(4) 0.25984(19) 0.0446(10) Uani 1 1 d . . . . .
C31 C 1.0460(4) 0.1967(3) 0.41892(18) 0.0388(9) Uani 1 1 d . . . . .
H31 H 1.102583 0.141847 0.456949 0.047 Uiso 1 1 calc R U . . .
C32 C 1.1143(4) 0.1825(3) 0.35751(17) 0.0364(9) Uani 1 1 d . . . . .
H32 H 1.218129 0.118676 0.353359 0.044 Uiso 1 1 calc R U . . .
C33 C 1.0326(4) 0.2608(3) 0.30130(17) 0.0330(8) Uani 1 1 d . . . . .
C34 C 0.8838(4) 0.3540(4) 0.31051(18) 0.0414(9) Uani 1 1 d . . . . .
H34 H 0.825071 0.410851 0.273354 0.050 Uiso 1 1 calc R U . . .
C35 C 0.8212(5) 0.3647(4) 0.37236(19) 0.0461(10) Uani 1 1 d . . . . .
H35 H 0.718519 0.429017 0.377571 0.055 Uiso 1 1 calc R U . . .
C36 C 1.3233(4) 0.1540(3) 0.16121(18) 0.0392(9) Uani 1 1 d . . . . .
H36 H 1.429484 0.094442 0.155196 0.047 Uiso 1 1 calc R U . . .
C37 C 1.2586(4) 0.1615(3) 0.22380(17) 0.0362(9) Uani 1 1 d . . . . .
H37 H 1.320467 0.107091 0.260632 0.043 Uiso 1 1 calc R U . . .
C38 C 1.1021(4) 0.2484(3) 0.23421(18) 0.0351(8) Uani 1 1 d . . . . .
C39 C 1.0166(4) 0.3230(3) 0.17782(17) 0.0372(9) Uani 1 1 d . . . . .
H39 H 0.908593 0.381155 0.182477 0.045 Uiso 1 1 calc R U . . .
C40 C 1.0852(4) 0.3140(4) 0.11615(18) 0.0409(9) Uani 1 1 d . . . . .
H40 H 1.025637 0.366694 0.078459 0.049 Uiso 1 1 calc R U . . .
C41 C 0.8208(5) 0.2925(4) 0.49300(18) 0.0437(10) Uani 1 1 d . . . . .
H41 H 0.744334 0.380846 0.492483 0.052 Uiso 1 1 calc R U . . .
H41A H 0.906245 0.272404 0.524628 0.052 Uiso 1 1 calc R U . . .
C42 C 0.7274(5) 0.1967(4) 0.51494(18) 0.0432(9) Uani 1 1 d . . . . .
H42 H 0.687009 0.195042 0.561440 0.052 Uiso 1 1 calc R U . . .
H42A H 0.804348 0.109406 0.513371 0.052 Uiso 1 1 calc R U . . .
C43 C 0.5819(5) 0.2250(4) 0.4740(2) 0.0578(12) Uani 1 1 d . . . . .
H43 H 0.505770 0.312004 0.474419 0.087 Uiso 1 1 calc R U . . .
H43A H 0.524816 0.161222 0.492706 0.087 Uiso 1 1 calc R U . . .
H43B H 0.621274 0.220219 0.428528 0.087 Uiso 1 1 calc R U . . .
C44 C 1.3136(5) 0.2259(4) 0.04073(18) 0.0442(10) Uani 1 1 d . . . . .
H44 H 1.227379 0.237525 0.011046 0.053 Uiso 1 1 calc R U . . .
H44A H 1.397637 0.140297 0.041453 0.053 Uiso 1 1 calc R U . . .
C45 C 1.3935(5) 0.3315(4) 0.0141(2) 0.0575(12) Uani 1 1 d . . . . .
H45 H 1.310001 0.416358 0.015713 0.069 Uiso 1 1 calc R U . . .
H45A H 1.429840 0.332621 -0.032713 0.069 Uiso 1 1 calc R U . . .
C46 C 1.5408(6) 0.3143(5) 0.0520(2) 0.0730(14) Uani 1 1 d . . . . .
H46 H 1.502261 0.333795 0.095259 0.110 Uiso 1 1 calc R U . . .
H46A H 1.600385 0.373230 0.027145 0.110 Uiso 1 1 calc R U . . .
H46B H 1.614547 0.224748 0.057947 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.151(4) . ?
N2 C12 1.152(5) . ?
N3 C14 1.143(4) . ?
N4 C15 1.156(4) . ?
N5 C26 1.166(5) . ?
N6 C27 1.154(5) . ?
N7 C29 1.142(4) . ?
N8 C30 1.156(5) . ?
N9 C35 1.338(5) . ?
N9 C31 1.347(4) . ?
N9 C41 1.483(4) . ?
N10 C36 1.340(4) . ?
N10 C40 1.361(4) . ?
N10 C44 1.486(4) . ?
C1 C2 1.395(5) . ?
C1 C9 1.404(5) . ?
C1 H1 0.99(4) . ?
C2 C10 1.389(5) . ?
C2 C3 1.485(5) . ?
C3 C4 1.383(5) . ?
C3 C8 1.415(5) . ?
C4 C5 1.395(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.489(5) . ?
C9 C13 1.396(5) . ?
C10 C11 1.417(5) . ?
C10 C12 1.426(5) . ?
C13 C15 1.413(5) . ?
C13 C14 1.435(5) . ?
C16 C24 1.399(5) . ?
C16 C17 1.401(5) . ?
C16 H16 0.9500 . ?
C17 C25 1.386(5) . ?
C17 C18 1.478(5) . ?
C18 C19 1.380(5) . ?
C18 C23 1.416(5) . ?
C19 C20 1.395(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.484(5) . ?
C24 C28 1.401(5) . ?
C25 C26 1.422(6) . ?
C25 C27 1.427(5) . ?
C28 C30 1.411(5) . ?
C28 C29 1.420(5) . ?
C31 C32 1.371(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(5) . ?
C33 C38 1.479(5) . ?
C34 C35 1.358(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.371(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.403(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.397(5) . ?
C39 C40 1.365(5) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.507(5) . ?
C41 H41 0.9900 . ?
C41 H41A 0.9900 . ?
C42 C43 1.517(5) . ?
C42 H42 0.9900 . ?
C42 H42A 0.9900 . ?
C43 H43 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C44 C45 1.524(6) . ?
C44 H44 0.9900 . ?
C44 H44A 0.9900 . ?
C45 C46 1.524(6) . ?
C45 H45 0.9900 . ?
C45 H45A 0.9900 . ?
C46 H46 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 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
C35 N9 C31 119.2(3) . . ?
C35 N9 C41 120.7(3) . . ?
C31 N9 C41 119.9(3) . . ?
C36 N10 C40 120.4(3) . . ?
C36 N10 C44 120.4(3) . . ?
C40 N10 C44 119.2(3) . . ?
C2 C1 C9 110.7(3) . . ?
C2 C1 H1 128(2) . . ?
C9 C1 H1 121(2) . . ?
C10 C2 C1 124.9(3) . . ?
C10 C2 C3 127.7(3) . . ?
C1 C2 C3 107.4(3) . . ?
C4 C3 C8 120.5(3) . . ?
C4 C3 C2 131.9(3) . . ?
C8 C3 C2 107.5(3) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.0(3) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C3 120.8(3) . . ?
C7 C8 C9 131.9(3) . . ?
C3 C8 C9 107.2(3) . . ?
C13 C9 C1 125.9(3) . . ?
C13 C9 C8 126.9(3) . . ?
C1 C9 C8 107.1(3) . . ?
C2 C10 C11 118.0(3) . . ?
C2 C10 C12 125.6(3) . . ?
C11 C10 C12 116.2(3) . . ?
N1 C11 C10 177.6(4) . . ?
N2 C12 C10 177.3(4) . . ?
C9 C13 C15 125.2(3) . . ?
C9 C13 C14 117.9(3) . . ?
C15 C13 C14 116.9(3) . . ?
N3 C14 C13 177.2(4) . . ?
N4 C15 C13 177.2(4) . . ?
C24 C16 C17 110.7(3) . . ?
C24 C16 H16 124.7 . . ?
C17 C16 H16 124.7 . . ?
C25 C17 C16 125.7(3) . . ?
C25 C17 C18 126.9(3) . . ?
C16 C17 C18 107.4(3) . . ?
C19 C18 C23 120.5(3) . . ?
C19 C18 C17 132.2(3) . . ?
C23 C18 C17 107.3(3) . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.8(4) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 118.1(3) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C22 C23 C18 120.5(3) . . ?
C22 C23 C24 132.0(3) . . ?
C18 C23 C24 107.5(3) . . ?
C16 C24 C28 125.5(3) . . ?
C16 C24 C23 107.0(3) . . ?
C28 C24 C23 127.5(3) . . ?
C17 C25 C26 119.1(3) . . ?
C17 C25 C27 125.5(3) . . ?
C26 C25 C27 115.3(3) . . ?
N5 C26 C25 178.5(4) . . ?
N6 C27 C25 176.9(4) . . ?
C24 C28 C30 123.1(3) . . ?
C24 C28 C29 118.5(3) . . ?
C30 C28 C29 118.3(3) . . ?
N7 C29 C28 176.0(4) . . ?
N8 C30 C28 179.2(5) . . ?
N9 C31 C32 121.0(3) . . ?
N9 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 117.1(3) . . ?
C34 C33 C38 120.9(3) . . ?
C32 C33 C38 122.0(3) . . ?
C35 C34 C33 120.4(4) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
N9 C35 C34 121.9(3) . . ?
N9 C35 H35 119.0 . . ?
C34 C35 H35 119.0 . . ?
N10 C36 C37 120.8(3) . . ?
N10 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C36 C37 C38 120.9(3) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C39 C38 C37 116.4(3) . . ?
C39 C38 C33 122.0(3) . . ?
C37 C38 C33 121.6(3) . . ?
C40 C39 C38 121.2(3) . . ?
C40 C39 H39 119.4 . . ?
C38 C39 H39 119.4 . . ?
N10 C40 C39 120.3(3) . . ?
N10 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
N9 C41 C42 110.5(3) . . ?
N9 C41 H41 109.5 . . ?
C42 C41 H41 109.5 . . ?
N9 C41 H41A 109.5 . . ?
C42 C41 H41A 109.5 . . ?
H41 C41 H41A 108.1 . . ?
C41 C42 C43 114.5(3) . . ?
C41 C42 H42 108.6 . . ?
C43 C42 H42 108.6 . . ?
C41 C42 H42A 108.6 . . ?
C43 C42 H42A 108.6 . . ?
H42 C42 H42A 107.6 . . ?
C42 C43 H43 109.5 . . ?
C42 C43 H43A 109.5 . . ?
H43 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
N10 C44 C45 111.3(3) . . ?
N10 C44 H44 109.4 . . ?
C45 C44 H44 109.4 . . ?
N10 C44 H44A 109.4 . . ?
C45 C44 H44A 109.4 . . ?
H44 C44 H44A 108.0 . . ?
C44 C45 C46 113.7(4) . . ?
C44 C45 H45 108.8 . . ?
C46 C45 H45 108.8 . . ?
C44 C45 H45A 108.8 . . ?
C46 C45 H45A 108.8 . . ?
H45 C45 H45A 107.7 . . ?
C45 C46 H46 109.5 . . ?
C45 C46 H46A 109.5 . . ?
H46 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46 C46 H46B 109.5 . . ?
H46A C46 H46B 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
C9 C1 C2 C10 177.7(3) . . . . ?
C9 C1 C2 C3 -1.5(4) . . . . ?
C10 C2 C3 C4 3.9(6) . . . . ?
C1 C2 C3 C4 -177.0(4) . . . . ?
C10 C2 C3 C8 -177.4(3) . . . . ?
C1 C2 C3 C8 1.7(4) . . . . ?
C8 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 -1.8(6) . . . . ?
C5 C6 C7 C8 1.7(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
C4 C3 C8 C7 -0.4(5) . . . . ?
C2 C3 C8 C7 -179.3(3) . . . . ?
