# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_opda-dicf3-nco-TBACO3-5
_database_code_depnum_ccdc_archive 'CCDC 1525840'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         '2(C24 H14 F12 N4 O2), 2(C16 H36 N), C O3'
_chemical_formula_sum            'C81 H100 F24 N10 O7'
_chemical_formula_weight         1781.71

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6918(6)
_cell_length_b                   24.9364(16)
_cell_length_c                   40.194(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8711.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      63.12

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             3712.0
_exptl_transmission_factor_min   0.788
_exptl_transmission_factor_max   0.817
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.063
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            135729
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.2189
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         68.397
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7901
_reflns_number_gt                4659
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0650P)²+14.0930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7901
_refine_ls_number_parameters     581
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.003

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
F2 F 0.9300(4) 0.34610(18) 0.42843(9) 0.1275(16) Uani 1 1 d . . . A 23
F1 F 1.1535(4) 0.31624(12) 0.42554(7) 0.0962(11) Uani 1 1 d . . . B 23
F3 F 1.1072(5) 0.38669(12) 0.45226(7) 0.1078(13) Uani 1 1 d . . . C 23
F5D F 0.9675(13) 0.14057(16) 0.47156(11) 0.156(3) Uani 0.8 1 d D . P D 1
F5E F 0.9010(7) 0.13691(14) 0.52147(14) 0.1013(16) Uani 0.8 1 d D . P D 1
F5F F 1.1317(6) 0.14092(15) 0.51052(19) 0.128(2) Uani 0.8 1 d D . P D 1
F23E F 0.3607(9) 0.14023(18) 0.78339(13) 0.110(2) Uani 0.75 1 d . . P E 1
F23D F 0.3148(7) 0.15271(18) 0.73226(16) 0.1246(18) Uani 0.75 1 d . . P E 1
F23F F 0.5396(6) 0.12757(15) 0.74732(18) 0.0921(17) Uani 0.75 1 d . . P E 1
F6 F 0.3726(4) 0.32170(15) 0.83761(7) 0.1042(12) Uani 1 1 d . . . . .
F5 F 0.6080(4) 0.30568(12) 0.84465(7) 0.0922(10) Uani 1 1 d . . . . .
F4 F 0.5420(5) 0.37686(11) 0.82075(7) 0.0985(12) Uani 1 1 d . . . . .
O1 O 0.9625(4) 0.41073(11) 0.55692(7) 0.0543(8) Uani 1 1 d . . . . .
O2 O 0.5967(4) 0.40638(12) 0.71354(8) 0.0627(9) Uani 1 1 d . . . . .
N1 N 0.9053(4) 0.32227(13) 0.56464(8) 0.0486(9) Uani 1 1 d . . . . .
H1N H 0.8758 0.2998 0.5796 0.058 Uiso 1 1 d R U . . .
N2 N 0.8395(4) 0.38257(13) 0.60410(8) 0.0480(9) Uani 1 1 d . . . . .
H2N H 0.8038 0.3548 0.6141 0.058 Uiso 1 1 d R U . . .
N3 N 0.7532(4) 0.37976(13) 0.67050(7) 0.0483(8) Uani 1 1 d . . . . .
H3N H 0.8011 0.3527 0.6621 0.058 Uiso 1 1 d R U . . .
N4 N 0.6421(5) 0.31714(14) 0.70375(8) 0.0595(10) Uani 1 1 d . . . . .
H4N H 0.6659 0.2955 0.6879 0.071 Uiso 1 1 d R U . . .
C1 C 1.0536(6) 0.33797(19) 0.44639(11) 0.0580(12) Uani 1 1 d . . . . .
C2 C 1.0236(5) 0.30547(16) 0.47656(10) 0.0455(10) Uani 1 1 d . . . . .
C3 C 1.0281(5) 0.25014(18) 0.47423(10) 0.0514(10) Uani 1 1 d . . . . .
H27 H 1.0546 0.2334 0.4544 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9923(5) 0.22047(17) 0.50221(11) 0.0537(11) Uani 1 1 d . . . . .
C5 C 0.9975(7) 0.1605(2) 0.50057(13) 0.0700(14) Uani 1 1 d D . . . .
C6 C 0.9540(5) 0.24504(17) 0.53165(10) 0.0515(11) Uani 1 1 d . . . . .
H30 H 0.9305 0.2244 0.5502 0.062 Uiso 1 1 calc R U . . .
C7 C 0.9503(5) 0.30113(15) 0.53384(10) 0.0437(10) Uani 1 1 d . . . . .
C8 C 0.9861(5) 0.33153(16) 0.50588(9) 0.0439(10) Uani 1 1 d . . . . .
H32 H 0.9850 0.3688 0.5069 0.053 Uiso 1 1 calc R U . . .
C9 C 0.9064(4) 0.37480(16) 0.57368(9) 0.0407(9) Uani 1 1 d . . . . .
C10 C 0.8256(4) 0.43152(15) 0.62175(9) 0.0389(9) Uani 1 1 d . . . . .
C11 C 0.8487(4) 0.48138(16) 0.60689(10) 0.0417(9) Uani 1 1 d . . . . .
H35 H 0.8723 0.4832 0.5844 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8371(4) 0.52825(16) 0.62513(10) 0.0447(10) Uani 1 1 d . . . . .
H36 H 0.8531 0.5612 0.6148 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8020(5) 0.52633(17) 0.65849(10) 0.0477(10) Uani 1 1 d . . . . .
H37 H 0.7967 0.5578 0.6709 0.057 Uiso 1 1 calc R U . . .
C14 C 0.7746(5) 0.47735(16) 0.67354(10) 0.0483(10) Uani 1 1 d . . . . .
H38 H 0.7497 0.4762 0.6960 0.058 Uiso 1 1 calc R U . . .
C15 C 0.7839(4) 0.42993(16) 0.65556(9) 0.0395(9) Uani 1 1 d . . . . .
C16 C 0.6592(5) 0.37140(17) 0.69755(10) 0.0485(10) Uani 1 1 d . . . . .
C17 C 0.5784(5) 0.29534(17) 0.73230(10) 0.0508(11) Uani 1 1 d . . . . .
C18 C 0.5682(5) 0.32278(17) 0.76264(10) 0.0487(10) Uani 1 1 d . . . . .
H42 H 0.5980 0.3585 0.7640 0.058 Uiso 1 1 calc R U . . .
C19 C 0.5137(5) 0.29652(17) 0.79032(10) 0.0507(11) Uani 1 1 d . . . . .
C20 C 0.5071(6) 0.32531(19) 0.82289(12) 0.0585(12) Uani 1 1 d . . . . .
C21 C 0.4669(5) 0.24327(18) 0.78915(11) 0.0568(12) Uani 1 1 d . . . . .
H45 H 0.4307 0.2260 0.8081 0.068 Uiso 1 1 calc R U . . .
C22 C 0.4755(5) 0.21658(18) 0.75905(12) 0.0614(13) Uani 1 1 d D . . . .
C24 C 0.5293(6) 0.24177(18) 0.73096(11) 0.0609(13) Uani 1 1 d . . . . .
H47 H 0.5333 0.2232 0.7109 0.073 Uiso 1 1 calc R U . . .
C23B C 0.4191(9) 0.1597(3) 0.7550(2) 0.0621(18) Uiso 0.75 1 d D . P E 1
O4 O 0.8369(5) 0.28259(17) 0.64783(9) 0.1075(16) Uani 1 1 d . . . F 2
O3 O 0.7500 0.2500 0.60109(12) 0.109(2) Uani 1 2 d S T P F 2
C41 C 0.7500 0.2500 0.63276(17) 0.070(2) Uani 1 2 d S T P F 2
N5 N 0.3280(3) 0.49398(12) 0.61319(8) 0.0402(8) Uani 1 1 d . . . G 2
C29 C 0.4500(4) 0.53690(16) 0.61505(10) 0.0432(10) Uani 1 1 d . . . G 2
H49A H 0.5176 0.5330 0.5960 0.052 Uiso 1 1 calc R U . G 2
H49B H 0.5113 0.5308 0.6349 0.052 Uiso 1 1 calc R U . G 2
C30 C 0.3914(5) 0.59424(17) 0.61583(11) 0.0517(11) Uani 1 1 d . . . G 2
H50A H 0.3292 0.6011 0.5962 0.062 Uiso 1 1 calc R U . G 2
H50B H 0.3272 0.5994 0.6353 0.062 Uiso 1 1 calc R U . G 2
C31 C 0.5251(5) 0.63316(18) 0.61676(12) 0.0614(12) Uani 1 1 d . . . G 2
H51A H 0.5863 0.6263 0.6365 0.074 Uiso 1 1 calc R U . G 2
H51B H 0.5900 0.6272 0.5975 0.074 Uiso 1 1 calc R U . G 2
C32 C 0.4727(6) 0.69083(19) 0.61705(13) 0.0738(15) Uani 1 1 d . . . G 2
H52A H 0.4153 0.6977 0.6370 0.111 Uiso 1 1 d R U . G 2
H52B H 0.4086 0.6975 0.5980 0.111 Uiso 1 1 d R U . G 2
H52C H 0.5608 0.7140 0.6163 0.111 Uiso 1 1 d R U . G 2
C25 C 0.2229(4) 0.49678(16) 0.64347(9) 0.0427(10) Uani 1 1 d . . . G 2
H53A H 0.1652 0.5300 0.6424 0.051 Uiso 1 1 calc R U . G 2
H53B H 0.1495 0.4676 0.6421 0.051 Uiso 1 1 calc R U . G 2
C26 C 0.3017(5) 0.49395(18) 0.67706(10) 0.0512(11) Uani 1 1 d . . . G 2
H54A H 0.3721 0.4638 0.6774 0.061 Uiso 1 1 calc R U . G 2
H54B H 0.3608 0.5264 0.6807 0.061 Uiso 1 1 calc R U . G 2
C27 C 0.1838(5) 0.48765(19) 0.70452(10) 0.0553(11) Uani 1 1 d . . . G 2
H55A H 0.1133 0.5178 0.7038 0.066 Uiso 1 1 calc R U . G 2
H55B H 0.1248 0.4552 0.7006 0.066 Uiso 1 1 calc R U . G 2
C28 C 0.2560(6) 0.4847(2) 0.73865(10) 0.0668(13) Uani 1 1 d . . . G 2
H56A H 0.3069 0.5179 0.7435 0.100 Uiso 1 1 d R U . G 2
H56B H 0.3294 0.4560 0.7392 0.100 Uiso 1 1 d R U . G 2
H56C H 0.1774 0.4783 0.7550 0.100 Uiso 1 1 d R U . G 2
C37 C 0.4112(5) 0.44018(16) 0.61207(11) 0.0476(10) Uani 1 1 d . . . G 2
H57A H 0.4883 0.4417 0.5947 0.057 Uiso 1 1 calc R U . G 2
H57B H 0.4649 0.4353 0.6330 0.057 Uiso 1 1 calc R U . G 2
C38 C 0.3111(6) 0.39142(18) 0.60603(14) 0.0710(14) Uani 1 1 d D . . . .
H58A H 0.2717 0.3922 0.5835 0.085 Uiso 1 1 d R U . G .
H58B H 0.2243 0.3919 0.6212 0.085 Uiso 1 1 d R U . . .
C39B C 0.384(3) 0.3402(4) 0.6150(4) 0.071(2) Uiso 0.48(5) 1 d D . P G 1
H59A H 0.3479 0.3124 0.6000 0.085 Uiso 0.48(5) 1 calc R U P G 1
H59B H 0.4942 0.3433 0.6126 0.085 Uiso 0.48(5) 1 calc R U P G 1
C40A C 0.3289(12) 0.2899(3) 0.6059(3) 0.081(3) Uani 0.5 1 d D . P G 2
H60A H 0.3997 0.2605 0.6076 0.122 Uiso 0.5 1 calc R U P G 2
H60B H 0.2548 0.2877 0.6235 0.122 Uiso 0.5 1 calc R U P G 2
H60C H 0.2769 0.2883 0.5848 0.122 Uiso 0.5 1 calc R U P G 2
C33 C 0.2288(4) 0.50091(16) 0.58249(9) 0.0411(9) Uani 1 1 d . . . . .
H61A H 0.1521 0.4726 0.5824 0.049 Uiso 1 1 calc R U . G 2
H61B H 0.1745 0.5348 0.5844 0.049 Uiso 1 1 calc R U . G 2
C34 C 0.3112(4) 0.50008(17) 0.54962(9) 0.0445(10) Uani 1 1 d . . . . .
H62A H 0.3672 0.4666 0.5474 0.053 Uiso 1 1 calc R U . . .
H62B H 0.3850 0.5292 0.5488 0.053 Uiso 1 1 calc R U . . .
C35 C 0.1990(5) 0.5057(2) 0.52117(10) 0.0560(12) Uani 1 1 d . . . . .
H63A H 0.1483 0.5402 0.5228 0.067 Uiso 1 1 calc R U . . .
H63B H 0.1208 0.4781 0.5231 0.067 Uiso 1 1 calc R U . . .
C36 C 0.2754(5) 0.50109(19) 0.48745(10) 0.0591(12) Uani 1 1 d . . . . .
H64A H 0.3296 0.4676 0.4861 0.089 Uiso 1 1 d R U . . .
H64B H 0.3467 0.5301 0.4846 0.089 Uiso 1 1 d R U . . .
H64C H 0.1985 0.5026 0.4703 0.089 Uiso 1 1 d R U . . .
C40B C 0.3474(17) 0.3251(5) 0.6491(3) 0.104(4) Uani 0.5 1 d D . P G 1
H80A H 0.3962 0.2915 0.6543 0.156 Uiso 0.5 1 calc R U P G 1
H80B H 0.3842 0.3523 0.6641 0.156 Uiso 0.5 1 calc R U P G 1
H80C H 0.2381 0.3214 0.6516 0.156 Uiso 0.5 1 calc R U P G 1
F23A F 0.528(2) 0.1306(6) 0.7872(5) 0.1246(18) Uani 0.25 1 d . . P E 2
F23B F 0.3148(19) 0.1454(7) 0.7652(5) 0.084(5) Uiso 0.25 1 d . . P E 2
F23C F 0.475(2) 0.1324(8) 0.7332(5) 0.099(7) Uiso 0.25 1 d . . P E 2
C23A C 0.475(3) 0.1552(6) 0.7644(6) 0.0621(18) Uiso 0.25 1 d D . P E 2
F5A F 1.1045(18) 0.1457(6) 0.4803(4) 0.067(4) Uiso 0.2 1 d D . P D 2
F5B F 0.8735(18) 0.1422(8) 0.4865(5) 0.088(6) Uiso 0.2 1 d D . P D 2
F5C F 1.005(3) 0.1356(8) 0.5285(4) 0.102(7) Uiso 0.2 1 d D . P D 2
C39A C 0.415(2) 0.3415(4) 0.6085(6) 0.071(2) Uiso 0.52(5) 1 d D . P G 2
H59C H 0.4908 0.3429 0.5909 0.085 Uiso 0.52(5) 1 calc R U P G 2
H59D H 0.4687 0.3423 0.6296 0.085 Uiso 0.52(5) 1 calc R U P G 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
F2 C1 1.310(6) . ?
F1 C1 1.323(5) . ?
F3 C1 1.323(5) . ?
F5D C5 1.294(6) . ?
F5E C5 1.325(6) . ?
F5F C5 1.326(7) . ?
F23E C23B 1.341(9) . ?
F23D C23B 1.298(8) . ?
F23F C23B 1.354(9) . ?
F6 C20 1.313(5) . ?
F5 C20 1.332(5) . ?
F4 C20 1.323(5) . ?
O1 C9 1.222(4) . ?
O2 C16 1.212(5) . ?
N1 C9 1.359(5) . ?
N1 C7 1.401(5) . ?
N1 H1N 0.8613 . ?
N2 C9 1.368(5) . ?
N2 C10 1.417(5) . ?
N2 H2N 0.8588 . ?
N3 C16 1.376(5) . ?
N3 C15 1.413(5) . ?
N3 H3N 0.8605 . ?
N4 C16 1.384(5) . ?
N4 C17 1.385(5) . ?
N4 H4N 0.8603 . ?
C1 C2 1.482(6) . ?
C2 C3 1.384(6) . ?
C2 C8 1.384(5) . ?
C3 C4 1.382(6) . ?
C3 H27 0.9300 . ?
C4 C6 1.373(5) . ?
C4 C5 1.498(6) . ?
C5 F5C 1.283(13) . ?
C5 F5A 1.291(12) . ?
C5 F5B 1.300(13) . ?
C6 C7 1.402(5) . ?
C6 H30 0.9300 . ?
C7 C8 1.391(5) . ?
C8 H32 0.9300 . ?
C10 C11 1.394(5) . ?
C10 C15 1.407(5) . ?
C11 C12 1.383(5) . ?
C11 H35 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H36 0.9300 . ?
C13 C14 1.383(5) . ?
C13 H37 0.9300 . ?
C14 C15 1.388(5) . ?
C14 H38 0.9300 . ?
C17 C18 1.401(5) . ?
C17 C24 1.404(6) . ?
C18 C19 1.375(5) . ?
C18 H42 0.9300 . ?
C19 C21 1.390(6) . ?
C19 C20 1.494(6) . ?
C21 C22 1.383(6) . ?
C21 H45 0.9300 . ?
C22 C24 1.374(6) . ?
C22 C23B 1.511(8) . ?
C22 C23A 1.544(16) . ?
C24 H47 0.9300 . ?
O4 C41 1.264(4) . ?
O3 C41 1.273(7) . ?
C41 O4 1.264(4) 2_655 ?
N5 C29 1.508(5) . ?
N5 C33 1.515(4) . ?
N5 C25 1.524(5) . ?
N5 C37 1.525(5) . ?
C29 C30 1.518(6) . ?
C29 H49A 0.9700 . ?
C29 H49B 0.9700 . ?
C30 C31 1.515(6) . ?
C30 H50A 0.9700 . ?
C30 H50B 0.9700 . ?
C31 C32 1.509(6) . ?
C31 H51A 0.9700 . ?
C31 H51B 0.9700 . ?
C32 H52A 0.9601 . ?
C32 H52B 0.9597 . ?
C32 H52C 0.9599 . ?
C25 C26 1.515(5) . ?
C25 H53A 0.9700 . ?
C25 H53B 0.9700 . ?
C26 C27 1.514(6) . ?
C26 H54A 0.9700 . ?
C26 H54B 0.9700 . ?
C27 C28 1.510(6) . ?
C27 H55A 0.9700 . ?
C27 H55B 0.9700 . ?
C28 H56A 0.9600 . ?
C28 H56B 0.9599 . ?
C28 H56C 0.9602 . ?
C37 C38 1.515(6) . ?
C37 H57A 0.9700 . ?
C37 H57B 0.9700 . ?
C38 C39B 1.469(11) . ?
C38 C39A 1.539(11) . ?
C38 H58A 0.9702 . ?
C38 H58B 0.9700 . ?
C39B C40B 1.455(14) . ?
C39B H59A 0.9700 . ?
C39B H59B 0.9700 . ?
C40A C39A 1.489(14) . ?
C40A H60A 0.9600 . ?
C40A H60B 0.9600 . ?
C40A H60C 0.9600 . ?
C33 C34 1.503(5) . ?
C33 H61A 0.9700 . ?
C33 H61B 0.9700 . ?
C34 C35 1.509(5) . ?
C34 H62A 0.9700 . ?
C34 H62B 0.9700 . ?
C35 C36 1.513(5) . ?
C35 H63A 0.9700 . ?
C35 H63B 0.9700 . ?
C36 H64A 0.9598 . ?
C36 H64B 0.9601 . ?
C36 H64C 0.9599 . ?
C40B H80A 0.9600 . ?
C40B H80B 0.9600 . ?
C40B H80C 0.9600 . ?
F23A C23A 1.20(2) . ?
F23B C23A 1.41(3) . ?
F23C C23A 1.38(3) . ?
C39A H59C 0.9700 . ?
C39A H59D 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
C9 N1 C7 126.6(3) . . ?
C9 N1 H1N 116.1 . . ?
C7 N1 H1N 117.2 . . ?
C9 N2 C10 127.3(3) . . ?
C9 N2 H2N 117.2 . . ?
C10 N2 H2N 115.4 . . ?
C16 N3 C15 125.6(3) . . ?
C16 N3 H3N 118.5 . . ?
C15 N3 H3N 115.9 . . ?
C16 N4 C17 125.2(4) . . ?
C16 N4 H4N 117.0 . . ?
C17 N4 H4N 117.6 . . ?
F2 C1 F3 104.2(4) . . ?
F2 C1 F1 104.6(4) . . ?
F3 C1 F1 104.9(4) . . ?
F2 C1 C2 113.1(4) . . ?
F3 C1 C2 114.7(4) . . ?
F1 C1 C2 114.2(4) . . ?
C3 C2 C8 122.2(4) . . ?
C3 C2 C1 119.0(4) . . ?
C8 C2 C1 118.8(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 H27 120.9 . . ?
C2 C3 H27 120.9 . . ?
C6 C4 C3 121.1(4) . . ?
C6 C4 C5 119.4(4) . . ?
C3 C4 C5 119.5(4) . . ?
F5C C5 F5A 112.3(14) . . ?
F5C C5 F5B 104.6(14) . . ?
F5A C5 F5B 102.9(12) . . ?
F5D C5 F5E 105.8(6) . . ?
F5D C5 F5F 108.0(6) . . ?
F5E C5 F5F 101.7(5) . . ?
F5C C5 C4 116.5(11) . . ?
F5A C5 C4 109.6(8) . . ?
F5D C5 C4 114.6(5) . . ?
F5B C5 C4 110.1(10) . . ?
F5E C5 C4 113.3(4) . . ?
F5F C5 C4 112.4(5) . . ?
C4 C6 C7 120.3(4) . . ?
C4 C6 H30 119.8 . . ?
C7 C6 H30 119.8 . . ?
C8 C7 N1 124.8(4) . . ?
C8 C7 C6 119.2(4) . . ?
N1 C7 C6 115.9(3) . . ?
C2 C8 C7 119.0(4) . . ?
C2 C8 H32 120.5 . . ?
C7 C8 H32 120.5 . . ?
O1 C9 N1 124.2(4) . . ?
O1 C9 N2 123.9(4) . . ?
N1 C9 N2 111.9(3) . . ?
C11 C10 C15 118.4(4) . . ?
C11 C10 N2 122.8(3) . . ?
C15 C10 N2 118.8(3) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H35 119.5 . . ?
C10 C11 H35 119.5 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H36 119.9 . . ?
C11 C12 H36 119.9 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H37 120.2 . . ?
C14 C13 H37 120.2 . . ?
C13 C14 C15 121.0(4) . . ?
C13 C14 H38 119.5 . . ?
C15 C14 H38 119.5 . . ?
C14 C15 C10 119.6(4) . . ?
C14 C15 N3 121.5(3) . . ?
C10 C15 N3 118.9(3) . . ?
O2 C16 N3 125.2(4) . . ?
O2 C16 N4 124.0(4) . . ?
N3 C16 N4 110.7(4) . . ?
N4 C17 C18 123.7(4) . . ?
N4 C17 C24 117.6(4) . . ?
C18 C17 C24 118.6(4) . . ?
C19 C18 C17 119.6(4) . . ?
C19 C18 H42 120.2 . . ?
C17 C18 H42 120.2 . . ?
C18 C19 C21 121.9(4) . . ?
C18 C19 C20 119.6(4) . . ?
C21 C19 C20 118.5(4) . . ?
F6 C20 F4 107.4(4) . . ?
F6 C20 F5 105.4(4) . . ?
F4 C20 F5 104.4(4) . . ?
F6 C20 C19 113.3(4) . . ?
F4 C20 C19 113.6(4) . . ?
F5 C20 C19 111.9(4) . . ?
C22 C21 C19 118.3(4) . . ?
C22 C21 H45 120.9 . . ?
C19 C21 H45 120.9 . . ?
C24 C22 C21 121.1(4) . . ?
C24 C22 C23B 116.8(5) . . ?
C21 C22 C23B 122.0(5) . . ?
C24 C22 C23A 124.6(10) . . ?
C21 C22 C23A 110.8(10) . . ?
C22 C24 C17 120.5(4) . . ?
C22 C24 H47 119.8 . . ?
C17 C24 H47 119.8 . . ?
F23D C23B F23E 106.6(7) . . ?
F23D C23B F23F 107.6(7) . . ?
F23E C23B F23F 105.8(6) . . ?
F23D C23B C22 115.4(6) . . ?
F23E C23B C22 111.7(6) . . ?
F23F C23B C22 109.2(6) . . ?
O4 C41 O4 122.8(7) 2_655 . ?
O4 C41 O3 118.6(4) 2_655 . ?
O4 C41 O3 118.6(4) . . ?
C29 N5 C33 111.1(3) . . ?
C29 N5 C25 110.5(3) . . ?
C33 N5 C25 107.7(3) . . ?
C29 N5 C37 107.0(3) . . ?
C33 N5 C37 110.3(3) . . ?
C25 N5 C37 110.4(3) . . ?
N5 C29 C30 115.7(3) . . ?
N5 C29 H49A 108.4 . . ?
C30 C29 H49A 108.4 . . ?
N5 C29 H49B 108.4 . . ?
C30 C29 H49B 108.4 . . ?
H49A C29 H49B 107.4 . . ?
C31 C30 C29 110.2(3) . . ?
C31 C30 H50A 109.6 . . ?
C29 C30 H50A 109.6 . . ?
C31 C30 H50B 109.6 . . ?
C29 C30 H50B 109.6 . . ?
H50A C30 H50B 108.1 . . ?
C32 C31 C30 112.3(4) . . ?
C32 C31 H51A 109.1 . . ?
C30 C31 H51A 109.1 . . ?
C32 C31 H51B 109.1 . . ?
C30 C31 H51B 109.1 . . ?
H51A C31 H51B 107.9 . . ?
C31 C32 H52A 109.5 . . ?
C31 C32 H52B 109.5 . . ?
H52A C32 H52B 109.5 . . ?
C31 C32 H52C 109.4 . . ?
H52A C32 H52C 109.5 . . ?
H52B C32 H52C 109.5 . . ?
C26 C25 N5 116.0(3) . . ?
C26 C25 H53A 108.3 . . ?
N5 C25 H53A 108.3 . . ?
C26 C25 H53B 108.3 . . ?
N5 C25 H53B 108.3 . . ?
H53A C25 H53B 107.4 . . ?
C27 C26 C25 110.4(3) . . ?
C27 C26 H54A 109.6 . . ?
C25 C26 H54A 109.6 . . ?
C27 C26 H54B 109.6 . . ?
C25 C26 H54B 109.6 . . ?
H54A C26 H54B 108.1 . . ?
C28 C27 C26 112.7(4) . . ?
C28 C27 H55A 109.0 . . ?
C26 C27 H55A 109.0 . . ?
C28 C27 H55B 109.0 . . ?
C26 C27 H55B 109.0 . . ?
H55A C27 H55B 107.8 . . ?
C27 C28 H56A 109.5 . . ?
C27 C28 H56B 109.5 . . ?
H56A C28 H56B 109.5 . . ?
C27 C28 H56C 109.4 . . ?
H56A C28 H56C 109.5 . . ?
H56B C28 H56C 109.5 . . ?
C38 C37 N5 116.0(3) . . ?
C38 C37 H57A 108.3 . . ?
N5 C37 H57A 108.3 . . ?
C38 C37 H57B 108.3 . . ?
N5 C37 H57B 108.3 . . ?
H57A C37 H57B 107.4 . . ?
C37 C38 C39A 107.7(6) . . ?
C39B C38 H58A 113.5 . . ?
C37 C38 H58A 109.7 . . ?
C39A C38 H58A 106.3 . . ?
C39B C38 H58B 100.9 . . ?
C37 C38 H58B 109.7 . . ?
C39A C38 H58B 115.1 . . ?
H58A C38 H58B 108.2 . . ?
C40B C39B C38 111.4(13) . . ?
C40B C39B H59A 109.3 . . ?
C38 C39B H59A 109.3 . . ?
C40B C39B H59B 109.3 . . ?
C38 C39B H59B 109.3 . . ?
H59A C39B H59B 108.0 . . ?
C39A C40A H60A 109.5 . . ?
C39A C40A H60B 109.5 . . ?
H60A C40A H60B 109.5 . . ?
C39A C40A H60C 109.5 . . ?
H60A C40A H60C 109.5 . . ?
H60B C40A H60C 109.5 . . ?
C34 C33 N5 116.3(3) . . ?
C34 C33 H61A 108.2 . . ?
N5 C33 H61A 108.2 . . ?
C34 C33 H61B 108.2 . . ?
N5 C33 H61B 108.2 . . ?
H61A C33 H61B 107.4 . . ?
C33 C34 C35 110.9(3) . . ?
C33 C34 H62A 109.5 . . ?
C35 C34 H62A 109.5 . . ?
C33 C34 H62B 109.5 . . ?
C35 C34 H62B 109.5 . . ?
H62A C34 H62B 108.0 . . ?
C34 C35 C36 112.8(4) . . ?
C34 C35 H63A 109.0 . . ?
C36 C35 H63A 109.0 . . ?
C34 C35 H63B 109.0 . . ?
C36 C35 H63B 109.0 . . ?
H63A C35 H63B 107.8 . . ?
C35 C36 H64A 109.4 . . ?
C35 C36 H64B 109.5 . . ?
H64A C36 H64B 109.5 . . ?
C35 C36 H64C 109.5 . . ?
H64A C36 H64C 109.5 . . ?
H64B C36 H64C 109.5 . . ?
C39B C40B H80A 109.5 . . ?
C39B C40B H80B 109.5 . . ?
H80A C40B H80B 109.5 . . ?
C39B C40B H80C 109.5 . . ?
H80A C40B H80C 109.5 . . ?
H80B C40B H80C 109.5 . . ?
F23A C23A F23C 119(2) . . ?
F23A C23A F23B 106(2) . . ?
F23C C23A F23B 87.3(18) . . ?
F23A C23A C22 127.7(19) . . ?
F23C C23A C22 106.5(16) . . ?
F23B C23A C22 100.3(15) . . ?
C40A C39A C38 113.7(11) . . ?
C40A C39A H59C 108.8 . . ?
C38 C39A H59C 108.8 . . ?
C40A C39A H59D 108.8 . . ?
C38 C39A H59D 108.8 . . ?
H59C C39A H59D 107.7 . . ?

