# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1824277'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H10 F10 I4 N2 O'
_chemical_formula_weight         1136.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.9014(2)
_cell_length_b                   16.0841(4)
_cell_length_c                   18.1379(4)
_cell_angle_alpha                79.028(2)
_cell_angle_beta                 83.942(2)
_cell_angle_gamma                67.838(2)
_cell_volume                     3419.61(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18447
_cell_measurement_theta_min      4.3150
_cell_measurement_theta_max      76.0680

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_F_000             2104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    29.397
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.047
_exptl_absorpt_correction_T_max  0.377
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2977
_diffrn_reflns_number            42308
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.574
_diffrn_reflns_theta_max         76.180
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             14185
_reflns_number_gt                12240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+1.5933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14185
_refine_ls_number_parameters     883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2164(6) 0.4666(5) 0.3178(4) 0.0845(16) Uani 1 1 d . . . . .
H1 H 0.2434 0.4398 0.2751 0.101 Uiso 1 1 calc R U . . .
C2 C 0.2846(6) 0.4463(5) 0.3770(4) 0.0857(16) Uani 1 1 d . . . . .
H2 H 0.3580 0.4053 0.3744 0.103 Uiso 1 1 calc R U . . .
C3 C 0.2455(5) 0.4863(4) 0.4405(3) 0.0740(12) Uani 1 1 d . . . . .
H3 H 0.2924 0.4725 0.4803 0.089 Uiso 1 1 calc R U . . .
C4 C 0.1361(4) 0.5469(4) 0.4446(3) 0.0643(10) Uani 1 1 d . . . . .
C5 C 0.0665(5) 0.5679(5) 0.3847(3) 0.0821(16) Uani 1 1 d . . . . .
H5 H -0.0069 0.6089 0.3869 0.099 Uiso 1 1 calc R U . . .
C6 C 0.1077(6) 0.5271(6) 0.3220(4) 0.0919(19) Uani 1 1 d . . . . .
H6 H 0.0614 0.5406 0.2820 0.110 Uiso 1 1 calc R U . . .
C7 C 0.0945(4) 0.5905(4) 0.5111(3) 0.0662(11) Uani 1 1 d . . . . .
C8 C -0.0260(5) 0.6712(4) 0.5835(3) 0.0683(11) Uani 1 1 d . . . . .
C9 C -0.1351(5) 0.7299(4) 0.6100(3) 0.0727(12) Uani 1 1 d . . . . .
C10 C -0.1425(8) 0.7595(6) 0.6781(4) 0.108(2) Uani 1 1 d . . . . .
H10 H -0.0786 0.7451 0.7048 0.129 Uiso 1 1 calc R U . . .
C11 C -0.2467(9) 0.8110(7) 0.7053(6) 0.141(4) Uani 1 1 d . . . . .
H11 H -0.2534 0.8310 0.7510 0.170 Uiso 1 1 calc R U . . .
C12 C -0.3412(8) 0.8328(7) 0.6646(6) 0.128(3) Uani 1 1 d . . . . .
H12 H -0.4110 0.8666 0.6838 0.153 Uiso 1 1 calc R U . . .
C13 C -0.3332(6) 0.8058(6) 0.5974(5) 0.102(2) Uani 1 1 d . . . . .
H13 H -0.3969 0.8218 0.5701 0.123 Uiso 1 1 calc R U . . .
C14 C -0.2287(5) 0.7535(4) 0.5695(4) 0.0812(14) Uani 1 1 d . . . . .
H14 H -0.2225 0.7345 0.5234 0.097 Uiso 1 1 calc R U . . .
C15 C 0.7387(7) -0.0729(5) 0.3293(5) 0.101(2) Uani 1 1 d . . . . .
H15 H 0.7017 -0.0714 0.2875 0.121 Uiso 1 1 calc R U . . .
C16 C 0.6796(6) -0.0262(6) 0.3857(6) 0.108(3) Uani 1 1 d . . . . .
H16 H 0.6029 0.0059 0.3821 0.129 Uiso 1 1 calc R U . . .
C17 C 0.7339(5) -0.0268(5) 0.4481(4) 0.0925(18) Uani 1 1 d . . . . .
H17 H 0.6938 0.0048 0.4862 0.111 Uiso 1 1 calc R U . . .
C18 C 0.8476(4) -0.0744(4) 0.4530(3) 0.0645(10) Uani 1 1 d . . . . .
C19 C 0.9066(5) -0.1223(5) 0.3957(3) 0.0778(14) Uani 1 1 d . . . . .
H19 H 0.9832 -0.1549 0.3990 0.093 Uiso 1 1 calc R U . . .
C20 C 0.8515(6) -0.1215(5) 0.3340(4) 0.0909(18) Uani 1 1 d . . . . .
H20 H 0.8907 -0.1538 0.2960 0.109 Uiso 1 1 calc R U . . .
C21 C 0.9061(4) -0.0747(3) 0.5170(3) 0.0622(10) Uani 1 1 d . . . . .
C22 C 1.0436(4) -0.1122(4) 0.5880(3) 0.0651(10) Uani 1 1 d . . . . .
C23 C 1.1589(4) -0.1593(4) 0.6124(3) 0.0677(11) Uani 1 1 d . . . . .
C24 C 1.1862(6) -0.1507(6) 0.6819(4) 0.103(2) Uani 1 1 d . . . . .
H24 H 1.1310 -0.1182 0.7139 0.124 Uiso 1 1 calc R U . . .
C25 C 1.2965(7) -0.1909(7) 0.7029(4) 0.112(3) Uani 1 1 d . . . . .
H25 H 1.3153 -0.1851 0.7493 0.134 Uiso 1 1 calc R U . . .
C26 C 1.3779(6) -0.2390(5) 0.6567(4) 0.0920(18) Uani 1 1 d . . . . .
H26 H 1.4519 -0.2649 0.6712 0.110 Uiso 1 1 calc R U . . .
C27 C 1.3509(5) -0.2492(5) 0.5883(4) 0.0914(18) Uani 1 1 d . . . . .
