# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Gross95
_database_code_depnum_ccdc_archive 'CCDC 1888512'
loop_
_audit_author_name
_audit_author_address
'Fridman Natalia '
;Technion
Israel
;
_audit_update_record             
;
2019-01-03 deposited with the CCDC.	2019-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gross95 (Zhenya)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H4 F17 I4 N4 P, 2(C Cl2)'
_chemical_formula_sum            'C39 H4 Cl4 F17 I4 N4 P'
_chemical_formula_weight         1531.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.2430(13)
_cell_length_b                   7.806(5)
_cell_length_c                   17.503(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.42(3)
_cell_angle_gamma                90
_cell_volume                     2207.9(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3932
_cell_measurement_theta_min      2.055
_cell_measurement_theta_max      24.710

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_F_000             1428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.211
_shelx_estimated_absorpt_T_min   0.552
_shelx_estimated_absorpt_T_max   0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_process_details   
; 
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'  
;
_exptl_special_details           
;  
 ?  
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            3932
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        24.710
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3932
_reflns_number_gt                3128
_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       'Collect (Nonius, 2006)'
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.10.1'
_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)+(0.0857P)²+30.3420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0036(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     370
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.1059
_refine_ls_wR_factor_ref         0.2458
_refine_ls_wR_factor_gt          0.2335
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
# start Validation Reply Form
_vrf_PLAT260_Gross95
;
PROBLEM: Large Average Ueq of Residue Including       Cl1      0.186 Check 
RESPONSE: Partly disordered DCM solvent
;
_vrf_PLAT342_Gross95             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02509 Ang.  
RESPONSE: Partly disordered pentafluorophenyl groups in the complex
;
_vrf_PLAT971_Gross95             
;
PROBLEM: Check Calcd Resid. Dens.  1.75A   From Cl1             2.59 eA-3  
RESPONSE: Partly disordered DCM solvent
;
# end Validation Reply Form

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 0.43595(8) 0.2500 0.27367(10) 0.0809(6) Uani 1 2 d S T P . .
I2 I 0.36618(8) 0.2500 0.04596(11) 0.0891(7) Uani 1 2 d S T P . .
I3 I 0.4282(3) 0.2500 -0.1360(3) 0.078(4) Uani 0.53(4) 2 d S T P A 1
I3A I 0.4195(12) 0.2500 -0.115(2) 0.235(8) Uani 0.47(4) 2 d S T P A 2
I4A I 0.582(3) 0.2500 -0.2010(12) 0.116(4) Uani 0.53(10) 2 d S T P A 2
I4 I 0.5977(7) 0.2500 -0.2069(6) 0.074(5) Uani 0.47(10) 2 d S T P A 1
P1 P 0.7285(2) 0.2500 0.1610(3) 0.0472(11) Uani 1 2 d S T P . .
F1 F 0.7947(8) 0.5519 -0.0886(7) 0.123(4) Uani 1 1 d . . . . .
F2 F 0.8329(11) 0.554(2) -0.2229(8) 0.174(7) Uani 1 1 d . . . . .
F3 F 0.8521(16) 0.2500 -0.2890(12) 0.216(14) Uani 1 2 d S T P . .
F4 F 1.0188(5) -0.0485(12) 0.3311(7) 0.104(3) Uani 1 1 d . . . . .
F5 F 1.1804(6) -0.0474(14) 0.4236(7) 0.117(4) Uani 1 1 d . . . . .
F6 F 1.2606(6) 0.2500 0.4697(7) 0.087(4) Uani 1 2 d S T P . .
F7 F 0.6295(7) 0.5446 0.3921(7) 0.129(5) Uani 1 1 d . . . . .
F8 F 0.5879(7) 0.5645 0.5215(8) 0.182(8) Uani 1 1 d . . . . .
F9 F 0.5745(10) 0.2500 0.5984(10) 0.181(12) Uani 1 2 d S T P . .
F10 F 0.7314(4) 0.0442(11) 0.1629(5) 0.070(2) Uani 1 1 d . . . . .
N1 N 0.8243(8) 0.2500 0.1382(8) 0.044(3) Uani 1 2 d S T P . .
N2 N 0.7808(7) 0.2500 0.2712(7) 0.043(3) Uani 1 2 d S T P . .
N3 N 0.6275(9) 0.2500 0.1723(9) 0.058(4) Uani 1 2 d S T P . .
N4 N 0.6674(8) 0.2500 0.0543(9) 0.053(4) Uani 1 2 d S T P A .
C1 C 0.7667(11) 0.2500 -0.0106(12) 0.066(5) Uani 1 2 d S T P A .
