# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_FF4I
_database_code_depnum_ccdc_archive 'CCDC 1840351'
_audit_update_record             
;
2018-04-29 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 F4 I N O2, 0.333(C3 H6 O), 0.333(H2 O)'
_chemical_formula_sum            'C10 H8.67 F4 I N O2.67'
_chemical_formula_weight         388.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4630 1.7726 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_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'

_cell_length_a                   18.049(4)
_cell_length_b                   5.593(1)
_cell_length_c                   18.384(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.36(3)
_cell_angle_gamma                90
_cell_volume                     1854.3(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1666
_cell_measurement_theta_min      1.092
_cell_measurement_theta_max      29.085

_exptl_crystal_description       Rods
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.503
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700

_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12396
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_av_R_equivalents  0.0442

_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.092
_diffrn_reflns_theta_max         29.085
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             8997
_reflns_number_gt                6660
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.798
_reflns_Friedel_fraction_full    0.819

_reflns_special_details          
;
 _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.
;


_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for water hydrogens, methyl and 
protonated amino groups). Anisotropic thermal motion modeling has 
been applied to all atoms with full occupancy. Minor thermal 
restrains (SIMU) have been used to prevent phenyl ring carbons of 
residue 3, to become NPD. Model refined as a 2-component twin.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1362P)²+27.3387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8997
_refine_ls_number_parameters     481
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0983
_refine_ls_wR_factor_ref         0.2826
_refine_ls_wR_factor_gt          0.2614
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.010
_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
O_1 O 0.8622(10) 0.570(3) -0.0511(8) 0.036(4) Uani 1 1 d . . . . .
C_1 C 0.8359(15) 0.607(4) 0.0114(10) 0.033(5) Uani 1 1 d . . . . .
OXT_1 O 0.8209(11) 0.466(3) 0.0579(10) 0.040(4) Uani 1 1 d . . . . .
CA_1 C 0.8151(16) 0.879(5) 0.0258(13) 0.042(5) Uani 1 1 d . . . . .
HA_1 H 0.819296 0.912366 0.079264 0.050 Uiso 1 1 calc R U . . .
N_1 N 0.8685(11) 1.032(4) -0.0121(11) 0.036(4) Uani 1 1 d . . . . .
H0A_1 H 0.867597 1.182936 0.006638 0.055 Uiso 1 1 calc R U . . .
H0B_1 H 0.855692 1.037609 -0.060498 0.055 Uiso 1 1 calc R U . . .
H0C_1 H 0.914967 0.970689 -0.005768 0.055 Uiso 1 1 calc R U . . .
CB_1 C 0.7379(14) 0.944(4) -0.0030(14) 0.039(5) Uani 1 1 d . . . . .
HB1_1 H 0.734280 0.920903 -0.056394 0.047 Uiso 1 1 calc R U . . .
HB2_1 H 0.727779 1.114413 0.007418 0.047 Uiso 1 1 calc R U . . .
CG_1 C 0.6797(9) 0.783(3) 0.0339(9) 0.043(6) Uani 1 1 d G . . . .
CD1_1 C 0.6602(10) 0.831(3) 0.1048(9) 0.045(6) Uani 1 1 d G . . . .
CE1_1 C 0.6091(11) 0.685(4) 0.1381(7) 0.053(7) Uani 1 1 d G . . . .
