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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_TCDP-EtOAc
_database_code_depnum_ccdc_archive 'CCDC 2429929'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 2(C4 H8 O2)'
_chemical_formula_sum            'C38 H38 N10 O4'
_chemical_formula_weight         698.78
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   26.3360(19)
_cell_length_b                   9.3587(5)
_cell_length_c                   15.4039(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3796.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      28.3300
_cell_measurement_theta_min      2.9820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16645
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         2.980
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   2.00   0.50    3.40    --   21.12  19.00 -90.00   52
  2  ω     69.00 109.00   0.50    3.40    --   21.12  -9.00-127.00   80
  3  ω     68.00  94.00   0.50    3.40    --   21.12 153.00 -44.00   52
  4  ω    -72.00  11.00   0.50    3.40    --   21.12  -9.00-127.00  166
  5  ω     16.00  86.00   0.50    3.40    --   21.12-128.00 167.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0111909000
_diffrn_orient_matrix_UB_12      -0.0416610000
_diffrn_orient_matrix_UB_13      -0.0071592000
_diffrn_orient_matrix_UB_21      0.0242902000
_diffrn_orient_matrix_UB_22      -0.0195181000
_diffrn_orient_matrix_UB_23      0.0062670000
_diffrn_orient_matrix_UB_31      -0.0030770000
_diffrn_orient_matrix_UB_32      -0.0022777000
_diffrn_orient_matrix_UB_33      0.0751993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    0.694
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                4575
_reflns_number_total             7049
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7049
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.5017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1392
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C50(H50A,H50B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C28(H28), C26(H26), C17(H17)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C46(H46A,H46B,H46C), C52(H52A,
 H52B,H52C), C45(H45A,H45B,H45C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N13 N 0.38811(13) 0.4377(3) 0.3945(2) 0.0260(7) Uani 1 1 d . . . . .
N1 N 0.41880(13) 0.6606(3) 0.4336(2) 0.0255(8) Uani 1 1 d . . . . .
N6 N 0.35286(13) 0.9604(3) 0.5356(2) 0.0281(8) Uani 1 1 d . . . . .
N41 N 0.32167(13) 0.7391(3) 0.4932(2) 0.0255(7) Uani 1 1 d . . . . .
N3 N 0.45045(14) 0.8799(3) 0.4786(2) 0.0281(8) Uani 1 1 d . . . . .
O41 O 0.31609(14) 0.6091(4) 0.2483(2) 0.0522(9) Uani 1 1 d . . . . .
N10 N 0.29003(13) 0.5203(3) 0.4483(2) 0.0282(8) Uani 1 1 d . . . . .
N34 N 0.36578(15) 0.0918(4) 0.3322(3) 0.0396(10) Uani 1 1 d . . . . .
O43 O 0.28646(17) 0.6886(4) 0.1204(3) 0.0676(11) Uani 1 1 d . . . . .
N36 N 0.22023(17) 0.2301(4) 0.3919(3) 0.0472(11) Uani 1 1 d . . . . .
N38 N 0.37584(16) 1.3009(4) 0.6053(3) 0.0452(10) Uani 1 1 d . . . . .
N40 N 0.51965(17) 1.1727(4) 0.5372(3) 0.0478(11) Uani 1 1 d . . . . .
C12 C 0.34755(16) 0.3492(4) 0.3875(3) 0.0260(9) Uani 1 1 d . . . . .
O49 O 0.44756(18) 0.9323(5) 0.8198(3) 0.0768(13) Uani 1 1 d . . . . .
C9 C 0.32951(16) 0.6053(4) 0.4557(3) 0.0236(9) Uani 1 1 d . . . . .
C2 C 0.41121(16) 0.7940(4) 0.4716(2) 0.0255(9) Uani 1 1 d . . . . .
C14 C 0.37902(16) 0.5649(4) 0.4271(3) 0.0249(9) Uani 1 1 d . . . . .
C33 C 0.35746(17) 0.2065(5) 0.3555(3) 0.0295(10) Uani 1 1 d . . . . .
C7 C 0.36152(16) 0.8341(4) 0.5010(3) 0.0254(9) Uani 1 1 d . . . . .
C29 C 0.23699(16) 0.8397(4) 0.4732(3) 0.0274(9) Uani 1 1 d . . . . .
C19 C 0.52825(17) 0.6098(5) 0.2861(3) 0.0333(10) Uani 1 1 d . . . . .
H19 H 0.537818 0.631995 0.228242 0.040 Uiso 1 1 calc R U . . .
C20 C 0.48139(17) 0.6557(4) 0.3169(3) 0.0295(10) Uani 1 1 d . . . . .
C24 C 0.27184(16) 0.7728(4) 0.5271(3) 0.0259(9) Uani 1 1 d . . . . .
C15 C 0.46883(16) 0.6214(4) 0.4023(3) 0.0261(9) Uani 1 1 d . . . . .
C16 C 0.50099(16) 0.5467(4) 0.4574(3) 0.0265(9) Uani 1 1 d . . . . .
C28 C 0.18866(17) 0.8633(4) 0.5072(3) 0.0319(10) Uani 1 1 d . . . . .
H28 H 0.164181 0.910945 0.472355 0.038 Uiso 1 1 calc R U . . .
C11 C 0.29963(17) 0.3904(4) 0.4127(3) 0.0288(10) Uani 1 1 d . . . . .
C39 C 0.48498(18) 1.1010(4) 0.5268(3) 0.0332(10) Uani 1 1 d . . . . .
C37 C 0.38366(17) 1.1896(5) 0.5791(3) 0.0320(10) Uani 1 1 d . . . . .
C18 C 0.56133(17) 0.5323(4) 0.3379(3) 0.0329(10) Uani 1 1 d . . . . .
O47 O 0.43108(19) 0.8432(5) 0.6889(3) 0.0821(14) Uani 1 1 d . . . . .
C5 C 0.39343(17) 1.0485(4) 0.5424(3) 0.0269(9) Uani 1 1 d . . . . .
C25 C 0.26049(17) 0.7297(4) 0.6116(3) 0.0309(10) Uani 1 1 d . . . . .
C4 C 0.44129(17) 1.0085(4) 0.5154(3) 0.0294(9) Uani 1 1 d . . . . .
C27 C 0.17500(17) 0.8197(4) 0.5899(3) 0.0334(10) Uani 1 1 d . . . . .
C35 C 0.25569(18) 0.2982(5) 0.4024(3) 0.0343(10) Uani 1 1 d . . . . .
C26 C 0.21162(17) 0.7544(4) 0.6414(3) 0.0341(10) Uani 1 1 d . . . . .
H26 H 0.202900 0.725963 0.698725 0.041 Uiso 1 1 calc R U . . .
C21 C 0.48606(18) 0.5184(5) 0.5504(3) 0.0348(11) Uani 1 1 d . . . . .
H21A H 0.480075 0.609423 0.580188 0.052 Uiso 1 1 calc R U . . .
H21B H 0.513451 0.466529 0.579783 0.052 Uiso 1 1 calc R U . . .
H21C H 0.454975 0.460901 0.551738 0.052 Uiso 1 1 calc R U . . .
C17 C 0.54736(17) 0.5015(4) 0.4230(3) 0.0323(10) Uani 1 1 d . . . . .
H17 H 0.569944 0.448325 0.458608 0.039 Uiso 1 1 calc R U . . .
C31 C 0.25111(19) 0.8812(5) 0.3824(3) 0.0389(11) Uani 1 1 d . . . . .
H31A H 0.278756 0.951275 0.384040 0.058 Uiso 1 1 calc R U . . .
H31B H 0.221565 0.923283 0.353327 0.058 Uiso 1 1 calc R U . . .
H31C H 0.262234 0.796318 0.350391 0.058 Uiso 1 1 calc R U . . .
C42 C 0.2811(2) 0.6271(5) 0.1991(4) 0.0512(14) Uani 1 1 d . . . . .
C22 C 0.4452(2) 0.7404(5) 0.2607(3) 0.0467(13) Uani 1 1 d . . . . .
H22A H 0.440984 0.836519 0.284970 0.070 Uiso 1 1 calc R U . . .
H22B H 0.412165 0.692193 0.258955 0.070 Uiso 1 1 calc R U . . .
H22C H 0.458915 0.747514 0.201727 0.070 Uiso 1 1 calc R U . . .
C48 C 0.4590(2) 0.8576(6) 0.7494(4) 0.0564(15) Uani 1 1 d . . . . .
C23 C 0.61118(19) 0.4796(6) 0.3019(4) 0.0493(13) Uani 1 1 d . . . . .
H23A H 0.604738 0.416652 0.252215 0.074 Uiso 1 1 calc R U . . .
H23B H 0.629500 0.426536 0.346899 0.074 Uiso 1 1 calc R U . . .
H23C H 0.631679 0.561284 0.283045 0.074 Uiso 1 1 calc R U . . .
C32 C 0.12158(18) 0.8384(5) 0.6241(4) 0.0481(13) Uani 1 1 d . . . . .
H32A H 0.098914 0.864357 0.576167 0.072 Uiso 1 1 calc R U . . .
H32B H 0.121191 0.914257 0.667947 0.072 Uiso 1 1 calc R U . . .
H32C H 0.110014 0.748703 0.650301 0.072 Uiso 1 1 calc R U . . .
C30 C 0.2996(2) 0.6542(6) 0.6672(3) 0.0484(13) Uani 1 1 d . . . . .
H30A H 0.307773 0.561443 0.641260 0.073 Uiso 1 1 calc R U . . .
H30B H 0.285809 0.639746 0.725640 0.073 Uiso 1 1 calc R U . . .
H30C H 0.330375 0.712636 0.670625 0.073 Uiso 1 1 calc R U . . .
C44 C 0.3374(3) 0.7435(6) 0.0952(4) 0.0689(18) Uani 1 1 d . . . . .
H44A H 0.364143 0.684393 0.122700 0.083 Uiso 1 1 calc R U . . .
H44B H 0.341553 0.737044 0.031461 0.083 Uiso 1 1 calc R U . . .
C46 C 0.2283(2) 0.5814(6) 0.2125(5) 0.0648(16) Uani 1 1 d . . . . .
H46A H 0.225921 0.526332 0.266406 0.097 Uiso 1 1 calc R U . . .
H46B H 0.217499 0.521752 0.163555 0.097 Uiso 1 1 calc R U . . .
H46C H 0.206357 0.665672 0.216328 0.097 Uiso 1 1 calc R U . . .
C52 C 0.5105(2) 0.7949(8) 0.7569(5) 0.086(2) Uani 1 1 d . . . . .
H52A H 0.535687 0.871756 0.761347 0.129 Uiso 1 1 calc R U . . .
H52B H 0.517729 0.736725 0.705487 0.129 Uiso 1 1 calc R U . . .
H52C H 0.512281 0.734780 0.808953 0.129 Uiso 1 1 calc R U . . .
C45 C 0.3428(3) 0.8927(7) 0.1231(5) 0.091(2) Uani 1 1 d . . . . .
H45A H 0.317075 0.951368 0.094187 0.136 Uiso 1 1 calc R U . . .
H45B H 0.376735 0.927455 0.107530 0.136 Uiso 1 1 calc R U . . .
H45C H 0.338324 0.898751 0.186120 0.136 Uiso 1 1 calc R U . . .
C50 C 0.3976(4) 0.9988(10) 0.8204(6) 0.119(3) Uani 1 1 d . . . . .
H50A H 0.394055 1.063623 0.769919 0.143 Uiso 1 1 calc R U . . .
H50B H 0.370864 0.924700 0.816506 0.143 Uiso 1 1 calc R U . . .
C51 C 0.3922(4) 1.0784(10) 0.9001(6) 0.132(4) Uani 1 1 d . . . . .
H51A H 0.419854 1.147977 0.904857 0.198 Uiso 1 1 calc R U . . .
H51B H 0.393487 1.012580 0.949517 0.198 Uiso 1 1 calc R U . . .
H51C H 0.359542 1.128676 0.900018 0.198 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
N13 C12 1.356(5) . ?
N13 C14 1.314(5) . ?
N1 C2 1.393(5) . ?
N1 C14 1.382(5) . ?
N1 C15 1.450(5) . ?
N6 C7 1.316(5) . ?
N6 C5 1.354(5) . ?
N41 C9 1.394(5) . ?
N41 C7 1.381(5) . ?
N41 C24 1.447(5) . ?
N3 C2 1.314(5) . ?
N3 C4 1.352(5) . ?
O41 C42 1.204(6) . ?
N10 C9 1.314(5) . ?
N10 C11 1.357(5) . ?
N34 C33 1.153(5) . ?
O43 C42 1.348(7) . ?
O43 C44 1.488(8) . ?
N36 C35 1.142(6) . ?
N38 C37 1.136(5) . ?
N40 C39 1.144(5) . ?
C12 C33 1.448(6) . ?
C12 C11 1.376(6) . ?
O49 C48 1.324(7) . ?
O49 C50 1.456(9) . ?
C9 C14 1.427(6) . ?
C2 C7 1.435(6) . ?
C29 C24 1.387(6) . ?
C29 C28 1.394(6) . ?
C29 C31 1.499(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(6) . ?
C19 C18 1.386(6) . ?
C20 C15 1.394(6) . ?
C20 C22 1.513(6) . ?
C24 C25 1.395(6) . ?
C15 C16 1.387(6) . ?
C16 C21 1.510(6) . ?
C16 C17 1.397(6) . ?
C28 H28 0.9500 . ?
C28 C27 1.386(6) . ?
C11 C35 1.452(6) . ?
C39 C4 1.451(6) . ?
C37 C5 1.459(6) . ?
C18 C17 1.391(6) . ?
C18 C23 1.508(6) . ?
O47 C48 1.195(7) . ?
C5 C4 1.379(6) . ?
C25 C26 1.386(6) . ?
C25 C30 1.513(6) . ?
C27 C26 1.390(6) . ?
C27 C32 1.512(6) . ?
C26 H26 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C17 H17 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C42 C46 1.470(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C48 C52 1.485(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.468(8) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.443(12) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 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
C14 N13 C12 116.1(4) . . ?
C2 N1 C15 119.8(3) . . ?
C14 N1 C2 120.1(3) . . ?
C14 N1 C15 120.0(3) . . ?
C7 N6 C5 116.2(4) . . ?
C9 N41 C24 118.7(3) . . ?
C7 N41 C9 120.1(3) . . ?
C7 N41 C24 121.2(3) . . ?
C2 N3 C4 116.0(4) . . ?
C9 N10 C11 115.5(4) . . ?
C42 O43 C44 118.4(5) . . ?
N13 C12 C33 116.6(4) . . ?
N13 C12 C11 121.9(3) . . ?
C11 C12 C33 121.4(4) . . ?
C48 O49 C50 115.8(6) . . ?
N41 C9 C14 120.1(3) . . ?
N10 C9 N41 117.6(4) . . ?
N10 C9 C14 122.4(3) . . ?
N1 C2 C7 119.9(4) . . ?
N3 C2 N1 118.0(4) . . ?
N3 C2 C7 122.1(3) . . ?
N13 C14 N1 118.5(4) . . ?
N13 C14 C9 121.6(4) . . ?
N1 C14 C9 119.9(3) . . ?
N34 C33 C12 178.1(5) . . ?
N6 C7 N41 118.8(4) . . ?
N6 C7 C2 121.4(4) . . ?
N41 C7 C2 119.8(3) . . ?
C24 C29 C28 116.8(4) . . ?
C24 C29 C31 120.8(4) . . ?
C28 C29 C31 122.4(4) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.6(4) . . ?
C19 C20 C15 117.5(4) . . ?
C19 C20 C22 121.8(4) . . ?
C15 C20 C22 120.8(4) . . ?
C29 C24 N41 118.8(4) . . ?
C29 C24 C25 123.2(4) . . ?
C25 C24 N41 117.9(4) . . ?
C20 C15 N1 118.1(4) . . ?
C16 C15 N1 118.7(4) . . ?
C16 C15 C20 123.2(4) . . ?
C15 C16 C21 120.6(4) . . ?
C15 C16 C17 117.0(4) . . ?
C17 C16 C21 122.3(4) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 C29 122.4(4) . . ?
C27 C28 H28 118.8 . . ?
N10 C11 C12 122.4(4) . . ?
N10 C11 C35 115.4(4) . . ?
C12 C11 C35 122.2(4) . . ?
N40 C39 C4 178.7(5) . . ?
N38 C37 C5 178.0(5) . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 C23 120.4(4) . . ?
C17 C18 C23 120.6(4) . . ?
N6 C5 C37 116.2(4) . . ?
N6 C5 C4 122.2(3) . . ?
C4 C5 C37 121.6(4) . . ?
C24 C25 C30 121.1(4) . . ?
C26 C25 C24 117.4(4) . . ?
C26 C25 C30 121.4(4) . . ?
N3 C4 C39 116.1(4) . . ?
N3 C4 C5 122.1(4) . . ?
C5 C4 C39 121.8(4) . . ?
C28 C27 C26 118.3(4) . . ?
C28 C27 C32 121.8(4) . . ?
C26 C27 C32 119.9(4) . . ?
N36 C35 C11 177.0(5) . . ?
C25 C26 C27 121.9(4) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.7(4) . . ?
C18 C17 H17 119.1 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C42 O43 123.1(6) . . ?
O41 C42 C46 126.4(5) . . ?
O43 C42 C46 110.4(5) . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O49 C48 C52 110.6(6) . . ?
O47 C48 O49 124.0(6) . . ?
O47 C48 C52 125.3(6) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
C25 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O43 C44 H44A 109.7 . . ?
O43 C44 H44B 109.7 . . ?
H44A C44 H44B 108.2 . . ?
C45 C44 O43 109.8(5) . . ?
C45 C44 H44A 109.7 . . ?
C45 C44 H44B 109.7 . . ?
C42 C46 H46A 109.5 . . ?
C42 C46 H46B 109.5 . . ?
C42 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C52 H52A 109.5 . . ?
C48 C52 H52B 109.5 . . ?
C48 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O49 C50 H50A 110.0 . . ?
O49 C50 H50B 110.0 . . ?
H50A C50 H50B 108.4 . . ?
C51 C50 O49 108.4(8) . . ?
C51 C50 H50A 110.0 . . ?
C51 C50 H50B 110.0 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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
N13 C12 C11 N10 -1.8(6) . . . . ?
N13 C12 C11 C35 177.6(4) . . . . ?
N1 C2 C7 N6 -178.6(4) . . . . ?
N1 C2 C7 N41 1.4(6) . . . . ?
N1 C15 C16 C21 -5.3(5) . . . . ?
N1 C15 C16 C17 175.4(3) . . . . ?
N6 C5 C4 N3 1.6(6) . . . . ?
N6 C5 C4 C39 -177.0(4) . . . . ?
N41 C9 C14 N13 177.5(4) . . . . ?
N41 C9 C14 N1 -2.4(5) . . . . ?
N41 C24 C25 C26 -176.0(4) . . . . ?
N41 C24 C25 C30 1.9(6) . . . . ?
N3 C2 C7 N6 0.8(6) . . . . ?
N3 C2 C7 N41 -179.1(4) . . . . ?
N10 C9 C14 N13 -2.5(6) . . . . ?
N10 C9 C14 N1 177.5(4) . . . . ?
C12 N13 C14 N1 -178.3(3) . . . . ?
C12 N13 C14 C9 1.7(6) . . . . ?
C9 N41 C7 N6 179.1(4) . . . . ?
C9 N41 C7 C2 -0.9(5) . . . . ?
C9 N41 C24 C29 -91.9(4) . . . . ?
C9 N41 C24 C25 85.1(5) . . . . ?
C9 N10 C11 C12 1.1(6) . . . . ?
C9 N10 C11 C35 -178.4(4) . . . . ?
C2 N1 C14 N13 -176.9(4) . . . . ?
C2 N1 C14 C9 3.0(5) . . . . ?
C2 N1 C15 C20 -89.3(4) . . . . ?
C2 N1 C15 C16 93.3(4) . . . . ?
C2 N3 C4 C39 177.3(4) . . . . ?
C2 N3 C4 C5 -1.3(6) . . . . ?
C14 N13 C12 C33 -177.2(4) . . . . ?
C14 N13 C12 C11 0.3(6) . . . . ?
C14 N1 C2 N3 178.1(3) . . . . ?
C14 N1 C2 C7 -2.5(5) . . . . ?
C14 N1 C15 C20 92.0(4) . . . . ?
C14 N1 C15 C16 -85.5(5) . . . . ?
C33 C12 C11 N10 175.6(4) . . . . ?
C33 C12 C11 C35 -5.0(6) . . . . ?
C7 N6 C5 C37 178.8(4) . . . . ?
C7 N6 C5 C4 -0.5(6) . . . . ?
C7 N41 C9 N10 -178.6(4) . . . . ?
C7 N41 C9 C14 1.4(5) . . . . ?
C7 N41 C24 C29 91.1(5) . . . . ?
C7 N41 C24 C25 -91.9(4) . . . . ?
C29 C24 C25 C26 0.8(6) . . . . ?
C29 C24 C25 C30 178.7(4) . . . . ?
C29 C28 C27 C26 2.2(6) . . . . ?
C29 C28 C27 C32 -176.4(4) . . . . ?
C19 C20 C15 N1 -176.2(4) . . . . ?
C19 C20 C15 C16 1.2(6) . . . . ?
C19 C18 C17 C16 -0.1(6) . . . . ?
C20 C19 C18 C17 -0.8(6) . . . . ?
C20 C19 C18 C23 178.0(4) . . . . ?
C20 C15 C16 C21 177.3(4) . . . . ?
C20 C15 C16 C17 -1.9(6) . . . . ?
C24 N41 C9 N10 4.4(5) . . . . ?
C24 N41 C9 C14 -175.6(4) . . . . ?
C24 N41 C7 N6 -3.9(6) . . . . ?
C24 N41 C7 C2 176.1(4) . . . . ?
C24 C29 C28 C27 -1.5(6) . . . . ?
C24 C25 C26 C27 -0.1(6) . . . . ?
C15 N1 C2 N3 -0.7(6) . . . . ?
C15 N1 C2 C7 178.8(4) . . . . ?
C15 N1 C14 N13 1.8(5) . . . . ?
C15 N1 C14 C9 -178.3(4) . . . . ?
C15 C16 C17 C18 1.3(6) . . . . ?
C28 C29 C24 N41 176.7(3) . . . . ?
C28 C29 C24 C25 0.0(6) . . . . ?
C28 C27 C26 C25 -1.3(6) . . . . ?
C11 N10 C9 N41 -179.0(3) . . . . ?
C11 N10 C9 C14 1.0(6) . . . . ?
C37 C5 C4 N3 -177.7(4) . . . . ?
C37 C5 C4 C39 3.8(6) . . . . ?
C18 C19 C20 C15 0.2(6) . . . . ?
C18 C19 C20 C22 179.9(4) . . . . ?
C5 N6 C7 N41 179.4(4) . . . . ?
C5 N6 C7 C2 -0.6(6) . . . . ?
C4 N3 C2 N1 179.6(4) . . . . ?
C4 N3 C2 C7 0.2(6) . . . . ?
C21 C16 C17 C18 -177.9(4) . . . . ?
C31 C29 C24 N41 -2.1(5) . . . . ?
C31 C29 C24 C25 -178.9(4) . . . . ?
C31 C29 C28 C27 177.3(4) . . . . ?
C42 O43 C44 C45 -89.5(6) . . . . ?
C22 C20 C15 N1 4.1(6) . . . . ?
C22 C20 C15 C16 -178.5(4) . . . . ?
C48 O49 C50 C51 -178.4(7) . . . . ?
C23 C18 C17 C16 -178.8(4) . . . . ?
C32 C27 C26 C25 177.3(4) . . . . ?
C30 C25 C26 C27 -178.0(4) . . . . ?
C44 O43 C42 O41 -3.2(8) . . . . ?
C44 O43 C42 C46 179.4(5) . . . . ?
C50 O49 C48 O47 0.0(10) . . . . ?
C50 O49 C48 C52 -179.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_HC-TCDP-RT
_database_code_depnum_ccdc_archive 'CCDC 2431197'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10'
_chemical_formula_sum            'C30 H22 N10'
_chemical_formula_weight         522.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2859(7)
_cell_length_b                   8.7094(9)
_cell_length_c                   11.0860(9)
_cell_angle_alpha                102.350(8)
_cell_angle_beta                 100.096(7)
_cell_angle_gamma                105.742(8)
_cell_volume                     728.67(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1471
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      70.0750
_cell_measurement_theta_min      5.4460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4979
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.527
_diffrn_reflns_theta_min         5.490
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 8.1195
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -6.00   1.00   24.00    --   35.13 -19.00-120.00   28
  2  ω     79.00 104.00   1.00   24.00    --   35.13  37.00 120.00   25
  3  ω      8.00  35.00   1.00   24.00    --   35.13 -57.00 120.00   27
  4  ω     69.00  96.00   1.00   24.00    --   35.13  37.00  30.00   27
  5  ω     56.00  87.00   1.00   24.00    --   35.13-125.00  60.00   31
  6  ω     20.00  45.00   1.00   24.00    --   35.13 -19.00-150.00   25
  7  ω     33.00  61.00   1.00   24.00    --   35.13-125.00-180.00   28
  8  ω      9.00  59.00   1.00   24.00    --   35.13  19.00 -60.00   50
  9  ω     -9.00  18.00   1.00   24.00    --   35.13 -77.00-150.00   27
 10  ω     21.00  66.00   1.00   24.00    --   35.13 -99.00  90.00   45
 11  ω    -29.00  -2.00   1.00   24.00    --   35.13 -19.00  60.00   27
 12  ω     31.00  58.00   1.00   24.00    --   35.13  37.00 120.00   27
 13  ω     11.00  36.00   1.00   24.00    --   35.13 -99.00  60.00   25
 14  ω     11.00  36.00   1.00   24.00    --   35.13 -19.00  60.00   25
 15  ω    -34.00  -4.00   1.00   24.00    --   35.13 -19.00  30.00   30
 16  ω     69.00  94.00   1.00   24.00    --   35.13  57.00  60.00   25
 17  ω    -20.00  46.00   1.00   24.00    --   35.13 -19.00 -90.00   66
 18  ω     24.00  52.00   1.00   24.00    --   35.13 -99.00  30.00   28
 19  ω     20.00  84.00   1.00   24.00    --   35.13  57.00-150.00   64
 20  ω     10.00  43.00   1.00   24.00    --   35.13 -77.00 -30.00   33
 21  ω    -35.00  -9.00   1.00   24.00    --   35.13 -19.00   0.00   26
 22  ω     72.00  97.00   1.00   24.00    --   35.13  57.00  90.00   25
 23  ω     27.00  71.00   1.00   24.00    --   35.13 -99.00-120.00   44
 24  ω     10.00  35.00   1.00   24.00    --   35.13 -99.00 -30.00   25
 25  ω     46.00  71.00   1.00   24.00    --   35.13 -99.00 -30.00   25
 26  ω     41.00  70.00   1.00   24.00    --  107.04 -45.00   0.00   29
 27  ω     54.00 105.00   1.00   24.00    --  107.04 -94.00   0.00   51
 28  ω     41.00  72.00   1.00   24.00    --  107.04 -45.00-180.00   31
 29  ω     63.00 107.00   1.00   24.00    --  107.04-111.00 -30.00   44
 30  ω     39.00 176.00   1.00   24.00    --  107.04   0.00-120.00  137
 31  ω    100.00 152.00   1.00   24.00    --  107.04  61.00 -90.00   52
 32  ω    123.00 174.00   1.00   24.00    --  107.04  77.00-120.00   51
 33  ω     66.00 106.00   1.00   24.00    --  107.04 -94.00-180.00   40
 34  ω     41.00  72.00   1.00   24.00    --  107.04 -45.00 150.00   31
 35  ω     41.00  72.00   1.00   24.00    --  107.04 -45.00 120.00   31
 36  ω    143.00 175.00   1.00   24.00    --  107.04  77.00  90.00   32
 37  ω     41.00  71.00   1.00   24.00    --  107.04 -45.00 -30.00   30
 38  ω     41.00  72.00   1.00   24.00    --  107.04 -45.00 -60.00   31
 39  ω     44.00 100.00   1.00   24.00    --  107.04 -94.00  90.00   56
 40  ω     39.00  71.00   1.00   24.00    --  107.04 -45.00-150.00   32
 41  ω     41.00  71.00   1.00   24.00    --  107.04 -45.00-120.00   30
 42  ω    123.00 150.00   1.00   24.00    --  107.04 111.00-150.00   27
 43  ω     62.00 101.00   1.00   24.00    --  107.04-111.00-180.00   39
 44  ω     41.00  71.00   1.00   24.00    --  107.04 -45.00  90.00   30
 45  ω    113.00 138.00   1.00   24.00    --  107.04  77.00  90.00   25
 46  ω     82.00 109.00   1.00   24.00    --  107.04 -77.00   0.00   27
 47  ω     87.00 114.00   1.00   24.00    --  107.04 -77.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1735
_reflns_number_total             2756
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0819P)²+0.0062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.5203(3) 0.4321(2) 0.37867(18) 0.0502(5) Uani 1 1 d . . . . .
N9 N 0.6658(3) 0.6955(2) 0.37086(19) 0.0537(5) Uani 1 1 d . . . . .
N2 N 0.6047(3) 0.8321(2) 0.60539(19) 0.0534(5) Uani 1 1 d . . . . .
C12 C 0.5409(3) 0.3635(3) 0.2521(2) 0.0475(6) Uani 1 1 d . . . . .
C10 C 0.5823(3) 0.6024(3) 0.4335(2) 0.0475(6) Uani 1 1 d . . . . .
C1 C 0.5565(3) 0.6714(3) 0.5544(2) 0.0485(6) Uani 1 1 d . . . . .
C6 C 0.7212(3) 0.8613(3) 0.4258(2) 0.0525(6) Uani 1 1 d . . . . .
C13 C 0.7010(3) 0.3504(3) 0.2413(2) 0.0498(6) Uani 1 1 d . . . . .
C3 C 0.6868(3) 0.9283(3) 0.5389(2) 0.0533(6) Uani 1 1 d . . . . .
N5 N 0.7690(4) 1.2459(3) 0.6270(2) 0.0869(9) Uani 1 1 d . . . . .
C19 C 0.4000(3) 0.3159(3) 0.1481(2) 0.0601(7) Uani 1 1 d . . . . .
C15 C 0.7162(4) 0.2837(3) 0.1198(3) 0.0612(7) Uani 1 1 d . . . . .
H15 H 0.821970 0.272506 0.109910 0.073 Uiso 1 1 calc R U . . .
N8 N 0.9143(4) 1.0386(3) 0.3151(3) 0.0883(9) Uani 1 1 d . . . . .
C4 C 0.7354(4) 1.1053(3) 0.5910(3) 0.0626(8) Uani 1 1 d . . . . .
C7 C 0.8253(4) 0.9613(3) 0.3626(3) 0.0600(7) Uani 1 1 d . . . . .
C16 C 0.5794(4) 0.2334(4) 0.0129(3) 0.0679(8) Uani 1 1 d . . . . .
C14 C 0.8539(3) 0.4094(4) 0.3544(3) 0.0659(7) Uani 1 1 d . . . . .
H14A H 0.900733 0.528209 0.376931 0.099 Uiso 1 1 calc R U . . .
H14B H 0.940815 0.361951 0.333499 0.099 Uiso 1 1 calc R U . . .
H14C H 0.817977 0.375671 0.425088 0.099 Uiso 1 1 calc R U . . .
C18 C 0.4239(4) 0.2516(4) 0.0292(3) 0.0722(8) Uani 1 1 d . . . . .
H18 H 0.331562 0.219719 -0.042055 0.087 Uiso 1 1 calc R U . . .
C20 C 0.2275(4) 0.3337(4) 0.1623(3) 0.0890(11) Uani 1 1 d . . . . .
H20A H 0.168844 0.247185 0.195540 0.134 Uiso 1 1 calc R U . . .
H20B H 0.158251 0.325343 0.080644 0.134 Uiso 1 1 calc R U . . .
H20C H 0.245664 0.439742 0.219847 0.134 Uiso 1 1 calc R U . . .
C17 C 0.6008(5) 0.1614(5) -0.1178(3) 0.1026(13) Uani 1 1 d . . . . .
H17A H 0.716215 0.156178 -0.110533 0.154 Uiso 1 1 calc R U . . .
H17B H 0.580624 0.230564 -0.171706 0.154 Uiso 1 1 calc R U . . .
H17C H 0.519103 0.051733 -0.154122 0.154 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
N11 C12 1.461(3) . ?
N11 C10 1.388(3) . ?
N11 C1 1.381(3) 2_666 ?
N9 C10 1.312(3) . ?
N9 C6 1.354(3) . ?
N2 C1 1.310(3) . ?
N2 C3 1.357(3) . ?
C12 C13 1.386(3) . ?
C12 C19 1.388(3) . ?
C10 C1 1.425(3) . ?
C6 C3 1.376(3) . ?
C6 C7 1.435(3) . ?
C13 C15 1.390(3) . ?
C13 C14 1.502(4) . ?
C3 C4 1.439(3) . ?
N5 C4 1.142(3) . ?
C19 C18 1.388(3) . ?
C19 C20 1.510(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
N8 C7 1.138(3) . ?
C16 C18 1.378(4) . ?
C16 C17 1.511(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C10 N11 C12 119.71(19) . . ?
C1 N11 C12 120.59(19) 2_666 . ?
C1 N11 C10 119.68(19) 2_666 . ?
C10 N9 C6 116.2(2) . . ?
C1 N2 C3 116.1(2) . . ?
C13 C12 N11 118.4(2) . . ?
C13 C12 C19 122.9(2) . . ?
C19 C12 N11 118.7(2) . . ?
N11 C10 C1 120.3(2) . . ?
N9 C10 N11 117.8(2) . . ?
N9 C10 C1 121.9(2) . . ?
N11 C1 C10 119.9(2) 2_666 . ?
N2 C1 N11 118.3(2) . 2_666 ?
N2 C1 C10 121.8(2) . . ?
N9 C6 C3 121.8(2) . . ?
N9 C6 C7 115.8(2) . . ?
C3 C6 C7 122.3(2) . . ?
C12 C13 C15 117.0(2) . . ?
C12 C13 C14 122.1(2) . . ?
C15 C13 C14 120.8(2) . . ?
N2 C3 C6 122.0(2) . . ?
N2 C3 C4 117.0(2) . . ?
C6 C3 C4 121.0(2) . . ?
C12 C19 C18 117.2(3) . . ?
C12 C19 C20 121.9(2) . . ?
C18 C19 C20 120.9(3) . . ?
C13 C15 H15 118.8 . . ?
C16 C15 C13 122.3(3) . . ?
C16 C15 H15 118.8 . . ?
N5 C4 C3 176.6(3) . . ?
N8 C7 C6 176.8(3) . . ?
C15 C16 C17 120.8(3) . . ?
C18 C16 C15 118.0(2) . . ?
C18 C16 C17 121.1(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C18 H18 118.8 . . ?
C16 C18 C19 122.4(3) . . ?
C16 C18 H18 118.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C12 C13 C15 179.6(2) . . . . ?
N11 C12 C13 C14 -2.1(3) . . . . ?
N11 C12 C19 C18 179.9(2) . . . . ?
N11 C12 C19 C20 0.2(4) . . . . ?
N11 C10 C1 N11 4.3(4) . . . 2_666 ?
N11 C10 C1 N2 -176.1(2) . . . . ?
N9 C10 C1 N11 -175.1(2) . . . 2_666 ?
N9 C10 C1 N2 4.6(4) . . . . ?
N9 C6 C3 N2 4.0(4) . . . . ?
N9 C6 C3 C4 -175.3(2) . . . . ?
C12 N11 C10 N9 -3.3(3) . . . . ?
C12 N11 C10 C1 177.3(2) . . . . ?
C12 C13 C15 C16 0.6(4) . . . . ?
C12 C19 C18 C16 0.5(5) . . . . ?
C10 N11 C12 C13 78.3(3) . . . . ?
C10 N11 C12 C19 -101.1(3) . . . . ?
C10 N9 C6 C3 -2.1(4) . . . . ?
C10 N9 C6 C7 174.7(2) . . . . ?
C1 N11 C12 C13 -100.1(3) 2_666 . . . ?
C1 N11 C12 C19 80.5(3) 2_666 . . . ?
C1 N11 C10 N9 175.1(2) 2_666 . . . ?
C1 N11 C10 C1 -4.3(4) 2_666 . . . ?
C1 N2 C3 C6 -1.4(4) . . . . ?
C1 N2 C3 C4 177.9(2) . . . . ?
C6 N9 C10 N11 178.6(2) . . . . ?
C6 N9 C10 C1 -2.0(4) . . . . ?
C13 C12 C19 C18 0.5(4) . . . . ?
C13 C12 C19 C20 -179.2(2) . . . . ?
C13 C15 C16 C18 0.3(4) . . . . ?
C13 C15 C16 C17 -180.0(3) . . . . ?
C3 N2 C1 N11 177.0(2) . . . 2_666 ?
C3 N2 C1 C10 -2.6(4) . . . . ?
C19 C12 C13 C15 -1.0(4) . . . . ?
C19 C12 C13 C14 177.3(2) . . . . ?
C15 C16 C18 C19 -0.9(5) . . . . ?
C7 C6 C3 N2 -172.6(3) . . . . ?
C7 C6 C3 C4 8.1(4) . . . . ?
C14 C13 C15 C16 -177.8(3) . . . . ?
C20 C19 C18 C16 -179.8(3) . . . . ?
C17 C16 C18 C19 179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-MeCN
_database_code_depnum_ccdc_archive 'CCDC 2429941'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 2(C2 H3 N)'
_chemical_formula_sum            'C34 H28 N12'
_chemical_formula_weight         604.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.1575(5)
_cell_length_b                   8.9502(4)
_cell_length_c                   16.0650(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.969(4)
_cell_angle_gamma                90
_cell_volume                     1604.05(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4771
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      30.1490
_cell_measurement_theta_min      2.9240
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         2.918
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  63.00   0.50    1.90    --   21.12 -86.00 156.00  172
  2  ω     39.00 109.00   0.50    1.90    --   21.12 179.00 120.00  140
  3  ω     47.00  86.00   0.50    1.90    --   21.12  37.00  30.00   78
  4  ω    -30.00  28.00   0.50    1.90    --   21.12  37.00  30.00  116
  5  ω      6.00  32.00   0.50    1.90    --  -19.87 -99.00 -60.00   52
  6  ω    -14.00  11.00   0.50    1.90    --  -19.87 -99.00   0.00   50
  7  ω    -53.00 -27.00   0.50    1.90    --  -19.87  86.00 -85.00   52
  8  ω      2.00  28.00   0.50    1.90    --  -19.87  86.00 -85.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0433413000
_diffrn_orient_matrix_UB_12      -0.0577800000
_diffrn_orient_matrix_UB_13      -0.0023532000
_diffrn_orient_matrix_UB_21      -0.0309100000
_diffrn_orient_matrix_UB_22      -0.0411587000
_diffrn_orient_matrix_UB_23      0.0307111000
_diffrn_orient_matrix_UB_31      -0.0347102000
_diffrn_orient_matrix_UB_32      -0.0354502000
_diffrn_orient_matrix_UB_33      -0.0316284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             3549
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.2472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C9(H9a,H9b,H9c), C8(H8a,H8b,H8c), C23(H23a,H23b,H23c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N13 N 1.03222(10) 0.37519(13) 0.34859(7) 0.0223(3) Uani 1 1 d . . . . .
N10 N 0.88941(10) 0.56348(13) 0.52189(7) 0.0211(3) Uani 1 1 d . . . . .
N16 N 0.80965(10) 0.49437(13) 0.39345(7) 0.0231(3) Uani 1 1 d . . . . .
N18 N 0.96781(11) 0.24925(15) 0.15242(8) 0.0326(3) Uani 1 1 d . . . . .
N20 N 0.63801(12) 0.40948(16) 0.22299(9) 0.0378(3) Uani 1 1 d . . . . .
C11 C 0.90239(11) 0.49758(15) 0.44456(8) 0.0200(3) Uani 1 1 d . . . . .
C12 C 1.01559(12) 0.43470(14) 0.42184(8) 0.0199(3) Uani 1 1 d . . . . .
C14 C 0.93636(12) 0.37373(15) 0.29586(9) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.77656(11) 0.63522(16) 0.54321(8) 0.0214(3) Uani 1 1 d . . . . .
C15 C 0.82674(12) 0.43035(15) 0.31809(9) 0.0225(3) Uani 1 1 d . . . . .
C17 C 0.95403(12) 0.30443(16) 0.21580(9) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.77133(12) 0.79102(16) 0.54127(9) 0.0243(3) Uani 1 1 d . . . . .
C19 C 0.72242(13) 0.41957(16) 0.26421(9) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.67985(12) 0.54588(16) 0.56542(9) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.57298(13) 0.61826(17) 0.58428(9) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.505048 0.560125 0.598398 0.034 Uiso 1 1 calc R U . . .
C4 C 0.56310(13) 0.77305(18) 0.58301(9) 0.0295(3) Uani 1 1 d . . . . .
N21 N 0.82501(15) 0.06016(19) 0.31844(12) 0.0556(5) Uani 1 1 d . . . . .
C3 C 0.66263(13) 0.85707(17) 0.56171(9) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.656411 0.962929 0.561062 0.033 Uiso 1 1 calc R U . . .
C7 C 0.87799(14) 0.88659(17) 0.52132(10) 0.0327(4) Uani 1 1 d . . . . .
H7A H 0.932670 0.890075 0.569664 0.049 Uiso 1 1 calc R U . . .
H7B H 0.851012 0.987990 0.507613 0.049 Uiso 1 1 calc R U . . .
H7C H 0.919756 0.843973 0.473683 0.049 Uiso 1 1 calc R U . . .
C9 C 0.68939(14) 0.37837(17) 0.57150(11) 0.0330(4) Uani 1 1 d . . . . .
H9A H 0.713863 0.337658 0.517771 0.049 Uiso 1 1 calc R U . . .
H9B H 0.611394 0.336602 0.586279 0.049 Uiso 1 1 calc R U . . .
H9C H 0.749125 0.351837 0.614421 0.049 Uiso 1 1 calc R U . . .
C22 C 0.77102(15) -0.0448(2) 0.30483(11) 0.0387(4) Uani 1 1 d . . . . .
C8 C 0.44866(14) 0.8491(2) 0.60846(11) 0.0404(4) Uani 1 1 d . . . . .
H8A H 0.379983 0.786019 0.593118 0.061 Uiso 1 1 calc R U . . .
H8B H 0.441520 0.945605 0.579970 0.061 Uiso 1 1 calc R U . . .
H8C H 0.450168 0.865107 0.668819 0.061 Uiso 1 1 calc R U . . .
C23 C 0.70281(18) -0.1799(2) 0.28892(13) 0.0491(5) Uani 1 1 d . . . . .
H23A H 0.730256 -0.226510 0.237436 0.074 Uiso 1 1 calc R U . . .
H23B H 0.617538 -0.155017 0.283124 0.074 Uiso 1 1 calc R U . . .
H23C H 0.714491 -0.249529 0.335430 0.074 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
N13 C12 1.3078(17) . ?
N13 C14 1.3531(17) . ?
N10 C11 1.3851(17) . ?
N10 C12 1.3815(17) 3_766 ?
N10 C1 1.4593(16) . ?
N16 C11 1.3103(17) . ?
N16 C15 1.3559(18) . ?
N18 C17 1.1443(18) . ?
N20 C19 1.1456(18) . ?
C11 C12 1.4355(18) . ?
C14 C15 1.3766(19) . ?
C14 C17 1.445(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.3943(19) . ?
C15 C19 1.442(2) . ?
C2 C3 1.3935(19) . ?
C2 C7 1.505(2) . ?
C6 C5 1.395(2) . ?
C6 C9 1.506(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(2) . ?
C4 C3 1.389(2) . ?
C4 C8 1.510(2) . ?
N21 C22 1.135(2) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C22 C23 1.449(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C12 N13 C14 116.39(12) . . ?
C11 N10 C1 120.11(11) . . ?
C12 N10 C11 120.08(11) 3_766 . ?
C12 N10 C1 119.79(11) 3_766 . ?
C11 N16 C15 116.56(12) . . ?
N10 C11 C12 120.05(12) . . ?
N16 C11 N10 118.55(12) . . ?
N16 C11 C12 121.41(12) . . ?
N13 C12 N10 118.33(12) . 3_766 ?
N13 C12 C11 121.82(12) . . ?
N10 C12 C11 119.85(12) 3_766 . ?
N13 C14 C15 122.04(13) . . ?
N13 C14 C17 116.31(12) . . ?
C15 C14 C17 121.62(12) . . ?
C2 C1 N10 118.05(12) . . ?
C6 C1 N10 118.83(12) . . ?
C6 C1 C2 123.12(12) . . ?
N16 C15 C14 121.75(12) . . ?
N16 C15 C19 116.10(12) . . ?
C14 C15 C19 122.10(13) . . ?
N18 C17 C14 179.82(18) . . ?
C1 C2 C7 122.67(13) . . ?
C3 C2 C1 117.05(13) . . ?
C3 C2 C7 120.25(13) . . ?
N20 C19 C15 178.30(17) . . ?
C1 C6 C5 117.22(13) . . ?
C1 C6 C9 122.23(13) . . ?
C5 C6 C9 120.53(13) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.84(14) . . ?
C4 C5 H5 119.1 . . ?
C5 C4 C8 120.85(14) . . ?
C3 C4 C5 118.67(13) . . ?
C3 C4 C8 120.40(14) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.08(14) . . ?
C4 C3 H3 119.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N21 C22 C23 179.0(2) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
N13 C14 C15 N16 1.8(2) . . . . ?
N13 C14 C15 C19 -175.60(13) . . . . ?
N10 C11 C12 N13 -178.12(12) . . . . ?
N10 C11 C12 N10 1.7(2) . . . 3_766 ?
N10 C1 C2 C3 179.89(12) . . . . ?
N10 C1 C2 C7 -2.3(2) . . . . ?
N10 C1 C6 C5 -179.14(12) . . . . ?
N10 C1 C6 C9 2.5(2) . . . . ?
N16 C11 C12 N13 1.9(2) . . . . ?
N16 C11 C12 N10 -178.29(12) . . . 3_766 ?
C11 N10 C1 C2 -103.20(15) . . . . ?
C11 N10 C1 C6 77.54(16) . . . . ?
C11 N16 C15 C14 -1.0(2) . . . . ?
C11 N16 C15 C19 176.51(12) . . . . ?
C12 N13 C14 C15 -0.62(19) . . . . ?
C12 N13 C14 C17 -178.43(12) . . . . ?
C12 N10 C11 N16 178.29(12) 3_766 . . . ?
C12 N10 C11 C12 -1.7(2) 3_766 . . . ?
C12 N10 C1 C2 74.91(16) 3_766 . . . ?
C12 N10 C1 C6 -104.35(15) 3_766 . . . ?
C14 N13 C12 N10 179.05(11) . . . 3_766 ?
C14 N13 C12 C11 -1.11(19) . . . . ?
C1 N10 C11 N16 -3.61(18) . . . . ?
C1 N10 C11 C12 176.38(12) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 C5 C4 -1.4(2) . . . . ?
C15 N16 C11 N10 179.27(12) . . . . ?
C15 N16 C11 C12 -0.72(19) . . . . ?
C17 C14 C15 N16 179.46(13) . . . . ?
C17 C14 C15 C19 2.1(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
C2 C1 C6 C9 -176.68(13) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C2 C7 176.90(13) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C6 C5 C4 C8 -176.44(14) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C7 C2 C3 C4 -177.98(14) . . . . ?
C9 C6 C5 C4 176.94(14) . . . . ?
C8 C4 C3 C2 177.27(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_TCDP-PhMe
_database_code_depnum_ccdc_archive 'CCDC 2429942'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, C7 H8'
_chemical_formula_sum            'C37 H30 N10'
_chemical_formula_weight         614.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O '
_chemical_oxdiff_usercomment     'C N O H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.6712(2)
_cell_length_b                   18.7282(3)
_cell_length_c                   24.0317(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.377(2)
_cell_angle_gamma                90
_cell_volume                     5110.35(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    23638
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.9540
_cell_measurement_theta_min      2.5020
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1932
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            58548
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  14.00   0.50   20.98    --    7.34 -37.00  60.00  148
  2  ω    -12.00  18.00   0.50   20.98    --    7.34 -99.00  90.00   60
  3  ω     -3.00  22.00   0.50   20.98    --    7.34-105.00 140.00   50
  4  ω    -11.00  29.00   0.50   20.98    --    7.34 -99.00 -60.00   80
  5  ω      0.00  25.00   0.50   20.98    --    7.34 -99.00 -90.00   50
  6  ω    -77.00   3.00   0.50   20.98    --   -5.93 -57.00-180.00  160
  7  ω     -1.00  35.00   0.50   20.98    --    7.34  37.00-150.00   72
  8  ω     55.00  80.00   0.50   20.98    --    7.34  37.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0161091000
_diffrn_orient_matrix_UB_12      -0.0359873000
_diffrn_orient_matrix_UB_13      -0.0033519000
_diffrn_orient_matrix_UB_21      0.0008853000
_diffrn_orient_matrix_UB_22      -0.0067142000
_diffrn_orient_matrix_UB_23      0.0291405000
_diffrn_orient_matrix_UB_31      -0.0603716000
_diffrn_orient_matrix_UB_32      -0.0096758000
_diffrn_orient_matrix_UB_33      -0.0077242000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9879
_reflns_number_total             12179
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         12179
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+1.5946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C23
 1.51 with sigma of 0.02
 N5-C44 \\sim N5-C44A
 with sigma of 0.02
 C44-C45 \\sim C44A-C45A
 with sigma of 0.02
 C44-C49 \\sim C44A-C49A
 with sigma of 0.02
 C45-C51 \\sim C45A-C51A
 with sigma of 0.02
 C45-C46 \\sim C45A-C46A
 with sigma of 0.02
 C49-C48 \\sim C49A-C48A
 with sigma of 0.02
 C49-C52 \\sim C49A-C52A
 with sigma of 0.02
 C48-C47 \\sim C48A-C47A
 with sigma of 0.02
 C46-C47 \\sim C46A-C47A
 with sigma of 0.02
 C47-C50 \\sim C47A-C50A
 with sigma of 0.02
 N5-C45 \\sim N5-C45A
 with sigma of 0.04
 N5-C49 \\sim N5-C49A
 with sigma of 0.04
 C44-C48 \\sim C44A-C48A
 with sigma of 0.04
 C44-C51 \\sim C44A-C51A
 with sigma of 0.04
 C44-C46 \\sim C44A-C46A
 with sigma of 0.04
 C44-C52 \\sim C44A-C52A
 with sigma of 0.04
 C45-C49 \\sim C45A-C49A
 with sigma of 0.04
 C45-C47 \\sim C45A-C47A
 with sigma of 0.04
 C49-C47 \\sim C49A-C47A
 with sigma of 0.04
 C48-C46 \\sim C48A-C46A
 with sigma of 0.04
 C48-C52 \\sim C48A-C52A
 with sigma of 0.04
 C48-C50 \\sim C48A-C50A
 with sigma of 0.04
 C51-C46 \\sim C51A-C46A
 with sigma of 0.04
 C46-C50 \\sim C46A-C50A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C68) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C48)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C47) \\sim Ueq,
Uanis(C50) \\sim Ueq, Uanis(C45A) \\sim Ueq, Uanis(C46A) \\sim Ueq, Uanis(C47A)
\\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C48A) \\sim Ueq, Uanis(C49A) \\sim Ueq,
Uanis(C44A) \\sim Ueq, Uanis(C52A) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C51A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C68, C17, C7, C14, C10, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(C62A)=Sof(C67A)=Sof(H67A)=
 Sof(C61A)=Sof(H61A)=Sof(C65A)=Sof(H65A)=Sof(C64A)=Sof(H64A)=Sof(C63A)=
 Sof(H63A)=1-FVAR(1)
 Sof(C62)=Sof(C67)=Sof(H67)=Sof(C61)=Sof(H61)=Sof(C65)=Sof(H65)=Sof(C64)=
 Sof(H64)=Sof(C63)=Sof(H63)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=FVAR(1)
 Fixed Sof: C44(0.5) C45(0.5) C49(0.5) C48(0.5) H48(0.5) C51(0.5) H51A(0.5)
 H51B(0.5) H51C(0.5) C46(0.5) H46(0.5) C52(0.5) H52A(0.5) H52B(0.5) H52C(0.5)
 C47(0.5) C50(0.5) H50A(0.5) H50B(0.5) H50C(0.5) C7(0.5) C14(0.5) H14(0.5)
 C10(0.5) H10(0.5) C21(0.5) H21(0.5) C68(0.5) H68(0.5) C17(0.5) H17(0.5)
 C23(0.5) H23A(0.5) H23B(0.5) H23C(0.5) C51A(0.5) H51D(0.5) H51E(0.5) H51F(0.5)
 C45A(0.5) C46A(0.5) H46A(0.5) C47A(0.5) C50A(0.5) H50D(0.5) H50E(0.5)
 H50F(0.5) C48A(0.5) H48A(0.5) C49A(0.5) C44A(0.5) C52A(0.5) H52D(0.5)
 H52E(0.5) H52F(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C39(H39), C37(H37), C5(H5), C3(H3), C48(H48), C46(H46), C67(H67), C61(H61),
 C65(H65), C64(H64), C63(H63), C67A(H67A), C61A(H61A), C65A(H65A), C64A(H64A),
 C63A(H63A), C14(H14), C10(H10), C21(H21), C68(H68), C17(H17), C46A(H46A),
 C48A(H48A)
6.b Fitted hexagon refined as free rotating group:
 C62(C67,C61,C65,C64,C63), C62A(C67A,C61A,C65A,C64A,C63A), C7(C14,C10,C21,C68,
 C17)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C42(H42A,H42B,H42C), C19(H19A,H19B,H19C), C41(H41A,H41B,
 H41C), C43(H43A,H43B,H43C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C20(H20A,
 H20B,H20C), C50(H50A,H50B,H50C), C66(H66A,H66B,H66C), C66A(H66D,H66E,H66F),
 C23(H23A,H23B,H23C), C51A(H51D,H51E,H51F), C50A(H50D,H50E,H50F), C52A(H52D,
 H52E,H52F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N15 N 0.02822(9) 0.56907(5) 0.52148(4) 0.0247(2) Uani 1 1 d . . . . .
N1 N 0.24275(9) 0.06181(6) 0.80043(4) 0.0277(2) Uani 1 1 d . . . . .
N6 N 0.37758(9) 0.14051(5) 0.77628(4) 0.0264(2) Uani 1 1 d . . . . .
N13 N 0.11662(9) 0.38438(6) 0.55165(5) 0.0302(2) Uani 1 1 d . . . . .
N2 N 0.20438(10) 0.00006(6) 0.69096(5) 0.0312(2) Uani 1 1 d . . . . .
N8 N 0.49183(10) 0.14463(6) 0.64746(5) 0.0317(2) Uani 1 1 d . . . . .
N14 N 0.17405(9) 0.52259(6) 0.59488(5) 0.0314(2) Uani 1 1 d . . . . .
N5 N 0.35393(10) 0.06896(6) 0.67085(4) 0.0317(2) Uani 1 1 d D . . . .
N7 N 0.50795(9) 0.22001(6) 0.74997(5) 0.0313(2) Uani 1 1 d . . . . .
N4 N 0.04662(12) -0.03853(7) 0.85539(6) 0.0437(3) Uani 1 1 d . . . . .
C8 C 0.06054(10) 0.44086(6) 0.52714(5) 0.0245(2) Uani 1 1 d . . . . .
C9 C 0.08965(10) 0.51127(6) 0.54911(5) 0.0248(2) Uani 1 1 d . . . . .
C22 C 0.30160(10) 0.08302(6) 0.76294(5) 0.0254(2) Uani 1 1 d . . . . .
N3 N -0.02553(15) -0.11070(8) 0.69379(7) 0.0583(4) Uani 1 1 d . . . . .
C35 C 0.37749(10) 0.18413(6) 0.82657(5) 0.0264(2) Uani 1 1 d . . . . .
C34 C 0.16250(11) 0.00918(6) 0.78334(5) 0.0281(3) Uani 1 1 d . . . . .
C40 C 0.28991(11) 0.23546(7) 0.82220(6) 0.0310(3) Uani 1 1 d . . . . .
C53 C 0.09862(12) -0.01649(7) 0.82412(6) 0.0330(3) Uani 1 1 d . . . . .
C1 C 0.06145(11) 0.64165(6) 0.53995(5) 0.0266(2) Uani 1 1 d . . . . .
C29 C 0.43160(11) 0.12561(7) 0.68477(5) 0.0281(2) Uani 1 1 d . . . . .
C33 C 0.14136(12) -0.01947(6) 0.72913(6) 0.0299(3) Uani 1 1 d . . . . .
C11 C 0.20290(11) 0.39639(7) 0.59893(6) 0.0338(3) Uani 1 1 d . . . . .
C24 C 0.44154(10) 0.16315(6) 0.73756(5) 0.0263(2) Uani 1 1 d . . . . .
C31 C 0.28552(11) 0.04901(6) 0.70797(5) 0.0278(2) Uani 1 1 d . . . . .
N11 N 0.31534(13) 0.28380(8) 0.64444(7) 0.0585(4) Uani 1 1 d . . . . .
C2 C 0.15291(12) 0.67247(7) 0.52008(5) 0.0313(3) Uani 1 1 d . . . . .
C59 C 0.04911(14) -0.07111(8) 0.70969(6) 0.0395(3) Uani 1 1 d . . . . .
C27 C 0.55913(11) 0.20378(7) 0.66029(6) 0.0320(3) Uani 1 1 d . . . . .
C26 C 0.56569(11) 0.24144(7) 0.71009(6) 0.0331(3) Uani 1 1 d . . . . .
C15 C 0.23128(11) 0.46363(8) 0.62014(6) 0.0350(3) Uani 1 1 d . . . . .
C39 C 0.28961(12) 0.27629(7) 0.87042(7) 0.0380(3) Uani 1 1 d . . . . .
H39 H 0.230987 0.311996 0.868438 0.046 Uiso 1 1 calc R U . . .
N10 N 0.65888(14) 0.24286(9) 0.57995(6) 0.0600(4) Uani 1 1 d . . . . .
N9 N 0.67660(15) 0.36187(9) 0.72690(8) 0.0673(5) Uani 1 1 d . . . . .
C38 C 0.37265(14) 0.26632(8) 0.92140(7) 0.0428(3) Uani 1 1 d . . . . .
C6 C -0.00217(13) 0.67742(7) 0.57340(6) 0.0351(3) Uani 1 1 d . . . . .
C36 C 0.46568(12) 0.17477(8) 0.87565(6) 0.0378(3) Uani 1 1 d . . . . .
C12 C 0.26592(13) 0.33374(8) 0.62499(7) 0.0437(3) Uani 1 1 d . . . . .
C55 C 0.61756(13) 0.22650(8) 0.61670(6) 0.0398(3) Uani 1 1 d . . . . .
C18 C 0.21548(13) 0.63085(8) 0.48245(6) 0.0367(3) Uani 1 1 d . . . . .
H18A H 0.247825 0.586865 0.502038 0.055 Uiso 1 1 calc R U . . .
H18B H 0.279639 0.659768 0.474296 0.055 Uiso 1 1 calc R U . . .
H18C H 0.159720 0.618800 0.446506 0.055 Uiso 1 1 calc R U . . .
C44 C 0.3239(8) 0.0414(6) 0.6127(3) 0.0337(17) Uani 0.5 1 d D U P A 1
C57 C 0.62893(14) 0.30833(9) 0.72050(7) 0.0446(4) Uani 1 1 d . . . . .
C37 C 0.46019(14) 0.21658(10) 0.92288(6) 0.0469(4) Uani 1 1 d . . . . .
H37 H 0.518813 0.210589 0.957277 0.056 Uiso 1 1 calc R U . . .
C5 C 0.02968(17) 0.74781(8) 0.58780(7) 0.0474(4) Uani 1 1 d . . . . .
H5 H -0.011975 0.773823 0.610762 0.057 Uiso 1 1 calc R U . . .
C3 C 0.18125(16) 0.74286(8) 0.53576(7) 0.0462(4) Uani 1 1 d . . . . .
H3 H 0.243531 0.765521 0.523141 0.055 Uiso 1 1 calc R U . . .
C16 C 0.32544(15) 0.47536(10) 0.67021(7) 0.0513(4) Uani 1 1 d . . . . .
N12 N 0.40164(16) 0.48501(11) 0.70859(8) 0.0797(6) Uani 1 1 d . . . . .
C42 C 0.19734(14) 0.24509(10) 0.76798(7) 0.0499(4) Uani 1 1 d . . . . .
H42A H 0.235152 0.251930 0.735962 0.075 Uiso 1 1 calc R U . . .
H42B H 0.149310 0.287040 0.771493 0.075 Uiso 1 1 calc R U . . .
H42C H 0.147025 0.202609 0.761038 0.075 Uiso 1 1 calc R U . . .
C19 C -0.10211(15) 0.64287(8) 0.59293(8) 0.0504(4) Uani 1 1 d . . . . .
H19A H -0.177077 0.658380 0.568308 0.076 Uiso 1 1 calc R U . . .
H19B H -0.099141 0.656836 0.632537 0.076 Uiso 1 1 calc R U . . .
H19C H -0.095369 0.590847 0.590691 0.076 Uiso 1 1 calc R U . . .
C4 C 0.12046(19) 0.78089(8) 0.56952(8) 0.0549(5) Uani 1 1 d . . . . .
C45 C 0.3983(7) -0.0115(5) 0.6022(3) 0.0443(18) Uani 0.5 1 d D U P A 1
C49 C 0.2337(6) 0.0699(4) 0.5715(3) 0.0354(15) Uani 0.5 1 d D U P A 1
C41 C 0.56395(16) 0.12228(12) 0.87777(7) 0.0622(5) Uani 1 1 d . . . . .
H41A H 0.531329 0.076851 0.860977 0.093 Uiso 1 1 calc R U . . .
H41B H 0.605830 0.114594 0.917622 0.093 Uiso 1 1 calc R U . . .
H41C H 0.618774 0.141147 0.856076 0.093 Uiso 1 1 calc R U . . .
C48 C 0.2195(5) 0.0415(3) 0.5167(2) 0.0466(14) Uani 0.5 1 d D U P A 1
H48 H 0.156477 0.058273 0.487193 0.056 Uiso 0.5 1 calc R U P A 1
C43 C 0.3650(2) 0.30792(13) 0.97445(9) 0.0705(6) Uani 1 1 d . . . . .
H43A H 0.343325 0.357502 0.963974 0.106 Uiso 1 1 calc R U . . .
H43B H 0.441621 0.306857 1.001850 0.106 Uiso 1 1 calc R U . . .
H43C H 0.305275 0.286322 0.991858 0.106 Uiso 1 1 calc R U . . .
C51 C 0.4969(10) -0.0414(7) 0.6490(5) 0.061(2) Uani 0.5 1 d D U P A 1
H51A H 0.542792 -0.075774 0.632299 0.091 Uiso 0.5 1 calc R U P A 1
H51B H 0.463276 -0.065421 0.677752 0.091 Uiso 0.5 1 calc R U P A 1
H51C H 0.548247 -0.002428 0.666981 0.091 Uiso 0.5 1 calc R U P A 1
C46 C 0.3811(6) -0.0370(4) 0.5460(3) 0.0540(16) Uani 0.5 1 d D U P A 1
H46 H 0.430890 -0.073300 0.537170 0.065 Uiso 0.5 1 calc R U P A 1
C52 C 0.1560(11) 0.1271(6) 0.5851(5) 0.066(2) Uani 0.5 1 d D U P A 1
H52A H 0.204210 0.164090 0.608180 0.098 Uiso 0.5 1 calc R U P A 1
H52B H 0.101930 0.106666 0.606514 0.098 Uiso 0.5 1 calc R U P A 1
H52C H 0.110592 0.148217 0.549442 0.098 Uiso 0.5 1 calc R U P A 1
C47 C 0.2929(6) -0.0096(4) 0.5039(3) 0.0491(15) Uani 0.5 1 d D U P A 1
C20 C 0.1537(3) 0.85771(11) 0.58658(12) 0.0978(10) Uani 1 1 d . . . . .
H20A H 0.085437 0.882498 0.594715 0.147 Uiso 1 1 calc R U . . .
H20B H 0.178575 0.881957 0.555202 0.147 Uiso 1 1 calc R U . . .
H20C H 0.218470 0.858164 0.620802 0.147 Uiso 1 1 calc R U . . .
C50 C 0.2787(8) -0.0401(5) 0.4433(3) 0.090(3) Uani 0.5 1 d D U P A 1
H50A H 0.254831 -0.090288 0.442881 0.135 Uiso 0.5 1 calc R U P A 1
H50B H 0.353883 -0.036570 0.431836 0.135 Uiso 0.5 1 calc R U P A 1
H50C H 0.218469 -0.012874 0.416441 0.135 Uiso 0.5 1 calc R U P A 1
C62 C 0.9134(3) 0.1912(3) 0.67857(19) 0.0524(15) Uani 0.540(7) 1 d G . P B 1
C67 C 0.8874(3) 0.23192(19) 0.7224(3) 0.0638(14) Uani 0.540(7) 1 d G . P B 1
H67 H 0.893477 0.282471 0.721636 0.077 Uiso 0.540(7) 1 calc R U P B 1
C61 C 0.8524(5) 0.1986(4) 0.7675(2) 0.080(2) Uani 0.540(7) 1 d G . P B 1
H61 H 0.834619 0.226414 0.797480 0.096 Uiso 0.540(7) 1 calc R U P B 1
C65 C 0.8434(5) 0.1247(4) 0.7687(2) 0.082(2) Uani 0.540(7) 1 d G . P B 1
H65 H 0.819543 0.101893 0.799463 0.098 Uiso 0.540(7) 1 calc R U P B 1
C64 C 0.8694(5) 0.08398(19) 0.7248(3) 0.0747(19) Uani 0.540(7) 1 d G . P B 1
H64 H 0.863327 0.033429 0.725602 0.090 Uiso 0.540(7) 1 calc R U P B 1
C63 C 0.9044(4) 0.1173(3) 0.67974(17) 0.0617(16) Uani 0.540(7) 1 d G . P B 1
H63 H 0.922186 0.089485 0.649757 0.074 Uiso 0.540(7) 1 calc R U P B 1
C66 C 0.9541(4) 0.2301(4) 0.6315(3) 0.093(2) Uani 0.540(7) 1 d . . P B 1
H66A H 0.928782 0.280084 0.630469 0.139 Uiso 0.540(7) 1 calc R U P B 1
H66B H 0.919633 0.207435 0.594648 0.139 Uiso 0.540(7) 1 calc R U P B 1
H66C H 1.040153 0.227994 0.638773 0.139 Uiso 0.540(7) 1 calc R U P B 1
C66A C 0.9365(5) 0.2709(3) 0.6686(3) 0.077(2) Uani 0.460(7) 1 d . . P B 2
H66D H 0.907414 0.265831 0.627165 0.116 Uiso 0.460(7) 1 calc R U P B 2
H66E H 1.022313 0.276225 0.677782 0.116 Uiso 0.460(7) 1 calc R U P B 2
H66F H 0.900830 0.313158 0.681783 0.116 Uiso 0.460(7) 1 calc R U P B 2
C62A C 0.9040(4) 0.2058(3) 0.6979(2) 0.0489(16) Uani 0.460(7) 1 d G . P B 2
C67A C 0.8817(5) 0.2108(3) 0.7522(3) 0.0640(18) Uani 0.460(7) 1 d G . P B 2
H67A H 0.888658 0.255472 0.771317 0.077 Uiso 0.460(7) 1 calc R U P B 2
C61A C 0.8491(5) 0.1503(5) 0.77834(16) 0.070(2) Uani 0.460(7) 1 d G . P B 2
H61A H 0.833790 0.153749 0.815399 0.084 Uiso 0.460(7) 1 calc R U P B 2
C65A C 0.8389(6) 0.0849(3) 0.7503(3) 0.080(2) Uani 0.460(7) 1 d G . P B 2
H65A H 0.816583 0.043615 0.768206 0.096 Uiso 0.460(7) 1 calc R U P B 2
C64A C 0.8612(6) 0.0799(2) 0.6961(3) 0.085(3) Uani 0.460(7) 1 d G . P B 2
H64A H 0.854243 0.035202 0.676931 0.102 Uiso 0.460(7) 1 calc R U P B 2
C63A C 0.8938(5) 0.1403(4) 0.66990(13) 0.070(2) Uani 0.460(7) 1 d G . P B 2
H63A H 0.909111 0.136925 0.632849 0.084 Uiso 0.460(7) 1 calc R U P B 2
C7 C 0.4766(3) -0.02520(19) 0.96334(15) 0.0753(12) Uani 0.5 1 d DG U P C -1
C14 C 0.4067(4) 0.0340(2) 0.9668(2) 0.0833(14) Uani 0.5 1 d G U P C -1
H14 H 0.342840 0.045567 0.935775 0.100 Uiso 0.5 1 calc R U P C -1
C10 C 0.4302(6) 0.07613(19) 1.0158(3) 0.1072(17) Uani 0.5 1 d G U P C -1
H10 H 0.382445 0.116558 1.018137 0.129 Uiso 0.5 1 calc R U P C -1
C21 C 0.5237(7) 0.0591(3) 1.06119(19) 0.122(2) Uani 0.5 1 d G U P C -1
H21 H 0.539761 0.087961 1.094631 0.146 Uiso 0.5 1 calc R U P C -1
C68 C 0.5936(5) 0.0000(3) 1.05771(15) 0.128(2) Uani 0.5 1 d G U P C -1
H68 H 0.657475 -0.011626 1.088765 0.153 Uiso 0.5 1 calc R U P C -1
C17 C 0.5701(3) -0.0422(2) 1.00879(19) 0.0948(16) Uani 0.5 1 d G U P C -1
H17 H 0.617873 -0.082618 1.006403 0.114 Uiso 0.5 1 calc R U P C -1
C23 C 0.4326(5) -0.0616(4) 0.9080(2) 0.0965(18) Uani 0.5 1 d D . P C -1
H23A H 0.351439 -0.077495 0.905057 0.145 Uiso 0.5 1 calc R U P C -1
H23B H 0.482466 -0.103090 0.905493 0.145 Uiso 0.5 1 calc R U P C -1
H23C H 0.434836 -0.028513 0.876681 0.145 Uiso 0.5 1 calc R U P C -1
C51A C 0.5206(12) -0.0462(9) 0.6590(5) 0.065(2) Uani 0.5 1 d D U P A 2
H51D H 0.485942 -0.055207 0.691802 0.097 Uiso 0.5 1 calc R U P A 2
H51E H 0.582155 -0.009754 0.669246 0.097 Uiso 0.5 1 calc R U P A 2
H51F H 0.555037 -0.090449 0.648433 0.097 Uiso 0.5 1 calc R U P A 2
C45A C 0.4281(6) -0.0208(4) 0.6101(3) 0.0332(13) Uani 0.5 1 d D U P A 2
C46A C 0.4187(5) -0.0485(4) 0.5551(3) 0.0432(12) Uani 0.5 1 d D U P A 2
H46A H 0.474153 -0.083516 0.549729 0.052 Uiso 0.5 1 calc R U P A 2
C47A C 0.3331(5) -0.0275(3) 0.5084(2) 0.0363(11) Uani 0.5 1 d D U P A 2
C50A C 0.3263(7) -0.0595(5) 0.4497(3) 0.0680(18) Uani 0.5 1 d D U P A 2
H50D H 0.405384 -0.073614 0.446494 0.102 Uiso 0.5 1 calc R U P A 2
H50E H 0.294423 -0.023977 0.420257 0.102 Uiso 0.5 1 calc R U P A 2
H50F H 0.274895 -0.101473 0.444560 0.102 Uiso 0.5 1 calc R U P A 2
C48A C 0.2536(5) 0.0240(3) 0.5158(3) 0.0362(11) Uani 0.5 1 d D U P A 2
H48A H 0.193532 0.039014 0.484185 0.043 Uiso 0.5 1 calc R U P A 2
C49A C 0.2610(6) 0.0546(4) 0.5701(3) 0.0308(12) Uani 0.5 1 d D U P A 2
C44A C 0.3489(7) 0.0319(5) 0.6157(3) 0.0248(12) Uani 0.5 1 d D U P A 2
C52A C 0.1740(9) 0.1122(5) 0.5774(4) 0.0455(15) Uani 0.5 1 d D U P A 2
H52D H 0.116112 0.119187 0.541159 0.068 Uiso 0.5 1 calc R U P A 2
H52E H 0.216286 0.157046 0.588801 0.068 Uiso 0.5 1 calc R U P A 2
H52F H 0.133415 0.097639 0.607023 0.068 Uiso 0.5 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N15 C8 1.3831(15) 3_566 ?
N15 C9 1.3807(15) . ?
N15 C1 1.4545(14) . ?
N1 C22 1.3144(16) . ?
N1 C34 1.3563(16) . ?
N6 C22 1.3845(16) . ?
N6 C35 1.4590(15) . ?
N6 C24 1.3872(16) . ?
N13 C8 1.3098(15) . ?
N13 C11 1.3513(17) . ?
N2 C33 1.3522(16) . ?
N2 C31 1.3135(16) . ?
N8 C29 1.3101(16) . ?
N8 C27 1.3517(17) . ?
N14 C9 1.3129(16) . ?
N14 C15 1.3588(17) . ?
N5 C29 1.3852(16) . ?
N5 C31 1.3793(16) . ?
N5 C44 1.454(8) . ?
N5 C44A 1.486(7) . ?
N7 C24 1.3103(16) . ?
N7 C26 1.3538(17) . ?
N4 C53 1.1464(18) . ?
C8 C9 1.4317(16) . ?
C22 C31 1.4391(16) . ?
N3 C59 1.140(2) . ?
C35 C40 1.3893(17) . ?
C35 C36 1.3854(18) . ?
C34 C53 1.4442(17) . ?
C34 C33 1.3773(18) . ?
C40 C39 1.3890(19) . ?
C40 C42 1.499(2) . ?
C1 C2 1.3916(17) . ?
C1 C6 1.3864(18) . ?
C29 C24 1.4317(17) . ?
C33 C59 1.4423(19) . ?
C11 C15 1.370(2) . ?
C11 C12 1.4481(18) . ?
N11 C12 1.1406(19) . ?
C2 C18 1.5047(19) . ?
C2 C3 1.3899(19) . ?
C27 C26 1.3760(19) . ?
C27 C55 1.4402(19) . ?
C26 C57 1.4461(19) . ?
C15 C16 1.446(2) . ?
C39 H39 0.9500 . ?
C39 C38 1.388(2) . ?
N10 C55 1.142(2) . ?
N9 C57 1.140(2) . ?
C38 C37 1.377(2) . ?
C38 C43 1.514(2) . ?
C6 C5 1.3916(19) . ?
C6 C19 1.501(2) . ?
C36 C37 1.392(2) . ?
C36 C41 1.503(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C44 C45 1.378(8) . ?
C44 C49 1.376(8) . ?
C37 H37 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C16 N12 1.138(2) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 C20 1.521(2) . ?
C45 C51 1.517(9) . ?
C45 C46 1.404(8) . ?
C49 C48 1.395(8) . ?
C49 C52 1.487(8) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C48 H48 0.9500 . ?
C48 C47 1.366(7) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C46 H46 0.9500 . ?
C46 C47 1.365(7) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C47 C50 1.538(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C62 C67 1.3900 . ?
C62 C63 1.3900 . ?
C62 C66 1.511(5) . ?
C67 H67 0.9500 . ?
C67 C61 1.3900 . ?
C61 H61 0.9500 . ?
C61 C65 1.3900 . ?
C65 H65 0.9500 . ?
C65 C64 1.3900 . ?
C64 H64 0.9500 . ?
C64 C63 1.3900 . ?
C63 H63 0.9500 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C66A H66D 0.9800 . ?
C66A H66E 0.9800 . ?
C66A H66F 0.9800 . ?
C66A C62A 1.500(6) . ?
C62A C67A 1.3900 . ?
C62A C63A 1.3900 . ?
C67A H67A 0.9500 . ?
C67A C61A 1.3900 . ?
C61A H61A 0.9500 . ?
C61A C65A 1.3900 . ?
C65A H65A 0.9500 . ?
C65A C64A 1.3900 . ?
C64A H64A 0.9500 . ?
C64A C63A 1.3900 . ?
C63A H63A 0.9500 . ?
C7 C14 1.3900 . ?
C7 C17 1.3900 . ?
C7 C23 1.478(7) . ?
C14 H14 0.9500 . ?
C14 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C21 1.3900 . ?
C21 H21 0.9500 . ?
C21 C68 1.3900 . ?
C68 H68 0.9500 . ?
C68 C17 1.3900 . ?
C17 H17 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C51A H51D 0.9800 . ?
C51A H51E 0.9800 . ?
C51A H51F 0.9800 . ?
C51A C45A 1.479(9) . ?
C45A C46A 1.401(7) . ?
C45A C44A 1.380(8) . ?
C46A H46A 0.9500 . ?
C46A C47A 1.376(7) . ?
C47A C50A 1.517(7) . ?
C47A C48A 1.378(6) . ?
C50A H50D 0.9800 . ?
C50A H50E 0.9800 . ?
C50A H50F 0.9800 . ?
C48A H48A 0.9500 . ?
C48A C49A 1.409(8) . ?
C49A C44A 1.382(8) . ?
C49A C52A 1.521(8) . ?
C52A H52D 0.9800 . ?
C52A H52E 0.9800 . ?
C52A H52F 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
C8 N15 C1 118.56(9) 3_566 . ?
C9 N15 C8 120.33(10) . 3_566 ?
C9 N15 C1 120.92(10) . . ?
C22 N1 C34 116.46(10) . . ?
C22 N6 C35 120.27(10) . . ?
C22 N6 C24 119.85(10) . . ?
C24 N6 C35 119.21(10) . . ?
C8 N13 C11 116.19(11) . . ?
C31 N2 C33 116.35(11) . . ?
C29 N8 C27 116.25(11) . . ?
C9 N14 C15 116.05(11) . . ?
C29 N5 C44 120.2(5) . . ?
C29 N5 C44A 117.5(4) . . ?
C31 N5 C29 119.71(10) . . ?
C31 N5 C44 118.6(5) . . ?
C31 N5 C44A 122.8(5) . . ?
C24 N7 C26 116.42(11) . . ?
N15 C8 C9 120.18(10) 3_566 . ?
N13 C8 N15 118.03(11) . 3_566 ?
N13 C8 C9 121.78(11) . . ?
N15 C9 C8 119.49(10) . . ?
N14 C9 N15 118.79(11) . . ?
N14 C9 C8 121.71(11) . . ?
N1 C22 N6 118.98(11) . . ?
N1 C22 C31 121.18(11) . . ?
N6 C22 C31 119.82(11) . . ?
C40 C35 N6 117.80(11) . . ?
C36 C35 N6 119.45(11) . . ?
C36 C35 C40 122.72(11) . . ?
N1 C34 C53 117.71(11) . . ?
N1 C34 C33 121.99(11) . . ?
C33 C34 C53 120.30(12) . . ?
C35 C40 C42 121.25(12) . . ?
C39 C40 C35 117.50(12) . . ?
C39 C40 C42 121.23(12) . . ?
N4 C53 C34 177.94(15) . . ?
C2 C1 N15 117.02(11) . . ?
C6 C1 N15 119.19(11) . . ?
C6 C1 C2 123.70(11) . . ?
N8 C29 N5 117.89(11) . . ?
N8 C29 C24 121.78(11) . . ?
N5 C29 C24 120.29(11) . . ?
N2 C33 C34 121.98(12) . . ?
N2 C33 C59 116.37(11) . . ?
C34 C33 C59 121.64(12) . . ?
N13 C11 C15 122.32(11) . . ?
N13 C11 C12 115.73(13) . . ?
C15 C11 C12 121.93(13) . . ?
N6 C24 C29 119.90(11) . . ?
N7 C24 N6 118.53(11) . . ?
N7 C24 C29 121.55(11) . . ?
N2 C31 N5 118.12(11) . . ?
N2 C31 C22 121.74(11) . . ?
N5 C31 C22 120.12(11) . . ?
C1 C2 C18 120.59(11) . . ?
C3 C2 C1 116.97(12) . . ?
C3 C2 C18 122.43(12) . . ?
N3 C59 C33 178.42(19) . . ?
N8 C27 C26 122.07(12) . . ?
N8 C27 C55 115.11(12) . . ?
C26 C27 C55 122.73(12) . . ?
N7 C26 C27 121.82(12) . . ?
N7 C26 C57 116.87(12) . . ?
C27 C26 C57 121.21(13) . . ?
N14 C15 C11 121.94(12) . . ?
N14 C15 C16 116.66(13) . . ?
C11 C15 C16 121.39(13) . . ?
C40 C39 H39 119.1 . . ?
C38 C39 C40 121.76(12) . . ?
C38 C39 H39 119.1 . . ?
C39 C38 C43 120.61(15) . . ?
C37 C38 C39 118.44(13) . . ?
C37 C38 C43 120.94(16) . . ?
C1 C6 C5 116.98(12) . . ?
C1 C6 C19 122.16(12) . . ?
C5 C6 C19 120.85(13) . . ?
C35 C36 C37 117.23(12) . . ?
C35 C36 C41 121.49(13) . . ?
C37 C36 C41 121.27(13) . . ?
N11 C12 C11 178.60(19) . . ?
N10 C55 C27 176.20(16) . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C45 C44 N5 114.2(6) . . ?
C49 C44 N5 121.8(6) . . ?
C49 C44 C45 123.8(7) . . ?
N9 C57 C26 177.6(2) . . ?
C38 C37 C36 122.23(14) . . ?
C38 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.70(14) . . ?
C4 C5 H5 119.2 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.49(13) . . ?
C4 C3 H3 119.3 . . ?
N12 C16 C15 178.0(2) . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C4 C3 119.15(13) . . ?
C5 C4 C20 120.28(16) . . ?
C3 C4 C20 120.57(16) . . ?
C44 C45 C51 122.1(7) . . ?
C44 C45 C46 117.7(7) . . ?
C46 C45 C51 120.1(7) . . ?
C44 C49 C48 115.8(6) . . ?
C44 C49 C52 121.8(7) . . ?
C48 C49 C52 122.4(6) . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C49 C48 H48 118.8 . . ?
C47 C48 C49 122.5(5) . . ?
C47 C48 H48 118.8 . . ?
C38 C43 H43A 109.5 . . ?
C38 C43 H43B 109.5 . . ?
C38 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C51 H51A 109.5 . . ?
C45 C51 H51B 109.5 . . ?
C45 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C45 C46 H46 120.0 . . ?
C47 C46 C45 120.1(6) . . ?
C47 C46 H46 120.0 . . ?
C49 C52 H52A 109.5 . . ?
C49 C52 H52B 109.5 . . ?
C49 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C48 C47 C50 122.6(6) . . ?
C46 C47 C48 120.0(5) . . ?
C46 C47 C50 117.4(7) . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C67 C62 C63 120.0 . . ?
C67 C62 C66 117.8(5) . . ?
C63 C62 C66 122.2(5) . . ?
C62 C67 H67 120.0 . . ?
C62 C67 C61 120.0 . . ?
C61 C67 H67 120.0 . . ?
C67 C61 H61 120.0 . . ?
C65 C61 C67 120.0 . . ?
C65 C61 H61 120.0 . . ?
C61 C65 H65 120.0 . . ?
C64 C65 C61 120.0 . . ?
C64 C65 H65 120.0 . . ?
C65 C64 H64 120.0 . . ?
C65 C64 C63 120.0 . . ?
C63 C64 H64 120.0 . . ?
C62 C63 H63 120.0 . . ?
C64 C63 C62 120.0 . . ?
C64 C63 H63 120.0 . . ?
C62 C66 H66A 109.5 . . ?
C62 C66 H66B 109.5 . . ?
C62 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
H66D C66A H66E 109.5 . . ?
H66D C66A H66F 109.5 . . ?
H66E C66A H66F 109.5 . . ?
C62A C66A H66D 109.5 . . ?
C62A C66A H66E 109.5 . . ?
C62A C66A H66F 109.5 . . ?
C67A C62A C66A 120.5(6) . . ?
C67A C62A C63A 120.0 . . ?
C63A C62A C66A 119.5(6) . . ?
C62A C67A H67A 120.0 . . ?
C62A C67A C61A 120.0 . . ?
C61A C67A H67A 120.0 . . ?
C67A C61A H61A 120.0 . . ?
C67A C61A C65A 120.0 . . ?
C65A C61A H61A 120.0 . . ?
C61A C65A H65A 120.0 . . ?
C64A C65A C61A 120.0 . . ?
C64A C65A H65A 120.0 . . ?
C65A C64A H64A 120.0 . . ?
C65A C64A C63A 120.0 . . ?
C63A C64A H64A 120.0 . . ?
C62A C63A H63A 120.0 . . ?
C64A C63A C62A 120.0 . . ?
C64A C63A H63A 120.0 . . ?
C14 C7 C17 120.0 . . ?
C14 C7 C23 109.6(4) . . ?
C17 C7 C23 130.4(4) . . ?
C7 C14 H14 120.0 . . ?
C10 C14 C7 120.0 . . ?
C10 C14 H14 120.0 . . ?
C14 C10 H10 120.0 . . ?
C21 C10 C14 120.0 . . ?
C21 C10 H10 120.0 . . ?
C10 C21 H21 120.0 . . ?
C68 C21 C10 120.0 . . ?
C68 C21 H21 120.0 . . ?
C21 C68 H68 120.0 . . ?
C21 C68 C17 120.0 . . ?
C17 C68 H68 120.0 . . ?
C7 C17 H17 120.0 . . ?
C68 C17 C7 120.0 . . ?
C68 C17 H17 120.0 . . ?
C7 C23 H23A 109.5 . . ?
C7 C23 H23B 109.5 . . ?
C7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H51D C51A H51E 109.5 . . ?
H51D C51A H51F 109.5 . . ?
H51E C51A H51F 109.5 . . ?
C45A C51A H51D 109.5 . . ?
C45A C51A H51E 109.5 . . ?
C45A C51A H51F 109.5 . . ?
C46A C45A C51A 120.9(8) . . ?
C44A C45A C51A 122.3(8) . . ?
C44A C45A C46A 116.7(6) . . ?
C45A C46A H46A 118.5 . . ?
C47A C46A C45A 123.1(5) . . ?
C47A C46A H46A 118.5 . . ?
C46A C47A C50A 121.1(5) . . ?
C46A C47A C48A 118.6(5) . . ?
C48A C47A C50A 120.3(5) . . ?
C47A C50A H50D 109.5 . . ?
C47A C50A H50E 109.5 . . ?
C47A C50A H50F 109.5 . . ?
H50D C50A H50E 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?
C47A C48A H48A 119.8 . . ?
C47A C48A C49A 120.3(5) . . ?
C49A C48A H48A 119.8 . . ?
C48A C49A C52A 119.7(6) . . ?
C44A C49A C48A 119.0(5) . . ?
C44A C49A C52A 121.3(6) . . ?
C45A C44A N5 122.1(6) . . ?
C45A C44A C49A 122.2(6) . . ?
C49A C44A N5 115.6(5) . . ?
C49A C52A H52D 109.5 . . ?
C49A C52A H52E 109.5 . . ?
C49A C52A H52F 109.5 . . ?
H52D C52A H52E 109.5 . . ?
H52D C52A H52F 109.5 . . ?
H52E C52A H52F 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
N15 C8 C9 N15 0.19(18) 3_566 . . . ?
N15 C8 C9 N14 -179.43(11) 3_566 . . . ?
N15 C1 C2 C18 -1.55(18) . . . . ?
N15 C1 C2 C3 177.33(12) . . . . ?
N15 C1 C6 C5 -177.17(13) . . . . ?
N15 C1 C6 C19 2.1(2) . . . . ?
N1 C22 C31 N2 6.24(19) . . . . ?
N1 C22 C31 N5 -175.63(11) . . . . ?
N1 C34 C33 N2 4.2(2) . . . . ?
N1 C34 C33 C59 -174.72(12) . . . . ?
N6 C22 C31 N2 -171.81(11) . . . . ?
N6 C22 C31 N5 6.32(18) . . . . ?
N6 C35 C40 C39 179.34(11) . . . . ?
N6 C35 C40 C42 0.93(19) . . . . ?
N6 C35 C36 C37 -178.61(13) . . . . ?
N6 C35 C36 C41 2.0(2) . . . . ?
N13 C8 C9 N15 179.65(11) . . . . ?
N13 C8 C9 N14 0.03(18) . . . . ?
N13 C11 C15 N14 0.1(2) . . . . ?
N13 C11 C15 C16 -178.83(14) . . . . ?
N8 C29 C24 N6 -178.96(11) . . . . ?
N8 C29 C24 N7 2.71(19) . . . . ?
N8 C27 C26 N7 2.2(2) . . . . ?
N8 C27 C26 C57 -173.91(13) . . . . ?
N5 C29 C24 N6 3.28(18) . . . . ?
N5 C29 C24 N7 -175.06(12) . . . . ?
N5 C44 C45 C51 4.3(16) . . . . ?
N5 C44 C45 C46 -175.0(8) . . . . ?
N5 C44 C49 C48 175.9(8) . . . . ?
N5 C44 C49 C52 -4.6(16) . . . . ?
C8 N15 C9 N14 179.44(11) 3_566 . . . ?
C8 N15 C9 C8 -0.19(18) 3_566 . . . ?
C8 N15 C1 C2 -92.39(14) 3_566 . . . ?
C8 N15 C1 C6 84.35(15) 3_566 . . . ?
C8 N13 C11 C15 -0.42(19) . . . . ?
C8 N13 C11 C12 -178.78(12) . . . . ?
C9 N15 C1 C2 82.67(15) . . . . ?
C9 N15 C1 C6 -100.59(14) . . . . ?
C9 N14 C15 C11 0.29(19) . . . . ?
C9 N14 C15 C16 179.27(13) . . . . ?
C22 N1 C34 C53 178.45(11) . . . . ?
C22 N1 C34 C33 -1.57(18) . . . . ?
C22 N6 C35 C40 -79.81(15) . . . . ?
C22 N6 C35 C36 102.35(14) . . . . ?
C22 N6 C24 N7 176.39(11) . . . . ?
C22 N6 C24 C29 -2.00(17) . . . . ?
C35 N6 C22 N1 -10.22(16) . . . . ?
C35 N6 C22 C31 167.86(11) . . . . ?
C35 N6 C24 N7 5.74(17) . . . . ?
C35 N6 C24 C29 -172.65(11) . . . . ?
C35 C40 C39 C38 -0.5(2) . . . . ?
C35 C36 C37 C38 -1.1(3) . . . . ?
C34 N1 C22 N6 174.74(10) . . . . ?
C34 N1 C22 C31 -3.32(17) . . . . ?
C40 C35 C36 C37 3.7(2) . . . . ?
C40 C35 C36 C41 -175.72(16) . . . . ?
C40 C39 C38 C37 2.9(2) . . . . ?
C40 C39 C38 C43 -175.60(16) . . . . ?
C53 C34 C33 N2 -175.87(12) . . . . ?
C53 C34 C33 C59 5.3(2) . . . . ?
C1 N15 C9 N14 4.46(17) . . . . ?
C1 N15 C9 C8 -175.17(11) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C29 N8 C27 C26 0.95(19) . . . . ?
C29 N8 C27 C55 -175.63(12) . . . . ?
C29 N5 C31 N2 173.14(12) . . . . ?
C29 N5 C31 C22 -5.06(18) . . . . ?
C29 N5 C44 C45 88.8(10) . . . . ?
C29 N5 C44 C49 -86.9(10) . . . . ?
C29 N5 C44A C45A 83.1(10) . . . . ?
C29 N5 C44A C49A -95.8(8) . . . . ?
C33 N2 C31 N5 178.24(11) . . . . ?
C33 N2 C31 C22 -3.60(18) . . . . ?
C11 N13 C8 N15 179.82(11) . . . 3_566 ?
C11 N13 C8 C9 0.35(17) . . . . ?
C24 N6 C22 N1 179.23(11) . . . . ?
C24 N6 C22 C31 -2.69(17) . . . . ?
C24 N6 C35 C40 90.80(14) . . . . ?
C24 N6 C35 C36 -87.04(15) . . . . ?
C24 N7 C26 C27 -2.76(19) . . . . ?
C24 N7 C26 C57 173.49(12) . . . . ?
C31 N2 C33 C34 -1.33(19) . . . . ?
C31 N2 C33 C59 177.60(12) . . . . ?
C31 N5 C29 N8 -177.51(12) . . . . ?
C31 N5 C29 C24 0.34(18) . . . . ?
C31 N5 C44 C45 -105.3(9) . . . . ?
C31 N5 C44 C49 79.0(11) . . . . ?
C31 N5 C44A C45A -96.6(9) . . . . ?
C31 N5 C44A C49A 84.5(9) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C19 178.58(14) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C20 179.5(2) . . . . ?
C27 N8 C29 N5 174.55(11) . . . . ?
C27 N8 C29 C24 -3.27(18) . . . . ?
C26 N7 C24 N6 -177.91(11) . . . . ?
C26 N7 C24 C29 0.45(18) . . . . ?
C15 N14 C9 N15 -179.98(11) . . . . ?
C15 N14 C9 C8 -0.35(18) . . . . ?
C39 C38 C37 C36 -2.0(3) . . . . ?
C6 C1 C2 C18 -178.14(13) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C6 C5 C4 C20 -179.4(2) . . . . ?
C36 C35 C40 C39 -2.9(2) . . . . ?
C36 C35 C40 C42 178.70(14) . . . . ?
C12 C11 C15 N14 178.36(13) . . . . ?
C12 C11 C15 C16 -0.6(2) . . . . ?
C55 C27 C26 N7 178.50(13) . . . . ?
C55 C27 C26 C57 2.4(2) . . . . ?
C18 C2 C3 C4 178.51(16) . . . . ?
C44 N5 C29 N8 -11.8(4) . . . . ?
C44 N5 C29 C24 166.1(4) . . . . ?
C44 N5 C31 N2 7.2(4) . . . . ?
C44 N5 C31 C22 -171.0(4) . . . . ?
C44 C45 C46 C47 -0.2(14) . . . . ?
C44 C49 C48 C47 -2.4(12) . . . . ?
C42 C40 C39 C38 177.94(15) . . . . ?
C19 C6 C5 C4 -179.08(18) . . . . ?
C45 C44 C49 C48 0.6(16) . . . . ?
C45 C44 C49 C52 -179.9(11) . . . . ?
C45 C46 C47 C48 -1.5(11) . . . . ?
C45 C46 C47 C50 -179.8(8) . . . . ?
C49 C44 C45 C51 179.9(11) . . . . ?
C49 C44 C45 C46 0.6(17) . . . . ?
C49 C48 C47 C46 2.9(11) . . . . ?
C49 C48 C47 C50 -178.9(7) . . . . ?
C41 C36 C37 C38 178.27(17) . . . . ?
C43 C38 C37 C36 176.42(17) . . . . ?
C51 C45 C46 C47 -179.5(9) . . . . ?
C52 C49 C48 C47 178.1(8) . . . . ?
C62 C67 C61 C65 0.0 . . . . ?
C67 C62 C63 C64 0.0 . . . . ?
C67 C61 C65 C64 0.0 . . . . ?
C61 C65 C64 C63 0.0 . . . . ?
C65 C64 C63 C62 0.0 . . . . ?
C63 C62 C67 C61 0.0 . . . . ?
C66 C62 C67 C61 -178.4(4) . . . . ?
C66 C62 C63 C64 178.3(4) . . . . ?
C66A C62A C67A C61A 178.5(5) . . . . ?
C66A C62A C63A C64A -178.5(5) . . . . ?
C62A C67A C61A C65A 0.0 . . . . ?
C67A C62A C63A C64A 0.0 . . . . ?
C67A C61A C65A C64A 0.0 . . . . ?
C61A C65A C64A C63A 0.0 . . . . ?
C65A C64A C63A C62A 0.0 . . . . ?
C63A C62A C67A C61A 0.0 . . . . ?
C7 C14 C10 C21 0.0 . . . . ?
C14 C7 C17 C68 0.0 . . . . ?
C14 C10 C21 C68 0.0 . . . . ?
C10 C21 C68 C17 0.0 . . . . ?
C21 C68 C17 C7 0.0 . . . . ?
C17 C7 C14 C10 0.0 . . . . ?
C23 C7 C14 C10 179.0(4) . . . . ?
C23 C7 C17 C68 -178.7(5) . . . . ?
C51A C45A C46A C47A 178.9(10) . . . . ?
C51A C45A C44A N5 2.5(17) . . . . ?
C51A C45A C44A C49A -178.7(11) . . . . ?
C45A C46A C47A C50A -179.7(8) . . . . ?
C45A C46A C47A C48A 0.9(11) . . . . ?
C46A C45A C44A N5 -176.1(8) . . . . ?
C46A C45A C44A C49A 2.7(15) . . . . ?
C46A C47A C48A C49A 0.4(10) . . . . ?
C47A C48A C49A C44A -0.2(11) . . . . ?
C47A C48A C49A C52A 179.0(7) . . . . ?
C50A C47A C48A C49A -179.0(7) . . . . ?
C48A C49A C44A N5 177.4(7) . . . . ?
C48A C49A C44A C45A -1.5(15) . . . . ?
C44A N5 C29 N8 2.7(4) . . . . ?
C44A N5 C29 C24 -179.4(3) . . . . ?
C44A N5 C31 N2 -7.1(4) . . . . ?
C44A N5 C31 C22 174.7(3) . . . . ?
C44A C45A C46A C47A -2.5(13) . . . . ?
C52A C49A C44A N5 -1.7(13) . . . . ?
C52A C49A C44A C45A 179.4(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_TCDP-DCM
_database_code_depnum_ccdc_archive 'CCDC 2429939'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, C H2 Cl2'
_chemical_formula_sum            'C31 H24 Cl2 N10'
_chemical_formula_weight         607.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.1431(5)
_cell_length_b                   9.8855(3)
_cell_length_c                   22.1824(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.036(4)
_cell_angle_gamma                90
_cell_volume                     2980.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6124
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.7330
_cell_measurement_theta_min      2.5690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14879
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  37.00   0.50   65.00    --   12.51-118.00 -35.00   50
  2  ω     40.00  81.00   0.50   65.00    --   12.51-159.00 171.00   82
  3  ω    -84.00  12.00   0.50   65.00    --  -11.11 -57.00 -90.00  192
  4  ω    -10.00  78.00   0.50   65.00    --   12.51  57.00-180.00  176
  5  ω     42.00  75.00   0.50   65.00    --   12.51 179.00 -30.00   66
  6  ω     39.00  64.00   0.50   65.00    --   12.51 179.00 -90.00   50
  7  ω    -73.00 -47.00   0.50   65.00    --  -11.11 179.00  60.00   52
  8  ω    -90.00 -64.00   0.50   65.00    --  -11.11 179.00 150.00   52
  9  ω    -85.00 -60.00   0.50   65.00    --  -11.11 159.00-156.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2681
_reflns_number_total             3278
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+3.3969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl22(0.5) Cl23(0.5) C21(0.5) H21A(0.5) H21B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.56735(9) 0.52580(13) 0.55857(6) 0.0190(3) Uani 1 1 d . . . . .
N12 N 0.50169(9) 0.74042(13) 0.55873(6) 0.0215(3) Uani 1 1 d . . . . .
N15 N 0.45336(12) 1.07526(16) 0.57331(8) 0.0373(4) Uani 1 1 d . . . . .
N18 N 0.21104(11) 0.96044(15) 0.43355(7) 0.0323(3) Uani 1 1 d . . . . .
N19 N 0.35630(9) 0.67898(13) 0.44739(6) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.51802(13) 0.3988(2) 0.66132(8) 0.0309(4) Uani 1 1 d . . . . .
H1A H 0.517212 0.326454 0.630971 0.046 Uiso 1 1 calc R U . . .
H1B H 0.460626 0.457385 0.645456 0.046 Uiso 1 1 calc R U . . .
H1C H 0.515966 0.359072 0.701412 0.046 Uiso 1 1 calc R U . . .
C2 C 0.61056(12) 0.48091(17) 0.67070(7) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.67738(13) 0.49537(19) 0.72979(8) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.664291 0.451517 0.764741 0.036 Uiso 1 1 calc R U . . .
C4 C 0.76215(13) 0.5717(2) 0.73894(8) 0.0326(4) Uani 1 1 d . . . . .
C5 C 0.83369(16) 0.5841(3) 0.80340(9) 0.0509(6) Uani 1 1 d . . . . .
H5A H 0.820010 0.667272 0.823498 0.076 Uiso 1 1 calc R U . . .
H5B H 0.901056 0.587009 0.799577 0.076 Uiso 1 1 calc R U . . .
H5C H 0.826409 0.505913 0.828931 0.076 Uiso 1 1 calc R U . . .
C6 C 0.78024(13) 0.63721(18) 0.68769(8) 0.0289(4) Uani 1 1 d . . . . .
H6 H 0.837780 0.691026 0.693866 0.035 Uiso 1 1 calc R U . . .
C7 C 0.71639(11) 0.62605(16) 0.62766(7) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.73625(13) 0.69792(18) 0.57271(8) 0.0290(4) Uani 1 1 d . . . . .
H8A H 0.687849 0.770325 0.558625 0.044 Uiso 1 1 calc R U . . .
H8B H 0.731300 0.633482 0.538405 0.044 Uiso 1 1 calc R U . . .
H8C H 0.802550 0.736810 0.585279 0.044 Uiso 1 1 calc R U . . .
C9 C 0.63347(11) 0.54650(15) 0.62102(7) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.49894(11) 0.62293(15) 0.53084(7) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.43127(11) 0.83048(15) 0.53086(7) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.44167(12) 0.96565(17) 0.55669(8) 0.0261(4) Uani 1 1 d . . . . .
C16 C 0.35743(11) 0.79854(15) 0.47759(7) 0.0205(3) Uani 1 1 d . . . . .
C17 C 0.27682(12) 0.88961(16) 0.45189(7) 0.0235(3) Uani 1 1 d . . . . .
C20 C 0.42732(11) 0.59407(15) 0.47240(7) 0.0184(3) Uani 1 1 d . . . . .
Cl22 Cl 0.4095(5) 0.1660(4) 0.1988(3) 0.111(2) Uani 0.5 1 d . . P A -1
Cl23 Cl 0.5854(4) 0.2130(5) 0.3046(2) 0.1092(14) Uani 0.5 1 d . . P A -1
C21 C 0.4880(6) 0.2547(8) 0.2708(3) 0.091(2) Uani 0.5 1 d . . P A -1
H21A H 0.493528 0.349926 0.258465 0.109 Uiso 0.5 1 calc R U P A -1
H21B H 0.448978 0.255831 0.301650 0.109 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C9 1.4560(19) . ?
N10 C11 1.3812(19) . ?
N10 C20 1.3822(19) 5_666 ?
N12 C11 1.311(2) . ?
N12 C13 1.352(2) . ?
N15 C14 1.142(2) . ?
N18 C17 1.145(2) . ?
N19 C16 1.3564(19) . ?
N19 C20 1.309(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.505(2) . ?
C2 C3 1.396(2) . ?
C2 C9 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 C5 1.511(2) . ?
C4 C6 1.392(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C7 1.392(2) . ?
C7 C8 1.503(2) . ?
C7 C9 1.386(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C20 1.436(2) . ?
C13 C14 1.445(2) . ?
C13 C16 1.380(2) . ?
C16 C17 1.441(2) . ?
Cl22 C21 1.890(10) . ?
Cl23 C21 1.435(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N10 C9 120.85(12) . . ?
C11 N10 C20 120.16(12) . 5_666 ?
C20 N10 C9 118.98(12) 5_666 . ?
C11 N12 C13 116.45(13) . . ?
C20 N19 C16 116.52(13) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.51(15) . . ?
C9 C2 C1 121.71(14) . . ?
C9 C2 C3 116.78(15) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.89(16) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 120.63(17) . . ?
C3 C4 C6 118.77(16) . . ?
C6 C4 C5 120.61(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6 119.1 . . ?
C7 C6 C4 121.84(16) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 121.42(15) . . ?
C9 C7 C6 116.95(15) . . ?
C9 C7 C8 121.63(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 N10 117.33(14) . . ?
C7 C9 N10 118.90(13) . . ?
C7 C9 C2 123.75(14) . . ?
N10 C11 C20 119.77(13) . . ?
N12 C11 N10 118.67(13) . . ?
N12 C11 C20 121.56(14) . . ?
N12 C13 C14 116.50(14) . . ?
N12 C13 C16 121.91(14) . . ?
C16 C13 C14 121.41(14) . . ?
N15 C14 C13 174.39(19) . . ?
N19 C16 C13 121.68(14) . . ?
N19 C16 C17 116.67(13) . . ?
C13 C16 C17 121.64(14) . . ?
N18 C17 C16 177.00(17) . . ?
N10 C20 C11 119.81(13) 5_666 . ?
N19 C20 N10 118.69(13) . 5_666 ?
N19 C20 C11 121.50(13) . . ?
Cl22 C21 H21A 106.2 . . ?
Cl22 C21 H21B 106.2 . . ?
Cl23 C21 Cl22 124.3(4) . . ?
Cl23 C21 H21A 106.2 . . ?
Cl23 C21 H21B 106.2 . . ?
H21A C21 H21B 106.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 C11 C20 N10 -5.8(2) . . . 5_666 ?
N10 C11 C20 N19 174.14(13) . . . . ?
N12 C11 C20 N10 173.75(14) . . . 5_666 ?
N12 C11 C20 N19 -6.3(2) . . . . ?
N12 C13 C16 N19 -5.6(2) . . . . ?
N12 C13 C16 C17 173.35(14) . . . . ?
C1 C2 C3 C4 -179.36(17) . . . . ?
C1 C2 C9 N10 -3.8(2) . . . . ?
C1 C2 C9 C7 178.23(15) . . . . ?
C2 C3 C4 C5 -179.26(18) . . . . ?
C2 C3 C4 C6 0.9(3) . . . . ?
C3 C2 C9 N10 176.49(14) . . . . ?
C3 C2 C9 C7 -1.5(2) . . . . ?
C3 C4 C6 C7 -1.1(3) . . . . ?
C4 C6 C7 C8 179.58(16) . . . . ?
C4 C6 C7 C9 0.0(2) . . . . ?
C5 C4 C6 C7 179.05(18) . . . . ?
C6 C7 C9 N10 -176.66(13) . . . . ?
C6 C7 C9 C2 1.3(2) . . . . ?
C8 C7 C9 N10 3.8(2) . . . . ?
C8 C7 C9 C2 -178.24(15) . . . . ?
C9 N10 C11 N12 7.4(2) . . . . ?
C9 N10 C11 C20 -173.01(13) . . . . ?
C9 C2 C3 C4 0.4(3) . . . . ?
C11 N10 C9 C2 101.61(17) . . . . ?
C11 N10 C9 C7 -80.28(18) . . . . ?
C11 N12 C13 C14 -172.05(14) . . . . ?
C11 N12 C13 C16 3.1(2) . . . . ?
C13 N12 C11 N10 -177.88(13) . . . . ?
C13 N12 C11 C20 2.6(2) . . . . ?
C14 C13 C16 N19 169.30(15) . . . . ?
C14 C13 C16 C17 -11.8(2) . . . . ?
C16 N19 C20 N10 -176.28(13) . . . 5_666 ?
C16 N19 C20 C11 3.8(2) . . . . ?
C20 N10 C9 C2 -77.24(18) 5_666 . . . ?
C20 N10 C9 C7 100.87(16) 5_666 . . . ?
C20 N10 C11 N12 -173.74(13) 5_666 . . . ?
C20 N10 C11 C20 5.8(2) 5_666 . . . ?
C20 N19 C16 C13 1.9(2) . . . . ?
C20 N19 C16 C17 -177.14(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-Ph2O
_database_code_depnum_ccdc_archive 'CCDC 2429937'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H10 O), C30 H22 N10'
_chemical_formula_sum            'C54 H42 N10 O2'
_chemical_formula_weight         862.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6542(6)
_cell_length_b                   11.4847(10)
_cell_length_c                   11.5991(9)
_cell_angle_alpha                112.246(8)
_cell_angle_beta                 95.182(6)
_cell_angle_gamma                103.220(7)
_cell_volume                     1136.23(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      25.3180
_cell_measurement_theta_min      3.2150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.1516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.636
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  28.00   0.50   24.88    --   12.51  57.00 -30.00   60
  2  ω    -39.00  44.00   0.50   24.88    --  -11.11  76.00-132.00  166
  3  ω     54.00  79.00   0.50   24.88    --   12.51  37.00-150.00   50
  4  ω     12.00  46.00   0.50   24.88    --   12.51  37.00-150.00   68
  5  ω     39.00  64.00   0.50   24.88    --   12.51 179.00-150.00   50
  6  ω     55.00  81.00   0.50   24.88    --   12.51 179.00-120.00   52
  7  ω    -90.00 -65.00   0.50   24.88    --  -11.11 179.00-120.00   50
  8  ω    -81.00 -44.00   0.50   24.88    --  -11.11 179.00 -90.00   74
  9  ω    -90.00 -65.00   0.50   24.88    --  -11.11 179.00  90.00   50
 10  ω    -85.00 -44.00   0.50   24.88    --  -11.11 179.00 120.00   82
 11  ω    -67.00  12.00   0.50   24.88    --  -11.11 -57.00 -60.00  158
 12  ω     62.00  90.00   0.50   24.88    --   12.51-179.00 120.00   56
 13  ω    -85.00  16.00   0.50   24.88    --  -11.11 -76.00 101.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2886
_reflns_number_total             5008
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2316
_refine_ls_R_factor_gt           0.1422
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0968P)²+1.0514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2521
_refine_ls_wR_factor_ref         0.2901
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C21(H21), C24(H24), C25(H25), C5(H5), C22(H22), C29(H29), C23(H23),
 C33(H33), C32(H32), C30(H30), C31(H31)
1.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O27 O 0.2010(4) 0.4823(4) 0.1346(4) 0.0407(10) Uani 1 1 d . . . . .
N16 N 0.2572(4) 0.5609(4) 0.4297(4) 0.0256(10) Uani 1 1 d . . . . .
N10 N 0.0673(4) 0.6292(4) 0.5144(4) 0.0277(10) Uani 1 1 d . . . . .
N13 N 0.1092(4) 0.2998(4) 0.3785(4) 0.0283(10) Uani 1 1 d . . . . .
N18 N 0.3379(5) 0.1388(4) 0.2183(5) 0.0457(13) Uani 1 1 d . . . . .
N20 N 0.5728(5) 0.5167(4) 0.3289(5) 0.0446(13) Uani 1 1 d . . . . .
C6 C 0.0747(5) 0.7907(5) 0.4255(5) 0.0262(12) Uani 1 1 d . . . . .
C11 C 0.1305(5) 0.5295(5) 0.4608(5) 0.0241(11) Uani 1 1 d . . . . .
C1 C 0.1293(5) 0.7600(4) 0.5222(5) 0.0248(12) Uani 1 1 d . . . . .
C3 C 0.3007(6) 0.9680(5) 0.6242(5) 0.0353(13) Uani 1 1 d . . . . .
H3 H 0.378530 1.028952 0.691474 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0606(5) 0.3995(5) 0.4398(5) 0.0268(12) Uani 1 1 d . . . . .
C17 C 0.2936(6) 0.2235(5) 0.2727(5) 0.0327(13) Uani 1 1 d . . . . .
C2 C 0.2413(5) 0.8458(5) 0.6228(5) 0.0285(12) Uani 1 1 d . . . . .
C15 C 0.3115(5) 0.4593(5) 0.3726(5) 0.0271(12) Uani 1 1 d . . . . .
C26 C 0.2593(5) 0.5834(5) 0.1003(5) 0.0296(12) Uani 1 1 d . . . . .
C28 C 0.1698(5) 0.3521(5) 0.0493(5) 0.0311(12) Uani 1 1 d . . . . .
C21 C 0.2907(5) 0.7079(5) 0.1956(5) 0.0349(13) Uani 1 1 d . . . . .
H21 H 0.278140 0.718912 0.278963 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2391(5) 0.3323(4) 0.3420(5) 0.0263(12) Uani 1 1 d . . . . .
C4 C 0.2510(6) 1.0049(5) 0.5313(5) 0.0342(13) Uani 1 1 d . . . . .
C24 C 0.3357(6) 0.6748(6) -0.0442(6) 0.0376(14) Uani 1 1 d . . . . .
H24 H 0.351562 0.664163 -0.126773 0.045 Uiso 1 1 calc R U . . .
C25 C 0.2845(5) 0.5653(5) -0.0209(5) 0.0338(13) Uani 1 1 d . . . . .
H25 H 0.266919 0.479641 -0.085789 0.041 Uiso 1 1 calc R U . . .
C19 C 0.4579(6) 0.4929(5) 0.3458(5) 0.0300(12) Uani 1 1 d . . . . .
C5 C 0.1377(6) 0.9164(5) 0.4344(5) 0.0314(12) Uani 1 1 d . . . . .
H5 H 0.101272 0.941948 0.371643 0.038 Uiso 1 1 calc R U . . .
C22 C 0.3398(6) 0.8155(6) 0.1705(6) 0.0387(14) Uani 1 1 d . . . . .
H22 H 0.357091 0.900966 0.235510 0.046 Uiso 1 1 calc R U . . .
C29 C 0.0296(6) 0.2740(6) 0.0167(5) 0.0387(14) Uani 1 1 d . . . . .
H29 H -0.045674 0.311138 0.046129 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2909(6) 0.8075(5) 0.7264(5) 0.0384(14) Uani 1 1 d . . . . .
H7A H 0.209513 0.786937 0.766976 0.058 Uiso 1 1 calc R U . . .
H7B H 0.369537 0.880375 0.789808 0.058 Uiso 1 1 calc R U . . .
H7C H 0.325915 0.730176 0.689973 0.058 Uiso 1 1 calc R U . . .
C9 C -0.0442(6) 0.6930(6) 0.3146(5) 0.0414(14) Uani 1 1 d . . . . .
H9A H -0.010313 0.618033 0.266131 0.062 Uiso 1 1 calc R U . . .
H9B H -0.069442 0.735129 0.259561 0.062 Uiso 1 1 calc R U . . .
H9C H -0.129874 0.662622 0.346202 0.062 Uiso 1 1 calc R U . . .
C23 C 0.3644(5) 0.8004(6) 0.0504(6) 0.0411(15) Uani 1 1 d . . . . .
H23 H 0.400544 0.875046 0.033082 0.049 Uiso 1 1 calc R U . . .
C33 C 0.2796(6) 0.2985(6) 0.0051(5) 0.0412(14) Uani 1 1 d . . . . .
H33 H 0.376977 0.352469 0.027620 0.049 Uiso 1 1 calc R U . . .
C32 C 0.2471(6) 0.1675(6) -0.0710(6) 0.0452(15) Uani 1 1 d . . . . .
H32 H 0.321729 0.130322 -0.102076 0.054 Uiso 1 1 calc R U . . .
C30 C -0.0024(6) 0.1427(6) -0.0583(6) 0.0449(15) Uani 1 1 d . . . . .
H30 H -0.099468 0.088439 -0.079706 0.054 Uiso 1 1 calc R U . . .
C31 C 0.1059(7) 0.0894(6) -0.1026(6) 0.0485(16) Uani 1 1 d . . . . .
H31 H 0.083401 -0.001614 -0.155325 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3217(8) 1.1397(6) 0.5377(7) 0.0550(18) Uani 1 1 d . . . . .
H8A H 0.358338 1.201807 0.626709 0.082 Uiso 1 1 calc R U . . .
H8B H 0.250100 1.168739 0.498387 0.082 Uiso 1 1 calc R U . . .
H8C H 0.402405 1.135936 0.492195 0.082 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
O27 C26 1.383(6) . ?
O27 C28 1.388(6) . ?
N16 C11 1.316(6) . ?
N16 C15 1.354(6) . ?
N10 C11 1.385(6) . ?
N10 C1 1.449(6) . ?
N10 C12 1.407(6) 2_566 ?
N13 C12 1.315(6) . ?
N13 C14 1.375(6) . ?
N18 C17 1.140(6) . ?
N20 C19 1.133(6) . ?
C6 C1 1.391(7) . ?
C6 C5 1.392(7) . ?
C6 C9 1.511(8) . ?
C11 C12 1.406(7) . ?
C1 C2 1.384(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.383(7) . ?
C3 C4 1.384(8) . ?
C17 C14 1.449(7) . ?
C2 C7 1.504(8) . ?
C15 C14 1.357(7) . ?
C15 C19 1.470(7) . ?
C26 C21 1.379(7) . ?
C26 C25 1.394(7) . ?
C28 C29 1.369(7) . ?
C28 C33 1.387(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.366(7) . ?
C4 C5 1.378(8) . ?
C4 C8 1.513(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(7) . ?
C24 C23 1.387(8) . ?
C25 H25 0.9500 . ?
C5 H5 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.387(8) . ?
C29 H29 0.9500 . ?
C29 C30 1.368(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C23 H23 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.367(8) . ?
C32 H32 0.9500 . ?
C32 C31 1.378(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.372(8) . ?
C31 H31 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C26 O27 C28 121.0(4) . . ?
C11 N16 C15 115.4(4) . . ?
C11 N10 C1 121.3(4) . . ?
C11 N10 C12 118.5(4) . 2_566 ?
C12 N10 C1 120.2(4) 2_566 . ?
C12 N13 C14 115.1(4) . . ?
C1 C6 C5 116.5(5) . . ?
C1 C6 C9 122.4(5) . . ?
C5 C6 C9 121.1(5) . . ?
N16 C11 N10 117.6(4) . . ?
N16 C11 C12 121.6(4) . . ?
N10 C11 C12 120.8(4) . . ?
C6 C1 N10 117.7(5) . . ?
C2 C1 N10 118.5(5) . . ?
C2 C1 C6 123.8(5) . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(5) . . ?
C4 C3 H3 118.8 . . ?
N13 C12 N10 116.6(4) . 2_566 ?
N13 C12 C11 123.1(4) . . ?
C11 C12 N10 120.3(4) . 2_566 ?
N18 C17 C14 179.2(5) . . ?
C1 C2 C7 120.8(5) . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 C7 122.5(5) . . ?
N16 C15 C14 123.4(4) . . ?
N16 C15 C19 116.4(4) . . ?
C14 C15 C19 120.2(4) . . ?
O27 C26 C25 124.2(5) . . ?
C21 C26 O27 115.2(5) . . ?
C21 C26 C25 120.6(5) . . ?
C29 C28 O27 118.8(4) . . ?
C29 C28 C33 120.1(5) . . ?
C33 C28 O27 120.9(5) . . ?
C26 C21 H21 119.9 . . ?
C22 C21 C26 120.3(5) . . ?
C22 C21 H21 119.9 . . ?
N13 C14 C17 115.9(4) . . ?
C15 C14 N13 121.1(4) . . ?
C15 C14 C17 123.0(4) . . ?
C3 C4 C8 119.8(5) . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 C8 121.6(6) . . ?
C25 C24 H24 119.3 . . ?
C25 C24 C23 121.4(5) . . ?
C23 C24 H24 119.3 . . ?
C26 C25 H25 120.9 . . ?
C24 C25 C26 118.3(5) . . ?
C24 C25 H25 120.9 . . ?
N20 C19 C15 176.9(6) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.1(5) . . ?
C4 C5 H5 119.0 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(5) . . ?
C23 C22 H22 119.9 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.1(5) . . ?
C30 C29 H29 119.9 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C24 C23 H23 120.5 . . ?
C22 C23 C24 119.1(5) . . ?
C22 C23 H23 120.5 . . ?
C28 C33 H33 120.2 . . ?
C32 C33 C28 119.6(5) . . ?
C32 C33 H33 120.2 . . ?
C33 C32 H32 120.0 . . ?
C33 C32 C31 119.9(5) . . ?
C31 C32 H32 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0(5) . . ?
C31 C30 H30 120.0 . . ?
C32 C31 H31 119.9 . . ?
C30 C31 C32 120.3(6) . . ?
C30 C31 H31 119.9 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O27 C26 C21 C22 -175.7(5) . . . . ?
O27 C26 C25 C24 176.4(5) . . . . ?
O27 C28 C29 C30 -174.2(5) . . . . ?
O27 C28 C33 C32 174.9(5) . . . . ?
N16 C11 C12 N10 173.5(5) . . . 2_566 ?
N16 C11 C12 N13 -6.2(8) . . . . ?
N16 C15 C14 N13 -6.1(8) . . . . ?
N16 C15 C14 C17 175.4(5) . . . . ?
N10 C11 C12 N10 -6.9(8) . . . 2_566 ?
N10 C11 C12 N13 173.4(5) . . . . ?
N10 C1 C2 C3 177.8(4) . . . . ?
N10 C1 C2 C7 -4.0(6) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C6 C1 C2 C7 177.7(4) . . . . ?
C11 N16 C15 C14 3.5(7) . . . . ?
C11 N16 C15 C19 -175.4(5) . . . . ?
C11 N10 C1 C6 94.8(5) . . . . ?
C11 N10 C1 C2 -83.6(6) . . . . ?
C1 N10 C11 N16 7.2(7) . . . . ?
C1 N10 C11 C12 -172.3(5) . . . . ?
C1 C6 C5 C4 1.9(7) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
C12 N10 C11 N16 -173.6(4) 2_566 . . . ?
C12 N10 C11 C12 6.8(8) 2_566 . . . ?
C12 N10 C1 C6 -84.4(5) 2_566 . . . ?
C12 N10 C1 C2 97.3(5) 2_566 . . . ?
C12 N13 C14 C17 -179.1(5) . . . . ?
C12 N13 C14 C15 2.2(7) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C2 C3 C4 C8 -179.4(5) . . . . ?
C15 N16 C11 N10 -177.2(4) . . . . ?
C15 N16 C11 C12 2.3(7) . . . . ?
C26 O27 C28 C29 -119.7(5) . . . . ?
C26 O27 C28 C33 65.3(7) . . . . ?
C26 C21 C22 C23 -2.8(8) . . . . ?
C28 O27 C26 C21 -177.4(4) . . . . ?
C28 O27 C26 C25 3.4(7) . . . . ?
C28 C29 C30 C31 -1.1(9) . . . . ?
C28 C33 C32 C31 -0.5(9) . . . . ?
C21 C26 C25 C24 -2.7(7) . . . . ?
C21 C22 C23 C24 1.3(8) . . . . ?
C14 N13 C12 N10 -176.1(4) . . . 2_566 ?
C14 N13 C12 C11 3.6(7) . . . . ?
C4 C3 C2 C1 0.7(7) . . . . ?
C4 C3 C2 C7 -177.4(5) . . . . ?
C25 C26 C21 C22 3.5(8) . . . . ?
C25 C24 C23 C22 -0.6(8) . . . . ?
C19 C15 C14 N13 172.8(5) . . . . ?
C19 C15 C14 C17 -5.7(8) . . . . ?
C5 C6 C1 N10 -179.1(4) . . . . ?
C5 C6 C1 C2 -0.8(6) . . . . ?
C29 C28 C33 C32 0.0(9) . . . . ?
C29 C30 C31 C32 0.6(10) . . . . ?
C9 C6 C1 N10 -0.5(6) . . . . ?
C9 C6 C1 C2 177.8(4) . . . . ?
C9 C6 C5 C4 -176.8(5) . . . . ?
C23 C24 C25 C26 1.2(8) . . . . ?
C33 C28 C29 C30 0.8(8) . . . . ?
C33 C32 C31 C30 0.2(9) . . . . ?
C8 C4 C5 C6 178.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-DCE
_database_code_depnum_ccdc_archive 'CCDC 2429940'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 H4 Cl2), C30 H22 N10'
_chemical_formula_sum            'C34 H30 Cl4 N10'
_chemical_formula_weight         720.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.2866(4)
_cell_length_b                   8.6175(3)
_cell_length_c                   16.7215(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.982(3)
_cell_angle_gamma                90
_cell_volume                     1770.21(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6286
_cell_measurement_temperature    200.15
_cell_measurement_theta_max      31.3060
_cell_measurement_theta_min      2.8790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13167
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  36.00   0.50   12.00    --    5.08 -99.00  60.00   74
  2  ω    -11.00  14.00   0.50   12.00    --    5.08 -99.00 -60.00   50
  3  ω     -9.00  35.00   0.50   12.00    --    5.08  57.00 150.00   88
  4  ω    -53.00  27.00   0.50   12.00    --    5.08 -77.00 -30.00  160
  5  ω     -3.00  61.00   0.50   12.00    --    5.08  37.00  60.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2809
_reflns_number_total             3239
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+1.4252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl21-C22 \\sim Cl25-C24A \\sim Cl1-C23 \\sim Cl24-C23A
 with sigma of 0.01
 C24A-C23 \\sim C23A-C22
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl25 \\sim C24A \\sim C23 \\sim Cl1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Others
 Sof(Cl1)=Sof(C23)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(Cl25)=
 1-FVAR(1)
 Sof(Cl21)=Sof(Cl24)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23A)=Sof(H23A)=
 Sof(H23B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23A(H23A,H23B), C23(H23C,H23D), C24A(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl21 Cl 0.21708(8) 1.07428(10) 0.31103(11) 0.0552(3) Uani 0.863(3) 1 d D . P A
1
Cl24 Cl 0.42556(7) 0.87319(10) 0.39444(5) 0.0570(3) Uani 0.863(3) 1 d D . P A 1
N10 N 0.10565(11) 0.54500(17) 0.52378(8) 0.0192(3) Uani 1 1 d . . . . .
N13 N -0.04397(12) 0.40134(17) 0.34912(8) 0.0214(3) Uani 1 1 d . . . . .
N16 N 0.16477(11) 0.50622(17) 0.39464(8) 0.0210(3) Uani 1 1 d . . . . .
N18 N 0.00261(13) 0.2919(2) 0.15591(10) 0.0345(4) Uani 1 1 d . . . . .
C11 C 0.08462(14) 0.50123(19) 0.44553(10) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.21690(13) 0.5818(2) 0.54851(10) 0.0200(4) Uani 1 1 d . . . . .
C12 C -0.02227(13) 0.45148(19) 0.42175(10) 0.0185(4) Uani 1 1 d . . . . .
C15 C 0.14125(14) 0.4587(2) 0.31913(10) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.03994(14) 0.4042(2) 0.29710(10) 0.0216(4) Uani 1 1 d . . . . .
C2 C 0.28790(14) 0.4587(2) 0.56341(10) 0.0235(4) Uani 1 1 d . . . . .
N20 N 0.29890(15) 0.4755(2) 0.21887(11) 0.0420(5) Uani 1 1 d . . . . .
C6 C 0.24780(14) 0.7366(2) 0.55382(10) 0.0245(4) Uani 1 1 d . . . . .
C17 C 0.01816(14) 0.3432(2) 0.21808(11) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.39514(15) 0.4957(2) 0.58388(11) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.445565 0.414230 0.594116 0.035 Uiso 1 1 calc R U . . .
C19 C 0.22933(15) 0.4671(2) 0.26301(11) 0.0269(4) Uani 1 1 d . . . . .
C5 C 0.35604(15) 0.7671(2) 0.57550(11) 0.0298(4) Uani 1 1 d . . . . .
H5 H 0.379424 0.871754 0.580635 0.036 Uiso 1 1 calc R U . . .
C4 C 0.43038(15) 0.6483(3) 0.58974(11) 0.0318(5) Uani 1 1 d . . . . .
C7 C 0.25238(16) 0.2924(2) 0.55626(13) 0.0326(5) Uani 1 1 d . . . . .
H7A H 0.185103 0.277190 0.585923 0.049 Uiso 1 1 calc R U . . .
H7B H 0.309429 0.224609 0.578414 0.049 Uiso 1 1 calc R U . . .
H7C H 0.239442 0.266773 0.499792 0.049 Uiso 1 1 calc R U . . .
C9 C 0.16938(17) 0.8663(2) 0.53559(13) 0.0342(5) Uani 1 1 d . . . . .
H9A H 0.132420 0.846400 0.484213 0.051 Uiso 1 1 calc R U . . .
H9B H 0.209247 0.964599 0.532752 0.051 Uiso 1 1 calc R U . . .
H9C H 0.115371 0.872472 0.577924 0.051 Uiso 1 1 calc R U . . .
C22 C 0.2690(2) 0.8903(4) 0.27821(16) 0.0382(7) Uani 0.863(3) 1 d D . P A 1
H22A H 0.231768 0.805979 0.307160 0.046 Uiso 0.863(3) 1 calc R U P A 1
H22B H 0.252605 0.877550 0.220421 0.046 Uiso 0.863(3) 1 calc R U P A 1
C8 C 0.54763(17) 0.6848(3) 0.61124(15) 0.0482(6) Uani 1 1 d . . . . .
H8A H 0.553551 0.710873 0.668195 0.072 Uiso 1 1 calc R U . . .
H8B H 0.572189 0.773129 0.579309 0.072 Uiso 1 1 calc R U . . .
H8C H 0.593133 0.594232 0.600134 0.072 Uiso 1 1 calc R U . . .
C23A C 0.3885(2) 0.8767(4) 0.29217(15) 0.0482(7) Uani 0.863(3) 1 d D . P A 1
H23A H 0.425095 0.965325 0.266302 0.058 Uiso 0.863(3) 1 calc R U P A 1
H23B H 0.414583 0.780321 0.266562 0.058 Uiso 0.863(3) 1 calc R U P A 1
Cl1 Cl 0.4643(5) 0.8971(7) 0.3494(4) 0.068(2) Uiso 0.137(3) 1 d D U P A 2
C23 C 0.3344(8) 0.8158(16) 0.3265(9) 0.033(3) Uiso 0.137(3) 1 d D U P A 2
H23C H 0.340705 0.721208 0.293304 0.040 Uiso 0.137(3) 1 calc R U P A 2
H23D H 0.294123 0.790778 0.375631 0.040 Uiso 0.137(3) 1 calc R U P A 2
C24A C 0.281(2) 0.947(2) 0.2803(11) 0.064(10) Uiso 0.137(3) 1 d D U P A 2
H24A H 0.227746 0.902762 0.241383 0.077 Uiso 0.137(3) 1 calc R U P A 2
H24B H 0.337035 1.002606 0.249758 0.077 Uiso 0.137(3) 1 calc R U P A 2
Cl25 Cl 0.2124(8) 1.0826(11) 0.3423(5) 0.066(3) Uiso 0.137(3) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl21 C22 1.798(3) . ?
Cl24 C23A 1.763(3) . ?
N10 C11 1.382(2) . ?
N10 C1 1.456(2) . ?
N10 C12 1.383(2) 3_566 ?
N13 C12 1.312(2) . ?
N13 C14 1.361(2) . ?
N16 C11 1.313(2) . ?
N16 C15 1.354(2) . ?
N18 C17 1.143(2) . ?
C11 C12 1.431(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.390(3) . ?
C15 C14 1.375(3) . ?
C15 C19 1.446(2) . ?
C14 C17 1.443(2) . ?
C2 C3 1.393(3) . ?
C2 C7 1.502(3) . ?
N20 C19 1.141(2) . ?
C6 C5 1.397(3) . ?
C6 C9 1.504(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.390(3) . ?
C4 C8 1.512(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23A 1.487(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
Cl1 C23 1.779(8) . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C23 C24A 1.514(10) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C24A Cl25 1.782(9) . ?

