# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1488032'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_audit_creation_date             2015-11-18
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C34 H33 F4 I N4 O'
_chemical_formula_moiety         'C27 H25 F4 I N4 O, C7 H8'
_chemical_formula_weight         716.56
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.469(3)
_cell_length_b                   17.723(4)
_cell_length_c                   15.596(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.991(4)
_cell_angle_gamma                90.0000
_cell_volume                     3172.8(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8873
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448.00
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.416
_exptl_absorpt_correction_T_max  0.808

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            36305
_diffrn_reflns_av_R_equivalents  0.1242
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         1.825
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5647
_reflns_number_gt                4641
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5647
_refine_ls_number_parameters     404
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0848P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         3.25
_refine_diff_density_min         -1.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.09471(2) 0.10994(2) 0.02261(2) 0.02072(12) Uani 1 1 d . . . . .
F21 F 0.1422(2) 0.01794(14) -0.17758(19) 0.0283(6) Uani 1 1 d . . . . .
F22 F 0.1783(2) 0.09284(14) -0.31437(18) 0.0277(6) Uani 1 1 d . . . . .
F24 F 0.5101(2) 0.20951(13) -0.09054(18) 0.0258(6) Uani 1 1 d . . . . .
F25 F 0.4813(2) 0.12809(14) 0.04392(18) 0.0248(6) Uani 1 1 d . . . . .
O29 O 0.4155(3) 0.28889(19) -0.4961(2) 0.0327(8) Uani 1 1 d . . . . .
N17 N 0.3008(3) 0.02519(19) 0.0065(3) 0.0219(8) Uani 1 1 d . . . . .
N18 N 0.3761(3) -0.0342(2) 0.0402(3) 0.0264(8) Uani 1 1 d . . . . .
N19 N 0.3523(3) -0.0642(2) 0.1074(3) 0.0237(8) Uani 1 1 d . . . . .
N26 N 0.3648(3) 0.19147(19) -0.2785(3) 0.0209(8) Uani 1 1 d . . . . .
C1 C 0.2190(4) -0.0450(2) 0.1912(3) 0.0200(9) Uani 1 1 d . . . . .
C2 C 0.1994(4) 0.0108(2) 0.2452(3) 0.0203(9) Uani 1 1 d . . . . .
H2 H 0.2189 0.0616 0.2380 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1514(4) -0.0063(2) 0.3103(3) 0.0200(9) Uani 1 1 d . . . . .
C4 C 0.1240(4) -0.0821(2) 0.3186(3) 0.0204(9) Uani 1 1 d . . . . .
H4 H 0.0901 -0.0948 0.3617 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1451(3) -0.1396(2) 0.2652(3) 0.0193(9) Uani 1 1 d . . . . .
C6 C 0.1934(4) -0.1203(2) 0.2015(3) 0.0190(9) Uani 1 1 d . . . . .
H6 H 0.2089 -0.1583 0.1650 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1304(4) 0.0580(2) 0.3686(3) 0.0231(9) Uani 1 1 d . . . . .
C8 C 0.0565(4) 0.1198(2) 0.3021(4) 0.0285(11) Uani 1 1 d . . . . .
H8A H 0.0440 0.1614 0.3386 0.034 Uiso 1 1 calc R U . . .
H8B H -0.0189 0.0987 0.2615 0.034 Uiso 1 1 calc R U . . .
H8C H 0.0974 0.1387 0.2640 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2487(4) 0.0907(3) 0.4331(4) 0.0303(11) Uani 1 1 d . . . . .
H9A H 0.2948 0.0513 0.4757 0.036 Uiso 1 1 calc R U . . .
H9B H 0.2361 0.1326 0.4692 0.036 Uiso 1 1 calc R U . . .
H9C H 0.2906 0.1091 0.3956 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0663(4) 0.0307(3) 0.4295(4) 0.0286(10) Uani 1 1 d . . . . .
H10A H 0.0522 0.0737 0.4632 0.034 Uiso 1 1 calc R U . . .
H10B H 0.1142 -0.0068 0.4742 0.034 Uiso 1 1 calc R U . . .
H10C H -0.0082 0.0080 0.3899 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1096(4) -0.2213(2) 0.2752(3) 0.0217(9) Uani 1 1 d . . . . .
C12 C 0.1532(5) -0.2438(3) 0.3778(3) 0.0316(11) Uani 1 1 d . . . . .
H12A H 0.1160 -0.2118 0.4096 0.038 Uiso 1 1 calc R U . . .
H12B H 0.2379 -0.2372 0.4070 0.038 Uiso 1 1 calc R U . . .
H12C H 0.1336 -0.2967 0.3827 0.038 Uiso 1 1 calc R U . . .
C13 C -0.0240(4) -0.2270(3) 0.2328(4) 0.0312(11) Uani 1 1 d . . . . .
H13A H -0.0533 -0.2130 0.1668 0.037 Uiso 1 1 calc R U . . .
H13B H -0.0564 -0.1927 0.2658 0.037 Uiso 1 1 calc R U . . .
H13C H -0.0474 -0.2789 0.2387 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1584(4) -0.2779(3) 0.2255(4) 0.0277(10) Uani 1 1 d . . . . .
H14A H 0.1268 -0.2669 0.1586 0.033 Uiso 1 1 calc R U . . .
H14B H 0.1361 -0.3292 0.2355 0.033 Uiso 1 1 calc R U . . .
H14C H 0.2435 -0.2740 0.2506 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2637(4) -0.0245(2) 0.1196(3) 0.0197(9) Uani 1 1 d . . . . .
C16 C 0.2299(4) 0.0322(2) 0.0552(3) 0.0200(9) Uani 1 1 d . . . . .
C20 C 0.3111(4) 0.0711(2) -0.0647(3) 0.0210(9) Uani 1 1 d . . . . .
C21 C 0.2339(4) 0.0646(2) -0.1554(3) 0.0224(9) Uani 1 1 d . . . . .
C22 C 0.2510(4) 0.1035(2) -0.2264(3) 0.0206(9) Uani 1 1 d . . . . .
C23 C 0.3453(4) 0.1528(2) -0.2059(3) 0.0208(9) Uani 1 1 d . . . . .
C24 C 0.4203(4) 0.1606(2) -0.1138(3) 0.0222(9) Uani 1 1 d . . . . .
C25 C 0.4058(4) 0.1199(2) -0.0437(3) 0.0200(9) Uani 1 1 d . . . . .
C27 C 0.2808(4) 0.2372(2) -0.3394(3) 0.0229(9) Uani 1 1 d . . . . .
H27 H 0.2104 0.2451 -0.3306 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2953(4) 0.2711(2) -0.4112(3) 0.0257(10) Uani 1 1 d . . . . .
H28 H 0.2353 0.3026 -0.4519 0.031 Uiso 1 1 calc R U . . .
C29 C 0.4022(4) 0.2602(2) -0.4280(3) 0.0245(10) Uani 1 1 d . . . . .
C30 C 0.4874(4) 0.2130(2) -0.3605(3) 0.0252(10) Uani 1 1 d . . . . .
H30 H 0.5598 0.2047 -0.3659 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4686(4) 0.1799(2) -0.2897(3) 0.0226(9) Uani 1 1 d . . . . .
H31 H 0.5268 0.1484 -0.2471 0.027 Uiso 1 1 calc R U . . .
C41 C 0.5752(5) 0.0970(3) 0.4726(4) 0.0436(14) Uani 1 1 d . . . . .
H41A H 0.5419 0.1473 0.4712 0.052 Uiso 1 1 calc R U . . .
H41B H 0.6403 0.0893 0.5327 0.052 Uiso 1 1 calc R U . . .
H41C H 0.5154 0.0587 0.4642 0.052 Uiso 1 1 calc R U . . .
C42 C 0.6186(4) 0.0906(3) 0.3952(4) 0.0314(11) Uani 1 1 d . . . . .
C43 C 0.5560(4) 0.0519(3) 0.3123(4) 0.0365(12) Uani 1 1 d . . . . .
H43 H 0.4869 0.0257 0.3061 0.044 Uiso 1 1 calc R U . . .
C44 C 0.5923(5) 0.0512(3) 0.2403(4) 0.0368(12) Uani 1 1 d . . . . .
H44 H 0.5484 0.0245 0.1848 0.044 Uiso 1 1 calc R U . . .
C45 C 0.6937(5) 0.0894(3) 0.2480(4) 0.0360(12) Uani 1 1 d . . . . .
H45 H 0.7173 0.0902 0.1970 0.043 Uiso 1 1 calc R U . . .
C46 C 0.7592(4) 0.1259(3) 0.3294(4) 0.0339(12) Uani 1 1 d . . . . .
H46 H 0.8297 0.1504 0.3359 0.041 Uiso 1 1 calc R U . . .
C47 C 0.7211(4) 0.1265(3) 0.4024(4) 0.0348(12) Uani 1 1 d . . . . .
H47 H 0.7662 0.1521 0.4584 0.042 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C16 2.081(4) . ?
F21 C21 1.343(5) . ?
F22 C22 1.329(5) . ?
F24 C24 1.350(5) . ?
F25 C25 1.330(5) . ?
O29 C29 1.246(5) . ?
N17 N18 1.371(5) . ?
N17 C16 1.377(5) . ?
N17 C20 1.423(5) . ?
N18 N19 1.308(5) . ?
N19 C15 1.384(5) . ?
N26 C27 1.371(6) . ?
N26 C31 1.387(5) . ?
N26 C23 1.423(5) . ?
C1 C2 1.382(6) . ?
C1 C6 1.395(6) . ?
C1 C15 1.475(6) . ?
C2 C3 1.399(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(6) . ?
C3 C7 1.542(6) . ?
C4 C5 1.406(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(6) . ?
C5 C11 1.540(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.538(6) . ?
C7 C10 1.539(6) . ?
C7 C8 1.542(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.528(7) . ?
C11 C14 1.532(6) . ?
C11 C13 1.537(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.366(6) . ?
C20 C21 1.370(7) . ?
C20 C25 1.395(6) . ?
C21 C22 1.389(6) . ?
C22 C23 1.398(6) . ?
C23 C24 1.381(6) . ?
C24 C25 1.380(6) . ?
C27 C28 1.344(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.467(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.437(7) . ?
C30 C31 1.350(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C41 C42 1.508(7) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C47 1.392(7) . ?
C42 C43 1.401(8) . ?
C43 C44 1.364(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.399(8) . ?
C44 H44 0.9500 . ?
C45 C46 1.373(8) . ?
C45 H45 0.9500 . ?
C46 C47 1.394(7) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N18 N17 C16 110.4(3) . . ?
N18 N17 C20 118.7(3) . . ?
C16 N17 C20 130.7(4) . . ?
N19 N18 N17 106.5(3) . . ?
N18 N19 C15 110.3(3) . . ?
C27 N26 C31 119.9(4) . . ?
C27 N26 C23 121.0(3) . . ?
C31 N26 C23 119.1(3) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 C15 119.6(4) . . ?
C6 C1 C15 119.7(4) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 117.6(4) . . ?
C2 C3 C7 119.1(4) . . ?
C4 C3 C7 123.3(4) . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 C11 121.8(4) . . ?
C4 C5 C11 119.6(4) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C9 C7 C10 108.1(4) . . ?
C9 C7 C8 109.9(4) . . ?
C10 C7 C8 108.7(4) . . ?
C9 C7 C3 108.9(3) . . ?
C10 C7 C3 112.3(3) . . ?
C8 C7 C3 108.9(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 108.1(4) . . ?
C12 C11 C13 108.5(4) . . ?
C14 C11 C13 108.5(4) . . ?
C12 C11 C5 110.7(4) . . ?
C14 C11 C5 112.2(3) . . ?
C13 C11 C5 108.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N19 107.8(4) . . ?
C16 C15 C1 129.8(4) . . ?
N19 C15 C1 122.5(4) . . ?
C15 C16 N17 105.0(4) . . ?
C15 C16 I1 130.8(3) . . ?
N17 C16 I1 124.0(3) . . ?
C21 C20 C25 118.9(4) . . ?
C21 C20 N17 121.1(4) . . ?
C25 C20 N17 119.8(4) . . ?
F21 C21 C20 120.1(4) . . ?
F21 C21 C22 118.7(4) . . ?
C20 C21 C22 121.1(4) . . ?
F22 C22 C21 119.8(4) . . ?
F22 C22 C23 119.9(4) . . ?
C21 C22 C23 120.3(4) . . ?
C24 C23 C22 117.9(4) . . ?
C24 C23 N26 121.5(4) . . ?
C22 C23 N26 120.6(4) . . ?
F24 C24 C25 118.4(4) . . ?
F24 C24 C23 119.9(4) . . ?
C25 C24 C23 121.8(4) . . ?
F25 C25 C24 119.8(4) . . ?
F25 C25 C20 120.2(4) . . ?
C24 C25 C20 119.9(4) . . ?
C28 C27 N26 121.8(4) . . ?
C28 C27 H27 119.1 . . ?
N26 C27 H27 119.1 . . ?
C27 C28 C29 121.2(4) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
O29 C29 C30 123.7(4) . . ?
O29 C29 C28 122.1(4) . . ?
C30 C29 C28 114.2(4) . . ?
C31 C30 C29 122.5(4) . . ?
C31 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
C30 C31 N26 120.5(4) . . ?
C30 C31 H31 119.7 . . ?
N26 C31 H31 119.7 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C47 C42 C43 117.4(5) . . ?
C47 C42 C41 120.4(5) . . ?
C43 C42 C41 122.1(5) . . ?
C44 C43 C42 121.3(5) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 H43 119.3 . . ?
C43 C44 C45 120.3(5) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 119.8(5) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C47 119.3(5) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C42 C47 C46 121.7(5) . . ?
C42 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N17 N18 N19 0.8(5) . . . . ?
C20 N17 N18 N19 176.8(4) . . . . ?
N17 N18 N19 C15 -1.2(5) . . . . ?
C6 C1 C2 C3 -1.2(7) . . . . ?
C15 C1 C2 C3 176.6(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C2 C3 C7 -179.6(4) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C7 C3 C4 C5 -179.4(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C4 C5 C11 -178.1(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C11 C5 C6 C1 176.8(4) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
C15 C1 C6 C5 -176.4(4) . . . . ?
C2 C3 C7 C9 -65.9(5) . . . . ?
C4 C3 C7 C9 114.6(5) . . . . ?
C2 C3 C7 C10 174.4(4) . . . . ?
C4 C3 C7 C10 -5.2(6) . . . . ?
C2 C3 C7 C8 53.9(5) . . . . ?
C4 C3 C7 C8 -125.6(4) . . . . ?
C6 C5 C11 C12 133.8(4) . . . . ?
C4 C5 C11 C12 -49.0(5) . . . . ?
C6 C5 C11 C14 13.0(6) . . . . ?
C4 C5 C11 C14 -169.8(4) . . . . ?
C6 C5 C11 C13 -107.1(5) . . . . ?
C4 C5 C11 C13 70.1(5) . . . . ?
N18 N19 C15 C16 1.2(5) . . . . ?
N18 N19 C15 C1 -179.4(4) . . . . ?
C2 C1 C15 C16 -45.2(7) . . . . ?
C6 C1 C15 C16 132.7(5) . . . . ?
C2 C1 C15 N19 135.5(4) . . . . ?
C6 C1 C15 N19 -46.6(6) . . . . ?
N19 C15 C16 N17 -0.6(5) . . . . ?
C1 C15 C16 N17 -180.0(4) . . . . ?
N19 C15 C16 I1 174.6(3) . . . . ?
C1 C15 C16 I1 -4.7(7) . . . . ?
N18 N17 C16 C15 -0.1(5) . . . . ?
C20 N17 C16 C15 -175.5(4) . . . . ?
N18 N17 C16 I1 -175.7(3) . . . . ?
C20 N17 C16 I1 8.9(7) . . . . ?
N18 N17 C20 C21 104.1(5) . . . . ?
C16 N17 C20 C21 -80.8(6) . . . . ?
N18 N17 C20 C25 -71.4(5) . . . . ?
C16 N17 C20 C25 103.7(5) . . . . ?
C25 C20 C21 F21 179.9(4) . . . . ?
N17 C20 C21 F21 4.4(6) . . . . ?
C25 C20 C21 C22 2.5(6) . . . . ?
N17 C20 C21 C22 -173.1(4) . . . . ?
F21 C21 C22 F22 -1.3(6) . . . . ?
C20 C21 C22 F22 176.2(4) . . . . ?
F21 C21 C22 C23 179.7(4) . . . . ?
C20 C21 C22 C23 -2.8(6) . . . . ?
F22 C22 C23 C24 -178.3(3) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
F22 C22 C23 N26 -0.5(6) . . . . ?
C21 C22 C23 N26 178.6(4) . . . . ?
C27 N26 C23 C24 -124.8(4) . . . . ?
C31 N26 C23 C24 58.0(6) . . . . ?
C27 N26 C23 C22 57.5(5) . . . . ?
C31 N26 C23 C22 -119.8(4) . . . . ?
C22 C23 C24 F24 -177.8(4) . . . . ?
N26 C23 C24 F24 4.4(6) . . . . ?
C22 C23 C24 C25 1.7(6) . . . . ?
N26 C23 C24 C25 -176.1(4) . . . . ?
F24 C24 C25 F25 -1.8(6) . . . . ?
C23 C24 C25 F25 178.8(4) . . . . ?
F24 C24 C25 C20 177.4(3) . . . . ?
C23 C24 C25 C20 -2.1(6) . . . . ?
C21 C20 C25 F25 179.1(4) . . . . ?
N17 C20 C25 F25 -5.3(6) . . . . ?
C21 C20 C25 C24 -0.1(6) . . . . ?
N17 C20 C25 C24 175.5(4) . . . . ?
C31 N26 C27 C28 0.7(6) . . . . ?
C23 N26 C27 C28 -176.5(4) . . . . ?
N26 C27 C28 C29 0.3(7) . . . . ?
C27 C28 C29 O29 177.3(4) . . . . ?
C27 C28 C29 C30 -1.5(6) . . . . ?
O29 C29 C30 C31 -176.9(4) . . . . ?
C28 C29 C30 C31 1.9(6) . . . . ?
C29 C30 C31 N26 -1.0(7) . . . . ?
C27 N26 C31 C30 -0.4(6) . . . . ?
C23 N26 C31 C30 176.9(4) . . . . ?
C47 C42 C43 C44 -1.7(7) . . . . ?
C41 C42 C43 C44 175.3(5) . . . . ?
C42 C43 C44 C45 0.0(7) . . . . ?
C43 C44 C45 C46 2.1(7) . . . . ?
C44 C45 C46 C47 -2.3(7) . . . . ?
C43 C42 C47 C46 1.5(7) . . . . ?
C41 C42 C47 C46 -175.5(5) . . . . ?
C45 C46 C47 C42 0.5(7) . . . . ?