CZ_1 C 0.5776(10) 0.492(3) 0.1005(9) 0.056(8) Uani 1 1 d G . . . .
CE2_1 C 0.5971(10) 0.445(3) 0.0295(8) 0.040(5) Uani 1 1 d G . . . .
CD2_1 C 0.6482(11) 0.591(3) -0.0037(7) 0.055(8) Uani 1 1 d G . . . .
FD1_1 F 0.6875(11) 1.004(3) 0.1409(9) 0.054(4) Uani 1 1 d . . . . .
FE1_1 F 0.5909(10) 0.722(4) 0.2055(8) 0.062(5) Uani 1 1 d . . . . .
IZ_1 I 0.50119(12) 0.2626(3) 0.14915(14) 0.0619(6) Uani 1 1 d . . . . .
FE2_1 F 0.5696(11) 0.248(5) -0.0087(12) 0.079(7) Uani 1 1 d . . . . .
FD2_1 F 0.6686(10) 0.536(3) -0.0689(8) 0.049(4) Uani 1 1 d . . . . .
O_2 O 0.8723(12) 1.038(3) -0.1610(8) 0.042(4) Uani 1 1 d . . . . .
C_2 C 0.8375(13) 0.995(5) -0.2243(11) 0.037(5) Uani 1 1 d . . . . .
OXT_2 O 0.8201(10) 1.156(3) -0.2657(9) 0.041(4) Uani 1 1 d . . . . .
CA_2 C 0.8229(11) 0.743(4) -0.2462(11) 0.029(4) Uani 1 1 d . . . . .
HA_2 H 0.836116 0.722360 -0.298093 0.035 Uiso 1 1 calc R U . . .
N_2 N 0.8672(12) 0.573(4) -0.2003(10) 0.034(4) Uani 1 1 d . . . . .
H0A_2 H 0.906712 0.650933 -0.178908 0.050 Uiso 1 1 calc R U . . .
H0B_2 H 0.883694 0.452274 -0.228536 0.050 Uiso 1 1 calc R U . . .
H0C_2 H 0.838472 0.512077 -0.165289 0.050 Uiso 1 1 calc R U . . .
CB_2 C 0.7411(12) 0.683(5) -0.2392(12) 0.035(5) Uani 1 1 d . . . . .
HB1_2 H 0.728811 0.689809 -0.187260 0.042 Uiso 1 1 calc R U . . .
HB2_2 H 0.731912 0.517864 -0.256697 0.042 Uiso 1 1 calc R U . . .
CG_2 C 0.6899(8) 0.859(2) -0.2837(7) 0.037(5) Uani 1 1 d G . . . .
CD1_2 C 0.6786(9) 0.828(2) -0.3583(7) 0.034(5) Uani 1 1 d G . . . .
CE1_2 C 0.6331(9) 0.985(3) -0.3981(5) 0.037(5) Uani 1 1 d G . . . .
CZ_2 C 0.5988(8) 1.173(2) -0.3633(7) 0.040(5) Uani 1 1 d G . . . .
CE2_2 C 0.6101(9) 1.204(2) -0.2886(7) 0.038(5) Uani 1 1 d G . . . .
CD2_2 C 0.6556(9) 1.047(3) -0.2488(5) 0.035(5) Uani 1 1 d G . . . .
FD1_2 F 0.7123(9) 0.657(3) -0.3938(8) 0.043(4) Uani 1 1 d . . . . .
FE1_2 F 0.6268(9) 0.959(3) -0.4688(7) 0.047(4) Uani 1 1 d . . . . .
IZ_2 I 0.52872(10) 1.4016(3) -0.42554(10) 0.0454(4) Uani 1 1 d . . . . .
FE2_2 F 0.5768(9) 1.371(3) -0.2550(9) 0.055(4) Uani 1 1 d . . . . .
FD2_2 F 0.6661(9) 1.087(3) -0.1792(7) 0.045(3) Uani 1 1 d . . . . .
O_3 O 0.8570(10) 0.083(4) 0.2016(9) 0.039(4) Uani 1 1 d . . . . .
C_3 C 0.9194(13) 0.173(5) 0.2013(10) 0.034(5) Uani 1 1 d . . . . .
OXT_3 O 0.9804(10) 0.058(3) 0.1962(9) 0.041(4) Uani 1 1 d . . . . .
CA_3 C 0.9281(15) 0.445(4) 0.2092(10) 0.035(5) Uani 1 1 d . . . . .
HA_3 H 0.957137 0.502610 0.167534 0.042 Uiso 1 1 calc R U . . .
N_3 N 0.8537(12) 0.556(4) 0.2027(9) 0.036(4) Uani 1 1 d . . . . .
H0A_3 H 0.818932 0.440010 0.194179 0.054 Uiso 1 1 calc R U . . .
H0B_3 H 0.852199 0.661661 0.165166 0.054 Uiso 1 1 calc R U . . .
H0C_3 H 0.844218 0.633237 0.244830 0.054 Uiso 1 1 calc R U . . .
CB_3 C 0.9708(13) 0.517(4) 0.2800(11) 0.034(5) Uani 1 1 d . . . . .
HB1_3 H 1.021506 0.449448 0.279095 0.041 Uiso 1 1 calc R U . . .
HB2_3 H 0.975432 0.692968 0.281107 0.041 Uiso 1 1 calc R U . . .
CG_3 C 0.9361(9) 0.436(3) 0.3488(6) 0.038(5) Uani 1 1 d G . . . .
CD1_3 C 0.9610(8) 0.227(3) 0.3827(7) 0.036(5) Uani 1 1 d G . . . .
CE1_3 C 0.9324(8) 0.158(2) 0.4485(7) 0.042(5) Uani 1 1 d G U . . .
CZ_3 C 0.8789(8) 0.297(2) 0.4804(6) 0.030(4) Uani 1 1 d G U . . .
CE2_3 C 0.8539(8) 0.506(2) 0.4465(7) 0.032(4) Uani 1 1 d G U . . .
CD2_3 C 0.8825(9) 0.576(2) 0.3807(7) 0.037(5) Uani 1 1 d G . . . .
FD1_3 F 1.0125(9) 0.094(3) 0.3545(8) 0.043(3) Uani 1 1 d . . . . .
FE1_3 F 0.9548(9) -0.040(3) 0.4783(7) 0.043(3) Uani 1 1 d . . . . .