H27 H 1.4061 -0.2830 0.5570 0.110 Uiso 1 1 calc R U . . .
C28 C 1.2410(5) -0.2090(4) 0.5667(3) 0.0758(13) Uani 1 1 d . . . . .
H28 H 1.2227 -0.2157 0.5206 0.091 Uiso 1 1 calc R U . . .
C29 C 0.5444(4) 0.4117(3) 0.6797(3) 0.0569(9) Uani 1 1 d . . . . .
C30 C 0.6282(4) 0.3599(3) 0.6351(3) 0.0647(10) Uani 1 1 d . . . . .
C31 C 0.7333(4) 0.3108(3) 0.6615(3) 0.0673(11) Uani 1 1 d . . . . .
C32 C 0.7572(4) 0.3137(3) 0.7320(3) 0.0625(10) Uani 1 1 d . . . . .
C33 C 0.6744(3) 0.3648(3) 0.7787(2) 0.0537(8) Uani 1 1 d . . . . .
C34 C 0.5672(3) 0.4144(3) 0.7525(2) 0.0506(8) Uani 1 1 d . . . . .
C35 C 0.4777(3) 0.4690(3) 0.8021(2) 0.0506(8) Uani 1 1 d . . . . .
C36 C 0.3959(3) 0.4382(3) 0.8387(2) 0.0526(8) Uani 1 1 d . . . . .
C37 C 0.3116(3) 0.4855(3) 0.8864(2) 0.0533(8) Uani 1 1 d . . . . .
C38 C 0.3125(3) 0.5684(3) 0.8965(3) 0.0575(9) Uani 1 1 d . . . . .
C39 C 0.3909(4) 0.6024(3) 0.8610(3) 0.0567(9) Uani 1 1 d . . . . .
C40 C 0.4715(3) 0.5533(3) 0.8136(2) 0.0534(8) Uani 1 1 d . . . . .
C41 C 0.2241(3) 0.4498(3) 0.9225(3) 0.0559(9) Uani 1 1 d . . . . .
C42 C 0.1282(4) 0.4687(4) 0.8826(3) 0.0658(11) Uani 1 1 d . . . . .
C43 C 0.0485(4) 0.4327(4) 0.9150(4) 0.0763(14) Uani 1 1 d . . . . .
C44 C 0.0620(4) 0.3810(4) 0.9849(4) 0.0809(16) Uani 1 1 d . . . . .
C45 C 0.1546(4) 0.3642(4) 1.0244(3) 0.0692(12) Uani 1 1 d . . . . .
C46 C 0.2359(4) 0.3988(3) 0.9935(3) 0.0607(10) Uani 1 1 d . . . . .
C47 C 0.4819(3) 0.1767(3) 0.6753(2) 0.0562(9) Uani 1 1 d . . . . .
C48 C 0.4022(4) 0.2402(4) 0.6277(3) 0.0648(10) Uani 1 1 d . . . . .
C49 C 0.2972(4) 0.2858(4) 0.6545(3) 0.0697(12) Uani 1 1 d . . . . .
C50 C 0.2687(4) 0.2687(3) 0.7286(3) 0.0645(11) Uani 1 1 d . . . . .
C51 C 0.3466(3) 0.2054(3) 0.7784(2) 0.0544(8) Uani 1 1 d . . . . .
C52 C 0.4545(3) 0.1593(3) 0.7520(2) 0.0494(7) Uani 1 1 d . . . . .
C53 C 0.5391(3) 0.0906(3) 0.8037(2) 0.0482(7) Uani 1 1 d . . . . .
C54 C 0.6186(3) 0.1114(3) 0.8346(2) 0.0510(8) Uani 1 1 d . . . . .
C55 C 0.7011(3) 0.0490(3) 0.8824(2) 0.0500(8) Uani 1 1 d . . . . .
C56 C 0.7002(3) -0.0385(3) 0.8987(2) 0.0530(8) Uani 1 1 d . . . . .
C57 C 0.6235(3) -0.0623(3) 0.8696(3) 0.0547(8) Uani 1 1 d . . . . .
C58 C 0.5450(3) 0.0021(3) 0.8219(2) 0.0513(8) Uani 1 1 d . . . . .
C59 C 0.7882(3) 0.0732(3) 0.9105(2) 0.0523(8) Uani 1 1 d . . . . .
C60 C 0.8870(4) 0.0648(3) 0.8681(3) 0.0588(9) Uani 1 1 d . . . . .
C61 C 0.9666(4) 0.0886(4) 0.8945(3) 0.0697(12) Uani 1 1 d . . . . .
C62 C 0.9511(4) 0.1193(4) 0.9618(3) 0.0727(13) Uani 1 1 d . . . . .
C63 C 0.8548(4) 0.1270(3) 1.0043(3) 0.0669(11) Uani 1 1 d . . . . .
C64 C 0.7723(4) 0.1041(3) 0.9792(3) 0.0583(9) Uani 1 1 d . . . . .
F1 F 0.6098(3) 0.3563(3) 0.56473(18) 0.0889(10) Uani 1 1 d . . . . .
F2 F 0.8137(3) 0.2617(3) 0.6170(2) 0.0897(10) Uani 1 1 d . . . . .
F3 F 0.8609(2) 0.2662(2) 0.7560(2) 0.0822(8) Uani 1 1 d . . . . .
F4 F 0.3977(2) 0.3577(2) 0.82751(18) 0.0703(7) Uani 1 1 d . . . . .
F5 F 0.5472(2) 0.58740(19) 0.78010(18) 0.0671(6) Uani 1 1 d . . . . .
F6 F 0.3886(3) 0.6834(2) 0.8721(2) 0.0756(8) Uani 1 1 d . . . . .
F7 F 0.2347(2) 0.6178(2) 0.94162(19) 0.0750(8) Uani 1 1 d . . . . .
F8 F -0.0432(3) 0.4487(4) 0.8789(3) 0.1084(14) Uani 1 1 d . . . . .
F9 F -0.0154(3) 0.3465(3) 1.0153(3) 0.1110(14) Uani 1 1 d . . . . .
