# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1203DM_a
_database_code_depnum_ccdc_archive 'CCDC 1996098'
loop_
_audit_author_name
_audit_author_address
'Tomoki Yoneda'
;Hokkaido University
Japan
;
_audit_update_record             
;
2020-04-10 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C55 H33 Cl3 F15 N5 O'
_chemical_formula_weight         1171.21

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'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 '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                   13.2433(3)
_cell_length_b                   13.7134(3)
_cell_length_c                   15.7312(4)
_cell_angle_alpha                70.8480(10)
_cell_angle_beta                 80.5960(10)
_cell_angle_gamma                66.0900(10)
_cell_volume                     2465.69(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    14145
_cell_measurement_theta_min      2.975
_cell_measurement_theta_max      78.245

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   0.578248
_exptl_transmission_factor_max   1.000000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rugaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            26697
_diffrn_reflns_av_unetI/netI     0.1021
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             8822
_reflns_number_gt                5878
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1111P)²+1.8400P] 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         8822
_refine_ls_number_parameters     722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2495
_refine_ls_wR_factor_gt          0.2201
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 0.7357(4) 0.4426(3) 0.5597(3) 0.0356(10) Uani 1 1 d . . . . .
C2 C 0.6759(4) 0.3866(3) 0.6264(3) 0.0355(10) Uani 1 1 d . . . . .
C3 C 0.6062(4) 0.3495(4) 0.5992(3) 0.0445(11) Uani 1 1 d . . . . .
H1 H 0.5658 0.3128 0.6414 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5987(4) 0.3687(4) 0.5078(3) 0.0470(12) Uani 1 1 d . . . . .
H2 H 0.5535 0.3437 0.4882 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6582(4) 0.4249(4) 0.4456(3) 0.0407(11) Uani 1 1 d . . . . .
N1 N 0.7252(3) 0.4624(3) 0.4721(2) 0.0416(9) Uani 1 1 d . . . . .
C6 C 0.6575(4) 0.4497(4) 0.3482(3) 0.0381(10) Uani 1 1 d . . . . .
C7 C 0.6293(4) 0.4038(4) 0.2924(3) 0.0416(11) Uani 1 1 d . . . . .
C8 C 0.6565(4) 0.4551(3) 0.2034(3) 0.0354(10) Uani 1 1 d . . . . .
C9 C 0.7011(3) 0.5325(3) 0.2056(3) 0.0307(9) Uani 1 1 d . . . . .
N2 N 0.6995(3) 0.5268(3) 0.2948(2) 0.0365(8) Uani 1 1 d . . . . .
H26 H 0.7218 0.5661 0.3143 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7410(4) 0.6056(3) 0.1350(3) 0.0324(9) Uani 1 1 d . . . . .
C11 C 0.7662(3) 0.6945(3) 0.1363(3) 0.0313(9) Uani 1 1 d . . . . .
C12 C 0.8007(4) 0.7634(3) 0.0564(3) 0.0327(9) Uani 1 1 d . . . . .
H3 H 0.8174 0.7509 0.0002 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8044(4) 0.8492(3) 0.0775(3) 0.0343(9) Uani 1 1 d . . . . .
H4 H 0.8220 0.9080 0.0383 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7760(3) 0.8331(3) 0.1723(3) 0.0302(9) Uani 1 1 d . . . . .
N3 N 0.7533(3) 0.7396(3) 0.2071(2) 0.0322(8) Uani 1 1 d . . . . .
H27 H 0.7345 0.7131 0.2621 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7792(3) 0.9078(3) 0.2164(3) 0.0317(9) Uani 1 1 d . . . . .
C16 C 0.7970(3) 0.8902(3) 0.3058(3) 0.0313(9) Uani 1 1 d . . . . .
C17 C 0.8120(4) 0.9682(4) 0.3398(3) 0.0415(11) Uani 1 1 d . . . . .
H5 H 0.8007 1.0420 0.3082 0.050 Uiso 1 1 calc R U . . .
C18 C 0.8454(4) 0.9169(4) 0.4254(3) 0.0403(11) Uani 1 1 d . . . . .
H6 H 0.8624 0.9492 0.4618 0.048 Uiso 1 1 calc R U . . .
C19 C 0.8503(4) 0.8046(3) 0.4512(3) 0.0328(9) Uani 1 1 d . . . . .
N4 N 0.8147(3) 0.7945(3) 0.3763(2) 0.0300(7) Uani 1 1 d . . . . .
H28 H 0.8054 0.7366 0.3748 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8867(4) 0.7235(3) 0.5313(3) 0.0335(9) Uani 1 1 d . . . . .
C21 C 0.8807(4) 0.6147(3) 0.5622(3) 0.0320(9) Uani 1 1 d . . . . .
C22 C 0.9383(4) 0.5200(3) 0.6301(3) 0.0323(9) Uani 1 1 d . . . . .
C23 C 0.8922(3) 0.4395(3) 0.6424(3) 0.0300(9) Uani 1 1 d . . . . .
C24 C 0.8084(4) 0.4867(3) 0.5819(3) 0.0339(9) Uani 1 1 d . . . . .
N5 N 0.8043(3) 0.5904(3) 0.5316(2) 0.0343(8) Uani 1 1 d . . . . .
H29 H 0.7610 0.6337 0.4878 0.041 Uiso 1 1 calc R U . . .
O1 O 0.6874(3) 0.3780(2) 0.71313(18) 0.0391(7) Uani 1 1 d . . . . .
C25 C 0.6113(4) 0.3430(4) 0.7809(3) 0.0427(11) Uani 1 1 d . . . . .
H7 H 0.5373 0.3832 0.7580 0.051 Uiso 1 1 calc R U . . .
H8 H 0.6125 0.3644 0.8336 0.051 Uiso 1 1 calc R U . . .
C26 C 0.6342(4) 0.2203(3) 0.8095(3) 0.0357(10) Uani 1 1 d . . . . .
C27 C 0.7407(4) 0.1416(4) 0.8161(3) 0.0451(11) Uani 1 1 d . . . . .
H9 H 0.8000 0.1646 0.8009 0.054 Uiso 1 1 calc R U . . .
C28 C 0.7602(5) 0.0290(4) 0.8451(3) 0.0537(13) Uani 1 1 d . . . . .
H10 H 0.8323 -0.0233 0.8495 0.064 Uiso 1 1 calc R U . . .
C29 C 0.6724(5) -0.0056(4) 0.8676(4) 0.0579(14) Uani 1 1 d . . . . .
H11 H 0.6851 -0.0812 0.8858 0.069 Uiso 1 1 calc R U . . .
C30 C 0.5661(5) 0.0721(5) 0.8629(3) 0.0596(15) Uani 1 1 d . . . . .
H12 H 0.5069 0.0489 0.8803 0.072 Uiso 1 1 calc R U . . .
C31 C 0.5465(4) 0.1860(4) 0.8320(3) 0.0464(12) Uani 1 1 d . . . . .
H13 H 0.4745 0.2384 0.8267 0.056 Uiso 1 1 calc R U . . .
C32 C 0.5784(5) 0.3177(4) 0.3220(3) 0.0537(13) Uani 1 1 d . . . . .
H14 H 0.5009 0.3524 0.3352 0.081 Uiso 1 1 calc R U . . .
H15 H 0.6135 0.2613 0.3749 0.081 Uiso 1 1 calc R U . . .
H16 H 0.5881 0.2844 0.2747 0.081 Uiso 1 1 calc R U . . .
C33 C 0.6318(4) 0.4334(4) 0.1228(3) 0.0475(12) Uani 1 1 d . . . . .
H17 H 0.5914 0.3850 0.1421 0.071 Uiso 1 1 calc R U . . .
H18 H 0.6998 0.3986 0.0928 0.071 Uiso 1 1 calc R U . . .
H19 H 0.5884 0.5026 0.0820 0.071 Uiso 1 1 calc R U . . .
C34 C 0.7572(3) 0.5862(3) 0.0448(3) 0.0303(9) Uani 1 1 d . . . . .
C35 C 0.8468(4) 0.5006(3) 0.0238(3) 0.0354(10) Uani 1 1 d . . . . .
C36 C 0.8609(4) 0.4793(3) -0.0585(3) 0.0401(10) Uani 1 1 d . . . . .
C37 C 0.7808(4) 0.5440(4) -0.1215(3) 0.0387(10) Uani 1 1 d . . . . .
C38 C 0.6915(4) 0.6312(4) -0.1037(3) 0.0396(10) Uani 1 1 d . . . . .
C39 C 0.6822(4) 0.6528(3) -0.0228(3) 0.0346(9) Uani 1 1 d . . . . .
F1 F 0.9262(2) 0.4335(2) 0.08459(18) 0.0491(7) Uani 1 1 d . . . . .
F2 F 0.9503(2) 0.3961(2) -0.07676(19) 0.0553(8) Uani 1 1 d . . . . .
C41 C 0.8793(4) 1.0314(3) 0.1223(3) 0.0357(10) Uani 1 1 d . . . . .
C44 C 0.6890(4) 1.1952(3) 0.0470(3) 0.0363(10) Uani 1 1 d . . . . .
C48 C 1.0791(4) 0.7978(4) 0.6312(3) 0.0428(11) Uani 1 1 d . . . . .
C49 C 1.0332(4) 0.7946(4) 0.7164(3) 0.0458(12) Uani 1 1 d . . . . .
C50 C 0.9380(4) 0.7717(3) 0.7407(3) 0.0417(11) Uani 1 1 d . . . . .
C52 C 1.0365(4) 0.5012(4) 0.6785(3) 0.0382(10) Uani 1 1 d . . . . .
H20 H 1.0818 0.5374 0.6378 0.057 Uiso 1 1 calc R U . . .
H21 H 1.0789 0.4227 0.6999 0.057 Uiso 1 1 calc R U . . .
H22 H 1.0117 0.5316 0.7285 0.057 Uiso 1 1 calc R U . . .
F3 F 0.7894(3) 0.5205(2) -0.19828(17) 0.0587(8) Uani 1 1 d . . . . .