C2 C 0.8320(11) 0.2500 0.0625(9) 0.054(4) Uani 1 2 d S T P . .
C3 C 0.9145(12) 0.2500 0.0725(14) 0.082(7) Uani 1 2 d S T P . .
H3 H 0.9361 0.2500 0.0294 0.098 Uiso 1 2 calc R U P . .
C4 C 0.9600(11) 0.2500 0.1522(10) 0.062(5) Uani 1 2 d S T P . .
H4 H 1.0187 0.2500 0.1749 0.074 Uiso 1 2 calc R U P . .
C5 C 0.9055(9) 0.2500 0.1965(10) 0.054(5) Uani 1 2 d S T P . .
C6 C 0.9238(9) 0.2500 0.2777(11) 0.047(4) Uani 1 2 d S T P . .
C7 C 0.8632(11) 0.2500 0.3119(11) 0.055(4) Uani 1 2 d S T P . .
C8 C 0.8793(10) 0.2500 0.3992(10) 0.067(6) Uani 1 2 d S T P . .
H8 H 0.9316 0.2500 0.4419 0.080 Uiso 1 2 calc R U P . .
C9 C 0.8057(13) 0.2500 0.4063(12) 0.083(7) Uani 1 2 d S T P . .
H9 H 0.7972 0.2500 0.4571 0.100 Uiso 1 2 calc R U P . .
C10 C 0.7415(10) 0.2500 0.3305(10) 0.057(5) Uani 1 2 d S T P . .
C11 C 0.6597(11) 0.2500 0.3180(11) 0.066(5) Uani 1 2 d S T P . .
C12 C 0.6007(11) 0.2500 0.2381(11) 0.057(5) Uani 1 2 d S T P . .
C13 C 0.5124(11) 0.2500 0.2077(15) 0.070(6) Uani 1 2 d S T P . .
C14 C 0.4864(11) 0.2500 0.1243(15) 0.066(5) Uani 1 2 d S T P . .
C15 C 0.5610(10) 0.2500 0.1019(10) 0.058(5) Uani 1 2 d S T P . .
C16 C 0.5822(10) 0.2500 0.0312(11) 0.051(4) Uani 1 2 d S T P A .
C17 C 0.5462(12) 0.2500 -0.0543(12) 0.065(5) Uani 1 2 d S T P . .
C18 C 0.6101(13) 0.2500 -0.0810(13) 0.068(5) Uani 1 2 d S T P A .
C19 C 0.6872(11) 0.2500 -0.0160(10) 0.054(4) Uani 1 2 d S T P . .
C20 C 0.7870(13) 0.2500 -0.0884(12) 0.082(7) Uani 1 2 d S T P . .
C21 C 0.7998(11) 0.404(3) -0.1222(10) 0.094(6) Uani 1 1 d . . . . .
C22 C 0.8214(16) 0.4067 -0.1891(12) 0.142(10) Uani 1 1 d . . . . .
C23 C 0.827(3) 0.2500 -0.227(2) 0.18(2) Uani 1 2 d S T P . .
C24 C 1.0121(10) 0.2500 0.3274(10) 0.048(4) Uani 1 2 d S T P . .
C25 C 1.0577(7) 0.099(2) 0.3549(8) 0.064(4) Uani 1 1 d . . . . .
C26 C 1.1394(7) 0.101(2) 0.4003(8) 0.064(4) Uani 1 1 d . . . . .
C27 C 1.1811(9) 0.2500 0.4239(9) 0.051(5) Uani 1 2 d S T P . .
C28 C 0.6358(11) 0.2500 0.3880(13) 0.076(6) Uani 1 2 d DS T P . .
C29 C 0.6228(9) 0.4000(17) 0.4257(11) 0.093(6) Uani 1 1 d D . . . .
C30 C 0.6022(9) 0.3986 0.4933(10) 0.116(7) Uani 1 1 d D . . . .
C31 C 0.5932(14) 0.2500 0.5331(11) 0.116(7) Uani 1 2 d DS T P . .
Cl2 Cl 1.2504(5) 0.2500 0.6786(6) 0.138(3) Uani 1 2 d DS T P . .
Cl1 Cl 1.0837(5) 0.2500 0.5705(4) 0.208(7) Uani 1 2 d DS T P . .
C32 C 1.1489(4) 0.2500 0.6692(5) 0.208(7) Uani 1 2 d DS T P . .
Cl3 Cl 0.8370(6) 0.6787(14) 0.1192(7) 0.118(3) Uiso 0.5 1 d D . P . .
Cl4 Cl 0.9642(12) 0.7500 0.0664(10) 0.252(8) Uiso 1 2 d DS . P . .