C4 C3 C8 C9 177.6(3) . . . . ?
C2 C3 C8 C9 -1.3(4) . . . . ?
C2 C1 C9 C13 -178.0(3) . . . . ?
C2 C1 C9 C8 0.7(4) . . . . ?
C7 C8 C9 C13 -3.3(6) . . . . ?
C3 C8 C9 C13 179.0(3) . . . . ?
C7 C8 C9 C1 178.1(4) . . . . ?
C3 C8 C9 C1 0.4(4) . . . . ?
C1 C2 C10 C11 1.5(5) . . . . ?
C3 C2 C10 C11 -179.6(3) . . . . ?
C1 C2 C10 C12 -173.5(4) . . . . ?
C3 C2 C10 C12 5.4(6) . . . . ?
C1 C9 C13 C15 176.9(3) . . . . ?
C8 C9 C13 C15 -1.4(6) . . . . ?
C1 C9 C13 C14 -2.0(5) . . . . ?
C8 C9 C13 C14 179.6(3) . . . . ?
C24 C16 C17 C25 -176.0(3) . . . . ?
C24 C16 C17 C18 2.3(4) . . . . ?
C25 C17 C18 C19 -4.5(6) . . . . ?
C16 C17 C18 C19 177.3(4) . . . . ?
C25 C17 C18 C23 176.4(3) . . . . ?
C16 C17 C18 C23 -1.8(4) . . . . ?
C23 C18 C19 C20 0.2(5) . . . . ?
C17 C18 C19 C20 -178.7(4) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C19 C20 C21 C22 0.0(6) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C21 C22 C23 C24 177.9(3) . . . . ?
C19 C18 C23 C22 -0.2(5) . . . . ?
C17 C18 C23 C22 179.0(3) . . . . ?
C19 C18 C23 C24 -178.5(3) . . . . ?
C17 C18 C23 C24 0.7(4) . . . . ?
C17 C16 C24 C28 177.4(3) . . . . ?
C17 C16 C24 C23 -1.8(4) . . . . ?
C22 C23 C24 C16 -177.4(4) . . . . ?
C18 C23 C24 C16 0.6(4) . . . . ?
C22 C23 C24 C28 3.4(6) . . . . ?
C18 C23 C24 C28 -178.6(3) . . . . ?
C16 C17 C25 C26 -0.4(6) . . . . ?
C18 C17 C25 C26 -178.3(3) . . . . ?
C16 C17 C25 C27 174.8(4) . . . . ?
C18 C17 C25 C27 -3.1(6) . . . . ?
C16 C24 C28 C30 -176.9(4) . . . . ?
C23 C24 C28 C30 2.2(6) . . . . ?
C16 C24 C28 C29 -0.4(5) . . . . ?
C23 C24 C28 C29 178.7(3) . . . . ?
C35 N9 C31 C32 -0.3(5) . . . . ?
C41 N9 C31 C32 174.0(3) . . . . ?
N9 C31 C32 C33 -0.7(5) . . . . ?
C31 C32 C33 C34 1.5(5) . . . . ?
C31 C32 C33 C38 -180.0(3) . . . . ?
C32 C33 C34 C35 -1.4(5) . . . . ?
C38 C33 C34 C35 -179.9(3) . . . . ?
C31 N9 C35 C34 0.5(6) . . . . ?
C41 N9 C35 C34 -173.8(4) . . . . ?
C33 C34 C35 N9 0.4(6) . . . . ?
C40 N10 C36 C37 -1.2(5) . . . . ?
C44 N10 C36 C37 176.7(3) . . . . ?
N10 C36 C37 C38 0.1(6) . . . . ?
C36 C37 C38 C39 1.5(5) . . . . ?
C36 C37 C38 C33 -178.0(3) . . . . ?
C34 C33 C38 C39 -4.6(5) . . . . ?
C32 C33 C38 C39 177.0(3) . . . . ?
C34 C33 C38 C37 174.9(3) . . . . ?
C32 C33 C38 C37 -3.5(5) . . . . ?
C37 C38 C39 C40 -2.1(5) . . . . ?
C33 C38 C39 C40 177.4(3) . . . . ?
C36 N10 C40 C39 0.6(5) . . . . ?
C44 N10 C40 C39 -177.3(3) . . . . ?
C38 C39 C40 N10 1.1(6) . . . . ?
C35 N9 C41 C42 91.3(4) . . . . ?
C31 N9 C41 C42 -82.9(4) . . . . ?
N9 C41 C42 C43 -64.8(4) . . . . ?
C36 N10 C44 C45 -94.9(4) . . . . ?
C40 N10 C44 C45 82.9(4) . . . . ?
N10 C44 C45 C46 65.3(4) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_20170411_EtV_-180
_database_code_depnum_ccdc_archive 'CCDC 2268734'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H5 N4, 0.5(C14 H18 N2)'
_chemical_formula_sum            'C22 H14 N5'
_chemical_formula_weight         348.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1502(3)
_cell_length_b                   10.8528(3)
_cell_length_c                   10.8895(3)
_cell_angle_alpha                73.506(2)
_cell_angle_beta                 71.656(3)
_cell_angle_gamma                89.385(2)
_cell_volume                     873.35(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    7980
_cell_measurement_theta_min      1.9930
_cell_measurement_theta_max      30.4150

_exptl_crystal_description       platelet
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             362
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.897
_oxdiff_exptl_absorpt_empirical_full_max 1.138
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 'CCD plate'
_diffrn_reflns_number            11949
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3969
_reflns_number_gt                3375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43(Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.2828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3969
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 1.15648(15) 0.74873(11) -0.08513(12) 0.0185(2) Uani 1 1 d . . . . .
H1 H 1.2440(19) 0.8027(14) -0.1691(15) 0.022 Uiso 1 1 d . U . . .
C2 C 0.99493(15) 0.69547(11) -0.07717(12) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.90659(15) 0.62041(11) 0.06622(12) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.74469(16) 0.55270(11) 0.13052(12) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.6687 0.5475 0.0812 0.025 Uiso 1 1 calc R U . . .
C5 C 0.69595(16) 0.49191(12) 0.27074(13) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.5852 0.4454 0.3167 0.029 Uiso 1 1 calc R U . . .
C6 C 0.80653(17) 0.49860(12) 0.34326(13) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.7714 0.4558 0.4377 0.028 Uiso 1 1 calc R U . . .
C7 C 0.97067(16) 0.56847(11) 0.27789(12) 0.0207(3) Uani 1 1 d . . . . .
H7 H 1.0463 0.5737 0.3274 0.025 Uiso 1 1 calc R U . . .
C8 C 1.01922(15) 0.62920(11) 0.14016(12) 0.0177(2) Uani 1 1 d . . . . .
C9 C 1.17794(15) 0.71099(11) 0.04271(12) 0.0176(2) Uani 1 1 d . . . . .
C10 C 0.93047(15) 0.71211(11) -0.18443(12) 0.0191(2) Uani 1 1 d . . . . .
C11 C 1.02988(16) 0.79132(12) -0.31638(13) 0.0216(3) Uani 1 1 d . . . . .
C12 C 0.77229(16) 0.64919(12) -0.17527(12) 0.0214(3) Uani 1 1 d . . . . .
C13 C 1.32051(15) 0.74850(12) 0.07309(12) 0.0196(3) Uani 1 1 d . . . . .
C14 C 1.45841(15) 0.83441(12) -0.03097(13) 0.0211(3) Uani 1 1 d . . . . .
C15 C 1.33520(16) 0.71228(12) 0.20534(13) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.97105(15) 0.89431(11) 0.30115(12) 0.0189(2) Uani 1 1 d . . . . .
H16 H 1.0322 0.8910 0.3631 0.023 Uiso 1 1 calc R U . . .
C17 C 1.04848(15) 0.95954(11) 0.16569(12) 0.0183(2) Uani 1 1 d . . . . .
H17 H 1.1624 1.0007 0.1350 0.022 Uiso 1 1 calc R U . . .
C18 C 0.95964(15) 0.96527(11) 0.07338(11) 0.0167(2) Uani 1 1 d . . . . .
C19 C 0.79218(16) 0.90268(12) 0.12404(12) 0.0202(3) Uani 1 1 d . . . . .
H19 H 0.7280 0.9043 0.0644 0.024 Uiso 1 1 calc R U . . .
C20 C 0.72029(16) 0.83881(12) 0.26010(12) 0.0215(3) Uani 1 1 d . . . . .
H20 H 0.6065 0.7968 0.2936 0.026 Uiso 1 1 calc R U . . .
C21 C 0.72574(16) 0.76547(12) 0.49294(12) 0.0223(3) Uani 1 1 d . . . . .
H21 H 0.8159 0.7471 0.5374 0.027 Uiso 1 1 calc R U . . .
H21A H 0.6675 0.6821 0.5025 0.027 Uiso 1 1 calc R U . . .
C22 C 0.59427(19) 0.84424(14) 0.56227(13) 0.0313(3) Uani 1 1 d . . . . .
H22 H 0.5415 0.7963 0.6582 0.047 Uiso 1 1 calc R U . . .
H22A H 0.6522 0.9262 0.5542 0.047 Uiso 1 1 calc R U . . .
H22B H 0.5039 0.8613 0.5193 0.047 Uiso 1 1 calc R U . . .
N1 N 1.10854(15) 0.85672(11) -0.42277(11) 0.0294(3) Uani 1 1 d . . . . .
N2 N 0.64772(15) 0.59882(11) -0.17381(12) 0.0277(3) Uani 1 1 d . . . . .
N3 N 1.56657(14) 0.90596(11) -0.11541(12) 0.0281(3) Uani 1 1 d . . . . .
N4 N 1.34828(15) 0.68629(13) 0.31187(12) 0.0317(3) Uani 1 1 d . . . . .
N5 N 0.80926(13) 0.83518(10) 0.34633(10) 0.0189(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.4015(16) . ?
C1 C2 1.4111(16) . ?
C1 H1 0.991(15) . ?
C2 C10 1.3919(16) . ?
C2 C3 1.4842(16) . ?
C3 C4 1.3851(16) . ?
C3 C8 1.4180(16) . ?
C4 C5 1.4058(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3867(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4097(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3824(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4876(16) . ?
C9 C13 1.3979(16) . ?
C10 C12 1.4274(17) . ?
C10 C11 1.4285(17) . ?
C11 N1 1.1543(17) . ?
C12 N2 1.1518(17) . ?
C13 C15 1.4244(17) . ?
C13 C14 1.4274(17) . ?
C14 N3 1.1509(17) . ?
C15 N4 1.1525(17) . ?
C16 N5 1.3503(15) . ?
C16 C17 1.3806(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.4001(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.4005(17) . ?
C18 C18 1.490(2) 2_775 ?
C19 C20 1.3778(17) . ?
C19 H19 0.9500 . ?
C20 N5 1.3475(16) . ?
C20 H20 0.9500 . ?
C21 N5 1.4919(15) . ?
C21 C22 1.5121(18) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 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
C9 C1 C2 110.08(10) . . ?
C9 C1 H1 124.7(8) . . ?
C2 C1 H1 125.2(8) . . ?
C10 C2 C1 125.94(11) . . ?
C10 C2 C3 126.64(11) . . ?
C1 C2 C3 107.42(10) . . ?
C4 C3 C8 120.86(11) . . ?
C4 C3 C2 131.58(11) . . ?
C8 C3 C2 107.55(10) . . ?
C3 C4 C5 118.17(11) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.24(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.52(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 118.61(11) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C3 120.59(11) . . ?
C7 C8 C9 132.23(11) . . ?
C3 C8 C9 107.18(10) . . ?
C13 C9 C1 125.67(11) . . ?
C13 C9 C8 126.52(11) . . ?
C1 C9 C8 107.76(10) . . ?
C2 C10 C12 124.59(11) . . ?
C2 C10 C11 119.71(11) . . ?
C12 C10 C11 115.61(11) . . ?
N1 C11 C10 178.99(14) . . ?
N2 C12 C10 177.00(13) . . ?
C9 C13 C15 124.22(11) . . ?
