# 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. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2389266'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C57.80 H52.80 Br2 Cl2.39 N4 O11'
_chemical_formula_weight         1223.90

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7752(10)
_cell_length_b                   11.4458(12)
_cell_length_c                   24.731(3)
_cell_angle_alpha                94.352(3)
_cell_angle_beta                 93.154(3)
_cell_angle_gamma                108.044(3)
_cell_volume                     2614.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.655
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7498
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            36841
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         79.695
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             10481
_reflns_number_gt                10049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+4.0575P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10481
_refine_ls_number_parameters     782
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C60 C 0.1795(18) 0.0966(14) 0.2104(6) 0.019(3) Uani 0.132(3) 1 d D U P A -3
H60 H 0.248828 0.063967 0.190705 0.023 Uiso 0.132(3) 1 calc R U P A -3
Cl7 Cl 0.1360(10) -0.0099(10) 0.2392(4) 0.089(3) Uani 0.132(3) 1 d D U P A -3
Cl8 Cl 0.0833(16) 0.0891(13) 0.1545(5) 0.088(4) Uani 0.132(3) 1 d D U P A -3
Cl9 Cl 0.3036(14) 0.2182(13) 0.2326(9) 0.152(8) Uani 0.132(3) 1 d D U P A -3
C58 C 0.2521(7) 0.1525(6) 0.2047(3) 0.0318(15) Uani 0.514(7) 1 d . . P B -2
H58 H 0.305609 0.093870 0.193922 0.038 Uiso 0.514(7) 1 calc R U P B -2
Cl1 Cl 0.3343(6) 0.2945(4) 0.17839(18) 0.0380(9) Uani 0.514(7) 1 d . . P B -2
Cl2 Cl 0.2682(6) 0.1789(5) 0.2758(2) 0.0624(15) Uani 0.514(7) 1 d . . P B -2
Cl3 Cl 0.0713(2) 0.0879(2) 0.17860(10) 0.0423(7) Uani 0.514(7) 1 d . . P B -2
C59 C 0.211(3) 0.1805(15) 0.2173(7) 0.043(6) Uani 0.149(7) 1 d D U P C -1
H59 H 0.130868 0.216436 0.222954 0.052 Uiso 0.149(7) 1 calc R U P C -1
Cl4 Cl 0.2678(12) 0.1690(10) 0.2824(5) 0.030(2) Uani 0.149(7) 1 d D U P C -1
Cl5 Cl 0.1194(10) 0.0386(10) 0.1848(4) 0.064(4) Uani 0.149(7) 1 d D U P C -1
Cl6 Cl 0.319(2) 0.2841(16) 0.1780(5) 0.043(4) Uani 0.149(7) 1 d D U P C -1
C1 C 0.7392(2) 0.70803(19) 0.04008(8) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.5875(2) 0.68769(17) 0.05963(8) 0.0144(4) Uani 1 1 d . . . . .
H2A H 0.521983 0.606777 0.043168 0.017 Uiso 1 1 calc R U . . .
H2AB H 0.592211 0.686408 0.099658 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5270(2) 0.79058(17) 0.04381(8) 0.0150(4) Uani 1 1 d . . . . .
C4 C 0.5206(2) 0.7906(2) -0.01830(8) 0.0207(4) Uani 1 1 d . . . . .
H4A H 0.482038 0.856518 -0.029223 0.025 Uiso 1 1 calc R U . . .
H4AB H 0.454716 0.710466 -0.035386 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6715(3) 0.8121(2) -0.03826(9) 0.0261(5) Uani 1 1 d . . . . .
H5 H 0.665500 0.812001 -0.078763 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7295(2) 0.7084(2) -0.02216(9) 0.0236(4) Uani 1 1 d . . . . .
H6A H 0.826310 0.720974 -0.035409 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.664481 0.627768 -0.039148 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6300(2) 0.91562(19) 0.06962(9) 0.0207(4) Uani 1 1 d . . . . .
H7A H 0.592224 0.982713 0.059771 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.635923 0.916446 0.109746 0.025 Uiso 1 1 calc R U . . .
C8 C 0.7810(2) 0.9377(2) 0.04965(10) 0.0255(5) Uani 1 1 d . . . . .
H8 H 0.846860 1.019303 0.066573 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8396(2) 0.83439(19) 0.06598(9) 0.0207(4) Uani 1 1 d . . . . .
H9A H 0.846438 0.834920 0.106087 0.025 Uiso 1 1 calc R U . . .
H9AB H 0.937695 0.848753 0.053693 0.025 Uiso 1 1 calc R U . . .
C10 C 0.7727(3) 0.9369(2) -0.01237(11) 0.0325(5) Uani 1 1 d . . . . .
H10A H 0.870241 0.951206 -0.025172 0.039 Uiso 1 1 calc R U . . .
H10B H 0.736289 1.003950 -0.023318 0.039 Uiso 1 1 calc R U . . .
C11 C 0.7982(2) 0.60395(19) 0.05466(8) 0.0190(4) Uani 1 1 d . . . . .
H11A H 0.734649 0.524986 0.035599 0.023 Uiso 1 1 calc R U . . .
H11B H 0.895281 0.619551 0.041315 0.023 Uiso 1 1 calc R U . . .
C12 C 0.9312(2) 0.6500(2) 0.14825(9) 0.0197(4) Uani 1 1 d . . . . .
C13 C 0.8899(2) 0.61679(19) 0.20380(9) 0.0183(4) Uani 1 1 d . . . . .
C14 C 0.7490(2) 0.53596(18) 0.19868(8) 0.0178(4) Uani 1 1 d . . . . .
C15 C 0.6969(2) 0.51617(18) 0.13993(8) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.9689(2) 0.65690(19) 0.25346(9) 0.0196(4) Uani 1 1 d . . . . .
H16 H 1.065084 0.711721 0.256989 0.023 Uiso 1 1 calc R U . . .
C17 C 0.8959(2) 0.61032(19) 0.29811(9) 0.0188(4) Uani 1 1 d . . . . .
C18 C 0.7559(2) 0.52939(18) 0.29279(8) 0.0177(4) Uani 1 1 d . . . . .
C19 C 0.6767(2) 0.48863(18) 0.24295(9) 0.0182(4) Uani 1 1 d . . . . .
H19 H 0.580998 0.432953 0.239352 0.022 Uiso 1 1 calc R U . . .
C20 C 0.9449(2) 0.63645(19) 0.35724(9) 0.0195(4) Uani 1 1 d . . . . .
C21 C 0.7114(2) 0.50057(18) 0.34838(8) 0.0182(4) Uani 1 1 d . . . . .
C22 C 0.8244(2) 0.57525(19) 0.44357(8) 0.0183(4) Uani 1 1 d . . . . .
H22A H 0.923383 0.588347 0.459944 0.022 Uiso 1 1 calc R U . . .
H22B H 0.762835 0.493782 0.452587 0.022 Uiso 1 1 calc R U . . .
C23 C 0.7677(2) 0.67577(18) 0.46941(8) 0.0147(4) Uani 1 1 d . . . . .
C24 C 0.7613(2) 0.6602(2) 0.53059(8) 0.0214(4) Uani 1 1 d . . . . .
H24A H 0.695961 0.577076 0.535671 0.026 Uiso 1 1 calc R U . . .
H24B H 0.858697 0.667699 0.546977 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7067(2) 0.7586(2) 0.55919(9) 0.0244(5) Uani 1 1 d . . . . .
H25 H 0.703196 0.747487 0.598861 0.029 Uiso 1 1 calc R U . . .
C26 C 0.8087(2) 0.8877(2) 0.55173(9) 0.0270(5) Uani 1 1 d . . . . .
H26A H 0.774074 0.951537 0.570340 0.032 Uiso 1 1 calc R U . . .
H26B H 0.906844 0.897314 0.568054 0.032 Uiso 1 1 calc R U . . .
C27 C 0.8135(2) 0.90407(19) 0.49089(9) 0.0212(4) Uani 1 1 d . . . . .
H27 H 0.879961 0.988004 0.485952 0.025 Uiso 1 1 calc R U . . .
C28 C 0.8687(2) 0.80547(18) 0.46222(8) 0.0178(4) Uani 1 1 d . . . . .
H28A H 0.872941 0.816778 0.422983 0.021 Uiso 1 1 calc R U . . .
H28B H 0.967360 0.814733 0.477803 0.021 Uiso 1 1 calc R U . . .
C29 C 0.6618(2) 0.89053(18) 0.46582(9) 0.0180(4) Uani 1 1 d . . . . .
H29A H 0.665258 0.902192 0.426601 0.022 Uiso 1 1 calc R U . . .
H29B H 0.626319 0.954645 0.483703 0.022 Uiso 1 1 calc R U . . .
C30 C 0.5583(2) 0.76163(18) 0.47310(8) 0.0151(4) Uani 1 1 d . . . . .
C31 C 0.6151(2) 0.66309(17) 0.44501(8) 0.0138(4) Uani 1 1 d . . . . .
H31A H 0.549212 0.579821 0.449553 0.017 Uiso 1 1 calc R U . . .
H31B H 0.617252 0.672488 0.405571 0.017 Uiso 1 1 calc R U . . .
C32 C 0.5547(2) 0.7459(2) 0.53416(8) 0.0206(4) Uani 1 1 d . . . . .
H32A H 0.487691 0.663615 0.539529 0.025 Uiso 1 1 calc R U . . .
H32B H 0.519171 0.809357 0.552592 0.025 Uiso 1 1 calc R U . . .
C33 C 0.4047(2) 0.74775(19) 0.44986(8) 0.0164(4) Uani 1 1 d . . . . .
H33A H 0.338502 0.668643 0.459388 0.020 Uiso 1 1 calc R U . . .
H33B H 0.373965 0.815199 0.467347 0.020 Uiso 1 1 calc R U . . .
C34 C 0.4019(2) 0.85633(18) 0.36486(8) 0.0166(4) Uani 1 1 d . . . . .
C35 C 0.3734(2) 0.81439(18) 0.30530(8) 0.0152(4) Uani 1 1 d . . . . .
C36 C 0.3468(2) 0.68733(18) 0.29894(8) 0.0158(4) Uani 1 1 d . . . . .
C37 C 0.3484(2) 0.64364(18) 0.35426(8) 0.0161(4) Uani 1 1 d . . . . .
C38 C 0.3791(2) 0.88432(18) 0.26175(8) 0.0166(4) Uani 1 1 d . . . . .
H38 H 0.394940 0.970792 0.266188 0.020 Uiso 1 1 calc R U . . .
C39 C 0.3600(2) 0.81799(18) 0.21111(8) 0.0158(4) Uani 1 1 d . . . . .
C40 C 0.3351(2) 0.69079(18) 0.20439(8) 0.0152(4) Uani 1 1 d . . . . .
C41 C 0.3273(2) 0.62062(18) 0.24816(8) 0.0158(4) Uani 1 1 d . . . . .
H41 H 0.309956 0.533932 0.243788 0.019 Uiso 1 1 calc R U . . .
C42 C 0.3721(2) 0.86413(18) 0.15605(8) 0.0164(4) Uani 1 1 d . . . . .
C43 C 0.3258(2) 0.65245(18) 0.14477(8) 0.0165(4) Uani 1 1 d . . . . .
C44 C 0.3729(2) 0.76682(19) 0.06111(8) 0.0172(4) Uani 1 1 d . . . . .
H44A H 0.335956 0.832991 0.049365 0.021 Uiso 1 1 calc R U . . .
H44B H 0.310087 0.687564 0.042079 0.021 Uiso 1 1 calc R U . . .
C45 C -0.2606(2) 0.20733(18) 0.30842(9) 0.0185(4) Uani 1 1 d . . . . .
C46 C -0.1570(2) 0.25853(19) 0.35076(8) 0.0186(4) Uani 1 1 d . . . . .
C47 C -0.0187(2) 0.3360(2) 0.34223(9) 0.0219(4) Uani 1 1 d . . . . .
H47 H 0.050786 0.370439 0.372262 0.026 Uiso 1 1 calc R U . . .
C48 C 0.0158(2) 0.3617(2) 0.29062(9) 0.0223(4) Uani 1 1 d . . . . .
H48 H 0.109260 0.414182 0.284885 0.027 Uiso 1 1 calc R U . . .
C49 C -0.0872(2) 0.31030(18) 0.24579(8) 0.0183(4) Uani 1 1 d . . . . .
C50 C -0.0537(2) 0.33562(19) 0.19165(9) 0.0205(4) Uani 1 1 d . . . . .
C51 C -0.1560(2) 0.28298(18) 0.14914(8) 0.0184(4) Uani 1 1 d . . . . .
C52 C -0.2954(2) 0.20705(19) 0.15765(9) 0.0208(4) Uani 1 1 d . . . . .
H52 H -0.364890 0.172841 0.127609 0.025 Uiso 1 1 calc R U . . .
C53 C -0.3304(2) 0.18270(19) 0.20934(9) 0.0206(4) Uani 1 1 d . . . . .
H53 H -0.424543 0.131717 0.215097 0.025 Uiso 1 1 calc R U . . .
C54 C -0.2272(2) 0.23292(18) 0.25431(8) 0.0170(4) Uani 1 1 d . . . . .
C55 C 0.7536(3) 0.8753(3) 0.22982(14) 0.0448(7) Uani 1 1 d . . . . .
H55A H 0.843856 0.879039 0.213532 0.067 Uiso 1 1 calc R U . . .
H55B H 0.726059 0.948074 0.222175 0.067 Uiso 1 1 calc R U . . .
H55C H 0.677226 0.800446 0.214308 0.067 Uiso 1 1 calc R U . . .
C56 C 0.7752(3) 0.8724(3) 0.29188(12) 0.0380(6) Uani 1 1 d . . . . .
C57 C 0.9154(4) 0.9684(3) 0.31884(14) 0.0563(9) Uani 1 1 d . . . . .
H57A H 0.997042 0.937385 0.313437 0.084 Uiso 1 1 calc R U . . .
H57B H 0.906511 0.982403 0.357894 0.084 Uiso 1 1 calc R U . . .
H57C H 0.931614 1.046168 0.302309 0.084 Uiso 1 1 calc R U . . .
N1 N 0.80832(19) 0.59164(16) 0.11302(7) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.82753(18) 0.57262(16) 0.38447(7) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.39044(17) 0.75045(15) 0.39093(7) 0.0153(3) Uani 1 1 d . . . . .
N4 N 0.36299(18) 0.76214(15) 0.11957(7) 0.0156(3) Uani 1 1 d . . . . .
O1 O 1.04580(16) 0.71345(16) 0.13510(6) 0.0264(3) Uani 1 1 d . . . . .
O2 O 1.06221(16) 0.69880(15) 0.37811(6) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.60064(16) 0.43005(14) 0.36089(6) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.58240(17) 0.44950(13) 0.11849(6) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.43129(16) 0.96031(13) 0.38678(6) 0.0207(3) Uani 1 1 d . . . . .
O6 O 0.38825(17) 0.96785(13) 0.14412(6) 0.0212(3) Uani 1 1 d . . . . .
O7 O 0.29225(17) 0.54963(13) 0.12127(6) 0.0217(3) Uani 1 1 d . . . . .
O8 O 0.31832(16) 0.53897(13) 0.36623(6) 0.0212(3) Uani 1 1 d . . . . .
O9 O -0.39482(17) 0.13096(15) 0.31393(6) 0.0275(4) Uani 1 1 d . . . . .
H9 H -0.404398 0.120678 0.346951 0.041 Uiso 1 1 calc R U . . .
O10 O 0.08028(18) 0.41198(17) 0.18646(7) 0.0334(4) Uani 1 1 d . . . . .
H10 H 0.094082 0.415314 0.153311 0.050 Uiso 1 1 calc R U . . .
O11 O 0.69450(19) 0.79623(18) 0.31625(8) 0.0373(4) Uani 1 1 d . . . . .
Br1 Br -0.20134(2) 0.22006(2) 0.42229(2) 0.02372(7) Uani 1 1 d . . . . .
Br2 Br -0.10639(2) 0.31448(2) 0.07717(2) 0.02300(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
C60 Cl7 1.422(14) . ?
C60 Cl9 1.573(15) . ?
C60 Cl8 1.610(14) . ?
C60 H60 1.0000 . ?
C58 Cl2 1.750(7) . ?
C58 Cl3 1.755(7) . ?
C58 Cl1 1.767(8) . ?
C58 H58 1.0000 . ?
C59 Cl5 1.704(16) . ?
C59 Cl4 1.705(17) . ?
C59 Cl6 1.724(17) . ?
C59 H59 1.0000 . ?
C1 C11 1.533(3) . ?
C1 C6 1.537(3) . ?
C1 C2 1.540(3) . ?
C1 C9 1.541(3) . ?
C2 C3 1.538(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.534(3) . ?
C3 C44 1.536(3) . ?
C3 C7 1.539(3) . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C10 1.531(4) . ?
C5 C6 1.534(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C10 1.531(3) . ?
C8 C9 1.536(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.462(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O1 1.208(3) . ?
C12 N1 1.395(3) . ?
C12 C13 1.497(3) . ?
C13 C16 1.380(3) . ?
C13 C14 1.394(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.490(3) . ?
C15 O4 1.208(3) . ?
C15 N1 1.400(3) . ?
C16 C17 1.398(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 C20 1.492(3) . ?
C18 C19 1.386(3) . ?
C18 C21 1.495(3) . ?
C19 H19 0.9500 . ?
C20 O2 1.209(3) . ?
C20 N2 1.394(3) . ?
C21 O3 1.205(3) . ?
C21 N2 1.401(3) . ?
C22 N2 1.462(3) . ?
C22 C23 1.537(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.537(3) . ?
C23 C31 1.537(3) . ?
C23 C24 1.539(3) . ?
C24 C25 1.532(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.536(3) . ?
C25 C32 1.537(3) . ?
C25 H25 1.0000 . ?
C26 C27 1.532(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C29 1.532(3) . ?
C27 C28 1.538(3) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.539(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C33 1.535(3) . ?
C30 C32 1.535(3) . ?
C30 C31 1.541(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 N3 1.460(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O5 1.211(2) . ?
C34 N3 1.392(3) . ?
C34 C35 1.498(3) . ?
C35 C38 1.383(3) . ?
C35 C36 1.391(3) . ?
C36 C41 1.391(3) . ?
C36 C37 1.493(3) . ?
C37 O8 1.206(2) . ?
C37 N3 1.402(3) . ?
C38 C39 1.386(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(3) . ?
C39 C42 1.495(3) . ?
C40 C41 1.388(3) . ?
C40 C43 1.496(3) . ?
C41 H41 0.9500 . ?
C42 O6 1.210(3) . ?
C42 N4 1.397(2) . ?
C43 O7 1.211(2) . ?
C43 N4 1.399(3) . ?
C44 N4 1.458(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 O9 1.353(2) . ?
C45 C46 1.374(3) . ?
C45 C54 1.425(3) . ?
C46 C47 1.406(3) . ?
C46 Br1 1.896(2) . ?
C47 C48 1.368(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.415(3) . ?
C48 H48 0.9500 . ?
C49 C54 1.418(3) . ?
C49 C50 1.426(3) . ?
C50 O10 1.350(3) . ?
C50 C51 1.373(3) . ?
C51 C52 1.408(3) . ?
C51 Br2 1.902(2) . ?
C52 C53 1.368(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.416(3) . ?
C53 H53 0.9500 . ?
C55 C56 1.542(4) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 O11 1.205(3) . ?
C56 C57 1.544(4) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?

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
Cl7 C60 Cl9 123.6(13) . . ?
Cl7 C60 Cl8 115.0(11) . . ?
Cl9 C60 Cl8 121.2(12) . . ?
Cl7 C60 H60 91.4 . . ?
Cl9 C60 H60 91.4 . . ?
Cl8 C60 H60 91.4 . . ?
Cl2 C58 Cl3 111.9(4) . . ?
Cl2 C58 Cl1 108.0(4) . . ?
Cl3 C58 Cl1 111.2(4) . . ?
Cl2 C58 H58 108.6 . . ?
Cl3 C58 H58 108.6 . . ?
Cl1 C58 H58 108.6 . . ?
Cl5 C59 Cl4 111.0(11) . . ?
Cl5 C59 Cl6 115.8(13) . . ?
Cl4 C59 Cl6 120.9(13) . . ?
Cl5 C59 H59 101.8 . . ?
Cl4 C59 H59 101.8 . . ?
Cl6 C59 H59 101.8 . . ?
C11 C1 C6 108.26(16) . . ?
C11 C1 C2 110.98(16) . . ?
C6 C1 C2 108.72(17) . . ?
C11 C1 C9 110.94(17) . . ?
C6 C1 C9 109.14(17) . . ?
C2 C1 C9 108.76(16) . . ?
C3 C2 C1 110.94(16) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2AB 109.5 . . ?
C1 C2 H2AB 109.5 . . ?
H2A C2 H2AB 108.0 . . ?
C4 C3 C44 107.95(16) . . ?
C4 C3 C2 108.45(16) . . ?
C44 C3 C2 110.77(16) . . ?
C4 C3 C7 108.81(16) . . ?
C44 C3 C7 111.99(16) . . ?
C2 C3 C7 108.79(16) . . ?
C3 C4 C5 110.46(17) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4AB 109.6 . . ?
C5 C4 H4AB 109.6 . . ?
H4A C4 H4AB 108.1 . . ?
C10 C5 C6 109.8(2) . . ?
C10 C5 C4 109.46(19) . . ?
C6 C5 C4 109.31(18) . . ?
C10 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C5 C6 C1 109.72(17) . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6AB 109.7 . . ?
C1 C6 H6AB 109.7 . . ?
H6A C6 H6AB 108.2 . . ?
C8 C7 C3 110.27(17) . . ?
C8 C7 H7A 109.6 . . ?
C3 C7 H7A 109.6 . . ?
C8 C7 H7AB 109.6 . . ?
C3 C7 H7AB 109.6 . . ?
H7A C7 H7AB 108.1 . . ?
C10 C8 C7 109.88(19) . . ?
C10 C8 C9 109.08(19) . . ?
C7 C8 C9 109.17(17) . . ?
C10 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
C8 C9 C1 110.15(17) . . ?
C8 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
C8 C9 H9AB 109.6 . . ?
C1 C9 H9AB 109.6 . . ?
H9A C9 H9AB 108.1 . . ?
C8 C10 C5 109.56(18) . . ?
C8 C10 H10A 109.8 . . ?
C5 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C5 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
N1 C11 C1 113.51(16) . . ?
N1 C11 H11A 108.9 . . ?
C1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O1 C12 N1 125.6(2) . . ?
O1 C12 C13 128.6(2) . . ?
N1 C12 C13 105.75(17) . . ?
C16 C13 C14 122.6(2) . . ?
C16 C13 C12 129.19(19) . . ?
C14 C13 C12 108.15(18) . . ?
C19 C14 C13 122.91(19) . . ?
C19 C14 C15 129.27(19) . . ?
C13 C14 C15 107.81(18) . . ?
O4 C15 N1 125.47(19) . . ?
O4 C15 C14 128.36(19) . . ?
N1 C15 C14 106.18(17) . . ?
C13 C16 C17 114.56(19) . . ?
C13 C16 H16 122.7 . . ?
C17 C16 H16 122.7 . . ?
C18 C17 C16 122.59(19) . . ?
C18 C17 C20 108.05(18) . . ?
C16 C17 C20 129.34(19) . . ?
C19 C18 C17 122.9(2) . . ?
C19 C18 C21 128.85(19) . . ?
C17 C18 C21 108.24(18) . . ?
C18 C19 C14 114.40(19) . . ?
C18 C19 H19 122.8 . . ?
C14 C19 H19 122.8 . . ?
O2 C20 N2 126.1(2) . . ?
O2 C20 C17 127.9(2) . . ?
N2 C20 C17 105.96(17) . . ?
O3 C21 N2 125.87(19) . . ?
O3 C21 C18 128.62(19) . . ?
N2 C21 C18 105.51(17) . . ?
N2 C22 C23 114.12(16) . . ?
N2 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
N2 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C28 C23 C22 111.19(16) . . ?
C28 C23 C31 108.91(16) . . ?
C22 C23 C31 111.72(16) . . ?
C28 C23 C24 108.93(16) . . ?
C22 C23 C24 107.56(16) . . ?
C31 C23 C24 108.44(16) . . ?
C25 C24 C23 110.43(17) . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 109.59(18) . . ?
C24 C25 C32 109.49(18) . . ?
C26 C25 C32 109.08(19) . . ?
C24 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C32 C25 H25 109.6 . . ?
C27 C26 C25 109.25(17) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 C29 109.76(17) . . ?
C26 C27 C28 109.67(18) . . ?
C29 C27 C28 109.28(16) . . ?
C26 C27 H27 109.4 . . ?
C29 C27 H27 109.4 . . ?
C28 C27 H27 109.4 . . ?
C23 C28 C27 110.08(16) . . ?
C23 C28 H28A 109.6 . . ?
C27 C28 H28A 109.6 . . ?
C23 C28 H28B 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.2 . . ?
C27 C29 C30 109.92(17) . . ?
C27 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
C27 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C33 C30 C32 108.25(16) . . ?
C33 C30 C29 110.70(17) . . ?
C32 C30 C29 108.68(16) . . ?
C33 C30 C31 111.08(15) . . ?
C32 C30 C31 109.10(17) . . ?
C29 C30 C31 108.97(15) . . ?
C23 C31 C30 110.75(15) . . ?
C23 C31 H31A 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C30 C32 C25 110.08(17) . . ?
C30 C32 H32A 109.6 . . ?
C25 C32 H32A 109.6 . . ?
C30 C32 H32B 109.6 . . ?
C25 C32 H32B 109.6 . . ?
H32A C32 H32B 108.2 . . ?
N3 C33 C30 113.90(16) . . ?
N3 C33 H33A 108.8 . . ?
C30 C33 H33A 108.8 . . ?
N3 C33 H33B 108.8 . . ?
C30 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
O5 C34 N3 126.01(19) . . ?
O5 C34 C35 128.15(19) . . ?
N3 C34 C35 105.83(16) . . ?
C38 C35 C36 122.86(18) . . ?
C38 C35 C34 128.95(18) . . ?
C36 C35 C34 108.08(17) . . ?
C35 C36 C41 122.62(19) . . ?
C35 C36 C37 107.95(17) . . ?
C41 C36 C37 129.41(18) . . ?
O8 C37 N3 125.86(19) . . ?
O8 C37 C36 128.36(18) . . ?
N3 C37 C36 105.78(16) . . ?
C35 C38 C39 114.56(18) . . ?
C35 C38 H38 122.7 . . ?
C39 C38 H38 122.7 . . ?
C38 C39 C40 122.93(19) . . ?
C38 C39 C42 129.08(18) . . ?
C40 C39 C42 107.84(17) . . ?
C41 C40 C39 122.36(18) . . ?
C41 C40 C43 129.64(18) . . ?
C39 C40 C43 107.96(17) . . ?
C40 C41 C36 114.65(18) . . ?
C40 C41 H41 122.7 . . ?
C36 C41 H41 122.7 . . ?
O6 C42 N4 125.55(19) . . ?
O6 C42 C39 128.50(18) . . ?
N4 C42 C39 105.95(16) . . ?
O7 C43 N4 125.10(19) . . ?
O7 C43 C40 129.21(19) . . ?
N4 C43 C40 105.68(16) . . ?
N4 C44 C3 113.69(16) . . ?
N4 C44 H44A 108.8 . . ?
C3 C44 H44A 108.8 . . ?
N4 C44 H44B 108.8 . . ?
C3 C44 H44B 108.8 . . ?
H44A C44 H44B 107.7 . . ?
O9 C45 C46 124.55(19) . . ?
O9 C45 C54 116.15(18) . . ?
C46 C45 C54 119.29(18) . . ?
C45 C46 C47 121.78(19) . . ?
C45 C46 Br1 118.78(15) . . ?
C47 C46 Br1 119.42(16) . . ?
C48 C47 C46 119.9(2) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C47 C48 C49 120.18(19) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
C48 C49 C54 120.01(19) . . ?
C48 C49 C50 121.18(19) . . ?
C54 C49 C50 118.81(19) . . ?
O10 C50 C51 124.7(2) . . ?
O10 C50 C49 115.84(18) . . ?
C51 C50 C49 119.48(19) . . ?
C50 C51 C52 121.68(19) . . ?
C50 C51 Br2 118.57(16) . . ?
C52 C51 Br2 119.74(16) . . ?
C53 C52 C51 119.77(19) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 120.48(19) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C53 C54 C49 119.76(19) . . ?
C53 C54 C45 121.45(19) . . ?
C49 C54 C45 118.80(19) . . ?
C56 C55 H55A 109.5 . . ?
C56 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C56 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O11 C56 C55 122.5(3) . . ?
O11 C56 C57 123.3(3) . . ?
C55 C56 C57 114.0(3) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C12 N1 C15 111.86(17) . . ?
C12 N1 C11 124.33(18) . . ?
C15 N1 C11 123.78(17) . . ?
C20 N2 C21 112.03(17) . . ?
C20 N2 C22 125.17(17) . . ?
C21 N2 C22 122.78(17) . . ?
C34 N3 C37 112.02(16) . . ?
C34 N3 C33 124.52(16) . . ?
C37 N3 C33 123.15(16) . . ?
C42 N4 C43 111.74(16) . . ?
C42 N4 C44 124.14(17) . . ?
C43 N4 C44 123.71(16) . . ?
C45 O9 H9 109.5 . . ?
C50 O10 H10 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
C11 C1 C2 C3 -178.68(16) . . . . ?
C6 C1 C2 C3 -59.7(2) . . . . ?
C9 C1 C2 C3 59.0(2) . . . . ?
C1 C2 C3 C4 59.2(2) . . . . ?
C1 C2 C3 C44 177.46(15) . . . . ?
C1 C2 C3 C7 -59.0(2) . . . . ?
C44 C3 C4 C5 -179.17(17) . . . . ?
C2 C3 C4 C5 -59.1(2) . . . . ?
C7 C3 C4 C5 59.1(2) . . . . ?
C3 C4 C5 C10 -60.0(2) . . . . ?
C3 C4 C5 C6 60.3(2) . . . . ?
C10 C5 C6 C1 59.8(2) . . . . ?
C4 C5 C6 C1 -60.2(2) . . . . ?
C11 C1 C6 C5 -179.70(18) . . . . ?
C2 C1 C6 C5 59.6(2) . . . . ?
C9 C1 C6 C5 -58.9(2) . . . . ?
C4 C3 C7 C8 -58.7(2) . . . . ?
C44 C3 C7 C8 -177.90(17) . . . . ?
C2 C3 C7 C8 59.3(2) . . . . ?
C3 C7 C8 C10 59.4(2) . . . . ?
C3 C7 C8 C9 -60.2(2) . . . . ?
C10 C8 C9 C1 -60.0(2) . . . . ?
C7 C8 C9 C1 60.1(2) . . . . ?
C11 C1 C9 C8 178.47(17) . . . . ?
C6 C1 C9 C8 59.3(2) . . . . ?
C2 C1 C9 C8 -59.2(2) . . . . ?