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




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Toluene
####################################################################### 
# 
# 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_2-H
_database_code_depnum_ccdc_archive 'CCDC 1488033'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-27
_audit_creation_method           'by CrystalStructure 4.1'

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

_chemical_formula_sum            'C32 H34 F4 I N3 O2'
_chemical_formula_moiety         'C28 H26 F4 I N3 O, C4 H8 O'
_chemical_formula_weight         695.54
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4431(6)
_cell_length_b                   11.7892(12)
_cell_length_c                   31.416(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3127.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10264
_cell_measurement_theta_min      1.30
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408.00
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.927

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            38083
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         1.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             5690
_reflns_number_gt                5442
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0624
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5690
_refine_ls_number_parameters     388
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0370P)²+1.5440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.38709(3) 0.80209(2) 0.72163(2) 0.03584(9) Uani 1 1 d . . . . .
F7 F 0.1381(3) 0.5779(2) 0.64798(9) 0.0530(7) Uani 1 1 d . . . . .
F8 F -0.0534(3) 0.6792(2) 0.59267(9) 0.0503(7) Uani 1 1 d . . . . .
F10 F 0.3776(3) 0.9014(2) 0.54431(8) 0.0474(6) Uani 1 1 d . . . . .
F11 F 0.5648(3) 0.7970(3) 0.59971(9) 0.0509(7) Uani 1 1 d . . . . .
O15 O -0.2348(4) 1.0346(3) 0.45083(11) 0.0541(9) Uani 1 1 d D . . . .
H15 H -0.336(4) 1.044(6) 0.4633(19) 0.081 Uiso 1 1 d D U . . .
O41 O 0.9569(7) 0.4225(7) 0.54056(17) 0.123(3) Uani 1 1 d . . . . .
N2 N 0.4582(4) 0.6313(3) 0.65427(10) 0.0327(8) Uani 1 1 d . . . . .
N3 N 0.5464(5) 0.5405(3) 0.64221(11) 0.0425(9) Uani 1 1 d . . . . .
N4 N 0.6340(5) 0.5130(3) 0.67470(10) 0.0382(8) Uani 1 1 d . . . . .
C1 C 0.4934(5) 0.6622(3) 0.69513(12) 0.0272(8) Uani 1 1 d . . . . .
C5 C 0.6082(5) 0.5851(3) 0.70798(11) 0.0271(7) Uani 1 1 d . . . . .
C6 C 0.3549(5) 0.6856(3) 0.62489(12) 0.0325(8) Uani 1 1 d . . . . .
C7 C 0.1973(6) 0.6576(3) 0.62233(13) 0.0363(9) Uani 1 1 d . . . . .
C8 C 0.0992(5) 0.7113(3) 0.59354(12) 0.0355(8) Uani 1 1 d . . . . .
C9 C 0.1522(5) 0.7960(4) 0.56602(11) 0.0322(8) Uani 1 1 d . . . . .
C10 C 0.3137(5) 0.8209(3) 0.56923(12) 0.0338(9) Uani 1 1 d . . . . .
C11 C 0.4111(5) 0.7680(3) 0.59810(13) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.0466(5) 0.8550(3) 0.53588(12) 0.0301(8) Uani 1 1 d . . . . .
C13 C -0.1056(6) 0.8876(4) 0.54749(12) 0.0364(9) Uani 1 1 d . . . . .
H13 H -0.1442 0.8685 0.5750 0.044 Uiso 1 1 calc R U . . .
C14 C -0.2021(5) 0.9474(4) 0.51973(14) 0.0402(10) Uani 1 1 d . . . . .
H14 H -0.3055 0.9695 0.5284 0.048 Uiso 1 1 calc R U . . .
C15 C -0.1483(5) 0.9748(4) 0.47959(13) 0.0381(10) Uani 1 1 d . . . . .
C16 C 0.0024(6) 0.9421(4) 0.46712(13) 0.0408(11) Uani 1 1 d . . . . .
H16 H 0.0394 0.9609 0.4394 0.049 Uiso 1 1 calc R U . . .
C17 C 0.0993(6) 0.8825(4) 0.49463(12) 0.0375(9) Uani 1 1 d . . . . .
H17 H 0.2020 0.8599 0.4856 0.045 Uiso 1 1 calc R U . . .
C18 C 0.6975(4) 0.5736(3) 0.74743(11) 0.0245(8) Uani 1 1 d . . . . .
C19 C 0.6460(4) 0.6194(3) 0.78582(11) 0.0271(8) Uani 1 1 d . . . . .
H19 H 0.5474 0.6581 0.7869 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7371(5) 0.6093(3) 0.82275(12) 0.0293(8) Uani 1 1 d . . . . .
C21 C 0.8789(5) 0.5502(3) 0.82019(11) 0.0296(8) Uani 1 1 d . . . . .
H21 H 0.9414 0.5422 0.8452 0.036 Uiso 1 1 calc R U . . .
C22 C 0.9328(4) 0.5024(3) 0.78237(13) 0.0282(8) Uani 1 1 d . . . . .
C23 C 0.8421(5) 0.5156(3) 0.74623(12) 0.0271(8) Uani 1 1 d . . . . .
H23 H 0.8783 0.4847 0.7200 0.033 Uiso 1 1 calc R U . . .
C24 C 0.6775(6) 0.6635(4) 0.86437(14) 0.0426(11) Uani 1 1 d . . . . .
C25 C 0.7969(7) 0.6485(6) 0.90070(16) 0.0642(16) Uani 1 1 d . . . . .
H25A H 0.7542 0.6824 0.9268 0.077 Uiso 1 1 calc R U . . .
H25B H 0.8966 0.6860 0.8932 0.077 Uiso 1 1 calc R U . . .
H25C H 0.8162 0.5675 0.9054 0.077 Uiso 1 1 calc R U . . .
C26 C 0.5226(7) 0.6050(6) 0.87731(17) 0.0635(15) Uani 1 1 d . . . . .
H26A H 0.4411 0.6203 0.8558 0.076 Uiso 1 1 calc R U . . .
H26B H 0.4876 0.6342 0.9049 0.076 Uiso 1 1 calc R U . . .
H26C H 0.5401 0.5230 0.8794 0.076 Uiso 1 1 calc R U . . .
C27 C 0.6485(9) 0.7879(5) 0.85781(17) 0.0728(19) Uani 1 1 d . . . . .
H27A H 0.6131 0.8220 0.8846 0.087 Uiso 1 1 calc R U . . .
H27B H 0.5667 0.7983 0.8360 0.087 Uiso 1 1 calc R U . . .
H27C H 0.7468 0.8245 0.8485 0.087 Uiso 1 1 calc R U . . .
C28 C 1.0925(5) 0.4396(3) 0.78132(14) 0.0376(9) Uani 1 1 d . . . . .
C29 C 1.1202(11) 0.3799(9) 0.7401(2) 0.130(4) Uani 1 1 d . . . . .
H29A H 1.0336 0.3264 0.7348 0.156 Uiso 1 1 calc R U . . .
H29B H 1.2208 0.3386 0.7414 0.156 Uiso 1 1 calc R U . . .
H29C H 1.1244 0.4356 0.7169 0.156 Uiso 1 1 calc R U . . .
C30 C 1.2191(7) 0.5247(7) 0.7868(6) 0.199(8) Uani 1 1 d . . . . .
H30A H 1.3183 0.4864 0.7942 0.238 Uiso 1 1 calc R U . . .
H30B H 1.1899 0.5772 0.8097 0.238 Uiso 1 1 calc R U . . .
H30C H 1.2330 0.5671 0.7603 0.238 Uiso 1 1 calc R U . . .
C31 C 1.1019(10) 0.3531(7) 0.8156(2) 0.110(3) Uani 1 1 d . . . . .
H31A H 1.0854 0.3897 0.8433 0.131 Uiso 1 1 calc R U . . .
H31B H 1.2065 0.3171 0.8151 0.131 Uiso 1 1 calc R U . . .
H31C H 1.0200 0.2954 0.8111 0.131 Uiso 1 1 calc R U . . .
C42 C 0.9029(18) 0.3496(10) 0.5136(3) 0.149(5) Uani 1 1 d . . . . .
H42A H 0.9918 0.3152 0.4976 0.179 Uiso 1 1 calc R U . . .
H42B H 0.8319 0.3878 0.4930 0.179 Uiso 1 1 calc R U . . .
C43 C 0.817(2) 0.2630(8) 0.5359(4) 0.194(8) Uani 1 1 d . . . . .
H43A H 0.8819 0.1932 0.5386 0.233 Uiso 1 1 calc R U . . .
H43B H 0.7174 0.2444 0.5211 0.233 Uiso 1 1 calc R U . . .
C44 C 0.7856(8) 0.3131(7) 0.5782(3) 0.096(2) Uani 1 1 d . . . . .
H44A H 0.6737 0.3373 0.5805 0.115 Uiso 1 1 calc R U . . .
H44B H 0.8084 0.2577 0.6011 0.115 Uiso 1 1 calc R U . . .
C45 C 0.8917(8) 0.4108(6) 0.5812(2) 0.0759(17) Uani 1 1 d . . . . .
H45A H 0.8323 0.4798 0.5893 0.091 Uiso 1 1 calc R U . . .
H45B H 0.9758 0.3970 0.6025 0.091 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.054(4) . ?
F7 C7 1.336(5) . ?
F8 C8 1.343(5) . ?
F10 C10 1.344(5) . ?
F11 C11 1.343(5) . ?
O15 C15 1.359(5) . ?
O15 H15 0.95(3) . ?
O41 C42 1.290(11) . ?
O41 C45 1.396(8) . ?
N2 N3 1.357(5) . ?
N2 C1 1.367(5) . ?
N2 C6 1.422(5) . ?
N3 N4 1.301(5) . ?
N4 C5 1.365(5) . ?
C1 C5 1.389(5) . ?
C5 C18 1.457(5) . ?
C6 C11 1.370(6) . ?
C6 C7 1.374(6) . ?
C7 C8 1.380(6) . ?
C8 C9 1.394(6) . ?
C9 C10 1.399(6) . ?
C9 C12 1.475(5) . ?
C10 C11 1.374(6) . ?
C12 C13 1.390(7) . ?
C12 C17 1.408(6) . ?
C13 C14 1.386(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(7) . ?
C16 C17 1.382(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.391(5) . ?
C18 C23 1.399(6) . ?
C19 C20 1.397(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(6) . ?
C20 C24 1.540(6) . ?
C21 C22 1.392(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 C28 1.538(5) . ?
C23 H23 0.9500 . ?
C24 C27 1.501(7) . ?
C24 C25 1.533(7) . ?
C24 C26 1.534(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C30 1.476(8) . ?
C28 C31 1.486(7) . ?
C28 C29 1.493(8) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C42 C43 1.433(16) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.478(15) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.462(10) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O15 H15 106(4) . . ?
C42 O41 C45 113.3(7) . . ?
N3 N2 C1 110.7(3) . . ?
N3 N2 C6 120.7(3) . . ?
C1 N2 C6 128.5(3) . . ?
N4 N3 N2 106.8(3) . . ?
N3 N4 C5 110.8(3) . . ?
N2 C1 C5 104.5(3) . . ?
N2 C1 I1 120.0(3) . . ?
C5 C1 I1 135.4(3) . . ?
N4 C5 C1 107.2(3) . . ?
N4 C5 C18 120.7(3) . . ?
C1 C5 C18 132.1(3) . . ?
C11 C6 C7 118.0(4) . . ?
C11 C6 N2 120.4(4) . . ?
C7 C6 N2 121.6(4) . . ?
F7 C7 C6 119.7(4) . . ?
F7 C7 C8 119.6(4) . . ?
C6 C7 C8 120.7(4) . . ?
F8 C8 C7 117.4(4) . . ?
F8 C8 C9 119.8(4) . . ?
C7 C8 C9 122.8(4) . . ?
C8 C9 C10 114.7(3) . . ?
C8 C9 C12 122.8(4) . . ?
C10 C9 C12 122.4(4) . . ?
F10 C10 C11 117.7(4) . . ?
F10 C10 C9 119.9(3) . . ?
C11 C10 C9 122.4(4) . . ?
F11 C11 C6 119.5(4) . . ?
F11 C11 C10 119.2(4) . . ?
C6 C11 C10 121.4(4) . . ?
C13 C12 C17 118.0(4) . . ?
C13 C12 C9 121.4(4) . . ?
C17 C12 C9 120.6(4) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O15 C15 C14 123.5(4) . . ?
O15 C15 C16 116.7(4) . . ?
C14 C15 C16 119.7(4) . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 119.1(3) . . ?
C19 C18 C5 122.6(3) . . ?
C23 C18 C5 118.3(3) . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 118.0(3) . . ?
C21 C20 C24 122.6(4) . . ?
C19 C20 C24 119.4(4) . . ?
C20 C21 C22 122.4(4) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C23 C22 C21 118.4(3) . . ?
C23 C22 C28 121.6(4) . . ?
C21 C22 C28 120.0(4) . . ?
C22 C23 C18 121.2(4) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
C27 C24 C25 108.8(5) . . ?
C27 C24 C26 109.7(5) . . ?
C25 C24 C26 108.1(4) . . ?
C27 C24 C20 110.0(4) . . ?
C25 C24 C20 111.7(4) . . ?
C26 C24 C20 108.5(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C28 C31 110.0(8) . . ?
C30 C28 C29 108.0(8) . . ?
C31 C28 C29 107.3(6) . . ?
C30 C28 C22 107.8(4) . . ?
C31 C28 C22 111.2(4) . . ?
C29 C28 C22 112.5(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C42 C43 109.3(8) . . ?
O41 C42 H42A 109.8 . . ?
C43 C42 H42A 109.8 . . ?
O41 C42 H42B 109.8 . . ?
C43 C42 H42B 109.8 . . ?
H42A C42 H42B 108.3 . . ?
C42 C43 C44 104.3(7) . . ?
C42 C43 H43A 110.9 . . ?
C44 C43 H43A 110.9 . . ?
C42 C43 H43B 110.9 . . ?
C44 C43 H43B 110.9 . . ?
H43A C43 H43B 108.9 . . ?
C45 C44 C43 105.1(8) . . ?
C45 C44 H44A 110.7 . . ?
C43 C44 H44A 110.7 . . ?
C45 C44 H44B 110.7 . . ?
C43 C44 H44B 110.7 . . ?
H44A C44 H44B 108.8 . . ?
O41 C45 C44 105.1(6) . . ?
O41 C45 H45A 110.7 . . ?
C44 C45 H45A 110.7 . . ?
O41 C45 H45B 110.7 . . ?
C44 C45 H45B 110.7 . . ?
H45A C45 H45B 108.8 . . ?