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
F2 C1 C2 C3 86.5(5) . . . . ?
F3 C1 C2 C3 -154.2(4) . . . . ?
F1 C1 C2 C3 -33.0(6) . . . . ?
F2 C1 C2 C8 -91.1(5) . . . . ?
F3 C1 C2 C8 28.2(6) . . . . ?
F1 C1 C2 C8 149.4(4) . . . . ?
C8 C2 C3 C4 0.7(7) . . . . ?
C1 C2 C3 C4 -176.8(4) . . . . ?
C2 C3 C4 C6 -0.4(7) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C6 C4 C5 F5C -17.4(16) . . . . ?
C3 C4 C5 F5C 161.6(14) . . . . ?
C6 C4 C5 F5A -146.2(10) . . . . ?
C3 C4 C5 F5A 32.9(12) . . . . ?
C6 C4 C5 F5D 151.2(7) . . . . ?
C3 C4 C5 F5D -29.7(9) . . . . ?
C6 C4 C5 F5B 101.4(12) . . . . ?
C3 C4 C5 F5B -79.6(12) . . . . ?
C6 C4 C5 F5E 29.6(8) . . . . ?
C3 C4 C5 F5E -151.4(6) . . . . ?
C6 C4 C5 F5F -85.0(7) . . . . ?
C3 C4 C5 F5F 94.0(6) . . . . ?
C3 C4 C6 C7 0.2(7) . . . . ?
C5 C4 C6 C7 179.2(4) . . . . ?
C9 N1 C7 C8 -8.3(7) . . . . ?
C9 N1 C7 C6 173.6(4) . . . . ?
C4 C6 C7 C8 -0.2(7) . . . . ?
C4 C6 C7 N1 178.1(4) . . . . ?
C3 C2 C8 C7 -0.7(6) . . . . ?
C1 C2 C8 C7 176.8(4) . . . . ?
N1 C7 C8 C2 -177.7(4) . . . . ?
C6 C7 C8 C2 0.4(6) . . . . ?
C7 N1 C9 O1 -7.9(7) . . . . ?
C7 N1 C9 N2 173.2(4) . . . . ?
C10 N2 C9 O1 -1.4(7) . . . . ?
C10 N2 C9 N1 177.5(4) . . . . ?
C9 N2 C10 C11 15.0(6) . . . . ?
C9 N2 C10 C15 -166.2(4) . . . . ?
C15 C10 C11 C12 2.5(5) . . . . ?
N2 C10 C11 C12 -178.7(4) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C10 1.7(6) . . . . ?
C13 C14 C15 N3 -178.7(4) . . . . ?
C11 C10 C15 C14 -3.3(5) . . . . ?
N2 C10 C15 C14 177.9(4) . . . . ?
C11 C10 C15 N3 177.1(3) . . . . ?
N2 C10 C15 N3 -1.7(5) . . . . ?
C16 N3 C15 C14 26.6(6) . . . . ?
C16 N3 C15 C10 -153.8(4) . . . . ?
C15 N3 C16 O2 -4.6(7) . . . . ?
C15 N3 C16 N4 174.0(4) . . . . ?
C17 N4 C16 O2 -13.6(7) . . . . ?
C17 N4 C16 N3 167.8(4) . . . . ?
C16 N4 C17 C18 -21.4(7) . . . . ?
C16 N4 C17 C24 162.2(4) . . . . ?
N4 C17 C18 C19 -175.1(4) . . . . ?
C24 C17 C18 C19 1.3(7) . . . . ?
C17 C18 C19 C21 -0.5(7) . . . . ?
C17 C18 C19 C20 178.2(4) . . . . ?
C18 C19 C20 F6 129.5(5) . . . . ?
C21 C19 C20 F6 -51.7(6) . . . . ?
C18 C19 C20 F4 6.5(6) . . . . ?
C21 C19 C20 F4 -174.7(4) . . . . ?
C18 C19 C20 F5 -111.5(5) . . . . ?
C21 C19 C20 F5 67.3(6) . . . . ?
C18 C19 C21 C22 -0.3(7) . . . . ?
C20 C19 C21 C22 -179.0(4) . . . . ?
C19 C21 C22 C24 0.3(7) . . . . ?
C19 C21 C22 C23B -176.6(5) . . . . ?
C19 C21 C22 C23A 160.2(11) . . . . ?
C21 C22 C24 C17 0.6(8) . . . . ?
C23B C22 C24 C17 177.6(5) . . . . ?
C23A C22 C24 C17 -156.5(12) . . . . ?
N4 C17 C24 C22 175.3(5) . . . . ?
C18 C17 C24 C22 -1.4(7) . . . . ?
C24 C22 C23B F23D -54.2(9) . . . . ?
C21 C22 C23B F23D 122.8(7) . . . . ?
C24 C22 C23B F23E -176.2(6) . . . . ?
C21 C22 C23B F23E 0.8(10) . . . . ?
C24 C22 C23B F23F 67.1(8) . . . . ?
C21 C22 C23B F23F -116.0(7) . . . . ?
C33 N5 C29 C30 58.6(4) . . . . ?
C25 N5 C29 C30 -60.8(4) . . . . ?
C37 N5 C29 C30 179.0(3) . . . . ?
N5 C29 C30 C31 -178.5(3) . . . . ?
C29 C30 C31 C32 179.1(4) . . . . ?
C29 N5 C25 C26 -55.1(4) . . . . ?
C33 N5 C25 C26 -176.5(3) . . . . ?
C37 N5 C25 C26 63.1(4) . . . . ?
N5 C25 C26 C27 -170.4(3) . . . . ?
C25 C26 C27 C28 -179.9(4) . . . . ?
C29 N5 C37 C38 -173.0(4) . . . . ?
C33 N5 C37 C38 -52.1(5) . . . . ?
C25 N5 C37 C38 66.7(4) . . . . ?
N5 C37 C38 C39A -175.8(10) . . . . ?
C29 N5 C33 C34 58.2(4) . . . . ?
C25 N5 C33 C34 179.3(3) . . . . ?
C37 N5 C33 C34 -60.3(4) . . . . ?
N5 C33 C34 C35 178.3(3) . . . . ?
C33 C34 C35 C36 -175.9(4) . . . . ?
C24 C22 C23A F23A 126(3) . . . . ?
C21 C22 C23A F23A -33(3) . . . . ?
C24 C22 C23A F23C -24(2) . . . . ?
C21 C22 C23A F23C 176.9(15) . . . . ?
C24 C22 C23A F23B -114.3(15) . . . . ?
C21 C22 C23A F23B 86.6(16) . . . . ?
C37 C38 C39A C40A 175.2(14) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_opda-dicf3-nco-L
_database_code_depnum_ccdc_archive 'CCDC 1525834'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, 2(C2 H6 O S)'
_chemical_formula_sum            'C28 H26 F12 N4 O4 S2'
_chemical_formula_weight         774.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   9.6670(8)
_cell_length_b                   13.2167(11)
_cell_length_c                   13.9113(12)
_cell_angle_alpha                104.440(7)
_cell_angle_beta                 92.993(7)
_cell_angle_gamma                90.220(7)
_cell_volume                     1718.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      3.7550
_cell_measurement_theta_max      21.9250

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             788.0
_exptl_transmission_factor_min   0.928
_exptl_transmission_factor_max   0.950
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.259
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11963
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.883
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6060
_reflns_number_gt                3510
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0720P)²+0.9340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0048(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6060
_refine_ls_number_parameters     563
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.2069
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
F4A F 0.8938(14) -0.2559(16) 0.640(2) 0.157(9) Uani 0.5 1 d D . P A 1
F5A F 1.024(3) -0.217(2) 0.7642(8) 0.168(8) Uani 0.5 1 d D . P A 1
F6A F 1.037(2) -0.1371(11) 0.653(2) 0.162(5) Uani 0.5 1 d D . P A 1
F20A F 0.1119(14) 0.7592(7) 0.9873(12) 0.151(4) Uani 0.5 1 d D . P B 1
F20B F 0.0275(15) 0.6154(19) 0.9501(13) 0.250(10) Uani 0.5 1 d D . P B 1
F20C F 0.145(2) 0.6692(18) 1.0754(9) 0.240(9) Uani 0.5 1 d D . P B 1
C5A C 0.9492(12) -0.1746(9) 0.7043(10) 0.0766(15) Uani 0.5 1 d D . P A 1
C20 C 0.1339(7) 0.6664(5) 0.9845(4) 0.1071(19) Uani 1 1 d D . . . .
S1A S 0.1929(2) 0.10352(16) 0.72197(14) 0.0730(6) Uani 0.58 1 d D . P C 1
S2A S 0.9148(3) 0.4292(4) 0.6078(3) 0.1091(11) Uani 0.5 1 d D . P D 1
C27A C 0.8588(15) 0.4594(17) 0.6897(14) 0.207(13) Uani 0.5 1 d D . P D 2
H27A H 0.7631 0.4479 0.6996 0.311 Uiso 0.5 1 calc DR U P D 2
H27B H 0.9133 0.4611 0.7498 0.311 Uiso 0.5 1 calc R U P D 2
H27C H 0.8694 0.5248 0.6724 0.311 Uiso 0.5 1 calc R U P D 2
F5B F 0.919(2) -0.2071(16) 0.6113(7) 0.123(8) Uani 0.5 1 d D . P A 2
F6B F 0.917(2) -0.2708(8) 0.7318(16) 0.135(3) Uani 0.5 1 d D . P A 2
F4B F 1.0631(8) -0.1563(15) 0.7305(15) 0.122(4) Uani 0.5 1 d D . P A 2
F20E F 0.1671(16) 0.7299(16) 1.0681(12) 0.250(10) Uani 0.5 1 d D . P B 2
F20D F 0.0586(13) 0.6037(9) 1.0103(11) 0.151(4) Uani 0.5 1 d D . P B 2
F20F F 0.055(2) 0.712(2) 0.9358(9) 0.240(9) Uani 0.5 1 d D . P B 2
C5B C 0.9354(12) -0.1847(9) 0.7071(9) 0.0766(15) Uani 0.5 1 d D . P A 2
S1B S 0.1692(3) 0.1977(2) 0.7133(2) 0.0771(8) Uani 0.42 1 d D . P C 2
S2B S 0.9155(3) 0.3569(3) 0.5925(3) 0.1037(13) Uani 0.5 1 d D . P D 2
C27B C 0.8444(16) 0.3555(17) 0.6821(15) 0.158(8) Uani 0.5 1 d D . P D 1
H27D H 0.7509 0.3766 0.6954 0.237 Uiso 0.5 1 calc R U P D 1
H27E H 0.8447 0.2827 0.6481 0.237 Uiso 0.5 1 calc R U P D 1
H27F H 0.8988 0.3666 0.7437 0.237 Uiso 0.5 1 calc R U P D 1
F1A F 0.6506(5) -0.0632(4) 1.0356(2) 0.1228(13) Uani 0.9 1 d D . P E 1
F1C F 0.8409(4) 0.0217(5) 1.0612(2) 0.1380(16) Uani 0.9 1 d D . P E 1
F1B F 0.6512(6) 0.0994(3) 1.0476(3) 0.1281(18) Uani 0.9 1 d D . P E 1
F23B F 0.6573(9) 0.6629(6) 1.0559(3) 0.182(4) Uani 0.85 1 d D . P F 1
F23C F 0.7034(5) 0.7025(4) 0.9232(4) 0.1382(18) Uani 0.85 1 d D . P F 1
O1 O 0.7319(3) 0.0822(3) 0.5618(2) 0.0778(9) Uani 1 1 d . . . . .
O3 O 0.3225(3) 0.1687(3) 0.7194(2) 0.0980(11) Uani 1 1 d D . . . .
O4 O 1.0623(3) 0.3905(3) 0.5907(3) 0.1217(15) Uani 1 1 d D . . . .
O2 O 0.5402(3) 0.4016(3) 0.6384(2) 0.0902(11) Uani 1 1 d . . . . .
N4 N 0.3217(3) 0.4427(3) 0.6887(2) 0.0691(10) Uani 1 1 d . . . . .
H4N H 0.2358 0.4320 0.6693 0.083 Uiso 1 1 calc R U . . .
N1 N 0.5933(3) 0.0877(2) 0.6908(2) 0.0592(8) Uani 1 1 d . . . . .
H1N H 0.5186 0.1138 0.7168 0.071 Uiso 1 1 calc R U . . .
N3 N 0.3558(3) 0.3243(2) 0.5417(2) 0.0597(8) Uani 1 1 d . . . . .
H3N H 0.2676 0.3136 0.5374 0.072 Uiso 1 1 calc R U . . .
N2 N 0.5183(3) 0.1549(2) 0.5614(2) 0.0579(8) Uani 1 1 d . . . . .
H2N H 0.4445 0.1670 0.5941 0.070 Uiso 1 1 calc R U . . .
C9 C 0.6227(4) 0.1057(3) 0.6003(3) 0.0535(9) Uani 1 1 d . . . . .
C10 C 0.5201(4) 0.1878(3) 0.4725(3) 0.0518(9) Uani 1 1 d . . . . .
C7 C 0.6753(4) 0.0304(3) 0.7436(3) 0.0527(9) Uani 1 1 d . . . . .
C15 C 0.4374(4) 0.2714(3) 0.4621(3) 0.0546(9) Uani 1 1 d . . . . .
C16 C 0.4155(4) 0.3914(3) 0.6242(3) 0.0614(10) Uani 1 1 d . . . . .
C6 C 0.7678(4) -0.0444(3) 0.6989(3) 0.0594(10) Uani 1 1 d . . . . .
H6 H 0.7793 -0.0574 0.6310 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3495(4) 0.5108(3) 0.7826(3) 0.0598(10) Uani 1 1 d . . . . .
C8 C 0.6585(4) 0.0480(3) 0.8453(3) 0.0603(10) Uani 1 1 d . . . . .
H8 H 0.5960 0.0974 0.8759 0.072 Uiso 1 1 calc R U . . .
F23A F 0.7318(4) 0.5508(3) 0.9392(4) 0.1307(16) Uani 0.85 1 d D . P F 1
C2 C 0.7349(4) -0.0080(3) 0.9011(3) 0.0625(11) Uani 1 1 d . . . . .
C11 C 0.5974(4) 0.1373(3) 0.3940(3) 0.0629(10) Uani 1 1 d . . . . .
H11 H 0.6535 0.0822 0.4005 0.076 Uiso 1 1 calc R U . . .
C24 C 0.4833(4) 0.5349(3) 0.8246(3) 0.0637(11) Uani 1 1 d . . . . .
H24 H 0.5594 0.5059 0.7902 0.076 Uiso 1 1 calc R U . . .
C4 C 0.8429(4) -0.0997(3) 0.7558(3) 0.0607(10) Uani 1 1 d D . . . .
C14 C 0.4339(5) 0.3017(3) 0.3733(3) 0.0729(12) Uani 1 1 d . . . . .
H14 H 0.3797 0.3577 0.3664 0.087 Uiso 1 1 calc R U . . .
C22 C 0.5015(5) 0.6028(3) 0.9186(3) 0.0674(11) Uani 1 1 d . . . . .
C18 C 0.2384(4) 0.5550(3) 0.8352(3) 0.0683(11) Uani 1 1 d . . . . .
H18 H 0.1489 0.5397 0.8074 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5918(5) 0.1685(4) 0.3061(3) 0.0747(12) Uani 1 1 d . . . . .
H12 H 0.6439 0.1342 0.2538 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8272(5) -0.0819(3) 0.8568(3) 0.0685(11) Uani 1 1 d . . . . .
H3A H 0.8784 -0.1192 0.8944 0.082 Uiso 1 1 calc R U . . .
C19 C 0.2587(5) 0.6212(3) 0.9283(3) 0.0724(12) Uani 1 1 d D . . . .
C13 C 0.5095(5) 0.2501(4) 0.2959(3) 0.0821(14) Uani 1 1 d . . . . .
H13 H 0.5050 0.2703 0.2364 0.099 Uiso 1 1 calc R U . . .
C21 C 0.3908(5) 0.6460(3) 0.9710(3) 0.0759(13) Uani 1 1 d . . . . .
H21 H 0.4043 0.6910 1.0339 0.091 Uiso 1 1 calc R U . . .
C1 C 0.7193(6) 0.0117(5) 1.0111(4) 0.0897(15) Uani 1 1 d D . . . .
C23 C 0.6463(6) 0.6313(4) 0.9584(4) 0.0887(15) Uani 1 1 d D . . . .
C25 C 0.0993(7) 0.1055(6) 0.6069(4) 0.105(2) Uani 1 1 d D . . . .
H25A H 0.0144 0.0660 0.6011 0.157 Uiso 0.58 1 calc R U P C 1
H25B H 0.0788 0.1764 0.6063 0.157 Uiso 0.58 1 calc R U P C 1
H25C H 0.1548 0.0752 0.5521 0.157 Uiso 0.58 1 calc R U P C 1
H25D H -0.018(17) 0.108(11) 0.614(11) 0.157 Uiso 0.42 1 d . U P G 2
H25E H 0.142(17) 0.140(13) 0.567(12) 0.157 Uiso 0.42 1 d . U P H 2
H25F H 0.126(16) 0.030(12) 0.602(12) 0.157 Uiso 0.42 1 d . U P I 2
C26B C 0.102(4) 0.140(2) 0.802(2) 0.128(11) Uani 0.42 1 d D . P C 2
H26A H 0.0040 0.1527 0.8052 0.192 Uiso 0.42 1 calc R U P C 2
H26B H 0.1164 0.0659 0.7830 0.192 Uiso 0.42 1 calc R U P C 2
H26C H 0.1473 0.1694 0.8657 0.192 Uiso 0.42 1 calc R U P C 2
C28 C 0.8203(6) 0.3810(8) 0.4977(5) 0.143(3) Uani 1 1 d D . . . .
H28A H 0.7262 0.4033 0.5049 0.214 Uiso 0.5 1 calc R U P D 1
H28B H 0.8595 0.4066 0.4462 0.214 Uiso 0.5 1 calc R U P D 1
H28C H 0.8223 0.3060 0.4806 0.214 Uiso 0.5 1 calc R U P D 1
H28D H 0.736(18) 0.363(14) 0.508(13) 0.214 Uiso 0.5 1 d . U P J 2
H28E H 0.831(18) 0.455(2) 0.533(7) 0.214 Uiso 0.5 1 d D U P D 2
H28F H 0.866(18) 0.377(13) 0.434(13) 0.214 Uiso 0.5 1 d . U P K 2
C26A C 0.088(2) 0.1915(14) 0.8005(14) 0.114(7) Uani 0.58 1 d D . P C 1
H26D H 0.0025 0.1573 0.8069 0.171 Uiso 0.58 1 calc R U P C 1
H26E H 0.1350 0.2156 0.8647 0.171 Uiso 0.58 1 calc R U P C 1
H26F H 0.0690 0.2500 0.7728 0.171 Uiso 0.58 1 calc R U P C 1
F23E F 0.644(3) 0.7330(12) 0.997(3) 0.1307(16) Uani 0.15 1 d D . P F 2
F23D F 0.7399(19) 0.606(2) 0.8926(15) 0.1307(16) Uani 0.15 1 d D . P F 2
F23F F 0.675(5) 0.618(3) 1.047(2) 0.1382(18) Uani 0.15 1 d D . P F 2
F1D F 0.782(6) -0.065(3) 1.041(2) 0.1281(18) Uani 0.1 1 d D . P E 2
F1F F 0.798(5) 0.094(3) 1.054(2) 0.1228(13) Uani 0.1 1 d D . P E 2
F1E F 0.603(3) 0.047(5) 1.050(3) 0.1380(16) Uani 0.1 1 d D . P E 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
F4A C5A 1.308(11) . ?
F5A C5A 1.304(11) . ?
F6A C5A 1.314(11) . ?
F20A C20 1.236(10) . ?
F20B C20 1.235(11) . ?
F20C C20 1.255(11) . ?
C5A C4 1.510(11) . ?
C20 F20D 1.232(10) . ?
C20 F20F 1.246(10) . ?
C20 F20E 1.277(11) . ?
C20 C19 1.514(7) . ?
S1A O3 1.525(4) . ?
S1A C26A 1.751(12) . ?
S1A C25 1.803(6) . ?
S2A O4 1.527(5) . ?
S2A C28 1.717(7) . ?
S2A C27B 1.746(12) . ?
C27A S2B 1.770(11) . ?
F5B C5B 1.293(11) . ?
F6B C5B 1.283(11) . ?
F4B C5B 1.289(11) . ?
C5B C4 1.487(11) . ?
S1B O3 1.536(4) . ?
S1B C26B 1.754(15) . ?
S1B C25 1.767(6) . ?
S2B O4 1.489(4) . ?
S2B C28 1.665(8) . ?
F1A C1 1.314(6) . ?
F1C C1 1.325(6) . ?
F1B C1 1.335(6) . ?
F23B C23 1.314(6) . ?
F23C C23 1.299(6) . ?
O1 C9 1.215(4) . ?
O2 C16 1.213(4) . ?
N4 C16 1.369(5) . ?
N4 C17 1.402(5) . ?
N1 C9 1.381(5) . ?
N1 C7 1.401(4) . ?
N3 C16 1.362(5) . ?
N3 C15 1.431(5) . ?
N2 C9 1.363(4) . ?
N2 C10 1.411(5) . ?
C10 C11 1.386(5) . ?
C10 C15 1.398(5) . ?
C7 C6 1.386(5) . ?
C7 C8 1.394(5) . ?
C15 C14 1.389(6) . ?
C6 C4 1.387(5) . ?
C17 C18 1.379(5) . ?
C17 C24 1.393(5) . ?
C8 C2 1.387(5) . ?
F23A C23 1.332(6) . ?
C2 C3 1.376(6) . ?
C2 C1 1.503(6) . ?
C11 C12 1.382(5) . ?
C24 C22 1.392(5) . ?
C4 C3 1.382(5) . ?
C14 C13 1.371(6) . ?
C22 C21 1.372(6) . ?
C22 C23 1.489(6) . ?
C18 C19 1.374(6) . ?
C12 C13 1.374(6) . ?
C19 C21 1.383(6) . ?
C1 F1E 1.310(16) . ?
C1 F1F 1.317(16) . ?
C1 F1D 1.322(16) . ?
C23 F23F 1.297(16) . ?
C23 F23D 1.307(15) . ?
C23 F23E 1.317(15) . ?
C28 H28E 0.9800(13) . ?

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
F5A C5A F4A 103.0(13) . . ?
F5A C5A F6A 105.8(12) . . ?
F4A C5A F6A 103.5(12) . . ?
F5A C5A C4 113.6(10) . . ?
F4A C5A C4 113.1(10) . . ?
F6A C5A C4 116.5(9) . . ?
F20A C20 F20B 108.0(14) . . ?
F20D C20 F20F 104.9(15) . . ?
F20A C20 F20C 101.3(10) . . ?
F20B C20 F20C 106.9(14) . . ?
F20D C20 F20E 101.2(11) . . ?
F20F C20 F20E 108.4(13) . . ?
F20D C20 C19 116.1(6) . . ?
F20A C20 C19 115.0(8) . . ?
F20B C20 C19 111.2(8) . . ?
F20F C20 C19 112.5(8) . . ?
F20C C20 C19 113.7(8) . . ?
F20E C20 C19 112.8(9) . . ?
O3 S1A C26A 103.2(8) . . ?
O3 S1A C25 102.7(3) . . ?
C26A S1A C25 96.7(9) . . ?
O4 S2A C28 106.4(4) . . ?
O4 S2A C27B 105.8(7) . . ?
C28 S2A C27B 100.7(8) . . ?
F6B C5B F4B 107.0(12) . . ?
F6B C5B F5B 105.9(11) . . ?
F4B C5B F5B 107.6(13) . . ?
F6B C5B C4 113.9(9) . . ?
F4B C5B C4 109.8(9) . . ?
F5B C5B C4 112.3(10) . . ?
O3 S1B C26B 101.3(13) . . ?
O3 S1B C25 103.9(3) . . ?
C26B S1B C25 96.9(14) . . ?
O4 S2B C28 111.0(4) . . ?
O4 S2B C27A 100.0(6) . . ?
C28 S2B C27A 99.3(8) . . ?
C16 N4 C17 127.5(3) . . ?
C9 N1 C7 125.4(3) . . ?
C16 N3 C15 121.0(3) . . ?
C9 N2 C10 126.1(3) . . ?
O1 C9 N2 124.3(4) . . ?
O1 C9 N1 122.9(3) . . ?
N2 C9 N1 112.8(3) . . ?
C11 C10 C15 119.2(4) . . ?
C11 C10 N2 121.9(3) . . ?
C15 C10 N2 118.9(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 N1 123.1(3) . . ?
C8 C7 N1 117.7(3) . . ?
C14 C15 C10 119.4(4) . . ?
C14 C15 N3 120.3(4) . . ?
C10 C15 N3 120.3(3) . . ?
O2 C16 N3 122.1(4) . . ?
O2 C16 N4 124.4(4) . . ?
N3 C16 N4 113.5(3) . . ?
C7 C6 C4 119.7(4) . . ?
C18 C17 C24 119.2(4) . . ?
C18 C17 N4 117.9(4) . . ?
C24 C17 N4 122.9(4) . . ?
C2 C8 C7 120.2(4) . . ?
C3 C2 C8 120.6(4) . . ?
C3 C2 C1 118.8(4) . . ?
C8 C2 C1 120.6(4) . . ?
C12 C11 C10 120.5(4) . . ?
C22 C24 C17 119.2(4) . . ?
C3 C4 C6 121.2(4) . . ?
C3 C4 C5B 118.9(6) . . ?
C6 C4 C5B 119.8(6) . . ?
C3 C4 C5A 121.5(6) . . ?
C6 C4 C5A 117.2(6) . . ?
C13 C14 C15 120.7(4) . . ?
C21 C22 C24 121.5(4) . . ?
C21 C22 C23 121.0(4) . . ?
C24 C22 C23 117.5(4) . . ?
C19 C18 C17 120.7(4) . . ?
C13 C12 C11 120.2(4) . . ?
C2 C3 C4 119.1(4) . . ?
C18 C19 C21 120.8(4) . . ?
C18 C19 C20 119.1(4) . . ?
C21 C19 C20 120.0(4) . . ?
C14 C13 C12 120.1(4) . . ?
C22 C21 C19 118.6(4) . . ?
F1E C1 F1F 97(3) . . ?
F1E C1 F1D 119(3) . . ?
F1F C1 F1D 103(3) . . ?
F1A C1 F1C 106.9(5) . . ?
F1A C1 F1B 105.9(5) . . ?
F1C C1 F1B 106.3(5) . . ?
F1E C1 C2 120.6(18) . . ?
F1A C1 C2 113.1(4) . . ?
F1F C1 C2 106.8(16) . . ?
F1D C1 C2 107.4(14) . . ?
F1C C1 C2 111.8(5) . . ?
F1B C1 C2 112.3(4) . . ?
F23F C23 F23D 118(3) . . ?
F23C C23 F23B 107.6(5) . . ?
F23F C23 F23E 89(2) . . ?
F23D C23 F23E 112(2) . . ?
F23C C23 F23A 105.2(5) . . ?
F23B C23 F23A 102.9(6) . . ?
F23F C23 C22 115(2) . . ?
F23C C23 C22 114.0(4) . . ?
F23D C23 C22 114.4(11) . . ?
F23B C23 C22 113.1(6) . . ?
F23E C23 C22 104.4(11) . . ?
F23A C23 C22 113.2(4) . . ?
H28E C28 S2B 86(7) . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_opda-dicf3-nco-TBASO4-6
_database_code_depnum_ccdc_archive 'CCDC 1525841'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         '2(C24 H14 F12 N4 O2), 2(C16 H36 N), O4 S'
_chemical_formula_sum            'C80 H100 F24 N10 O8 S'
_chemical_formula_weight         1817.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   14.8485(8)
_cell_length_b                   17.8004(11)
_cell_length_c                   20.1415(12)
_cell_angle_alpha                113.187(6)
_cell_angle_beta                 98.384(5)
_cell_angle_gamma                105.077(5)
_cell_volume                     4536.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3478
_cell_measurement_theta_min      3.1910
_cell_measurement_theta_max      19.6870

