# Electronic Supplementary Material (ESI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 2314579'
loop_
_audit_author_name
_audit_author_address
'Daisuke Sakamaki'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C33 H18 Cl2 N2 O2'
_chemical_formula_moiety         'C33 H18 Cl2 N2 O2'
_chemical_formula_weight         545.42
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.4675(4)
_cell_length_b                   23.5001(15)
_cell_length_c                   26.7405(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4692.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7105
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      76.31
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240.00
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  0.946

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18824
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_theta_max         77.416
_diffrn_reflns_theta_min         2.503
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8733
_reflns_number_gt                7522
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_max     0.773
_reflns_Friedel_fraction_full    0.856

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1376
_refine_ls_R_factor_gt           0.1275
_refine_ls_wR_factor_ref         0.3537
_refine_ls_wR_factor_gt          0.3395
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8733
_refine_ls_number_parameters     703
_refine_ls_goodness_of_fit_ref   1.555
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         3.20
_refine_diff_density_min         -1.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.486(13)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.9988(5) 0.45036(14) 0.04191(11) 0.0510(8) Uani 1 1 d . . . . .
Cl2 Cl 0.8971(6) 0.53519(15) 0.11677(16) 0.0656(10) Uani 1 1 d . . . . .
Cl3 Cl 0.5067(5) 0.44989(14) 0.08375(13) 0.0547(8) Uani 1 1 d . . . . .
Cl4 Cl 0.3775(7) 0.56692(16) 0.08126(16) 0.0704(11) Uani 1 1 d . . . . .
O1 O 0.6162(9) 0.5695(3) 0.2912(2) 0.0245(13) Uani 1 1 d . . . . .
O2 O 0.3184(9) 0.8597(3) 0.3450(3) 0.0278(15) Uani 1 1 d . . . . .
O3 O 0.1178(9) 0.4561(3) 0.2970(2) 0.0246(13) Uani 1 1 d . . . . .
O4 O -0.1661(9) 0.1676(3) 0.3578(3) 0.0261(14) Uani 1 1 d . . . . .
N1 N 0.4861(9) 0.6603(3) 0.3416(2) 0.0150(13) Uani 1 1 d . . . . .
N2 N 0.4572(9) 0.7663(3) 0.2928(3) 0.0204(15) Uani 1 1 d . . . . .
N3 N -0.0121(10) 0.3662(3) 0.3498(3) 0.0186(14) Uani 1 1 d . . . . .
N4 N -0.0355(10) 0.2588(3) 0.3028(3) 0.0203(15) Uani 1 1 d . . . . .
C1 C 0.6074(11) 0.6243(4) 0.3679(3) 0.0178(16) Uani 1 1 d . . . . .
C2 C 0.6634(11) 0.6313(4) 0.4158(3) 0.0204(17) Uani 1 1 d . . . . .
H2 H 0.622491 0.663040 0.434617 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7818(11) 0.5920(4) 0.4378(3) 0.0219(18) Uani 1 1 d . . . . .
H3 H 0.819264 0.597031 0.471439 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8438(12) 0.5460(4) 0.4106(3) 0.0266(19) Uani 1 1 d . . . . .
H4 H 0.922830 0.519252 0.425531 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7899(11) 0.5392(4) 0.3613(3) 0.0211(17) Uani 1 1 d . . . . .
H5 H 0.833199 0.508019 0.342124 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6745(11) 0.5774(4) 0.3404(3) 0.0188(16) Uani 1 1 d . . . . .
C7 C 0.5943(11) 0.6201(3) 0.2650(3) 0.0170(16) Uani 1 1 d . . . . .
C8 C 0.6411(11) 0.6220(4) 0.2145(3) 0.0208(18) Uani 1 1 d . . . . .
H8 H 0.681285 0.588904 0.197474 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6266(10) 0.6750(4) 0.1896(3) 0.0181(16) Uani 1 1 d . . . . .
C10 C 0.6803(13) 0.6801(5) 0.1383(3) 0.028(2) Uani 1 1 d . . . . .
H10 H 0.723277 0.647891 0.120552 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6688(12) 0.7319(4) 0.1153(3) 0.0239(18) Uani 1 1 d . . . . .
H11 H 0.705101 0.735276 0.081348 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6049(11) 0.7801(4) 0.1404(3) 0.0237(18) Uani 1 1 d . . . . .
H12 H 0.600350 0.815599 0.123469 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5484(10) 0.7766(4) 0.1896(3) 0.0179(16) Uani 1 1 d . . . . .
C14 C 0.5625(11) 0.7229(4) 0.2145(3) 0.0199(17) Uani 1 1 d . . . . .
C15 C 0.5147(10) 0.7187(3) 0.2656(3) 0.0141(14) Uani 1 1 d . . . . .
C16 C 0.5261(11) 0.6669(4) 0.2899(3) 0.0184(16) Uani 1 1 d . . . . .
C17 C 0.4320(11) 0.8185(4) 0.2692(3) 0.0195(17) Uani 1 1 d . . . . .
C18 C 0.4791(11) 0.8245(4) 0.2173(3) 0.0211(17) Uani 1 1 d . . . . .
C19 C 0.4541(12) 0.8800(4) 0.1959(4) 0.0267(19) Uani 1 1 d . . . . .
H19 H 0.481512 0.886035 0.161600 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3920(14) 0.9241(4) 0.2239(4) 0.032(2) Uani 1 1 d . . . . .
H20 H 0.379751 0.960588 0.208991 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3458(13) 0.9168(4) 0.2740(4) 0.029(2) Uani 1 1 d . . . . .
H21 H 0.300331 0.948042 0.292638 0.035 Uiso 1 1 calc R U . . .
C22 C 0.3654(11) 0.8653(4) 0.2964(4) 0.0244(19) Uani 1 1 d . . . . .
C23 C 0.3141(12) 0.8064(4) 0.3665(3) 0.0220(18) Uani 1 1 d . . . . .
C24 C 0.2368(13) 0.8006(4) 0.4122(3) 0.0245(19) Uani 1 1 d . . . . .
H24 H 0.193745 0.833281 0.429298 0.029 Uiso 1 1 calc R U . . .
C25 C 0.2200(13) 0.7467(5) 0.4344(3) 0.029(2) Uani 1 1 d . . . . .
C26 C 0.1282(13) 0.7386(4) 0.4793(3) 0.0258(19) Uani 1 1 d . . . . .
H26 H 0.079227 0.770527 0.496233 0.031 Uiso 1 1 calc R U . . .
C27 C 0.1076(12) 0.6858(5) 0.4992(4) 0.032(2) Uani 1 1 d . . . . .
H27 H 0.044505 0.681424 0.529771 0.039 Uiso 1 1 calc R U . . .
C28 C 0.1772(12) 0.6380(5) 0.4755(3) 0.028(2) Uani 1 1 d . . . . .
H28 H 0.161879 0.601447 0.489995 0.034 Uiso 1 1 calc R U . . .
C29 C 0.2686(11) 0.6438(5) 0.4309(3) 0.026(2) Uani 1 1 d . . . . .
H29 H 0.313369 0.610872 0.414473 0.031 Uiso 1 1 calc R U . . .
C30 C 0.2964(13) 0.6980(4) 0.4094(3) 0.0252(19) Uani 1 1 d . . . . .
C31 C 0.3959(12) 0.7066(4) 0.3651(3) 0.0205(17) Uani 1 1 d . . . . .
C32 C 0.3911(11) 0.7583(4) 0.3407(3) 0.0174(16) Uani 1 1 d . . . . .
C33 C 0.1078(11) 0.4038(4) 0.3743(3) 0.0212(17) Uani 1 1 d . . . . .
C34 C 0.1663(11) 0.3984(4) 0.4239(3) 0.0213(17) Uani 1 1 d . . . . .
H34 H 0.129016 0.366834 0.443503 0.026 Uiso 1 1 calc R U . . .