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
C1 N2 N3 N4 0.9(5) . . . . ?
C6 N2 N3 N4 176.9(4) . . . . ?
N2 N3 N4 C5 -1.2(5) . . . . ?
N3 N2 C1 C5 -0.2(5) . . . . ?
C6 N2 C1 C5 -175.8(4) . . . . ?
N3 N2 C1 I1 177.0(3) . . . . ?
C6 N2 C1 I1 1.4(6) . . . . ?
N3 N4 C5 C1 1.1(5) . . . . ?
N3 N4 C5 C18 -177.7(4) . . . . ?
N2 C1 C5 N4 -0.5(4) . . . . ?
I1 C1 C5 N4 -177.0(3) . . . . ?
N2 C1 C5 C18 178.1(4) . . . . ?
I1 C1 C5 C18 1.5(7) . . . . ?
N3 N2 C6 C11 -85.4(5) . . . . ?
C1 N2 C6 C11 89.8(5) . . . . ?
N3 N2 C6 C7 94.6(5) . . . . ?
C1 N2 C6 C7 -90.2(5) . . . . ?
C11 C6 C7 F7 -179.9(4) . . . . ?
N2 C6 C7 F7 0.2(6) . . . . ?
C11 C6 C7 C8 0.0(6) . . . . ?
N2 C6 C7 C8 -179.9(4) . . . . ?
F7 C7 C8 F8 -0.4(6) . . . . ?
C6 C7 C8 F8 179.6(4) . . . . ?
F7 C7 C8 C9 179.5(4) . . . . ?
C6 C7 C8 C9 -0.4(7) . . . . ?
F8 C8 C9 C10 -178.9(4) . . . . ?
C7 C8 C9 C10 1.2(6) . . . . ?
F8 C8 C9 C12 1.2(6) . . . . ?
C7 C8 C9 C12 -178.7(4) . . . . ?
C8 C9 C10 F10 -179.8(4) . . . . ?
C12 C9 C10 F10 0.1(6) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C12 C9 C10 C11 178.2(4) . . . . ?
C7 C6 C11 F11 -179.8(4) . . . . ?
N2 C6 C11 F11 0.2(6) . . . . ?
C7 C6 C11 C10 -0.5(6) . . . . ?
N2 C6 C11 C10 179.5(4) . . . . ?
F10 C10 C11 F11 -1.2(6) . . . . ?
C9 C10 C11 F11 -179.3(4) . . . . ?
F10 C10 C11 C6 179.5(4) . . . . ?
C9 C10 C11 C6 1.4(7) . . . . ?
C8 C9 C12 C13 40.7(6) . . . . ?
C10 C9 C12 C13 -139.2(4) . . . . ?
C8 C9 C12 C17 -140.8(4) . . . . ?
C10 C9 C12 C17 39.3(6) . . . . ?
C17 C12 C13 C14 -1.3(6) . . . . ?
C9 C12 C13 C14 177.2(4) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C13 C14 C15 O15 -179.0(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
O15 C15 C16 C17 179.0(4) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C12 -0.6(7) . . . . ?
C13 C12 C17 C16 1.3(6) . . . . ?
C9 C12 C17 C16 -177.2(4) . . . . ?
N4 C5 C18 C19 -160.0(4) . . . . ?
C1 C5 C18 C19 21.6(6) . . . . ?
N4 C5 C18 C23 21.1(5) . . . . ?
C1 C5 C18 C23 -157.3(4) . . . . ?
C23 C18 C19 C20 0.8(6) . . . . ?
C5 C18 C19 C20 -178.2(3) . . . . ?
C18 C19 C20 C21 -1.3(6) . . . . ?
C18 C19 C20 C24 178.7(4) . . . . ?
C19 C20 C21 C22 0.6(6) . . . . ?
C24 C20 C21 C22 -179.4(4) . . . . ?
C20 C21 C22 C23 0.7(6) . . . . ?
C20 C21 C22 C28 178.9(4) . . . . ?
C21 C22 C23 C18 -1.3(6) . . . . ?
C28 C22 C23 C18 -179.5(3) . . . . ?
C19 C18 C23 C22 0.6(5) . . . . ?
C5 C18 C23 C22 179.6(3) . . . . ?
C21 C20 C24 C27 123.7(5) . . . . ?
C19 C20 C24 C27 -56.3(6) . . . . ?
C21 C20 C24 C25 2.8(6) . . . . ?
C19 C20 C24 C25 -177.2(4) . . . . ?
C21 C20 C24 C26 -116.3(5) . . . . ?
C19 C20 C24 C26 63.7(5) . . . . ?
C23 C22 C28 C30 108.9(8) . . . . ?
C21 C22 C28 C30 -69.3(8) . . . . ?
C23 C22 C28 C31 -130.4(6) . . . . ?
C21 C22 C28 C31 51.4(6) . . . . ?
C23 C22 C28 C29 -10.0(7) . . . . ?
C21 C22 C28 C29 171.8(6) . . . . ?
C45 O41 C42 C43 -12.4(16) . . . . ?
O41 C42 C43 C44 17.2(17) . . . . ?
C42 C43 C44 C45 -15.3(14) . . . . ?
C42 O41 C45 C44 1.9(11) . . . . ?
C43 C44 C45 O41 8.8(10) . . . . ?

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




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_2-2-DBUH2
_database_code_depnum_ccdc_archive 'CCDC 1488034'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-27
_audit_creation_method           'by CrystalStructure 4.1'

# start Validation Reply Form
_vrf_PLAT431_2-2-DBUH2           
;
PROBLEM: Short Inter HL..A  Contact I1     ..  O15     ..       2.59 Ang.  
RESPONSE: This is an interesting interaction, of an apparent halogen-bonding
 type.
;

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

_chemical_formula_sum            'C37 H42 F4 I N5 O'
_chemical_formula_moiety         'C28 H25 F4 I N3 O, C9 H17 N2'
_chemical_formula_weight         775.67
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        I2/a
_space_group_name_Hall           '-I 2ya'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   20.258(3)
_cell_length_b                   13.9884(13)
_cell_length_c                   26.734(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.187(10)
_cell_angle_gamma                90.0000
_cell_volume                     7376.1(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7313
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3168.00
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.895