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1892.0
_exptl_transmission_factor_min   0.965
_exptl_transmission_factor_max   0.978
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.141
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealead tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36260
_diffrn_reflns_av_unetI/netI     0.1366
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.928
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             15942
_reflns_number_gt                13480
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0100P)²+4.5695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00083(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         15942
_refine_ls_number_parameters     1197
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.2439
_refine_ls_R_factor_gt           0.0994
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002

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
C25A C 0.3063(15) 0.6037(10) 0.4244(15) 0.206(8) Uani 0.5 1 d D . P A 1
F15A F 0.3348(12) 0.5641(14) 0.4629(12) 0.212(6) Uani 0.5 1 d D . P A 1
F14A F 0.2132(15) 0.576(3) 0.422(4) 0.230(12) Uani 0.5 1 d D . P A 1
F13A F 0.336(2) 0.6903(10) 0.4615(11) 0.210(9) Uani 0.5 1 d D . P A 1
C20A C 0.1810(9) -0.1575(10) 0.3862(9) 0.181(6) Uani 0.5 1 d D . P B 1
F8A F 0.2624(10) -0.1721(11) 0.4040(10) 0.185(7) Uani 0.5 1 d D . P B 1
F9A F 0.0968(12) -0.1955(12) 0.3950(17) 0.218(7) Uani 0.5 1 d D . P B 1
F7A F 0.215(14) -0.095(4) 0.4574(16) 0.252(5) Uani 0.5 1 d D . P B 1
C66A C 0.7800(14) 0.2483(8) 0.1248(14) 0.149(15) Uani 0.5 1 d D . P C 1
H66A H 0.8052 0.2880 0.1781 0.179 Uiso 0.5 1 calc R U P C 1
H66B H 0.8331 0.2538 0.1021 0.179 Uiso 0.5 1 calc R U P C 1
C68A C 0.735(4) 0.3541(14) 0.0772(18) 0.28(3) Uani 0.5 1 d D . P C 1
H68A H 0.7936 0.3947 0.1158 0.427 Uiso 0.5 1 calc R U P C 1
H68B H 0.6857 0.3804 0.0800 0.427 Uiso 0.5 1 calc R U P C 1
H68C H 0.7467 0.3386 0.0288 0.427 Uiso 0.5 1 calc R U P C 1
C67A C 0.6999(13) 0.2716(12) 0.0882(13) 0.150(8) Uani 0.5 1 d D . P C 1
H67A H 0.6636 0.2226 0.0395 0.179 Uiso 0.5 1 calc R U P C 1
H67B H 0.6554 0.2790 0.1191 0.179 Uiso 0.5 1 calc R U P C 1
C80A C 0.7589(19) 0.1933(15) 0.3984(13) 0.25(2) Uani 0.5 1 d D . P D 1
H80A H 0.6926 0.1908 0.3904 0.374 Uiso 0.5 1 calc R U P D 1
H80B H 0.7918 0.2254 0.4512 0.374 Uiso 0.5 1 calc R U P D 1
H80C H 0.7606 0.1352 0.3799 0.374 Uiso 0.5 1 calc R U P D 1
C25B C 0.2915(14) 0.6033(12) 0.4285(13) 0.206(8) Uani 0.5 1 d D . P A 2
F15B F 0.2755(14) 0.5383(12) 0.4473(13) 0.212(6) Uani 0.5 1 d D . P A 2
F14B F 0.2040(15) 0.610(3) 0.417(4) 0.230(12) Uani 0.5 1 d D . P A 2
F13B F 0.359(2) 0.6627(12) 0.4923(10) 0.210(9) Uani 0.5 1 d D . P A 2
C20B C 0.1933(14) -0.1425(8) 0.3962(10) 0.181(6) Uani 0.5 1 d D . P B 2
F8B F 0.1892(13) -0.2250(9) 0.3660(10) 0.185(7) Uani 0.5 1 d D . P B 2
F9B F 0.1145(14) -0.1471(13) 0.4207(17) 0.218(7) Uani 0.5 1 d D . P B 2
F7B F 0.237(14) -0.081(4) 0.4672(16) 0.252(5) Uani 0.5 1 d D . P B 2
C66B C 0.744(2) 0.2453(8) 0.1293(12) 0.178(16) Uani 0.5 1 d D . P C 2
H66C H 0.7992 0.2864 0.1726 0.214 Uiso 0.5 1 calc R U P C 2
H66D H 0.6859 0.2547 0.1412 0.214 Uiso 0.5 1 calc R U P C 2
C68B C 0.745(3) 0.3516(16) 0.095(2) 0.31(4) Uani 0.5 1 d D . P C 2
H68D H 0.7016 0.3517 0.1255 0.461 Uiso 0.5 1 calc R U P C 2
H68E H 0.7200 0.3636 0.0549 0.461 Uiso 0.5 1 calc R U P C 2
H68F H 0.8076 0.3955 0.1250 0.461 Uiso 0.5 1 calc R U P C 2
C67B C 0.757(3) 0.2615(14) 0.0609(12) 0.248(18) Uani 0.5 1 d D . P C 2
H67C H 0.7056 0.2196 0.0151 0.298 Uiso 0.5 1 calc R U P C 2
H67D H 0.8199 0.2645 0.0528 0.298 Uiso 0.5 1 calc R U P C 2
C80B C 0.7319(13) 0.2358(18) 0.3988(12) 0.161(11) Uani 0.5 1 d D . P D 2
H80D H 0.7019 0.2776 0.3988 0.242 Uiso 0.5 1 calc R U P D 2
H80E H 0.7616 0.2492 0.4496 0.242 Uiso 0.5 1 calc R U P D 2
H80F H 0.6835 0.1784 0.3743 0.242 Uiso 0.5 1 calc R U P D 2
C79 C 0.8098(7) 0.2392(9) 0.3563(6) 0.207(6) Uani 1 1 d D . . . .
H79A H 0.7981 0.2934 0.3668 0.249 Uiso 0.5 1 calc DR U P D 1
H79C H 0.8793 0.2517 0.3705 0.249 Uiso 0.5 1 calc DR U P D 1
H79B H 0.797(4) 0.288(3) 0.392(4) 0.249 Uiso 0.5 1 d D U P D 2
H79D H 0.797(4) 0.288(3) 0.392(4) 0.249 Uiso 0.5 1 d D U P D 2
F5 F -0.0535(6) 0.5989(5) 0.2610(4) 0.266(4) Uani 1 1 d D . . . .
F17 F 0.3906(7) 0.7558(5) 0.2720(5) 0.286(5) Uani 1 1 d . . . . .
F6 F 0.0257(6) 0.6535(4) 0.2041(6) 0.287(4) Uani 1 1 d D . . . .
F16 F 0.4272(8) 0.6753(6) 0.1855(7) 0.337(7) Uani 1 1 d D . . . .
F19 F 0.6140(4) -0.0938(4) 0.3402(3) 0.195(3) Uani 1 1 d D . . . .
F21 F 0.5694(6) -0.1247(5) 0.2303(4) 0.231(4) Uani 1 1 d . . . . .
F20 F 0.6890(5) -0.0178(5) 0.2957(6) 0.268(5) Uani 1 1 d D . . . .
F23 F 0.3623(4) 0.1255(4) 0.4655(3) 0.170(2) Uani 1 1 d . . . . .
F24 F 0.4156(6) 0.0430(5) 0.4873(3) 0.233(4) Uani 1 1 d D . . . .
F22 F 0.5052(4) 0.1690(5) 0.5191(3) 0.262(5) Uani 1 1 d D . . . .
F18 F 0.2877(8) 0.6620(7) 0.1779(7) 0.324(7) Uani 1 1 d . . . . .
O4 O 0.5189(3) 0.0853(3) 0.1478(2) 0.0826(13) Uani 1 1 d . . . . .
O3 O 0.4538(3) 0.4135(3) 0.1382(2) 0.0929(14) Uani 1 1 d . . . . .
N5 N 0.3508(3) 0.3906(3) 0.2083(3) 0.0812(15) Uani 1 1 d . . . . .
H5N H 0.3212 0.3522 0.2210 0.097 Uiso 1 1 d R U . . .
N6 N 0.3685(3) 0.2755(3) 0.1181(3) 0.0751(14) Uani 1 1 d . . . . .
H6N H 0.3221 0.2470 0.1294 0.090 Uiso 1 1 d R U . . .
N7 N 0.3900(3) 0.1251(3) 0.1189(2) 0.0699(13) Uani 1 1 d . . . . .
H7N H 0.3339 0.1243 0.1255 0.084 Uiso 1 1 d R U . . .
N8 N 0.4138(3) 0.0988(3) 0.2207(3) 0.0764(14) Uani 1 1 d . . . . .
H8N H 0.3651 0.1155 0.2273 0.092 Uiso 1 1 d R U . . .
C44 C 0.6002(5) -0.0578(6) 0.2948(5) 0.147(4) Uani 1 1 d D . . . .
C43 C 0.5412(5) -0.0033(4) 0.3121(4) 0.091(2) Uani 1 1 d . . . . .
C45 C 0.5186(5) 0.0224(5) 0.3789(4) 0.096(2) Uani 1 1 d . . . . .
H45 H 0.5409 0.0059 0.4147 0.116 Uiso 1 1 calc R U . . .
C46 C 0.4616(5) 0.0737(5) 0.3913(4) 0.086(2) Uani 1 1 d . . . . .
C48 C 0.4280(4) 0.0991(4) 0.3395(3) 0.0768(18) Uani 1 1 d . . . . .
H48 H 0.3894 0.1336 0.3495 0.092 Uiso 1 1 calc R U . . .
C41 C 0.4520(4) 0.0728(4) 0.2722(3) 0.0701(17) Uani 1 1 d . . . . .
C42 C 0.5095(5) 0.0212(4) 0.2574(3) 0.085(2) Uani 1 1 d . . . . .
H42 H 0.5265 0.0035 0.2124 0.103 Uiso 1 1 calc R U . . .
C40 C 0.4467(5) 0.1008(4) 0.1611(3) 0.0685(17) Uani 1 1 d . . . . .
C39 C 0.4179(4) 0.1494(4) 0.0642(3) 0.0683(16) Uani 1 1 d . . . . .
C38 C 0.4546(4) 0.0999(4) 0.0106(4) 0.0852(19) Uani 1 1 d . . . . .
H38 H 0.4596 0.0485 0.0096 0.102 Uiso 1 1 calc R U . . .
C37 C 0.4842(6) 0.1259(6) -0.0415(4) 0.112(3) Uani 1 1 d . . . . .
H37 H 0.5088 0.0921 -0.0773 0.135 Uiso 1 1 calc R U . . .
C36 C 0.4771(6) 0.2008(6) -0.0399(4) 0.113(3) Uani 1 1 d . . . . .
H36 H 0.4984 0.2186 -0.0742 0.136 Uiso 1 1 calc R U . . .
C35 C 0.4387(5) 0.2516(5) 0.0120(4) 0.095(2) Uani 1 1 d . . . . .
H35 H 0.4324 0.3020 0.0113 0.114 Uiso 1 1 calc R U . . .
C34 C 0.4100(4) 0.2266(4) 0.0645(3) 0.0730(17) Uani 1 1 d . . . . .
C33 C 0.3966(5) 0.3644(4) 0.1521(4) 0.0715(17) Uani 1 1 d . . . . .
C31 C 0.3513(4) 0.4751(4) 0.2475(4) 0.0837(19) Uani 1 1 d . . . . .
C30 C 0.3636(5) 0.5334(5) 0.2171(4) 0.103(2) Uani 1 1 d . . . . .
H30 H 0.3764 0.5191 0.1706 0.123 Uiso 1 1 calc R U . . .
C28 C 0.3562(7) 0.6141(6) 0.2583(8) 0.136(4) Uani 1 1 d . . . . .
C32 C 0.3316(4) 0.4992(5) 0.3161(4) 0.099(2) Uani 1 1 d . . . . .
H32 H 0.3242 0.4608 0.3372 0.119 Uiso 1 1 calc R U . . .
C26 C 0.3224(6) 0.5799(7) 0.3544(6) 0.125(3) Uani 1 1 d . . . . .
C29 C 0.3640(11) 0.6739(10) 0.2258(9) 0.207(7) Uani 1 1 d D . . . .
C47 C 0.4382(6) 0.1008(4) 0.4613(4) 0.129(3) Uani 1 1 d D . . . .
C27 C 0.3358(7) 0.6370(7) 0.3254(8) 0.160(5) Uani 1 1 d . . . . .
H27 H 0.3312 0.6915 0.3511 0.192 Uiso 1 1 calc R U . . .
N10 N 0.8159(4) 0.1309(5) 0.1529(4) 0.107(2) Uani 1 1 d . . . . .
C73 C 0.7750(6) 0.0346(6) 0.1328(4) 0.123(3) Uani 1 1 d . . . . .
H74A H 0.7149 0.0237 0.1468 0.148 Uiso 1 1 calc R U . . .
H73B H 0.7592 0.0012 0.0786 0.148 Uiso 1 1 calc R U . . .
C75 C 0.7980(7) -0.0973(7) 0.1374(6) 0.167(4) Uani 1 1 d . . . . .
H75B H 0.7936 -0.1237 0.0842 0.201 Uiso 1 1 calc R U . . .
H75A H 0.7327 -0.1133 0.1425 0.201 Uiso 1 1 calc R U . . .
C76 C 0.8578(9) -0.1331(7) 0.1766(6) 0.214(6) Uani 1 1 d . . . . .
H76A H 0.8601 -0.1091 0.2289 0.321 Uiso 1 1 calc R U . . .
H76B H 0.9226 -0.1174 0.1717 0.321 Uiso 1 1 calc R U . . .
H76C H 0.8287 -0.1955 0.1538 0.321 Uiso 1 1 calc R U . . .
C77 C 0.8462(5) 0.1867(5) 0.2378(4) 0.122(3) Uani 1 1 d . . . . .
H77B H 0.8979 0.1730 0.2603 0.146 Uiso 1 1 calc R U . . .
H77A H 0.8721 0.2476 0.2486 0.146 Uiso 1 1 calc R U . . .
C69 C 0.9070(6) 0.1495(6) 0.1276(6) 0.124(3) Uani 1 1 d . . . . .
H69B H 0.928(6) 0.211(5) 0.143(4) 0.149 Uiso 1 1 d . U . . .
H69A H 0.966(5) 0.149(5) 0.165(4) 0.149 Uiso 1 1 d . U . . .
C70 C 0.8948(6) 0.0976(6) 0.0445(6) 0.148(3) Uani 1 1 d . . . . .
H70A H 0.8413 0.1020 0.0143 0.177 Uiso 1 1 calc R U . . .
H70B H 0.8829 0.0366 0.0314 0.177 Uiso 1 1 calc R U . . .
C65 C 0.7374(7) 0.1539(6) 0.1132(4) 0.138(3) Uani 1 1 d D . . . .
H65A H 0.6823 0.1478 0.1338 0.165 Uiso 0.5 1 calc DR U P C 1
H65C H 0.7149 0.1141 0.0599 0.165 Uiso 0.5 1 calc DR U P C 1
H65B H 0.729(7) 0.103(3) 0.068(2) 0.165 Uiso 0.5 1 d D U P C 2
H65D H 0.689(3) 0.116(3) 0.124(3) 0.165 Uiso 0.5 1 d D U P E 2
C78 C 0.7649(6) 0.1749(6) 0.2744(5) 0.139(3) Uani 1 1 d . . . . .
H78B H 0.7113 0.1872 0.2524 0.167 Uiso 1 1 calc R U . . .
H78A H 0.7411 0.1157 0.2683 0.167 Uiso 1 1 calc R U . . .
C74 C 0.8410(6) 0.0007(6) 0.1692(4) 0.122(3) Uani 1 1 d . . . . .
H74B H 0.9041 0.0168 0.1605 0.147 Uiso 1 1 calc R U . . .
H74C H 0.8498 0.0273 0.2231 0.147 Uiso 1 1 calc R U . . .
C71 C 0.9918(7) 0.1392(7) 0.0327(5) 0.190(5) Uani 1 1 d D . . . .
H71A H 1.0452 0.1380 0.0659 0.228 Uiso 1 1 calc R U . . .
H71B H 1.0015 0.1995 0.0440 0.228 Uiso 1 1 calc R U . . .
C72 C 0.9888(7) 0.0871(8) -0.0499(5) 0.253(7) Uani 1 1 d D . . . .
H72A H 0.9878 0.0298 -0.0588 0.379 Uiso 1 1 calc R U . . .
H72B H 1.0452 0.1165 -0.0599 0.379 Uiso 1 1 calc R U . . .
H72C H 0.9313 0.0826 -0.0824 0.379 Uiso 1 1 calc R U . . .
F2 F 0.1591(9) 0.4645(7) 0.0155(6) 0.324(6) Uani 1 1 d D . . . .
F3 F 0.0612(7) 0.3489(8) -0.0247(4) 0.324(6) Uani 1 1 d D . . . .
F1 F 0.1920(7) 0.3714(9) 0.0316(4) 0.296(5) Uani 1 1 d D . . . .
F10 F 0.2475(4) -0.0986(4) 0.1222(3) 0.174(2) Uani 1 1 d . . . . .
F12 F 0.1669(4) -0.2204(4) 0.1090(3) 0.229(4) Uani 1 1 d D . . . .
F11 F 0.3125(5) -0.1624(4) 0.1673(3) 0.178(2) Uani 1 1 d . . . . .
O2 O 0.1147(3) 0.1225(3) 0.4398(2) 0.0936(14) Uani 1 1 d . . . . .
O1 O -0.0024(3) 0.4078(3) 0.3325(2) 0.0838(13) Uani 1 1 d . . . . .
N3 N 0.0762(3) 0.1907(3) 0.3700(3) 0.0718(14) Uani 1 1 d . . . . .
H3N H 0.0673 0.1881 0.3259 0.086 Uiso 1 1 d R U . . .
N4 N 0.1146(4) 0.0691(3) 0.3161(3) 0.0809(15) Uani 1 1 d . . . . .
H4N H 0.1012 0.0766 0.2766 0.097 Uiso 1 1 d R U . . .
N1 N 0.0964(3) 0.3739(3) 0.2570(3) 0.0746(14) Uani 1 1 d . . . . .
H1N H 0.1334 0.3436 0.2460 0.090 Uiso 1 1 d R U . . .
N2 N 0.1053(3) 0.3452(3) 0.3580(2) 0.0706(14) Uani 1 1 d . . . . .
H2N H 0.1507 0.3268 0.3446 0.085 Uiso 1 1 d R U . . .
C19 C 0.1822(5) -0.1052(5) 0.3431(4) 0.098(2) Uani 1 1 d D . . . .
C18 C 0.1507(4) -0.0348(4) 0.3588(4) 0.087(2) Uani 1 1 d . . . . .
H18 H 0.1325 -0.0113 0.4027 0.104 Uiso 1 1 calc R U . . .
C17 C 0.1466(4) 0.0002(4) 0.3081(4) 0.0754(17) Uani 1 1 d . . . . .
C24 C 0.1740(4) -0.0370(4) 0.2423(4) 0.0816(19) Uani 1 1 d . . . . .
H24 H 0.1715 -0.0141 0.2080 0.098 Uiso 1 1 calc R U . . .
C16 C 0.1029(4) 0.1261(4) 0.3806(4) 0.0705(17) Uani 1 1 d . . . . .
C15 C 0.0624(4) 0.2608(4) 0.4268(3) 0.0693(16) Uani 1 1 d . . . . .
C13 C 0.0142(5) 0.3247(5) 0.5391(4) 0.089(2) Uani 1 1 d . . . . .
H13 H -0.0094 0.3191 0.5778 0.107 Uiso 1 1 calc R U . . .
C12 C 0.0351(5) 0.4022(5) 0.5360(4) 0.095(2) Uani 1 1 d . . . . .
H12 H 0.0286 0.4500 0.5736 0.114 Uiso 1 1 calc R U . . .
C11 C 0.0666(4) 0.4091(4) 0.4759(4) 0.0822(19) Uani 1 1 d . . . . .
H11 H 0.0796 0.4615 0.4730 0.099 Uiso 1 1 calc R U . . .
C10 C 0.0784(4) 0.3392(4) 0.4209(3) 0.0687(16) Uani 1 1 d . . . . .
C9 C 0.0611(5) 0.3794(4) 0.3177(3) 0.0693(17) Uani 1 1 d . . . . .
C8 C 0.1084(5) 0.3889(5) 0.1477(4) 0.098(2) Uani 1 1 d . . . . .
H8 H 0.1380 0.3471 0.1351 0.118 Uiso 1 1 calc R U . . .
C2 C 0.0927(6) 0.4300(7) 0.1026(5) 0.122(3) Uani 1 1 d . . . . .
C4 C 0.0225(6) 0.5142(5) 0.1831(5) 0.109(3) Uani 1 1 d . . . . .
C6 C 0.0350(5) 0.4763(4) 0.2297(3) 0.087(2) Uani 1 1 d . . . . .
H6 H 0.0146 0.4928 0.2731 0.104 Uiso 1 1 calc R U . . .
C5 C -0.0197(5) 0.5772(5) 0.2018(4) 0.166(5) Uani 1 1 d D . . . .
C21 C 0.2086(5) -0.1421(5) 0.2776(5) 0.106(2) Uani 1 1 d . . . . .
H21 H 0.2286 -0.1899 0.2673 0.128 Uiso 1 1 calc R U . . .
C7 C 0.0778(4) 0.4140(4) 0.2119(3) 0.0725(17) Uani 1 1 d . . . . .
C3 C 0.0509(6) 0.4935(7) 0.1192(5) 0.130(3) Uani 1 1 d . . . . .
H3 H 0.0428 0.5204 0.0886 0.156 Uiso 1 1 calc R U . . .
C14 C 0.0277(4) 0.2543(5) 0.4855(4) 0.0828(19) Uani 1 1 d . . . . .
H14 H 0.0134 0.2019 0.4887 0.099 Uiso 1 1 calc R U . . .
C22 C 0.2044(5) -0.1065(5) 0.2282(4) 0.090(2) Uani 1 1 d . . . . .
C1 C 0.1250(6) 0.4079(5) 0.0407(4) 0.218(6) Uani 1 1 d D . . . .
C23 C 0.2335(6) -0.1445(4) 0.1594(5) 0.129(3) Uani 1 1 d D . . . .
N9 N 0.6917(4) 0.6390(4) 0.3307(3) 0.0902(16) Uani 1 1 d . . . . .
C57 C 0.7192(5) 0.5596(5) 0.3226(4) 0.103(2) Uani 1 1 d . . . . .
H57B H 0.7554 0.5484 0.2856 0.123 Uiso 1 1 calc R U . . .
H57A H 0.7620 0.5734 0.3703 0.123 Uiso 1 1 calc R U . . .
C58 C 0.6343(6) 0.4770(5) 0.2995(4) 0.129(3) Uani 1 1 d . . . . .
H58A H 0.5913 0.4899 0.3309 0.154 Uiso 1 1 calc R U . . .
H58B H 0.5980 0.4561 0.2478 0.154 Uiso 1 1 calc R U . . .
C59 C 0.6671(7) 0.4071(6) 0.3065(5) 0.164(4) Uani 1 1 d . . . . .
H59A H 0.7033 0.4281 0.3583 0.196 Uiso 1 1 calc R U . . .
H59B H 0.7105 0.3946 0.2754 0.196 Uiso 1 1 calc R U . . .
C60 C 0.5823(7) 0.3232(5) 0.2830(5) 0.186(4) Uani 1 1 d . . . . .
H60C H 0.5279 0.3207 0.2488 0.279 Uiso 1 1 calc R U . . .
H60B H 0.5644 0.3225 0.3267 0.279 Uiso 1 1 calc R U . . .
H60A H 0.6012 0.2739 0.2586 0.279 Uiso 1 1 calc R U . . .
C61 C 0.6306(5) 0.6222(5) 0.2558(4) 0.104(2) Uani 1 1 d . . . . .
H61A H 0.5677 0.5716 0.2380 0.125 Uiso 1 1 d R U . . .
H61B H 0.6088 0.6714 0.2598 0.125 Uiso 1 1 d R U . . .
C62 C 0.6789(6) 0.6046(6) 0.1929(5) 0.135(3) Uani 1 1 d . . . . .
H62A H 0.6922 0.5508 0.1802 0.163 Uiso 1 1 calc R U . . .
H62B H 0.7396 0.6519 0.2076 0.163 Uiso 1 1 calc R U . . .
C63 C 0.6057(6) 0.5971(6) 0.1247(5) 0.159(4) Uani 1 1 d D . . . .
H11K H 0.5430 0.5538 0.1135 0.191 Uiso 1 1 calc R U . . .
H11L H 0.5973 0.6527 0.1361 0.191 Uiso 1 1 calc R U . . .
C53 C 0.6304(5) 0.6579(5) 0.3849(5) 0.104(2) Uani 1 1 d . . . . .
H53A H 0.5687 0.6102 0.3638 0.125 Uiso 1 1 calc R U . . .
H53B H 0.6173 0.7103 0.3901 0.125 Uiso 1 1 calc R U . . .
C51 C 0.8810(5) 0.8664(5) 0.3870(4) 0.111(3) Uani 1 1 d . . . . .
H51B H 0.9218 0.8683 0.4303 0.133 Uiso 1 1 calc R U . . .
H51A H 0.9081 0.8452 0.3451 0.133 Uiso 1 1 calc R U . . .
C52 C 0.8843(6) 0.9552(5) 0.4036(5) 0.153(3) Uani 1 1 d . . . . .
H52B H 0.8627 0.9786 0.4475 0.229 Uiso 1 1 calc R U . . .
H52A H 0.8426 0.9539 0.3616 0.229 Uiso 1 1 calc R U . . .
H52C H 0.9497 0.9913 0.4125 0.229 Uiso 1 1 calc R U . . .
C54 C 0.6783(6) 0.6704(6) 0.4629(5) 0.137(3) Uani 1 1 d . . . . .
H54A H 0.7102 0.6284 0.4593 0.165 Uiso 1 1 calc R U . . .
H54B H 0.7253 0.7288 0.4934 0.165 Uiso 1 1 calc R U . . .
C49 C 0.7870(4) 0.7158(5) 0.3584(4) 0.095(2) Uani 1 1 d . . . . .
H49A H 0.8229 0.7244 0.4067 0.113 Uiso 1 1 calc R U . . .
H49B H 0.8252 0.6996 0.3235 0.113 Uiso 1 1 calc R U . . .
C50 C 0.7793(5) 0.8021(5) 0.3675(4) 0.103(2) Uani 1 1 d . . . . .
H50A H 0.7494 0.8241 0.4073 0.124 Uiso 1 1 calc R U . . .
H50B H 0.7393 0.7946 0.3212 0.124 Uiso 1 1 calc R U . . .
C55 C 0.5939(8) 0.6551(8) 0.4945(6) 0.219(6) Uani 1 1 d D . . . .
H55A H 0.5393 0.6064 0.4554 0.263 Uiso 1 1 calc R U . . .
H55B H 0.5750 0.7063 0.5104 0.263 Uiso 1 1 calc R U . . .
C64 C 0.6481(7) 0.5700(7) 0.0572(5) 0.231(6) Uani 1 1 d D . . . .
H19K H 0.6539 0.5140 0.0454 0.347 Uiso 1 1 calc R U . . .
H19L H 0.7110 0.6124 0.0696 0.347 Uiso 1 1 calc R U . . .
H19M H 0.6058 0.5667 0.0146 0.347 Uiso 1 1 calc R U . . .
C56 C 0.6168(9) 0.6357(9) 0.5618(7) 0.285(8) Uani 1 1 d D . . . .
H56A H 0.6176 0.5774 0.5440 0.428 Uiso 1 1 calc R U . . .
H56B H 0.5678 0.6413 0.5879 0.428 Uiso 1 1 calc R U . . .
H56C H 0.6791 0.6763 0.5954 0.428 Uiso 1 1 calc R U . . .
S1 S 0.20633(12) 0.19342(12) 0.22211(10) 0.0755(5) Uani 1 1 d . . . . .
O5 O 0.1052(3) 0.1521(3) 0.2204(2) 0.0821(12) Uani 1 1 d . . . . .
O7 O 0.2167(3) 0.1694(3) 0.1458(2) 0.0938(14) Uani 1 1 d . . . . .
O6 O 0.2330(3) 0.2899(3) 0.2627(2) 0.0891(13) Uani 1 1 d . . . . .
O8 O 0.2717(3) 0.1662(3) 0.2619(2) 0.0937(13) Uani 1 1 d . . . . .
F4 F -0.1000(6) 0.5648(5) 0.1537(4) 0.260(4) Uani 1 1 d 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
C25A F15A 1.3300(10) . ?
C25A F13A 1.3300(11) . ?
C25A F14A 1.3301(11) . ?
C25A C26 1.38(3) . ?
C20A F9A 1.3301(10) . ?
C20A F8A 1.3300(10) . ?
C20A F7A 1.338(17) . ?
C20A C19 1.5000(10) . ?
F8A F7A 1.75(17) . ?
C66A C67A 1.5397(10) . ?
C66A C65 1.5401(10) . ?
C66A H66A 0.9700 . ?
C66A H66B 0.9700 . ?
C68A C67A 1.5400(10) . ?
C68A H68A 0.9600 . ?
C68A H68B 0.9600 . ?
C68A H68C 0.9600 . ?
C67A H67A 0.9700 . ?
C67A H67B 0.9700 . ?
C80A C79 1.5397(10) . ?
C80A H80A 0.9600 . ?
C80A H80B 0.9600 . ?
C80A H80C 0.9600 . ?
C25B F13B 1.3300(11) . ?
C25B F15B 1.3300(10) . ?
C25B F14B 1.3301(10) . ?
C25B C26 1.55(3) . ?
C20B F9B 1.3301(10) . ?
C20B F8B 1.3300(10) . ?
C20B F7B 1.338(18) . ?
