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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_s4860x
_database_code_depnum_ccdc_archive 'CCDC 1576088'
_audit_update_record             
;
2017-09-22 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_audit_creation_date             2017-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 F9 N2'
_chemical_formula_sum            'C24 H15 F9 N2'
_chemical_formula_weight         502.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0730 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   10.9162(2)
_cell_length_b                   10.9162(2)
_cell_length_c                   19.1285(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2279.42(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15549
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.1110
_cell_measurement_theta_min      2.3190
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26788
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         4.050
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     69.67 257.67   1.00   15.00    --   99.46  73.87 157.22  188
  2  ω    -81.29 105.71   1.00   15.00    --  -51.50  73.87 -25.89  187
  3  ω     74.39 262.39   1.00   15.00    --  104.18  73.87 -82.86  188
  4  ω     82.65 270.65   1.00   15.00    --  112.44  73.87  61.96  188
  5  φ   -249.79  -9.60   1.00   15.00  73.16 102.95  73.87    --   240
  6  ω   -104.82  82.18   1.00   15.00    --  -75.03  73.87  -7.40  187
  7  ω    -34.43 152.57   1.00   15.00    --   -4.63  73.87-102.66  187
  8  ω     74.96 261.96   1.00   15.00    --  104.75  73.87 -11.33  187
  9  ω     64.79 252.79   1.00   15.00    --   94.58  73.87-112.72  188
 10  φ   -117.29  32.83   1.00   15.00 115.04 -43.16  73.87    --   150
 11  ω   -108.77  78.23   1.00   15.00    --  -78.98  73.87-144.46  187
 12  ω     70.76 257.76   1.00   15.00    --  100.55  73.87  77.69  187
 13  ω     73.15 261.15   1.00   15.00    --  102.94  73.87  23.67  188
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241048000
_diffrn_orient_matrix_UB_12      -0.1279407000
_diffrn_orient_matrix_UB_13      0.0307480000
_diffrn_orient_matrix_UB_21      -0.1147004000
_diffrn_orient_matrix_UB_22      0.0126475000
_diffrn_orient_matrix_UB_23      0.0463971000
_diffrn_orient_matrix_UB_31      -0.0788696000
_diffrn_orient_matrix_UB_32      -0.0578475000
_diffrn_orient_matrix_UB_33      -0.0582107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3911
_reflns_number_total             4163
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+1.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          
'Poor data to parameter ratio flag due to Laue group averaging in PLATON and is not representative of the actual number of data used in the refinement. Highly disodered CF3 group treated as isotropic to maintain good data to parameter ratio. In addition, refining as anisotropic introduces errors to the model that require strong restraints to mitigate, therefore it was deemed unnecessary to refine anisotropically.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(3)
 -0.0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Others
 1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F4)+Sof(F5)+Sof(F6)]+1*[Sof(F7)+Sof(F8)+
 Sof(F9)]=1 with esd of 0.0001
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
4.a Riding coordinates:
 N1(H1)
4.b Ternary CH refined with riding coordinates:
 C9(H9), C7(H7)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C5(H5), C4(H4), C23(H23), C18(H18), C16(H16), C24(H24),
 C19(H19), C15(H15), C22(H22), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F13 F 0.8095(3) 1.0203(3) 0.6924(2) 0.0805(11) Uani 1 1 d . . . . .
F10 F 0.3211(3) 1.1905(3) 0.3045(2) 0.0780(12) Uani 1 1 d . . . . .
F11 F 0.4103(4) 1.2548(3) 0.39678(19) 0.0828(12) Uani 1 1 d . . . . .
F12 F 0.5133(4) 1.2137(3) 0.3069(2) 0.0830(12) Uani 1 1 d . . . . .
F14 F 0.6369(4) 1.1015(4) 0.7029(2) 0.0948(15) Uani 1 1 d . . . . .
F15 F 0.7484(6) 1.1390(3) 0.6143(2) 0.1112(19) Uani 1 1 d . . . . .
F1 F 0.9972(8) 0.1697(7) 0.2892(4) 0.0417(17) Uiso 0.371(4) 1 d . . P A 1
F2 F 1.0217(10) 0.1139(10) 0.3957(5) 0.060(2) Uiso 0.371(4) 1 d . . P A 1
F3 F 0.8734(9) 0.0363(9) 0.3348(7) 0.067(3) Uiso 0.371(4) 1 d . . P A 1
F4 F 0.8801(11) 0.0703(12) 0.2986(7) 0.071(3) Uiso 0.334(4) 1 d . . P A 2
F5 F 1.0373(10) 0.1911(9) 0.3170(7) 0.059(3) Uiso 0.334(4) 1 d . . P A 2
F6 F 0.9751(10) 0.0694(9) 0.3976(5) 0.043(2) Uiso 0.334(4) 1 d . . P A 2
F7 F 0.9203(14) 0.0416(12) 0.3764(8) 0.072(3) Uiso 0.296(4) 1 d . . P A 3
F8 F 0.9384(12) 0.1272(11) 0.2797(6) 0.059(3) Uiso 0.296(4) 1 d . . P A 3
F9 F 1.0573(14) 0.1811(14) 0.3690(9) 0.086(4) Uiso 0.296(4) 1 d . . P A 3
N2 N 0.5753(3) 0.5337(3) 0.50658(15) 0.0261(6) Uani 1 1 d . . . . .
N1 N 0.5543(3) 0.6030(3) 0.39598(15) 0.0293(7) Uani 1 1 d . . . . .
H1 H 0.546021 0.585043 0.351006 0.035 Uiso 1 1 d R . . . .
C8 C 0.6042(3) 0.5204(3) 0.44100(18) 0.0250(7) Uani 1 1 d . . . . .
C17 C 0.6890(3) 0.4241(3) 0.41637(19) 0.0271(7) Uani 1 1 d . . . . .
C10 C 0.5522(3) 0.7470(3) 0.54931(18) 0.0248(7) Uani 1 1 d . . . . .
C6 C 0.4518(3) 0.8032(3) 0.41226(18) 0.0264(7) Uani 1 1 d . . . . .
C11 C 0.6748(4) 0.7760(4) 0.5399(2) 0.0329(8) Uani 1 1 d . . . . .
H11 H 0.724032 0.726803 0.510057 0.040 Uiso 1 1 calc R . . . .
C12 C 0.7260(4) 0.8753(4) 0.5734(2) 0.0372(9) Uani 1 1 d . . . . .
H12 H 0.809643 0.895267 0.565741 0.045 Uiso 1 1 calc R . . . .
C9 C 0.4934(3) 0.6413(4) 0.51108(17) 0.0262(7) Uani 1 1 d . . . . .
H9 H 0.417388 0.616917 0.536753 0.031 Uiso 1 1 calc R . . . .
C13 C 0.6558(4) 0.9462(4) 0.6183(2) 0.0369(9) Uani 1 1 d . . . . .
C3 C 0.4324(4) 1.0460(4) 0.3701(2) 0.0376(9) Uani 1 1 d . . . . .
C2 C 0.4194(5) 1.1746(4) 0.3457(3) 0.0484(11) Uani 1 1 d . . . . .
C7 C 0.4585(3) 0.6699(3) 0.43293(18) 0.0279(8) Uani 1 1 d . . . . .
H7 H 0.377866 0.630526 0.422410 0.034 Uiso 1 1 calc R . . . .
C5 C 0.3433(4) 0.8675(4) 0.4213(2) 0.0336(8) Uani 1 1 d . . . . .
H5 H 0.274847 0.827720 0.441935 0.040 Uiso 1 1 calc R . . . .
C4 C 0.3334(4) 0.9876(4) 0.4008(2) 0.0388(9) Uani 1 1 d . . . . .
H4 H 0.258733 1.030714 0.407703 0.047 Uiso 1 1 calc R . . . .
C20 C 0.8509(4) 0.2427(4) 0.3717(2) 0.0418(10) Uani 1 1 d . . . . .
C23 C 0.5520(4) 0.8639(4) 0.3839(2) 0.0359(9) Uani 1 1 d . . . . .
H23 H 0.627786 0.822047 0.378902 0.043 Uiso 1 1 calc R . . . .
C18 C 0.7323(4) 0.3361(4) 0.4626(2) 0.0420(10) Uani 1 1 d . . . . .
H18 H 0.706734 0.338277 0.510063 0.050 Uiso 1 1 calc R . . . .
C16 C 0.4825(4) 0.8192(4) 0.5938(2) 0.0352(9) Uani 1 1 d . . . . .
H16 H 0.398221 0.800726 0.600535 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5422(4) 0.9852(4) 0.3628(2) 0.0420(10) Uani 1 1 d . . . . .
H24 H 0.610993 1.026206 0.343414 0.050 Uiso 1 1 calc R . . . .
C19 C 0.8118(5) 0.2455(4) 0.4407(2) 0.0482(12) Uani 1 1 d . . . . .
H19 H 0.839618 0.185257 0.472830 0.058 Uiso 1 1 calc R . . . .
C14 C 0.7129(5) 1.0511(5) 0.6553(3) 0.0501(11) Uani 1 1 d . . . . .
C15 C 0.5341(4) 0.9176(4) 0.6286(2) 0.0435(10) Uani 1 1 d . . . . .
H15 H 0.485683 0.965374 0.659585 0.052 Uiso 1 1 calc R . . . .
C22 C 0.7281(5) 0.4195(4) 0.3471(2) 0.0426(10) Uani 1 1 d . . . . .
H22 H 0.699419 0.478801 0.314622 0.051 Uiso 1 1 calc R . . . .
C1 C 0.9365(6) 0.1461(5) 0.3480(3) 0.0572(14) Uani 1 1 d . . . . .
C21 C 0.8079(5) 0.3296(4) 0.3254(2) 0.0489(12) Uani 1 1 d . . . . .
H21 H 0.833751 0.327282 0.277947 0.059 Uiso 1 1 calc R . . . .


_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
F13 C14 1.315(6) . ?
F10 C2 1.342(6) . ?
F11 C2 1.316(6) . ?
F12 C2 1.335(6) . ?
F14 C14 1.348(6) . ?
F15 C14 1.300(7) . ?
F1 C1 1.330(9) . ?
F2 C1 1.349(11) . ?
F3 C1 1.406(12) . ?
F4 C1 1.398(13) . ?
F5 C1 1.343(12) . ?
F6 C1 1.335(10) . ?
F7 C1 1.277(14) . ?
F8 C1 1.323(12) . ?
F9 C1 1.430(16) . ?
N2 C8 1.302(5) . ?
N2 C9 1.479(5) . ?
N1 H1 0.8870 . ?
N1 C8 1.361(5) . ?
N1 C7 1.458(5) . ?
C8 C17 1.478(5) . ?
C17 C18 1.388(6) . ?
C17 C22 1.393(6) . ?
C10 C11 1.387(5) . ?
C10 C9 1.510(5) . ?
C10 C16 1.388(5) . ?
C6 C7 1.510(5) . ?
C6 C5 1.388(5) . ?
C6 C23 1.388(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(6) . ?
C9 H9 1.0000 . ?
C9 C7 1.574(5) . ?
C13 C14 1.484(6) . ?
C13 C15 1.379(6) . ?
C3 C2 1.487(6) . ?
C3 C4 1.385(7) . ?
C3 C24 1.376(6) . ?
C7 H7 1.0000 . ?
C5 H5 0.9500 . ?
C5 C4 1.373(6) . ?
C4 H4 0.9500 . ?
C20 C19 1.387(6) . ?
C20 C1 1.481(7) . ?
C20 C21 1.380(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(6) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(6) . ?