C7 C8 C10 C5 -59.4(2) . . . . ?
C9 C8 C10 C5 60.2(2) . . . . ?
C6 C5 C10 C8 -60.5(2) . . . . ?
C4 C5 C10 C8 59.5(2) . . . . ?
C6 C1 C11 N1 -178.22(17) . . . . ?
C2 C1 C11 N1 -59.0(2) . . . . ?
C9 C1 C11 N1 62.1(2) . . . . ?
O1 C12 C13 C16 4.8(4) . . . . ?
N1 C12 C13 C16 -175.4(2) . . . . ?
O1 C12 C13 C14 -176.7(2) . . . . ?
N1 C12 C13 C14 3.2(2) . . . . ?
C16 C13 C14 C19 -0.3(3) . . . . ?
C12 C13 C14 C19 -178.99(18) . . . . ?
C16 C13 C14 C15 178.38(19) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C19 C14 C15 O4 -4.0(4) . . . . ?
C13 C14 C15 O4 177.4(2) . . . . ?
C19 C14 C15 N1 175.9(2) . . . . ?
C13 C14 C15 N1 -2.7(2) . . . . ?
C14 C13 C16 C17 -0.3(3) . . . . ?
C12 C13 C16 C17 178.1(2) . . . . ?
C13 C16 C17 C18 0.6(3) . . . . ?
C13 C16 C17 C20 -177.7(2) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C20 C17 C18 C19 178.32(19) . . . . ?
C16 C17 C18 C21 -179.05(19) . . . . ?
C20 C17 C18 C21 -0.4(2) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C21 C18 C19 C14 178.16(19) . . . . ?
C13 C14 C19 C18 0.6(3) . . . . ?
C15 C14 C19 C18 -177.82(19) . . . . ?
C18 C17 C20 O2 176.9(2) . . . . ?
C16 C17 C20 O2 -4.6(4) . . . . ?
C18 C17 C20 N2 -2.4(2) . . . . ?
C16 C17 C20 N2 176.2(2) . . . . ?
C19 C18 C21 O3 5.0(4) . . . . ?
C17 C18 C21 O3 -176.4(2) . . . . ?
C19 C18 C21 N2 -175.6(2) . . . . ?
C17 C18 C21 N2 3.0(2) . . . . ?
N2 C22 C23 C28 -64.7(2) . . . . ?
N2 C22 C23 C31 57.2(2) . . . . ?
N2 C22 C23 C24 176.09(16) . . . . ?
C28 C23 C24 C25 58.9(2) . . . . ?
C22 C23 C24 C25 179.49(17) . . . . ?
C31 C23 C24 C25 -59.5(2) . . . . ?
C23 C24 C25 C26 -59.7(2) . . . . ?
C23 C24 C25 C32 59.9(2) . . . . ?
C24 C25 C26 C27 59.8(2) . . . . ?
C32 C25 C26 C27 -60.1(2) . . . . ?
C25 C26 C27 C29 60.1(2) . . . . ?
C25 C26 C27 C28 -60.0(2) . . . . ?
C22 C23 C28 C27 -177.17(16) . . . . ?
C31 C23 C28 C27 59.3(2) . . . . ?
C24 C23 C28 C27 -58.8(2) . . . . ?
C26 C27 C28 C23 60.0(2) . . . . ?
C29 C27 C28 C23 -60.3(2) . . . . ?
C26 C27 C29 C30 -60.1(2) . . . . ?
C28 C27 C29 C30 60.3(2) . . . . ?
C27 C29 C30 C33 178.18(16) . . . . ?
C27 C29 C30 C32 59.4(2) . . . . ?
C27 C29 C30 C31 -59.4(2) . . . . ?
C28 C23 C31 C30 -59.0(2) . . . . ?
C22 C23 C31 C30 177.78(15) . . . . ?
C24 C23 C31 C30 59.4(2) . . . . ?
C33 C30 C31 C23 -178.70(15) . . . . ?
C32 C30 C31 C23 -59.5(2) . . . . ?
C29 C30 C31 C23 59.1(2) . . . . ?
C33 C30 C32 C25 179.79(18) . . . . ?
C29 C30 C32 C25 -59.9(2) . . . . ?
C31 C30 C32 C25 58.8(2) . . . . ?
C24 C25 C32 C30 -59.3(2) . . . . ?
C26 C25 C32 C30 60.6(2) . . . . ?
C32 C30 C33 N3 -175.14(16) . . . . ?
C29 C30 C33 N3 65.8(2) . . . . ?
C31 C30 C33 N3 -55.4(2) . . . . ?
O5 C34 C35 C38 2.6(4) . . . . ?
N3 C34 C35 C38 -176.31(19) . . . . ?
O5 C34 C35 C36 178.9(2) . . . . ?
N3 C34 C35 C36 0.0(2) . . . . ?
C38 C35 C36 C41 1.6(3) . . . . ?
C34 C35 C36 C41 -174.96(18) . . . . ?
C38 C35 C36 C37 -179.95(18) . . . . ?
C34 C35 C36 C37 3.5(2) . . . . ?
C35 C36 C37 O8 173.3(2) . . . . ?
C41 C36 C37 O8 -8.4(4) . . . . ?
C35 C36 C37 N3 -5.7(2) . . . . ?
C41 C36 C37 N3 172.64(19) . . . . ?
C36 C35 C38 C39 -1.6(3) . . . . ?
C34 C35 C38 C39 174.17(19) . . . . ?
C35 C38 C39 C40 0.8(3) . . . . ?
C35 C38 C39 C42 -174.14(19) . . . . ?
C38 C39 C40 C41 0.1(3) . . . . ?
C42 C39 C40 C41 175.98(18) . . . . ?
C38 C39 C40 C43 -177.73(18) . . . . ?
C42 C39 C40 C43 -1.9(2) . . . . ?
C39 C40 C41 C36 -0.2(3) . . . . ?
C43 C40 C41 C36 177.10(19) . . . . ?
C35 C36 C41 C40 -0.6(3) . . . . ?
C37 C36 C41 C40 -178.68(19) . . . . ?
C38 C39 C42 O6 -7.5(4) . . . . ?
C40 C39 C42 O6 177.0(2) . . . . ?
C38 C39 C42 N4 171.8(2) . . . . ?
C40 C39 C42 N4 -3.8(2) . . . . ?
C41 C40 C43 O7 10.0(4) . . . . ?
C39 C40 C43 O7 -172.4(2) . . . . ?
C41 C40 C43 N4 -170.82(19) . . . . ?
C39 C40 C43 N4 6.8(2) . . . . ?
C4 C3 C44 N4 178.92(16) . . . . ?
C2 C3 C44 N4 60.3(2) . . . . ?
C7 C3 C44 N4 -61.3(2) . . . . ?
O9 C45 C46 C47 179.1(2) . . . . ?
C54 C45 C46 C47 0.2(3) . . . . ?
O9 C45 C46 Br1 0.6(3) . . . . ?
C54 C45 C46 Br1 -178.33(15) . . . . ?
C45 C46 C47 C48 -0.3(3) . . . . ?
Br1 C46 C47 C48 178.23(17) . . . . ?
C46 C47 C48 C49 -0.1(3) . . . . ?
C47 C48 C49 C54 0.6(3) . . . . ?
C47 C48 C49 C50 -179.9(2) . . . . ?
C48 C49 C50 O10 -0.8(3) . . . . ?
C54 C49 C50 O10 178.6(2) . . . . ?
C48 C49 C50 C51 179.3(2) . . . . ?
C54 C49 C50 C51 -1.2(3) . . . . ?
O10 C50 C51 C52 -178.0(2) . . . . ?
C49 C50 C51 C52 1.9(3) . . . . ?
O10 C50 C51 Br2 2.0(3) . . . . ?
C49 C50 C51 Br2 -178.18(16) . . . . ?
C50 C51 C52 C53 -1.1(3) . . . . ?
Br2 C51 C52 C53 178.92(16) . . . . ?
C51 C52 C53 C54 -0.2(3) . . . . ?
C52 C53 C54 C49 0.8(3) . . . . ?
C52 C53 C54 C45 -179.1(2) . . . . ?
C48 C49 C54 C53 179.41(19) . . . . ?
C50 C49 C54 C53 -0.1(3) . . . . ?
C48 C49 C54 C45 -0.7(3) . . . . ?
C50 C49 C54 C45 179.82(19) . . . . ?
O9 C45 C54 C53 1.2(3) . . . . ?
C46 C45 C54 C53 -179.8(2) . . . . ?
O9 C45 C54 C49 -178.70(19) . . . . ?
C46 C45 C54 C49 0.3(3) . . . . ?
O1 C12 N1 C15 174.8(2) . . . . ?
C13 C12 N1 C15 -5.1(2) . . . . ?
O1 C12 N1 C11 -3.2(3) . . . . ?
C13 C12 N1 C11 176.95(17) . . . . ?
O4 C15 N1 C12 -175.2(2) . . . . ?
C14 C15 N1 C12 5.0(2) . . . . ?
O4 C15 N1 C11 2.8(3) . . . . ?
C14 C15 N1 C11 -177.09(17) . . . . ?
C1 C11 N1 C12 -92.2(2) . . . . ?
C1 C11 N1 C15 90.1(2) . . . . ?
O2 C20 N2 C21 -174.8(2) . . . . ?
C17 C20 N2 C21 4.5(2) . . . . ?
O2 C20 N2 C22 3.2(3) . . . . ?
C17 C20 N2 C22 -177.54(18) . . . . ?
O3 C21 N2 C20 174.7(2) . . . . ?
C18 C21 N2 C20 -4.7(2) . . . . ?
O3 C21 N2 C22 -3.3(3) . . . . ?
C18 C21 N2 C22 177.27(17) . . . . ?
C23 C22 N2 C20 91.5(2) . . . . ?
C23 C22 N2 C21 -90.7(2) . . . . ?
O5 C34 N3 C37 177.26(19) . . . . ?
C35 C34 N3 C37 -3.8(2) . . . . ?
O5 C34 N3 C33 3.5(3) . . . . ?
C35 C34 N3 C33 -177.49(17) . . . . ?
O8 C37 N3 C34 -173.16(19) . . . . ?
C36 C37 N3 C34 5.9(2) . . . . ?
O8 C37 N3 C33 0.7(3) . . . . ?
C36 C37 N3 C33 179.67(16) . . . . ?
C30 C33 N3 C34 -93.0(2) . . . . ?
C30 C33 N3 C37 94.0(2) . . . . ?
O6 C42 N4 C43 -172.3(2) . . . . ?
C39 C42 N4 C43 8.4(2) . . . . ?
O6 C42 N4 C44 0.5(3) . . . . ?
C39 C42 N4 C44 -178.74(17) . . . . ?
O7 C43 N4 C42 169.7(2) . . . . ?
C40 C43 N4 C42 -9.5(2) . . . . ?
O7 C43 N4 C44 -3.2(3) . . . . ?
C40 C43 N4 C44 177.61(17) . . . . ?
C3 C44 N4 C42 92.0(2) . . . . ?
C3 C44 N4 C43 -96.1(2) . . . . ?

_refine_diff_density_max         1.340
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 2444562'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2025-04-17 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H50 N4 O9'
_chemical_formula_weight         826.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.4443(5)
_cell_length_b                   16.6197(5)
_cell_length_c                   17.6078(6)
_cell_angle_alpha                113.668(2)
_cell_angle_beta                 105.994(2)
_cell_angle_gamma                92.943(2)
_cell_volume                     4164.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8224
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            45481
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         78.807
_diffrn_reflns_theta_full        3.125
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.250
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.250
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.250
_reflns_number_total             15905
_reflns_number_gt                9797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX4 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0914P)²+16.7317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         15905
_refine_ls_number_parameters     1104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_ref         0.2668
_refine_ls_wR_factor_gt          0.2143
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3544(3) 0.8029(3) 0.8331(3) 0.0325(10) Uani 1 1 d . . . . .
H1 H 0.392876 0.855413 0.839468 0.039 Uiso 1 1 calc R U . . .
C2 C 0.2605(3) 0.8095(3) 0.7977(3) 0.0291(9) Uani 1 1 d . . . . .
H2A H 0.249535 0.810775 0.740056 0.035 Uiso 1 1 calc R U . . .
H2B H 0.248850 0.865842 0.838237 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1996(3) 0.7293(3) 0.7877(3) 0.0264(9) Uani 1 1 d . . . . .
C4 C 0.2183(3) 0.6432(3) 0.7236(3) 0.0270(9) Uani 1 1 d . . . . .
H4A H 0.205762 0.643508 0.665469 0.032 Uiso 1 1 calc R U . . .
H4B H 0.180131 0.590966 0.716880 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3129(3) 0.6344(3) 0.7566(3) 0.0293(9) Uani 1 1 d . . . . .
C6 C 0.3711(3) 0.7163(3) 0.7677(3) 0.0301(10) Uani 1 1 d . . . . .
H6A H 0.432159 0.711400 0.788861 0.036 Uiso 1 1 calc R U . . .
H6B H 0.360014 0.718079 0.710246 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3719(3) 0.8005(4) 0.9211(3) 0.0404(12) Uani 1 1 d . . . . .
H7A H 0.361245 0.856331 0.963424 0.048 Uiso 1 1 calc R U . . .
H7B H 0.432971 0.796377 0.943877 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2189(3) 0.7278(3) 0.8778(3) 0.0319(10) Uani 1 1 d . . . . .
H8A H 0.207469 0.783251 0.919831 0.038 Uiso 1 1 calc R U . . .
H8B H 0.180854 0.676378 0.872509 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3136(3) 0.7201(4) 0.9118(3) 0.0367(11) Uani 1 1 d . . . . .
H9 H 0.325623 0.718847 0.970101 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3301(3) 0.6341(3) 0.8469(3) 0.0356(11) Uani 1 1 d . . . . .
H10A H 0.292158 0.582233 0.841083 0.043 Uiso 1 1 calc R U . . .
H10B H 0.390514 0.627930 0.869246 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1049(3) 0.7375(3) 0.7569(3) 0.0256(9) Uani 1 1 d . . . . .
H11A H 0.068605 0.689686 0.759198 0.031 Uiso 1 1 calc R U . . .
H11B H 0.096517 0.795626 0.797792 0.031 Uiso 1 1 calc R U . . .
C12 C 0.0818(3) 0.8033(3) 0.6475(3) 0.0254(9) Uani 1 1 d . . . . .
C13 C 0.0497(2) 0.7645(3) 0.5498(3) 0.0241(9) Uani 1 1 d . . . . .
C14 C 0.0448(3) 0.8074(3) 0.4966(3) 0.0263(9) Uani 1 1 d . . . . .
H14 H 0.062352 0.870157 0.518916 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0121(2) 0.7515(3) 0.4077(3) 0.0225(8) Uani 1 1 d . . . . .
C16 C -0.0011(2) 0.7752(3) 0.3325(3) 0.0244(9) Uani 1 1 d . . . . .
C17 C -0.0396(3) 0.6216(3) 0.2762(3) 0.0258(9) Uani 1 1 d . . . . .
C18 C -0.0134(2) 0.6593(3) 0.3740(3) 0.0246(9) Uani 1 1 d . . . . .
C19 C -0.0107(2) 0.6160(3) 0.4275(3) 0.0247(9) Uani 1 1 d . . . . .
H19 H -0.029556 0.553478 0.405045 0.030 Uiso 1 1 calc R U . . .
C20 C 0.0222(2) 0.6723(3) 0.5169(3) 0.0236(8) Uani 1 1 d . . . . .
C21 C 0.0356(2) 0.6508(3) 0.5935(3) 0.0232(8) Uani 1 1 d . . . . .
C22 C -0.0420(3) 0.6904(3) 0.1698(3) 0.0272(9) Uani 1 1 d . . . . .
H22A H -0.068786 0.741527 0.166681 0.033 Uiso 1 1 calc R U . . .
H22B H -0.083567 0.634938 0.126809 0.033 Uiso 1 1 calc R U . . .
C23 C 0.0395(3) 0.6912(3) 0.1432(3) 0.0273(9) Uani 1 1 d . . . . .
C24 C 0.1045(3) 0.7793(3) 0.2015(3) 0.0304(10) Uani 1 1 d . . . . .
H24A H 0.122649 0.787709 0.263106 0.037 Uiso 1 1 calc R U . . .
H24B H 0.076855 0.830020 0.198753 0.037 Uiso 1 1 calc R U . . .
C25 C 0.1838(3) 0.7780(3) 0.1711(3) 0.0336(10) Uani 1 1 d . . . . .
H25 H 0.225566 0.835441 0.209742 0.040 Uiso 1 1 calc R U . . .
C26 C 0.2266(3) 0.6999(3) 0.1761(3) 0.0332(10) Uani 1 1 d . . . . .
H26A H 0.245530 0.707583 0.237438 0.040 Uiso 1 1 calc R U . . .
H26B H 0.277960 0.699219 0.157101 0.040 Uiso 1 1 calc R U . . .
C27 C 0.1632(3) 0.6111(3) 0.1172(3) 0.0304(10) Uani 1 1 d . . . . .
C28 C 0.0835(3) 0.6135(3) 0.1475(3) 0.0276(9) Uani 1 1 d . . . . .
H28A H 0.042209 0.556498 0.109800 0.033 Uiso 1 1 calc R U . . .
H28B H 0.101179 0.619945 0.208475 0.033 Uiso 1 1 calc R U . . .
C29 C 0.0127(3) 0.6809(3) 0.0488(3) 0.0335(10) Uani 1 1 d . . . . .
H29A H -0.015471 0.731153 0.045469 0.040 Uiso 1 1 calc R U . . .
H29B H -0.029394 0.624622 0.009877 0.040 Uiso 1 1 calc R U . . .
C30 C 0.0912(3) 0.6794(4) 0.0175(3) 0.0384(11) Uani 1 1 d . . . . .
H30 H 0.072295 0.671883 -0.044364 0.046 Uiso 1 1 calc R U . . .
C31 C 0.1351(3) 0.6012(3) 0.0227(3) 0.0360(11) Uani 1 1 d . . . . .
H31A H 0.094591 0.543926 -0.016587 0.043 Uiso 1 1 calc R U . . .
H31B H 0.185966 0.600438 0.002843 0.043 Uiso 1 1 calc R U . . .
C32 C 0.1547(3) 0.7670(4) 0.0760(3) 0.0407(12) Uani 1 1 d . . . . .
H32A H 0.127116 0.817608 0.072901 0.049 Uiso 1 1 calc R U . . .
H32B H 0.205219 0.766791 0.055754 0.049 Uiso 1 1 calc R U . . .
C33 C 0.2056(3) 0.5312(3) 0.1192(3) 0.0336(10) Uani 1 1 d . . . . .
H33A H 0.166164 0.475184 0.073836 0.040 Uiso 1 1 calc R U . . .
H33B H 0.258928 0.534253 0.103894 0.040 Uiso 1 1 calc R U . . .
C34 C 0.3053(3) 0.5667(3) 0.2704(3) 0.0320(10) Uani 1 1 d . . . . .
C35 C 0.2972(3) 0.5512(3) 0.3458(3) 0.0293(10) Uani 1 1 d . . . . .
C36 C 0.3571(3) 0.5771(3) 0.4280(3) 0.0288(9) Uani 1 1 d . . . . .
H36 H 0.413935 0.607726 0.444076 0.035 Uiso 1 1 calc R U . . .
C37 C 0.3280(3) 0.5551(3) 0.4847(3) 0.0302(10) Uani 1 1 d . . . . .
C38 C 0.3746(3) 0.5713(3) 0.5763(3) 0.0313(10) Uani 1 1 d . . . . .
C39 C 0.2358(3) 0.4981(3) 0.5380(3) 0.0282(9) Uani 1 1 d . . . . .
C40 C 0.2444(3) 0.5105(3) 0.4611(3) 0.0287(9) Uani 1 1 d . . . . .
C41 C 0.1847(3) 0.4827(3) 0.3787(3) 0.0279(9) Uani 1 1 d . . . . .
H41 H 0.128250 0.451212 0.362685 0.033 Uiso 1 1 calc R U . . .
C42 C 0.2136(3) 0.5046(3) 0.3210(3) 0.0277(9) Uani 1 1 d . . . . .
C43 C 0.1694(3) 0.4838(3) 0.2281(3) 0.0305(10) Uani 1 1 d . . . . .
C44 C 0.3308(3) 0.5468(3) 0.6936(3) 0.0322(10) Uani 1 1 d . . . . .
H44A H 0.391611 0.542694 0.717560 0.039 Uiso 1 1 calc R U . . .
H44B H 0.294219 0.495917 0.690960 0.039 Uiso 1 1 calc R U . . .
C46 C 0.7780(3) 0.9908(3) 0.9509(3) 0.0368(11) Uani 1 1 d . . . . .
H46 H 0.768779 1.053837 0.967911 0.044 Uiso 1 1 calc R U . . .
C47 C 0.6953(3) 0.9263(3) 0.8818(3) 0.0346(11) Uani 1 1 d . . . . .
H47A H 0.680495 0.938359 0.829406 0.042 Uiso 1 1 calc R U . . .
H47B H 0.647040 0.935899 0.905962 0.042 Uiso 1 1 calc R U . . .
C48 C 0.7087(3) 0.8290(3) 0.8558(3) 0.0289(9) Uani 1 1 d . . . . .
C49 C 0.7837(3) 0.8159(3) 0.8189(3) 0.0256(9) Uani 1 1 d . . . . .
H49A H 0.769021 0.826150 0.765436 0.031 Uiso 1 1 calc R U . . .
H49B H 0.792940 0.753533 0.802202 0.031 Uiso 1 1 calc R U . . .
C50 C 0.8667(3) 0.8802(3) 0.8861(3) 0.0258(9) Uani 1 1 d . . . . .
C51 C 0.8516(3) 0.9766(3) 0.9109(3) 0.0335(10) Uani 1 1 d . . . . .
H51A H 0.836329 0.988039 0.858189 0.040 Uiso 1 1 calc R U . . .
H51B H 0.904900 1.018984 0.953909 0.040 Uiso 1 1 calc R U . . .
C52 C 0.8011(3) 0.9724(4) 1.0318(4) 0.0425(12) Uani 1 1 d . . . . .
H52A H 0.753898 0.981686 1.057442 0.051 Uiso 1 1 calc R U . . .
H52B H 0.853924 1.014457 1.076474 0.051 Uiso 1 1 calc R U . . .
C53 C 0.7335(3) 0.8120(3) 0.9385(3) 0.0336(10) Uani 1 1 d . . . . .
H53A H 0.686105 0.820386 0.963892 0.040 Uiso 1 1 calc R U . . .
H53B H 0.742425 0.749636 0.922388 0.040 Uiso 1 1 calc R U . . .
C54 C 0.8159(3) 0.8763(3) 1.0065(3) 0.0358(11) Uani 1 1 d . . . . .
H54 H 0.830985 0.864628 1.059727 0.043 Uiso 1 1 calc R U . . .
C55 C 0.8896(3) 0.8628(3) 0.9681(3) 0.0330(10) Uani 1 1 d . . . . .
H55A H 0.900098 0.800966 0.952485 0.040 Uiso 1 1 calc R U . . .
H55B H 0.942930 0.904387 1.012184 0.040 Uiso 1 1 calc R U . . .
C56 C 0.6262(3) 0.7633(3) 0.7904(3) 0.0273(9) Uani 1 1 d . . . . .
H56A H 0.633379 0.702468 0.784377 0.033 Uiso 1 1 calc R U . . .
H56B H 0.578276 0.778851 0.814269 0.033 Uiso 1 1 calc R U . . .
C57 C 0.5448(3) 0.8110(3) 0.6752(3) 0.0286(9) Uani 1 1 d . . . . .
C58 C 0.5372(3) 0.7854(3) 0.5815(3) 0.0273(9) Uani 1 1 d . . . . .
C59 C 0.4938(3) 0.8194(3) 0.5245(3) 0.0298(10) Uani 1 1 d . . . . .
H59 H 0.460557 0.864686 0.540865 0.036 Uiso 1 1 calc R U . . .
C60 C 0.5028(3) 0.7822(3) 0.4420(3) 0.0289(9) Uani 1 1 d . . . . .
C61 C 0.4700(3) 0.8044(3) 0.3665(3) 0.0316(10) Uani 1 1 d . . . . .
C62 C 0.5466(3) 0.6904(3) 0.3255(3) 0.0287(9) Uani 1 1 d . . . . .
C64 C 0.5505(3) 0.7146(3) 0.4179(3) 0.0275(9) Uani 1 1 d . . . . .
C65 C 0.5931(3) 0.6801(3) 0.4741(3) 0.0268(9) Uani 1 1 d . . . . .
H65 H 0.625237 0.633923 0.457193 0.032 Uiso 1 1 calc R U . . .
C66 C 0.5853(3) 0.7184(3) 0.5575(3) 0.0270(9) Uani 1 1 d . . . . .
C67 C 0.6246(3) 0.7002(3) 0.6340(3) 0.0263(9) Uani 1 1 d . . . . .
C68 C 0.4836(3) 0.7507(3) 0.2162(3) 0.0313(10) Uani 1 1 d . . . . .
H68A H 0.426695 0.767813 0.200840 0.038 Uiso 1 1 calc R U . . .
H68B H 0.479573 0.688989 0.172398 0.038 Uiso 1 1 calc R U . . .
C69 C 0.5508(3) 0.8139(3) 0.2098(3) 0.0265(9) Uani 1 1 d . . . . .
C70 C 0.5465(3) 0.9121(3) 0.2602(3) 0.0322(10) Uani 1 1 d . . . . .
H70A H 0.487818 0.922491 0.237466 0.039 Uiso 1 1 calc R U . . .
H70B H 0.558580 0.926578 0.322961 0.039 Uiso 1 1 calc R U . . .
C71 C 0.6119(3) 0.9728(3) 0.2504(3) 0.0336(10) Uani 1 1 d . . . . .
H71 H 0.608368 1.036752 0.283600 0.040 Uiso 1 1 calc R U . . .
C72 C 0.7026(3) 0.9566(3) 0.2872(3) 0.0303(10) Uani 1 1 d . . . . .
H72A H 0.745708 0.996205 0.282004 0.036 Uiso 1 1 calc R U . . .
H72B H 0.715206 0.971299 0.350107 0.036 Uiso 1 1 calc R U . . .
C73 C 0.7091(2) 0.8592(3) 0.2373(3) 0.0234(8) Uani 1 1 d . . . . .
C74 C 0.6417(2) 0.7985(3) 0.2455(3) 0.0246(9) Uani 1 1 d . . . . .
H74A H 0.645140 0.735241 0.212657 0.029 Uiso 1 1 calc R U . . .
H74B H 0.654208 0.810949 0.307912 0.029 Uiso 1 1 calc R U . . .
C75 C 0.5320(3) 0.7924(3) 0.1130(3) 0.0321(10) Uani 1 1 d . . . . .
H75A H 0.473202 0.801552 0.088700 0.039 Uiso 1 1 calc R U . . .
H75B H 0.535081 0.729068 0.079777 0.039 Uiso 1 1 calc R U . . .
C76 C 0.5979(3) 0.8533(4) 0.1036(3) 0.0366(11) Uani 1 1 d . . . . .
H76 H 0.585137 0.838939 0.040203 0.044 Uiso 1 1 calc R U . . .
C77 C 0.6890(3) 0.8375(3) 0.1397(3) 0.0290(9) Uani 1 1 d . . . . .
H77A H 0.692782 0.774358 0.106490 0.035 Uiso 1 1 calc R U . . .
H77B H 0.731619 0.875983 0.132777 0.035 Uiso 1 1 calc R U . . .
C78 C 0.5930(3) 0.9510(4) 0.1536(4) 0.0411(12) Uani 1 1 d . . . . .
H78A H 0.534935 0.961873 0.129613 0.049 Uiso 1 1 calc R U . . .
H78B H 0.635541 0.989941 0.147035 0.049 Uiso 1 1 calc R U . . .
C79 C 0.7992(3) 0.8414(3) 0.2710(3) 0.0255(9) Uani 1 1 d . . . . .
H79A H 0.803771 0.781602 0.229625 0.031 Uiso 1 1 calc R U . . .
H79B H 0.841858 0.885994 0.271351 0.031 Uiso 1 1 calc R U . . .
C80 C 0.8623(3) 0.9226(3) 0.4360(3) 0.0263(9) Uani 1 1 d . . . . .
C81 C 0.8720(3) 0.8972(3) 0.5094(3) 0.0260(9) Uani 1 1 d . . . . .
C82 C 0.9088(3) 0.9492(3) 0.5990(3) 0.0260(9) Uani 1 1 d . . . . .
H82 H 0.932313 1.011010 0.623349 0.031 Uiso 1 1 calc R U . . .
C83 C 0.9085(2) 0.9043(3) 0.6500(3) 0.0241(8) Uani 1 1 d . . . . .
C84 C 0.9410(3) 0.9379(3) 0.7475(3) 0.0233(8) Uani 1 1 d . . . . .
C85 C 0.8896(2) 0.7855(3) 0.6859(3) 0.0239(8) Uani 1 1 d . . . . .
C86 C 0.8755(2) 0.8126(3) 0.6134(3) 0.0231(8) Uani 1 1 d . . . . .
C87 C 0.8405(3) 0.7602(3) 0.5242(3) 0.0258(9) Uani 1 1 d . . . . .
H87 H 0.819291 0.697872 0.499679 0.031 Uiso 1 1 calc R U . . .
C88 C 0.8389(2) 0.8062(3) 0.4735(3) 0.0238(8) Uani 1 1 d . . . . .
C89 C 0.8089(2) 0.7710(3) 0.3760(3) 0.0232(8) Uani 1 1 d . . . . .
C90 C 0.9428(3) 0.8644(3) 0.8496(3) 0.0263(9) Uani 1 1 d . . . . .
H90A H 0.993062 0.911940 0.891419 0.032 Uiso 1 1 calc R U . . .
H90B H 0.958329 0.806596 0.846156 0.032 Uiso 1 1 calc R U . . .
C91 C 0.2748(3) 0.7865(4) 0.5511(4) 0.0467(13) Uani 1 1 d . . . . .
H91A H 0.245447 0.725339 0.531151 0.070 Uiso 1 1 calc R U . . .
H91B H 0.251667 0.828279 0.593960 0.070 Uiso 1 1 calc R U . . .
H91C H 0.336594 0.791680 0.578310 0.070 Uiso 1 1 calc R U . . .
C92 C 0.2604(3) 0.8085(3) 0.4741(4) 0.0412(12) Uani 1 1 d . . . . .
H92A H 0.282635 0.765860 0.430069 0.049 Uiso 1 1 calc R U . . .
H92B H 0.198006 0.803449 0.446341 0.049 Uiso 1 1 calc R U . . .
C93 C 0.2763(3) 0.9294(3) 0.4386(3) 0.0366(11) Uani 1 1 d . . . . .
H93A H 0.214674 0.933676 0.427433 0.044 Uiso 1 1 calc R U . . .
H93B H 0.283629 0.887845 0.383021 0.044 Uiso 1 1 calc R U . . .