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            44203
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_theta_max         25.382
_diffrn_reflns_theta_min         1.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             6762
_reflns_number_gt                4925
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0761
_refine_ls_number_restraints     19
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         6762
_refine_ls_number_parameters     473
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0297P)²+21.2857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.05834(2) 0.20270(2) 0.38473(2) 0.03867(9) Uani 1 1 d . . . . .
F7 F 0.20242(12) 0.35399(17) 0.43427(8) 0.0589(6) Uani 1 1 d . . . . .
F8 F 0.17470(12) 0.49111(18) 0.49514(8) 0.0617(7) Uani 1 1 d . . . . .
F10 F 0.01264(12) 0.61760(16) 0.35730(8) 0.0526(6) Uani 1 1 d . . . . .
F11 F 0.04184(12) 0.48165(16) 0.29624(8) 0.0555(6) Uani 1 1 d . . . . .
O15 O 0.01327(12) 0.84450(18) 0.55018(9) 0.0411(6) Uani 1 1 d . . . . .
N2 N 0.13397(15) 0.3383(2) 0.33176(11) 0.0381(7) Uani 1 1 d . . . . .
N3 N 0.16663(17) 0.3545(2) 0.29351(12) 0.0455(8) Uani 1 1 d . . . . .
N4 N 0.16686(16) 0.2738(2) 0.26964(12) 0.0424(8) Uani 1 1 d . . . . .
N41 N 0.39658(17) -0.0720(2) 0.38037(12) 0.0495(9) Uani 1 1 d D . . . .
H41 H 0.4278(18) -0.104(3) 0.4087(12) 0.074 Uiso 1 1 d D U . . .
N45 N 0.33732(16) 0.0616(2) 0.34682(12) 0.0470(8) Uani 1 1 d . . . . .
C1 C 0.11300(17) 0.2465(3) 0.33154(13) 0.0343(8) Uani 1 1 d . . . . .
C5 C 0.13473(17) 0.2051(3) 0.29136(13) 0.0347(8) Uani 1 1 d . . . . .
C6 C 0.12228(18) 0.4148(3) 0.36361(13) 0.0364(9) Uani 1 1 d . . . . .
C7 C 0.15611(19) 0.4199(3) 0.41459(14) 0.0425(9) Uani 1 1 d . . . . .
C8 C 0.14142(19) 0.4908(3) 0.44569(13) 0.0406(9) Uani 1 1 d . . . . .
C9 C 0.09323(18) 0.5595(3) 0.42840(13) 0.0349(8) Uani 1 1 d . . . . .
C10 C 0.06064(19) 0.5536(3) 0.37730(14) 0.0382(9) Uani 1 1 d . . . . .
C11 C 0.07519(19) 0.4837(3) 0.34536(13) 0.0375(9) Uani 1 1 d . . . . .
C12 C 0.07367(18) 0.6332(3) 0.46212(13) 0.0353(8) Uani 1 1 d . . . . .
C13 C 0.1179(2) 0.7048(3) 0.48399(15) 0.0484(10) Uani 1 1 d . . . . .
H13 H 0.1628 0.7052 0.4789 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0979(2) 0.7758(3) 0.51318(15) 0.0482(10) Uani 1 1 d . . . . .
H14 H 0.1289 0.8251 0.5271 0.058 Uiso 1 1 calc R U . . .
C15 C 0.03308(19) 0.7766(3) 0.52263(13) 0.0361(9) Uani 1 1 d . . . . .
C16 C -0.01008(19) 0.7023(3) 0.50177(14) 0.0413(9) Uani 1 1 d . . . . .
H16 H -0.0542 0.6994 0.5083 0.050 Uiso 1 1 calc R U . . .
C17 C 0.00993(19) 0.6330(3) 0.47183(14) 0.0417(9) Uani 1 1 d . . . . .
H17 H -0.0210 0.5839 0.4575 0.050 Uiso 1 1 calc R U . . .
C18 C 0.12943(17) 0.1072(3) 0.27112(13) 0.0347(8) Uani 1 1 d . . . . .
C19 C 0.14354(17) 0.0899(3) 0.22327(13) 0.0357(8) Uani 1 1 d . . . . .
H19 H 0.1549 0.1420 0.2040 0.043 Uiso 1 1 calc R U . . .
C20 C 0.14131(17) -0.0016(3) 0.20316(13) 0.0353(8) Uani 1 1 d . . . . .
C21 C 0.12407(19) -0.0762(3) 0.23210(14) 0.0427(9) Uani 1 1 d . . . . .
H21 H 0.1226 -0.1392 0.2187 0.051 Uiso 1 1 calc R U . . .
C22 C 0.10889(19) -0.0625(3) 0.27963(14) 0.0428(9) Uani 1 1 d . . . . .
C23 C 0.11224(18) 0.0309(3) 0.29858(14) 0.0407(9) Uani 1 1 d . . . . .
H23 H 0.1025 0.0424 0.3312 0.049 Uiso 1 1 calc R U . . .
C24 C 0.15649(19) -0.0234(3) 0.15080(14) 0.0401(9) Uani 1 1 d . . . . .
C25 C 0.1658(2) 0.0684(3) 0.12219(14) 0.0521(11) Uani 1 1 d . . . . .
H25A H 0.2058 0.1027 0.1413 0.063 Uiso 1 1 calc R U . . .
H25B H 0.1256 0.1089 0.1191 0.063 Uiso 1 1 calc R U . . .
H25C H 0.1720 0.0523 0.0879 0.063 Uiso 1 1 calc R U . . .
C26 C 0.0980(2) -0.0793(3) 0.11735(15) 0.0496(10) Uani 1 1 d . . . . .
H26A H 0.0562 -0.0416 0.1125 0.060 Uiso 1 1 calc R U . . .
H26B H 0.0921 -0.1399 0.1342 0.060 Uiso 1 1 calc R U . . .
H26C H 0.1081 -0.0922 0.0839 0.060 Uiso 1 1 calc R U . . .
C27 C 0.2211(2) -0.0826(3) 0.15824(15) 0.0558(11) Uani 1 1 d . . . . .
H27A H 0.2158 -0.1417 0.1766 0.067 Uiso 1 1 calc R U . . .
H27B H 0.2593 -0.0458 0.1783 0.067 Uiso 1 1 calc R U . . .
H27C H 0.2299 -0.0984 0.1246 0.067 Uiso 1 1 calc R U . . .
C28 C 0.0885(2) -0.1456(3) 0.30971(17) 0.0558(11) Uani 1 1 d . . . . .
C29 C 0.0874(14) -0.2395(9) 0.2824(8) 0.141(11) Uani 0.495(15) 1 d . U P A 1
H29A H 0.0613 -0.2328 0.2469 0.211 Uiso 0.495(15) 1 calc R U P A 1
H29B H 0.0662 -0.2881 0.3000 0.211 Uiso 0.495(15) 1 calc R U P A 1
H29C H 0.1339 -0.2588 0.2824 0.211 Uiso 0.495(15) 1 calc R U P A 1
C30 C 0.1421(8) -0.1517(13) 0.3603(6) 0.120(7) Uani 0.495(15) 1 d . U P A 1
H30A H 0.1874 -0.1449 0.3535 0.180 Uiso 0.495(15) 1 calc R U P A 1
H30B H 0.1387 -0.2138 0.3765 0.180 Uiso 0.495(15) 1 calc R U P A 1
H30C H 0.1345 -0.1005 0.3834 0.180 Uiso 0.495(15) 1 calc R U P A 1
C31 C 0.0213(8) -0.1233(9) 0.3223(6) 0.087(5) Uani 0.495(15) 1 d . U P A 1
H31A H 0.0260 -0.0668 0.3445 0.131 Uiso 0.495(15) 1 calc R U P A 1
H31B H 0.0068 -0.1780 0.3401 0.131 Uiso 0.495(15) 1 calc R U P A 1
H31C H -0.0127 -0.1107 0.2905 0.131 Uiso 0.495(15) 1 calc R U P A 1
C29A C 0.0279(7) -0.2012(11) 0.2747(5) 0.094(6) Uani 0.505(15) 1 d . U P A 2
H29D H -0.0118 -0.1592 0.2659 0.142 Uiso 0.505(15) 1 calc R U P A 2
H29E H 0.0169 -0.2573 0.2932 0.142 Uiso 0.505(15) 1 calc R U P A 2
H29F H 0.0407 -0.2219 0.2432 0.142 Uiso 0.505(15) 1 calc R U P A 2
C30A C 0.1458(6) -0.2155(9) 0.3241(6) 0.077(5) Uani 0.505(15) 1 d . U P A 2
H30D H 0.1599 -0.2363 0.2931 0.116 Uiso 0.505(15) 1 calc R U P A 2
H30E H 0.1309 -0.2711 0.3409 0.116 Uiso 0.505(15) 1 calc R U P A 2
H30F H 0.1842 -0.1849 0.3477 0.116 Uiso 0.505(15) 1 calc R U P A 2
C31A C 0.0661(9) -0.1174(8) 0.3581(6) 0.091(6) Uani 0.505(15) 1 d . U P A 2
H31D H 0.1053 -0.0949 0.3840 0.136 Uiso 0.505(15) 1 calc R U P A 2
H31E H 0.0461 -0.1730 0.3715 0.136 Uiso 0.505(15) 1 calc R U P A 2
H31F H 0.0323 -0.0662 0.3501 0.136 Uiso 0.505(15) 1 calc R U P A 2
C42 C 0.3652(3) -0.1313(3) 0.33654(18) 0.0716(14) Uani 1 1 d . . . . .
H42A H 0.3991 -0.1771 0.3292 0.086 Uiso 1 1 calc R U . . .
H42B H 0.3277 -0.1686 0.3451 0.086 Uiso 1 1 calc R U . . .
C43 C 0.3396(3) -0.0749(4) 0.2921(2) 0.104(2) Uani 1 1 d . . . . .
H43A H 0.3099 -0.1154 0.2659 0.125 Uiso 1 1 calc R U . . .
H43B H 0.3781 -0.0536 0.2778 0.125 Uiso 1 1 calc R U . . .
C44 C 0.3009(2) 0.0097(3) 0.30166(15) 0.0548(11) Uani 1 1 d . . . . .
H44A H 0.2932 0.0524 0.2713 0.066 Uiso 1 1 calc R U . . .
H44B H 0.2561 -0.0106 0.3069 0.066 Uiso 1 1 calc R U . . .
C46 C 0.3164(2) 0.1602(3) 0.35242(18) 0.0603(12) Uani 1 1 d . . . . .
H46A H 0.2878 0.1823 0.3193 0.072 Uiso 1 1 calc R U . . .
H46B H 0.3572 0.2015 0.3608 0.072 Uiso 1 1 calc R U . . .
C47 C 0.2776(2) 0.1703(4) 0.39360(18) 0.0692(14) Uani 1 1 d . . . . .
H47A H 0.2473 0.1143 0.3920 0.083 Uiso 1 1 calc R U . . .
H47B H 0.2486 0.2279 0.3862 0.083 Uiso 1 1 calc R U . . .
C48 C 0.3205(3) 0.1783(4) 0.44715(19) 0.0778(16) Uani 1 1 d . . . . .
H48A H 0.2904 0.1881 0.4711 0.093 Uiso 1 1 calc R U . . .
H48B H 0.3497 0.2355 0.4491 0.093 Uiso 1 1 calc R U . . .
C49 C 0.3654(2) 0.0911(4) 0.46486(17) 0.0705(14) Uani 1 1 d . . . . .
H49A H 0.3914 0.1022 0.5005 0.085 Uiso 1 1 calc R U . . .
H49B H 0.3360 0.0348 0.4653 0.085 Uiso 1 1 calc R U . . .
C50 C 0.4148(2) 0.0686(3) 0.43139(16) 0.0528(11) Uani 1 1 d . . . . .
H50A H 0.4346 0.1290 0.4222 0.063 Uiso 1 1 calc R U . . .
H50B H 0.4522 0.0289 0.4512 0.063 Uiso 1 1 calc R U . . .
C51 C 0.38192(18) 0.0175(3) 0.38376(14) 0.0404(9) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.084(3) . ?
F7 C7 1.335(4) . ?
F8 C8 1.340(4) . ?
F10 C10 1.340(4) . ?
F11 C11 1.333(4) . ?
O15 C15 1.319(4) . ?
N2 C1 1.353(5) . ?
N2 N3 1.357(4) . ?
N2 C6 1.421(4) . ?
N3 N4 1.297(4) . ?
N4 C5 1.363(4) . ?
N41 C51 1.295(5) . ?
N41 C42 1.458(5) . ?
N41 H41 0.978(19) . ?
N45 C51 1.328(5) . ?
N45 C44 1.456(5) . ?
N45 C46 1.461(5) . ?
C1 C5 1.378(5) . ?
C5 C18 1.468(5) . ?
C6 C11 1.365(5) . ?
C6 C7 1.381(5) . ?
C7 C8 1.370(5) . ?
C8 C9 1.373(5) . ?
C9 C10 1.377(5) . ?
C9 C12 1.481(5) . ?
C10 C11 1.373(5) . ?
C12 C17 1.374(5) . ?
C12 C13 1.383(5) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(5) . ?
C16 C17 1.376(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.383(5) . ?
C18 C19 1.394(5) . ?
C19 C20 1.385(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(5) . ?
C20 C24 1.531(5) . ?
C21 C22 1.387(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(5) . ?
C22 C28 1.522(5) . ?
C23 H23 0.9500 . ?
C24 C27 1.524(5) . ?
C24 C26 1.527(5) . ?