C24 H24 0.9500 . ?
C19 H19 0.9500 . ?
C15 H15 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.377(6) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C9 107.0(3) . . ?
C8 N1 H1 120.5 . . ?
C8 N1 C7 108.2(3) . . ?
C7 N1 H1 120.5 . . ?
N2 C8 N1 116.0(3) . . ?
N2 C8 C17 122.6(3) . . ?
N1 C8 C17 121.4(3) . . ?
C18 C17 C8 120.1(3) . . ?
C18 C17 C22 118.5(4) . . ?
C22 C17 C8 121.4(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 C16 118.7(3) . . ?
C16 C10 C9 119.8(3) . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 C23 118.7(4) . . ?
C23 C6 C7 121.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
N2 C9 C10 112.2(3) . . ?
N2 C9 H9 108.6 . . ?
N2 C9 C7 104.4(3) . . ?
C10 C9 H9 108.6 . . ?
C10 C9 C7 114.3(3) . . ?
C7 C9 H9 108.6 . . ?
C12 C13 C14 119.6(4) . . ?
C15 C13 C12 119.6(4) . . ?
C15 C13 C14 120.7(4) . . ?
C4 C3 C2 119.5(4) . . ?
C24 C3 C2 120.4(4) . . ?
C24 C3 C4 120.1(4) . . ?
F10 C2 C3 112.5(4) . . ?
F11 C2 F10 106.8(4) . . ?
F11 C2 F12 104.9(4) . . ?
F11 C2 C3 113.7(4) . . ?
F12 C2 F10 104.3(4) . . ?
F12 C2 C3 113.8(4) . . ?
N1 C7 C6 112.9(3) . . ?
N1 C7 C9 100.8(3) . . ?
N1 C7 H7 108.6 . . ?
C6 C7 C9 116.8(3) . . ?
C6 C7 H7 108.6 . . ?
C9 C7 H7 108.6 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C19 C20 C1 120.1(4) . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 C1 120.4(4) . . ?
C6 C23 H23 119.7 . . ?
C6 C23 C24 120.5(4) . . ?
C24 C23 H23 119.7 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(4) . . ?
C19 C18 H18 119.5 . . ?
C10 C16 H16 119.6 . . ?
C15 C16 C10 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C3 C24 C23 119.8(4) . . ?
C3 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
F13 C14 F14 103.5(4) . . ?
F13 C14 C13 113.4(4) . . ?
F14 C14 C13 112.3(4) . . ?
F15 C14 F13 105.9(5) . . ?
F15 C14 F14 106.8(5) . . ?
F15 C14 C13 114.0(4) . . ?
C13 C15 C16 120.0(4) . . ?
C13 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.4(4) . . ?
C21 C22 H22 119.8 . . ?
F1 C1 F2 106.1(7) . . ?
F1 C1 F3 104.9(7) . . ?
F1 C1 C20 115.9(5) . . ?
F2 C1 F3 103.7(7) . . ?
F2 C1 C20 114.4(6) . . ?
F3 C1 C20 110.7(6) . . ?
F4 C1 C20 110.5(6) . . ?
F5 C1 F4 106.2(8) . . ?
F5 C1 C20 113.1(6) . . ?
F6 C1 F4 104.3(8) . . ?
F6 C1 F5 106.5(8) . . ?
F6 C1 C20 115.4(5) . . ?
F7 C1 F8 106.4(10) . . ?
F7 C1 F9 104.3(10) . . ?
F7 C1 C20 114.7(7) . . ?
F8 C1 F9 107.7(9) . . ?
F8 C1 C20 115.1(6) . . ?
F9 C1 C20 107.8(7) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(4) . . ?
C22 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C8 C17 C18 6.1(6) . . . . ?
N2 C8 C17 C22 -173.4(4) . . . . ?
N2 C9 C7 N1 -17.8(3) . . . . ?
N2 C9 C7 C6 -140.6(3) . . . . ?
N1 C8 C17 C18 -175.8(4) . . . . ?
N1 C8 C17 C22 4.6(6) . . . . ?
C8 N2 C9 C10 -112.5(3) . . . . ?
C8 N2 C9 C7 11.8(4) . . . . ?
C8 N1 C7 C6 143.4(3) . . . . ?
C8 N1 C7 C9 17.9(4) . . . . ?
C8 C17 C18 C19 -179.9(4) . . . . ?
C8 C17 C22 C21 179.5(4) . . . . ?
C17 C18 C19 C20 0.9(8) . . . . ?
C17 C22 C21 C20 -0.1(8) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C10 C9 C7 N1 105.2(3) . . . . ?
C10 C9 C7 C6 -17.6(5) . . . . ?
C10 C16 C15 C13 1.1(7) . . . . ?
C6 C5 C4 C3 0.5(6) . . . . ?
C6 C23 C24 C3 0.1(7) . . . . ?
C11 C10 C9 N2 39.7(5) . . . . ?
C11 C10 C9 C7 -78.9(4) . . . . ?
C11 C10 C16 C15 -0.4(6) . . . . ?
C11 C12 C13 C14 178.5(4) . . . . ?
C11 C12 C13 C15 -0.7(7) . . . . ?
C12 C13 C14 F13 -55.7(7) . . . . ?
C12 C13 C14 F14 -172.7(5) . . . . ?
C12 C13 C14 F15 65.7(6) . . . . ?
C12 C13 C15 C16 -0.6(7) . . . . ?
C9 N2 C8 N1 -0.4(4) . . . . ?
C9 N2 C8 C17 177.8(3) . . . . ?
C9 C10 C11 C12 177.8(4) . . . . ?
C9 C10 C16 C15 -179.0(4) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
C2 C3 C24 C23 -178.0(4) . . . . ?
C7 N1 C8 N2 -12.4(5) . . . . ?
C7 N1 C8 C17 169.4(3) . . . . ?
C7 C6 C5 C4 -177.8(4) . . . . ?
C7 C6 C23 C24 177.5(4) . . . . ?
C5 C6 C7 N1 156.3(3) . . . . ?
C5 C6 C7 C9 -87.4(4) . . . . ?
C5 C6 C23 C24 -2.2(6) . . . . ?
C4 C3 C2 F10 -51.1(6) . . . . ?
C4 C3 C2 F11 70.5(6) . . . . ?
C4 C3 C2 F12 -169.4(4) . . . . ?
C4 C3 C24 C23 2.4(7) . . . . ?
C23 C6 C7 N1 -23.4(5) . . . . ?
C23 C6 C7 C9 92.9(4) . . . . ?
C23 C6 C5 C4 1.9(6) . . . . ?
C18 C17 C22 C21 -0.1(7) . . . . ?
C16 C10 C11 C12 -0.8(6) . . . . ?
C16 C10 C9 N2 -141.7(3) . . . . ?
C16 C10 C9 C7 99.7(4) . . . . ?
C24 C3 C2 F10 129.3(5) . . . . ?
C24 C3 C2 F11 -109.1(6) . . . . ?
C24 C3 C2 F12 10.9(6) . . . . ?
C24 C3 C4 C5 -2.7(7) . . . . ?
C19 C20 C1 F1 -160.6(7) . . . . ?
C19 C20 C1 F2 -36.5(9) . . . . ?
C19 C20 C1 F3 80.1(8) . . . . ?
C19 C20 C1 F4 115.1(8) . . . . ?
C19 C20 C1 F5 -125.9(8) . . . . ?
C19 C20 C1 F6 -2.9(10) . . . . ?
C19 C20 C1 F7 35.7(12) . . . . ?
C19 C20 C1 F8 159.7(9) . . . . ?
C19 C20 C1 F9 -80.0(9) . . . . ?
C19 C20 C21 C22 0.8(8) . . . . ?
C14 C13 C15 C16 -179.7(5) . . . . ?
C15 C13 C14 F13 123.4(5) . . . . ?
C15 C13 C14 F14 6.4(7) . . . . ?
C15 C13 C14 F15 -115.2(6) . . . . ?
C22 C17 C18 C19 -0.3(7) . . . . ?
C1 C20 C19 C18 179.7(5) . . . . ?
C1 C20 C21 C22 179.9(5) . . . . ?
C21 C20 C19 C18 -1.1(8) . . . . ?
C21 C20 C1 F1 20.3(9) . . . . ?
C21 C20 C1 F2 144.4(8) . . . . ?
C21 C20 C1 F3 -99.0(8) . . . . ?
C21 C20 C1 F4 -64.0(9) . . . . ?
C21 C20 C1 F5 55.0(9) . . . . ?
C21 C20 C1 F6 178.0(8) . . . . ?
C21 C20 C1 F7 -143.4(11) . . . . ?
C21 C20 C1 F8 -19.4(10) . . . . ?
C21 C20 C1 F9 100.9(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.299
_oxdiff_exptl_absorpt_empirical_full_min 0.536
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(3)
2 -0.0(3)

####################################################################### 
# 
# 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_s4866l
_database_code_depnum_ccdc_archive 'CCDC 1576089'
_audit_update_record             
;
2017-09-22 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 F15 N2 S3'
_chemical_formula_sum            'C21 H15 F15 N2 S3'
_chemical_formula_weight         676.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.2146(2)
_cell_length_b                   9.99845(16)
_cell_length_c                   20.3665(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.4162(15)
_cell_angle_gamma                90
_cell_volume                     2486.54(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14317
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      26.3450
_cell_measurement_theta_min      1.9050
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.21a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
16 6 -1 0.1046
-16 -6 1 0.1046
-8 12 1 0.1873
8 -12 -1 0.1873
0 1 -29 0.1913
0 -1 29 0.1913
4 14 -1 0.1070
17 0 0 0.0692

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.209
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
16.0000 5.9999 -0.9997 -0.1483 -1.0086 0.0722
-16.0000 -5.9999 0.9997 0.1483 1.0086 -0.0722
-8.0001 12.0000 1.0003 0.0481 -0.0075 -0.9687
8.0001 -12.0000 -1.0003 -0.0481 0.0075 0.9687
0.0001 0.9999 -28.9999 -1.0041 0.0997 -0.0889
-0.0001 -0.9999 28.9999 1.0041 -0.0997 0.0889
3.9999 14.0000 -0.9996 -0.0991 -0.6733 -0.7602
17.0000 -0.0000 0.0001 -0.1025 -0.8600 0.4743

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.269
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00   7.00   1.00    1.00    --   17.60  29.00  -4.00   78
  2  ω    -71.00  27.00   1.00    1.00    --   17.60  43.00-180.00   98
  3  ω    -59.00 -33.00   1.00    1.00    --   17.60  60.00-120.00   26
  4  ω    -17.00 107.00   1.00    1.00    --   17.60  60.00-120.00  124
  5  ω    -72.00 107.00   1.00    1.00    --   17.60  14.00 120.00  179
  6  ω     17.00  97.00   1.00    1.00    --   17.60  60.00-150.00   80
  7  ω     72.00  98.00   1.00    1.00    --   17.60  29.00  -4.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0060308000
_diffrn_orient_matrix_UB_12      -0.0028886000
_diffrn_orient_matrix_UB_13      0.0345242000
_diffrn_orient_matrix_UB_21      -0.0505895000
_diffrn_orient_matrix_UB_22      -0.0339661000
_diffrn_orient_matrix_UB_23      -0.0046092000
_diffrn_orient_matrix_UB_31      0.0278971000
_diffrn_orient_matrix_UB_32      -0.0622056000
_diffrn_orient_matrix_UB_33      0.0009198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4490
_reflns_number_total             5087
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.21a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+2.2032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
S1 S 1.49317(4) 0.50732(5) 0.19054(3) 0.03205(13) Uani 1 1 d . . . . .