C20B C19 1.47(2) . ?
C66B C65 1.5003(10) . ?
C66B C67B 1.5398(10) . ?
C66B H66C 0.9700 . ?
C66B H66D 0.9700 . ?
C68B C67B 1.5403(11) . ?
C68B H68D 0.9600 . ?
C68B H68E 0.9600 . ?
C68B H68F 0.9600 . ?
C67B H67C 0.9700 . ?
C67B H67D 0.9700 . ?
C80B C79 1.5396(10) . ?
C80B H80D 0.9600 . ?
C80B H80E 0.9600 . ?
C80B H80F 0.9600 . ?
C80B H79B 1.23(7) . ?
C80B H79D 1.23(7) . ?
C79 H79B 0.9700(11) . ?
C79 H79D 0.9700(11) . ?
C79 C78 1.507(11) . ?
C79 H79A 0.9700 . ?
C79 H79C 0.9700 . ?
C79 H79B 0.9700(11) . ?
C79 H79D 0.9700(11) . ?
F5 C5 1.3190(10) . ?
F17 C29 1.293(14) . ?
F6 C5 1.3296(10) . ?
F16 C29 1.3295(10) . ?
F19 C44 1.3290(10) . ?
F21 C44 1.281(10) . ?
F20 C44 1.3196(10) . ?
F23 C47 1.316(9) . ?
F24 C47 1.3191(10) . ?
F22 C47 1.3189(11) . ?
F18 C29 1.288(15) . ?
O4 C40 1.217(6) . ?
O3 C33 1.200(6) . ?
N5 C33 1.391(7) . ?
N5 C31 1.395(7) . ?
N5 H5N 0.8596 . ?
N6 C33 1.365(7) . ?
N6 C34 1.429(7) . ?
N6 H6N 0.8587 . ?
N7 C40 1.374(6) . ?
N7 C39 1.409(6) . ?
N7 H7N 0.8600 . ?
N8 C40 1.370(6) . ?
N8 C41 1.398(6) . ?
N8 H8N 0.8596 . ?
C44 C43 1.446(9) . ?
C43 C45 1.363(8) . ?
C43 C42 1.401(7) . ?
C45 C46 1.377(8) . ?
C45 H45 0.9300 . ?
C46 C48 1.371(7) . ?
C46 C47 1.426(9) . ?
C48 C41 1.383(7) . ?
C48 H48 0.9300 . ?
C41 C42 1.389(7) . ?
C42 H42 0.9300 . ?
C39 C38 1.382(7) . ?
C39 C34 1.407(7) . ?
C38 C37 1.386(8) . ?
C38 H38 0.9300 . ?
C37 C36 1.353(9) . ?
C37 H37 0.9300 . ?
C36 C35 1.391(9) . ?
C36 H36 0.9300 . ?
C35 C34 1.379(7) . ?
C35 H35 0.9300 . ?
C31 C32 1.376(8) . ?
C31 C30 1.387(8) . ?
C30 C28 1.390(10) . ?
C30 H30 0.9300 . ?
C28 C27 1.355(12) . ?
C28 C29 1.442(15) . ?
C32 C26 1.392(10) . ?
C32 H32 0.9300 . ?
C26 C27 1.345(12) . ?
C27 H27 0.9300 . ?
N10 C69 1.517(10) . ?
N10 C73 1.520(9) . ?
N10 C77 1.523(8) . ?
N10 C65 1.549(9) . ?
C73 C74 1.519(9) . ?
C73 H74A 0.9700 . ?
C73 H73B 0.9700 . ?
C75 C74 1.511(10) . ?
C75 C76 1.518(11) . ?
C75 H75B 0.9700 . ?
C75 H75A 0.9700 . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
C77 C78 1.514(9) . ?
C77 H77B 0.9700 . ?
C77 H77A 0.9700 . ?
C69 C70 1.515(11) . ?
C69 H69B 0.95(7) . ?
C69 H69A 1.07(7) . ?
C70 C71 1.538(10) . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C65 H65B 0.9600(11) . ?
C65 H65A 0.9700 . ?
C65 H65C 0.9700 . ?
C65 H65B 0.9600(11) . ?
C65 H65D 0.9601(11) . ?
C78 H78B 0.9700 . ?
C78 H78A 0.9700 . ?
C74 H74B 0.9700 . ?
C74 H74C 0.9700 . ?
C71 C72 1.5385(10) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
F2 C1 1.3197(10) . ?
F3 C1 1.3294(11) . ?
F1 C1 1.3196(10) . ?
F10 C23 1.309(9) . ?
F12 C23 1.3291(11) . ?
F11 C23 1.297(9) . ?
O2 C16 1.209(6) . ?
O1 C9 1.202(6) . ?
N3 C16 1.389(7) . ?
N3 C15 1.408(7) . ?
N3 H3N 0.8598 . ?
N4 C16 1.367(7) . ?
N4 C17 1.389(7) . ?
N4 H4N 0.8596 . ?
N1 C9 1.377(6) . ?
N1 C7 1.396(6) . ?
N1 H1N 0.8591 . ?
N2 C9 1.381(6) . ?
N2 C10 1.417(6) . ?
N2 H2N 0.8569 . ?
C19 C21 1.387(9) . ?
C19 C18 1.388(8) . ?
C18 C17 1.393(7) . ?
C18 H18 0.9300 . ?
C17 C24 1.401(7) . ?
C24 C22 1.366(8) . ?
C24 H24 0.9300 . ?
C15 C14 1.391(7) . ?
C15 C10 1.408(7) . ?
C13 C12 1.361(8) . ?
C13 C14 1.380(8) . ?
C13 H13 0.9300 . ?
C12 C11 1.398(7) . ?
C12 H12 0.9300 . ?
C11 C10 1.374(7) . ?
C11 H11 0.9300 . ?
C8 C7 1.378(8) . ?
C8 C2 1.403(10) . ?
C8 H8 0.9300 . ?
C2 C1 1.350(10) . ?
C2 C3 1.378(11) . ?
C4 C3 1.355(9) . ?
C4 C6 1.372(8) . ?
C4 C5 1.375(9) . ?
C6 C7 1.372(8) . ?
C6 H6 0.9300 . ?
C5 F4 1.3295(10) . ?
C21 C22 1.377(8) . ?
C21 H21 0.9300 . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C22 C23 1.467(10) . ?
N9 C53 1.513(7) . ?
N9 C61 1.515(7) . ?
N9 C57 1.526(7) . ?
N9 C49 1.531(7) . ?
C57 C58 1.514(8) . ?
C57 H57B 0.9700 . ?
C57 H57A 0.9700 . ?
C58 C59 1.496(9) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
C59 C60 1.527(9) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60C 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60A 0.9600 . ?
C61 C62 1.513(8) . ?
C61 H61A 1.0117 . ?
C61 H61B 0.9873 . ?
C62 C63 1.559(9) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.5384(10) . ?
C63 H11K 0.9700 . ?
C63 H11L 0.9700 . ?
C53 C54 1.531(9) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C51 C52 1.468(9) . ?
C51 C50 1.523(8) . ?
C51 H51B 0.9700 . ?
C51 H51A 0.9700 . ?
C52 H52B 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52C 0.9600 . ?
C54 C55 1.497(11) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C49 C50 1.510(8) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C55 C56 1.5376(10) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C64 H19K 0.9600 . ?
C64 H19L 0.9600 . ?
C64 H19M 0.9600 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
S1 O8 1.464(4) . ?
S1 O7 1.469(4) . ?
S1 O5 1.479(4) . ?
S1 O6 1.490(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F15A C25A F13A 116(2) . . ?
F15A C25A F14A 96(2) . . ?
F13A C25A F14A 105(3) . . ?
F15A C25A C26 116.0(19) . . ?
F13A C25A C26 109(2) . . ?
F14A C25A C26 114(3) . . ?
F9A C20A F8A 124.3(13) . . ?
F9A C20A F7A 94(8) . . ?
F8A C20A F7A 82(9) . . ?
F9A C20A C19 118.6(12) . . ?
F8A C20A C19 116.5(11) . . ?
F7A C20A C19 102(4) . . ?
C20A F8A F7A 49(4) . . ?
C20A F7A F8A 49(5) . . ?
C67A C66A C65 109.2(13) . . ?
C67A C66A H66A 109.9 . . ?
C65 C66A H66A 109.9 . . ?
C67A C66A H66B 109.8 . . ?
C65 C66A H66B 109.8 . . ?
H66A C66A H66B 108.3 . . ?
C67A C68A H68A 109.4 . . ?
C67A C68A H68B 109.5 . . ?
H68A C68A H68B 109.5 . . ?
C67A C68A H68C 109.5 . . ?
H68A C68A H68C 109.5 . . ?
H68B C68A H68C 109.5 . . ?
C68A C67A C66A 116(2) . . ?
C68A C67A H67A 108.3 . . ?
C66A C67A H67A 108.4 . . ?
C68A C67A H67B 108.3 . . ?
C66A C67A H67B 108.3 . . ?
H67A C67A H67B 107.4 . . ?
C79 C80A H80A 109.5 . . ?
C79 C80A H80B 109.5 . . ?
H80A C80A H80B 109.5 . . ?
C79 C80A H80C 109.5 . . ?
H80A C80A H80C 109.5 . . ?
H80B C80A H80C 109.5 . . ?
F13B C25B F15B 96.2(15) . . ?
F13B C25B F14B 118(3) . . ?
F15B C25B F14B 101(3) . . ?
F13B C25B C26 118(2) . . ?
F15B C25B C26 112.0(18) . . ?
F14B C25B C26 110(3) . . ?
F9B C20B F8B 102.7(16) . . ?
F9B C20B F7B 82(9) . . ?
F8B C20B F7B 128(6) . . ?
F9B C20B C19 105.5(17) . . ?
F8B C20B C19 115.6(15) . . ?
F7B C20B C19 112(4) . . ?
C65 C66B C67B 110.6(16) . . ?
C65 C66B H66C 109.5 . . ?
C67B C66B H66C 109.5 . . ?
C65 C66B H66D 109.5 . . ?
C67B C66B H66D 109.5 . . ?
H66C C66B H66D 108.1 . . ?
C67B C68B H68D 109.5 . . ?
C67B C68B H68E 109.3 . . ?
H68D C68B H68E 109.5 . . ?
C67B C68B H68F 109.6 . . ?
H68D C68B H68F 109.5 . . ?
H68E C68B H68F 109.5 . . ?
C66B C67B C68B 94(2) . . ?
C66B C67B H67C 112.9 . . ?
C68B C67B H67C 113.1 . . ?
C66B C67B H67D 112.8 . . ?
C68B C67B H67D 112.9 . . ?
H67C C67B H67D 110.3 . . ?
C79 C80B H80D 109.5 . . ?
C79 C80B H80E 109.5 . . ?
H80D C80B H80E 109.5 . . ?
C79 C80B H80F 109.5 . . ?
H80D C80B H80F 109.5 . . ?
H80E C80B H80F 109.5 . . ?
C79 C80B H79B 39.03(12) . . ?
H80D C80B H79B 79.4 . . ?
H80E C80B H79B 98.0 . . ?
H80F C80B H79B 145.3 . . ?
C79 C80B H79D 39.03(12) . . ?
H80D C80B H79D 79.4 . . ?
H80E C80B H79D 98.0 . . ?
H80F C80B H79D 145.3 . . ?
H79B C80B H79D 0(6) . . ?
H79B C79 H79D 0(4) . . ?
H79B C79 C78 135(5) . . ?
H79D C79 C78 135(5) . . ?
H79B C79 C80B 53(4) . . ?
H79D C79 C80B 53(4) . . ?
C78 C79 C80B 109.5(12) . . ?
C78 C79 C80A 104.3(13) . . ?
C78 C79 H79A 110.9 . . ?
C80A C79 H79A 110.9 . . ?
C78 C79 H79C 110.9 . . ?
C80A C79 H79C 110.9 . . ?
H79A C79 H79C 108.9 . . ?
H79B C79 H79B 0(5) . . ?
H79D C79 H79B 0(4) . . ?
C78 C79 H79B 135(5) . . ?
C80B C79 H79B 53(4) . . ?
H79B C79 H79D 0(4) . . ?
H79D C79 H79D 0(5) . . ?
C78 C79 H79D 135(5) . . ?
C80B C79 H79D 53(4) . . ?
H79B C79 H79D 0(4) . . ?
C33 N5 C31 125.1(6) . . ?
C33 N5 H5N 117.8 . . ?
C31 N5 H5N 117.0 . . ?
C33 N6 C34 124.6(5) . . ?
C33 N6 H6N 117.8 . . ?
C34 N6 H6N 117.6 . . ?
C40 N7 C39 123.6(5) . . ?
C40 N7 H7N 118.2 . . ?
C39 N7 H7N 118.3 . . ?
C40 N8 C41 126.5(5) . . ?
C40 N8 H8N 116.7 . . ?
C41 N8 H8N 116.8 . . ?
F21 C44 F20 102.2(8) . . ?
F21 C44 F19 101.2(7) . . ?
F20 C44 F19 103.8(6) . . ?
F21 C44 C43 117.2(6) . . ?
F20 C44 C43 114.7(7) . . ?
F19 C44 C43 115.7(7) . . ?
C45 C43 C42 122.5(6) . . ?
C45 C43 C44 120.7(6) . . ?
C42 C43 C44 116.8(6) . . ?
C43 C45 C46 117.6(6) . . ?
C43 C45 H45 121.2 . . ?
C46 C45 H45 121.2 . . ?
C48 C46 C45 122.4(7) . . ?
C48 C46 C47 120.1(7) . . ?
C45 C46 C47 117.6(6) . . ?
C46 C48 C41 119.3(6) . . ?
C46 C48 H48 120.4 . . ?
C41 C48 H48 120.4 . . ?
C48 C41 C42 120.3(5) . . ?
C48 C41 N8 116.8(6) . . ?
C42 C41 N8 122.8(6) . . ?
C41 C42 C43 118.0(6) . . ?
C41 C42 H42 121.0 . . ?
C43 C42 H42 121.0 . . ?
O4 C40 N8 124.4(5) . . ?
O4 C40 N7 123.5(6) . . ?
N8 C40 N7 112.1(5) . . ?
C38 C39 C34 118.7(6) . . ?
C38 C39 N7 121.7(6) . . ?
C34 C39 N7 119.6(5) . . ?
C39 C38 C37 121.0(7) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C36 C37 C38 119.5(7) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C36 C35 121.5(7) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C34 C35 C36 119.3(7) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C34 C39 120.0(6) . . ?
C35 C34 N6 121.5(6) . . ?
C39 C34 N6 118.4(5) . . ?
O3 C33 N6 126.4(6) . . ?
O3 C33 N5 124.3(6) . . ?
N6 C33 N5 109.2(6) . . ?
C32 C31 C30 118.8(7) . . ?
C32 C31 N5 118.9(7) . . ?
C30 C31 N5 122.0(7) . . ?
C31 C30 C28 117.8(8) . . ?
C31 C30 H30 121.1 . . ?
C28 C30 H30 121.1 . . ?
C27 C28 C30 123.0(10) . . ?
C27 C28 C29 118.3(11) . . ?
C30 C28 C29 118.5(12) . . ?
C31 C32 C26 121.4(8) . . ?
C31 C32 H32 119.3 . . ?
C26 C32 H32 119.3 . . ?
C27 C26 C25A 120.0(13) . . ?
C27 C26 C32 119.8(11) . . ?
C25A C26 C32 120.1(13) . . ?
C27 C26 C25B 119.3(13) . . ?
C32 C26 C25B 120.9(13) . . ?
F18 C29 F17 102.5(14) . . ?
F18 C29 F16 99.6(12) . . ?
F17 C29 F16 101.1(11) . . ?
F18 C29 C28 117.4(12) . . ?
F17 C29 C28 116.9(12) . . ?
F16 C29 C28 116.5(13) . . ?
F23 C47 F22 100.3(7) . . ?
F23 C47 F24 98.6(7) . . ?
F22 C47 F24 103.2(6) . . ?
F23 C47 C46 118.0(5) . . ?
F22 C47 C46 116.1(7) . . ?
F24 C47 C46 117.7(7) . . ?
C26 C27 C28 119.2(12) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C69 N10 C73 109.9(7) . . ?
C69 N10 C77 106.3(6) . . ?
C73 N10 C77 110.8(6) . . ?
C69 N10 C65 110.4(7) . . ?
C73 N10 C65 108.3(6) . . ?
C77 N10 C65 111.1(6) . . ?
C74 C73 N10 115.9(7) . . ?
C74 C73 H74A 108.3 . . ?
N10 C73 H74A 108.3 . . ?
C74 C73 H73B 108.3 . . ?
N10 C73 H73B 108.3 . . ?
H74A C73 H73B 107.4 . . ?
C74 C75 C76 112.4(9) . . ?
C74 C75 H75B 109.1 . . ?
C76 C75 H75B 109.1 . . ?
C74 C75 H75A 109.1 . . ?
C76 C75 H75A 109.1 . . ?
H75B C75 H75A 107.9 . . ?
C75 C76 H76A 109.5 . . ?
C75 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C75 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
C78 C77 N10 114.3(6) . . ?
C78 C77 H77B 108.7 . . ?
N10 C77 H77B 108.7 . . ?
C78 C77 H77A 108.7 . . ?
N10 C77 H77A 108.7 . . ?
H77B C77 H77A 107.6 . . ?
C70 C69 N10 115.5(7) . . ?
C70 C69 H69B 112(5) . . ?
N10 C69 H69B 104(5) . . ?
C70 C69 H69A 115(4) . . ?
N10 C69 H69A 110(4) . . ?
H69B C69 H69A 98(6) . . ?
C69 C70 C71 104.5(7) . . ?
C69 C70 H70A 110.9 . . ?
C71 C70 H70A 110.9 . . ?
C69 C70 H70B 110.9 . . ?
C71 C70 H70B 110.9 . . ?
H70A C70 H70B 108.9 . . ?
H65B C65 C66B 133(5) . . ?
H65B C65 N10 88(6) . . ?
C66B C65 N10 123.9(13) . . ?
N10 C65 C66A 109.8(9) . . ?
N10 C65 H65A 109.7 . . ?
C66A C65 H65A 109.7 . . ?
N10 C65 H65C 109.7 . . ?
C66A C65 H65C 109.7 . . ?
H65A C65 H65C 108.2 . . ?
H65B C65 H65B 0(5) . . ?
C66B C65 H65B 133(5) . . ?
N10 C65 H65B 88(6) . . ?
H65B C65 H65D 86(6) . . ?
C66B C65 H65D 124(4) . . ?
N10 C65 H65D 88(4) . . ?
H65B C65 H65D 86(6) . . ?
C79 C78 C77 104.9(7) . . ?
C79 C78 H78B 110.8 . . ?
C77 C78 H78B 110.8 . . ?
C79 C78 H78A 110.8 . . ?
C77 C78 H78A 110.8 . . ?
H78B C78 H78A 108.8 . . ?
C75 C74 C73 110.8(8) . . ?
C75 C74 H74B 109.5 . . ?
C73 C74 H74B 109.5 . . ?
C75 C74 H74C 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74B C74 H74C 108.1 . . ?
C70 C71 C72 108.4(9) . . ?
C70 C71 H71A 110.0 . . ?
C72 C71 H71A 110.0 . . ?
C70 C71 H71B 110.0 . . ?
C72 C71 H71B 110.0 . . ?
H71A C71 H71B 108.4 . . ?
C71 C72 H72A 109.5 . . ?
C71 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C71 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C16 N3 C15 124.5(5) . . ?
C16 N3 H3N 118.2 . . ?
C15 N3 H3N 117.2 . . ?
C16 N4 C17 126.2(5) . . ?
C16 N4 H4N 117.2 . . ?
C17 N4 H4N 116.6 . . ?
C9 N1 C7 125.6(5) . . ?
C9 N1 H1N 117.4 . . ?
C7 N1 H1N 117.0 . . ?
C9 N2 C10 122.5(5) . . ?
C9 N2 H2N 118.9 . . ?
C10 N2 H2N 118.6 . . ?
C21 C19 C18 121.5(6) . . ?
C21 C19 C20B 116.5(8) . . ?
C18 C19 C20B 122.0(8) . . ?
C21 C19 C20A 111.4(10) . . ?
C18 C19 C20A 126.6(9) . . ?
C19 C18 C17 119.1(6) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N4 C17 C18 125.0(6) . . ?
N4 C17 C24 115.9(6) . . ?
C18 C17 C24 119.1(6) . . ?
C22 C24 C17 120.5(6) . . ?
C22 C24 H24 119.8 . . ?
C17 C24 H24 119.8 . . ?
O2 C16 N4 125.4(6) . . ?
O2 C16 N3 123.5(6) . . ?
N4 C16 N3 111.1(5) . . ?
C14 C15 N3 123.0(6) . . ?
C14 C15 C10 118.5(6) . . ?
N3 C15 C10 118.3(6) . . ?
C12 C13 C14 120.9(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C12 C11 119.3(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C10 C15 119.7(6) . . ?
C11 C10 N2 120.4(6) . . ?
C15 C10 N2 119.9(6) . . ?
O1 C9 N1 124.6(5) . . ?
O1 C9 N2 123.9(6) . . ?
N1 C9 N2 111.5(5) . . ?
C7 C8 C2 116.3(7) . . ?
C7 C8 H8 121.8 . . ?
C2 C8 H8 121.8 . . ?
C1 C2 C3 118.8(9) . . ?
C1 C2 C8 116.8(10) . . ?
C3 C2 C8 124.3(8) . . ?
C3 C4 C6 123.2(8) . . ?
C3 C4 C5 117.5(7) . . ?
C6 C4 C5 119.3(8) . . ?
C4 C6 C7 119.7(7) . . ?
C4 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
F5 C5 F4 95.4(6) . . ?
F5 C5 F6 103.4(7) . . ?
F4 C5 F6 92.0(6) . . ?
F5 C5 C4 121.9(6) . . ?
F4 C5 C4 119.0(7) . . ?
F6 C5 C4 119.1(6) . . ?
C22 C21 C19 118.6(7) . . ?
C22 C21 H21 120.7 . . ?
C19 C21 H21 120.7 . . ?
C6 C7 C8 120.8(6) . . ?
C6 C7 N1 123.8(6) . . ?
C8 C7 N1 115.4(6) . . ?
C4 C3 C2 115.7(8) . . ?
C4 C3 H3 122.2 . . ?
C2 C3 H3 122.2 . . ?
C13 C14 C15 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C24 C22 C21 121.2(7) . . ?
C24 C22 C23 120.0(7) . . ?
C21 C22 C23 118.7(8) . . ?
F1 C1 F2 96.7(8) . . ?
F1 C1 F3 95.0(8) . . ?
F2 C1 F3 94.6(8) . . ?
F1 C1 C2 123.8(7) . . ?
F2 C1 C2 122.2(8) . . ?
F3 C1 C2 117.8(7) . . ?
F11 C23 F10 103.3(8) . . ?
F11 C23 F12 103.7(8) . . ?
F10 C23 F12 103.7(7) . . ?
F11 C23 C22 116.2(7) . . ?
F10 C23 C22 116.4(7) . . ?
F12 C23 C22 111.9(8) . . ?
C53 N9 C61 106.2(6) . . ?
C53 N9 C57 111.7(5) . . ?
C61 N9 C57 110.1(5) . . ?
C53 N9 C49 111.0(5) . . ?
C61 N9 C49 111.2(5) . . ?
C57 N9 C49 106.7(5) . . ?
C58 C57 N9 115.0(6) . . ?
C58 C57 H57B 108.5 . . ?
N9 C57 H57B 108.5 . . ?
C58 C57 H57A 108.5 . . ?
N9 C57 H57A 108.5 . . ?
H57B C57 H57A 107.5 . . ?
C59 C58 C57 111.8(7) . . ?
C59 C58 H58A 109.3 . . ?
C57 C58 H58A 109.3 . . ?
C59 C58 H58B 109.3 . . ?
C57 C58 H58B 109.3 . . ?
H58A C58 H58B 107.9 . . ?
C58 C59 C60 112.3(8) . . ?
C58 C59 H59A 109.1 . . ?
C60 C59 H59A 109.1 . . ?
C58 C59 H59B 109.1 . . ?
C60 C59 H59B 109.1 . . ?
H59A C59 H59B 107.9 . . ?
C59 C60 H60C 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60C C60 H60B 109.5 . . ?
C59 C60 H60A 109.5 . . ?
H60C C60 H60A 109.5 . . ?
H60B C60 H60A 109.5 . . ?
C62 C61 N9 115.6(6) . . ?
C62 C61 H61A 107.9 . . ?
N9 C61 H61A 110.6 . . ?
C62 C61 H61B 106.5 . . ?
N9 C61 H61B 112.0 . . ?
H61A C61 H61B 103.5 . . ?
C61 C62 C63 105.8(7) . . ?
C61 C62 H62A 110.6 . . ?
C63 C62 H62A 110.6 . . ?
C61 C62 H62B 110.6 . . ?
C63 C62 H62B 110.6 . . ?
H62A C62 H62B 108.7 . . ?
C64 C63 C62 107.2(7) . . ?
C64 C63 H11K 110.3 . . ?
C62 C63 H11K 110.3 . . ?
C64 C63 H11L 110.3 . . ?
C62 C63 H11L 110.3 . . ?
H11K C63 H11L 108.5 . . ?
N9 C53 C54 113.5(6) . . ?
N9 C53 H53A 108.9 . . ?
C54 C53 H53A 108.9 . . ?
N9 C53 H53B 108.9 . . ?
C54 C53 H53B 108.9 . . ?
H53A C53 H53B 107.7 . . ?
C52 C51 C50 113.9(7) . . ?
C52 C51 H51B 108.8 . . ?
C50 C51 H51B 108.8 . . ?
C52 C51 H51A 108.8 . . ?
C50 C51 H51A 108.8 . . ?
H51B C51 H51A 107.7 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52A 109.5 . . ?
H52B C52 H52A 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
C55 C54 C53 102.8(7) . . ?
C55 C54 H54A 111.2 . . ?
C53 C54 H54A 111.2 . . ?
C55 C54 H54B 111.2 . . ?
C53 C54 H54B 111.2 . . ?
H54A C54 H54B 109.1 . . ?
C50 C49 N9 117.1(5) . . ?
C50 C49 H49A 108.0 . . ?
N9 C49 H49A 108.0 . . ?
C50 C49 H49B 108.0 . . ?
N9 C49 H49B 108.0 . . ?
H49A C49 H49B 107.3 . . ?
C49 C50 C51 108.6(6) . . ?
C49 C50 H50A 110.0 . . ?
C51 C50 H50A 110.0 . . ?
C49 C50 H50B 110.0 . . ?
C51 C50 H50B 110.0 . . ?
H50A C50 H50B 108.3 . . ?
C54 C55 C56 112.7(10) . . ?
C54 C55 H55A 109.0 . . ?
C56 C55 H55A 109.0 . . ?
C54 C55 H55B 109.0 . . ?
C56 C55 H55B 109.0 . . ?
H55A C55 H55B 107.8 . . ?
C63 C64 H19K 109.5 . . ?
C63 C64 H19L 109.5 . . ?
H19K C64 H19L 109.5 . . ?
C63 C64 H19M 109.5 . . ?
H19K C64 H19M 109.5 . . ?
H19L C64 H19M 109.5 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O8 S1 O7 109.2(3) . . ?
O8 S1 O5 109.6(2) . . ?
O7 S1 O5 111.3(2) . . ?
O8 S1 O6 109.3(3) . . ?
O7 S1 O6 108.9(2) . . ?
O5 S1 O6 108.5(2) . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_opda-dicf3-TBACl-2a
_database_code_depnum_ccdc_archive 'CCDC 1525836'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, C16 H36 N, Cl'
_chemical_formula_sum            'C40 H50 Cl F12 N5 O2'
_chemical_formula_weight         896.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   17.6943(9)
_cell_length_b                   14.5220(10)
_cell_length_c                   18.0327(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.309(6)
_cell_angle_gamma                90
_cell_volume                     4509.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3341
_cell_measurement_theta_min      3.6340
_cell_measurement_theta_max      23.4000