F4 F 0.6138(2) 0.6961(2) -0.16567(17) 0.0542(7) Uani 1 1 d . . . . .
F5 F 0.5953(2) 0.7409(2) -0.00725(16) 0.0448(6) Uani 1 1 d . . . . .
C40 C 0.7808(4) 1.0157(3) 0.1522(3) 0.0319(9) Uani 1 1 d . . . . .
C42 C 0.8852(4) 1.1234(4) 0.0556(3) 0.0409(11) Uani 1 1 d . . . . .
C43 C 0.7885(4) 1.2056(3) 0.0171(3) 0.0387(10) Uani 1 1 d . . . . .
C45 C 0.6856(3) 1.1017(3) 0.1123(3) 0.0325(9) Uani 1 1 d . . . . .
F6 F 0.9755(2) 0.9506(2) 0.15636(19) 0.0539(7) Uani 1 1 d . . . . .
F7 F 0.9819(2) 1.1343(2) 0.0269(2) 0.0633(9) Uani 1 1 d . . . . .
F8 F 0.7922(2) 1.2958(2) -0.04891(17) 0.0499(7) Uani 1 1 d . . . . .
F9 F 0.5967(2) 1.2783(2) 0.01019(17) 0.0492(7) Uani 1 1 d . . . . .
F10 F 0.5875(2) 1.0923(2) 0.13785(18) 0.0480(7) Uani 1 1 d . . . . .
C46 C 0.9361(4) 0.7522(3) 0.5937(3) 0.0323(9) Uani 1 1 d . . . . .
C47 C 1.0319(4) 0.7763(4) 0.5711(3) 0.0382(10) Uani 1 1 d . . . . .
C51 C 0.8908(4) 0.7534(3) 0.6794(3) 0.0369(10) Uani 1 1 d . . . . .
F11 F 1.0805(2) 0.7780(2) 0.48942(17) 0.0492(7) Uani 1 1 d . . . . .
F12 F 1.1698(2) 0.8226(2) 0.6063(2) 0.0596(8) Uani 1 1 d . . . . .
F13 F 1.0800(3) 0.8146(2) 0.77523(19) 0.0649(9) Uani 1 1 d . . . . .
F14 F 0.8923(3) 0.7702(2) 0.82366(17) 0.0571(8) Uani 1 1 d . . . . .
F15 F 0.7972(2) 0.7339(2) 0.70543(16) 0.0465(6) Uani 1 1 d . . . . .
C53 C 0.9275(4) 0.3249(3) 0.7077(3) 0.0366(10) Uani 1 1 d . . . . .
H23 H 0.8808 0.3260 0.7612 0.055 Uiso 1 1 calc R U . . .
H24 H 1.0028 0.3013 0.7231 0.055 Uiso 1 1 calc R U . . .
H25 H 0.9218 0.2740 0.6808 0.055 Uiso 1 1 calc R U . . .
Cl1A Cl 0.61705(19) 0.72963(18) 0.38470(14) 0.0486(7) Uani 0.543(4) 1 d . . P A
1
Cl3A Cl 0.2266(8) 0.9504(6) 0.3933(5) 0.190(3) Uiso 0.543(4) 1 d . . P A 1
Cl2A Cl 0.5088(12) 0.9788(12) 0.3676(9) 0.306(6) Uiso 0.543(4) 1 d . . P A 1
C54A C 0.3792(17) 1.0171(18) 0.3736(18) 0.116(6) Uiso 0.543(4) 1 d . . P A 1
H30 H 0.3548 1.0480 0.4240 0.140 Uiso 0.543(4) 1 calc R U P A 1
H31 H 0.3529 1.0793 0.3201 0.140 Uiso 0.543(4) 1 calc R U P A 1
C55A C 0.3248(15) 0.9578(14) 0.3812(12) 0.092(6) Uiso 0.543(4) 1 d . . P A 1
H32 H 0.3642 0.8930 0.4290 0.110 Uiso 0.543(4) 1 calc R U P A 1
H33 H 0.3508 0.9345 0.3270 0.110 Uiso 0.543(4) 1 calc R U P A 1
Cl1B Cl 0.5455(5) 0.8319(6) 0.4778(5) 0.177(4) Uani 0.457(4) 1 d . . P A 2
Cl3B Cl 0.2894(3) 0.9485(3) 0.3885(2) 0.0480(8) Uiso 0.457(4) 1 d . . P A 2
C54B C 0.427(2) 1.026(2) 0.3301(15) 0.115(7) Uiso 0.457(4) 1 d . . P A 2
H34 H 0.3710 1.0896 0.2926 0.138 Uiso 0.457(4) 1 calc R U P A 2
H35 H 0.4609 0.9684 0.2997 0.138 Uiso 0.457(4) 1 calc R U P A 2
C55B C 0.3792(16) 0.9818(17) 0.4235(14) 0.094(6) Uiso 0.457(4) 1 d . . P A 2
H36 H 0.3434 1.0389 0.4540 0.113 Uiso 0.457(4) 1 calc R U P A 2
H37 H 0.4341 0.9175 0.4615 0.113 Uiso 0.457(4) 1 calc R U P A 2
Cl2B Cl 0.5342(4) 1.0666(4) 0.3620(3) 0.1091(17) Uiso 0.457(4) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.334(5) . ?
C1 C2 1.417(6) . ?
C1 C24 1.462(6) . ?
C2 O1 1.359(5) . ?
C2 C3 1.394(6) . ?
C3 C4 1.387(6) . ?
C3 H1 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H2 0.9300 . ?
C5 N1 1.363(5) . ?
C5 C6 1.457(6) . ?
C6 N2 1.369(5) . ?
C6 C7 1.402(6) . ?
C7 C8 1.407(6) . ?
C7 C32 1.499(6) . ?
C8 C9 1.420(5) . ?
C8 C33 1.506(6) . ?
C9 N2 1.376(5) . ?
C9 C10 1.424(5) . ?
N2 H26 0.8600 . ?
C10 C11 1.394(5) . ?
C10 C34 1.494(5) . ?
C11 N3 1.399(5) . ?
C11 C12 1.438(5) . ?
C12 C13 1.343(6) . ?
C12 H3 0.9300 . ?
C13 C14 1.442(5) . ?
C13 H4 0.9300 . ?
C14 N3 1.353(5) . ?
C14 C15 1.430(5) . ?
N3 H27 0.8600 . ?
C15 C16 1.391(5) . ?
C15 C40 1.499(5) . ?
C16 N4 1.374(5) . ?
C16 C17 1.433(6) . ?
C17 C18 1.350(6) . ?
C17 H5 0.9300 . ?
C18 C19 1.435(5) . ?
C18 H6 0.9300 . ?
C19 C20 1.379(5) . ?
C19 N4 1.403(5) . ?
N4 H28 0.8600 . ?
C20 C21 1.441(5) . ?
C20 C46 1.489(5) . ?
C21 N5 1.379(5) . ?
C21 C22 1.401(5) . ?
C22 C23 1.414(5) . ?
C22 C52 1.503(6) . ?
C23 C24 1.383(6) . ?
C23 C53 1.499(5) . ?
C24 N5 1.366(5) . ?
N5 H29 0.8600 . ?
O1 C25 1.444(5) . ?
C25 C26 1.503(6) . ?
C25 H7 0.9700 . ?
C25 H8 0.9700 . ?
C26 C31 1.376(6) . ?
C26 C27 1.380(6) . ?
C27 C28 1.383(6) . ?
C27 H9 0.9300 . ?
C28 C29 1.380(7) . ?
C28 H10 0.9300 . ?
C29 C30 1.374(8) . ?
C29 H11 0.9300 . ?
C30 C31 1.400(7) . ?
C30 H12 0.9300 . ?
C31 H13 0.9300 . ?
C32 H14 0.9600 . ?
C32 H15 0.9600 . ?
C32 H16 0.9600 . ?
C33 H17 0.9600 . ?
C33 H18 0.9600 . ?
C33 H19 0.9600 . ?
C34 C35 1.375(6) . ?
C34 C39 1.388(6) . ?
C35 F1 1.354(5) . ?
C35 C36 1.385(6) . ?
C36 F2 1.340(5) . ?
C36 C37 1.377(7) . ?
C37 F3 1.325(5) . ?
C37 C38 1.369(6) . ?
C38 F4 1.349(5) . ?
C38 C39 1.375(5) . ?
C39 F5 1.348(5) . ?
C41 F6 1.352(5) . ?
C41 C42 1.372(6) . ?
C41 C40 1.389(6) . ?
C44 F9 1.341(5) . ?
C44 C45 1.367(5) . ?
C44 C43 1.372(6) . ?
C48 F12 1.342(5) . ?
C48 C49 1.373(7) . ?
C48 C47 1.377(6) . ?
C49 F13 1.345(5) . ?
C49 C50 1.385(7) . ?
C50 F14 1.344(5) . ?
C50 C51 1.366(6) . ?
C52 H20 0.9600 . ?
C52 H21 0.9600 . ?
C52 H22 0.9600 . ?
C40 C45 1.394(6) . ?
C42 F7 1.336(5) . ?
C42 C43 1.383(6) . ?
C43 F8 1.343(4) . ?
C45 F10 1.341(5) . ?
C46 C51 1.386(6) . ?
C46 C47 1.399(6) . ?
C47 F11 1.337(5) . ?
C51 F15 1.344(5) . ?
C53 H23 0.9600 . ?
C53 H24 0.9600 . ?
C53 H25 0.9600 . ?
Cl3A C55A 1.324(18) . ?
Cl2A C54A 1.57(2) . ?
C54A C55A 1.26(2) . ?
C54A H30 0.9700 . ?
C54A H31 0.9700 . ?
C55A H32 0.9700 . ?
C55A H33 0.9700 . ?
Cl3B C55B 1.657(19) . ?
C54B C55B 1.53(3) . ?
C54B Cl2B 1.91(2) . ?
C54B H34 0.9700 . ?
C54B H35 0.9700 . ?
C55B H36 0.9700 . ?
C55B H37 0.9700 . ?

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
N1 C1 C2 121.7(4) . . ?
N1 C1 C24 115.7(4) . . ?