S3 S 0.81242(5) 0.11857(6) 0.53406(3) 0.03782(14) Uani 1 1 d . . . . .
S2 S 0.67851(8) 0.65116(6) 0.56365(3) 0.0693(3) Uani 1 1 d . . . . .
F2 F 1.61994(10) 0.50259(15) 0.17630(8) 0.0492(4) Uani 1 1 d . . . . .
F1 F 1.48813(10) 0.35352(12) 0.17132(7) 0.0421(3) Uani 1 1 d . . . . .
F5 F 1.47291(10) 0.54616(15) 0.11633(7) 0.0449(3) Uani 1 1 d . . . . .
F4 F 1.52428(10) 0.46602(14) 0.26407(7) 0.0456(3) Uani 1 1 d . . . . .
F13 F 0.70426(10) 0.04495(14) 0.51203(6) 0.0440(3) Uani 1 1 d . . . . .
F11 F 0.92121(15) 0.1844(2) 0.56195(8) 0.0849(7) Uani 1 1 d . . . . .
F12 F 0.80412(13) 0.04430(18) 0.60222(7) 0.0608(4) Uani 1 1 d . . . . .
F3 F 1.50951(10) 0.65974(13) 0.20938(8) 0.0481(3) Uani 1 1 d . . . . .
F9 F 0.60002(19) 0.76855(18) 0.54463(9) 0.0923(7) Uani 1 1 d . . . . .
F15 F 0.88075(13) -0.00545(16) 0.50905(8) 0.0622(5) Uani 1 1 d . . . . .
F10 F 0.7552(2) 0.53513(19) 0.58894(8) 0.1020(9) Uani 1 1 d . . . . .
F14 F 0.74234(17) 0.23526(16) 0.56354(7) 0.0699(5) Uani 1 1 d . . . . .
N2 N 0.95009(12) 0.40368(15) 0.24005(7) 0.0222(3) Uani 1 1 d . . . . .
F8 F 0.5852(2) 0.5460(2) 0.54822(12) 0.1085(9) Uani 1 1 d . . . . .
F6 F 0.7696(2) 0.75722(19) 0.58493(8) 0.0908(7) Uani 1 1 d . . . . .
F7 F 0.6340(2) 0.66072(19) 0.63568(9) 0.1158(10) Uani 1 1 d . . . . .
N1 N 0.96552(12) 0.61435(14) 0.28035(8) 0.0238(3) Uani 1 1 d . . . . .
C1 C 1.34924(14) 0.51279(18) 0.20765(9) 0.0246(4) Uani 1 1 d . . . . .
C7 C 1.01258(14) 0.51412(17) 0.25283(8) 0.0211(3) Uani 1 1 d . . . . .
C19 C 0.82389(15) 0.20309(18) 0.45619(9) 0.0260(4) Uani 1 1 d . . . . .
C16 C 0.84178(14) 0.33379(16) 0.33644(8) 0.0202(3) Uani 1 1 d . . . . .
C15 C 0.84768(14) 0.41785(17) 0.27479(9) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.80955(14) 0.60885(16) 0.35641(9) 0.0231(4) Uani 1 1 d . . . . .
C3 C 1.20455(16) 0.58125(19) 0.27679(9) 0.0263(4) Uani 1 1 d . . . . .
C17 C 0.73960(14) 0.31218(17) 0.36397(9) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.69872(16) 0.62881(19) 0.36568(11) 0.0299(4) Uani 1 1 d . . . . .
C8 C 0.85046(14) 0.57454(17) 0.28934(9) 0.0222(4) Uani 1 1 d . . . . .
C6 C 1.27530(15) 0.45140(18) 0.16481(10) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.72992(15) 0.24941(18) 0.42409(10) 0.0255(4) Uani 1 1 d . . . . .
C21 C 0.93430(14) 0.28509(18) 0.36946(9) 0.0234(4) Uani 1 1 d . . . . .
C4 C 1.12947(14) 0.51562(17) 0.23547(9) 0.0218(4) Uani 1 1 d . . . . .
C20 C 0.92584(15) 0.21841(19) 0.42895(10) 0.0274(4) Uani 1 1 d . . . . .
C2 C 1.31514(16) 0.57929(19) 0.26357(10) 0.0286(4) Uani 1 1 d . . . . .
C12 C 0.7298(2) 0.63869(19) 0.48177(11) 0.0392(5) Uani 1 1 d . . . . .
C5 C 1.16512(15) 0.45111(18) 0.17944(9) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.88066(17) 0.60857(19) 0.41083(10) 0.0293(4) Uani 1 1 d . . . . .
C13 C 0.65801(19) 0.6433(2) 0.42824(12) 0.0393(5) Uani 1 1 d . . . . .
C11 C 0.8406(2) 0.6231(2) 0.47357(11) 0.0377(5) Uani 1 1 d . . . . .
H8 H 0.8045(16) 0.619(2) 0.2560(10) 0.021(5) Uiso 1 1 d . . . . .
H6 H 1.2976(16) 0.410(2) 0.1262(11) 0.024(5) Uiso 1 1 d . . . . .
H15 H 0.7856(16) 0.396(2) 0.2466(10) 0.020(5) Uiso 1 1 d . . . . .
H5 H 1.1145(16) 0.408(2) 0.1495(10) 0.019(5) Uiso 1 1 d . . . . .
H18 H 0.6614(18) 0.237(2) 0.4423(11) 0.032(6) Uiso 1 1 d . . . . .
H17 H 0.6744(18) 0.341(2) 0.3408(11) 0.031(6) Uiso 1 1 d . . . . .
H3 H 1.1791(17) 0.626(2) 0.3159(11) 0.026(5) Uiso 1 1 d . . . . .
H2 H 0.9770(17) 0.326(2) 0.2332(10) 0.026(5) Uiso 1 1 d . . . . .
H21 H 1.0039(18) 0.293(2) 0.3505(11) 0.031(6) Uiso 1 1 d . . . . .
H10 H 0.9586(19) 0.597(2) 0.4050(11) 0.037(6) Uiso 1 1 d . . . . .
H20 H 0.9875(18) 0.186(2) 0.4507(11) 0.034(6) Uiso 1 1 d . . . . .
H2A H 1.3679(19) 0.621(2) 0.2945(12) 0.039(6) Uiso 1 1 d . . . . .
H13 H 0.586(2) 0.656(3) 0.4328(14) 0.057(8) Uiso 1 1 d . . . . .
H14 H 0.6489(18) 0.629(2) 0.3289(11) 0.031(6) Uiso 1 1 d . . . . .
H11 H 0.890(2) 0.622(3) 0.5104(14) 0.051(7) Uiso 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
S1 F2 1.5832(12) . ?
S1 F1 1.5876(13) . ?
S1 F5 1.5742(14) . ?
S1 F4 1.5904(14) . ?
S1 F3 1.5830(14) . ?
S1 C1 1.8015(18) . ?
S3 F13 1.5682(13) . ?
S3 F11 1.5761(15) . ?
S3 F12 1.5799(13) . ?
S3 F15 1.5857(17) . ?
S3 F14 1.5749(17) . ?
S3 C19 1.8055(19) . ?
S2 F9 1.5583(19) . ?
S2 F10 1.570(2) . ?
S2 F8 1.576(3) . ?
S2 F6 1.590(2) . ?
S2 F7 1.5799(16) . ?
S2 C12 1.800(2) . ?
N2 C7 1.364(2) . ?
N2 C15 1.459(2) . ?
N1 C7 1.290(2) . ?
N1 C8 1.476(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.391(3) . ?
C7 C4 1.479(2) . ?
C19 C18 1.386(3) . ?
C19 C20 1.384(3) . ?
C16 C15 1.514(2) . ?
C16 C17 1.398(2) . ?
C16 C21 1.389(2) . ?
C15 C8 1.595(2) . ?
C9 C14 1.386(3) . ?
C9 C8 1.506(2) . ?
C9 C10 1.391(3) . ?
C3 C4 1.393(3) . ?
C3 C2 1.384(3) . ?
C17 C18 1.384(3) . ?
C14 C13 1.387(3) . ?
C6 C5 1.386(3) . ?
C21 C20 1.389(3) . ?
C4 C5 1.390(3) . ?
C12 C13 1.383(4) . ?
C12 C11 1.377(3) . ?
C10 C11 1.387(3) . ?

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
F2 S1 F1 87.60(7) . . ?
F2 S1 F4 87.29(8) . . ?
F2 S1 C1 179.40(9) . . ?
F1 S1 F4 89.29(8) . . ?
F1 S1 C1 92.58(8) . . ?
F5 S1 F2 87.86(7) . . ?
F5 S1 F1 89.89(8) . . ?
F5 S1 F4 175.11(7) . . ?
F5 S1 F3 90.64(8) . . ?
F5 S1 C1 92.71(8) . . ?
F4 S1 C1 92.14(8) . . ?
F3 S1 F2 87.43(7) . . ?
F3 S1 F1 174.97(7) . . ?
F3 S1 F4 89.77(8) . . ?
F3 S1 C1 92.39(8) . . ?
F13 S3 F11 174.80(8) . . ?
F13 S3 F12 87.64(7) . . ?
F13 S3 F15 89.28(9) . . ?
F13 S3 F14 89.70(10) . . ?
F13 S3 C19 92.95(8) . . ?
F11 S3 F12 87.21(8) . . ?
F11 S3 F15 89.80(12) . . ?
F11 S3 C19 92.19(8) . . ?
F12 S3 F15 87.73(9) . . ?
F12 S3 C19 179.23(9) . . ?
F15 S3 C19 91.78(8) . . ?
F14 S3 F11 90.84(12) . . ?
F14 S3 F12 88.04(9) . . ?
F14 S3 F15 175.69(8) . . ?
F14 S3 C19 92.46(9) . . ?
F9 S2 F10 175.22(10) . . ?
F9 S2 F8 90.91(14) . . ?
F9 S2 F6 89.29(13) . . ?
F9 S2 F7 87.80(11) . . ?
F9 S2 C12 92.75(10) . . ?
F10 S2 F8 89.72(15) . . ?
F10 S2 F6 89.72(14) . . ?
F10 S2 F7 87.49(11) . . ?
F10 S2 C12 91.96(10) . . ?
F8 S2 F6 175.57(10) . . ?
F8 S2 F7 87.82(13) . . ?
F8 S2 C12 92.04(11) . . ?
F6 S2 C12 92.38(10) . . ?
F7 S2 F6 87.76(13) . . ?
F7 S2 C12 179.43(11) . . ?
C7 N2 C15 108.14(14) . . ?
C7 N1 C8 106.27(14) . . ?
C6 C1 S1 119.30(15) . . ?
C6 C1 C2 121.61(17) . . ?
C2 C1 S1 119.09(14) . . ?
N2 C7 C4 120.10(15) . . ?
N1 C7 N2 117.29(16) . . ?
N1 C7 C4 122.61(16) . . ?
C18 C19 S3 119.29(14) . . ?
C20 C19 S3 119.60(14) . . ?
C20 C19 C18 121.10(17) . . ?
C17 C16 C15 118.67(15) . . ?
C21 C16 C15 122.78(15) . . ?
C21 C16 C17 118.39(16) . . ?
N2 C15 C16 114.03(14) . . ?
N2 C15 C8 99.84(13) . . ?
C16 C15 C8 113.11(14) . . ?
C14 C9 C8 120.24(17) . . ?
C14 C9 C10 118.97(18) . . ?
C10 C9 C8 120.51(16) . . ?