C33 C 0.9363(7) 0.7500 0.1505(11) 0.34(4) Uiso 1 2 d DS . P . .


_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 C13 2.03(2) . ?
I2 C14 2.05(2) . ?
I3 C17 2.038(19) . ?
I3A I3A 0.00(4) 4_565 ?
I3A C17 2.07(2) . ?
I4A C18 1.98(3) . ?
I4 C18 2.14(3) . ?
P1 F10 1.607(8) 4_565 ?
P1 F10 1.607(8) . ?
P1 N4 1.797(15) . ?
P1 N2 1.821(12) . ?
P1 N3 1.821(14) . ?
P1 N1 1.829(12) . ?
F1 C21 1.31(2) . ?
F2 C22 1.342(18) . ?
F3 C23 1.30(3) . ?
F4 C25 1.325(17) . ?
F5 C26 1.341(17) . ?
F6 C27 1.324(18) . ?
F7 C29 1.297(16) . ?
F8 C30 1.438(7) . ?
F9 C31 1.29(2) . ?
N1 C2 1.377(19) . ?
N1 C5 1.416(19) . ?
N2 C7 1.35(2) . ?
N2 C10 1.42(2) . ?
N3 C15 1.36(2) . ?
N3 C12 1.38(2) . ?
N4 C16 1.38(2) . ?
N4 C19 1.39(2) . ?
C1 C19 1.34(3) . ?
C1 C2 1.38(2) . ?
C1 C20 1.52(3) . ?
C2 C3 1.37(3) . ?
C3 C4 1.34(3) . ?
C4 C5 1.41(2) . ?
C5 C6 1.35(2) . ?
C6 C7 1.37(2) . ?
C6 C24 1.47(2) . ?
C7 C8 1.45(2) . ?
C8 C9 1.32(3) . ?
C9 C10 1.40(3) . ?
C10 C11 1.35(2) . ?
C11 C12 1.41(3) . ?
C11 C28 1.42(3) . ?
C12 C13 1.43(3) . ?
C13 C14 1.37(3) . ?
C14 C15 1.47(2) . ?
C15 C16 1.41(2) . ?
C16 C17 1.40(3) . ?
C17 C18 1.34(3) . ?
C17 I3A 2.07(2) 4_565 ?
C18 C19 1.42(3) . ?
C20 C21 1.39(2) 4_565 ?
C20 C21 1.39(2) . ?
C21 C22 1.35(3) . ?
C22 C23 1.412(16) . ?
C23 C22 1.412(16) 4_565 ?
C24 C25 1.404(17) . ?
C24 C25 1.404(17) 4_565 ?
C25 C26 1.355(17) . ?
C26 C27 1.357(17) . ?
C27 C26 1.357(17) 4_565 ?
C28 C29 1.3999(12) . ?
C28 C29 1.4000(12) 4_565 ?
C29 C30 1.35(2) . ?
C30 C31 1.3898(12) . ?
C31 C30 1.3897(12) 4_565 ?
Cl2 C32 1.7000(11) . ?
Cl1 C32 1.7001(12) . ?
Cl3 Cl3 1.11(2) 4_575 ?
Cl3 C33 1.7000(11) . ?
Cl4 C33 1.7000(11) . ?
C33 Cl3 1.7000(11) 4_575 ?

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
I3A I3A C17 0(10) 4_565 . ?
F10 P1 F10 176.5(6) 4_565 . ?
F10 P1 N4 91.4(3) 4_565 . ?
F10 P1 N4 91.3(3) . . ?
F10 P1 N2 88.8(3) 4_565 . ?
F10 P1 N2 88.8(3) . . ?
N4 P1 N2 174.3(6) . . ?
F10 P1 N3 91.2(3) 4_565 . ?
F10 P1 N3 91.3(3) . . ?
N4 P1 N3 82.9(7) . . ?
N2 P1 N3 91.4(6) . . ?
F10 P1 N1 88.9(3) 4_565 . ?
F10 P1 N1 88.9(3) . . ?
N4 P1 N1 91.2(6) . . ?
N2 P1 N1 94.6(6) . . ?
N3 P1 N1 174.0(7) . . ?
C2 N1 C5 106.8(13) . . ?
C2 N1 P1 127.4(11) . . ?
C5 N1 P1 125.8(11) . . ?
C7 N2 C10 107.2(12) . . ?
C7 N2 P1 126.9(11) . . ?
C10 N2 P1 125.8(10) . . ?
C15 N3 C12 109.6(14) . . ?
C15 N3 P1 116.0(12) . . ?