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
C11 N10 C1 119.19(13) . . ?
C11 N10 C12 120.06(14) . 3_566 ?
C12 N10 C1 120.71(14) 3_566 . ?
C12 N13 C14 116.21(15) . . ?
C11 N16 C15 116.35(15) . . ?
N10 C11 C12 120.04(15) . . ?
N16 C11 N10 118.32(15) . . ?
N16 C11 C12 121.64(15) . . ?
C2 C1 N10 117.84(15) . . ?
C6 C1 N10 118.76(16) . . ?
C6 C1 C2 123.38(16) . . ?
N10 C12 C11 119.81(15) 3_566 . ?
N13 C12 N10 118.41(15) . 3_566 ?
N13 C12 C11 121.78(15) . . ?
N16 C15 C14 122.08(15) . . ?
N16 C15 C19 116.10(16) . . ?
C14 C15 C19 121.82(16) . . ?
N13 C14 C15 121.83(15) . . ?
N13 C14 C17 116.63(15) . . ?
C15 C14 C17 121.52(15) . . ?
C1 C2 C7 122.15(16) . . ?
C3 C2 C1 117.14(17) . . ?
C3 C2 C7 120.70(17) . . ?
C1 C6 C5 117.06(17) . . ?
C1 C6 C9 121.83(16) . . ?
C5 C6 C9 121.09(17) . . ?
N18 C17 C14 178.3(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.83(18) . . ?
C4 C3 H3 119.1 . . ?
N20 C19 C15 179.2(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.71(18) . . ?
C4 C5 H5 119.1 . . ?
C3 C4 C5 118.86(17) . . ?
C3 C4 C8 120.6(2) . . ?
C5 C4 C8 120.5(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Cl21 C22 H22A 109.2 . . ?
Cl21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C23A C22 Cl21 112.1(2) . . ?
C23A C22 H22A 109.2 . . ?
C23A C22 H22B 109.2 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Cl24 C23A H23A 109.0 . . ?
Cl24 C23A H23B 109.0 . . ?
C22 C23A Cl24 113.1(2) . . ?
C22 C23A H23A 109.0 . . ?
C22 C23A H23B 109.0 . . ?
H23A C23A H23B 107.8 . . ?
Cl1 C23 H23C 111.5 . . ?
Cl1 C23 H23D 111.5 . . ?
H23C C23 H23D 109.3 . . ?
C24A C23 Cl1 101.3(14) . . ?
C24A C23 H23C 111.5 . . ?
C24A C23 H23D 111.5 . . ?
C23 C24A H24A 108.9 . . ?
C23 C24A H24B 108.9 . . ?
C23 C24A Cl25 113.5(12) . . ?
H24A C24A H24B 107.7 . . ?
Cl25 C24A H24A 108.9 . . ?
Cl25 C24A H24B 108.9 . . ?