C2 C3 C4 120.45(18) . . ?
C18 C17 C16 121.45(17) . . ?
C9 C14 C13 120.9(2) . . ?
N1 C8 C15 104.94(13) . . ?
N1 C8 C9 112.92(15) . . ?
C9 C8 C15 112.73(14) . . ?
C1 C6 C5 119.19(17) . . ?
C17 C18 C19 118.75(17) . . ?
C16 C21 C20 120.90(17) . . ?
C3 C4 C7 119.02(16) . . ?
C5 C4 C7 121.01(16) . . ?
C5 C4 C3 119.97(17) . . ?
C19 C20 C21 119.33(17) . . ?
C3 C2 C1 118.64(18) . . ?
C13 C12 S2 119.97(18) . . ?
C11 C12 S2 119.07(19) . . ?
C11 C12 C13 120.95(19) . . ?
C6 C5 C4 120.08(17) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C13 C14 119.1(2) . . ?
C12 C11 C10 119.6(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# 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_s4980l
_database_code_depnum_ccdc_archive 'CCDC 1582071'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 F9 N2'
_chemical_formula_sum            'C24 H15 F9 N2'
_chemical_formula_weight         502.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.08130(17)
_cell_length_b                   20.6490(4)
_cell_length_c                   21.8088(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4539.89(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5818
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      67.9120
_cell_measurement_theta_min      4.0380
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    1.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16281
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         4.054
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     69.00  95.00   1.00    2.00    --   55.00  57.00 129.00   26
  2  ω     31.00  56.00   1.00    2.00    --   55.00  57.00 129.00   25
  3  ω    -33.00  -7.00   1.00    2.00    --   55.00  49.00-104.00   26
  4  ω    -22.00   3.00   1.00    2.00    --   55.00  59.00  16.00   25
  5  ω     86.00 111.00   1.00    5.00    --  110.00  59.00  16.00   25
  6  ω     86.00 111.00   1.00    5.00    --  110.00  49.00-104.00   25
  7  ω    174.00 199.00   1.00    5.00    --  110.00  59.00  16.00   25
  8  ω     99.00 124.00   1.00    5.00    --  110.00  57.00 129.00   25
  9  ω    -71.00 -19.00   1.00    1.00    --    0.00  60.00-180.00   52
 10  ω     33.00  83.00   1.00    1.00    --    0.00  60.00-180.00   50
 11  ω    -24.00   1.00   1.00    1.00    --    0.00  59.00  16.00   25
 12  ω    -24.00   1.00   1.00    1.00    --    0.00  49.00-104.00   25
 13  ω    -33.00 142.00   1.00    2.00    --   55.00  29.00  60.00  175
 14  ω    -32.00  24.00   1.00    2.00    --   55.00  57.00 -90.00   56
 15  ω     55.00  80.00   1.00    2.00    --   55.00  59.00  16.00   25
 16  ω     47.00  75.00   1.00    2.00    --   55.00  57.00 -90.00   28
 17  ω     57.00 198.00   1.00    5.00    --  110.00  48.00-150.00  141
 18  ω     22.00  52.00   1.00    5.00    --  110.00  10.00 -60.00   30
 19  ω    173.00 199.00   1.00    5.00    --  110.00  60.00   0.00   26
 20  ω    106.00 186.00   1.00    5.00    --  110.00  10.00  60.00   80
 21  ω     21.00 121.00   1.00    5.00    --  110.00  60.00   0.00  100
 22  ω     58.00  84.00   1.00    5.00    --  110.00  10.00 -60.00   26
 23  ω     42.00  80.00   1.00    5.00    --  110.00  10.00  60.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0365385000
_diffrn_orient_matrix_UB_12      -0.0477326000
_diffrn_orient_matrix_UB_13      0.0515977000
_diffrn_orient_matrix_UB_21      0.1263812000
_diffrn_orient_matrix_UB_22      -0.0394334000
_diffrn_orient_matrix_UB_23      -0.0135549000
_diffrn_orient_matrix_UB_31      0.0777506000
_diffrn_orient_matrix_UB_32      0.0416254000
_diffrn_orient_matrix_UB_33      0.0463030000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3579
_reflns_number_total             4146
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+6.1064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.1952
_refine_special_details          
'R1 is a little higher than desired due to the modelling of the highly disordred CF3 groups. If allowed to refine unconstrained while split into parts, unrealistic ellipsoids and bond distances develop and even though it does make the R1 value drop to 4% it was felt more appropriate to model with realistic geometries. Additional collections of other crystals show the same effect.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F5-C14 = F5A-C14 = F4-C14 = F4A-C14 = F6-C14 = F6A-C14
 1.35 with sigma of 0.01
 F5A-F4A = F4A-F6 = F6-F5A
 2.36 with sigma of 0.01
 F5-F4 = F4-F6A = F6A-F5
 2.36 with sigma of 0.01
 F8-F9 = F9-F7 = F7-F8
 2.36 with sigma of 0.01
 F8A-F9A = F9A-F7A = F7A-F8A
 2.36 with sigma of 0.01
 F8-C22 = F9-C22 = F7-C22 = F8A-C22A = F9A-C22A = F7A-C22A
 1.35 with sigma of 0.01
 F2-C1 = F1A-C1 = F1-C1 = F3A-C1 = F3-C1 = F2A-C1
 1.35 with sigma of 0.01
 C22A-C21 \\sim C22-C21
 with sigma of 0.01
3. Rigid bond restraints
 F5, F5A, F4, F4A, F6A, F6, C14
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 F7, F9, F8, C22, F7A, F8A, F9A, C22A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 F3, F1, C1, F2, F2A, F1A, F3A, F2B, F3B, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F5 \\sim F5A \\sim F4 \\sim F4A \\sim F6A \\sim F6 \\sim C14: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.01
F7 \\sim F9 \\sim F8 \\sim C22 \\sim F7A \\sim F8A \\sim F9A \\sim C22A: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.01
F3 \\sim F1 \\sim C1 \\sim F2 \\sim F2A \\sim F1A \\sim F3A \\sim F2B \\sim F3B
\\sim F1B: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01
5. Others
 1*[Sof(F2A)+Sof(F1A)+Sof(F3A)]+1*[Sof(F3)+Sof(F1)+Sof(F2)]+1*[Sof(F3B)+
 Sof(F2B)+Sof(F1B)]=1 with esd of 0.0001
 Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(C22A)=1-FVAR(1)
 Sof(F7)=Sof(F9)=Sof(F8)=Sof(C22)=FVAR(1)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F5)=Sof(F6)=Sof(F4)=FVAR(2)
 Sof(F2A)=Sof(F1A)=Sof(F3A)=FVAR(3)
 Sof(F3)=Sof(F1)=Sof(F2)=FVAR(4)
 Sof(F3B)=Sof(F2B)=Sof(F1B)=FVAR(5)
6.a Ternary CH refined with riding coordinates:
 C17(H17), C9(H9)
6.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C6(H6), C23(H23), C11(H11), C19(H19), C4(H4), C7(H7), C16(H16),
 C12(H12), C3(H3), C20(H20), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.4935(2) 0.51112(10) 0.74432(10) 0.0273(5) Uani 1 1 d . . . . .
N2 N 0.2722(2) 0.50133(11) 0.73895(10) 0.0285(5) Uani 1 1 d . . . . .
F7 F 0.7591(4) 0.1984(3) 0.8024(2) 0.0667(13) Uani 0.708(4) 1 d D U P A 1
F5 F 0.1051(9) 0.6058(4) 0.4559(5) 0.069(2) Uani 0.499(14) 1 d D U P B 1
F6 F 0.1268(12) 0.5137(6) 0.4124(5) 0.083(2) Uani 0.499(14) 1 d D U P B 1
C8 C 0.3788(2) 0.53155(12) 0.76323(11) 0.0247(5) Uani 1 1 d . . . . .
C18 C 0.5117(2) 0.39334(12) 0.73424(11) 0.0264(5) Uani 1 1 d . . . . .
C10 C 0.2820(2) 0.48212(12) 0.62740(12) 0.0276(5) Uani 1 1 d . . . . .
C17 C 0.4674(2) 0.45521(12) 0.70343(11) 0.0262(5) Uani 1 1 d . . . . .
H17 H 0.515910 0.460862 0.664871 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3651(2) 0.58252(13) 0.81030(12) 0.0280(5) Uani 1 1 d . . . . .
C9 C 0.3146(2) 0.45721(12) 0.69059(11) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.275459 0.414269 0.696801 0.032 Uiso 1 1 calc R . . . .
F9 F 0.5522(3) 0.16957(13) 0.80831(16) 0.0651(10) Uani 0.708(4) 1 d D U P A 1
C24 C 0.4749(3) 0.37975(14) 0.79405(13) 0.0367(6) Uani 1 1 d . . . . .
H24 H 0.420785 0.408754 0.815007 0.044 Uiso 1 1 calc R . . . .
C21 C 0.5986(3) 0.28130(14) 0.79249(13) 0.0368(6) Uani 1 1 d D . . . .
C6 C 0.2416(3) 0.60225(15) 0.83159(13) 0.0383(7) Uani 1 1 d . . . . .
H6 H 0.165017 0.584745 0.814548 0.046 Uiso 1 1 calc R . . . .
C23 C 0.5169(3) 0.32405(14) 0.82324(13) 0.0375(6) Uani 1 1 d . . . . .
H23 H 0.490324 0.315386 0.863252 0.045 Uiso 1 1 calc R . . . .
C2 C 0.3453(3) 0.67411(14) 0.90329(14) 0.0398(7) Uani 1 1 d . . . . .
F8 F 0.6401(6) 0.22278(18) 0.88269(13) 0.0884(14) Uani 0.708(4) 1 d D U P A 1
C13 C 0.2220(3) 0.52862(15) 0.51114(13) 0.0410(7) Uani 1 1 d . . . . .
C11 C 0.3072(4) 0.54599(14) 0.61146(14) 0.0454(8) Uani 1 1 d . . . . .
H11 H 0.344737 0.573716 0.640248 0.055 Uiso 1 1 calc R . . . .
C19 C 0.5930(3) 0.34968(15) 0.70412(14) 0.0433(7) Uani 1 1 d . . . . .
H19 H 0.618587 0.357921 0.663900 0.052 Uiso 1 1 calc R . . . .
C4 C 0.4772(3) 0.60985(16) 0.83610(16) 0.0450(8) Uani 1 1 d . . . . .
H4 H 0.560361 0.597387 0.821914 0.054 Uiso 1 1 calc R . . . .
C7 C 0.2318(3) 0.64775(16) 0.87796(15) 0.0445(7) Uani 1 1 d . . . . .
H7 H 0.148787 0.660583 0.892088 0.053 Uiso 1 1 calc R . . . .
F4 F 0.3017(6) 0.5757(5) 0.4201(4) 0.085(2) Uani 0.499(14) 1 d D U P B 1
C16 C 0.2285(4) 0.44204(15) 0.58368(14) 0.0470(8) Uani 1 1 d . . . . .
H16 H 0.212336 0.398861 0.593234 0.056 Uiso 1 1 calc R . . . .
C12 C 0.2779(4) 0.56900(15) 0.55407(14) 0.0483(8) Uani 1 1 d . . . . .
H12 H 0.295775 0.611934 0.544195 0.058 Uiso 1 1 calc R . . . .
F3 F 0.4183(8) 0.7737(3) 0.9454(3) 0.0621(15) Uani 0.452(3) 1 d D U P C 1
C3 C 0.4685(3) 0.65500(17) 0.88221(17) 0.0520(9) Uani 1 1 d . . . . .