C2 C1 C24 122.5(4) . . ?
O1 C2 C3 124.7(4) . . ?
O1 C2 C1 116.4(4) . . ?
C3 C2 C1 118.8(4) . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H1 120.8 . . ?
C2 C3 H1 120.8 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H2 119.9 . . ?
C3 C4 H2 119.9 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 113.4(4) . . ?
C4 C5 C6 125.3(4) . . ?
C1 N1 C5 119.5(4) . . ?
N2 C6 C7 108.1(4) . . ?
N2 C6 C5 118.5(4) . . ?
C7 C6 C5 133.2(4) . . ?
C6 C7 C8 107.0(4) . . ?
C6 C7 C32 126.4(4) . . ?
C8 C7 C32 126.6(4) . . ?
C7 C8 C9 108.1(4) . . ?
C7 C8 C33 123.1(4) . . ?
C9 C8 C33 128.7(4) . . ?
N2 C9 C8 106.3(3) . . ?
N2 C9 C10 122.7(3) . . ?
C8 C9 C10 131.0(4) . . ?
C6 N2 C9 110.6(3) . . ?
C6 N2 H26 124.7 . . ?
C9 N2 H26 124.7 . . ?
C11 C10 C9 130.0(4) . . ?
C11 C10 C34 114.4(3) . . ?
C9 C10 C34 115.6(3) . . ?
C10 C11 N3 129.1(4) . . ?
C10 C11 C12 122.2(4) . . ?
N3 C11 C12 108.4(3) . . ?
C13 C12 C11 107.7(3) . . ?
C13 C12 H3 126.2 . . ?
C11 C12 H3 126.2 . . ?
C12 C13 C14 107.3(3) . . ?
C12 C13 H4 126.3 . . ?
C14 C13 H4 126.3 . . ?
N3 C14 C15 129.5(4) . . ?
N3 C14 C13 109.8(3) . . ?
C15 C14 C13 120.6(3) . . ?
C14 N3 C11 106.7(3) . . ?
C14 N3 H27 126.6 . . ?
C11 N3 H27 126.6 . . ?
C16 C15 C14 130.3(4) . . ?
C16 C15 C40 115.7(3) . . ?
C14 C15 C40 113.2(3) . . ?
N4 C16 C15 128.5(3) . . ?
N4 C16 C17 106.3(3) . . ?
C15 C16 C17 125.0(4) . . ?
C18 C17 C16 108.7(4) . . ?
C18 C17 H5 125.6 . . ?
C16 C17 H5 125.6 . . ?
C17 C18 C19 109.1(4) . . ?
C17 C18 H6 125.4 . . ?
C19 C18 H6 125.4 . . ?
C20 C19 N4 127.9(4) . . ?
C20 C19 C18 126.8(4) . . ?
N4 C19 C18 105.2(3) . . ?
C16 N4 C19 110.4(3) . . ?
C16 N4 H28 124.8 . . ?
C19 N4 H28 124.8 . . ?
C19 C20 C21 127.3(4) . . ?
C19 C20 C46 116.4(3) . . ?
C21 C20 C46 116.3(3) . . ?
N5 C21 C22 107.3(3) . . ?
N5 C21 C20 122.7(4) . . ?
C22 C21 C20 129.8(4) . . ?
C21 C22 C23 107.7(4) . . ?
C21 C22 C52 127.6(4) . . ?
C23 C22 C52 124.7(4) . . ?
C24 C23 C22 106.7(3) . . ?
C24 C23 C53 126.6(4) . . ?
C22 C23 C53 126.7(4) . . ?
N5 C24 C23 109.2(4) . . ?
N5 C24 C1 118.5(4) . . ?
C23 C24 C1 132.1(4) . . ?
C24 N5 C21 109.1(3) . . ?
C24 N5 H29 125.5 . . ?
C21 N5 H29 125.5 . . ?
C2 O1 C25 118.0(3) . . ?
O1 C25 C26 115.4(4) . . ?
O1 C25 H7 108.4 . . ?
C26 C25 H7 108.4 . . ?
O1 C25 H8 108.4 . . ?
C26 C25 H8 108.4 . . ?
H7 C25 H8 107.5 . . ?
C31 C26 C27 119.4(4) . . ?
C31 C26 C25 118.9(4) . . ?
C27 C26 C25 121.6(4) . . ?
C26 C27 C28 120.9(5) . . ?
C26 C27 H9 119.6 . . ?
C28 C27 H9 119.6 . . ?
C29 C28 C27 119.8(5) . . ?
C29 C28 H10 120.1 . . ?
C27 C28 H10 120.1 . . ?
C30 C29 C28 119.8(5) . . ?
C30 C29 H11 120.1 . . ?
C28 C29 H11 120.1 . . ?
C29 C30 C31 120.2(5) . . ?
C29 C30 H12 119.9 . . ?
C31 C30 H12 119.9 . . ?
C26 C31 C30 119.8(5) . . ?
C26 C31 H13 120.1 . . ?
C30 C31 H13 120.1 . . ?
C7 C32 H14 109.5 . . ?
C7 C32 H15 109.5 . . ?
H14 C32 H15 109.5 . . ?
C7 C32 H16 109.5 . . ?
H14 C32 H16 109.5 . . ?
H15 C32 H16 109.5 . . ?
C8 C33 H17 109.5 . . ?
C8 C33 H18 109.5 . . ?
H17 C33 H18 109.5 . . ?
C8 C33 H19 109.5 . . ?
H17 C33 H19 109.5 . . ?
H18 C33 H19 109.5 . . ?
C35 C34 C39 115.8(4) . . ?
C35 C34 C10 122.2(4) . . ?
C39 C34 C10 122.0(4) . . ?
F1 C35 C34 119.9(4) . . ?
F1 C35 C36 117.3(4) . . ?
C34 C35 C36 122.8(4) . . ?
F2 C36 C37 119.9(4) . . ?
F2 C36 C35 120.9(4) . . ?
C37 C36 C35 119.2(4) . . ?
F3 C37 C38 120.2(4) . . ?
F3 C37 C36 120.1(4) . . ?
C38 C37 C36 119.6(4) . . ?
F4 C38 C37 120.0(4) . . ?
F4 C38 C39 120.3(4) . . ?
C37 C38 C39 119.7(4) . . ?
F5 C39 C38 118.9(4) . . ?
F5 C39 C34 118.3(3) . . ?
C38 C39 C34 122.7(4) . . ?
F6 C41 C42 117.3(4) . . ?
F6 C41 C40 119.4(3) . . ?
C42 C41 C40 123.2(4) . . ?
F9 C44 C45 121.6(4) . . ?
F9 C44 C43 118.3(4) . . ?
C45 C44 C43 120.1(4) . . ?
F12 C48 C49 119.9(4) . . ?
F12 C48 C47 120.0(4) . . ?
C49 C48 C47 120.1(4) . . ?
F13 C49 C48 120.0(5) . . ?
F13 C49 C50 120.5(4) . . ?
C48 C49 C50 119.4(4) . . ?
F14 C50 C51 121.1(4) . . ?
F14 C50 C49 119.3(4) . . ?
C51 C50 C49 119.6(4) . . ?
C22 C52 H20 109.5 . . ?
C22 C52 H21 109.5 . . ?
H20 C52 H21 109.5 . . ?
C22 C52 H22 109.5 . . ?
H20 C52 H22 109.5 . . ?
H21 C52 H22 109.5 . . ?
C41 C40 C45 115.9(3) . . ?
C41 C40 C15 121.6(4) . . ?
C45 C40 C15 122.3(4) . . ?
F7 C42 C41 121.5(4) . . ?
F7 C42 C43 119.8(4) . . ?
C41 C42 C43 118.6(4) . . ?
F8 C43 C44 120.2(4) . . ?
F8 C43 C42 119.8(4) . . ?
C44 C43 C42 120.0(4) . . ?
F10 C45 C44 118.7(4) . . ?
F10 C45 C40 119.2(3) . . ?
C44 C45 C40 122.1(4) . . ?
C51 C46 C47 115.9(4) . . ?
C51 C46 C20 121.3(4) . . ?
C47 C46 C20 122.7(4) . . ?
F11 C47 C48 118.2(4) . . ?
F11 C47 C46 119.9(4) . . ?
C48 C47 C46 121.9(4) . . ?
F15 C51 C50 117.4(4) . . ?
F15 C51 C46 119.6(4) . . ?
C50 C51 C46 123.0(4) . . ?
C23 C53 H23 109.5 . . ?
C23 C53 H24 109.5 . . ?
H23 C53 H24 109.5 . . ?
C23 C53 H25 109.5 . . ?
H23 C53 H25 109.5 . . ?
H24 C53 H25 109.5 . . ?
C55A C54A Cl2A 126.8(18) . . ?
C55A C54A H30 105.6 . . ?
Cl2A C54A H30 105.6 . . ?
C55A C54A H31 105.6 . . ?
Cl2A C54A H31 105.6 . . ?
H30 C54A H31 106.1 . . ?
C54A C55A Cl3A 147.2(18) . . ?
C54A C55A H32 100.0 . . ?
Cl3A C55A H32 100.0 . . ?
C54A C55A H33 100.0 . . ?
Cl3A C55A H33 100.0 . . ?
H32 C55A H33 104.2 . . ?
C55B C54B Cl2B 100.5(14) . . ?
C55B C54B H34 111.7 . . ?
Cl2B C54B H34 111.7 . . ?
C55B C54B H35 111.7 . . ?
Cl2B C54B H35 111.7 . . ?
H34 C54B H35 109.4 . . ?
C54B C55B Cl3B 96.5(15) . . ?
C54B C55B H36 112.4 . . ?
Cl3B C55B H36 112.4 . . ?
C54B C55B H37 112.4 . . ?
Cl3B C55B H37 112.4 . . ?
H36 C55B H37 110.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -175.5(4) . . . . ?
C24 C1 C2 O1 1.5(6) . . . . ?
N1 C1 C2 C3 1.4(7) . . . . ?
C24 C1 C2 C3 178.4(4) . . . . ?
O1 C2 C3 C4 176.8(4) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
C3 C4 C5 N1 0.1(8) . . . . ?