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
Cl21 C22 C23A Cl24 66.4(3) . . . . ?
N10 C11 C12 N10 3.3(3) . . . 3_566 ?
N10 C11 C12 N13 -176.36(15) . . . . ?
N10 C1 C2 C3 177.49(15) . . . . ?
N10 C1 C2 C7 -1.2(2) . . . . ?
N10 C1 C6 C5 -178.20(15) . . . . ?
N10 C1 C6 C9 0.6(2) . . . . ?
N16 C11 C12 N10 -176.90(15) . . . 3_566 ?
N16 C11 C12 N13 3.4(3) . . . . ?
N16 C15 C14 N13 3.0(3) . . . . ?
N16 C15 C14 C17 -175.33(16) . . . . ?
C11 N10 C1 C2 -78.0(2) . . . . ?
C11 N10 C1 C6 100.12(19) . . . . ?
C11 N16 C15 C14 -1.7(2) . . . . ?
C11 N16 C15 C19 178.92(16) . . . . ?
C1 N10 C11 N16 -5.3(2) . . . . ?
C1 N10 C11 C12 174.49(15) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C6 C5 C4 1.2(3) . . . . ?
C12 N10 C11 N16 176.88(15) 3_566 . . . ?
C12 N10 C11 C12 -3.3(3) 3_566 . . . ?
C12 N10 C1 C2 99.78(19) 3_566 . . . ?
C12 N10 C1 C6 -82.1(2) 3_566 . . . ?
C12 N13 C14 C15 -0.9(2) . . . . ?
C12 N13 C14 C17 177.46(16) . . . . ?
C15 N16 C11 N10 178.42(15) . . . . ?
C15 N16 C11 C12 -1.3(2) . . . . ?
C14 N13 C12 N10 178.20(15) . . . 3_566 ?
C14 N13 C12 C11 -2.1(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C9 178.68(17) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C8 -179.35(18) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C1 C2 C7 -179.29(17) . . . . ?
C6 C5 C4 C3 -1.4(3) . . . . ?
C6 C5 C4 C8 178.57(18) . . . . ?
C19 C15 C14 N13 -177.66(17) . . . . ?
C19 C15 C14 C17 4.0(3) . . . . ?
C7 C2 C3 C4 179.05(18) . . . . ?
C9 C6 C5 C4 -177.67(18) . . . . ?
Cl1 C23 C24A Cl25 -88.0(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-PhI
_database_code_depnum_ccdc_archive 'CCDC 2429931'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, C6 H5 I'
_chemical_formula_sum            'C36 H27 I N10'
_chemical_formula_weight         726.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1750(4)
_cell_length_b                   9.1048(5)
_cell_length_c                   11.3499(6)
_cell_angle_alpha                81.725(4)
_cell_angle_beta                 77.867(4)
_cell_angle_gamma                76.129(4)
_cell_volume                     797.93(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      28.2300
_cell_measurement_theta_min      3.1000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.815
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  60.00   0.50    1.08    --  -19.87  57.00  90.00  208
  2  ω     57.00  83.00   0.50    1.08    --   21.12  77.00  30.00   52
  3  ω    -16.00  42.00   0.50    1.08    --   21.12  77.00  30.00  116
  4  ω    -43.00  34.00   0.50    1.08    --   21.12 -57.00 -90.00  154
  5  ω     -1.00  26.00   0.50    1.08    --   21.12-105.00 -95.00   54
  6  ω    -10.00  26.00   0.50    1.08    --  -19.87 -99.00-120.00   72
  7  ω      3.00  34.00   0.50    1.08    --  -19.87 -99.00  30.00   62
  8  ω    -44.00  55.00   0.50    1.08    --   21.12 -57.00 150.00  198
  9  ω    -69.00  -5.00   0.50    1.08    --  -19.87 105.00   4.00  128
 10  ω    -97.00 -13.00   0.50    1.08    --  -19.87 -57.00-180.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2594
_reflns_number_total             3512
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(I21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 I21, C22, C23, C24, C25, C26, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: I21(0.5) C22(0.5) C27(0.5) H27(0.5) C26(0.5) H26(0.5) C25(0.5)
 H25(0.5) C24(0.5) H24(0.5) C23(0.5) H23(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C27(H27), C26(H26), C25(H25), C24(H24), C23(H23)
5.b Fitted hexagon refined as free rotating group:
 C22(C27,C26,C25,C24,C23)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N15 N 0.5955(3) 0.5420(2) 0.88758(18) 0.0238(5) Uani 1 1 d . . . . .
N13 N 0.4582(3) 0.7942(2) 0.90567(19) 0.0259(5) Uani 1 1 d . . . . .
N17 N 0.7453(3) 0.2934(3) 0.87572(19) 0.0267(5) Uani 1 1 d . . . . .
N20 N 1.0198(3) -0.0489(3) 0.8216(2) 0.0413(6) Uani 1 1 d . . . . .
N10 N 0.3057(4) 1.1809(3) 0.8904(2) 0.0442(7) Uani 1 1 d . . . . .
C14 C 0.4767(3) 0.6517(3) 0.9511(2) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.6839(3) 0.5840(3) 0.7659(2) 0.0240(6) Uani 1 1 d . . . . .
C16 C 0.6243(3) 0.3920(3) 0.9357(2) 0.0232(5) Uani 1 1 d . . . . .
C6 C 0.5995(3) 0.5924(3) 0.6708(2) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.8476(3) 0.6132(3) 0.7516(2) 0.0274(6) Uani 1 1 d . . . . .
C12 C 0.3367(3) 0.8961(3) 0.9693(2) 0.0261(6) Uani 1 1 d . . . . .
C18 C 0.7662(3) 0.1469(3) 0.9244(2) 0.0278(6) Uani 1 1 d . . . . .
C19 C 0.9060(3) 0.0388(3) 0.8644(2) 0.0305(6) Uani 1 1 d . . . . .
C5 C 0.6839(3) 0.6341(3) 0.5551(2) 0.0294(6) Uani 1 1 d . . . . .
H5 H 0.629654 0.639843 0.487817 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3187(3) 1.0549(3) 0.9233(2) 0.0316(6) Uani 1 1 d . . . . .
C3 C 0.9234(3) 0.6571(3) 0.6342(3) 0.0306(6) Uani 1 1 d . . . . .
H3 H 1.033280 0.680726 0.621261 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8451(4) 0.6676(3) 0.5356(2) 0.0324(7) Uani 1 1 d . . . . .
C7 C 0.9390(4) 0.5922(4) 0.8562(3) 0.0359(7) Uani 1 1 d . . . . .
H7A H 0.859138 0.634847 0.926359 0.054 Uiso 1 1 calc R U . . .
H7B H 1.034511 0.644478 0.834179 0.054 Uiso 1 1 calc R U . . .
H7C H 0.983224 0.483528 0.876447 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4230(3) 0.5595(4) 0.6918(3) 0.0374(7) Uani 1 1 d . . . . .
H9A H 0.425204 0.457116 0.733205 0.056 Uiso 1 1 calc R U . . .
H9B H 0.386870 0.566046 0.613802 0.056 Uiso 1 1 calc R U . . .
H9C H 0.342112 0.634108 0.741970 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9295(4) 0.7176(4) 0.4098(3) 0.0443(8) Uani 1 1 d . . . . .
H8A H 0.869310 0.695663 0.350425 0.067 Uiso 1 1 calc R U . . .
H8B H 1.049381 0.662491 0.394482 0.067 Uiso 1 1 calc R U . . .
H8C H 0.924578 0.827027 0.402615 0.067 Uiso 1 1 calc R U . . .
I21 I 1.69918(9) 1.09311(8) 0.58410(6) 0.0480(3) Uani 0.5 1 d . U P A -1
C22 C 1.5214(5) 1.0131(6) 0.5174(4) 0.0289(14) Uani 0.5 1 d G U P A -1
C27 C 1.5308(5) 1.0199(5) 0.3931(3) 0.0350(14) Uani 0.5 1 d G U P A -1
H27 H 1.620076 1.057971 0.338924 0.042 Uiso 0.5 1 calc R U P A -1
C26 C 1.4095(6) 0.9710(6) 0.3481(3) 0.0442(15) Uani 0.5 1 d G U P A -1
H26 H 1.415934 0.975626 0.263154 0.053 Uiso 0.5 1 calc R U P A -1
C25 C 1.2789(6) 0.9153(7) 0.4274(4) 0.045(4) Uani 0.5 1 d G U P A -1
H25 H 1.196028 0.881834 0.396654 0.054 Uiso 0.5 1 calc R U P A -1
C24 C 1.2695(5) 0.9085(5) 0.5517(4) 0.0374(13) Uani 0.5 1 d G U P A -1
H24 H 1.180259 0.870389 0.605925 0.045 Uiso 0.5 1 calc R U P A -1
C23 C 1.3908(5) 0.9574(5) 0.5967(3) 0.0352(14) Uani 0.5 1 d G U P A -1
H23 H 1.384400 0.952734 0.681698 0.042 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N15 C14 1.381(3) . ?
N15 C1 1.462(3) . ?
N15 C16 1.379(3) . ?
N13 C14 1.311(3) . ?
N13 C12 1.348(3) . ?
N17 C16 1.309(3) . ?
N17 C18 1.353(3) . ?
N20 C19 1.143(4) . ?
N10 C11 1.142(4) . ?
C14 C16 1.434(3) 2_667 ?
C1 C6 1.382(4) . ?
C1 C2 1.398(3) . ?
C6 C5 1.395(4) . ?
C6 C9 1.507(3) . ?
C2 C3 1.393(4) . ?
C2 C7 1.497(4) . ?
C12 C18 1.383(3) 2_667 ?
C12 C11 1.448(4) . ?
C18 C19 1.437(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 C8 1.507(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
I21 C22 2.084(3) . ?
C22 C27 1.3900 . ?
C22 C23 1.3900 . ?
C27 H27 0.9500 . ?
C27 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C24 1.3900 . ?
C24 H24 0.9500 . ?
C24 C23 1.3900 . ?
C23 H23 0.9500 . ?