IZ_3 I 0.84232(9) 0.2084(3) 0.58417(7) 0.0356(3) Uani 1 1 d . . . . .
FE2_3 F 0.8036(9) 0.646(3) 0.4761(7) 0.044(4) Uani 1 1 d . . . . .
FD2_3 F 0.8617(9) 0.776(2) 0.3510(6) 0.039(3) Uani 1 1 d . . . . .
O_4 O 1.0044(10) 0.365(4) -0.0597(10) 0.046(4) Uani 1 1 d . . . . .
H1_4 H 1.01(2) 0.41(8) -0.10(2) 0.068 Uiso 1 1 d . U . . .
H2_4 H 0.96(2) 0.39(8) -0.05(2) 0.068 Uiso 1 1 d . U . . .
O_5 O 0.7319(14) 0.495(4) 0.2909(14) 0.062(6) Uani 1 1 d . . . . .
C_5 C 0.698(2) 0.350(6) 0.3269(15) 0.059(9) Uani 1 1 d . . . . .
C2_5 C 0.715(3) 0.090(6) 0.327(2) 0.078(13) Uani 1 1 d . . . . .
H2A_5 H 0.760704 0.062553 0.301281 0.117 Uiso 1 1 calc R U . . .
H2B_5 H 0.673918 0.004094 0.301500 0.117 Uiso 1 1 calc R U . . .
H2C_5 H 0.720721 0.032652 0.376842 0.117 Uiso 1 1 calc R U . . .
C1_5 C 0.629(3) 0.432(10) 0.369(4) 0.13(3) Uani 1 1 d . . . . .
H1A_5 H 0.585975 0.446571 0.335466 0.196 Uiso 1 1 calc R U . . .
H1B_5 H 0.639455 0.586503 0.392524 0.196 Uiso 1 1 calc R U . . .
H1C_5 H 0.618547 0.312910 0.406808 0.196 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
O_1 C_1 1.28(2) . ?
C_1 OXT_1 1.20(2) . ?
C_1 CA_1 1.59(3) . ?
CA_1 N_1 1.48(3) . ?
CA_1 CB_1 1.51(4) . ?
CA_1 HA_1 1.0000 . ?
N_1 H0A_1 0.9100 . ?
N_1 H0B_1 0.9100 . ?
N_1 H0C_1 0.9100 . ?
CB_1 CG_1 1.56(3) . ?
CB_1 HB1_1 0.9900 . ?
CB_1 HB2_1 0.9900 . ?
CG_1 CD1_1 1.3900 . ?
CG_1 CD2_1 1.3900 . ?
CD1_1 FD1_1 1.26(2) . ?
CD1_1 CE1_1 1.3900 . ?
CE1_1 FE1_1 1.311(17) . ?
CE1_1 CZ_1 1.3900 . ?
CZ_1 CE2_1 1.3900 . ?
CZ_1 IZ_1 2.111(12) . ?
CE2_1 FE2_1 1.39(3) . ?
CE2_1 CD2_1 1.3900 . ?
CD2_1 FD2_1 1.304(17) . ?
O_2 C_2 1.32(3) . ?
C_2 OXT_2 1.21(3) . ?
C_2 CA_2 1.48(3) . ?
CA_2 N_2 1.48(3) . ?
CA_2 CB_2 1.52(3) . ?
CA_2 HA_2 1.0000 . ?
N_2 H0A_2 0.9100 . ?
N_2 H0B_2 0.9100 . ?
N_2 H0C_2 0.9100 . ?
CB_2 CG_2 1.56(3) . ?
CB_2 HB1_2 0.9900 . ?
CB_2 HB2_2 0.9900 . ?
CG_2 CD1_2 1.3900 . ?
CG_2 CD2_2 1.3900 . ?
CD1_2 FD1_2 1.319(18) . ?
CD1_2 CE1_2 1.3900 . ?
CE1_2 FE1_2 1.307(16) . ?
CE1_2 CZ_2 1.3900 . ?
CZ_2 CE2_2 1.3900 . ?
CZ_2 IZ_2 2.105(11) . ?
CE2_2 FE2_2 1.282(18) . ?
CE2_2 CD2_2 1.3900 . ?
CD2_2 FD2_2 1.306(15) . ?
O_3 C_3 1.23(3) . ?
C_3 OXT_3 1.28(3) . ?
C_3 CA_3 1.54(3) . ?
CA_3 N_3 1.48(3) . ?
CA_3 CB_3 1.54(3) . ?
CA_3 HA_3 1.0000 . ?
N_3 H0A_3 0.9100 . ?
N_3 H0B_3 0.9100 . ?
N_3 H0C_3 0.9100 . ?
CB_3 CG_3 1.50(2) . ?
CB_3 HB1_3 0.9900 . ?
CB_3 HB2_3 0.9900 . ?
CG_3 CD1_3 1.3900 . ?
CG_3 CD2_3 1.3900 . ?
CD1_3 FD1_3 1.315(17) . ?
CD1_3 CE1_3 1.3900 . ?
CE1_3 FE1_3 1.294(18) . ?
CE1_3 CZ_3 1.3900 . ?
CZ_3 CE2_3 1.3900 . ?
CZ_3 IZ_3 2.103(8) . ?
CE2_3 FE2_3 1.332(16) . ?
CE2_3 CD2_3 1.3900 . ?
CD2_3 FD2_3 1.295(17) . ?
O_4 H1_4 0.8(4) . ?
O_4 H2_4 0.8(4) . ?
O_5 C_5 1.23(4) . ?
C_5 C2_5 1.48(5) . ?
C_5 C1_5 1.56(5) . ?
C2_5 H2A_5 0.9800 . ?
C2_5 H2B_5 0.9800 . ?
C2_5 H2C_5 0.9800 . ?
C1_5 H1A_5 0.9800 . ?
C1_5 H1B_5 0.9800 . ?
C1_5 H1C_5 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
OXT_1 C_1 O_1 129(2) . . ?
OXT_1 C_1 CA_1 116.6(18) . . ?
O_1 C_1 CA_1 113.8(17) . . ?
N_1 CA_1 CB_1 108(2) . . ?
N_1 CA_1 C_1 108.2(18) . . ?
CB_1 CA_1 C_1 113(2) . . ?
N_1 CA_1 HA_1 109.3 . . ?
CB_1 CA_1 HA_1 109.3 . . ?
C_1 CA_1 HA_1 109.3 . . ?
CA_1 N_1 H0A_1 109.5 . . ?
CA_1 N_1 H0B_1 109.5 . . ?
H0A_1 N_1 H0B_1 109.5 . . ?
CA_1 N_1 H0C_1 109.5 . . ?
H0A_1 N_1 H0C_1 109.5 . . ?
H0B_1 N_1 H0C_1 109.5 . . ?
CA_1 CB_1 CG_1 110(2) . . ?
CA_1 CB_1 HB1_1 109.7 . . ?
CG_1 CB_1 HB1_1 109.7 . . ?