C94 C 0.3295(4) 1.0199(4) 0.4712(4) 0.0462(13) Uani 1 1 d . . . . .
H94A H 0.390444 1.015251 0.482616 0.069 Uiso 1 1 calc R U . . .
H94B H 0.320903 1.061029 0.525514 0.069 Uiso 1 1 calc R U . . .
H94C H 0.311874 1.042636 0.426837 0.069 Uiso 1 1 calc R U . . .
C95 C 0.5797(4) 0.5889(4) -0.1473(4) 0.0506(14) Uani 1 1 d . . . . .
H95A H 0.634230 0.582648 -0.159605 0.076 Uiso 1 1 calc R U . . .
H95B H 0.579016 0.652384 -0.114685 0.076 Uiso 1 1 calc R U . . .
H95C H 0.531809 0.563737 -0.202688 0.076 Uiso 1 1 calc R U . . .
C96 C 0.5705(3) 0.5401(4) -0.0939(4) 0.0473(13) Uani 1 1 d . . . . .
H96A H 0.518180 0.550477 -0.076586 0.057 Uiso 1 1 calc R U . . .
H96B H 0.565454 0.475055 -0.128442 0.057 Uiso 1 1 calc R U . . .
C97 C 0.6397(4) 0.5403(4) 0.0432(4) 0.0471(13) Uani 1 1 d . . . . .
H97A H 0.624409 0.474199 0.014063 0.057 Uiso 1 1 calc R U . . .
H97B H 0.594733 0.564007 0.068925 0.057 Uiso 1 1 calc R U . . .
C98 C 0.7250(4) 0.5693(4) 0.1135(4) 0.0553(16) Uani 1 1 d . . . . .
H98A H 0.766925 0.536424 0.089791 0.083 Uiso 1 1 calc R U . . .
H98B H 0.719640 0.556980 0.161997 0.083 Uiso 1 1 calc R U . . .
H98C H 0.744583 0.633516 0.134755 0.083 Uiso 1 1 calc R U . . .
N1 N 0.0761(2) 0.7312(2) 0.6684(2) 0.0253(7) Uani 1 1 d . . . . .
N2 N -0.0268(2) 0.6956(2) 0.2575(2) 0.0248(7) Uani 1 1 d . . . . .
N3 N 0.2271(2) 0.5275(2) 0.2041(3) 0.0310(8) Uani 1 1 d . . . . .
N4 N 0.3148(2) 0.5388(2) 0.6049(3) 0.0301(8) Uani 1 1 d . . . . .
N5 N 0.6026(2) 0.7620(2) 0.7033(2) 0.0252(7) Uani 1 1 d . . . . .
N6 N 0.5025(2) 0.7512(2) 0.3021(3) 0.0294(8) Uani 1 1 d . . . . .
N7 N 0.8214(2) 0.8451(2) 0.3588(2) 0.0249(7) Uani 1 1 d . . . . .
N8 N 0.9256(2) 0.8635(2) 0.7638(2) 0.0241(7) Uani 1 1 d . . . . .
O1 O 0.10766(19) 0.8808(2) 0.6993(2) 0.0326(7) Uani 1 1 d . . . . .
O2 O 0.00667(19) 0.8493(2) 0.3349(2) 0.0305(7) Uani 1 1 d . . . . .
O3 O -0.0672(2) 0.5453(2) 0.2218(2) 0.0327(7) Uani 1 1 d . . . . .
O4 O 0.01677(19) 0.5803(2) 0.5955(2) 0.0313(7) Uani 1 1 d . . . . .
O5 O 0.36704(19) 0.6062(2) 0.2663(2) 0.0367(8) Uani 1 1 d . . . . .
O6 O 0.44938(19) 0.6049(2) 0.6187(2) 0.0373(8) Uani 1 1 d . . . . .
O7 O 0.17520(19) 0.4589(2) 0.5435(2) 0.0324(7) Uani 1 1 d . . . . .
O8 O 0.1001(2) 0.4382(2) 0.1798(2) 0.0372(8) Uani 1 1 d . . . . .
O9 O 0.5088(2) 0.8626(2) 0.7194(2) 0.0369(8) Uani 1 1 d . . . . .
O10 O 0.4238(2) 0.8575(3) 0.3603(2) 0.0406(8) Uani 1 1 d . . . . .
O11 O 0.5744(2) 0.6315(2) 0.2788(2) 0.0328(7) Uani 1 1 d . . . . .
O12 O 0.6676(2) 0.6441(2) 0.6383(2) 0.0331(7) Uani 1 1 d . . . . .
O13 O 0.8854(2) 0.9941(2) 0.4391(2) 0.0386(8) Uani 1 1 d . . . . .
O14 O 0.9746(2) 1.0127(2) 0.8031(2) 0.0324(7) Uani 1 1 d . . . . .
O15 O 0.8763(2) 0.71117(19) 0.6817(2) 0.0302(7) Uani 1 1 d . . . . .
O16 O 0.78188(19) 0.69485(19) 0.3216(2) 0.0295(7) Uani 1 1 d . . . . .
O17 O 0.3035(2) 0.8968(2) 0.5031(2) 0.0361(7) Uani 1 1 d . . . . .
O18 O 0.6444(2) 0.5728(2) -0.0188(2) 0.0400(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.513(7) . ?
C1 C2 1.526(6) . ?
C1 C6 1.535(7) . ?
C2 C3 1.545(6) . ?
C3 C11 1.534(5) . ?
C3 C4 1.535(6) . ?
C3 C8 1.540(6) . ?
C4 C5 1.541(6) . ?
C5 C6 1.536(6) . ?
C5 C44 1.537(7) . ?
C5 C10 1.538(6) . ?
C7 C9 1.530(7) . ?
C8 C9 1.538(6) . ?
C9 C10 1.524(7) . ?
C11 N1 1.456(5) . ?
C12 O1 1.208(5) . ?
C12 N1 1.394(5) . ?
C12 C13 1.492(6) . ?
C13 C14 1.377(6) . ?
C13 C20 1.400(6) . ?
C14 C15 1.384(6) . ?
C15 C18 1.394(5) . ?
C15 C16 1.492(6) . ?
C16 O2 1.214(5) . ?
C16 N2 1.380(6) . ?
C17 O3 1.207(5) . ?
C17 N2 1.415(5) . ?
C17 C18 1.497(6) . ?
C18 C19 1.390(6) . ?
C19 C20 1.394(6) . ?
C20 C21 1.491(6) . ?
C21 O4 1.213(5) . ?
C21 N1 1.406(5) . ?
C22 N2 1.461(5) . ?
C22 C23 1.538(6) . ?
C23 C28 1.531(6) . ?
C23 C29 1.531(6) . ?
C23 C24 1.538(6) . ?
C24 C25 1.539(6) . ?
C25 C26 1.529(7) . ?
C25 C32 1.538(7) . ?
C26 C27 1.536(6) . ?
C27 C31 1.536(6) . ?
C27 C33 1.540(6) . ?
C27 C28 1.543(6) . ?
C29 C30 1.534(6) . ?
C30 C32 1.522(7) . ?
C30 C31 1.541(7) . ?
C33 N3 1.466(6) . ?
C34 O5 1.216(5) . ?
C34 N3 1.385(6) . ?
C34 C35 1.488(6) . ?
C35 C36 1.387(7) . ?
C35 C42 1.403(6) . ?
C36 C37 1.377(6) . ?
C37 C40 1.395(6) . ?
C37 C38 1.486(7) . ?
C38 O6 1.212(5) . ?
C38 N4 1.398(5) . ?
C39 O7 1.209(5) . ?
C39 N4 1.399(6) . ?
C39 C40 1.491(6) . ?
C40 C41 1.384(6) . ?
C41 C42 1.390(6) . ?
C42 C43 1.480(7) . ?
C43 O8 1.207(5) . ?
C43 N3 1.414(5) . ?
C44 N4 1.460(6) . ?
C46 C52 1.527(7) . ?
C46 C47 1.540(7) . ?
C46 C51 1.543(6) . ?
C47 C48 1.540(6) . ?
C48 C56 1.529(6) . ?
C48 C49 1.533(6) . ?
C48 C53 1.542(6) . ?
C49 C50 1.534(6) . ?
C50 C55 1.534(6) . ?
C50 C51 1.535(6) . ?
C50 C90 1.546(6) . ?
C52 C54 1.528(7) . ?
C53 C54 1.530(6) . ?
C54 C55 1.529(6) . ?
C56 N5 1.465(5) . ?
C57 O9 1.209(5) . ?
C57 N5 1.398(5) . ?
C57 C58 1.496(6) . ?
C58 C66 1.393(6) . ?
C58 C59 1.394(6) . ?
C59 C60 1.386(6) . ?
C60 C64 1.396(6) . ?
C60 C61 1.487(6) . ?
C61 O10 1.211(5) . ?
C61 N6 1.391(6) . ?
C62 O11 1.204(5) . ?
C62 N6 1.399(5) . ?
C62 C64 1.493(6) . ?
C64 C65 1.384(6) . ?
C65 C66 1.391(6) . ?
C66 C67 1.481(6) . ?
C67 O12 1.212(5) . ?
C67 N5 1.397(6) . ?
C68 N6 1.454(6) . ?
C68 C69 1.544(6) . ?
C69 C75 1.529(6) . ?
C69 C70 1.529(6) . ?
C69 C74 1.531(5) . ?
C70 C71 1.528(6) . ?
C71 C78 1.527(7) . ?
C71 C72 1.539(6) . ?
C72 C73 1.527(6) . ?
C73 C79 1.528(5) . ?
C73 C74 1.535(5) . ?
C73 C77 1.539(6) . ?
C75 C76 1.532(6) . ?
C76 C78 1.524(7) . ?
C76 C77 1.539(6) . ?
C79 N7 1.462(5) . ?
C80 O13 1.205(5) . ?
C80 N7 1.401(5) . ?
C80 C81 1.484(6) . ?
C81 C82 1.389(6) . ?
C81 C88 1.393(6) . ?
C82 C83 1.380(6) . ?
C83 C86 1.402(6) . ?
C83 C84 1.496(6) . ?
C84 O14 1.210(5) . ?
C84 N8 1.402(5) . ?
C85 O15 1.212(5) . ?
C85 N8 1.400(5) . ?
C85 C86 1.481(6) . ?
C86 C87 1.382(6) . ?
C87 C88 1.385(6) . ?
C88 C89 1.494(6) . ?
C89 O16 1.205(5) . ?
C89 N7 1.399(5) . ?
C90 N8 1.453(5) . ?
C91 C92 1.501(7) . ?
C92 O17 1.417(6) . ?
C93 O17 1.422(6) . ?
C93 C94 1.501(7) . ?
C95 C96 1.499(7) . ?
C96 O18 1.411(6) . ?
C97 O18 1.416(6) . ?
C97 C98 1.492(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 110.0(4) . . ?
C7 C1 C6 109.5(4) . . ?
C2 C1 C6 108.2(4) . . ?
C1 C2 C3 110.8(3) . . ?
C11 C3 C4 111.6(4) . . ?
C11 C3 C8 108.0(3) . . ?
C4 C3 C8 108.9(4) . . ?
C11 C3 C2 111.5(3) . . ?
C4 C3 C2 108.3(3) . . ?
C8 C3 C2 108.5(4) . . ?
C3 C4 C5 111.1(4) . . ?
C6 C5 C44 111.6(4) . . ?
C6 C5 C10 108.5(4) . . ?
C44 C5 C10 108.9(4) . . ?
C6 C5 C4 108.7(3) . . ?
C44 C5 C4 111.0(4) . . ?
C10 C5 C4 108.0(4) . . ?
C1 C6 C5 110.8(4) . . ?
C1 C7 C9 110.0(4) . . ?
C9 C8 C3 109.9(4) . . ?
C10 C9 C7 109.8(4) . . ?
C10 C9 C8 109.1(4) . . ?
C7 C9 C8 109.3(4) . . ?
C9 C10 C5 110.7(4) . . ?
N1 C11 C3 113.4(3) . . ?
O1 C12 N1 125.9(4) . . ?
O1 C12 C13 128.3(4) . . ?
N1 C12 C13 105.8(3) . . ?
C14 C13 C20 122.8(4) . . ?
C14 C13 C12 128.7(4) . . ?
C20 C13 C12 108.5(4) . . ?
C13 C14 C15 114.4(4) . . ?
C14 C15 C18 123.4(4) . . ?
C14 C15 C16 128.6(4) . . ?
C18 C15 C16 108.0(4) . . ?
O2 C16 N2 125.6(4) . . ?
O2 C16 C15 127.7(4) . . ?
N2 C16 C15 106.6(3) . . ?
O3 C17 N2 124.9(4) . . ?
O3 C17 C18 129.5(4) . . ?
N2 C17 C18 105.6(3) . . ?
C19 C18 C15 122.4(4) . . ?
C19 C18 C17 129.8(4) . . ?
C15 C18 C17 107.8(3) . . ?
C18 C19 C20 114.2(4) . . ?
C19 C20 C13 122.7(4) . . ?
C19 C20 C21 129.8(4) . . ?
C13 C20 C21 107.4(4) . . ?
O4 C21 N1 124.1(4) . . ?
O4 C21 C20 129.8(4) . . ?
N1 C21 C20 106.1(3) . . ?
N2 C22 C23 114.3(3) . . ?
C28 C23 C29 109.0(4) . . ?
C28 C23 C22 110.5(3) . . ?
C29 C23 C22 108.1(3) . . ?
C28 C23 C24 108.9(3) . . ?
C29 C23 C24 108.0(3) . . ?
C22 C23 C24 112.3(4) . . ?
C23 C24 C25 110.5(4) . . ?
C26 C25 C32 109.9(4) . . ?
C26 C25 C24 109.3(4) . . ?
C32 C25 C24 108.9(4) . . ?
C25 C26 C27 110.3(4) . . ?
C31 C27 C26 108.3(4) . . ?
C31 C27 C33 108.5(4) . . ?
C26 C27 C33 111.2(4) . . ?
C31 C27 C28 109.0(4) . . ?
C26 C27 C28 108.9(4) . . ?
C33 C27 C28 110.9(4) . . ?
C23 C28 C27 111.1(3) . . ?
C23 C29 C30 110.7(4) . . ?
C32 C30 C29 109.4(4) . . ?
C32 C30 C31 109.3(4) . . ?
C29 C30 C31 109.6(4) . . ?
C27 C31 C30 110.1(4) . . ?
C30 C32 C25 109.3(4) . . ?
N3 C33 C27 113.9(4) . . ?
O5 C34 N3 125.7(4) . . ?
O5 C34 C35 128.1(4) . . ?
N3 C34 C35 106.2(4) . . ?
C36 C35 C42 122.9(4) . . ?
C36 C35 C34 129.3(4) . . ?
C42 C35 C34 107.7(4) . . ?
C37 C36 C35 114.9(4) . . ?
C36 C37 C40 122.4(4) . . ?
C36 C37 C38 129.2(4) . . ?
C40 C37 C38 108.3(4) . . ?
O6 C38 N4 125.8(5) . . ?
O6 C38 C37 128.2(4) . . ?
N4 C38 C37 106.0(4) . . ?
O7 C39 N4 125.1(4) . . ?
O7 C39 C40 128.7(4) . . ?
N4 C39 C40 106.2(4) . . ?
C41 C40 C37 123.1(4) . . ?
C41 C40 C39 129.3(4) . . ?
C37 C40 C39 107.6(4) . . ?
C40 C41 C42 114.8(4) . . ?
C41 C42 C35 121.8(4) . . ?
C41 C42 C43 129.9(4) . . ?
C35 C42 C43 108.3(4) . . ?
O8 C43 N3 125.2(4) . . ?
O8 C43 C42 129.4(4) . . ?
N3 C43 C42 105.4(4) . . ?
N4 C44 C5 113.8(3) . . ?
C52 C46 C47 109.9(4) . . ?
C52 C46 C51 109.9(4) . . ?
C47 C46 C51 108.7(4) . . ?
C46 C47 C48 109.8(4) . . ?
C56 C48 C49 111.7(4) . . ?
C56 C48 C47 111.1(4) . . ?
C49 C48 C47 108.8(3) . . ?
C56 C48 C53 108.2(3) . . ?
C49 C48 C53 107.9(4) . . ?
C47 C48 C53 109.0(4) . . ?
C48 C49 C50 111.2(4) . . ?
C49 C50 C55 109.0(3) . . ?
C49 C50 C51 108.9(4) . . ?
C55 C50 C51 109.5(4) . . ?
C49 C50 C90 111.0(4) . . ?
C55 C50 C90 107.4(3) . . ?
C51 C50 C90 111.1(3) . . ?
C50 C51 C46 109.4(4) . . ?
C46 C52 C54 109.8(4) . . ?
C54 C53 C48 110.5(4) . . ?
C52 C54 C55 109.4(4) . . ?
C52 C54 C53 109.2(4) . . ?
C55 C54 C53 109.8(4) . . ?
C54 C55 C50 109.7(4) . . ?
N5 C56 C48 114.1(3) . . ?
O9 C57 N5 125.5(4) . . ?
O9 C57 C58 128.4(4) . . ?
N5 C57 C58 106.1(4) . . ?
C66 C58 C59 122.8(4) . . ?
C66 C58 C57 107.3(4) . . ?
C59 C58 C57 129.9(4) . . ?
C60 C59 C58 114.8(4) . . ?
C59 C60 C64 122.3(4) . . ?
C59 C60 C61 130.0(4) . . ?
C64 C60 C61 107.7(4) . . ?
O10 C61 N6 125.6(4) . . ?
O10 C61 C60 128.1(4) . . ?
N6 C61 C60 106.3(4) . . ?
O11 C62 N6 125.7(4) . . ?
O11 C62 C64 128.8(4) . . ?
N6 C62 C64 105.6(4) . . ?
C65 C64 C60 123.0(4) . . ?
C65 C64 C62 128.9(4) . . ?
C60 C64 C62 108.1(4) . . ?
C64 C65 C66 114.9(4) . . ?
C65 C66 C58 122.2(4) . . ?
C65 C66 C67 129.1(4) . . ?
C58 C66 C67 108.6(4) . . ?
O12 C67 N5 125.3(4) . . ?
O12 C67 C66 128.6(4) . . ?
N5 C67 C66 106.0(3) . . ?
N6 C68 C69 114.3(4) . . ?
C75 C69 C70 109.0(4) . . ?
C75 C69 C74 108.7(3) . . ?
C70 C69 C74 109.1(4) . . ?
C75 C69 C68 107.8(4) . . ?
C70 C69 C68 111.7(4) . . ?
C74 C69 C68 110.4(3) . . ?
C71 C70 C69 110.5(4) . . ?
C78 C71 C70 109.7(4) . . ?
C78 C71 C72 109.4(4) . . ?
C70 C71 C72 108.7(4) . . ?
C73 C72 C71 110.4(4) . . ?
C72 C73 C79 111.7(4) . . ?
C72 C73 C74 109.1(3) . . ?
C79 C73 C74 110.4(3) . . ?
C72 C73 C77 108.9(3) . . ?
C79 C73 C77 108.4(3) . . ?
C74 C73 C77 108.3(3) . . ?
C69 C74 C73 111.0(3) . . ?
C69 C75 C76 109.5(4) . . ?
C78 C76 C75 110.3(4) . . ?
C78 C76 C77 109.5(4) . . ?
C75 C76 C77 109.6(4) . . ?
C73 C77 C76 109.5(4) . . ?
C76 C78 C71 109.2(4) . . ?
N7 C79 C73 114.2(3) . . ?
O13 C80 N7 124.8(4) . . ?
O13 C80 C81 128.7(4) . . ?
N7 C80 C81 106.4(3) . . ?
C82 C81 C88 122.6(4) . . ?
C82 C81 C80 129.5(4) . . ?
C88 C81 C80 107.9(4) . . ?
C83 C82 C81 114.8(4) . . ?
C82 C83 C86 122.2(4) . . ?
C82 C83 C84 129.9(4) . . ?
C86 C83 C84 107.8(3) . . ?
O14 C84 N8 125.1(4) . . ?
O14 C84 C83 129.0(4) . . ?
N8 C84 C83 105.9(3) . . ?
O15 C85 N8 124.7(4) . . ?
O15 C85 C86 128.7(4) . . ?
N8 C85 C86 106.5(3) . . ?
C87 C86 C83 123.1(4) . . ?
C87 C86 C85 128.9(4) . . ?
C83 C86 C85 108.0(4) . . ?
C86 C87 C88 114.4(4) . . ?
C87 C88 C81 122.8(4) . . ?
C87 C88 C89 129.0(4) . . ?
C81 C88 C89 108.1(3) . . ?
O16 C89 N7 125.6(4) . . ?
O16 C89 C88 128.5(4) . . ?
N7 C89 C88 105.9(3) . . ?
N8 C90 C50 114.4(3) . . ?
O17 C92 C91 109.3(4) . . ?
O17 C93 C94 108.8(4) . . ?
O18 C96 C95 107.6(4) . . ?
O18 C97 C98 108.9(4) . . ?
C12 N1 C21 111.8(3) . . ?
C12 N1 C11 124.8(4) . . ?
C21 N1 C11 123.3(3) . . ?
C16 N2 C17 111.8(3) . . ?
C16 N2 C22 123.2(3) . . ?
C17 N2 C22 125.0(4) . . ?
C34 N3 C43 112.1(4) . . ?
C34 N3 C33 124.3(4) . . ?
C43 N3 C33 123.6(4) . . ?
C38 N4 C39 111.7(4) . . ?
C38 N4 C44 125.0(4) . . ?
C39 N4 C44 123.3(4) . . ?
C67 N5 C57 111.5(4) . . ?
C67 N5 C56 123.0(3) . . ?
C57 N5 C56 124.7(4) . . ?
C61 N6 C62 111.9(4) . . ?
C61 N6 C68 123.9(4) . . ?
C62 N6 C68 123.7(4) . . ?
C89 N7 C80 111.5(3) . . ?
C89 N7 C79 124.4(4) . . ?
C80 N7 C79 124.0(3) . . ?
C85 N8 C84 111.7(3) . . ?
C85 N8 C90 122.5(3) . . ?
C84 N8 C90 125.8(3) . . ?
C92 O17 C93 112.0(4) . . ?
C96 O18 C97 113.7(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
C7 C1 C2 C3 -58.9(5) . . . . ?
C6 C1 C2 C3 60.7(5) . . . . ?
C1 C2 C3 C11 176.9(4) . . . . ?
C1 C2 C3 C4 -59.9(5) . . . . ?
C1 C2 C3 C8 58.2(5) . . . . ?
C11 C3 C4 C5 -178.4(3) . . . . ?
C8 C3 C4 C5 -59.3(4) . . . . ?
C2 C3 C4 C5 58.5(4) . . . . ?
C3 C4 C5 C6 -58.5(5) . . . . ?
C3 C4 C5 C44 178.5(3) . . . . ?
C3 C4 C5 C10 59.1(5) . . . . ?
C7 C1 C6 C5 59.5(5) . . . . ?
C2 C1 C6 C5 -60.4(5) . . . . ?
C44 C5 C6 C1 -178.1(4) . . . . ?
C10 C5 C6 C1 -58.1(5) . . . . ?
C4 C5 C6 C1 59.2(5) . . . . ?
C2 C1 C7 C9 59.5(5) . . . . ?
C6 C1 C7 C9 -59.3(5) . . . . ?
C11 C3 C8 C9 -179.7(4) . . . . ?
C4 C3 C8 C9 59.0(5) . . . . ?
C2 C3 C8 C9 -58.7(5) . . . . ?
C1 C7 C9 C10 59.5(5) . . . . ?
C1 C7 C9 C8 -60.2(5) . . . . ?
C3 C8 C9 C10 -59.9(5) . . . . ?
C3 C8 C9 C7 60.2(5) . . . . ?
C7 C9 C10 C5 -59.2(5) . . . . ?
C8 C9 C10 C5 60.7(5) . . . . ?
C6 C5 C10 C9 58.1(5) . . . . ?
C44 C5 C10 C9 179.7(4) . . . . ?
C4 C5 C10 C9 -59.7(5) . . . . ?
C4 C3 C11 N1 -54.9(5) . . . . ?
C8 C3 C11 N1 -174.5(4) . . . . ?
C2 C3 C11 N1 66.3(5) . . . . ?
O1 C12 C13 C14 2.3(7) . . . . ?
N1 C12 C13 C14 -177.7(4) . . . . ?
O1 C12 C13 C20 -176.9(4) . . . . ?
N1 C12 C13 C20 3.0(4) . . . . ?
C20 C13 C14 C15 -1.3(6) . . . . ?
C12 C13 C14 C15 179.6(4) . . . . ?
C13 C14 C15 C18 -0.4(6) . . . . ?
C13 C14 C15 C16 -179.3(4) . . . . ?
C14 C15 C16 O2 -7.8(7) . . . . ?
C18 C15 C16 O2 173.2(4) . . . . ?
C14 C15 C16 N2 174.0(4) . . . . ?
C18 C15 C16 N2 -5.0(4) . . . . ?
C14 C15 C18 C19 2.2(6) . . . . ?
C16 C15 C18 C19 -178.8(4) . . . . ?
C14 C15 C18 C17 -176.5(4) . . . . ?
C16 C15 C18 C17 2.6(4) . . . . ?
O3 C17 C18 C19 3.1(7) . . . . ?
N2 C17 C18 C19 -177.9(4) . . . . ?
O3 C17 C18 C15 -178.4(4) . . . . ?
N2 C17 C18 C15 0.6(4) . . . . ?
C15 C18 C19 C20 -2.0(6) . . . . ?
C17 C18 C19 C20 176.3(4) . . . . ?
C18 C19 C20 C13 0.3(6) . . . . ?
C18 C19 C20 C21 -179.5(4) . . . . ?
C14 C13 C20 C19 1.4(6) . . . . ?
C12 C13 C20 C19 -179.3(4) . . . . ?
C14 C13 C20 C21 -178.8(4) . . . . ?
C12 C13 C20 C21 0.5(4) . . . . ?
C19 C20 C21 O4 -4.5(7) . . . . ?
C13 C20 C21 O4 175.7(4) . . . . ?
C19 C20 C21 N1 175.9(4) . . . . ?
C13 C20 C21 N1 -3.9(4) . . . . ?
N2 C22 C23 C28 58.1(5) . . . . ?
N2 C22 C23 C29 177.3(4) . . . . ?
N2 C22 C23 C24 -63.7(5) . . . . ?
C28 C23 C24 C25 58.7(5) . . . . ?
C29 C23 C24 C25 -59.5(5) . . . . ?
C22 C23 C24 C25 -178.6(4) . . . . ?
C23 C24 C25 C26 -59.6(5) . . . . ?
C23 C24 C25 C32 60.5(5) . . . . ?
C32 C25 C26 C27 -59.7(5) . . . . ?
C24 C25 C26 C27 59.8(5) . . . . ?
C25 C26 C27 C31 59.3(5) . . . . ?
C25 C26 C27 C33 178.4(4) . . . . ?
C25 C26 C27 C28 -59.1(5) . . . . ?
C29 C23 C28 C27 58.9(5) . . . . ?
C22 C23 C28 C27 177.5(4) . . . . ?
C24 C23 C28 C27 -58.7(5) . . . . ?
C31 C27 C28 C23 -59.0(5) . . . . ?
C26 C27 C28 C23 59.0(5) . . . . ?
C33 C27 C28 C23 -178.4(4) . . . . ?
C28 C23 C29 C30 -58.8(5) . . . . ?
C22 C23 C29 C30 -179.0(4) . . . . ?
C24 C23 C29 C30 59.3(5) . . . . ?
C23 C29 C30 C32 -60.6(5) . . . . ?
C23 C29 C30 C31 59.2(5) . . . . ?
C26 C27 C31 C30 -59.9(5) . . . . ?
C33 C27 C31 C30 179.3(4) . . . . ?
C28 C27 C31 C30 58.5(5) . . . . ?
C32 C30 C31 C27 60.9(5) . . . . ?
C29 C30 C31 C27 -58.9(5) . . . . ?
C29 C30 C32 C25 60.2(5) . . . . ?
C31 C30 C32 C25 -59.8(5) . . . . ?
C26 C25 C32 C30 59.6(5) . . . . ?
C24 C25 C32 C30 -60.2(5) . . . . ?
C31 C27 C33 N3 -173.8(3) . . . . ?
C26 C27 C33 N3 67.2(5) . . . . ?
C28 C27 C33 N3 -54.1(5) . . . . ?
O5 C34 C35 C36 -0.3(8) . . . . ?
N3 C34 C35 C36 -179.8(4) . . . . ?
O5 C34 C35 C42 178.4(5) . . . . ?
N3 C34 C35 C42 -1.0(5) . . . . ?
C42 C35 C36 C37 -1.1(6) . . . . ?
C34 C35 C36 C37 177.5(4) . . . . ?
C35 C36 C37 C40 -0.2(6) . . . . ?
C35 C36 C37 C38 179.1(4) . . . . ?
C36 C37 C38 O6 -2.7(8) . . . . ?
C40 C37 C38 O6 176.7(4) . . . . ?
C36 C37 C38 N4 178.0(4) . . . . ?
C40 C37 C38 N4 -2.7(5) . . . . ?
C36 C37 C40 C41 1.5(7) . . . . ?
C38 C37 C40 C41 -177.9(4) . . . . ?
C36 C37 C40 C39 -180.0(4) . . . . ?
C38 C37 C40 C39 0.6(5) . . . . ?
O7 C39 C40 C41 2.2(7) . . . . ?
N4 C39 C40 C41 -180.0(4) . . . . ?
O7 C39 C40 C37 -176.2(4) . . . . ?
N4 C39 C40 C37 1.7(5) . . . . ?
C37 C40 C41 C42 -1.4(6) . . . . ?
C39 C40 C41 C42 -179.5(4) . . . . ?
C40 C41 C42 C35 0.0(6) . . . . ?
C40 C41 C42 C43 177.8(4) . . . . ?
C36 C35 C42 C41 1.2(7) . . . . ?
C34 C35 C42 C41 -177.6(4) . . . . ?
C36 C35 C42 C43 -176.9(4) . . . . ?
C34 C35 C42 C43 4.2(5) . . . . ?
C41 C42 C43 O8 -5.1(8) . . . . ?
C35 C42 C43 O8 172.9(5) . . . . ?
C41 C42 C43 N3 176.3(4) . . . . ?
C35 C42 C43 N3 -5.8(5) . . . . ?
C6 C5 C44 N4 -61.5(5) . . . . ?
C10 C5 C44 N4 178.7(4) . . . . ?
C4 C5 C44 N4 59.9(5) . . . . ?
C52 C46 C47 C48 -59.3(5) . . . . ?
C51 C46 C47 C48 61.0(5) . . . . ?
C46 C47 C48 C56 177.4(4) . . . . ?
C46 C47 C48 C49 -59.3(5) . . . . ?
C46 C47 C48 C53 58.2(5) . . . . ?
C56 C48 C49 C50 -178.2(3) . . . . ?
C47 C48 C49 C50 58.8(5) . . . . ?
C53 C48 C49 C50 -59.4(5) . . . . ?