C35 C 0.2791(11) 0.4392(5) 0.4441(3) 0.026(2) Uani 1 1 d . . . . .
H35 H 0.314481 0.436054 0.478100 0.032 Uiso 1 1 calc R U . . .
C36 C 0.3414(12) 0.4845(4) 0.4160(4) 0.0247(19) Uani 1 1 d . . . . .
H36 H 0.419009 0.511848 0.430614 0.030 Uiso 1 1 calc R U . . .
C37 C 0.2895(12) 0.4897(4) 0.3659(4) 0.0237(18) Uani 1 1 d . . . . .
H37 H 0.332690 0.520109 0.345803 0.028 Uiso 1 1 calc R U . . .
C38 C 0.1730(11) 0.4492(4) 0.3463(3) 0.0214(17) Uani 1 1 d . . . . .
C39 C 0.0980(11) 0.4045(4) 0.2718(3) 0.0215(18) Uani 1 1 d . . . . .
C40 C 0.1472(10) 0.4013(4) 0.2220(3) 0.0194(17) Uani 1 1 d . . . . .
H40 H 0.187971 0.434119 0.204677 0.023 Uiso 1 1 calc R U . . .
C41 C 0.1355(12) 0.3480(4) 0.1975(4) 0.0227(18) Uani 1 1 d . . . . .
C42 C 0.1908(12) 0.3419(4) 0.1475(3) 0.0218(18) Uani 1 1 d . . . . .
H42 H 0.236124 0.373573 0.129404 0.026 Uiso 1 1 calc R U . . .
C43 C 0.1782(12) 0.2883(4) 0.1247(3) 0.0220(18) Uani 1 1 d . . . . .
H43 H 0.218389 0.283678 0.091207 0.026 Uiso 1 1 calc R U . . .
C44 C 0.1065(12) 0.2411(4) 0.1507(3) 0.0241(18) Uani 1 1 d . . . . .
H44 H 0.095806 0.205391 0.134273 0.029 Uiso 1 1 calc R U . . .
C45 C 0.0520(10) 0.2467(4) 0.1997(3) 0.0188(17) Uani 1 1 d . . . . .
C46 C 0.0693(11) 0.3000(4) 0.2235(3) 0.0188(17) Uani 1 1 d . . . . .
C47 C 0.0168(11) 0.3063(4) 0.2750(3) 0.0174(16) Uani 1 1 d . . . . .
C48 C 0.0307(10) 0.3586(4) 0.2983(3) 0.0176(16) Uani 1 1 d . . . . .
C49 C -0.0608(11) 0.2068(4) 0.2791(4) 0.0221(18) Uani 1 1 d . . . . .
C50 C -0.0231(11) 0.1986(4) 0.2282(3) 0.0188(16) Uani 1 1 d . . . . .
C51 C -0.0526(13) 0.1449(4) 0.2085(4) 0.028(2) Uani 1 1 d . . . . .
H51 H -0.026895 0.138699 0.174118 0.034 Uiso 1 1 calc R U . . .
C52 C -0.1182(14) 0.0998(4) 0.2367(4) 0.028(2) Uani 1 1 d . . . . .
H52 H -0.137271 0.063523 0.221927 0.034 Uiso 1 1 calc R U . . .
C53 C -0.1547(14) 0.1089(4) 0.2863(4) 0.031(2) Uani 1 1 d . . . . .
H53 H -0.199187 0.078344 0.306008 0.037 Uiso 1 1 calc R U . . .
C54 C -0.1282(11) 0.1614(4) 0.3082(3) 0.0226(18) Uani 1 1 d . . . . .
C55 C -0.1761(12) 0.2214(4) 0.3778(3) 0.0203(17) Uani 1 1 d . . . . .
C56 C -0.2516(13) 0.2278(4) 0.4234(4) 0.028(2) Uani 1 1 d . . . . .
H56 H -0.291560 0.195306 0.441293 0.033 Uiso 1 1 calc R U . . .
C57 C -0.2715(12) 0.2826(4) 0.4445(3) 0.0236(18) Uani 1 1 d . . . . .
C58 C -0.3637(13) 0.2913(5) 0.4896(4) 0.029(2) Uani 1 1 d . . . . .
H58 H -0.406218 0.259205 0.507722 0.035 Uiso 1 1 calc R U . . .
C59 C -0.3938(13) 0.3444(5) 0.5081(3) 0.028(2) Uani 1 1 d . . . . .
H59 H -0.458701 0.349085 0.538357 0.034 Uiso 1 1 calc R U . . .
C60 C -0.3279(11) 0.3928(4) 0.4820(4) 0.0253(19) Uani 1 1 d . . . . .
H60 H -0.348404 0.429946 0.494815 0.030 Uiso 1 1 calc R U . . .
C61 C -0.2339(11) 0.3855(4) 0.4379(3) 0.0239(19) Uani 1 1 d . . . . .
H61 H -0.192549 0.418106 0.420347 0.029 Uiso 1 1 calc R U . . .
C62 C -0.1971(11) 0.3300(4) 0.4181(3) 0.0226(18) Uani 1 1 d . . . . .
C63 C -0.0988(12) 0.3208(4) 0.3737(3) 0.0195(17) Uani 1 1 d . . . . .
C64 C -0.1003(11) 0.2681(4) 0.3514(3) 0.0199(17) Uani 1 1 d . . . . .
C65 C 0.988(2) 0.4669(6) 0.1055(5) 0.056(3) Uani 1 1 d . . . . .
H65A H 1.109601 0.464978 0.119909 0.068 Uiso 1 1 calc R U . . .
H65B H 0.913033 0.438076 0.122637 0.068 Uiso 1 1 calc R U . . .
C66 C 0.4801(19) 0.5106(5) 0.0458(5) 0.049(3) Uani 1 1 d . . . . .
H66A H 0.404265 0.501159 0.016631 0.058 Uiso 1 1 calc R U . . .
H66B H 0.598426 0.523247 0.033355 0.058 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C65 1.745(14) . ?
Cl2 C65 1.768(14) . ?
Cl3 C66 1.762(12) . ?
Cl4 C66 1.799(14) . ?
O1 C7 1.388(11) . ?
O1 C6 1.399(10) . ?
O2 C22 1.355(12) . ?
O2 C23 1.379(12) . ?
O3 C38 1.391(11) . ?
O3 C39 1.393(11) . ?
O4 C54 1.365(11) . ?
O4 C55 1.374(11) . ?
N1 C16 1.423(10) . ?
N1 C31 1.424(11) . ?
N1 C1 1.426(11) . ?
N2 C32 1.385(11) . ?
N2 C17 1.393(12) . ?
N2 C15 1.403(11) . ?
N3 C63 1.402(11) . ?
N3 C33 1.419(11) . ?
N3 C48 1.425(11) . ?
N4 C49 1.389(12) . ?
N4 C47 1.398(11) . ?
N4 C64 1.404(11) . ?
C1 C2 1.357(12) . ?
C1 C6 1.417(12) . ?
C2 C3 1.408(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.364(12) . ?
C5 H5 0.9500 . ?
C7 C16 1.384(12) . ?
C7 C8 1.394(12) . ?
C8 C9 1.417(13) . ?
C8 H8 0.9500 . ?
C9 C14 1.392(12) . ?
C9 C10 1.435(12) . ?
C10 C11 1.366(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.431(13) . ?
C13 C18 1.443(13) . ?
C14 C15 1.414(11) . ?
C15 C16 1.382(12) . ?
C17 C22 1.409(12) . ?
C17 C18 1.437(12) . ?
C18 C19 1.438(14) . ?
C19 C20 1.359(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.358(14) . ?
C21 H21 0.9500 . ?
C23 C24 1.359(12) . ?
C23 C32 1.442(12) . ?
C24 C25 1.404(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(13) . ?
C25 C30 1.442(13) . ?