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   0.949
_exptl_transmission_factor_max   0.964
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.173
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19062
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.036
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7932
_reflns_number_gt                4585
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0880P)²+2.4810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7932
_refine_ls_number_parameters     595
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29248(14) 0.17931(17) 0.38008(16) 0.0730(8) Uani 1 1 d . . . A 4
O2 O 0.66172(15) 0.29489(18) 0.52223(15) 0.0727(7) Uani 1 1 d . . . B 4
N2 N 0.41851(15) 0.13324(18) 0.40016(16) 0.0549(7) Uani 1 1 d . . . C 4
H2N H 0.4499 0.0883 0.4157 0.066 Uiso 1 1 calc R U . C 4
N4 N 0.63260(16) 0.1759(2) 0.59453(16) 0.0586(8) Uani 1 1 d . . . D 4
H4N H 0.5949 0.1411 0.5999 0.070 Uiso 1 1 calc R U . D 4
N1 N 0.33302(15) 0.04803(18) 0.44768(17) 0.0576(8) Uani 1 1 d . . . E 4
H1N H 0.3741 0.0183 0.4696 0.069 Uiso 1 1 calc R U . E 4
F1C F 0.9024(2) 0.3392(2) 0.7199(3) 0.1189(13) Uani 0.8 1 d D . P F 1
N3 N 0.54737(16) 0.2152(2) 0.48449(16) 0.0592(8) Uani 1 1 d . . . . .
H3N H 0.5193 0.1747 0.5003 0.071 Uiso 1 1 calc R U . . .
C16 C 0.34384(19) 0.1247(2) 0.40664(19) 0.0516(8) Uani 1 1 d . . . . .
F1A F 0.9257(3) 0.2498(6) 0.6354(3) 0.156(2) Uani 0.8 1 d D . P F 1
C10 C 0.51513(19) 0.2532(2) 0.41257(19) 0.0518(8) Uani 1 1 d . . . . .
F23B F 0.2677(3) -0.2028(3) 0.6085(3) 0.1102(11) Uani 0.88 1 d D . P G 1
N5 N 0.24767(18) 0.4405(2) 0.36358(19) 0.0670(8) Uani 1 1 d . . . . .
C9 C 0.6175(2) 0.2339(2) 0.53289(19) 0.0530(8) Uani 1 1 d . . . . .
C15 C 0.44798(18) 0.2119(2) 0.36921(19) 0.0498(8) Uani 1 1 d . . . . .
F23C F 0.1542(6) -0.2351(6) 0.5557(5) 0.201(5) Uani 0.88 1 d D . P G 1
C17 C 0.26259(18) 0.0135(2) 0.4574(2) 0.0531(8) Uani 1 1 d . . . . .
C7 C 0.70178(19) 0.1666(2) 0.6495(2) 0.0552(9) Uani 1 1 d . . . . .
F1B F 0.97186(19) 0.2231(3) 0.7500(4) 0.1378(18) Uani 0.8 1 d D . P F 1
F20C F 0.0385(4) 0.0134(10) 0.3037(3) 0.184(3) Uani 0.8 1 d D . P H 1
C11 C 0.5467(2) 0.3282(3) 0.3819(2) 0.0641(10) Uani 1 1 d . . . . .
H11 H 0.5916 0.3564 0.4097 0.077 Uiso 1 1 calc R U . . .
F23A F 0.1744(5) -0.1358(6) 0.6399(4) 0.171(4) Uani 0.88 1 d D . P G 1
F20B F -0.01344(19) 0.0004(7) 0.3932(4) 0.159(2) Uani 0.8 1 d D . P H 1
C12 C 0.5115(2) 0.3608(3) 0.3100(2) 0.0681(10) Uani 1 1 d . . . . .
H12 H 0.5326 0.4110 0.2900 0.082 Uiso 1 1 calc R U . . .
C24 C 0.2642(2) -0.0539(2) 0.5123(2) 0.0589(9) Uani 1 1 d . . . . .
H24 H 0.3115 -0.0722 0.5431 0.071 Uiso 1 1 calc R U . . .
C13 C 0.4456(2) 0.3195(3) 0.2681(2) 0.0655(10) Uani 1 1 d . . . . .
H13 H 0.4223 0.3417 0.2199 0.079 Uiso 1 1 calc R U . . .
C14 C 0.4143(2) 0.2452(2) 0.2978(2) 0.0600(9) Uani 1 1 d . . . . .
H14 H 0.3698 0.2171 0.2692 0.072 Uiso 1 1 calc R U . . .
C8 C 0.7695(2) 0.2137(3) 0.6477(2) 0.0602(9) Uani 1 1 d . . . . .
H8 H 0.7707 0.2554 0.6088 0.072 Uiso 1 1 calc R U . . .
C25 C 0.3131(2) 0.3963(3) 0.4227(2) 0.0732(11) Uani 1 1 d . . . . .
H25A H 0.2945 0.3381 0.4381 0.088 Uiso 1 1 calc R U . . .
H25B H 0.3555 0.3827 0.3986 0.088 Uiso 1 1 calc R U . . .
C18 C 0.1913(2) 0.0410(3) 0.4130(2) 0.0649(10) Uani 1 1 d . . . . .
H18 H 0.1888 0.0863 0.3760 0.078 Uiso 1 1 calc R U . . .
C6 C 0.7020(2) 0.1043(3) 0.7075(2) 0.0642(10) Uani 1 1 d . . . . .
H6 H 0.6568 0.0723 0.7088 0.077 Uiso 1 1 calc R U . . .
C2 C 0.8357(2) 0.1977(3) 0.7050(2) 0.0666(10) Uani 1 1 d . . . . .
C19 C 0.1241(2) 0.0006(3) 0.4240(3) 0.0721(11) Uani 1 1 d . . . . .
C22 C 0.1963(2) -0.0941(3) 0.5215(2) 0.0678(10) Uani 1 1 d . . . . .
F20A F 0.0387(4) 0.1196(4) 0.3785(8) 0.218(5) Uani 0.8 1 d D . P H 1
C21 C 0.1254(2) -0.0665(3) 0.4777(3) 0.0782(12) Uani 1 1 d . . . . .
H21 H 0.0795 -0.0928 0.4845 0.094 Uiso 1 1 calc R U . . .
C37 C 0.2734(2) 0.5314(3) 0.3371(3) 0.0733(11) Uani 1 1 d . . . . .
H37A H 0.2298 0.5588 0.3014 0.088 Uiso 1 1 calc R U . . .
H37B H 0.2873 0.5722 0.3807 0.088 Uiso 1 1 calc R U . . .
C29 C 0.2285(2) 0.3719(3) 0.2979(2) 0.0736(11) Uani 1 1 d . . . . .
H29A H 0.2745 0.3633 0.2780 0.088 Uiso 1 1 calc R U . . .
H29B H 0.2164 0.3131 0.3179 0.088 Uiso 1 1 calc R U . . .
C4 C 0.7679(3) 0.0893(3) 0.7629(2) 0.0754(11) Uani 1 1 d . . . . .
C33 C 0.1771(2) 0.4599(3) 0.3955(3) 0.0850(13) Uani 1 1 d . . . . .
H33A H 0.1919 0.5048 0.4360 0.102 Uiso 1 1 calc R U . . .
H33B H 0.1378 0.4881 0.3556 0.102 Uiso 1 1 calc R U . . .
C3 C 0.8355(3) 0.1364(3) 0.7626(2) 0.0829(13) Uani 1 1 d . . . . .
H3A H 0.8801 0.1267 0.8008 0.099 Uiso 1 1 calc R U . . .
C38 C 0.3409(3) 0.5260(3) 0.2997(3) 0.0936(14) Uani 1 1 d . . . . .
H38A H 0.3826 0.4910 0.3318 0.112 Uiso 1 1 calc R U . . .
H38B H 0.3250 0.4941 0.2513 0.112 Uiso 1 1 calc R U . . .
C1 C 0.9078(3) 0.2519(4) 0.7020(3) 0.0899(14) Uani 1 1 d D . . . .
F5C F 0.7023(6) -0.0247(10) 0.8226(6) 0.192(4) Uani 0.65 1 d D . P I 1
C26 C 0.3448(3) 0.4529(3) 0.4936(3) 0.0983(16) Uani 1 1 d . . . . .
H26A H 0.3048 0.4610 0.5219 0.118 Uiso 1 1 calc R U . . .
H26B H 0.3601 0.5132 0.4793 0.118 Uiso 1 1 calc R U . . .
C27 C 0.4153(3) 0.4041(4) 0.5440(3) 0.1092(18) Uani 1 1 d . . . . .
H27A H 0.4535 0.3927 0.5142 0.131 Uiso 1 1 calc R U . . .
H27B H 0.4388 0.4445 0.5858 0.131 Uiso 1 1 calc R U . . .
C30 C 0.1619(3) 0.3984(3) 0.2325(3) 0.1039(17) Uani 1 1 d . . . . .
H30A H 0.1726 0.4576 0.2121 0.125 Uiso 1 1 calc R U . . .
H30B H 0.1146 0.4040 0.2506 0.125 Uiso 1 1 calc R U . . .
C20 C 0.0479(3) 0.0329(4) 0.3739(4) 0.1110(19) Uani 1 1 d D . . . .
C5 C 0.7666(4) 0.0186(7) 0.8236(4) 0.136(3) Uani 1 1 d D . . . .
C40 C 0.4301(3) 0.6176(4) 0.2415(3) 0.1152(18) Uani 1 1 d D . . . .
H40A H 0.4789 0.5985 0.2732 0.173 Uiso 1 1 d R U . . .
H40B H 0.4353 0.6783 0.2222 0.173 Uiso 1 1 d R U . . .
H40C H 0.4150 0.5754 0.1997 0.173 Uiso 1 1 d R U . . .
C39 C 0.3696(3) 0.6190(3) 0.2865(3) 0.1006(15) Uani 1 1 d D . . . .
H39A H 0.3908 0.6480 0.3353 0.121 Uiso 1 1 calc R U . . .
H39B H 0.3262 0.6562 0.2598 0.121 Uiso 1 1 calc R U . . .
C23 C 0.1978(3) -0.1663(4) 0.5803(3) 0.0980(16) Uani 1 1 d D . . . .
C34 C 0.1408(3) 0.3794(4) 0.4263(4) 0.1176(18) Uani 1 1 d . . . . .
H34A H 0.1771 0.3540 0.4702 0.141 Uiso 1 1 calc R U . . .
H34B H 0.1283 0.3317 0.3878 0.141 Uiso 1 1 calc R U . . .
C35 C 0.0659(4) 0.4113(5) 0.4496(4) 0.143(2) Uani 1 1 d D . . . .
H35A H 0.0792 0.4597 0.4873 0.172 Uiso 1 1 calc R U . . .
H35B H 0.0305 0.4370 0.4053 0.172 Uiso 1 1 calc R U . . .
C31 C 0.1514(4) 0.3259(5) 0.1706(4) 0.132(2) Uani 1 1 d D . . . .
H31A H 0.1515 0.2656 0.1937 0.158 Uiso 1 1 calc R U . . .
H31B H 0.1012 0.3346 0.1359 0.158 Uiso 1 1 calc R U . . .
C28 C 0.3952(4) 0.3156(4) 0.5755(3) 0.138(2) Uani 1 1 d . . . . .
H28A H 0.3493 0.3229 0.5949 0.207 Uiso 1 1 d R U . . .
H28B H 0.4374 0.2956 0.6158 0.207 Uiso 1 1 d R U . . .
H28C H 0.3857 0.2704 0.5355 0.207 Uiso 1 1 d R U . . .
F5B F 0.7848(10) 0.0441(9) 0.8923(4) 0.216(6) Uani 0.65 1 d D . P I 1
C36 C 0.0257(5) 0.3361(6) 0.4812(5) 0.208(4) Uani 1 1 d D . . . .
H36A H 0.0592 0.3136 0.5272 0.312 Uiso 1 1 d R U . . .
H36B H 0.0137 0.2869 0.4448 0.312 Uiso 1 1 d R U . . .
H36C H -0.0214 0.3592 0.4920 0.312 Uiso 1 1 d R U . . .
C32 C 0.2118(5) 0.3285(8) 0.1271(5) 0.212(4) Uani 1 1 d D . . . .
H32A H 0.2015 0.3795 0.0923 0.318 Uiso 1 1 d R U . . .
H32B H 0.2116 0.2723 0.0990 0.318 Uiso 1 1 d R U . . .
H32C H 0.2616 0.3366 0.1613 0.318 Uiso 1 1 d R U . . .
Cl1 Cl 0.48231(5) 0.05269(6) 0.59325(5) 0.0553(3) Uani 1 1 d . . . . .
F5A F 0.8186(8) -0.0435(8) 0.8289(9) 0.211(4) Uani 0.65 1 d D . P I 1
F5D F 0.7171(17) 0.0541(16) 0.8605(14) 0.211(4) Uani 0.35 1 d D . P I 2
F5E F 0.752(2) -0.0595(12) 0.7913(7) 0.216(6) Uani 0.35 1 d D . P I 2
F5F F 0.8303(11) 0.032(2) 0.8747(11) 0.192(4) Uani 0.35 1 d D . P I 2
F1E F 0.8955(9) 0.3176(16) 0.6495(15) 0.1378(18) Uani 0.2 1 d D . P F 2
F1F F 0.9566(10) 0.1986(10) 0.6797(17) 0.1189(13) Uani 0.2 1 d D . P F 2
F1D F 0.9427(12) 0.270(2) 0.7718(9) 0.156(2) Uani 0.2 1 d D . P F 2
F20F F 0.0605(11) 0.092(3) 0.3249(19) 0.159(2) Uani 0.2 1 d D . P H 2
F20E F 0.014(2) 0.085(3) 0.4125(13) 0.184(3) Uani 0.2 1 d D . P H 2
F20D F 0.0101(17) -0.0386(13) 0.345(3) 0.218(5) Uani 0.2 1 d D . P H 2
F23D F 0.200(3) -0.2475(15) 0.5514(19) 0.14(3) Uani 0.12 1 d D . P G 2
F23E F 0.1240(11) -0.181(2) 0.580(3) 0.124(17) Uani 0.12 1 d D . P G 2
F23F F 0.227(5) -0.136(3) 0.6493(15) 0.25(4) Uani 0.12 1 d D . P G 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
O1 C16 1.218(4) . ?
O2 C9 1.226(4) . ?
N2 C16 1.359(4) . ?
N2 C15 1.422(4) . ?
N4 C9 1.371(4) . ?
N4 C7 1.393(4) . ?
N1 C16 1.375(4) . ?
N1 C17 1.391(4) . ?
F1C C1 1.318(5) . ?
N3 C9 1.369(4) . ?
N3 C10 1.404(4) . ?
F1A C1 1.311(6) . ?
C10 C11 1.396(5) . ?
C10 C15 1.398(4) . ?
F23B C23 1.334(6) . ?
N5 C37 1.509(5) . ?
N5 C33 1.516(5) . ?
N5 C25 1.524(5) . ?
N5 C29 1.525(5) . ?
C15 C14 1.377(5) . ?
F23C C23 1.277(7) . ?
C17 C18 1.388(5) . ?
C17 C24 1.388(5) . ?
C7 C6 1.383(5) . ?
C7 C8 1.387(5) . ?
F1B C1 1.325(5) . ?
F20C C20 1.269(7) . ?
C11 C12 1.386(5) . ?
F23A C23 1.315(7) . ?
F20B C20 1.303(6) . ?
C12 C13 1.372(5) . ?
C24 C22 1.379(5) . ?
C13 C14 1.378(5) . ?
C8 C2 1.391(5) . ?
C25 C26 1.515(6) . ?
C18 C19 1.380(5) . ?
C6 C4 1.368(5) . ?
C2 C3 1.369(6) . ?
C2 C1 1.510(6) . ?
C19 C21 1.370(6) . ?
C19 C20 1.515(7) . ?
C22 C21 1.380(6) . ?
C22 C23 1.487(6) . ?
F20A C20 1.275(7) . ?
C37 C38 1.503(6) . ?
C29 C30 1.512(5) . ?
C4 C3 1.379(6) . ?
C4 C5 1.504(8) . ?
C33 C34 1.500(6) . ?
C38 C39 1.481(6) . ?
C1 F1F 1.290(13) . ?
C1 F1D 1.297(13) . ?
C1 F1E 1.326(13) . ?
F5C C5 1.296(8) . ?
C26 C27 1.537(6) . ?
C27 C28 1.481(7) . ?
C30 C31 1.514(7) . ?
C20 F20E 1.267(15) . ?
C20 F20D 1.280(15) . ?
C20 F20F 1.283(16) . ?
C5 F5B 1.261(8) . ?
C5 F5E 1.274(13) . ?
C5 F5A 1.277(9) . ?
C5 F5F 1.296(13) . ?
C5 F5D 1.321(14) . ?
C40 C39 1.484(6) . ?
C23 F23D 1.294(16) . ?
C23 F23F 1.312(16) . ?
C23 F23E 1.321(15) . ?
C34 C35 1.551(7) . ?
C35 C36 1.486(7) . ?
C31 C32 1.465(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N2 C15 124.0(3) . . ?
C9 N4 C7 127.7(3) . . ?
C16 N1 C17 126.8(3) . . ?
C9 N3 C10 128.8(3) . . ?
O1 C16 N2 124.0(3) . . ?
O1 C16 N1 123.7(3) . . ?
N2 C16 N1 112.3(3) . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 N3 123.9(3) . . ?
C15 C10 N3 117.4(3) . . ?
C37 N5 C33 107.0(3) . . ?
C37 N5 C25 110.7(3) . . ?
C33 N5 C25 111.8(3) . . ?
C37 N5 C29 110.8(3) . . ?
C33 N5 C29 111.2(3) . . ?
C25 N5 C29 105.4(3) . . ?
O2 C9 N3 124.1(3) . . ?
O2 C9 N4 123.9(3) . . ?
N3 C9 N4 112.0(3) . . ?
C14 C15 C10 120.2(3) . . ?
C14 C15 N2 122.0(3) . . ?
C10 C15 N2 117.8(3) . . ?
C18 C17 C24 118.8(3) . . ?
C18 C17 N1 123.0(3) . . ?
C24 C17 N1 118.2(3) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 N4 116.8(3) . . ?
C8 C7 N4 123.9(3) . . ?
C12 C11 C10 120.1(3) . . ?
C13 C12 C11 120.5(4) . . ?
C22 C24 C17 120.6(3) . . ?
C12 C13 C14 119.7(3) . . ?
C15 C14 C13 120.8(3) . . ?
C7 C8 C2 119.0(4) . . ?
C26 C25 N5 115.9(3) . . ?
C19 C18 C17 119.5(4) . . ?
C4 C6 C7 120.7(4) . . ?
C3 C2 C8 121.6(4) . . ?
C3 C2 C1 121.0(4) . . ?
C8 C2 C1 117.4(4) . . ?
C21 C19 C18 122.0(4) . . ?
C21 C19 C20 120.6(4) . . ?
C18 C19 C20 117.4(4) . . ?
C24 C22 C21 120.7(4) . . ?
C24 C22 C23 120.7(4) . . ?
C21 C22 C23 118.5(4) . . ?
C19 C21 C22 118.4(4) . . ?
C38 C37 N5 115.2(3) . . ?
C30 C29 N5 115.7(3) . . ?
C6 C4 C3 120.8(4) . . ?
C6 C4 C5 119.1(4) . . ?
C3 C4 C5 120.0(4) . . ?
C34 C33 N5 117.1(4) . . ?
C2 C3 C4 118.6(4) . . ?
C39 C38 C37 111.2(4) . . ?
F1F C1 F1D 102.9(15) . . ?
F1A C1 F1C 107.1(6) . . ?
F1A C1 F1B 103.9(5) . . ?
F1C C1 F1B 104.0(4) . . ?
F1F C1 F1E 102.8(15) . . ?
F1D C1 F1E 120.5(18) . . ?
F1F C1 C2 109.3(8) . . ?
F1D C1 C2 106.8(9) . . ?
F1A C1 C2 113.9(4) . . ?
F1C C1 C2 112.5(4) . . ?
F1B C1 C2 114.5(4) . . ?
F1E C1 C2 113.5(8) . . ?
C25 C26 C27 110.0(4) . . ?
C28 C27 C26 113.1(5) . . ?
C29 C30 C31 109.8(4) . . ?
F20C C20 F20A 107.2(9) . . ?
F20E C20 F20D 116(3) . . ?
F20E C20 F20F 99(2) . . ?
F20D C20 F20F 115(3) . . ?
F20C C20 F20B 105.1(6) . . ?
F20A C20 F20B 102.3(7) . . ?
F20E C20 C19 108.9(13) . . ?
F20C C20 C19 114.9(5) . . ?
F20A C20 C19 112.1(5) . . ?
F20D C20 C19 107.5(12) . . ?
F20F C20 C19 110.2(10) . . ?
F20B C20 C19 114.2(6) . . ?
F5B C5 F5A 96.8(9) . . ?
F5B C5 F5C 100.4(9) . . ?
F5A C5 F5C 105.9(10) . . ?
F5E C5 F5F 120.8(19) . . ?
F5E C5 F5D 119.4(18) . . ?
F5F C5 F5D 98.7(18) . . ?
F5B C5 C4 118.1(8) . . ?
F5E C5 C4 108.1(8) . . ?
F5A C5 C4 113.9(6) . . ?
F5C C5 C4 118.8(5) . . ?
F5F C5 C4 104.9(8) . . ?
F5D C5 C4 102.9(9) . . ?
C38 C39 C40 113.0(4) . . ?
F23D C23 F23F 130(3) . . ?
F23C C23 F23A 105.6(7) . . ?
F23D C23 F23E 89(3) . . ?
F23F C23 F23E 103(4) . . ?
F23C C23 F23B 104.8(7) . . ?
F23A C23 F23B 105.1(6) . . ?
F23C C23 C22 113.2(5) . . ?
F23D C23 C22 110.7(17) . . ?
F23F C23 C22 112(2) . . ?
F23A C23 C22 112.8(6) . . ?
F23E C23 C22 104.8(14) . . ?
F23B C23 C22 114.5(4) . . ?
C33 C34 C35 109.4(5) . . ?
C36 C35 C34 113.5(6) . . ?
C32 C31 C30 113.3(7) . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045