C9 C13 C14 119.63(11) . . ?
C15 C13 C14 116.06(11) . . ?
N3 C14 C13 178.24(14) . . ?
N4 C15 C13 178.21(14) . . ?
N5 C16 C17 120.60(11) . . ?
N5 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.23(11) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 117.51(11) . . ?
C17 C18 C18 121.31(13) . 2_775 ?
C19 C18 C18 121.18(13) . 2_775 ?
C20 C19 C18 120.17(11) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
N5 C20 C19 120.85(11) . . ?
N5 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N5 C21 C22 111.19(10) . . ?
N5 C21 H21 109.4 . . ?
C22 C21 H21 109.4 . . ?
N5 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
H21 C21 H21A 108.0 . . ?
C21 C22 H22 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 N5 C16 120.64(10) . . ?
C20 N5 C21 118.96(10) . . ?
C16 N5 C21 120.40(10) . . ?

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
C9 C1 C2 C10 -179.75(11) . . . . ?
C9 C1 C2 C3 0.95(13) . . . . ?
C10 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 177.68(12) . . . . ?
C10 C2 C3 C8 179.84(11) . . . . ?
C1 C2 C3 C8 -0.87(12) . . . . ?
C8 C3 C4 C5 -0.64(17) . . . . ?
C2 C3 C4 C5 -179.03(11) . . . . ?
C3 C4 C5 C6 -0.30(18) . . . . ?
C4 C5 C6 C7 0.84(19) . . . . ?
C5 C6 C7 C8 -0.43(18) . . . . ?
C6 C7 C8 C3 -0.49(17) . . . . ?
C6 C7 C8 C9 178.64(11) . . . . ?
C4 C3 C8 C7 1.04(17) . . . . ?
C2 C3 C8 C7 179.78(10) . . . . ?
C4 C3 C8 C9 -178.28(10) . . . . ?
C2 C3 C8 C9 0.46(12) . . . . ?
C2 C1 C9 C13 -178.26(11) . . . . ?
C2 C1 C9 C8 -0.68(13) . . . . ?
C7 C8 C9 C13 -1.5(2) . . . . ?
C3 C8 C9 C13 177.67(11) . . . . ?
C7 C8 C9 C1 -179.10(12) . . . . ?
C3 C8 C9 C1 0.11(12) . . . . ?
C1 C2 C10 C12 175.07(11) . . . . ?
C3 C2 C10 C12 -5.77(19) . . . . ?
C1 C2 C10 C11 -1.29(18) . . . . ?
C3 C2 C10 C11 177.88(11) . . . . ?
C1 C9 C13 C15 177.48(12) . . . . ?
C8 C9 C13 C15 0.34(19) . . . . ?
C1 C9 C13 C14 1.18(18) . . . . ?
C8 C9 C13 C14 -175.96(11) . . . . ?
N5 C16 C17 C18 0.09(18) . . . . ?
C16 C17 C18 C19 -0.15(17) . . . . ?
C16 C17 C18 C18 -179.84(12) . . . 2_775 ?
C17 C18 C19 C20 0.17(17) . . . . ?
C18 C18 C19 C20 179.86(13) 2_775 . . . ?
C18 C19 C20 N5 -0.13(19) . . . . ?
C19 C20 N5 C16 0.07(18) . . . . ?
C19 C20 N5 C21 179.66(11) . . . . ?
C17 C16 N5 C20 -0.05(17) . . . . ?
C17 C16 N5 C21 -179.64(10) . . . . ?
C22 C21 N5 C20 -76.92(14) . . . . ?
C22 C21 N5 C16 102.67(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16 N1 0.95 2.53 3.4459(16) 163.3 1_556
C17 H17 N3 0.95 2.36 3.2920(16) 166.1 2_875
C19 H19 N3 0.95 2.68 3.6257(17) 176.2 1_455
C20 H20 N4 0.95 2.36 3.2791(17) 163.1 1_455
C16 H16 N1 0.95 2.53 3.4459(16) 163.3 1_556
C17 H17 N3 0.95 2.36 3.2920(16) 166.1 2_875

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_20190315_OV_-123
_database_code_depnum_ccdc_archive 'CCDC 2268739'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H42 N2, 2(C15 H5 N4), 2(C3 H6 O)'
_chemical_formula_sum            'C62 H64 N10 O2'
_chemical_formula_weight         981.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6158(5)
_cell_length_b                   12.9796(7)
_cell_length_c                   13.0395(6)
_cell_angle_alpha                65.171(5)
_cell_angle_beta                 87.992(4)
_cell_angle_gamma                69.283(5)
_cell_volume                     1369.11(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    3084
_cell_measurement_theta_min      1.7960
_cell_measurement_theta_max      25.9900

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             522
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.67069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.774
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            16839
_diffrn_reflns_av_unetI/netI     0.1049
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5349
_reflns_number_gt                2864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.1852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5349
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1999
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6275(3) -0.1091(3) 0.1948(3) 0.0620(9) Uani 1 1 d . . . . .
N2 N 0.2133(3) -0.0590(3) 0.0119(3) 0.0582(8) Uani 1 1 d . . . . .
N3 N 0.5162(4) 0.1735(3) 0.4413(3) 0.0688(10) Uani 1 1 d . . . . .
N4 N 0.0288(3) 0.3587(3) 0.4416(2) 0.0545(8) Uani 1 1 d . . . . .
N5 N 0.9734(3) 0.1425(2) 0.6817(2) 0.0383(6) Uani 1 1 d . . . . .
O1 O 0.5834(3) 0.3636(3) 0.6529(3) 0.0949(11) Uani 1 1 d . . . . .
C1 C 0.3272(4) 0.0983(3) 0.2680(3) 0.0409(8) Uani 1 1 d . . . . .
H1 H 0.439(3) 0.063(3) 0.295(2) 0.049 Uiso 1 1 d . U . . .
C2 C 0.2622(3) 0.0703(3) 0.1931(2) 0.0377(7) Uani 1 1 d . . . . .
C3 C 0.0974(3) 0.1368(3) 0.1774(2) 0.0373(7) Uani 1 1 d . . . . .
C4 C -0.0204(3) 0.1425(3) 0.1157(3) 0.0400(8) Uani 1 1 d . . . . .
H4 H -0.002244 0.099762 0.069630 0.048 Uiso 1 1 calc R U . . .
C5 C -0.1661(4) 0.2112(3) 0.1214(3) 0.0442(8) Uani 1 1 d . . . . .
H5 H -0.247819 0.214583 0.079609 0.053 Uiso 1 1 calc R U . . .
C6 C -0.1936(4) 0.2748(3) 0.1874(3) 0.0450(8) Uani 1 1 d . . . . .
H6 H -0.293914 0.321891 0.189822 0.054 Uiso 1 1 calc R U . . .
C7 C -0.0756(3) 0.2705(3) 0.2502(2) 0.0397(8) Uani 1 1 d . . . . .
H7 H -0.094873 0.314470 0.295084 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0693(3) 0.2014(3) 0.2462(2) 0.0355(7) Uani 1 1 d . . . . .
C9 C 0.2164(3) 0.1765(3) 0.3020(2) 0.0372(7) Uani 1 1 d . . . . .
C10 C 0.3393(3) -0.0070(3) 0.1442(3) 0.0409(8) Uani 1 1 d . . . . .
C11 C 0.4986(4) -0.0640(3) 0.1704(3) 0.0458(8) Uani 1 1 d . . . . .
C12 C 0.2697(4) -0.0346(3) 0.0702(3) 0.0443(8) Uani 1 1 d . . . . .
C13 C 0.2410(3) 0.2245(3) 0.3757(3) 0.0414(8) Uani 1 1 d . . . . .
C14 C 0.3917(4) 0.1967(3) 0.4146(3) 0.0517(9) Uani 1 1 d . . . . .
C15 C 0.1240(4) 0.2992(3) 0.4119(3) 0.0440(8) Uani 1 1 d . . . . .
C16 C 1.1082(3) 0.0716(3) 0.6706(3) 0.0400(8) Uani 1 1 d . . . . .
H16 H 1.195578 0.059502 0.712987 0.048 Uiso 1 1 calc R U . . .
C17 C 1.1224(3) 0.0158(3) 0.5987(3) 0.0404(8) Uani 1 1 d . . . . .
H17 H 1.218791 -0.033384 0.591372 0.048 Uiso 1 1 calc R U . . .
C18 C 0.9946(3) 0.0321(3) 0.5372(2) 0.0334(7) Uani 1 1 d . . . . .
C19 C 0.8566(3) 0.1078(3) 0.5489(3) 0.0394(8) Uani 1 1 d . . . . .
H19 H 0.767475 0.121985 0.507080 0.047 Uiso 1 1 calc R U . . .
C20 C 0.8486(3) 0.1622(3) 0.6208(3) 0.0406(8) Uani 1 1 d . . . . .
H20 H 0.753954 0.214309 0.627536 0.049 Uiso 1 1 calc R U . . .
C21 C 0.9614(4) 0.1994(3) 0.7619(3) 0.0435(8) Uani 1 1 d . . . . .
H21 H 1.029487 0.138870 0.833483 0.052 Uiso 1 1 calc R U . . .
H21A H 0.857599 0.222232 0.780822 0.052 Uiso 1 1 calc R U . . .
C22 C 1.0012(4) 0.3114(3) 0.7112(3) 0.0439(8) Uani 1 1 d . . . . .
H22 H 0.927689 0.374661 0.643333 0.053 Uiso 1 1 calc R U . . .
H22A H 1.101571 0.290029 0.686012 0.053 Uiso 1 1 calc R U . . .
C23 C 1.0022(3) 0.3635(3) 0.7973(3) 0.0453(8) Uani 1 1 d . . . . .
H23 H 1.061669 0.295704 0.869947 0.054 Uiso 1 1 calc R U . . .
H23A H 1.053758 0.422159 0.768156 0.054 Uiso 1 1 calc R U . . .
C24 C 0.8476(3) 0.4281(3) 0.8219(3) 0.0442(8) Uani 1 1 d . . . . .
H24 H 0.799430 0.367965 0.858775 0.053 Uiso 1 1 calc R U . . .
H24A H 0.784283 0.491425 0.748992 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8552(3) 0.4883(3) 0.8992(3) 0.0417(8) Uani 1 1 d . . . . .
H25 H 0.913735 0.423774 0.973450 0.050 Uiso 1 1 calc R U . . .
H25A H 0.910259 0.543658 0.864462 0.050 Uiso 1 1 calc R U . . .
C26 C 0.7036(3) 0.5611(3) 0.9205(3) 0.0433(8) Uani 1 1 d . . . . .
H26 H 0.647884 0.506347 0.955397 0.052 Uiso 1 1 calc R U . . .
H26A H 0.644882 0.626662 0.846658 0.052 Uiso 1 1 calc R U . . .
C27 C 0.7185(3) 0.6186(3) 0.9990(3) 0.0449(8) Uani 1 1 d . . . . .
H27 H 0.771813 0.552325 1.074253 0.054 Uiso 1 1 calc R U . . .
H27A H 0.780673 0.668365 0.966518 0.054 Uiso 1 1 calc R U . . .
C28 C 0.5701(4) 0.6986(3) 1.0161(3) 0.0593(10) Uani 1 1 d . . . . .
H28 H 0.517671 0.766085 0.942324 0.089 Uiso 1 1 calc R U . . .
H28A H 0.588064 0.731813 1.067140 0.089 Uiso 1 1 calc R U . . .
H28B H 0.508438 0.649784 1.049852 0.089 Uiso 1 1 calc R U . . .
C29 C 0.3449(5) 0.3971(4) 0.5778(4) 0.0875(14) Uani 1 1 d . . . . .
H29 H 0.324070 0.452607 0.496225 0.131 Uiso 1 1 calc R U . . .
H29A H 0.251045 0.409379 0.611417 0.131 Uiso 1 1 calc R U . . .
H29B H 0.389673 0.312231 0.588228 0.131 Uiso 1 1 calc R U . . .
C30 C 0.4499(4) 0.4228(3) 0.6344(3) 0.0587(10) Uani 1 1 d . . . . .