CA_1 CB_1 HB2_1 109.7 . . ?
CG_1 CB_1 HB2_1 109.7 . . ?
HB1_1 CB_1 HB2_1 108.2 . . ?
CD1_1 CG_1 CD2_1 120.0 . . ?
CD1_1 CG_1 CB_1 120.0(14) . . ?
CD2_1 CG_1 CB_1 120.0(14) . . ?
FD1_1 CD1_1 CG_1 122.0(13) . . ?
FD1_1 CD1_1 CE1_1 118.0(13) . . ?
CG_1 CD1_1 CE1_1 120.0 . . ?
FE1_1 CE1_1 CZ_1 118.7(15) . . ?
FE1_1 CE1_1 CD1_1 121.3(15) . . ?
CZ_1 CE1_1 CD1_1 120.0 . . ?
CE1_1 CZ_1 CE2_1 120.0 . . ?
CE1_1 CZ_1 IZ_1 121.5(9) . . ?
CE2_1 CZ_1 IZ_1 118.5(9) . . ?
FE2_1 CE2_1 CD2_1 118.2(13) . . ?
FE2_1 CE2_1 CZ_1 121.8(13) . . ?
CD2_1 CE2_1 CZ_1 120.0 . . ?
FD2_1 CD2_1 CE2_1 118.9(13) . . ?
FD2_1 CD2_1 CG_1 121.0(13) . . ?
CE2_1 CD2_1 CG_1 120.0 . . ?
OXT_2 C_2 O_2 121(3) . . ?
OXT_2 C_2 CA_2 120(2) . . ?
O_2 C_2 CA_2 119(2) . . ?
N_2 CA_2 C_2 111.6(18) . . ?
N_2 CA_2 CB_2 108.1(18) . . ?
C_2 CA_2 CB_2 110.4(17) . . ?
N_2 CA_2 HA_2 108.9 . . ?
C_2 CA_2 HA_2 108.9 . . ?
CB_2 CA_2 HA_2 108.9 . . ?
CA_2 N_2 H0A_2 109.5 . . ?
CA_2 N_2 H0B_2 109.5 . . ?
H0A_2 N_2 H0B_2 109.5 . . ?
CA_2 N_2 H0C_2 109.5 . . ?
H0A_2 N_2 H0C_2 109.5 . . ?
H0B_2 N_2 H0C_2 109.5 . . ?
CA_2 CB_2 CG_2 111.9(18) . . ?
CA_2 CB_2 HB1_2 109.2 . . ?
CG_2 CB_2 HB1_2 109.2 . . ?
CA_2 CB_2 HB2_2 109.2 . . ?
CG_2 CB_2 HB2_2 109.2 . . ?
HB1_2 CB_2 HB2_2 107.9 . . ?
CD1_2 CG_2 CD2_2 120.0 . . ?
CD1_2 CG_2 CB_2 119.9(12) . . ?
CD2_2 CG_2 CB_2 120.1(12) . . ?
FD1_2 CD1_2 CG_2 121.8(11) . . ?
FD1_2 CD1_2 CE1_2 118.1(11) . . ?
CG_2 CD1_2 CE1_2 120.0 . . ?
FE1_2 CE1_2 CD1_2 118.5(12) . . ?
FE1_2 CE1_2 CZ_2 121.4(12) . . ?
CD1_2 CE1_2 CZ_2 120.0 . . ?
CE1_2 CZ_2 CE2_2 120.0 . . ?
CE1_2 CZ_2 IZ_2 118.6(7) . . ?
CE2_2 CZ_2 IZ_2 121.4(7) . . ?
FE2_2 CE2_2 CD2_2 119.0(13) . . ?
FE2_2 CE2_2 CZ_2 120.9(13) . . ?
CD2_2 CE2_2 CZ_2 120.0 . . ?
FD2_2 CD2_2 CE2_2 117.8(12) . . ?
FD2_2 CD2_2 CG_2 122.2(12) . . ?
CE2_2 CD2_2 CG_2 120.0 . . ?
O_3 C_3 OXT_3 126(2) . . ?
O_3 C_3 CA_3 120(2) . . ?
OXT_3 C_3 CA_3 115(2) . . ?
N_3 CA_3 CB_3 112.3(17) . . ?
N_3 CA_3 C_3 109(2) . . ?
CB_3 CA_3 C_3 112.7(19) . . ?
N_3 CA_3 HA_3 107.7 . . ?
CB_3 CA_3 HA_3 107.7 . . ?
C_3 CA_3 HA_3 107.7 . . ?
CA_3 N_3 H0A_3 109.5 . . ?
CA_3 N_3 H0B_3 109.5 . . ?
H0A_3 N_3 H0B_3 109.5 . . ?
CA_3 N_3 H0C_3 109.5 . . ?
H0A_3 N_3 H0C_3 109.5 . . ?
H0B_3 N_3 H0C_3 109.5 . . ?
CG_3 CB_3 CA_3 115.0(19) . . ?
CG_3 CB_3 HB1_3 108.5 . . ?
CA_3 CB_3 HB1_3 108.5 . . ?
CG_3 CB_3 HB2_3 108.5 . . ?
CA_3 CB_3 HB2_3 108.5 . . ?
HB1_3 CB_3 HB2_3 107.5 . . ?
CD1_3 CG_3 CD2_3 120.0 . . ?
CD1_3 CG_3 CB_3 119.3(14) . . ?
CD2_3 CG_3 CB_3 120.6(13) . . ?
FD1_3 CD1_3 CG_3 121.4(12) . . ?
FD1_3 CD1_3 CE1_3 118.6(12) . . ?
CG_3 CD1_3 CE1_3 120.0 . . ?
FE1_3 CE1_3 CZ_3 120.8(11) . . ?
FE1_3 CE1_3 CD1_3 119.1(11) . . ?
CZ_3 CE1_3 CD1_3 120.0 . . ?
CE2_3 CZ_3 CE1_3 120.0 . . ?
CE2_3 CZ_3 IZ_3 119.8(7) . . ?
CE1_3 CZ_3 IZ_3 120.0(7) . . ?
FE2_3 CE2_3 CZ_3 121.7(11) . . ?
FE2_3 CE2_3 CD2_3 118.3(11) . . ?
CZ_3 CE2_3 CD2_3 120.0 . . ?
FD2_3 CD2_3 CE2_3 119.8(11) . . ?
FD2_3 CD2_3 CG_3 120.1(11) . . ?
CE2_3 CD2_3 CG_3 120.0 . . ?
H1_4 O_4 H2_4 106(10) . . ?
O_5 C_5 C2_5 123(3) . . ?
O_5 C_5 C1_5 120(3) . . ?
C2_5 C_5 C1_5 117(3) . . ?
C_5 C2_5 H2A_5 109.5 . . ?
C_5 C2_5 H2B_5 109.5 . . ?
H2A_5 C2_5 H2B_5 109.5 . . ?
C_5 C2_5 H2C_5 109.5 . . ?
H2A_5 C2_5 H2C_5 109.5 . . ?
H2B_5 C2_5 H2C_5 109.5 . . ?
C_5 C1_5 H1A_5 109.5 . . ?
C_5 C1_5 H1B_5 109.5 . . ?
H1A_5 C1_5 H1B_5 109.5 . . ?
C_5 C1_5 H1C_5 109.5 . . ?
H1A_5 C1_5 H1C_5 109.5 . . ?
H1B_5 C1_5 H1C_5 109.5 . . ?