C3 C4 C5 C6 179.8(5) . . . . ?
C2 C1 N1 C5 -2.2(7) . . . . ?
C24 C1 N1 C5 -179.5(4) . . . . ?
C4 C5 N1 C1 1.5(7) . . . . ?
C6 C5 N1 C1 -178.2(4) . . . . ?
N1 C5 C6 N2 -15.0(6) . . . . ?
C4 C5 C6 N2 165.3(5) . . . . ?
N1 C5 C6 C7 159.0(5) . . . . ?
C4 C5 C6 C7 -20.8(9) . . . . ?
N2 C6 C7 C8 0.4(5) . . . . ?
C5 C6 C7 C8 -174.0(5) . . . . ?
N2 C6 C7 C32 -178.8(5) . . . . ?
C5 C6 C7 C32 6.8(9) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C32 C7 C8 C9 179.1(5) . . . . ?
C6 C7 C8 C33 -175.9(4) . . . . ?
C32 C7 C8 C33 3.3(8) . . . . ?
C7 C8 C9 N2 -0.3(5) . . . . ?
C33 C8 C9 N2 175.3(4) . . . . ?
C7 C8 C9 C10 -179.8(5) . . . . ?
C33 C8 C9 C10 -4.3(8) . . . . ?
C7 C6 N2 C9 -0.6(5) . . . . ?
C5 C6 N2 C9 174.7(4) . . . . ?
C8 C9 N2 C6 0.6(5) . . . . ?
C10 C9 N2 C6 -179.8(4) . . . . ?
N2 C9 C10 C11 -12.3(7) . . . . ?
C8 C9 C10 C11 167.2(5) . . . . ?
N2 C9 C10 C34 168.7(4) . . . . ?
C8 C9 C10 C34 -11.8(7) . . . . ?
C9 C10 C11 N3 -3.8(8) . . . . ?
C34 C10 C11 N3 175.2(4) . . . . ?
C9 C10 C11 C12 -176.7(4) . . . . ?
C34 C10 C11 C12 2.3(6) . . . . ?
C10 C11 C12 C13 172.0(4) . . . . ?
N3 C11 C12 C13 -2.2(5) . . . . ?
C11 C12 C13 C14 2.0(5) . . . . ?
C12 C13 C14 N3 -1.3(5) . . . . ?
C12 C13 C14 C15 176.2(4) . . . . ?
C15 C14 N3 C11 -177.3(4) . . . . ?
C13 C14 N3 C11 -0.1(5) . . . . ?
C10 C11 N3 C14 -172.3(4) . . . . ?
C12 C11 N3 C14 1.4(5) . . . . ?
N3 C14 C15 C16 24.4(8) . . . . ?
C13 C14 C15 C16 -152.6(4) . . . . ?
N3 C14 C15 C40 -166.2(4) . . . . ?
C13 C14 C15 C40 16.8(6) . . . . ?
C14 C15 C16 N4 -1.2(8) . . . . ?
C40 C15 C16 N4 -170.4(4) . . . . ?
C14 C15 C16 C17 171.7(5) . . . . ?
C40 C15 C16 C17 2.5(6) . . . . ?
N4 C16 C17 C18 4.3(5) . . . . ?
C15 C16 C17 C18 -169.9(4) . . . . ?
C16 C17 C18 C19 -1.6(6) . . . . ?
C17 C18 C19 C20 175.9(5) . . . . ?
C17 C18 C19 N4 -1.6(5) . . . . ?
C15 C16 N4 C19 168.5(4) . . . . ?
C17 C16 N4 C19 -5.4(5) . . . . ?
C20 C19 N4 C16 -173.1(4) . . . . ?
C18 C19 N4 C16 4.4(5) . . . . ?
N4 C19 C20 C21 -10.5(7) . . . . ?
C18 C19 C20 C21 172.5(4) . . . . ?
N4 C19 C20 C46 170.7(4) . . . . ?
C18 C19 C20 C46 -6.3(7) . . . . ?
C19 C20 C21 N5 -23.7(7) . . . . ?
C46 C20 C21 N5 155.1(4) . . . . ?
C19 C20 C21 C22 162.5(5) . . . . ?
C46 C20 C21 C22 -18.7(7) . . . . ?
N5 C21 C22 C23 -2.3(5) . . . . ?
C20 C21 C22 C23 172.3(4) . . . . ?
N5 C21 C22 C52 174.0(4) . . . . ?
C20 C21 C22 C52 -11.4(7) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C52 C22 C23 C24 -176.3(4) . . . . ?
C21 C22 C23 C53 179.8(4) . . . . ?
C52 C22 C23 C53 3.3(7) . . . . ?
C22 C23 C24 N5 2.1(5) . . . . ?
C53 C23 C24 N5 -177.5(4) . . . . ?
C22 C23 C24 C1 176.2(5) . . . . ?
C53 C23 C24 C1 -3.4(8) . . . . ?
N1 C1 C24 N5 40.7(6) . . . . ?
C2 C1 C24 N5 -136.5(4) . . . . ?
N1 C1 C24 C23 -132.9(5) . . . . ?
C2 C1 C24 C23 49.8(7) . . . . ?
C23 C24 N5 C21 -3.6(5) . . . . ?
C1 C24 N5 C21 -178.6(4) . . . . ?
C22 C21 N5 C24 3.6(5) . . . . ?
C20 C21 N5 C24 -171.4(4) . . . . ?
C3 C2 O1 C25 -9.4(6) . . . . ?
C1 C2 O1 C25 167.3(4) . . . . ?
C2 O1 C25 C26 77.2(5) . . . . ?
O1 C25 C26 C31 -145.7(4) . . . . ?
O1 C25 C26 C27 36.2(6) . . . . ?
C31 C26 C27 C28 -0.1(7) . . . . ?
C25 C26 C27 C28 178.1(4) . . . . ?
C26 C27 C28 C29 0.2(8) . . . . ?
C27 C28 C29 C30 -1.4(8) . . . . ?
C28 C29 C30 C31 2.6(8) . . . . ?
C27 C26 C31 C30 1.2(7) . . . . ?
C25 C26 C31 C30 -177.0(4) . . . . ?
C29 C30 C31 C26 -2.5(8) . . . . ?
C11 C10 C34 C35 103.5(5) . . . . ?
C9 C10 C34 C35 -77.3(5) . . . . ?
C11 C10 C34 C39 -77.0(5) . . . . ?
C9 C10 C34 C39 102.1(5) . . . . ?
C39 C34 C35 F1 177.8(4) . . . . ?
C10 C34 C35 F1 -2.7(6) . . . . ?
C39 C34 C35 C36 -1.7(6) . . . . ?
C10 C34 C35 C36 177.8(4) . . . . ?
F1 C35 C36 F2 -0.6(6) . . . . ?
C34 C35 C36 F2 179.0(4) . . . . ?
F1 C35 C36 C37 178.5(4) . . . . ?
C34 C35 C36 C37 -1.9(6) . . . . ?
F2 C36 C37 F3 3.4(6) . . . . ?
C35 C36 C37 F3 -175.7(4) . . . . ?
F2 C36 C37 C38 -177.8(4) . . . . ?
C35 C36 C37 C38 3.1(6) . . . . ?
F3 C37 C38 F4 -2.4(6) . . . . ?
C36 C37 C38 F4 178.8(4) . . . . ?
F3 C37 C38 C39 178.2(4) . . . . ?
C36 C37 C38 C39 -0.5(6) . . . . ?
F4 C38 C39 F5 -1.2(6) . . . . ?
C37 C38 C39 F5 178.2(4) . . . . ?
F4 C38 C39 C34 177.3(4) . . . . ?
C37 C38 C39 C34 -3.4(7) . . . . ?
C35 C34 C39 F5 -177.1(3) . . . . ?
C10 C34 C39 F5 3.4(6) . . . . ?
C35 C34 C39 C38 4.4(6) . . . . ?
C10 C34 C39 C38 -175.1(4) . . . . ?
F12 C48 C49 F13 -1.0(7) . . . . ?
C47 C48 C49 F13 179.4(4) . . . . ?
F12 C48 C49 C50 178.4(4) . . . . ?
C47 C48 C49 C50 -1.3(7) . . . . ?
F13 C49 C50 F14 0.3(6) . . . . ?
C48 C49 C50 F14 -179.0(4) . . . . ?
F13 C49 C50 C51 178.9(4) . . . . ?
C48 C49 C50 C51 -0.4(7) . . . . ?
F6 C41 C40 C45 -178.5(4) . . . . ?
C42 C41 C40 C45 -2.0(6) . . . . ?
F6 C41 C40 C15 -4.6(6) . . . . ?
C42 C41 C40 C15 171.9(4) . . . . ?
C16 C15 C40 C41 76.7(5) . . . . ?
C14 C15 C40 C41 -94.4(5) . . . . ?
C16 C15 C40 C45 -109.8(5) . . . . ?
C14 C15 C40 C45 79.1(5) . . . . ?
F6 C41 C42 F7 -1.6(7) . . . . ?
C40 C41 C42 F7 -178.2(4) . . . . ?
F6 C41 C42 C43 177.6(4) . . . . ?
C40 C41 C42 C43 1.0(7) . . . . ?
F9 C44 C43 F8 -1.7(6) . . . . ?
C45 C44 C43 F8 178.0(4) . . . . ?
F9 C44 C43 C42 177.7(4) . . . . ?
C45 C44 C43 C42 -2.7(7) . . . . ?
F7 C42 C43 F8 0.0(7) . . . . ?
C41 C42 C43 F8 -179.2(4) . . . . ?
F7 C42 C43 C44 -179.4(4) . . . . ?
C41 C42 C43 C44 1.4(7) . . . . ?
F9 C44 C45 F10 1.9(6) . . . . ?
C43 C44 C45 F10 -177.7(4) . . . . ?
F9 C44 C45 C40 -178.8(4) . . . . ?
C43 C44 C45 C40 1.6(6) . . . . ?
C41 C40 C45 F10 180.0(4) . . . . ?
C15 C40 C45 F10 6.1(6) . . . . ?
