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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d8-0405_a
_database_code_depnum_ccdc_archive 'CCDC 1830915'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 I7 P'
_chemical_formula_weight         1189.62

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.8007(9)
_cell_length_b                   12.2538(9)
_cell_length_c                   21.8576(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.261(3)
_cell_angle_gamma                90
_cell_volume                     2884.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      33.17

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.739
_exptl_crystal_F_000             2120
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.169
_exptl_absorpt_coefficient_mu    7.595
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8024
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55007
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7313
_reflns_number_gt                6607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+1.5883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7313
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0555
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_restrained_S_all      1.239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.67562(2) 0.73216(2) 0.87866(2) 0.02088(5) Uani 1 1 d . . . . .
I2 I 0.88999(2) 0.72584(2) 0.96459(2) 0.02606(6) Uani 1 1 d . . . . .
I3 I 0.45514(2) 0.73339(2) 0.78972(2) 0.03041(6) Uani 1 1 d . . . . .
I4 I 0.61913(2) 0.72445(2) 0.65623(2) 0.01906(5) Uani 1 1 d . . . . .
I5 I 0.68006(2) 0.92910(2) 0.54670(2) 0.02252(5) Uani 1 1 d . . . . .
I6 I 0.81879(2) 0.53763(2) 0.58444(2) 0.02332(6) Uani 1 1 d . . . . .
I7 I 0.87732(3) 0.74063(2) 0.47185(2) 0.03181(6) Uani 1 1 d . . . . .
P1 P 0.48241(7) 0.37137(6) 0.73426(3) 0.01315(14) Uani 1 1 d . . . . .
C1 C 0.4333(3) 0.3816(2) 0.81062(13) 0.0142(5) Uani 1 1 d . . . . .
C2 C 0.3303(3) 0.3221(2) 0.82628(14) 0.0186(6) Uani 1 1 d . . . . .
H2A H 0.2868 0.2770 0.7966 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2916(3) 0.3289(2) 0.88484(14) 0.0205(6) Uani 1 1 d . . . . .
H3A H 0.2207 0.2894 0.8955 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3570(3) 0.3938(3) 0.92824(15) 0.0225(7) Uani 1 1 d . . . . .
H4A H 0.3311 0.3974 0.9688 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4588(3) 0.4529(3) 0.91326(15) 0.0237(7) Uani 1 1 d . . . . .
H5A H 0.5024 0.4973 0.9432 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4976(3) 0.4473(2) 0.85408(14) 0.0188(6) Uani 1 1 d . . . . .
H6A H 0.5677 0.4881 0.8434 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3858(3) 0.4488(2) 0.68018(13) 0.0149(6) Uani 1 1 d . . . . .
C8 C 0.2708(3) 0.4873(2) 0.69482(15) 0.0206(6) Uani 1 1 d . . . . .
H8A H 0.2446 0.4780 0.7350 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1943(3) 0.5399(3) 0.64989(16) 0.0267(7) Uani 1 1 d . . . . .
H9A H 0.1152 0.5664 0.6593 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2336(3) 0.5536(3) 0.59158(16) 0.0269(7) Uani 1 1 d . . . . .
H10A H 0.1810 0.5890 0.5609 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3481(3) 0.5163(3) 0.57766(15) 0.0244(7) Uani 1 1 d . . . . .
H11A H 0.3745 0.5267 0.5376 0.029 Uiso 1 1 calc R U . . .
C12 C 0.4254(3) 0.4637(2) 0.62166(14) 0.0193(6) Uani 1 1 d . . . . .
H12A H 0.5046 0.4381 0.6120 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4731(3) 0.2303(2) 0.71180(14) 0.0148(6) Uani 1 1 d . . . . .
C14 C 0.3867(3) 0.1971(2) 0.66592(14) 0.0208(6) Uani 1 1 d . . . . .
H14A H 0.3344 0.2491 0.6447 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3767(3) 0.0861(3) 0.65085(15) 0.0250(7) Uani 1 1 d . . . . .
H15A H 0.3168 0.0624 0.6196 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4537(3) 0.0118(3) 0.68130(17) 0.0252(7) Uani 1 1 d . . . . .
H16A H 0.4477 -0.0632 0.6706 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5400(3) 0.0451(3) 0.72752(19) 0.0317(8) Uani 1 1 d . . . . .
H17A H 0.5920 -0.0072 0.7487 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5508(3) 0.1544(3) 0.74289(18) 0.0269(7) Uani 1 1 d . . . . .
H18A H 0.6105 0.1776 0.7743 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6392(3) 0.4193(2) 0.73409(15) 0.0201(6) Uani 1 1 d . . . . .
H19A H 0.6924 0.3770 0.7637 0.030 Uiso 1 1 calc R U . . .
H19B H 0.6684 0.4103 0.6930 0.030 Uiso 1 1 calc R U . . .
H19C H 0.6426 0.4966 0.7455 0.030 Uiso 1 1 calc R U . . .
C20A C 0.7132(6) 0.7654(6) 0.5753(3) 0.0152(12) Uani 0.5 1 d . . P A 1
C21A C 0.7871(6) 0.6968(5) 0.5493(3) 0.0181(12) Uani 0.5 1 d . . P A 1
C20B C 0.7361(6) 0.6961(6) 0.5861(3) 0.0177(12) Uani 0.5 1 d . . P A 2
C21B C 0.7586(7) 0.7721(5) 0.5462(4) 0.0201(13) Uani 0.5 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8720(4) . ?
I1 I3 2.9600(4) . ?
I1 I6 3.8285(4) 2_656 ?
I1 I7 3.9517(4) 4_576 ?
I1 I5 4.3017(4) 2_646 ?
I1 I4 4.8557(5) . ?
I2 I5 3.7186(4) 2_646 ?
I2 I5 3.9758(4) 4_676 ?
I2 I6 4.5245(4) 2_656 ?
I2 I4 4.7436(5) 4_676 ?
I2 I7 5.2702(6) 4_676 ?
I3 I4 3.5259(4) . ?
I3 I7 4.1416(5) 4_576 ?
I3 I6 5.1408(4) 2_656 ?
I4 C20B 2.086(7) . ?
I4 C20A 2.163(8) . ?
I4 C21B 2.989(9) . ?
I4 C21A 3.082(7) . ?
I4 I5 3.5618(3) . ?
I4 I6 3.5855(3) . ?
I4 I2 4.7437(5) 4_575 ?
I5 C21B 2.102(7) . ?
I5 C20A 2.123(7) . ?
I5 C20B 3.031(7) . ?
I5 C21A 3.071(6) . ?
I5 I7 3.6149(4) . ?
I5 I2 3.7186(4) 2_656 ?
I5 I2 3.9758(4) 4_575 ?
I6 C21A 2.115(6) . ?
I6 C20B 2.139(7) . ?
I6 C20A 3.017(7) . ?
I6 C21B 3.049(7) . ?
I6 I7 3.5881(4) . ?
I6 I1 3.8286(4) 2_646 ?
I6 I2 4.5244(4) 2_646 ?
I7 C21A 2.086(7) . ?
I7 C21B 2.178(9) . ?
I7 C20A 2.991(7) . ?
I7 C20B 3.071(7) . ?
I7 I1 3.9518(4) 4_675 ?
I7 I3 4.1416(5) 4_675 ?
P1 C7 1.790(3) . ?
P1 C1 1.793(3) . ?
P1 C19 1.793(3) . ?
P1 C13 1.797(3) . ?
C1 C6 1.391(4) . ?
C1 C2 1.394(4) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(4) . ?
C7 C12 1.390(4) . ?
C8 C9 1.394(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.374(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.379(4) . ?
C13 C18 1.395(4) . ?
C14 C15 1.402(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.371(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.384(5) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20A C21A 1.317(10) . ?
C20B C21B 1.312(10) . ?