F10 F 0.1642(3) 0.3150(3) 1.0935(2) 0.0965(11) Uani 1 1 d . . . . .
F11 F 0.4258(3) 0.2575(3) 0.55381(18) 0.0889(10) Uani 1 1 d . . . . .
F12 F 0.2204(3) 0.3462(3) 0.6068(2) 0.0932(11) Uani 1 1 d . . . . .
F13 F 0.1634(2) 0.3125(2) 0.7525(2) 0.0865(9) Uani 1 1 d . . . . .
F14 F 0.6176(2) 0.19632(18) 0.81666(18) 0.0674(7) Uani 1 1 d . . . . .
F15 F 0.4730(2) -0.02363(19) 0.79281(18) 0.0674(6) Uani 1 1 d . . . . .
F16 F 0.6256(3) -0.14769(19) 0.8866(2) 0.0761(8) Uani 1 1 d . . . . .
F17 F 0.7775(2) -0.1027(2) 0.94342(17) 0.0702(7) Uani 1 1 d . . . . .
F18 F 1.0625(3) 0.0818(4) 0.8547(3) 0.1045(13) Uani 1 1 d . . . . .
F19 F 1.0293(3) 0.1418(3) 0.9862(3) 0.1060(13) Uani 1 1 d . . . . .
F20 F 0.8422(4) 0.1567(3) 1.0692(2) 0.0964(11) Uani 1 1 d . . . . .
I1 I 0.38784(3) 0.48758(2) 0.63343(2) 0.07179(9) Uani 1 1 d . . . . .
I2 I 0.71704(3) 0.36347(2) 0.88628(2) 0.07504(9) Uani 1 1 d . . . . .
I3 I 0.10268(3) 0.54771(3) 0.77649(2) 0.08035(10) Uani 1 1 d . . . . .
I4 I 0.37471(4) 0.36850(3) 1.05512(3) 0.08774(12) Uani 1 1 d . . . . .
I5 I 0.63912(2) 0.10282(2) 0.62992(2) 0.06947(9) Uani 1 1 d . . . . .
I6 I 0.29574(3) 0.18012(2) 0.88979(2) 0.07370(9) Uani 1 1 d . . . . .
I7 I 0.91649(3) 0.01855(3) 0.76509(2) 0.07429(9) Uani 1 1 d . . . . .
I8 I 0.62741(4) 0.12171(4) 1.04370(3) 0.09563(14) Uani 1 1 d . . . . .
N1 N 0.1472(4) 0.5863(4) 0.5683(3) 0.0812(12) Uani 1 1 d . . . . .
N2 N 0.0691(4) 0.6394(4) 0.6164(3) 0.0834(13) Uani 1 1 d . . . . .
N3 N 0.8696(4) -0.0283(3) 0.5713(3) 0.0728(10) Uani 1 1 d . . . . .
N4 N 0.9598(4) -0.0536(4) 0.6183(2) 0.0723(11) Uani 1 1 d . . . . .
O1 O -0.0159(3) 0.6443(2) 0.51654(19) 0.0660(7) Uani 1 1 d . . . . .
O2 O 1.0161(3) -0.1298(2) 0.52349(18) 0.0643(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(10) . ?
C1 C6 1.376(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(7) . ?
C4 C7 1.461(7) . ?
C5 C6 1.377(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.276(7) . ?
C7 O1 1.364(6) . ?
C8 N2 1.299(8) . ?
C8 O1 1.343(6) . ?
C8 C9 1.460(8) . ?
C9 C14 1.369(9) . ?
C9 C10 1.388(10) . ?
C10 C11 1.382(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.351(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.371(11) . ?
C15 C16 1.372(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(8) . ?
C18 C21 1.449(7) . ?
C19 C20 1.383(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N3 1.292(7) . ?
C21 O2 1.363(6) . ?
C22 N4 1.289(7) . ?
C22 O2 1.365(6) . ?
C22 C23 1.464(7) . ?
C23 C28 1.369(8) . ?
C23 C24 1.390(8) . ?
C24 C25 1.384(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.361(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.382(8) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.382(6) . ?
C29 C34 1.396(6) . ?
C29 I1 2.092(4) . ?
C30 F1 1.338(6) . ?
C30 C31 1.371(8) . ?
C31 F2 1.341(5) . ?
C31 C32 1.360(8) . ?
C32 F3 1.337(5) . ?
C32 C33 1.395(6) . ?
C33 C34 1.392(6) . ?
C33 I2 2.077(4) . ?
C34 C35 1.494(5) . ?
C35 C40 1.383(6) . ?
C35 C36 1.386(6) . ?
C36 F4 1.339(5) . ?
C36 C37 1.392(6) . ?
C37 C38 1.385(6) . ?
C37 C41 1.490(6) . ?
C38 F7 1.334(5) . ?
C38 C39 1.373(7) . ?
C39 F6 1.344(5) . ?
C39 C40 1.375(6) . ?
C40 F5 1.333(5) . ?
C41 C46 1.378(7) . ?
C41 C42 1.403(6) . ?
C42 C43 1.389(7) . ?
C42 I3 2.078(6) . ?
C43 F8 1.329(7) . ?
C43 C44 1.366(10) . ?
C44 F9 1.339(6) . ?
C44 C45 1.371(9) . ?
C45 F10 1.338(7) . ?
C45 C46 1.387(7) . ?
C46 I4 2.062(5) . ?
C47 C48 1.380(6) . ?
C47 C52 1.399(6) . ?
C47 I5 2.099(4) . ?
C48 F11 1.343(6) . ?
C48 C49 1.363(8) . ?
C49 F12 1.344(5) . ?
C49 C50 1.359(8) . ?
C50 F13 1.342(5) . ?
C50 C51 1.390(6) . ?
C51 C52 1.390(6) . ?
C51 I6 2.071(4) . ?
C52 C53 1.485(5) . ?
C53 C58 1.373(6) . ?
C53 C54 1.389(5) . ?
C54 F14 1.337(5) . ?
C54 C55 1.396(5) . ?