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
C14 N15 C1 119.6(2) . . ?
C16 N15 C14 120.4(2) . . ?
C16 N15 C1 119.9(2) . . ?
C14 N13 C12 116.5(2) . . ?
C16 N17 C18 116.4(2) . . ?
N15 C14 C16 119.7(2) . 2_667 ?
N13 C14 N15 118.9(2) . . ?
N13 C14 C16 121.4(2) . 2_667 ?
C6 C1 N15 117.5(2) . . ?
C6 C1 C2 123.7(2) . . ?
C2 C1 N15 118.9(2) . . ?
N15 C16 C14 119.8(2) . 2_667 ?
N17 C16 N15 118.3(2) . . ?
N17 C16 C14 121.9(2) . 2_667 ?
C1 C6 C5 117.1(2) . . ?
C1 C6 C9 121.3(2) . . ?
C5 C6 C9 121.6(3) . . ?
C1 C2 C7 121.8(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 C7 121.9(2) . . ?
N13 C12 C18 122.1(2) . 2_667 ?
N13 C12 C11 117.5(2) . . ?
C18 C12 C11 120.4(3) 2_667 . ?
N17 C18 C12 121.6(2) . 2_667 ?
N17 C18 C19 117.2(2) . . ?
C12 C18 C19 121.2(2) 2_667 . ?
N20 C19 C18 176.9(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
N10 C11 C12 177.8(3) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C8 120.2(3) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C8 121.3(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C27 C22 I21 119.7(2) . . ?
C27 C22 C23 120.0 . . ?
C23 C22 I21 120.2(2) . . ?
C22 C27 H27 120.0 . . ?
C22 C27 C26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?