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
I2 I1 I3 178.730(10) . . ?
I2 I1 I6 83.643(7) . 2_656 ?
I3 I1 I6 97.627(8) . 2_656 ?
I2 I1 I7 108.282(10) . 4_576 ?
I3 I1 I7 72.010(10) . 4_576 ?
I6 I1 I7 79.025(6) 2_656 4_576 ?
I2 I1 I5 58.459(7) . 2_646 ?
I3 I1 I5 120.303(8) . 2_646 ?
I6 I1 I5 139.867(8) 2_656 2_646 ?
I7 I1 I5 99.420(7) 4_576 2_646 ?
I2 I1 I4 133.591(8) . . ?
I3 I1 I4 46.168(7) . . ?
I6 I1 I4 103.227(6) 2_656 . ?
I7 I1 I4 118.111(8) 4_576 . ?
I5 I1 I4 112.206(6) 2_646 . ?
I1 I2 I5 80.375(7) . 2_646 ?
I1 I2 I5 151.413(9) . 4_676 ?
I5 I2 I5 73.298(7) 2_646 4_676 ?
I1 I2 I6 57.244(7) . 2_656 ?
I5 I2 I6 135.614(8) 2_646 2_656 ?
I5 I2 I6 150.733(7) 4_676 2_656 ?
I1 I2 I4 156.406(8) . 4_676 ?
I5 I2 I4 105.927(7) 2_646 4_676 ?
I5 I2 I4 47.212(5) 4_676 4_676 ?
I6 I2 I4 108.595(6) 2_656 4_676 ?
I1 I2 I7 140.573(9) . 4_676 ?
I5 I2 I7 106.024(6) 2_646 4_676 ?
I5 I2 I7 43.268(6) 4_676 4_676 ?
I6 I2 I7 114.859(7) 2_656 4_676 ?
I4 I2 I7 60.592(6) 4_676 4_676 ?
I1 I3 I4 96.558(11) . . ?
I1 I3 I7 65.164(9) . 4_576 ?
I4 I3 I7 161.472(9) . 4_576 ?
I1 I3 I6 47.574(6) . 2_656 ?
I4 I3 I6 102.560(8) . 2_656 ?
I7 I3 I6 63.399(7) 4_576 2_656 ?
C20B I4 C21B 22.0(2) . . ?
C20A I4 C21A 21.1(2) . . ?
C20B I4 I3 169.07(19) . . ?
C20A I4 I3 164.74(18) . . ?
C21B I4 I3 166.92(13) . . ?
C21A I4 I3 172.40(12) . . ?
C20B I4 I5 58.10(19) . . ?
C20A I4 I5 33.44(19) . . ?
C21B I4 I5 36.12(13) . . ?
C21A I4 I5 54.49(12) . . ?
I3 I4 I5 131.576(8) . . ?
C20B I4 I6 32.38(19) . . ?
C20A I4 I6 57.06(19) . . ?
C21B I4 I6 54.36(13) . . ?
C21A I4 I6 35.99(12) . . ?
I3 I4 I6 137.514(8) . . ?
I5 I4 I6 90.472(8) . . ?
C20B I4 I2 71.19(18) . 4_575 ?
C20A I4 I2 59.60(17) . 4_575 ?
C21B I4 I2 61.67(13) . 4_575 ?
C21A I4 I2 69.04(12) . 4_575 ?
I3 I4 I2 117.748(9) . 4_575 ?
I5 I4 I2 55.001(6) . 4_575 ?
I6 I4 I2 89.247(8) . 4_575 ?
C21B I5 C20B 21.2(3) . . ?
C20A I5 C21A 20.6(2) . . ?
C21B I5 I4 56.9(2) . . ?
C20A I5 I4 34.2(2) . . ?
C20B I5 I4 35.76(12) . . ?
C21A I5 I4 54.77(12) . . ?
C21B I5 I7 33.0(2) . . ?
C20A I5 I7 55.8(2) . . ?
C20B I5 I7 54.18(12) . . ?
C21A I5 I7 35.17(12) . . ?
I4 I5 I7 89.938(8) . . ?
C21B I5 I2 167.0(2) . 2_656 ?
C20A I5 I2 166.46(19) . 2_656 ?
C20B I5 I2 167.30(12) . 2_656 ?
C21A I5 I2 169.11(12) . 2_656 ?
I4 I5 I2 133.332(8) . 2_656 ?
I7 I5 I2 135.935(8) . 2_656 ?
C21B I5 I2 82.27(17) . 4_575 ?
C20A I5 I2 77.97(17) . 4_575 ?
C20B I5 I2 79.20(12) . 4_575 ?
C21A I5 I2 81.29(11) . 4_575 ?
I4 I5 I2 77.787(7) . 4_575 ?
I7 I5 I2 87.808(9) . 4_575 ?
I2 I5 I2 106.703(7) 2_656 4_575 ?
C21A I6 C20A 21.9(2) . . ?
C20B I6 C21B 21.3(2) . . ?
C21A I6 I4 58.91(18) . . ?
C20B I6 I4 31.50(18) . . ?
C20A I6 I4 36.99(14) . . ?
C21B I6 I4 52.80(16) . . ?
C21A I6 I7 31.08(18) . . ?
C20B I6 I7 58.50(18) . . ?
C20A I6 I7 53.00(14) . . ?
C21B I6 I7 37.20(16) . . ?
I4 I6 I7 89.991(9) . . ?
C21A I6 I1 167.90(17) . 2_646 ?
C20B I6 I1 152.14(18) . 2_646 ?
C20A I6 I1 156.72(14) . 2_646 ?
C21B I6 I1 168.18(12) . 2_646 ?
I4 I6 I1 122.182(8) . 2_646 ?
I7 I6 I1 145.232(8) . 2_646 ?
C21A I6 I2 128.92(17) . 2_646 ?
C20B I6 I2 124.71(17) . 2_646 ?
C20A I6 I2 125.90(12) . 2_646 ?
C21B I6 I2 129.68(12) . 2_646 ?
I4 I6 I2 109.719(8) . 2_646 ?
I7 I6 I2 122.213(8) . 2_646 ?
I1 I6 I2 39.113(5) 2_646 2_646 ?
C21A I7 C20A 22.1(2) . . ?
C21B I7 C20B 21.4(2) . . ?
C21A I7 I6 31.57(18) . . ?
C21B I7 I6 57.84(18) . . ?
C20A I7 I6 53.65(14) . . ?
C20B I7 I6 36.43(13) . . ?
C21A I7 I5 58.03(18) . . ?
C21B I7 I5 31.74(18) . . ?
C20A I7 I5 35.95(14) . . ?
C20B I7 I5 53.16(13) . . ?
I6 I7 I5 89.583(9) . . ?
C21A I7 I1 152.66(18) . 4_675 ?
C21B I7 I1 156.55(16) . 4_675 ?
C20A I7 I1 158.91(12) . 4_675 ?
C20B I7 I1 155.17(12) . 4_675 ?
I6 I7 I1 127.155(9) . 4_675 ?
I5 I7 I1 135.228(8) . 4_675 ?
C21A I7 I3 160.13(17) . 4_675 ?
C21B I7 I3 151.20(18) . 4_675 ?
C20A I7 I3 153.25(13) . 4_675 ?
C20B I7 I3 160.75(12) . 4_675 ?
I6 I7 I3 140.464(9) . 4_675 ?
I5 I7 I3 123.671(8) . 4_675 ?
I1 I7 I3 42.825(6) 4_675 4_675 ?
C7 P1 C1 112.32(13) . . ?
C7 P1 C19 109.24(14) . . ?
C1 P1 C19 108.91(15) . . ?
C7 P1 C13 108.12(14) . . ?
C1 P1 C13 107.87(13) . . ?
C19 P1 C13 110.37(14) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 P1 120.6(2) . . ?
C2 C1 P1 119.3(2) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C8 C7 C12 120.6(3) . . ?
C8 C7 P1 121.0(2) . . ?
C12 C7 P1 118.3(2) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C7 119.3(3) . . ?
C11 C12 H12A 120.3 . . ?
C7 C12 H12A 120.3 . . ?
C14 C13 C18 120.5(3) . . ?
C14 C13 P1 120.2(2) . . ?
C18 C13 P1 119.2(2) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C13 119.4(3) . . ?
C17 C18 H18A 120.3 . . ?
C13 C18 H18A 120.3 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21A C20A I5 124.7(6) . . ?
C21A C20A I4 122.8(6) . . ?
I5 C20A I4 112.4(3) . . ?
C21A C20A I7 36.5(4) . . ?
I5 C20A I7 88.3(2) . . ?
I4 C20A I7 159.3(3) . . ?
C21A C20A I6 36.8(4) . . ?
I5 C20A I6 161.5(3) . . ?
I4 C20A I6 86.0(2) . . ?
I7 C20A I6 73.35(16) . . ?
C20A C21A I7 121.4(6) . . ?
C20A C21A I6 121.3(6) . . ?
I7 C21A I6 117.4(3) . . ?
C20A C21A I5 34.6(4) . . ?
I7 C21A I5 86.8(2) . . ?
I6 C21A I5 155.8(3) . . ?
C20A C21A I4 36.2(4) . . ?
I7 C21A I4 157.5(3) . . ?
I6 C21A I4 85.1(2) . . ?
I5 C21A I4 70.74(14) . . ?
C21B C20B I4 121.5(6) . . ?
C21B C20B I6 122.4(6) . . ?
I4 C20B I6 116.1(3) . . ?
C21B C20B I5 35.4(4) . . ?
I4 C20B I5 86.1(2) . . ?
I6 C20B I5 157.7(3) . . ?
C21B C20B I7 37.3(4) . . ?
I4 C20B I7 158.8(3) . . ?
I6 C20B I7 85.1(2) . . ?
I5 C20B I7 72.66(15) . . ?
C20B C21B I5 123.5(7) . . ?
C20B C21B I7 121.3(6) . . ?
I5 C21B I7 115.2(3) . . ?
C20B C21B I4 36.5(4) . . ?
I5 C21B I4 87.0(3) . . ?
I7 C21B I4 157.7(3) . . ?
C20B C21B I6 36.3(4) . . ?
I5 C21B I6 159.8(4) . . ?
I7 C21B I6 85.0(2) . . ?
I4 C21B I6 72.84(17) . . ?