C48 C49 C50 C55 60.0(5) . . . . ?
C48 C49 C50 C51 -59.4(4) . . . . ?
C48 C49 C50 C90 178.0(3) . . . . ?
C49 C50 C51 C46 60.1(5) . . . . ?
C55 C50 C51 C46 -59.0(5) . . . . ?
C90 C50 C51 C46 -177.4(4) . . . . ?
C52 C46 C51 C50 59.0(5) . . . . ?
C47 C46 C51 C50 -61.3(5) . . . . ?
C47 C46 C52 C54 60.1(5) . . . . ?
C51 C46 C52 C54 -59.5(5) . . . . ?
C56 C48 C53 C54 -179.9(4) . . . . ?
C49 C48 C53 C54 59.0(5) . . . . ?
C47 C48 C53 C54 -59.0(5) . . . . ?
C46 C52 C54 C55 60.0(5) . . . . ?
C46 C52 C54 C53 -60.1(5) . . . . ?
C48 C53 C54 C52 59.9(5) . . . . ?
C48 C53 C54 C55 -60.0(5) . . . . ?
C52 C54 C55 C50 -60.3(5) . . . . ?
C53 C54 C55 C50 59.5(5) . . . . ?
C49 C50 C55 C54 -58.9(5) . . . . ?
C51 C50 C55 C54 60.1(5) . . . . ?
C90 C50 C55 C54 -179.3(4) . . . . ?
C49 C48 C56 N5 -52.0(5) . . . . ?
C47 C48 C56 N5 69.7(5) . . . . ?
C53 C48 C56 N5 -170.6(4) . . . . ?
O9 C57 C58 C66 -175.1(4) . . . . ?
N5 C57 C58 C66 4.3(4) . . . . ?
O9 C57 C58 C59 6.4(8) . . . . ?
N5 C57 C58 C59 -174.2(4) . . . . ?
C66 C58 C59 C60 -0.7(6) . . . . ?
C57 C58 C59 C60 177.7(4) . . . . ?
C58 C59 C60 C64 1.2(6) . . . . ?
C58 C59 C60 C61 -176.6(4) . . . . ?
C59 C60 C61 O10 -4.6(8) . . . . ?
C64 C60 C61 O10 177.4(5) . . . . ?
C59 C60 C61 N6 175.9(4) . . . . ?
C64 C60 C61 N6 -2.2(5) . . . . ?
C59 C60 C64 C65 -0.7(7) . . . . ?
C61 C60 C64 C65 177.5(4) . . . . ?
C59 C60 C64 C62 180.0(4) . . . . ?
C61 C60 C64 C62 -1.8(5) . . . . ?
O11 C62 C64 C65 6.1(7) . . . . ?
N6 C62 C64 C65 -174.2(4) . . . . ?
O11 C62 C64 C60 -174.6(4) . . . . ?
N6 C62 C64 C60 5.1(4) . . . . ?
C60 C64 C65 C66 -0.3(6) . . . . ?
C62 C64 C65 C66 178.9(4) . . . . ?
C64 C65 C66 C58 0.8(6) . . . . ?
C64 C65 C66 C67 -177.6(4) . . . . ?
C59 C58 C66 C65 -0.3(6) . . . . ?
C57 C58 C66 C65 -179.0(4) . . . . ?
C59 C58 C66 C67 178.4(4) . . . . ?
C57 C58 C66 C67 -0.3(4) . . . . ?
C65 C66 C67 O12 -5.1(7) . . . . ?
C58 C66 C67 O12 176.4(4) . . . . ?
C65 C66 C67 N5 174.7(4) . . . . ?
C58 C66 C67 N5 -3.8(4) . . . . ?
N6 C68 C69 C75 169.0(4) . . . . ?
N6 C68 C69 C70 -71.2(5) . . . . ?
N6 C68 C69 C74 50.4(5) . . . . ?
C75 C69 C70 C71 -59.2(5) . . . . ?
C74 C69 C70 C71 59.3(5) . . . . ?
C68 C69 C70 C71 -178.3(4) . . . . ?
C69 C70 C71 C78 59.5(5) . . . . ?
C69 C70 C71 C72 -60.0(5) . . . . ?
C78 C71 C72 C73 -59.8(5) . . . . ?
C70 C71 C72 C73 60.0(5) . . . . ?
C71 C72 C73 C79 178.6(3) . . . . ?
C71 C72 C73 C74 -59.0(5) . . . . ?
C71 C72 C73 C77 59.0(4) . . . . ?
C75 C69 C74 C73 60.4(5) . . . . ?
C70 C69 C74 C73 -58.4(4) . . . . ?
C68 C69 C74 C73 178.5(4) . . . . ?
C72 C73 C74 C69 58.4(5) . . . . ?
C79 C73 C74 C69 -178.5(4) . . . . ?
C77 C73 C74 C69 -60.0(4) . . . . ?
C70 C69 C75 C76 59.0(5) . . . . ?
C74 C69 C75 C76 -59.8(5) . . . . ?
C68 C69 C75 C76 -179.5(4) . . . . ?
C69 C75 C76 C78 -60.1(5) . . . . ?
C69 C75 C76 C77 60.6(5) . . . . ?
C72 C73 C77 C76 -59.2(4) . . . . ?
C79 C73 C77 C76 179.1(4) . . . . ?
C74 C73 C77 C76 59.3(4) . . . . ?
C78 C76 C77 C73 60.7(5) . . . . ?
C75 C76 C77 C73 -60.4(5) . . . . ?
C75 C76 C78 C71 59.8(5) . . . . ?
C77 C76 C78 C71 -61.0(5) . . . . ?
C70 C71 C78 C76 -59.1(5) . . . . ?
C72 C71 C78 C76 60.1(5) . . . . ?
C72 C73 C79 N7 69.6(4) . . . . ?
C74 C73 C79 N7 -52.0(5) . . . . ?
C77 C73 C79 N7 -170.4(3) . . . . ?
O13 C80 C81 C82 0.8(8) . . . . ?
N7 C80 C81 C82 179.6(4) . . . . ?
O13 C80 C81 C88 -177.3(5) . . . . ?
N7 C80 C81 C88 1.5(5) . . . . ?
C88 C81 C82 C83 -1.3(6) . . . . ?
C80 C81 C82 C83 -179.1(4) . . . . ?
C81 C82 C83 C86 1.6(6) . . . . ?
C81 C82 C83 C84 -179.2(4) . . . . ?
C82 C83 C84 O14 0.2(7) . . . . ?
C86 C83 C84 O14 179.5(4) . . . . ?
C82 C83 C84 N8 -179.1(4) . . . . ?
C86 C83 C84 N8 0.2(4) . . . . ?
C82 C83 C86 C87 -0.4(6) . . . . ?
C84 C83 C86 C87 -179.7(4) . . . . ?
C82 C83 C86 C85 177.0(4) . . . . ?
C84 C83 C86 C85 -2.4(4) . . . . ?
O15 C85 C86 C87 3.2(7) . . . . ?
N8 C85 C86 C87 -179.1(4) . . . . ?
O15 C85 C86 C83 -174.0(4) . . . . ?
N8 C85 C86 C83 3.7(4) . . . . ?
C83 C86 C87 C88 -1.3(6) . . . . ?
C85 C86 C87 C88 -178.1(4) . . . . ?
C86 C87 C88 C81 1.7(6) . . . . ?
C86 C87 C88 C89 177.6(4) . . . . ?
C82 C81 C88 C87 -0.4(6) . . . . ?
C80 C81 C88 C87 177.8(4) . . . . ?
C82 C81 C88 C89 -177.1(4) . . . . ?
C80 C81 C88 C89 1.1(4) . . . . ?
C87 C88 C89 O16 -2.0(7) . . . . ?
C81 C88 C89 O16 174.5(4) . . . . ?
C87 C88 C89 N7 -179.8(4) . . . . ?
C81 C88 C89 N7 -3.3(4) . . . . ?
C49 C50 C90 N8 51.1(5) . . . . ?
C55 C50 C90 N8 170.2(4) . . . . ?
C51 C50 C90 N8 -70.1(5) . . . . ?
O1 C12 N1 C21 174.3(4) . . . . ?
C13 C12 N1 C21 -5.7(4) . . . . ?
O1 C12 N1 C11 -3.4(6) . . . . ?
C13 C12 N1 C11 176.7(3) . . . . ?
O4 C21 N1 C12 -173.6(4) . . . . ?
C20 C21 N1 C12 6.0(4) . . . . ?
O4 C21 N1 C11 4.1(6) . . . . ?
C20 C21 N1 C11 -176.3(3) . . . . ?
C3 C11 N1 C12 -88.7(5) . . . . ?
C3 C11 N1 C21 93.9(4) . . . . ?
O2 C16 N2 C17 -172.7(4) . . . . ?
C15 C16 N2 C17 5.5(4) . . . . ?
O2 C16 N2 C22 5.0(6) . . . . ?
C15 C16 N2 C22 -176.8(3) . . . . ?
O3 C17 N2 C16 175.2(4) . . . . ?
C18 C17 N2 C16 -3.9(4) . . . . ?
O3 C17 N2 C22 -2.5(6) . . . . ?
C18 C17 N2 C22 178.4(3) . . . . ?
C23 C22 N2 C16 84.3(5) . . . . ?
C23 C22 N2 C17 -98.4(5) . . . . ?
O5 C34 N3 C43 177.7(4) . . . . ?
C35 C34 N3 C43 -2.8(5) . . . . ?
O5 C34 N3 C33 -2.8(7) . . . . ?
C35 C34 N3 C33 176.7(4) . . . . ?
O8 C43 N3 C34 -173.5(4) . . . . ?
C42 C43 N3 C34 5.3(5) . . . . ?
O8 C43 N3 C33 7.1(7) . . . . ?
C42 C43 N3 C33 -174.2(4) . . . . ?
C27 C33 N3 C34 -91.0(5) . . . . ?
C27 C33 N3 C43 88.5(5) . . . . ?
O6 C38 N4 C39 -175.5(4) . . . . ?
C37 C38 N4 C39 3.9(5) . . . . ?
O6 C38 N4 C44 5.5(7) . . . . ?
C37 C38 N4 C44 -175.1(4) . . . . ?
O7 C39 N4 C38 174.4(4) . . . . ?
C40 C39 N4 C38 -3.5(5) . . . . ?
O7 C39 N4 C44 -6.5(7) . . . . ?
C40 C39 N4 C44 175.5(4) . . . . ?
C5 C44 N4 C38 87.0(5) . . . . ?
C5 C44 N4 C39 -91.8(5) . . . . ?
O12 C67 N5 C57 -173.4(4) . . . . ?
C66 C67 N5 C57 6.8(4) . . . . ?
O12 C67 N5 C56 -3.1(6) . . . . ?
C66 C67 N5 C56 177.1(3) . . . . ?
O9 C57 N5 C67 172.4(4) . . . . ?
C58 C57 N5 C67 -7.0(4) . . . . ?
O9 C57 N5 C56 2.3(7) . . . . ?
C58 C57 N5 C56 -177.1(3) . . . . ?
C48 C56 N5 C67 95.7(5) . . . . ?
C48 C56 N5 C57 -95.3(5) . . . . ?
O10 C61 N6 C62 -173.9(4) . . . . ?
C60 C61 N6 C62 5.7(5) . . . . ?
O10 C61 N6 C68 -1.4(7) . . . . ?
C60 C61 N6 C68 178.2(4) . . . . ?
O11 C62 N6 C61 173.0(4) . . . . ?
C64 C62 N6 C61 -6.7(5) . . . . ?
O11 C62 N6 C68 0.5(7) . . . . ?
C64 C62 N6 C68 -179.3(3) . . . . ?
C69 C68 N6 C61 94.2(5) . . . . ?
C69 C68 N6 C62 -94.1(5) . . . . ?
O16 C89 N7 C80 -173.5(4) . . . . ?
C88 C89 N7 C80 4.4(4) . . . . ?
O16 C89 N7 C79 3.2(6) . . . . ?
C88 C89 N7 C79 -178.9(3) . . . . ?
O13 C80 N7 C89 175.1(4) . . . . ?
C81 C80 N7 C89 -3.8(5) . . . . ?
O13 C80 N7 C79 -1.6(7) . . . . ?
C81 C80 N7 C79 179.6(3) . . . . ?
C73 C79 N7 C89 92.6(5) . . . . ?
C73 C79 N7 C80 -91.2(5) . . . . ?
O15 C85 N8 C84 174.1(4) . . . . ?
C86 C85 N8 C84 -3.7(4) . . . . ?
O15 C85 N8 C90 -6.7(6) . . . . ?
C86 C85 N8 C90 175.5(3) . . . . ?
O14 C84 N8 C85 -177.1(4) . . . . ?
C83 C84 N8 C85 2.3(4) . . . . ?
O14 C84 N8 C90 3.7(6) . . . . ?
C83 C84 N8 C90 -176.9(3) . . . . ?
C50 C90 N8 C85 -88.8(5) . . . . ?
C50 C90 N8 C84 90.3(5) . . . . ?
C91 C92 O17 C93 -166.0(4) . . . . ?
C94 C93 O17 C92 -175.7(4) . . . . ?
C95 C96 O18 C97 172.7(5) . . . . ?
C98 C97 O18 C96 172.6(5) . . . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2389268'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C59 H51 Br2 Cl15 N4 O10'
_chemical_formula_weight         1667.60

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.6670(8)
_cell_length_b                   22.9197(19)
_cell_length_c                   15.4712(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.877(3)
_cell_angle_gamma                90
_cell_volume                     3386.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       plate
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             1676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    7.457
_shelx_estimated_absorpt_T_min   0.523
_shelx_estimated_absorpt_T_max   0.707
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5363
_exptl_absorpt_correction_T_max  0.8526
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            44054
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.475
_diffrn_reflns_theta_max         78.900
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             7202
_reflns_number_gt                6548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+12.2921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7202
_refine_ls_number_parameters     498
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C34 C 0.2225(17) 0.5096(6) 0.1068(9) 0.024(4) Uani 0.380(19) 1 d . . P A -4
H34 H 0.144885 0.535209 0.120410 0.029 Uiso 0.380(19) 1 calc R U P A -4
Cl6 Cl 0.1899(17) 0.4642(9) 0.0159(12) 0.081(5) Uani 0.380(19) 1 d . . P A -4
Cl7 Cl 0.3981(10) 0.5429(6) 0.1073(5) 0.091(4) Uani 0.380(19) 1 d . . P A -4
Cl8 Cl 0.2909(12) 0.4614(6) 0.1817(8) 0.097(3) Uani 0.380(19) 1 d . . P A -4
C33 C 0.219(3) 0.5080(10) 0.1081(14) 0.109(9) Uani 0.620(19) 1 d . . P A -3
H33 H 0.127109 0.525614 0.115524 0.131 Uiso 0.620(19) 1 calc R U P A -3
Cl3 Cl 0.1824(7) 0.4749(4) 0.0046(6) 0.0530(11) Uani 0.620(19) 1 d . . P A -3
Cl4 Cl 0.3233(18) 0.5691(4) 0.0991(6) 0.140(4) Uani 0.620(19) 1 d . . P A -3
Cl5 Cl 0.2624(7) 0.4664(2) 0.2039(5) 0.0672(13) Uani 0.620(19) 1 d . . P A -3
C36 C 0.191(2) 0.6430(8) -0.1223(9) 0.070(5) Uani 0.483(4) 1 d D U P B -2
H36 H 0.200368 0.680418 -0.154116 0.084 Uiso 0.483(4) 1 calc R U P B -2
Cl12 Cl 0.0397(4) 0.61423(18) -0.1534(3) 0.0604(10) Uani 0.483(4) 1 d . . P B
-2
Cl13 Cl 0.3307(4) 0.59505(13) -0.1357(2) 0.0394(7) Uani 0.483(4) 1 d . . P B -2
Cl14 Cl 0.2001(4) 0.65641(19) -0.0056(2) 0.0884(14) Uani 0.483(4) 1 d D . P B
-2
C35 C 0.202(2) 0.6537(13) -0.1537(12) 0.117(9) Uani 0.517(4) 1 d . . P B -1
H35 H 0.207217 0.671837 -0.211876 0.140 Uiso 0.517(4) 1 calc R U P B -1
Cl9 Cl 0.2336(4) 0.70676(18) -0.0717(2) 0.0859(12) Uani 0.517(4) 1 d . . P B -1
Cl10 Cl 0.3314(10) 0.6015(6) -0.1309(6) 0.197(5) Uani 0.517(4) 1 d . . P B -1
Cl11 Cl 0.0194(9) 0.6216(6) -0.1541(6) 0.216(6) Uani 0.517(4) 1 d . . P B -1
C1 C 0.7174(5) 0.750000 0.5612(3) 0.0196(8) Uani 1 2 d S T P . .
H1 H 0.761130 0.749999 0.506656 0.024 Uiso 1 2 calc R U P . .
C2 C 0.6269(3) 0.69526(13) 0.5633(2) 0.0201(6) Uani 1 1 d . . . . .
H2A H 0.685666 0.660017 0.561703 0.024 Uiso 1 1 calc R U . . .
H2B H 0.553180 0.694638 0.511262 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5585(3) 0.69466(13) 0.6473(2) 0.0187(6) Uani 1 1 d . . . . .
C4 C 0.6754(3) 0.69527(15) 0.7268(2) 0.0235(7) Uani 1 1 d . . . . .
H4A H 0.633638 0.694635 0.781348 0.028 Uiso 1 1 calc R U . . .
H4B H 0.734430 0.660050 0.725922 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7657(5) 0.750000 0.7250(3) 0.0216(9) Uani 1 2 d S T P . .
H5 H 0.841060 0.749999 0.777115 0.026 Uiso 1 2 calc R U P . .
C6 C 0.8323(5) 0.750000 0.6414(3) 0.0221(9) Uani 1 2 d S T P . .
H6A H 0.892052 0.715010 0.640280 0.027 Uiso 0.5 1 calc R U P . .
H6B H 0.892052 0.784990 0.640280 0.027 Uiso 0.5 1 calc R U P . .
C7 C 0.4695(5) 0.750000 0.6491(3) 0.0192(8) Uani 1 2 d S T P . .
H7A H 0.394058 0.750000 0.597970 0.023 Uiso 1 2 calc R U P . .
H7B H 0.425230 0.749999 0.702693 0.023 Uiso 1 2 calc R U P . .
C8 C 0.4717(3) 0.63944(14) 0.6527(2) 0.0242(7) Uani 1 1 d . . . . .
H8A H 0.532913 0.605066 0.650078 0.029 Uiso 1 1 calc R U . . .
H8B H 0.438358 0.638715 0.710060 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3523(3) 0.60498(14) 0.5057(2) 0.0246(7) Uani 1 1 d . . . . .
C10 C 0.2110(3) 0.61228(13) 0.4532(2) 0.0221(6) Uani 1 1 d . . . . .
C11 C 0.1634(4) 0.59460(14) 0.3684(2) 0.0243(7) Uani 1 1 d . . . . .
H11 H 0.219169 0.572602 0.334716 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0273(4) 0.61173(14) 0.3366(2) 0.0230(7) Uani 1 1 d . . . . .
C13 C -0.0556(4) 0.60322(14) 0.2481(2) 0.0262(7) Uani 1 1 d . . . . .
C14 C -0.1921(4) 0.65526(15) 0.3318(2) 0.0233(7) Uani 1 1 d . . . . .
C15 C -0.0541(3) 0.64334(13) 0.3871(2) 0.0213(6) Uani 1 1 d . . . . .
C16 C -0.0068(3) 0.66000(14) 0.4730(2) 0.0218(6) Uani 1 1 d . . . . .
H16 H -0.063330 0.680834 0.507572 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1298(3) 0.64362(13) 0.5039(2) 0.0206(6) Uani 1 1 d . . . . .
C18 C 0.2170(3) 0.65585(14) 0.5902(2) 0.0215(6) Uani 1 1 d . . . . .
C19 C -0.2884(4) 0.63927(16) 0.1723(2) 0.0270(7) Uani 1 1 d . . . . .
H19A H -0.381268 0.640778 0.191651 0.032 Uiso 1 1 calc R U . . .
H19B H -0.286854 0.604592 0.134314 0.032 Uiso 1 1 calc R U . . .
C20 C -0.2819(5) 0.750000 0.1732(3) 0.0221(9) Uani 1 2 d S T P . .
H20A H -0.373347 0.750000 0.194524 0.027 Uiso 1 2 calc R U P . .
H20B H -0.207215 0.750000 0.224766 0.027 Uiso 1 2 calc R U P . .
C21 C -0.2694(4) 0.69440(15) 0.1185(2) 0.0253(7) Uani 1 1 d . . . . .
C22 C -0.1262(4) 0.69530(16) 0.0866(2) 0.0292(7) Uani 1 1 d . . . . .
H22A H -0.050326 0.694900 0.137475 0.035 Uiso 1 1 calc R U . . .
H22B H -0.116297 0.660061 0.050998 0.035 Uiso 1 1 calc R U . . .
C23 C -0.1133(6) 0.750000 0.0316(3) 0.0340(12) Uani 1 2 d S T P . .
H23 H -0.020116 0.750000 0.011120 0.041 Uiso 1 2 calc R U P . .
C24 C -0.2286(7) 0.750000 -0.0475(3) 0.0419(14) Uani 1 2 d S T P . .
H24A H -0.219644 0.715011 -0.083713 0.050 Uiso 0.5 1 calc R U P . .
H24B H -0.219643 0.784989 -0.083713 0.050 Uiso 0.5 1 calc R U P . .
C25 C -0.3718(6) 0.750000 -0.0170(3) 0.0395(13) Uani 1 2 d S T P . .
H25 H -0.447350 0.750000 -0.069017 0.047 Uiso 1 2 calc R U P . .
C26 C -0.3850(4) 0.80481(19) 0.0383(2) 0.0353(9) Uani 1 1 d . . . . .
H26A H -0.477913 0.805294 0.057710 0.042 Uiso 1 1 calc R U . . .
H26B H -0.377345 0.840076 0.002384 0.042 Uiso 1 1 calc R U . . .
C27 C 0.8131(3) 0.52442(13) 0.4745(2) 0.0230(7) Uani 1 1 d . . . . .
C28 C 0.7813(4) 0.50499(14) 0.3893(2) 0.0251(7) Uani 1 1 d . . . . .
C29 C 0.8796(4) 0.47514(15) 0.3481(2) 0.0273(7) Uani 1 1 d . . . . .
H29 H 0.854382 0.461895 0.289638 0.033 Uiso 1 1 calc R U . . .
C30 C 1.0112(4) 0.46499(14) 0.3915(2) 0.0238(7) Uani 1 1 d . . . . .
H30 H 1.077232 0.444574 0.363346 0.029 Uiso 1 1 calc R U . . .
C31 C 1.0493(3) 0.48501(13) 0.4788(2) 0.0219(6) Uani 1 1 d . . . . .
C32 C 0.3835(6) 0.750000 0.2946(4) 0.0370(12) Uani 1 2 d S T P . .
H32 H 0.486165 0.750000 0.317151 0.044 Uiso 1 2 calc R U P . .
Br1 Br 0.60172(4) 0.51906(2) 0.32533(2) 0.02977(14) Uani 1 1 d . . . . .
Cl1 Cl 0.34199(14) 0.68685(6) 0.23093(8) 0.0563(3) Uani 1 1 d . . . . .
Cl2 Cl 0.29084(16) 0.750000 0.38437(9) 0.0396(3) Uani 1 2 d S T P . .
N1 N 0.3510(3) 0.63422(12) 0.58370(19) 0.0230(6) Uani 1 1 d . . . . .
N2 N -0.1808(3) 0.63266(12) 0.24885(18) 0.0246(6) Uani 1 1 d . . . . .
O1 O 0.4502(3) 0.57836(11) 0.48381(19) 0.0329(6) Uani 1 1 d . . . . .
O2 O -0.0233(3) 0.57631(12) 0.18692(17) 0.0344(6) Uani 1 1 d . . . . .
O3 O -0.2933(2) 0.67952(11) 0.35190(15) 0.0262(5) Uani 1 1 d . . . . .
O4 O 0.1835(2) 0.67921(11) 0.65392(16) 0.0266(5) Uani 1 1 d . . . . .
O5 O 0.7259(3) 0.55300(11) 0.51998(18) 0.0305(6) Uani 1 1 d . . . . .
H5A H 0.656(5) 0.555(2) 0.494(2) 0.046 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
C34 Cl8 1.663(14) . ?
C34 Cl6 1.74(2) . ?
C34 Cl7 1.859(16) . ?
C33 Cl4 1.74(2) . ?
C33 Cl3 1.76(2) . ?
C33 Cl5 1.76(2) . ?
C36 Cl12 1.61(2) . ?
C36 Cl13 1.775(18) . ?
C36 Cl14 1.820(14) . ?
C35 Cl10 1.73(3) . ?
C35 Cl9 1.75(3) . ?
C35 Cl11 1.91(2) . ?
C1 C6 1.533(6) . ?
C1 C2 1.533(4) . ?
C1 C2 1.533(4) 4_575 ?
C2 C3 1.546(4) . ?
C3 C8 1.528(4) . ?
C3 C7 1.535(4) . ?
C3 C4 1.537(4) . ?
C4 C5 1.531(4) . ?
C5 C6 1.531(6) . ?
C8 N1 1.459(4) . ?
C9 O1 1.217(4) . ?
C9 N1 1.382(4) . ?
C9 C10 1.487(5) . ?
C10 C11 1.382(5) . ?
C10 C17 1.392(4) . ?
C11 C12 1.389(5) . ?
C12 C15 1.395(4) . ?
C12 C13 1.488(5) . ?
C13 O2 1.210(4) . ?
C13 N2 1.387(5) . ?
C14 O3 1.206(4) . ?
C14 N2 1.404(4) . ?
C14 C15 1.495(5) . ?
C15 C16 1.391(5) . ?
C16 C17 1.385(5) . ?
C17 C18 1.491(4) . ?
C18 O4 1.210(4) . ?
C18 N1 1.405(4) . ?
C19 N2 1.459(4) . ?
C19 C21 1.539(5) . ?
C20 C21 1.544(4) 4_575 ?
C20 C21 1.545(4) . ?
C21 C26 1.537(5) 4_575 ?
C21 C22 1.540(5) . ?
C22 C23 1.531(5) . ?
C23 C24 1.522(8) . ?
C24 C25 1.529(9) . ?
C25 C26 1.536(5) . ?
C25 C26 1.536(5) 4_575 ?
C27 O5 1.348(4) . ?
C27 C28 1.380(5) . ?
C27 C31 1.429(5) 3_766 ?
C28 C29 1.401(5) . ?
C28 Br1 1.889(3) . ?
C29 C30 1.363(5) . ?
C30 C31 1.421(5) . ?
C31 C31 1.415(6) 3_766 ?
C32 Cl1 1.762(4) . ?
C32 Cl1 1.762(4) 4_575 ?
C32 Cl2 1.764(6) . ?

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
Cl8 C34 Cl6 99.7(13) . . ?
Cl8 C34 Cl7 90.3(9) . . ?
Cl6 C34 Cl7 107.5(11) . . ?
Cl4 C33 Cl3 108.2(13) . . ?
Cl4 C33 Cl5 116.0(15) . . ?
Cl3 C33 Cl5 121.4(13) . . ?
Cl12 C36 Cl13 112.6(10) . . ?
Cl12 C36 Cl14 105.4(10) . . ?
Cl13 C36 Cl14 107.5(9) . . ?
Cl10 C35 Cl9 107.0(11) . . ?
Cl10 C35 Cl11 112.0(16) . . ?
Cl9 C35 Cl11 109.2(11) . . ?
C6 C1 C2 109.1(2) . . ?
C6 C1 C2 109.1(2) . 4_575 ?
C2 C1 C2 109.9(4) . 4_575 ?
C1 C2 C3 110.2(3) . . ?
C8 C3 C7 111.7(3) . . ?
C8 C3 C4 107.8(3) . . ?
C7 C3 C4 108.8(3) . . ?
C8 C3 C2 111.3(3) . . ?
C7 C3 C2 108.8(3) . . ?
C4 C3 C2 108.4(3) . . ?
C5 C4 C3 110.1(3) . . ?
C6 C5 C4 109.3(2) . 4_575 ?
C6 C5 C4 109.3(2) . . ?
C4 C5 C4 110.0(4) 4_575 . ?
C5 C6 C1 109.7(4) . . ?
C3 C7 C3 111.5(4) 4_575 . ?
N1 C8 C3 114.3(3) . . ?
O1 C9 N1 126.7(3) . . ?
O1 C9 C10 126.3(3) . . ?
N1 C9 C10 106.9(3) . . ?
C11 C10 C17 123.5(3) . . ?
C11 C10 C9 128.9(3) . . ?
C17 C10 C9 107.5(3) . . ?
C10 C11 C12 114.3(3) . . ?
C11 C12 C15 122.3(3) . . ?
C11 C12 C13 129.4(3) . . ?
C15 C12 C13 108.3(3) . . ?
O2 C13 N2 125.8(3) . . ?
O2 C13 C12 128.2(3) . . ?
N2 C13 C12 106.0(3) . . ?
O3 C14 N2 125.9(3) . . ?
O3 C14 C15 128.6(3) . . ?
N2 C14 C15 105.5(3) . . ?
C16 C15 C12 123.2(3) . . ?
C16 C15 C14 129.0(3) . . ?
C12 C15 C14 107.8(3) . . ?
C17 C16 C15 114.3(3) . . ?
C16 C17 C10 122.4(3) . . ?
C16 C17 C18 129.4(3) . . ?
C10 C17 C18 108.2(3) . . ?
O4 C18 N1 125.5(3) . . ?
O4 C18 C17 128.8(3) . . ?
N1 C18 C17 105.7(3) . . ?
N2 C19 C21 113.2(3) . . ?
C21 C20 C21 111.2(4) 4_575 . ?
C26 C21 C19 108.3(3) 4_575 . ?
C26 C21 C22 108.5(3) 4_575 . ?
C19 C21 C22 111.9(3) . . ?
C26 C21 C20 108.9(3) 4_575 . ?
C19 C21 C20 110.8(3) . . ?
C22 C21 C20 108.4(3) . . ?
C23 C22 C21 110.1(3) . . ?
C24 C23 C22 109.5(3) . 4_575 ?
C24 C23 C22 109.5(3) . . ?
C22 C23 C22 110.0(4) 4_575 . ?
C23 C24 C25 109.7(4) . . ?
C24 C25 C26 109.2(3) . . ?
C24 C25 C26 109.2(3) . 4_575 ?
C26 C25 C26 109.7(5) . 4_575 ?
C25 C26 C21 110.3(3) . 4_575 ?
O5 C27 C28 126.2(3) . . ?
O5 C27 C31 114.7(3) . 3_766 ?
C28 C27 C31 119.1(3) . 3_766 ?
C27 C28 C29 121.7(3) . . ?
C27 C28 Br1 119.8(3) . . ?
C29 C28 Br1 118.5(3) . . ?
C30 C29 C28 120.4(3) . . ?