C55 C56 1.387(6) . ?
C55 C59 1.483(5) . ?
C56 F17 1.338(5) . ?
C56 C57 1.370(6) . ?
C57 F16 1.339(5) . ?
C57 C58 1.379(6) . ?
C58 F15 1.338(5) . ?
C59 C60 1.393(6) . ?
C59 C64 1.396(6) . ?
C60 C61 1.378(6) . ?
C60 I7 2.087(5) . ?
C61 F18 1.343(6) . ?
C61 C62 1.370(8) . ?
C62 F19 1.331(6) . ?
C62 C63 1.368(8) . ?
C63 F20 1.325(6) . ?
C63 C64 1.392(7) . ?
C64 I8 2.051(5) . ?
N1 N2 1.399(7) . ?
N3 N4 1.402(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.5(6) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 C7 120.0(5) . . ?
C5 C4 C7 120.0(5) . . ?
C6 C5 C4 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 121.0(6) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C7 O1 111.8(5) . . ?
N1 C7 C4 129.3(5) . . ?
O1 C7 C4 118.9(4) . . ?
N2 C8 O1 111.9(5) . . ?
N2 C8 C9 128.5(5) . . ?
O1 C8 C9 119.6(5) . . ?
C14 C9 C10 120.6(6) . . ?
C14 C9 C8 120.9(5) . . ?
C10 C9 C8 118.5(6) . . ?
C11 C10 C9 118.6(9) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 120.2(8) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 121.0(8) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.4(8) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.2(7) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C20 C15 C16 120.8(6) . . ?
C20 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.5(7) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 119.7(5) . . ?
C17 C18 C21 120.4(5) . . ?
C19 C18 C21 119.9(5) . . ?
C20 C19 C18 120.2(6) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C15 C20 C19 119.5(7) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
N3 C21 O2 112.2(4) . . ?
N3 C21 C18 129.3(5) . . ?
O2 C21 C18 118.6(4) . . ?
N4 C22 O2 112.2(4) . . ?
N4 C22 C23 129.7(5) . . ?
O2 C22 C23 118.2(4) . . ?
C28 C23 C24 119.4(5) . . ?
C28 C23 C22 121.1(5) . . ?
C24 C23 C22 119.4(5) . . ?
C25 C24 C23 119.3(6) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 120.9(7) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.1(6) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 119.4(6) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 120.9(6) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C34 119.6(4) . . ?
C30 C29 I1 118.2(3) . . ?
C34 C29 I1 122.2(3) . . ?
F1 C30 C31 117.7(4) . . ?
F1 C30 C29 121.3(5) . . ?
C31 C30 C29 121.0(5) . . ?
F2 C31 C32 119.9(5) . . ?
F2 C31 C30 119.9(5) . . ?
C32 C31 C30 120.1(4) . . ?
F3 C32 C31 119.0(4) . . ?
F3 C32 C33 120.6(5) . . ?
C31 C32 C33 120.4(4) . . ?
C34 C33 C32 119.8(4) . . ?
C34 C33 I2 122.2(3) . . ?
C32 C33 I2 118.0(3) . . ?
C33 C34 C29 119.1(4) . . ?
C33 C34 C35 120.3(4) . . ?
C29 C34 C35 120.6(4) . . ?
C40 C35 C36 116.4(4) . . ?
C40 C35 C34 121.7(4) . . ?
C36 C35 C34 121.9(4) . . ?
F4 C36 C35 118.0(3) . . ?
F4 C36 C37 117.7(4) . . ?
C35 C36 C37 124.3(4) . . ?
C38 C37 C36 115.9(4) . . ?
C38 C37 C41 122.3(4) . . ?
C36 C37 C41 121.7(4) . . ?
F7 C38 C39 118.3(4) . . ?
F7 C38 C37 119.6(4) . . ?
C39 C38 C37 122.0(4) . . ?
F6 C39 C38 120.2(4) . . ?
F6 C39 C40 120.3(4) . . ?
C38 C39 C40 119.6(4) . . ?
F5 C40 C39 118.5(4) . . ?
F5 C40 C35 119.7(4) . . ?
C39 C40 C35 121.7(4) . . ?
C46 C41 C42 119.8(4) . . ?
C46 C41 C37 121.5(4) . . ?
C42 C41 C37 118.7(4) . . ?
C43 C42 C41 118.8(5) . . ?
C43 C42 I3 119.2(4) . . ?
C41 C42 I3 122.0(4) . . ?
F8 C43 C44 118.5(5) . . ?
F8 C43 C42 120.6(6) . . ?
C44 C43 C42 120.8(5) . . ?
F9 C44 C43 120.2(6) . . ?
F9 C44 C45 119.6(7) . . ?
C43 C44 C45 120.3(5) . . ?
F10 C45 C44 118.9(5) . . ?
F10 C45 C46 120.9(5) . . ?
C44 C45 C46 120.2(5) . . ?
C41 C46 C45 120.0(5) . . ?
C41 C46 I4 121.8(3) . . ?
C45 C46 I4 118.2(4) . . ?
C48 C47 C52 119.6(4) . . ?
C48 C47 I5 119.0(3) . . ?
C52 C47 I5 121.3(3) . . ?
F11 C48 C49 118.4(4) . . ?
F11 C48 C47 120.9(4) . . ?
C49 C48 C47 120.7(5) . . ?
F12 C49 C50 119.9(5) . . ?
F12 C49 C48 119.7(5) . . ?
C50 C49 C48 120.4(4) . . ?
F13 C50 C49 118.8(4) . . ?
F13 C50 C51 120.5(5) . . ?
C49 C50 C51 120.6(4) . . ?
C52 C51 C50 119.5(4) . . ?
C52 C51 I6 122.1(3) . . ?
C50 C51 I6 118.4(3) . . ?
C51 C52 C47 119.1(4) . . ?
C51 C52 C53 120.7(4) . . ?
C47 C52 C53 120.1(3) . . ?
C58 C53 C54 116.3(4) . . ?
C58 C53 C52 121.6(3) . . ?