_refine_diff_density_max         1.060
_refine_diff_density_min         -1.495
_refine_diff_density_rms         0.218

####################################################################### 
# 
# 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_d8-0409_a
_database_code_depnum_ccdc_archive 'CCDC 1830919'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H36 F12 I12 P2'
_chemical_formula_weight         2521.59

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+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                   18.6366(9)
_cell_length_b                   18.7492(8)
_cell_length_c                   19.4096(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6782.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9162
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      31.77

_exptl_crystal_description       tabular
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.470
_exptl_crystal_F_000             4584
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    5.595
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8304
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75702
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7022
_reflns_number_gt                5892
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²+13.3657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7022
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0436
_refine_ls_wR_factor_gt          0.0404
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.24011(2) 0.24204(2) 0.87477(2) 0.01899(5) Uani 1 1 d . . . . .
I2 I 0.27016(2) 0.23989(2) 1.02189(2) 0.03077(7) Uani 1 1 d . . . . .
I3 I 0.21049(2) 0.23838(2) 0.72590(2) 0.02448(6) Uani 1 1 d . . . . .
I4 I 0.35690(2) 0.35500(2) 0.70494(2) 0.01995(6) Uani 1 1 d . . . . .
I5 I 0.62087(2) 0.61663(2) 0.65780(2) 0.02111(6) Uani 1 1 d . . . . .
I6 I 0.35678(2) 0.62017(2) 0.50930(2) 0.02788(6) Uani 1 1 d . . . . .
P1 P 0.51599(5) 0.12733(5) 0.59308(5) 0.01792(19) Uani 1 1 d . . . . .
F1 F 0.53113(11) 0.34795(10) 0.70339(11) 0.0270(5) Uani 1 1 d . . . . .
F2 F 0.63060(10) 0.44685(10) 0.68223(11) 0.0250(5) Uani 1 1 d . . . . .
F3 F 0.45026(11) 0.62373(10) 0.67023(10) 0.0236(5) Uani 1 1 d . . . . .
F4 F 0.34996(10) 0.52379(10) 0.68272(10) 0.0212(4) Uani 1 1 d . . . . .
F5 F 0.36747(12) 0.45135(11) 0.53477(11) 0.0315(5) Uani 1 1 d . . . . .
F6 F 0.47775(13) 0.36020(10) 0.53039(11) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.5003(2) 0.15552(17) 0.50597(19) 0.0210(8) Uani 1 1 d . . . . .
C2 C 0.4379(2) 0.13721(19) 0.47121(19) 0.0246(8) Uani 1 1 d . . . . .
H2A H 0.4020 0.1095 0.4934 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4283(2) 0.1598(2) 0.4035(2) 0.0301(9) Uani 1 1 d . . . . .
H3A H 0.3858 0.1475 0.3793 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4812(2) 0.2004(2) 0.3712(2) 0.0321(10) Uani 1 1 d . . . . .
H4A H 0.4748 0.2156 0.3249 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5425(2) 0.2186(2) 0.4063(2) 0.0345(10) Uani 1 1 d . . . . .
H5A H 0.5782 0.2465 0.3842 0.041 Uiso 1 1 calc R U . . .
C6 C 0.5526(2) 0.19656(19) 0.4738(2) 0.0286(9) Uani 1 1 d . . . . .
H6A H 0.5951 0.2094 0.4979 0.034 Uiso 1 1 calc R U . . .
C7 C 0.44270(19) 0.07324(18) 0.62271(17) 0.0178(7) Uani 1 1 d . . . . .
C8 C 0.37573(19) 0.10536(18) 0.63288(18) 0.0210(8) Uani 1 1 d . . . . .
H8A H 0.3703 0.1554 0.6270 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3173(2) 0.0639(2) 0.65165(19) 0.0267(9) Uani 1 1 d . . . . .
H9A H 0.2716 0.0853 0.6580 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3258(2) -0.0091(2) 0.66119(19) 0.0277(9) Uani 1 1 d . . . . .
H10A H 0.2857 -0.0376 0.6736 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3928(2) -0.04059(19) 0.65270(19) 0.0252(8) Uani 1 1 d . . . . .
H11A H 0.3985 -0.0903 0.6602 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4515(2) 0.00078(17) 0.63322(17) 0.0193(8) Uani 1 1 d . . . . .
H12A H 0.4973 -0.0206 0.6272 0.023 Uiso 1 1 calc R U . . .
C13 C 0.59774(19) 0.07739(17) 0.59606(18) 0.0183(8) Uani 1 1 d . . . . .
C14 C 0.63284(19) 0.06653(19) 0.65871(18) 0.0223(8) Uani 1 1 d . . . . .
H14A H 0.6147 0.0877 0.6996 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6941(2) 0.0249(2) 0.6611(2) 0.0281(9) Uani 1 1 d . . . . .
H15A H 0.7174 0.0163 0.7039 0.034 Uiso 1 1 calc R U . . .
C16 C 0.7212(2) -0.0040(2) 0.6017(2) 0.0275(9) Uani 1 1 d . . . . .
H16A H 0.7634 -0.0324 0.6036 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6880(2) 0.0076(2) 0.5393(2) 0.0317(10) Uani 1 1 d . . . . .
H17A H 0.7078 -0.0121 0.4984 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6259(2) 0.0478(2) 0.5359(2) 0.0269(9) Uani 1 1 d . . . . .
H18A H 0.6026 0.0552 0.4930 0.032 Uiso 1 1 calc R U . . .
C19 C 0.5233(2) 0.20470(19) 0.6471(2) 0.0288(9) Uani 1 1 d . . . . .
H19A H 0.4784 0.2318 0.6453 0.043 Uiso 1 1 calc R U . . .
H19B H 0.5326 0.1898 0.6947 0.043 Uiso 1 1 calc R U . . .
H19C H 0.5629 0.2347 0.6309 0.043 Uiso 1 1 calc R U . . .
C20 C 0.43715(19) 0.43236(18) 0.69360(17) 0.0173(7) Uani 1 1 d . . . . .
C21 C 0.50926(19) 0.41579(17) 0.69322(17) 0.0182(8) Uani 1 1 d . . . . .
C22 C 0.56102(18) 0.46724(18) 0.68300(17) 0.0172(7) Uani 1 1 d . . . . .
C23 C 0.54337(18) 0.53829(17) 0.67490(16) 0.0162(7) Uani 1 1 d . . . . .
C24 C 0.47131(19) 0.55506(17) 0.67640(17) 0.0174(7) Uani 1 1 d . . . . .
C25 C 0.41942(18) 0.50343(18) 0.68421(17) 0.0161(7) Uani 1 1 d . . . . .
C26 C 0.4419(2) 0.54812(19) 0.50208(18) 0.0246(9) Uani 1 1 d . . . . .
C27 C 0.4329(2) 0.47632(19) 0.51691(18) 0.0246(9) Uani 1 1 d . . . . .
C28 C 0.4895(2) 0.42962(18) 0.51504(18) 0.0256(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9102(4) . ?
I1 I3 2.9427(3) . ?
I1 I5 3.5553(3) 3_646 ?
I1 I6 4.0931(3) 2_565 ?
I1 I4 4.4821(3) . ?
I2 I6 3.5414(4) 2_565 ?
I2 I3 4.1330(4) 7_566 ?
I2 I4 4.2897(4) 7_566 ?
I2 I5 4.6508(4) 3_646 ?
I3 I4 3.5202(3) . ?
I3 I2 4.1329(4) 7_565 ?
I3 I5 4.4925(4) 3_646 ?
I3 I6 4.9152(4) 8_655 ?
I4 C20 2.095(3) . ?
I4 C25 3.044(3) . ?
I4 C21 3.068(4) . ?
I4 F4 3.1965(19) . ?
I4 F1 3.250(2) . ?
I5 C23 2.087(3) . ?
I5 C24 3.038(3) . ?
I5 C22 3.054(3) . ?
I5 F3 3.191(2) . ?
I5 F2 3.223(2) . ?
I5 I1 3.5554(3) 3_656 ?
I6 C26 2.088(4) . ?
I6 C28 3.049(4) 5_666 ?
I6 C27 3.051(4) . ?
I6 F6 3.200(2) 5_666 ?
I6 F5 3.210(2) . ?
I6 I2 3.5413(4) 2_564 ?
P1 C13 1.789(4) . ?
P1 C1 1.795(4) . ?
P1 C19 1.796(4) . ?
P1 C7 1.796(4) . ?
F1 C21 1.350(4) . ?
F2 C22 1.352(4) . ?
F3 C24 1.351(4) . ?
F4 C25 1.350(4) . ?
F5 C27 1.351(4) . ?
F6 C28 1.353(4) . ?
F6 I6 3.200(2) 5_666 ?
C1 C2 1.388(5) . ?
C1 C6 1.390(5) . ?
C2 C3 1.392(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.373(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(6) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C12 1.383(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.387(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.394(5) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.396(5) . ?
C13 C14 1.396(5) . ?
C14 C15 1.385(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.370(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.378(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.381(5) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.379(5) . ?
C20 C25 1.385(5) . ?
C21 C22 1.379(5) . ?
C22 C23 1.381(5) . ?
C23 C24 1.380(5) . ?
C24 C25 1.377(5) . ?
C26 C28 1.385(5) 5_666 ?
C26 C27 1.387(5) . ?
C27 C28 1.372(5) . ?
C28 C26 1.385(5) 5_666 ?
C28 I6 3.049(4) 5_666 ?