C26 C27 1.359(16) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(15) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(12) . ?
C28 H28 0.9500 . ?
C29 C30 1.414(15) . ?
C29 H29 0.9500 . ?
C30 C31 1.413(13) . ?
C31 C32 1.381(13) . ?
C33 C38 1.392(12) . ?
C33 C34 1.400(12) . ?
C34 C35 1.387(14) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(14) . ?
C35 H35 0.9500 . ?
C36 C37 1.400(13) . ?
C36 H36 0.9500 . ?
C37 C38 1.391(12) . ?
C37 H37 0.9500 . ?
C39 C40 1.383(12) . ?
C39 C48 1.385(12) . ?
C40 C41 1.417(13) . ?
C40 H40 0.9500 . ?
C41 C42 1.409(13) . ?
C41 C46 1.413(12) . ?
C42 C43 1.401(13) . ?
C42 H42 0.9500 . ?
C43 C44 1.415(13) . ?
C43 H43 0.9500 . ?
C44 C45 1.378(12) . ?
C44 H44 0.9500 . ?
C45 C46 1.411(13) . ?
C45 C50 1.476(12) . ?
C46 C47 1.440(11) . ?
C47 C48 1.381(12) . ?
C49 C50 1.403(13) . ?
C49 C54 1.413(12) . ?
C50 C51 1.384(13) . ?
C51 C52 1.391(14) . ?
C51 H51 0.9500 . ?
C52 C53 1.371(15) . ?
C52 H52 0.9500 . ?
C53 C54 1.380(14) . ?
C53 H53 0.9500 . ?
C55 C56 1.352(14) . ?
C55 C64 1.422(12) . ?
C56 C57 1.414(15) . ?
C56 H56 0.9500 . ?
C57 C58 1.404(14) . ?
C57 C62 1.431(12) . ?
C58 C59 1.361(15) . ?
C58 H58 0.9500 . ?
C59 C60 1.423(13) . ?
C59 H59 0.9500 . ?
C60 C61 1.382(13) . ?
C60 H60 0.9500 . ?
C61 C62 1.435(14) . ?
C61 H61 0.9500 . ?
C62 C63 1.414(13) . ?
C63 C64 1.374(13) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 H66A 0.9900 . ?
C66 H66B 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
C7 O1 C6 113.5(6) . . ?
C22 O2 C23 119.5(7) . . ?
C38 O3 C39 112.9(7) . . ?
C54 O4 C55 119.2(7) . . ?
C16 N1 C31 116.4(7) . . ?
C16 N1 C1 114.3(6) . . ?
C31 N1 C1 122.5(7) . . ?
C32 N2 C17 119.4(7) . . ?
C32 N2 C15 118.8(7) . . ?
C17 N2 C15 120.6(7) . . ?
C63 N3 C33 123.6(7) . . ?
C63 N3 C48 116.6(7) . . ?
C33 N3 C48 112.7(7) . . ?
C49 N4 C47 119.9(7) . . ?
C49 N4 C64 120.9(7) . . ?
C47 N4 C64 117.6(7) . . ?
C2 C1 C6 118.4(8) . . ?
C2 C1 N1 126.1(8) . . ?
C6 C1 N1 115.5(7) . . ?
C1 C2 C3 120.5(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.3(8) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.5(8) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.7(8) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 O1 119.7(7) . . ?
C5 C6 C1 121.6(8) . . ?
O1 C6 C1 118.8(7) . . ?
C16 C7 O1 118.8(7) . . ?
C16 C7 C8 122.2(8) . . ?
O1 C7 C8 119.1(7) . . ?
C7 C8 C9 117.6(8) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C14 C9 C8 120.8(8) . . ?
C14 C9 C10 119.1(8) . . ?
C8 C9 C10 120.1(8) . . ?
C11 C10 C9 119.2(9) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.7(9) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 120.8(9) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 118.2(8) . . ?
C12 C13 C18 123.4(8) . . ?
C14 C13 C18 118.4(7) . . ?
C9 C14 C15 119.5(8) . . ?
C9 C14 C13 121.0(8) . . ?
C15 C14 C13 119.5(8) . . ?
C16 C15 N2 118.4(7) . . ?
C16 C15 C14 120.1(7) . . ?
N2 C15 C14 121.5(7) . . ?
C15 C16 C7 119.7(7) . . ?
C15 C16 N1 122.7(7) . . ?
C7 C16 N1 117.3(7) . . ?
N2 C17 C22 120.0(8) . . ?
N2 C17 C18 119.4(8) . . ?
C22 C17 C18 120.6(8) . . ?
C17 C18 C19 116.2(8) . . ?
C17 C18 C13 120.4(8) . . ?
C19 C18 C13 123.4(8) . . ?
C20 C19 C18 121.1(9) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 121.3(9) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 120.4(9) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
O2 C22 C21 118.7(8) . . ?
O2 C22 C17 120.9(9) . . ?
C21 C22 C17 120.4(9) . . ?
C24 C23 O2 118.3(8) . . ?
C24 C23 C32 121.4(9) . . ?
O2 C23 C32 120.3(8) . . ?
C23 C24 C25 120.5(8) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 122.0(9) . . ?
C26 C25 C30 119.0(10) . . ?
C24 C25 C30 119.0(9) . . ?
C27 C26 C25 121.1(9) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 121.2(9) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 120.0(10) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.8(9) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 123.1(9) . . ?
C31 C30 C25 118.9(9) . . ?
C29 C30 C25 118.0(9) . . ?
C32 C31 C30 120.5(8) . . ?
C32 C31 N1 118.4(8) . . ?
C30 C31 N1 120.7(8) . . ?
C31 C32 N2 123.1(8) . . ?
C31 C32 C23 118.3(8) . . ?
N2 C32 C23 118.6(8) . . ?
C38 C33 C34 118.0(8) . . ?
C38 C33 N3 116.7(7) . . ?
C34 C33 N3 125.3(8) . . ?
C35 C34 C33 119.7(9) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C36 C35 C34 121.7(9) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C35 C36 C37 119.7(9) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C38 C37 C36 118.2(9) . . ?
C38 C37 H37 120.9 . . ?
C36 C37 H37 120.9 . . ?
C37 C38 O3 117.6(8) . . ?
C37 C38 C33 122.8(8) . . ?
O3 C38 C33 119.7(8) . . ?
C40 C39 C48 123.0(8) . . ?
C40 C39 O3 119.0(8) . . ?
C48 C39 O3 118.0(8) . . ?
C39 C40 C41 118.5(8) . . ?
C39 C40 H40 120.7 . . ?
C41 C40 H40 120.7 . . ?
C42 C41 C46 119.2(8) . . ?
C42 C41 C40 120.8(8) . . ?
C46 C41 C40 120.0(8) . . ?
C43 C42 C41 119.0(8) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C42 C43 C44 121.1(8) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C45 C44 C43 120.3(9) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 119.1(8) . . ?
C44 C45 C50 122.1(8) . . ?
C46 C45 C50 118.8(7) . . ?
C45 C46 C41 121.3(8) . . ?
C45 C46 C47 119.8(8) . . ?
C41 C46 C47 118.9(8) . . ?
C48 C47 N4 119.5(7) . . ?
C48 C47 C46 120.1(7) . . ?
N4 C47 C46 120.2(8) . . ?
C47 C48 C39 119.4(8) . . ?
C47 C48 N3 122.1(7) . . ?
C39 C48 N3 118.4(8) . . ?
N4 C49 C50 122.4(8) . . ?
N4 C49 C54 117.5(8) . . ?
C50 C49 C54 120.1(9) . . ?
C51 C50 C49 117.6(8) . . ?
C51 C50 C45 124.1(8) . . ?
C49 C50 C45 118.2(8) . . ?
C50 C51 C52 122.9(10) . . ?
C50 C51 H51 118.5 . . ?
C52 C51 H51 118.5 . . ?