C54 C53 C52 122.1(4) . . ?
F14 C54 C53 118.1(3) . . ?
F14 C54 C55 117.6(3) . . ?
C53 C54 C55 124.3(4) . . ?
C56 C55 C54 115.7(4) . . ?
C56 C55 C59 121.9(4) . . ?
C54 C55 C59 122.2(4) . . ?
F17 C56 C57 118.4(4) . . ?
F17 C56 C55 119.4(4) . . ?
C57 C56 C55 122.1(4) . . ?
F16 C57 C56 120.4(4) . . ?
F16 C57 C58 120.3(4) . . ?
C56 C57 C58 119.4(4) . . ?
F15 C58 C53 119.8(4) . . ?
F15 C58 C57 118.1(4) . . ?
C53 C58 C57 122.2(4) . . ?
C60 C59 C64 119.5(4) . . ?
C60 C59 C55 119.8(4) . . ?
C64 C59 C55 120.7(4) . . ?
C61 C60 C59 119.2(4) . . ?
C61 C60 I7 119.3(4) . . ?
C59 C60 I7 121.5(3) . . ?
F18 C61 C62 118.0(5) . . ?
F18 C61 C60 120.5(5) . . ?
C62 C61 C60 121.5(5) . . ?
F19 C62 C63 119.6(5) . . ?
F19 C62 C61 120.4(5) . . ?
C63 C62 C61 119.9(4) . . ?
F20 C63 C62 118.6(5) . . ?
F20 C63 C64 121.2(5) . . ?
C62 C63 C64 120.2(5) . . ?
C63 C64 C59 119.7(4) . . ?
C63 C64 I8 118.3(4) . . ?
C59 C64 I8 121.9(3) . . ?
C7 N1 N2 106.8(5) . . ?
C8 N2 N1 106.0(4) . . ?
C21 N3 N4 106.4(4) . . ?
C22 N4 N3 106.5(4) . . ?
C8 O1 C7 103.5(4) . . ?
C21 O2 C22 102.8(4) . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1824278'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H12 F20 I8 N2 O'
_chemical_formula_weight         2063.83

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

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

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

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

_cell_length_a                   11.0666(3)
_cell_length_b                   11.7332(3)
_cell_length_c                   22.9011(6)
_cell_angle_alpha                90.760(2)
_cell_angle_beta                 99.480(2)
_cell_angle_gamma                98.949(2)
_cell_volume                     2895.01(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14827
_cell_measurement_theta_min      1.7970
_cell_measurement_theta_max      25.3390

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.368
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    4.389
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1268
_diffrn_reflns_number            49854
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         28.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13462
_reflns_number_gt                8975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+9.8456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13462
_refine_ls_number_parameters     739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8365(11) 0.0338(9) 0.5419(7) 0.124(4) Uani 1 1 d . . . . .
H1 H 0.9086 0.0037 0.5553 0.149 Uiso 1 1 calc R U . . .
C2 C 0.8095(10) 0.0659(8) 0.4842(5) 0.109(3) Uani 1 1 d . . . . .
H2 H 0.8626 0.0553 0.4578 0.130 Uiso 1 1 calc R U . . .
C3 C 0.7043(9) 0.1135(7) 0.4654(4) 0.096(3) Uani 1 1 d . . . . .
H3 H 0.6878 0.1361 0.4265 0.116 Uiso 1 1 calc R U . . .
C4 C 0.6231(7) 0.1282(6) 0.5035(4) 0.076(2) Uani 1 1 d . . . . .
C5 C 0.6497(8) 0.0947(8) 0.5615(4) 0.099(3) Uani 1 1 d . . . . .
H5 H 0.5973 0.1041 0.5884 0.119 Uiso 1 1 calc R U . . .
C6 C 0.7561(11) 0.0472(10) 0.5781(5) 0.123(4) Uani 1 1 d . . . . .
H6 H 0.7728 0.0231 0.6167 0.147 Uiso 1 1 calc R U . . .
C7 C 0.5129(7) 0.1768(6) 0.4833(3) 0.0687(18) Uani 1 1 d . . . . .
C8 C 0.3432(7) 0.2378(6) 0.4900(3) 0.0670(18) Uani 1 1 d . . . . .
C9 C 0.2435(8) 0.2654(6) 0.5188(3) 0.0710(19) Uani 1 1 d . . . . .
C10 C 0.1505(9) 0.3185(8) 0.4885(4) 0.093(2) Uani 1 1 d . . . . .
H10 H 0.1515 0.3360 0.4491 0.112 Uiso 1 1 calc R U . . .
C11 C 0.0567(9) 0.3456(8) 0.5158(4) 0.102(3) Uani 1 1 d . . . . .
H11 H -0.0056 0.3807 0.4946 0.123 Uiso 1 1 calc R U . . .
C12 C 0.0539(10) 0.3212(8) 0.5745(5) 0.097(3) Uani 1 1 d . . . . .
C13 C 0.1444(10) 0.2683(8) 0.6036(4) 0.097(3) Uani 1 1 d . . . . .
H13 H 0.1434 0.2516 0.6431 0.116 Uiso 1 1 calc R U . . .
C14 C 0.2371(8) 0.2383(7) 0.5773(3) 0.085(2) Uani 1 1 d . . . . .
H14 H 0.2964 0.1996 0.5984 0.102 Uiso 1 1 calc R U . . .
C15 C -0.0474(13) 0.3551(11) 0.6026(6) 0.162(5) Uani 1 1 d . . . . .
H15A H -0.1014 0.3913 0.5741 0.243 Uiso 1 1 calc R U . . .
H15B H -0.0126 0.4082 0.6355 0.243 Uiso 1 1 calc R U . . .
H15C H -0.0938 0.2877 0.6163 0.243 Uiso 1 1 calc R U . . .
C16 C 0.3932(7) 0.5250(6) 0.5869(3) 0.0643(18) Uani 1 1 d . . . . .
C17 C 0.4680(6) 0.4591(5) 0.6186(3) 0.0583(16) Uani 1 1 d . . . . .