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
I2 I1 I3 177.852(11) . . ?
I2 I1 I5 91.439(9) . 3_646 ?
I3 I1 I5 86.940(8) . 3_646 ?
I2 I1 I6 57.839(8) . 2_565 ?
I3 I1 I6 123.945(9) . 2_565 ?
I5 I1 I6 148.470(8) 3_646 2_565 ?
I2 I1 I4 129.399(9) . . ?
I3 I1 I4 51.678(7) . . ?
I5 I1 I4 80.084(7) 3_646 . ?
I6 I1 I4 112.653(7) 2_565 . ?
I1 I2 I6 78.080(8) . 2_565 ?
I1 I2 I3 152.490(11) . 7_566 ?
I6 I2 I3 79.243(7) 2_565 7_566 ?
I1 I2 I4 152.991(10) . 7_566 ?
I6 I2 I4 128.040(9) 2_565 7_566 ?
I3 I2 I4 49.366(6) 7_566 7_566 ?
I1 I2 I5 49.837(7) . 3_646 ?
I6 I2 I5 127.451(8) 2_565 3_646 ?
I3 I2 I5 152.249(8) 7_566 3_646 ?
I4 I2 I5 104.508(8) 7_566 3_646 ?
I1 I3 I4 87.340(8) . . ?
I1 I3 I2 152.628(10) . 7_565 ?
I4 I3 I2 67.637(7) . 7_565 ?
I1 I3 I5 52.210(6) . 3_646 ?
I4 I3 I5 80.293(8) . 3_646 ?
I2 I3 I5 110.075(8) 7_565 3_646 ?
I1 I3 I6 153.930(9) . 8_655 ?
I4 I3 I6 112.271(8) . 8_655 ?
I2 I3 I6 45.059(6) 7_565 8_655 ?
I5 I3 I6 112.277(7) 3_646 8_655 ?
C20 I4 C25 23.05(11) . . ?
C20 I4 C21 22.23(11) . . ?
C25 I4 C21 45.27(9) . . ?
C20 I4 F4 47.88(10) . . ?
C25 I4 F4 24.83(7) . . ?
C21 I4 F4 70.10(7) . . ?
C20 I4 F1 46.68(10) . . ?
C25 I4 F1 69.73(7) . . ?
C21 I4 F1 24.46(7) . . ?
F4 I4 F1 94.56(5) . . ?
C20 I4 I3 174.58(9) . . ?
C25 I4 I3 151.63(6) . . ?
C21 I4 I3 163.07(6) . . ?
F4 I4 I3 126.81(3) . . ?
F1 I4 I3 138.61(3) . . ?
C23 I5 C24 22.88(11) . . ?
C23 I5 C22 22.51(11) . . ?
C24 I5 C22 45.38(9) . . ?
C23 I5 F3 47.76(10) . . ?
C24 I5 F3 24.90(7) . . ?
C22 I5 F3 70.26(7) . . ?
C23 I5 F2 47.18(10) . . ?
C24 I5 F2 70.06(7) . . ?
C22 I5 F2 24.69(7) . . ?
F3 I5 F2 94.94(5) . . ?
C23 I5 I1 176.61(9) . 3_656 ?
C24 I5 I1 160.20(6) . 3_656 ?
C22 I5 I1 154.30(6) . 3_656 ?
F3 I5 I1 135.39(3) . 3_656 ?
F2 I5 I1 129.66(4) . 3_656 ?
C26 I6 C28 22.79(12) . 5_666 ?
C26 I6 C27 22.81(13) . . ?
C28 I6 C27 45.59(10) 5_666 . ?
C26 I6 F6 47.64(11) . 5_666 ?
C28 I6 F6 24.86(7) 5_666 5_666 ?
C27 I6 F6 70.45(8) . 5_666 ?
C26 I6 F5 47.57(11) . . ?
C28 I6 F5 70.35(8) 5_666 . ?
C27 I6 F5 24.76(8) . . ?
F6 I6 F5 95.21(5) 5_666 . ?
C26 I6 I2 172.48(10) . 2_564 ?
C28 I6 I2 149.88(6) 5_666 2_564 ?
C27 I6 I2 164.20(7) . 2_564 ?
F6 I6 I2 125.11(4) 5_666 2_564 ?
F5 I6 I2 139.59(4) . 2_564 ?
C13 P1 C1 108.85(17) . . ?
C13 P1 C19 109.81(17) . . ?
C1 P1 C19 108.97(17) . . ?
C13 P1 C7 109.98(16) . . ?
C1 P1 C7 110.13(16) . . ?
C19 P1 C7 109.09(17) . . ?
C21 F1 I4 70.20(17) . . ?
C22 F2 I5 70.64(17) . . ?
C24 F3 I5 71.20(17) . . ?
C25 F4 I4 71.23(16) . . ?
C27 F5 I6 71.02(18) . . ?
C28 F6 I6 71.3(2) . 5_666 ?
C2 C1 C6 120.4(3) . . ?
C2 C1 P1 121.4(3) . . ?
C6 C1 P1 118.2(3) . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C12 C7 C8 120.5(3) . . ?
C12 C7 P1 120.8(3) . . ?
C8 C7 P1 118.7(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C7 C12 C11 119.5(3) . . ?
C7 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C18 C13 C14 119.6(3) . . ?
C18 C13 P1 120.1(3) . . ?
C14 C13 P1 120.2(3) . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C13 119.5(3) . . ?
C17 C18 H18A 120.3 . . ?
C13 C18 H18A 120.3 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 116.7(3) . . ?
C21 C20 I4 122.7(2) . . ?
C25 C20 I4 120.6(3) . . ?
F1 C21 C22 118.0(3) . . ?
F1 C21 C20 120.4(3) . . ?
C22 C21 C20 121.7(3) . . ?
F1 C21 I4 85.33(18) . . ?
C22 C21 I4 156.7(2) . . ?
C20 C21 I4 35.08(17) . . ?
F2 C22 C21 118.3(3) . . ?
F2 C22 C23 120.0(3) . . ?
C21 C22 C23 121.6(3) . . ?
F2 C22 I5 84.68(18) . . ?
C21 C22 I5 157.0(2) . . ?
C23 C22 I5 35.33(17) . . ?
C24 C23 C22 116.7(3) . . ?
C24 C23 I5 121.1(2) . . ?
C22 C23 I5 122.2(3) . . ?
F3 C24 C25 118.4(3) . . ?
F3 C24 C23 119.9(3) . . ?
C25 C24 C23 121.7(3) . . ?
F3 C24 I5 83.90(17) . . ?
C25 C24 I5 157.6(2) . . ?
C23 C24 I5 36.01(17) . . ?
F4 C25 C24 118.2(3) . . ?
F4 C25 C20 120.3(3) . . ?
C24 C25 C20 121.6(3) . . ?
F4 C25 I4 83.94(17) . . ?
C24 C25 I4 157.9(2) . . ?
C20 C25 I4 36.32(17) . . ?
C28 C26 C27 117.0(4) 5_666 . ?
C28 C26 I6 121.5(3) 5_666 . ?
C27 C26 I6 121.5(3) . . ?
F5 C27 C28 118.7(3) . . ?
F5 C27 C26 119.9(4) . . ?
C28 C27 C26 121.4(4) . . ?
F5 C27 I6 84.2(2) . . ?
C28 C27 I6 157.0(3) . . ?
C26 C27 I6 35.7(2) . . ?
F6 C28 C27 118.9(4) . . ?
F6 C28 C26 119.5(3) . 5_666 ?
C27 C28 C26 121.6(3) . 5_666 ?
F6 C28 I6 83.8(2) . 5_666 ?
C27 C28 I6 157.2(3) . 5_666 ?
C26 C28 I6 35.73(19) 5_666 5_666 ?