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

data_opda-dicf3-nco-TBAF-1
_database_code_depnum_ccdc_archive 'CCDC 1525835'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, C16 H36 N, F, H2O'
_chemical_formula_sum            'C40 H52 F13 N5 O3'
_chemical_formula_weight         897.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   14.9024(10)
_cell_length_b                   18.280(2)
_cell_length_c                   16.8119(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.476(6)
_cell_angle_gamma                90
_cell_volume                     4578.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2312
_cell_measurement_theta_min      3.5210
_cell_measurement_theta_max      19.7100

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   0.969
_exptl_transmission_factor_max   0.979
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.118
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD and area dector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19533
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             8040
_reflns_number_gt                2939
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0470P)²+2.7660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8040
_refine_ls_number_parameters     682
_refine_ls_number_restraints     185
_refine_ls_R_factor_all          0.2164
_refine_ls_R_factor_gt           0.0976
_refine_ls_wR_factor_ref         0.2454
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.003

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
C17A C 0.2082(5) 0.7302(6) 0.5202(8) 0.096(6) Uani 0.5 1 d G U P A 1
C18A C 0.2761(8) 0.6781(4) 0.5203(9) 0.112(5) Uani 0.5 1 d G U P A 1
H18A H 0.2622 0.6290 0.5125 0.134 Uiso 0.5 1 calc R U P A 1
C19A C 0.3650(7) 0.6995(6) 0.5319(8) 0.133(5) Uani 0.5 1 d DG U P A 1
C21A C 0.3859(5) 0.7729(7) 0.5436(8) 0.138(7) Uani 0.5 1 d G U P A 1
H21A H 0.4454 0.7871 0.5514 0.165 Uiso 0.5 1 calc R U P A 1
C22A C 0.3179(8) 0.8249(5) 0.5436(8) 0.141(6) Uani 0.5 1 d DG U P A 1
C24A C 0.2290(7) 0.8036(5) 0.5319(7) 0.102(4) Uani 0.5 1 d G U P A 1
H24A H 0.1836 0.8384 0.5318 0.122 Uiso 0.5 1 calc R U P A 1
C1A C -0.2082(7) 0.2894(6) 0.2489(8) 0.127(13) Uani 0.5 1 d D . P B 1
F1A F -0.1231(9) 0.2840(14) 0.2742(11) 0.164(8) Uani 0.5 1 d D . P B 1
F2A F -0.1988(19) 0.2718(12) 0.1728(7) 0.184(9) Uani 0.5 1 d D . P B 1
F3A F -0.2566(9) 0.2367(6) 0.2815(8) 0.147(4) Uani 0.5 1 d D . P B 1
C20A C 0.4302(9) 0.6370(8) 0.5286(7) 0.134(9) Uani 0.5 1 d D . P A 1
F7A F 0.4060(10) 0.5670(7) 0.5309(11) 0.209(7) Uani 0.5 1 d D . P A 1
F8A F 0.4872(10) 0.6655(18) 0.4775(11) 0.36(2) Uani 0.5 1 d D . P A 1
F9A F 0.4825(11) 0.6315(12) 0.5936(9) 0.252(8) Uani 0.5 1 d D . P A 1
C40A C 0.6353(15) 0.5160(11) 0.6064(11) 0.263(14) Uani 0.5 1 d D . P C 1
H40A H 0.5808 0.5129 0.6355 0.394 Uiso 0.5 1 calc R U P C 1
H40B H 0.6293 0.4875 0.5587 0.394 Uiso 0.5 1 calc R U P C 1
H40C H 0.6465 0.5662 0.5928 0.394 Uiso 0.5 1 calc R U P C 1
C1B C -0.2002(11) 0.2957(8) 0.2364(9) 0.139(15) Uani 0.5 1 d D . P B 2
F1B F -0.2560(11) 0.2494(10) 0.1994(17) 0.203(9) Uani 0.5 1 d D . P B 2
F2B F -0.1592(19) 0.2658(14) 0.2996(10) 0.197(11) Uani 0.5 1 d D . P B 2
F3B F -0.1376(10) 0.3009(11) 0.1818(13) 0.169(7) Uani 0.5 1 d D . P B 2
C20B C 0.4221(9) 0.6873(9) 0.5151(9) 0.155(10) Uani 0.5 1 d D . P A 2
F7B F 0.4482(16) 0.6497(12) 0.4521(10) 0.272(12) Uani 0.5 1 d D . P A 2
F8B F 0.4927(8) 0.7093(10) 0.5587(16) 0.287(11) Uani 0.5 1 d D . P A 2
F9B F 0.4036(13) 0.6261(12) 0.5541(19) 0.280(14) Uani 0.5 1 d D . P A 2
C40B C 0.6815(12) 0.4176(8) 0.6783(8) 0.174(8) Uani 0.5 1 d D . P C 2
H40D H 0.7299 0.3910 0.7035 0.261 Uiso 0.5 1 calc R U P C 2
H40E H 0.6606 0.3917 0.6317 0.261 Uiso 0.5 1 calc R U P C 2
H40F H 0.6332 0.4224 0.7147 0.261 Uiso 0.5 1 calc R U P C 2
C19B C 0.3421(6) 0.7339(6) 0.5195(8) 0.133(5) Uani 0.5 1 d DG U P A 2
C18B C 0.2558(7) 0.7058(4) 0.5111(8) 0.085(4) Uani 0.5 1 d DG U P A 2
H18B H 0.2471 0.6556 0.5061 0.102 Uiso 0.5 1 calc R U P A 2
C17B C 0.1823(5) 0.7527(5) 0.5102(8) 0.083(5) Uani 0.5 1 d DG U P A 2
C24B C 0.1952(5) 0.8277(4) 0.5177(7) 0.094(4) Uani 0.5 1 d DG U P A 2
H24B H 0.1461 0.8590 0.5171 0.113 Uiso 0.5 1 calc R U P A 2
C22B C 0.2816(6) 0.8558(4) 0.5261(7) 0.140(8) Uani 0.5 1 d DG . P A 2
C21B C 0.3550(4) 0.8089(6) 0.5270(8) 0.139(7) Uani 0.5 1 d DG U P A 2
H21B H 0.4128 0.8278 0.5327 0.166 Uiso 0.5 1 calc R U P A 2
N2 N -0.1852(3) 0.6167(3) 0.4759(2) 0.0810(12) Uani 1 1 d . . . . .
H2N H -0.1477 0.5893 0.5017 0.097 Uiso 1 1 calc R U . . .
N3 N -0.0435(3) 0.7108(3) 0.5158(2) 0.0865(13) Uani 1 1 d . . . . .
H3N H -0.0348 0.6643 0.5146 0.104 Uiso 1 1 calc R U . . .
C10 C -0.2030(3) 0.6888(3) 0.5042(3) 0.0717(14) Uani 1 1 d . . . . .
N4 N 0.1070(4) 0.7146(3) 0.5085(3) 0.113(2) Uani 1 1 d D . . . .
H4NA H 0.0965 0.6693 0.4980 0.135 Uiso 0.5 1 calc R U P A 1
H4NB H 0.109(9) 0.6706(14) 0.527(4) 0.135 Uiso 0.5 1 d D U P D 2
O1 O -0.2752(3) 0.6291(2) 0.3650(2) 0.1050(13) Uani 1 1 d . . . . .
N1 N -0.2111(3) 0.5191(3) 0.3935(2) 0.0847(13) Uani 1 1 d . . . . .
H1N H -0.1746 0.4971 0.4259 0.102 Uiso 1 1 calc R U . . .
N5 N 0.8113(3) 0.6495(3) 0.7766(3) 0.1013(16) Uani 1 1 d . . . . .
C15 C -0.1329(4) 0.7353(4) 0.5228(3) 0.0779(15) Uani 1 1 d . . . . .
C7 C -0.2479(3) 0.4777(3) 0.3309(3) 0.0797(15) Uani 1 1 d . . . . .
C11 C -0.2901(4) 0.7114(3) 0.5133(3) 0.0863(16) Uani 1 1 d . . . . .
H11 H -0.3367 0.6789 0.5019 0.104 Uiso 1 1 calc R U . . .
C9 C -0.2275(3) 0.5908(3) 0.4079(3) 0.0798(15) Uani 1 1 d . . . . .
F5 F -0.4691(3) 0.4338(3) 0.1279(3) 0.194(2) Uani 1 1 d D . . . .
F6 F -0.4188(4) 0.5368(3) 0.1355(4) 0.218(3) Uani 1 1 d D . . . .
C6 C -0.3221(3) 0.4995(3) 0.2851(3) 0.0876(16) Uani 1 1 d . . . . .
H6 H -0.3489 0.5445 0.2946 0.105 Uiso 1 1 calc R U . . .
C37 C 0.7865(5) 0.5996(4) 0.7065(3) 0.112(2) Uani 1 1 d . . . . .
H37A H 0.7512 0.6275 0.6679 0.134 Uiso 1 1 calc R U . . .
H37B H 0.8413 0.5847 0.6810 0.134 Uiso 1 1 calc R U . . .
C14 C -0.1530(5) 0.8057(4) 0.5504(3) 0.0923(18) Uani 1 1 d . . . . .
H14 H -0.1067 0.8379 0.5638 0.111 Uiso 1 1 calc R U . . .
O2 O 0.0267(4) 0.8212(4) 0.5059(4) 0.169(3) Uani 1 1 d . . . . .
C2 C -0.2457(4) 0.3653(4) 0.2558(4) 0.0957(18) Uani 1 1 d D . . . .
C31 C 0.9499(5) 0.8272(4) 0.7576(4) 0.124(2) Uani 1 1 d . . . . .
H31A H 0.9884 0.8077 0.7171 0.149 Uiso 1 1 calc R U . . .
H31B H 0.9030 0.8556 0.7311 0.149 Uiso 1 1 calc R U . . .
C30 C 0.9077(4) 0.7646(4) 0.8018(3) 0.107(2) Uani 1 1 d . . . . .
H30A H 0.8620 0.7832 0.8365 0.129 Uiso 1 1 calc R U . . .
H30B H 0.9531 0.7400 0.8345 0.129 Uiso 1 1 calc R U . . .
C8 C -0.2100(4) 0.4099(4) 0.3148(3) 0.0931(17) Uani 1 1 d . . . . .
H8 H -0.1598 0.3943 0.3442 0.112 Uiso 1 1 calc R U . . .
C33 C 0.8647(4) 0.6077(4) 0.8413(3) 0.119(2) Uani 1 1 d . . . . .
H33A H 0.8754 0.6404 0.8860 0.143 Uiso 1 1 calc R U . . .
H33B H 0.8278 0.5678 0.8598 0.143 Uiso 1 1 calc R U . . .
C13 C -0.2409(5) 0.8273(4) 0.5580(3) 0.106(2) Uani 1 1 d . . . . .
H13 H -0.2535 0.8741 0.5763 0.127 Uiso 1 1 calc R U . . .
C34 C 0.9543(5) 0.5765(4) 0.8168(3) 0.144(3) Uani 1 1 d . . . . .
H34A H 0.9956 0.6159 0.8053 0.172 Uiso 1 1 calc R U . . .
H34B H 0.9463 0.5469 0.7693 0.172 Uiso 1 1 calc R U . . .
C4 C -0.3562(4) 0.4548(4) 0.2257(3) 0.0937(18) Uani 1 1 d . . . . .
C12 C -0.3098(4) 0.7807(4) 0.5387(4) 0.1017(19) Uani 1 1 d . . . . .
H12 H -0.3691 0.7958 0.5428 0.122 Uiso 1 1 calc R U . . .
C29 C 0.8660(4) 0.7108(4) 0.7427(3) 0.0999(19) Uani 1 1 d . . . . .
H29A H 0.8277 0.7381 0.7057 0.120 Uiso 1 1 calc R U . . .
H29B H 0.9138 0.6894 0.7123 0.120 Uiso 1 1 calc R U . . .
C16 C 0.0301(5) 0.7548(5) 0.5106(4) 0.112(3) Uani 1 1 d . . . . .
C26 C 0.6620(4) 0.7189(4) 0.7624(3) 0.109(2) Uani 1 1 d . . . . .
H26A H 0.6445 0.6875 0.7181 0.131 Uiso 1 1 calc R U . . .
H26B H 0.6900 0.7624 0.7411 0.131 Uiso 1 1 calc R U . . .
C25 C 0.7278(4) 0.6794(4) 0.8160(3) 0.109(2) Uani 1 1 d . . . . .
H25A H 0.6969 0.6389 0.8406 0.131 Uiso 1 1 calc R U . . .
H25B H 0.7469 0.7126 0.8581 0.131 Uiso 1 1 calc R U . . .
C32 C 1.0043(4) 0.8768(4) 0.8119(4) 0.147(3) Uani 1 1 d . . . . .
H32A H 0.9647 0.9054 0.8436 0.220 Uiso 1 1 calc R U . . .
H32B H 1.0403 0.9088 0.7806 0.220 Uiso 1 1 calc R U . . .
H32C H 1.0426 0.8478 0.8462 0.220 Uiso 1 1 calc R U . . .
C27 C 0.5796(4) 0.7404(4) 0.8078(4) 0.131(2) Uani 1 1 d . . . . .
H27A H 0.5528 0.6965 0.8293 0.157 Uiso 1 1 calc R U . . .
H27B H 0.5982 0.7711 0.8523 0.157 Uiso 1 1 calc R U . . .
C3 C -0.3197(4) 0.3873(4) 0.2102(3) 0.103(2) Uani 1 1 d . . . . .
H3A H -0.3439 0.3573 0.1704 0.124 Uiso 1 1 calc R U . . .
C5 C -0.4372(6) 0.4809(6) 0.1793(5) 0.145(3) Uani 1 1 d D . . . .
F4 F -0.5010(3) 0.4964(5) 0.2219(4) 0.302(5) Uani 1 1 d D . . . .
C36 C 1.0886(6) 0.5082(5) 0.8732(5) 0.194(4) Uani 1 1 d . . . . .
H36A H 1.0930 0.4822 0.8238 0.291 Uiso 1 1 calc R U . . .
H36B H 1.1092 0.4774 0.9162 0.291 Uiso 1 1 calc R U . . .
H36C H 1.1251 0.5514 0.8717 0.291 Uiso 1 1 calc R U . . .
C38 C 0.7350(6) 0.5324(4) 0.7278(4) 0.151(3) Uani 1 1 d . . . . .
H38A H 0.7706 0.5033 0.7650 0.181 Uiso 1 1 calc R U . . .
H38B H 0.6804 0.5467 0.7538 0.181 Uiso 1 1 calc R U . . .
C28 C 0.5107(5) 0.7798(5) 0.7599(5) 0.189(4) Uani 1 1 d . . . . .
H28A H 0.5323 0.8277 0.7472 0.284 Uiso 1 1 calc R U . . .
H28B H 0.4569 0.7840 0.7897 0.284 Uiso 1 1 calc R U . . .
H28C H 0.4980 0.7532 0.7116 0.284 Uiso 1 1 calc R U . . .
C35 C 0.9926(6) 0.5294(4) 0.8856(4) 0.161(3) Uani 1 1 d . . . . .
H35A H 0.9887 0.5565 0.9350 0.193 Uiso 1 1 calc R U . . .
H35B H 0.9565 0.4855 0.8903 0.193 Uiso 1 1 calc R U . . .
F13 F 0.0978(2) 0.5693(2) 0.51648(19) 0.1367(14) Uani 1 1 d . . . . .
C23A C 0.3619(8) 0.8999(6) 0.5598(8) 0.161(7) Uani 0.33 1 d D U P A 1
F10A F 0.4151(11) 0.9564(8) 0.5450(13) 0.259(5) Uani 0.33 1 d D . P A 1
F11A F 0.3448(11) 0.9000(10) 0.6370(8) 0.210(8) Uani 0.33 1 d D . P A 1
F12A F 0.2849(10) 0.9213(16) 0.5254(16) 0.468(12) Uani 0.33 1 d D . P A 1
C23B C 0.3124(5) 0.9332(4) 0.5382(6) 0.161(7) Uani 0.67 1 d D U P A 2
F10B F 0.2926(7) 0.9726(5) 0.4737(6) 0.259(5) Uani 0.67 1 d D . P A 2
F11B F 0.2640(9) 0.9614(6) 0.5959(7) 0.329(8) Uani 0.67 1 d D . P A 2
F12B F 0.4004(6) 0.9304(7) 0.5531(10) 0.468(12) Uani 0.67 1 d D . P A 2
O3 O 0.0576(2) 0.4586(3) 0.4199(2) 0.1384(18) Uani 1 1 d . . . . .
H3OB H 0.0095 0.4419 0.4390 0.208 Uiso 1 1 d R U . . .
H3OA H 0.0603 0.5026 0.4362 0.208 Uiso 1 1 d R U . . .
C39 C 0.7116(8) 0.4874(5) 0.6565(5) 0.175(4) Uani 1 1 d D . . . .
H39 H 0.7637 0.4861 0.6231 0.210 Uiso 1 1 d R U . C .
H39A H 0.6992 0.4377 0.6731 0.210 Uiso 0.5 1 d R U P C 1
H39B H 0.6651 0.5117 0.6249 0.210 Uiso 0.5 1 d R U P C 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
C17A C18A 1.3900 . ?
C17A C24A 1.3900 . ?
C17A N4 1.542(9) . ?
C18A C19A 1.3900 . ?
C19A C21A 1.3900 . ?
C19A C20A 1.501(15) . ?
C21A C22A 1.3900 . ?
C22A C24A 1.3900 . ?
C22A C23A 1.5406(11) . ?
C22A F12A 1.85(3) . ?
C1A F3A 1.3299(10) . ?
C1A F2A 1.3299(10) . ?
C1A F1A 1.3300(11) . ?
C1A C2 1.503(12) . ?
C20A F9A 1.3300(11) . ?
C20A F7A 1.3301(11) . ?
C20A F8A 1.3301(11) . ?
C40A C39 1.493(17) . ?
C1B F1B 1.3298(10) . ?
C1B F2B 1.3299(10) . ?
C1B F3B 1.3299(11) . ?
C1B C2 1.483(14) . ?
C20B F8B 1.3298(11) . ?
C20B F9B 1.3298(11) . ?
C20B F7B 1.3299(11) . ?
C20B C19B 1.468(14) . ?
C40B C39 1.405(13) . ?
C19B C18B 1.3900 . ?
C19B C21B 1.3900 . ?
C18B C17B 1.3900 . ?
C17B N4 1.321(7) . ?
C17B C24B 1.3900 . ?
C24B C22B 1.3900 . ?
C22B C21B 1.3900 . ?
C22B C23B 1.4989(11) . ?
N2 C9 1.376(6) . ?
N2 C10 1.428(6) . ?
N3 C16 1.364(7) . ?
N3 C15 1.413(6) . ?
C10 C11 1.373(6) . ?
C10 C15 1.377(6) . ?
N4 C16 1.363(9) . ?
O1 C9 1.220(6) . ?
N1 C9 1.356(6) . ?
N1 C7 1.397(6) . ?
N5 C29 1.506(7) . ?
N5 C25 1.526(6) . ?
N5 C37 1.529(7) . ?
N5 C33 1.534(6) . ?
C15 C14 1.402(7) . ?
C7 C6 1.390(6) . ?
C7 C8 1.392(7) . ?
C11 C12 1.373(7) . ?
F5 C5 1.300(8) . ?
F6 C5 1.293(8) . ?
C6 C4 1.377(7) . ?
C37 C38 1.496(8) . ?
C14 C13 1.379(7) . ?
O2 C16 1.217(9) . ?
C2 C8 1.379(7) . ?
C2 C3 1.386(8) . ?
C31 C32 1.508(8) . ?
C31 C30 1.511(8) . ?
C30 C29 1.520(7) . ?
C33 C34 1.519(7) . ?
C13 C12 1.365(7) . ?
C34 C35 1.539(8) . ?
C4 C3 1.377(8) . ?
C4 C5 1.498(9) . ?
C26 C25 1.500(7) . ?
C26 C27 1.514(7) . ?
C27 C28 1.476(8) . ?
C5 F4 1.239(8) . ?
C36 C35 1.503(9) . ?
C38 C39 1.487(9) . ?
C23A F11A 1.3299(11) . ?
C23A F10A 1.3301(11) . ?
C23A F12A 1.3305(11) . ?
C23B F11B 1.3287(10) . ?
C23B F10B 1.3288(10) . ?
C23B F12B 1.3293(11) . ?

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
C18A C17A C24A 120.0 . . ?
C18A C17A N4 125.7(8) . . ?
C24A C17A N4 114.3(8) . . ?
C17A C18A C19A 120.0 . . ?
C18A C19A C21A 120.0 . . ?
C18A C19A C20A 113.3(10) . . ?
C21A C19A C20A 126.6(10) . . ?
C19A C21A C22A 120.0 . . ?
C24A C22A C21A 120.0 . . ?
C24A C22A C23A 132.4(9) . . ?
C21A C22A C23A 107.6(9) . . ?
C24A C22A F12A 89.7(7) . . ?
C21A C22A F12A 147.3(9) . . ?
C23A C22A F12A 45.0(6) . . ?
C22A C24A C17A 120.0 . . ?
F3A C1A F2A 107.0(14) . . ?
F3A C1A F1A 109.7(15) . . ?
F2A C1A F1A 99.6(13) . . ?
F3A C1A C2 115.5(9) . . ?
F2A C1A C2 110.2(12) . . ?
F1A C1A C2 113.4(14) . . ?
F9A C20A F7A 93.3(17) . . ?
F9A C20A F8A 100.9(17) . . ?
F7A C20A F8A 125(2) . . ?
F9A C20A C19A 113.2(13) . . ?
F7A C20A C19A 123.7(12) . . ?
F8A C20A C19A 98.7(16) . . ?
F1B C1B F2B 112(2) . . ?
F1B C1B F3B 99.4(13) . . ?
F2B C1B F3B 105.4(18) . . ?
F1B C1B C2 111.5(13) . . ?
F2B C1B C2 112.4(14) . . ?
F3B C1B C2 115.1(14) . . ?
F8B C20B F9B 98.8(19) . . ?
F8B C20B F7B 110.5(16) . . ?
F9B C20B F7B 91.5(18) . . ?
F8B C20B C19B 115.4(13) . . ?
F9B C20B C19B 106.6(14) . . ?
F7B C20B C19B 126.6(16) . . ?
C18B C19B C21B 120.0 . . ?
C18B C19B C20B 122.0(10) . . ?
C21B C19B C20B 117.8(10) . . ?
C19B C18B C17B 120.0 . . ?
N4 C17B C24B 129.6(7) . . ?
N4 C17B C18B 110.1(7) . . ?
C24B C17B C18B 120.0 . . ?
C17B C24B C22B 120.0 . . ?
C24B C22B C21B 120.0 . . ?
C24B C22B C23B 130.0(7) . . ?
C21B C22B C23B 110.0(7) . . ?
C22B C21B C19B 120.0 . . ?
C9 N2 C10 120.6(4) . . ?
C16 N3 C15 125.4(6) . . ?
C11 C10 C15 120.2(6) . . ?
C11 C10 N2 119.9(5) . . ?
C15 C10 N2 119.9(5) . . ?
C17B N4 C16 115.4(7) . . ?
C16 N4 C17A 135.7(7) . . ?
C9 N1 C7 126.0(5) . . ?
C29 N5 C25 110.7(5) . . ?
C29 N5 C37 105.9(4) . . ?
C25 N5 C37 111.4(5) . . ?
C29 N5 C33 111.3(5) . . ?
C25 N5 C33 106.6(4) . . ?
C37 N5 C33 111.1(5) . . ?
C10 C15 C14 118.3(5) . . ?
C10 C15 N3 119.8(6) . . ?
C14 C15 N3 121.9(5) . . ?
C6 C7 C8 117.9(5) . . ?
C6 C7 N1 123.6(5) . . ?
C8 C7 N1 118.4(5) . . ?
C12 C11 C10 121.5(6) . . ?
O1 C9 N1 123.7(5) . . ?
O1 C9 N2 122.7(6) . . ?
N1 C9 N2 113.6(5) . . ?
C4 C6 C7 120.4(6) . . ?
C38 C37 N5 114.9(5) . . ?
C13 C14 C15 120.3(6) . . ?
C8 C2 C3 120.9(6) . . ?
C8 C2 C1B 119.6(8) . . ?
C3 C2 C1B 119.2(8) . . ?
C8 C2 C1A 117.6(7) . . ?
C3 C2 C1A 121.1(8) . . ?
C32 C31 C30 112.4(6) . . ?
C31 C30 C29 109.6(5) . . ?
C2 C8 C7 121.0(6) . . ?
C34 C33 N5 116.0(4) . . ?
C12 C13 C14 120.7(6) . . ?
C33 C34 C35 108.5(5) . . ?
C6 C4 C3 121.9(5) . . ?
C6 C4 C5 117.8(6) . . ?
C3 C4 C5 120.2(6) . . ?
C13 C12 C11 119.0(6) . . ?
N5 C29 C30 116.7(5) . . ?
O2 C16 N4 124.8(7) . . ?
O2 C16 N3 124.0(9) . . ?
N4 C16 N3 111.2(8) . . ?
C25 C26 C27 110.4(5) . . ?
C26 C25 N5 116.1(5) . . ?
C28 C27 C26 114.4(7) . . ?
C4 C3 C2 117.8(6) . . ?
F4 C5 F6 109.0(10) . . ?
F4 C5 F5 105.3(8) . . ?
F6 C5 F5 102.9(7) . . ?
F4 C5 C4 113.1(7) . . ?
F6 C5 C4 111.6(7) . . ?
F5 C5 C4 114.3(8) . . ?
C39 C38 C37 111.8(6) . . ?
C36 C35 C34 112.1(6) . . ?
F11A C23A F10A 108.1(9) . . ?
F11A C23A F12A 103.8(11) . . ?
F10A C23A F12A 101.7(9) . . ?
F11A C23A C22A 94.8(11) . . ?
F10A C23A C22A 155.7(14) . . ?
F12A C23A C22A 80.0(14) . . ?
C23A F12A C22A 55.0(8) . . ?
F11B C23B F10B 105.8(8) . . ?
F11B C23B F12B 115.4(9) . . ?
F10B C23B F12B 111.8(7) . . ?
F11B C23B C22B 107.1(8) . . ?
F10B C23B C22B 109.9(8) . . ?
F12B C23B C22B 106.7(7) . . ?
C40B C39 C38 111.2(9) . . ?
C38 C39 C40A 114.9(12) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_opda-dicf3-TEACl-2b
_database_code_depnum_ccdc_archive 'CCDC 1525837'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, C8 H20 N, Cl'
_chemical_formula_sum            'C32 H34 Cl F12 N5 O2'
_chemical_formula_weight         784.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.0555(9)
_cell_length_b                   13.4392(13)
_cell_length_c                   14.8575(13)
_cell_angle_alpha                77.996(8)
_cell_angle_beta                 87.728(7)
_cell_angle_gamma                70.382(8)
_cell_volume                     1848.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3336
_cell_measurement_theta_min      3.4690
_cell_measurement_theta_max      24.2490

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   0.947
_exptl_transmission_factor_max   0.963
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealead tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12746
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.116
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6486
_reflns_number_gt                3800
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0640P)²+2.6710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6486
_refine_ls_number_parameters     587
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0871
_refine_ls_wR_factor_ref         0.2353
_refine_ls_wR_factor_gt          0.2054
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.004