C41 C40 C45 C44 0.7(6) . . . . ?
C15 C40 C45 C44 -173.1(4) . . . . ?
C19 C20 C46 C51 119.5(4) . . . . ?
C21 C20 C46 C51 -59.4(5) . . . . ?
C19 C20 C46 C47 -62.4(6) . . . . ?
C21 C20 C46 C47 118.7(4) . . . . ?
F12 C48 C47 F11 1.7(6) . . . . ?
C49 C48 C47 F11 -178.6(4) . . . . ?
F12 C48 C47 C46 -178.8(4) . . . . ?
C49 C48 C47 C46 0.9(7) . . . . ?
C51 C46 C47 F11 -179.4(4) . . . . ?
C20 C46 C47 F11 2.4(6) . . . . ?
C51 C46 C47 C48 1.1(6) . . . . ?
C20 C46 C47 C48 -177.0(4) . . . . ?
F14 C50 C51 F15 0.0(6) . . . . ?
C49 C50 C51 F15 -178.6(4) . . . . ?
F14 C50 C51 C46 -178.8(4) . . . . ?
C49 C50 C51 C46 2.6(7) . . . . ?
C47 C46 C51 F15 178.3(4) . . . . ?
C20 C46 C51 F15 -3.5(6) . . . . ?
C47 C46 C51 C50 -2.9(6) . . . . ?
C20 C46 C51 C50 175.3(4) . . . . ?
Cl2A C54A C55A Cl3A 174(2) . . . . ?
Cl2B C54B C55B Cl3B -179.6(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H1 Cl1A 0.93 2.83 3.488(5) 129.0 2_666
C13 H4 F7 0.93 2.54 3.086(5) 118.1 2_775
C18 H6 Cl3A 0.93 2.89 3.669(9) 142.3 2_676
C3 H1 Cl1A 0.93 2.83 3.488(5) 129.0 2_666
C13 H4 F7 0.93 2.54 3.086(5) 118.1 2_775
C25 H8 F9 0.97 2.65 3.413(5) 136.0 1_546
N2 H26 N3 0.86 2.57 3.107(5) 121.2 .
N2 H26 Cl1A 0.86 2.61 3.248(4) 132.4 .
N3 H27 N2 0.86 2.65 3.107(5) 114.4 .
N3 H27 Cl1A 0.86 2.28 3.063(4) 150.9 .
N4 H28 N5 0.86 2.62 3.087(4) 115.3 .
N4 H28 Cl1A 0.86 2.51 3.060(4) 122.3 .
N5 H29 N4 0.86 2.60 3.087(4) 116.9 .
N5 H29 Cl1A 0.86 2.36 3.205(4) 167.1 .
C54A H31 F15 0.97 2.48 3.22(2) 133.1 2_676
C54B H34 F15 0.97 2.55 3.37(3) 143.4 2_676
Cl1B H37 Cl3B 1.46 2.22 3.424(7) 136.0 .
C55B H37 Cl1B 0.97 1.46 2.37(2) 152.4 .
C55B H37 Cl2B 0.97 2.96 3.51(2) 116.9 2_676

_refine_diff_density_max         0.898
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_1117ty_a
_database_code_depnum_ccdc_archive 'CCDC 1996099'
loop_
_audit_author_name
_audit_author_address
'Tomoki Yoneda'
;Hokkaido University
Japan
;
_audit_update_record             
;
2020-04-10 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H24 Cl6 F15 N5 O'
_chemical_formula_weight         1184.42

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'
F F 0.0727 0.0534 '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                   12.2776(3)
_cell_length_b                   13.0559(3)
_cell_length_c                   16.5083(4)
_cell_angle_alpha                105.2410(10)
_cell_angle_beta                 110.6130(10)
_cell_angle_gamma                98.939(2)
_cell_volume                     2297.85(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4860
_cell_measurement_theta_min      3.045
_cell_measurement_theta_max      68.240

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   0.620
_exptl_transmission_factor_max   0.803
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.388
_shelx_estimated_absorpt_T_min   0.474
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rugaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            24539
_diffrn_reflns_av_unetI/netI     0.1611
_diffrn_reflns_av_R_equivalents  0.1320
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             8211
_reflns_number_gt                4860
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1239P)²] 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         8211
_refine_ls_number_parameters     680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2705
_refine_ls_wR_factor_gt          0.2355
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.8939(5) 0.7630(5) 0.9809(4) 0.0239(12) Uani 1 1 d . . . . .
C2 C 0.8605(5) 0.8618(5) 1.0026(4) 0.0254(12) Uani 1 1 d . . . . .
C3 C 0.7379(4) 0.8411(5) 0.9458(4) 0.0237(12) Uani 1 1 d . . . . .
C4 C 0.6958(5) 0.7282(5) 0.8886(3) 0.0223(12) Uani 1 1 d . . . . .
C5 C 0.5776(5) 0.6660(4) 0.8212(4) 0.0216(12) Uani 1 1 d . . . . .
C6 C 0.5408(5) 0.5625(5) 0.7523(4) 0.0222(12) Uani 1 1 d . . . . .
C7 C 0.4187(5) 0.5009(5) 0.6954(4) 0.0255(13) Uani 1 1 d . . . . .
H3 H 0.3495 0.5199 0.7012 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4170(5) 0.4108(5) 0.6318(4) 0.0225(12) Uani 1 1 d . . . . .
H4 H 0.3464 0.3569 0.5845 0.027 Uiso 1 1 calc R U . . .
N1 N 0.6117(4) 0.5036(4) 0.7221(3) 0.0246(11) Uani 1 1 d . . . . .
H5 H 0.6913 0.5232 0.7470 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5397(5) 0.4096(5) 0.6471(4) 0.0247(13) Uani 1 1 d . . . . .
C10 C 0.5714(4) 0.3308(5) 0.5905(4) 0.0211(12) Uani 1 1 d . . . . .
C11 C 0.6845(5) 0.3124(5) 0.6002(4) 0.0239(12) Uani 1 1 d . . . . .
C12 C 0.7073(5) 0.2454(5) 0.5280(4) 0.0232(12) Uani 1 1 d . . . . .
H6 H 0.6501 0.2095 0.4658 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8233(4) 0.2411(5) 0.5620(4) 0.0247(12) Uani 1 1 d . . . . .
H7 H 0.8610 0.2017 0.5278 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8798(4) 0.3057(5) 0.6581(4) 0.0225(12) Uani 1 1 d . . . . .
N2 N 0.7925(4) 0.3505(4) 0.6779(3) 0.0242(10) Uani 1 1 d . . . . .
H8 H 0.8043 0.3962 0.7319 0.029 Uiso 1 1 calc R U . . .
C15 C 0.9999(5) 0.3154(5) 0.7156(4) 0.0250(13) Uani 1 1 d . . . . .
C16 C 1.0735(4) 0.3829(5) 0.8070(4) 0.0226(12) Uani 1 1 d . . . . .
C17 C 1.1951(5) 0.3905(5) 0.8646(4) 0.0247(12) Uani 1 1 d . . . . .
C18 C 1.2265(5) 0.4710(5) 0.9493(4) 0.0234(12) Uani 1 1 d . . . . .
C19 C 1.1258(4) 0.5113(4) 0.9465(4) 0.0221(12) Uani 1 1 d . . . . .
N3 N 1.0364(4) 0.4584(4) 0.8597(3) 0.0229(10) Uani 1 1 d . . . . .
H9 H 0.9649 0.4709 0.8400 0.027 Uiso 1 1 calc R U . . .
C20 C 1.1082(4) 0.6005(4) 1.0084(4) 0.0206(12) Uani 1 1 d . . . . .
C21 C 1.1756(4) 0.6381(5) 1.1074(4) 0.0244(12) Uani 1 1 d . . . . .
C22 C 1.1756(4) 0.7474(4) 1.1554(3) 0.0217(12) Uani 1 1 d . . . . .
H10 H 1.2348 0.7874 1.2163 0.026 Uiso 1 1 calc R U . . .
C23 C 1.0899(5) 0.7930(5) 1.1128(4) 0.0269(13) Uani 1 1 d . . . . .
H11 H 1.0879 0.8644 1.1443 0.032 Uiso 1 1 calc R U . . .
C24 C 1.0031(4) 0.7333(5) 1.0204(4) 0.0226(12) Uani 1 1 d . . . . .
N4 N 1.0179(4) 0.6426(4) 0.9687(3) 0.0246(11) Uani 1 1 d . . . . .
N5 N 0.7943(3) 0.6838(4) 0.9102(3) 0.0228(10) Uani 1 1 d . . . . .
H12 H 0.7930 0.6157 0.8827 0.027 Uiso 1 1 calc R U . . .
C25 C 0.9411(5) 0.9721(5) 1.0738(4) 0.0293(14) Uani 1 1 d . . . . .
H13 H 0.9127 1.0315 1.0546 0.044 Uiso 1 1 calc R U . . .
H14 H 1.0244 0.9792 1.0798 0.044 Uiso 1 1 calc R U . . .
H15 H 0.9384 0.9771 1.1334 0.044 Uiso 1 1 calc R U . . .
C26 C 0.6727(5) 0.9283(5) 0.9431(4) 0.0323(14) Uani 1 1 d . . . . .
H16 H 0.6205 0.9225 0.9759 0.048 Uiso 1 1 calc R U . . .
H17 H 0.6231 0.9185 0.8789 0.048 Uiso 1 1 calc R U . . .
H18 H 0.7316 1.0012 0.9728 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4766(4) 0.7146(5) 0.8233(4) 0.0238(12) Uani 1 1 d . . . . .
C28 C 0.4365(5) 0.7250(5) 0.8932(4) 0.0281(13) Uani 1 1 d . . . . .
C29 C 0.3434(5) 0.7730(5) 0.8955(4) 0.0331(14) Uani 1 1 d . . . . .
C30 C 0.2865(5) 0.8102(5) 0.8258(4) 0.0299(14) Uani 1 1 d . . . . .
C31 C 0.3224(5) 0.7994(5) 0.7544(4) 0.0310(14) Uani 1 1 d . . . . .