_refine_diff_density_max         0.959
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_d8-1412_a
_database_code_depnum_ccdc_archive 'CCDC 1830916'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 F4 I5 P'
_chemical_formula_weight         1059.86

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4326(12)
_cell_length_b                   11.7996(12)
_cell_length_c                   12.7273(13)
_cell_angle_alpha                112.483(3)
_cell_angle_beta                 97.094(4)
_cell_angle_gamma                97.777(3)
_cell_volume                     1542.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      30.54

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.282
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    5.129
_shelx_estimated_absorpt_T_min   0.428
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8492
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70867
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6719
_reflns_number_gt                6194
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+0.8442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6719
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0456
_refine_ls_wR_factor_gt          0.0446
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.26505(2) 0.78556(2) 1.04563(2) 0.02543(4) Uani 1 1 d . . . . .
I2 I 1.31767(2) 0.75283(2) 1.25793(2) 0.03537(5) Uani 1 1 d . . . . .
I3 I 1.22807(2) 0.81126(2) 0.82308(2) 0.03608(5) Uani 1 1 d . . . . .
I4 I 1.03960(2) 0.51815(2) 0.67217(2) 0.02796(5) Uani 1 1 d . . . . .
I5 I 0.60214(2) -0.02253(2) 0.35360(2) 0.02923(5) Uani 1 1 d . . . . .
P1 P 0.34790(5) 0.25684(6) 0.11171(5) 0.02180(12) Uani 1 1 d . . . . .
F1 F 1.04891(13) 0.22575(14) 0.58118(14) 0.0340(3) Uani 1 1 d . . . . .
F2 F 0.88389(14) 0.01918(13) 0.45248(14) 0.0350(3) Uani 1 1 d . . . . .
F3 F 0.59888(13) 0.26800(15) 0.43165(15) 0.0404(4) Uani 1 1 d . . . . .
F4 F 0.76488(14) 0.47369(14) 0.55494(15) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.4567(2) 0.3992(2) 0.1915(2) 0.0248(5) Uani 1 1 d . . . . .
C2 C 0.4685(3) 0.4625(2) 0.3108(2) 0.0335(6) Uani 1 1 d . . . . .
H2A H 0.4161 0.4326 0.3509 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5567(3) 0.5692(3) 0.3708(3) 0.0415(7) Uani 1 1 d . . . . .
H3A H 0.5645 0.6125 0.4523 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6329(2) 0.6127(3) 0.3131(3) 0.0421(7) Uani 1 1 d . . . . .
H4A H 0.6940 0.6853 0.3550 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6211(3) 0.5515(3) 0.1946(3) 0.0450(7) Uani 1 1 d . . . . .
H5A H 0.6734 0.5826 0.1550 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5330(2) 0.4445(3) 0.1332(3) 0.0366(6) Uani 1 1 d . . . . .
H6A H 0.5248 0.4023 0.0517 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2345(2) 0.2803(2) 0.0164(2) 0.0237(5) Uani 1 1 d . . . . .
C8 C 0.2134(2) 0.3991(2) 0.0379(2) 0.0314(6) Uani 1 1 d . . . . .
H8A H 0.2610 0.4694 0.1023 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1222(2) 0.4155(3) -0.0349(3) 0.0363(6) Uani 1 1 d . . . . .
H9A H 0.1080 0.4972 -0.0202 0.044 Uiso 1 1 calc R U . . .
C10 C 0.0530(2) 0.3150(3) -0.1275(2) 0.0367(6) Uani 1 1 d . . . . .
H10A H -0.0095 0.3269 -0.1764 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0737(3) 0.1966(3) -0.1500(3) 0.0530(9) Uani 1 1 d . . . . .
H11A H 0.0257 0.1269 -0.2146 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1645(3) 0.1785(3) -0.0787(3) 0.0447(8) Uani 1 1 d . . . . .
H12A H 0.1789 0.0966 -0.0946 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2800(2) 0.2045(2) 0.2089(2) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.1634(3) 0.2163(3) 0.2235(3) 0.0417(7) Uani 1 1 d . . . . .
H14A H 0.1175 0.2521 0.1815 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1146(3) 0.1753(4) 0.2998(3) 0.0532(9) Uani 1 1 d . . . . .
H15A H 0.0347 0.1830 0.3099 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1802(3) 0.1234(3) 0.3614(3) 0.0408(7) Uani 1 1 d . . . . .
H16A H 0.1456 0.0957 0.4137 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2968(3) 0.1118(3) 0.3470(2) 0.0367(6) Uani 1 1 d . . . . .
H17A H 0.3424 0.0763 0.3895 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3464(2) 0.1518(3) 0.2709(2) 0.0322(6) Uani 1 1 d . . . . .
H18A H 0.4261 0.1433 0.2606 0.039 Uiso 1 1 calc R U . . .
C19 C 0.4232(2) 0.1397(2) 0.0283(2) 0.0322(6) Uani 1 1 d . . . . .
H19A H 0.4854 0.1266 0.0804 0.048 Uiso 1 1 calc R U . . .
H19B H 0.3649 0.0611 -0.0155 0.048 Uiso 1 1 calc R U . . .
H19C H 0.4604 0.1672 -0.0254 0.048 Uiso 1 1 calc R U . . .
C20 C 0.9122(2) 0.3557(2) 0.5713(2) 0.0234(5) Uani 1 1 d . . . . .
C21 C 0.9384(2) 0.2379(2) 0.5432(2) 0.0238(5) Uani 1 1 d . . . . .
C22 C 0.8528(2) 0.1314(2) 0.4773(2) 0.0245(5) Uani 1 1 d . . . . .
C23 C 0.7369(2) 0.1374(2) 0.4385(2) 0.0235(5) Uani 1 1 d . . . . .
C24 C 0.7104(2) 0.2553(2) 0.4662(2) 0.0256(5) Uani 1 1 d . . . . .
C25 C 0.7961(2) 0.3619(2) 0.5304(2) 0.0258(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8760(3) . ?
I1 I3 2.9479(4) . ?
I1 I5 4.7394(5) 1_666 ?
I1 I4 4.7428(5) . ?
I2 C24 3.601(3) 2_767 ?
I2 I5 3.6478(4) 1_666 ?
I2 I5 4.6336(5) 2_767 ?
I2 I4 5.2190(5) 2_767 ?
I3 I4 3.4891(4) . ?
I3 C24 3.639(3) 2_766 ?
I3 C23 3.663(2) 2_766 ?
I3 I5 4.3697(4) 2_766 ?
I4 C20 2.084(2) . ?
I4 C25 3.038(2) . ?
I4 C21 3.051(2) . ?
I4 F4 3.1881(16) . ?
I4 F1 3.2141(15) . ?
I4 I4 4.2057(5) 2_766 ?
I5 C23 2.084(2) . ?
I5 C24 3.034(3) . ?
I5 C22 3.046(3) . ?
I5 F3 3.1905(16) . ?
I5 F2 3.2090(16) . ?
I5 I2 3.6477(4) 1_444 ?
I5 I3 4.3697(4) 2_766 ?
I5 I5 4.5382(5) 2_656 ?
P1 C7 1.787(2) . ?
P1 C19 1.790(2) . ?
P1 C13 1.790(2) . ?
P1 C1 1.794(2) . ?
F1 C21 1.342(3) . ?
F2 C22 1.347(3) . ?
F3 C24 1.344(3) . ?
F4 C25 1.344(3) . ?
C1 C6 1.390(4) . ?
C1 C2 1.391(4) . ?
C2 C3 1.384(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C12 1.392(4) . ?
C8 C9 1.392(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.367(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.375(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.387(4) . ?
C13 C18 1.394(3) . ?
C14 C15 1.381(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.376(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.382(3) . ?
C20 C25 1.386(3) . ?
C21 C22 1.378(3) . ?
C22 C23 1.377(3) . ?
C23 C24 1.384(3) . ?
C23 I3 3.663(2) 2_766 ?
C24 C25 1.375(3) . ?
C24 I2 3.601(3) 2_767 ?
C24 I3 3.639(3) 2_766 ?