C53 C52 C51 118.4(9) . . ?
C53 C52 H52 120.8 . . ?
C51 C52 H52 120.8 . . ?
C52 C53 C54 121.4(9) . . ?
C52 C53 H53 119.3 . . ?
C54 C53 H53 119.3 . . ?
O4 C54 C53 118.6(8) . . ?
O4 C54 C49 121.8(9) . . ?
C53 C54 C49 119.5(9) . . ?
C56 C55 O4 118.4(8) . . ?
C56 C55 C64 121.8(9) . . ?
O4 C55 C64 119.8(8) . . ?
C55 C56 C57 120.4(8) . . ?
C55 C56 H56 119.8 . . ?
C57 C56 H56 119.8 . . ?
C58 C57 C56 121.8(8) . . ?
C58 C57 C62 120.1(9) . . ?
C56 C57 C62 118.1(8) . . ?
C59 C58 C57 121.7(9) . . ?
C59 C58 H58 119.1 . . ?
C57 C58 H58 119.1 . . ?
C58 C59 C60 119.9(9) . . ?
C58 C59 H59 120.0 . . ?
C60 C59 H59 120.0 . . ?
C61 C60 C59 119.6(9) . . ?
C61 C60 H60 120.2 . . ?
C59 C60 H60 120.2 . . ?
C60 C61 C62 121.6(9) . . ?
C60 C61 H61 119.2 . . ?
C62 C61 H61 119.2 . . ?
C63 C62 C57 119.8(9) . . ?
C63 C62 C61 123.3(8) . . ?
C57 C62 C61 116.8(8) . . ?
C64 C63 N3 119.5(8) . . ?
C64 C63 C62 119.9(8) . . ?
N3 C63 C62 120.5(8) . . ?
C63 C64 N4 122.6(7) . . ?
C63 C64 C55 119.0(8) . . ?
N4 C64 C55 118.3(8) . . ?
Cl1 C65 Cl2 112.8(8) . . ?
Cl1 C65 H65A 109.0 . . ?
Cl2 C65 H65A 109.0 . . ?
Cl1 C65 H65B 109.0 . . ?
Cl2 C65 H65B 109.0 . . ?
H65A C65 H65B 107.8 . . ?
Cl3 C66 Cl4 109.9(7) . . ?
Cl3 C66 H66A 109.7 . . ?
Cl4 C66 H66A 109.7 . . ?
Cl3 C66 H66B 109.7 . . ?
Cl4 C66 H66B 109.7 . . ?
H66A C66 H66B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 C2 144.1(8) . . . . ?
C31 N1 C1 C2 -5.8(12) . . . . ?
C16 N1 C1 C6 -35.3(10) . . . . ?
C31 N1 C1 C6 174.9(7) . . . . ?
C6 C1 C2 C3 -1.6(12) . . . . ?
N1 C1 C2 C3 179.0(8) . . . . ?
C1 C2 C3 C4 0.7(13) . . . . ?
C2 C3 C4 C5 0.6(14) . . . . ?
C3 C4 C5 C6 -0.9(14) . . . . ?
C4 C5 C6 O1 -178.2(8) . . . . ?
C4 C5 C6 C1 0.0(13) . . . . ?
C7 O1 C6 C5 -144.2(8) . . . . ?
C7 O1 C6 C1 37.5(10) . . . . ?
C2 C1 C6 C5 1.3(12) . . . . ?
N1 C1 C6 C5 -179.3(8) . . . . ?
C2 C1 C6 O1 179.5(7) . . . . ?
N1 C1 C6 O1 -1.1(11) . . . . ?
C6 O1 C7 C16 -37.8(10) . . . . ?
C6 O1 C7 C8 142.4(7) . . . . ?
C16 C7 C8 C9 3.7(12) . . . . ?
O1 C7 C8 C9 -176.5(7) . . . . ?
C7 C8 C9 C14 -1.9(11) . . . . ?
C7 C8 C9 C10 177.3(8) . . . . ?
C14 C9 C10 C11 0.6(12) . . . . ?
C8 C9 C10 C11 -178.6(8) . . . . ?
C9 C10 C11 C12 -0.4(14) . . . . ?
C10 C11 C12 C13 -1.0(14) . . . . ?
C11 C12 C13 C14 2.0(12) . . . . ?
C11 C12 C13 C18 -179.1(8) . . . . ?
C8 C9 C14 C15 1.2(11) . . . . ?
C10 C9 C14 C15 -178.0(7) . . . . ?
C8 C9 C14 C13 179.7(7) . . . . ?
C10 C9 C14 C13 0.5(12) . . . . ?
C12 C13 C14 C9 -1.8(11) . . . . ?
C18 C13 C14 C9 179.3(7) . . . . ?
C12 C13 C14 C15 176.7(7) . . . . ?
C18 C13 C14 C15 -2.2(11) . . . . ?
C32 N2 C15 C16 -8.8(11) . . . . ?
C17 N2 C15 C16 -175.7(7) . . . . ?
C32 N2 C15 C14 172.0(7) . . . . ?
C17 N2 C15 C14 5.1(11) . . . . ?
C9 C14 C15 C16 -2.1(11) . . . . ?
C13 C14 C15 C16 179.4(7) . . . . ?
C9 C14 C15 N2 177.1(7) . . . . ?
C13 C14 C15 N2 -1.4(11) . . . . ?
N2 C15 C16 C7 -175.5(7) . . . . ?
C14 C15 C16 C7 3.8(12) . . . . ?
N2 C15 C16 N1 -1.5(12) . . . . ?
C14 C15 C16 N1 177.7(7) . . . . ?
O1 C7 C16 C15 175.6(7) . . . . ?
C8 C7 C16 C15 -4.6(12) . . . . ?
O1 C7 C16 N1 1.3(11) . . . . ?
C8 C7 C16 N1 -178.9(7) . . . . ?
C31 N1 C16 C15 13.4(11) . . . . ?
C1 N1 C16 C15 -138.3(8) . . . . ?
C31 N1 C16 C7 -172.5(7) . . . . ?
C1 N1 C16 C7 35.8(10) . . . . ?
C32 N2 C17 C22 9.9(12) . . . . ?
C15 N2 C17 C22 176.7(7) . . . . ?
C32 N2 C17 C18 -171.8(7) . . . . ?
C15 N2 C17 C18 -4.9(12) . . . . ?
N2 C17 C18 C19 -178.3(7) . . . . ?
C22 C17 C18 C19 0.1(12) . . . . ?
N2 C17 C18 C13 1.3(12) . . . . ?
C22 C17 C18 C13 179.6(7) . . . . ?
C12 C13 C18 C17 -176.5(8) . . . . ?
C14 C13 C18 C17 2.3(11) . . . . ?
C12 C13 C18 C19 2.9(13) . . . . ?
C14 C13 C18 C19 -178.2(7) . . . . ?
C17 C18 C19 C20 1.0(13) . . . . ?
C13 C18 C19 C20 -178.5(8) . . . . ?
C18 C19 C20 C21 -1.7(15) . . . . ?
C19 C20 C21 C22 1.3(15) . . . . ?
C23 O2 C22 C21 171.2(8) . . . . ?
C23 O2 C22 C17 -8.2(12) . . . . ?
C20 C21 C22 O2 -179.7(8) . . . . ?
C20 C21 C22 C17 -0.2(14) . . . . ?
N2 C17 C22 O2 -2.7(12) . . . . ?
C18 C17 C22 O2 179.0(8) . . . . ?
N2 C17 C22 C21 177.9(8) . . . . ?
C18 C17 C22 C21 -0.4(13) . . . . ?
C22 O2 C23 C24 -168.5(8) . . . . ?
C22 O2 C23 C32 11.8(12) . . . . ?
O2 C23 C24 C25 176.4(8) . . . . ?
C32 C23 C24 C25 -3.9(13) . . . . ?
C23 C24 C25 C26 -174.5(9) . . . . ?