C24 C25 1.528(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C30A 1.500(11) . ?
C28 C29 1.501(13) . ?
C28 C31 1.509(13) . ?
C28 C31A 1.519(12) . ?
C28 C30 1.532(15) . ?
C28 C29A 1.570(11) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?
C31A H31D 0.9800 . ?
C31A H31E 0.9800 . ?
C31A H31F 0.9800 . ?
C42 C43 1.421(7) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.474(6) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C46 C47 1.499(6) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.499(6) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.531(7) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.520(6) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.480(5) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 N3 111.2(3) . . ?
C1 N2 C6 128.5(3) . . ?
N3 N2 C6 120.1(3) . . ?
N4 N3 N2 106.4(3) . . ?
N3 N4 C5 110.4(3) . . ?
C51 N41 C42 122.8(3) . . ?
C51 N41 H41 121(3) . . ?
C42 N41 H41 116(3) . . ?
C51 N45 C44 121.0(3) . . ?
C51 N45 C46 121.7(3) . . ?
C44 N45 C46 116.8(3) . . ?
N2 C1 C5 104.3(3) . . ?
N2 C1 I1 119.4(2) . . ?
C5 C1 I1 136.3(3) . . ?
N4 C5 C1 107.7(3) . . ?
N4 C5 C18 120.2(3) . . ?
C1 C5 C18 132.0(3) . . ?
C11 C6 C7 117.7(3) . . ?
C11 C6 N2 121.1(3) . . ?
C7 C6 N2 121.2(3) . . ?
F7 C7 C8 119.4(3) . . ?
F7 C7 C6 120.0(3) . . ?
C8 C7 C6 120.6(3) . . ?
F8 C8 C7 118.1(3) . . ?
F8 C8 C9 119.3(3) . . ?
C7 C8 C9 122.6(3) . . ?
C8 C9 C10 115.8(3) . . ?
C8 C9 C12 123.4(3) . . ?
C10 C9 C12 120.8(3) . . ?
F10 C10 C11 117.8(3) . . ?
F10 C10 C9 119.7(3) . . ?
C11 C10 C9 122.5(3) . . ?
F11 C11 C6 119.5(3) . . ?
F11 C11 C10 119.7(3) . . ?
C6 C11 C10 120.8(3) . . ?
C17 C12 C13 117.9(3) . . ?
C17 C12 C9 120.5(3) . . ?
C13 C12 C9 121.6(3) . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
O15 C15 C16 121.2(3) . . ?
O15 C15 C14 121.8(3) . . ?
C16 C15 C14 117.0(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C12 C17 C16 121.5(3) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C23 C18 C19 118.9(3) . . ?
C23 C18 C5 122.0(3) . . ?
C19 C18 C5 119.1(3) . . ?
C20 C19 C18 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 117.9(3) . . ?
C19 C20 C24 122.9(3) . . ?
C21 C20 C24 119.2(3) . . ?
C22 C21 C20 122.9(3) . . ?
C22 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
C21 C22 C23 117.2(3) . . ?
C21 C22 C28 121.5(3) . . ?
C23 C22 C28 121.2(3) . . ?
C18 C23 C22 121.7(3) . . ?
C18 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C27 C24 C26 109.1(3) . . ?
C27 C24 C25 108.7(3) . . ?
C26 C24 C25 107.8(3) . . ?
C27 C24 C20 109.6(3) . . ?
C26 C24 C20 110.3(3) . . ?
C25 C24 C20 111.4(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C31 112.0(11) . . ?
C30A C28 C31A 108.4(8) . . ?
C30A C28 C22 110.2(5) . . ?
C29 C28 C22 112.7(6) . . ?
C31 C28 C22 109.2(5) . . ?
C31A C28 C22 115.0(5) . . ?
C29 C28 C30 108.1(12) . . ?
C31 C28 C30 107.9(9) . . ?
C22 C28 C30 106.7(6) . . ?
C30A C28 C29A 106.5(8) . . ?
C31A C28 C29A 106.9(9) . . ?
C22 C28 C29A 109.5(5) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C29A H29D 109.5 . . ?
C28 C29A H29E 109.5 . . ?
H29D C29A H29E 109.5 . . ?
C28 C29A H29F 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
C28 C30A H30D 109.5 . . ?
C28 C30A H30E 109.5 . . ?
H30D C30A H30E 109.5 . . ?
C28 C30A H30F 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
C28 C31A H31D 109.5 . . ?
C28 C31A H31E 109.5 . . ?
H31D C31A H31E 109.5 . . ?
C28 C31A H31F 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
C43 C42 N41 111.3(4) . . ?
C43 C42 H42A 109.4 . . ?
N41 C42 H42A 109.4 . . ?
C43 C42 H42B 109.4 . . ?
N41 C42 H42B 109.4 . . ?
H42A C42 H42B 108.0 . . ?
C42 C43 C44 114.2(5) . . ?
C42 C43 H43A 108.7 . . ?
C44 C43 H43A 108.7 . . ?
C42 C43 H43B 108.7 . . ?
C44 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?
N45 C44 C43 110.8(4) . . ?
N45 C44 H44A 109.5 . . ?
C43 C44 H44A 109.5 . . ?
N45 C44 H44B 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 108.1 . . ?
N45 C46 C47 112.2(4) . . ?
N45 C46 H46A 109.2 . . ?
C47 C46 H46A 109.2 . . ?
N45 C46 H46B 109.2 . . ?
C47 C46 H46B 109.2 . . ?
H46A C46 H46B 107.9 . . ?
C46 C47 C48 114.9(4) . . ?
C46 C47 H47A 108.5 . . ?
C48 C47 H47A 108.5 . . ?
C46 C47 H47B 108.5 . . ?
C48 C47 H47B 108.5 . . ?
H47A C47 H47B 107.5 . . ?
C47 C48 C49 114.2(4) . . ?
C47 C48 H48A 108.7 . . ?
C49 C48 H48A 108.7 . . ?
C47 C48 H48B 108.7 . . ?
C49 C48 H48B 108.7 . . ?
H48A C48 H48B 107.6 . . ?
C50 C49 C48 114.1(4) . . ?
C50 C49 H49A 108.7 . . ?
C48 C49 H49A 108.7 . . ?
C50 C49 H49B 108.7 . . ?
C48 C49 H49B 108.7 . . ?
H49A C49 H49B 107.6 . . ?
C51 C50 C49 112.3(3) . . ?
C51 C50 H50A 109.2 . . ?
C49 C50 H50A 109.2 . . ?
C51 C50 H50B 109.2 . . ?
C49 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
N41 C51 N45 121.6(4) . . ?
N41 C51 C50 117.5(3) . . ?
N45 C51 C50 120.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 N4 -0.5(4) . . . . ?
C6 N2 N3 N4 -176.8(3) . . . . ?
N2 N3 N4 C5 0.3(4) . . . . ?
N3 N2 C1 C5 0.6(4) . . . . ?
C6 N2 C1 C5 176.5(3) . . . . ?
N3 N2 C1 I1 -177.9(2) . . . . ?
C6 N2 C1 I1 -2.0(5) . . . . ?
N3 N4 C5 C1 0.1(4) . . . . ?
N3 N4 C5 C18 -179.2(3) . . . . ?
N2 C1 C5 N4 -0.4(4) . . . . ?
I1 C1 C5 N4 177.7(3) . . . . ?
N2 C1 C5 C18 178.8(4) . . . . ?
I1 C1 C5 C18 -3.1(6) . . . . ?
C1 N2 C6 C11 -103.3(4) . . . . ?
N3 N2 C6 C11 72.3(5) . . . . ?
C1 N2 C6 C7 74.0(5) . . . . ?
N3 N2 C6 C7 -110.4(4) . . . . ?
C11 C6 C7 F7 179.7(3) . . . . ?
N2 C6 C7 F7 2.3(5) . . . . ?
C11 C6 C7 C8 1.4(6) . . . . ?
N2 C6 C7 C8 -176.0(3) . . . . ?
F7 C7 C8 F8 0.2(6) . . . . ?
C6 C7 C8 F8 178.5(3) . . . . ?
F7 C7 C8 C9 -178.3(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
F8 C8 C9 C10 -179.1(3) . . . . ?
C7 C8 C9 C10 -0.6(6) . . . . ?
F8 C8 C9 C12 -2.4(6) . . . . ?
C7 C8 C9 C12 176.1(4) . . . . ?
C8 C9 C10 F10 179.7(3) . . . . ?
C12 C9 C10 F10 2.8(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C12 C9 C10 C11 -177.0(3) . . . . ?
C7 C6 C11 F11 179.5(3) . . . . ?
N2 C6 C11 F11 -3.1(5) . . . . ?
C7 C6 C11 C10 -2.1(5) . . . . ?
N2 C6 C11 C10 175.3(3) . . . . ?
F10 C10 C11 F11 0.1(5) . . . . ?
C9 C10 C11 F11 179.9(3) . . . . ?
F10 C10 C11 C6 -178.3(3) . . . . ?
C9 C10 C11 C6 1.6(6) . . . . ?
C8 C9 C12 C17 -113.1(4) . . . . ?
C10 C9 C12 C17 63.5(5) . . . . ?
C8 C9 C12 C13 68.0(5) . . . . ?
C10 C9 C12 C13 -115.3(4) . . . . ?
C17 C12 C13 C14 -2.2(6) . . . . ?
C9 C12 C13 C14 176.6(4) . . . . ?
C12 C13 C14 C15 1.5(6) . . . . ?
C13 C14 C15 O15 -179.5(4) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
O15 C15 C16 C17 178.1(3) . . . . ?
C14 C15 C16 C17 -2.0(6) . . . . ?
C13 C12 C17 C16 0.9(6) . . . . ?
C9 C12 C17 C16 -178.0(3) . . . . ?
C15 C16 C17 C12 1.3(6) . . . . ?
N4 C5 C18 C23 164.3(3) . . . . ?
C1 C5 C18 C23 -14.8(6) . . . . ?
N4 C5 C18 C19 -14.3(5) . . . . ?
C1 C5 C18 C19 166.6(4) . . . . ?
C23 C18 C19 C20 -0.6(5) . . . . ?
C5 C18 C19 C20 178.0(3) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C18 C19 C20 C24 -180.0(3) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C24 C20 C21 C22 -179.3(3) . . . . ?
C20 C21 C22 C23 -0.7(6) . . . . ?
C20 C21 C22 C28 178.5(4) . . . . ?
C19 C18 C23 C22 0.2(5) . . . . ?
C5 C18 C23 C22 -178.4(3) . . . . ?
C21 C22 C23 C18 0.5(5) . . . . ?
C28 C22 C23 C18 -178.7(4) . . . . ?
C19 C20 C24 C27 113.8(4) . . . . ?
C21 C20 C24 C27 -66.6(4) . . . . ?
C19 C20 C24 C26 -126.2(4) . . . . ?
C21 C20 C24 C26 53.5(4) . . . . ?
C19 C20 C24 C25 -6.6(5) . . . . ?
C21 C20 C24 C25 173.0(3) . . . . ?
C21 C22 C28 C30A 63.6(9) . . . . ?
C23 C22 C28 C30A -117.2(8) . . . . ?
C21 C22 C28 C29 0.2(14) . . . . ?
C23 C22 C28 C29 179.4(13) . . . . ?
C21 C22 C28 C31 -125.0(8) . . . . ?
C23 C22 C28 C31 54.2(9) . . . . ?
C21 C22 C28 C31A -173.5(9) . . . . ?
C23 C22 C28 C31A 5.7(10) . . . . ?
C21 C22 C28 C30 118.6(9) . . . . ?
C23 C22 C28 C30 -62.2(9) . . . . ?
C21 C22 C28 C29A -53.2(9) . . . . ?
C23 C22 C28 C29A 126.0(9) . . . . ?
C51 N41 C42 C43 22.8(7) . . . . ?
N41 C42 C43 C44 -45.7(7) . . . . ?
C51 N45 C44 C43 -25.1(6) . . . . ?
C46 N45 C44 C43 162.2(4) . . . . ?
C42 C43 C44 N45 47.2(7) . . . . ?
C51 N45 C46 C47 -66.1(5) . . . . ?
C44 N45 C46 C47 106.5(4) . . . . ?
N45 C46 C47 C48 82.5(5) . . . . ?
C46 C47 C48 C49 -61.4(6) . . . . ?
C47 C48 C49 C50 59.0(6) . . . . ?
C48 C49 C50 C51 -79.4(5) . . . . ?
C42 N41 C51 N45 -0.7(6) . . . . ?
C42 N41 C51 C50 177.0(4) . . . . ?
C44 N45 C51 N41 2.4(6) . . . . ?
C46 N45 C51 N41 174.7(4) . . . . ?
C44 N45 C51 C50 -175.2(4) . . . . ?
C46 N45 C51 C50 -2.9(6) . . . . ?
C49 C50 C51 N41 -108.4(4) . . . . ?
C49 C50 C51 N45 69.4(5) . . . . ?