C18 C 0.4659(5) 0.4438(5) 0.6785(2) 0.0501(13) Uani 1 1 d . . . . .
C19 C 0.3886(5) 0.5008(5) 0.7073(2) 0.0489(13) Uani 1 1 d . . . . .
C20 C 0.3122(6) 0.5677(5) 0.6737(3) 0.0548(14) Uani 1 1 d . . . . .
C21 C 0.3142(6) 0.5768(6) 0.6135(3) 0.0620(16) Uani 1 1 d . . . . .
C22 C 0.3921(5) 0.4922(5) 0.7721(2) 0.0480(13) Uani 1 1 d . . . . .
C23 C 0.3093(5) 0.4123(5) 0.7961(2) 0.0509(13) Uani 1 1 d . . . . .
C24 C 0.3137(5) 0.4051(5) 0.8564(3) 0.0521(14) Uani 1 1 d . . . . .
C25 C 0.4024(5) 0.4802(5) 0.8938(2) 0.0507(13) Uani 1 1 d . . . . .
C26 C 0.4866(5) 0.5624(5) 0.8730(2) 0.0480(13) Uani 1 1 d . . . . .
C27 C 0.4787(5) 0.5639(5) 0.8125(2) 0.0488(13) Uani 1 1 d . . . . .
C28 C 0.5824(6) 0.6426(5) 0.9145(2) 0.0507(14) Uani 1 1 d . . . . .
C29 C 0.6968(6) 0.6120(5) 0.9372(3) 0.0536(14) Uani 1 1 d . . . . .
C30 C 0.7829(6) 0.6874(6) 0.9756(3) 0.0659(17) Uani 1 1 d . . . . .
C31 C 0.7571(7) 0.7919(6) 0.9915(3) 0.072(2) Uani 1 1 d . . . . .
C32 C 0.6456(8) 0.8232(6) 0.9696(3) 0.0686(19) Uani 1 1 d . . . . .
C33 C 0.5572(6) 0.7497(5) 0.9316(3) 0.0589(15) Uani 1 1 d . . . . .
C34 C 0.6513(6) 1.1033(5) 0.8572(3) 0.0631(16) Uani 1 1 d . . . . .
C35 C 0.5413(9) 1.1294(6) 0.8715(4) 0.082(2) Uani 1 1 d . . . . .
C36 C 0.4314(8) 1.0956(7) 0.8341(4) 0.084(2) Uani 1 1 d . . . . .
C37 C 0.4285(7) 1.0359(7) 0.7820(4) 0.080(2) Uani 1 1 d . . . . .
C38 C 0.5351(6) 1.0070(5) 0.7670(3) 0.0605(16) Uani 1 1 d . . . . .
C39 C 0.6477(5) 1.0410(5) 0.8041(3) 0.0521(14) Uani 1 1 d . . . . .
C40 C 0.7641(5) 1.0090(5) 0.7883(3) 0.0475(13) Uani 1 1 d . . . . .
C41 C 0.8392(6) 1.0799(5) 0.7572(3) 0.0634(17) Uani 1 1 d . . . . .
C42 C 0.9432(6) 1.0475(6) 0.7402(3) 0.0697(19) Uani 1 1 d . . . . .
C43 C 0.9706(5) 0.9407(5) 0.7540(3) 0.0583(15) Uani 1 1 d . . . . .
C44 C 0.8996(5) 0.8656(5) 0.7857(2) 0.0460(12) Uani 1 1 d . . . . .
C45 C 0.7984(5) 0.9041(5) 0.8020(2) 0.0465(12) Uani 1 1 d . . . . .
C46 C 0.9306(5) 0.7494(5) 0.8009(3) 0.0490(13) Uani 1 1 d . . . . .
C47 C 0.8895(5) 0.6558(5) 0.7606(3) 0.0522(14) Uani 1 1 d . . . . .
C48 C 0.9217(6) 0.5490(5) 0.7757(3) 0.0637(17) Uani 1 1 d . . . . .
C49 C 0.9909(6) 0.5346(6) 0.8291(4) 0.0686(18) Uani 1 1 d . . . . .
C50 C 1.0309(6) 0.6257(7) 0.8686(3) 0.0698(18) Uani 1 1 d . . . . .
C51 C 1.0027(5) 0.7337(5) 0.8547(3) 0.0567(15) Uani 1 1 d . . . . .
F1 F 0.5442(4) 0.4073(4) 0.59146(18) 0.0857(12) Uani 1 1 d . . . . .
F2 F 0.3937(5) 0.5355(4) 0.52875(15) 0.0920(14) Uani 1 1 d . . . . .
F3 F 0.2385(4) 0.6380(4) 0.58068(19) 0.0934(13) Uani 1 1 d . . . . .
F4 F 0.5606(3) 0.6413(3) 0.79023(15) 0.0704(10) Uani 1 1 d . . . . .
F5 F 0.2242(3) 0.3397(3) 0.75981(15) 0.0728(11) Uani 1 1 d . . . . .
F6 F 0.2336(3) 0.3268(3) 0.87810(16) 0.0674(10) Uani 1 1 d . . . . .
F7 F 0.4034(4) 0.4723(3) 0.95167(14) 0.0729(10) Uani 1 1 d . . . . .
F8 F 0.6242(5) 0.9271(4) 0.9869(2) 0.1013(15) Uani 1 1 d . . . . .
F9 F 0.8430(4) 0.8642(4) 1.0294(2) 0.1040(15) Uani 1 1 d . . . . .
F10 F 0.8933(4) 0.6590(4) 0.9988(2) 0.0954(14) Uani 1 1 d . . . . .
F11 F 0.5422(5) 1.1871(4) 0.9224(2) 0.1175(18) Uani 1 1 d . . . . .
F12 F 0.3266(5) 1.1226(5) 0.8486(3) 0.136(2) Uani 1 1 d . . . . .
F13 F 0.3195(4) 1.0062(5) 0.7469(3) 0.1203(19) Uani 1 1 d . . . . .