C23 C24 C25 C30 4.0(14) . . . . ?
C24 C25 C26 C27 177.5(9) . . . . ?
C30 C25 C26 C27 -1.0(13) . . . . ?
C25 C26 C27 C28 0.0(14) . . . . ?
C26 C27 C28 C29 -0.2(14) . . . . ?
C27 C28 C29 C30 1.5(13) . . . . ?
C28 C29 C30 C31 177.0(8) . . . . ?
C28 C29 C30 C25 -2.5(13) . . . . ?
C26 C25 C30 C31 -177.3(8) . . . . ?
C24 C25 C30 C31 4.1(13) . . . . ?
C26 C25 C30 C29 2.3(12) . . . . ?
C24 C25 C30 C29 -176.3(8) . . . . ?
C29 C30 C31 C32 167.8(8) . . . . ?
C25 C30 C31 C32 -12.7(12) . . . . ?
C29 C30 C31 N1 -4.9(13) . . . . ?
C25 C30 C31 N1 174.6(8) . . . . ?
C16 N1 C31 C32 -15.0(11) . . . . ?
C1 N1 C31 C32 134.3(8) . . . . ?
C16 N1 C31 C30 157.9(7) . . . . ?
C1 N1 C31 C30 -52.9(11) . . . . ?
C30 C31 C32 N2 -167.5(8) . . . . ?
N1 C31 C32 N2 5.3(12) . . . . ?
C30 C31 C32 C23 12.7(12) . . . . ?
N1 C31 C32 C23 -174.4(7) . . . . ?
C17 N2 C32 C31 174.0(8) . . . . ?
C15 N2 C32 C31 7.0(12) . . . . ?
C17 N2 C32 C23 -6.3(11) . . . . ?
C15 N2 C32 C23 -173.3(7) . . . . ?
C24 C23 C32 C31 -4.5(12) . . . . ?
O2 C23 C32 C31 175.2(8) . . . . ?
C24 C23 C32 N2 175.8(8) . . . . ?
O2 C23 C32 N2 -4.5(12) . . . . ?
C63 N3 C33 C38 -175.5(8) . . . . ?
C48 N3 C33 C38 35.1(10) . . . . ?
C63 N3 C33 C34 5.3(13) . . . . ?
C48 N3 C33 C34 -144.0(8) . . . . ?
C38 C33 C34 C35 3.1(12) . . . . ?
N3 C33 C34 C35 -177.8(8) . . . . ?
C33 C34 C35 C36 -2.5(13) . . . . ?
C34 C35 C36 C37 0.3(14) . . . . ?
C35 C36 C37 C38 1.2(13) . . . . ?
C36 C37 C38 O3 177.9(8) . . . . ?
C36 C37 C38 C33 -0.5(13) . . . . ?
C39 O3 C38 C37 144.2(8) . . . . ?
C39 O3 C38 C33 -37.4(11) . . . . ?
C34 C33 C38 C37 -1.6(13) . . . . ?
N3 C33 C38 C37 179.2(8) . . . . ?
C34 C33 C38 O3 -180.0(7) . . . . ?
N3 C33 C38 O3 0.8(12) . . . . ?
C38 O3 C39 C40 -142.4(8) . . . . ?
C38 O3 C39 C48 37.0(10) . . . . ?
C48 C39 C40 C41 -2.8(12) . . . . ?
O3 C39 C40 C41 176.7(8) . . . . ?
C39 C40 C41 C42 -177.4(8) . . . . ?
C39 C40 C41 C46 2.0(12) . . . . ?
C46 C41 C42 C43 0.2(13) . . . . ?
C40 C41 C42 C43 179.6(8) . . . . ?
C41 C42 C43 C44 1.7(14) . . . . ?
C42 C43 C44 C45 -1.8(14) . . . . ?
C43 C44 C45 C46 -0.2(12) . . . . ?
C43 C44 C45 C50 -179.9(7) . . . . ?
C44 C45 C46 C41 2.2(12) . . . . ?
C50 C45 C46 C41 -178.1(7) . . . . ?
C44 C45 C46 C47 -178.6(8) . . . . ?
C50 C45 C46 C47 1.1(11) . . . . ?
C42 C41 C46 C45 -2.2(13) . . . . ?
C40 C41 C46 C45 178.4(8) . . . . ?
C42 C41 C46 C47 178.6(8) . . . . ?
C40 C41 C46 C47 -0.8(12) . . . . ?
C49 N4 C47 C48 175.9(7) . . . . ?
C64 N4 C47 C48 10.3(12) . . . . ?
C49 N4 C47 C46 -8.9(12) . . . . ?
C64 N4 C47 C46 -174.5(7) . . . . ?
C45 C46 C47 C48 -179.0(8) . . . . ?
C41 C46 C47 C48 0.3(12) . . . . ?
C45 C46 C47 N4 5.9(12) . . . . ?
C41 C46 C47 N4 -174.9(8) . . . . ?
N4 C47 C48 C39 174.2(7) . . . . ?
C46 C47 C48 C39 -0.9(12) . . . . ?
N4 C47 C48 N3 -2.0(12) . . . . ?
C46 C47 C48 N3 -177.1(7) . . . . ?
C40 C39 C48 C47 2.3(13) . . . . ?
O3 C39 C48 C47 -177.2(7) . . . . ?
C40 C39 C48 N3 178.6(7) . . . . ?
O3 C39 C48 N3 -0.8(11) . . . . ?
C63 N3 C48 C47 -10.9(11) . . . . ?
C33 N3 C48 C47 140.8(8) . . . . ?
C63 N3 C48 C39 172.9(7) . . . . ?
C33 N3 C48 C39 -35.5(10) . . . . ?
C47 N4 C49 C50 4.8(12) . . . . ?
C64 N4 C49 C50 169.9(8) . . . . ?
C47 N4 C49 C54 -174.8(7) . . . . ?
C64 N4 C49 C54 -9.7(11) . . . . ?
N4 C49 C50 C51 179.7(8) . . . . ?
C54 C49 C50 C51 -0.6(12) . . . . ?
N4 C49 C50 C45 2.2(12) . . . . ?
C54 C49 C50 C45 -178.2(7) . . . . ?
C44 C45 C50 C51 -2.8(12) . . . . ?
C46 C45 C50 C51 177.6(8) . . . . ?
C44 C45 C50 C49 174.7(8) . . . . ?
C46 C45 C50 C49 -5.0(11) . . . . ?
C49 C50 C51 C52 0.4(13) . . . . ?
C45 C50 C51 C52 177.8(8) . . . . ?
C50 C51 C52 C53 -0.2(15) . . . . ?
C51 C52 C53 C54 0.2(15) . . . . ?
C55 O4 C54 C53 -166.7(8) . . . . ?
C55 O4 C54 C49 14.1(11) . . . . ?
C52 C53 C54 O4 -179.6(8) . . . . ?
C52 C53 C54 C49 -0.4(14) . . . . ?
N4 C49 C54 O4 -0.6(12) . . . . ?
C50 C49 C54 O4 179.8(7) . . . . ?
N4 C49 C54 C53 -179.7(8) . . . . ?
C50 C49 C54 C53 0.7(13) . . . . ?
C54 O4 C55 C56 165.5(8) . . . . ?
C54 O4 C55 C64 -17.4(11) . . . . ?
O4 C55 C56 C57 -177.4(8) . . . . ?
C64 C55 C56 C57 5.5(13) . . . . ?
C55 C56 C57 C58 174.1(9) . . . . ?
C55 C56 C57 C62 -4.8(13) . . . . ?
C56 C57 C58 C59 -175.2(9) . . . . ?
C62 C57 C58 C59 3.7(14) . . . . ?
C57 C58 C59 C60 -1.3(15) . . . . ?
C58 C59 C60 C61 0.1(14) . . . . ?
C59 C60 C61 C62 -1.4(13) . . . . ?