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
OXT_1 C_1 CA_1 N_1 151(2) . . . . ?
O_1 C_1 CA_1 N_1 -33(3) . . . . ?
OXT_1 C_1 CA_1 CB_1 -90(3) . . . . ?
O_1 C_1 CA_1 CB_1 86(3) . . . . ?
N_1 CA_1 CB_1 CG_1 178.6(17) . . . . ?
C_1 CA_1 CB_1 CG_1 59(2) . . . . ?
CA_1 CB_1 CG_1 CD1_1 77(2) . . . . ?
CA_1 CB_1 CG_1 CD2_1 -102(2) . . . . ?
CD2_1 CG_1 CD1_1 FD1_1 -180(2) . . . . ?
CB_1 CG_1 CD1_1 FD1_1 1(2) . . . . ?
CD2_1 CG_1 CD1_1 CE1_1 0.0 . . . . ?
CB_1 CG_1 CD1_1 CE1_1 -179.0(19) . . . . ?
FD1_1 CD1_1 CE1_1 FE1_1 -2(2) . . . . ?
CG_1 CD1_1 CE1_1 FE1_1 178(2) . . . . ?
FD1_1 CD1_1 CE1_1 CZ_1 180.0(19) . . . . ?
CG_1 CD1_1 CE1_1 CZ_1 0.0 . . . . ?
FE1_1 CE1_1 CZ_1 CE2_1 -179(2) . . . . ?
CD1_1 CE1_1 CZ_1 CE2_1 0.0 . . . . ?
FE1_1 CE1_1 CZ_1 IZ_1 0.4(18) . . . . ?
CD1_1 CE1_1 CZ_1 IZ_1 178.9(14) . . . . ?
CE1_1 CZ_1 CE2_1 FE2_1 177(2) . . . . ?
IZ_1 CZ_1 CE2_1 FE2_1 -2(2) . . . . ?
CE1_1 CZ_1 CE2_1 CD2_1 0.0 . . . . ?
IZ_1 CZ_1 CE2_1 CD2_1 -179.0(14) . . . . ?
FE2_1 CE2_1 CD2_1 FD2_1 -1(2) . . . . ?
CZ_1 CE2_1 CD2_1 FD2_1 176(2) . . . . ?
FE2_1 CE2_1 CD2_1 CG_1 -177(2) . . . . ?
CZ_1 CE2_1 CD2_1 CG_1 0.0 . . . . ?
CD1_1 CG_1 CD2_1 FD2_1 -176(2) . . . . ?
CB_1 CG_1 CD2_1 FD2_1 3(2) . . . . ?
CD1_1 CG_1 CD2_1 CE2_1 0.0 . . . . ?
CB_1 CG_1 CD2_1 CE2_1 179.0(19) . . . . ?
OXT_2 C_2 CA_2 N_2 162.7(19) . . . . ?
O_2 C_2 CA_2 N_2 -15(3) . . . . ?
OXT_2 C_2 CA_2 CB_2 -77(2) . . . . ?
O_2 C_2 CA_2 CB_2 106(2) . . . . ?
N_2 CA_2 CB_2 CG_2 178.0(16) . . . . ?
C_2 CA_2 CB_2 CG_2 56(2) . . . . ?
CA_2 CB_2 CG_2 CD1_2 80.0(19) . . . . ?
CA_2 CB_2 CG_2 CD2_2 -99.7(17) . . . . ?
CD2_2 CG_2 CD1_2 FD1_2 177.5(16) . . . . ?
CB_2 CG_2 CD1_2 FD1_2 -2.3(18) . . . . ?
CD2_2 CG_2 CD1_2 CE1_2 0.0 . . . . ?
CB_2 CG_2 CD1_2 CE1_2 -179.8(16) . . . . ?
FD1_2 CD1_2 CE1_2 FE1_2 -1.2(17) . . . . ?
CG_2 CD1_2 CE1_2 FE1_2 176.4(16) . . . . ?
FD1_2 CD1_2 CE1_2 CZ_2 -177.5(15) . . . . ?
CG_2 CD1_2 CE1_2 CZ_2 0.0 . . . . ?
FE1_2 CE1_2 CZ_2 CE2_2 -176.3(16) . . . . ?
CD1_2 CE1_2 CZ_2 CE2_2 0.0 . . . . ?
FE1_2 CE1_2 CZ_2 IZ_2 4.9(15) . . . . ?
CD1_2 CE1_2 CZ_2 IZ_2 -178.8(11) . . . . ?
CE1_2 CZ_2 CE2_2 FE2_2 -177.4(17) . . . . ?
IZ_2 CZ_2 CE2_2 FE2_2 1.4(16) . . . . ?
CE1_2 CZ_2 CE2_2 CD2_2 0.0 . . . . ?
IZ_2 CZ_2 CE2_2 CD2_2 178.8(11) . . . . ?
FE2_2 CE2_2 CD2_2 FD2_2 -4.5(18) . . . . ?
CZ_2 CE2_2 CD2_2 FD2_2 178.1(16) . . . . ?
FE2_2 CE2_2 CD2_2 CG_2 177.4(17) . . . . ?
CZ_2 CE2_2 CD2_2 CG_2 0.0 . . . . ?
CD1_2 CG_2 CD2_2 FD2_2 -178.0(17) . . . . ?
CB_2 CG_2 CD2_2 FD2_2 1.8(18) . . . . ?
CD1_2 CG_2 CD2_2 CE2_2 0.0 . . . . ?
CB_2 CG_2 CD2_2 CE2_2 179.8(16) . . . . ?
O_3 C_3 CA_3 N_3 -10(2) . . . . ?
OXT_3 C_3 CA_3 N_3 171.1(15) . . . . ?
O_3 C_3 CA_3 CB_3 115(2) . . . . ?
OXT_3 C_3 CA_3 CB_3 -64(2) . . . . ?
N_3 CA_3 CB_3 CG_3 63(2) . . . . ?
C_3 CA_3 CB_3 CG_3 -60(3) . . . . ?
CA_3 CB_3 CG_3 CD1_3 97(2) . . . . ?
CA_3 CB_3 CG_3 CD2_3 -87(2) . . . . ?
CD2_3 CG_3 CD1_3 FD1_3 -178.8(17) . . . . ?
CB_3 CG_3 CD1_3 FD1_3 -2.4(19) . . . . ?
CD2_3 CG_3 CD1_3 CE1_3 0.0 . . . . ?
CB_3 CG_3 CD1_3 CE1_3 176.4(17) . . . . ?
FD1_3 CD1_3 CE1_3 FE1_3 -3.0(18) . . . . ?
CG_3 CD1_3 CE1_3 FE1_3 178.2(16) . . . . ?
FD1_3 CD1_3 CE1_3 CZ_3 178.8(17) . . . . ?
CG_3 CD1_3 CE1_3 CZ_3 0.0 . . . . ?
FE1_3 CE1_3 CZ_3 CE2_3 -178.1(16) . . . . ?
CD1_3 CE1_3 CZ_3 CE2_3 0.0 . . . . ?
FE1_3 CE1_3 CZ_3 IZ_3 7.2(15) . . . . ?
CD1_3 CE1_3 CZ_3 IZ_3 -174.7(11) . . . . ?
CE1_3 CZ_3 CE2_3 FE2_3 -178.8(17) . . . . ?
IZ_3 CZ_3 CE2_3 FE2_3 -4.1(16) . . . . ?
CE1_3 CZ_3 CE2_3 CD2_3 0.0 . . . . ?
IZ_3 CZ_3 CE2_3 CD2_3 174.7(11) . . . . ?
FE2_3 CE2_3 CD2_3 FD2_3 2.0(17) . . . . ?
CZ_3 CE2_3 CD2_3 FD2_3 -176.8(17) . . . . ?
FE2_3 CE2_3 CD2_3 CG_3 178.8(16) . . . . ?
CZ_3 CE2_3 CD2_3 CG_3 0.0 . . . . ?
CD1_3 CG_3 CD2_3 FD2_3 176.8(16) . . . . ?
CB_3 CG_3 CD2_3 FD2_3 0.5(18) . . . . ?
CD1_3 CG_3 CD2_3 CE2_3 0.0 . . . . ?
CB_3 CG_3 CD2_3 CE2_3 -176.4(17) . . . . ?