C12 N3 P1 134.5(12) . . ?
C16 N4 C19 107.8(14) . . ?
C16 N4 P1 118.9(12) . . ?
C19 N4 P1 133.2(12) . . ?
C19 C1 C2 123.3(18) . . ?
C19 C1 C20 119.1(17) . . ?
C2 C1 C20 117.6(17) . . ?
C3 C2 N1 108.8(15) . . ?
C3 C2 C1 126.4(17) . . ?
N1 C2 C1 124.8(16) . . ?
C4 C3 C2 109.7(18) . . ?
C3 C4 C5 108.1(16) . . ?
C6 C5 C4 128.7(14) . . ?
C6 C5 N1 124.7(14) . . ?
C4 C5 N1 106.6(14) . . ?
C5 C6 C7 121.8(15) . . ?
C5 C6 C24 116.0(13) . . ?
C7 C6 C24 122.2(16) . . ?
N2 C7 C6 126.2(16) . . ?
N2 C7 C8 109.6(14) . . ?
C6 C7 C8 124.2(16) . . ?
C9 C8 C7 105.2(15) . . ?
C8 C9 C10 112.3(16) . . ?
C11 C10 C9 126.1(16) . . ?
C11 C10 N2 128.2(16) . . ?
C9 C10 N2 105.7(14) . . ?
C10 C11 C12 120.7(17) . . ?
C10 C11 C28 117.5(17) . . ?
C12 C11 C28 121.8(17) . . ?
N3 C12 C11 119.3(15) . . ?
N3 C12 C13 108.2(16) . . ?
C11 C12 C13 132.5(18) . . ?
C14 C13 C12 107.9(18) . . ?
C14 C13 I1 124.6(14) . . ?
C12 C13 I1 127.4(17) . . ?
C13 C14 C15 107.0(17) . . ?
C13 C14 I2 126.4(13) . . ?
C15 C14 I2 126.7(16) . . ?
N3 C15 C16 113.7(14) . . ?
N3 C15 C14 107.3(16) . . ?
C16 C15 C14 138.9(17) . . ?
N4 C16 C17 110.0(16) . . ?
N4 C16 C15 108.5(15) . . ?
C17 C16 C15 141.5(17) . . ?
C18 C17 C16 105.1(17) . . ?
C18 C17 I3 119.7(15) . . ?
C16 C17 I3 135.2(16) . . ?
C18 C17 I3A 132(2) . 4_565 ?
C16 C17 I3A 123(2) . 4_565 ?
C18 C17 I3A 132(2) . . ?
C16 C17 I3A 123(2) . . ?
I3A C17 I3A 0(2) 4_565 . ?
C17 C18 C19 112.1(19) . . ?
C17 C18 I4A 116(2) . . ?
C19 C18 I4A 132(2) . . ?
C17 C18 I4 124.2(15) . . ?
C19 C18 I4 123.8(16) . . ?
C1 C19 N4 120.0(16) . . ?
C1 C19 C18 135.0(19) . . ?
N4 C19 C18 105.0(16) . . ?
C21 C20 C21 120(2) 4_565 . ?
C21 C20 C1 120.1(11) 4_565 . ?
C21 C20 C1 120.1(11) . . ?
F1 C21 C22 117.4(17) . . ?
F1 C21 C20 121.6(14) . . ?
C22 C21 C20 120.9(19) . . ?
F2 C22 C21 121.5(14) . . ?
F2 C22 C23 119.5(17) . . ?
C21 C22 C23 118.8(16) . . ?
F3 C23 C22 119.3(14) . 4_565 ?
F3 C23 C22 119.3(14) . . ?
C22 C23 C22 120(2) 4_565 . ?
C25 C24 C25 114.0(16) . 4_565 ?
C25 C24 C6 123.0(8) . . ?
C25 C24 C6 123.0(8) 4_565 . ?
F4 C25 C26 120.0(14) . . ?
F4 C25 C24 117.4(11) . . ?
C26 C25 C24 122.5(15) . . ?
F5 C26 C25 120.1(14) . . ?
F5 C26 C27 118.7(10) . . ?
C25 C26 C27 121.2(14) . . ?
F6 C27 C26 120.7(7) . . ?
F6 C27 C26 120.7(7) . 4_565 ?
C26 C27 C26 118.6(15) . 4_565 ?
C29 C28 C29 113(2) . 4_565 ?
C29 C28 C11 123.3(10) . . ?
C29 C28 C11 123.3(10) 4_565 . ?
F7 C29 C30 119.9(9) . . ?
F7 C29 C28 117.3(11) . . ?
C30 C29 C28 122.8(16) . . ?