C58 C57 C62 C63 177.7(8) . . . . ?
C56 C57 C62 C63 -3.4(13) . . . . ?
C58 C57 C62 C61 -4.7(12) . . . . ?
C56 C57 C62 C61 174.3(8) . . . . ?
C60 C61 C62 C63 -178.9(8) . . . . ?
C60 C61 C62 C57 3.6(12) . . . . ?
C33 N3 C63 C64 -133.0(9) . . . . ?
C48 N3 C63 C64 15.2(11) . . . . ?
C33 N3 C63 C62 52.4(12) . . . . ?
C48 N3 C63 C62 -159.3(7) . . . . ?
C57 C62 C63 C64 11.0(13) . . . . ?
C61 C62 C63 C64 -166.5(8) . . . . ?
C57 C62 C63 N3 -174.4(8) . . . . ?
C61 C62 C63 N3 8.1(13) . . . . ?
N3 C63 C64 N4 -7.2(13) . . . . ?
C62 C63 C64 N4 167.4(8) . . . . ?
N3 C63 C64 C55 175.0(7) . . . . ?
C62 C63 C64 C55 -10.4(13) . . . . ?
C49 N4 C64 C63 -171.4(8) . . . . ?
C47 N4 C64 C63 -5.9(12) . . . . ?
C49 N4 C64 C55 6.4(11) . . . . ?
C47 N4 C64 C55 171.8(7) . . . . ?
C56 C55 C64 C63 2.2(13) . . . . ?
O4 C55 C64 C63 -174.9(7) . . . . ?
C56 C55 C64 N4 -175.7(8) . . . . ?
O4 C55 C64 N4 7.3(12) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_xcalibur_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2314580'
loop_
_audit_author_name
_audit_author_address
'Daisuke Sakamaki'
;Osaka Metropolitan University
Japan
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C40 H20 N2 O2'
_chemical_formula_moiety         'C40 H20 N2 O2'
_chemical_formula_weight         560.61
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,+Y,1/2+Z
4 1/2+X,-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.2040(13)
_cell_length_b                   27.327(3)
_cell_length_c                   7.5073(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2503.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3489
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      75.89
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            darkbrown
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160.00
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.245
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8908
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_theta_max         77.723
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3804
_reflns_number_gt                3215
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.382
_reflns_Friedel_fraction_max     0.428
_reflns_Friedel_fraction_full    0.481

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2225
_refine_ls_wR_factor_gt          0.1954
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     397
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1496P)²+1.2517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 0.5779(3) 0.34825(13) 0.4565(6) 0.0352(9) Uani 1 1 d . . . . .
O2 O 0.1713(3) 0.15206(13) 0.4678(6) 0.0313(8) Uani 1 1 d . . . . .
N1 N 0.3762(3) 0.30046(15) 0.4940(6) 0.0285(10) Uani 1 1 d . . . . .
N2 N 0.3691(3) 0.19806(14) 0.4584(7) 0.0275(9) Uani 1 1 d . . . . .
C1 C 0.3826(4) 0.35124(18) 0.5152(7) 0.0288(11) Uani 1 1 d . . . . .
C2 C 0.2882(4) 0.37942(19) 0.5445(7) 0.0288(11) Uani 1 1 d . . . . .
C3 C 0.3022(4) 0.42962(19) 0.6004(8) 0.0312(11) Uani 1 1 d . . . . .
C4 C 0.2197(4) 0.4585(2) 0.6782(8) 0.0357(13) Uani 1 1 d . . . . .
H4 H 0.150249 0.444062 0.700568 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2354(5) 0.5065(2) 0.7229(8) 0.0367(12) Uani 1 1 d . . . . .
H5 H 0.177240 0.524406 0.776091 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3349(5) 0.5295(2) 0.6919(9) 0.0366(12) Uani 1 1 d . . . . .
H6 H 0.343704 0.563605 0.712352 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4210(4) 0.5012(2) 0.6303(8) 0.0365(12) Uani 1 1 d . . . . .
H7 H 0.491196 0.515779 0.616445 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4074(4) 0.45165(19) 0.5877(8) 0.0306(11) Uani 1 1 d . . . . .
C9 C 0.4973(4) 0.4227(2) 0.5331(8) 0.0343(12) Uani 1 1 d . . . . .
H9 H 0.567163 0.437467 0.517972 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4849(4) 0.37442(19) 0.5024(8) 0.0304(11) Uani 1 1 d . . . . .
C11 C 0.5674(4) 0.29970(19) 0.4118(8) 0.0309(11) Uani 1 1 d . . . . .
C12 C 0.6571(4) 0.2766(2) 0.3409(8) 0.0331(12) Uani 1 1 d . . . . .
H12 H 0.723754 0.294068 0.326475 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6511(4) 0.2272(2) 0.2894(8) 0.0331(12) Uani 1 1 d . . . . .
C14 C 0.7392(4) 0.2041(2) 0.1978(9) 0.0360(12) Uani 1 1 d . . . . .
H14 H 0.805801 0.221376 0.179000 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7282(4) 0.1571(2) 0.1368(9) 0.0358(13) Uani 1 1 d . . . . .
H15 H 0.787032 0.142459 0.073503 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6329(4) 0.1305(2) 0.1652(8) 0.0353(12) Uani 1 1 d . . . . .
H16 H 0.626895 0.098035 0.121176 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5465(4) 0.15148(19) 0.2583(8) 0.0317(12) Uani 1 1 d . . . . .
H17 H 0.481263 0.133233 0.277182 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5546(4) 0.19968(19) 0.3252(7) 0.0282(11) Uani 1 1 d . . . . .
C19 C 0.4655(4) 0.22373(19) 0.4156(8) 0.0288(12) Uani 1 1 d . . . . .
C20 C 0.4706(4) 0.2735(2) 0.4431(8) 0.0296(11) Uani 1 1 d . . . . .
C21 C 0.3640(4) 0.15258(17) 0.5460(7) 0.0267(11) Uani 1 1 d . . . . .
C22 C 0.4508(4) 0.12900(19) 0.6253(8) 0.0288(11) Uani 1 1 d . . . . .
H22 H 0.520799 0.144196 0.628564 0.035 Uiso 1 1 calc R U . . .
C23 C 0.4361(4) 0.08212(18) 0.7021(8) 0.0296(11) Uani 1 1 d . . . . .
C24 C 0.5253(4) 0.05695(19) 0.7871(8) 0.0305(11) Uani 1 1 d . . . . .
H24 H 0.595633 0.071800 0.791263 0.037 Uiso 1 1 calc R U . . .
C25 C 0.5100(5) 0.01170(19) 0.8624(8) 0.0338(12) Uani 1 1 d . . . . .
H25 H 0.569373 -0.004085 0.920666 0.041 Uiso 1 1 calc R U . . .
C26 C 0.4077(4) -0.01145(19) 0.8541(8) 0.0335(11) Uani 1 1 d . . . . .
H26 H 0.398493 -0.042968 0.905312 0.040 Uiso 1 1 calc R U . . .
C27 C 0.3205(4) 0.01122(19) 0.7722(8) 0.0337(12) Uani 1 1 d . . . . .
H27 H 0.251574 -0.004832 0.766055 0.040 Uiso 1 1 calc R U . . .
C28 C 0.3334(4) 0.05839(18) 0.6973(8) 0.0300(11) Uani 1 1 d . . . . .
C29 C 0.2446(4) 0.08450(17) 0.6193(8) 0.0286(11) Uani 1 1 d . . . . .
H29 H 0.173478 0.070361 0.617921 0.034 Uiso 1 1 calc R U . . .
C30 C 0.2606(4) 0.12923(18) 0.5471(7) 0.0268(11) Uani 1 1 d . . . . .
C31 C 0.1733(4) 0.20231(18) 0.4661(8) 0.0277(11) Uani 1 1 d . . . . .