H3 H 0.545093 0.672601 0.899140 0.062 Uiso 1 1 calc R . . . .
C20 C 0.6368(4) 0.29404(16) 0.73294(15) 0.0525(9) Uani 1 1 d . . . . .
H20 H 0.691785 0.265251 0.712243 0.063 Uiso 1 1 calc R . . . .
F1 F 0.3745(9) 0.6961(3) 1.0076(3) 0.0636(15) Uani 0.452(3) 1 d D U P C 1
C1 C 0.3355(4) 0.72231(17) 0.95416(16) 0.0572(8) Uani 1 1 d D U . . .
C15 C 0.1981(4) 0.46474(17) 0.52569(15) 0.0586(10) Uani 1 1 d . . . . .
H15 H 0.161754 0.436982 0.496620 0.070 Uiso 1 1 calc R . . . .
C22 C 0.6388(5) 0.2190(2) 0.8218(2) 0.0520(12) Uani 0.708(4) 1 d D U P A 1
C14 C 0.1895(4) 0.55445(18) 0.44888(15) 0.0642(10) Uani 1 1 d D U . . .
F2 F 0.2146(6) 0.7474(4) 0.9620(4) 0.0723(15) Uani 0.452(3) 1 d D U P C 1
F2A F 0.2570(13) 0.7726(5) 0.9344(5) 0.0622(19) Uani 0.248(3) 1 d D U P C 2
F1A F 0.2807(17) 0.6973(5) 1.0036(4) 0.068(2) Uani 0.248(3) 1 d D U P C 2
F3A F 0.4508(9) 0.7514(7) 0.9675(6) 0.071(2) Uani 0.248(3) 1 d D U P C 2
F7A F 0.7585(9) 0.2509(4) 0.8733(3) 0.073(2) Uani 0.292(4) 1 d D U P A 2
F8A F 0.5681(8) 0.1946(4) 0.8617(5) 0.083(2) Uani 0.292(4) 1 d D U P A 2
F9A F 0.7293(11) 0.1869(7) 0.7898(5) 0.055(2) Uani 0.292(4) 1 d D U P A 2
H2 H 0.194(3) 0.5116(13) 0.7450(13) 0.024(7) Uiso 1 1 d . . . . .
F4A F 0.2863(8) 0.5400(6) 0.4078(3) 0.090(2) Uani 0.501(14) 1 d D U P B 2
F5A F 0.1473(11) 0.6149(3) 0.4466(5) 0.0671(19) Uani 0.501(14) 1 d D U P B 2
F6A F 0.0887(8) 0.5188(6) 0.4225(5) 0.0616(18) Uani 0.501(14) 1 d D U P B 2
C22A C 0.6664(10) 0.2284(5) 0.8307(5) 0.067(2) Uani 0.292(4) 1 d D U P A 2
F3B F 0.3541(15) 0.7808(5) 0.9382(5) 0.070(2) Uani 0.300(3) 1 d . U P C 3
F2B F 0.2188(11) 0.7177(6) 0.9861(5) 0.0624(18) Uani 0.300(3) 1 d . U P C 3
F1B F 0.4274(11) 0.7113(6) 0.9998(5) 0.066(2) Uani 0.300(3) 1 d . U P C 3


_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
N1 C8 1.298(3) . ?
N1 C17 1.482(3) . ?
N2 C8 1.351(3) . ?
N2 C9 1.458(3) . ?
N2 H2 0.82(3) . ?
F7 C22 1.353(6) . ?
F5 C14 1.368(7) . ?
F6 C14 1.320(8) . ?
C8 C5 1.477(4) . ?
C18 C17 1.511(3) . ?
C18 C24 1.385(4) . ?
C18 C19 1.384(4) . ?
C10 C9 1.507(3) . ?
C10 C11 1.388(4) . ?
C10 C16 1.373(4) . ?
C17 H17 0.9800 . ?
C17 C9 1.566(3) . ?
C5 C6 1.389(4) . ?
C5 C4 1.383(4) . ?
C9 H9 0.9800 . ?
F9 C22 1.374(6) . ?
C24 H24 0.9300 . ?
C24 C23 1.381(4) . ?
C21 C23 1.381(4) . ?
C21 C20 1.380(4) . ?
C21 C22 1.493(5) . ?
C21 C22A 1.535(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C23 H23 0.9300 . ?
C2 C7 1.382(4) . ?
C2 C3 1.382(4) . ?
C2 C1 1.494(4) . ?
F8 C22 1.330(5) . ?
C13 C12 1.375(4) . ?
C13 C15 1.378(5) . ?
C13 C14 1.495(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(4) . ?
C7 H7 0.9300 . ?
F4 C14 1.365(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.383(4) . ?
C12 H12 0.9300 . ?
F3 C1 1.365(6) . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
F1 C1 1.345(6) . ?
C1 F2 1.336(6) . ?
C1 F2A 1.375(8) . ?
C1 F1A 1.317(8) . ?
C1 F3A 1.341(8) . ?
C1 F3B 1.271(12) . ?
C1 F2B 1.370(10) . ?
C1 F1B 1.378(11) . ?
C15 H15 0.9300 . ?
C14 F4A 1.358(6) . ?
C14 F5A 1.320(7) . ?
C14 F6A 1.380(7) . ?
F7A C22A 1.393(9) . ?
F8A C22A 1.387(9) . ?
F9A C22A 1.390(9) . ?

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
C8 N1 C17 106.6(2) . . ?
C8 N2 C9 109.8(2) . . ?
C8 N2 H2 125(2) . . ?
C9 N2 H2 124(2) . . ?
N1 C8 N2 115.7(2) . . ?
N1 C8 C5 122.4(2) . . ?
N2 C8 C5 121.8(2) . . ?
C24 C18 C17 120.7(2) . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 C24 118.3(2) . . ?
C11 C10 C9 120.9(2) . . ?
C16 C10 C9 121.0(2) . . ?
C16 C10 C11 118.1(3) . . ?
N1 C17 C18 109.8(2) . . ?
N1 C17 H17 109.5 . . ?
N1 C17 C9 105.19(19) . . ?
C18 C17 H17 109.5 . . ?
C18 C17 C9 113.1(2) . . ?
C9 C17 H17 109.5 . . ?
C6 C5 C8 121.7(2) . . ?
C4 C5 C8 119.8(2) . . ?
C4 C5 C6 118.5(3) . . ?
N2 C9 C10 112.6(2) . . ?
N2 C9 C17 100.12(19) . . ?
N2 C9 H9 110.3 . . ?
C10 C9 C17 112.8(2) . . ?
C10 C9 H9 110.3 . . ?
C17 C9 H9 110.3 . . ?
C18 C24 H24 119.3 . . ?
C23 C24 C18 121.4(3) . . ?
C23 C24 H24 119.3 . . ?
C23 C21 C22 120.3(3) . . ?
C23 C21 C22A 117.2(5) . . ?
C20 C21 C23 120.1(3) . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 C22A 121.5(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C24 C23 C21 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C21 C23 H23 120.3 . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 119.8(3) . . ?
C12 C13 C15 119.7(3) . . ?
C12 C13 C14 119.5(3) . . ?
C15 C13 C14 120.8(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 H7 120.0 . . ?
C10 C16 H16 119.4 . . ?
C10 C16 C15 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
F3 C1 C2 112.0(4) . . ?
F1 C1 C2 110.9(4) . . ?
F1 C1 F3 104.8(5) . . ?
F2 C1 C2 114.5(4) . . ?
F2 C1 F3 105.9(5) . . ?
F2 C1 F1 108.2(6) . . ?
F2A C1 C2 108.0(5) . . ?
F1A C1 C2 112.0(5) . . ?
F1A C1 F2A 108.2(8) . . ?
F1A C1 F3A 111.2(9) . . ?
F3A C1 C2 113.7(5) . . ?
F3A C1 F2A 103.1(8) . . ?
F3B C1 C2 114.8(6) . . ?
F3B C1 F2B 109.4(8) . . ?
F3B C1 F1B 104.8(8) . . ?
F2B C1 C2 112.8(5) . . ?
F2B C1 F1B 101.5(7) . . ?
F1B C1 C2 112.4(5) . . ?
C13 C15 C16 119.8(3) . . ?
C13 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
F7 C22 F9 105.6(4) . . ?
F7 C22 C21 112.4(5) . . ?
F9 C22 C21 112.1(4) . . ?
F8 C22 F7 108.8(5) . . ?
F8 C22 F9 105.3(4) . . ?
F8 C22 C21 112.3(4) . . ?
F5 C14 C13 108.1(6) . . ?
F6 C14 F5 105.3(8) . . ?
F6 C14 C13 115.2(7) . . ?
F6 C14 F4 108.9(6) . . ?
F4 C14 F5 108.5(5) . . ?
F4 C14 C13 110.5(4) . . ?
F4A C14 C13 111.3(4) . . ?
F4A C14 F6A 97.9(6) . . ?
F5A C14 C13 116.3(5) . . ?
F5A C14 F4A 114.5(5) . . ?
F5A C14 F6A 104.6(7) . . ?
F6A C14 C13 110.4(6) . . ?
F7A C22A C21 114.9(7) . . ?
F8A C22A C21 107.7(7) . . ?
F8A C22A F7A 108.6(8) . . ?
F8A C22A F9A 109.2(8) . . ?
F9A C22A C21 107.1(9) . . ?
F9A C22A F7A 109.2(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.759
####################################################################### 
# 
# 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_s4935l
_database_code_depnum_ccdc_archive 'CCDC 1576090'
_audit_update_record             
;
2017-09-22 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_s4935l              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O82 Check
RESPONSE: Hydrogens for the disordered solvent water molecules could not be localised and were therefore not modelled.