C29 C30 C31 123.8(6) . . ?
C29 C30 F8 115.1(9) . . ?
C31 C30 F8 121.1(6) . . ?
F9 C31 C30 123.38(12) . 4_565 ?
F9 C31 C30 123.38(12) . . ?
C30 C31 C30 113.16(14) 4_565 . ?
Cl2 C32 Cl1 113.2(7) . . ?
Cl3 Cl3 C33 70.9(4) 4_575 . ?
Cl3 C33 Cl3 38.2(8) 4_575 . ?
Cl3 C33 Cl4 106.1(12) 4_575 . ?
Cl3 C33 Cl4 106.1(12) . . ?

_refine_diff_density_max         2.573
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.153

####################################################################### 
# 
# 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_Gross99
_database_code_depnum_ccdc_archive 'CCDC 1888513'
loop_
_audit_author_name
_audit_author_address
'Fridman Natalia '
;Technion
Israel
;
_audit_update_record             
;
2019-01-03 deposited with the CCDC.	2019-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Gross99 (Zhenya)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H13 F8 I4 N4 P, C H2 Cl2'
_chemical_formula_sum            'C38 H15 Cl2 F8 I4 N4 P'
_chemical_formula_weight         1289.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   21.925(2)
_cell_length_b                   13.1020(11)
_cell_length_c                   13.146(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.96(5)
_cell_angle_gamma                90
_cell_volume                     3740.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6114
_cell_measurement_theta_min      1.876
_cell_measurement_theta_max      24.529

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.289
_exptl_crystal_F_000             2416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.596
_shelx_estimated_absorpt_T_min   0.358
_shelx_estimated_absorpt_T_max   0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.338
_exptl_absorpt_correction_T_max  0.651
_exptl_absorpt_process_details   
; 
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'  
;
_exptl_special_details           
;  
 ?  
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean 95
_diffrn_reflns_number            6114
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         24.529
_diffrn_reflns_theta_full        24.529
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6114
_reflns_number_gt                5373
_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       'Collect (Nonius, 2006)'
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.10.1'
_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)+(0.0545P)²+34.6741P] 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         6114
_refine_ls_number_parameters     488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.45491(3) 0.03975(5) 0.10171(5) 0.04151(19) Uani 1 1 d . . . . .
I2 I 0.46100(3) -0.17168(5) 0.28310(6) 0.0510(2) Uani 1 1 d . . . . .
I3 I 0.36922(18) -0.3299(3) 0.4393(3) 0.0532(10) Uani 0.84(4) 1 d . . P A 1
I3A I 0.361(2) -0.344(3) 0.420(4) 0.093(7) Uani 0.16(4) 1 d . . P A 2
I4 I 0.23230(3) -0.34191(4) 0.56477(5) 0.04286(19) Uani 1 1 d . . . . .
P1 P 0.23104(9) 0.04546(15) 0.31873(14) 0.0248(4) Uani 1 1 d . . . . .
F1 F 0.2000(3) -0.0658(4) 0.6915(4) 0.0502(14) Uani 1 1 d . . . . .
F2 F 0.0675(3) -0.2413(4) 0.4433(4) 0.0509(14) Uani 1 1 d . . . . .
F3 F 0.1494(3) 0.3690(5) 0.5014(4) 0.0558(15) Uani 1 1 d . . . . .
F4 F 0.0471(3) 0.3081(5) 0.1716(4) 0.0497(13) Uani 1 1 d . . . . .
F5 F 0.3911(3) 0.3033(4) 0.1491(4) 0.0478(13) Uani 1 1 d . . . . .
F6 F 0.2739(3) 0.0712(4) -0.0645(4) 0.0488(13) Uani 1 1 d . . . . .
F7 F 0.2724(2) 0.1042(3) 0.4108(3) 0.0323(10) Uani 1 1 d . . . . .
F8 F 0.1877(2) -0.0117(3) 0.2272(3) 0.0314(10) Uani 1 1 d . . . . .
N1 N 0.1648(3) 0.0665(5) 0.3847(5) 0.0249(13) Uani 1 1 d . . . . .
N2 N 0.2220(3) 0.1631(5) 0.2467(5) 0.0252(14) Uani 1 1 d . . . . .
N3 N 0.2992(3) 0.0123(5) 0.2615(5) 0.0276(14) Uani 1 1 d . . . . .
N4 N 0.2468(3) -0.0756(5) 0.3828(5) 0.0298(15) Uani 1 1 d . . . . .
C1 C 0.1638(4) -0.0953(6) 0.4827(6) 0.0273(17) Uani 1 1 d . . . . .