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




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Acetonitrile
####################################################################### 
# 
# 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_S3
_database_code_depnum_ccdc_archive 'CCDC 1488035'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_S3                  
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: Poor quality crystals - many tried - best result presented.
;
_vrf_PLAT971_S3                  
;
PROBLEM: Check Calcd Residual Density  2.24A From     C48       3.75 eA-3  
RESPONSE: Poor quality crystals - many tried - best result presented.
;
# end Validation Reply Form

_audit_creation_date             2016-06-27
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C29 H28 F4 I N3 O'
_chemical_formula_moiety         'C29 H28 F4 I N3 O'
_chemical_formula_weight         637.46
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   25.213(7)
_cell_length_b                   13.978(3)
_cell_length_c                   27.637(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.879(4)
_cell_angle_gamma                90.0000
_cell_volume                     8974(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    19353
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3840.00
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.967

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            109125
_diffrn_reflns_av_R_equivalents  0.2103
_diffrn_reflns_theta_max         25.380
_diffrn_reflns_theta_min         1.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             16446
_reflns_number_gt                8588
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.1077
_refine_ls_wR_factor_ref         0.3145
_refine_ls_wR_factor_gt          0.2707
_refine_ls_number_restraints     30
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         16446
_refine_ls_number_parameters     1027
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1362P)²+110.0794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.038
_refine_diff_density_max         3.73
_refine_diff_density_min         -1.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I16 I 0.19092(5) 0.05687(6) 0.04383(4) 0.0457(3) Uani 1 1 d . . . . .
I56 I 0.17071(4) 0.55598(6) 0.01090(4) 0.0343(3) Uani 1 1 d . . . . .
I96 I 0.22320(5) 0.91601(7) 0.72589(4) 0.0448(3) Uani 1 1 d . . . . .
F21 F 0.1751(4) 0.1766(6) 0.1571(3) 0.049(2) Uani 1 1 d . . . . .
F22 F 0.2436(4) 0.1348(6) 0.2555(4) 0.050(2) Uani 1 1 d . . . . .
F24 F 0.4033(4) 0.2340(7) 0.2204(3) 0.052(2) Uani 1 1 d . . . . .
F25 F 0.3349(4) 0.2763(6) 0.1231(3) 0.044(2) Uani 1 1 d . . . . .
F61 F 0.0268(4) 0.7928(6) -0.0015(3) 0.053(2) Uani 1 1 d . . . . .
F62 F -0.0762(4) 0.7422(7) -0.0704(3) 0.052(2) Uani 1 1 d . . . . .
F64 F 0.0084(4) 0.6133(7) -0.1804(4) 0.055(2) Uani 1 1 d . . . . .
F65 F 0.1118(4) 0.6651(6) -0.1121(3) 0.052(2) Uani 1 1 d . . . . .
F101 F 0.2530(4) 0.7402(9) 0.6024(4) 0.078(3) Uani 1 1 d . . . . .
F102 F 0.1852(4) 0.7846(9) 0.5053(4) 0.073(3) Uani 1 1 d . . . . .
F104 F 0.0260(4) 0.7783(8) 0.5537(4) 0.066(3) Uani 1 1 d . . . . .
F105 F 0.0961(5) 0.7379(8) 0.6518(4) 0.071(3) Uani 1 1 d . . . . .
O29 O 0.4732(4) 0.1074(7) 0.4513(4) 0.044(3) Uani 1 1 d . . . . .
O69 O -0.2608(5) 0.5797(9) -0.2714(5) 0.061(3) Uani 1 1 d . . . . .
O109 O -0.0366(5) 0.8762(9) 0.3153(4) 0.062(3) Uani 1 1 d . . . . .
N17 N 0.2173(5) 0.2577(8) 0.0862(4) 0.035(3) Uani 1 1 d . . . . .
N18 N 0.2103(5) 0.3522(8) 0.0742(4) 0.035(3) Uani 1 1 d . . . . .
N19 N 0.1761(5) 0.3557(8) 0.0235(4) 0.031(3) Uani 1 1 d . . . . .
N57 N 0.1260(5) 0.7576(8) -0.0186(5) 0.040(3) Uani 1 1 d . . . . .
N58 N 0.1358(6) 0.8508(8) -0.0092(5) 0.051(4) Uani 1 1 d . . . . .
N59 N 0.1870(5) 0.8568(7) 0.0289(5) 0.045(4) Uani 1 1 d . . . . .
N97 N 0.2127(6) 0.7154(9) 0.6820(5) 0.050(4) Uani 1 1 d . . . . .
N98 N 0.2299(6) 0.6203(9) 0.6944(6) 0.055(4) Uani 1 1 d . . . . .
N99 N 0.2621(6) 0.6201(8) 0.7431(5) 0.049(4) Uani 1 1 d . . . . .
C1 C 0.1211(6) 0.2494(10) -0.0505(6) 0.040(4) Uani 1 1 d . . . . .
C2 C 0.1276(6) 0.3055(10) -0.0902(5) 0.035(3) Uani 1 1 d . . . . .
H2 H 0.1552 0.3555 -0.0815 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0935(7) 0.2870(11) -0.1415(6) 0.043(4) Uani 1 1 d . . . . .
C4 C 0.0533(6) 0.2124(12) -0.1526(6) 0.047(4) Uani 1 1 d . . . . .
H4 H 0.0294 0.1995 -0.1882 0.056 Uiso 1 1 calc R U . . .
C5 C 0.0472(7) 0.1576(11) -0.1141(6) 0.042(4) Uani 1 1 d . . . . .
C6 C 0.0810(6) 0.1792(10) -0.0621(5) 0.037(3) Uani 1 1 d . . . . .
H6 H 0.0760 0.1446 -0.0346 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0999(8) 0.3409(12) -0.1873(6) 0.053(5) Uani 1 1 d . . . . .
C8 C 0.1429(8) 0.4227(14) -0.1690(8) 0.069(6) Uani 1 1 d . . . . .
H8A H 0.1800 0.3983 -0.1442 0.083 Uiso 1 1 calc R U . . .
H8B H 0.1480 0.4511 -0.1994 0.083 Uiso 1 1 calc R U . . .
H8C H 0.1286 0.4714 -0.1516 0.083 Uiso 1 1 calc R U . . .
C9 C 0.0433(8) 0.3793(15) -0.2252(7) 0.069(6) Uani 1 1 d . . . . .
H9A H 0.0152 0.3270 -0.2372 0.083 Uiso 1 1 calc R U . . .
H9B H 0.0291 0.4281 -0.2077 0.083 Uiso 1 1 calc R U . . .
H9C H 0.0485 0.4077 -0.2555 0.083 Uiso 1 1 calc R U . . .
C10 C 0.1233(9) 0.2718(16) -0.2177(7) 0.071(6) Uani 1 1 d . . . . .
H10A H 0.1603 0.2457 -0.1938 0.086 Uiso 1 1 calc R U . . .
H10B H 0.0959 0.2195 -0.2323 0.086 Uiso 1 1 calc R U . . .
H10C H 0.1287 0.3065 -0.2463 0.086 Uiso 1 1 calc R U . . .
C11 C 0.0037(7) 0.0718(11) -0.1280(7) 0.054(5) Uani 1 1 d . . . . .
C12 C -0.0543(8) 0.1049(14) -0.1673(8) 0.068(5) Uani 1 1 d . . . . .
H12A H -0.0692 0.1556 -0.1516 0.082 Uiso 1 1 calc R U . . .
H12B H -0.0499 0.1295 -0.1987 0.082 Uiso 1 1 calc R U . . .
H12C H -0.0812 0.0509 -0.1769 0.082 Uiso 1 1 calc R U . . .
C13 C 0.0273(9) -0.0063(13) -0.1514(8) 0.077(6) Uani 1 1 d . . . . .
H13A H 0.0648 -0.0271 -0.1257 0.092 Uiso 1 1 calc R U . . .
H13B H 0.0007 -0.0606 -0.1611 0.092 Uiso 1 1 calc R U . . .
H13C H 0.0319 0.0180 -0.1829 0.092 Uiso 1 1 calc R U . . .
C14 C -0.0109(10) 0.0383(16) -0.0787(9) 0.082(6) Uani 1 1 d . U . . .
H14A H -0.0260 0.0928 -0.0657 0.098 Uiso 1 1 calc R U . . .
H14B H -0.0398 -0.0127 -0.0898 0.098 Uiso 1 1 calc R U . . .
H14C H 0.0242 0.0146 -0.0507 0.098 Uiso 1 1 calc R U . . .
C15 C 0.1609(6) 0.2681(9) 0.0054(5) 0.027(3) Uani 1 1 d . U . . .
C16 C 0.1870(7) 0.2047(9) 0.0446(6) 0.038(4) Uani 1 1 d . . . . .
C20 C 0.2532(7) 0.2292(9) 0.1378(6) 0.037(4) Uani 1 1 d . . . . .
C21 C 0.2319(6) 0.1915(10) 0.1725(6) 0.040(4) Uani 1 1 d . . . . .
C22 C 0.2676(6) 0.1698(11) 0.2230(5) 0.037(4) Uani 1 1 d . . . . .
C23 C 0.3267(6) 0.1810(10) 0.2418(5) 0.033(3) Uani 1 1 d . . . . .
C24 C 0.3469(6) 0.2181(10) 0.2057(5) 0.036(3) Uani 1 1 d . . . . .
C25 C 0.3118(6) 0.2424(10) 0.1552(5) 0.036(4) Uani 1 1 d . . . . .
C26 C 0.3654(7) 0.1589(9) 0.2963(5) 0.036(3) Uani 1 1 d . . . . .
C27 C 0.3504(6) 0.1868(10) 0.3379(5) 0.037(4) Uani 1 1 d . . . . .
H27 H 0.3149 0.2187 0.3312 0.045 Uiso 1 1 calc R U . . .
C28 C 0.3879(7) 0.1674(11) 0.3892(6) 0.043(4) Uani 1 1 d . . . . .
H28 H 0.3776 0.1852 0.4176 0.052 Uiso 1 1 calc R U . . .
C29 C 0.4392(6) 0.1232(10) 0.3992(5) 0.035(3) Uani 1 1 d . . . . .
C30 C 0.4538(6) 0.0927(11) 0.3596(7) 0.044(4) Uani 1 1 d . . . . .
H30 H 0.4888 0.0591 0.3670 0.053 Uiso 1 1 calc R U . . .
C31 C 0.4170(6) 0.1108(10) 0.3078(5) 0.034(3) Uani 1 1 d . . . . .
H31 H 0.4275 0.0900 0.2799 0.041 Uiso 1 1 calc R U . . .
C32 C 0.5277(6) 0.0643(11) 0.4634(6) 0.040(4) Uani 1 1 d . . . . .
H32A H 0.5472 0.0573 0.5016 0.048 Uiso 1 1 calc R U . . .
H32B H 0.5226 0.0012 0.4468 0.048 Uiso 1 1 calc R U . . .
H32C H 0.5509 0.1047 0.4503 0.048 Uiso 1 1 calc R U . . .
C41 C 0.2717(6) 0.7616(10) 0.0817(5) 0.037(4) Uani 1 1 d . . . . .
C42 C 0.3079(6) 0.8405(9) 0.0896(5) 0.036(3) Uani 1 1 d . . . . .
H42 H 0.2929 0.8985 0.0716 0.043 Uiso 1 1 calc R U . . .
C43 C 0.3659(6) 0.8357(10) 0.1234(5) 0.037(3) Uani 1 1 d . . . . .
C44 C 0.3846(6) 0.7484(10) 0.1483(6) 0.039(4) Uani 1 1 d . . . . .
H44 H 0.4242 0.7424 0.1703 0.047 Uiso 1 1 calc R U . . .
C45 C 0.3499(7) 0.6698(10) 0.1434(6) 0.045(4) Uani 1 1 d . . . . .
C46 C 0.2935(7) 0.6808(10) 0.1096(5) 0.042(4) Uani 1 1 d . . . . .
H46 H 0.2681 0.6284 0.1055 0.051 Uiso 1 1 calc R U . . .
C47 C 0.4057(7) 0.9239(12) 0.1300(6) 0.047(4) Uani 1 1 d . . . . .
C48 C 0.4091(9) 0.9461(14) 0.0793(8) 0.071(6) Uani 1 1 d . . . . .
H48A H 0.3703 0.9570 0.0528 0.085 Uiso 1 1 calc R U . . .
H48B H 0.4324 1.0038 0.0828 0.085 Uiso 1 1 calc R U . . .
H48C H 0.4269 0.8924 0.0684 0.085 Uiso 1 1 calc R U . . .
C49 C 0.3763(9) 1.0107(13) 0.1470(8) 0.073(6) Uani 1 1 d . . . . .
H49A H 0.3739 0.9963 0.1808 0.088 Uiso 1 1 calc R U . . .
H49B H 0.3994 1.0687 0.1504 0.088 Uiso 1 1 calc R U . . .
H49C H 0.3375 1.0209 0.1204 0.088 Uiso 1 1 calc R U . . .
C50 C 0.4649(8) 0.9068(14) 0.1714(8) 0.072(6) Uani 1 1 d . . . . .
H50A H 0.4618 0.8921 0.2049 0.087 Uiso 1 1 calc R U . . .
H50B H 0.4829 0.8529 0.1609 0.087 Uiso 1 1 calc R U . . .
H50C H 0.4884 0.9643 0.1754 0.087 Uiso 1 1 calc R U . . .
C51 C 0.3751(7) 0.5736(11) 0.1703(6) 0.049(4) Uani 1 1 d . . . . .
C52 C 0.3915(19) 0.520(3) 0.1352(17) 0.196(10) Uani 1 1 d . U . . .
H52A H 0.4205 0.5553 0.1270 0.235 Uiso 1 1 calc R U . . .
H52B H 0.4078 0.4584 0.1514 0.235 Uiso 1 1 calc R U . . .
H52C H 0.3577 0.5081 0.1028 0.235 Uiso 1 1 calc R U . . .
C53 C 0.3323(12) 0.519(2) 0.1815(11) 0.113(7) Uani 1 1 d . U . . .
H53A H 0.3201 0.5547 0.2059 0.136 Uiso 1 1 calc R U . . .
H53B H 0.2989 0.5071 0.1488 0.136 Uiso 1 1 calc R U . . .
H53C H 0.3489 0.4575 0.1974 0.136 Uiso 1 1 calc R U . . .
C54 C 0.4090(17) 0.599(3) 0.2299(15) 0.172(10) Uani 1 1 d . U . . .
H54A H 0.3845 0.6378 0.2424 0.207 Uiso 1 1 calc R U . . .
H54B H 0.4196 0.5396 0.2505 0.207 Uiso 1 1 calc R U . . .
H54C H 0.4439 0.6346 0.2340 0.207 Uiso 1 1 calc R U . . .
C55 C 0.2117(6) 0.7701(9) 0.0437(5) 0.035(3) Uani 1 1 d . . . . .
C56 C 0.1724(6) 0.7045(9) 0.0139(5) 0.032(3) Uani 1 1 d . . . . .
C60 C 0.0711(6) 0.7285(9) -0.0554(6) 0.037(4) Uani 1 1 d . . . . .
C61 C 0.0241(7) 0.7473(10) -0.0446(6) 0.039(4) Uani 1 1 d . . . . .
C62 C -0.0310(7) 0.7202(10) -0.0810(6) 0.042(4) Uani 1 1 d . . . . .
C63 C -0.0378(7) 0.6737(11) -0.1273(5) 0.042(4) Uani 1 1 d . . . . .
C64 C 0.0123(6) 0.6572(10) -0.1364(5) 0.037(4) Uani 1 1 d . . . . .
C65 C 0.0653(7) 0.6830(11) -0.1007(6) 0.040(4) Uani 1 1 d . . . . .
C66 C -0.0958(7) 0.6486(10) -0.1670(6) 0.041(4) Uani 1 1 d . . . . .
C67 C -0.1366(7) 0.6051(11) -0.1507(6) 0.045(4) Uani 1 1 d . . . . .
H67 H -0.1263 0.5916 -0.1145 0.054 Uiso 1 1 calc R U . . .
C68 C -0.1895(7) 0.5824(12) -0.1850(7) 0.050(4) Uani 1 1 d . . . . .
H68 H -0.2161 0.5524 -0.1732 0.060 Uiso 1 1 calc R U . . .
C69 C -0.2056(7) 0.6040(12) -0.2398(6) 0.047(4) Uani 1 1 d . . . . .
C70 C -0.1668(7) 0.6457(11) -0.2555(6) 0.047(4) Uani 1 1 d . . . . .
H70 H -0.1771 0.6605 -0.2916 0.056 Uiso 1 1 calc R U . . .
C71 C -0.1117(7) 0.6672(11) -0.2193(6) 0.042(4) Uani 1 1 d . . . . .
H71 H -0.0847 0.6955 -0.2312 0.050 Uiso 1 1 calc R U . . .
C72 C -0.2752(8) 0.5745(12) -0.3249(6) 0.055(5) Uani 1 1 d . . . . .
H72A H -0.3158 0.5565 -0.3424 0.066 Uiso 1 1 calc R U . . .
H72B H -0.2690 0.6369 -0.3379 0.066 Uiso 1 1 calc R U . . .
H72C H -0.2511 0.5263 -0.3323 0.066 Uiso 1 1 calc R U . . .
C81 C 0.3022(7) 0.7280(11) 0.8215(6) 0.041(4) Uani 1 1 d . . . . .
C82 C 0.3001(7) 0.6626(10) 0.8580(6) 0.042(4) Uani 1 1 d . . . . .
H82 H 0.2775 0.6064 0.8466 0.051 Uiso 1 1 calc R U . . .
C83 C 0.3305(7) 0.6777(11) 0.9108(6) 0.043(4) Uani 1 1 d . . . . .
C84 C 0.3634(7) 0.7595(11) 0.9255(6) 0.040(4) Uani 1 1 d . . . . .
H84 H 0.3837 0.7716 0.9619 0.048 Uiso 1 1 calc R U . . .
C85 C 0.3684(6) 0.8260(11) 0.8893(5) 0.040(4) Uani 1 1 d . . . . .
C86 C 0.3350(5) 0.8090(10) 0.8360(5) 0.031(3) Uani 1 1 d . . . . .
H86 H 0.3353 0.8535 0.8101 0.038 Uiso 1 1 calc R U . . .