C29 C30 C31 119.9(3) . . ?
C31 C31 C30 120.2(4) 3_766 . ?
C31 C31 C27 118.7(4) 3_766 3_766 ?
C30 C31 C27 121.1(3) . 3_766 ?
Cl1 C32 Cl1 110.5(3) . 4_575 ?
Cl1 C32 Cl2 109.9(2) . . ?
Cl1 C32 Cl2 109.9(2) 4_575 . ?
C9 N1 C18 111.5(3) . . ?
C9 N1 C8 124.4(3) . . ?
C18 N1 C8 124.1(3) . . ?
C13 N2 C14 112.2(3) . . ?
C13 N2 C19 123.9(3) . . ?
C14 N2 C19 123.9(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
C6 C1 C2 C3 60.1(4) . . . . ?
C2 C1 C2 C3 -59.5(4) 4_575 . . . ?
C1 C2 C3 C8 -178.0(3) . . . . ?
C1 C2 C3 C7 58.5(3) . . . . ?
C1 C2 C3 C4 -59.6(3) . . . . ?
C8 C3 C4 C5 -179.8(3) . . . . ?
C7 C3 C4 C5 -58.4(3) . . . . ?
C2 C3 C4 C5 59.7(3) . . . . ?
C3 C4 C5 C6 -60.5(4) . . . . ?
C3 C4 C5 C4 59.6(4) . . . 4_575 ?
C4 C5 C6 C1 -60.3(2) 4_575 . . . ?
C4 C5 C6 C1 60.3(2) . . . . ?
C2 C1 C6 C5 -60.0(2) . . . . ?
C2 C1 C6 C5 60.0(2) 4_575 . . . ?
C8 C3 C7 C3 177.8(2) . . . 4_575 ?
C4 C3 C7 C3 58.8(4) . . . 4_575 ?
C2 C3 C7 C3 -59.0(4) . . . 4_575 ?
C7 C3 C8 N1 57.3(4) . . . . ?
C4 C3 C8 N1 176.8(3) . . . . ?
C2 C3 C8 N1 -64.5(3) . . . . ?
O1 C9 C10 C11 -4.8(6) . . . . ?
N1 C9 C10 C11 175.1(3) . . . . ?
O1 C9 C10 C17 177.7(3) . . . . ?
N1 C9 C10 C17 -2.4(4) . . . . ?
C17 C10 C11 C12 1.2(5) . . . . ?
C9 C10 C11 C12 -175.9(3) . . . . ?
C10 C11 C12 C15 -0.9(5) . . . . ?
C10 C11 C12 C13 176.8(3) . . . . ?
C11 C12 C13 O2 4.9(6) . . . . ?
C15 C12 C13 O2 -177.2(4) . . . . ?
C11 C12 C13 N2 -175.3(3) . . . . ?
C15 C12 C13 N2 2.7(4) . . . . ?
C11 C12 C15 C16 -0.4(5) . . . . ?
C13 C12 C15 C16 -178.5(3) . . . . ?
C11 C12 C15 C14 178.7(3) . . . . ?
C13 C12 C15 C14 0.5(4) . . . . ?
O3 C14 C15 C16 -3.8(6) . . . . ?
N2 C14 C15 C16 175.5(3) . . . . ?
O3 C14 C15 C12 177.2(3) . . . . ?
N2 C14 C15 C12 -3.5(3) . . . . ?
C12 C15 C16 C17 1.3(5) . . . . ?
C14 C15 C16 C17 -177.5(3) . . . . ?
C15 C16 C17 C10 -1.0(5) . . . . ?
C15 C16 C17 C18 177.1(3) . . . . ?
C11 C10 C17 C16 -0.2(5) . . . . ?
C9 C10 C17 C16 177.4(3) . . . . ?
C11 C10 C17 C18 -178.7(3) . . . . ?
C9 C10 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 O4 5.9(6) . . . . ?
C10 C17 C18 O4 -175.8(3) . . . . ?
C16 C17 C18 N1 -174.3(3) . . . . ?
C10 C17 C18 N1 4.1(3) . . . . ?
N2 C19 C21 C26 177.8(3) . . . 4_575 ?
N2 C19 C21 C22 58.3(4) . . . . ?
N2 C19 C21 C20 -62.8(4) . . . . ?
C21 C20 C21 C26 -58.6(5) 4_575 . . 4_575 ?
C21 C20 C21 C19 -177.5(2) 4_575 . . . ?
C21 C20 C21 C22 59.3(4) 4_575 . . . ?
C26 C21 C22 C23 59.2(4) 4_575 . . . ?
C19 C21 C22 C23 178.6(3) . . . . ?
C20 C21 C22 C23 -58.9(4) . . . . ?
C21 C22 C23 C24 -60.2(4) . . . . ?
C21 C22 C23 C22 60.2(5) . . . 4_575 ?
C22 C23 C24 C25 -60.3(3) 4_575 . . . ?
C22 C23 C24 C25 60.3(3) . . . . ?
C23 C24 C25 C26 60.0(3) . . . . ?
C23 C24 C25 C26 -60.0(3) . . . 4_575 ?
C24 C25 C26 C21 -59.9(4) . . . 4_575 ?
C26 C25 C26 C21 59.8(6) 4_575 . . 4_575 ?
O5 C27 C28 C29 -179.4(3) . . . . ?
C31 C27 C28 C29 1.4(5) 3_766 . . . ?
O5 C27 C28 Br1 1.0(5) . . . . ?
C31 C27 C28 Br1 -178.1(2) 3_766 . . . ?
C27 C28 C29 C30 -0.7(5) . . . . ?
Br1 C28 C29 C30 178.8(3) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
C29 C30 C31 C31 0.5(6) . . . 3_766 ?
C29 C30 C31 C27 -179.3(3) . . . 3_766 ?
O1 C9 N1 C18 -174.9(3) . . . . ?
C10 C9 N1 C18 5.2(4) . . . . ?
O1 C9 N1 C8 2.2(5) . . . . ?
C10 C9 N1 C8 -177.8(3) . . . . ?
O4 C18 N1 C9 174.1(3) . . . . ?
C17 C18 N1 C9 -5.8(3) . . . . ?
O4 C18 N1 C8 -3.0(5) . . . . ?
C17 C18 N1 C8 177.2(3) . . . . ?
C3 C8 N1 C9 93.2(4) . . . . ?
C3 C8 N1 C18 -90.1(4) . . . . ?
O2 C13 N2 C14 174.7(3) . . . . ?
C12 C13 N2 C14 -5.1(4) . . . . ?
O2 C13 N2 C19 -5.2(6) . . . . ?
C12 C13 N2 C19 175.0(3) . . . . ?
O3 C14 N2 C13 -175.2(3) . . . . ?
C15 C14 N2 C13 5.5(4) . . . . ?
O3 C14 N2 C19 4.7(5) . . . . ?
C15 C14 N2 C19 -174.6(3) . . . . ?
C21 C19 N2 C13 -89.8(4) . . . . ?
C21 C19 N2 C14 90.3(4) . . . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2389267'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H58 Br2 N4 O12'
_chemical_formula_weight         1186.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7166(6)
_cell_length_b                   11.3692(7)
_cell_length_c                   24.7966(16)
_cell_angle_alpha                94.639(2)
_cell_angle_beta                 92.734(2)
_cell_angle_gamma                107.934(2)
_cell_volume                     2590.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellowish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.577
_shelx_estimated_absorpt_T_min   0.747
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8008
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            38075
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         79.641
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10549
_reflns_number_gt                10351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+1.7499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10549
_refine_ls_number_parameters     709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.47821(15) 0.21229(12) 0.95721(5) 0.0122(3) Uani 1 1 d . . . . .
C2 C 0.41964(14) 0.31621(12) 0.94040(5) 0.0116(2) Uani 1 1 d . . . . .
H2A H 0.414111 0.314686 0.900369 0.014 Uiso 1 1 calc R U . . .
H2AB H 0.487125 0.397815 0.955758 0.014 Uiso 1 1 calc R U . . .
C3 C 0.26804(14) 0.30020(12) 0.96058(5) 0.0126(3) Uani 1 1 d . . . . .
C4 C 0.16443(15) 0.17317(13) 0.93655(6) 0.0153(3) Uani 1 1 d . . . . .
H4A H 0.066595 0.161746 0.949315 0.018 Uiso 1 1 calc R U . . .
H4AB H 0.156648 0.169666 0.896462 0.018 Uiso 1 1 calc R U . . .
C5 C 0.22111(15) 0.06888(13) 0.95399(6) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.153099 -0.013323 0.938146 0.020 Uiso 1 1 calc R U . . .
C6 C 0.37192(15) 0.08650(12) 0.93309(6) 0.0150(3) Uani 1 1 d . . . . .
H6A H 0.408321 0.018529 0.943453 0.018 Uiso 1 1 calc R U . . .
H6AB H 0.364861 0.083042 0.892993 0.018 Uiso 1 1 calc R U . . .
C7 C 0.23053(17) 0.07353(14) 1.01598(6) 0.0201(3) Uani 1 1 d . . . . .
H7A H 0.133304 0.062498 1.029268 0.024 Uiso 1 1 calc R U . . .
H7AB H 0.265093 0.005453 1.027499 0.024 Uiso 1 1 calc R U . . .
C8 C 0.33566(16) 0.19903(13) 1.04006(6) 0.0165(3) Uani 1 1 d . . . . .
H8 H 0.342709 0.202185 1.080545 0.020 Uiso 1 1 calc R U . . .
C9 C 0.48613(15) 0.21560(13) 1.01929(5) 0.0145(3) Uani 1 1 d . . . . .
H9A H 0.554634 0.295988 1.035483 0.017 Uiso 1 1 calc R U . . .
H9AB H 0.522718 0.148395 1.030534 0.017 Uiso 1 1 calc R U . . .
C10 C 0.27956(15) 0.30373(13) 1.02275(6) 0.0155(3) Uani 1 1 d . . . . .
H10A H 0.346594 0.385051 1.038638 0.019 Uiso 1 1 calc R U . . .
H10B H 0.183040 0.293933 1.036480 0.019 Uiso 1 1 calc R U . . .
C11 C 0.63229(15) 0.23160(13) 0.93922(5) 0.0140(3) Uani 1 1 d . . . . .
H11A H 0.698076 0.310398 0.958031 0.017 Uiso 1 1 calc R U . . .
H11B H 0.666615 0.163214 0.950510 0.017 Uiso 1 1 calc R U . . .
C12 C 0.67857(14) 0.34534(13) 0.85572(6) 0.0134(3) Uani 1 1 d . . . . .
C13 C 0.66565(14) 0.30702(13) 0.79621(6) 0.0128(3) Uani 1 1 d . . . . .
C14 C 0.63885(14) 0.17889(13) 0.78945(6) 0.0131(3) Uani 1 1 d . . . . .
C15 C 0.62861(14) 0.13248(13) 0.84422(6) 0.0136(3) Uani 1 1 d . . . . .
C16 C 0.67260(14) 0.37771(13) 0.75271(6) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.690490 0.465035 0.757313 0.016 Uiso 1 1 calc R U . . .
C17 C 0.65137(14) 0.31088(13) 0.70201(6) 0.0129(3) Uani 1 1 d . . . . .
C18 C 0.62363(14) 0.18303(13) 0.69542(6) 0.0130(3) Uani 1 1 d . . . . .
C19 C 0.61807(14) 0.11207(13) 0.73887(6) 0.0135(3) Uani 1 1 d . . . . .
H19 H 0.601387 0.024906 0.734239 0.016 Uiso 1 1 calc R U . . .
C20 C 0.65021(14) 0.35532(13) 0.64704(6) 0.0139(3) Uani 1 1 d . . . . .
C21 C 0.59557(14) 0.14187(13) 0.63611(6) 0.0136(3) Uani 1 1 d . . . . .
C22 C 0.59604(14) 0.25183(13) 0.55144(5) 0.0141(3) Uani 1 1 d . . . . .
H22A H 0.627154 0.183923 0.533821 0.017 Uiso 1 1 calc R U . . .
H22B H 0.663061 0.331463 0.542257 0.017 Uiso 1 1 calc R U . . .
C23 C 0.44204(14) 0.23864(12) 0.52811(5) 0.0122(3) Uani 1 1 d . . . . .
C24 C 0.44701(15) 0.25429(14) 0.46712(6) 0.0172(3) Uani 1 1 d . . . . .
H24A H 0.514933 0.336842 0.461850 0.021 Uiso 1 1 calc R U . . .
H24B H 0.482825 0.190047 0.448746 0.021 Uiso 1 1 calc R U . . .
C25 C 0.29500(16) 0.24225(15) 0.44194(6) 0.0191(3) Uani 1 1 d . . . . .
H25 H 0.299621 0.253250 0.402391 0.023 Uiso 1 1 calc R U . . .
C26 C 0.19144(16) 0.11302(15) 0.44929(6) 0.0216(3) Uani 1 1 d . . . . .
H26A H 0.093278 0.104060 0.432994 0.026 Uiso 1 1 calc R U . . .
H26B H 0.225991 0.048224 0.430691 0.026 Uiso 1 1 calc R U . . .
C27 C 0.18526(15) 0.09671(13) 0.50992(6) 0.0173(3) Uani 1 1 d . . . . .
H27 H 0.117917 0.012447 0.514730 0.021 Uiso 1 1 calc R U . . .
C28 C 0.33714(15) 0.10955(12) 0.53519(6) 0.0150(3) Uani 1 1 d . . . . .
H28A H 0.372849 0.044569 0.517428 0.018 Uiso 1 1 calc R U . . .
H28B H 0.332478 0.097991 0.574286 0.018 Uiso 1 1 calc R U . . .
C29 C 0.12957(14) 0.19599(13) 0.53831(6) 0.0146(3) Uani 1 1 d . . . . .
H29A H 0.124105 0.184782 0.577421 0.017 Uiso 1 1 calc R U . . .
H29B H 0.030837 0.187052 0.522615 0.017 Uiso 1 1 calc R U . . .
C30 C 0.23190(14) 0.32622(12) 0.53126(5) 0.0128(3) Uani 1 1 d . . . . .
C31 C 0.38476(14) 0.33815(12) 0.55600(5) 0.0120(2) Uani 1 1 d . . . . .
H31A H 0.451656 0.421752 0.551674 0.014 Uiso 1 1 calc R U . . .
H31B H 0.381217 0.328656 0.595292 0.014 Uiso 1 1 calc R U . . .
C32 C 0.23980(16) 0.34188(14) 0.47042(6) 0.0172(3) Uani 1 1 d . . . . .
H32A H 0.142314 0.334759 0.454008 0.021 Uiso 1 1 calc R U . . .
H32B H 0.305909 0.425398 0.465473 0.021 Uiso 1 1 calc R U . . .
C33 C 0.17491(15) 0.42761(13) 0.55702(6) 0.0156(3) Uani 1 1 d . . . . .
H33A H 0.236297 0.509355 0.547663 0.019 Uiso 1 1 calc R U . . .
H33B H 0.075142 0.414021 0.541144 0.019 Uiso 1 1 calc R U . . .
C34 C 0.05580(15) 0.36684(13) 0.64371(6) 0.0156(3) Uani 1 1 d . . . . .
C35 C 0.10615(15) 0.39419(13) 0.70264(6) 0.0146(3) Uani 1 1 d . . . . .
C36 C 0.24682(15) 0.47581(13) 0.70712(6) 0.0145(3) Uani 1 1 d . . . . .
C37 C 0.29049(15) 0.50409(13) 0.65153(6) 0.0149(3) Uani 1 1 d . . . . .
C38 C 0.03420(15) 0.34726(13) 0.74722(6) 0.0152(3) Uani 1 1 d . . . . .
H38 H -0.062043 0.291496 0.744126 0.018 Uiso 1 1 calc R U . . .
C39 C 0.11513(15) 0.38890(13) 0.79667(6) 0.0147(3) Uani 1 1 d . . . . .
C40 C 0.25649(15) 0.47007(12) 0.80085(6) 0.0143(3) Uani 1 1 d . . . . .
C41 C 0.32787(15) 0.51714(12) 0.75640(6) 0.0147(3) Uani 1 1 d . . . . .
H41 H 0.424085 0.572949 0.759458 0.018 Uiso 1 1 calc R U . . .
C42 C 0.07554(15) 0.35637(13) 0.85226(6) 0.0154(3) Uani 1 1 d . . . . .
C43 C 0.31167(15) 0.49074(12) 0.85900(6) 0.0144(3) Uani 1 1 d . . . . .
C44 C 0.21114(15) 0.40566(13) 0.94504(5) 0.0152(3) Uani 1 1 d . . . . .
H44A H 0.113999 0.392507 0.958713 0.018 Uiso 1 1 calc R U . . .
H44B H 0.276415 0.485332 0.963288 0.018 Uiso 1 1 calc R U . . .
C45 C 1.04332(15) 0.67125(13) 0.80855(6) 0.0148(3) Uani 1 1 d . . . . .
C46 C 1.14762(15) 0.71985(13) 0.85074(6) 0.0149(3) Uani 1 1 d . . . . .
C47 C 1.28910(15) 0.79373(13) 0.84234(6) 0.0161(3) Uani 1 1 d . . . . .
H47 H 1.358951 0.826165 0.872318 0.019 Uiso 1 1 calc R U . . .
C48 C 1.32573(15) 0.81870(13) 0.79097(6) 0.0157(3) Uani 1 1 d . . . . .
H48 H 1.420926 0.869106 0.785327 0.019 Uiso 1 1 calc R U . . .
C49 C 1.22205(15) 0.76957(12) 0.74609(6) 0.0140(3) Uani 1 1 d . . . . .
C50 C 1.25835(15) 0.79312(13) 0.69215(6) 0.0150(3) Uani 1 1 d . . . . .
C51 C 1.15454(15) 0.74296(13) 0.64986(6) 0.0153(3) Uani 1 1 d . . . . .
C52 C 1.01328(15) 0.66829(13) 0.65829(6) 0.0171(3) Uani 1 1 d . . . . .
H52 H 0.944018 0.634289 0.628257 0.021 Uiso 1 1 calc R U . . .
C53 C 0.97610(15) 0.64489(13) 0.70966(6) 0.0168(3) Uani 1 1 d . . . . .
H53 H 0.880810 0.594743 0.715342 0.020 Uiso 1 1 calc R U . . .
C54 C 1.07943(15) 0.69527(12) 0.75458(6) 0.0140(3) Uani 1 1 d . . . . .
C55 C 0.9011(2) -0.07947(18) 0.84450(8) 0.0323(4) Uani 1 1 d . . . . .
H55A H 1.004665 -0.066005 0.840727 0.048 Uiso 1 1 calc R U . . .
H55B H 0.858804 -0.158533 0.859665 0.048 Uiso 1 1 calc R U . . .
H55C H 0.889157 -0.011511 0.868800 0.048 Uiso 1 1 calc R U . . .
C56 C 0.82605(19) -0.08306(19) 0.79001(8) 0.0343(4) Uani 1 1 d . . . . .
C57 C 0.7047(3) -0.2003(2) 0.77176(12) 0.0631(8) Uani 1 1 d . . . . .
H57A H 0.667076 -0.195880 0.734861 0.095 Uiso 1 1 calc R U . . .
H57B H 0.626861 -0.209837 0.796359 0.095 Uiso 1 1 calc R U . . .
H57C H 0.741071 -0.271647 0.772157 0.095 Uiso 1 1 calc R U . . .
C58 C 0.2393(2) 0.12481(16) 0.76729(7) 0.0291(4) Uani 1 1 d . . . . .
H58A H 0.264649 0.050190 0.774427 0.044 Uiso 1 1 calc R U . . .
H58B H 0.147375 0.121438 0.782753 0.044 Uiso 1 1 calc R U . . .
H58C H 0.315974 0.198700 0.783961 0.044 Uiso 1 1 calc R U . . .
C59 C 0.22390(17) 0.13112(14) 0.70710(7) 0.0222(3) Uani 1 1 d . . . . .
C60 C 0.09748(19) 0.03566(16) 0.67592(7) 0.0284(4) Uani 1 1 d . . . . .
H60A H 0.121073 0.021645 0.638442 0.043 Uiso 1 1 calc R U . . .
H60B H 0.012715 0.065107 0.676033 0.043 Uiso 1 1 calc R U . . .
H60C H 0.075830 -0.042319 0.692856 0.043 Uiso 1 1 calc R U . . .
N1 N 0.64088(12) 0.23560(11) 0.88080(5) 0.0128(2) Uani 1 1 d . . . . .
N2 N 0.60856(12) 0.24836(11) 0.61025(5) 0.0129(2) Uani 1 1 d . . . . .
N3 N 0.17300(13) 0.43117(11) 0.61595(5) 0.0148(2) Uani 1 1 d . . . . .
N4 N 0.20044(13) 0.41531(11) 0.88672(5) 0.0146(2) Uani 1 1 d . . . . .
O1 O 0.61168(11) 0.02808(9) 0.85612(4) 0.0170(2) Uani 1 1 d . . . . .
O2 O 0.56537(11) 0.03704(9) 0.61409(4) 0.0181(2) Uani 1 1 d . . . . .
O3 O 0.68050(11) 0.46074(9) 0.63536(4) 0.0185(2) Uani 1 1 d . . . . .
O4 O 0.71502(11) 0.44893(9) 0.87929(4) 0.0180(2) Uani 1 1 d . . . . .
O5 O 0.40102(11) 0.57494(9) 0.63856(4) 0.0194(2) Uani 1 1 d . . . . .
O6 O -0.06208(11) 0.30326(10) 0.62344(4) 0.0212(2) Uani 1 1 d . . . . .
O7 O -0.03914(11) 0.29388(11) 0.86642(4) 0.0217(2) Uani 1 1 d . . . . .
O8 O 0.42729(11) 0.55772(9) 0.87948(4) 0.0184(2) Uani 1 1 d . . . . .
O9 O 0.90490(11) 0.60096(10) 0.81368(4) 0.0205(2) Uani 1 1 d . . . . .
H9 H 0.894233 0.588161 0.846337 0.031 Uiso 1 1 calc R U . . .
O10 O 1.39527(11) 0.86604(10) 0.68668(4) 0.0214(2) Uani 1 1 d . . . . .
H10 H 1.406015 0.876026 0.653769 0.032 Uiso 1 1 calc R U . . .
O11 O 0.86227(17) 0.00484(19) 0.76374(6) 0.0539(4) Uani 1 1 d . . . . .
O12 O 0.30880(14) 0.21107(13) 0.68480(6) 0.0354(3) Uani 1 1 d . . . . .
Br1 Br 1.09754(2) 0.68719(2) 0.92246(2) 0.01846(5) Uani 1 1 d . . . . .
Br2 Br 1.20180(2) 0.77927(2) 0.57848(2) 0.01901(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.5346(18) . ?
C1 C6 1.5372(18) . ?
C1 C2 1.5377(18) . ?
C1 C11 1.5381(19) . ?
C2 C3 1.5405(18) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C44 1.5344(18) . ?
C3 C10 1.5367(18) . ?
C3 C4 1.5370(19) . ?
C4 C5 1.5358(19) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C7 1.531(2) . ?
C5 C6 1.538(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.530(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.5349(19) . ?
C8 C10 1.536(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.4586(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O4 1.2108(17) . ?
C12 N1 1.3940(18) . ?
C12 C13 1.4926(19) . ?
C13 C16 1.3882(19) . ?
C13 C14 1.3931(19) . ?
C14 C19 1.3850(19) . ?
C14 C15 1.4929(19) . ?
C15 O1 1.2101(17) . ?
C15 N1 1.3940(17) . ?
C16 C17 1.3873(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3886(19) . ?
C17 C20 1.4923(19) . ?
C18 C19 1.3907(19) . ?
C18 C21 1.4927(19) . ?
C19 H19 0.9500 . ?
C20 O3 1.2057(17) . ?
C20 N2 1.3991(18) . ?
C21 O2 1.2120(17) . ?
C21 N2 1.3900(18) . ?
C22 N2 1.4622(17) . ?
C22 C23 1.5367(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.5366(18) . ?
C23 C31 1.5381(19) . ?
C23 C24 1.5383(18) . ?
C24 C25 1.5374(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C32 1.533(2) . ?
C25 C26 1.535(2) . ?
C25 H25 1.0000 . ?
C26 C27 1.531(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C29 1.5319(19) . ?
C27 C28 1.5350(19) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.5373(18) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C33 1.5333(19) . ?
C30 C32 1.5360(18) . ?
C30 C31 1.5415(18) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 N3 1.4597(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O6 1.2098(18) . ?
C34 N3 1.3960(18) . ?
C34 C35 1.4953(19) . ?
C35 C36 1.389(2) . ?
C35 C38 1.391(2) . ?
C36 C41 1.386(2) . ?
C36 C37 1.4924(19) . ?
C37 O5 1.2032(18) . ?
C37 N3 1.4042(18) . ?
C38 C39 1.390(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.393(2) . ?
C39 C42 1.494(2) . ?
C40 C41 1.386(2) . ?
C40 C43 1.4885(19) . ?
C41 H41 0.9500 . ?
C42 O7 1.2082(18) . ?
C42 N4 1.3999(18) . ?
C43 O8 1.2067(18) . ?
C43 N4 1.4042(18) . ?
C44 N4 1.4602(17) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 O9 1.3544(17) . ?
C45 C46 1.374(2) . ?
C45 C54 1.426(2) . ?
C46 C47 1.408(2) . ?
C46 Br1 1.9015(14) . ?
C47 C48 1.367(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.4183(19) . ?
C48 H48 0.9500 . ?
C49 C54 1.419(2) . ?
C49 C50 1.425(2) . ?
C50 O10 1.3534(17) . ?
C50 C51 1.375(2) . ?
C51 C52 1.410(2) . ?
C51 Br2 1.8956(14) . ?
C52 C53 1.365(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.4187(19) . ?
C53 H53 0.9500 . ?
C55 C56 1.496(3) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 O11 1.207(3) . ?
C56 C57 1.502(3) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 C59 1.503(2) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 O12 1.215(2) . ?
C59 C60 1.496(2) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
O9 H9 0.8400 . ?
O10 H10 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C6 108.55(11) . . ?
C9 C1 C2 108.91(11) . . ?
C6 C1 C2 108.64(11) . . ?
C9 C1 C11 107.77(11) . . ?
C6 C1 C11 111.97(11) . . ?
C2 C1 C11 110.94(11) . . ?
C1 C2 C3 111.00(11) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2AB 109.4 . . ?
C3 C2 H2AB 109.4 . . ?
H2A C2 H2AB 108.0 . . ?
C44 C3 C10 108.49(11) . . ?
C44 C3 C4 110.89(11) . . ?
C10 C3 C4 108.96(11) . . ?
C44 C3 C2 111.03(11) . . ?
C10 C3 C2 108.48(11) . . ?
C4 C3 C2 108.93(11) . . ?
C5 C4 C3 110.00(11) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4AB 109.7 . . ?
C3 C4 H4AB 109.7 . . ?
H4A C4 H4AB 108.2 . . ?
C7 C5 C4 109.38(12) . . ?
C7 C5 C6 110.11(12) . . ?
C4 C5 C6 109.10(11) . . ?
C7 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C1 C6 C5 110.16(11) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6AB 109.6 . . ?
C5 C6 H6AB 109.6 . . ?
H6A C6 H6AB 108.1 . . ?
C8 C7 C5 109.24(12) . . ?
C8 C7 H7A 109.8 . . ?
C5 C7 H7A 109.8 . . ?
C8 C7 H7AB 109.8 . . ?
C5 C7 H7AB 109.8 . . ?
H7A C7 H7AB 108.3 . . ?
C7 C8 C9 109.58(12) . . ?
C7 C8 C10 109.35(12) . . ?
C9 C8 C10 109.41(11) . . ?
C7 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C10 C8 H8 109.5 . . ?
C1 C9 C8 110.42(11) . . ?
C1 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C1 C9 H9AB 109.6 . . ?
C8 C9 H9AB 109.6 . . ?
H9A C9 H9AB 108.1 . . ?
C8 C10 C3 110.17(11) . . ?
C8 C10 H10A 109.6 . . ?
C3 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
C3 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N1 C11 C1 113.29(11) . . ?
N1 C11 H11A 108.9 . . ?
C1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O4 C12 N1 124.96(13) . . ?
O4 C12 C13 129.00(13) . . ?
N1 C12 C13 106.03(11) . . ?
C16 C13 C14 122.60(13) . . ?
C16 C13 C12 129.91(13) . . ?
C14 C13 C12 107.46(12) . . ?
C19 C14 C13 122.70(13) . . ?
C19 C14 C15 129.00(13) . . ?
C13 C14 C15 108.19(12) . . ?
O1 C15 N1 125.35(13) . . ?
O1 C15 C14 128.95(13) . . ?
N1 C15 C14 105.70(11) . . ?
C17 C16 C13 114.78(12) . . ?
C17 C16 H16 122.6 . . ?
C13 C16 H16 122.6 . . ?
C16 C17 C18 122.48(13) . . ?
C16 C17 C20 129.44(13) . . ?
C18 C17 C20 108.07(12) . . ?
C17 C18 C19 122.92(13) . . ?
C17 C18 C21 107.79(12) . . ?
C19 C18 C21 129.23(13) . . ?
C14 C19 C18 114.51(12) . . ?
C14 C19 H19 122.7 . . ?
C18 C19 H19 122.7 . . ?
O3 C20 N2 125.76(13) . . ?
O3 C20 C17 128.42(13) . . ?
N2 C20 C17 105.81(11) . . ?
O2 C21 N2 125.91(13) . . ?
O2 C21 C18 127.79(13) . . ?
N2 C21 C18 106.30(11) . . ?
N2 C22 C23 113.87(11) . . ?
N2 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
N2 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C28 C23 C22 110.79(11) . . ?
C28 C23 C31 108.85(11) . . ?
C22 C23 C31 111.18(11) . . ?
C28 C23 C24 108.61(11) . . ?
C22 C23 C24 108.34(11) . . ?
C31 C23 C24 109.02(11) . . ?
C25 C24 C23 110.25(11) . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C32 C25 C26 109.41(12) . . ?
C32 C25 C24 109.52(12) . . ?
C26 C25 C24 109.15(12) . . ?
C32 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C24 C25 H25 109.6 . . ?
C27 C26 C25 109.29(11) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 C29 109.57(12) . . ?
C26 C27 C28 109.92(12) . . ?
C29 C27 C28 109.38(11) . . ?
C26 C27 H27 109.3 . . ?
C29 C27 H27 109.3 . . ?
C28 C27 H27 109.3 . . ?
C27 C28 C23 109.96(11) . . ?
C27 C28 H28A 109.7 . . ?
C23 C28 H28A 109.7 . . ?
C27 C28 H28B 109.7 . . ?
C23 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C27 C29 C30 109.99(11) . . ?
C27 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
C27 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C33 C30 C32 107.50(11) . . ?
C33 C30 C29 111.11(11) . . ?
C32 C30 C29 109.02(11) . . ?
C33 C30 C31 111.64(11) . . ?
C32 C30 C31 108.71(11) . . ?
C29 C30 C31 108.80(11) . . ?