_refine_diff_density_max         3.967
_refine_diff_density_min         -2.556
_refine_diff_density_rms         0.295




# start Validation Reply Form

_vrf_PLAT342_FF4I                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02721 Ang.
RESPONSE: Crystals were prone to radiation damage. This phenomena introduced 
          electron density maps distortions close to heavy atoms and give 
          rise to quite high model e.s.d.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_dmab_ditfb_0m
_database_code_depnum_ccdc_archive 'CCDC 1841117'
_audit_update_record             
;
2018-05-03 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_dmab_ditfb_0m       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         17 Note  
RESPONSE: long cell axis
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          354.3
_chemical_formula_moiety         'C12 F8 I4, C18 H22 N2 O2'
_chemical_formula_sum            'C30 H22 F8 I4 N2 O2'
_chemical_formula_weight         1102.09

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

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

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

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

_cell_length_a                   16.6735(4)
_cell_length_b                   7.2738(2)
_cell_length_c                   29.1480(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.2300(10)
_cell_angle_gamma                90
_cell_volume                     3514.18(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9277
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      28.14

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_F_000             2064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.619
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5873
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41129
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.506
_diffrn_reflns_theta_max         30.802
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10820
_reflns_number_gt                6633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;     
 ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565
 Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E.,
 Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).
 J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL
_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)+(0.0265P)²+1.8410P] 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         10820
_refine_ls_number_parameters     413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
I1 I 0.11729(2) 0.71775(5) 0.51613(2) 0.07251(9) Uani 1 1 d . . . . .
I2 I 0.43594(2) 0.60074(4) 0.38223(2) 0.06130(8) Uani 1 1 d . . . . .
I3 I 0.93042(2) 0.77576(5) 0.39452(2) 0.08324(11) Uani 1 1 d . . . . .
I4 I 0.57134(2) 0.95857(4) 0.25783(2) 0.05923(8) Uani 1 1 d . . . . .
O1 O 0.55936(16) 0.5042(4) 0.32268(9) 0.0686(7) Uani 1 1 d . . . . .
F2 F 0.42864(14) 0.6316(5) 0.49141(8) 0.0975(9) Uani 1 1 d . . . . .
F3 F 0.12650(13) 0.6980(5) 0.40696(9) 0.0963(9) Uani 1 1 d . . . . .
F4 F 0.30746(16) 0.6778(5) 0.54184(8) 0.1005(7) Uani 1 1 d . . . . .
F5 F 0.88358(13) 0.7827(4) 0.28589(9) 0.0814(7) Uani 1 1 d . . . . .
F8 F 0.61819(14) 0.9589(4) 0.36733(8) 0.0845(8) Uani 1 1 d . . . . .
F6 F 0.74714(14) 0.8547(4) 0.23397(7) 0.0767(7) Uani 1 1 d . . . . .
F7 F 0.75435(16) 0.8861(5) 0.41937(7) 0.0974(9) Uani 1 1 d . . . . .
O2 O 0.0142(2) 0.2533(6) 0.42556(14) 0.1009(12) Uani 1 1 d . . . . .
C23 C 0.4005(3) 0.0996(7) 0.34852(14) 0.0735(12) Uani 1 1 d . . . . .
H23A H 0.374026 -0.007619 0.334941 0.110 Uiso 1 1 calc R U . . .
H23B H 0.457263 0.092127 0.345824 0.110 Uiso 1 1 calc R U . . .
H23C H 0.378654 0.207423 0.332780 0.110 Uiso 1 1 calc R U . . .
C1 C 0.7665(2) 0.3707(5) 0.35162(12) 0.0542(9) Uani 1 1 d . . . . .
H1 H 0.765806 0.376203 0.383452 0.065 Uiso 1 1 calc R U . . .
F1 F 0.24843(16) 0.6553(5) 0.35661(8) 0.1005(7) Uani 1 1 d . . . . .
C8 C 0.9092(3) 0.2401(8) 0.21896(16) 0.0861(15) Uani 1 1 d . . . . .
H8A H 0.874570 0.139257 0.208918 0.129 Uiso 1 1 calc R U . . .
H8B H 0.963293 0.213536 0.212525 0.129 Uiso 1 1 calc R U . . .
H8C H 0.890572 0.349782 0.202853 0.129 Uiso 1 1 calc R U . . .
N1 N 0.90816(19) 0.2671(5) 0.26819(12) 0.0690(9) Uani 1 1 d . . . . .