C32 C 0.0771(4) 0.2278(2) 0.4564(8) 0.0325(11) Uani 1 1 d . . . . .
H32 H 0.009708 0.210674 0.444501 0.039 Uiso 1 1 calc R U . . .
C33 C 0.0774(4) 0.2793(2) 0.4639(8) 0.0312(11) Uani 1 1 d . . . . .
C34 C -0.0181(4) 0.3080(2) 0.4467(8) 0.0324(12) Uani 1 1 d . . . . .
H34 H -0.087004 0.292322 0.432146 0.039 Uiso 1 1 calc R U . . .
C35 C -0.0131(4) 0.3574(2) 0.4504(9) 0.0375(13) Uani 1 1 d . . . . .
H35 H -0.078186 0.375728 0.432151 0.045 Uiso 1 1 calc R U . . .
C36 C 0.0861(4) 0.38225(19) 0.4807(8) 0.0317(11) Uani 1 1 d . . . . .
H36 H 0.087349 0.417013 0.480495 0.038 Uiso 1 1 calc R U . . .
C37 C 0.1816(4) 0.3564(2) 0.5108(7) 0.0299(11) Uani 1 1 d . . . . .
C38 C 0.1782(4) 0.3046(2) 0.4907(7) 0.0303(11) Uani 1 1 d . . . . .
C39 C 0.2766(4) 0.27648(19) 0.4899(8) 0.0291(11) Uani 1 1 d . . . . .
C40 C 0.2723(4) 0.2268(2) 0.4708(8) 0.0292(11) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O1 C11 1.375(6) . ?
O1 C10 1.385(6) . ?
O2 C31 1.373(6) . ?
O2 C30 1.390(6) . ?
N1 C39 1.381(6) . ?
N1 C1 1.399(6) . ?
N1 C20 1.420(6) . ?
N2 C19 1.407(6) . ?
N2 C21 1.408(6) . ?
N2 C40 1.422(6) . ?
C1 C2 1.403(7) . ?
C1 C10 1.404(7) . ?
C2 C3 1.445(7) . ?
C2 C37 1.467(7) . ?
C3 C4 1.406(8) . ?
C3 C8 1.421(7) . ?
C4 C5 1.368(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(8) . ?
C9 C10 1.349(7) . ?
C9 H9 0.9500 . ?
C11 C12 1.371(8) . ?
C11 C20 1.402(7) . ?
C12 C13 1.407(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.422(8) . ?
C13 C18 1.423(7) . ?
C14 C15 1.370(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.441(7) . ?
C19 C20 1.376(7) . ?
C21 C22 1.375(7) . ?
C21 C30 1.414(7) . ?
C22 C23 1.416(7) . ?
C22 H22 0.9500 . ?
C23 C28 1.412(7) . ?
C23 C24 1.437(7) . ?
C24 C25 1.372(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.415(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.423(7) . ?
C29 C30 1.351(7) . ?
C29 H29 0.9500 . ?
C31 C32 1.367(7) . ?
C31 C40 1.382(7) . ?
C32 C33 1.408(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.410(7) . ?
C33 C38 1.427(7) . ?
C34 C35 1.351(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.407(8) . ?
C35 H35 0.9500 . ?
C36 C37 1.382(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.423(8) . ?
C38 C39 1.425(7) . ?
C39 C40 1.366(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 O1 C10 118.9(4) . . ?
C31 O2 C30 116.0(4) . . ?
C39 N1 C1 121.5(4) . . ?
C39 N1 C20 117.5(4) . . ?
C1 N1 C20 120.1(4) . . ?
C19 N2 C21 125.7(4) . . ?
C19 N2 C40 115.7(4) . . ?
C21 N2 C40 114.9(4) . . ?
N1 C1 C2 121.1(5) . . ?
N1 C1 C10 119.3(4) . . ?
C2 C1 C10 119.6(5) . . ?
C1 C2 C3 118.0(5) . . ?
C1 C2 C37 117.7(5) . . ?
C3 C2 C37 124.2(4) . . ?
C4 C3 C8 115.9(5) . . ?
C4 C3 C2 124.7(5) . . ?
C8 C3 C2 119.3(5) . . ?
C5 C4 C3 122.7(5) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.9(5) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 121.8(5) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 121.0(5) . . ?
C7 C8 C3 120.1(5) . . ?
C9 C8 C3 118.9(5) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 O1 117.2(5) . . ?
C9 C10 C1 122.0(5) . . ?
O1 C10 C1 120.9(5) . . ?
C12 C11 O1 117.7(5) . . ?
C12 C11 C20 120.1(5) . . ?
O1 C11 C20 122.1(5) . . ?
C11 C12 C13 120.5(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 C18 119.8(5) . . ?
C14 C13 C18 118.9(5) . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.5(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 118.9(5) . . ?
C17 C18 C19 122.7(4) . . ?
C13 C18 C19 118.2(5) . . ?
C20 C19 N2 119.7(4) . . ?
C20 C19 C18 119.2(5) . . ?
N2 C19 C18 120.7(5) . . ?
C19 C20 C11 121.2(5) . . ?
C19 C20 N1 121.2(4) . . ?
C11 C20 N1 117.6(5) . . ?
C22 C21 N2 125.6(4) . . ?
C22 C21 C30 118.3(5) . . ?
N2 C21 C30 116.1(4) . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C28 C23 C22 121.2(5) . . ?
C28 C23 C24 117.7(5) . . ?
C22 C23 C24 121.2(4) . . ?
C25 C24 C23 120.7(5) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.7(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 120.4(5) . . ?
C23 C28 C29 117.2(5) . . ?
C27 C28 C29 122.4(5) . . ?
C30 C29 C28 120.5(5) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 O2 117.7(4) . . ?
C29 C30 C21 122.7(5) . . ?
O2 C30 C21 119.7(4) . . ?
C32 C31 O2 119.6(4) . . ?
C32 C31 C40 120.4(5) . . ?
O2 C31 C40 120.0(4) . . ?
C31 C32 C33 120.3(5) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 123.4(5) . . ?
C32 C33 C38 119.5(5) . . ?
C34 C33 C38 117.1(5) . . ?
C35 C34 C33 121.1(5) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C36 121.7(5) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C37 C36 C35 120.3(5) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 117.8(5) . . ?
C36 C37 C2 123.8(5) . . ?
C38 C37 C2 118.1(4) . . ?
C37 C38 C39 120.8(5) . . ?
C37 C38 C33 121.5(5) . . ?
C39 C38 C33 117.6(5) . . ?
C40 C39 N1 120.5(5) . . ?
C40 C39 C38 120.3(5) . . ?
N1 C39 C38 119.0(5) . . ?
C39 C40 C31 121.1(5) . . ?
C39 C40 N2 121.6(4) . . ?
C31 C40 N2 117.2(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
C39 N1 C1 C2 4.1(8) . . . . ?
C20 N1 C1 C2 172.4(5) . . . . ?
C39 N1 C1 C10 -174.2(5) . . . . ?
C20 N1 C1 C10 -6.0(8) . . . . ?
N1 C1 C2 C3 167.8(5) . . . . ?
C10 C1 C2 C3 -13.8(8) . . . . ?
N1 C1 C2 C37 -14.1(8) . . . . ?
C10 C1 C2 C37 164.3(5) . . . . ?
C1 C2 C3 C4 -162.9(6) . . . . ?
C37 C2 C3 C4 19.2(9) . . . . ?
C1 C2 C3 C8 13.1(8) . . . . ?
C37 C2 C3 C8 -164.8(5) . . . . ?
C8 C3 C4 C5 6.4(9) . . . . ?
C2 C3 C4 C5 -177.5(6) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C4 C5 C6 C7 -6.1(9) . . . . ?
C5 C6 C7 C8 4.5(9) . . . . ?
C6 C7 C8 C9 -176.9(6) . . . . ?
C6 C7 C8 C3 2.6(9) . . . . ?