C31 C 0.3877(5) 0.5257(4) 0.6671(4) 0.0890(15) Uani 1 1 d . . . . .
H31 H 0.319071 0.508111 0.723524 0.134 Uiso 1 1 calc R U . . .
H31A H 0.333249 0.601492 0.599404 0.134 Uiso 1 1 calc R U . . .
H31B H 0.469974 0.535122 0.699973 0.134 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.157(4) . ?
N2 C12 1.151(4) . ?
N3 C14 1.154(4) . ?
N4 C15 1.145(4) . ?
N5 C16 1.343(4) . ?
N5 C20 1.347(4) . ?
N5 C21 1.494(3) . ?
O1 C30 1.211(4) . ?
C1 C9 1.394(4) . ?
C1 C2 1.405(4) . ?
C1 H1 1.01(3) . ?
C2 C10 1.393(4) . ?
C2 C3 1.485(4) . ?
C3 C4 1.375(4) . ?
C3 C8 1.426(4) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.478(4) . ?
C9 C13 1.410(4) . ?
C10 C12 1.419(4) . ?
C10 C11 1.426(5) . ?
C13 C15 1.416(4) . ?
C13 C14 1.419(5) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(4) . ?
C18 C18 1.503(5) 2_756 ?
C19 C20 1.377(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.505(4) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.538(4) . ?
C22 H22 0.9900 . ?
C22 H22A 0.9900 . ?
C23 C24 1.526(4) . ?
C23 H23 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.529(4) . ?
C24 H24 0.9900 . ?
C24 H24A 0.9900 . ?
C25 C26 1.520(4) . ?
C25 H25 0.9900 . ?
C25 H25A 0.9900 . ?
C26 C27 1.534(4) . ?
C26 H26 0.9900 . ?
C26 H26A 0.9900 . ?
C27 C28 1.512(4) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 H28 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 C30 1.474(5) . ?
C29 H29 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C30 C31 1.489(5) . ?
C31 H31 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 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
C16 N5 C20 120.1(2) . . ?
C16 N5 C21 120.1(3) . . ?
C20 N5 C21 119.9(2) . . ?
C9 C1 C2 110.4(3) . . ?
C9 C1 H1 126.0(17) . . ?
C2 C1 H1 123.6(17) . . ?
C10 C2 C1 125.9(3) . . ?
C10 C2 C3 126.7(3) . . ?
C1 C2 C3 107.4(3) . . ?
C4 C3 C8 120.0(3) . . ?
C4 C3 C2 132.9(3) . . ?
C8 C3 C2 107.0(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C3 120.1(3) . . ?
C7 C8 C9 132.7(3) . . ?
C3 C8 C9 107.2(3) . . ?
C1 C9 C13 125.8(3) . . ?
C1 C9 C8 108.0(3) . . ?
C13 C9 C8 126.2(3) . . ?
C2 C10 C12 124.3(3) . . ?
C2 C10 C11 118.6(3) . . ?
C12 C10 C11 117.1(3) . . ?
N1 C11 C10 177.6(3) . . ?
N2 C12 C10 178.7(4) . . ?
C9 C13 C15 123.6(3) . . ?
C9 C13 C14 117.8(3) . . ?
C15 C13 C14 118.6(3) . . ?
N3 C14 C13 176.5(4) . . ?
N4 C15 C13 179.3(4) . . ?
N5 C16 C17 121.3(3) . . ?
N5 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 117.8(3) . . ?
C19 C18 C18 121.2(3) . 2_756 ?
C17 C18 C18 121.0(3) . 2_756 ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 C20 C19 120.8(3) . . ?
N5 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N5 C21 C22 111.6(2) . . ?
N5 C21 H21 109.3 . . ?
C22 C21 H21 109.3 . . ?
N5 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
H21 C21 H21A 108.0 . . ?
C21 C22 C23 111.6(3) . . ?
C21 C22 H22 109.3 . . ?
C23 C22 H22 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
H22 C22 H22A 108.0 . . ?
C24 C23 C22 114.9(3) . . ?
C24 C23 H23 108.5 . . ?
C22 C23 H23 108.5 . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23A 108.5 . . ?
H23 C23 H23A 107.5 . . ?
C23 C24 C25 112.4(3) . . ?
C23 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
H24 C24 H24A 107.9 . . ?
C26 C25 C24 114.7(3) . . ?
C26 C25 H25 108.6 . . ?
C24 C25 H25 108.6 . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
H25 C25 H25A 107.6 . . ?
C25 C26 C27 112.3(2) . . ?
C25 C26 H26 109.1 . . ?
C27 C26 H26 109.1 . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
H26 C26 H26A 107.9 . . ?
C28 C27 C26 113.9(3) . . ?
C28 C27 H27 108.8 . . ?
C26 C27 H27 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
H27 C27 H27A 107.7 . . ?
C27 C28 H28 109.5 . . ?
C27 C28 H28A 109.5 . . ?
H28 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C30 C29 H29 109.5 . . ?
C30 C29 H29A 109.5 . . ?
H29 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O1 C30 C29 121.5(4) . . ?
O1 C30 C31 120.3(4) . . ?
C29 C30 C31 118.2(4) . . ?
C30 C31 H31 109.5 . . ?
C30 C31 H31A 109.5 . . ?
H31 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31 C31 H31B 109.5 . . ?
H31A C31 H31B 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
C9 C1 C2 C10 -178.7(3) . . . . ?
C9 C1 C2 C3 0.5(3) . . . . ?
C10 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -179.1(3) . . . . ?
C10 C2 C3 C8 178.2(3) . . . . ?
C1 C2 C3 C8 -1.0(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C3 0.8(4) . . . . ?
C6 C7 C8 C9 -179.3(3) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
C2 C3 C8 C7 -179.0(3) . . . . ?
C4 C3 C8 C9 179.4(3) . . . . ?
C2 C3 C8 C9 1.1(3) . . . . ?
C2 C1 C9 C13 -179.2(3) . . . . ?
C2 C1 C9 C8 0.2(4) . . . . ?
C7 C8 C9 C1 179.3(3) . . . . ?
C3 C8 C9 C1 -0.8(3) . . . . ?
C7 C8 C9 C13 -1.4(5) . . . . ?
C3 C8 C9 C13 178.6(3) . . . . ?
C1 C2 C10 C12 179.0(3) . . . . ?
C3 C2 C10 C12 -0.1(5) . . . . ?
C1 C2 C10 C11 -0.3(5) . . . . ?
C3 C2 C10 C11 -179.4(3) . . . . ?
C1 C9 C13 C15 -176.9(3) . . . . ?
C8 C9 C13 C15 3.9(5) . . . . ?
C1 C9 C13 C14 3.6(5) . . . . ?
C8 C9 C13 C14 -175.6(3) . . . . ?
C20 N5 C16 C17 -1.1(4) . . . . ?
C21 N5 C16 C17 178.7(3) . . . . ?
N5 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C19 1.7(4) . . . . ?
C16 C17 C18 C18 -177.0(3) . . . 2_756 ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C18 C19 C20 177.6(3) 2_756 . . . ?
C16 N5 C20 C19 1.8(4) . . . . ?
C21 N5 C20 C19 -178.1(3) . . . . ?
C18 C19 C20 N5 -0.6(5) . . . . ?
C16 N5 C21 C22 79.2(3) . . . . ?
C20 N5 C21 C22 -101.0(3) . . . . ?
N5 C21 C22 C23 -175.1(2) . . . . ?
C21 C22 C23 C24 -72.9(4) . . . . ?
C22 C23 C24 C25 -174.6(3) . . . . ?
C23 C24 C25 C26 176.3(3) . . . . ?
C24 C25 C26 C27 179.7(3) . . . . ?
C25 C26 C27 C28 176.2(3) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_20190317_PnV_-123
_database_code_depnum_ccdc_archive 'CCDC 2268737'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H30 N2, 2(C15 H5 N4)'
_chemical_formula_sum            'C50 H40 N10'
_chemical_formula_weight         780.92

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2406(2)
_cell_length_b                   13.7520(3)
_cell_length_c                   14.5481(3)
_cell_angle_alpha                68.229(2)
_cell_angle_beta                 75.915(2)
_cell_angle_gamma                85.545(2)
_cell_volume                     2025.47(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    11029
_cell_measurement_theta_min      2.2020
_cell_measurement_theta_max      30.3400

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.93860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.908
_oxdiff_exptl_absorpt_empirical_full_max 1.078
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            28031
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.549
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9221
_reflns_number_gt                6763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+0.4669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9221
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.62412(17) 0.44320(13) -0.17880(13) 0.0468(4) Uani 1 1 d . . . . .
N2 N 0.53542(16) 0.69458(16) -0.44878(12) 0.0524(5) Uani 1 1 d . . . . .
N3 N 0.72308(16) 0.58751(11) 0.10147(11) 0.0404(4) Uani 1 1 d . . . . .
N4 N 0.63727(16) 0.92258(12) 0.04161(12) 0.0438(4) Uani 1 1 d . . . . .
N5 N 0.69788(12) 0.21140(10) 0.04345(10) 0.0279(3) Uani 1 1 d . . . . .
N6 N 0.78413(12) 0.30883(10) 0.46514(10) 0.0289(3) Uani 1 1 d . . . . .
N7 N 0.78492(16) -0.07118(12) 0.39810(12) 0.0438(4) Uani 1 1 d . . . . .
N8 N 0.87633(15) -0.40462(12) 0.44533(12) 0.0414(4) Uani 1 1 d . . . . .
N9 N 0.86675(16) 0.05945(13) 0.69066(13) 0.0450(4) Uani 1 1 d . . . . .
N10 N 0.97028(16) -0.20280(14) 0.95103(12) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.62928(15) 0.67773(13) -0.13130(12) 0.0285(3) Uani 1 1 d . . . . .
H1 H 0.6490(16) 0.6044(15) -0.0883(13) 0.034 Uiso 1 1 d . U . . .
C2 C 0.60048(14) 0.70659(13) -0.22612(12) 0.0283(3) Uani 1 1 d . . . . .
C3 C 0.57786(14) 0.82099(13) -0.26166(12) 0.0290(3) Uani 1 1 d . . . . .
C4 C 0.54766(16) 0.88972(15) -0.34983(13) 0.0372(4) Uani 1 1 d . . . . .
H4 H 0.542644 0.866761 -0.402851 0.045 Uiso 1 1 calc R U . . .
C5 C 0.52468(17) 0.99419(15) -0.35877(14) 0.0428(5) Uani 1 1 d . . . . .
H5 H 0.503179 1.042513 -0.418421 0.051 Uiso 1 1 calc R U . . .
C6 C 0.53289(17) 1.02779(14) -0.28194(15) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.514589 1.098398 -0.288767 0.051 Uiso 1 1 calc R U . . .
C7 C 0.56789(16) 0.95919(13) -0.19381(14) 0.0354(4) Uani 1 1 d . . . . .
H7 H 0.576147 0.983056 -0.142165 0.042 Uiso 1 1 calc R U . . .
C8 C 0.58992(14) 0.85603(12) -0.18454(12) 0.0289(3) Uani 1 1 d . . . . .
C9 C 0.62557(14) 0.76449(12) -0.10214(11) 0.0262(3) Uani 1 1 d . . . . .
C10 C 0.59068(15) 0.63837(14) -0.27502(12) 0.0316(4) Uani 1 1 d . . . . .
C11 C 0.60905(16) 0.52954(14) -0.22375(13) 0.0350(4) Uani 1 1 d . . . . .
C12 C 0.56102(16) 0.66913(15) -0.37149(13) 0.0364(4) Uani 1 1 d . . . . .
C13 C 0.65238(14) 0.76346(12) -0.01335(12) 0.0276(3) Uani 1 1 d . . . . .
C14 C 0.69155(16) 0.66745(12) 0.05273(12) 0.0300(4) Uani 1 1 d . . . . .
C15 C 0.64528(15) 0.85200(13) 0.01590(13) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.70013(17) 0.31077(13) 0.03984(13) 0.0350(4) Uani 1 1 d . . . . .