C23 C31 C30 110.74(11) . . ?
C23 C31 H31A 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C25 C32 C30 110.26(12) . . ?
C25 C32 H32A 109.6 . . ?
C30 C32 H32A 109.6 . . ?
C25 C32 H32B 109.6 . . ?
C30 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N3 C33 C30 113.84(11) . . ?
N3 C33 H33A 108.8 . . ?
C30 C33 H33A 108.8 . . ?
N3 C33 H33B 108.8 . . ?
C30 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
O6 C34 N3 126.16(13) . . ?
O6 C34 C35 127.91(13) . . ?
N3 C34 C35 105.93(12) . . ?
C36 C35 C38 122.92(13) . . ?
C36 C35 C34 107.91(12) . . ?
C38 C35 C34 129.14(13) . . ?
C41 C36 C35 122.89(13) . . ?
C41 C36 C37 128.61(13) . . ?
C35 C36 C37 108.47(12) . . ?
O5 C37 N3 125.84(13) . . ?
O5 C37 C36 128.66(13) . . ?
N3 C37 C36 105.49(12) . . ?
C39 C38 C35 114.26(13) . . ?
C39 C38 H38 122.9 . . ?
C35 C38 H38 122.9 . . ?
C38 C39 C40 122.53(13) . . ?
C38 C39 C42 129.25(13) . . ?
C40 C39 C42 108.19(12) . . ?
C41 C40 C39 123.14(13) . . ?
C41 C40 C43 128.73(13) . . ?
C39 C40 C43 108.11(12) . . ?
C40 C41 C36 114.25(13) . . ?
C40 C41 H41 122.9 . . ?
C36 C41 H41 122.9 . . ?
O7 C42 N4 125.32(13) . . ?
O7 C42 C39 128.92(13) . . ?
N4 C42 C39 105.75(12) . . ?
O8 C43 N4 125.58(13) . . ?
O8 C43 C40 128.49(13) . . ?
N4 C43 C40 105.94(12) . . ?
N4 C44 C3 113.88(11) . . ?
N4 C44 H44A 108.8 . . ?
C3 C44 H44A 108.8 . . ?
N4 C44 H44B 108.8 . . ?
C3 C44 H44B 108.8 . . ?
H44A C44 H44B 107.7 . . ?
O9 C45 C46 125.13(13) . . ?
O9 C45 C54 115.71(12) . . ?
C46 C45 C54 119.16(13) . . ?
C45 C46 C47 121.94(13) . . ?
C45 C46 Br1 118.61(11) . . ?
C47 C46 Br1 119.45(11) . . ?
C48 C47 C46 119.87(13) . . ?
C48 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C47 C48 C49 120.20(13) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
C48 C49 C54 119.90(13) . . ?
C48 C49 C50 121.16(13) . . ?
C54 C49 C50 118.94(13) . . ?
O10 C50 C51 124.63(13) . . ?
O10 C50 C49 116.25(12) . . ?
C51 C50 C49 119.12(13) . . ?
C50 C51 C52 121.89(13) . . ?
C50 C51 Br2 118.84(11) . . ?
C52 C51 Br2 119.24(11) . . ?
C53 C52 C51 119.94(13) . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 C54 120.15(13) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C53 C54 C49 119.96(13) . . ?
C53 C54 C45 121.11(13) . . ?
C49 C54 C45 118.92(13) . . ?
C56 C55 H55A 109.5 . . ?
C56 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C56 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O11 C56 C55 120.57(19) . . ?
O11 C56 C57 123.8(2) . . ?
C55 C56 C57 115.7(2) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59 C58 H58A 109.5 . . ?
C59 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C59 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O12 C59 C60 121.40(16) . . ?
O12 C59 C58 121.67(16) . . ?
C60 C59 C58 116.92(14) . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C15 N1 C12 111.73(11) . . ?
C15 N1 C11 124.23(11) . . ?
C12 N1 C11 123.67(11) . . ?
C21 N2 C20 111.76(11) . . ?
C21 N2 C22 124.85(11) . . ?
C20 N2 C22 123.10(11) . . ?
C34 N3 C37 112.02(12) . . ?
C34 N3 C33 125.10(12) . . ?
C37 N3 C33 122.87(12) . . ?
C42 N4 C43 111.77(12) . . ?
C42 N4 C44 124.20(12) . . ?
C43 N4 C44 123.93(12) . . ?
C45 O9 H9 109.5 . . ?
C50 O10 H10 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -59.06(14) . . . . ?
C6 C1 C2 C3 59.00(14) . . . . ?
C11 C1 C2 C3 -177.51(11) . . . . ?
C1 C2 C3 C44 178.60(11) . . . . ?
C1 C2 C3 C10 59.47(14) . . . . ?
C1 C2 C3 C4 -59.01(14) . . . . ?
C44 C3 C4 C5 -178.33(11) . . . . ?
C10 C3 C4 C5 -58.98(14) . . . . ?
C2 C3 C4 C5 59.20(14) . . . . ?
C3 C4 C5 C7 60.23(15) . . . . ?
C3 C4 C5 C6 -60.27(15) . . . . ?
C9 C1 C6 C5 58.81(14) . . . . ?
C2 C1 C6 C5 -59.48(14) . . . . ?
C11 C1 C6 C5 177.66(11) . . . . ?
C7 C5 C6 C1 -59.51(15) . . . . ?
C4 C5 C6 C1 60.55(14) . . . . ?
C4 C5 C7 C8 -60.64(15) . . . . ?
C6 C5 C7 C8 59.25(15) . . . . ?
C5 C7 C8 C9 -59.45(15) . . . . ?
C5 C7 C8 C10 60.46(15) . . . . ?
C6 C1 C9 C8 -59.51(14) . . . . ?
C2 C1 C9 C8 58.61(14) . . . . ?
C11 C1 C9 C8 179.03(11) . . . . ?
C7 C8 C9 C1 60.42(15) . . . . ?
C10 C8 C9 C1 -59.46(15) . . . . ?
C7 C8 C10 C3 -60.02(15) . . . . ?
C9 C8 C10 C3 60.00(15) . . . . ?
C44 C3 C10 C8 179.76(11) . . . . ?
C4 C3 C10 C8 58.93(14) . . . . ?
C2 C3 C10 C8 -59.53(14) . . . . ?
C9 C1 C11 N1 -177.59(11) . . . . ?
C6 C1 C11 N1 63.11(15) . . . . ?
C2 C1 C11 N1 -58.44(15) . . . . ?
O4 C12 C13 C16 -9.8(2) . . . . ?
N1 C12 C13 C16 170.86(13) . . . . ?
O4 C12 C13 C14 172.22(14) . . . . ?
N1 C12 C13 C14 -7.16(14) . . . . ?
C16 C13 C14 C19 0.5(2) . . . . ?
C12 C13 C14 C19 178.68(12) . . . . ?
C16 C13 C14 C15 -176.10(12) . . . . ?
C12 C13 C14 C15 2.10(14) . . . . ?
C19 C14 C15 O1 6.7(2) . . . . ?
C13 C14 C15 O1 -177.03(14) . . . . ?
C19 C14 C15 N1 -172.60(13) . . . . ?
C13 C14 C15 N1 3.70(14) . . . . ?
C14 C13 C16 C17 -0.26(19) . . . . ?
C12 C13 C16 C17 -178.02(13) . . . . ?
C13 C16 C17 C18 0.74(19) . . . . ?
C13 C16 C17 C20 179.47(13) . . . . ?
C16 C17 C18 C19 -1.5(2) . . . . ?
C20 C17 C18 C19 179.55(12) . . . . ?
C16 C17 C18 C21 175.73(12) . . . . ?
C20 C17 C18 C21 -3.24(15) . . . . ?
C13 C14 C19 C18 -1.1(2) . . . . ?
C15 C14 C19 C18 174.75(13) . . . . ?
C17 C18 C19 C14 1.6(2) . . . . ?
C21 C18 C19 C14 -175.01(13) . . . . ?
C16 C17 C20 O3 7.4(2) . . . . ?
C18 C17 C20 O3 -173.78(14) . . . . ?
C16 C17 C20 N2 -173.73(13) . . . . ?
C18 C17 C20 N2 5.14(14) . . . . ?
C17 C18 C21 O2 -178.92(14) . . . . ?
C19 C18 C21 O2 -1.9(2) . . . . ?
C17 C18 C21 N2 0.16(15) . . . . ?
C19 C18 C21 N2 177.13(13) . . . . ?
N2 C22 C23 C28 -65.43(15) . . . . ?
N2 C22 C23 C31 55.76(15) . . . . ?
N2 C22 C23 C24 175.53(11) . . . . ?
C28 C23 C24 C25 59.78(15) . . . . ?
C22 C23 C24 C25 -179.81(12) . . . . ?
C31 C23 C24 C25 -58.69(15) . . . . ?
C23 C24 C25 C32 59.30(16) . . . . ?
C23 C24 C25 C26 -60.45(15) . . . . ?
C32 C25 C26 C27 -59.99(15) . . . . ?
C24 C25 C26 C27 59.83(15) . . . . ?
C25 C26 C27 C29 60.32(15) . . . . ?
C25 C26 C27 C28 -59.91(15) . . . . ?
C26 C27 C28 C23 59.97(15) . . . . ?
C29 C27 C28 C23 -60.37(15) . . . . ?
C22 C23 C28 C27 -178.08(11) . . . . ?
C31 C23 C28 C27 59.37(14) . . . . ?
C24 C23 C28 C27 -59.20(14) . . . . ?
C26 C27 C29 C30 -60.17(14) . . . . ?
C28 C27 C29 C30 60.39(15) . . . . ?
C27 C29 C30 C33 177.33(11) . . . . ?
C27 C29 C30 C32 59.03(14) . . . . ?
C27 C29 C30 C31 -59.37(14) . . . . ?
C28 C23 C31 C30 -59.17(14) . . . . ?
C22 C23 C31 C30 178.51(11) . . . . ?
C24 C23 C31 C30 59.14(14) . . . . ?
C33 C30 C31 C23 -177.88(11) . . . . ?
C32 C30 C31 C23 -59.46(14) . . . . ?
C29 C30 C31 C23 59.15(14) . . . . ?
C26 C25 C32 C30 59.78(15) . . . . ?
C24 C25 C32 C30 -59.81(15) . . . . ?
C33 C30 C32 C25 -179.51(11) . . . . ?
C29 C30 C32 C25 -58.98(14) . . . . ?
C31 C30 C32 C25 59.49(15) . . . . ?
C32 C30 C33 N3 -175.11(11) . . . . ?
C29 C30 C33 N3 65.68(15) . . . . ?
C31 C30 C33 N3 -55.96(15) . . . . ?
O6 C34 C35 C36 -177.29(14) . . . . ?
N3 C34 C35 C36 2.12(15) . . . . ?
O6 C34 C35 C38 4.8(2) . . . . ?
N3 C34 C35 C38 -175.82(13) . . . . ?
C38 C35 C36 C41 0.3(2) . . . . ?
C34 C35 C36 C41 -177.83(12) . . . . ?
C38 C35 C36 C37 178.57(12) . . . . ?
C34 C35 C36 C37 0.47(15) . . . . ?
C41 C36 C37 O5 -5.6(2) . . . . ?
C35 C36 C37 O5 176.22(14) . . . . ?
C41 C36 C37 N3 175.31(13) . . . . ?
C35 C36 C37 N3 -2.86(15) . . . . ?
C36 C35 C38 C39 -0.1(2) . . . . ?
C34 C35 C38 C39 177.60(13) . . . . ?
C35 C38 C39 C40 -0.4(2) . . . . ?
C35 C38 C39 C42 -178.32(13) . . . . ?
C38 C39 C40 C41 0.7(2) . . . . ?
C42 C39 C40 C41 178.99(12) . . . . ?
C38 C39 C40 C43 -177.77(12) . . . . ?
C42 C39 C40 C43 0.54(15) . . . . ?
C39 C40 C41 C36 -0.4(2) . . . . ?
C43 C40 C41 C36 177.67(13) . . . . ?
C35 C36 C41 C40 0.0(2) . . . . ?
C37 C36 C41 C40 -177.95(13) . . . . ?
C38 C39 C42 O7 -5.9(2) . . . . ?
C40 C39 C42 O7 175.90(14) . . . . ?
C38 C39 C42 N4 174.81(14) . . . . ?
C40 C39 C42 N4 -3.34(15) . . . . ?
C41 C40 C43 O8 4.2(2) . . . . ?
C39 C40 C43 O8 -177.51(14) . . . . ?
C41 C40 C43 N4 -175.88(13) . . . . ?
C39 C40 C43 N4 2.46(15) . . . . ?
C10 C3 C44 N4 177.80(11) . . . . ?
C4 C3 C44 N4 -62.57(15) . . . . ?
C2 C3 C44 N4 58.69(15) . . . . ?
O9 C45 C46 C47 -179.09(13) . . . . ?
C54 C45 C46 C47 0.6(2) . . . . ?
O9 C45 C46 Br1 0.23(19) . . . . ?
C54 C45 C46 Br1 179.88(10) . . . . ?
C45 C46 C47 C48 -0.1(2) . . . . ?
Br1 C46 C47 C48 -179.39(11) . . . . ?
C46 C47 C48 C49 -0.5(2) . . . . ?
C47 C48 C49 C54 0.6(2) . . . . ?
C47 C48 C49 C50 -179.22(13) . . . . ?
C48 C49 C50 O10 -1.1(2) . . . . ?
C54 C49 C50 O10 179.06(12) . . . . ?
C48 C49 C50 C51 179.62(13) . . . . ?
C54 C49 C50 C51 -0.2(2) . . . . ?
O10 C50 C51 C52 -179.55(13) . . . . ?
C49 C50 C51 C52 -0.3(2) . . . . ?
O10 C50 C51 Br2 -1.3(2) . . . . ?
C49 C50 C51 Br2 177.93(10) . . . . ?
C50 C51 C52 C53 0.5(2) . . . . ?
Br2 C51 C52 C53 -177.72(11) . . . . ?
C51 C52 C53 C54 -0.2(2) . . . . ?
C52 C53 C54 C49 -0.4(2) . . . . ?
C52 C53 C54 C45 -179.51(13) . . . . ?
C48 C49 C54 C53 -179.27(12) . . . . ?
C50 C49 C54 C53 0.6(2) . . . . ?
C48 C49 C54 C45 -0.1(2) . . . . ?
C50 C49 C54 C45 179.71(12) . . . . ?
O9 C45 C54 C53 -1.6(2) . . . . ?
C46 C45 C54 C53 178.69(13) . . . . ?
O9 C45 C54 C49 179.23(12) . . . . ?
C46 C45 C54 C49 -0.4(2) . . . . ?
O1 C15 N1 C12 172.10(13) . . . . ?
C14 C15 N1 C12 -8.60(14) . . . . ?
O1 C15 N1 C11 -1.2(2) . . . . ?
C14 C15 N1 C11 178.13(11) . . . . ?
O4 C12 N1 C15 -169.52(13) . . . . ?
C13 C12 N1 C15 9.90(14) . . . . ?
O4 C12 N1 C11 3.8(2) . . . . ?
C13 C12 N1 C11 -176.79(11) . . . . ?
C1 C11 N1 C15 -92.69(15) . . . . ?
C1 C11 N1 C12 94.83(15) . . . . ?
O2 C21 N2 C20 -177.63(13) . . . . ?
C18 C21 N2 C20 3.27(15) . . . . ?
O2 C21 N2 C22 -3.8(2) . . . . ?
C18 C21 N2 C22 177.10(11) . . . . ?
O3 C20 N2 C21 173.77(13) . . . . ?
C17 C20 N2 C21 -5.19(14) . . . . ?
O3 C20 N2 C22 -0.2(2) . . . . ?
C17 C20 N2 C22 -179.14(11) . . . . ?
C23 C22 N2 C21 92.75(15) . . . . ?
C23 C22 N2 C20 -94.09(15) . . . . ?
O6 C34 N3 C37 175.32(14) . . . . ?
C35 C34 N3 C37 -4.10(15) . . . . ?
O6 C34 N3 C33 -3.1(2) . . . . ?
C35 C34 N3 C33 177.51(12) . . . . ?
O5 C37 N3 C34 -174.75(13) . . . . ?
C36 C37 N3 C34 4.36(15) . . . . ?
O5 C37 N3 C33 3.7(2) . . . . ?
C36 C37 N3 C33 -177.21(12) . . . . ?
C30 C33 N3 C34 -91.28(16) . . . . ?
C30 C33 N3 C37 90.50(15) . . . . ?
O7 C42 N4 C43 -174.21(13) . . . . ?
C39 C42 N4 C43 5.07(15) . . . . ?
O7 C42 N4 C44 2.3(2) . . . . ?
C39 C42 N4 C44 -178.39(12) . . . . ?
O8 C43 N4 C42 175.20(13) . . . . ?
C40 C43 N4 C42 -4.77(15) . . . . ?
O8 C43 N4 C44 -1.3(2) . . . . ?
C40 C43 N4 C44 178.68(11) . . . . ?
C3 C44 N4 C42 92.09(15) . . . . ?
C3 C44 N4 C43 -91.79(15) . . . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2389270'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C103.50 H93.75 Br2 Cl9.75 N8 O16.75'
_chemical_formula_weight         2223.03

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'
Br Br -0.6763 1.2805 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.590(2)
_cell_length_b                   15.202(4)
_cell_length_c                   18.069(3)
_cell_angle_alpha                107.935(14)
_cell_angle_beta                 95.420(14)
_cell_angle_gamma                92.865(17)
_cell_volume                     2486.5(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.033
_shelx_estimated_absorpt_T_min   0.499
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            35907
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.333
_diffrn_reflns_theta_max         79.101
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             10087
_reflns_number_gt                9339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+3.6213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10087
_refine_ls_number_parameters     708
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C54 C 0.1991(9) 1.1399(8) 0.4007(6) 0.0539(14) Uani 0.375(3) 1 d D U P A -4
C55 C 0.2349(11) 1.1590(10) 0.4852(6) 0.0480(17) Uani 0.375(3) 1 d . U P A -4
H55A H 0.155208 1.137363 0.507096 0.072 Uiso 0.375(3) 1 calc R U P A -4
H55B H 0.256320 1.225860 0.510518 0.072 Uiso 0.375(3) 1 calc R U P A -4
H55C H 0.317153 1.126394 0.494501 0.072 Uiso 0.375(3) 1 calc R U P A -4
C56 C 0.1668(11) 1.0617(10) 0.3331(7) 0.0589(17) Uani 0.375(3) 1 d . U P A -4
H56A H 0.115050 1.012561 0.346608 0.088 Uiso 0.375(3) 1 calc R U P A -4
H56B H 0.254056 1.039109 0.312933 0.088 Uiso 0.375(3) 1 calc R U P A -4
H56C H 0.108893 1.079071 0.293029 0.088 Uiso 0.375(3) 1 calc R U P A -4
O9 O 0.2213(5) 1.2008(5) 0.3828(3) 0.0446(13) Uani 0.375(3) 1 d D U P A -4
C50 C 0.1451(6) 1.0744(4) 0.4316(3) 0.0493(14) Uani 0.625(3) 1 d . . P A -3
H50 H 0.187171 1.013376 0.419265 0.059 Uiso 0.625(3) 1 calc R U P A -3
Cl1 Cl 0.1359(5) 1.1083(3) 0.35104(17) 0.1369(16) Uani 0.625(3) 1 d . . P A -3
Cl2 Cl -0.0292(2) 1.05743(12) 0.44939(18) 0.1157(12) Uani 0.625(3) 1 d . . P A
-3
Cl3 Cl 0.23637(16) 1.14916(13) 0.51770(11) 0.0620(6) Uani 0.625(3) 1 d . . P A
-3
C52 C 0.6887(6) 0.1049(4) 0.0556(4) 0.0368(13) Uani 0.482(3) 1 d . . P B -2
H52 H 0.688356 0.123681 0.113660 0.044 Uiso 0.482(3) 1 calc R U P B -2
Cl7 Cl 0.53060(17) 0.04187(13) 0.00574(12) 0.0515(5) Uani 0.482(3) 1 d . . P B
-2
Cl8 Cl 0.8258(2) 0.04001(15) 0.02565(12) 0.0247(4) Uani 0.482(3) 1 d . . P B -2
Cl9 Cl 0.7127(7) 0.2130(5) 0.0187(3) 0.0551(11) Uani 0.482(3) 1 d . . P B -2
C51 C 0.7429(7) 0.0974(5) -0.0351(4) 0.0481(15) Uani 0.518(3) 1 d . . P B -1
H51 H 0.651814 0.060628 -0.059853 0.058 Uiso 0.518(3) 1 calc R U P B -1
Cl4 Cl 0.8225(6) 0.0440(4) 0.0218(4) 0.1133(19) Uani 0.518(3) 1 d . . P B -1
Cl5 Cl 0.6989(5) 0.2160(3) 0.0427(2) 0.0434(7) Uani 0.518(3) 1 d . . P B -1
Cl6 Cl 0.84822(17) 0.09536(12) -0.11019(9) 0.0492(5) Uani 0.518(3) 1 d . . P B
-1
C1 C 0.8580(3) 0.81519(17) 0.86656(14) 0.0257(5) Uani 1 1 d . . . . .
H1 H 0.897399 0.881373 0.883148 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9487(2) 0.75481(17) 0.80816(14) 0.0239(5) Uani 1 1 d . . . . .
H2A H 1.046753 0.760958 0.833042 0.029 Uiso 1 1 calc R U . . .
H2B H 0.949126 0.776402 0.761779 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8904(2) 0.65240(17) 0.78235(13) 0.0213(5) Uani 1 1 d . . . . .
C4 C 0.8903(3) 0.61955(19) 0.85514(14) 0.0272(5) Uani 1 1 d . . . . .
H4A H 0.852596 0.553786 0.839175 0.033 Uiso 1 1 calc R U . . .
H4B H 0.987675 0.624363 0.880600 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7991(3) 0.6800(2) 0.91322(14) 0.0293(5) Uani 1 1 d . . . . .
H5 H 0.798902 0.658345 0.960184 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8594(3) 0.7816(2) 0.93874(14) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.956874 0.787298 0.964262 0.037 Uiso 1 1 calc R U . . .
H6B H 0.802287 0.820520 0.977008 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7077(3) 0.80717(17) 0.82733(14) 0.0242(5) Uani 1 1 d . . . . .
H7A H 0.707191 0.829421 0.781267 0.029 Uiso 1 1 calc R U . . .
H7B H 0.649167 0.846405 0.864505 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7384(2) 0.64392(16) 0.74383(13) 0.0196(4) Uani 1 1 d . . . . .
H8A H 0.699626 0.578356 0.727760 0.024 Uiso 1 1 calc R U . . .
H8B H 0.737189 0.663395 0.696312 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6459(2) 0.70505(16) 0.80122(13) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.6482(3) 0.67180(18) 0.87367(14) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.589132 0.709814 0.911261 0.031 Uiso 1 1 calc R U . . .
H10B H 0.608695 0.606412 0.857695 0.031 Uiso 1 1 calc R U . . .
C11 C 0.9828(2) 0.58967(17) 0.72628(13) 0.0231(5) Uani 1 1 d . . . . .
H11A H 1.081341 0.601021 0.751056 0.028 Uiso 1 1 calc R U . . .
H11B H 0.951678 0.523967 0.718216 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0678(2) 0.66669(17) 0.62995(13) 0.0219(5) Uani 1 1 d . . . . .
C13 C 1.0183(2) 0.65891(16) 0.54675(13) 0.0208(4) Uani 1 1 d . . . . .
C14 C 1.0687(2) 0.70752(17) 0.49972(14) 0.0226(5) Uani 1 1 d . . . . .
H14 H 1.146761 0.752731 0.517045 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9956(2) 0.68458(16) 0.42520(13) 0.0212(4) Uani 1 1 d . . . . .
C16 C 1.0161(2) 0.72408(17) 0.36028(14) 0.0239(5) Uani 1 1 d . . . . .
C17 C 0.8309(3) 0.61043(16) 0.31718(13) 0.0229(5) Uani 1 1 d . . . . .
C18 C 0.8827(2) 0.61708(16) 0.39955(13) 0.0215(5) Uani 1 1 d . . . . .
C19 C 0.8322(2) 0.56823(16) 0.44628(13) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.754667 0.522615 0.428871 0.025 Uiso 1 1 calc R U . . .
C20 C 0.9052(2) 0.59206(16) 0.52087(13) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.8816(2) 0.55368(16) 0.58592(13) 0.0210(5) Uani 1 1 d . . . . .
C22 C 0.8922(3) 0.69585(18) 0.22349(14) 0.0258(5) Uani 1 1 d . . . . .
H22A H 0.857131 0.636682 0.182696 0.031 Uiso 1 1 calc R U . . .
H22B H 0.985160 0.715174 0.211331 0.031 Uiso 1 1 calc R U . . .
C23 C 0.7903(3) 0.77001(17) 0.21905(14) 0.0240(5) Uani 1 1 d . . . . .
C24 C 0.8523(3) 0.86786(18) 0.26990(16) 0.0302(5) Uani 1 1 d . . . . .
H24A H 0.867875 0.870112 0.325427 0.036 Uiso 1 1 calc R U . . .
H24B H 0.944224 0.881807 0.253437 0.036 Uiso 1 1 calc R U . . .
C25 C 0.7519(3) 0.94119(19) 0.26170(18) 0.0339(6) Uani 1 1 d . . . . .
H25 H 0.793549 1.004294 0.294712 0.041 Uiso 1 1 calc R U . . .
C26 C 0.7281(3) 0.9378(2) 0.1756(2) 0.0432(7) Uani 1 1 d . . . . .
H26A H 0.663586 0.984801 0.170158 0.052 Uiso 1 1 calc R U . . .
H26B H 0.818581 0.952183 0.157965 0.052 Uiso 1 1 calc R U . . .
C27 C 0.6649(3) 0.8412(2) 0.12497(17) 0.0383(7) Uani 1 1 d . . . . .
H27 H 0.649599 0.839439 0.069000 0.046 Uiso 1 1 calc R U . . .
C28 C 0.7658(3) 0.7674(2) 0.13266(15) 0.0328(6) Uani 1 1 d . . . . .
H28A H 0.724842 0.705070 0.099581 0.039 Uiso 1 1 calc R U . . .
H28B H 0.856617 0.780075 0.114410 0.039 Uiso 1 1 calc R U . . .
C29 C 0.6477(2) 0.74949(16) 0.24519(13) 0.0211(4) Uani 1 1 d . . . . .
H29A H 0.661591 0.749471 0.300172 0.025 Uiso 1 1 calc R U . . .
H29B H 0.606307 0.687191 0.212200 0.025 Uiso 1 1 calc R U . . .
C30 C 0.6112(3) 0.91960(17) 0.28905(16) 0.0276(5) Uani 1 1 d . . . . .
H30A H 0.546158 0.966939 0.285076 0.033 Uiso 1 1 calc R U . . .
H30B H 0.626337 0.921694 0.344551 0.033 Uiso 1 1 calc R U . . .
C31 C 0.5459(3) 0.82295(17) 0.23826(13) 0.0227(5) Uani 1 1 d . . . . .
C32 C 0.5243(3) 0.8203(2) 0.15195(15) 0.0324(6) Uani 1 1 d . . . . .
H32A H 0.482077 0.758278 0.118816 0.039 Uiso 1 1 calc R U . . .
H32B H 0.458869 0.866804 0.146228 0.039 Uiso 1 1 calc R U . . .
C33 C 0.4017(3) 0.80260(17) 0.26219(14) 0.0240(5) Uani 1 1 d . . . . .
H33A H 0.344048 0.855019 0.262951 0.029 Uiso 1 1 calc R U . . .
H33B H 0.353854 0.746404 0.222255 0.029 Uiso 1 1 calc R U . . .
C34 C 0.3987(2) 0.85712(16) 0.40916(14) 0.0216(5) Uani 1 1 d . . . . .
C35 C 0.4113(2) 0.81041(15) 0.47092(13) 0.0199(4) Uani 1 1 d . . . . .
C36 C 0.4192(2) 0.84903(15) 0.55209(13) 0.0214(4) Uani 1 1 d . . . . .
H36 H 0.412710 0.913255 0.577390 0.026 Uiso 1 1 calc R U . . .
C37 C 0.4374(2) 0.78522(16) 0.59302(13) 0.0201(4) Uani 1 1 d . . . . .
C38 C 0.4535(2) 0.80050(16) 0.67968(14) 0.0218(5) Uani 1 1 d . . . . .
C39 C 0.4671(2) 0.64377(16) 0.61655(13) 0.0203(4) Uani 1 1 d . . . . .
C40 C 0.4464(2) 0.69057(15) 0.55528(13) 0.0193(4) Uani 1 1 d . . . . .
C41 C 0.4387(2) 0.65164(15) 0.47442(13) 0.0203(4) Uani 1 1 d . . . . .
H41 H 0.445569 0.587445 0.449233 0.024 Uiso 1 1 calc R U . . .
C42 C 0.4199(2) 0.71543(15) 0.43355(13) 0.0199(4) Uani 1 1 d . . . . .
C43 C 0.4108(2) 0.69928(16) 0.34737(14) 0.0213(4) Uani 1 1 d . . . . .
C44 C 0.4933(2) 0.69485(17) 0.76341(13) 0.0229(5) Uani 1 1 d . . . . .
H44A H 0.452765 0.630893 0.755110 0.027 Uiso 1 1 calc R U . . .
H44B H 0.438148 0.737877 0.800089 0.027 Uiso 1 1 calc R U . . .
C45 C 0.6238(3) 0.44980(17) -0.07371(14) 0.0244(5) Uani 1 1 d . . . . .
H45 H 0.629248 0.434331 -0.128400 0.029 Uiso 1 1 calc R U . . .
C46 C 0.7318(3) 0.43503(17) -0.02507(15) 0.0263(5) Uani 1 1 d . . . . .
C47 C 0.7281(3) 0.45764(18) 0.05661(15) 0.0279(5) Uani 1 1 d . . . . .
H47 H 0.805380 0.447298 0.088948 0.034 Uiso 1 1 calc R U . . .
C48 C 0.6124(3) 0.49445(17) 0.08866(14) 0.0261(5) Uani 1 1 d . . . . .
H48 H 0.609171 0.508997 0.143468 0.031 Uiso 1 1 calc R U . . .
C49 C 0.4969(2) 0.51129(16) 0.04100(13) 0.0210(5) Uani 1 1 d . . . . .
Br1 Br 0.89376(3) 0.38184(2) -0.06783(2) 0.04025(12) Uani 1 1 d . . . . .
N1 N 0.9774(2) 0.60512(14) 0.64984(11) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.9104(2) 0.67943(14) 0.29975(11) 0.0229(4) Uani 1 1 d . . . . .
N3 N 0.4786(2) 0.71381(13) 0.68844(11) 0.0196(4) Uani 1 1 d . . . . .
N4 N 0.4092(2) 0.78842(13) 0.33868(11) 0.0208(4) Uani 1 1 d . . . . .