C3 C 0.8388(2) 0.3124(5) 0.28626(12) 0.0505(8) Uani 1 1 d . . . . .
C2 C 0.8365(2) 0.3235(5) 0.33460(12) 0.0536(9) Uani 1 1 d . . . . .
H2 H 0.882600 0.298756 0.354586 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6958(2) 0.4111(5) 0.32333(12) 0.0486(8) Uani 1 1 d . . . . .
C7 C 0.6235(2) 0.4628(6) 0.34365(13) 0.0599(9) Uani 1 1 d . . . . .
H7 H 0.626588 0.464149 0.375704 0.072 Uiso 1 1 calc R U . . .
C9 C 0.9822(2) 0.2327(8) 0.29818(16) 0.0815(14) Uani 1 1 d . . . . .
H9A H 0.991411 0.331372 0.319976 0.122 Uiso 1 1 calc R U . . .
H9B H 1.026662 0.224826 0.279928 0.122 Uiso 1 1 calc R U . . .
H9C H 0.977358 0.119069 0.314419 0.122 Uiso 1 1 calc R U . . .
C4 C 0.7670(2) 0.3511(5) 0.25766(12) 0.0542(9) Uani 1 1 d . . . . .
H4 H 0.766671 0.342877 0.225801 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6982(2) 0.4001(5) 0.27572(12) 0.0528(8) Uani 1 1 d . . . . .
H5 H 0.652043 0.426788 0.255999 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3536(2) 0.6496(6) 0.46972(12) 0.0567(9) Uani 1 1 d . . . . .
C11 C 0.3420(2) 0.6424(5) 0.42236(12) 0.0495(8) Uani 1 1 d . . . . .
C12 C 0.2638(2) 0.6622(6) 0.40279(11) 0.0549(9) Uani 1 1 d . . . . .
C13 C 0.2010(2) 0.6837(6) 0.42886(13) 0.0569(9) Uani 1 1 d . . . . .
C14 C 0.2124(2) 0.6892(5) 0.47601(12) 0.0536(9) Uani 1 1 d . . . . .
C15 C 0.2906(2) 0.6724(6) 0.49557(12) 0.0610(10) Uani 1 1 d . . . . .
C16 C 0.8181(2) 0.8257(5) 0.30701(13) 0.0524(8) Uani 1 1 d . . . . .
C17 C 0.8233(2) 0.8316(5) 0.35407(13) 0.0519(8) Uani 1 1 d . . . . .
C18 C 0.7540(2) 0.8767(6) 0.37330(12) 0.0571(9) Uani 1 1 d . . . . .
C19 C 0.6835(2) 0.9146(5) 0.34636(12) 0.0526(8) Uani 1 1 d . . . . .
C21 C 0.7478(2) 0.8632(5) 0.28018(11) 0.0492(8) Uani 1 1 d . . . . .
C20 C 0.67840(19) 0.9086(5) 0.29916(11) 0.0454(7) Uani 1 1 d . . . . .
C22 C 0.4576(3) 0.1023(7) 0.43112(16) 0.0776(12) Uani 1 1 d . . . . .
H22A H 0.460309 0.212269 0.449441 0.116 Uiso 1 1 calc R U . . .
H22B H 0.505481 0.092162 0.415715 0.116 Uiso 1 1 calc R U . . .
H22C H 0.453520 -0.002592 0.450705 0.116 Uiso 1 1 calc R U . . .
N2 N 0.38756(19) 0.1101(5) 0.39716(11) 0.0616(8) Uani 1 1 d . . . . .
C24 C 0.3124(2) 0.1405(5) 0.41003(11) 0.0519(8) Uani 1 1 d . . . . .
C25 C 0.2987(3) 0.1573(6) 0.45658(12) 0.0621(10) Uani 1 1 d . . . . .
H25 H 0.341687 0.147958 0.479602 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2222(3) 0.1874(6) 0.46828(13) 0.0656(11) Uani 1 1 d . . . . .
H26 H 0.214683 0.198393 0.499317 0.079 Uiso 1 1 calc R U . . .
C27 C 0.1565(2) 0.2018(6) 0.43590(13) 0.0611(10) Uani 1 1 d . . . . .
C28 C 0.0762(3) 0.2331(7) 0.45066(18) 0.0791(13) Uani 1 1 d . . . . .
H28 H 0.072725 0.237899 0.482269 0.095 Uiso 1 1 calc R U . . .
C30 C 0.2444(2) 0.1566(6) 0.37716(12) 0.0630(10) Uani 1 1 d . . . . .
H30 H 0.250935 0.147012 0.345965 0.076 Uiso 1 1 calc R U . . .
C29 C 0.1693(2) 0.1859(6) 0.38999(13) 0.0668(11) Uani 1 1 d . . . . .
H29 H 0.125691 0.195477 0.367363 0.080 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 C14 2.080(4) . ?
I2 C11 2.077(3) . ?
I3 C17 2.071(3) . ?
I4 C20 2.075(3) . ?
O1 C7 1.210(4) . ?
F2 C10 1.345(4) . ?
F3 C13 1.337(4) . ?
F4 C15 1.348(4) . ?
F5 C16 1.347(4) . ?
F8 C19 1.345(4) . ?
F6 C21 1.347(4) . ?
F7 C18 1.344(4) . ?
O2 C28 1.210(6) . ?
C23 N2 1.459(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C1 C2 1.361(5) . ?
C1 C6 1.395(5) . ?
C1 H1 0.9300 . ?
F1 C12 1.343(4) . ?
C8 N1 1.450(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N1 C3 1.363(5) . ?
N1 C9 1.455(5) . ?
C3 C4 1.411(5) . ?
C3 C2 1.416(5) . ?
C2 H2 0.9300 . ?
C6 C5 1.395(5) . ?
C6 C7 1.450(5) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 C5 1.360(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C10 C15 1.368(5) . ?
C10 C11 1.374(5) . ?
C11 C12 1.373(5) . ?
C12 C13 1.368(5) . ?
C13 C14 1.368(5) . ?
C14 C15 1.371(5) . ?
C16 C21 1.364(5) . ?
C16 C17 1.366(5) . ?
C17 C18 1.376(5) . ?
C18 C19 1.369(5) . ?
C19 C20 1.370(5) . ?
C21 C20 1.376(5) . ?
C22 N2 1.448(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N2 C24 1.364(5) . ?
C24 C25 1.406(5) . ?
C24 C30 1.407(5) . ?
C25 C26 1.373(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(6) . ?
C26 H26 0.9300 . ?
C27 C29 1.383(5) . ?
C27 C28 1.468(6) . ?
C28 H28 0.9300 . ?
C30 C29 1.362(5) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?