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
N15 C1 C6 C5 179.3(2) . . . . ?
N15 C1 C6 C9 0.0(4) . . . . ?
N15 C1 C2 C3 -178.1(2) . . . . ?
N15 C1 C2 C7 4.3(4) . . . . ?
C14 N15 C1 C6 -82.6(3) . . . . ?
C14 N15 C1 C2 97.5(3) . . . . ?
C14 N15 C16 N17 -175.9(2) . . . . ?
C14 N15 C16 C14 3.7(4) . . . 2_667 ?
C14 N13 C12 C18 -1.4(4) . . . 2_667 ?
C14 N13 C12 C11 177.6(2) . . . . ?
C1 N15 C14 N13 -6.8(3) . . . . ?
C1 N15 C14 C16 172.9(2) . . . 2_667 ?
C1 N15 C16 N17 7.5(3) . . . . ?
C1 N15 C16 C14 -172.9(2) . . . 2_667 ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C16 N15 C14 N13 176.7(2) . . . . ?
C16 N15 C14 C16 -3.7(4) . . . 2_667 ?
C16 N15 C1 C6 94.0(3) . . . . ?
C16 N15 C1 C2 -85.9(3) . . . . ?
C16 N17 C18 C12 0.9(4) . . . 2_667 ?
C16 N17 C18 C19 -175.8(2) . . . . ?
C6 C1 C2 C3 1.9(4) . . . . ?
C6 C1 C2 C7 -175.7(3) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C6 C5 C4 C8 -177.9(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C9 180.0(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C8 179.1(3) . . . . ?
C12 N13 C14 N15 177.9(2) . . . . ?
C12 N13 C14 C16 -1.7(4) . . . 2_667 ?
C18 N17 C16 N15 -178.2(2) . . . . ?
C18 N17 C16 C14 2.2(4) . . . 2_667 ?
C7 C2 C3 C4 175.8(3) . . . . ?
C9 C6 C5 C4 178.6(3) . . . . ?
I21 C22 C27 C26 -178.1(4) . . . . ?
I21 C22 C23 C24 178.0(4) . . . . ?
C22 C27 C26 C25 0.0 . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-o-DCB
_database_code_depnum_ccdc_archive 'CCDC 2429943'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 Cl2, C30 H22 N10'
_chemical_formula_sum            'C36 H26 Cl2 N10'
_chemical_formula_weight         669.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7987(4)
_cell_length_b                   19.0987(4)
_cell_length_c                   23.8997(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.244(3)
_cell_angle_gamma                90
_cell_volume                     5242.3(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    14428
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      31.2230
_cell_measurement_theta_min      2.4410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2076
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            53311
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  57.00   0.50   10.00    --  -11.26  57.00 -30.00  124
  2  ω     -2.00  90.00   0.50   10.00    --   12.67  37.00 -90.00  184
  3  ω     39.00  90.00   0.50   10.00    --   12.67 179.00-120.00  102
  4  ω    -54.00 -29.00   0.50   10.00    --   12.67 -37.00  60.00   50
  5  ω    -82.00  16.00   0.50   10.00    --  -11.26 -77.00 -30.00  196
  6  ω     22.00  47.00   0.50   10.00    --   12.67-136.00  -2.00   50
  7  ω     33.00  67.00   0.50   10.00    --   12.67-133.00 175.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7710
_reflns_number_total             11561
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         11561
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1217P)²+4.7722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C69 = Cl9-C68
 1.74 with sigma of 0.01
 C73-Cl1 \\sim Cl1-C68
 with sigma of 0.02
 Cl7-C1 \\sim Cl8-C6
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C70 \\sim C68 \\sim C69 \\sim C73 \\sim C72 \\sim C71 \\sim Cl1 \\sim Cl9:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
Uanis(Cl9) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C69) \\sim Ueq,
Uanis(Cl1) \\sim Ueq, Uanis(Cl9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(Cl8) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(Cl7)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: Cl9(0.5) C68(0.5) C69(0.5) C73(0.5) H73(0.5) C72(0.5) H72(0.5)
 C71(0.5) H71(0.5) C70(0.5) H70(0.5) Cl1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C54(H54), C13(H13), C56(H56), C47(H47), C11(H11), C45(H45), C5(H5), C4(H4),
 C3(H3), C2(H2), C73(H73), C72(H72), C71(H71), C70(H70)
5.b Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2), C68(C69,C73,C72,C71,C70)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C50(H50A,H50B,H50C), C26(H26A,H26B,H26C), C59(H59A,H59B,
 H59C), C60(H60A,H60B,H60C), C58(H58A,H58B,H58C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl7 Cl 0.93407(12) 0.30342(8) 0.61464(6) 0.0907(4) Uani 1 1 d D U . . .
Cl8 Cl 0.93063(16) 0.46597(8) 0.63857(8) 0.1256(7) Uani 1 1 d D U . . .
N15 N -0.03445(19) 0.06752(11) 0.47996(9) 0.0241(5) Uani 1 1 d . . . . .
N29 N 0.37088(19) 0.36504(11) 0.77377(9) 0.0250(5) Uani 1 1 d . . . . .
N41 N 0.2411(2) 0.44367(11) 0.79866(9) 0.0268(5) Uani 1 1 d . . . . .
N31 N 0.4933(2) 0.28378(12) 0.74591(10) 0.0284(5) Uani 1 1 d . . . . .
N36 N 0.3651(2) 0.44213(11) 0.67243(10) 0.0290(5) Uani 1 1 d . . . . .
N38 N 0.2297(2) 0.51743(11) 0.69575(10) 0.0282(5) Uani 1 1 d . . . . .
N71 N 0.1094(2) 0.11501(11) 0.55201(10) 0.0288(5) Uani 1 1 d . . . . .
N34 N 0.4828(2) 0.35936(12) 0.64405(10) 0.0326(5) Uani 1 1 d . . . . .
N22 N 0.1801(2) -0.02003(12) 0.59148(10) 0.0291(5) Uani 1 1 d . . . . .
N66 N 0.0425(3) 0.53926(14) 0.85245(12) 0.0436(7) Uani 1 1 d . . . . .
N68 N 0.0265(3) 0.64137(15) 0.70697(13) 0.0516(8) Uani 1 1 d . . . . .
C16 C 0.0566(2) 0.05889(13) 0.52714(11) 0.0239(5) Uani 1 1 d . . . . .
C35 C 0.4296(2) 0.38121(13) 0.68313(12) 0.0275(6) Uani 1 1 d . . . . .
C30 C 0.4338(2) 0.34232(13) 0.73505(11) 0.0254(5) Uani 1 1 d . . . . .
C40 C 0.1715(2) 0.50025(13) 0.78403(11) 0.0259(6) Uani 1 1 d . . . . .
C17 C 0.0926(2) -0.00995(13) 0.54741(11) 0.0239(5) Uani 1 1 d . . . . .
C65 C 0.1008(3) 0.52184(14) 0.82311(12) 0.0317(6) Uani 1 1 d . . . . .
C43 C 0.3608(2) 0.31900(13) 0.82103(11) 0.0264(6) Uani 1 1 d . . . . .
C37 C 0.2987(2) 0.46332(13) 0.70976(11) 0.0252(5) Uani 1 1 d . . . . .
C32 C 0.5460(2) 0.26113(14) 0.70497(12) 0.0301(6) Uani 1 1 d . . . . .
C39 C 0.1653(2) 0.53616(13) 0.73344(12) 0.0269(6) Uani 1 1 d . . . . .
N21 N 0.3026(3) 0.21732(16) 0.64219(13) 0.0552(8) Uani 1 1 d . . . . .
C19 C 0.1992(3) 0.10423(15) 0.59753(12) 0.0329(6) Uani 1 1 d . . . . .
C42 C 0.3032(2) 0.42498(13) 0.76223(11) 0.0253(5) Uani 1 1 d . . . . .
C9 C -0.0722(2) 0.13829(13) 0.46163(11) 0.0261(6) Uani 1 1 d . . . . .
N64 N 0.6491(3) 0.14084(16) 0.71808(14) 0.0564(8) Uani 1 1 d . . . . .
C23 C 0.2348(3) 0.03828(15) 0.61715(12) 0.0317(6) Uani 1 1 d . . . . .
C52 C 0.3569(3) 0.47765(14) 0.61731(12) 0.0295(6) Uani 1 1 d . . . . .
C33 C 0.5406(3) 0.29756(14) 0.65472(13) 0.0318(6) Uani 1 1 d . . . . .
C53 C 0.2745(3) 0.45399(15) 0.57019(12) 0.0347(7) Uani 1 1 d . . . . .
C67 C 0.0889(3) 0.59509(15) 0.71823(13) 0.0347(6) Uani 1 1 d . . . . .
C48 C 0.2654(3) 0.27473(15) 0.81260(13) 0.0326(6) Uani 1 1 d . . . . .
C14 C -0.1583(3) 0.16809(15) 0.48456(12) 0.0324(6) Uani 1 1 d . . . . .
C20 C 0.2569(3) 0.16705(17) 0.62331(14) 0.0410(7) Uani 1 1 d . . . . .
N25 N 0.4122(3) 0.0140(2) 0.70024(14) 0.0682(10) Uani 1 1 d . . . . .
N62 N 0.6225(3) 0.24978(16) 0.57113(14) 0.0609(9) Uani 1 1 d . . . . .
C63 C 0.6039(3) 0.19417(16) 0.71375(13) 0.0364(7) Uani 1 1 d . . . . .
C54 C 0.2741(3) 0.48511(16) 0.51729(13) 0.0383(7) Uani 1 1 d . . . . .
H54 H 0.217913 0.470326 0.484257 0.046 Uiso 1 1 calc R U . . .
C57 C 0.4354(3) 0.53050(16) 0.61413(13) 0.0384(7) Uani 1 1 d . . . . .
C55 C 0.3522(3) 0.53645(16) 0.51140(13) 0.0390(7) Uani 1 1 d . . . . .
C10 C -0.0175(3) 0.17266(15) 0.42417(13) 0.0347(7) Uani 1 1 d . . . . .
C27 C -0.2139(3) 0.12822(17) 0.52519(15) 0.0447(8) Uani 1 1 d . . . . .
H27A H -0.244893 0.083865 0.507411 0.067 Uiso 1 1 calc R U . . .
H27B H -0.277528 0.156018 0.533940 0.067 Uiso 1 1 calc R U . . .
H27C H -0.155771 0.118701 0.560787 0.067 Uiso 1 1 calc R U . . .
C24 C 0.3330(3) 0.02616(18) 0.66404(14) 0.0434(8) Uani 1 1 d . . . . .
C13 C -0.1897(3) 0.23695(16) 0.46883(14) 0.0444(8) Uani 1 1 d . . . . .
H13 H -0.248621 0.259008 0.483804 0.053 Uiso 1 1 calc R U . . .
C61 C 0.5887(3) 0.27101(16) 0.60886(14) 0.0405(7) Uani 1 1 d . . . . .
C44 C 0.4476(3) 0.32038(16) 0.87140(12) 0.0377(7) Uani 1 1 d . . . . .
C56 C 0.4309(3) 0.55892(17) 0.55996(14) 0.0434(8) Uani 1 1 d . . . . .
H56 H 0.484081 0.595088 0.556369 0.052 Uiso 1 1 calc R U . . .
C47 C 0.2565(3) 0.23121(16) 0.85819(16) 0.0445(8) Uani 1 1 d . . . . .
H47 H 0.192725 0.199672 0.853387 0.053 Uiso 1 1 calc R U . . .
C12 C -0.1369(4) 0.27396(17) 0.43184(16) 0.0531(10) Uani 1 1 d . . . . .
C46 C 0.3375(3) 0.23241(19) 0.91029(16) 0.0513(9) Uani 1 1 d . . . . .
C11 C -0.0523(3) 0.24131(16) 0.40965(15) 0.0464(8) Uani 1 1 d . . . . .
H11 H -0.016909 0.266325 0.383806 0.056 Uiso 1 1 calc R U . . .
C45 C 0.4333(3) 0.2757(2) 0.91561(14) 0.0505(9) Uani 1 1 d . . . . .
H45 H 0.491320 0.275073 0.950484 0.061 Uiso 1 1 calc R U . . .
C50 C 0.1740(3) 0.27462(19) 0.75765(15) 0.0484(8) Uani 1 1 d . . . . .
H50A H 0.127322 0.317442 0.755192 0.073 Uiso 1 1 calc R U . . .
H50B H 0.123413 0.233719 0.756741 0.073 Uiso 1 1 calc R U . . .
H50C H 0.211268 0.272615 0.725022 0.073 Uiso 1 1 calc R U . . .
C26 C 0.0755(3) 0.13873(17) 0.39970(17) 0.0504(9) Uani 1 1 d . . . . .
H26A H 0.151678 0.146483 0.425702 0.076 Uiso 1 1 calc R U . . .
H26B H 0.074991 0.159246 0.362060 0.076 Uiso 1 1 calc R U . . .
H26C H 0.060401 0.088328 0.395378 0.076 Uiso 1 1 calc R U . . .
C59 C 0.1915(4) 0.39597(19) 0.57510(15) 0.0512(9) Uani 1 1 d . . . . .
H59A H 0.235168 0.352497 0.585918 0.077 Uiso 1 1 calc R U . . .
H59B H 0.136200 0.389550 0.538049 0.077 Uiso 1 1 calc R U . . .
H59C H 0.149040 0.407997 0.604526 0.077 Uiso 1 1 calc R U . . .
C60 C 0.5234(4) 0.5552(2) 0.66635(16) 0.0631(11) Uani 1 1 d . . . . .
H60A H 0.482909 0.572598 0.695084 0.095 Uiso 1 1 calc R U . . .
H60B H 0.570305 0.592870 0.655396 0.095 Uiso 1 1 calc R U . . .
H60C H 0.574176 0.516089 0.682581 0.095 Uiso 1 1 calc R U . . .
C58 C 0.3516(4) 0.5690(2) 0.45415(15) 0.0541(9) Uani 1 1 d . . . . .
H58A H 0.323762 0.534685 0.423593 0.081 Uiso 1 1 calc R U . . .
H58B H 0.430732 0.583690 0.453234 0.081 Uiso 1 1 calc R U . . .
H58C H 0.299916 0.609811 0.448248 0.081 Uiso 1 1 calc R U . . .
C49 C 0.5530(3) 0.3662(2) 0.87838(17) 0.0593(10) Uani 1 1 d . . . . .
H49A H 0.604088 0.348027 0.854726 0.089 Uiso 1 1 calc R U . . .
H49B H 0.594922 0.366658 0.918825 0.089 Uiso 1 1 calc R U . . .
H49C H 0.528809 0.413984 0.866137 0.089 Uiso 1 1 calc R U . . .
C51 C 0.3204(5) 0.1882(3) 0.9604(2) 0.0859(17) Uani 1 1 d . . . . .
H51A H 0.258014 0.208400 0.976220 0.129 Uiso 1 1 calc R U . . .
H51B H 0.392877 0.187378 0.990289 0.129 Uiso 1 1 calc R U . . .
H51C H 0.299406 0.140404 0.947204 0.129 Uiso 1 1 calc R U . . .
C1 C 0.8912(2) 0.33557(14) 0.67399(10) 0.0696(12) Uani 1 1 d DG U . . .
C6 C 0.8864(3) 0.40707(12) 0.68407(13) 0.0736(12) Uani 1 1 d DG U . . .
C5 C 0.8515(3) 0.43113(10) 0.73238(16) 0.0992(18) Uani 1 1 d G U . . .
H5 H 0.848276 0.479998 0.739263 0.119 Uiso 1 1 calc R U . . .
C4 C 0.8213(3) 0.38369(17) 0.77062(12) 0.0869(15) Uani 1 1 d G U . . .
H4 H 0.797469 0.400133 0.803636 0.104 Uiso 1 1 calc R U . . .
C3 C 0.8261(3) 0.31219(15) 0.76055(11) 0.0854(15) Uani 1 1 d G U . . .
H3 H 0.805453 0.279763 0.786681 0.102 Uiso 1 1 calc R U . . .
C2 C 0.8610(3) 0.28813(9) 0.71223(13) 0.0627(10) Uani 1 1 d G U . . .
H2 H 0.864243 0.239257 0.705351 0.075 Uiso 1 1 calc R U . . .
C28 C -0.1724(6) 0.3493(2) 0.4158(2) 0.100(2) Uani 1 1 d . . . . .
H28A H -0.233892 0.349754 0.380388 0.149 Uiso 1 1 calc R U . . .
H28B H -0.104790 0.375416 0.409628 0.149 Uiso 1 1 calc R U . . .
H28C H -0.201265 0.371081 0.446907 0.149 Uiso 1 1 calc R U . . .
Cl9 Cl 0.5674(2) 0.44486(12) 1.09752(10) 0.0733(6) Uani 0.5 1 d D U P A -1
C68 C 0.5465(7) 0.4969(4) 1.0376(2) 0.083(2) Uani 0.5 1 d DG U P A -1
C69 C 0.4563(7) 0.4845(4) 0.9899(3) 0.094(2) Uani 0.5 1 d DG U P A -1
C73 C 0.4411(6) 0.5282(4) 0.9423(2) 0.100(2) Uani 0.5 1 d DG U P A -1
H73 H 0.379489 0.519687 0.909677 0.120 Uiso 0.5 1 calc R U P A -1
C72 C 0.5161(7) 0.5843(4) 0.9423(3) 0.094(2) Uani 0.5 1 d G U P A -1
H72 H 0.505740 0.614200 0.909775 0.112 Uiso 0.5 1 calc R U P A -1
C71 C 0.6063(6) 0.5968(3) 0.9900(3) 0.091(2) Uani 0.5 1 d G U P A -1
H71 H 0.657533 0.635125 0.990076 0.109 Uiso 0.5 1 calc R U P A -1
C70 C 0.6215(6) 0.5530(4) 1.0377(3) 0.084(2) Uani 0.5 1 d G U P A -1
H70 H 0.683077 0.561538 1.070279 0.101 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.3533(4) 0.4212(3) 0.9910(2) 0.168(2) Uani 0.5 1 d D U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl7 C1 1.725(2) . ?
Cl8 C6 1.726(2) . ?
N15 C16 1.377(3) . ?
N15 C17 1.379(3) 3_556 ?
N15 C9 1.459(3) . ?
N29 C30 1.382(3) . ?
N29 C43 1.458(3) . ?
N29 C42 1.387(3) . ?
N41 C40 1.354(3) . ?
N41 C42 1.309(3) . ?
N31 C30 1.314(3) . ?
N31 C32 1.345(4) . ?
N36 C35 1.382(3) . ?
N36 C37 1.376(3) . ?
N36 C52 1.465(3) . ?
N38 C37 1.311(3) . ?
N38 C39 1.353(3) . ?
N71 C16 1.312(3) . ?
N71 C19 1.349(4) . ?
N34 C35 1.307(3) . ?
N34 C33 1.358(3) . ?
N22 C17 1.310(3) . ?
N22 C23 1.360(4) . ?
N66 C65 1.139(4) . ?
N68 C67 1.142(4) . ?
C16 C17 1.431(3) . ?
C35 C30 1.437(4) . ?
C40 C65 1.447(4) . ?
C40 C39 1.377(4) . ?
C43 C48 1.385(4) . ?
C43 C44 1.390(4) . ?
C37 C42 1.443(4) . ?
C32 C33 1.377(4) . ?
C32 C63 1.443(4) . ?
C39 C67 1.436(4) . ?
N21 C20 1.142(4) . ?
C19 C23 1.376(4) . ?
C19 C20 1.446(4) . ?
C9 C14 1.383(4) . ?
C9 C10 1.383(4) . ?
N64 C63 1.143(4) . ?
C23 C24 1.435(4) . ?
C52 C53 1.384(4) . ?
C52 C57 1.383(4) . ?
C33 C61 1.437(4) . ?
C53 C54 1.396(4) . ?
C53 C59 1.501(4) . ?
C48 C47 1.394(4) . ?
C48 C50 1.497(5) . ?
C14 C27 1.498(4) . ?
C14 C13 1.394(4) . ?
N25 C24 1.142(4) . ?
N62 C61 1.141(4) . ?
C54 H54 0.9500 . ?
C54 C55 1.375(5) . ?
C57 C56 1.394(4) . ?
C57 C60 1.505(5) . ?
C55 C56 1.378(5) . ?
C55 C58 1.501(4) . ?
C10 C11 1.394(4) . ?
C10 C26 1.503(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.386(5) . ?
C44 C45 1.398(5) . ?
C44 C49 1.499(5) . ?
C56 H56 0.9500 . ?
C47 H47 0.9500 . ?
C47 C46 1.385(5) . ?
C12 C11 1.382(5) . ?
C12 C28 1.522(5) . ?
C46 C45 1.382(6) . ?
C46 C51 1.516(5) . ?
C11 H11 0.9500 . ?
C45 H45 0.9500 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C6 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C2 1.3900 . ?
C2 H2 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
Cl9 C68 1.714(5) . ?
C68 C69 1.3900 . ?
C68 C70 1.3900 . ?
C69 C73 1.3900 . ?
C69 Cl1 1.719(6) . ?
C73 H73 0.9500 . ?
C73 C72 1.3900 . ?
C72 H72 0.9500 . ?
C72 C71 1.3900 . ?
C71 H71 0.9500 . ?
C71 C70 1.3900 . ?
C70 H70 0.9500 . ?

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 N15 C17 120.2(2) . 3_556 ?
C16 N15 C9 118.9(2) . . ?
C17 N15 C9 120.8(2) 3_556 . ?
C30 N29 C43 118.7(2) . . ?
C30 N29 C42 120.0(2) . . ?
C42 N29 C43 120.4(2) . . ?
C42 N41 C40 116.4(2) . . ?
C30 N31 C32 116.4(2) . . ?
C35 N36 C52 118.4(2) . . ?
C37 N36 C35 119.9(2) . . ?
C37 N36 C52 121.1(2) . . ?
C37 N38 C39 116.7(2) . . ?
C16 N71 C19 116.4(2) . . ?
C35 N34 C33 116.5(2) . . ?
C17 N22 C23 116.6(2) . . ?
N15 C16 C17 120.1(2) . . ?
N71 C16 N15 118.3(2) . . ?
N71 C16 C17 121.6(2) . . ?
N36 C35 C30 120.2(2) . . ?
N34 C35 N36 118.1(2) . . ?
N34 C35 C30 121.6(2) . . ?
N29 C30 C35 119.9(2) . . ?
N31 C30 N29 118.7(2) . . ?
N31 C30 C35 121.4(2) . . ?
N41 C40 C65 117.8(2) . . ?
N41 C40 C39 122.1(2) . . ?
C39 C40 C65 120.1(2) . . ?
N15 C17 C16 119.7(2) 3_556 . ?
N22 C17 N15 118.6(2) . 3_556 ?
N22 C17 C16 121.7(2) . . ?
N66 C65 C40 177.9(3) . . ?
C48 C43 N29 117.6(2) . . ?
C48 C43 C44 123.4(3) . . ?
C44 C43 N29 119.0(2) . . ?
N36 C37 C42 120.1(2) . . ?
N38 C37 N36 118.6(2) . . ?
N38 C37 C42 121.3(2) . . ?
N31 C32 C33 122.4(2) . . ?
N31 C32 C63 117.5(2) . . ?
C33 C32 C63 120.0(3) . . ?
N38 C39 C40 121.9(2) . . ?
N38 C39 C67 117.0(2) . . ?
C40 C39 C67 121.1(2) . . ?
N71 C19 C23 122.5(2) . . ?
N71 C19 C20 115.0(3) . . ?
C23 C19 C20 122.5(3) . . ?
N29 C42 C37 119.8(2) . . ?
N41 C42 N29 118.5(2) . . ?
N41 C42 C37 121.7(2) . . ?
C14 C9 N15 117.6(2) . . ?
C14 C9 C10 123.7(2) . . ?
C10 C9 N15 118.6(2) . . ?
N22 C23 C19 121.3(3) . . ?
N22 C23 C24 115.8(3) . . ?
C19 C23 C24 122.9(3) . . ?
C53 C52 N36 118.0(2) . . ?
C57 C52 N36 118.7(3) . . ?
C57 C52 C53 123.2(3) . . ?
N34 C33 C32 121.6(2) . . ?
N34 C33 C61 115.6(2) . . ?
C32 C33 C61 122.7(3) . . ?
C52 C53 C54 117.0(3) . . ?
C52 C53 C59 121.8(3) . . ?
C54 C53 C59 121.2(3) . . ?
N68 C67 C39 178.4(3) . . ?
C43 C48 C47 117.0(3) . . ?
C43 C48 C50 121.8(3) . . ?
C47 C48 C50 121.1(3) . . ?
C9 C14 C27 121.2(2) . . ?
C9 C14 C13 117.1(3) . . ?
C13 C14 C27 121.7(3) . . ?
N21 C20 C19 178.1(4) . . ?
N64 C63 C32 176.9(3) . . ?
C53 C54 H54 118.9 . . ?
C55 C54 C53 122.2(3) . . ?
C55 C54 H54 118.9 . . ?
C52 C57 C56 116.9(3) . . ?
C52 C57 C60 121.7(3) . . ?
C56 C57 C60 121.4(3) . . ?
C54 C55 C56 118.3(3) . . ?
C54 C55 C58 121.7(3) . . ?
C56 C55 C58 120.0(3) . . ?
C9 C10 C11 116.9(3) . . ?
C9 C10 C26 122.5(3) . . ?
C11 C10 C26 120.6(3) . . ?
C14 C27 H27A 109.5 . . ?
C14 C27 H27B 109.5 . . ?
C14 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N25 C24 C23 177.2(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
N62 C61 C33 177.3(4) . . ?
C43 C44 C45 116.8(3) . . ?
C43 C44 C49 122.3(3) . . ?
C45 C44 C49 120.9(3) . . ?
C57 C56 H56 118.8 . . ?
C55 C56 C57 122.4(3) . . ?
C55 C56 H56 118.8 . . ?
C48 C47 H47 118.9 . . ?
C46 C47 C48 122.2(3) . . ?
C46 C47 H47 118.9 . . ?
C13 C12 C28 120.3(3) . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 C28 120.7(3) . . ?
C47 C46 C51 120.8(4) . . ?
C45 C46 C47 118.3(3) . . ?
C45 C46 C51 120.9(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C44 C45 H45 118.9 . . ?
C46 C45 C44 122.2(3) . . ?
C46 C45 H45 118.9 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C10 C26 H26A 109.5 . . ?
C10 C26 H26B 109.5 . . ?
C10 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C53 C59 H59A 109.5 . . ?
C53 C59 H59B 109.5 . . ?
C53 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C44 C49 H49A 109.5 . . ?
C44 C49 H49B 109.5 . . ?
C44 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C46 C51 H51A 109.5 . . ?
C46 C51 H51B 109.5 . . ?
C46 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C6 C1 Cl7 121.55(19) . . ?
C6 C1 C2 120.0 . . ?
C2 C1 Cl7 118.45(19) . . ?
C1 C6 Cl8 120.1(2) . . ?
C5 C6 Cl8 119.8(2) . . ?
C5 C6 C1 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C12 C28 H28A 109.5 . . ?
C12 C28 H28B 109.5 . . ?
C12 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C69 C68 Cl9 121.5(4) . . ?
C69 C68 C70 120.0 . . ?
C70 C68 Cl9 118.5(4) . . ?
C68 C69 C73 120.0 . . ?
C68 C69 Cl1 121.2(4) . . ?
C73 C69 Cl1 118.4(4) . . ?
C69 C73 H73 120.0 . . ?
C69 C73 C72 120.0 . . ?
C72 C73 H73 120.0 . . ?
C73 C72 H72 120.0 . . ?
C71 C72 C73 120.0 . . ?
C71 C72 H72 120.0 . . ?
C72 C71 H71 120.0 . . ?
C72 C71 C70 120.0 . . ?
C70 C71 H71 120.0 . . ?
C68 C70 H70 120.0 . . ?
C71 C70 C68 120.0 . . ?
C71 C70 H70 120.0 . . ?

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
Cl7 C1 C6 Cl8 -3.1(2) . . . . ?
Cl7 C1 C6 C5 -180.0(2) . . . . ?
Cl7 C1 C2 C3 180.0(2) . . . . ?
Cl8 C6 C5 C4 -176.8(2) . . . . ?
N15 C16 C17 N15 -1.1(4) . . . 3_556 ?
N15 C16 C17 N22 178.7(2) . . . . ?
N15 C9 C14 C27 -2.1(4) . . . . ?
N15 C9 C14 C13 177.0(3) . . . . ?
N15 C9 C10 C11 -177.2(3) . . . . ?
N15 C9 C10 C26 2.7(5) . . . . ?
N29 C43 C48 C47 -179.7(2) . . . . ?
N29 C43 C48 C50 -1.2(4) . . . . ?
N29 C43 C44 C45 179.4(3) . . . . ?
N29 C43 C44 C49 -1.7(4) . . . . ?
N41 C40 C39 N38 -0.9(4) . . . . ?
N41 C40 C39 C67 178.6(3) . . . . ?
N31 C32 C33 N34 1.0(5) . . . . ?
N31 C32 C33 C61 -174.9(3) . . . . ?
N36 C35 C30 N29 1.5(4) . . . . ?
N36 C35 C30 N31 179.1(3) . . . . ?
N36 C37 C42 N29 -2.6(4) . . . . ?
N36 C37 C42 N41 -180.0(2) . . . . ?
N36 C52 C53 C54 -175.4(2) . . . . ?
N36 C52 C53 C59 2.8(4) . . . . ?
N36 C52 C57 C56 174.8(3) . . . . ?
N36 C52 C57 C60 -3.8(5) . . . . ?
N38 C37 C42 N29 175.4(2) . . . . ?
N38 C37 C42 N41 -1.9(4) . . . . ?
N71 C16 C17 N15 179.9(2) . . . 3_556 ?
N71 C16 C17 N22 -0.3(4) . . . . ?
N71 C19 C23 N22 -0.3(4) . . . . ?
N71 C19 C23 C24 177.4(3) . . . . ?
N34 C35 C30 N29 -176.2(3) . . . . ?
N34 C35 C30 N31 1.4(4) . . . . ?
C16 N15 C9 C14 -90.5(3) . . . . ?
C16 N15 C9 C10 87.3(3) . . . . ?
C16 N71 C19 C23 0.3(4) . . . . ?
C16 N71 C19 C20 178.9(3) . . . . ?
C35 N36 C37 N38 -173.4(3) . . . . ?
C35 N36 C37 C42 4.7(4) . . . . ?
C35 N36 C52 C53 83.1(3) . . . . ?
C35 N36 C52 C57 -93.6(3) . . . . ?
C35 N34 C33 C32 -2.1(4) . . . . ?
C35 N34 C33 C61 174.1(3) . . . . ?
C30 N29 C43 C48 -92.3(3) . . . . ?
C30 N29 C43 C44 86.3(3) . . . . ?
C30 N29 C42 N41 177.4(2) . . . . ?
C30 N29 C42 C37 0.0(4) . . . . ?
C30 N31 C32 C33 1.3(4) . . . . ?
C30 N31 C32 C63 -175.1(3) . . . . ?
C40 N41 C42 N29 -176.4(2) . . . . ?
C40 N41 C42 C37 0.9(4) . . . . ?
C17 N15 C16 N71 -179.9(2) 3_556 . . . ?
C17 N15 C16 C17 1.1(4) 3_556 . . . ?
C17 N15 C9 C14 86.1(3) 3_556 . . . ?
C17 N15 C9 C10 -96.2(3) 3_556 . . . ?
C17 N22 C23 C19 0.0(4) . . . . ?
C17 N22 C23 C24 -177.9(3) . . . . ?
C65 C40 C39 N38 -179.8(3) . . . . ?
C65 C40 C39 C67 -0.3(4) . . . . ?
C43 N29 C30 N31 -7.8(4) . . . . ?
C43 N29 C30 C35 169.9(2) . . . . ?
C43 N29 C42 N41 8.2(4) . . . . ?
C43 N29 C42 C37 -169.2(2) . . . . ?
C43 C48 C47 C46 1.2(4) . . . . ?
C43 C44 C45 C46 -0.5(5) . . . . ?
C37 N36 C35 N34 173.7(3) . . . . ?
C37 N36 C35 C30 -4.1(4) . . . . ?
C37 N36 C52 C53 -88.7(3) . . . . ?
C37 N36 C52 C57 94.6(3) . . . . ?
C37 N38 C39 C40 -0.1(4) . . . . ?
C37 N38 C39 C67 -179.6(3) . . . . ?
C32 N31 C30 N29 175.2(2) . . . . ?
C32 N31 C30 C35 -2.4(4) . . . . ?
C39 N38 C37 N36 179.5(2) . . . . ?
C39 N38 C37 C42 1.4(4) . . . . ?
C19 N71 C16 N15 -179.0(2) . . . . ?
C19 N71 C16 C17 0.0(4) . . . . ?
C42 N29 C30 N31 -177.2(2) . . . . ?
C42 N29 C30 C35 0.5(4) . . . . ?
C42 N29 C43 C48 77.0(3) . . . . ?
C42 N29 C43 C44 -104.4(3) . . . . ?
C42 N41 C40 C65 179.3(2) . . . . ?
C42 N41 C40 C39 0.4(4) . . . . ?
C9 N15 C16 N71 -3.3(3) . . . . ?
C9 N15 C16 C17 177.6(2) . . . . ?
C9 C14 C13 C12 0.0(5) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C23 N22 C17 N15 -179.9(2) . . . 3_556 ?
C23 N22 C17 C16 0.3(4) . . . . ?
C52 N36 C35 N34 1.8(4) . . . . ?
C52 N36 C35 C30 -176.0(3) . . . . ?
C52 N36 C37 N38 -1.8(4) . . . . ?
C52 N36 C37 C42 176.3(2) . . . . ?
C52 C53 C54 C55 0.7(4) . . . . ?
C52 C57 C56 C55 0.4(5) . . . . ?
C33 N34 C35 N36 -176.8(3) . . . . ?
C33 N34 C35 C30 1.0(4) . . . . ?
C53 C52 C57 C56 -1.7(4) . . . . ?
C53 C52 C57 C60 179.7(3) . . . . ?
C53 C54 C55 C56 -1.9(5) . . . . ?
C53 C54 C55 C58 179.4(3) . . . . ?
C48 C43 C44 C45 -2.0(4) . . . . ?
C48 C43 C44 C49 176.9(3) . . . . ?
C48 C47 C46 C45 -3.6(5) . . . . ?
C48 C47 C46 C51 175.4(3) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
C14 C9 C10 C26 -179.7(3) . . . . ?
C14 C13 C12 C11 0.8(6) . . . . ?
C14 C13 C12 C28 -179.6(4) . . . . ?
C20 C19 C23 N22 -178.9(3) . . . . ?
C20 C19 C23 C24 -1.1(5) . . . . ?
C63 C32 C33 N34 177.3(3) . . . . ?
C63 C32 C33 C61 1.4(5) . . . . ?
C54 C55 C56 C57 1.3(5) . . . . ?
C57 C52 C53 C54 1.2(4) . . . . ?
C57 C52 C53 C59 179.4(3) . . . . ?
C10 C9 C14 C27 -179.7(3) . . . . ?
C10 C9 C14 C13 -0.6(5) . . . . ?
C27 C14 C13 C12 179.1(4) . . . . ?
C13 C12 C11 C10 -1.0(6) . . . . ?
C44 C43 C48 C47 1.7(4) . . . . ?
C44 C43 C48 C50 -179.8(3) . . . . ?
C47 C46 C45 C44 3.2(5) . . . . ?
C50 C48 C47 C46 -177.3(3) . . . . ?
C26 C10 C11 C12 -179.5(4) . . . . ?
C59 C53 C54 C55 -177.5(3) . . . . ?
C60 C57 C56 C55 179.0(3) . . . . ?
C58 C55 C56 C57 -179.9(3) . . . . ?
C49 C44 C45 C46 -179.5(3) . . . . ?
C51 C46 C45 C44 -175.8(3) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 Cl8 176.8(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C28 C12 C11 C10 179.3(4) . . . . ?
Cl9 C68 C69 C73 179.3(6) . . . . ?
Cl9 C68 C69 Cl1 6.0(5) . . . . ?
Cl9 C68 C70 C71 -179.3(6) . . . . ?
C68 C69 C73 C72 0.0 . . . . ?
C69 C68 C70 C71 0.0 . . . . ?
C69 C73 C72 C71 0.0 . . . . ?
C73 C72 C71 C70 0.0 . . . . ?
C72 C71 C70 C68 0.0 . . . . ?
C70 C68 C69 C73 0.0 . . . . ?
C70 C68 C69 Cl1 -173.4(7) . . . . ?
Cl1 C69 C73 C72 173.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-pyridine
_database_code_depnum_ccdc_archive 'CCDC 2429938'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H11 N5), 2(C5 H5 N)'
_chemical_formula_sum            'C40 H32 N12'
_chemical_formula_weight         680.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3409(8)
_cell_length_b                   12.7905(11)
_cell_length_c                   16.1963(14)
_cell_angle_alpha                70.868(8)
_cell_angle_beta                 83.072(7)
_cell_angle_gamma                82.513(7)
_cell_volume                     1806.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    143.19(13)
_cell_measurement_theta_max      71.4310
_cell_measurement_theta_min      3.6740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6592
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.898
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 8.1195
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  32.00   1.00    9.55    --  -34.65  37.00 150.00   44
  2  ω     -6.00  22.00   1.00    9.55    --  -34.65  37.00 120.00   28
  3  ω     19.00  47.00   1.00    9.55    --   34.65 -57.00 -60.00   28
  4  ω     56.00 102.00   1.00    9.55    --   34.65  57.00   0.00   46
  5  ω      7.00  73.00   1.00    9.55    --   34.65 -99.00 -60.00   66
  6  ω     26.00  53.00   1.00    9.55    --   34.65  57.00 -90.00   27
  7  ω      7.00  34.00   1.00    9.55    --   34.65 -19.00 -60.00   27
  8  ω    -10.00  17.00   1.00    9.55    --   34.65 -77.00 150.00   27
  9  ω      7.00  71.00   1.00    9.55    --   34.65 -99.00-180.00   64
 10  ω     38.00  65.00   1.00    9.55    --   34.65-125.00-180.00   27
 11  ω    -33.00  29.00   1.00    9.55    --   34.65 -57.00 -90.00   62
 12  ω     17.00  43.00   1.00    9.55    --   34.65  37.00-150.00   26
 13  ω     76.00 102.00   1.00    9.55    --   34.65  57.00 -90.00   26
 14  ω     42.00  85.00   1.00    9.55    --   34.65-125.00  90.00   43
 15  ω    -29.00   1.00   1.00    9.55    --   34.65 -19.00 -60.00   30
 16  ω    -20.00  53.00   1.00    9.55    --   34.65 -77.00  60.00   73
 17  ω    -25.00  44.00   1.00    9.55    --   34.65 -37.00-180.00   69
 18  ω     40.00  71.00   1.00   38.21    --  107.04 -45.00 120.00   31
 19  ω     39.00  72.00   1.00   38.21    --  107.04 -45.00 -60.00   33
 20  ω     44.00  71.00   1.00   38.21    --  107.04 -45.00  30.00   27
 21  ω     39.00 173.00   1.00   38.21    --  107.04   0.00   0.00  134
 22  ω     90.00 151.00   1.00   38.21    --  107.04  61.00-150.00   61
 23  ω     40.00 109.00   1.00   38.21    --  107.04-111.00 -30.00   69
 24  ω     40.00  67.00   1.00   38.21    --  107.04 -45.00 -30.00   27
 25  ω     43.00 102.00   1.00   38.21    --  107.04-111.00 -90.00   59
 26  ω     48.00  75.00   1.00   38.21    --  107.04 -94.00 120.00   27
 27  ω    119.00 168.00   1.00   38.21    --  107.04  77.00-180.00   49
 28  ω    114.00 156.00   1.00   38.21    --  107.04  77.00  30.00   42
 29  ω     40.00  72.00   1.00   38.21    --  107.04 -45.00  90.00   32
 30  ω     40.00  71.00   1.00   38.21    --  107.04 -45.00 -90.00   31
 31  ω     41.00  72.00   1.00   38.21    --  107.04 -45.00  60.00   31
 32  ω     40.00  74.00   1.00   38.21    --  107.04 -61.00  30.00   34
 33  ω     39.00  64.00   1.00   38.21    --  107.04 -45.00 150.00   25
 34  ω     69.00 109.00   1.00   38.21    --  107.04-111.00  90.00   40
 35  ω     45.00  70.00   1.00   38.21    --  107.04 -45.00-150.00   25
 36  ω     65.00 109.00   1.00   38.21    --  107.04-111.00-180.00   44
 37  ω     39.00  70.00   1.00   38.21    --  107.04 -45.00-120.00   31
 38  ω     67.00 109.00   1.00   38.21    --  107.04 -77.00 -60.00   42
 39  ω     90.00 117.00   1.00   38.21    --  107.04 -77.00 120.00   27
 40  ω     52.00  77.00   1.00   38.21    --  107.04 -77.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4295
_reflns_number_total             6592
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1398P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2491
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.695(8)
 0.305(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C25(H25), C5(H5), C3(H3), C48(H48), C45(H45), C49(H49), C46(H46),
 C42(H42), C43(H43), C52(H52), C51(H51), C44(H44), C50(H50)
3.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C),
 C28(H28A,H28B,H28C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N36 N 0.7400(3) 0.0713(2) 0.93200(19) 0.0352(6) Uani 1 1 d . . . . .
N30 N 0.9800(3) 0.0014(2) 0.91524(19) 0.0360(6) Uani 1 1 d . . . . .
N33 N 0.7860(3) 0.0789(2) 1.09802(19) 0.0364(6) Uani 1 1 d . . . . .
N16 N 0.7590(3) 0.5760(2) 0.42732(19) 0.0350(6) Uani 1 1 d . . . . .
N10 N 0.5175(3) 0.6139(2) 0.4710(2) 0.0356(6) Uani 1 1 d . . . . .
N20 N 1.1227(3) 0.5663(3) 0.3652(2) 0.0460(8) Uani 1 1 d . . . . .
N40 N 0.3835(3) 0.1687(3) 0.9200(2) 0.0488(8) Uani 1 1 d . . . . .
C32 C 0.8880(4) 0.0401(3) 1.0504(2) 0.0342(7) Uani 1 1 d . . . . .
C31 C 0.8670(4) 0.0383(3) 0.9647(2) 0.0346(7) Uani 1 1 d . . . . .
N38 N 0.4643(4) 0.2052(3) 1.1539(2) 0.0536(9) Uani 1 1 d . . . . .
C1 C 0.5389(3) 0.7316(3) 0.4433(2) 0.0350(7) Uani 1 1 d . . . . .
C22 C 0.8926(4) -0.0798(3) 0.8161(2) 0.0366(7) Uani 1 1 d . . . . .
C35 C 0.6342(4) 0.1103(3) 0.9820(2) 0.0361(7) Uani 1 1 d . . . . .
N47 N 0.8202(4) 0.3159(3) 0.9298(2) 0.0548(9) Uani 1 1 d . . . . .
C19 C 1.0088(4) 0.5375(3) 0.3858(2) 0.0374(8) Uani 1 1 d . . . . .
C34 C 0.6570(4) 0.1162(3) 1.0625(2) 0.0378(8) Uani 1 1 d . . . . .
C6 C 0.5968(4) 0.7705(3) 0.5011(2) 0.0374(8) Uani 1 1 d . . . . .
C23 C 0.8590(4) -0.0672(3) 0.7324(2) 0.0393(8) Uani 1 1 d . . . . .
H23 H 0.812691 -0.123791 0.723143 0.047 Uiso 1 1 calc R U . . .
C15 C 0.8679(4) 0.4987(3) 0.4174(2) 0.0358(7) Uani 1 1 d . . . . .
C11 C 0.6336(4) 0.5393(3) 0.4609(2) 0.0343(7) Uani 1 1 d . . . . .
C37 C 0.5485(4) 0.1652(3) 1.1128(3) 0.0404(8) Uani 1 1 d . . . . .
C26 C 1.0021(4) 0.0975(3) 0.7572(2) 0.0367(7) Uani 1 1 d . . . . .
C2 C 0.5053(4) 0.7975(3) 0.3598(2) 0.0379(8) Uani 1 1 d . . . . .
C39 C 0.4940(4) 0.1444(3) 0.9464(2) 0.0390(8) Uani 1 1 d . . . . .
C24 C 0.8908(4) 0.0256(3) 0.6611(2) 0.0382(8) Uani 1 1 d . . . . .
C21 C 0.9591(4) 0.0064(3) 0.8266(2) 0.0363(7) Uani 1 1 d . . . . .
C25 C 0.9666(4) 0.1057(3) 0.6749(2) 0.0400(8) Uani 1 1 d . . . . .
H25 H 0.994255 0.167056 0.626198 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6289(4) 0.8809(3) 0.4706(3) 0.0439(9) Uani 1 1 d . . . . .
H5 H 0.668324 0.910568 0.508591 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5405(4) 0.9075(3) 0.3324(3) 0.0422(8) Uani 1 1 d . . . . .
H3 H 0.519800 0.955010 0.275441 0.051 Uiso 1 1 calc R U . . .
N41 N 0.3365(4) 0.5316(3) 0.7430(3) 0.0644(11) Uani 1 1 d . . . . .
C4 C 0.6046(4) 0.9482(3) 0.3862(3) 0.0432(8) Uani 1 1 d . . . . .
C29 C 1.0854(4) 0.1830(3) 0.7711(3) 0.0456(9) Uani 1 1 d . . . . .
H29A H 1.029366 0.215247 0.813608 0.068 Uiso 1 1 calc R U . . .
H29B H 1.102495 0.241807 0.715293 0.068 Uiso 1 1 calc R U . . .
H29C H 1.178536 0.147359 0.793576 0.068 Uiso 1 1 calc R U . . .
C27 C 0.8602(4) -0.1804(3) 0.8925(3) 0.0445(8) Uani 1 1 d . . . . .
H27A H 0.788371 -0.158480 0.934673 0.067 Uiso 1 1 calc R U . . .
H27B H 0.949306 -0.214185 0.920939 0.067 Uiso 1 1 calc R U . . .
H27C H 0.821639 -0.234243 0.871884 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4313(5) 0.7546(3) 0.3018(3) 0.0509(9) Uani 1 1 d . . . . .
H7A H 0.491021 0.690617 0.291266 0.076 Uiso 1 1 calc R U . . .
H7B H 0.417779 0.813412 0.245747 0.076 Uiso 1 1 calc R U . . .
H7C H 0.336665 0.731895 0.330460 0.076 Uiso 1 1 calc R U . . .
C9 C 0.6228(4) 0.6966(3) 0.5929(3) 0.0460(9) Uani 1 1 d . . . . .
H9A H 0.534931 0.660803 0.620628 0.069 Uiso 1 1 calc R U . . .
H9B H 0.647612 0.741441 0.626995 0.069 Uiso 1 1 calc R U . . .
H9C H 0.702874 0.639626 0.590708 0.069 Uiso 1 1 calc R U . . .
C28 C 0.8436(5) 0.0404(3) 0.5726(3) 0.0487(9) Uani 1 1 d . . . . .
H28A H 0.847516 -0.032365 0.564166 0.073 Uiso 1 1 calc R U . . .
H28B H 0.908239 0.087151 0.527273 0.073 Uiso 1 1 calc R U . . .
H28C H 0.744193 0.076155 0.568473 0.073 Uiso 1 1 calc R U . . .
C48 C 0.7627(5) 0.3536(4) 0.8530(3) 0.0548(10) Uani 1 1 d . . . . .
H48 H 0.786230 0.311736 0.813595 0.066 Uiso 1 1 calc R U . . .
C8 C 0.6500(5) 1.0654(3) 0.3530(3) 0.0560(11) Uani 1 1 d . . . . .
H8A H 0.675862 1.085669 0.402318 0.084 Uiso 1 1 calc R U . . .
H8B H 0.569640 1.117309 0.325456 0.084 Uiso 1 1 calc R U . . .
H8C H 0.733952 1.069107 0.309914 0.084 Uiso 1 1 calc R U . . .
C45 C 0.1392(6) 0.4492(4) 0.8366(4) 0.0692(13) Uani 1 1 d . . . . .
H45 H 0.097846 0.383118 0.871486 0.083 Uiso 1 1 calc R U . . .
C49 C 0.6721(5) 0.4487(4) 0.8277(4) 0.0668(13) Uani 1 1 d . . . . .
H49 H 0.632085 0.471343 0.772600 0.080 Uiso 1 1 calc R U . . .
C46 C 0.2684(5) 0.4442(4) 0.7915(3) 0.0622(12) Uani 1 1 d . . . . .
H46 H 0.314923 0.372643 0.794396 0.075 Uiso 1 1 calc R U . . .
C42 C 0.2680(5) 0.6304(4) 0.7409(3) 0.0609(11) Uani 1 1 d . . . . .
H42 H 0.315143 0.694616 0.708194 0.073 Uiso 1 1 calc R U . . .
C43 C 0.1358(6) 0.6457(4) 0.7823(4) 0.0682(13) Uani 1 1 d . . . . .
H43 H 0.090970 0.718177 0.777900 0.082 Uiso 1 1 calc R U . . .
C52 C 0.7871(6) 0.3753(4) 0.9834(4) 0.0657(12) Uani 1 1 d . . . . .
H52 H 0.827738 0.349427 1.038396 0.079 Uiso 1 1 calc R U . . .
C51 C 0.6976(6) 0.4723(6) 0.9643(5) 0.0840(17) Uani 1 1 d . . . . .
H51 H 0.675384 0.512101 1.005255 0.101 Uiso 1 1 calc R U . . .
C44 C 0.0680(6) 0.5514(5) 0.8316(4) 0.0782(16) Uani 1 1 d . . . . .
H44 H -0.025467 0.557793 0.861084 0.094 Uiso 1 1 calc R U . . .
C50 C 0.6399(7) 0.5108(5) 0.8830(5) 0.0894(19) Uani 1 1 d . . . . .
H50 H 0.579531 0.578815 0.866434 0.107 Uiso 1 1 calc R U . . .
C14 C 0.8476(4) 0.3880(3) 0.4404(2) 0.0358(7) Uani 1 1 d . . . . .
C17 C 0.9621(4) 0.3084(3) 0.4247(3) 0.0408(8) Uani 1 1 d . . . . .
N13 N 0.7187(3) 0.3486(2) 0.4774(2) 0.0358(6) Uani 1 1 d . . . . .
N18 N 1.0535(4) 0.2450(3) 0.4114(3) 0.0558(9) Uani 1 1 d . . . . .
C12 C 0.6139(4) 0.4224(3) 0.4886(2) 0.0339(7) 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
N36 C31 1.320(4) . ?
N36 C35 1.350(5) . ?
N30 C32 1.384(4) 2_757 ?
N30 C31 1.376(4) . ?
N30 C21 1.451(4) . ?
N33 C32 1.304(5) . ?
N33 C34 1.359(5) . ?
N16 C15 1.357(4) . ?
N16 C11 1.308(5) . ?
N10 C1 1.457(4) . ?
N10 C11 1.379(4) . ?
N10 C12 1.380(4) 2_666 ?
N20 C19 1.147(5) . ?
N40 C39 1.131(5) . ?
C32 C31 1.433(5) . ?
N38 C37 1.147(5) . ?
C1 C6 1.383(5) . ?
C1 C2 1.387(5) . ?
C22 C23 1.381(5) . ?
C22 C21 1.399(5) . ?
C22 C27 1.498(5) . ?
C35 C34 1.373(5) . ?
C35 C39 1.452(5) . ?
N47 C48 1.329(6) . ?
N47 C52 1.317(6) . ?
C19 C15 1.443(5) . ?
C34 C37 1.434(5) . ?
C6 C5 1.395(5) . ?
C6 C9 1.505(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(5) . ?
C15 C14 1.374(5) . ?
C11 C12 1.443(5) . ?
C26 C21 1.391(5) . ?
C26 C25 1.381(5) . ?
C26 C29 1.509(5) . ?
C2 C3 1.401(5) . ?
C2 C7 1.502(5) . ?
C24 C25 1.406(5) . ?
C24 C28 1.495(5) . ?
C25 H25 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(6) . ?
N41 C46 1.326(6) . ?
N41 C42 1.332(6) . ?
C4 C8 1.517(5) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C48 H48 0.9500 . ?
C48 C49 1.361(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C45 H45 0.9500 . ?
C45 C46 1.339(7) . ?
C45 C44 1.369(7) . ?
C49 H49 0.9500 . ?
C49 C50 1.365(8) . ?
C46 H46 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.355(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.393(8) . ?
C52 H52 0.9500 . ?
C52 C51 1.369(8) . ?
C51 H51 0.9500 . ?
C51 C50 1.394(9) . ?
C44 H44 0.9500 . ?
C50 H50 0.9500 . ?
C14 C17 1.437(5) . ?
C14 N13 1.359(5) . ?
C17 N18 1.150(5) . ?
N13 C12 1.308(4) . ?