C32 C 0.4157(5) 0.7534(5) 0.7539(4) 0.0257(13) Uani 1 1 d . . . . .
F1 F 0.4915(3) 0.6907(3) 0.9630(2) 0.0368(9) Uani 1 1 d . . . . .
F2 F 0.3088(3) 0.7820(3) 0.9653(2) 0.0426(9) Uani 1 1 d . . . . .
F3 F 0.1987(3) 0.8582(3) 0.8287(2) 0.0441(10) Uani 1 1 d . . . . .
F4 F 0.2674(3) 0.8366(3) 0.6854(2) 0.0436(10) Uani 1 1 d . . . . .
F5 F 0.4479(3) 0.7461(3) 0.6835(2) 0.0366(9) Uani 1 1 d . . . . .
C33 C 0.4697(5) 0.2539(5) 0.5034(4) 0.0238(12) Uani 1 1 d . . . . .
C34 C 0.4268(5) 0.1435(5) 0.4865(4) 0.0262(13) Uani 1 1 d . . . . .
C35 C 0.3324(5) 0.0722(5) 0.4054(4) 0.0280(13) Uani 1 1 d . . . . .
C36 C 0.2784(5) 0.1136(5) 0.3373(4) 0.0286(14) Uani 1 1 d . . . . .
C37 C 0.3172(5) 0.2235(5) 0.3512(4) 0.0259(13) Uani 1 1 d . . . . .
C38 C 0.4100(5) 0.2915(5) 0.4311(4) 0.0239(12) Uani 1 1 d . . . . .
F6 F 0.4764(3) 0.1001(3) 0.5529(2) 0.0340(8) Uani 1 1 d . . . . .
F7 F 0.2928(3) -0.0351(3) 0.3926(2) 0.0366(9) Uani 1 1 d . . . . .
F8 F 0.1879(3) 0.0463(3) 0.2585(2) 0.0400(9) Uani 1 1 d . . . . .
F9 F 0.2655(3) 0.2620(3) 0.2831(2) 0.0369(9) Uani 1 1 d . . . . .
F10 F 0.4498(3) 0.3983(3) 0.4406(2) 0.0327(8) Uani 1 1 d . . . . .
C39 C 1.0547(4) 0.2368(5) 0.6677(4) 0.0260(13) Uani 1 1 d . . . . .
C40 C 1.0513(5) 0.1338(5) 0.6778(4) 0.0311(14) Uani 1 1 d . . . . .
C41 C 1.0952(5) 0.0580(6) 0.6328(5) 0.0377(16) Uani 1 1 d . . . . .
C42 C 1.1413(5) 0.0843(6) 0.5730(5) 0.0378(16) Uani 1 1 d . . . . .
C43 C 1.1421(5) 0.1819(6) 0.5587(4) 0.0351(15) Uani 1 1 d . . . . .
C44 C 1.1021(5) 0.2583(5) 0.6077(4) 0.0268(13) Uani 1 1 d . . . . .
F11 F 1.0050(3) 0.1061(3) 0.7335(2) 0.0440(10) Uani 1 1 d . . . . .
F12 F 1.0911(3) -0.0401(3) 0.6436(3) 0.0535(11) Uani 1 1 d . . . . .
F13 F 1.1837(3) 0.0098(3) 0.5267(3) 0.0551(11) Uani 1 1 d . . . . .
F14 F 1.1811(3) 0.2047(3) 0.4970(3) 0.0506(11) Uani 1 1 d . . . . .
F15 F 1.1083(3) 0.3563(3) 0.5954(2) 0.0404(9) Uani 1 1 d . . . . .
C45 C 1.2817(5) 0.3306(6) 0.8420(4) 0.0411(17) Uani 1 1 d . . . . .
H19 H 1.3614 0.3606 0.8939 0.062 Uiso 1 1 calc R U . . .
H20 H 1.2883 0.3404 0.7869 0.062 Uiso 1 1 calc R U . . .
H21 H 1.2516 0.2518 0.8305 0.062 Uiso 1 1 calc R U . . .
C46 C 1.3512(4) 0.5142(5) 1.0274(4) 0.0259(13) Uani 1 1 d . . . . .
H22 H 1.3630 0.4631 1.0617 0.039 Uiso 1 1 calc R U . . .
H23 H 1.3590 0.5869 1.0687 0.039 Uiso 1 1 calc R U . . .
H24 H 1.4124 0.5207 1.0023 0.039 Uiso 1 1 calc R U . . .
O1 O 1.2243(3) 0.5775(3) 1.1505(2) 0.0248(9) Uani 1 1 d . . . . .
Cl1 Cl 0.48034(14) 0.22573(14) 0.75352(11) 0.0421(4) Uani 1 1 d . . . . .
Cl2 Cl 0.52977(16) 0.01342(15) 0.72995(12) 0.0474(5) Uani 1 1 d . . . . .
Cl3 Cl 0.41035(16) 0.08768(15) 0.84849(12) 0.0499(5) Uani 1 1 d . . . . .
Cl4 Cl -0.19962(17) 0.54213(19) 0.55192(16) 0.0717(7) Uani 1 1 d . . . . .
Cl5 Cl -0.0309(2) 0.63058(19) 0.74400(16) 0.0810(7) Uani 1 1 d . . . . .
Cl6 Cl 0.0559(2) 0.6277(3) 0.60048(19) 0.1132(11) Uani 1 1 d . . . . .
C47 C 0.5170(6) 0.1286(6) 0.8065(4) 0.0382(16) Uani 1 1 d . . . . .
H1 H 0.5975 0.1639 0.8601 0.046 Uiso 1 1 calc R U . . .
C48 C -0.0576(9) 0.5627(9) 0.6273(6) 0.090(3) Uani 1 1 d . . . . .
H2 H -0.0469 0.4875 0.6237 0.108 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
C1 N5 1.377(6) . ?
C1 C2 1.408(8) . ?
C1 C24 1.433(7) . ?
C2 C3 1.402(7) . ?
C2 C25 1.511(7) . ?
C3 C4 1.421(7) . ?
C3 C26 1.492(8) . ?
C4 N5 1.396(6) . ?
C4 C5 1.422(7) . ?
C5 C6 1.402(7) . ?
C5 C27 1.485(7) . ?
C6 N1 1.382(7) . ?
C6 C7 1.419(7) . ?
C7 C8 1.346(7) . ?
C7 H3 0.9500 . ?
C8 C9 1.441(7) . ?
C8 H4 0.9500 . ?
N1 C9 1.383(7) . ?
N1 H5 0.8800 . ?
C9 C10 1.400(8) . ?
C10 C11 1.407(7) . ?
C10 C33 1.491(7) . ?
C11 N2 1.383(6) . ?
C11 C12 1.424(7) . ?
C12 C13 1.351(7) . ?
C12 H6 0.9500 . ?
C13 C14 1.432(7) . ?
C13 H7 0.9500 . ?
C14 N2 1.393(6) . ?
C14 C15 1.409(7) . ?
N2 H8 0.8800 . ?
C15 C16 1.401(7) . ?
C15 C39 1.515(8) . ?
C16 N3 1.378(7) . ?
C16 C17 1.431(7) . ?
C17 C18 1.389(7) . ?
C17 C45 1.505(8) . ?
C18 C19 1.408(7) . ?
C18 C46 1.511(7) . ?
C19 N3 1.368(6) . ?
C19 C20 1.434(7) . ?
N3 H9 0.8800 . ?
C20 N4 1.352(6) . ?
C20 C21 1.448(7) . ?
C21 O1 1.278(6) . ?
C21 C22 1.439(8) . ?
C22 C23 1.360(7) . ?
C22 H10 0.9500 . ?
C23 C24 1.428(7) . ?
C23 H11 0.9500 . ?
C24 N4 1.345(7) . ?
N5 H12 0.8800 . ?
C25 H13 0.9800 . ?
C25 H14 0.9800 . ?
C25 H15 0.9800 . ?
C26 H16 0.9800 . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?
C27 C28 1.389(8) . ?
C27 C32 1.396(7) . ?
C28 F1 1.342(6) . ?
C28 C29 1.394(8) . ?
C29 F2 1.344(7) . ?
C29 C30 1.372(8) . ?
C30 F3 1.337(6) . ?
C30 C31 1.379(8) . ?
C31 F4 1.356(6) . ?
C31 C32 1.374(7) . ?
C32 F5 1.340(6) . ?
C33 C34 1.373(8) . ?
C33 C38 1.415(7) . ?
C34 F6 1.362(6) . ?
C34 C35 1.386(7) . ?
C35 F7 1.344(6) . ?
C35 C36 1.378(8) . ?
C36 F8 1.333(6) . ?
C36 C37 1.369(8) . ?
C37 F9 1.347(6) . ?
C37 C38 1.356(7) . ?
C38 F10 1.351(6) . ?
C39 C44 1.378(8) . ?
C39 C40 1.394(8) . ?
C40 F11 1.334(7) . ?
C40 C41 1.373(8) . ?
C41 F12 1.335(7) . ?
C41 C42 1.386(9) . ?
C42 C43 1.355(9) . ?
C42 F13 1.359(7) . ?
C43 F14 1.345(7) . ?
C43 C44 1.380(8) . ?
C44 F15 1.342(6) . ?
C45 H19 0.9800 . ?
C45 H20 0.9800 . ?
C45 H21 0.9800 . ?
C46 H22 0.9800 . ?
C46 H23 0.9800 . ?
C46 H24 0.9800 . ?
Cl1 C47 1.750(7) . ?
Cl2 C47 1.760(7) . ?
Cl3 C47 1.760(7) . ?
Cl4 C48 1.677(9) . ?
Cl5 C48 1.780(10) . ?
Cl6 C48 1.767(10) . ?
C47 H1 1.0000 . ?
C48 H2 1.0000 . ?

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
N5 C1 C2 107.8(5) . . ?
N5 C1 C24 119.4(5) . . ?
C2 C1 C24 132.7(5) . . ?
C3 C2 C1 108.2(5) . . ?
C3 C2 C25 125.0(5) . . ?
C1 C2 C25 126.9(5) . . ?
C2 C3 C4 107.3(5) . . ?