C4 C3 C8 C7 -7.8(8) . . . . ?
C2 C3 C8 C7 175.9(5) . . . . ?
C4 C3 C8 C9 171.7(5) . . . . ?
C2 C3 C8 C9 -4.7(8) . . . . ?
C7 C8 C9 C10 176.1(5) . . . . ?
C3 C8 C9 C10 -3.4(8) . . . . ?
C8 C9 C10 O1 -177.4(5) . . . . ?
C8 C9 C10 C1 2.8(9) . . . . ?
C11 O1 C10 C9 -175.4(5) . . . . ?
C11 O1 C10 C1 4.4(8) . . . . ?
N1 C1 C10 C9 -175.6(5) . . . . ?
C2 C1 C10 C9 6.0(9) . . . . ?
N1 C1 C10 O1 4.7(8) . . . . ?
C2 C1 C10 O1 -173.7(5) . . . . ?
C10 O1 C11 C12 170.2(5) . . . . ?
C10 O1 C11 C20 -12.4(8) . . . . ?
O1 C11 C12 C13 -178.9(5) . . . . ?
C20 C11 C12 C13 3.7(9) . . . . ?
C11 C12 C13 C14 173.0(6) . . . . ?
C11 C12 C13 C18 -5.5(9) . . . . ?
C12 C13 C14 C15 -174.9(6) . . . . ?
C18 C13 C14 C15 3.6(9) . . . . ?
C13 C14 C15 C16 -1.4(10) . . . . ?
C14 C15 C16 C17 -0.3(9) . . . . ?
C15 C16 C17 C18 -0.3(9) . . . . ?
C16 C17 C18 C13 2.6(8) . . . . ?
C16 C17 C18 C19 177.2(5) . . . . ?
C12 C13 C18 C17 174.4(5) . . . . ?
C14 C13 C18 C17 -4.2(8) . . . . ?
C12 C13 C18 C19 -0.5(8) . . . . ?
C14 C13 C18 C19 -179.1(5) . . . . ?
C21 N2 C19 C20 -136.9(5) . . . . ?
C40 N2 C19 C20 20.3(7) . . . . ?
C21 N2 C19 C18 50.1(8) . . . . ?
C40 N2 C19 C18 -152.8(5) . . . . ?
C17 C18 C19 C20 -166.2(5) . . . . ?
C13 C18 C19 C20 8.4(7) . . . . ?
C17 C18 C19 N2 6.9(8) . . . . ?
C13 C18 C19 N2 -178.5(5) . . . . ?
N2 C19 C20 C11 176.2(5) . . . . ?
C18 C19 C20 C11 -10.6(8) . . . . ?
N2 C19 C20 N1 -7.6(8) . . . . ?
C18 C19 C20 N1 165.6(5) . . . . ?
C12 C11 C20 C19 4.6(8) . . . . ?
O1 C11 C20 C19 -172.8(5) . . . . ?
C12 C11 C20 N1 -171.8(5) . . . . ?
O1 C11 C20 N1 10.9(8) . . . . ?
C39 N1 C20 C19 -9.1(8) . . . . ?
C1 N1 C20 C19 -177.8(5) . . . . ?
C39 N1 C20 C11 167.2(5) . . . . ?
C1 N1 C20 C11 -1.5(8) . . . . ?
C19 N2 C21 C22 9.3(9) . . . . ?
C40 N2 C21 C22 -148.0(5) . . . . ?
C19 N2 C21 C30 -169.0(5) . . . . ?
C40 N2 C21 C30 33.7(6) . . . . ?
N2 C21 C22 C23 -177.0(5) . . . . ?
C30 C21 C22 C23 1.3(8) . . . . ?
C21 C22 C23 C28 0.8(8) . . . . ?
C21 C22 C23 C24 -179.4(5) . . . . ?
C28 C23 C24 C25 -0.7(8) . . . . ?
C22 C23 C24 C25 179.5(6) . . . . ?
C23 C24 C25 C26 1.6(9) . . . . ?
C24 C25 C26 C27 -0.9(9) . . . . ?
C25 C26 C27 C28 -0.6(9) . . . . ?
C22 C23 C28 C27 179.0(5) . . . . ?
C24 C23 C28 C27 -0.8(8) . . . . ?
C22 C23 C28 C29 -2.7(8) . . . . ?
C24 C23 C28 C29 177.5(5) . . . . ?
C26 C27 C28 C23 1.5(8) . . . . ?
C26 C27 C28 C29 -176.7(6) . . . . ?
C23 C28 C29 C30 2.6(8) . . . . ?
C27 C28 C29 C30 -179.2(5) . . . . ?
C28 C29 C30 O2 177.9(5) . . . . ?
C28 C29 C30 C21 -0.6(8) . . . . ?
C31 O2 C30 C29 152.7(5) . . . . ?
C31 O2 C30 C21 -28.8(7) . . . . ?
C22 C21 C30 C29 -1.4(8) . . . . ?
N2 C21 C30 C29 177.0(5) . . . . ?
C22 C21 C30 O2 -179.9(5) . . . . ?
N2 C21 C30 O2 -1.5(7) . . . . ?
C30 O2 C31 C32 -155.1(5) . . . . ?
C30 O2 C31 C40 26.2(7) . . . . ?
O2 C31 C32 C33 176.7(5) . . . . ?
C40 C31 C32 C33 -4.6(9) . . . . ?
C31 C32 C33 C34 177.0(5) . . . . ?
C31 C32 C33 C38 -3.1(9) . . . . ?
C32 C33 C34 C35 -178.3(6) . . . . ?
C38 C33 C34 C35 1.8(9) . . . . ?
C33 C34 C35 C36 -3.3(10) . . . . ?
C34 C35 C36 C37 -1.1(10) . . . . ?
C35 C36 C37 C38 6.7(8) . . . . ?
C35 C36 C37 C2 -179.6(6) . . . . ?
C1 C2 C37 C36 -159.5(5) . . . . ?
C3 C2 C37 C36 18.4(9) . . . . ?
C1 C2 C37 C38 14.2(8) . . . . ?
C3 C2 C37 C38 -167.9(5) . . . . ?
C36 C37 C38 C39 169.3(5) . . . . ?
C2 C37 C38 C39 -4.7(8) . . . . ?
C36 C37 C38 C33 -8.2(8) . . . . ?
C2 C37 C38 C33 177.8(5) . . . . ?
C32 C33 C38 C37 -175.9(5) . . . . ?
C34 C33 C38 C37 4.0(8) . . . . ?
C32 C33 C38 C39 6.5(8) . . . . ?
C34 C33 C38 C39 -173.6(5) . . . . ?
C1 N1 C39 C40 -179.3(5) . . . . ?
C20 N1 C39 C40 12.1(7) . . . . ?
C1 N1 C39 C38 5.9(7) . . . . ?
C20 N1 C39 C38 -162.7(5) . . . . ?
C37 C38 C39 C40 179.9(5) . . . . ?
C33 C38 C39 C40 -2.5(7) . . . . ?
C37 C38 C39 N1 -5.3(8) . . . . ?
C33 C38 C39 N1 172.3(5) . . . . ?
N1 C39 C40 C31 -179.9(5) . . . . ?
C38 C39 C40 C31 -5.2(8) . . . . ?
N1 C39 C40 N2 1.3(8) . . . . ?
C38 C39 C40 N2 176.0(5) . . . . ?
C32 C31 C40 C39 8.8(8) . . . . ?
O2 C31 C40 C39 -172.4(5) . . . . ?
C32 C31 C40 N2 -172.3(5) . . . . ?
O2 C31 C40 N2 6.4(8) . . . . ?
C19 N2 C40 C39 -17.6(8) . . . . ?
C21 N2 C40 C39 142.1(5) . . . . ?
C19 N2 C40 C31 163.6(5) . . . . ?
C21 N2 C40 C31 -36.7(7) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