;
# Added during the CSD deposition process: Friday 22 September 2017 01:59 PM
# end Validation Reply Form

_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(I), 2.5(O), C30 H42 N5'
_chemical_formula_sum            'C30 H44 I3 N5 O2.50'
_chemical_formula_weight         895.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H44I3N5O2.5
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1338(3)
_cell_length_b                   30.1549(9)
_cell_length_c                   18.5852(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.647(2)
_cell_angle_gamma                90
_cell_volume                     7917.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13411
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      26.1980
_cell_measurement_theta_min      1.9540
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.558
_exptl_absorpt_coefficient_mu    2.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3505
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 36 -13 0.0252
-3 -36 13 0.0252
-19 -2 -8 0.1368
19 2 8 0.1368
6 -22 -21 0.0288
-6 22 21 0.0288

_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0170 36.0422 -12.9906 0.8384 -0.5287 -0.0220
-3.0170 -36.0422 12.9906 -0.8384 0.5287 0.0220
-19.0185 -2.0383 -8.0044 -0.0004 -0.0025 1.0120
19.0185 2.0383 8.0044 0.0004 0.0025 -1.0120
6.0226 -22.0040 -20.9848 0.5274 0.8424 0.0024
-6.0226 22.0040 20.9848 -0.5274 -0.8424 -0.0024

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         2.239
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     67.00 106.00   1.00   30.00    --   17.50  43.00   0.00   39
  2  ω    -71.00  42.00   1.00   30.00    --   17.50  60.00  90.00  113
  3  ω    -68.00  89.00   1.00   30.00    --   17.50  43.00-180.00  157
  4  ω    -46.00 -20.00   1.00   30.00    --   17.50  60.00-120.00   26
  5  ω    -71.00 -44.00   1.00   30.00    --   17.50  43.00   0.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0125841000
_diffrn_orient_matrix_UB_12      0.0104882000
_diffrn_orient_matrix_UB_13      -0.0325203000
_diffrn_orient_matrix_UB_21      0.0089246000
_diffrn_orient_matrix_UB_22      -0.0210169000
_diffrn_orient_matrix_UB_23      -0.0155432000
_diffrn_orient_matrix_UB_31      -0.0477779000
_diffrn_orient_matrix_UB_32      -0.0011564000
_diffrn_orient_matrix_UB_33      -0.0126139000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10348
_reflns_number_total             16200
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.690
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         16200
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0843P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1507
_refine_special_details          
'In this structure four of the iodides are well defined. However, the other two are not, and appear to be highly disordered around a voidspace along with some solvent molecules. Unfortunately, due to the nature of this disorder it was not possible to refine the solvent molecules in the presence of the disordered iodide, therefore these have not been resolved or refined. The two iodides were treated by refining a number of sites agaisnt a SUMP restraint, totalling two iodides. Although this may be seen as a fudge factor, the degree of disorder made the refinement incredibly challenging. Hydrogens for the solvent water molecules could not be localised and were therefore not modelled.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N15-H15 \\sim N50_$1-H50_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(I77) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O83) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 1*[Sof(I75)]+1*[Sof(I76)]+1*[Sof(I81)]+1*[Sof(I78)]+1*[Sof(I77)]+1*[Sof(I79)]+
 1*[Sof(I80)]=2 with esd of 0.001
5.a Ternary CH refined with riding coordinates:
 C49(H49), C48(H48), C14(H14), C13(H13)
5.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C44(H44), C45(H45), C63(H63), C62(H62), C65(H65), C52(H52),
 C56(H56), C53(H53), C66(H66), C41(H41), C55(H55), C17(H17), C30(H30), C18(H18),
  C28(H28), C9(H9), C10(H10), C7(H7), C6(H6), C31(H31), C21(H21), C27(H27),
 C20(H20)
5.c Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C68(H68A,H68B,H68C), C60(H60A,H60B,H60C), C70(H70A,H70B,H70C), C58(H58A,
 H58B,H58C), C59(H59A,H59B,H59C), C1(H1A,H1B,H1C), C24(H24A,H24B,H24C),
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C3(H3A,H3B,H3C), C34(H34A,H34B,H34C),
  C23(H23A,H23B,H23C), C2(H2A,H2B,H2C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I73 I -0.01191(3) 0.15422(2) 0.23443(2) 0.04758(12) Uani 1 1 d . . . . .
I75 I -0.2265(8) 0.3858(8) 0.2368(8) 0.095(3) Uani 0.234(18) 1 d . . P . .
I76 I -0.2203(2) 0.37396(8) 0.22530(15) 0.0552(6) Uani 0.732(18) 1 d . . P . .
I72 I 0.18166(3) 0.46405(2) -0.01265(2) 0.05057(12) Uani 1 1 d . . . . .
I81 I 0.554(2) 0.4801(7) 0.3564(11) 0.190(14) Uani 0.048(2) 1 d . . P . .
I71 I 0.35366(3) 0.58491(2) 0.13391(3) 0.05935(14) Uani 1 1 d . . . . .
I74 I 0.69918(4) 0.21778(2) -0.02070(2) 0.06881(16) Uani 1 1 d . . . . .
O83 O -0.1896(10) 0.4843(4) 0.3197(8) 0.273(6) Uani 1 1 d . U . . .
I78 I 0.23860(7) 0.50079(3) 0.42038(7) 0.0745(4) Uani 0.655(3) 1 d . . P . .
O82 O 0.4103(7) 0.5190(5) 0.2865(6) 0.254(6) Uani 1 1 d . . . . .
O85 O 0.0423(4) 0.2441(2) 0.3584(3) 0.1033(19) Uani 1 1 d . . . . .
O84 O -0.1130(4) 0.3049(2) 0.3611(3) 0.108(2) Uani 1 1 d . . . . .
O86 O 0.4038(7) 0.4464(4) -0.0974(6) 0.203(4) Uani 1 1 d . . . . .
N67 N -0.1081(3) 0.36144(14) -0.0001(2) 0.0373(10) Uani 1 1 d . . . . .
N50 N 0.2593(3) 0.27246(17) 0.1722(2) 0.0410(11) Uani 1 1 d D . . . .
H50 H 0.268(3) 0.2648(16) 0.135(2) 0.027(14) Uiso 1 1 d D . . . .
N57 N 0.0711(4) 0.49527(15) 0.2154(3) 0.0473(12) Uani 1 1 d . . . . .
N39 N 0.7013(3) 0.21291(14) 0.2269(2) 0.0351(10) Uani 1 1 d . . . . .
N47 N 0.2936(3) 0.30761(14) 0.2763(2) 0.0338(10) Uani 1 1 d . . . . .
C61 C 0.0982(3) 0.30018(16) 0.1414(2) 0.0286(11) Uani 1 1 d . . . . .
C43 C 0.4230(3) 0.26825(17) 0.2205(2) 0.0314(11) Uani 1 1 d . . . . .
C40 C 0.6036(3) 0.23229(17) 0.2226(3) 0.0319(11) Uani 1 1 d . . . . .
C46 C 0.3240(3) 0.28437(16) 0.2230(2) 0.0307(11) Uani 1 1 d . . . . .
C64 C -0.0358(3) 0.33876(16) 0.0476(2) 0.0326(11) Uani 1 1 d . . . . .
C49 C 0.1650(3) 0.28184(17) 0.1975(2) 0.0316(11) Uani 1 1 d . . . . .
H49 H 0.138109 0.254339 0.216254 0.038 Uiso 1 1 calc R . . . .
C42 C 0.4960(4) 0.28969(17) 0.2571(3) 0.0356(12) Uani 1 1 d . . . . .
H42 H 0.484475 0.316241 0.280781 0.043 Uiso 1 1 calc R . . . .
C44 C 0.4420(3) 0.22978(17) 0.1832(2) 0.0339(12) Uani 1 1 d . . . . .
H44 H 0.393619 0.215668 0.157108 0.041 Uiso 1 1 calc R . . . .
C51 C 0.1632(3) 0.36167(17) 0.2544(2) 0.0321(11) Uani 1 1 d . . . . .
C45 C 0.5336(4) 0.21176(17) 0.1844(3) 0.0354(12) Uani 1 1 d . . . . .
H45 H 0.546009 0.185903 0.159045 0.042 Uiso 1 1 calc R . . . .
C63 C 0.0563(4) 0.35382(17) 0.0491(3) 0.0375(12) Uani 1 1 d . . . . .
H63 H 0.073543 0.376915 0.019034 0.045 Uiso 1 1 calc R . . . .
C48 C 0.1896(3) 0.31372(17) 0.2632(2) 0.0327(11) Uani 1 1 d . . . . .
H48 H 0.157306 0.302313 0.305360 0.039 Uiso 1 1 calc R . . . .
C62 C 0.1225(4) 0.33494(18) 0.0947(3) 0.0376(12) Uani 1 1 d . . . . .
H62 H 0.184520 0.345214 0.094911 0.045 Uiso 1 1 calc R . . . .
C65 C -0.0616(4) 0.30326(19) 0.0898(3) 0.0452(14) Uani 1 1 d . . . . .
H65 H -0.123056 0.292168 0.087322 0.054 Uiso 1 1 calc R . . . .
C52 C 0.2271(4) 0.39450(19) 0.2375(3) 0.0462(14) Uani 1 1 d . . . . .
H52 H 0.290810 0.387220 0.234780 0.055 Uiso 1 1 calc R . . . .
C56 C 0.0679(4) 0.37443(18) 0.2588(3) 0.0418(13) Uani 1 1 d . . . . .
H56 H 0.023170 0.353232 0.270795 0.050 Uiso 1 1 calc R . . . .
C53 C 0.1994(4) 0.43779(19) 0.2244(3) 0.0498(15) Uani 1 1 d . . . . .
H53 H 0.243920 0.459194 0.213103 0.060 Uiso 1 1 calc R . . . .
C69 C -0.1143(5) 0.41016(19) 0.0192(3) 0.0548(16) Uani 1 1 d . . . . .
H69A H -0.052990 0.423562 0.015500 0.082 Uiso 1 1 calc GR . . . .
H69B H -0.135454 0.413142 0.067544 0.082 Uiso 1 1 calc GR . . . .
H69C H -0.158283 0.424647 -0.013362 0.082 Uiso 1 1 calc GR . . . .
C36 C 0.7677(4) 0.2435(2) 0.1883(3) 0.0514(16) Uani 1 1 d . . . . .
H36A H 0.768315 0.271985 0.211218 0.077 Uiso 1 1 calc GR . . . .
H36B H 0.746508 0.246612 0.139009 0.077 Uiso 1 1 calc GR . . . .
H36C H 0.830375 0.231181 0.190073 0.077 Uiso 1 1 calc GR . . . .
C37 C 0.7341(4) 0.2072(2) 0.3034(3) 0.0466(14) Uani 1 1 d . . . . .
H37A H 0.689910 0.188897 0.328092 0.070 Uiso 1 1 calc GR . . . .
H37B H 0.738274 0.235655 0.326372 0.070 Uiso 1 1 calc GR . . . .
H37C H 0.795276 0.193300 0.304928 0.070 Uiso 1 1 calc GR . . . .
C38 C 0.7064(4) 0.16840(19) 0.1898(3) 0.0485(14) Uani 1 1 d . . . . .
H38A H 0.688875 0.171772 0.139819 0.073 Uiso 1 1 calc GR . . . .
H38B H 0.663638 0.148090 0.211865 0.073 Uiso 1 1 calc GR . . . .
H38C H 0.769726 0.157057 0.194194 0.073 Uiso 1 1 calc GR . . . .
C68 C -0.0794(5) 0.3572(2) -0.0770(3) 0.0652(19) Uani 1 1 d . . . . .
H68A H -0.064575 0.326767 -0.087012 0.098 Uiso 1 1 calc GR . . . .
H68B H -0.024824 0.375296 -0.084683 0.098 Uiso 1 1 calc GR . . . .
H68C H -0.130596 0.366711 -0.108351 0.098 Uiso 1 1 calc GR . . . .
C60 C -0.0011(5) 0.4963(2) 0.1537(3) 0.0591(17) Uani 1 1 d . . . . .
H60A H -0.053189 0.477216 0.164514 0.089 Uiso 1 1 calc GR . . . .
H60B H 0.027840 0.486175 0.110521 0.089 Uiso 1 1 calc GR . . . .
H60C H -0.023654 0.526036 0.146812 0.089 Uiso 1 1 calc GR . . . .
C70 C -0.2055(4) 0.3427(3) 0.0067(4) 0.070(2) Uani 1 1 d . . . . .
H70A H -0.224916 0.345671 0.055590 0.105 Uiso 1 1 calc GR . . . .
H70B H -0.205276 0.311924 -0.006382 0.105 Uiso 1 1 calc GR . . . .
H70C H -0.248834 0.358538 -0.024611 0.105 Uiso 1 1 calc GR . . . .
C58 C 0.1499(5) 0.5261(2) 0.1966(4) 0.069(2) Uani 1 1 d . . . . .
H58A H 0.197240 0.526033 0.234631 0.104 Uiso 1 1 calc GR . . . .
H58B H 0.125259 0.555563 0.190334 0.104 Uiso 1 1 calc GR . . . .
H58C H 0.177491 0.516424 0.152672 0.104 Uiso 1 1 calc GR . . . .
C59 C 0.0240(6) 0.5125(2) 0.2813(4) 0.076(2) Uani 1 1 d . . . . .