F14 F 0.7289(3) 0.8336(3) 0.83364(15) 0.0603(9) Uani 1 1 d . . . . .
F15 F 0.8114(4) 1.1841(3) 0.7422(2) 0.0936(14) Uani 1 1 d . . . . .
F16 F 1.0141(4) 1.1188(4) 0.7100(3) 0.1159(19) Uani 1 1 d . . . . .
F17 F 1.0699(4) 0.9086(4) 0.7362(2) 0.0893(13) Uani 1 1 d . . . . .
F18 F 0.8862(4) 0.4583(3) 0.7377(2) 0.0880(13) Uani 1 1 d . . . . .
F19 F 1.0197(5) 0.4305(4) 0.8431(2) 0.1040(16) Uani 1 1 d . . . . .
F20 F 1.0995(4) 0.6089(4) 0.9211(2) 0.1000(15) Uani 1 1 d . . . . .
I1 I 0.57535(5) 0.33314(5) 0.72210(2) 0.08345(16) Uani 1 1 d . . . . .
I2 I 0.19584(5) 0.65869(5) 0.71109(3) 0.09282(18) Uani 1 1 d . . . . .
I3 I 0.74108(5) 0.45183(4) 0.91951(2) 0.07868(15) Uani 1 1 d . . . . .
I4 I 0.38827(6) 0.80193(5) 0.90459(3) 0.09866(19) Uani 1 1 d . . . . .
I5 I 0.81683(6) 1.15440(5) 0.91458(3) 0.0988(2) Uani 1 1 d . . . . .
I6 I 0.52252(4) 0.91014(5) 0.68832(2) 0.07782(15) Uani 1 1 d . . . . .
I7 I 0.78293(4) 0.67504(4) 0.67803(2) 0.06660(13) Uani 1 1 d . . . . .
I8 I 1.06899(5) 0.87237(5) 0.91496(2) 0.08728(17) Uani 1 1 d . . . . .
N1 N 0.4733(6) 0.2141(5) 0.4321(3) 0.0724(15) Uani 1 1 d . . . . .
N2 N 0.3625(6) 0.2540(5) 0.4370(2) 0.0709(15) Uani 1 1 d . . . . .
O1 O 0.4345(5) 0.1890(4) 0.5224(2) 0.0719(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.336(15) . ?
C1 C2 1.377(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(11) . ?
C4 C7 1.436(11) . ?
C5 C6 1.380(13) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.290(8) . ?
C7 O1 1.366(9) . ?
C8 N2 1.279(8) . ?
C8 O1 1.357(8) . ?
C8 C9 1.450(10) . ?
C9 C10 1.379(11) . ?
C9 C14 1.391(10) . ?
C10 C11 1.371(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(13) . ?
C12 C15 1.482(14) . ?
C13 C14 1.360(12) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 F2 1.339(7) . ?
C16 C17 1.352(9) . ?
C16 C21 1.355(9) . ?
C17 F1 1.338(7) . ?
C17 C18 1.390(8) . ?
C18 C19 1.402(8) . ?
C18 I1 2.067(6) . ?
C19 C20 1.390(8) . ?
C19 C22 1.483(7) . ?
C20 C21 1.389(8) . ?
C20 I2 2.072(6) . ?
C21 F3 1.332(7) . ?
C22 C27 1.386(7) . ?
C22 C23 1.390(7) . ?
C23 F5 1.333(6) . ?
C23 C24 1.378(8) . ?
C24 F6 1.334(6) . ?
C24 C25 1.381(8) . ?
C25 F7 1.329(6) . ?
C25 C26 1.380(7) . ?
C26 C27 1.373(7) . ?
C26 C28 1.499(8) . ?
C27 F4 1.347(6) . ?
C28 C29 1.390(9) . ?
C28 C33 1.393(8) . ?
C29 C30 1.381(8) . ?
C29 I3 2.066(6) . ?
C30 F10 1.343(8) . ?
C30 C31 1.359(10) . ?
C31 F9 1.354(7) . ?
C31 C32 1.361(11) . ?
C32 F8 1.345(8) . ?
C32 C33 1.376(9) . ?
C33 I4 2.059(7) . ?
C34 C35 1.387(10) . ?
C34 C39 1.404(9) . ?
C34 I5 2.070(7) . ?
C35 F11 1.340(9) . ?
C35 C36 1.366(12) . ?
C36 F12 1.340(8) . ?
C36 C37 1.369(11) . ?
C37 F13 1.328(9) . ?
C37 C38 1.371(9) . ?
C38 C39 1.386(9) . ?
C38 I6 2.091(7) . ?
C39 C40 1.493(8) . ?
C40 C45 1.369(7) . ?
C40 C41 1.374(8) . ?
C41 F15 1.342(7) . ?
C41 C42 1.378(9) . ?
C42 F16 1.336(7) . ?
C42 C43 1.363(9) . ?
C43 F17 1.338(7) . ?
C43 C44 1.383(8) . ?
C44 C45 1.374(8) . ?
C44 C46 1.489(8) . ?
C45 F14 1.343(6) . ?
C46 C51 1.384(8) . ?
C46 C47 1.395(8) . ?
C47 C48 1.387(9) . ?
C47 I7 2.093(6) . ?
C48 F18 1.334(7) . ?
C48 C49 1.360(10) . ?
C49 F19 1.339(7) . ?
C49 C50 1.360(10) . ?
C50 F20 1.346(8) . ?
C50 C51 1.381(9) . ?
C51 I8 2.079(6) . ?
N1 N2 1.400(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.0(11) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C3 C2 C1 120.4(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.9(10) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.7(9) . . ?
C3 C4 C7 120.5(8) . . ?
C5 C4 C7 120.8(9) . . ?
C6 C5 C4 118.1(10) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 123.9(11) . . ?
C1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
N1 C7 O1 111.4(7) . . ?
N1 C7 C4 130.0(8) . . ?
O1 C7 C4 118.6(7) . . ?
N2 C8 O1 111.6(7) . . ?
N2 C8 C9 130.1(7) . . ?
O1 C8 C9 118.4(6) . . ?