C2 C 0.1401(4) -0.0016(6) 0.4509(6) 0.0304(17) Uani 1 1 d . . . . .
C3 C 0.0895(4) 0.0467(6) 0.4876(6) 0.0308(18) Uani 1 1 d . . . . .
H3 H 0.0639 0.0171 0.5323 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0838(4) 0.1425(6) 0.4481(6) 0.0333(19) Uani 1 1 d . . . . .
H4 H 0.0541 0.1918 0.4612 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1301(4) 0.1559(6) 0.3834(6) 0.0263(16) Uani 1 1 d . . . . .
C6 C 0.1386(4) 0.2416(6) 0.3272(6) 0.0291(17) Uani 1 1 d . . . . .
C7 C 0.1828(4) 0.2434(6) 0.2590(6) 0.0289(17) Uani 1 1 d . . . . .
C8 C 0.1911(4) 0.3220(6) 0.1893(6) 0.0295(17) Uani 1 1 d . . . . .
H8 H 0.1705 0.3861 0.1845 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2327(4) 0.2908(6) 0.1316(6) 0.0326(18) Uani 1 1 d . . . . .
H9 H 0.2456 0.3278 0.0762 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2545(4) 0.1932(6) 0.1664(6) 0.0282(17) Uani 1 1 d . . . . .
C11 C 0.3045(4) 0.1435(6) 0.1355(6) 0.0266(16) Uani 1 1 d . . . . .
C12 C 0.3290(3) 0.0588(6) 0.1877(6) 0.0266(16) Uani 1 1 d . . . . .
C13 C 0.3852(4) 0.0034(6) 0.1848(6) 0.0300(17) Uani 1 1 d . . . . .
C14 C 0.3868(4) -0.0761(6) 0.2538(6) 0.0338(19) Uani 1 1 d . . . . .
C15 C 0.3324(4) -0.0714(6) 0.2998(6) 0.0292(17) Uani 1 1 d . . . . .
C16 C 0.3001(4) -0.1250(6) 0.3677(6) 0.0324(18) Uani 1 1 d . . . . .
C17 C 0.3032(4) -0.2178(6) 0.4230(6) 0.0308(18) Uani 1 1 d . . . . .
C18 C 0.2518(4) -0.2222(6) 0.4727(6) 0.0300(17) Uani 1 1 d . . . . .
C19 C 0.2168(4) -0.1304(6) 0.4500(6) 0.0285(17) Uani 1 1 d . . . . .
C20 C 0.1344(2) -0.1511(4) 0.5646(3) 0.0298(18) Uani 1 1 d G . . . .
C21 C 0.1577(2) -0.1342(4) 0.6670(4) 0.039(2) Uani 1 1 d G . . . .
C22 C 0.1351(3) -0.1894(5) 0.7439(3) 0.046(2) Uani 1 1 d G . . . .
H22 H 0.1510 -0.1778 0.8138 0.056 Uiso 1 1 calc R U . . .
C23 C 0.0890(3) -0.2616(4) 0.7184(3) 0.043(2) Uani 1 1 d G . . . .
H23 H 0.0736 -0.2994 0.7709 0.052 Uiso 1 1 calc R U . . .
C24 C 0.0657(2) -0.2786(4) 0.6160(4) 0.039(2) Uani 1 1 d G . . . .
H24 H 0.0343 -0.3280 0.5986 0.047 Uiso 1 1 calc R U . . .
C25 C 0.0884(2) -0.2234(4) 0.5391(3) 0.0343(19) Uani 1 1 d G . . . .
C26 C 0.1003(2) 0.3358(3) 0.3356(4) 0.0297(17) Uani 1 1 d G . . . .
C27 C 0.1097(2) 0.3955(4) 0.4237(4) 0.039(2) Uani 1 1 d G . . . .
C28 C 0.0759(3) 0.4846(4) 0.4295(4) 0.051(3) Uani 1 1 d G . . . .
H28 H 0.0823 0.5254 0.4897 0.061 Uiso 1 1 calc R U . . .
C29 C 0.0327(3) 0.5138(4) 0.3472(5) 0.058(3) Uani 1 1 d G . . . .
H29 H 0.0096 0.5747 0.3511 0.070 Uiso 1 1 calc R U . . .
C30 C 0.0233(2) 0.4540(5) 0.2590(4) 0.053(3) Uani 1 1 d G . . . .
H30 H -0.0062 0.4740 0.2028 0.063 Uiso 1 1 calc R U . . .
C31 C 0.0571(3) 0.3650(4) 0.2532(3) 0.040(2) Uani 1 1 d G . . . .