H59A H 0.068643 0.512579 0.321215 0.113 Uiso 1 1 calc GR . . . .
H59B H -0.028669 0.493876 0.292217 0.113 Uiso 1 1 calc GR . . . .
H59C H 0.002008 0.542229 0.272484 0.113 Uiso 1 1 calc GR . . . .
C66 C 0.0071(4) 0.28434(18) 0.1363(3) 0.0394(13) Uani 1 1 d . . . . .
H66 H -0.009557 0.260308 0.164664 0.047 Uiso 1 1 calc R . . . .
C54 C 0.1043(4) 0.44902(17) 0.2283(3) 0.0353(12) Uani 1 1 d . . . . .
C41 C 0.5867(4) 0.27176(19) 0.2589(3) 0.0392(13) Uani 1 1 d . . . . .
H41 H 0.635722 0.286020 0.284081 0.047 Uiso 1 1 calc R . . . .
C55 C 0.0388(4) 0.41702(18) 0.2460(3) 0.0391(13) Uani 1 1 d . . . . .
H55 H -0.024797 0.424462 0.249281 0.047 Uiso 1 1 calc R . . . .
N12 N 0.3216(3) 0.24215(14) 0.0297(2) 0.0319(9) Uani 1 1 d . . . . .
N4 N -0.0276(4) 0.10140(16) -0.0009(3) 0.0517(13) Uani 1 1 d . . . . .
N32 N 0.2957(3) 0.39548(17) -0.2544(3) 0.0547(13) Uani 1 1 d . . . . .
N22 N 0.5096(4) 0.43432(17) 0.1083(3) 0.0643(16) Uani 1 1 d . . . . .
N15 N 0.3576(3) 0.21022(14) -0.0762(2) 0.0328(10) Uani 1 1 d D . . . .
H15 H 0.342(4) 0.1995(17) -0.111(2) 0.035(16) Uiso 1 1 d D . . . .
C14 C 0.4201(3) 0.24877(16) -0.0727(2) 0.0316(11) Uani 1 1 d . . . . .
H14 H 0.484386 0.240243 -0.085521 0.038 Uiso 1 1 calc R . . . .
C26 C 0.3848(3) 0.28678(16) -0.1208(2) 0.0294(11) Uani 1 1 d . . . . .
C16 C 0.4385(3) 0.30413(17) 0.0352(2) 0.0303(11) Uani 1 1 d . . . . .
C11 C 0.2975(4) 0.21398(16) -0.0208(2) 0.0334(11) Uani 1 1 d . . . . .
C17 C 0.3720(4) 0.33810(18) 0.0298(3) 0.0381(12) Uani 1 1 d . . . . .
H17 H 0.311990 0.331980 0.010499 0.046 Uiso 1 1 calc R . . . .
C13 C 0.4164(3) 0.25810(17) 0.0100(2) 0.0323(11) Uani 1 1 d . . . . .
H13 H 0.462822 0.238401 0.033637 0.039 Uiso 1 1 calc R . . . .
C8 C 0.2118(4) 0.18582(17) -0.0181(2) 0.0338(12) Uani 1 1 d . . . . .
C19 C 0.4840(4) 0.38947(18) 0.0822(3) 0.0415(13) Uani 1 1 d . . . . .
C30 C 0.2629(4) 0.32656(18) -0.1863(3) 0.0398(13) Uani 1 1 d . . . . .
H30 H 0.199856 0.329155 -0.201347 0.048 Uiso 1 1 calc R . . . .
C18 C 0.3930(4) 0.38050(18) 0.0523(3) 0.0419(13) Uani 1 1 d . . . . .
H18 H 0.348045 0.402918 0.047838 0.050 Uiso 1 1 calc R . . . .
C28 C 0.4218(4) 0.35423(18) -0.1845(3) 0.0410(13) Uani 1 1 d . . . . .
H28 H 0.465778 0.375385 -0.197998 0.049 Uiso 1 1 calc R . . . .
C9 C 0.1325(4) 0.2002(2) 0.0178(3) 0.0520(16) Uani 1 1 d . . . . .
H9 H 0.132536 0.228186 0.038695 0.062 Uiso 1 1 calc R . . . .
C10 C 0.0541(4) 0.1736(2) 0.0228(4) 0.0588(18) Uani 1 1 d . . . . .
H10 H 0.001722 0.183761 0.047098 0.071 Uiso 1 1 calc R . . . .
C7 C 0.2089(4) 0.14531(19) -0.0504(3) 0.0482(15) Uani 1 1 d . . . . .
H7 H 0.260694 0.135868 -0.076078 0.058 Uiso 1 1 calc R . . . .
C6 C 0.1310(5) 0.1179(2) -0.0462(3) 0.0591(18) Uani 1 1 d . . . . .
H6 H 0.130802 0.090247 -0.068413 0.071 Uiso 1 1 calc R . . . .
C1 C -0.1115(4) 0.1229(2) 0.0330(4) 0.070(2) Uani 1 1 d . . . . .
H1A H -0.092868 0.134502 0.079397 0.105 Uiso 1 1 calc GR . . . .
H1B H -0.160651 0.101273 0.038504 0.105 Uiso 1 1 calc GR . . . .
H1C H -0.134527 0.146585 0.002804 0.105 Uiso 1 1 calc GR . . . .
C24 C 0.6044(4) 0.4482(2) 0.0851(4) 0.0666(19) Uani 1 1 d . . . . .
H24A H 0.652016 0.431329 0.110909 0.100 Uiso 1 1 calc GR . . . .
H24B H 0.613289 0.479161 0.095052 0.100 Uiso 1 1 calc GR . . . .
H24C H 0.609479 0.443014 0.034414 0.100 Uiso 1 1 calc GR . . . .
C31 C 0.2910(4) 0.29159(16) -0.1434(3) 0.0345(12) Uani 1 1 d . . . . .
H31 H 0.246434 0.270844 -0.129412 0.041 Uiso 1 1 calc R . . . .
C21 C 0.5270(4) 0.31349(17) 0.0648(3) 0.0353(12) Uani 1 1 d . . . . .
H21 H 0.571995 0.291053 0.068551 0.042 Uiso 1 1 calc R . . . .
C27 C 0.4491(4) 0.31850(18) -0.1416(3) 0.0374(12) Uani 1 1 d . . . . .
H27 H 0.512110 0.315840 -0.126549 0.045 Uiso 1 1 calc R . . . .
C5 C 0.0525(4) 0.13195(19) -0.0081(3) 0.0441(14) Uani 1 1 d . . . . .
C20 C 0.5501(4) 0.35622(18) 0.0895(3) 0.0401(13) Uani 1 1 d . . . . .
H20 H 0.609429 0.361982 0.110377 0.048 Uiso 1 1 calc R . . . .
C29 C 0.3276(4) 0.35775(18) -0.2069(3) 0.0395(12) Uani 1 1 d . . . . .
C33 C 0.2194(5) 0.4211(2) -0.2178(4) 0.069(2) Uani 1 1 d . . . . .
H33A H 0.163882 0.402912 -0.214644 0.103 Uiso 1 1 calc GR . . . .
H33B H 0.204452 0.447284 -0.245071 0.103 Uiso 1 1 calc GR . . . .
H33C H 0.241244 0.429291 -0.170237 0.103 Uiso 1 1 calc GR . . . .
C35 C 0.2560(5) 0.3775(3) -0.3244(4) 0.075(2) Uani 1 1 d . . . . .
H35A H 0.302846 0.359426 -0.346721 0.113 Uiso 1 1 calc GR . . . .
H35B H 0.238854 0.401632 -0.355809 0.113 Uiso 1 1 calc GR . . . .
H35C H 0.201007 0.359868 -0.315461 0.113 Uiso 1 1 calc GR . . . .
C3 C -0.0572(6) 0.0816(3) -0.0698(4) 0.096(3) Uani 1 1 d . . . . .
H3A H -0.068685 0.104669 -0.104588 0.144 Uiso 1 1 calc GR . . . .
H3B H -0.114250 0.064877 -0.063786 0.144 Uiso 1 1 calc GR . . . .
H3C H -0.008288 0.062350 -0.086167 0.144 Uiso 1 1 calc GR . . . .
C34 C 0.3749(5) 0.4264(3) -0.2714(5) 0.090(3) Uani 1 1 d . . . . .
H34A H 0.400801 0.438851 -0.227581 0.134 Uiso 1 1 calc GR . . . .
H34B H 0.351251 0.449788 -0.302022 0.134 Uiso 1 1 calc GR . . . .
H34C H 0.423369 0.410392 -0.295562 0.134 Uiso 1 1 calc GR . . . .
C23 C 0.5161(6) 0.4322(3) 0.1931(5) 0.102(3) Uani 1 1 d . . . . .
H23A H 0.460842 0.417651 0.210595 0.153 Uiso 1 1 calc GR . . . .
H23B H 0.519744 0.461709 0.212219 0.153 Uiso 1 1 calc GR . . . .
H23C H 0.571541 0.415852 0.207992 0.153 Uiso 1 1 calc GR . . . .
C2 C 0.0058(6) 0.0646(3) 0.0486(5) 0.090(3) Uani 1 1 d . . . . .
H2A H 0.035678 0.077186 0.090984 0.136 Uiso 1 1 calc GR . . . .
H2B H 0.050285 0.046327 0.024335 0.136 Uiso 1 1 calc GR . . . .
H2C H -0.047423 0.047023 0.062163 0.136 Uiso 1 1 calc GR . . . .
C25 C 0.4396(7) 0.4682(3) 0.0888(9) 0.166(7) Uani 1 1 d . . . . .
H25A H 0.424971 0.466556 0.038069 0.249 Uiso 1 1 calc GR . . . .
H25B H 0.464720 0.496970 0.100312 0.249 Uiso 1 1 calc GR . . . .
H25C H 0.383083 0.463270 0.115081 0.249 Uiso 1 1 calc GR . . . .
I77 I 0.2401(3) 0.49725(17) 0.4794(7) 0.147(4) Uani 0.176(4) 1 d . U P . .
I79 I 0.6121(16) 0.3784(7) 0.3704(12) 0.133(10) Uani 0.040(2) 1 d . . P . .
I80 I 0.4575(8) 0.3707(4) 0.5640(6) 0.208(6) Uani 0.119(3) 1 d . . 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
I78 I77 1.101(13) . ?
N67 C64 1.498(6) . ?
N67 C69 1.515(7) . ?
N67 C68 1.502(7) . ?
N67 C70 1.497(7) . ?
N50 H50 0.75(4) . ?
N50 C46 1.345(7) . ?
N50 C49 1.455(6) . ?
N57 C60 1.514(8) . ?
N57 C58 1.499(8) . ?
N57 C59 1.503(7) . ?
N57 C54 1.489(7) . ?
N39 C40 1.500(6) . ?
N39 C36 1.511(6) . ?
N39 C37 1.492(7) . ?
N39 C38 1.512(7) . ?
N47 C46 1.297(6) . ?
N47 C48 1.494(6) . ?
C61 C49 1.492(7) . ?
C61 C62 1.409(7) . ?
C61 C66 1.375(7) . ?
C43 C46 1.483(7) . ?
C43 C42 1.381(7) . ?
C43 C44 1.381(7) . ?
C40 C45 1.351(7) . ?
C40 C41 1.392(7) . ?
C64 C63 1.379(7) . ?
C64 C65 1.382(7) . ?
C49 H49 0.9800 . ?
C49 C48 1.585(7) . ?
C42 H42 0.9300 . ?
C42 C41 1.391(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.404(7) . ?
C51 C48 1.501(7) . ?
C51 C52 1.382(7) . ?