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
C31 N36 C35 116.5(3) . . ?
C32 N30 C21 120.4(3) 2_757 . ?
C31 N30 C32 120.4(3) . 2_757 ?
C31 N30 C21 119.3(3) . . ?
C32 N33 C34 116.2(3) . . ?
C11 N16 C15 116.4(3) . . ?
C11 N10 C1 118.6(3) . . ?
C11 N10 C12 120.9(3) . 2_666 ?
C12 N10 C1 120.4(3) 2_666 . ?
N30 C32 C31 119.4(3) 2_757 . ?
N33 C32 N30 118.4(3) . 2_757 ?
N33 C32 C31 122.2(3) . . ?
N36 C31 N30 118.9(3) . . ?
N36 C31 C32 121.0(3) . . ?
N30 C31 C32 120.1(3) . . ?
C6 C1 N10 117.7(3) . . ?
C6 C1 C2 123.7(3) . . ?
C2 C1 N10 118.6(3) . . ?
C23 C22 C21 116.7(3) . . ?
C23 C22 C27 122.2(3) . . ?
C21 C22 C27 121.1(3) . . ?
N36 C35 C34 122.1(3) . . ?
N36 C35 C39 116.2(3) . . ?
C34 C35 C39 121.7(3) . . ?
C52 N47 C48 117.3(4) . . ?
N20 C19 C15 176.4(4) . . ?
N33 C34 C35 121.8(3) . . ?
N33 C34 C37 115.8(3) . . ?
C35 C34 C37 122.3(3) . . ?
C1 C6 C5 116.9(3) . . ?
C1 C6 C9 121.2(3) . . ?
C5 C6 C9 121.8(3) . . ?
C22 C23 H23 118.9 . . ?
C22 C23 C24 122.3(3) . . ?
C24 C23 H23 118.9 . . ?
N16 C15 C19 116.7(3) . . ?
N16 C15 C14 122.0(3) . . ?
C14 C15 C19 121.3(3) . . ?
N16 C11 N10 119.3(3) . . ?
N16 C11 C12 121.6(3) . . ?
N10 C11 C12 119.1(3) . . ?
N38 C37 C34 178.3(4) . . ?
C21 C26 C29 121.5(3) . . ?
C25 C26 C21 117.1(3) . . ?
C25 C26 C29 121.4(3) . . ?
C1 C2 C3 116.9(3) . . ?
C1 C2 C7 122.0(3) . . ?
C3 C2 C7 121.1(3) . . ?
N40 C39 C35 178.3(4) . . ?
C23 C24 C25 118.2(3) . . ?
C23 C24 C28 120.8(3) . . ?
C25 C24 C28 121.0(3) . . ?
C22 C21 N30 117.7(3) . . ?
C26 C21 N30 118.6(3) . . ?
C26 C21 C22 123.6(3) . . ?
C26 C25 C24 121.8(3) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C46 N41 C42 115.6(4) . . ?
C5 C4 C8 120.1(4) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 C8 120.4(4) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N47 C48 H48 118.1 . . ?
N47 C48 C49 123.8(5) . . ?
C49 C48 H48 118.1 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C46 C45 H45 120.6 . . ?
C46 C45 C44 118.7(5) . . ?
C44 C45 H45 120.6 . . ?
C48 C49 H49 120.7 . . ?
C48 C49 C50 118.7(5) . . ?
C50 C49 H49 120.7 . . ?
N41 C46 C45 125.0(5) . . ?
N41 C46 H46 117.5 . . ?
C45 C46 H46 117.5 . . ?
N41 C42 H42 117.7 . . ?
N41 C42 C43 124.6(5) . . ?
C43 C42 H42 117.7 . . ?
C42 C43 H43 121.2 . . ?
C42 C43 C44 117.6(5) . . ?
C44 C43 H43 121.2 . . ?
N47 C52 H52 118.2 . . ?
N47 C52 C51 123.7(5) . . ?
C51 C52 H52 118.2 . . ?
C52 C51 H51 121.0 . . ?
C52 C51 C50 118.0(5) . . ?
C50 C51 H51 121.0 . . ?
C45 C44 C43 118.4(5) . . ?
C45 C44 H44 120.8 . . ?
C43 C44 H44 120.8 . . ?
C49 C50 C51 118.6(5) . . ?
C49 C50 H50 120.7 . . ?
C51 C50 H50 120.7 . . ?
C15 C14 C17 121.1(3) . . ?
N13 C14 C15 122.1(3) . . ?
N13 C14 C17 116.9(3) . . ?
N18 C17 C14 179.5(4) . . ?
C12 N13 C14 116.3(3) . . ?
N10 C12 C11 119.9(3) 2_666 . ?
N13 C12 N10 118.5(3) . 2_666 ?
N13 C12 C11 121.6(3) . . ?

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
N36 C35 C34 N33 -2.7(5) . . . . ?
N36 C35 C34 C37 175.1(3) . . . . ?
N30 C32 C31 N36 176.1(3) 2_757 . . . ?
N30 C32 C31 N30 -3.7(5) 2_757 . . . ?
N33 C32 C31 N36 -3.3(5) . . . . ?
N33 C32 C31 N30 176.9(3) . . . . ?
N16 C15 C14 C17 176.4(3) . . . . ?
N16 C15 C14 N13 -2.4(6) . . . . ?
N16 C11 C12 N10 175.8(3) . . . 2_666 ?
N16 C11 C12 N13 -3.5(5) . . . . ?
N10 C1 C6 C5 174.3(3) . . . . ?
N10 C1 C6 C9 -6.1(5) . . . . ?
N10 C1 C2 C3 -173.9(3) . . . . ?
N10 C1 C2 C7 7.6(5) . . . . ?
N10 C11 C12 N10 -3.5(5) . . . 2_666 ?
N10 C11 C12 N13 177.2(3) . . . . ?
C32 N30 C31 N36 -176.1(3) 2_757 . . . ?
C32 N30 C31 C32 3.7(5) 2_757 . . . ?
C32 N30 C21 C22 97.5(4) 2_757 . . . ?
C32 N30 C21 C26 -84.3(4) 2_757 . . . ?
C32 N33 C34 C35 1.8(5) . . . . ?
C32 N33 C34 C37 -176.2(3) . . . . ?
C31 N36 C35 C34 0.4(5) . . . . ?
C31 N36 C35 C39 -178.8(3) . . . . ?
C31 N30 C21 C22 -82.4(4) . . . . ?
C31 N30 C21 C26 95.8(4) . . . . ?
C1 N10 C11 N16 0.3(5) . . . . ?
C1 N10 C11 C12 179.6(3) . . . . ?
C1 C6 C5 C4 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C22 C23 C24 C25 3.5(5) . . . . ?
C22 C23 C24 C28 -175.6(3) . . . . ?
C35 N36 C31 N30 -177.8(3) . . . . ?
C35 N36 C31 C32 2.4(5) . . . . ?
N47 C48 C49 C50 1.4(8) . . . . ?
N47 C52 C51 C50 -0.9(9) . . . . ?
C19 C15 C14 C17 -7.0(5) . . . . ?
C19 C15 C14 N13 174.2(3) . . . . ?
C34 N33 C32 N30 -178.4(3) . . . 2_757 ?
C34 N33 C32 C31 1.1(5) . . . . ?
C6 C1 C2 C3 3.7(5) . . . . ?
C6 C1 C2 C7 -174.9(3) . . . . ?
C6 C5 C4 C3 3.4(6) . . . . ?
C6 C5 C4 C8 -175.9(4) . . . . ?
C23 C22 C21 N30 173.0(3) . . . . ?
C23 C22 C21 C26 -5.1(5) . . . . ?
C23 C24 C25 C26 -3.8(5) . . . . ?
C15 N16 C11 N10 -178.6(3) . . . . ?
C15 N16 C11 C12 2.1(5) . . . . ?
C15 C14 N13 C12 1.0(5) . . . . ?
C11 N16 C15 C19 -176.0(3) . . . . ?
C11 N16 C15 C14 0.7(5) . . . . ?
C11 N10 C1 C6 -83.0(4) . . . . ?
C11 N10 C1 C2 94.6(4) . . . . ?
C2 C1 C6 C5 -3.3(5) . . . . ?
C2 C1 C6 C9 176.3(3) . . . . ?
C2 C3 C4 C5 -3.0(6) . . . . ?
C2 C3 C4 C8 176.3(4) . . . . ?
C39 C35 C34 N33 176.5(3) . . . . ?
C39 C35 C34 C37 -5.6(6) . . . . ?
C21 N30 C31 N36 3.9(5) . . . . ?
C21 N30 C31 C32 -176.3(3) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C21 C26 C25 C24 -0.2(5) . . . . ?
C25 C26 C21 N30 -173.2(3) . . . . ?
C25 C26 C21 C22 4.9(5) . . . . ?
N41 C42 C43 C44 1.1(9) . . . . ?
C29 C26 C21 N30 7.5(5) . . . . ?
C29 C26 C21 C22 -174.4(3) . . . . ?
C29 C26 C25 C24 179.1(3) . . . . ?
C27 C22 C23 C24 -179.1(3) . . . . ?
C27 C22 C21 N30 -7.1(5) . . . . ?
C27 C22 C21 C26 174.8(3) . . . . ?
C7 C2 C3 C4 178.1(4) . . . . ?
C9 C6 C5 C4 -180.0(4) . . . . ?
C28 C24 C25 C26 175.3(3) . . . . ?
C48 N47 C52 C51 0.2(8) . . . . ?
C48 C49 C50 C51 -2.0(9) . . . . ?
C46 N41 C42 C43 -1.8(8) . . . . ?
C46 C45 C44 C43 -2.4(9) . . . . ?
C42 N41 C46 C45 0.3(8) . . . . ?
C42 C43 C44 C45 1.1(9) . . . . ?
C52 N47 C48 C49 -0.4(7) . . . . ?
C52 C51 C50 C49 1.8(10) . . . . ?
C44 C45 C46 N41 1.8(9) . . . . ?
C14 N13 C12 N10 -177.6(3) . . . 2_666 ?
C14 N13 C12 C11 1.7(5) . . . . ?
C17 C14 N13 C12 -177.8(3) . . . . ?
C12 N10 C1 C6 93.1(4) 2_666 . . . ?
C12 N10 C1 C2 -89.2(4) 2_666 . . . ?
C12 N10 C11 N16 -175.8(3) 2_666 . . . ?
C12 N10 C11 C12 3.5(6) 2_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.695(8)
2 0.305(8)
####################################################################### 
# 
# 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_TCDP-THF
_database_code_depnum_ccdc_archive 'CCDC 2429934'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 2(C4 H8 O)'
_chemical_formula_sum            'C38 H38 N10 O2'
_chemical_formula_weight         666.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0161(4)
_cell_length_b                   12.1980(6)
_cell_length_c                   16.1054(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.256(4)
_cell_angle_gamma                90
_cell_volume                     1748.18(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      27.6090
_cell_measurement_theta_min      3.0540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.954
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  23.00   0.50   40.00    --   21.12  57.00 120.00   52
  2  ω     75.00 101.00   0.50   40.00    --   21.12  57.00 120.00   52
  3  ω     61.00  87.00   0.50   40.00    --   21.12 179.00 -60.00   52
  4  ω     39.00 108.00   0.50   40.00    --   21.12 179.00 -90.00  138
  5  ω    -39.00  31.00   0.50   40.00    --   21.12 -57.00-150.00  140
  6  ω     30.00  55.00   0.50   40.00    --   21.12-127.00 -73.00   50
  7  ω    -14.00  34.00   0.50   40.00    --  -19.87 -99.00 -90.00   96
  8  ω     28.00  65.00   0.50   40.00    --   21.12-143.00 116.00   74
  9  ω    -99.00  -9.00   0.50   40.00    --  -19.87 -57.00  60.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0251938000
_diffrn_orient_matrix_UB_12      -0.0471310000
_diffrn_orient_matrix_UB_13      0.0194467000
_diffrn_orient_matrix_UB_21      -0.0296613000
_diffrn_orient_matrix_UB_22      0.0339877000
_diffrn_orient_matrix_UB_23      0.0290820000
_diffrn_orient_matrix_UB_31      -0.0695528000
_diffrn_orient_matrix_UB_32      0.0025336000
_diffrn_orient_matrix_UB_33      -0.0276936000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             3855
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.9186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C22 = C25-C24A
 1.473 with sigma of 0.005
 C24B-C23 = C24A-C23
 1.484 with sigma of 0.005
 C23-C24B \\sim C23-C24A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24B \\sim O21: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C24A \\sim C25 \\sim O21: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(H25C)=Sof(H25D)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(C24B)=Sof(H24A)=Sof(H24B)=Sof(H25A)=Sof(H25B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C23(H23C,H23D), C24B(H24A,H24B), C24A(H24C,
 H24D), C25(H25A,H25B), C25(H25C,H25D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.47022(17) 0.60770(13) 0.52325(9) 0.0234(4) Uani 1 1 d . . . . .
N16 N 0.25140(17) 0.54908(13) 0.56760(9) 0.0244(4) Uani 1 1 d . . . . .
N13 N 0.31385(17) 0.33282(14) 0.52316(10) 0.0251(4) Uani 1 1 d . . . . .
O21 O 0.47982(18) 0.39600(15) 0.72710(10) 0.0485(5) Uani 1 1 d . U . . .
N20 N -0.0837(2) 0.50681(17) 0.63880(11) 0.0388(5) Uani 1 1 d . . . . .
N18 N 0.0219(2) 0.19563(17) 0.58650(13) 0.0442(5) Uani 1 1 d . . . . .
C11 C 0.3720(2) 0.52466(16) 0.53513(11) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.4027(2) 0.41482(16) 0.51197(11) 0.0227(4) Uani 1 1 d . . . . .
C1 C 0.4436(2) 0.71961(16) 0.54944(12) 0.0230(4) Uani 1 1 d . . . . .
C14 C 0.1913(2) 0.35824(17) 0.55789(11) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.1602(2) 0.46403(16) 0.57912(11) 0.0242(4) Uani 1 1 d . . . . .
C19 C 0.0253(2) 0.48957(17) 0.61344(12) 0.0275(5) Uani 1 1 d . . . . .
C6 C 0.4910(2) 0.74754(17) 0.63309(12) 0.0266(4) Uani 1 1 d . . . . .
C5 C 0.4690(2) 0.85547(18) 0.65589(13) 0.0310(5) Uani 1 1 d . . . . .
H5 H 0.502160 0.877248 0.712458 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0956(2) 0.26769(18) 0.57293(12) 0.0297(5) Uani 1 1 d . . . . .
C2 C 0.3757(2) 0.79305(17) 0.48949(12) 0.0278(5) Uani 1 1 d . . . . .
C4 C 0.4004(2) 0.93242(18) 0.59909(14) 0.0345(5) Uani 1 1 d . . . . .
C3 C 0.3546(2) 0.89943(18) 0.51618(14) 0.0347(5) Uani 1 1 d . . . . .
H3 H 0.307360 0.951344 0.476550 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3295(2) 0.7593(2) 0.39949(12) 0.0362(5) Uani 1 1 d . . . . .
H7A H 0.417904 0.734295 0.376545 0.054 Uiso 1 1 calc R U . . .
H7B H 0.284287 0.822057 0.366730 0.054 Uiso 1 1 calc R U . . .
H7C H 0.256021 0.699672 0.396400 0.054 Uiso 1 1 calc R U . . .
C9 C 0.5623(3) 0.66454(19) 0.69599(13) 0.0365(5) Uani 1 1 d . . . . .
H9A H 0.492616 0.603424 0.698545 0.055 Uiso 1 1 calc R U . . .
H9B H 0.585801 0.698939 0.751539 0.055 Uiso 1 1 calc R U . . .
H9C H 0.655019 0.637076 0.678932 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3719(3) 1.0473(2) 0.62695(18) 0.0519(7) Uani 1 1 d . . . . .
H8A H 0.274274 1.050185 0.646240 0.078 Uiso 1 1 calc R U . . .
H8B H 0.371579 1.097848 0.579636 0.078 Uiso 1 1 calc R U . . .
H8C H 0.451245 1.068545 0.673086 0.078 Uiso 1 1 calc R U . . .
C22 C 0.3754(3) 0.3366(2) 0.76583(15) 0.0542(7) Uani 1 1 d D . . . .
H22A H 0.347832 0.267660 0.734652 0.065 Uiso 1 1 calc R U . . .
H22B H 0.282991 0.380428 0.765750 0.065 Uiso 1 1 calc R U . . .
C23 C 0.4463(3) 0.3114(3) 0.85423(17) 0.0734(10) Uani 1 1 d D . . . .
H23A H 0.376650 0.328592 0.894095 0.088 Uiso 0.489(13) 1 calc R U P A 1
H23B H 0.474949 0.233134 0.860222 0.088 Uiso 0.489(13) 1 calc R U P A 1
H23C H 0.412987 0.363997 0.894294 0.088 Uiso 0.511(13) 1 calc R U P A 2
H23D H 0.421607 0.236071 0.870309 0.088 Uiso 0.511(13) 1 calc R U P A 2
C24B C 0.5809(8) 0.3826(7) 0.8697(4) 0.054(2) Uani 0.489(13) 1 d D . P A 1
H24A H 0.558481 0.452311 0.896588 0.065 Uiso 0.489(13) 1 calc R U P A 1
H24B H 0.664784 0.345337 0.906079 0.065 Uiso 0.489(13) 1 calc R U P A 1
C24A C 0.6065(5) 0.3228(9) 0.8521(5) 0.056(2) Uani 0.511(13) 1 d D U P A 2
H24C H 0.650529 0.251442 0.839640 0.067 Uiso 0.511(13) 1 calc R U P A 2
H24D H 0.659860 0.349955 0.906776 0.067 Uiso 0.511(13) 1 calc R U P A 2
C25 C 0.6179(3) 0.4023(2) 0.78486(16) 0.0578(8) Uani 1 1 d D U . . .
H25A H 0.664130 0.475533 0.782098 0.069 Uiso 0.489(13) 1 calc R U P A 1
H25B H 0.689510 0.346227 0.771069 0.069 Uiso 0.489(13) 1 calc R U P A 1
H25C H 0.632761 0.477194 0.808384 0.069 Uiso 0.511(13) 1 calc R U P A 2
H25D H 0.703833 0.383983 0.756113 0.069 Uiso 0.511(13) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C11 1.379(2) . ?
N10 C12 1.385(2) 3_666 ?
N10 C1 1.460(2) . ?
N16 C11 1.314(2) . ?
N16 C15 1.355(2) . ?
N13 C12 1.312(2) . ?
N13 C14 1.352(2) . ?
O21 C22 1.411(3) . ?
O21 C25 1.431(3) . ?
N20 C19 1.143(3) . ?
N18 C17 1.144(3) . ?
C11 C12 1.430(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.385(3) . ?
C14 C15 1.375(3) . ?
C14 C17 1.446(3) . ?
C15 C19 1.448(3) . ?
C6 C5 1.389(3) . ?
C6 C9 1.502(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.500(3) . ?
C4 C3 1.392(3) . ?
C4 C8 1.506(3) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.496(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
C23 C24B 1.480(4) . ?
C23 C24A 1.457(4) . ?
C24B H24A 0.9900 . ?
C24B H24B 0.9900 . ?
C24B C25 1.477(7) . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?
C24A C25 1.470(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 H25C 0.9900 . ?
C25 H25D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N10 C12 120.20(16) . 3_666 ?
C11 N10 C1 120.51(15) . . ?
C12 N10 C1 119.27(16) 3_666 . ?
C11 N16 C15 116.12(17) . . ?
C12 N13 C14 116.10(17) . . ?
C22 O21 C25 108.22(17) . . ?
N10 C11 C12 119.74(16) . . ?
N16 C11 N10 118.66(17) . . ?
N16 C11 C12 121.60(17) . . ?
N10 C12 C11 120.05(17) 3_666 . ?
N13 C12 N10 117.95(17) . 3_666 ?
N13 C12 C11 122.00(17) . . ?
C6 C1 N10 118.07(17) . . ?
C2 C1 N10 118.55(16) . . ?
C2 C1 C6 123.37(18) . . ?
N13 C14 C15 122.06(18) . . ?
N13 C14 C17 116.32(18) . . ?
C15 C14 C17 121.60(18) . . ?
N16 C15 C14 122.11(17) . . ?
N16 C15 C19 116.94(18) . . ?
C14 C15 C19 120.94(18) . . ?
N20 C19 C15 177.5(2) . . ?
C1 C6 C5 117.01(18) . . ?
C1 C6 C9 121.37(18) . . ?
C5 C6 C9 121.63(18) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.36(19) . . ?
C4 C5 H5 118.8 . . ?
N18 C17 C14 178.5(2) . . ?
C1 C2 C3 117.08(18) . . ?
C1 C2 C7 121.29(19) . . ?
C3 C2 C7 121.62(19) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C8 120.9(2) . . ?
C3 C4 C8 121.1(2) . . ?
C2 C3 C4 122.2(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O21 C22 H22A 110.1 . . ?
O21 C22 H22B 110.1 . . ?
O21 C22 C23 108.2(2) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110.1 . . ?
C23 C22 H22B 110.1 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
C22 C23 H23C 111.1 . . ?
C22 C23 H23D 111.1 . . ?
H23A C23 H23B 108.9 . . ?
H23C C23 H23D 109.0 . . ?
C24B C23 C22 104.7(3) . . ?
C24B C23 H23A 110.8 . . ?
C24B C23 H23B 110.8 . . ?
C24A C23 C22 103.4(3) . . ?
C24A C23 H23C 111.1 . . ?
C24A C23 H23D 111.1 . . ?
C23 C24B H24A 111.0 . . ?
C23 C24B H24B 111.0 . . ?
H24A C24B H24B 109.0 . . ?
C25 C24B C23 104.0(4) . . ?
C25 C24B H24A 111.0 . . ?
C25 C24B H24B 111.0 . . ?
C23 C24A H24C 110.6 . . ?
C23 C24A H24D 110.6 . . ?
C23 C24A C25 105.5(3) . . ?
H24C C24A H24D 108.8 . . ?
C25 C24A H24C 110.6 . . ?
C25 C24A H24D 110.6 . . ?
O21 C25 C24B 106.9(3) . . ?
O21 C25 C24A 106.7(3) . . ?
O21 C25 H25A 110.3 . . ?
O21 C25 H25B 110.3 . . ?
O21 C25 H25C 110.4 . . ?
O21 C25 H25D 110.4 . . ?
C24B C25 H25A 110.3 . . ?
C24B C25 H25B 110.3 . . ?
C24A C25 H25C 110.4 . . ?
C24A C25 H25D 110.4 . . ?
H25A C25 H25B 108.6 . . ?
H25C C25 H25D 108.6 . . ?