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
F4A F 0.5419(8) 0.7704(8) -0.0421(4) 0.137(3) Uani 0.6 1 d D . P A 1
C20 C 0.8134(9) 0.3557(8) 0.9189(5) 0.119(3) Uani 1 1 d D . . . .
F10A F 0.741(3) 0.3060(19) 0.973(3) 0.191(12) Uani 0.5 1 d D . P B 1
F11A F 0.718(4) 0.425(3) 0.8605(13) 0.230(16) Uani 0.5 1 d D . P B 1
F12A F 0.8629(19) 0.402(2) 0.971(2) 0.187(11) Uani 0.5 1 d D . P B 1
C5 C 0.6588(8) 0.7002(6) 0.0009(5) 0.125(3) Uani 1 1 d D . . . .
F5A F 0.6362(17) 0.6138(8) -0.0175(8) 0.198(6) Uani 0.6 1 d D . P A 1
F6A F 0.7759(13) 0.7116(15) -0.0312(6) 0.210(7) Uani 0.6 1 d D . P A 1
F10B F 0.6927(19) 0.342(3) 0.922(3) 0.192(12) Uani 0.5 1 d D . P B 2
F11B F 0.786(3) 0.4553(12) 0.8731(18) 0.168(12) Uani 0.5 1 d D . P B 2
F12B F 0.830(3) 0.354(3) 1.0054(12) 0.245(18) Uani 0.5 1 d D . P B 2
Cl1 Cl 0.84176(13) 0.45802(10) 0.52461(8) 0.0639(4) Uani 1 1 d . . . . .
O2 O 0.9865(4) 0.4063(3) 0.2132(2) 0.0730(10) Uani 1 1 d . . . . .
O1 O 1.2470(4) 0.1012(3) 0.6278(3) 0.0942(12) Uani 1 1 d . . . . .
N2 N 1.1048(4) 0.3902(3) 0.3464(2) 0.0618(10) Uani 1 1 d . . . . .
H2N H 1.1138 0.4251 0.3868 0.074 Uiso 1 1 calc R U . . .
N1 N 0.9003(4) 0.5297(3) 0.3042(2) 0.0630(10) Uani 1 1 d . . . . .
H1N H 0.9133 0.5445 0.3560 0.076 Uiso 1 1 calc R U . . .
N4 N 1.0619(4) 0.2464(3) 0.6523(3) 0.0702(11) Uani 1 1 d . . . . .
H4N H 0.9982 0.3036 0.6234 0.084 Uiso 1 1 calc R U . . .
N3 N 1.1542(4) 0.2470(3) 0.5108(3) 0.0717(12) Uani 1 1 d . . . . .
H3N H 1.0953 0.3119 0.4999 0.086 Uiso 1 1 calc R U . . .
C10 C 1.2023(5) 0.2848(4) 0.3501(3) 0.0566(11) Uani 1 1 d . . . . .
F1 F 0.4549(5) 0.8093(4) 0.3661(3) 0.1365(15) Uani 1 1 d . . . . .
C11 C 1.2661(5) 0.2519(4) 0.2721(3) 0.0706(13) Uani 1 1 d . . . . .
H11 H 1.2462 0.2999 0.2155 0.085 Uiso 1 1 calc R U . . .
C9 C 0.9968(5) 0.4392(4) 0.2815(3) 0.0567(11) Uani 1 1 d . . . . .
N5 N 0.7233(6) 0.2505(5) 0.3397(4) 0.0962(16) Uani 1 1 d . . . . .
C16 C 1.1620(5) 0.1905(4) 0.5992(3) 0.0646(12) Uani 1 1 d . . . . .
C7 C 0.7818(5) 0.6000(4) 0.2493(3) 0.0582(11) Uani 1 1 d . . . . .
F8A F 1.2149(14) 0.0091(11) 1.0459(4) 0.251(6) Uani 0.8 1 d D . P C 1
C8 C 0.6665(5) 0.6577(4) 0.2920(3) 0.0668(13) Uani 1 1 d . . . . .
H8 H 0.6677 0.6482 0.3559 0.080 Uiso 1 1 calc R U . . .
C15 C 1.2307(5) 0.2120(4) 0.4354(3) 0.0609(12) Uani 1 1 d . . . . .
C17 C 1.0511(5) 0.2214(4) 0.7478(3) 0.0649(12) Uani 1 1 d . . . . .
C2 C 0.5487(6) 0.7297(4) 0.2410(4) 0.0745(14) Uani 1 1 d . . . . .
F9A F 1.3640(8) 0.0150(8) 0.9473(8) 0.188(4) Uani 0.8 1 d D . P C 1
F2 F 0.3414(6) 0.7309(6) 0.3164(6) 0.216(4) Uani 1 1 d . . . . .
C6 C 0.7789(6) 0.6144(4) 0.1539(3) 0.0686(13) Uani 1 1 d . . . . .
H6 H 0.8561 0.5759 0.1241 0.082 Uiso 1 1 calc R U . . .
C18 C 0.9403(5) 0.2921(4) 0.7855(4) 0.0708(13) Uani 1 1 d . . . . .
H18 H 0.8750 0.3506 0.7475 0.085 Uiso 1 1 calc R U . . .
C3 C 0.5457(6) 0.7448(4) 0.1458(4) 0.0833(16) Uani 1 1 d . . . . .
H3A H 0.4673 0.7938 0.1110 0.100 Uiso 1 1 calc R U . . .
F7A F 1.2254(11) -0.0702(5) 0.9452(8) 0.200(4) Uani 0.8 1 d D . P C 1
C14 C 1.3295(5) 0.1088(4) 0.4407(4) 0.0751(14) Uani 1 1 d . . . . .
H14 H 1.3530 0.0607 0.4971 0.090 Uiso 1 1 calc R U . . .
C12 C 1.3593(6) 0.1483(5) 0.2779(4) 0.0780(15) Uani 1 1 d . . . . .
H12 H 1.3996 0.1259 0.2249 0.094 Uiso 1 1 calc R U . . .
C4 C 0.6604(6) 0.6863(4) 0.1039(3) 0.0786(15) Uani 1 1 d . . . . .
C19 C 0.9275(6) 0.2749(5) 0.8799(4) 0.0832(16) Uani 1 1 d . . . . .
C24 C 1.1463(6) 0.1327(4) 0.8049(4) 0.0786(15) Uani 1 1 d . . . . .
H24 H 1.2200 0.0840 0.7802 0.094 Uiso 1 1 calc R U . . .
C13 C 1.3924(6) 0.0786(4) 0.3613(4) 0.0807(16) Uani 1 1 d . . . . .
H13 H 1.4580 0.0099 0.3649 0.097 Uiso 1 1 calc R U . . .
C21 C 1.0224(8) 0.1883(6) 0.9372(4) 0.101(2) Uani 1 1 d . . . . .
H21 H 1.0135 0.1777 1.0007 0.121 Uiso 1 1 calc R U . . .
C22 C 1.1297(7) 0.1182(5) 0.8990(4) 0.0941(18) Uani 1 1 d . . . . .
C1 C 0.4250(8) 0.7893(7) 0.2874(6) 0.113(2) Uani 1 1 d . . . . .
C32 C 0.8540(16) 0.1455(9) 0.4923(9) 0.183(5) Uani 1 1 d D . . . .
H32A H 0.8696 0.0874 0.5451 0.274 Uiso 0.5 1 calc R U P D 1
H32B H 0.9398 0.1369 0.4593 0.274 Uiso 0.5 1 calc R U P D 1
H32C H 0.8251 0.2131 0.5119 0.274 Uiso 0.5 1 calc R U P D 1
H32D H 0.84(2) 0.142(18) 0.619(17) 0.274 Uiso 0.5 1 d . U P E 2
H32E H 0.79(3) 0.12(3) 0.51(2) 0.274 Uiso 0.5 1 d . U P F 2
H32F H 0.86(3) 0.09(2) 0.45(2) 0.274 Uiso 0.5 1 d . U P G 2
F3 F 0.3473(8) 0.8768(6) 0.2417(4) 0.263(5) Uani 1 1 d . . . . .
C26 C 0.5335(12) 0.3778(10) 0.4181(10) 0.175(5) Uani 1 1 d D . . . .
H26D H 0.4441 0.3900 0.4473 0.263 Uiso 0.5 1 calc R U P H 2
H26E H 0.6036 0.3763 0.4609 0.263 Uiso 0.5 1 calc R U P H 2
H26F H 0.5254 0.4350 0.3655 0.263 Uiso 0.5 1 calc R U P H 2
H26A H 0.49(3) 0.34(2) 0.393(19) 0.263 Uiso 0.5 1 d . U P I 1
H26B H 0.46(3) 0.42(2) 0.334(17) 0.263 Uiso 0.5 1 d . U P J 1
H26C H 0.52(3) 0.31(2) 0.473(18) 0.263 Uiso 0.5 1 d . U P K 1
C23 C 1.2354(13) 0.0193(8) 0.9590(5) 0.137(3) Uani 1 1 d D . . . .
C28B C 0.638(6) 0.321(3) 0.182(2) 0.26(3) Uani 0.45 1 d D . P L 1
H28A H 0.5918 0.3078 0.1325 0.397 Uiso 0.45 1 calc R U P L 1
H28B H 0.5817 0.3883 0.1972 0.397 Uiso 0.45 1 calc R U P L 1
H28C H 0.7291 0.3238 0.1636 0.397 Uiso 0.45 1 calc R U P L 1
C30B C 0.883(3) 0.135(2) 0.2458(18) 0.155(9) Uani 0.55 1 d . . P M 2
H30A H 0.8919 0.0759 0.2170 0.232 Uiso 0.55 1 calc R U P M 2
H30B H 0.8837 0.1970 0.1997 0.232 Uiso 0.55 1 calc R U P M 2
H30C H 0.9598 0.1160 0.2893 0.232 Uiso 0.55 1 calc R U P M 2
C25A C 0.5785(11) 0.2661(10) 0.3863(8) 0.095(3) Uani 0.55 1 d D . P N 2
H25A H 0.5869 0.2077 0.4390 0.114 Uiso 0.55 1 calc R U P N 2
H25B H 0.5083 0.2666 0.3431 0.114 Uiso 0.55 1 calc R U P N 2
C27A C 0.6962(12) 0.3608(9) 0.2630(9) 0.099(4) Uani 0.55 1 d D . P N 2
H27A H 0.6807 0.4192 0.2954 0.118 Uiso 0.55 1 calc R U P N 2
H27B H 0.7827 0.3545 0.2298 0.118 Uiso 0.55 1 calc R U P N 2
C29A C 0.8997(19) 0.2039(17) 0.3169(13) 0.132(7) Uani 0.45 1 d . . P N 1
H29A H 0.9169 0.2574 0.2673 0.158 Uiso 0.45 1 calc R U P N 1
H29B H 0.9516 0.2029 0.3709 0.158 Uiso 0.45 1 calc R U P N 1
C31A C 0.733(2) 0.1436(14) 0.4267(14) 0.152(10) Uani 0.45 1 d D . P N 1
H31A H 0.6447 0.1536 0.4577 0.183 Uiso 0.45 1 calc R U P N 1
H31B H 0.7605 0.0767 0.4046 0.183 Uiso 0.45 1 calc R U P N 1
C25B C 0.6920(18) 0.3440(13) 0.3731(12) 0.125(6) Uani 0.45 1 d D . P N 1
H25C H 0.6960 0.4024 0.3234 0.151 Uiso 0.45 1 calc R U P N 1
H25D H 0.7627 0.3341 0.4198 0.151 Uiso 0.45 1 calc R U P N 1
C27B C 0.655(3) 0.224(3) 0.2712(19) 0.185(15) Uani 0.45 1 d D . P L 1
H27C H 0.5640 0.2203 0.2911 0.222 Uiso 0.45 1 calc R U P L 1
H27D H 0.7124 0.1555 0.2573 0.222 Uiso 0.45 1 calc R U P L 1
C29B C 0.7475(18) 0.1624(13) 0.2942(13) 0.107(5) Uani 0.55 1 d . . P M 2
H29C H 0.6705 0.1800 0.2500 0.128 Uiso 0.55 1 calc R U P M 2
H29D H 0.7466 0.0991 0.3394 0.128 Uiso 0.55 1 calc R U P M 2
C31B C 0.8283(10) 0.2476(8) 0.4027(7) 0.078(3) Uani 0.55 1 d D . P N 2
H31C H 0.7994 0.3149 0.4242 0.094 Uiso 0.55 1 calc R U P N 2
H31D H 0.9164 0.2407 0.3713 0.094 Uiso 0.55 1 calc R U P N 2
F5B F 0.621(2) 0.8044(10) -0.0366(10) 0.198(6) Uani 0.4 1 d D . P A 2
F6B F 0.596(2) 0.645(2) -0.0309(11) 0.210(7) Uani 0.4 1 d D . P A 2
F4B F 0.7747(14) 0.6581(13) -0.0375(8) 0.137(3) Uani 0.4 1 d D . P A 2
F9B F 1.289(6) 0.057(2) 1.017(3) 0.200(4) Uani 0.2 1 d D . P C 2
F7B F 1.310(7) -0.047(3) 0.9102(17) 0.251(6) Uani 0.2 1 d D . P C 2
F8B F 1.159(3) -0.015(5) 1.021(3) 0.188(4) Uani 0.2 1 d D . P C 2
C28A C 0.581(4) 0.394(2) 0.1950(18) 0.172(12) Uani 0.55 1 d . . P N 2
H28D H 0.5779 0.4600 0.1545 0.259 Uiso 0.55 1 calc R U P N 2
H28E H 0.5954 0.3385 0.1599 0.259 Uiso 0.55 1 calc R U P N 2
H28F H 0.4928 0.4036 0.2258 0.259 Uiso 0.55 1 calc R U P N 2
C30A C 0.966(4) 0.096(3) 0.291(3) 0.190(16) Uani 0.45 1 d . . P N 1
H30D H 1.0643 0.0831 0.2808 0.285 Uiso 0.45 1 calc R U P N 1
H30E H 0.9548 0.0401 0.3400 0.285 Uiso 0.45 1 calc R U P N 1
H30F H 0.9198 0.0949 0.2358 0.285 Uiso 0.45 1 calc R U P N 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4A C5 1.320(8) . ?
C20 F10B 1.287(13) . ?
C20 F11A 1.291(13) . ?
C20 F12B 1.296(12) . ?
C20 F12A 1.295(12) . ?
C20 F10A 1.297(13) . ?
C20 F11B 1.310(13) . ?
C20 C19 1.484(9) . ?
C5 F4B 1.282(13) . ?
C5 F6B 1.289(13) . ?
C5 F6A 1.298(10) . ?
C5 F5B 1.324(12) . ?
C5 F5A 1.337(11) . ?
C5 C4 1.503(9) . ?
O2 C9 1.210(5) . ?
O1 C16 1.215(5) . ?
N2 C9 1.371(5) . ?
N2 C10 1.417(5) . ?
N1 C9 1.373(6) . ?
N1 C7 1.406(5) . ?
N4 C16 1.369(6) . ?
N4 C17 1.398(6) . ?
N3 C16 1.364(6) . ?
N3 C15 1.406(6) . ?
C10 C11 1.383(6) . ?
C10 C15 1.404(6) . ?
F1 C1 1.320(8) . ?
C11 C12 1.381(7) . ?
N5 C25B 1.381(15) . ?
N5 C27B 1.41(2) . ?
N5 C31B 1.424(10) . ?
N5 C29B 1.430(15) . ?
N5 C25A 1.555(12) . ?
N5 C27A 1.619(11) . ?
N5 C31A 1.698(19) . ?
N5 C29A 1.717(19) . ?
C7 C8 1.376(6) . ?
C7 C6 1.390(6) . ?
F8A C23 1.286(9) . ?
C8 C2 1.382(7) . ?
C15 C14 1.397(6) . ?
C17 C18 1.385(7) . ?
C17 C24 1.390(6) . ?
C2 C3 1.387(7) . ?
C2 C1 1.469(9) . ?
F9A C23 1.281(10) . ?
F2 C1 1.334(10) . ?
C6 C4 1.380(7) . ?
C18 C19 1.382(7) . ?
C3 C4 1.368(7) . ?
F7A C23 1.298(10) . ?
C14 C13 1.386(7) . ?
C12 C13 1.365(8) . ?
C19 C21 1.377(8) . ?
C24 C22 1.382(8) . ?
C21 C22 1.365(9) . ?
C22 C23 1.524(10) . ?
C1 F3 1.244(9) . ?
C32 C31A 1.594(16) . ?
C32 C31B 1.658(13) . ?
C26 C25A 1.582(13) . ?
C26 C25B 1.659(15) . ?
C23 F7B 1.284(17) . ?
C23 F8B 1.284(16) . ?
C23 F9B 1.295(17) . ?
C28B C27B 1.618(18) . ?
C30B C29B 1.48(3) . ?
C27A C28A 1.46(3) . ?
C29A C30A 1.51(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F10B C20 F12B 98.9(19) . . ?
F11A C20 F12A 112(2) . . ?
F11A C20 F10A 102.7(19) . . ?
F12A C20 F10A 104.7(19) . . ?
F10B C20 F11B 103.6(19) . . ?
F12B C20 F11B 109(2) . . ?
F10B C20 C19 114.8(15) . . ?
F11A C20 C19 115.7(12) . . ?
F12B C20 C19 115.3(13) . . ?
F12A C20 C19 112.1(11) . . ?
F10A C20 C19 108.6(14) . . ?
F11B C20 C19 114.0(13) . . ?
F4B C5 F6B 92.7(14) . . ?
F6A C5 F4A 115.7(11) . . ?
F4B C5 F5B 104.1(14) . . ?
F6B C5 F5B 117.1(13) . . ?
F6A C5 F5A 113.3(11) . . ?
F4A C5 F5A 94.9(9) . . ?
F4B C5 C4 118.3(7) . . ?
F6B C5 C4 115.0(11) . . ?
F6A C5 C4 110.2(7) . . ?
F4A C5 C4 115.0(7) . . ?
F5B C5 C4 108.9(8) . . ?
F5A C5 C4 106.5(8) . . ?
C9 N2 C10 123.3(4) . . ?
C9 N1 C7 125.2(4) . . ?
C16 N4 C17 127.6(4) . . ?
C16 N3 C15 127.9(4) . . ?
C11 C10 C15 119.9(4) . . ?
C11 C10 N2 121.8(4) . . ?
C15 C10 N2 118.3(4) . . ?
C12 C11 C10 120.4(5) . . ?
O2 C9 N2 124.3(4) . . ?
O2 C9 N1 123.9(4) . . ?
N2 C9 N1 111.8(4) . . ?
C25B N5 C27B 131.3(17) . . ?
C31B N5 C29B 119.3(9) . . ?
C31B N5 C25A 111.0(7) . . ?
C29B N5 C25A 106.4(8) . . ?
C31B N5 C27A 106.2(6) . . ?
C29B N5 C27A 109.0(10) . . ?
C25A N5 C27A 103.8(7) . . ?
C25B N5 C31A 110.6(10) . . ?
C27B N5 C31A 99.4(15) . . ?
C25B N5 C29A 110.1(10) . . ?
C27B N5 C29A 104.7(14) . . ?
C31A N5 C29A 94.2(9) . . ?
O1 C16 N3 124.4(5) . . ?
O1 C16 N4 123.8(5) . . ?
N3 C16 N4 111.8(4) . . ?
C8 C7 C6 119.3(4) . . ?
C8 C7 N1 118.4(4) . . ?
C6 C7 N1 122.2(4) . . ?
C7 C8 C2 120.6(5) . . ?
C14 C15 C10 119.0(4) . . ?
C14 C15 N3 123.6(4) . . ?
C10 C15 N3 117.4(4) . . ?
C18 C17 C24 119.9(5) . . ?
C18 C17 N4 116.5(4) . . ?
C24 C17 N4 123.6(5) . . ?
C8 C2 C3 120.2(5) . . ?
C8 C2 C1 120.2(5) . . ?
C3 C2 C1 119.6(6) . . ?
C4 C6 C7 119.4(5) . . ?
C19 C18 C17 119.4(5) . . ?
C4 C3 C2 118.8(5) . . ?
C13 C14 C15 119.6(5) . . ?
C13 C12 C11 120.0(5) . . ?
C3 C4 C6 121.7(5) . . ?
C3 C4 C5 119.7(5) . . ?
C6 C4 C5 118.6(5) . . ?
C21 C19 C18 121.1(6) . . ?
C21 C19 C20 120.4(6) . . ?
C18 C19 C20 118.4(6) . . ?
C22 C24 C17 118.9(5) . . ?
C12 C13 C14 121.0(5) . . ?
C22 C21 C19 118.8(6) . . ?
C21 C22 C24 121.8(6) . . ?
C21 C22 C23 121.0(6) . . ?
C24 C22 C23 117.2(7) . . ?
F3 C1 F1 106.3(8) . . ?
F3 C1 F2 106.1(8) . . ?
F1 C1 F2 100.4(7) . . ?
F3 C1 C2 116.3(8) . . ?
F1 C1 C2 114.4(6) . . ?
F2 C1 C2 111.8(7) . . ?
F7B C23 F8B 118(4) . . ?
F9A C23 F8A 107.0(12) . . ?
F7B C23 F9B 123(5) . . ?
F8B C23 F9B 92(3) . . ?
F9A C23 F7A 107.8(11) . . ?
F8A C23 F7A 100.7(12) . . ?
F9A C23 C22 113.4(8) . . ?
F7B C23 C22 111.3(16) . . ?
F8B C23 C22 104(2) . . ?
F8A C23 C22 114.8(8) . . ?
F9B C23 C22 105.4(16) . . ?
F7A C23 C22 112.2(8) . . ?
N5 C25A C26 107.3(8) . . ?
C28A C27A N5 119.1(14) . . ?
C30A C29A N5 120.9(19) . . ?
C32 C31A N5 101.6(9) . . ?
N5 C25B C26 112.2(10) . . ?
N5 C27B C28B 105.3(17) . . ?
N5 C29B C30B 114.0(14) . . ?
N5 C31B C32 111.6(7) . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_opda-dicf3-TBAI-4
_database_code_depnum_ccdc_archive 'CCDC 1525839'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, C16 H36 N, I'
_chemical_formula_sum            'C40 H50 F12 I N5 O2'
_chemical_formula_weight         987.75


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.6440(6)
_cell_length_b                   14.9266(6)
_cell_length_c                   18.2352(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.787(3)
_cell_angle_gamma                90
_cell_volume                     4717.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6617
_cell_measurement_theta_min      3.5450
_cell_measurement_theta_max      25.4420

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             2008.0
_exptl_transmission_factor_min   0.795
_exptl_transmission_factor_max   0.852
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.763
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealead tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20609
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.972
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8292
_reflns_number_gt                6099
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0650P)²+2.1900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8292
_refine_ls_number_parameters     591
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002

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
C36A C 0.3601(9) 0.6548(13) 0.4145(7) 0.209(8) Uani 0.55 1 d D U P A 1
H36A H 0.3700 0.5941 0.4309 0.313 Uiso 0.55 1 calc R U P A 1
H36B H 0.3446 0.6892 0.4537 0.313 Uiso 0.55 1 calc R U P A 1
H36C H 0.4061 0.6802 0.4023 0.313 Uiso 0.55 1 calc R U P A 1
C36B C 0.3404(13) 0.7365(13) 0.3220(12) 0.261(14) Uani 0.45 1 d D U P A 2
H36D H 0.3909 0.7172 0.3164 0.391 Uiso 0.45 1 calc R U P A 2
H36E H 0.3450 0.7821 0.3596 0.391 Uiso 0.45 1 calc R U P A 2
H36F H 0.3135 0.7602 0.2754 0.391 Uiso 0.45 1 calc R U P A 2
I1 I 0.95613(2) 0.46332(2) 0.60522(2) 0.06023(12) Uani 1 1 d . . . . .
O2 O 1.15191(17) 0.2096(2) 0.52544(18) 0.0839(9) Uani 1 1 d . . . . .
O1 O 0.78656(16) 0.31693(19) 0.37700(19) 0.0777(9) Uani 1 1 d . . . . .
N4 N 1.12321(18) 0.3286(2) 0.59369(17) 0.0632(8) Uani 1 1 d . . . . .
H4N H 1.0874 0.3666 0.5971 0.076 Uiso 1 1 calc R U . . .
N2 N 0.91139(17) 0.3641(2) 0.40793(17) 0.0564(8) Uani 1 1 d . . . . .
H2N H 0.9407 0.4057 0.4302 0.068 Uiso 1 1 calc R U . . .
N3 N 1.03746(17) 0.2836(2) 0.49150(17) 0.0602(8) Uani 1 1 d . . . . .
H3N H 1.0063 0.3175 0.5098 0.072 Uiso 1 1 calc R U . . .
F23B F 1.3842(3) 0.1597(3) 0.7259(4) 0.1313(17) Uani 0.8 1 d D . P B 1
F23C F 1.4541(3) 0.2716(5) 0.7424(6) 0.175(3) Uani 0.8 1 d D . P B 1
F2 F 0.7101(5) 0.7192(4) 0.5526(4) 0.264(4) Uani 1 1 d . . . . .
C16 C 1.1076(2) 0.2693(3) 0.5355(2) 0.0573(9) Uani 1 1 d . . . . .
C10 C 0.9466(2) 0.2914(2) 0.3766(2) 0.0531(9) Uani 1 1 d . . . . .
N5 N 0.2303(2) 0.5498(2) 0.1479(2) 0.0749(10) Uani 1 1 d . . . . .
N1 N 0.81596(19) 0.4502(2) 0.4380(2) 0.0652(9) Uani 1 1 d . . . . .
H1N H 0.8542 0.4821 0.4597 0.078 Uiso 1 1 calc R U . . .
C9 C 0.8335(2) 0.3717(3) 0.4048(2) 0.0581(10) Uani 1 1 d . . . . .
C15 C 1.0101(2) 0.2496(2) 0.4198(2) 0.0533(9) Uani 1 1 d . . . . .
C17 C 1.1903(2) 0.3351(3) 0.6484(2) 0.0604(10) Uani 1 1 d . . . . .
C11 C 0.9192(2) 0.2645(3) 0.3039(2) 0.0637(10) Uani 1 1 d . . . . .
H11 H 0.8776 0.2939 0.2750 0.076 Uiso 1 1 calc R U . . .
C18 C 1.1889(2) 0.3956(3) 0.7056(2) 0.0699(11) Uani 1 1 d . . . . .
H18 H 1.1446 0.4289 0.7070 0.084 Uiso 1 1 calc R U . . .
C12 C 0.9541(3) 0.1939(3) 0.2744(2) 0.0738(12) Uani 1 1 d . . . . .
H12 H 0.9363 0.1758 0.2254 0.089 Uiso 1 1 calc R U . . .
C14 C 1.0437(2) 0.1773(3) 0.3894(2) 0.0656(10) Uani 1 1 d . . . . .
H14 H 1.0853 0.1472 0.4178 0.079 Uiso 1 1 calc R U . . .
C13 C 1.0149(3) 0.1506(3) 0.3174(2) 0.0722(12) Uani 1 1 d . . . . .
H13 H 1.0373 0.1021 0.2976 0.087 Uiso 1 1 calc R U . . .
C7 C 0.7417(2) 0.4828(3) 0.4396(3) 0.0661(11) Uani 1 1 d . . . . .
C6 C 0.6773(3) 0.4557(3) 0.3897(3) 0.0847(15) Uani 1 1 d . . . . .
H6 H 0.6816 0.4117 0.3547 0.102 Uiso 1 1 calc R U . . .
C24 C 1.2570(2) 0.2871(3) 0.6465(2) 0.0676(11) Uani 1 1 d . . . . .
H24 H 1.2592 0.2476 0.6076 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7343(3) 0.5491(3) 0.4915(3) 0.0782(13) Uani 1 1 d . . . . .
H8 H 0.7774 0.5682 0.5253 0.094 Uiso 1 1 calc R U . . .
C22 C 1.3203(2) 0.2986(3) 0.7034(3) 0.0773(13) Uani 1 1 d . . . . .
C37 C 0.3045(3) 0.5307(4) 0.1201(4) 0.1008(17) Uani 1 1 d . . . . .
H37A H 0.3407 0.5030 0.1603 0.121 Uiso 1 1 calc R U . . .
H37B H 0.2934 0.4873 0.0798 0.121 Uiso 1 1 calc R U . . .
C31 C 0.0993(4) 0.3716(4) 0.2213(4) 0.117(2) Uani 1 1 d . . . . .
H31A H 0.0479 0.3768 0.2325 0.140 Uiso 1 1 calc R U . . .
H31B H 0.0970 0.3297 0.1803 0.140 Uiso 1 1 calc R U . . .
F5C F 0.5290(5) 0.3764(5) 0.3437(9) 0.232(5) Uani 0.67 1 d D . P C 1
C29 C 0.2009(3) 0.4595(3) 0.1713(3) 0.0847(14) Uani 1 1 d . . . . .
H29A H 0.1955 0.4189 0.1291 0.102 Uiso 1 1 calc R U . . .
H29B H 0.2396 0.4346 0.2109 0.102 Uiso 1 1 calc R U . . .
C25 C 0.1703(3) 0.5931(3) 0.0872(3) 0.0772(12) Uani 1 1 d . . . . .
H25A H 0.1243 0.6047 0.1076 0.093 Uiso 1 1 calc R U . . .
H25B H 0.1902 0.6505 0.0746 0.093 Uiso 1 1 calc R U . . .
C19 C 1.2529(3) 0.4062(4) 0.7599(2) 0.0857(14) Uani 1 1 d D . . . .
C26 C 0.1472(4) 0.5394(3) 0.0156(3) 0.0950(16) Uani 1 1 d . . . . .
H26A H 0.1924 0.5282 -0.0062 0.114 Uiso 1 1 calc R U . . .
H26B H 0.1263 0.4820 0.0269 0.114 Uiso 1 1 calc R U . . .
C33 C 0.2437(3) 0.6160(3) 0.2116(3) 0.0871(14) Uani 1 1 d . U . . .
H33A H 0.1945 0.6276 0.2261 0.105 Uiso 1 1 calc R U . . .
H33B H 0.2609 0.6718 0.1930 0.105 Uiso 1 1 calc R U . . .
C30 C 0.1255(3) 0.4632(3) 0.1978(4) 0.0982(17) Uani 1 1 d . . . . .
H30A H 0.0862 0.4870 0.1581 0.118 Uiso 1 1 calc R U . . .
H30B H 0.1303 0.5040 0.2398 0.118 Uiso 1 1 calc R U . . .
F1 F 0.6649(3) 0.6260(4) 0.6156(3) 0.186(2) Uani 1 1 d . . . . .
C4 C 0.6066(3) 0.4935(5) 0.3914(5) 0.109(2) Uani 1 1 d . . . . .
C21 C 1.3192(3) 0.3580(4) 0.7604(3) 0.0948(16) Uani 1 1 d . . . . .
H21 H 1.3620 0.3653 0.7982 0.114 Uiso 1 1 calc R U . . .
C2 C 0.6631(4) 0.5863(4) 0.4927(3) 0.0961(16) Uani 1 1 d . . . . .
C3 C 0.5994(4) 0.5585(5) 0.4429(5) 0.119(2) Uani 1 1 d . . . . .
H3A H 0.5514 0.5836 0.4440 0.143 Uiso 1 1 calc R U . . .
C20 C 1.2495(3) 0.4713(4) 0.8203(3) 0.128(3) Uani 1 1 d D . . . .
C23 C 1.3905(3) 0.2423(5) 0.7020(4) 0.110(2) Uani 1 1 d D . . . .
F3 F 0.5900(4) 0.6952(5) 0.5378(4) 0.264(4) Uani 1 1 d . . . . .
F23A F 1.4074(5) 0.2350(7) 0.6355(4) 0.186(3) Uani 0.8 1 d D . P B 1
C28 C 0.1166(5) 0.6740(4) -0.0696(4) 0.133(2) Uani 1 1 d . . . . .
H28A H 0.1301 0.7164 -0.0298 0.199 Uiso 1 1 calc R U . . .
H28B H 0.0771 0.6988 -0.1075 0.199 Uiso 1 1 calc R U . . .
H28C H 0.1613 0.6606 -0.0907 0.199 Uiso 1 1 calc R U . . .
C27 C 0.0875(4) 0.5897(4) -0.0398(3) 0.1111(19) Uani 1 1 d . . . . .
H27A H 0.0682 0.5503 -0.0815 0.133 Uiso 1 1 calc R U . . .
H27B H 0.0445 0.6047 -0.0159 0.133 Uiso 1 1 calc R U . . .
C38 C 0.3429(4) 0.6097(5) 0.0927(5) 0.139(3) Uani 1 1 d . . . . .
H38A H 0.3553 0.6542 0.1319 0.167 Uiso 1 1 calc R U . . .
H38B H 0.3093 0.6369 0.0504 0.167 Uiso 1 1 calc R U . . .
C32 C 0.1509(5) 0.3375(5) 0.2857(4) 0.143(3) Uani 1 1 d . . . . .
H32A H 0.2015 0.3306 0.2742 0.215 Uiso 1 1 calc R U . . .
H32B H 0.1326 0.2805 0.2994 0.215 Uiso 1 1 calc R U . . .
H32C H 0.1532 0.3788 0.3264 0.215 Uiso 1 1 calc R U . . .
F20A F 1.2098(11) 0.5467(7) 0.8040(7) 0.225(7) Uani 0.6 1 d D . P D 1
F20C F 1.3136(4) 0.5074(11) 0.8588(9) 0.199(5) Uani 0.6 1 d D . P D 1
C35 C 0.2953(6) 0.6564(7) 0.3451(4) 0.190(4) Uani 1 1 d D U . . .
H35A H 0.2925 0.7165 0.3246 0.228 Uiso 0.5 1 calc R U P A 1
H35B H 0.2469 0.6451 0.3615 0.228 Uiso 0.5 1 calc R U P A 1
H35C H 0.278(4) 0.691(4) 0.383(2) 0.228 Uiso 0.5 1 d D U P A 2
H35D H 0.277(4) 0.691(4) 0.382(2) 0.228 Uiso 0.5 1 d D U P E 2
C39 C 0.4188(6) 0.5739(6) 0.0690(7) 0.207(4) Uani 1 1 d D . . . .
H39A H 0.4512 0.5451 0.1112 0.248 Uiso 1 1 calc R U . . .
H39B H 0.4057 0.5299 0.0295 0.248 Uiso 1 1 calc R U . . .
C34 C 0.3011(4) 0.5902(5) 0.2814(4) 0.134(2) Uani 1 1 d . U . . .
H34A H 0.3530 0.5911 0.2709 0.160 Uiso 1 1 calc R U . . .
H34B H 0.2903 0.5299 0.2964 0.160 Uiso 1 1 calc R U . . .
C1 C 0.6578(5) 0.6598(7) 0.5471(5) 0.140(3) Uani 1 1 d . . . . .
C40 C 0.4628(7) 0.6522(8) 0.0413(9) 0.309(8) Uani 1 1 d D . . . .
H40A H 0.5148 0.6338 0.0403 0.464 Uiso 1 1 calc R U . . .
H40B H 0.4637 0.7022 0.0745 0.464 Uiso 1 1 calc R U . . .
H40C H 0.4376 0.6692 -0.0080 0.464 Uiso 1 1 calc R U . . .
F20B F 1.2183(11) 0.4358(8) 0.8746(6) 0.213(5) Uani 0.6 1 d D . P D 1
F5A F 0.4732(3) 0.4902(10) 0.3498(8) 0.265(8) Uani 0.67 1 d D . P C 1
C5 C 0.5397(4) 0.4632(5) 0.3329(6) 0.169(5) Uani 1 1 d D . . . .
F5B F 0.5461(7) 0.4821(15) 0.2631(5) 0.277(7) Uani 0.67 1 d D . P C 1
F20D F 1.2808(18) 0.5484(12) 0.8063(12) 0.213(5) Uani 0.4 1 d D . P D 2
F20F F 1.2960(18) 0.4436(13) 0.8813(10) 0.225(7) Uani 0.4 1 d D . P D 2
F20E F 1.1796(7) 0.4921(17) 0.8267(15) 0.199(5) Uani 0.4 1 d D . P D 2
F23F F 1.4147(18) 0.228(3) 0.7748(9) 0.186(3) Uani 0.2 1 d D . P B 2
F23E F 1.4427(12) 0.2929(13) 0.685(2) 0.1313(17) Uani 0.2 1 d D . P B 2
F23D F 1.3808(13) 0.179(2) 0.652(2) 0.175(3) Uani 0.2 1 d D . P B 2
F5E F 0.5044(13) 0.5297(10) 0.2963(10) 0.159(7) Uiso 0.33 1 d D . P C 2
F5D F 0.5503(11) 0.4055(13) 0.2831(9) 0.146(6) Uiso 0.33 1 d D . P C 2
F5F F 0.4867(17) 0.444(3) 0.3706(17) 0.237(14) Uiso 0.33 1 d D . P C 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
C36A C35 1.5392(10) . ?
C36B C35 1.5396(10) . ?
O2 C16 1.221(5) . ?
O1 C9 1.206(4) . ?
N4 C16 1.370(5) . ?
N4 C17 1.402(5) . ?
N2 C9 1.369(5) . ?
N2 C10 1.422(5) . ?
N3 C16 1.360(5) . ?
N3 C15 1.402(4) . ?
F23B C23 1.319(7) . ?
F23C C23 1.297(6) . ?
F2 C1 1.269(10) . ?
C10 C11 1.384(5) . ?
C10 C15 1.392(5) . ?
N5 C33 1.511(6) . ?
N5 C37 1.517(6) . ?
N5 C25 1.525(5) . ?
N5 C29 1.532(5) . ?
N1 C9 1.380(5) . ?
N1 C7 1.404(5) . ?
C15 C14 1.394(5) . ?
C17 C24 1.383(6) . ?
C17 C18 1.383(6) . ?
C11 C12 1.379(6) . ?
C18 C19 1.365(6) . ?
C12 C13 1.367(6) . ?
C14 C13 1.375(5) . ?
C7 C6 1.377(6) . ?
C7 C8 1.391(6) . ?
C6 C4 1.374(7) . ?
C24 C22 1.385(6) . ?
C8 C2 1.377(7) . ?
C22 C21 1.369(7) . ?
C22 C23 1.502(8) . ?
C37 C38 1.492(8) . ?
C31 C32 1.438(9) . ?
C31 C30 1.531(7) . ?
F5C C5 1.3298(10) . ?
C29 C30 1.500(7) . ?
C25 C26 1.521(6) . ?
C19 C21 1.372(7) . ?
C19 C20 1.4794(10) . ?
C26 C27 1.516(7) . ?
C33 C34 1.520(7) . ?
F1 C1 1.332(9) . ?
C4 C3 1.371(10) . ?
C4 C5 1.505(11) . ?
C2 C3 1.371(9) . ?
C2 C1 1.495(10) . ?
C20 F20E 1.297(13) . ?
C20 F20F 1.319(12) . ?
C20 F20D 1.322(13) . ?
C20 F20C 1.3284(10) . ?
C20 F20B 1.3291(10) . ?
C20 F20A 1.3290(10) . ?
C23 F23E 1.271(15) . ?
C23 F23D 1.301(15) . ?
C23 F23A 1.307(8) . ?
C23 F23F 1.333(14) . ?
F3 C1 1.289(8) . ?
C28 C27 1.499(8) . ?
C38 C39 1.574(10) . ?
C35 H35C 0.9598(15) . ?
C35 C34 1.544(10) . ?
C39 C40 1.5391(10) . ?
F5A C5 1.3296(10) . ?
C5 F5D 1.290(13) . ?
C5 F5E 1.290(13) . ?
C5 F5F 1.290(15) . ?
C5 F5B 1.3294(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N4 C17 128.1(3) . . ?
C9 N2 C10 123.8(3) . . ?
C16 N3 C15 127.6(3) . . ?
O2 C16 N3 124.3(4) . . ?
O2 C16 N4 123.1(3) . . ?
N3 C16 N4 112.6(3) . . ?
C11 C10 C15 120.7(4) . . ?
C11 C10 N2 120.5(3) . . ?
C15 C10 N2 118.8(3) . . ?
C33 N5 C37 111.1(4) . . ?
C33 N5 C25 105.6(3) . . ?
C37 N5 C25 111.2(4) . . ?
C33 N5 C29 111.9(4) . . ?
C37 N5 C29 106.6(3) . . ?
C25 N5 C29 110.5(4) . . ?
C9 N1 C7 126.3(3) . . ?
O1 C9 N2 124.5(4) . . ?
O1 C9 N1 124.5(4) . . ?
N2 C9 N1 111.0(3) . . ?
C10 C15 C14 118.7(3) . . ?
C10 C15 N3 117.7(3) . . ?
C14 C15 N3 123.6(3) . . ?
C24 C17 C18 119.5(4) . . ?
C24 C17 N4 123.7(4) . . ?
C18 C17 N4 116.7(4) . . ?
C12 C11 C10 119.6(4) . . ?
C19 C18 C17 119.5(4) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C14 C15 119.7(4) . . ?
C12 C13 C14 121.4(4) . . ?
C6 C7 C8 119.2(4) . . ?
C6 C7 N1 122.8(4) . . ?
C8 C7 N1 117.9(4) . . ?
C4 C6 C7 120.3(6) . . ?
C17 C24 C22 119.2(4) . . ?
C2 C8 C7 119.9(5) . . ?
C21 C22 C24 121.7(5) . . ?
C21 C22 C23 120.2(5) . . ?
C24 C22 C23 118.1(5) . . ?
C38 C37 N5 116.0(4) . . ?
C32 C31 C30 111.5(6) . . ?
C30 C29 N5 115.1(4) . . ?
C26 C25 N5 115.9(4) . . ?
C18 C19 C21 122.2(4) . . ?
C18 C19 C20 118.2(5) . . ?
C21 C19 C20 119.6(5) . . ?
C27 C26 C25 110.6(4) . . ?
N5 C33 C34 117.5(4) . . ?
C29 C30 C31 113.0(4) . . ?
C3 C4 C6 120.4(6) . . ?
C3 C4 C5 122.5(6) . . ?
C6 C4 C5 117.1(7) . . ?
C22 C21 C19 117.9(4) . . ?
C3 C2 C8 120.4(6) . . ?
C3 C2 C1 121.1(6) . . ?
C8 C2 C1 118.5(6) . . ?
C4 C3 C2 119.8(5) . . ?
F20E C20 F20F 116.8(16) . . ?
F20E C20 F20D 104.4(15) . . ?
F20F C20 F20D 102.7(14) . . ?
F20C C20 F20B 101.4(9) . . ?
F20C C20 F20A 97.8(9) . . ?
F20B C20 F20A 103.4(10) . . ?
F20E C20 C19 113.3(8) . . ?
F20F C20 C19 108.4(8) . . ?
F20D C20 C19 110.6(8) . . ?
F20C C20 C19 120.7(6) . . ?
F20B C20 C19 111.9(6) . . ?
F20A C20 C19 118.9(6) . . ?
F23E C23 F23D 106(2) . . ?
F23C C23 F23A 103.5(8) . . ?
F23C C23 F23B 104.1(6) . . ?
F23A C23 F23B 106.0(7) . . ?
F23E C23 F23F 103(2) . . ?
F23D C23 F23F 124(3) . . ?
F23E C23 C22 108.0(11) . . ?
F23C C23 C22 115.5(6) . . ?
F23D C23 C22 114.7(11) . . ?
F23A C23 C22 113.2(5) . . ?
F23B C23 C22 113.4(6) . . ?
F23F C23 C22 100.6(11) . . ?
C28 C27 C26 114.5(6) . . ?
C37 C38 C39 106.7(6) . . ?
H35C C35 C36B 92(5) . . ?
H35C C35 C34 165(5) . . ?
C36A C35 C34 117.8(10) . . ?
C36B C35 C34 100.4(12) . . ?
C40 C39 C38 109.9(8) . . ?
C33 C34 C35 109.9(5) . . ?
F2 C1 F3 111.5(9) . . ?
F2 C1 F1 104.6(9) . . ?
F3 C1 F1 101.5(7) . . ?
F2 C1 C2 115.5(6) . . ?
F3 C1 C2 112.7(8) . . ?
F1 C1 C2 109.7(8) . . ?
F5D C5 F5E 105.6(14) . . ?
F5D C5 F5F 116.4(18) . . ?
F5E C5 F5F 96.6(18) . . ?
F5B C5 F5A 113.3(11) . . ?
F5B C5 F5C 112.9(13) . . ?
F5A C5 F5C 96.0(10) . . ?
F5D C5 C4 120.1(9) . . ?
F5E C5 C4 112.0(11) . . ?
F5F C5 C4 103.8(18) . . ?
F5B C5 C4 114.8(6) . . ?
F5A C5 C4 110.7(7) . . ?
F5C C5 C4 107.6(7) . . ?