C87 C 0.3284(8) 0.6103(12) 0.9529(6) 0.051(4) Uani 1 1 d . . . . .
C88 C 0.2818(11) 0.5269(16) 0.9281(9) 0.094(8) Uani 1 1 d . . . . .
H88A H 0.2920 0.4900 0.9028 0.113 Uiso 1 1 calc R U . . .
H88B H 0.2813 0.4844 0.9561 0.113 Uiso 1 1 calc R U . . .
H88C H 0.2436 0.5553 0.9102 0.113 Uiso 1 1 calc R U . . .
C89 C 0.3087(10) 0.6608(15) 0.9901(8) 0.078(6) Uani 1 1 d . . . . .
H89A H 0.2715 0.6915 0.9706 0.093 Uiso 1 1 calc R U . . .
H89B H 0.3044 0.6146 1.0151 0.093 Uiso 1 1 calc R U . . .
H89C H 0.3370 0.7095 1.0093 0.093 Uiso 1 1 calc R U . . .
C90 C 0.3850(13) 0.5609(19) 0.9790(13) 0.129(12) Uani 1 1 d . . . . .
H90A H 0.3955 0.5292 0.9523 0.155 Uiso 1 1 calc R U . . .
H90B H 0.4146 0.6080 0.9979 0.155 Uiso 1 1 calc R U . . .
H90C H 0.3820 0.5132 1.0037 0.155 Uiso 1 1 calc R U . . .
C91 C 0.4038(6) 0.9166(12) 0.9080(6) 0.046(4) Uani 1 1 d . . . . .
C92 C 0.3709(8) 0.9827(13) 0.9299(7) 0.063(5) Uani 1 1 d . . . . .
H92A H 0.3327 0.9957 0.9027 0.076 Uiso 1 1 calc R U . . .
H92B H 0.3666 0.9523 0.9601 0.076 Uiso 1 1 calc R U . . .
H92C H 0.3920 1.0430 0.9410 0.076 Uiso 1 1 calc R U . . .
C93 C 0.4623(7) 0.8952(14) 0.9483(8) 0.066(5) Uani 1 1 d . . . . .
H93A H 0.4586 0.8612 0.9779 0.079 Uiso 1 1 calc R U . . .
H93B H 0.4834 0.8551 0.9327 0.079 Uiso 1 1 calc R U . . .
H93C H 0.4833 0.9551 0.9609 0.079 Uiso 1 1 calc R U . . .
C94 C 0.4096(8) 0.9689(13) 0.8625(6) 0.062(5) Uani 1 1 d . . . . .
H94A H 0.3712 0.9830 0.8359 0.074 Uiso 1 1 calc R U . . .
H94B H 0.4306 1.0289 0.8750 0.074 Uiso 1 1 calc R U . . .
H94C H 0.4307 0.9288 0.8469 0.074 Uiso 1 1 calc R U . . .
C95 C 0.2671(7) 0.7104(10) 0.7637(6) 0.040(4) Uani 1 1 d . . . . .
C96 C 0.2354(6) 0.7711(10) 0.7258(6) 0.038(4) Uani 1 1 d . . . . .
C100 C 0.1762(7) 0.7394(11) 0.6293(6) 0.043(4) Uani 1 1 d . . . . .
C101 C 0.1974(7) 0.7481(12) 0.5919(7) 0.050(4) Uani 1 1 d . . . . .
C102 C 0.1606(7) 0.7710(12) 0.5404(6) 0.048(4) Uani 1 1 d . . . . .
C103 C 0.1025(6) 0.7837(11) 0.5259(6) 0.043(4) Uani 1 1 d . . . . .
C104 C 0.0840(7) 0.7694(11) 0.5649(6) 0.049(4) Uani 1 1 d . . . . .
C105 C 0.1180(7) 0.7490(11) 0.6159(6) 0.044(4) Uani 1 1 d . . . . .
C106 C 0.0653(6) 0.8069(12) 0.4701(7) 0.048(4) Uani 1 1 d . . . . .
C107 C 0.0708(7) 0.7638(11) 0.4283(5) 0.043(4) Uani 1 1 d . . . . .
H107 H 0.0991 0.7154 0.4344 0.051 Uiso 1 1 calc R U . . .
C108 C 0.0374(7) 0.7874(12) 0.3784(7) 0.049(4) Uani 1 1 d . . . . .
H108 H 0.0433 0.7571 0.3501 0.058 Uiso 1 1 calc R U . . .
C109 C -0.0052(7) 0.8549(12) 0.3680(6) 0.047(4) Uani 1 1 d . . . . .
C110 C -0.0160(8) 0.9013(16) 0.4098(7) 0.074(7) Uani 1 1 d . . . . .
H110 H -0.0462 0.9462 0.4036 0.088 Uiso 1 1 calc R U . . .
C111 C 0.0214(7) 0.8748(12) 0.4600(7) 0.053(4) Uani 1 1 d . . . . .
H111 H 0.0170 0.9045 0.4891 0.064 Uiso 1 1 calc R U . . .
C112 C -0.0807(8) 0.9434(14) 0.3041(7) 0.069(6) Uani 1 1 d . . . . .
H11C H -0.0995 0.9522 0.2660 0.083 Uiso 1 1 calc R U . . .
H11D H -0.1090 0.9207 0.3177 0.083 Uiso 1 1 calc R U . . .
H11E H -0.0646 1.0045 0.3207 0.083 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b31'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b31'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I16 C16 2.070(12) . ?
I56 C56 2.078(12) . ?
I96 C96 2.049(14) . ?
F21 C21 1.343(16) . ?
F22 C22 1.354(17) . ?
F24 C24 1.337(16) . ?
F25 C25 1.322(17) . ?
F61 C61 1.326(17) . ?
F62 C62 1.318(18) . ?
F64 C64 1.331(17) . ?
F65 C65 1.351(18) . ?
F101 C101 1.320(18) . ?
F102 C102 1.351(19) . ?
F104 C104 1.377(19) . ?
F105 C105 1.322(18) . ?
O29 C29 1.377(16) . ?
O29 C32 1.415(17) . ?
O69 C69 1.368(18) . ?
O69 C72 1.378(19) . ?
O109 C109 1.393(18) . ?
O109 C112 1.40(2) . ?
N17 C16 1.332(18) . ?
N17 N18 1.357(15) . ?
N17 C20 1.417(17) . ?
N18 N19 1.329(15) . ?
N19 C15 1.323(17) . ?
N57 N58 1.333(16) . ?
N57 C56 1.381(17) . ?
N57 C60 1.422(17) . ?
N58 N59 1.313(16) . ?
N59 C55 1.351(17) . ?
N97 C96 1.365(18) . ?
N97 N98 1.398(18) . ?
N97 C100 1.427(19) . ?
N98 N99 1.274(17) . ?
N99 C95 1.369(19) . ?
C1 C6 1.35(2) . ?
C1 C2 1.41(2) . ?
C1 C15 1.502(19) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.40(2) . ?
C3 C7 1.53(2) . ?
C4 C5 1.37(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(19) . ?
C5 C11 1.57(2) . ?
C6 H6 0.9500 . ?
C7 C9 1.50(2) . ?
C7 C8 1.52(2) . ?
C7 C10 1.54(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.50(2) . ?
C11 C12 1.52(2) . ?
C11 C14 1.61(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.355(19) . ?
C20 C21 1.37(2) . ?
C20 C25 1.38(2) . ?
C21 C22 1.368(19) . ?
C22 C23 1.38(2) . ?
C23 C24 1.38(2) . ?
C23 C26 1.474(19) . ?
C24 C25 1.373(19) . ?
C26 C31 1.39(2) . ?
C26 C27 1.40(2) . ?
C27 C28 1.391(19) . ?
C27 H27 0.9500 . ?
C28 C29 1.36(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.35(2) . ?
C30 C31 1.39(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C41 C46 1.358(19) . ?
C41 C42 1.395(19) . ?
C41 C55 1.472(19) . ?
C42 C43 1.398(19) . ?
C42 H42 0.9500 . ?
C43 C44 1.39(2) . ?
C43 C47 1.55(2) . ?
C44 C45 1.38(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.37(2) . ?
C45 C51 1.55(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.47(2) . ?
C47 C50 1.51(2) . ?
C47 C49 1.59(3) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.41(4) . ?
C51 C53 1.45(3) . ?
C51 C54 1.57(4) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 C56 1.367(18) . ?
C60 C61 1.35(2) . ?
C60 C65 1.36(2) . ?
C61 C62 1.41(2) . ?
C62 C63 1.39(2) . ?
C63 C64 1.40(2) . ?
C63 C66 1.49(2) . ?
C64 C65 1.37(2) . ?
C66 C71 1.37(2) . ?
C66 C67 1.41(2) . ?
C67 C68 1.34(2) . ?
C67 H67 0.9500 . ?
C68 C69 1.44(2) . ?
C68 H68 0.9500 . ?
C69 C70 1.35(2) . ?
C70 C71 1.39(2) . ?
C70 H70 0.9500 . ?
C71 H71 0.9500 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C81 C86 1.37(2) . ?
C81 C82 1.38(2) . ?
C81 C95 1.52(2) . ?
C82 C83 1.37(2) . ?
C82 H82 0.9500 . ?
C83 C84 1.38(2) . ?
C83 C87 1.52(2) . ?
C84 C85 1.41(2) . ?
C84 H84 0.9500 . ?
C85 C86 1.403(18) . ?
C85 C91 1.52(2) . ?
C86 H86 0.9500 . ?
C87 C89 1.48(3) . ?
C87 C90 1.49(3) . ?
C87 C88 1.61(3) . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 0.9800 . ?
C89 H89A 0.9800 . ?
C89 H89B 0.9800 . ?
C89 H89C 0.9800 . ?
C90 H90A 0.9800 . ?
C90 H90B 0.9800 . ?
C90 H90C 0.9800 . ?
C91 C93 1.49(2) . ?
C91 C94 1.51(2) . ?
C91 C92 1.52(2) . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C93 H93A 0.9800 . ?
C93 H93B 0.9800 . ?
C93 H93C 0.9800 . ?
C94 H94A 0.9800 . ?
C94 H94B 0.9800 . ?
C94 H94C 0.9800 . ?
C95 C96 1.343(19) . ?
C100 C101 1.34(2) . ?
C100 C105 1.37(2) . ?
C101 C102 1.40(2) . ?
C102 C103 1.37(2) . ?
C103 C104 1.35(2) . ?
C103 C106 1.50(2) . ?
C104 C105 1.36(2) . ?
C106 C107 1.36(2) . ?
C106 C111 1.40(2) . ?
C107 C108 1.35(2) . ?
C107 H107 0.9500 . ?
C108 C109 1.37(2) . ?
C108 H108 0.9500 . ?
C109 C110 1.44(3) . ?
C110 C111 1.39(2) . ?
C110 H110 0.9500 . ?
C111 H111 0.9500 . ?
C112 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 O29 C32 117.9(11) . . ?
C69 O69 C72 118.5(13) . . ?
C109 O109 C112 117.1(14) . . ?
C16 N17 N18 110.7(10) . . ?
C16 N17 C20 129.9(11) . . ?
N18 N17 C20 119.4(10) . . ?
N19 N18 N17 105.2(10) . . ?
C15 N19 N18 109.8(11) . . ?
N58 N57 C56 110.7(11) . . ?
N58 N57 C60 118.3(11) . . ?
C56 N57 C60 130.8(11) . . ?
N59 N58 N57 105.5(10) . . ?
N58 N59 C55 112.3(11) . . ?
C96 N97 N98 110.0(12) . . ?
C96 N97 C100 130.8(13) . . ?
N98 N97 C100 119.3(12) . . ?
N99 N98 N97 105.7(12) . . ?
N98 N99 C95 110.8(12) . . ?
C6 C1 C2 121.3(13) . . ?
C6 C1 C15 120.6(14) . . ?
C2 C1 C15 118.1(13) . . ?
C3 C2 C1 119.1(14) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.5(15) . . ?
C2 C3 C7 122.4(15) . . ?
C4 C3 C7 119.0(14) . . ?
C5 C4 C3 122.5(14) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 118.3(14) . . ?
C4 C5 C11 121.2(13) . . ?
C6 C5 C11 120.5(14) . . ?
C1 C6 C5 120.2(14) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C9 C7 C8 109.0(15) . . ?
C9 C7 C3 112.0(16) . . ?
C8 C7 C3 112.7(14) . . ?
C9 C7 C10 107.8(14) . . ?
C8 C7 C10 106.0(17) . . ?
C3 C7 C10 109.2(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 110.2(14) . . ?
C13 C11 C5 107.7(15) . . ?
C12 C11 C5 109.2(14) . . ?
C13 C11 C14 114.4(16) . . ?
C12 C11 C14 102.7(16) . . ?
C5 C11 C14 112.5(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N19 C15 C16 108.8(12) . . ?
N19 C15 C1 122.1(12) . . ?
C16 C15 C1 129.1(12) . . ?
N17 C16 C15 105.3(11) . . ?
N17 C16 I16 123.4(10) . . ?
C15 C16 I16 130.9(11) . . ?
C21 C20 C25 117.7(13) . . ?
C21 C20 N17 122.8(14) . . ?
C25 C20 N17 119.5(13) . . ?
F21 C21 C22 119.1(14) . . ?
F21 C21 C20 119.7(13) . . ?
C22 C21 C20 121.2(14) . . ?
F22 C22 C21 118.1(13) . . ?
F22 C22 C23 119.0(11) . . ?
C21 C22 C23 122.9(14) . . ?
C24 C23 C22 114.6(12) . . ?
C24 C23 C26 122.1(13) . . ?
C22 C23 C26 123.2(13) . . ?
F24 C24 C25 117.1(13) . . ?
F24 C24 C23 119.3(12) . . ?
C25 C24 C23 123.6(14) . . ?
F25 C25 C24 119.5(13) . . ?
F25 C25 C20 120.4(12) . . ?
C24 C25 C20 120.1(14) . . ?
C31 C26 C27 118.5(13) . . ?
C31 C26 C23 121.6(13) . . ?
C27 C26 C23 119.9(13) . . ?
C28 C27 C26 119.3(14) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C29 C28 C27 120.8(14) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 121.0(13) . . ?
C30 C29 O29 122.7(13) . . ?
C28 C29 O29 116.2(13) . . ?
C29 C30 C31 119.5(14) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C26 C31 C30 120.9(14) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
O29 C32 H32A 109.5 . . ?
O29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C46 C41 C42 118.2(14) . . ?
C46 C41 C55 123.4(13) . . ?
C42 C41 C55 118.4(12) . . ?
C41 C42 C43 121.2(13) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C44 C43 C42 116.0(13) . . ?
C44 C43 C47 124.1(13) . . ?
C42 C43 C47 120.0(12) . . ?
C45 C44 C43 124.9(14) . . ?
C45 C44 H44 117.6 . . ?
C43 C44 H44 117.6 . . ?
C46 C45 C44 115.3(14) . . ?
C46 C45 C51 123.2(14) . . ?
C44 C45 C51 121.2(14) . . ?
C41 C46 C45 124.4(15) . . ?
C41 C46 H46 117.8 . . ?
C45 C46 H46 117.8 . . ?
C48 C47 C50 110.5(16) . . ?
C48 C47 C43 109.3(13) . . ?
C50 C47 C43 111.5(14) . . ?
C48 C47 C49 109.1(15) . . ?
C50 C47 C49 109.6(15) . . ?
C43 C47 C49 106.7(13) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 C51 C53 108(2) . . ?
C52 C51 C45 108(2) . . ?
C53 C51 C45 111.1(17) . . ?
C52 C51 C54 131(3) . . ?
C53 C51 C54 92(2) . . ?
C45 C51 C54 105.2(19) . . ?
C51 C52 H52A 109.4 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N59 C55 C56 106.1(11) . . ?
N59 C55 C41 120.9(12) . . ?
C56 C55 C41 132.7(12) . . ?
C55 C56 N57 105.3(11) . . ?
C55 C56 I56 133.9(10) . . ?
N57 C56 I56 120.8(9) . . ?
C61 C60 C65 120.2(14) . . ?
C61 C60 N57 118.6(14) . . ?
C65 C60 N57 121.1(14) . . ?
F61 C61 C60 123.1(13) . . ?
F61 C61 C62 117.4(14) . . ?
C60 C61 C62 119.5(14) . . ?
F62 C62 C63 120.4(14) . . ?
F62 C62 C61 118.3(14) . . ?
C63 C62 C61 121.3(16) . . ?
C62 C63 C64 116.5(14) . . ?
C62 C63 C66 121.7(15) . . ?
C64 C63 C66 121.7(13) . . ?
F64 C64 C65 119.0(15) . . ?
F64 C64 C63 119.3(13) . . ?
C65 C64 C63 121.6(14) . . ?
F65 C65 C64 118.4(14) . . ?
F65 C65 C60 120.6(13) . . ?
C64 C65 C60 120.9(15) . . ?
C71 C66 C67 117.9(14) . . ?
C71 C66 C63 122.4(15) . . ?
C67 C66 C63 119.8(14) . . ?
C68 C67 C66 121.8(15) . . ?
C68 C67 H67 119.1 . . ?
C66 C67 H67 119.1 . . ?
C67 C68 C69 119.3(16) . . ?
C67 C68 H68 120.3 . . ?
C69 C68 H68 120.3 . . ?
C70 C69 O69 126.0(15) . . ?
C70 C69 C68 119.1(14) . . ?
O69 C69 C68 114.9(14) . . ?
C69 C70 C71 120.5(14) . . ?
C69 C70 H70 119.7 . . ?
C71 C70 H70 119.7 . . ?
C66 C71 C70 121.3(15) . . ?
C66 C71 H71 119.3 . . ?
C70 C71 H71 119.3 . . ?
O69 C72 H72A 109.5 . . ?
O69 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
O69 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C86 C81 C82 121.8(14) . . ?
C86 C81 C95 118.8(14) . . ?
C82 C81 C95 119.4(14) . . ?
C83 C82 C81 120.7(14) . . ?
C83 C82 H82 119.7 . . ?
C81 C82 H82 119.7 . . ?
C84 C83 C82 117.7(14) . . ?
C84 C83 C87 119.0(14) . . ?
C82 C83 C87 123.3(15) . . ?
C83 C84 C85 123.2(13) . . ?
C83 C84 H84 118.4 . . ?
C85 C84 H84 118.4 . . ?