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
N10 C11 C12 N10 -0.8(3) . . . 3_666 ?
N10 C11 C12 N13 179.01(16) . . . . ?
N10 C1 C6 C5 177.90(17) . . . . ?
N10 C1 C6 C9 -2.3(3) . . . . ?
N10 C1 C2 C3 -178.83(17) . . . . ?
N10 C1 C2 C7 0.2(3) . . . . ?
N16 C11 C12 N10 179.03(16) . . . 3_666 ?
N16 C11 C12 N13 -1.1(3) . . . . ?
N13 C14 C15 N16 -0.9(3) . . . . ?
N13 C14 C15 C19 177.77(17) . . . . ?
O21 C22 C23 C24B 13.5(5) . . . . ?
O21 C22 C23 C24A -20.3(6) . . . . ?
C11 N10 C1 C6 83.3(2) . . . . ?
C11 N10 C1 C2 -98.2(2) . . . . ?
C11 N16 C15 C14 -0.2(3) . . . . ?
C11 N16 C15 C19 -178.93(16) . . . . ?
C12 N10 C11 N16 -179.03(16) 3_666 . . . ?
C12 N10 C11 C12 0.8(3) 3_666 . . . ?
C12 N10 C1 C6 -95.3(2) 3_666 . . . ?
C12 N10 C1 C2 83.3(2) 3_666 . . . ?
C12 N13 C14 C15 0.9(3) . . . . ?
C12 N13 C14 C17 -178.02(16) . . . . ?
C1 N10 C11 N16 2.5(2) . . . . ?
C1 N10 C11 C12 -177.67(16) . . . . ?
C1 C6 C5 C4 1.3(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C14 N13 C12 N10 179.85(15) . . . 3_666 ?
C14 N13 C12 C11 0.0(2) . . . . ?
C15 N16 C11 N10 -178.96(16) . . . . ?
C15 N16 C11 C12 1.2(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C1 C2 C7 178.72(18) . . . . ?
C6 C5 C4 C3 -1.0(3) . . . . ?
C6 C5 C4 C8 177.1(2) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C17 C14 C15 N16 178.01(17) . . . . ?
C17 C14 C15 C19 -3.3(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C9 179.21(19) . . . . ?
C7 C2 C3 C4 -178.4(2) . . . . ?
C9 C6 C5 C4 -178.5(2) . . . . ?
C8 C4 C3 C2 -178.1(2) . . . . ?
C22 O21 C25 C24B -20.9(5) . . . . ?
C22 O21 C25 C24A 13.3(6) . . . . ?
C22 C23 C24B C25 -25.3(7) . . . . ?
C22 C23 C24A C25 27.9(8) . . . . ?
C23 C24B C25 O21 28.7(7) . . . . ?
C23 C24A C25 O21 -26.2(8) . . . . ?
C25 O21 C22 C23 4.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.628
_oxdiff_exptl_absorpt_empirical_full_min 0.805
####################################################################### 
# 
# 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_TCDP-DMF
_database_code_depnum_ccdc_archive 'CCDC 2429933'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 2(C3 H7 N O)'
_chemical_formula_sum            'C36 H36 N12 O2'
_chemical_formula_weight         668.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0545(2)
_cell_length_b                   12.3215(3)
_cell_length_c                   16.3699(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.908(2)
_cell_angle_gamma                90
_cell_volume                     1823.96(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3313
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      70.7220
_cell_measurement_theta_min      4.4770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6480
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         4.494
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 8.1195
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  20.00   1.00    3.59    --  -34.90  19.00-120.00   25
  2  ω     -5.00  20.00   1.00    3.59    --  -34.90  19.00 120.00   25
  3  ω    -33.00  30.00   1.00    3.59    --   34.90 -37.00  90.00   63
  4  ω     48.00  73.00   1.00    3.59    --   34.90 -99.00 -90.00   25
  5  ω     32.00  94.00   1.00    3.59    --   34.90  57.00-180.00   62
  6  ω     18.00  65.00   1.00    3.59    --   34.90  57.00  30.00   47
  7  ω    -20.00  48.00   1.00    3.59    --   34.90 -57.00  30.00   68
  8  ω     42.00  71.00   1.00    3.59    --   34.90-125.00 -90.00   29
  9  ω     47.00  72.00   1.00    3.59    --   34.90 -99.00  60.00   25
 10  ω     49.00  98.00   1.00   14.35    --  107.04 -94.00-150.00   49
 11  ω     43.00  71.00   1.00   14.35    --  107.04 -45.00  60.00   28
 12  ω     41.00  69.00   1.00   14.35    --  107.04 -45.00  30.00   28
 13  ω     41.00 104.00   1.00   14.35    --  107.04 -94.00 -90.00   63
 14  ω     42.00  67.00   1.00   14.35    --  107.04 -45.00 -30.00   25
 15  ω     43.00  69.00   1.00   14.35    --  107.04 -45.00 120.00   26
 16  ω     54.00  89.00   1.00   14.35    --  107.04 -61.00 -90.00   35
 17  ω     98.00 127.00   1.00   14.35    --  107.04  61.00 150.00   29
 18  ω     39.00  72.00   1.00   14.35    --  107.04 -45.00   0.00   33
 19  ω     39.00  71.00   1.00   14.35    --  107.04 -45.00 -60.00   32
 20  ω     56.00  83.00   1.00   14.35    --  107.04 -61.00  90.00   27
 21  ω     46.00 148.00   1.00   14.35    --  107.04   0.00 -90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2803
_reflns_number_total             3330
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+0.3488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O22A-C21A = O25-C24
 1.22 with sigma of 0.005
 N19A-C21A = N22-C24
 1.32 with sigma of 0.01
 N19A-C20A = N19A-C18A = N22-C23 = N22-C21
 1.45 with sigma of 0.01
 N19A-C18A \\sim N19A-C20A \\sim N19A-C21A
 with sigma of 0.02
 N22-C23 \\sim N22-C21 \\sim N22-C24
 with sigma of 0.02
 C18A-C21A \\sim C21A-C20A
 with sigma of 0.02
 O22A-C21A \\sim O25-C24
 with sigma of 0.02
 C23-C24 \\sim C24-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O22A) \\sim Ueq, Uanis(O25) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(N22)
\\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(N19A) \\sim Ueq, Uanis(C23) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C18A) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: O25(0.5) C21A(0.5) H21D(0.5) C24(0.5) H24(0.5) N19A(0.5) C18A(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5) C20A(0.5) H20A(0.5) H20B(0.5) H20C(0.5) C23(0.5)
 H23A(0.5) H23B(0.5) H23C(0.5) O22A(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
 N22(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C21A(H21D), C24(H24)
5.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C18A(H18A,H18B,H18C),
 C20A(H20A,H20B,H20C), C23(H23A,H23B,H23C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.96839(13) 0.39176(10) 0.51926(8) 0.0357(3) Uani 1 1 d . . . . .
N13 N 0.80898(13) 0.66174(10) 0.53051(8) 0.0363(3) Uani 1 1 d . . . . .
N16 N 0.74011(13) 0.44412(11) 0.56400(8) 0.0377(3) Uani 1 1 d . . . . .
C11 C 0.86670(15) 0.47185(12) 0.53374(9) 0.0332(3) Uani 1 1 d . . . . .
C12 C 0.89972(15) 0.58254(12) 0.51538(8) 0.0325(3) Uani 1 1 d . . . . .
C14 C 0.68211(15) 0.63311(13) 0.56553(9) 0.0361(4) Uani 1 1 d . . . . .
C15 C 0.64774(15) 0.52678(14) 0.58048(9) 0.0371(4) Uani 1 1 d . . . . .
N18 N 0.51524(17) 0.79133(14) 0.60760(11) 0.0592(4) Uani 1 1 d . . . . .
C1 C 0.93747(16) 0.27944(13) 0.53978(10) 0.0396(4) Uani 1 1 d . . . . .
C17 C 0.58788(17) 0.72083(15) 0.58848(10) 0.0429(4) Uani 1 1 d . . . . .
N20 N 0.39776(18) 0.47955(16) 0.64069(13) 0.0696(5) Uani 1 1 d . . . . .
C19 C 0.50921(17) 0.49873(15) 0.61502(11) 0.0462(4) Uani 1 1 d . . . . .
C2 C 0.87091(17) 0.21391(14) 0.47996(12) 0.0476(4) Uani 1 1 d . . . . .
C6 C 0.9769(2) 0.24353(16) 0.61784(11) 0.0511(4) Uani 1 1 d . . . . .
C3 C 0.8395(2) 0.10734(16) 0.50260(16) 0.0638(6) Uani 1 1 d . . . . .
H3 H 0.793344 0.060192 0.463097 0.077 Uiso 1 1 calc R U . . .
C5 C 0.9435(2) 0.13619(18) 0.63638(15) 0.0651(6) Uani 1 1 d . . . . .
H5 H 0.970163 0.109124 0.689428 0.078 Uiso 1 1 calc R U . . .
C7 C 0.8390(2) 0.2548(2) 0.39465(13) 0.0618(5) Uani 1 1 d . . . . .
H7A H 0.770641 0.316433 0.395891 0.093 Uiso 1 1 calc R U . . .
H7B H 0.794069 0.196698 0.360949 0.093 Uiso 1 1 calc R U . . .
H7C H 0.931375 0.278179 0.371343 0.093 Uiso 1 1 calc R U . . .
C4 C 0.8731(2) 0.06821(16) 0.58029(18) 0.0694(7) Uani 1 1 d . . . . .
C9 C 1.0524(3) 0.3171(2) 0.67978(13) 0.0765(7) Uani 1 1 d . . . . .
H9A H 1.145442 0.343254 0.658861 0.115 Uiso 1 1 calc R U . . .
H9B H 1.073056 0.277034 0.730815 0.115 Uiso 1 1 calc R U . . .
H9C H 0.988056 0.378976 0.690157 0.115 Uiso 1 1 calc R U . . .
C8 C 0.8337(3) -0.04635(19) 0.6038(3) 0.1075(13) Uani 1 1 d . . . . .
H8A H 0.732633 -0.047800 0.622607 0.161 Uiso 1 1 calc R U . . .
H8B H 0.902636 -0.071522 0.647851 0.161 Uiso 1 1 calc R U . . .
H8C H 0.840158 -0.094048 0.556217 0.161 Uiso 1 1 calc R U . . .
O25 O 0.9073(11) 0.5618(5) 0.7040(3) 0.0873(19) Uani 0.5 1 d D U P A 1
C21A C 0.9038(5) 0.6455(4) 0.7712(3) 0.0674(12) Uani 0.5 1 d D U P B 2
H21D H 0.825888 0.690485 0.788133 0.081 Uiso 0.5 1 calc R U P B 2
C24 C 0.9674(7) 0.5640(4) 0.7714(3) 0.0859(15) Uani 0.5 1 d D U P A 1
H24 H 1.011411 0.498745 0.791761 0.103 Uiso 0.5 1 calc R U P A 1
N19A N 1.0206(6) 0.6324(5) 0.8239(4) 0.0544(13) Uani 0.5 1 d D U P B 2
C18A C 1.0116(8) 0.6849(6) 0.9024(4) 0.0769(17) Uani 0.5 1 d D U P B 2
H18A H 0.927201 0.734739 0.900559 0.115 Uiso 0.5 1 calc R U P B 2
H18B H 1.102872 0.725574 0.915104 0.115 Uiso 0.5 1 calc R U P B 2
H18C H 0.998634 0.629903 0.944674 0.115 Uiso 0.5 1 calc R U P B 2
C20A C 1.1391(5) 0.5653(4) 0.8050(3) 0.0796(14) Uani 0.5 1 d D U P B 2
H20A H 1.128286 0.494452 0.831270 0.119 Uiso 0.5 1 calc R U P B 2
H20B H 1.232280 0.598810 0.824856 0.119 Uiso 0.5 1 calc R U P B 2
H20C H 1.139661 0.555593 0.745567 0.119 Uiso 0.5 1 calc R U P B 2
C23 C 0.8987(8) 0.7460(5) 0.7915(5) 0.116(2) Uani 0.5 1 d D U P A 1
H23A H 0.969986 0.802088 0.777554 0.175 Uiso 0.5 1 calc R U P A 1
H23B H 0.837713 0.772826 0.834941 0.175 Uiso 0.5 1 calc R U P A 1
H23C H 0.835300 0.728410 0.743016 0.175 Uiso 0.5 1 calc R U P A 1
O22A O 0.8890(9) 0.6052(7) 0.7041(4) 0.107(2) Uani 0.5 1 d D U P B 2
C21 C 1.0511(14) 0.6429(10) 0.8998(6) 0.157(5) Uani 0.5 1 d D U P A 1
H21A H 1.050958 0.567189 0.918183 0.235 Uiso 0.5 1 calc R U P A 1
H21B H 0.999263 0.687997 0.938486 0.235 Uiso 0.5 1 calc R U P A 1
H21C H 1.153320 0.668228 0.897056 0.235 Uiso 0.5 1 calc R U P A 1
N22 N 0.9765(9) 0.6507(6) 0.8192(4) 0.073(2) Uani 0.5 1 d D U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C11 1.3784(19) . ?
N10 C12 1.3844(17) 3_766 ?
N10 C1 1.455(2) . ?
N13 C12 1.307(2) . ?
N13 C14 1.3563(18) . ?
N16 C11 1.3166(18) . ?
N16 C15 1.354(2) . ?
C11 C12 1.431(2) . ?
C14 C15 1.371(2) . ?
C14 C17 1.439(2) . ?
C15 C19 1.444(2) . ?
N18 C17 1.143(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.382(3) . ?
N20 C19 1.137(2) . ?
C2 C3 1.398(3) . ?
C2 C7 1.499(3) . ?
C6 C5 1.394(3) . ?
C6 C9 1.498(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.375(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C8 1.511(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O25 C24 1.206(4) . ?
C21A H21D 0.9500 . ?
C21A N19A 1.340(6) . ?
C21A O22A 1.206(4) . ?
C24 H24 0.9500 . ?
C24 N22 1.323(6) . ?
N19A C18A 1.444(6) . ?
N19A C20A 1.401(6) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 N22 1.432(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 N22 1.455(7) . ?

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
C11 N10 C12 120.29(13) . 3_766 ?
C11 N10 C1 120.22(11) . . ?
C12 N10 C1 119.49(13) 3_766 . ?
C12 N13 C14 116.09(13) . . ?
C11 N16 C15 115.98(13) . . ?
N10 C11 C12 119.84(12) . . ?
N16 C11 N10 118.73(14) . . ?
N16 C11 C12 121.43(14) . . ?
N10 C12 C11 119.84(14) 3_766 . ?
N13 C12 N10 118.06(13) . 3_766 ?
N13 C12 C11 122.10(12) . . ?
N13 C14 C15 121.91(14) . . ?
N13 C14 C17 116.18(14) . . ?
C15 C14 C17 121.88(13) . . ?
N16 C15 C14 122.35(13) . . ?
N16 C15 C19 117.11(14) . . ?
C14 C15 C19 120.54(15) . . ?
C2 C1 N10 118.28(15) . . ?
C6 C1 N10 118.32(15) . . ?
C6 C1 C2 123.40(16) . . ?
N18 C17 C14 178.7(2) . . ?
N20 C19 C15 177.6(2) . . ?
C1 C2 C3 116.62(19) . . ?
C1 C2 C7 121.30(16) . . ?
C3 C2 C7 122.06(19) . . ?
C1 C6 C5 117.15(19) . . ?
C1 C6 C9 121.31(17) . . ?
C5 C6 C9 121.5(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 H3 118.8 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 H5 119.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C8 121.2(3) . . ?
C5 C4 C3 118.40(18) . . ?
C5 C4 C8 120.4(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N19A C21A H21D 117.1 . . ?
O22A C21A H21D 117.1 . . ?
O22A C21A N19A 125.7(6) . . ?
O25 C24 H24 117.6 . . ?
O25 C24 N22 124.8(6) . . ?
N22 C24 H24 117.6 . . ?
C21A N19A C18A 116.1(5) . . ?
C21A N19A C20A 121.1(5) . . ?
C20A N19A C18A 122.6(5) . . ?
N19A C18A H18A 109.5 . . ?
N19A C18A H18B 109.5 . . ?
N19A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N19A C20A H20A 109.5 . . ?
N19A C20A H20B 109.5 . . ?
N19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N22 C23 H23A 109.5 . . ?
N22 C23 H23B 109.5 . . ?
N22 C23 H23C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N22 C21 H21A 109.5 . . ?
N22 C21 H21B 109.5 . . ?
N22 C21 H21C 109.5 . . ?
C24 N22 C23 117.4(6) . . ?
C24 N22 C21 119.7(7) . . ?
C23 N22 C21 122.6(7) . . ?

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
N10 C11 C12 N10 2.1(2) . . . 3_766 ?
N10 C11 C12 N13 -177.72(13) . . . . ?
N10 C1 C2 C3 -178.38(13) . . . . ?
N10 C1 C2 C7 3.5(2) . . . . ?
N10 C1 C6 C5 178.79(14) . . . . ?
N10 C1 C6 C9 -1.2(3) . . . . ?
N13 C14 C15 N16 2.4(2) . . . . ?
N13 C14 C15 C19 -177.66(14) . . . . ?
N16 C11 C12 N10 -177.57(13) . . . 3_766 ?
N16 C11 C12 N13 2.7(2) . . . . ?
C11 N10 C1 C2 92.27(17) . . . . ?
C11 N10 C1 C6 -88.12(18) . . . . ?
C11 N16 C15 C14 1.0(2) . . . . ?
C11 N16 C15 C19 -178.98(14) . . . . ?
C12 N10 C11 N16 177.57(13) 3_766 . . . ?
C12 N10 C11 C12 -2.1(2) 3_766 . . . ?
C12 N10 C1 C2 -87.32(18) 3_766 . . . ?
C12 N10 C1 C6 92.29(18) 3_766 . . . ?
C12 N13 C14 C15 -3.1(2) . . . . ?
C12 N13 C14 C17 174.98(14) . . . . ?
C14 N13 C12 N10 -179.08(13) . . . 3_766 ?
C14 N13 C12 C11 0.7(2) . . . . ?
C15 N16 C11 N10 177.01(13) . . . . ?
C15 N16 C11 C12 -3.4(2) . . . . ?
C1 N10 C11 N16 -2.0(2) . . . . ?
C1 N10 C11 C12 178.34(14) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C17 C14 C15 N16 -175.59(15) . . . . ?
C17 C14 C15 C19 4.4(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C9 178.39(18) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C4 C8 178.14(18) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
C6 C1 C2 C7 -176.08(16) . . . . ?
C6 C5 C4 C3 2.2(3) . . . . ?
C6 C5 C4 C8 -177.70(19) . . . . ?
C7 C2 C3 C4 177.82(17) . . . . ?
C9 C6 C5 C4 179.4(2) . . . . ?
O25 C24 N22 C23 5.5(14) . . . . ?
O25 C24 N22 C21 179.5(10) . . . . ?
O22A C21A N19A C18A -177.5(7) . . . . ?
O22A C21A N19A C20A -1.6(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-benzene
_database_code_depnum_ccdc_archive 'CCDC 2429935'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 4(C6 H6)'
_chemical_formula_sum            'C54 H46 N10'
_chemical_formula_weight         835.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.4303(7)
_cell_length_b                   11.1097(10)
_cell_length_c                   11.7866(10)
_cell_angle_alpha                65.920(9)
_cell_angle_beta                 69.939(7)
_cell_angle_gamma                85.587(7)
_cell_volume                     1168.12(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      68.9610
_cell_measurement_theta_min      4.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7472
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         4.371
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 8.1195
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   1.00   30.50    --  -34.90  19.00-180.00   26
  2  ω     37.00  70.00   1.00   30.50    --   34.90-125.00-150.00   33
  3  ω     50.00 104.00   1.00   30.50    --   34.90  19.00   0.00   54
  4  ω      0.00  62.00   1.00   30.50    --   34.90 -77.00 120.00   62
  5  ω     28.00  99.00   1.00   30.50    --   34.90  37.00  30.00   71
  6  ω    -36.00  44.00   1.00   30.50    --   34.90 -19.00  30.00   80
  7  ω    -19.00  28.00   1.00   30.50    --   34.90 -77.00 -60.00   47
  8  ω    -10.00  15.00   1.00   30.50    --   34.90 -19.00-150.00   25
  9  ω    -28.00  44.00   1.00   30.50    --   34.90 -19.00 150.00   72
 10  ω     39.00  83.00   1.00   30.50    --   34.90-125.00  60.00   44
 11  ω     33.00  84.00   1.00   30.50    --   34.90-125.00 -60.00   51
 12  ω     31.00  57.00   1.00   30.50    --   34.90 -99.00  90.00   26
 13  ω     39.00  71.00   1.00   30.50    --  107.04 -45.00  30.00   32
 14  ω    110.00 175.00   1.00   30.50    --  107.04  77.00 -30.00   65
 15  ω     64.00 100.00   1.00   30.50    --  107.04-111.00-180.00   36
 16  ω    129.00 160.00   1.00   30.50    --  107.04  45.00   0.00   31
 17  ω     87.00 113.00   1.00   30.50    --  107.04 -77.00-180.00   26
 18  ω     40.00  70.00   1.00   30.50    --  107.04 -45.00-180.00   30
 19  ω     40.00  67.00   1.00   30.50    --  107.04 -45.00  60.00   27
 20  ω     39.00  64.00   1.00   30.50    --  107.04 -45.00 -30.00   25
 21  ω     61.00 105.00   1.00   30.50    --  107.04-111.00 -30.00   44
 22  ω     61.00 109.00   1.00   30.50    --  107.04-111.00  90.00   48
 23  ω     40.00  72.00   1.00   30.50    --  107.04 -45.00 -90.00   32
 24  ω    104.00 172.00   1.00   30.50    --  107.04  77.00-180.00   68
 25  ω     44.00  71.00   1.00   30.50    --  107.04 -45.00-120.00   27
 26  ω     42.00  72.00   1.00   30.50    --  107.04 -45.00-150.00   30
 27  ω     40.00  70.00   1.00   30.50    --  107.04 -45.00 120.00   30
 28  ω     63.00  93.00   1.00   30.50    --  107.04 -61.00  60.00   30
 29  ω     42.00  69.00   1.00   30.50    --  107.04 -45.00 -60.00   27
 30  ω     57.00  99.00   1.00   30.50    --  107.04 -94.00   0.00   42
 31  ω     71.00 106.00   1.00   30.50    --  107.04 -94.00-180.00   35
 32  ω    123.00 149.00   1.00   30.50    --  107.04 111.00 -90.00   26
 33  ω     38.00 172.00   1.00   30.50    --  107.04   0.00 150.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2550
_reflns_number_total             4263
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1704
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C21(H21), C22(H22), C26(H26), C24(H24), C29(H29), C23(H23),
 C28(H28), C25(H25), C31(H31), C27(H27), C32(H32), C30(H30)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.55279(19) 0.60935(19) 0.8783(2) 0.0346(5) Uani 1 1 d . . . . .
N16 N 0.37594(19) 0.57338(19) 0.8165(2) 0.0370(5) Uani 1 1 d . . . . .
N13 N 0.26020(19) 0.36734(19) 1.0670(2) 0.0366(5) Uani 1 1 d . . . . .
C12 C 0.3777(2) 0.4306(2) 1.0329(2) 0.0328(6) Uani 1 1 d . . . . .
N18 N -0.0426(2) 0.2999(2) 1.0432(3) 0.0571(7) Uani 1 1 d . . . . .
C11 C 0.4336(2) 0.5382(2) 0.9073(2) 0.0322(5) Uani 1 1 d . . . . .
C14 C 0.1976(2) 0.4075(2) 0.9758(3) 0.0354(6) Uani 1 1 d . . . . .
C1 C 0.5984(2) 0.7313(2) 0.7584(2) 0.0350(6) Uani 1 1 d . . . . .
C15 C 0.2558(2) 0.5064(2) 0.8520(3) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.7041(3) 0.7270(2) 0.6501(3) 0.0408(6) Uani 1 1 d . . . . .
N20 N 0.1343(3) 0.5662(2) 0.6807(3) 0.0657(8) Uani 1 1 d . . . . .
C17 C 0.0637(3) 0.3451(2) 1.0150(3) 0.0411(6) Uani 1 1 d . . . . .
C2 C 0.5334(3) 0.8441(2) 0.7587(3) 0.0405(6) Uani 1 1 d . . . . .
C19 C 0.1905(3) 0.5419(3) 0.7538(3) 0.0459(7) Uani 1 1 d . . . . .
C5 C 0.7451(3) 0.8451(3) 0.5374(3) 0.0492(7) Uani 1 1 d . . . . .
H5 H 0.817803 0.846004 0.461532 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6834(3) 0.9607(3) 0.5326(3) 0.0500(8) Uani 1 1 d . . . . .
C3 C 0.5786(3) 0.9593(3) 0.6431(3) 0.0496(7) Uani 1 1 d . . . . .
H3 H 0.536171 1.038760 0.640387 0.060 Uiso 1 1 calc R U . . .
C7 C 0.4166(3) 0.8430(3) 0.8772(3) 0.0568(8) Uani 1 1 d . . . . .
H7A H 0.334617 0.798560 0.884812 0.085 Uiso 1 1 calc R U . . .
H7B H 0.398751 0.934118 0.867051 0.085 Uiso 1 1 calc R U . . .
H7C H 0.440321 0.795707 0.957152 0.085 Uiso 1 1 calc R U . . .
C9 C 0.7704(3) 0.6017(3) 0.6532(3) 0.0574(8) Uani 1 1 d . . . . .
H9A H 0.831677 0.582241 0.704660 0.086 Uiso 1 1 calc R U . . .
H9B H 0.823131 0.612056 0.562748 0.086 Uiso 1 1 calc R U . . .
H9C H 0.699722 0.528796 0.694345 0.086 Uiso 1 1 calc R U . . .
C21 C 0.4072(3) 0.1906(3) 0.8604(3) 0.0622(8) Uani 1 1 d . . . . .
H21 H 0.393086 0.144196 0.952051 0.075 Uiso 1 1 calc R U . . .
C22 C 0.5342(3) 0.2473(3) 0.7733(3) 0.0623(9) Uani 1 1 d . . . . .
H22 H 0.608284 0.240470 0.804631 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2999(3) 0.2010(3) 0.8146(4) 0.0661(9) Uani 1 1 d . . . . .
H26 H 0.211662 0.161314 0.874574 0.079 Uiso 1 1 calc R U . . .
C24 C 0.4482(4) 0.3244(3) 0.5949(4) 0.0716(10) Uani 1 1 d . . . . .
H24 H 0.462673 0.369768 0.503064 0.086 Uiso 1 1 calc R U . . .
C29 C 0.0798(3) 0.7460(4) 0.2307(4) 0.0699(10) Uani 1 1 d . . . . .
H29 H 0.066388 0.675564 0.208944 0.084 Uiso 1 1 calc R U . . .
C23 C 0.5548(3) 0.3143(3) 0.6405(4) 0.0686(9) Uani 1 1 d . . . . .
H23 H 0.643092 0.353581 0.580249 0.082 Uiso 1 1 calc R U . . .
C28 C 0.0904(3) 0.7196(4) 0.3497(4) 0.0752(11) Uani 1 1 d . . . . .
H28 H 0.085082 0.630503 0.410991 0.090 Uiso 1 1 calc R U . . .
C25 C 0.3207(4) 0.2690(4) 0.6820(4) 0.0705(10) Uani 1 1 d . . . . .
H25 H 0.246400 0.277539 0.650730 0.085 Uiso 1 1 calc R U . . .
C8 C 0.7318(3) 1.0861(3) 0.4079(3) 0.0754(11) Uani 1 1 d . . . . .
H8A H 0.822850 1.117281 0.395870 0.113 Uiso 1 1 calc R U . . .
H8B H 0.667633 1.154024 0.415111 0.113 Uiso 1 1 calc R U . . .
H8C H 0.736290 1.068254 0.331803 0.113 Uiso 1 1 calc R U . . .
C31 C 0.1073(4) 0.9733(4) 0.1749(4) 0.0841(12) Uani 1 1 d . . . . .
H31 H 0.113540 1.062362 0.113267 0.101 Uiso 1 1 calc R U . . .
C27 C 0.1083(4) 0.8189(5) 0.3822(4) 0.0812(11) Uani 1 1 d . . . . .
H27 H 0.114713 0.798868 0.466481 0.097 Uiso 1 1 calc R U . . .
C32 C 0.1174(4) 0.9470(4) 0.2960(5) 0.0791(11) Uani 1 1 d . . . . .
H32 H 0.130462 1.016848 0.318655 0.095 Uiso 1 1 calc R U . . .
C30 C 0.0884(4) 0.8736(4) 0.1421(4) 0.0798(11) Uani 1 1 d . . . . .
H30 H 0.081300 0.892702 0.058290 0.096 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
N10 C12 1.382(3) 2_667 ?
N10 C11 1.389(3) . ?
N10 C1 1.461(3) . ?
N16 C11 1.312(3) . ?
N16 C15 1.352(3) . ?
N13 C12 1.313(3) . ?
N13 C14 1.352(3) . ?
C12 C11 1.425(3) . ?
N18 C17 1.136(3) . ?
C14 C15 1.375(3) . ?
C14 C17 1.445(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.379(3) . ?
C15 C19 1.444(3) . ?
C6 C5 1.394(3) . ?
C6 C9 1.499(4) . ?
N20 C19 1.136(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.502(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(4) . ?
C4 C3 1.378(4) . ?
C4 C8 1.511(4) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.368(4) . ?
C21 C26 1.380(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(4) . ?
C26 H26 0.9500 . ?
C26 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.371(4) . ?
C24 C25 1.369(5) . ?
C29 H29 0.9500 . ?
C29 C28 1.354(5) . ?
C29 C30 1.362(5) . ?
C23 H23 0.9500 . ?
C28 H28 0.9500 . ?
C28 C27 1.351(5) . ?
C25 H25 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.375(5) . ?
C31 C30 1.360(5) . ?
C27 H27 0.9500 . ?
C27 C32 1.357(5) . ?
C32 H32 0.9500 . ?
C30 H30 0.9500 . ?

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
C12 N10 C11 119.85(19) 2_667 . ?
C12 N10 C1 120.43(18) 2_667 . ?
C11 N10 C1 119.58(18) . . ?
C11 N16 C15 115.9(2) . . ?
C12 N13 C14 116.5(2) . . ?
N10 C12 C11 120.25(19) 2_667 . ?
N13 C12 N10 118.5(2) . 2_667 ?
N13 C12 C11 121.2(2) . . ?
N10 C11 C12 119.71(19) . . ?
N16 C11 N10 118.1(2) . . ?
N16 C11 C12 122.2(2) . . ?
N13 C14 C15 121.9(2) . . ?
N13 C14 C17 117.2(2) . . ?
C15 C14 C17 120.9(2) . . ?
C6 C1 N10 118.2(2) . . ?
C2 C1 N10 118.3(2) . . ?
C2 C1 C6 123.5(2) . . ?
N16 C15 C14 122.0(2) . . ?
N16 C15 C19 117.3(2) . . ?
C14 C15 C19 120.7(2) . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 C9 121.8(2) . . ?
C5 C6 C9 121.5(3) . . ?
N18 C17 C14 177.8(3) . . ?
C1 C2 C3 117.3(3) . . ?
C1 C2 C7 121.6(2) . . ?
C3 C2 C7 121.1(3) . . ?
N20 C19 C15 177.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C5 C4 C8 119.9(3) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C8 121.2(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C22 C21 H21 120.1 . . ?
C22 C21 C26 119.8(3) . . ?
C26 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C26 H26 120.1 . . ?
C25 C26 C21 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C25 C24 C23 119.8(3) . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(4) . . ?
C30 C29 H29 120.0 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C29 C28 H28 119.7 . . ?
C27 C28 C29 120.6(4) . . ?
C27 C28 H28 119.7 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 121.0(4) . . ?
C28 C27 H27 119.6 . . ?
C28 C27 C32 120.8(4) . . ?
C32 C27 H27 119.6 . . ?
C31 C32 H32 120.8 . . ?
C27 C32 C31 118.4(4) . . ?
C27 C32 H32 120.8 . . ?
C29 C30 H30 120.4 . . ?
C31 C30 C29 119.3(4) . . ?
C31 C30 H30 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 C12 C11 N10 -5.0(4) 2_667 . . . ?
N10 C12 C11 N16 175.1(2) 2_667 . . . ?
N10 C1 C6 C5 -180.0(2) . . . . ?
N10 C1 C6 C9 0.5(3) . . . . ?
N10 C1 C2 C3 -179.9(2) . . . . ?
N10 C1 C2 C7 -1.3(3) . . . . ?
N13 C12 C11 N10 175.1(2) . . . . ?
N13 C12 C11 N16 -4.8(4) . . . . ?
N13 C14 C15 N16 -3.1(4) . . . . ?
N13 C14 C15 C19 176.2(2) . . . . ?
C12 N10 C11 N16 -175.1(2) 2_667 . . . ?
C12 N10 C11 C12 5.0(4) 2_667 . . . ?
C12 N10 C1 C6 82.5(3) 2_667 . . . ?
C12 N10 C1 C2 -98.0(3) 2_667 . . . ?
C12 N13 C14 C15 2.1(4) . . . . ?
C12 N13 C14 C17 -175.8(2) . . . . ?
C11 N10 C1 C6 -101.9(3) . . . . ?
C11 N10 C1 C2 77.6(3) . . . . ?
C11 N16 C15 C14 0.0(4) . . . . ?
C11 N16 C15 C19 -179.3(2) . . . . ?
C14 N13 C12 N10 -178.3(2) . . . 2_667 ?
C14 N13 C12 C11 1.6(3) . . . . ?
C1 N10 C11 N16 9.2(3) . . . . ?
C1 N10 C11 C12 -170.7(2) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C15 N16 C11 N10 -176.2(2) . . . . ?
C15 N16 C11 C12 3.7(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C1 C2 C7 178.2(2) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C6 C5 C4 C8 -180.0(2) . . . . ?
C17 C14 C15 N16 174.7(2) . . . . ?
C17 C14 C15 C19 -6.0(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C9 -179.0(2) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C7 C2 C3 C4 -178.3(2) . . . . ?
C9 C6 C5 C4 179.0(2) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C21 C26 C25 C24 1.1(5) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
C29 C28 C27 C32 -0.6(6) . . . . ?
C23 C24 C25 C26 -1.3(5) . . . . ?
C28 C29 C30 C31 -0.2(5) . . . . ?
C28 C27 C32 C31 0.3(6) . . . . ?
C25 C24 C23 C22 0.7(5) . . . . ?
C8 C4 C3 C2 -179.9(2) . . . . ?
C32 C31 C30 C29 -0.1(6) . . . . ?
C30 C29 C28 C27 0.5(5) . . . . ?
C30 C31 C32 C27 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-thiophene
_database_code_depnum_ccdc_archive 'CCDC 2429936'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C4 H4 S), C30 H22 N10'
_chemical_formula_sum            'C46 H38 N10 S4'
_chemical_formula_weight         859.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.4879(5)
_cell_length_b                   10.8573(5)
_cell_length_c                   11.2117(5)
_cell_angle_alpha                68.012(4)
_cell_angle_beta                 68.117(4)
_cell_angle_gamma                86.081(4)
_cell_volume                     1094.75(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      29.1590
_cell_measurement_theta_min      3.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.040
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  51.00   0.50    0.07    --  -19.87  23.00 -27.00   54
  2  ω     16.00  46.00   0.50    0.07    --   21.12 -57.00   0.00   60
  3  ω    -10.00  16.00   0.50    0.07    --  -19.87 -99.00 -90.00   52
  4  ω    -11.00  29.00   0.50    0.07    --  -19.87 -99.00 -30.00   80
  5  ω    -14.00  11.00   0.50    0.07    --  -19.87 -99.00  30.00   50
  6  ω    -12.00  29.00   0.50    0.07    --  -19.87 -99.00  90.00   82
  7  ω     -1.00  65.00   0.50    0.07    --  -19.87 -23.00 167.00  132
  8  ω    -12.00  14.00   0.50    0.07    --  -19.87 -99.00-180.00   52
  9  ω    -43.00 -11.00   0.50    0.07    --   21.12 -57.00   0.00   64
 10  ω    -77.00  15.00   0.50    0.07    --  -19.87 -57.00  90.00  184
 11  ω   -102.00  17.00   0.50    0.07    --  -19.87  23.00 -27.00  238
 12  ω   -108.00  -5.00   0.50    0.07    --  -19.87 -23.00 167.00  206
 13  ω   -115.00 -44.00   0.50    0.07    --  -19.87 179.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3282
_reflns_number_total             4471
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.514
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0997
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1619P)²+2.6623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2861
_refine_ls_wR_factor_ref         0.3140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S26-C30 = S26-C27 = S21-C22 = S21-C25
 1.73 with sigma of 0.01
 C29-C28
 1.53 with sigma of 0.01
 S26-C30 \\sim S26-C27
 with sigma of 0.001
 C30-C29 \\sim C28-C27
 with sigma of 0.001
 S21-C22 \\sim S21-C25
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C5(H5), C24(H24), C30(H30), C28(H28), C25(H25), C22(H22),
 C29(H29), C27(H27)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S21 S 0.30425(16) 0.20706(16) 0.7591(2) 0.0671(5) Uani 1 1 d D . . . .
S26 S 0.9097(3) 0.0588(3) 0.8662(3) 0.1397(14) Uani 1 1 d D . . . .
N16 N 0.3811(3) 0.5715(3) 0.8089(3) 0.0232(7) Uani 1 1 d . . . . .
N13 N 0.2575(3) 0.3673(3) 1.0712(3) 0.0222(7) Uani 1 1 d . . . . .
N10 N 0.5582(3) 0.6065(3) 0.8718(3) 0.0212(6) Uani 1 1 d . . . . .
C23 C 0.5245(4) 0.2535(4) 0.7842(4) 0.0260(8) Uani 1 1 d . . . . .
H23 H 0.592226 0.252783 0.821857 0.031 Uiso 1 1 calc R U . . .
N18 N -0.0415(4) 0.2943(4) 1.0431(4) 0.0400(9) Uani 1 1 d . . . . .
C1 C 0.6093(4) 0.7263(3) 0.7466(3) 0.0218(7) Uani 1 1 d . . . . .
N20 N 0.1420(4) 0.5628(4) 0.6686(4) 0.0409(9) Uani 1 1 d . . . . .
C12 C 0.3758(4) 0.4305(3) 1.0353(3) 0.0202(7) Uani 1 1 d . . . . .
C11 C 0.4374(3) 0.5373(3) 0.9028(3) 0.0208(7) Uani 1 1 d . . . . .
C15 C 0.2604(4) 0.5044(3) 0.8459(4) 0.0228(7) Uani 1 1 d . . . . .
C14 C 0.1976(4) 0.4058(3) 0.9762(4) 0.0234(8) Uani 1 1 d . . . . .
C2 C 0.7193(4) 0.7213(4) 0.6330(4) 0.0256(8) Uani 1 1 d . . . . .
C6 C 0.5428(4) 0.8419(4) 0.7482(4) 0.0241(8) Uani 1 1 d . . . . .
C17 C 0.0646(4) 0.3409(4) 1.0152(4) 0.0281(8) Uani 1 1 d . . . . .
C19 C 0.1961(4) 0.5396(4) 0.7452(4) 0.0279(8) Uani 1 1 d . . . . .
C4 C 0.7000(4) 0.9564(4) 0.5105(4) 0.0292(9) Uani 1 1 d . . . . .
C3 C 0.7634(4) 0.8389(4) 0.5149(4) 0.0282(8) Uani 1 1 d . . . . .
H3 H 0.839019 0.838496 0.435185 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5910(4) 0.9564(4) 0.6270(4) 0.0286(8) Uani 1 1 d . . . . .
H5 H 0.547381 1.036445 0.624914 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7884(4) 0.5952(4) 0.6333(4) 0.0343(9) Uani 1 1 d . . . . .
H7A H 0.848142 0.578574 0.686331 0.051 Uiso 1 1 calc R U . . .
H7B H 0.844028 0.604610 0.537610 0.051 Uiso 1 1 calc R U . . .
H7C H 0.718224 0.520315 0.675967 0.051 Uiso 1 1 calc R U . . .
C24 C 0.5446(5) 0.3267(4) 0.6313(4) 0.0372(10) Uani 1 1 d . . . . .
H24 H 0.626348 0.378571 0.561128 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4238(5) 0.8434(4) 0.8739(4) 0.0355(9) Uani 1 1 d . . . . .
H9A H 0.341672 0.796892 0.883296 0.053 Uiso 1 1 calc R U . . .
H9B H 0.405900 0.935816 0.863962 0.053 Uiso 1 1 calc R U . . .
H9C H 0.446082 0.798496 0.956672 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7508(5) 1.0808(4) 0.3816(5) 0.0420(11) Uani 1 1 d . . . . .
H8A H 0.841897 1.113242 0.368415 0.063 Uiso 1 1 calc R U . . .
H8B H 0.686205 1.149283 0.391240 0.063 Uiso 1 1 calc R U . . .
H8C H 0.757412 1.060918 0.301263 0.063 Uiso 1 1 calc R U . . .
C30 C 0.9128(5) 0.2316(5) 0.7795(5) 0.0584(16) Uani 1 1 d D . . . .
H30 H 0.929002 0.299161 0.808018 0.070 Uiso 1 1 calc R U . . .
C28 C 0.8594(5) 0.1305(5) 0.6467(6) 0.0526(13) Uani 1 1 d D . . . .
H28 H 0.837564 0.132828 0.570951 0.063 Uiso 1 1 calc R U . . .
C25 C 0.4281(5) 0.3071(4) 0.6093(5) 0.0487(12) Uani 1 1 d D . . . .
H25 H 0.418371 0.344582 0.522167 0.058 Uiso 1 1 calc R U . . .
C22 C 0.3988(5) 0.1912(5) 0.8565(5) 0.0476(12) Uani 1 1 d D . . . .
H22 H 0.365267 0.142419 0.953926 0.057 Uiso 1 1 calc R U . . .
C29 C 0.8888(5) 0.2494(5) 0.6687(6) 0.0680(19) Uani 1 1 d D . . . .
H29 H 0.890114 0.336456 0.603829 0.082 Uiso 1 1 calc R U . . .
C27 C 0.8674(6) 0.0220(6) 0.7450(6) 0.077(2) Uani 1 1 d D . . . .
H27 H 0.852369 -0.065586 0.750446 0.092 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
S21 C25 1.700(5) . ?
S21 C22 1.688(5) . ?
S26 C30 1.757(4) . ?
S26 C27 1.756(4) . ?
N16 C11 1.317(5) . ?
N16 C15 1.347(5) . ?
N13 C12 1.308(5) . ?
N13 C14 1.354(5) . ?
N10 C1 1.455(4) . ?
N10 C12 1.382(4) 2_667 ?
N10 C11 1.377(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.532(5) . ?
C23 C22 1.330(6) . ?
N18 C17 1.137(5) . ?
C1 C2 1.380(5) . ?
C1 C6 1.396(5) . ?
N20 C19 1.142(5) . ?
C12 C11 1.437(5) . ?
C15 C14 1.386(5) . ?
C15 C19 1.444(5) . ?
C14 C17 1.443(5) . ?
C2 C3 1.399(5) . ?
C2 C7 1.504(5) . ?
C6 C5 1.399(5) . ?
C6 C9 1.499(5) . ?
C4 C3 1.390(6) . ?
C4 C5 1.379(6) . ?
C4 C8 1.502(5) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.377(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C30 H30 0.9500 . ?
C30 C29 1.300(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.473(6) . ?
C28 C27 1.301(6) . ?
C25 H25 0.9500 . ?
C22 H22 0.9500 . ?
C29 H29 0.9500 . ?
C27 H27 0.9500 . ?