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_opda-dicf3-nco-TBBABr-3
_database_code_depnum_ccdc_archive 'CCDC 1525838'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-14 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         'C24 H14 F12 N4 O2, C16 H36 N, Br'
_chemical_formula_sum            'C40 H50 Br F12 N5 O2'
_chemical_formula_weight         940.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   17.5240(10)
_cell_length_b                   14.7884(8)
_cell_length_c                   17.9804(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.090(6)
_cell_angle_gamma                90
_cell_volume                     4572.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3696
_cell_measurement_theta_min      3.5850
_cell_measurement_theta_max      21.4750

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1936.0
_exptl_transmission_factor_min   0.759
_exptl_transmission_factor_max   0.829
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.986
_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   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22061
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8034
_reflns_number_gt                4642
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0880P)²+1.2490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8034
_refine_ls_number_parameters     584
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
C32A C 0.665(2) 0.661(2) 0.5846(15) 0.306(17) Uiso 0.5 1 d D U P A 1
H32A H 0.6487 0.7112 0.5520 0.459 Uiso 0.5 1 calc R U P A 1
H32B H 0.7182 0.6467 0.5840 0.459 Uiso 0.5 1 calc R U P A 1
H32C H 0.6330 0.6091 0.5670 0.459 Uiso 0.5 1 calc R U P A 1
C32B C 0.710(3) 0.7610(15) 0.657(3) 0.59(4) Uiso 0.5 1 d D U P B 2
H32D H 0.7210 0.7874 0.6115 0.891 Uiso 0.5 1 calc R U P B 2
H32E H 0.6624 0.7862 0.6674 0.891 Uiso 0.5 1 calc R U P B 2
H32F H 0.7517 0.7737 0.6986 0.891 Uiso 0.5 1 calc R U P B 2
F23B F 0.5363(7) 0.9946(14) -0.2102(6) 0.252(6) Uani 0.85 1 d D . P C 1
F23A F 0.5384(6) 0.8813(6) -0.1466(13) 0.280(7) Uani 0.85 1 d D . P C 1
C39 C 0.9071(5) 0.5928(5) 1.0372(4) 0.124(3) Uani 1 1 d . . . . .
H39A H 0.9272 0.5531 1.0794 0.148 Uiso 1 1 calc R U . . .
H39B H 0.9494 0.6057 1.0110 0.148 Uiso 1 1 calc R U . . .
Br1 Br 0.96935(3) 0.95279(3) 0.09880(3) 0.0605(2) Uani 1 1 d . . . . .
O2 O 0.7918(2) 0.8200(2) -0.1210(2) 0.0722(10) Uani 1 1 d . . . . .
O1 O 1.1563(2) 0.7051(3) 0.0241(2) 0.0787(11) Uani 1 1 d . . . . .
N3 N 0.9179(2) 0.8666(2) -0.0970(2) 0.0557(10) Uani 1 1 d . . . . .
H3N H 0.9486 0.9099 -0.0787 0.067 Uiso 1 1 calc R U . . .
N1 N 1.1272(2) 0.8251(3) 0.0950(2) 0.0640(11) Uani 1 1 d . . . . .
H1N H 1.0903 0.8616 0.0998 0.077 Uiso 1 1 calc R U . . .
N2 N 1.0430(2) 0.7837(3) -0.0120(2) 0.0612(11) Uani 1 1 d . . . . .
H2N H 1.0133 0.8217 0.0050 0.073 Uiso 1 1 calc R U . . .
N4 N 0.8263(2) 0.9531(2) -0.0569(2) 0.0595(11) Uani 1 1 d . . . . .
H4N H 0.8662 0.9835 -0.0351 0.071 Uiso 1 1 calc R U . . .
F5B F 1.4626(3) 0.7724(6) 0.2446(7) 0.165(3) Uani 0.8 1 d D . P D 1
F9 F 0.6690(4) 1.1316(4) 0.1305(3) 0.172(2) Uani 1 1 d . . . . .
C16 C 0.8406(3) 0.8748(3) -0.0949(3) 0.0542(12) Uani 1 1 d . . . . .
F5A F 1.4151(5) 0.7378(9) 0.1312(4) 0.178(4) Uani 0.8 1 d D . P D 1
F5C F 1.3942(3) 0.6586(3) 0.2219(4) 0.1218(18) Uani 0.8 1 d D . P D 1
F7 F 0.7386(5) 1.2131(4) 0.0804(5) 0.236(4) Uani 1 1 d . . . . .
C6 C 1.2631(3) 0.7838(3) 0.1471(3) 0.0658(14) Uani 1 1 d . . . . .
H6 H 1.2649 0.7429 0.1082 0.079 Uiso 1 1 calc R U . . .
F23C F 0.4818(3) 0.9920(9) -0.1205(6) 0.212(4) Uani 0.85 1 d D . P C 1
C9 C 1.1123(3) 0.7658(3) 0.0343(3) 0.0576(12) Uani 1 1 d . . . . .
C15 C 0.9502(3) 0.7905(3) -0.1278(3) 0.0523(12) Uani 1 1 d . . . . .
N5 N 0.7592(4) 0.5570(3) 0.8515(3) 0.0976(17) Uani 1 1 d . . . . .
C10 C 1.0141(3) 0.7475(3) -0.0840(3) 0.0549(12) Uani 1 1 d . . . . .
C7 C 1.1952(3) 0.8318(3) 0.1488(3) 0.0602(13) Uani 1 1 d . . . . .
C17 C 0.7539(3) 0.9869(3) -0.0506(3) 0.0585(13) Uani 1 1 d . . . . .
C33 C 0.7887(6) 0.4662(4) 0.8239(5) 0.128(3) Uani 1 1 d . . . . .
H33A H 0.7957 0.4238 0.8658 0.154 Uiso 1 1 calc R U . . .
H33B H 0.7483 0.4421 0.7843 0.154 Uiso 1 1 calc R U . . .
C14 C 0.9204(3) 0.7607(4) -0.2004(3) 0.0650(14) Uani 1 1 d . . . . .
H14 H 0.8783 0.7905 -0.2297 0.078 Uiso 1 1 calc R U . . .
C8 C 1.1948(3) 0.8928(4) 0.2078(3) 0.0658(14) Uani 1 1 d . . . . .
H8 H 1.1497 0.9248 0.2104 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7503(4) 1.0534(3) 0.0025(3) 0.0689(15) Uani 1 1 d . . . . .
H18 H 0.7956 1.0720 0.0347 0.083 Uiso 1 1 calc R U . . .
C11 C 1.0457(3) 0.6730(4) -0.1139(3) 0.0699(15) Uani 1 1 d . . . . .
H11 H 1.0875 0.6425 -0.0850 0.084 Uiso 1 1 calc R U . . .
C24 C 0.6860(3) 0.9599(4) -0.0974(3) 0.0734(16) Uani 1 1 d . . . . .
H24 H 0.6871 0.9152 -0.1335 0.088 Uiso 1 1 calc R U . . .
C37 C 0.8209(4) 0.5992(4) 0.9114(4) 0.0878(18) Uani 1 1 d . . . . .
H37A H 0.8023 0.6576 0.9248 0.105 Uiso 1 1 calc R U . . .
H37B H 0.8668 0.6097 0.8899 0.105 Uiso 1 1 calc R U . . .
C13 C 0.9527(4) 0.6871(4) -0.2296(3) 0.0712(15) Uani 1 1 d . . . . .
H13 H 0.9321 0.6670 -0.2783 0.085 Uiso 1 1 calc R U . . .
C4 C 1.3280(3) 0.7968(4) 0.2034(3) 0.0750(16) Uani 1 1 d . . . . .
C19 C 0.6806(4) 1.0926(4) 0.0085(4) 0.0845(18) Uani 1 1 d . . . . .
C29 C 0.7437(4) 0.6248(4) 0.7861(4) 0.104(2) Uani 1 1 d . . . . .
H29A H 0.7296 0.6818 0.8064 0.125 Uiso 1 1 calc R U . . .
H29B H 0.7924 0.6346 0.7692 0.125 Uiso 1 1 calc R U . . .
C12 C 1.0147(4) 0.6438(4) -0.1873(3) 0.0752(16) Uani 1 1 d . . . . .
H12 H 1.0366 0.5944 -0.2074 0.090 Uiso 1 1 calc R U . . .
C2 C 1.2601(4) 0.9057(5) 0.2618(3) 0.0809(17) Uani 1 1 d . . . . .
C38 C 0.8445(5) 0.5437(4) 0.9838(4) 0.114(3) Uani 1 1 d . . . . .
H38A H 0.7998 0.5346 1.0075 0.137 Uiso 1 1 calc R U . . .
H38B H 0.8634 0.4848 0.9718 0.137 Uiso 1 1 calc R U . . .
C40 C 0.8820(6) 0.6791(6) 1.0678(5) 0.150(3) Uani 1 1 d . . . . .
H40A H 0.8665 0.7211 1.0270 0.225 Uiso 1 1 calc R U . . .
H40B H 0.9243 0.7041 1.1037 0.225 Uiso 1 1 calc R U . . .
H40C H 0.8389 0.6676 1.0923 0.225 Uiso 1 1 calc R U . . .
C1 C 1.2569(5) 0.9735(7) 0.3240(4) 0.115(3) Uani 1 1 d D . . . .
F1C F 1.2686(19) 1.0538(6) 0.3018(7) 0.269(9) Uani 0.729(16) 1 d D . P E 1
C26 C 0.6495(5) 0.6163(7) 0.9099(6) 0.153(3) Uani 1 1 d D . . . .
H26A H 0.6362 0.6620 0.8709 0.183 Uiso 1 1 calc R U . . .
H26B H 0.6844 0.6426 0.9529 0.183 Uiso 1 1 calc R U . . .
C3 C 1.3275(4) 0.8575(5) 0.2606(3) 0.0865(18) Uani 1 1 d . . . . .
H3A H 1.3716 0.8662 0.2979 0.104 Uiso 1 1 calc R U . . .
C22 C 0.6158(3) 0.9996(5) -0.0903(4) 0.0904(19) Uani 1 1 d . . . . .
C5 C 1.3998(4) 0.7418(5) 0.1999(4) 0.096(2) Uani 1 1 d D . . . .
C20 C 0.6794(7) 1.1626(7) 0.0662(6) 0.129(3) Uani 1 1 d . . . . .
C25 C 0.6860(5) 0.5359(5) 0.8803(5) 0.127(3) Uani 1 1 d . . . . .
H25A H 0.6486 0.5091 0.8395 0.152 Uiso 1 1 calc R U . . .
H25B H 0.6980 0.4914 0.9205 0.152 Uiso 1 1 calc R U . . .
C21 C 0.6130(4) 1.0660(5) -0.0366(5) 0.095(2) Uani 1 1 d . . . . .
H21 H 0.5659 1.0919 -0.0316 0.114 Uiso 1 1 calc R U . . .
F1B F 1.1968(9) 0.9687(18) 0.3520(12) 0.281(10) Uani 0.729(16) 1 d D . P E 1
F8 F 0.6201(6) 1.2158(6) 0.0500(4) 0.279(5) Uani 1 1 d . . . . .
F1A F 1.3136(10) 0.9680(14) 0.3805(8) 0.230(7) Uani 0.729(16) 1 d D . P E 1
C35 C 0.9044(9) 0.3777(6) 0.7896(8) 0.226(7) Uani 1 1 d D . . . .
H35A H 0.9603 0.3836 0.7950 0.271 Uiso 1 1 calc R U . . .
H35B H 0.8925 0.3360 0.8274 0.271 Uiso 1 1 calc R U . . .
C23 C 0.5448(4) 0.9666(7) -0.1436(7) 0.141(4) Uani 1 1 d D . . . .
C34 C 0.8647(7) 0.4695(6) 0.7933(7) 0.211(6) Uani 1 1 d D . . . .
H34A H 0.8538 0.4954 0.7427 0.253 Uiso 1 1 calc R U . . .
H34B H 0.9008 0.5096 0.8251 0.253 Uiso 1 1 calc R U . . .
C27 C 0.5756(8) 0.5790(10) 0.9340(9) 0.233(7) Uani 1 1 d D . . . .
H27A H 0.5421 0.5513 0.8908 0.280 Uiso 1 1 calc R U . . .
H27B H 0.5899 0.5329 0.9726 0.280 Uiso 1 1 calc R U . . .
C28 C 0.5342(9) 0.6511(12) 0.9634(10) 0.297(9) Uani 1 1 d D . . . .
H28A H 0.4884 0.6272 0.9782 0.445 Uiso 1 1 calc R U . . .
H28B H 0.5672 0.6779 1.0066 0.445 Uiso 1 1 calc R U . . .
H28C H 0.5195 0.6962 0.9249 0.445 Uiso 1 1 calc R U . . .
C36 C 0.8685(11) 0.3513(10) 0.7145(8) 0.351(14) Uani 1 1 d D . . . .
H36A H 0.9060 0.3539 0.6821 0.527 Uiso 1 1 calc R U . . .
H36B H 0.8262 0.3916 0.6957 0.527 Uiso 1 1 calc R U . . .
H36C H 0.8490 0.2907 0.7153 0.527 Uiso 1 1 calc R U . . .
C30 C 0.6819(7) 0.6029(8) 0.7163(5) 0.165(4) Uani 1 1 d D . . . .
H30A H 0.7020 0.5563 0.6873 0.198 Uiso 0.5 1 calc R U P F 1
H30B H 0.6366 0.5784 0.7329 0.198 Uiso 0.5 1 calc R U P F 1
H30C H 0.6369(18) 0.595(15) 0.739(3) 0.198 Uiso 0.5 1 d D U P G 2
H30D H 0.682(12) 0.543(13) 0.703(10) 0.198 Uiso 0.5 1 d . U P H 2
C31B C 0.6563(11) 0.6833(12) 0.6641(9) 0.141(6) Uiso 0.5 1 d D U P A 1
H31A H 0.6025 0.6980 0.6648 0.169 Uiso 0.5 1 calc R U P A 1
H31B H 0.6879 0.7357 0.6819 0.169 Uiso 0.5 1 calc R U P A 1
F1F F 1.3184(11) 1.0203(17) 0.3358(19) 0.128(10) Uiso 0.271(16) 1 d D . P E 2
F1D F 1.2017(11) 1.0305(12) 0.3105(10) 0.082(6) Uiso 0.271(16) 1 d D . P E 2
F1E F 1.2582(19) 0.9313(14) 0.3872(11) 0.111(8) Uiso 0.271(16) 1 d D . P E 2
F5E F 1.4496(15) 0.7922(16) 0.1774(19) 0.116(8) Uiso 0.2 1 d D . P D 2
F5D F 1.4312(18) 0.722(2) 0.2685(10) 0.135(9) Uiso 0.2 1 d D . P D 2
F5F F 1.3896(15) 0.6750(17) 0.1523(17) 0.120(8) Uiso 0.2 1 d D . P D 2
C31A C 0.7007(11) 0.6598(11) 0.6469(9) 0.120(5) Uiso 0.5 1 d D . P B 2
H31C H 0.7484 0.6363 0.6345 0.145 Uiso 0.5 1 calc R U P B 2
H31D H 0.6595 0.6488 0.6035 0.145 Uiso 0.5 1 calc R U P B 2
F23F F 0.5604(16) 0.921(2) -0.1992(13) 0.073(7) Uiso 0.15 1 d D . P C 2
F23D F 0.504(3) 1.036(2) -0.168(3) 0.139(16) Uiso 0.15 1 d D . P C 2
F23E F 0.517(3) 0.901(2) -0.111(2) 0.116(13) Uiso 0.15 1 d D . P C 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
C32A C31B 1.504(17) . ?
C32B C31A 1.512(14) . ?
F23B C23 1.248(10) . ?
F23A C23 1.266(9) . ?
C39 C40 1.490(10) . ?
C39 C38 1.498(10) . ?
O2 C16 1.207(5) . ?
O1 C9 1.220(6) . ?
N3 C16 1.367(6) . ?
N3 C15 1.420(6) . ?
N1 C9 1.385(6) . ?
N1 C7 1.385(6) . ?
N2 C9 1.360(6) . ?
N2 C10 1.403(6) . ?
N4 C17 1.387(6) . ?
N4 C16 1.392(6) . ?
F5B C5 1.313(8) . ?
F9 C20 1.289(9) . ?
F5A C5 1.314(8) . ?
F5C C5 1.301(8) . ?
F7 C20 1.263(11) . ?
C6 C4 1.382(7) . ?
C6 C7 1.392(7) . ?
F23C C23 1.308(9) . ?
C15 C14 1.382(6) . ?
C15 C10 1.391(6) . ?
N5 C37 1.507(8) . ?
N5 C25 1.506(9) . ?
N5 C29 1.529(8) . ?
N5 C33 1.554(8) . ?
C10 C11 1.386(7) . ?
C7 C8 1.394(7) . ?
C17 C24 1.377(7) . ?
C17 C18 1.382(7) . ?
C33 C34 1.536(11) . ?
C14 C13 1.376(7) . ?
C8 C2 1.364(7) . ?
C18 C19 1.375(8) . ?
C11 C12 1.396(7) . ?
C24 C22 1.391(8) . ?
C37 C38 1.527(9) . ?
C13 C12 1.360(7) . ?
C4 C3 1.366(8) . ?
C4 C5 1.510(9) . ?
C19 C21 1.359(9) . ?
C19 C20 1.467(10) . ?
C29 C30 1.527(10) . ?
C2 C3 1.384(8) . ?
C2 C1 1.511(10) . ?
C1 F1B 1.253(9) . ?
C1 F1F 1.264(14) . ?
C1 F1D 1.270(12) . ?
C1 F1A 1.281(10) . ?
C1 F1C 1.281(10) . ?
C1 F1E 1.293(13) . ?
C26 C25 1.496(11) . ?
C26 C27 1.545(12) . ?
C22 C21 1.384(9) . ?
C22 C23 1.500(11) . ?
C5 F5E 1.271(14) . ?
C5 F5D 1.286(15) . ?
C5 F5F 1.296(14) . ?
C20 F8 1.292(10) . ?
C35 C36 1.430(9) . ?
C35 C34 1.532(8) . ?
C23 F23E 1.270(15) . ?
C23 F23F 1.277(14) . ?
C23 F23D 1.277(15) . ?
C27 C28 1.445(12) . ?
C30 C31B 1.527(14) . ?
C30 C31A 1.591(11) . ?

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
C40 C39 C38 114.8(8) . . ?
C16 N3 C15 123.6(4) . . ?
C9 N1 C7 127.0(4) . . ?
C9 N2 C10 127.7(4) . . ?
C17 N4 C16 126.4(4) . . ?
O2 C16 N3 124.2(4) . . ?
O2 C16 N4 124.6(5) . . ?
N3 C16 N4 111.1(4) . . ?
C4 C6 C7 120.0(5) . . ?
O1 C9 N2 124.6(5) . . ?
O1 C9 N1 123.7(5) . . ?
N2 C9 N1 111.7(4) . . ?
C14 C15 C10 120.4(4) . . ?
C14 C15 N3 120.9(4) . . ?
C10 C15 N3 118.7(4) . . ?
C37 N5 C25 112.4(6) . . ?
C37 N5 C29 106.0(4) . . ?
C25 N5 C29 111.3(6) . . ?
C37 N5 C33 110.4(6) . . ?
C25 N5 C33 106.8(6) . . ?
C29 N5 C33 110.0(6) . . ?
C11 C10 C15 118.8(4) . . ?
C11 C10 N2 124.1(5) . . ?
C15 C10 N2 117.2(4) . . ?
N1 C7 C8 116.7(5) . . ?
N1 C7 C6 124.9(5) . . ?
C8 C7 C6 118.4(5) . . ?
C24 C17 C18 118.6(5) . . ?
C24 C17 N4 122.8(5) . . ?
C18 C17 N4 118.5(5) . . ?
C34 C33 N5 116.9(6) . . ?
C13 C14 C15 120.2(5) . . ?
C2 C8 C7 120.5(5) . . ?
C19 C18 C17 121.0(6) . . ?
C10 C11 C12 120.0(5) . . ?
C17 C24 C22 119.8(6) . . ?
N5 C37 C38 115.3(5) . . ?
C12 C13 C14 120.2(5) . . ?
C3 C4 C6 121.3(6) . . ?
C3 C4 C5 120.8(6) . . ?
C6 C4 C5 118.0(6) . . ?
C21 C19 C18 121.0(6) . . ?
C21 C19 C20 119.9(7) . . ?
C18 C19 C20 119.1(8) . . ?
C30 C29 N5 119.1(6) . . ?
C13 C12 C11 120.4(5) . . ?
C8 C2 C3 121.2(6) . . ?
C8 C2 C1 118.3(6) . . ?
C3 C2 C1 120.5(6) . . ?
C39 C38 C37 109.3(6) . . ?
F1F C1 F1D 105.2(16) . . ?
F1B C1 F1A 105.2(12) . . ?
F1B C1 F1C 112.0(16) . . ?
F1A C1 F1C 99.2(12) . . ?
F1F C1 F1E 104.3(18) . . ?
F1D C1 F1E 111.9(14) . . ?
F1B C1 C2 114.4(8) . . ?
F1F C1 C2 109.6(15) . . ?
F1D C1 C2 115.7(9) . . ?
F1A C1 C2 114.3(9) . . ?
F1C C1 C2 110.7(7) . . ?
F1E C1 C2 109.4(13) . . ?
C25 C26 C27 104.8(9) . . ?
C4 C3 C2 118.7(6) . . ?
C21 C22 C24 120.9(6) . . ?
C21 C22 C23 122.8(7) . . ?
C24 C22 C23 116.3(7) . . ?
F5E C5 F5D 104(2) . . ?
F5E C5 F5F 104.7(18) . . ?
F5D C5 F5F 116(2) . . ?
F5C C5 F5B 104.0(7) . . ?
F5C C5 F5A 106.6(8) . . ?
F5B C5 F5A 107.1(9) . . ?
F5E C5 C4 109.0(14) . . ?
F5D C5 C4 106.9(14) . . ?
F5F C5 C4 115.3(13) . . ?
F5C C5 C4 112.6(6) . . ?
F5B C5 C4 113.3(6) . . ?
F5A C5 C4 112.6(6) . . ?
F7 C20 F9 106.3(10) . . ?
F7 C20 F8 106.2(9) . . ?
F9 C20 F8 99.9(8) . . ?
F7 C20 C19 116.0(7) . . ?
F9 C20 C19 114.0(8) . . ?
F8 C20 C19 113.0(9) . . ?
C26 C25 N5 114.2(6) . . ?
C19 C21 C22 118.6(6) . . ?
C36 C35 C34 99.3(11) . . ?
F23B C23 F23A 107.3(15) . . ?
F23E C23 F23F 96(3) . . ?
F23E C23 F23D 123(3) . . ?
F23F C23 F23D 110(3) . . ?
F23B C23 F23C 105.0(11) . . ?
F23A C23 F23C 103.1(12) . . ?
F23B C23 C22 115.9(8) . . ?
F23A C23 C22 114.0(9) . . ?
F23E C23 C22 107(2) . . ?
F23F C23 C22 113.3(13) . . ?
F23D C23 C22 107(2) . . ?
F23C C23 C22 110.5(9) . . ?
C35 C34 C33 114.8(9) . . ?
C28 C27 C26 110.2(12) . . ?
C31B C30 C29 114.7(10) . . ?
C29 C30 C31A 108.2(9) . . ?
C32A C31B C30 109.7(19) . . ?
C32B C31A C30 118(2) . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.060