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
I2 I1 I3 175.499(8) . . ?
I2 I1 I5 50.262(7) . 1_666 ?
I3 I1 I5 127.589(8) . 1_666 ?
I2 I1 I4 132.879(9) . . ?
I3 I1 I4 47.168(8) . . ?
I5 I1 I4 158.527(5) 1_666 . ?
I1 I2 C24 160.88(4) . 2_767 ?
I1 I2 I5 92.418(8) . 1_666 ?
C24 I2 I5 97.63(4) 2_767 1_666 ?
I1 I2 I5 133.893(9) . 2_767 ?
C24 I2 I5 40.88(4) 2_767 2_767 ?
I5 I2 I5 65.196(7) 1_666 2_767 ?
I1 I2 I4 113.396(8) . 2_767 ?
C24 I2 I4 55.36(4) 2_767 2_767 ?
I5 I2 I4 152.983(7) 1_666 2_767 ?
I5 I2 I4 90.022(8) 2_767 2_767 ?
I1 I3 I4 94.547(9) . . ?
I1 I3 C24 151.74(4) . 2_766 ?
I4 I3 C24 80.41(4) . 2_766 ?
I1 I3 C23 165.87(4) . 2_766 ?
I4 I3 C23 94.25(4) . 2_766 ?
C24 I3 C23 21.85(5) 2_766 2_766 ?
I1 I3 I5 140.158(7) . 2_766 ?
I4 I3 I5 122.230(9) . 2_766 ?
C24 I3 I5 43.34(4) 2_766 2_766 ?
C23 I3 I5 28.37(4) 2_766 2_766 ?
C20 I4 C25 23.05(8) . . ?
C20 I4 C21 22.58(8) . . ?
C25 I4 C21 45.63(6) . . ?
C20 I4 F4 47.82(7) . . ?
C25 I4 F4 24.77(5) . . ?
C21 I4 F4 70.40(5) . . ?
C20 I4 F1 47.14(7) . . ?
C25 I4 F1 70.19(5) . . ?
C21 I4 F1 24.56(5) . . ?
F4 I4 F1 94.96(4) . . ?
C20 I4 I3 171.90(6) . . ?
C25 I4 I3 149.34(4) . . ?
C21 I4 I3 164.61(4) . . ?
F4 I4 I3 124.65(3) . . ?
F1 I4 I3 140.26(3) . . ?
C20 I4 I4 69.33(6) . 2_766 ?
C25 I4 I4 63.32(5) . 2_766 ?
C21 I4 I4 78.46(4) . 2_766 ?
F4 I4 I4 61.63(3) . 2_766 ?
F1 I4 I4 90.02(3) . 2_766 ?
I3 I4 I4 105.046(8) . 2_766 ?
C20 I4 I1 147.29(6) . . ?
C25 I4 I1 146.39(5) . . ?
C21 I4 I1 135.82(4) . . ?
F4 I4 I1 132.66(3) . . ?
F1 I4 I1 117.27(3) . . ?
I3 I4 I1 38.286(5) . . ?
I4 I4 I1 143.270(8) 2_766 . ?
C23 I5 C24 23.10(8) . . ?
C23 I5 C22 22.55(8) . . ?
C24 I5 C22 45.60(6) . . ?
C23 I5 F3 47.84(7) . . ?
C24 I5 F3 24.77(5) . . ?
C22 I5 F3 70.37(5) . . ?
C23 I5 F2 47.21(7) . . ?
C24 I5 F2 70.29(5) . . ?
C22 I5 F2 24.70(5) . . ?
F3 I5 F2 95.05(4) . . ?
C23 I5 I2 163.90(7) . 1_444 ?
C24 I5 I2 142.96(5) . 1_444 ?
C22 I5 I2 164.73(4) . 1_444 ?
F3 I5 I2 119.23(3) . 1_444 ?
F2 I5 I2 143.80(3) . 1_444 ?
C23 I5 I3 56.62(6) . 2_766 ?
C24 I5 I3 55.40(5) . 2_766 ?
C22 I5 I3 65.18(4) . 2_766 ?
F3 I5 I3 59.36(3) . 2_766 ?
F2 I5 I3 76.60(3) . 2_766 ?
I2 I5 I3 129.410(8) 1_444 2_766 ?
C23 I5 I5 98.44(7) . 2_656 ?
C24 I5 I5 89.92(5) . 2_656 ?
C22 I5 I5 103.67(5) . 2_656 ?
F3 I5 I5 82.40(3) . 2_656 ?
F2 I5 I5 108.93(3) . 2_656 ?
I2 I5 I5 67.947(7) 1_444 2_656 ?
I3 I5 I5 141.766(8) 2_766 2_656 ?
C7 P1 C19 109.27(12) . . ?
C7 P1 C13 109.72(11) . . ?
C19 P1 C13 108.77(12) . . ?
C7 P1 C1 110.27(11) . . ?
C19 P1 C1 108.47(12) . . ?
C13 P1 C1 110.30(12) . . ?
C21 F1 I4 70.91(12) . . ?
C22 F2 I5 70.87(12) . . ?
C24 F3 I5 71.08(12) . . ?
C25 F4 I4 71.36(12) . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 P1 119.2(2) . . ?
C2 C1 P1 121.2(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 P1 120.46(19) . . ?
C12 C7 P1 120.1(2) . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
C14 C13 C18 119.9(2) . . ?
C14 C13 P1 121.12(19) . . ?
C18 C13 P1 119.01(19) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18A 119.9 . . ?
C13 C18 H18A 119.9 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.1(2) . . ?
C21 C20 I4 122.04(17) . . ?
C25 C20 I4 120.88(17) . . ?
F1 C21 C22 118.8(2) . . ?
F1 C21 C20 119.9(2) . . ?
C22 C21 C20 121.3(2) . . ?
F1 C21 I4 84.53(13) . . ?
C22 C21 I4 156.70(17) . . ?
C20 C21 I4 35.38(12) . . ?
F2 C22 C23 119.8(2) . . ?
F2 C22 C21 118.6(2) . . ?
C23 C22 C21 121.6(2) . . ?
F2 C22 I5 84.43(13) . . ?
C23 C22 I5 35.49(12) . . ?
C21 C22 I5 156.64(17) . . ?
C22 C23 C24 117.2(2) . . ?
C22 C23 I5 121.96(18) . . ?
C24 C23 I5 120.68(18) . . ?
C22 C23 I3 100.77(15) . 2_766 ?
C24 C23 I3 78.11(14) . 2_766 ?
I5 C23 I3 95.01(8) . 2_766 ?
F3 C24 C25 118.3(2) . . ?
F3 C24 C23 120.3(2) . . ?
C25 C24 C23 121.4(2) . . ?
F3 C24 I5 84.14(13) . . ?
C25 C24 I5 157.30(17) . . ?
C23 C24 I5 36.22(12) . . ?
F3 C24 I2 99.99(14) . 2_767 ?
C25 C24 I2 84.80(15) . 2_767 ?
C23 C24 I2 84.79(14) . 2_767 ?
I5 C24 I2 88.15(6) . 2_767 ?
F3 C24 I3 90.10(14) . 2_766 ?
C25 C24 I3 100.73(16) . 2_766 ?
C23 C24 I3 80.04(14) . 2_766 ?
I5 C24 I3 81.26(6) . 2_766 ?
I2 C24 I3 164.58(8) 2_767 2_766 ?
F4 C25 C24 118.7(2) . . ?
F4 C25 C20 119.9(2) . . ?
C24 C25 C20 121.4(2) . . ?
F4 C25 I4 83.87(13) . . ?
C24 C25 I4 157.43(17) . . ?
C20 C25 I4 36.07(12) . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.141