H16 H 0.688075 0.367227 -0.019083 0.042 Uiso 1 1 calc R U . . .
C17 C 0.71979(17) 0.33089(13) 0.12105(13) 0.0347(4) Uani 1 1 d . . . . .
H17 H 0.721176 0.401163 0.117595 0.042 Uiso 1 1 calc R U . . .
C18 C 0.73771(14) 0.24881(12) 0.20852(11) 0.0259(3) Uani 1 1 d . . . . .
C19 C 0.73808(14) 0.14700(12) 0.20810(12) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.752633 0.089074 0.264962 0.034 Uiso 1 1 calc R U . . .
C20 C 0.71732(14) 0.13090(12) 0.12513(12) 0.0287(3) Uani 1 1 d . . . . .
H20 H 0.716781 0.061564 0.125881 0.034 Uiso 1 1 calc R U . . .
C21 C 0.77047(15) 0.38904(12) 0.38041(12) 0.0299(3) Uani 1 1 d . . . . .
H21 H 0.771725 0.458844 0.378273 0.036 Uiso 1 1 calc R U . . .
C22 C 0.75470(14) 0.37137(12) 0.29678(12) 0.0285(3) Uani 1 1 d . . . . .
H22 H 0.744520 0.428817 0.237911 0.034 Uiso 1 1 calc R U . . .
C23 C 0.75366(14) 0.26904(12) 0.29841(11) 0.0262(3) Uani 1 1 d . . . . .
C24 C 0.76791(16) 0.18775(12) 0.38725(12) 0.0321(4) Uani 1 1 d . . . . .
H24 H 0.767398 0.117222 0.391312 0.039 Uiso 1 1 calc R U . . .
C25 C 0.78273(16) 0.20927(13) 0.46923(13) 0.0331(4) Uani 1 1 d . . . . .
H25 H 0.792080 0.153230 0.529376 0.040 Uiso 1 1 calc R U . . .
C26 C 0.67414(15) 0.19232(13) -0.04519(12) 0.0309(4) Uani 1 1 d . . . . .
H26 H 0.607474 0.238337 -0.069910 0.037 Uiso 1 1 calc R U . . .
H26A H 0.646863 0.118766 -0.023234 0.037 Uiso 1 1 calc R U . . .
C27 C 0.78827(16) 0.21347(13) -0.13110(12) 0.0352(4) Uani 1 1 d . . . . .
H27 H 0.765891 0.210365 -0.191710 0.042 Uiso 1 1 calc R U . . .
H27A H 0.818567 0.285355 -0.148844 0.042 Uiso 1 1 calc R U . . .
C28 C 0.89118(15) 0.13735(13) -0.10620(12) 0.0331(4) Uani 1 1 d . . . . .
H28 H 0.865755 0.067254 -0.099519 0.040 Uiso 1 1 calc R U . . .
H28A H 0.904604 0.131838 -0.039675 0.040 Uiso 1 1 calc R U . . .
C29 C 1.01172(16) 0.16896(13) -0.18584(13) 0.0367(4) Uani 1 1 d . . . . .
H29 H 0.998012 0.178135 -0.253246 0.044 Uiso 1 1 calc R U . . .
H29A H 1.040439 0.236935 -0.189722 0.044 Uiso 1 1 calc R U . . .
C30 C 1.10962(17) 0.08776(14) -0.16093(14) 0.0398(4) Uani 1 1 d . . . . .
H30 H 1.123508 0.078589 -0.094275 0.060 Uiso 1 1 calc R U . . .
H30A H 1.186045 0.111146 -0.212973 0.060 Uiso 1 1 calc R U . . .
H30B H 1.082678 0.020982 -0.159407 0.060 Uiso 1 1 calc R U . . .
C31 C 0.80230(16) 0.33265(14) 0.55315(12) 0.0325(4) Uani 1 1 d . . . . .
H31 H 0.875167 0.378986 0.530722 0.039 Uiso 1 1 calc R U . . .
H31A H 0.817693 0.266797 0.607065 0.039 Uiso 1 1 calc R U . . .
C32 C 0.68988(16) 0.38602(13) 0.59653(13) 0.0355(4) Uani 1 1 d . . . . .
H32 H 0.709433 0.408411 0.648551 0.043 Uiso 1 1 calc R U . . .
H32A H 0.672570 0.449725 0.541187 0.043 Uiso 1 1 calc R U . . .
C33 C 0.57504(16) 0.31706(14) 0.64433(13) 0.0358(4) Uani 1 1 d . . . . .
H33 H 0.583944 0.264057 0.710355 0.043 Uiso 1 1 calc R U . . .
H33A H 0.568031 0.279352 0.599607 0.043 Uiso 1 1 calc R U . . .
C34 C 0.45649(17) 0.37753(15) 0.66201(14) 0.0425(4) Uani 1 1 d . . . . .
H34 H 0.460865 0.412170 0.709855 0.051 Uiso 1 1 calc R U . . .
H34A H 0.448729 0.432711 0.596765 0.051 Uiso 1 1 calc R U . . .
C35 C 0.34441(18) 0.30629(16) 0.70482(14) 0.0457(5) Uani 1 1 d . . . . .
H35 H 0.339384 0.272346 0.657343 0.069 Uiso 1 1 calc R U . . .
H35A H 0.270602 0.347635 0.714450 0.069 Uiso 1 1 calc R U . . .
H35B H 0.350682 0.252767 0.770386 0.069 Uiso 1 1 calc R U . . .
C36 C 0.88218(15) -0.16835(13) 0.62786(12) 0.0287(3) Uani 1 1 d . . . . .
H36 H 0.8624(16) -0.0940(15) 0.5881(13) 0.034 Uiso 1 1 d . U . . .
C37 C 0.88608(14) -0.25344(12) 0.59592(12) 0.0265(3) Uani 1 1 d . . . . .
C38 C 0.91943(14) -0.34701(12) 0.67748(12) 0.0276(3) Uani 1 1 d . . . . .
C39 C 0.93800(15) -0.45019(13) 0.68513(13) 0.0329(4) Uani 1 1 d . . . . .
H39 H 0.929989 -0.471931 0.632075 0.039 Uiso 1 1 calc R U . . .
C40 C 0.96900(17) -0.52172(13) 0.77354(14) 0.0396(4) Uani 1 1 d . . . . .
H40 H 0.984647 -0.592377 0.779260 0.048 Uiso 1 1 calc R U . . .
C41 C 0.97724(16) -0.49161(14) 0.85230(14) 0.0400(4) Uani 1 1 d . . . . .
H41 H 0.995860 -0.542050 0.912214 0.048 Uiso 1 1 calc R U . . .
C42 C 0.95832(16) -0.38695(14) 0.84464(13) 0.0352(4) Uani 1 1 d . . . . .
H42 H 0.964087 -0.365978 0.898717 0.042 Uiso 1 1 calc R U . . .
C43 C 0.93109(14) -0.31510(12) 0.75664(12) 0.0277(3) Uani 1 1 d . . . . .
C44 C 0.90944(14) -0.20052(12) 0.72363(12) 0.0282(3) Uani 1 1 d . . . . .
C45 C 0.86010(15) -0.24895(12) 0.50549(12) 0.0278(3) Uani 1 1 d . . . . .
C46 C 0.81958(16) -0.15171(13) 0.44275(12) 0.0325(4) Uani 1 1 d . . . . .
C47 C 0.86786(15) -0.33517(13) 0.47273(12) 0.0314(4) Uani 1 1 d . . . . .
C48 C 0.91564(15) -0.13518(13) 0.77665(12) 0.0305(4) Uani 1 1 d . . . . .
C49 C 0.88986(16) -0.02664(14) 0.73108(13) 0.0339(4) Uani 1 1 d . . . . .
C50 C 0.94513(16) -0.17152(14) 0.87320(13) 0.0349(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.146(2) . ?
N2 C12 1.149(2) . ?
N3 C14 1.149(2) . ?
N4 C15 1.153(2) . ?
N5 C20 1.3409(19) . ?
N5 C16 1.350(2) . ?
N5 C26 1.494(2) . ?
N6 C21 1.348(2) . ?
N6 C25 1.349(2) . ?
N6 C31 1.496(2) . ?
N7 C46 1.150(2) . ?
N8 C47 1.153(2) . ?
N9 C49 1.151(2) . ?
N10 C50 1.150(2) . ?
C1 C2 1.399(2) . ?
C1 C9 1.402(2) . ?
C1 H1 1.011(19) . ?
C2 C10 1.396(2) . ?
C2 C3 1.485(2) . ?
C3 C4 1.384(2) . ?
C3 C8 1.412(2) . ?
C4 C5 1.403(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.489(2) . ?
C9 C13 1.391(2) . ?
C10 C12 1.423(2) . ?
C10 C11 1.427(2) . ?
C13 C15 1.422(2) . ?
C13 C14 1.427(2) . ?
C16 C17 1.379(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.402(2) . ?
C18 C23 1.487(2) . ?
C19 C20 1.380(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.379(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.400(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(2) . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.517(2) . ?
C26 H26 0.9900 . ?
C26 H26A 0.9900 . ?
C27 C28 1.516(2) . ?
C27 H27 0.9900 . ?
C27 H27A 0.9900 . ?
C28 C29 1.523(2) . ?
C28 H28 0.9900 . ?
C28 H28A 0.9900 . ?
C29 C30 1.514(2) . ?
C29 H29 0.9900 . ?
C29 H29A 0.9900 . ?
C30 H30 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C31 C32 1.531(2) . ?
C31 H31 0.9900 . ?
C31 H31A 0.9900 . ?
C32 C33 1.521(2) . ?
C32 H32 0.9900 . ?
C32 H32A 0.9900 . ?
C33 C34 1.534(3) . ?
C33 H33 0.9900 . ?
C33 H33A 0.9900 . ?
C34 C35 1.514(3) . ?
C34 H34 0.9900 . ?
C34 H34A 0.9900 . ?
C35 H35 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 C44 1.400(2) . ?
C36 C37 1.405(2) . ?
C36 H36 1.009(19) . ?
C37 C45 1.394(2) . ?
C37 C38 1.488(2) . ?
C38 C39 1.385(2) . ?
C38 C43 1.412(2) . ?
C39 C40 1.403(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.379(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.405(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.384(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.486(2) . ?
C44 C48 1.399(2) . ?
C45 C47 1.423(2) . ?
C45 C46 1.425(2) . ?
C48 C50 1.419(2) . ?
C48 C49 1.430(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N5 C16 120.56(14) . . ?
C20 N5 C26 120.39(13) . . ?
C16 N5 C26 119.05(13) . . ?
C21 N6 C25 120.15(14) . . ?
C21 N6 C31 118.75(13) . . ?
C25 N6 C31 121.10(13) . . ?
C2 C1 C9 110.82(14) . . ?
C2 C1 H1 125.4(10) . . ?
C9 C1 H1 123.8(10) . . ?
C10 C2 C1 125.49(15) . . ?
C10 C2 C3 127.17(15) . . ?
C1 C2 C3 107.30(14) . . ?
C4 C3 C8 120.87(16) . . ?
C4 C3 C2 131.74(16) . . ?
C8 C3 C2 107.38(13) . . ?
C3 C4 C5 118.21(17) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.89(16) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.13(17) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.08(17) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C3 120.76(15) . . ?
C7 C8 C9 131.70(16) . . ?
C3 C8 C9 107.54(13) . . ?
C13 C9 C1 125.57(14) . . ?
C13 C9 C8 127.51(14) . . ?
C1 C9 C8 106.91(13) . . ?
C2 C10 C12 124.72(16) . . ?
C2 C10 C11 117.77(14) . . ?
C12 C10 C11 117.50(15) . . ?
N1 C11 C10 176.86(18) . . ?
N2 C12 C10 178.9(2) . . ?
C9 C13 C15 124.64(14) . . ?
C9 C13 C14 118.04(14) . . ?
C15 C13 C14 117.32(14) . . ?
N3 C14 C13 175.75(17) . . ?
N4 C15 C13 178.3(2) . . ?
N5 C16 C17 120.47(15) . . ?