C2 C3 C26 123.8(5) . . ?
C4 C3 C26 128.7(5) . . ?
N5 C4 C5 123.5(5) . . ?
N5 C4 C3 107.1(4) . . ?
C5 C4 C3 129.4(5) . . ?
C6 C5 C4 129.2(5) . . ?
C6 C5 C27 113.8(4) . . ?
C4 C5 C27 117.0(5) . . ?
N1 C6 C5 128.4(5) . . ?
N1 C6 C7 106.6(5) . . ?
C5 C6 C7 124.9(5) . . ?
C8 C7 C6 108.7(5) . . ?
C8 C7 H3 125.7 . . ?
C6 C7 H3 125.7 . . ?
C7 C8 C9 109.0(5) . . ?
C7 C8 H4 125.5 . . ?
C9 C8 H4 125.5 . . ?
C6 N1 C9 110.4(4) . . ?
C6 N1 H5 124.8 . . ?
C9 N1 H5 124.8 . . ?
N1 C9 C10 130.3(5) . . ?
N1 C9 C8 105.3(5) . . ?
C10 C9 C8 124.2(5) . . ?
C9 C10 C11 131.1(5) . . ?
C9 C10 C33 115.6(4) . . ?
C11 C10 C33 113.3(5) . . ?
N2 C11 C10 129.1(5) . . ?
N2 C11 C12 106.4(5) . . ?
C10 C11 C12 124.5(5) . . ?
C13 C12 C11 109.1(5) . . ?
C13 C12 H6 125.5 . . ?
C11 C12 H6 125.5 . . ?
C12 C13 C14 108.6(5) . . ?
C12 C13 H7 125.7 . . ?
C14 C13 H7 125.7 . . ?
N2 C14 C15 130.6(5) . . ?
N2 C14 C13 106.0(4) . . ?
C15 C14 C13 123.5(5) . . ?
C11 N2 C14 109.9(5) . . ?
C11 N2 H8 125.0 . . ?
C14 N2 H8 125.0 . . ?
C16 C15 C14 131.3(5) . . ?
C16 C15 C39 116.7(5) . . ?
C14 C15 C39 112.0(5) . . ?
N3 C16 C15 123.5(5) . . ?
N3 C16 C17 106.2(4) . . ?
C15 C16 C17 130.3(5) . . ?
C18 C17 C16 107.4(5) . . ?
C18 C17 C45 123.2(5) . . ?
C16 C17 C45 129.3(5) . . ?
C17 C18 C19 108.4(5) . . ?
C17 C18 C46 125.1(5) . . ?
C19 C18 C46 126.2(5) . . ?
N3 C19 C18 107.0(5) . . ?
N3 C19 C20 118.9(4) . . ?
C18 C19 C20 133.4(5) . . ?
C19 N3 C16 110.9(4) . . ?
C19 N3 H9 124.5 . . ?
C16 N3 H9 124.5 . . ?
N4 C20 C19 115.3(5) . . ?
N4 C20 C21 121.7(5) . . ?
C19 C20 C21 122.8(5) . . ?
O1 C21 C22 121.8(5) . . ?
O1 C21 C20 123.5(5) . . ?
C22 C21 C20 114.5(5) . . ?
C23 C22 C21 119.3(5) . . ?
C23 C22 H10 120.3 . . ?
C21 C22 H10 120.3 . . ?
C22 C23 C24 119.9(5) . . ?
C22 C23 H11 120.1 . . ?
C24 C23 H11 120.1 . . ?
N4 C24 C23 120.8(5) . . ?
N4 C24 C1 117.2(5) . . ?
C23 C24 C1 121.9(5) . . ?
C24 N4 C20 119.1(4) . . ?
C1 N5 C4 109.5(4) . . ?
C1 N5 H12 125.2 . . ?
C4 N5 H12 125.2 . . ?
C2 C25 H13 109.5 . . ?
C2 C25 H14 109.5 . . ?
H13 C25 H14 109.5 . . ?
C2 C25 H15 109.5 . . ?
H13 C25 H15 109.5 . . ?
H14 C25 H15 109.5 . . ?
C3 C26 H16 109.5 . . ?
C3 C26 H17 109.5 . . ?
H16 C26 H17 109.5 . . ?
C3 C26 H18 109.5 . . ?
H16 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
C28 C27 C32 115.6(5) . . ?
C28 C27 C5 123.2(5) . . ?
C32 C27 C5 121.2(5) . . ?
F1 C28 C27 119.1(5) . . ?
F1 C28 C29 118.2(5) . . ?
C27 C28 C29 122.6(5) . . ?
F2 C29 C30 120.2(5) . . ?
F2 C29 C28 120.2(5) . . ?
C30 C29 C28 119.6(5) . . ?
F3 C30 C29 119.7(5) . . ?
F3 C30 C31 120.8(5) . . ?
C29 C30 C31 119.4(5) . . ?
F4 C31 C32 119.8(5) . . ?
F4 C31 C30 119.9(5) . . ?
C32 C31 C30 120.2(5) . . ?
F5 C32 C31 117.8(5) . . ?
F5 C32 C27 119.7(5) . . ?
C31 C32 C27 122.5(5) . . ?
C34 C33 C38 115.1(5) . . ?
C34 C33 C10 123.7(5) . . ?
C38 C33 C10 121.3(5) . . ?
F6 C34 C33 119.4(5) . . ?
F6 C34 C35 117.0(5) . . ?
C33 C34 C35 123.5(5) . . ?
F7 C35 C36 120.0(5) . . ?
F7 C35 C34 121.3(5) . . ?
C36 C35 C34 118.7(5) . . ?
F8 C36 C37 120.4(5) . . ?
F8 C36 C35 119.7(5) . . ?
C37 C36 C35 119.9(5) . . ?
F9 C37 C38 120.5(5) . . ?
F9 C37 C36 119.2(5) . . ?
C38 C37 C36 120.3(5) . . ?
F10 C38 C37 118.6(5) . . ?
F10 C38 C33 118.9(5) . . ?
C37 C38 C33 122.5(5) . . ?
C44 C39 C40 116.4(5) . . ?
C44 C39 C15 123.0(5) . . ?
C40 C39 C15 120.4(5) . . ?
F11 C40 C41 117.5(6) . . ?
F11 C40 C39 120.0(5) . . ?
C41 C40 C39 122.5(6) . . ?
F12 C41 C40 121.4(6) . . ?
F12 C41 C42 120.2(6) . . ?
C40 C41 C42 118.3(6) . . ?
C43 C42 F13 119.7(6) . . ?
C43 C42 C41 121.0(6) . . ?
F13 C42 C41 119.3(6) . . ?
F14 C43 C42 120.8(6) . . ?
F14 C43 C44 119.8(6) . . ?
C42 C43 C44 119.4(6) . . ?
F15 C44 C43 118.5(5) . . ?
F15 C44 C39 119.2(5) . . ?
C43 C44 C39 122.2(6) . . ?
C17 C45 H19 109.5 . . ?
C17 C45 H20 109.5 . . ?
H19 C45 H20 109.5 . . ?
C17 C45 H21 109.5 . . ?
H19 C45 H21 109.5 . . ?
H20 C45 H21 109.5 . . ?
C18 C46 H22 109.5 . . ?
C18 C46 H23 109.5 . . ?
H22 C46 H23 109.5 . . ?
C18 C46 H24 109.5 . . ?
H22 C46 H24 109.5 . . ?
H23 C46 H24 109.5 . . ?
Cl1 C47 Cl3 111.3(3) . . ?
Cl1 C47 Cl2 110.6(3) . . ?
Cl3 C47 Cl2 110.7(4) . . ?
Cl1 C47 H1 108.0 . . ?
Cl3 C47 H1 108.0 . . ?
Cl2 C47 H1 108.0 . . ?
Cl4 C48 Cl6 114.6(5) . . ?
Cl4 C48 Cl5 113.7(7) . . ?
Cl6 C48 Cl5 110.5(5) . . ?
Cl4 C48 H2 105.7 . . ?
Cl6 C48 H2 105.7 . . ?
Cl5 C48 H2 105.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C1 C2 C3 1.7(6) . . . . ?
C24 C1 C2 C3 -174.8(6) . . . . ?
N5 C1 C2 C25 -178.0(5) . . . . ?
C24 C1 C2 C25 5.5(11) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C25 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C3 C26 -174.7(5) . . . . ?
C25 C2 C3 C26 5.0(9) . . . . ?
C2 C3 C4 N5 -1.6(6) . . . . ?
C26 C3 C4 N5 172.7(5) . . . . ?
C2 C3 C4 C5 178.1(5) . . . . ?
C26 C3 C4 C5 -7.7(10) . . . . ?
N5 C4 C5 C6 -14.9(9) . . . . ?
C3 C4 C5 C6 165.6(6) . . . . ?
N5 C4 C5 C27 164.0(5) . . . . ?
C3 C4 C5 C27 -15.6(8) . . . . ?
C4 C5 C6 N1 -12.5(9) . . . . ?
C27 C5 C6 N1 168.6(5) . . . . ?
C4 C5 C6 C7 171.8(5) . . . . ?
C27 C5 C6 C7 -7.1(7) . . . . ?
N1 C6 C7 C8 -2.1(6) . . . . ?
C5 C6 C7 C8 174.5(5) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C5 C6 N1 C9 -174.6(5) . . . . ?
C7 C6 N1 C9 1.8(6) . . . . ?
C6 N1 C9 C10 174.7(5) . . . . ?
C6 N1 C9 C8 -0.9(6) . . . . ?
C7 C8 C9 N1 -0.4(6) . . . . ?
C7 C8 C9 C10 -176.4(5) . . . . ?
N1 C9 C10 C11 11.5(10) . . . . ?
C8 C9 C10 C11 -173.6(5) . . . . ?
N1 C9 C10 C33 -166.7(5) . . . . ?
C8 C9 C10 C33 8.2(8) . . . . ?
C9 C10 C11 N2 16.6(10) . . . . ?
C33 C10 C11 N2 -165.2(5) . . . . ?
C9 C10 C11 C12 -165.2(6) . . . . ?