C32 C 0.3318(2) 0.1871(4) 0.0450(3) 0.0308(18) Uani 1 1 d G . . . .
C33 C 0.3757(2) 0.2642(4) 0.0586(3) 0.0342(19) Uani 1 1 d G . . . .
C34 C 0.4038(2) 0.2973(4) -0.0240(4) 0.041(2) Uani 1 1 d G . . . .
H34 H 0.4338 0.3501 -0.0148 0.049 Uiso 1 1 calc R U . . .
C35 C 0.3880(3) 0.2533(4) -0.1203(3) 0.042(2) Uani 1 1 d G . . . .
H35 H 0.4072 0.2759 -0.1767 0.051 Uiso 1 1 calc R U . . .
C36 C 0.3441(3) 0.1761(4) -0.1339(3) 0.039(2) Uani 1 1 d G . . . .
H36 H 0.3333 0.1460 -0.1996 0.046 Uiso 1 1 calc R U . . .
C37 C 0.3160(2) 0.1430(4) -0.0513(4) 0.0331(19) Uani 1 1 d G . . . .
Cl1 Cl 0.33026(16) -0.4656(3) 0.1343(3) 0.0941(12) Uani 1 1 d . . . . .
Cl2 Cl 0.4478(2) -0.4275(3) 0.0686(4) 0.1033(13) Uani 1 1 d . . . . .
C38 C 0.4082(6) -0.4451(12) 0.1729(11) 0.081(4) Uani 1 1 d . . . . .
H38A H 0.4258 -0.5044 0.2136 0.097 Uiso 1 1 calc R U . . .
H38B H 0.4136 -0.3840 0.2176 0.097 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C13 2.054(8) . ?
I2 C14 2.046(8) . ?
I3 C17 2.053(8) . ?
I3A C17 2.09(2) . ?
I4 C18 2.062(7) . ?
P1 F7 1.605(5) . ?
P1 F8 1.611(5) . ?
P1 N2 1.806(6) . ?
P1 N4 1.807(7) . ?
P1 N1 1.813(6) . ?
P1 N3 1.817(7) . ?
F1 C21 1.297(6) . ?
F2 C25 1.300(6) . ?
F3 C27 1.294(7) . ?
F4 C31 1.300(7) . ?
F5 C33 1.296(6) . ?
F6 C37 1.312(6) . ?
N1 C5 1.395(10) . ?
N1 C2 1.407(10) . ?
N2 C7 1.382(10) . ?
N2 C10 1.409(10) . ?
N3 C15 1.373(10) . ?
N3 C12 1.384(10) . ?
N4 C16 1.372(10) . ?
N4 C19 1.376(10) . ?
C1 C19 1.372(11) . ?
C1 C2 1.375(12) . ?
C1 C20 1.517(8) . ?
C2 C3 1.420(11) . ?
C3 C4 1.357(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(11) . ?
C6 C7 1.408(11) . ?
C6 C26 1.505(8) . ?
C7 C8 1.407(11) . ?
C8 C9 1.330(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(11) . ?
C11 C12 1.374(11) . ?
C11 C32 1.515(8) . ?
C12 C13 1.436(11) . ?
C13 C14 1.378(12) . ?
C14 C15 1.412(11) . ?
C15 C16 1.403(11) . ?
C16 C17 1.413(11) . ?
C17 C18 1.379(11) . ?
C18 C19 1.436(11) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.3900 . ?
C29 H29 0.9500 . ?
C30 C31 1.3900 . ?
C30 H30 0.9500 . ?
C32 C33 1.3900 . ?
C32 C37 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
Cl1 C38 1.735(13) . ?
Cl2 C38 1.737(14) . ?
C38 H38A 0.9900 . ?
C38 H38B 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
F7 P1 F8 178.2(3) . . ?
F7 P1 N2 89.8(3) . . ?
F8 P1 N2 89.7(3) . . ?
F7 P1 N4 91.0(3) . . ?
F8 P1 N4 89.7(3) . . ?
N2 P1 N4 173.7(3) . . ?
F7 P1 N1 88.4(3) . . ?
F8 P1 N1 89.9(3) . . ?
N2 P1 N1 94.8(3) . . ?
N4 P1 N1 91.4(3) . . ?
F7 P1 N3 90.9(3) . . ?
F8 P1 N3 90.8(3) . . ?
N2 P1 N3 91.3(3) . . ?
N4 P1 N3 82.4(3) . . ?
N1 P1 N3 173.8(3) . . ?
C5 N1 C2 106.5(6) . . ?
C5 N1 P1 126.4(5) . . ?
C2 N1 P1 127.0(5) . . ?