C86 C85 C84 116.9(13) . . ?
C86 C85 C91 122.1(14) . . ?
C84 C85 C91 120.8(13) . . ?
C81 C86 C85 119.7(14) . . ?
C81 C86 H86 120.2 . . ?
C85 C86 H86 120.2 . . ?
C89 C87 C90 113.6(18) . . ?
C89 C87 C83 111.0(15) . . ?
C90 C87 C83 110.3(16) . . ?
C89 C87 C88 104.7(17) . . ?
C90 C87 C88 105.8(19) . . ?
C83 C87 C88 111.1(14) . . ?
C87 C88 H88A 109.5 . . ?
C87 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C87 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C87 C89 H89A 109.5 . . ?
C87 C89 H89B 109.5 . . ?
H89A C89 H89B 109.5 . . ?
C87 C89 H89C 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
C87 C90 H90A 109.5 . . ?
C87 C90 H90B 109.5 . . ?
H90A C90 H90B 109.5 . . ?
C87 C90 H90C 109.5 . . ?
H90A C90 H90C 109.5 . . ?
H90B C90 H90C 109.5 . . ?
C93 C91 C94 109.4(15) . . ?
C93 C91 C85 111.5(14) . . ?
C94 C91 C85 110.8(13) . . ?
C93 C91 C92 111.1(15) . . ?
C94 C91 C92 106.4(15) . . ?
C85 C91 C92 107.6(14) . . ?
C91 C92 H92A 109.5 . . ?
C91 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C91 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C91 C93 H93A 109.5 . . ?
C91 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
C91 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?
C91 C94 H94A 109.5 . . ?
C91 C94 H94B 109.5 . . ?
H94A C94 H94B 109.5 . . ?
C91 C94 H94C 109.5 . . ?
H94A C94 H94C 109.5 . . ?
H94B C94 H94C 109.5 . . ?
C96 C95 N99 109.2(12) . . ?
C96 C95 C81 130.2(13) . . ?
N99 C95 C81 120.6(12) . . ?
C95 C96 N97 104.4(13) . . ?
C95 C96 I96 131.9(11) . . ?
N97 C96 I96 123.6(10) . . ?
C101 C100 C105 119.1(14) . . ?
C101 C100 N97 121.1(15) . . ?
C105 C100 N97 119.8(16) . . ?
F101 C101 C100 121.9(15) . . ?
F101 C101 C102 118.1(16) . . ?
C100 C101 C102 119.9(15) . . ?
F102 C102 C103 120.6(13) . . ?
F102 C102 C101 116.9(15) . . ?
C103 C102 C101 122.4(16) . . ?
C104 C103 C102 114.3(14) . . ?
C104 C103 C106 125.7(15) . . ?
C102 C103 C106 120.0(15) . . ?
C103 C104 C105 125.7(16) . . ?
C103 C104 F104 118.3(13) . . ?
C105 C104 F104 116.0(16) . . ?
F105 C105 C104 121.4(16) . . ?
F105 C105 C100 120.0(15) . . ?
C104 C105 C100 118.5(16) . . ?
C107 C106 C111 117.7(15) . . ?
C107 C106 C103 123.4(15) . . ?
C111 C106 C103 118.9(16) . . ?
C108 C107 C106 122.2(16) . . ?
C108 C107 H107 118.9 . . ?
C106 C107 H107 118.9 . . ?
C107 C108 C109 120.5(16) . . ?
C107 C108 H108 119.7 . . ?
C109 C108 H108 119.7 . . ?
C108 C109 O109 116.4(16) . . ?
C108 C109 C110 121.3(15) . . ?
O109 C109 C110 122.3(15) . . ?
C111 C110 C109 114(2) . . ?
C111 C110 H110 122.8 . . ?
C109 C110 H110 122.8 . . ?
C110 C111 C106 123.8(19) . . ?
C110 C111 H111 118.1 . . ?
C106 C111 H111 118.1 . . ?
O109 C112 H11C 109.5 . . ?
O109 C112 H11D 109.5 . . ?
H11C C112 H11D 109.5 . . ?
O109 C112 H11E 109.5 . . ?
H11C C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N17 N18 N19 -1.7(16) . . . . ?
C20 N17 N18 N19 178.5(12) . . . . ?
N17 N18 N19 C15 2.1(15) . . . . ?
C56 N57 N58 N59 -0.6(18) . . . . ?
C60 N57 N58 N59 174.7(14) . . . . ?
N57 N58 N59 C55 1.6(19) . . . . ?
C96 N97 N98 N99 -1.0(19) . . . . ?
C100 N97 N98 N99 179.3(15) . . . . ?
N97 N98 N99 C95 -0.1(19) . . . . ?
C6 C1 C2 C3 -2(2) . . . . ?
C15 C1 C2 C3 177.2(13) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 C2 C3 C7 -176.6(13) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C7 C3 C4 C5 176.4(15) . . . . ?
C3 C4 C5 C6 2(2) . . . . ?
C3 C4 C5 C11 -177.3(15) . . . . ?
C2 C1 C6 C5 3(2) . . . . ?
C15 C1 C6 C5 -175.2(13) . . . . ?
C4 C5 C6 C1 -4(2) . . . . ?
C11 C5 C6 C1 175.7(14) . . . . ?
C2 C3 C7 C9 -129.6(17) . . . . ?
C4 C3 C7 C9 54(2) . . . . ?
C2 C3 C7 C8 -6(2) . . . . ?
C4 C3 C7 C8 177.2(15) . . . . ?
C2 C3 C7 C10 111.2(17) . . . . ?
C4 C3 C7 C10 -65(2) . . . . ?
C4 C5 C11 C13 70.8(19) . . . . ?
C6 C5 C11 C13 -108.7(17) . . . . ?
C4 C5 C11 C12 -49(2) . . . . ?
C6 C5 C11 C12 131.6(16) . . . . ?
C4 C5 C11 C14 -162.3(16) . . . . ?
C6 C5 C11 C14 18(2) . . . . ?
N18 N19 C15 C16 -1.7(16) . . . . ?
N18 N19 C15 C1 178.6(13) . . . . ?
C6 C1 C15 N19 -141.4(14) . . . . ?
C2 C1 C15 N19 40(2) . . . . ?
C6 C1 C15 C16 39(2) . . . . ?
C2 C1 C15 C16 -139.8(15) . . . . ?
N18 N17 C16 C15 0.7(17) . . . . ?
C20 N17 C16 C15 -179.5(15) . . . . ?
N18 N17 C16 I16 174.5(10) . . . . ?
C20 N17 C16 I16 -6(2) . . . . ?
N19 C15 C16 N17 0.6(16) . . . . ?
C1 C15 C16 N17 -179.7(14) . . . . ?
N19 C15 C16 I16 -172.5(11) . . . . ?
C1 C15 C16 I16 7(2) . . . . ?
C16 N17 C20 C21 -71(2) . . . . ?
N18 N17 C20 C21 108.3(16) . . . . ?
C16 N17 C20 C25 110.9(18) . . . . ?
N18 N17 C20 C25 -69.4(18) . . . . ?
C25 C20 C21 F21 -179.4(12) . . . . ?
N17 C20 C21 F21 3(2) . . . . ?
C25 C20 C21 C22 1(2) . . . . ?
N17 C20 C21 C22 -176.3(13) . . . . ?
F21 C21 C22 F22 -1(2) . . . . ?
C20 C21 C22 F22 178.6(13) . . . . ?
F21 C21 C22 C23 178.5(13) . . . . ?
C20 C21 C22 C23 -2(2) . . . . ?
F22 C22 C23 C24 -179.3(12) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
F22 C22 C23 C26 -2(2) . . . . ?
C21 C22 C23 C26 179.2(14) . . . . ?
C22 C23 C24 F24 178.3(13) . . . . ?
C26 C23 C24 F24 1(2) . . . . ?
C22 C23 C24 C25 0(2) . . . . ?
C26 C23 C24 C25 -177.8(13) . . . . ?
F24 C24 C25 F25 3(2) . . . . ?
C23 C24 C25 F25 -179.0(13) . . . . ?
F24 C24 C25 C20 -179.1(12) . . . . ?
C23 C24 C25 C20 -1(2) . . . . ?
C21 C20 C25 F25 178.4(13) . . . . ?
N17 C20 C25 F25 -4(2) . . . . ?
C21 C20 C25 C24 0(2) . . . . ?
N17 C20 C25 C24 177.8(13) . . . . ?
C24 C23 C26 C31 -45(2) . . . . ?
C22 C23 C26 C31 137.1(15) . . . . ?
C24 C23 C26 C27 134.5(15) . . . . ?
C22 C23 C26 C27 -43(2) . . . . ?
C31 C26 C27 C28 1(2) . . . . ?
C23 C26 C27 C28 -178.6(14) . . . . ?
C26 C27 C28 C29 1(2) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
C27 C28 C29 O29 179.9(14) . . . . ?
C32 O29 C29 C30 5(2) . . . . ?
C32 O29 C29 C28 -178.0(13) . . . . ?
C28 C29 C30 C31 3(2) . . . . ?
O29 C29 C30 C31 179.7(13) . . . . ?
C27 C26 C31 C30 -1(2) . . . . ?
C23 C26 C31 C30 178.4(13) . . . . ?
C29 C30 C31 C26 -1(2) . . . . ?
C46 C41 C42 C43 3(2) . . . . ?
C55 C41 C42 C43 -177.2(14) . . . . ?
C41 C42 C43 C44 0(2) . . . . ?
C41 C42 C43 C47 178.1(14) . . . . ?
C42 C43 C44 C45 -3(2) . . . . ?
C47 C43 C44 C45 179.2(15) . . . . ?
C43 C44 C45 C46 2(2) . . . . ?
C43 C44 C45 C51 176.6(15) . . . . ?
C42 C41 C46 C45 -3(2) . . . . ?
C55 C41 C46 C45 176.8(15) . . . . ?
C44 C45 C46 C41 1(2) . . . . ?
C51 C45 C46 C41 -173.4(15) . . . . ?
C44 C43 C47 C48 115.7(17) . . . . ?
C42 C43 C47 C48 -62(2) . . . . ?
C44 C43 C47 C50 -7(2) . . . . ?
C42 C43 C47 C50 175.1(15) . . . . ?
C44 C43 C47 C49 -126.4(16) . . . . ?
C42 C43 C47 C49 55.5(19) . . . . ?
C46 C45 C51 C52 85(3) . . . . ?
C44 C45 C51 C52 -89(3) . . . . ?
C46 C45 C51 C53 -33(2) . . . . ?
C44 C45 C51 C53 152.8(18) . . . . ?
C46 C45 C51 C54 -132(2) . . . . ?
C44 C45 C51 C54 54(2) . . . . ?
N58 N59 C55 C56 -2.0(19) . . . . ?
N58 N59 C55 C41 173.3(14) . . . . ?
C46 C41 C55 N59 159.9(15) . . . . ?
C42 C41 C55 N59 -20(2) . . . . ?
C46 C41 C55 C56 -26(3) . . . . ?
C42 C41 C55 C56 153.7(17) . . . . ?
N59 C55 C56 N57 1.4(17) . . . . ?
C41 C55 C56 N57 -173.0(16) . . . . ?
N59 C55 C56 I56 -177.3(12) . . . . ?
C41 C55 C56 I56 8(3) . . . . ?
N58 N57 C56 C55 -0.5(18) . . . . ?
C60 N57 C56 C55 -175.1(16) . . . . ?
N58 N57 C56 I56 178.4(11) . . . . ?
C60 N57 C56 I56 4(2) . . . . ?
N58 N57 C60 C61 -63.0(19) . . . . ?
C56 N57 C60 C61 111.2(18) . . . . ?
N58 N57 C60 C65 116.6(16) . . . . ?
C56 N57 C60 C65 -69(2) . . . . ?
C65 C60 C61 F61 -178.9(13) . . . . ?
N57 C60 C61 F61 1(2) . . . . ?
C65 C60 C61 C62 -1(2) . . . . ?
N57 C60 C61 C62 179.0(12) . . . . ?
F61 C61 C62 F62 0.6(19) . . . . ?
C60 C61 C62 F62 -177.7(12) . . . . ?
F61 C61 C62 C63 179.1(13) . . . . ?
C60 C61 C62 C63 1(2) . . . . ?
F62 C62 C63 C64 177.1(13) . . . . ?
C61 C62 C63 C64 -1(2) . . . . ?
F62 C62 C63 C66 1(2) . . . . ?
C61 C62 C63 C66 -177.3(13) . . . . ?
C62 C63 C64 F64 -179.6(13) . . . . ?
C66 C63 C64 F64 -4(2) . . . . ?
C62 C63 C64 C65 2(2) . . . . ?
C66 C63 C64 C65 177.9(14) . . . . ?
F64 C64 C65 F65 2(2) . . . . ?
C63 C64 C65 F65 -179.8(13) . . . . ?
F64 C64 C65 C60 179.6(13) . . . . ?
C63 C64 C65 C60 -2(2) . . . . ?
C61 C60 C65 F65 179.0(12) . . . . ?
N57 C60 C65 F65 -1(2) . . . . ?
C61 C60 C65 C64 1(2) . . . . ?
N57 C60 C65 C64 -178.4(13) . . . . ?
C62 C63 C66 C71 132.6(16) . . . . ?
C64 C63 C66 C71 -43(2) . . . . ?
C62 C63 C66 C67 -46(2) . . . . ?
C64 C63 C66 C67 137.8(15) . . . . ?
C71 C66 C67 C68 0(2) . . . . ?
C63 C66 C67 C68 179.2(15) . . . . ?
C66 C67 C68 C69 -1(2) . . . . ?
C72 O69 C69 C70 17(3) . . . . ?
C72 O69 C69 C68 -163.5(15) . . . . ?
C67 C68 C69 C70 1(3) . . . . ?
C67 C68 C69 O69 -178.8(15) . . . . ?
O69 C69 C70 C71 179.8(16) . . . . ?
C68 C69 C70 C71 0(3) . . . . ?
C67 C66 C71 C70 1(2) . . . . ?
C63 C66 C71 C70 -178.1(14) . . . . ?
C69 C70 C71 C66 -1(3) . . . . ?
C86 C81 C82 C83 1(2) . . . . ?
C95 C81 C82 C83 -178.7(14) . . . . ?
C81 C82 C83 C84 -1(2) . . . . ?
C81 C82 C83 C87 177.8(15) . . . . ?
C82 C83 C84 C85 -2(2) . . . . ?
C87 C83 C84 C85 179.5(15) . . . . ?
C83 C84 C85 C86 4(2) . . . . ?
C83 C84 C85 C91 178.1(14) . . . . ?
C82 C81 C86 C85 1(2) . . . . ?
C95 C81 C86 C85 -179.2(13) . . . . ?
C84 C85 C86 C81 -3(2) . . . . ?
C91 C85 C86 C81 -177.5(14) . . . . ?
C84 C83 C87 C89 57(2) . . . . ?
C82 C83 C87 C89 -121.9(18) . . . . ?
C84 C83 C87 C90 -70(2) . . . . ?
C82 C83 C87 C90 111(2) . . . . ?
C84 C83 C87 C88 172.8(16) . . . . ?
C82 C83 C87 C88 -6(2) . . . . ?
C86 C85 C91 C93 -136.2(16) . . . . ?
C84 C85 C91 C93 50(2) . . . . ?
C86 C85 C91 C94 -14(2) . . . . ?
C84 C85 C91 C94 171.8(15) . . . . ?
C86 C85 C91 C92 101.7(17) . . . . ?
C84 C85 C91 C92 -72.3(18) . . . . ?
N98 N99 C95 C96 1(2) . . . . ?
N98 N99 C95 C81 178.4(15) . . . . ?
C86 C81 C95 C96 -42(2) . . . . ?
C82 C81 C95 C96 137.7(18) . . . . ?
C86 C81 C95 N99 141.1(16) . . . . ?
C82 C81 C95 N99 -39(2) . . . . ?
N99 C95 C96 N97 -1.7(18) . . . . ?
C81 C95 C96 N97 -178.6(16) . . . . ?
N99 C95 C96 I96 -178.1(12) . . . . ?
C81 C95 C96 I96 5(3) . . . . ?
N98 N97 C96 C95 1.6(18) . . . . ?
C100 N97 C96 C95 -178.7(17) . . . . ?
N98 N97 C96 I96 178.5(11) . . . . ?
C100 N97 C96 I96 -2(3) . . . . ?
C96 N97 C100 C101 102(2) . . . . ?
N98 N97 C100 C101 -78(2) . . . . ?
C96 N97 C100 C105 -81(2) . . . . ?
N98 N97 C100 C105 98.7(18) . . . . ?
C105 C100 C101 F101 179.5(15) . . . . ?
N97 C100 C101 F101 -4(2) . . . . ?
C105 C100 C101 C102 3(2) . . . . ?
N97 C100 C101 C102 179.5(15) . . . . ?
F101 C101 C102 F102 -1(2) . . . . ?
C100 C101 C102 F102 176.0(15) . . . . ?
F101 C101 C102 C103 -178.0(16) . . . . ?
C100 C101 C102 C103 -1(3) . . . . ?
F102 C102 C103 C104 -178.9(15) . . . . ?
C101 C102 C103 C104 -2(2) . . . . ?
F102 C102 C103 C106 4(2) . . . . ?
C101 C102 C103 C106 -179.3(16) . . . . ?
C102 C103 C104 C105 3(2) . . . . ?
C106 C103 C104 C105 -179.4(16) . . . . ?
C102 C103 C104 F104 -178.5(14) . . . . ?
C106 C103 C104 F104 -1(2) . . . . ?
C103 C104 C105 F105 178.7(15) . . . . ?
F104 C104 C105 F105 1(2) . . . . ?
C103 C104 C105 C100 -2(3) . . . . ?
F104 C104 C105 C100 -180.0(13) . . . . ?
C101 C100 C105 F105 178.0(15) . . . . ?
N97 C100 C105 F105 1(2) . . . . ?
C101 C100 C105 C104 -1(2) . . . . ?
N97 C100 C105 C104 -178.2(14) . . . . ?
C104 C103 C106 C107 -134.7(19) . . . . ?
C102 C103 C106 C107 42(2) . . . . ?
C104 C103 C106 C111 44(2) . . . . ?
C102 C103 C106 C111 -139.3(17) . . . . ?
C111 C106 C107 C108 3(3) . . . . ?
C103 C106 C107 C108 -178.7(15) . . . . ?
C106 C107 C108 C109 -2(3) . . . . ?
C107 C108 C109 O109 178.5(15) . . . . ?
C107 C108 C109 C110 -1(2) . . . . ?
C112 O109 C109 C108 178.9(16) . . . . ?
C112 O109 C109 C110 -2(2) . . . . ?
C108 C109 C110 C111 3(2) . . . . ?
O109 C109 C110 C111 -176.8(15) . . . . ?
C109 C110 C111 C106 -2(3) . . . . ?
C107 C106 C111 C110 -1(3) . . . . ?
C103 C106 C111 C110 -179.4(16) . . . . ?

#==============================================================================

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





#==END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Acetonitrile