C51 C56 1.406(7) . ?
C45 H45 0.9300 . ?
C63 H63 0.9300 . ?
C63 C62 1.368(7) . ?
C48 H48 0.9800 . ?
C62 H62 0.9300 . ?
C65 H65 0.9300 . ?
C65 C66 1.404(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.382(8) . ?
C56 H56 0.9300 . ?
C56 C55 1.367(7) . ?
C53 H53 0.9300 . ?
C53 C54 1.390(7) . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C66 H66 0.9300 . ?
C54 C55 1.384(7) . ?
C41 H41 0.9300 . ?
C55 H55 0.9300 . ?
N12 C11 1.304(6) . ?
N12 C13 1.479(6) . ?
N4 C1 1.506(8) . ?
N4 C5 1.468(7) . ?
N4 C3 1.463(8) . ?
N4 C2 1.507(9) . ?
N32 C29 1.501(7) . ?
N32 C33 1.504(8) . ?
N32 C35 1.504(9) . ?
N32 C34 1.497(8) . ?
N22 C19 1.478(7) . ?
N22 C24 1.480(8) . ?
N22 C23 1.577(10) . ?
N22 C25 1.460(10) . ?
N15 H15 0.75(4) . ?
N15 C14 1.461(6) . ?
N15 C11 1.359(6) . ?
C14 H14 0.9800 . ?
C14 C26 1.529(7) . ?
C14 C13 1.564(6) . ?
C26 C31 1.387(7) . ?
C26 C27 1.382(7) . ?
C16 C17 1.391(7) . ?
C16 C13 1.495(7) . ?
C16 C21 1.381(7) . ?
C11 C8 1.481(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(7) . ?
C13 H13 0.9800 . ?
C8 C9 1.389(7) . ?
C8 C7 1.362(7) . ?
C19 C18 1.412(8) . ?
C19 C20 1.375(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.372(7) . ?
C30 C29 1.374(7) . ?
C18 H18 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.388(8) . ?
C28 C29 1.387(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(8) . ?
C10 H10 0.9300 . ?
C10 C5 1.382(8) . ?
C7 H7 0.9300 . ?
C7 C6 1.381(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.399(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C31 H31 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.403(7) . ?
C27 H27 0.9300 . ?
C20 H20 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C64 N67 C69 110.2(4) . . ?
C64 N67 C68 109.0(4) . . ?
C68 N67 C69 109.1(5) . . ?
C70 N67 C64 113.0(4) . . ?
C70 N67 C69 106.6(5) . . ?
C70 N67 C68 108.8(5) . . ?
C46 N50 H50 128(4) . . ?
C46 N50 C49 109.3(4) . . ?
C49 N50 H50 123(4) . . ?
C58 N57 C60 107.4(5) . . ?
C58 N57 C59 108.9(5) . . ?
C59 N57 C60 107.8(5) . . ?
C54 N57 C60 110.0(4) . . ?
C54 N57 C58 112.7(4) . . ?
C54 N57 C59 109.8(4) . . ?
C40 N39 C36 108.7(4) . . ?
C40 N39 C38 112.1(4) . . ?
C36 N39 C38 106.7(4) . . ?
C37 N39 C40 110.9(4) . . ?
C37 N39 C36 110.1(4) . . ?
C37 N39 C38 108.3(4) . . ?
C46 N47 C48 106.7(4) . . ?
C62 C61 C49 123.1(4) . . ?
C66 C61 C49 119.4(4) . . ?
C66 C61 C62 117.4(5) . . ?
C42 C43 C46 121.5(5) . . ?
C42 C43 C44 119.2(5) . . ?
C44 C43 C46 119.3(5) . . ?
C45 C40 N39 120.6(5) . . ?
C45 C40 C41 120.9(5) . . ?
C41 C40 N39 118.5(4) . . ?
N50 C46 C43 120.8(4) . . ?
N47 C46 N50 116.6(4) . . ?
N47 C46 C43 122.4(5) . . ?
C63 C64 N67 119.3(4) . . ?
C63 C64 C65 120.6(5) . . ?
C65 C64 N67 120.1(5) . . ?
N50 C49 C61 114.3(4) . . ?
N50 C49 H49 108.6 . . ?
N50 C49 C48 100.6(4) . . ?
C61 C49 H49 108.6 . . ?
C61 C49 C48 115.7(4) . . ?
C48 C49 H49 108.6 . . ?
C43 C42 H42 119.8 . . ?
C43 C42 C41 120.3(5) . . ?
C41 C42 H42 119.8 . . ?
C43 C44 H44 119.7 . . ?
C43 C44 C45 120.7(5) . . ?
C45 C44 H44 119.7 . . ?
C52 C51 C48 123.5(4) . . ?
C52 C51 C56 116.8(5) . . ?
C56 C51 C48 119.5(5) . . ?
C40 C45 C44 119.5(5) . . ?
C40 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
C64 C63 H63 119.9 . . ?
C62 C63 C64 120.3(5) . . ?
C62 C63 H63 119.9 . . ?
N47 C48 C49 104.1(3) . . ?
N47 C48 C51 112.2(4) . . ?
N47 C48 H48 107.8 . . ?
C49 C48 H48 107.8 . . ?
C51 C48 C49 116.8(4) . . ?
C51 C48 H48 107.8 . . ?
C61 C62 H62 119.4 . . ?
C63 C62 C61 121.1(5) . . ?
C63 C62 H62 119.4 . . ?
C64 C65 H65 120.8 . . ?
C64 C65 C66 118.4(5) . . ?
C66 C65 H65 120.8 . . ?
C51 C52 H52 118.9 . . ?
C51 C52 C53 122.2(5) . . ?
C53 C52 H52 118.9 . . ?
C51 C56 H56 119.0 . . ?
C55 C56 C51 122.0(5) . . ?
C55 C56 H56 119.0 . . ?
C52 C53 H53 120.3 . . ?
C52 C53 C54 119.4(5) . . ?
C54 C53 H53 120.3 . . ?
N67 C69 H69A 109.5 . . ?
N67 C69 H69B 109.5 . . ?
N67 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
N39 C36 H36A 109.5 . . ?
N39 C36 H36B 109.5 . . ?
N39 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N39 C37 H37A 109.5 . . ?
N39 C37 H37B 109.5 . . ?
N39 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N39 C38 H38A 109.5 . . ?
N39 C38 H38B 109.5 . . ?
N39 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N67 C68 H68A 109.5 . . ?
N67 C68 H68B 109.5 . . ?
N67 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
N57 C60 H60A 109.5 . . ?
N57 C60 H60B 109.5 . . ?
N57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
N67 C70 H70A 109.5 . . ?
N67 C70 H70B 109.5 . . ?
N67 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
N57 C58 H58A 109.5 . . ?
N57 C58 H58B 109.5 . . ?
N57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N57 C59 H59A 109.5 . . ?
N57 C59 H59B 109.5 . . ?
N57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C61 C66 C65 122.1(5) . . ?
C61 C66 H66 118.9 . . ?
C65 C66 H66 118.9 . . ?
C53 C54 N57 121.4(5) . . ?
C55 C54 N57 118.8(4) . . ?
C55 C54 C53 119.8(5) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.4(5) . . ?
C42 C41 H41 120.3 . . ?
C56 C55 C54 119.8(5) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C11 N12 C13 104.7(4) . . ?
C1 N4 C2 107.3(5) . . ?
C5 N4 C1 112.8(5) . . ?
C5 N4 C2 106.8(5) . . ?
C3 N4 C1 109.4(6) . . ?
C3 N4 C5 112.2(5) . . ?
C3 N4 C2 108.1(6) . . ?
C29 N32 C33 109.2(5) . . ?
C29 N32 C35 109.5(5) . . ?
C35 N32 C33 108.8(5) . . ?
C34 N32 C29 112.5(5) . . ?
C34 N32 C33 109.0(6) . . ?
C34 N32 C35 107.7(6) . . ?
C19 N22 C24 112.2(5) . . ?
C19 N22 C23 107.2(5) . . ?
C24 N22 C23 106.0(5) . . ?
C25 N22 C19 113.6(6) . . ?
C25 N22 C24 110.1(7) . . ?
C25 N22 C23 107.2(8) . . ?
C14 N15 H15 123(4) . . ?
C11 N15 H15 121(4) . . ?
C11 N15 C14 106.9(4) . . ?
N15 C14 H14 110.1 . . ?
N15 C14 C26 112.5(4) . . ?
N15 C14 C13 98.6(4) . . ?
C26 C14 H14 110.1 . . ?
C26 C14 C13 114.9(4) . . ?
C13 C14 H14 110.1 . . ?
C31 C26 C14 123.3(4) . . ?
C27 C26 C14 118.4(4) . . ?
C27 C26 C31 118.2(5) . . ?
C17 C16 C13 121.8(5) . . ?
C21 C16 C17 118.7(5) . . ?
C21 C16 C13 119.5(5) . . ?
N12 C11 N15 116.3(4) . . ?
N12 C11 C8 123.1(4) . . ?
N15 C11 C8 120.6(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(5) . . ?
C18 C17 H17 119.2 . . ?
N12 C13 C14 103.9(4) . . ?
N12 C13 C16 114.0(4) . . ?
N12 C13 H13 106.9 . . ?
C14 C13 H13 106.9 . . ?
C16 C13 C14 117.5(4) . . ?
C16 C13 H13 106.9 . . ?
C9 C8 C11 120.6(5) . . ?
C7 C8 C11 120.9(5) . . ?
C7 C8 C9 118.5(5) . . ?
C18 C19 N22 121.0(5) . . ?
C20 C19 N22 118.4(5) . . ?
C20 C19 C18 120.5(5) . . ?
C31 C30 H30 119.9 . . ?
C31 C30 C29 120.3(5) . . ?
C29 C30 H30 119.9 . . ?
C17 C18 C19 118.9(5) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C29 C28 C27 118.7(5) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C5 120.4(5) . . ?
C5 C10 H10 119.8 . . ?
C8 C7 H7 119.1 . . ?
C8 C7 C6 121.8(5) . . ?
C6 C7 H7 119.1 . . ?
C7 C6 H6 120.2 . . ?
C7 C6 C5 119.5(5) . . ?
C5 C6 H6 120.2 . . ?
N4 C1 H1A 109.5 . . ?
N4 C1 H1B 109.5 . . ?
N4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N22 C24 H24A 109.5 . . ?
N22 C24 H24B 109.5 . . ?
N22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C31 H31 119.5 . . ?
C30 C31 C26 120.9(5) . . ?
C30 C31 H31 119.5 . . ?
C16 C21 H21 119.4 . . ?
C16 C21 C20 121.2(5) . . ?
C20 C21 H21 119.4 . . ?
C26 C27 C28 121.6(5) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C10 C5 N4 122.4(5) . . ?
C10 C5 C6 118.8(5) . . ?
C6 C5 N4 118.7(5) . . ?
C19 C20 C21 119.1(5) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C30 C29 N32 119.5(5) . . ?
C30 C29 C28 120.3(5) . . ?
C28 C29 N32 120.2(5) . . ?
N32 C33 H33A 109.5 . . ?
N32 C33 H33B 109.5 . . ?
N32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N32 C35 H35A 109.5 . . ?
N32 C35 H35B 109.5 . . ?
N32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N32 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
N32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N22 C23 H23A 109.5 . . ?
N22 C23 H23B 109.5 . . ?
N22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N22 C25 H25A 109.5 . . ?
N22 C25 H25B 109.5 . . ?
N22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.349
_oxdiff_exptl_absorpt_empirical_full_min 0.406