N5 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 120.63(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 117.11(14) . . ?
C17 C18 C23 121.21(14) . . ?
C19 C18 C23 121.68(14) . . ?
C20 C19 C18 120.03(14) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N5 C20 C19 121.17(14) . . ?
N5 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
N6 C21 C22 121.05(14) . . ?
N6 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 120.18(14) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 117.38(14) . . ?
C24 C23 C18 121.83(14) . . ?
C22 C23 C18 120.79(14) . . ?
C25 C24 C23 120.35(15) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
N6 C25 C24 120.89(15) . . ?
N6 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N5 C26 C27 111.27(13) . . ?
N5 C26 H26 109.4 . . ?
C27 C26 H26 109.4 . . ?
N5 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
H26 C26 H26A 108.0 . . ?
C28 C27 C26 113.96(14) . . ?
C28 C27 H27 108.8 . . ?
C26 C27 H27 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
H27 C27 H27A 107.7 . . ?
C27 C28 C29 113.55(14) . . ?
C27 C28 H28 108.9 . . ?
C29 C28 H28 108.9 . . ?
C27 C28 H28A 108.9 . . ?
C29 C28 H28A 108.9 . . ?
H28 C28 H28A 107.7 . . ?
C30 C29 C28 111.70(14) . . ?
C30 C29 H29 109.3 . . ?
C28 C29 H29 109.3 . . ?
C30 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
H29 C29 H29A 107.9 . . ?
C29 C30 H30 109.5 . . ?
C29 C30 H30A 109.5 . . ?
H30 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N6 C31 C32 111.32(13) . . ?
N6 C31 H31 109.4 . . ?
C32 C31 H31 109.4 . . ?
N6 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
H31 C31 H31A 108.0 . . ?
C33 C32 C31 114.04(14) . . ?
C33 C32 H32 108.7 . . ?
C31 C32 H32 108.7 . . ?
C33 C32 H32A 108.7 . . ?
C31 C32 H32A 108.7 . . ?
H32 C32 H32A 107.6 . . ?
C32 C33 C34 113.84(15) . . ?
C32 C33 H33 108.8 . . ?
C34 C33 H33 108.8 . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
H33 C33 H33A 107.7 . . ?
C35 C34 C33 111.79(16) . . ?
C35 C34 H34 109.3 . . ?
C33 C34 H34 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34A 109.3 . . ?
H34 C34 H34A 107.9 . . ?
C34 C35 H35 109.5 . . ?
C34 C35 H35A 109.5 . . ?
H35 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C44 C36 C37 110.66(14) . . ?
C44 C36 H36 124.0(10) . . ?
C37 C36 H36 125.3(10) . . ?
C45 C37 C36 125.32(14) . . ?
C45 C37 C38 127.70(14) . . ?
C36 C37 C38 106.96(13) . . ?
C39 C38 C43 120.78(15) . . ?
C39 C38 C37 131.57(15) . . ?
C43 C38 C37 107.66(13) . . ?
C38 C39 C40 118.08(17) . . ?
C38 C39 H39 121.0 . . ?
C40 C39 H39 121.0 . . ?
C41 C40 C39 121.39(16) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C42 120.54(16) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C43 C42 C41 118.57(17) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C42 C43 C38 120.59(15) . . ?
C42 C43 C44 132.06(16) . . ?
C38 C43 C44 107.35(13) . . ?
C48 C44 C36 125.46(15) . . ?
C48 C44 C43 127.20(15) . . ?
C36 C44 C43 107.34(14) . . ?
C37 C45 C47 124.70(14) . . ?
C37 C45 C46 117.63(14) . . ?
C47 C45 C46 117.65(14) . . ?
N7 C46 C45 175.10(18) . . ?
N8 C47 C45 178.78(19) . . ?
C44 C48 C50 123.28(16) . . ?
C44 C48 C49 117.97(15) . . ?
C50 C48 C49 118.74(15) . . ?
N9 C49 C48 176.32(19) . . ?
N10 C50 C48 178.5(2) . . ?

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
C9 C1 C2 C10 -177.03(15) . . . . ?
C9 C1 C2 C3 0.72(18) . . . . ?
C10 C2 C3 C4 -3.1(3) . . . . ?
C1 C2 C3 C4 179.24(17) . . . . ?
C10 C2 C3 C8 175.71(15) . . . . ?
C1 C2 C3 C8 -1.99(17) . . . . ?
C8 C3 C4 C5 -2.5(2) . . . . ?
C2 C3 C4 C5 176.18(16) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C6 C7 C8 C3 0.2(2) . . . . ?
C6 C7 C8 C9 -178.81(16) . . . . ?
C4 C3 C8 C7 2.1(2) . . . . ?
C2 C3 C8 C7 -176.78(14) . . . . ?
C4 C3 C8 C9 -178.65(14) . . . . ?
C2 C3 C8 C9 2.42(17) . . . . ?
C2 C1 C9 C13 -178.35(15) . . . . ?
C2 C1 C9 C8 0.76(18) . . . . ?
C7 C8 C9 C13 -3.8(3) . . . . ?
C3 C8 C9 C13 177.07(15) . . . . ?
C7 C8 C9 C1 177.07(17) . . . . ?
C3 C8 C9 C1 -2.02(17) . . . . ?
C1 C2 C10 C12 179.87(16) . . . . ?
C3 C2 C10 C12 2.6(3) . . . . ?
C1 C2 C10 C11 1.3(2) . . . . ?
C3 C2 C10 C11 -176.00(15) . . . . ?
C1 C9 C13 C15 -178.47(16) . . . . ?
C8 C9 C13 C15 2.6(3) . . . . ?
C1 C9 C13 C14 2.5(2) . . . . ?
C8 C9 C13 C14 -176.44(15) . . . . ?
C20 N5 C16 C17 -1.4(2) . . . . ?
C26 N5 C16 C17 178.93(15) . . . . ?
N5 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 1.7(2) . . . . ?
C16 C17 C18 C23 -177.33(15) . . . . ?
C17 C18 C19 C20 -2.1(2) . . . . ?
C23 C18 C19 C20 176.98(14) . . . . ?
C16 N5 C20 C19 1.1(2) . . . . ?
C26 N5 C20 C19 -179.31(14) . . . . ?
C18 C19 C20 N5 0.7(2) . . . . ?
C25 N6 C21 C22 0.1(2) . . . . ?
C31 N6 C21 C22 179.34(14) . . . . ?
N6 C21 C22 C23 -0.5(2) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C21 C22 C23 C18 -179.52(14) . . . . ?
C17 C18 C23 C24 178.03(14) . . . . ?
C19 C18 C23 C24 -1.0(2) . . . . ?
C17 C18 C23 C22 -1.9(2) . . . . ?
C19 C18 C23 C22 179.12(14) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
C18 C23 C24 C25 179.88(15) . . . . ?
C21 N6 C25 C24 0.3(2) . . . . ?
C31 N6 C25 C24 -178.95(15) . . . . ?
C23 C24 C25 N6 -0.2(3) . . . . ?
C20 N5 C26 C27 -101.04(17) . . . . ?
C16 N5 C26 C27 78.60(18) . . . . ?
N5 C26 C27 C28 66.87(18) . . . . ?
C26 C27 C28 C29 -170.91(14) . . . . ?
C27 C28 C29 C30 -176.76(14) . . . . ?
C21 N6 C31 C32 63.67(19) . . . . ?
C25 N6 C31 C32 -117.10(17) . . . . ?
N6 C31 C32 C33 65.51(18) . . . . ?
C31 C32 C33 C34 -164.74(14) . . . . ?
C32 C33 C34 C35 177.20(15) . . . . ?
C44 C36 C37 C45 178.09(15) . . . . ?
C44 C36 C37 C38 -0.47(18) . . . . ?
C45 C37 C38 C39 2.8(3) . . . . ?
C36 C37 C38 C39 -178.73(17) . . . . ?
C45 C37 C38 C43 -176.97(15) . . . . ?
C36 C37 C38 C43 1.54(17) . . . . ?
C43 C38 C39 C40 -0.2(2) . . . . ?
C37 C38 C39 C40 -179.88(16) . . . . ?
C38 C39 C40 C41 2.0(3) . . . . ?
C39 C40 C41 C42 -2.0(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C38 1.7(2) . . . . ?
C41 C42 C43 C44 -178.24(16) . . . . ?
C39 C38 C43 C42 -1.6(2) . . . . ?
C37 C38 C43 C42 178.12(14) . . . . ?
C39 C38 C43 C44 178.28(14) . . . . ?
C37 C38 C43 C44 -1.96(17) . . . . ?
C37 C36 C44 C48 178.79(15) . . . . ?
C37 C36 C44 C43 -0.73(18) . . . . ?
C42 C43 C44 C48 2.1(3) . . . . ?
C38 C43 C44 C48 -177.81(15) . . . . ?
C42 C43 C44 C36 -178.40(17) . . . . ?
C38 C43 C44 C36 1.69(17) . . . . ?
C36 C37 C45 C47 178.09(16) . . . . ?
C38 C37 C45 C47 -3.7(3) . . . . ?
C36 C37 C45 C46 -3.7(2) . . . . ?
C38 C37 C45 C46 174.52(15) . . . . ?
C36 C44 C48 C50 -179.23(16) . . . . ?
C43 C44 C48 C50 0.2(3) . . . . ?
C36 C44 C48 C49 1.3(2) . . . . ?
C43 C44 C48 C49 -179.28(15) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_20190316_BV_-123
_database_code_depnum_ccdc_archive 'CCDC 2268736'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 N2, 2(C15 H5 N4)'
_chemical_formula_sum            'C48 H36 N10'
_chemical_formula_weight         752.87

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.8550(2)
_cell_length_b                   18.6894(3)
_cell_length_c                   10.1304(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.219(2)
_cell_angle_gamma                90
_cell_volume                     1963.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    19567
_cell_measurement_theta_min      2.1230
_cell_measurement_theta_max      30.5470

_exptl_crystal_description       Platelet
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.90179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.865
_oxdiff_exptl_absorpt_empirical_full_max 1.144
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            25997
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4450
_reflns_number_gt                4137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0852P)²+0.3892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4450
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.55816(11) 0.74508(6) 0.39608(13) 0.0398(3) Uani 1 1 d . . . . .
N2 N -0.14895(11) 0.67998(6) 0.49082(13) 0.0417(3) Uani 1 1 d . . . . .
N3 N -0.90029(10) 0.49591(6) 0.21694(12) 0.0388(3) Uani 1 1 d . . . . .
N4 N -0.67950(10) 0.29841(5) 0.25469(11) 0.0335(2) Uani 1 1 d . . . . .
N5 N 0.21658(8) 0.10205(5) 0.38145(9) 0.0236(2) Uani 1 1 d . . . . .
C1 C -0.56083(9) 0.55270(5) 0.32915(10) 0.0218(2) Uani 1 1 d . . . . .
H1 H -0.6357(13) 0.5837(7) 0.3193(13) 0.026 Uiso 1 1 d . U . . .
C2 C -0.43145(10) 0.57614(5) 0.37415(10) 0.0211(2) Uani 1 1 d . . . . .
C3 C -0.34837(10) 0.51225(5) 0.38005(10) 0.0221(2) Uani 1 1 d . . . . .
C4 C -0.21569(10) 0.50404(6) 0.41573(12) 0.0290(2) Uani 1 1 d . . . . .
H4 H -0.159840 0.543692 0.446698 0.035 Uiso 1 1 calc R U . . .
C5 C -0.16586(11) 0.43578(7) 0.40501(14) 0.0361(3) Uani 1 1 d . . . . .
H5 H -0.075145 0.429219 0.428629 0.043 Uiso 1 1 calc R U . . .
C6 C -0.24666(12) 0.37799(7) 0.36066(14) 0.0362(3) Uani 1 1 d . . . . .
H6 H -0.210772 0.332435 0.352495 0.043 Uiso 1 1 calc R U . . .
C7 C -0.38110(11) 0.38547(6) 0.32741(12) 0.0284(2) Uani 1 1 d . . . . .