O1 O 1.16678(17) 0.71437(13) 0.67199(10) 0.0283(4) Uani 1 1 d . . . . .
O2 O 1.10497(19) 0.78253(14) 0.35863(11) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.74150(19) 0.55591(12) 0.27285(10) 0.0278(4) Uani 1 1 d . . . . .
O4 O 0.80072(18) 0.48998(12) 0.58509(10) 0.0256(4) Uani 1 1 d . . . . .
O5 O 0.38393(19) 0.93892(12) 0.41724(10) 0.0265(4) Uani 1 1 d . . . . .
O6 O 0.4468(2) 0.87163(12) 0.73272(10) 0.0290(4) Uani 1 1 d . . . . .
O7 O 0.47079(18) 0.56108(11) 0.60760(10) 0.0252(4) Uani 1 1 d . . . . .
O8 O 0.40483(19) 0.62682(12) 0.29433(10) 0.0276(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C54 O9 1.088(11) . ?
C54 C56 1.414(17) . ?
C54 C55 1.467(14) . ?
C50 Cl1 1.683(6) . ?
C50 Cl3 1.742(6) . ?
C50 Cl2 1.753(7) . ?
C52 Cl8 1.712(7) . ?
C52 Cl7 1.759(6) . ?
C52 Cl9 1.965(9) . ?
C51 Cl4 1.652(9) . ?
C51 Cl6 1.760(7) . ?
C51 Cl5 2.007(9) . ?
C1 C7 1.527(3) . ?
C1 C6 1.539(3) . ?
C1 C2 1.539(3) . ?
C2 C3 1.540(3) . ?
C3 C8 1.536(3) . ?
C3 C11 1.543(3) . ?
C3 C4 1.544(3) . ?
C4 C5 1.539(4) . ?
C5 C10 1.534(4) . ?
C5 C6 1.535(4) . ?
C7 C9 1.545(3) . ?
C8 C9 1.546(3) . ?
C9 C44 1.535(3) . ?
C9 C10 1.540(3) . ?
C11 N1 1.467(3) . ?
C12 O1 1.208(3) . ?
C12 N1 1.393(3) . ?
C12 C13 1.500(3) . ?
C13 C20 1.389(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.391(3) . ?
C15 C18 1.393(3) . ?
C15 C16 1.497(3) . ?
C16 O2 1.209(3) . ?
C16 N2 1.396(3) . ?
C17 O3 1.206(3) . ?
C17 N2 1.396(3) . ?
C17 C18 1.495(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.494(3) . ?
C21 O4 1.206(3) . ?
C21 N1 1.400(3) . ?
C22 N2 1.471(3) . ?
C22 C23 1.544(3) . ?
C23 C29 1.536(3) . ?
C23 C24 1.542(4) . ?
C23 C28 1.544(3) . ?
C24 C25 1.541(4) . ?
C25 C30 1.534(4) . ?
C25 C26 1.534(4) . ?
C26 C27 1.529(5) . ?
C27 C32 1.528(4) . ?
C27 C28 1.547(4) . ?
C29 C31 1.545(3) . ?
C30 C31 1.537(3) . ?
C31 C33 1.532(3) . ?
C31 C32 1.542(3) . ?
C33 N4 1.459(3) . ?
C34 O5 1.224(3) . ?
C34 N4 1.392(3) . ?
C34 C35 1.495(3) . ?
C35 C36 1.395(3) . ?
C35 C42 1.403(3) . ?
C36 C37 1.397(3) . ?
C37 C40 1.401(3) . ?
C37 C38 1.502(3) . ?
C38 O6 1.213(3) . ?
C38 N3 1.405(3) . ?
C39 O7 1.220(3) . ?
C39 N3 1.394(3) . ?
C39 C40 1.493(3) . ?
C40 C41 1.390(3) . ?
C41 C42 1.397(3) . ?
C42 C43 1.493(3) . ?
C43 O8 1.212(3) . ?
C43 N4 1.412(3) . ?
C44 N3 1.465(3) . ?
C45 C46 1.367(4) . ?
C45 C49 1.422(3) 2_665 ?
C46 C47 1.413(4) . ?
C46 Br1 1.905(3) . ?
C47 C48 1.364(4) . ?
C48 C49 1.421(3) . ?
C49 C49 1.422(4) 2_665 ?

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
O9 C54 C56 109.0(11) . . ?
O9 C54 C55 112.0(11) . . ?
C56 C54 C55 137.9(11) . . ?
Cl1 C50 Cl3 118.0(4) . . ?
Cl1 C50 Cl2 105.8(3) . . ?
Cl3 C50 Cl2 107.5(3) . . ?
Cl8 C52 Cl7 108.8(3) . . ?
Cl8 C52 Cl9 105.3(4) . . ?
Cl7 C52 Cl9 106.9(4) . . ?
Cl4 C51 Cl6 107.8(5) . . ?
Cl4 C51 Cl5 102.3(4) . . ?
Cl6 C51 Cl5 122.6(4) . . ?
C7 C1 C6 110.0(2) . . ?
C7 C1 C2 109.40(19) . . ?
C6 C1 C2 109.1(2) . . ?
C1 C2 C3 110.3(2) . . ?
C8 C3 C2 109.03(19) . . ?
C8 C3 C11 111.10(18) . . ?
C2 C3 C11 111.39(19) . . ?
C8 C3 C4 108.69(19) . . ?
C2 C3 C4 109.11(19) . . ?
C11 C3 C4 107.45(19) . . ?
C5 C4 C3 109.6(2) . . ?
C10 C5 C6 109.4(2) . . ?
C10 C5 C4 109.5(2) . . ?
C6 C5 C4 109.5(2) . . ?
C5 C6 C1 109.4(2) . . ?
C1 C7 C9 109.9(2) . . ?
C3 C8 C9 110.68(18) . . ?
C44 C9 C10 108.42(19) . . ?
C44 C9 C7 111.26(19) . . ?
C10 C9 C7 108.80(19) . . ?
C44 C9 C8 110.69(18) . . ?
C10 C9 C8 108.08(19) . . ?
C7 C9 C8 109.51(19) . . ?
C5 C10 C9 110.4(2) . . ?
N1 C11 C3 113.28(19) . . ?
O1 C12 N1 125.8(2) . . ?
O1 C12 C13 128.3(2) . . ?
N1 C12 C13 105.93(19) . . ?
C20 C13 C14 122.6(2) . . ?
C20 C13 C12 108.0(2) . . ?
C14 C13 C12 129.4(2) . . ?
C13 C14 C15 114.5(2) . . ?
C14 C15 C18 122.5(2) . . ?
C14 C15 C16 129.6(2) . . ?
C18 C15 C16 107.9(2) . . ?
O2 C16 N2 125.6(2) . . ?
O2 C16 C15 128.4(2) . . ?
N2 C16 C15 106.0(2) . . ?
O3 C17 N2 125.8(2) . . ?
O3 C17 C18 128.2(2) . . ?
N2 C17 C18 106.1(2) . . ?
C19 C18 C15 123.1(2) . . ?
C19 C18 C17 129.0(2) . . ?
C15 C18 C17 107.9(2) . . ?
C18 C19 C20 114.0(2) . . ?
C13 C20 C19 123.3(2) . . ?
C13 C20 C21 108.0(2) . . ?
C19 C20 C21 128.8(2) . . ?
O4 C21 N1 125.4(2) . . ?
O4 C21 C20 128.6(2) . . ?
N1 C21 C20 105.99(19) . . ?
N2 C22 C23 114.49(19) . . ?
C29 C23 C24 108.9(2) . . ?
C29 C23 C22 111.5(2) . . ?
C24 C23 C22 111.4(2) . . ?
C29 C23 C28 108.3(2) . . ?
C24 C23 C28 109.1(2) . . ?
C22 C23 C28 107.49(19) . . ?
C25 C24 C23 110.5(2) . . ?
C30 C25 C26 109.5(2) . . ?
C30 C25 C24 108.8(2) . . ?
C26 C25 C24 109.5(2) . . ?
C27 C26 C25 109.8(2) . . ?
C32 C27 C26 109.2(2) . . ?
C32 C27 C28 109.5(2) . . ?
C26 C27 C28 110.0(3) . . ?
C23 C28 C27 109.6(2) . . ?
C23 C29 C31 110.77(19) . . ?
C25 C30 C31 110.0(2) . . ?
C33 C31 C30 110.5(2) . . ?
C33 C31 C32 107.7(2) . . ?
C30 C31 C32 109.1(2) . . ?
C33 C31 C29 111.71(19) . . ?
C30 C31 C29 109.3(2) . . ?
C32 C31 C29 108.38(19) . . ?
C27 C32 C31 110.1(2) . . ?
N4 C33 C31 113.47(19) . . ?
O5 C34 N4 125.8(2) . . ?
O5 C34 C35 128.2(2) . . ?
N4 C34 C35 105.99(19) . . ?
C36 C35 C42 122.8(2) . . ?
C36 C35 C34 129.3(2) . . ?
C42 C35 C34 107.8(2) . . ?
C35 C36 C37 114.3(2) . . ?
C36 C37 C40 122.5(2) . . ?
C36 C37 C38 129.8(2) . . ?
C40 C37 C38 107.67(19) . . ?
O6 C38 N3 125.5(2) . . ?
O6 C38 C37 128.7(2) . . ?
N3 C38 C37 105.75(19) . . ?
O7 C39 N3 125.5(2) . . ?
O7 C39 C40 128.3(2) . . ?
N3 C39 C40 106.22(19) . . ?
C41 C40 C37 123.5(2) . . ?
C41 C40 C39 128.5(2) . . ?
C37 C40 C39 108.06(19) . . ?
C40 C41 C42 113.9(2) . . ?
C41 C42 C35 122.9(2) . . ?
C41 C42 C43 128.8(2) . . ?
C35 C42 C43 108.3(2) . . ?
O8 C43 N4 125.5(2) . . ?
O8 C43 C42 129.3(2) . . ?
N4 C43 C42 105.21(19) . . ?
N3 C44 C9 113.76(19) . . ?
C46 C45 C49 118.8(2) . 2_665 ?
C45 C46 C47 122.3(2) . . ?
C45 C46 Br1 119.51(19) . . ?
C47 C46 Br1 118.21(19) . . ?
C48 C47 C46 119.5(2) . . ?
C47 C48 C49 120.8(2) . . ?
C48 C49 C45 121.3(2) . 2_665 ?
C48 C49 C49 118.9(3) . 2_665 ?
C45 C49 C49 119.7(3) 2_665 2_665 ?
C12 N1 C21 111.85(19) . . ?
C12 N1 C11 125.90(19) . . ?
C21 N1 C11 122.2(2) . . ?
C16 N2 C17 111.84(19) . . ?
C16 N2 C22 124.7(2) . . ?
C17 N2 C22 123.2(2) . . ?
C39 N3 C38 111.97(19) . . ?
C39 N3 C44 122.67(19) . . ?
C38 N3 C44 124.71(19) . . ?
C34 N4 C43 112.24(19) . . ?
C34 N4 C33 125.09(19) . . ?
C43 N4 C33 122.25(19) . . ?

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
C7 C1 C2 C3 -60.5(3) . . . . ?
C6 C1 C2 C3 59.8(2) . . . . ?
C1 C2 C3 C8 59.3(2) . . . . ?
C1 C2 C3 C11 -177.74(18) . . . . ?
C1 C2 C3 C4 -59.3(2) . . . . ?
C8 C3 C4 C5 -59.6(3) . . . . ?
C2 C3 C4 C5 59.2(3) . . . . ?
C11 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C10 59.7(3) . . . . ?
C3 C4 C5 C6 -60.3(3) . . . . ?
C10 C5 C6 C1 -59.4(3) . . . . ?
C4 C5 C6 C1 60.7(3) . . . . ?
C7 C1 C6 C5 59.8(3) . . . . ?
C2 C1 C6 C5 -60.2(3) . . . . ?
C6 C1 C7 C9 -59.9(3) . . . . ?
C2 C1 C7 C9 59.9(3) . . . . ?
C2 C3 C8 C9 -58.3(2) . . . . ?
C11 C3 C8 C9 178.52(18) . . . . ?
C4 C3 C8 C9 60.5(2) . . . . ?
C1 C7 C9 C44 178.51(19) . . . . ?
C1 C7 C9 C10 59.1(2) . . . . ?
C1 C7 C9 C8 -58.8(2) . . . . ?
C3 C8 C9 C44 -178.69(18) . . . . ?
C3 C8 C9 C10 -60.1(2) . . . . ?
C3 C8 C9 C7 58.3(2) . . . . ?
C6 C5 C10 C9 59.9(3) . . . . ?
C4 C5 C10 C9 -60.2(3) . . . . ?
C44 C9 C10 C5 179.6(2) . . . . ?
C7 C9 C10 C5 -59.3(3) . . . . ?
C8 C9 C10 C5 59.5(3) . . . . ?
C8 C3 C11 N1 53.6(3) . . . . ?
C2 C3 C11 N1 -68.1(2) . . . . ?
C4 C3 C11 N1 172.39(19) . . . . ?
O1 C12 C13 C20 176.9(2) . . . . ?
N1 C12 C13 C20 -1.7(2) . . . . ?
O1 C12 C13 C14 -3.9(4) . . . . ?
N1 C12 C13 C14 177.5(2) . . . . ?
C20 C13 C14 C15 0.8(3) . . . . ?
C12 C13 C14 C15 -178.4(2) . . . . ?
C13 C14 C15 C18 -1.1(3) . . . . ?
C13 C14 C15 C16 177.8(2) . . . . ?
C14 C15 C16 O2 2.9(4) . . . . ?
C18 C15 C16 O2 -178.1(2) . . . . ?
C14 C15 C16 N2 -177.2(2) . . . . ?
C18 C15 C16 N2 1.8(3) . . . . ?
C14 C15 C18 C19 1.1(4) . . . . ?
C16 C15 C18 C19 -178.0(2) . . . . ?
C14 C15 C18 C17 -179.6(2) . . . . ?
C16 C15 C18 C17 1.3(2) . . . . ?
O3 C17 C18 C19 -6.4(4) . . . . ?
N2 C17 C18 C19 175.3(2) . . . . ?
O3 C17 C18 C15 174.4(2) . . . . ?
N2 C17 C18 C15 -3.9(2) . . . . ?
C15 C18 C19 C20 -0.6(3) . . . . ?
C17 C18 C19 C20 -179.7(2) . . . . ?
C14 C13 C20 C19 -0.4(4) . . . . ?
C12 C13 C20 C19 178.9(2) . . . . ?
C14 C13 C20 C21 179.3(2) . . . . ?
C12 C13 C20 C21 -1.4(2) . . . . ?
C18 C19 C20 C13 0.2(3) . . . . ?
C18 C19 C20 C21 -179.3(2) . . . . ?
C13 C20 C21 O4 -174.0(2) . . . . ?
C19 C20 C21 O4 5.6(4) . . . . ?
C13 C20 C21 N1 4.0(2) . . . . ?
C19 C20 C21 N1 -176.4(2) . . . . ?
N2 C22 C23 C29 -52.8(3) . . . . ?
N2 C22 C23 C24 69.2(3) . . . . ?
N2 C22 C23 C28 -171.4(2) . . . . ?
C29 C23 C24 C25 -59.1(3) . . . . ?
C22 C23 C24 C25 177.5(2) . . . . ?
C28 C23 C24 C25 59.0(3) . . . . ?
C23 C24 C25 C30 60.4(3) . . . . ?
C23 C24 C25 C26 -59.3(3) . . . . ?
C30 C25 C26 C27 -59.8(3) . . . . ?
C24 C25 C26 C27 59.4(3) . . . . ?
C25 C26 C27 C32 60.2(3) . . . . ?
C25 C26 C27 C28 -59.9(3) . . . . ?
C29 C23 C28 C27 59.8(3) . . . . ?
C24 C23 C28 C27 -58.7(3) . . . . ?
C22 C23 C28 C27 -179.6(2) . . . . ?
C32 C27 C28 C23 -60.3(3) . . . . ?
C26 C27 C28 C23 59.7(3) . . . . ?
C24 C23 C29 C31 58.2(2) . . . . ?
C22 C23 C29 C31 -178.49(19) . . . . ?
C28 C23 C29 C31 -60.4(3) . . . . ?
C26 C25 C30 C31 59.2(3) . . . . ?
C24 C25 C30 C31 -60.4(3) . . . . ?
C25 C30 C31 C33 -177.0(2) . . . . ?
C25 C30 C31 C32 -58.7(3) . . . . ?
C25 C30 C31 C29 59.6(3) . . . . ?
C23 C29 C31 C33 178.65(19) . . . . ?
C23 C29 C31 C30 -58.7(2) . . . . ?
C23 C29 C31 C32 60.1(3) . . . . ?
C26 C27 C32 C31 -60.2(3) . . . . ?
C28 C27 C32 C31 60.3(3) . . . . ?
C33 C31 C32 C27 179.4(2) . . . . ?
C30 C31 C32 C27 59.4(3) . . . . ?
C29 C31 C32 C27 -59.5(3) . . . . ?
C30 C31 C33 N4 -70.0(3) . . . . ?
C32 C31 C33 N4 170.8(2) . . . . ?
C29 C31 C33 N4 51.9(3) . . . . ?
O5 C34 C35 C36 -5.0(4) . . . . ?
N4 C34 C35 C36 174.2(2) . . . . ?
O5 C34 C35 C42 177.2(2) . . . . ?
N4 C34 C35 C42 -3.5(2) . . . . ?
C42 C35 C36 C37 0.4(3) . . . . ?
C34 C35 C36 C37 -177.0(2) . . . . ?
C35 C36 C37 C40 -0.2(3) . . . . ?
C35 C36 C37 C38 178.5(2) . . . . ?
C36 C37 C38 O6 4.2(4) . . . . ?
C40 C37 C38 O6 -176.9(2) . . . . ?
C36 C37 C38 N3 -175.8(2) . . . . ?
C40 C37 C38 N3 3.0(2) . . . . ?
C36 C37 C40 C41 0.2(4) . . . . ?
C38 C37 C40 C41 -178.7(2) . . . . ?
C36 C37 C40 C39 179.4(2) . . . . ?
C38 C37 C40 C39 0.5(2) . . . . ?
O7 C39 C40 C41 -6.0(4) . . . . ?
N3 C39 C40 C41 175.3(2) . . . . ?
O7 C39 C40 C37 174.9(2) . . . . ?
N3 C39 C40 C37 -3.8(2) . . . . ?
C37 C40 C41 C42 -0.5(3) . . . . ?
C39 C40 C41 C42 -179.4(2) . . . . ?
C40 C41 C42 C35 0.7(3) . . . . ?
C40 C41 C42 C43 178.3(2) . . . . ?
C36 C35 C42 C41 -0.7(4) . . . . ?
C34 C35 C42 C41 177.2(2) . . . . ?
C36 C35 C42 C43 -178.8(2) . . . . ?
C34 C35 C42 C43 -0.9(2) . . . . ?
C41 C42 C43 O8 7.6(4) . . . . ?
C35 C42 C43 O8 -174.6(2) . . . . ?
C41 C42 C43 N4 -173.0(2) . . . . ?
C35 C42 C43 N4 4.9(2) . . . . ?
C10 C9 C44 N3 -173.12(19) . . . . ?
C7 C9 C44 N3 67.3(2) . . . . ?
C8 C9 C44 N3 -54.7(3) . . . . ?
C49 C45 C46 C47 -0.4(4) 2_665 . . . ?
C49 C45 C46 Br1 179.40(17) 2_665 . . . ?
C45 C46 C47 C48 0.8(4) . . . . ?
Br1 C46 C47 C48 -179.0(2) . . . . ?
C46 C47 C48 C49 -0.8(4) . . . . ?
C47 C48 C49 C45 -179.6(2) . . . 2_665 ?
C47 C48 C49 C49 0.3(4) . . . 2_665 ?
O1 C12 N1 C21 -174.2(2) . . . . ?
C13 C12 N1 C21 4.5(3) . . . . ?
O1 C12 N1 C11 2.5(4) . . . . ?
C13 C12 N1 C11 -178.9(2) . . . . ?
O4 C21 N1 C12 172.8(2) . . . . ?
C20 C21 N1 C12 -5.3(3) . . . . ?
O4 C21 N1 C11 -4.0(4) . . . . ?
C20 C21 N1 C11 177.88(19) . . . . ?
C3 C11 N1 C12 91.5(3) . . . . ?
C3 C11 N1 C21 -92.2(3) . . . . ?
O2 C16 N2 C17 175.4(2) . . . . ?
C15 C16 N2 C17 -4.5(3) . . . . ?
O2 C16 N2 C22 1.0(4) . . . . ?
C15 C16 N2 C22 -178.9(2) . . . . ?
O3 C17 N2 C16 -173.1(2) . . . . ?
C18 C17 N2 C16 5.3(3) . . . . ?
O3 C17 N2 C22 1.4(4) . . . . ?
C18 C17 N2 C22 179.8(2) . . . . ?
C23 C22 N2 C16 -92.9(3) . . . . ?
C23 C22 N2 C17 93.2(3) . . . . ?
O7 C39 N3 C38 -172.8(2) . . . . ?
C40 C39 N3 C38 5.9(2) . . . . ?
O7 C39 N3 C44 -1.7(3) . . . . ?
C40 C39 N3 C44 177.01(19) . . . . ?
O6 C38 N3 C39 174.3(2) . . . . ?
C37 C38 N3 C39 -5.6(2) . . . . ?
O6 C38 N3 C44 3.4(4) . . . . ?
C37 C38 N3 C44 -176.50(19) . . . . ?
C9 C44 N3 C39 96.9(2) . . . . ?
C9 C44 N3 C38 -93.1(3) . . . . ?
O5 C34 N4 C43 -173.8(2) . . . . ?
C35 C34 N4 C43 6.9(2) . . . . ?
O5 C34 N4 C33 -1.1(4) . . . . ?
C35 C34 N4 C33 179.7(2) . . . . ?
O8 C43 N4 C34 172.1(2) . . . . ?
C42 C43 N4 C34 -7.4(2) . . . . ?
O8 C43 N4 C33 -0.9(4) . . . . ?
C42 C43 N4 C33 179.62(19) . . . . ?
C31 C33 N4 C34 93.6(3) . . . . ?
C31 C33 N4 C43 -94.3(3) . . . . ?

_refine_diff_density_max         1.556
_refine_diff_density_min         -1.436
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2389269'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H52 Cl12 N4 O10'
_chemical_formula_weight         1390.43

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'
Cl Cl 0.3639 0.7018 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.3975(6)
_cell_length_b                   23.0975(14)
_cell_length_c                   27.7307(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.683(3)
_cell_angle_gamma                90
_cell_volume                     5965.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       plate
_exptl_crystal_colour            reddish-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.623
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8327
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            76857
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         78.940
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12549
_reflns_number_gt                9908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1818P)²+14.3227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12549
_refine_ls_number_parameters     796
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2905
_refine_ls_wR_factor_gt          0.2720
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C61 C 0.545(3) 0.4192(18) 0.5568(13) 0.112(7) Uani 0.411(5) 1 d . U P A -2
H61 H 0.617423 0.442231 0.541705 0.135 Uiso 0.411(5) 1 calc R U P A -2
Cl13 Cl 0.6140(6) 0.3927(2) 0.6134(2) 0.0887(17) Uani 0.411(5) 1 d . U P A -2
Cl14 Cl 0.3862(8) 0.4620(5) 0.5643(5) 0.182(5) Uani 0.411(5) 1 d . U P A -2
Cl15 Cl 0.4792(13) 0.3600(7) 0.5197(5) 0.194(8) Uani 0.411(5) 1 d . U P A -2
C60 C 0.5179(16) 0.4314(6) 0.5625(9) 0.077(5) Uani 0.589(5) 1 d . . P A -1
H60 H 0.621078 0.442933 0.569904 0.093 Uiso 0.589(5) 1 calc R U P A -1
Cl10 Cl 0.5047(5) 0.36081(15) 0.5377(2) 0.0968(18) Uani 0.589(5) 1 d . . P A -1
Cl11 Cl 0.4287(8) 0.4759(2) 0.51313(17) 0.145(3) Uani 0.589(5) 1 d . . P A -1
Cl12 Cl 0.4353(3) 0.44045(13) 0.61193(11) 0.0705(9) Uani 0.589(5) 1 d . . P A
-1
C1 C 0.3084(4) 0.66336(15) 0.80902(17) 0.0285(8) Uani 1 1 d . . . . .
H1 H 0.234278 0.663573 0.779567 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4019(4) 0.71752(15) 0.80876(15) 0.0248(7) Uani 1 1 d . . . . .
H2A H 0.341134 0.752525 0.808787 0.030 Uiso 1 1 calc R U . . .
H2AB H 0.448910 0.718108 0.778871 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5171(3) 0.71806(14) 0.85385(14) 0.0202(7) Uani 1 1 d . . . . .
C4 C 0.4421(4) 0.71718(17) 0.89980(16) 0.0287(8) Uani 1 1 d . . . . .
H4A H 0.382011 0.752257 0.900688 0.034 Uiso 1 1 calc R U . . .
H4AB H 0.515046 0.717317 0.929083 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3476(5) 0.66281(17) 0.90000(18) 0.0341(9) Uani 1 1 d . . . . .
H5 H 0.299409 0.662691 0.930036 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2332(4) 0.66321(16) 0.85498(19) 0.0350(10) Uani 1 1 d . . . . .
H6A H 0.171993 0.698027 0.855404 0.042 Uiso 1 1 calc R U . . .
H6AB H 0.171331 0.628543 0.855113 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4010(4) 0.60918(15) 0.80833(15) 0.0250(8) Uani 1 1 d . . . . .
H7A H 0.448038 0.608834 0.778441 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.339847 0.574264 0.808100 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4411(4) 0.60843(17) 0.89935(17) 0.0305(8) Uani 1 1 d . . . . .
H8A H 0.380466 0.573436 0.899819 0.037 Uiso 1 1 calc R U . . .
H8AB H 0.513869 0.607757 0.928662 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5162(4) 0.60815(15) 0.85349(14) 0.0219(7) Uani 1 1 d . . . . .
C10 C 0.6091(4) 0.66297(14) 0.85326(14) 0.0201(7) Uani 1 1 d . . . . .
H10A H 0.658318 0.663030 0.823840 0.024 Uiso 1 1 calc R U . . .
H10B H 0.683524 0.662754 0.882131 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6087(4) 0.77286(15) 0.85603(14) 0.0223(7) Uani 1 1 d . . . . .
H11A H 0.545220 0.807026 0.856344 0.027 Uiso 1 1 calc R U . . .
H11B H 0.675448 0.772917 0.886843 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6458(4) 0.80516(14) 0.77136(14) 0.0222(7) Uani 1 1 d . . . . .
C13 C 0.7617(3) 0.79782(14) 0.74015(14) 0.0205(7) Uani 1 1 d . . . . .
C14 C 0.7636(4) 0.81370(15) 0.69227(14) 0.0237(7) Uani 1 1 d . . . . .
H14 H 0.686754 0.834068 0.673977 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8864(4) 0.79762(15) 0.67292(14) 0.0227(7) Uani 1 1 d . . . . .
C16 C 0.9240(4) 0.80595(17) 0.62306(15) 0.0281(8) Uani 1 1 d . . . . .
C17 C 1.1116(4) 0.75692(15) 0.66747(14) 0.0225(7) Uani 1 1 d . . . . .
C18 C 1.0002(4) 0.76837(14) 0.69999(13) 0.0204(7) Uani 1 1 d . . . . .
C19 C 0.9997(3) 0.75334(14) 0.74851(13) 0.0188(6) Uani 1 1 d . . . . .
H19 H 1.077829 0.734156 0.767203 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8746(3) 0.76880(13) 0.76749(13) 0.0178(6) Uani 1 1 d . . . . .
C21 C 0.8347(3) 0.75791(14) 0.81662(14) 0.0205(7) Uani 1 1 d . . . . .
C22 C 1.1269(4) 0.77375(17) 0.57814(14) 0.0288(8) Uani 1 1 d . . . . .
H22A H 1.231961 0.772883 0.588207 0.035 Uiso 1 1 calc R U . . .
H22B H 1.104587 0.808906 0.558131 0.035 Uiso 1 1 calc R U . . .
C23 C 1.0839(5) 0.72034(17) 0.54666(14) 0.0307(8) Uani 1 1 d . . . . .
C24 C 0.9248(6) 0.7215(2) 0.52537(19) 0.0468(12) Uani 1 1 d . . . . .
H24A H 0.903958 0.757148 0.505831 0.056 Uiso 1 1 calc R U . . .
H24B H 0.864647 0.721872 0.552080 0.056 Uiso 1 1 calc R U . . .
C25 C 0.8884(8) 0.6682(3) 0.4932(2) 0.0621(17) Uani 1 1 d . . . . .
H25 H 0.784487 0.669460 0.479460 0.074 Uiso 1 1 calc R U . . .
C26 C 0.9791(11) 0.6683(3) 0.4515(2) 0.080(2) Uani 1 1 d . . . . .
H26A H 0.959784 0.703847 0.431747 0.096 Uiso 1 1 calc R U . . .
H26B H 0.954230 0.634406 0.430132 0.096 Uiso 1 1 calc R U . . .
C27 C 1.1389(9) 0.6658(2) 0.47292(19) 0.0607(17) Uani 1 1 d . . . . .
H27 H 1.198881 0.665692 0.445737 0.073 Uiso 1 1 calc R U . . .
C28 C 1.1769(7) 0.7194(2) 0.50507(16) 0.0464(12) Uani 1 1 d . . . . .
H28A H 1.279739 0.718235 0.518690 0.056 Uiso 1 1 calc R U . . .
H28B H 1.159711 0.754994 0.485253 0.056 Uiso 1 1 calc R U . . .
C29 C 0.9176(7) 0.6128(2) 0.5239(2) 0.0517(13) Uani 1 1 d . . . . .
H29A H 0.857028 0.612666 0.550521 0.062 Uiso 1 1 calc R U . . .
H29B H 0.892637 0.578316 0.503320 0.062 Uiso 1 1 calc R U . . .
C30 C 1.1137(4) 0.66425(15) 0.57657(14) 0.0250(7) Uani 1 1 d . . . . .
H30A H 1.216498 0.662818 0.590201 0.030 Uiso 1 1 calc R U . . .
H30B H 1.056524 0.664535 0.604083 0.030 Uiso 1 1 calc R U . . .
C31 C 1.0756(5) 0.61020(18) 0.54535(15) 0.0350(9) Uani 1 1 d . . . . .
C32 C 1.1713(8) 0.6107(2) 0.50390(18) 0.0563(15) Uani 1 1 d . . . . .
H32A H 1.273877 0.610132 0.517915 0.068 Uiso 1 1 calc R U . . .
H32B H 1.151528 0.575923 0.483246 0.068 Uiso 1 1 calc R U . . .
C33 C 1.1132(5) 0.55452(18) 0.57447(15) 0.0340(9) Uani 1 1 d . . . . .
H33A H 1.086151 0.520793 0.553176 0.041 Uiso 1 1 calc R U . . .