####################################################################### 
# 
# 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_d8-2496_a
_database_code_depnum_ccdc_archive 'CCDC 1830917'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 F4 I5 P'
_chemical_formula_weight         1059.86

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.7780(12)
_cell_length_b                   12.7956(13)
_cell_length_c                   20.095(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.703(4)
_cell_angle_gamma                90
_cell_volume                     2975.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9751
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.366
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    5.318
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7452
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            84947
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6164
_reflns_number_gt                5357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+1.6270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6164
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.15326(2) 0.22531(2) 0.87419(2) 0.02877(6) Uani 1 1 d . . . . .
I2 I 0.37835(2) 0.21809(2) 0.96180(2) 0.03697(6) Uani 1 1 d . . . . .
I3 I -0.07415(2) 0.22793(2) 0.78488(2) 0.04521(7) Uani 1 1 d . . . . .
I4 I 0.09730(2) 0.21350(2) 0.65976(2) 0.02775(6) Uani 1 1 d . . . . .
I5 I 0.17427(2) 0.43524(2) 0.55475(2) 0.03018(6) Uani 1 1 d . . . . .
P1 P 0.48725(6) 0.65853(6) 0.22681(4) 0.02031(16) Uani 1 1 d . . . . .
F1 F 0.35919(17) 0.34606(15) 0.47738(9) 0.0373(5) Uani 1 1 d . . . . .
F2 F 0.47912(18) 0.16799(16) 0.48558(10) 0.0454(5) Uani 1 1 d . . . . .
F3 F 0.43161(18) 0.01056(14) 0.56698(10) 0.0429(5) Uani 1 1 d . . . . .
F4 F 0.26097(17) 0.03037(14) 0.63684(10) 0.0372(4) Uani 1 1 d . . . . .
C1 C 0.4710(3) 0.7932(2) 0.20347(15) 0.0221(6) Uani 1 1 d . . . . .
C2 C 0.3712(3) 0.8273(2) 0.16211(16) 0.0278(7) Uani 1 1 d . . . . .
H2A H 0.3135 0.7785 0.1429 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3552(3) 0.9332(3) 0.14858(18) 0.0373(8) Uani 1 1 d . . . . .
H3A H 0.2861 0.9568 0.1204 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4384(3) 1.0040(3) 0.17566(18) 0.0396(8) Uani 1 1 d . . . . .
H4A H 0.4269 1.0764 0.1662 0.047 Uiso 1 1 calc R U . . .
C5 C 0.5392(3) 0.9701(3) 0.2167(2) 0.0475(10) Uani 1 1 d . . . . .
H5A H 0.5967 1.0193 0.2355 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5563(3) 0.8650(3) 0.23036(17) 0.0373(8) Uani 1 1 d . . . . .
H6A H 0.6260 0.8417 0.2580 0.045 Uiso 1 1 calc R U . . .
C7 C 0.3936(3) 0.5800(2) 0.16641(15) 0.0255(7) Uani 1 1 d . . . . .
C8 C 0.2900(3) 0.5441(3) 0.18016(19) 0.0392(8) Uani 1 1 d . . . . .
H8A H 0.2681 0.5597 0.2222 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2179(4) 0.4849(3) 0.1318(2) 0.0549(11) Uani 1 1 d . . . . .
H9A H 0.1454 0.4615 0.1403 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2509(4) 0.4602(3) 0.0720(2) 0.0567(12) Uani 1 1 d . . . . .
H10A H 0.2021 0.4179 0.0399 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3533(4) 0.4958(3) 0.05798(19) 0.0504(10) Uani 1 1 d . . . . .
H11A H 0.3749 0.4790 0.0160 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4259(3) 0.5564(3) 0.10502(17) 0.0381(8) Uani 1 1 d . . . . .
H12A H 0.4970 0.5815 0.0954 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4490(2) 0.6425(2) 0.30822(14) 0.0205(6) Uani 1 1 d . . . . .
C14 C 0.4927(3) 0.5573(2) 0.34851(15) 0.0253(6) Uani 1 1 d . . . . .
H14A H 0.5464 0.5111 0.3341 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4572(3) 0.5406(3) 0.40940(16) 0.0317(7) Uani 1 1 d . . . . .
H15A H 0.4872 0.4831 0.4370 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3785(3) 0.6072(3) 0.43032(16) 0.0325(7) Uani 1 1 d . . . . .
H16A H 0.3543 0.5950 0.4722 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3348(3) 0.6912(2) 0.39091(17) 0.0326(7) Uani 1 1 d . . . . .
H17A H 0.2805 0.7365 0.4055 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3703(3) 0.7096(2) 0.32953(16) 0.0277(7) Uani 1 1 d . . . . .
H18A H 0.3408 0.7678 0.3024 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6337(3) 0.6172(3) 0.23022(16) 0.0300(7) Uani 1 1 d . . . . .
H19A H 0.6412 0.5433 0.2431 0.045 Uiso 1 1 calc R U . . .
H19B H 0.6547 0.6266 0.1856 0.045 Uiso 1 1 calc R U . . .
H19C H 0.6852 0.6592 0.2638 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2232(3) 0.2041(2) 0.59799(15) 0.0231(6) Uani 1 1 d . . . . .
C21 C 0.2490(3) 0.2861(2) 0.55728(15) 0.0242(6) Uani 1 1 d . . . . .
C22 C 0.3339(3) 0.2709(2) 0.51908(16) 0.0278(7) Uani 1 1 d . . . . .
C23 C 0.3962(3) 0.1794(3) 0.52207(16) 0.0298(7) Uani 1 1 d . . . . .
C24 C 0.3718(3) 0.0998(2) 0.56300(16) 0.0299(7) Uani 1 1 d . . . . .
C25 C 0.2844(3) 0.1124(2) 0.59925(15) 0.0269(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8988(4) . ?
I1 I3 2.9343(4) . ?
I1 I4 4.2391(5) . ?
I1 I5 4.3433(4) 2_546 ?
I2 I5 3.6766(5) 2_546 ?
I2 I5 4.1312(5) 4_666 ?
I2 I4 4.4080(5) 4_666 ?
I3 I4 3.5099(4) . ?
I4 C20 2.107(3) . ?
I4 C25 3.000(3) . ?
I4 C21 3.109(3) . ?
I4 F4 3.1224(19) . ?
I4 I5 3.7464(4) . ?
I4 I2 4.4081(5) 4_565 ?
I5 C21 2.098(3) . ?
I5 C22 2.995(3) . ?
I5 C20 3.107(3) . ?
I5 F1 3.1178(19) . ?
I5 I2 3.6766(5) 2_556 ?
I5 I2 4.1313(4) 4_565 ?
I5 I1 4.3434(4) 2_556 ?
P1 C1 1.787(3) . ?
P1 C13 1.787(3) . ?
P1 C7 1.789(3) . ?
P1 C19 1.793(3) . ?
F1 C22 1.345(3) . ?
F2 C23 1.334(3) . ?
F3 C24 1.336(3) . ?
F4 C25 1.351(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.388(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.371(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.379(5) . ?
C7 C12 1.390(5) . ?
C8 C9 1.391(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.366(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.367(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.388(4) . ?
C13 C14 1.398(4) . ?
C14 C15 1.381(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.376(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.394(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.374(4) . ?
C20 C21 1.399(4) . ?
C21 C22 1.382(4) . ?
C22 C23 1.377(4) . ?
C23 C24 1.373(4) . ?
C24 C25 1.377(4) . ?