H7 H -0.436449 0.345442 0.298351 0.034 Uiso 1 1 calc R U . . .
C8 C -0.43091(9) 0.45272(5) 0.33807(10) 0.0216(2) Uani 1 1 d . . . . .
C9 C -0.56587(9) 0.47865(5) 0.30879(9) 0.0205(2) Uani 1 1 d . . . . .
C10 C -0.38999(10) 0.64609(5) 0.40604(10) 0.0240(2) Uani 1 1 d . . . . .
C11 C -0.48225(11) 0.70165(6) 0.39952(11) 0.0279(2) Uani 1 1 d . . . . .
C12 C -0.25686(11) 0.66559(6) 0.45275(12) 0.0288(2) Uani 1 1 d . . . . .
C13 C -0.67746(10) 0.43612(5) 0.26907(10) 0.0222(2) Uani 1 1 d . . . . .
C14 C -0.80083(10) 0.46872(6) 0.24118(11) 0.0260(2) Uani 1 1 d . . . . .
C15 C -0.67677(10) 0.36003(6) 0.26041(10) 0.0250(2) Uani 1 1 d . . . . .
C16 C 0.20876(10) 0.03059(6) 0.39878(11) 0.0269(2) Uani 1 1 d . . . . .
H16 H 0.126579 0.008328 0.378416 0.032 Uiso 1 1 calc R U . . .
C17 C 0.31856(10) -0.01010(6) 0.44558(11) 0.0256(2) Uani 1 1 d . . . . .
H17 H 0.311749 -0.060220 0.457384 0.031 Uiso 1 1 calc R U . . .
C18 C 0.44017(9) 0.02183(5) 0.47588(9) 0.0198(2) Uani 1 1 d . . . . .
C19 C 0.44451(10) 0.09588(6) 0.45926(11) 0.0245(2) Uani 1 1 d . . . . .
H19 H 0.525436 0.119620 0.481044 0.029 Uiso 1 1 calc R U . . .
C20 C 0.33196(10) 0.13482(6) 0.41139(11) 0.0255(2) Uani 1 1 d . . . . .
H20 H 0.336007 0.185093 0.399506 0.031 Uiso 1 1 calc R U . . .
C21 C 0.09470(10) 0.14412(6) 0.33309(12) 0.0290(2) Uani 1 1 d . . . . .
H21 H 0.034344 0.119894 0.252817 0.035 Uiso 1 1 calc R U . . .
H21A H 0.113600 0.192269 0.303216 0.035 Uiso 1 1 calc R U . . .
C22 C 0.03260(11) 0.15119(6) 0.44857(13) 0.0299(2) Uani 1 1 d . . . . .
H22 H 0.089646 0.179590 0.524947 0.036 Uiso 1 1 calc R U . . .
H22A H 0.022495 0.103085 0.484949 0.036 Uiso 1 1 calc R U . . .
C23 C -0.09851(12) 0.18723(8) 0.39841(17) 0.0448(3) Uani 1 1 d . . . . .
H23 H -0.157998 0.156778 0.327694 0.054 Uiso 1 1 calc R U . . .
H23A H -0.089719 0.233627 0.354919 0.054 Uiso 1 1 calc R U . . .
C24 C -0.15490(19) 0.19972(10) 0.5180(2) 0.0702(6) Uani 1 1 d . . . . .
H24 H -0.153857 0.154752 0.568068 0.105 Uiso 1 1 calc R U . . .
H24A H -0.243895 0.216821 0.481621 0.105 Uiso 1 1 calc R U . . .
H24B H -0.103104 0.235600 0.580967 0.105 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.1498(16) . ?
N2 C12 1.1514(16) . ?
N3 C14 1.1521(15) . ?
N4 C15 1.1530(15) . ?
N5 C20 1.3456(13) . ?
N5 C16 1.3529(14) . ?
N5 C21 1.4916(13) . ?
C1 C9 1.3980(14) . ?
C1 C2 1.4118(14) . ?
C1 H1 0.978(14) . ?
C2 C10 1.3892(14) . ?
C2 C3 1.4869(13) . ?
C3 C4 1.3857(14) . ?
C3 C8 1.4128(14) . ?
C4 C5 1.4025(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3799(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4041(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3850(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4872(13) . ?
C9 C13 1.4044(14) . ?
C10 C12 1.4284(15) . ?
C10 C11 1.4306(15) . ?
C13 C14 1.4214(14) . ?
C13 C15 1.4250(14) . ?
C16 C17 1.3745(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3974(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.3966(14) . ?
C18 C18 1.4886(18) 3_656 ?
C19 C20 1.3808(14) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.5191(16) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.5196(16) . ?
C22 H22 0.9900 . ?
C22 H22A 0.9900 . ?
C23 C24 1.528(2) . ?
C23 H23 0.9900 . ?
C23 H23A 0.9900 . ?
C24 H24 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 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
C20 N5 C16 120.66(9) . . ?
C20 N5 C21 120.66(9) . . ?
C16 N5 C21 118.64(9) . . ?
C9 C1 C2 110.28(9) . . ?
C9 C1 H1 125.2(8) . . ?
C2 C1 H1 124.5(8) . . ?
C10 C2 C1 126.15(9) . . ?
C10 C2 C3 126.55(9) . . ?
C1 C2 C3 107.30(8) . . ?
C4 C3 C8 120.59(9) . . ?
C4 C3 C2 132.11(10) . . ?
C8 C3 C2 107.29(9) . . ?
C3 C4 C5 118.38(10) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 120.98(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.03(11) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 118.27(10) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 120.71(9) . . ?
C7 C8 C9 131.64(10) . . ?
C3 C8 C9 107.63(9) . . ?
C1 C9 C13 126.54(9) . . ?
C1 C9 C8 107.46(9) . . ?
C13 C9 C8 126.01(9) . . ?
C2 C10 C12 122.93(10) . . ?
C2 C10 C11 119.88(9) . . ?
C12 C10 C11 117.12(9) . . ?
N1 C11 C10 178.12(12) . . ?
N2 C12 C10 178.72(13) . . ?
C9 C13 C14 119.76(9) . . ?
C9 C13 C15 124.24(9) . . ?
C14 C13 C15 115.93(9) . . ?
N3 C14 C13 178.81(12) . . ?
N4 C15 C13 177.94(12) . . ?
N5 C16 C17 120.64(9) . . ?
N5 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.38(10) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 117.39(9) . . ?
C19 C18 C18 121.70(11) . 3_656 ?
C17 C18 C18 120.92(11) . 3_656 ?
C20 C19 C18 120.44(9) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 C20 C19 120.47(10) . . ?
N5 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N5 C21 C22 110.22(9) . . ?
N5 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
N5 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
H21 C21 H21A 108.1 . . ?
C21 C22 C23 111.48(10) . . ?
C21 C22 H22 109.3 . . ?
C23 C22 H22 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
H22 C22 H22A 108.0 . . ?
C22 C23 C24 110.97(14) . . ?
C22 C23 H23 109.4 . . ?
C24 C23 H23 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
H23 C23 H23A 108.0 . . ?
C23 C24 H24 109.5 . . ?
C23 C24 H24A 109.5 . . ?
H24 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24 C24 H24B 109.5 . . ?
H24A C24 H24B 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
C9 C1 C2 C10 -179.19(9) . . . . ?
C9 C1 C2 C3 1.18(11) . . . . ?
C10 C2 C3 C4 -0.23(18) . . . . ?
C1 C2 C3 C4 179.40(11) . . . . ?
C10 C2 C3 C8 -179.51(10) . . . . ?
C1 C2 C3 C8 0.12(11) . . . . ?
C8 C3 C4 C5 1.94(16) . . . . ?
C2 C3 C4 C5 -177.27(11) . . . . ?
C3 C4 C5 C6 -0.29(19) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
C5 C6 C7 C8 1.04(18) . . . . ?
C6 C7 C8 C3 0.61(16) . . . . ?
C6 C7 C8 C9 178.74(11) . . . . ?
C4 C3 C8 C7 -2.13(15) . . . . ?
C2 C3 C8 C7 177.26(9) . . . . ?
C4 C3 C8 C9 179.34(9) . . . . ?
C2 C3 C8 C9 -1.28(10) . . . . ?
C2 C1 C9 C13 177.57(9) . . . . ?
C2 C1 C9 C8 -1.96(11) . . . . ?
C7 C8 C9 C1 -176.31(11) . . . . ?
C3 C8 C9 C1 2.01(11) . . . . ?
C7 C8 C9 C13 4.16(17) . . . . ?
C3 C8 C9 C13 -177.53(9) . . . . ?
C1 C2 C10 C12 179.19(10) . . . . ?
C3 C2 C10 C12 -1.24(16) . . . . ?
C1 C2 C10 C11 2.47(16) . . . . ?
C3 C2 C10 C11 -177.96(9) . . . . ?
C1 C9 C13 C14 2.08(15) . . . . ?
C8 C9 C13 C14 -178.47(9) . . . . ?
C1 C9 C13 C15 -174.76(9) . . . . ?
C8 C9 C13 C15 4.69(16) . . . . ?
C20 N5 C16 C17 -0.88(16) . . . . ?
C21 N5 C16 C17 -178.81(10) . . . . ?
N5 C16 C17 C18 -0.05(16) . . . . ?
C16 C17 C18 C19 1.24(15) . . . . ?
C16 C17 C18 C18 -178.85(11) . . . 3_656 ?
C17 C18 C19 C20 -1.55(15) . . . . ?
C18 C18 C19 C20 178.54(11) 3_656 . . . ?
C16 N5 C20 C19 0.56(15) . . . . ?
C21 N5 C20 C19 178.45(9) . . . . ?
C18 C19 C20 N5 0.68(16) . . . . ?
C20 N5 C21 C22 -104.80(11) . . . . ?
C16 N5 C21 C22 73.13(12) . . . . ?
N5 C21 C22 C23 -174.22(10) . . . . ?
C21 C22 C23 C24 -175.22(12) . . . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_20190318_HxV_-123
_database_code_depnum_ccdc_archive 'CCDC 2268738'
loop_
_audit_author_name
_audit_author_address
'Erika Saito'
;Yamagata University
Japan
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H34 N2, 2(C15 H5 N4)'
_chemical_formula_sum            'C52 H44 N10'
_chemical_formula_weight         808.97

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   8.25330(10)
_cell_length_b                   16.1442(3)
_cell_length_c                   17.4065(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.275(2)
_cell_angle_gamma                90
_cell_volume                     2175.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    19557
_cell_measurement_theta_min      1.8260
_cell_measurement_theta_max      30.5970

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.91708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.901
_oxdiff_exptl_absorpt_empirical_full_max 1.075
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            29170
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4952
_reflns_number_gt                4486
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.4450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4952
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.95053(12) 0.55782(6) 0.40171(6) 0.0395(2) Uani 1 1 d . . . . .
N2 N 1.03203(13) 0.70491(8) 0.61878(7) 0.0501(3) Uani 1 1 d . . . . .
N3 N 0.24560(13) 0.57159(7) 0.18458(6) 0.0415(2) Uani 1 1 d . . . . .
N4 N -0.08858(14) 0.73227(9) 0.27434(7) 0.0544(3) Uani 1 1 d . . . . .
N5 N 0.52906(10) 0.61529(5) 0.67604(5) 0.02586(18) Uani 1 1 d . . . . .
C1 C 0.52449(12) 0.65320(6) 0.37221(6) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.5550(16) 0.6198(7) 0.3328(8) 0.032 Uiso 1 1 d . U . . .
C2 C 0.64265(12) 0.67892(6) 0.44765(6) 0.0255(2) Uani 1 1 d . . . . .
C3 C 0.54621(12) 0.72913(6) 0.48932(6) 0.0262(2) Uani 1 1 d . . . . .
C4 C 0.59785(14) 0.76796(6) 0.56488(6) 0.0303(2) Uani 1 1 d . . . . .
H4 H 0.715293 0.766970 0.599966 0.036 Uiso 1 1 calc R U . . .
C5 C 0.47201(15) 0.80893(6) 0.58841(7) 0.0335(2) Uani 1 1 d . . . . .