H33B H 1.218356 0.553102 0.584235 0.041 Uiso 1 1 calc R U . . .
C34 C 0.9098(4) 0.52272(16) 0.61970(15) 0.0293(8) Uani 1 1 d . . . . .
C35 C 0.8757(4) 0.52886(14) 0.67022(14) 0.0248(7) Uani 1 1 d . . . . .
C36 C 0.7547(4) 0.51227(15) 0.68991(15) 0.0258(8) Uani 1 1 d . . . . .
H36 H 0.677291 0.492013 0.671822 0.031 Uiso 1 1 calc R U . . .
C37 C 0.7556(4) 0.52757(14) 0.73819(14) 0.0230(7) Uani 1 1 d . . . . .
C38 C 0.6411(4) 0.52031(15) 0.77001(15) 0.0248(8) Uani 1 1 d . . . . .
C39 C 0.8301(4) 0.56795(14) 0.81420(14) 0.0220(7) Uani 1 1 d . . . . .
C40 C 0.8698(4) 0.55661(14) 0.76517(14) 0.0212(7) Uani 1 1 d . . . . .
C41 C 0.9930(4) 0.57173(15) 0.74551(14) 0.0214(7) Uani 1 1 d . . . . .
H41 H 1.072263 0.590505 0.763975 0.026 Uiso 1 1 calc R U . . .
C42 C 0.9917(4) 0.55747(14) 0.69725(14) 0.0220(7) Uani 1 1 d . . . . .
C43 C 1.1012(4) 0.56898(15) 0.66422(14) 0.0252(7) Uani 1 1 d . . . . .
C44 C 0.6071(4) 0.55302(15) 0.85493(15) 0.0251(7) Uani 1 1 d . . . . .
H44A H 0.675033 0.552666 0.885475 0.030 Uiso 1 1 calc R U . . .
H44B H 0.543268 0.519006 0.855430 0.030 Uiso 1 1 calc R U . . .
C45 C -0.1864(4) 0.38387(15) 0.74388(15) 0.0243(7) Uani 1 1 d . . . . .
C46 C -0.0494(4) 0.40069(15) 0.73143(14) 0.0230(7) Uani 1 1 d . . . . .
C47 C -0.0097(4) 0.39352(15) 0.68429(14) 0.0233(7) Uani 1 1 d . . . . .
H47 H -0.075482 0.376322 0.659385 0.028 Uiso 1 1 calc R U . . .
C48 C 0.1212(4) 0.41096(16) 0.67426(15) 0.0270(8) Uani 1 1 d . . . . .
H48 H 0.145591 0.406152 0.642345 0.032 Uiso 1 1 calc R U . . .
C49 C 0.2227(4) 0.43645(16) 0.71117(15) 0.0275(8) Uani 1 1 d . . . . .
H49 H 0.314127 0.448678 0.704060 0.033 Uiso 1 1 calc R U . . .
C50 C 0.1857(4) 0.44291(14) 0.75687(14) 0.0223(7) Uani 1 1 d . . . . .
C51 C 0.0493(4) 0.42639(15) 0.76866(14) 0.0235(7) Uani 1 1 d . . . . .
C52 C 0.0089(4) 0.43373(15) 0.81610(14) 0.0243(7) Uani 1 1 d . . . . .
H52 H 0.074571 0.450860 0.841059 0.029 Uiso 1 1 calc R U . . .
C53 C -0.1225(4) 0.41653(18) 0.82600(16) 0.0316(8) Uani 1 1 d . . . . .
H53 H -0.147497 0.421914 0.857770 0.038 Uiso 1 1 calc R U . . .
C54 C -0.2228(4) 0.39063(17) 0.78951(16) 0.0305(8) Uani 1 1 d . . . . .
H54 H -0.313903 0.378189 0.796782 0.037 Uiso 1 1 calc R U . . .
C55 C 1.5116(5) 0.66215(17) 0.64698(18) 0.0353(9) Uani 1 1 d . . . . .
H55 H 1.413299 0.663150 0.657014 0.042 Uiso 1 1 calc R U . . .
C56 C 0.5572(6) 0.8886(2) 0.5706(2) 0.0475(12) Uani 1 1 d . . . . .
H56 H 0.656384 0.879959 0.586954 0.057 Uiso 1 1 calc R U . . .
C57 C 1.0201(10) 0.5802(4) 0.9534(3) 0.083(2) Uani 1 1 d . . . . .
H57 H 1.031292 0.603918 0.923983 0.099 Uiso 1 1 calc R U . . .
Cl1 Cl 1.64036(14) 0.66249(4) 0.69977(4) 0.0423(3) Uani 1 1 d . . . . .
Cl2 Cl 1.53455(13) 0.72363(5) 0.61131(5) 0.0459(3) Uani 1 1 d . . . . .
Cl3 Cl 1.52877(14) 0.59917(5) 0.61273(5) 0.0486(3) Uani 1 1 d . . . . .
Cl4 Cl 0.44252(14) 0.88785(6) 0.61601(5) 0.0483(3) Uani 1 1 d . . . . .
Cl5 Cl 0.5100(2) 0.83369(6) 0.52801(5) 0.0595(4) Uani 1 1 d . . . . .
Cl6 Cl 0.5625(2) 0.95544(7) 0.54388(7) 0.0813(6) Uani 1 1 d . . . . .
Cl7 Cl 1.1734(2) 0.58939(13) 0.99484(8) 0.1032(8) Uani 1 1 d . . . . .
Cl8 Cl 0.8702(3) 0.60517(11) 0.97701(8) 0.0960(7) Uani 1 1 d . . . . .
Cl9 Cl 1.0030(3) 0.50742(10) 0.93519(8) 0.1067(8) Uani 1 1 d . . . . .
N1 N 0.6923(3) 0.77831(12) 0.81514(11) 0.0202(6) Uani 1 1 d . . . . .
N2 N 1.0552(3) 0.77806(14) 0.62170(12) 0.0253(6) Uani 1 1 d . . . . .
N3 N 1.0417(4) 0.54965(14) 0.61808(12) 0.0282(7) Uani 1 1 d . . . . .
N4 N 0.6889(3) 0.54746(12) 0.81355(12) 0.0229(6) Uani 1 1 d . . . . .
O1 O 0.5316(3) 0.82984(11) 0.76065(11) 0.0285(6) Uani 1 1 d . . . . .
O2 O 0.8567(4) 0.83120(14) 0.58931(12) 0.0393(7) Uani 1 1 d . . . . .
O3 O 1.2272(3) 0.73381(12) 0.67755(10) 0.0266(6) Uani 1 1 d . . . . .
O4 O 0.9039(3) 0.73639(11) 0.85161(10) 0.0249(5) Uani 1 1 d . . . . .
O5 O 0.8378(4) 0.49899(13) 0.58501(11) 0.0387(7) Uani 1 1 d . . . . .
O6 O 0.5270(3) 0.49506(12) 0.76010(12) 0.0321(6) Uani 1 1 d . . . . .
O7 O 0.9002(3) 0.59079(12) 0.84842(11) 0.0303(6) Uani 1 1 d . . . . .
O8 O 1.2180(3) 0.59112(12) 0.67382(11) 0.0291(6) Uani 1 1 d . . . . .
O9 O -0.2775(3) 0.36085(14) 0.70620(11) 0.0351(7) Uani 1 1 d . . . . .
H9 H -0.356751 0.353345 0.715629 0.053 Uiso 1 1 calc R U . . .
O10 O 0.2772(3) 0.46499(13) 0.79458(11) 0.0343(6) Uani 1 1 d . . . . .
H10 H 0.347661 0.480346 0.783870 0.051 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
C61 Cl13 1.73(4) . ?
C61 Cl15 1.77(4) . ?
C61 Cl14 1.82(3) . ?
C60 Cl12 1.676(18) . ?
C60 Cl10 1.768(15) . ?
C60 Cl11 1.82(2) . ?
C1 C7 1.526(5) . ?
C1 C2 1.530(5) . ?
C1 C6 1.537(6) . ?
C2 C3 1.541(5) . ?
C3 C11 1.527(4) . ?
C3 C4 1.536(5) . ?
C3 C10 1.540(4) . ?
C4 C5 1.538(5) . ?
C5 C8 1.534(5) . ?
C5 C6 1.535(7) . ?
C7 C9 1.542(5) . ?
C8 C9 1.535(5) . ?
C9 C44 1.531(5) . ?
C9 C10 1.539(4) . ?
C11 N1 1.468(5) . ?
C12 O1 1.217(4) . ?
C12 N1 1.381(5) . ?
C12 C13 1.488(5) . ?
C13 C14 1.380(5) . ?
C13 C20 1.392(5) . ?
C14 C15 1.387(5) . ?
C15 C18 1.396(5) . ?
C15 C16 1.485(5) . ?
C16 O2 1.207(5) . ?
C16 N2 1.396(5) . ?
C17 O3 1.209(4) . ?
C17 N2 1.397(5) . ?
C17 C18 1.494(5) . ?
C18 C19 1.391(5) . ?
C19 C20 1.397(5) . ?
C20 C21 1.482(5) . ?
C21 O4 1.201(5) . ?
C21 N1 1.414(4) . ?
C22 N2 1.463(5) . ?
C22 C23 1.534(5) . ?
C23 C24 1.533(7) . ?
C23 C28 1.537(6) . ?
C23 C30 1.544(5) . ?
C24 C25 1.533(7) . ?
C25 C26 1.525(12) . ?
C25 C29 1.542(8) . ?
C26 C27 1.541(12) . ?
C27 C28 1.540(7) . ?
C27 C32 1.543(8) . ?
C29 C31 1.524(7) . ?
C30 C31 1.534(5) . ?
C31 C33 1.534(6) . ?
C31 C32 1.552(7) . ?
C33 N3 1.464(5) . ?
C34 O5 1.228(5) . ?
C34 N3 1.393(5) . ?
C34 C35 1.485(6) . ?
C35 C36 1.379(6) . ?
C35 C42 1.403(5) . ?
C36 C37 1.384(6) . ?
C37 C40 1.396(5) . ?
C37 C38 1.489(5) . ?
C38 O6 1.219(4) . ?
C38 N4 1.381(5) . ?
C39 O7 1.202(5) . ?
C39 N4 1.407(4) . ?
C39 C40 1.481(5) . ?
C40 C41 1.389(5) . ?
C41 C42 1.377(5) . ?
C42 C43 1.491(5) . ?
C43 O8 1.208(5) . ?
C43 N3 1.399(5) . ?
C44 N4 1.470(5) . ?
C45 C54 1.363(6) . ?
C45 O9 1.367(5) . ?
C45 C46 1.431(5) . ?
C46 C47 1.416(5) . ?
C46 C51 1.422(5) . ?
C47 C48 1.358(5) . ?
C48 C49 1.429(6) . ?
C49 C50 1.366(6) . ?
C50 O10 1.361(5) . ?
C50 C51 1.417(5) . ?
C51 C52 1.427(5) . ?
C52 C53 1.359(6) . ?
C53 C54 1.420(6) . ?
C55 Cl3 1.756(4) . ?
C55 Cl2 1.760(4) . ?
C55 Cl1 1.770(5) . ?
C56 Cl6 1.716(6) . ?
C56 Cl5 1.751(6) . ?
C56 Cl4 1.763(6) . ?
C57 Cl8 1.730(9) . ?
C57 Cl7 1.731(9) . ?
C57 Cl9 1.756(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
Cl13 C61 Cl15 108(2) . . ?
Cl13 C61 Cl14 107.6(17) . . ?
Cl15 C61 Cl14 105.0(17) . . ?
Cl12 C60 Cl10 114.6(8) . . ?
Cl12 C60 Cl11 109.1(8) . . ?
Cl10 C60 Cl11 103.1(12) . . ?
C7 C1 C2 110.0(3) . . ?
C7 C1 C6 109.5(3) . . ?
C2 C1 C6 109.5(3) . . ?
C1 C2 C3 110.2(3) . . ?
C11 C3 C4 107.3(3) . . ?
C11 C3 C10 111.8(3) . . ?
C4 C3 C10 108.6(3) . . ?
C11 C3 C2 111.7(3) . . ?
C4 C3 C2 108.8(3) . . ?
C10 C3 C2 108.6(3) . . ?
C3 C4 C5 110.1(3) . . ?
C8 C5 C6 109.6(4) . . ?
C8 C5 C4 109.7(3) . . ?
C6 C5 C4 109.5(3) . . ?
C5 C6 C1 109.0(3) . . ?
C1 C7 C9 110.0(3) . . ?
C5 C8 C9 109.9(3) . . ?
C44 C9 C8 107.4(3) . . ?
C44 C9 C10 111.7(3) . . ?
C8 C9 C10 108.9(3) . . ?
C44 C9 C7 111.3(3) . . ?
C8 C9 C7 108.8(3) . . ?
C10 C9 C7 108.7(3) . . ?
C9 C10 C3 111.1(3) . . ?
N1 C11 C3 113.4(3) . . ?
O1 C12 N1 126.2(3) . . ?
O1 C12 C13 127.0(4) . . ?
N1 C12 C13 106.9(3) . . ?
C14 C13 C20 123.0(3) . . ?
C14 C13 C12 129.4(3) . . ?
C20 C13 C12 107.6(3) . . ?
C13 C14 C15 114.8(3) . . ?
C14 C15 C18 122.6(3) . . ?
C14 C15 C16 129.8(3) . . ?
C18 C15 C16 107.6(3) . . ?
O2 C16 N2 125.1(4) . . ?
O2 C16 C15 128.3(4) . . ?
N2 C16 C15 106.6(3) . . ?
O3 C17 N2 125.8(3) . . ?
O3 C17 C18 128.2(3) . . ?
N2 C17 C18 106.0(3) . . ?
C19 C18 C15 122.6(3) . . ?
C19 C18 C17 129.3(3) . . ?
C15 C18 C17 108.0(3) . . ?
C18 C19 C20 114.4(3) . . ?
C13 C20 C19 122.5(3) . . ?
C13 C20 C21 108.3(3) . . ?
C19 C20 C21 129.2(3) . . ?
O4 C21 N1 124.7(3) . . ?
O4 C21 C20 129.5(3) . . ?
N1 C21 C20 105.8(3) . . ?
N2 C22 C23 114.2(3) . . ?
C24 C23 C22 111.9(4) . . ?
C24 C23 C28 109.5(4) . . ?
C22 C23 C28 107.8(4) . . ?
C24 C23 C30 108.6(4) . . ?
C22 C23 C30 110.7(3) . . ?
C28 C23 C30 108.1(3) . . ?
C23 C24 C25 109.9(5) . . ?
C26 C25 C24 109.7(5) . . ?
C26 C25 C29 110.2(6) . . ?
C24 C25 C29 109.6(4) . . ?
C25 C26 C27 108.8(5) . . ?
C28 C27 C26 109.4(5) . . ?
C28 C27 C32 109.1(4) . . ?
C26 C27 C32 110.8(6) . . ?
C23 C28 C27 109.6(5) . . ?
C31 C29 C25 109.9(5) . . ?
C31 C30 C23 111.6(3) . . ?
C29 C31 C30 109.2(4) . . ?
C29 C31 C33 112.4(4) . . ?
C30 C31 C33 111.4(3) . . ?
C29 C31 C32 110.0(4) . . ?
C30 C31 C32 107.3(4) . . ?
C33 C31 C32 106.3(4) . . ?
C27 C32 C31 109.1(5) . . ?
N3 C33 C31 113.6(3) . . ?
O5 C34 N3 125.0(4) . . ?
O5 C34 C35 128.0(4) . . ?
N3 C34 C35 107.0(3) . . ?
C36 C35 C42 122.8(4) . . ?
C36 C35 C34 129.8(3) . . ?
C42 C35 C34 107.4(3) . . ?
C35 C36 C37 114.4(3) . . ?
C36 C37 C40 123.1(3) . . ?
C36 C37 C38 129.3(3) . . ?
C40 C37 C38 107.5(3) . . ?
O6 C38 N4 126.0(4) . . ?
O6 C38 C37 127.1(4) . . ?
N4 C38 C37 106.9(3) . . ?
O7 C39 N4 125.0(4) . . ?
O7 C39 C40 128.6(3) . . ?
N4 C39 C40 106.4(3) . . ?
C41 C40 C37 122.2(4) . . ?
C41 C40 C39 129.9(3) . . ?
C37 C40 C39 107.9(3) . . ?
C42 C41 C40 114.9(3) . . ?
C41 C42 C35 122.5(3) . . ?
C41 C42 C43 129.6(3) . . ?
C35 C42 C43 107.9(3) . . ?
O8 C43 N3 125.3(4) . . ?
O8 C43 C42 128.5(4) . . ?
N3 C43 C42 106.3(3) . . ?
N4 C44 C9 113.6(3) . . ?
C54 C45 O9 123.0(3) . . ?
C54 C45 C46 122.6(4) . . ?
O9 C45 C46 114.4(3) . . ?
C47 C46 C51 119.5(3) . . ?
C47 C46 C45 123.2(3) . . ?
C51 C46 C45 117.3(3) . . ?
C48 C47 C46 120.8(3) . . ?
C47 C48 C49 120.8(4) . . ?
C50 C49 C48 118.8(3) . . ?
O10 C50 C49 122.8(3) . . ?
O10 C50 C51 114.9(3) . . ?
C49 C50 C51 122.3(3) . . ?
C50 C51 C46 117.9(3) . . ?
C50 C51 C52 122.7(3) . . ?
C46 C51 C52 119.4(3) . . ?
C53 C52 C51 120.8(4) . . ?
C52 C53 C54 120.9(4) . . ?
C45 C54 C53 119.0(4) . . ?
Cl3 C55 Cl2 109.7(3) . . ?
Cl3 C55 Cl1 110.4(2) . . ?
Cl2 C55 Cl1 109.8(2) . . ?
Cl6 C56 Cl5 112.3(3) . . ?
Cl6 C56 Cl4 111.9(3) . . ?
Cl5 C56 Cl4 110.5(3) . . ?
Cl8 C57 Cl7 110.8(5) . . ?
Cl8 C57 Cl9 112.3(5) . . ?
Cl7 C57 Cl9 110.2(5) . . ?
C12 N1 C21 111.2(3) . . ?
C12 N1 C11 125.3(3) . . ?
C21 N1 C11 123.4(3) . . ?
C16 N2 C17 111.5(3) . . ?
C16 N2 C22 124.0(3) . . ?
C17 N2 C22 124.4(3) . . ?
C34 N3 C43 111.2(3) . . ?
C34 N3 C33 124.7(3) . . ?
C43 N3 C33 124.0(3) . . ?
C38 N4 C39 111.1(3) . . ?
C38 N4 C44 125.4(3) . . ?
C39 N4 C44 123.5(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
C7 C1 C2 C3 -60.0(4) . . . . ?
C6 C1 C2 C3 60.4(4) . . . . ?
C1 C2 C3 C11 -177.5(3) . . . . ?
C1 C2 C3 C4 -59.3(4) . . . . ?
C1 C2 C3 C10 58.7(4) . . . . ?
C11 C3 C4 C5 -180.0(3) . . . . ?
C10 C3 C4 C5 -59.0(4) . . . . ?
C2 C3 C4 C5 59.0(4) . . . . ?
C3 C4 C5 C8 60.1(5) . . . . ?
C3 C4 C5 C6 -60.2(4) . . . . ?
C8 C5 C6 C1 -60.1(4) . . . . ?
C4 C5 C6 C1 60.2(4) . . . . ?
C7 C1 C6 C5 60.3(4) . . . . ?
C2 C1 C6 C5 -60.4(4) . . . . ?
C2 C1 C7 C9 60.0(4) . . . . ?
C6 C1 C7 C9 -60.4(4) . . . . ?
C6 C5 C8 C9 60.3(4) . . . . ?
C4 C5 C8 C9 -59.9(5) . . . . ?
C5 C8 C9 C44 -179.9(3) . . . . ?
C5 C8 C9 C10 59.0(4) . . . . ?
C5 C8 C9 C7 -59.4(4) . . . . ?
C1 C7 C9 C44 177.7(3) . . . . ?
C1 C7 C9 C8 59.6(4) . . . . ?
C1 C7 C9 C10 -58.9(4) . . . . ?
C44 C9 C10 C3 -177.8(3) . . . . ?
C8 C9 C10 C3 -59.3(4) . . . . ?
C7 C9 C10 C3 59.1(4) . . . . ?
C11 C3 C10 C9 177.3(3) . . . . ?
C4 C3 C10 C9 59.2(4) . . . . ?
C2 C3 C10 C9 -59.0(4) . . . . ?
C4 C3 C11 N1 177.5(3) . . . . ?
C10 C3 C11 N1 58.6(4) . . . . ?
C2 C3 C11 N1 -63.3(4) . . . . ?
O1 C12 C13 C14 -4.2(6) . . . . ?
N1 C12 C13 C14 175.6(3) . . . . ?
O1 C12 C13 C20 177.9(3) . . . . ?
N1 C12 C13 C20 -2.3(4) . . . . ?
C20 C13 C14 C15 1.1(5) . . . . ?
C12 C13 C14 C15 -176.6(3) . . . . ?
C13 C14 C15 C18 -0.9(5) . . . . ?
C13 C14 C15 C16 178.3(4) . . . . ?
C14 C15 C16 O2 3.8(7) . . . . ?
C18 C15 C16 O2 -176.9(4) . . . . ?
C14 C15 C16 N2 -175.7(4) . . . . ?
C18 C15 C16 N2 3.6(4) . . . . ?
C14 C15 C18 C19 -0.3(5) . . . . ?
C16 C15 C18 C19 -179.7(3) . . . . ?
C14 C15 C18 C17 178.7(3) . . . . ?
C16 C15 C18 C17 -0.7(4) . . . . ?
O3 C17 C18 C19 -3.0(6) . . . . ?
N2 C17 C18 C19 176.5(3) . . . . ?
O3 C17 C18 C15 178.1(4) . . . . ?
N2 C17 C18 C15 -2.4(4) . . . . ?
C15 C18 C19 C20 1.3(5) . . . . ?
C17 C18 C19 C20 -177.4(3) . . . . ?
C14 C13 C20 C19 0.0(5) . . . . ?
C12 C13 C20 C19 178.1(3) . . . . ?
C14 C13 C20 C21 -179.0(3) . . . . ?
C12 C13 C20 C21 -0.9(4) . . . . ?
C18 C19 C20 C13 -1.2(5) . . . . ?
C18 C19 C20 C21 177.5(3) . . . . ?
C13 C20 C21 O4 -176.5(3) . . . . ?
C19 C20 C21 O4 4.6(6) . . . . ?
C13 C20 C21 N1 3.7(4) . . . . ?
C19 C20 C21 N1 -175.2(3) . . . . ?
N2 C22 C23 C24 64.1(5) . . . . ?
N2 C22 C23 C28 -175.4(4) . . . . ?
N2 C22 C23 C30 -57.3(5) . . . . ?
C22 C23 C24 C25 178.5(4) . . . . ?
C28 C23 C24 C25 59.0(5) . . . . ?
C30 C23 C24 C25 -58.9(5) . . . . ?
C23 C24 C25 C26 -60.4(6) . . . . ?
C23 C24 C25 C29 60.6(7) . . . . ?
C24 C25 C26 C27 61.0(6) . . . . ?
C29 C25 C26 C27 -59.8(6) . . . . ?
C25 C26 C27 C28 -60.9(6) . . . . ?
C25 C26 C27 C32 59.5(6) . . . . ?
C24 C23 C28 C27 -58.8(5) . . . . ?
C22 C23 C28 C27 179.1(4) . . . . ?
C30 C23 C28 C27 59.4(5) . . . . ?
C26 C27 C28 C23 60.0(6) . . . . ?
C32 C27 C28 C23 -61.4(7) . . . . ?
C26 C25 C29 C31 60.5(6) . . . . ?
C24 C25 C29 C31 -60.3(7) . . . . ?
C24 C23 C30 C31 58.3(5) . . . . ?
C22 C23 C30 C31 -178.3(3) . . . . ?
C28 C23 C30 C31 -60.4(5) . . . . ?
C25 C29 C31 C30 58.5(6) . . . . ?
C25 C29 C31 C33 -177.3(4) . . . . ?
C25 C29 C31 C32 -59.0(6) . . . . ?
C23 C30 C31 C29 -58.4(5) . . . . ?
C23 C30 C31 C33 176.8(4) . . . . ?
C23 C30 C31 C32 60.8(5) . . . . ?
C28 C27 C32 C31 62.1(7) . . . . ?
C26 C27 C32 C31 -58.4(6) . . . . ?
C29 C31 C32 C27 57.9(6) . . . . ?
C30 C31 C32 C27 -60.8(6) . . . . ?
C33 C31 C32 C27 179.9(4) . . . . ?
C29 C31 C33 N3 -65.0(5) . . . . ?
C30 C31 C33 N3 58.0(5) . . . . ?
C32 C31 C33 N3 174.6(4) . . . . ?
O5 C34 C35 C36 -3.3(7) . . . . ?
N3 C34 C35 C36 176.4(4) . . . . ?
O5 C34 C35 C42 178.2(4) . . . . ?
N3 C34 C35 C42 -2.1(4) . . . . ?
C42 C35 C36 C37 1.7(5) . . . . ?
C34 C35 C36 C37 -176.7(3) . . . . ?
C35 C36 C37 C40 -0.9(5) . . . . ?
C35 C36 C37 C38 175.7(3) . . . . ?
C36 C37 C38 O6 6.0(6) . . . . ?
C40 C37 C38 O6 -176.9(4) . . . . ?
C36 C37 C38 N4 -174.4(3) . . . . ?
C40 C37 C38 N4 2.7(4) . . . . ?
C36 C37 C40 C41 -0.9(5) . . . . ?
C38 C37 C40 C41 -178.1(3) . . . . ?
C36 C37 C40 C39 177.4(3) . . . . ?
C38 C37 C40 C39 0.2(4) . . . . ?
O7 C39 C40 C41 -3.7(6) . . . . ?
N4 C39 C40 C41 175.2(3) . . . . ?
O7 C39 C40 C37 178.2(4) . . . . ?
N4 C39 C40 C37 -2.9(4) . . . . ?
C37 C40 C41 C42 1.9(5) . . . . ?
C39 C40 C41 C42 -176.1(3) . . . . ?
C40 C41 C42 C35 -1.1(5) . . . . ?
C40 C41 C42 C43 177.3(3) . . . . ?
C36 C35 C42 C41 -0.7(5) . . . . ?
C34 C35 C42 C41 178.0(3) . . . . ?
C36 C35 C42 C43 -179.4(3) . . . . ?
C34 C35 C42 C43 -0.8(4) . . . . ?
C41 C42 C43 O8 3.8(6) . . . . ?
C35 C42 C43 O8 -177.5(4) . . . . ?
C41 C42 C43 N3 -175.2(4) . . . . ?
C35 C42 C43 N3 3.4(4) . . . . ?
C8 C9 C44 N4 -178.6(3) . . . . ?
C10 C9 C44 N4 -59.2(4) . . . . ?
C7 C9 C44 N4 62.5(4) . . . . ?
C54 C45 C46 C47 179.5(3) . . . . ?
O9 C45 C46 C47 -0.8(5) . . . . ?
C54 C45 C46 C51 -1.3(5) . . . . ?
O9 C45 C46 C51 178.4(3) . . . . ?
C51 C46 C47 C48 -0.1(5) . . . . ?
C45 C46 C47 C48 179.1(3) . . . . ?
C46 C47 C48 C49 0.6(6) . . . . ?
C47 C48 C49 C50 0.1(6) . . . . ?
C48 C49 C50 O10 177.8(3) . . . . ?
C48 C49 C50 C51 -1.4(5) . . . . ?
O10 C50 C51 C46 -177.4(3) . . . . ?
C49 C50 C51 C46 1.9(5) . . . . ?
O10 C50 C51 C52 1.6(5) . . . . ?
C49 C50 C51 C52 -179.0(3) . . . . ?
C47 C46 C51 C50 -1.1(5) . . . . ?
C45 C46 C51 C50 179.6(3) . . . . ?
C47 C46 C51 C52 179.8(3) . . . . ?
C45 C46 C51 C52 0.5(5) . . . . ?
C50 C51 C52 C53 -179.1(4) . . . . ?
C46 C51 C52 C53 -0.1(5) . . . . ?
C51 C52 C53 C54 0.2(6) . . . . ?
O9 C45 C54 C53 -178.2(4) . . . . ?
C46 C45 C54 C53 1.5(6) . . . . ?
C52 C53 C54 C45 -0.9(6) . . . . ?
O1 C12 N1 C21 -175.4(3) . . . . ?
C13 C12 N1 C21 4.8(4) . . . . ?
O1 C12 N1 C11 2.6(6) . . . . ?
C13 C12 N1 C11 -177.2(3) . . . . ?
O4 C21 N1 C12 174.9(3) . . . . ?
C20 C21 N1 C12 -5.3(4) . . . . ?
O4 C21 N1 C11 -3.2(5) . . . . ?
C20 C21 N1 C11 176.7(3) . . . . ?
C3 C11 N1 C12 89.8(4) . . . . ?
C3 C11 N1 C21 -92.4(4) . . . . ?
O2 C16 N2 C17 175.2(4) . . . . ?
C15 C16 N2 C17 -5.3(4) . . . . ?
O2 C16 N2 C22 -2.5(6) . . . . ?
C15 C16 N2 C22 177.1(3) . . . . ?
O3 C17 N2 C16 -175.7(4) . . . . ?
C18 C17 N2 C16 4.8(4) . . . . ?
O3 C17 N2 C22 2.0(6) . . . . ?
C18 C17 N2 C22 -177.5(3) . . . . ?
C23 C22 N2 C16 -89.3(4) . . . . ?
C23 C22 N2 C17 93.3(4) . . . . ?
O5 C34 N3 C43 -175.8(4) . . . . ?
C35 C34 N3 C43 4.5(4) . . . . ?
O5 C34 N3 C33 1.1(6) . . . . ?
C35 C34 N3 C33 -178.6(3) . . . . ?
O8 C43 N3 C34 176.0(4) . . . . ?
C42 C43 N3 C34 -4.9(4) . . . . ?
O8 C43 N3 C33 -0.9(6) . . . . ?
C42 C43 N3 C33 178.2(3) . . . . ?
C31 C33 N3 C34 91.5(4) . . . . ?
C31 C33 N3 C43 -91.9(5) . . . . ?
O6 C38 N4 C39 175.0(3) . . . . ?
C37 C38 N4 C39 -4.7(4) . . . . ?
O6 C38 N4 C44 -3.1(6) . . . . ?
C37 C38 N4 C44 177.3(3) . . . . ?
O7 C39 N4 C38 -176.3(3) . . . . ?
C40 C39 N4 C38 4.8(4) . . . . ?
O7 C39 N4 C44 1.8(6) . . . . ?
C40 C39 N4 C44 -177.2(3) . . . . ?
C9 C44 N4 C38 -90.6(4) . . . . ?
C9 C44 N4 C39 91.6(4) . . . . ?

_refine_diff_density_max         0.866
_refine_diff_density_min         -1.611
_refine_diff_density_rms         0.137