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
C22 S21 C25 94.3(3) . . ?
C27 S26 C30 93.1(3) . . ?
C11 N16 C15 116.3(3) . . ?
C12 N13 C14 116.6(3) . . ?
C12 N10 C1 119.9(3) 2_667 . ?
C11 N10 C1 119.5(3) . . ?
C11 N10 C12 120.3(3) . 2_667 ?
C24 C23 H23 124.9 . . ?
C22 C23 H23 124.9 . . ?
C22 C23 C24 110.2(4) . . ?
C2 C1 N10 119.4(3) . . ?
C2 C1 C6 123.2(3) . . ?
C6 C1 N10 117.4(3) . . ?
N13 C12 N10 118.7(3) . 2_667 ?
N13 C12 C11 121.5(3) . . ?
N10 C12 C11 119.8(3) 2_667 . ?
N16 C11 N10 118.5(3) . . ?
N16 C11 C12 121.6(3) . . ?
N10 C11 C12 119.9(3) . . ?
N16 C15 C14 122.0(3) . . ?
N16 C15 C19 117.7(3) . . ?
C14 C15 C19 120.3(3) . . ?
N13 C14 C15 121.7(3) . . ?
N13 C14 C17 117.7(3) . . ?
C15 C14 C17 120.6(3) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 C7 122.2(3) . . ?
C3 C2 C7 120.7(4) . . ?
C1 C6 C5 117.2(3) . . ?
C1 C6 C9 121.6(3) . . ?
C5 C6 C9 121.2(3) . . ?
N18 C17 C14 177.4(4) . . ?
N20 C19 C15 177.3(4) . . ?
C3 C4 C8 120.4(4) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C8 121.0(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 119.0 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C23 C24 H24 124.6 . . ?
C25 C24 C23 110.9(4) . . ?
C25 C24 H24 124.6 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S26 C30 H30 126.6 . . ?
C29 C30 S26 106.9(4) . . ?
C29 C30 H30 126.6 . . ?
C29 C28 H28 124.6 . . ?
C27 C28 H28 124.6 . . ?
C27 C28 C29 110.9(5) . . ?
S21 C25 H25 124.5 . . ?
C24 C25 S21 110.9(3) . . ?
C24 C25 H25 124.5 . . ?
S21 C22 H22 123.2 . . ?
C23 C22 S21 113.7(4) . . ?
C23 C22 H22 123.2 . . ?
C30 C29 C28 118.1(5) . . ?
C30 C29 H29 121.0 . . ?
C28 C29 H29 121.0 . . ?
S26 C27 H27 124.5 . . ?
C28 C27 S26 111.0(4) . . ?
C28 C27 H27 124.5 . . ?

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
S26 C30 C29 C28 3.0(6) . . . . ?
N16 C15 C14 N13 -3.1(6) . . . . ?
N16 C15 C14 C17 176.6(3) . . . . ?
N13 C12 C11 N16 -3.7(5) . . . . ?
N13 C12 C11 N10 176.4(3) . . . . ?
N10 C1 C2 C3 179.3(3) . . . . ?
N10 C1 C2 C7 0.5(5) . . . . ?
N10 C1 C6 C5 -179.1(3) . . . . ?
N10 C1 C6 C9 0.4(5) . . . . ?
N10 C12 C11 N16 176.8(3) 2_667 . . . ?
N10 C12 C11 N10 -3.2(5) 2_667 . . . ?
C23 C24 C25 S21 -0.8(5) . . . . ?
C1 N10 C11 N16 9.0(5) . . . . ?
C1 N10 C11 C12 -171.0(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C6 C5 C4 -0.3(5) . . . . ?
C12 N13 C14 C15 1.9(5) . . . . ?
C12 N13 C14 C17 -177.8(3) . . . . ?
C12 N10 C1 C2 81.4(4) 2_667 . . . ?
C12 N10 C1 C6 -98.8(4) 2_667 . . . ?
C12 N10 C11 N16 -176.8(3) 2_667 . . . ?
C12 N10 C11 C12 3.2(6) 2_667 . . . ?
C11 N16 C15 C14 0.8(5) . . . . ?
C11 N16 C15 C19 180.0(3) . . . . ?
C11 N10 C1 C2 -104.4(4) . . . . ?
C11 N10 C1 C6 75.5(4) . . . . ?
C15 N16 C11 N10 -177.6(3) . . . . ?
C15 N16 C11 C12 2.4(5) . . . . ?
C14 N13 C12 N10 -179.1(3) . . . 2_667 ?
C14 N13 C12 C11 1.3(5) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C1 C6 C9 -179.8(4) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C6 C1 C2 C7 -179.4(4) . . . . ?
C19 C15 C14 N13 177.7(3) . . . . ?
C19 C15 C14 C17 -2.6(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C5 C4 C3 C2 0.5(6) . . . . ?
C7 C2 C3 C4 178.8(4) . . . . ?
C24 C23 C22 S21 2.0(5) . . . . ?
C9 C6 C5 C4 -179.8(4) . . . . ?
C8 C4 C3 C2 179.8(4) . . . . ?
C8 C4 C5 C6 -179.6(4) . . . . ?
C30 S26 C27 C28 1.2(5) . . . . ?
C25 S21 C22 C23 -2.2(4) . . . . ?
C22 S21 C25 C24 1.6(4) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C29 C28 C27 S26 0.1(6) . . . . ?
C27 S26 C30 C29 -2.4(4) . . . . ?
C27 C28 C29 C30 -2.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-acetone
_database_code_depnum_ccdc_archive 'CCDC 2429932'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, 2(C3 H6 O)'
_chemical_formula_sum            'C36 H34 N10 O2'
_chemical_formula_weight         638.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7836(4)
_cell_length_b                   12.5914(5)
_cell_length_c                   15.6251(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.763(5)
_cell_angle_gamma                90
_cell_volume                     1716.08(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      29.3710
_cell_measurement_theta_min      2.8410
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  21.00   0.50    1.58    --   21.12  57.00  30.00   52
  2  ω    -99.00  14.00   0.50    1.58    --  -19.87 -57.00 -30.00  226
  3  ω     -1.00  25.00   0.50    1.58    --   21.12 -99.00  60.00   52
  4  ω     22.00  47.00   0.50    1.58    --   21.12-141.00  22.00   50
  5  ω     16.00  88.00   0.50    1.58    --   21.12-128.00-165.00  144
  6  ω     43.00 100.00   0.50    1.58    --   21.12  57.00  30.00  114
  7  ω     39.00  93.00   0.50    1.58    --   21.12 179.00-150.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0189658000
_diffrn_orient_matrix_UB_12      0.0348059000
_diffrn_orient_matrix_UB_13      -0.0353179000
_diffrn_orient_matrix_UB_21      0.0101735000
_diffrn_orient_matrix_UB_22      0.0442094000
_diffrn_orient_matrix_UB_23      0.0282380000
_diffrn_orient_matrix_UB_31      0.0784408000
_diffrn_orient_matrix_UB_32      0.0026924000
_diffrn_orient_matrix_UB_33      -0.0066264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2513
_reflns_number_total             3772
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0968P)²+0.0653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1837
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C23(H23A,H23B,H23C),
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.46589(17) 0.60408(11) 0.52434(10) 0.0257(4) Uani 1 1 d . . . . .
N13 N 0.76214(17) 0.45554(12) 0.43084(10) 0.0276(4) Uani 1 1 d . . . . .
N16 N 0.69195(17) 0.66329(12) 0.48001(10) 0.0281(4) Uani 1 1 d . . . . .
O21 O 0.5945(2) 0.59880(14) 0.27314(11) 0.0594(5) Uani 1 1 d . . . . .
N18 N 1.11004(19) 0.50143(14) 0.35692(12) 0.0379(4) Uani 1 1 d . . . . .
N20 N 0.9935(2) 0.80288(14) 0.42321(13) 0.0433(5) Uani 1 1 d . . . . .
C12 C 0.6353(2) 0.47774(14) 0.46399(11) 0.0244(4) Uani 1 1 d . . . . .
C1 C 0.4352(2) 0.71230(14) 0.55041(12) 0.0267(4) Uani 1 1 d . . . . .
C15 C 0.8212(2) 0.64051(14) 0.44429(12) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.6004(2) 0.58343(14) 0.48901(12) 0.0250(4) Uani 1 1 d . . . . .
C14 C 0.8559(2) 0.53903(14) 0.42013(12) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.4731(2) 0.73987(15) 0.63654(13) 0.0311(4) Uani 1 1 d . . . . .
C6 C 0.3756(2) 0.78445(15) 0.48755(13) 0.0296(4) Uani 1 1 d . . . . .
C17 C 0.9963(2) 0.51659(14) 0.38421(12) 0.0285(4) Uani 1 1 d . . . . .
C19 C 0.9201(2) 0.72985(15) 0.43258(13) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.3504(2) 0.88771(15) 0.51497(14) 0.0351(5) Uani 1 1 d . . . . .
H5 H 0.308050 0.938396 0.473834 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3849(2) 0.91906(16) 0.60017(15) 0.0378(5) Uani 1 1 d . . . . .
C3 C 0.4469(2) 0.84357(16) 0.65963(14) 0.0380(5) Uani 1 1 d . . . . .
H3 H 0.472045 0.864181 0.718073 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3447(2) 0.75355(17) 0.39459(14) 0.0367(5) Uani 1 1 d . . . . .
H9A H 0.442020 0.739735 0.371747 0.055 Uiso 1 1 calc R U . . .
H9B H 0.290509 0.811413 0.361932 0.055 Uiso 1 1 calc R U . . .
H9C H 0.281334 0.689294 0.389246 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5332(3) 0.63853(17) 0.20774(16) 0.0465(6) Uani 1 1 d . . . . .
C7 C 0.5409(3) 0.65883(18) 0.70112(15) 0.0448(5) Uani 1 1 d . . . . .
H7A H 0.468156 0.600284 0.704137 0.067 Uiso 1 1 calc R U . . .
H7B H 0.561844 0.692220 0.757941 0.067 Uiso 1 1 calc R U . . .
H7C H 0.636595 0.631288 0.683280 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3561(3) 1.03100(18) 0.62837(19) 0.0543(7) Uani 1 1 d . . . . .
H8A H 0.340409 1.077352 0.577718 0.081 Uiso 1 1 calc R U . . .
H8B H 0.444624 1.056046 0.667144 0.081 Uiso 1 1 calc R U . . .
H8C H 0.264462 1.032378 0.658591 0.081 Uiso 1 1 calc R U . . .
C23 C 0.5666(3) 0.7491(2) 0.1823(2) 0.0631(8) Uani 1 1 d . . . . .
H23A H 0.472442 0.791432 0.178707 0.095 Uiso 1 1 calc R U . . .
H23B H 0.605441 0.748466 0.126038 0.095 Uiso 1 1 calc R U . . .
H23C H 0.643865 0.780179 0.225416 0.095 Uiso 1 1 calc R U . . .
C24 C 0.4192(4) 0.5790(2) 0.1469(2) 0.0918(12) Uani 1 1 d . . . . .
H24A H 0.418920 0.504067 0.163820 0.138 Uiso 1 1 calc R U . . .
H24B H 0.447294 0.584827 0.088215 0.138 Uiso 1 1 calc R U . . .
H24C H 0.316820 0.609175 0.148860 0.138 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
N10 C12 1.387(2) 3_666 ?
N10 C1 1.456(2) . ?
N10 C11 1.386(2) . ?
N13 C12 1.313(2) . ?
N13 C14 1.358(2) . ?
N16 C15 1.354(2) . ?
N16 C11 1.306(2) . ?
O21 C22 1.206(3) . ?
N18 C17 1.148(2) . ?
N20 C19 1.142(2) . ?
C12 C11 1.431(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.394(3) . ?
C15 C14 1.377(3) . ?
C15 C19 1.446(3) . ?
C14 C17 1.441(3) . ?
C2 C3 1.381(3) . ?
C2 C7 1.507(3) . ?
C6 C5 1.395(3) . ?
C6 C9 1.497(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(3) . ?
C4 C3 1.394(3) . ?
C4 C8 1.507(3) . ?
C3 H3 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C22 C23 1.486(3) . ?
C22 C24 1.498(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N10 C1 121.05(14) 3_666 . ?
C11 N10 C12 120.17(15) . 3_666 ?
C11 N10 C1 118.77(14) . . ?
C12 N13 C14 116.05(15) . . ?
C11 N16 C15 116.01(16) . . ?
N10 C12 C11 119.59(16) 3_666 . ?
N13 C12 N10 118.73(16) . 3_666 ?
N13 C12 C11 121.68(16) . . ?
C2 C1 N10 118.21(17) . . ?
C2 C1 C6 123.09(17) . . ?
C6 C1 N10 118.64(17) . . ?
N16 C15 C14 122.22(16) . . ?
N16 C15 C19 115.66(16) . . ?
C14 C15 C19 122.12(16) . . ?
N10 C11 C12 120.24(16) . . ?
N16 C11 N10 117.59(16) . . ?
N16 C11 C12 122.17(16) . . ?
N13 C14 C15 121.85(16) . . ?
N13 C14 C17 117.08(16) . . ?
C15 C14 C17 121.05(16) . . ?
C1 C2 C7 120.60(18) . . ?
C3 C2 C1 117.41(19) . . ?
C3 C2 C7 121.99(19) . . ?
C1 C6 C5 116.82(18) . . ?
C1 C6 C9 121.62(17) . . ?
C5 C6 C9 121.54(18) . . ?
N18 C17 C14 177.9(2) . . ?
N20 C19 C15 177.4(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.37(19) . . ?
C4 C5 H5 118.8 . . ?
C5 C4 C3 118.00(18) . . ?
C5 C4 C8 121.4(2) . . ?
C3 C4 C8 120.6(2) . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O21 C22 C23 122.2(2) . . ?
O21 C22 C24 121.9(2) . . ?
C23 C22 C24 115.9(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 C12 C11 N10 -0.3(3) 3_666 . . . ?
N10 C12 C11 N16 179.55(17) 3_666 . . . ?
N10 C1 C2 C3 178.34(16) . . . . ?
N10 C1 C2 C7 -1.3(3) . . . . ?
N10 C1 C6 C5 -178.91(16) . . . . ?
N10 C1 C6 C9 -0.8(3) . . . . ?
N13 C12 C11 N10 -179.58(16) . . . . ?
N13 C12 C11 N16 0.3(3) . . . . ?
N16 C15 C14 N13 -0.1(3) . . . . ?
N16 C15 C14 C17 -178.44(17) . . . . ?
C12 N10 C1 C2 82.3(2) 3_666 . . . ?
C12 N10 C1 C6 -100.4(2) 3_666 . . . ?
C12 N10 C11 N16 -179.55(16) 3_666 . . . ?
C12 N10 C11 C12 0.3(3) 3_666 . . . ?
C12 N13 C14 C15 1.3(3) . . . . ?
C12 N13 C14 C17 179.72(16) . . . . ?
C1 N10 C11 N16 -0.9(3) . . . . ?
C1 N10 C11 C12 178.99(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
C15 N16 C11 N10 -179.19(16) . . . . ?
C15 N16 C11 C12 1.0(3) . . . . ?
C11 N10 C1 C2 -96.4(2) . . . . ?
C11 N10 C1 C6 80.9(2) . . . . ?
C11 N16 C15 C14 -1.1(3) . . . . ?
C11 N16 C15 C19 178.52(17) . . . . ?
C14 N13 C12 N10 179.34(16) . . . 3_666 ?
C14 N13 C12 C11 -1.4(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C9 176.36(17) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C6 C1 C2 C7 -178.50(18) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C6 C5 C4 C8 -179.74(19) . . . . ?
C19 C15 C14 N13 -179.61(18) . . . . ?
C19 C15 C14 C17 2.0(3) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C9 C6 C5 C4 -176.97(18) . . . . ?
C7 C2 C3 C4 179.7(2) . . . . ?
C8 C4 C3 C2 179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.768
_oxdiff_exptl_absorpt_empirical_full_min 0.556
####################################################################### 
# 
# 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_TCDP-PhCl
_database_code_depnum_ccdc_archive 'CCDC 2429930'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10, C6 H5 Cl'
_chemical_formula_sum            'C36 H27 Cl N10'
_chemical_formula_weight         635.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1115(4)
_cell_length_b                   8.9633(6)
_cell_length_c                   11.3830(7)
_cell_angle_alpha                82.417(5)
_cell_angle_beta                 78.205(5)
_cell_angle_gamma                77.833(5)
_cell_volume                     788.51(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      30.2050
_cell_measurement_theta_min      2.6470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9331
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.335
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   5.00   0.50    2.86    --  -11.11  57.00  30.00   52
  2  ω    -12.00  80.00   0.50    2.86    --   12.51  72.00  42.00  184
  3  ω     32.00  57.00   0.50    2.86    --  -11.11  57.00  30.00   50
  4  ω     49.00  75.00   0.50    2.86    --   12.51 179.00  30.00   52
  5  ω     39.00  70.00   0.50    2.86    --   12.51 179.00-120.00   62
  6  ω     -5.00  49.00   0.50    2.86    --   12.51  57.00-150.00  108
  7  ω    -53.00  39.00   0.50    2.86    --   12.51 -72.00 -87.00  184
  8  ω     -1.00  51.00   0.50    2.86    --   12.51 -99.00-180.00  104
  9  ω    -90.00 -65.00   0.50    2.86    --  -11.11 179.00-120.00   50
 10  ω    -75.00 -47.00   0.50    2.86    --  -11.11 179.00 -90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2430
_reflns_number_total             3480
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.358
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0864
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1639P)²+0.6693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2622
_refine_ls_wR_factor_ref         0.2888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26-C25 = C26-C27 = C22-C23 = C27-C22 = C24-C23
 1.39 with sigma of 0.01
 C25-C24
 1.39 with sigma of 0.01
 C27-Cl21 \\sim Cl21-C23
 with sigma of 0.005
3. Rigid bond restraints
 Cl21, C22, C23, C25, C24, C26, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(Cl21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: Cl21(0.5) C23(0.5) H23(0.5) C22(0.5) C27(0.5) H27(0.5) C26(0.5)
 H26(0.5) C25(0.5) H25(0.5) C24(0.5) H24(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C23(H23), C27(H27), C26(H26), C25(H25), C24(H24)
6.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C23(C22,C27,C26,C25,C24)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N7 N 0.5950(3) 0.0436(3) 0.38727(19) 0.0259(5) Uani 1 1 d . . . . .
N10 N 0.4578(3) 0.2960(3) 0.4056(2) 0.0295(6) Uani 1 1 d . . . . .
N14 N 0.2576(3) 0.2064(3) 0.6247(2) 0.0299(6) Uani 1 1 d . . . . .
N13 N 0.3051(4) 0.6847(3) 0.3911(3) 0.0483(8) Uani 1 1 d . . . . .
C8 C 0.4761(3) 0.1531(3) 0.4508(2) 0.0257(6) Uani 1 1 d . . . . .
C9 C 0.3765(3) 0.1071(3) 0.5648(2) 0.0258(6) Uani 1 1 d . . . . .
N17 N -0.0150(4) 0.5483(3) 0.6811(3) 0.0460(8) Uani 1 1 d . . . . .
C15 C 0.2355(4) 0.3529(3) 0.5763(2) 0.0286(6) Uani 1 1 d . . . . .
C11 C 0.3365(4) 0.3986(3) 0.4695(2) 0.0299(6) Uani 1 1 d . . . . .
C12 C 0.3187(4) 0.5575(4) 0.4235(3) 0.0359(7) Uani 1 1 d . . . . .
C6 C 0.60524(18) 0.0979(2) 0.17062(15) 0.0317(7) Uani 1 1 d G . . . .
C1 C 0.6854(2) 0.0853(2) 0.26934(11) 0.0276(6) Uani 1 1 d G . . . .
C2 C 0.8498(2) 0.1161(2) 0.25356(13) 0.0299(6) Uani 1 1 d G . . . .
C3 C 0.93414(17) 0.1595(2) 0.13905(16) 0.0381(8) Uani 1 1 d G . . . .
H3 H 1.046528 0.180604 0.128263 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8540(2) 0.1721(2) 0.04033(12) 0.0388(8) Uani 1 1 d G . . . .
C5 C 0.6896(2) 0.1413(2) 0.05611(12) 0.0361(7) Uani 1 1 d G . . . .
H5 H 0.634816 0.149947 -0.011366 0.043 Uiso 1 1 calc R U . . .
C16 C 0.0972(4) 0.4614(3) 0.6374(3) 0.0342(7) Uani 1 1 d . . . . .
C18 C 0.9419(4) 0.0915(4) 0.3602(3) 0.0387(7) Uani 1 1 d . . . . .
H18A H 0.862265 0.132195 0.430734 0.058 Uiso 1 1 calc R U . . .
H18B H 1.039234 0.144742 0.340621 0.058 Uiso 1 1 calc R U . . .
H18C H 0.983433 -0.018420 0.378088 0.058 Uiso 1 1 calc R U . . .
C19 C 0.4244(4) 0.0643(5) 0.1887(3) 0.0459(9) Uani 1 1 d . . . . .
H19A H 0.423604 -0.040262 0.226865 0.069 Uiso 1 1 calc R U . . .
H19B H 0.388697 0.074135 0.110412 0.069 Uiso 1 1 calc R U . . .
H19C H 0.344939 0.137307 0.240501 0.069 Uiso 1 1 calc R U . . .
C20 C 0.9454(5) 0.2230(5) -0.0843(3) 0.0548(11) Uani 1 1 d . . . . .
H20A H 0.882273 0.207406 -0.145115 0.082 Uiso 1 1 calc R U . . .
H20B H 1.061938 0.162408 -0.099582 0.082 Uiso 1 1 calc R U . . .
H20C H 0.950717 0.331787 -0.088607 0.082 Uiso 1 1 calc R U . . .
Cl21 Cl 0.2920(7) 0.4116(6) -0.0617(5) 0.134(2) Uani 0.5 1 d D U P A -1
C23 C 0.5775(8) 0.5254(8) -0.0993(4) 0.0657(19) Uani 0.5 1 d DG U P A -1
H23 H 0.582179 0.521284 -0.182897 0.079 Uiso 0.5 1 calc R U P A -1
C22 C 0.4443(9) 0.4768(10) -0.0155(5) 0.0733(17) Uani 0.5 1 d DG U P A -1
C27 C 0.4375(8) 0.4828(8) 0.1068(4) 0.0620(19) Uani 0.5 1 d DG U P A -1
H27 H 0.346465 0.449652 0.164057 0.074 Uiso 0.5 1 calc R U P A -1
C26 C 0.5637(7) 0.5373(7) 0.1454(4) 0.0676(17) Uani 0.5 1 d DG U P A -1
H26 H 0.559028 0.541404 0.229023 0.081 Uiso 0.5 1 calc R U P A -1
C25 C 0.6969(7) 0.5858(8) 0.0617(5) 0.0482(18) Uani 0.5 1 d DG U P A -1
H25 H 0.783168 0.623096 0.088030 0.058 Uiso 0.5 1 calc R U P A -1
C24 C 0.7037(7) 0.5799(7) -0.0607(5) 0.0686(16) Uani 0.5 1 d DG U P A -1
H24 H 0.794745 0.613037 -0.117931 0.082 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N7 C8 1.385(3) . ?
N7 C9 1.379(4) 2_656 ?
N7 C1 1.435(2) . ?
N10 C8 1.306(4) . ?
N10 C11 1.359(4) . ?
N14 C9 1.311(4) . ?
N14 C15 1.346(4) . ?
N13 C12 1.141(4) . ?
C8 C9 1.441(4) . ?
N17 C16 1.140(4) . ?
C15 C11 1.385(4) . ?
C15 C16 1.445(4) . ?
C11 C12 1.439(4) . ?
C6 C1 1.3900 . ?
C6 C5 1.3900 . ?
C6 C19 1.527(3) . ?
C1 C2 1.3900 . ?
C2 C3 1.3900 . ?
C2 C18 1.520(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C20 1.520(3) . ?
C5 H5 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Cl21 C22 1.672(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.3900 . ?
C23 C24 1.3900 . ?
C22 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C25 1.3900 . ?
C25 H25 0.9500 . ?
C25 C24 1.3900 . ?
C24 H24 0.9500 . ?

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
C8 N7 C1 120.2(2) . . ?
C9 N7 C8 120.3(2) 2_656 . ?
C9 N7 C1 119.5(2) 2_656 . ?
C8 N10 C11 116.7(2) . . ?
C9 N14 C15 117.0(2) . . ?
N7 C8 C9 119.5(2) . . ?
N10 C8 N7 118.8(2) . . ?
N10 C8 C9 121.6(2) . . ?
N7 C9 C8 120.1(2) 2_656 . ?
N14 C9 N7 118.7(2) . 2_656 ?
N14 C9 C8 121.2(3) . . ?
N14 C15 C11 121.9(3) . . ?
N14 C15 C16 117.5(2) . . ?
C11 C15 C16 120.6(3) . . ?
N10 C11 C15 121.4(3) . . ?
N10 C11 C12 117.5(2) . . ?
C15 C11 C12 121.0(3) . . ?
N13 C12 C11 177.5(3) . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C19 119.69(16) . . ?
C5 C6 C19 120.31(16) . . ?
C6 C1 N7 119.28(14) . . ?
C2 C1 N7 120.71(14) . . ?
C2 C1 C6 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 C18 119.84(15) . . ?
C3 C2 C18 120.02(15) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C20 119.8(2) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C20 120.2(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
N17 C16 C15 177.0(3) . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C22 Cl21 120.12(18) . . ?
C27 C22 Cl21 119.88(18) . . ?
C27 C22 C23 120.0 . . ?
C22 C27 H27 120.0 . . ?
C22 C27 C26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?

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
N7 C8 C9 N7 2.8(4) . . . 2_656 ?
N7 C8 C9 N14 -177.0(2) . . . . ?
N7 C1 C2 C3 -178.6(2) . . . . ?
N7 C1 C2 C18 5.7(2) . . . . ?
N10 C8 C9 N7 -176.8(2) . . . 2_656 ?
N10 C8 C9 N14 3.5(4) . . . . ?
N14 C15 C11 N10 3.0(4) . . . . ?
N14 C15 C11 C12 -175.7(3) . . . . ?
C8 N7 C1 C6 -80.7(3) . . . . ?
C8 N7 C1 C2 97.9(2) . . . . ?
C8 N10 C11 C15 -1.0(4) . . . . ?
C8 N10 C11 C12 177.8(3) . . . . ?
C9 N7 C8 N10 176.8(2) 2_656 . . . ?
C9 N7 C8 C9 -2.8(4) 2_656 . . . ?
C9 N7 C1 C6 97.1(2) 2_656 . . . ?
C9 N7 C1 C2 -84.2(3) 2_656 . . . ?
C9 N14 C15 C11 -1.7(4) . . . . ?
C9 N14 C15 C16 175.9(3) . . . . ?
C15 N14 C9 N7 178.8(2) . . . 2_656 ?
C15 N14 C9 C8 -1.4(4) . . . . ?
C11 N10 C8 N7 178.3(2) . . . . ?
C11 N10 C8 C9 -2.1(4) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C2 C18 -175.7(2) . . . . ?
C1 N7 C8 N10 -5.4(4) . . . . ?
C1 N7 C8 C9 175.0(2) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C20 178.7(2) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C5 C6 C1 N7 178.64(19) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C16 C15 C11 N10 -174.5(3) . . . . ?
C16 C15 C11 C12 6.7(4) . . . . ?
C18 C2 C3 C4 175.7(2) . . . . ?
C19 C6 C1 N7 -1.2(3) . . . . ?
C19 C6 C1 C2 -179.9(2) . . . . ?
C19 C6 C5 C4 179.8(2) . . . . ?
C20 C4 C5 C6 -178.7(2) . . . . ?
Cl21 C22 C27 C26 -179.9(8) . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C22 C27 C26 C25 0.0 . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C24 C23 C22 Cl21 179.9(8) . . . . ?
C24 C23 C22 C27 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TCDP-SF
_database_code_depnum_ccdc_archive 'CCDC 2429944'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Institute for Molecular Science
Japan
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_audit_creation_date             2025-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N10'
_chemical_formula_sum            'C30 H22 N10'
_chemical_formula_weight         522.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1539(6)
_cell_length_b                   8.5097(5)
_cell_length_c                   10.9361(11)
_cell_angle_alpha                101.144(7)
_cell_angle_beta                 101.548(7)
_cell_angle_gamma                102.714(6)
_cell_volume                     702.52(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1819
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      28.0520
_cell_measurement_theta_min      2.5590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00   6.00   0.50   91.00    --   -3.75 -57.00 -60.00   72
  2  ω     -5.00  75.00   0.50   91.00    --    5.16  37.00 120.00  160
  3  ω      0.00  55.00   0.50   91.00    --    5.16  37.00   0.00  110
  4  ω      0.00  31.00   0.50   91.00    --    5.16 -99.00-180.00   62
  5  ω     -7.00  32.00   0.50   91.00    --    5.16 -99.00  60.00   78
  6  ω     -6.00  77.00   0.50   91.00    --    5.16  57.00-150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1745
_reflns_number_total             2863
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.0434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.52118(19) 0.43191(18) 0.37813(14) 0.0241(4) Uani 1 1 d . . . . .
N13 N 0.6055(2) 0.83211(18) 0.60485(16) 0.0266(4) Uani 1 1 d . . . . .
N16 N 0.66613(19) 0.69337(18) 0.36915(15) 0.0251(4) Uani 1 1 d . . . . .
N18 N 0.7715(2) 1.2465(2) 0.62595(18) 0.0405(5) Uani 1 1 d . . . . .
C1 C 0.5418(2) 0.3621(2) 0.25062(18) 0.0243(4) Uani 1 1 d . . . . .
N20 N 0.9148(2) 1.0310(2) 0.3091(2) 0.0425(5) Uani 1 1 d . . . . .
C15 C 0.7208(2) 0.8587(2) 0.42325(19) 0.0249(4) Uani 1 1 d . . . . .
C14 C 0.6882(2) 0.9274(2) 0.53761(19) 0.0265(5) Uani 1 1 d . . . . .
C11 C 0.5823(2) 0.6009(2) 0.43204(18) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.7193(3) 0.2774(2) 0.11835(19) 0.0295(5) Uani 1 1 d . . . . .
H5 H 0.828689 0.263235 0.108589 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5575(2) 0.6708(2) 0.55479(18) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.7372(3) 1.1051(2) 0.58956(19) 0.0292(5) Uani 1 1 d . . . . .
C6 C 0.7043(2) 0.3464(2) 0.24004(18) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.8600(2) 0.4061(3) 0.3536(2) 0.0311(5) Uani 1 1 d . . . . .
H9A H 0.908539 0.526212 0.368129 0.047 Uiso 1 1 calc R U . . .
H9B H 0.947909 0.348687 0.336401 0.047 Uiso 1 1 calc R U . . .
H9C H 0.825223 0.382433 0.430285 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5800(3) 0.2286(3) 0.0107(2) 0.0322(5) Uani 1 1 d . . . . .
C19 C 0.8255(3) 0.9562(2) 0.3583(2) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.3979(2) 0.3166(2) 0.1462(2) 0.0293(5) Uani 1 1 d . . . . .
C3 C 0.4209(3) 0.2498(3) 0.0263(2) 0.0342(5) Uani 1 1 d . . . . .
H3 H 0.324819 0.217820 -0.047135 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2232(3) 0.3361(3) 0.1602(2) 0.0421(6) Uani 1 1 d . . . . .
H7A H 0.169558 0.249483 0.198501 0.063 Uiso 1 1 calc R U . . .
H7B H 0.148454 0.325627 0.075218 0.063 Uiso 1 1 calc R U . . .
H7C H 0.237665 0.445789 0.216012 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6005(3) 0.1556(3) -0.1206(2) 0.0472(6) Uani 1 1 d . . . . .
H8A H 0.719091 0.144641 -0.112788 0.071 Uiso 1 1 calc R U . . .
H8B H 0.578396 0.228910 -0.177253 0.071 Uiso 1 1 calc R U . . .
H8C H 0.517419 0.045788 -0.157000 0.071 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
N10 C1 1.464(2) . ?
N10 C11 1.380(2) . ?
N10 C12 1.380(2) 2_666 ?
N13 C14 1.357(2) . ?
N13 C12 1.313(2) . ?
N16 C15 1.351(2) . ?
N16 C11 1.311(2) . ?
N18 C17 1.143(3) . ?
C1 C6 1.385(3) . ?
C1 C2 1.387(3) . ?
N20 C19 1.144(2) . ?
C15 C14 1.377(3) . ?
C15 C19 1.443(3) . ?
C14 C17 1.443(3) . ?
C11 C12 1.432(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C5 C4 1.384(3) . ?
C6 C9 1.501(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 C3 1.387(3) . ?
C4 C8 1.508(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.504(3) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C11 N10 C1 119.87(14) . . ?
C12 N10 C1 120.26(14) 2_666 . ?
C12 N10 C11 119.86(15) 2_666 . ?
C12 N13 C14 116.44(16) . . ?
C11 N16 C15 116.60(16) . . ?
C6 C1 N10 118.44(17) . . ?
C6 C1 C2 123.30(18) . . ?
C2 C1 N10 118.25(17) . . ?
N16 C15 C14 121.87(16) . . ?
N16 C15 C19 115.64(17) . . ?
C14 C15 C19 122.36(17) . . ?
N13 C14 C15 121.83(16) . . ?
N13 C14 C17 117.04(17) . . ?
C15 C14 C17 121.11(16) . . ?
N10 C11 C12 120.20(15) . . ?
N16 C11 N10 118.15(17) . . ?
N16 C11 C12 121.64(16) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.14(18) . . ?
N10 C12 C11 119.88(15) 2_666 . ?
N13 C12 N10 118.69(16) . 2_666 ?
N13 C12 C11 121.42(16) . . ?
N18 C17 C14 177.0(2) . . ?
C1 C6 C5 117.15(18) . . ?
C1 C6 C9 122.04(18) . . ?
C5 C6 C9 120.77(17) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 118.37(19) . . ?
C5 C4 C8 121.00(19) . . ?
C3 C4 C8 120.6(2) . . ?
N20 C19 C15 176.8(2) . . ?
C1 C2 C3 117.06(18) . . ?
C1 C2 C7 122.24(19) . . ?
C3 C2 C7 120.70(19) . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
N10 C1 C6 C5 179.03(15) . . . . ?
N10 C1 C6 C9 -3.0(3) . . . . ?
N10 C1 C2 C3 -179.68(16) . . . . ?
N10 C1 C2 C7 -0.3(3) . . . . ?
N10 C11 C12 N10 2.8(3) . . . 2_666 ?
N10 C11 C12 N13 -176.05(17) . . . . ?
N16 C15 C14 N13 2.7(3) . . . . ?
N16 C15 C14 C17 -175.73(17) . . . . ?
N16 C11 C12 N10 -175.69(17) . . . 2_666 ?
N16 C11 C12 N13 5.5(3) . . . . ?
C1 N10 C11 N16 -3.6(2) . . . . ?
C1 N10 C11 C12 177.92(17) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C15 N16 C11 N10 178.58(16) . . . . ?
C15 N16 C11 C12 -2.9(3) . . . . ?
C14 N13 C12 N10 177.56(16) . . . 2_666 ?
C14 N13 C12 C11 -3.6(3) . . . . ?
C11 N10 C1 C6 76.0(2) . . . . ?
C11 N10 C1 C2 -103.3(2) . . . . ?
C11 N16 C15 C14 -1.0(3) . . . . ?
C11 N16 C15 C19 174.87(17) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C12 N10 C1 C6 -103.3(2) 2_666 . . . ?
C12 N10 C1 C2 77.4(2) 2_666 . . . ?
C12 N10 C11 N16 175.74(16) 2_666 . . . ?
C12 N10 C11 C12 -2.8(3) 2_666 . . . ?
C12 N13 C14 C15 -0.3(3) . . . . ?
C12 N13 C14 C17 178.23(17) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C6 C1 C2 C7 -179.57(19) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C6 C5 C4 C8 179.38(19) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C9 -176.80(18) . . . . ?
C19 C15 C14 N13 -172.83(18) . . . . ?
C19 C15 C14 C17 8.7(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C9 176.24(18) . . . . ?
C7 C2 C3 C4 -179.2(2) . . . . ?
C8 C4 C3 C2 179.92(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