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
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 C1 C6 122.7(3) . . ?
C2 C1 H1 118.6 . . ?
C6 C1 H1 118.6 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 N1 C8 121.2(3) . . ?
C3 N1 C9 120.7(3) . . ?
C8 N1 C9 118.1(3) . . ?
N1 C3 C4 121.4(3) . . ?
N1 C3 C2 120.9(3) . . ?
C4 C3 C2 117.7(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C7 120.0(3) . . ?
C5 C6 C7 122.4(3) . . ?
O1 C7 C6 125.9(4) . . ?
O1 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
F2 C10 C15 118.9(3) . . ?
F2 C10 C11 119.4(3) . . ?
C15 C10 C11 121.7(3) . . ?
C12 C11 C10 116.0(3) . . ?
C12 C11 I2 121.5(3) . . ?
C10 C11 I2 122.6(3) . . ?
F1 C12 C13 119.1(3) . . ?
F1 C12 C11 118.8(3) . . ?
C13 C12 C11 122.1(3) . . ?
F3 C13 C14 119.9(3) . . ?
F3 C13 C12 118.1(3) . . ?
C14 C13 C12 122.0(3) . . ?
C13 C14 C15 116.0(3) . . ?
C13 C14 I1 122.4(3) . . ?
C15 C14 I1 121.6(3) . . ?
F4 C15 C10 117.7(3) . . ?
F4 C15 C14 119.9(3) . . ?
C10 C15 C14 122.3(3) . . ?
F5 C16 C21 118.2(3) . . ?
F5 C16 C17 120.1(3) . . ?
C21 C16 C17 121.7(3) . . ?
C16 C17 C18 116.9(3) . . ?
C16 C17 I3 121.4(3) . . ?
C18 C17 I3 121.6(3) . . ?
F7 C18 C19 118.2(3) . . ?
F7 C18 C17 120.4(3) . . ?
C19 C18 C17 121.3(3) . . ?
F8 C19 C18 118.3(3) . . ?
F8 C19 C20 119.9(3) . . ?
C18 C19 C20 121.7(3) . . ?
F6 C21 C16 118.5(3) . . ?
F6 C21 C20 119.8(3) . . ?
C16 C21 C20 121.7(3) . . ?
C19 C20 C21 116.6(3) . . ?
C19 C20 I4 122.2(2) . . ?
C21 C20 I4 121.1(2) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 N2 C22 121.0(3) . . ?
C24 N2 C23 120.8(3) . . ?
C22 N2 C23 118.0(3) . . ?
N2 C24 C25 122.0(3) . . ?
N2 C24 C30 121.5(3) . . ?
C25 C24 C30 116.5(3) . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 122.4(4) . . ?
C27 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C26 C27 C29 117.7(4) . . ?
C26 C27 C28 119.7(4) . . ?
C29 C27 C28 122.6(4) . . ?
O2 C28 C27 126.1(5) . . ?
O2 C28 H28 117.0 . . ?
C27 C28 H28 117.0 . . ?
C29 C30 C24 121.5(3) . . ?
C29 C30 H30 119.2 . . ?
C24 C30 H30 119.2 . . ?
C30 C29 C27 121.5(4) . . ?
C30 C29 H29 119.3 . . ?
C27 C29 H29 119.3 . . ?

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
C8 N1 C3 C4 -5.8(6) . . . . ?
C9 N1 C3 C4 178.3(4) . . . . ?
C8 N1 C3 C2 174.7(4) . . . . ?
C9 N1 C3 C2 -1.2(6) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
N1 C3 C2 C1 179.4(4) . . . . ?
C4 C3 C2 C1 -0.1(6) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C1 C6 C7 -179.2(4) . . . . ?
C1 C6 C7 O1 178.4(4) . . . . ?
C5 C6 C7 O1 -1.4(6) . . . . ?
N1 C3 C4 C5 -178.6(4) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C1 C6 C5 C4 0.3(6) . . . . ?
C7 C6 C5 C4 -179.9(4) . . . . ?
F2 C10 C11 C12 -179.9(4) . . . . ?
C15 C10 C11 C12 0.9(6) . . . . ?
F2 C10 C11 I2 0.9(5) . . . . ?
C15 C10 C11 I2 -178.3(3) . . . . ?
C10 C11 C12 F1 -179.6(4) . . . . ?
I2 C11 C12 F1 -0.4(5) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
I2 C11 C12 C13 177.8(3) . . . . ?
F1 C12 C13 F3 -0.4(6) . . . . ?
C11 C12 C13 F3 -178.5(4) . . . . ?
F1 C12 C13 C14 179.0(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
F3 C13 C14 C15 179.6(4) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
F3 C13 C14 I1 0.4(6) . . . . ?
C12 C13 C14 I1 -179.0(3) . . . . ?
F2 C10 C15 F4 0.8(6) . . . . ?
C11 C10 C15 F4 180.0(4) . . . . ?
F2 C10 C15 C14 -179.1(4) . . . . ?
C11 C10 C15 C14 0.1(7) . . . . ?
C13 C14 C15 F4 179.5(4) . . . . ?
I1 C14 C15 F4 -1.3(6) . . . . ?
C13 C14 C15 C10 -0.7(6) . . . . ?
I1 C14 C15 C10 178.6(3) . . . . ?
F5 C16 C17 C18 179.9(4) . . . . ?
C21 C16 C17 C18 0.2(6) . . . . ?
F5 C16 C17 I3 0.1(5) . . . . ?
C21 C16 C17 I3 -179.7(3) . . . . ?
C16 C17 C18 F7 -179.7(4) . . . . ?
I3 C17 C18 F7 0.1(5) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
I3 C17 C18 C19 179.6(3) . . . . ?
F7 C18 C19 F8 -0.2(6) . . . . ?
C17 C18 C19 F8 -179.6(4) . . . . ?
F7 C18 C19 C20 179.8(4) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
F5 C16 C21 F6 0.2(5) . . . . ?
C17 C16 C21 F6 180.0(3) . . . . ?
F5 C16 C21 C20 -179.9(3) . . . . ?
C17 C16 C21 C20 -0.1(6) . . . . ?
F8 C19 C20 C21 179.7(3) . . . . ?
C18 C19 C20 C21 -0.3(6) . . . . ?
F8 C19 C20 I4 -1.8(5) . . . . ?
C18 C19 C20 I4 178.3(3) . . . . ?
F6 C21 C20 C19 -180.0(3) . . . . ?
C16 C21 C20 C19 0.1(5) . . . . ?
F6 C21 C20 I4 1.5(5) . . . . ?
C16 C21 C20 I4 -178.4(3) . . . . ?
C22 N2 C24 C25 -2.9(6) . . . . ?
C23 N2 C24 C25 -177.8(4) . . . . ?
C22 N2 C24 C30 177.1(4) . . . . ?
C23 N2 C24 C30 2.2(6) . . . . ?
N2 C24 C25 C26 -179.8(4) . . . . ?
C30 C24 C25 C26 0.2(6) . . . . ?
C24 C25 C26 C27 0.2(7) . . . . ?
C25 C26 C27 C29 -0.3(7) . . . . ?
C25 C26 C27 C28 179.7(4) . . . . ?
C26 C27 C28 O2 177.8(5) . . . . ?
C29 C27 C28 O2 -2.1(8) . . . . ?
N2 C24 C30 C29 179.6(4) . . . . ?
C25 C24 C30 C29 -0.4(6) . . . . ?
C24 C30 C29 C27 0.2(7) . . . . ?
C26 C27 C29 C30 0.1(7) . . . . ?
C28 C27 C29 C30 -179.9(4) . . . . ?

_refine_diff_density_max         0.737
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.083