C10 C9 C14 117.8(8) . . ?
C10 C9 C8 120.7(7) . . ?
C14 C9 C8 121.5(8) . . ?
C11 C10 C9 120.9(8) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.6(10) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 118.1(9) . . ?
C13 C12 C15 123.2(10) . . ?
C11 C12 C15 118.7(12) . . ?
C12 C13 C14 122.4(9) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C9 120.1(9) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 C16 C17 120.1(7) . . ?
F2 C16 C21 120.0(7) . . ?
C17 C16 C21 119.8(6) . . ?
F1 C17 C16 119.1(6) . . ?
F1 C17 C18 119.8(6) . . ?
C16 C17 C18 121.1(6) . . ?
C17 C18 C19 119.7(6) . . ?
C17 C18 I1 118.3(5) . . ?
C19 C18 I1 122.0(4) . . ?
C20 C19 C18 118.2(5) . . ?
C20 C19 C22 121.5(5) . . ?
C18 C19 C22 120.3(5) . . ?
C19 C20 C21 119.9(6) . . ?
C19 C20 I2 122.0(4) . . ?
C21 C20 I2 118.1(5) . . ?
F3 C21 C16 118.6(6) . . ?
F3 C21 C20 120.3(6) . . ?
C16 C21 C20 121.2(6) . . ?
C27 C22 C23 115.8(5) . . ?
C27 C22 C19 121.8(5) . . ?
C23 C22 C19 122.4(5) . . ?
F5 C23 C24 119.0(5) . . ?
F5 C23 C22 119.1(5) . . ?
C24 C23 C22 121.9(5) . . ?
F6 C24 C23 120.4(5) . . ?
F6 C24 C25 120.8(5) . . ?
C23 C24 C25 118.7(5) . . ?
F7 C25 C26 120.1(5) . . ?
F7 C25 C24 117.5(5) . . ?
C26 C25 C24 122.5(5) . . ?
C27 C26 C25 115.9(5) . . ?
C27 C26 C28 122.6(5) . . ?
C25 C26 C28 121.5(5) . . ?
F4 C27 C26 118.1(5) . . ?
F4 C27 C22 116.8(5) . . ?
C26 C27 C22 125.2(5) . . ?
C29 C28 C33 118.6(5) . . ?
C29 C28 C26 121.3(5) . . ?
C33 C28 C26 120.1(6) . . ?
C30 C29 C28 120.0(6) . . ?
C30 C29 I3 117.6(5) . . ?
C28 C29 I3 122.3(4) . . ?
F10 C30 C31 118.4(6) . . ?
F10 C30 C29 121.0(7) . . ?
C31 C30 C29 120.6(7) . . ?
F9 C31 C30 119.5(8) . . ?
F9 C31 C32 120.3(7) . . ?
C30 C31 C32 120.1(6) . . ?
F8 C32 C31 117.9(6) . . ?
F8 C32 C33 121.4(7) . . ?
C31 C32 C33 120.7(6) . . ?
C32 C33 C28 119.9(6) . . ?
C32 C33 I4 117.6(5) . . ?
C28 C33 I4 122.4(5) . . ?
C35 C34 C39 119.0(7) . . ?
C35 C34 I5 120.0(6) . . ?
C39 C34 I5 121.1(5) . . ?
F11 C35 C36 119.5(8) . . ?
F11 C35 C34 120.0(8) . . ?
C36 C35 C34 120.5(7) . . ?
F12 C36 C35 119.4(8) . . ?
F12 C36 C37 120.2(9) . . ?
C35 C36 C37 120.3(7) . . ?
F13 C37 C38 121.2(8) . . ?
F13 C37 C36 118.1(7) . . ?
C38 C37 C36 120.7(7) . . ?
C37 C38 C39 119.9(7) . . ?
C37 C38 I6 118.6(5) . . ?
C39 C38 I6 121.5(4) . . ?
C38 C39 C34 119.6(6) . . ?
C38 C39 C40 120.2(5) . . ?
C34 C39 C40 120.2(6) . . ?
C45 C40 C41 116.4(5) . . ?
C45 C40 C39 121.1(5) . . ?
C41 C40 C39 122.4(5) . . ?
F15 C41 C40 119.7(6) . . ?
F15 C41 C42 118.2(5) . . ?
C40 C41 C42 122.1(6) . . ?
F16 C42 C43 121.0(6) . . ?
F16 C42 C41 120.4(6) . . ?
C43 C42 C41 118.6(5) . . ?
F17 C43 C42 118.4(5) . . ?
F17 C43 C44 119.4(5) . . ?
C42 C43 C44 122.2(6) . . ?
C45 C44 C43 116.1(5) . . ?
C45 C44 C46 122.0(5) . . ?
C43 C44 C46 121.9(5) . . ?
F14 C45 C40 118.1(5) . . ?
F14 C45 C44 117.4(5) . . ?
C40 C45 C44 124.5(5) . . ?
C51 C46 C47 119.3(5) . . ?
C51 C46 C44 120.3(5) . . ?
C47 C46 C44 120.3(5) . . ?
C48 C47 C46 119.0(6) . . ?
C48 C47 I7 120.0(5) . . ?
C46 C47 I7 121.0(4) . . ?
F18 C48 C49 118.5(6) . . ?
F18 C48 C47 120.5(7) . . ?
C49 C48 C47 121.0(6) . . ?
F19 C49 C48 120.0(7) . . ?
F19 C49 C50 119.8(7) . . ?
C48 C49 C50 120.2(6) . . ?
F20 C50 C49 118.9(6) . . ?
F20 C50 C51 120.6(7) . . ?
C49 C50 C51 120.4(6) . . ?
C50 C51 C46 120.0(6) . . ?
C50 C51 I8 119.7(5) . . ?
C46 C51 I8 120.3(4) . . ?
C7 N1 N2 106.1(6) . . ?
C8 N2 N1 107.3(6) . . ?
C8 O1 C7 103.6(5) . . ?

_refine_diff_density_max         2.059
_refine_diff_density_min         -1.603
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-4