C7 N2 C10 105.2(6) . . ?
C7 N2 P1 127.8(5) . . ?
C10 N2 P1 127.0(5) . . ?
C15 N3 C12 109.3(6) . . ?
C15 N3 P1 117.6(5) . . ?
C12 N3 P1 132.9(5) . . ?
C16 N4 C19 109.9(7) . . ?
C16 N4 P1 117.3(5) . . ?
C19 N4 P1 132.8(5) . . ?
C19 C1 C2 120.3(7) . . ?
C19 C1 C20 121.5(7) . . ?
C2 C1 C20 117.8(7) . . ?
C1 C2 N1 126.4(7) . . ?
C1 C2 C3 125.1(7) . . ?
N1 C2 C3 108.2(7) . . ?
C4 C3 C2 108.5(7) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 C5 108.0(7) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
C6 C5 N1 125.4(7) . . ?
C6 C5 C4 125.8(7) . . ?
N1 C5 C4 108.8(6) . . ?
C5 C6 C7 120.9(7) . . ?
C5 C6 C26 120.8(7) . . ?
C7 C6 C26 118.3(7) . . ?
N2 C7 C8 110.0(7) . . ?
N2 C7 C6 123.8(7) . . ?
C8 C7 C6 126.0(7) . . ?
C9 C8 C7 107.9(7) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
C8 C9 C10 108.7(7) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
C11 C10 N2 126.2(7) . . ?
C11 C10 C9 125.1(7) . . ?
N2 C10 C9 108.1(7) . . ?
C12 C11 C10 120.3(7) . . ?
C12 C11 C32 121.8(7) . . ?
C10 C11 C32 117.9(7) . . ?
C11 C12 N3 121.1(7) . . ?
C11 C12 C13 132.3(7) . . ?
N3 C12 C13 106.6(7) . . ?
C14 C13 C12 108.0(7) . . ?
C14 C13 I1 124.9(6) . . ?
C12 C13 I1 126.9(6) . . ?
C13 C14 C15 107.6(7) . . ?
C13 C14 I2 122.3(6) . . ?
C15 C14 I2 130.0(6) . . ?
N3 C15 C16 110.1(7) . . ?
N3 C15 C14 108.3(7) . . ?
C16 C15 C14 141.5(8) . . ?
N4 C16 C15 111.8(7) . . ?
N4 C16 C17 108.2(7) . . ?
C15 C16 C17 139.9(8) . . ?
C18 C17 C16 107.2(7) . . ?
C18 C17 I3 122.1(6) . . ?
C16 C17 I3 130.7(6) . . ?
C18 C17 I3A 120.7(9) . . ?
C16 C17 I3A 131.3(8) . . ?
C17 C18 C19 108.4(7) . . ?
C17 C18 I4 124.0(6) . . ?
C19 C18 I4 127.6(6) . . ?
C1 C19 N4 121.9(7) . . ?
C1 C19 C18 131.9(7) . . ?
N4 C19 C18 106.2(7) . . ?
C21 C20 C25 120.0 . . ?
C21 C20 C1 118.3(4) . . ?
C25 C20 C1 121.5(4) . . ?
F1 C21 C20 120.4(4) . . ?
F1 C21 C22 119.6(4) . . ?
C20 C21 C22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
F2 C25 C24 119.8(4) . . ?
F2 C25 C20 120.2(4) . . ?
C24 C25 C20 120.0 . . ?
C27 C26 C31 120.0 . . ?
C27 C26 C6 120.2(4) . . ?
C31 C26 C6 119.7(4) . . ?
F3 C27 C28 119.2(4) . . ?
F3 C27 C26 120.8(4) . . ?
C28 C27 C26 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
F4 C31 C30 119.7(4) . . ?
F4 C31 C26 120.3(4) . . ?
C30 C31 C26 120.0 . . ?
C33 C32 C37 120.0 . . ?
C33 C32 C11 121.0(4) . . ?
C37 C32 C11 118.8(4) . . ?
F5 C33 C34 120.5(4) . . ?
F5 C33 C32 119.5(4) . . ?
C34 C33 C32 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
F6 C37 C36 119.9(4) . . ?
F6 C37 C32 120.0(4) . . ?
C36 C37 C32 120.0 . . ?
Cl1 C38 Cl2 111.6(8) . . ?
Cl1 C38 H38A 109.3 . . ?
Cl2 C38 H38A 109.3 . . ?
Cl1 C38 H38B 109.3 . . ?
Cl2 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?

_refine_diff_density_max         1.209
_refine_diff_density_min         -1.161
_refine_diff_density_rms         0.155