H5 H 0.505258 0.836395 0.639818 0.040 Uiso 1 1 calc R U . . .
C6 C 0.30047(15) 0.80985(7) 0.53780(7) 0.0348(2) Uani 1 1 d . . . . .
H6 H 0.217533 0.837415 0.555228 0.042 Uiso 1 1 calc R U . . .
C7 C 0.24738(14) 0.77063(6) 0.46109(7) 0.0316(2) Uani 1 1 d . . . . .
H7 H 0.129615 0.771309 0.426410 0.038 Uiso 1 1 calc R U . . .
C8 C 0.37108(12) 0.73090(6) 0.43721(6) 0.0265(2) Uani 1 1 d . . . . .
C9 C 0.35766(12) 0.68312(6) 0.36237(6) 0.0261(2) Uani 1 1 d . . . . .
C10 C 0.81815(12) 0.65838(6) 0.47894(6) 0.0290(2) Uani 1 1 d . . . . .
C11 C 0.89097(12) 0.60365(7) 0.43510(6) 0.0308(2) Uani 1 1 d . . . . .
C12 C 0.93369(13) 0.68543(7) 0.55655(7) 0.0352(2) Uani 1 1 d . . . . .
C13 C 0.20954(13) 0.66870(6) 0.29493(6) 0.0292(2) Uani 1 1 d . . . . .
C14 C 0.22335(13) 0.61598(7) 0.23166(6) 0.0313(2) Uani 1 1 d . . . . .
C15 C 0.04445(14) 0.70378(8) 0.28405(7) 0.0368(3) Uani 1 1 d . . . . .
C16 C 0.67335(12) 0.58181(6) 0.66903(6) 0.0275(2) Uani 1 1 d . . . . .
H16 H 0.781470 0.590097 0.711432 0.033 Uiso 1 1 calc R U . . .
C17 C 0.66572(12) 0.53576(6) 0.60113(6) 0.0257(2) Uani 1 1 d . . . . .
H17 H 0.768030 0.512099 0.597295 0.031 Uiso 1 1 calc R U . . .
C18 C 0.50684(11) 0.52380(5) 0.53762(5) 0.02256(19) Uani 1 1 d . . . . .
C19 C 0.36074(12) 0.55902(6) 0.54735(6) 0.0273(2) Uani 1 1 d . . . . .
H19 H 0.250853 0.551993 0.505894 0.033 Uiso 1 1 calc R U . . .
C20 C 0.37482(13) 0.60390(6) 0.61666(6) 0.0287(2) Uani 1 1 d . . . . .
H20 H 0.274129 0.627165 0.622636 0.034 Uiso 1 1 calc R U . . .
C21 C 0.54035(14) 0.66638(6) 0.74927(6) 0.0301(2) Uani 1 1 d . . . . .
H21 H 0.442671 0.705935 0.734398 0.036 Uiso 1 1 calc R U . . .
H21A H 0.648852 0.698815 0.766208 0.036 Uiso 1 1 calc R U . . .
C22 C 0.53605(13) 0.61334(6) 0.82093(6) 0.0299(2) Uani 1 1 d . . . . .
H22 H 0.564920 0.648676 0.870346 0.036 Uiso 1 1 calc R U . . .
H22A H 0.626411 0.570173 0.831679 0.036 Uiso 1 1 calc R U . . .
C23 C 0.36281(15) 0.57132(7) 0.80743(7) 0.0357(2) Uani 1 1 d . . . . .
H23 H 0.341927 0.529113 0.763802 0.043 Uiso 1 1 calc R U . . .
H23A H 0.269461 0.613073 0.788713 0.043 Uiso 1 1 calc R U . . .
C24 C 0.35675(14) 0.52991(7) 0.88531(6) 0.0329(2) Uani 1 1 d . . . . .
H24 H 0.446287 0.486187 0.902091 0.039 Uiso 1 1 calc R U . . .
H24A H 0.385159 0.571628 0.929706 0.039 Uiso 1 1 calc R U . . .
C25 C 0.18259(17) 0.49159(9) 0.87556(8) 0.0486(3) Uani 1 1 d . . . . .
H25 H 0.158385 0.446656 0.834411 0.058 Uiso 1 1 calc R U . . .
H25A H 0.091659 0.534212 0.854576 0.058 Uiso 1 1 calc R U . . .
C26 C 0.17382(17) 0.45650(9) 0.95531(8) 0.0445(3) Uani 1 1 d . . . . .
H26 H 0.263756 0.414363 0.976580 0.067 Uiso 1 1 calc R U . . .
H26A H 0.060163 0.431380 0.945101 0.067 Uiso 1 1 calc R U . . .
H26B H 0.191883 0.501192 0.995519 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.1510(14) . ?
N2 C12 1.1497(15) . ?
N3 C14 1.1503(15) . ?
N4 C15 1.1475(15) . ?
N5 C20 1.3456(13) . ?
N5 C16 1.3513(12) . ?
N5 C21 1.4938(12) . ?
C1 C2 1.4000(14) . ?
C1 C9 1.4124(13) . ?
C1 H1 0.972(13) . ?
C2 C10 1.3993(13) . ?
C2 C3 1.4888(13) . ?
C3 C4 1.3844(14) . ?
C3 C8 1.4157(14) . ?
C4 C5 1.4066(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3843(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4038(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3858(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4847(14) . ?
C9 C13 1.3901(14) . ?
C10 C12 1.4254(15) . ?
C10 C11 1.4291(14) . ?
C13 C15 1.4263(14) . ?
C13 C14 1.4272(15) . ?
C16 C17 1.3790(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.4051(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.3955(13) . ?
C18 C18 1.4887(18) 3_666 ?
C19 C20 1.3772(14) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.5235(14) . ?
C21 H21 0.9900 . ?
C21 H21A 0.9900 . ?
C22 C23 1.5254(15) . ?
C22 H22 0.9900 . ?
C22 H22A 0.9900 . ?
C23 C24 1.5278(14) . ?
C23 H23 0.9900 . ?
C23 H23A 0.9900 . ?
C24 C25 1.5193(16) . ?
C24 H24 0.9900 . ?
C24 H24A 0.9900 . ?
C25 C26 1.5241(17) . ?
C25 H25 0.9900 . ?
C25 H25A 0.9900 . ?
C26 H26 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 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
C20 N5 C16 120.31(8) . . ?
C20 N5 C21 119.58(8) . . ?
C16 N5 C21 120.11(8) . . ?
C2 C1 C9 110.20(9) . . ?
C2 C1 H1 124.1(7) . . ?
C9 C1 H1 125.7(7) . . ?
C10 C2 C1 125.84(9) . . ?
C10 C2 C3 126.54(9) . . ?
C1 C2 C3 107.59(8) . . ?
C4 C3 C8 120.62(9) . . ?
C4 C3 C2 131.99(9) . . ?
C8 C3 C2 107.36(8) . . ?
C3 C4 C5 118.32(10) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 121.02(10) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.92(10) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 118.33(10) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C3 120.79(10) . . ?
C7 C8 C9 131.68(9) . . ?
C3 C8 C9 107.50(8) . . ?
C13 C9 C1 125.47(9) . . ?
C13 C9 C8 127.19(9) . . ?
C1 C9 C8 107.34(8) . . ?
C2 C10 C12 123.96(9) . . ?
C2 C10 C11 120.58(9) . . ?
C12 C10 C11 115.37(9) . . ?
N1 C11 C10 177.89(11) . . ?
N2 C12 C10 177.07(12) . . ?
C9 C13 C15 124.45(10) . . ?
C9 C13 C14 118.00(9) . . ?
C15 C13 C14 117.55(9) . . ?
N3 C14 C13 175.11(11) . . ?
N4 C15 C13 179.16(13) . . ?
N5 C16 C17 120.87(9) . . ?
N5 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 120.09(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 117.30(9) . . ?
C19 C18 C18 120.78(10) . 3_666 ?
C17 C18 C18 121.92(10) . 3_666 ?
C20 C19 C18 120.43(9) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N5 C20 C19 121.00(9) . . ?
N5 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N5 C21 C22 112.09(8) . . ?
N5 C21 H21 109.2 . . ?
C22 C21 H21 109.2 . . ?
N5 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
H21 C21 H21A 107.9 . . ?
C21 C22 C23 114.23(9) . . ?
C21 C22 H22 108.7 . . ?
C23 C22 H22 108.7 . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
H22 C22 H22A 107.6 . . ?
C22 C23 C24 112.03(9) . . ?
C22 C23 H23 109.2 . . ?
C24 C23 H23 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
H23 C23 H23A 107.9 . . ?
C25 C24 C23 113.55(9) . . ?
C25 C24 H24 108.9 . . ?
C23 C24 H24 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
H24 C24 H24A 107.7 . . ?
C24 C25 C26 113.04(10) . . ?
C24 C25 H25 109.0 . . ?
C26 C25 H25 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
H25 C25 H25A 107.8 . . ?
C25 C26 H26 109.5 . . ?
C25 C26 H26A 109.5 . . ?
H26 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26 C26 H26B 109.5 . . ?
H26A C26 H26B 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
C9 C1 C2 C10 177.70(9) . . . . ?
C9 C1 C2 C3 -0.26(10) . . . . ?
C10 C2 C3 C4 0.74(16) . . . . ?
C1 C2 C3 C4 178.68(10) . . . . ?
C10 C2 C3 C8 -177.20(9) . . . . ?
C1 C2 C3 C8 0.73(10) . . . . ?
C8 C3 C4 C5 0.10(14) . . . . ?
C2 C3 C4 C5 -177.62(9) . . . . ?
C3 C4 C5 C6 0.62(15) . . . . ?
C4 C5 C6 C7 -0.68(16) . . . . ?
C5 C6 C7 C8 0.00(15) . . . . ?
C6 C7 C8 C3 0.72(14) . . . . ?
C6 C7 C8 C9 178.60(9) . . . . ?
C4 C3 C8 C7 -0.78(14) . . . . ?
C2 C3 C8 C7 177.45(8) . . . . ?
C4 C3 C8 C9 -179.12(8) . . . . ?
C2 C3 C8 C9 -0.90(10) . . . . ?
C2 C1 C9 C13 -179.48(9) . . . . ?
C2 C1 C9 C8 -0.29(11) . . . . ?
C7 C8 C9 C13 1.83(17) . . . . ?
C3 C8 C9 C13 179.92(9) . . . . ?
C7 C8 C9 C1 -177.34(10) . . . . ?
C3 C8 C9 C1 0.75(10) . . . . ?
C1 C2 C10 C12 -179.43(10) . . . . ?
C3 C2 C10 C12 -1.86(16) . . . . ?
C1 C2 C10 C11 -2.98(15) . . . . ?
C3 C2 C10 C11 174.60(9) . . . . ?
C1 C9 C13 C15 -175.93(10) . . . . ?
C8 C9 C13 C15 5.04(16) . . . . ?
C1 C9 C13 C14 3.34(15) . . . . ?
C8 C9 C13 C14 -175.69(9) . . . . ?
C20 N5 C16 C17 0.23(14) . . . . ?
C21 N5 C16 C17 -178.79(8) . . . . ?
N5 C16 C17 C18 0.67(14) . . . . ?
C16 C17 C18 C19 -0.96(14) . . . . ?
C16 C17 C18 C18 178.58(10) . . . 3_666 ?
C17 C18 C19 C20 0.40(14) . . . . ?
C18 C18 C19 C20 -179.14(10) 3_666 . . . ?
C16 N5 C20 C19 -0.81(14) . . . . ?
C21 N5 C20 C19 178.22(9) . . . . ?
C18 C19 C20 N5 0.47(15) . . . . ?
C20 N5 C21 C22 95.85(11) . . . . ?
C16 N5 C21 C22 -85.11(11) . . . . ?
N5 C21 C22 C23 -68.53(11) . . . . ?
C21 C22 C23 C24 -171.34(9) . . . . ?
C22 C23 C24 C25 176.70(10) . . . . ?
C23 C24 C25 C26 -175.47(11) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037