C33 C10 C11 C12 13.0(8) . . . . ?
N2 C11 C12 C13 1.7(6) . . . . ?
C10 C11 C12 C13 -176.8(5) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C13 C14 N2 -1.7(6) . . . . ?
C12 C13 C14 C15 177.4(5) . . . . ?
C10 C11 N2 C14 175.6(5) . . . . ?
C12 C11 N2 C14 -2.8(6) . . . . ?
C15 C14 N2 C11 -176.2(6) . . . . ?
C13 C14 N2 C11 2.8(6) . . . . ?
N2 C14 C15 C16 -9.0(11) . . . . ?
C13 C14 C15 C16 172.2(6) . . . . ?
N2 C14 C15 C39 170.3(5) . . . . ?
C13 C14 C15 C39 -8.6(8) . . . . ?
C14 C15 C16 N3 -0.7(10) . . . . ?
C39 C15 C16 N3 -179.9(5) . . . . ?
C14 C15 C16 C17 179.2(6) . . . . ?
C39 C15 C16 C17 0.0(9) . . . . ?
N3 C16 C17 C18 -0.5(6) . . . . ?
C15 C16 C17 C18 179.6(6) . . . . ?
N3 C16 C17 C45 -177.3(6) . . . . ?
C15 C16 C17 C45 2.8(10) . . . . ?
C16 C17 C18 C19 1.7(6) . . . . ?
C45 C17 C18 C19 178.8(5) . . . . ?
C16 C17 C18 C46 -173.3(5) . . . . ?
C45 C17 C18 C46 3.7(9) . . . . ?
C17 C18 C19 N3 -2.3(6) . . . . ?
C46 C18 C19 N3 172.7(5) . . . . ?
C17 C18 C19 C20 -172.6(6) . . . . ?
C46 C18 C19 C20 2.4(9) . . . . ?
C18 C19 N3 C16 2.0(6) . . . . ?
C20 C19 N3 C16 174.0(5) . . . . ?
C15 C16 N3 C19 179.0(5) . . . . ?
C17 C16 N3 C19 -0.9(6) . . . . ?
N3 C19 C20 N4 -15.7(7) . . . . ?
C18 C19 C20 N4 153.7(6) . . . . ?
N3 C19 C20 C21 159.8(5) . . . . ?
C18 C19 C20 C21 -30.8(9) . . . . ?
N4 C20 C21 O1 151.1(5) . . . . ?
C19 C20 C21 O1 -24.1(8) . . . . ?
N4 C20 C21 C22 -23.9(7) . . . . ?
C19 C20 C21 C22 160.9(5) . . . . ?
O1 C21 C22 C23 -156.7(5) . . . . ?
C20 C21 C22 C23 18.5(7) . . . . ?
C21 C22 C23 C24 -1.5(8) . . . . ?
C22 C23 C24 N4 -12.8(8) . . . . ?
C22 C23 C24 C1 163.4(5) . . . . ?
N5 C1 C24 N4 21.9(7) . . . . ?
C2 C1 C24 N4 -161.9(6) . . . . ?
N5 C1 C24 C23 -154.5(5) . . . . ?
C2 C1 C24 C23 21.7(10) . . . . ?
C23 C24 N4 C20 7.9(8) . . . . ?
C1 C24 N4 C20 -168.5(5) . . . . ?
C19 C20 N4 C24 -173.5(5) . . . . ?
C21 C20 N4 C24 10.9(8) . . . . ?
C2 C1 N5 C4 -2.7(6) . . . . ?
C24 C1 N5 C4 174.4(5) . . . . ?
C5 C4 N5 C1 -177.0(5) . . . . ?
C3 C4 N5 C1 2.7(6) . . . . ?
C6 C5 C27 C28 109.7(6) . . . . ?
C4 C5 C27 C28 -69.3(7) . . . . ?
C6 C5 C27 C32 -70.6(7) . . . . ?
C4 C5 C27 C32 110.4(6) . . . . ?
C32 C27 C28 F1 -179.2(5) . . . . ?
C5 C27 C28 F1 0.5(8) . . . . ?
C32 C27 C28 C29 -1.2(8) . . . . ?
C5 C27 C28 C29 178.5(5) . . . . ?
F1 C28 C29 F2 -1.4(8) . . . . ?
C27 C28 C29 F2 -179.4(5) . . . . ?
F1 C28 C29 C30 179.2(5) . . . . ?
C27 C28 C29 C30 1.1(9) . . . . ?
F2 C29 C30 F3 1.9(9) . . . . ?
C28 C29 C30 F3 -178.7(5) . . . . ?
F2 C29 C30 C31 -179.4(5) . . . . ?
C28 C29 C30 C31 0.1(9) . . . . ?
F3 C30 C31 F4 -0.7(9) . . . . ?
C29 C30 C31 F4 -179.5(6) . . . . ?
F3 C30 C31 C32 177.7(5) . . . . ?
C29 C30 C31 C32 -1.1(9) . . . . ?
F4 C31 C32 F5 -0.8(8) . . . . ?
C30 C31 C32 F5 -179.2(5) . . . . ?
F4 C31 C32 C27 179.4(5) . . . . ?
C30 C31 C32 C27 1.0(9) . . . . ?
C28 C27 C32 F5 -179.7(5) . . . . ?
C5 C27 C32 F5 0.6(8) . . . . ?
C28 C27 C32 C31 0.2(8) . . . . ?
C5 C27 C32 C31 -179.6(5) . . . . ?
C9 C10 C33 C34 -111.0(6) . . . . ?
C11 C10 C33 C34 70.5(7) . . . . ?
C9 C10 C33 C38 69.0(7) . . . . ?
C11 C10 C33 C38 -109.5(6) . . . . ?
C38 C33 C34 F6 -178.3(5) . . . . ?
C10 C33 C34 F6 1.7(8) . . . . ?
C38 C33 C34 C35 0.1(8) . . . . ?
C10 C33 C34 C35 -179.9(5) . . . . ?
F6 C34 C35 F7 -0.8(8) . . . . ?
C33 C34 C35 F7 -179.2(5) . . . . ?
F6 C34 C35 C36 178.8(5) . . . . ?
C33 C34 C35 C36 0.3(9) . . . . ?
F7 C35 C36 F8 -0.9(8) . . . . ?
C34 C35 C36 F8 179.6(5) . . . . ?
F7 C35 C36 C37 178.6(5) . . . . ?
C34 C35 C36 C37 -0.9(9) . . . . ?
F8 C36 C37 F9 -2.2(8) . . . . ?
C35 C36 C37 F9 178.3(5) . . . . ?
F8 C36 C37 C38 -179.4(5) . . . . ?
C35 C36 C37 C38 1.2(9) . . . . ?
F9 C37 C38 F10 -0.4(8) . . . . ?
C36 C37 C38 F10 176.8(5) . . . . ?
F9 C37 C38 C33 -177.9(5) . . . . ?
C36 C37 C38 C33 -0.7(9) . . . . ?
C34 C33 C38 F10 -177.4(5) . . . . ?
C10 C33 C38 F10 2.6(8) . . . . ?
C34 C33 C38 C37 0.1(8) . . . . ?
C10 C33 C38 C37 -179.9(5) . . . . ?
C16 C15 C39 C44 -99.7(6) . . . . ?
C14 C15 C39 C44 80.9(7) . . . . ?
C16 C15 C39 C40 85.0(7) . . . . ?
C14 C15 C39 C40 -94.4(6) . . . . ?
C44 C39 C40 F11 -179.0(5) . . . . ?
C15 C39 C40 F11 -3.4(8) . . . . ?
C44 C39 C40 C41 1.7(8) . . . . ?
C15 C39 C40 C41 177.3(5) . . . . ?
F11 C40 C41 F12 0.5(9) . . . . ?
C39 C40 C41 F12 179.9(5) . . . . ?
F11 C40 C41 C42 178.6(5) . . . . ?
C39 C40 C41 C42 -2.0(9) . . . . ?
F12 C41 C42 C43 177.6(5) . . . . ?
C40 C41 C42 C43 -0.6(9) . . . . ?
F12 C41 C42 F13 -0.9(9) . . . . ?
C40 C41 C42 F13 -179.1(5) . . . . ?
F13 C42 C43 F14 2.0(8) . . . . ?
C41 C42 C43 F14 -176.5(5) . . . . ?
F13 C42 C43 C44 -178.2(5) . . . . ?
C41 C42 C43 C44 3.3(9) . . . . ?
F14 C43 C44 F15 -3.0(8) . . . . ?
C42 C43 C44 F15 177.3(5) . . . . ?
F14 C43 C44 C39 176.2(5) . . . . ?
C42 C43 C44 C39 -3.6(9) . . . . ?
C40 C39 C44 F15 -179.7(4) . . . . ?
C15 C39 C44 F15 4.8(8) . . . . ?
C40 C39 C44 C43 1.2(8) . . . . ?
C15 C39 C44 C43 -174.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H4 F14 0.95 2.31 3.237(6) 165.6 1_455
N1 H5 N5 0.88 2.66 3.134(6) 115.1 .
N1 H5 O1 0.88 2.45 2.908(5) 112.5 2_767
C12 H6 F5 0.95 2.60 3.379(6) 139.8 2_666
C13 H7 F13 0.95 2.57 3.190(7) 123.1 2_756
N2 H8 O1 0.88 2.04 2.832(6) 148.6 2_767
N3 H9 N2 0.88 2.62 3.177(6) 121.9 .
N3 H9 O1 0.88 2.38 3.100(5) 139.0 2_767
C23 H11 F8 0.95 2.41 3.273(7) 150.9 1_666
C23 H11 F11 0.95 2.62 3.214(7) 121.1 2_767
N5 H12 N1 0.88 2.63 3.134(6) 117.3 .
N5 H12 O1 0.88 2.39 3.240(6) 161.1 2_767
C47 H1 F2 1.00 2.54 3.372(7) 140.0 2_667
C8 H4 F14 0.95 2.31 3.237(6) 165.6 1_455
N1 H5 N5 0.88 2.66 3.134(6) 115.1 .

_refine_diff_density_max         1.550
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.111