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
I2 I1 I3 178.796(10) . . ?
I2 I1 I4 124.627(9) . . ?
I3 I1 I4 55.024(8) . . ?
I2 I1 I5 56.904(7) . 2_546 ?
I3 I1 I5 121.931(9) . 2_546 ?
I4 I1 I5 106.181(6) . 2_546 ?
I1 I2 I5 81.757(7) . 2_546 ?
I1 I2 I5 152.791(9) . 4_666 ?
I5 I2 I5 71.778(8) 2_546 4_666 ?
I1 I2 I4 149.042(9) . 4_666 ?
I5 I2 I4 109.734(7) 2_546 4_666 ?
I5 I2 I4 51.922(6) 4_666 4_666 ?
I1 I3 I4 81.739(11) . . ?
C20 I4 C25 23.97(10) . . ?
C20 I4 C21 21.98(10) . . ?
C25 I4 C21 45.94(8) . . ?
C20 I4 F4 49.35(9) . . ?
C25 I4 F4 25.40(6) . . ?
C21 I4 F4 71.33(6) . . ?
C20 I4 I3 170.64(8) . . ?
C25 I4 I3 151.22(6) . . ?
C21 I4 I3 159.52(5) . . ?
F4 I4 I3 126.75(3) . . ?
C20 I4 I5 56.02(8) . . ?
C25 I4 I5 79.95(6) . . ?
C21 I4 I5 34.06(5) . . ?
F4 I4 I5 105.35(3) . . ?
I3 I4 I5 126.532(9) . . ?
C20 I4 I1 127.41(8) . . ?
C25 I4 I1 116.11(6) . . ?
C21 I4 I1 131.51(6) . . ?
F4 I4 I1 101.13(4) . . ?
I3 I4 I1 43.237(8) . . ?
I5 I4 I1 122.505(8) . . ?
C20 I4 I2 80.64(8) . 4_565 ?
C25 I4 I2 94.04(6) . 4_565 ?
C21 I4 I2 69.80(6) . 4_565 ?
F4 I4 I2 106.84(4) . 4_565 ?
I3 I4 I2 108.546(10) . 4_565 ?
I5 I4 I2 60.230(7) . 4_565 ?
I1 I4 I2 149.851(7) . 4_565 ?
C21 I5 C22 24.21(10) . . ?
C21 I5 C20 21.89(10) . . ?
C22 I5 C20 46.08(8) . . ?
C21 I5 F1 49.48(9) . . ?
C22 I5 F1 25.32(7) . . ?
C20 I5 F1 71.37(6) . . ?
C21 I5 I2 163.81(8) . 2_556 ?
C22 I5 I2 140.56(6) . 2_556 ?
C20 I5 I2 169.12(5) . 2_556 ?
F1 I5 I2 115.90(3) . 2_556 ?
C21 I5 I4 56.08(8) . . ?
C22 I5 I4 80.29(6) . . ?
C20 I5 I4 34.21(5) . . ?
F1 I5 I4 105.56(3) . . ?
I2 I5 I4 137.911(9) 2_556 . ?
C21 I5 I2 83.92(8) . 4_565 ?
C22 I5 I2 94.16(6) . 4_565 ?
C20 I5 I2 76.78(5) . 4_565 ?
F1 I5 I2 102.10(4) . 4_565 ?
I2 I5 I2 108.224(8) 2_556 4_565 ?
I4 I5 I2 67.848(8) . 4_565 ?
C21 I5 I1 126.91(8) . 2_556 ?
C22 I5 I1 113.75(6) . 2_556 ?
C20 I5 I1 132.11(5) . 2_556 ?
F1 I5 I1 98.59(4) . 2_556 ?
I2 I5 I1 41.338(7) 2_556 2_556 ?
I4 I5 I1 127.539(9) . 2_556 ?
I2 I5 I1 149.122(7) 4_565 2_556 ?
C1 P1 C13 108.53(13) . . ?
C1 P1 C7 109.91(14) . . ?
C13 P1 C7 109.17(14) . . ?
C1 P1 C19 110.47(15) . . ?
C13 P1 C19 109.60(14) . . ?
C7 P1 C19 109.13(15) . . ?
C22 F1 I5 72.23(15) . . ?
C25 F4 I4 72.24(15) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 P1 120.1(2) . . ?
C6 C1 P1 120.0(2) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C8 C7 C12 120.2(3) . . ?
C8 C7 P1 120.5(3) . . ?
C12 C7 P1 119.3(3) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C7 119.4(4) . . ?
C11 C12 H12A 120.3 . . ?
C7 C12 H12A 120.3 . . ?
C18 C13 C14 119.9(3) . . ?
C18 C13 P1 120.5(2) . . ?
C14 C13 P1 119.4(2) . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C13 C18 C17 119.7(3) . . ?
C13 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.8(3) . . ?
C25 C20 I4 117.5(2) . . ?
C21 C20 I4 123.7(2) . . ?
C25 C20 I5 152.5(2) . . ?
C21 C20 I5 34.00(15) . . ?
I4 C20 I5 89.77(10) . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 I5 117.3(2) . . ?
C20 C21 I5 124.1(2) . . ?
C22 C21 I4 152.8(2) . . ?
C20 C21 I4 34.31(15) . . ?
I5 C21 I4 89.86(10) . . ?
F1 C22 C23 117.2(3) . . ?
F1 C22 C21 120.8(3) . . ?
C23 C22 C21 122.0(3) . . ?
F1 C22 I5 82.45(16) . . ?
C23 C22 I5 160.0(2) . . ?
C21 C22 I5 38.51(15) . . ?
F2 C23 C24 120.3(3) . . ?
F2 C23 C22 120.5(3) . . ?
C24 C23 C22 119.2(3) . . ?
F3 C24 C23 120.2(3) . . ?
F3 C24 C25 120.4(3) . . ?
C23 C24 C25 119.4(3) . . ?
F4 C25 C20 120.8(3) . . ?
F4 C25 C24 117.1(3) . . ?
C20 C25 C24 122.1(3) . . ?
F4 C25 I4 82.36(16) . . ?
C20 C25 I4 38.51(16) . . ?
C24 C25 I4 160.5(2) . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -1.195
_refine_diff_density_rms         0.157

####################################################################### 
# 
# 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_d8-0534_a
_database_code_depnum_ccdc_archive 'CCDC 1830918'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H18 F8 I7 P'
_chemical_formula_weight         1461.72

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.5541(8)
_cell_length_b                   11.6207(5)
_cell_length_c                   19.9618(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.693(2)
_cell_angle_gamma                90
_cell_volume                     3756.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.56

_exptl_crystal_description       tabular
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.584
_exptl_crystal_F_000             2648
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    5.888
_shelx_estimated_absorpt_T_min   0.216
_shelx_estimated_absorpt_T_max   0.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5715
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            105272
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7781
_reflns_number_gt                7412
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0156P)²+5.2563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7781
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0432
_refine_ls_wR_factor_gt          0.0426
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.00796(2) 0.81451(2) 0.44568(2) 0.01375(4) Uani 1 1 d . . . . .
I2 I -0.17748(2) 0.87752(2) 0.41792(2) 0.01729(5) Uani 1 1 d . . . . .
I3 I 0.16358(2) 0.75509(2) 0.47147(2) 0.01852(5) Uani 1 1 d . . . . .
I4 I 0.33770(2) 0.62262(2) 0.59441(2) 0.01471(4) Uani 1 1 d . . . . .
I5 I 0.35711(2) 0.31478(2) 0.64559(2) 0.01616(4) Uani 1 1 d . . . . .
I6 I 0.61365(2) 1.05015(2) 0.44160(2) 0.02819(5) Uani 1 1 d . . . . .
I7 I 0.39418(2) 0.99694(2) 0.32604(2) 0.02810(5) Uani 1 1 d . . . . .
P1 P 0.91913(4) 0.85104(6) 0.69637(4) 0.01079(13) Uani 1 1 d . . . . .
F1 F 0.54606(11) 0.27225(14) 0.73488(10) 0.0224(4) Uani 1 1 d . . . . .
F2 F 0.67985(11) 0.40706(16) 0.77366(10) 0.0267(4) Uani 1 1 d . . . . .
F3 F 0.66576(10) 0.63059(15) 0.72955(10) 0.0240(4) Uani 1 1 d . . . . .
F4 F 0.51751(10) 0.72003(14) 0.65228(9) 0.0198(4) Uani 1 1 d . . . . .
F5 F 0.35235(12) 0.75445(16) 0.37029(11) 0.0306(4) Uani 1 1 d . . . . .
F6 F 0.43895(13) 0.59882(15) 0.46874(11) 0.0317(4) Uani 1 1 d . . . . .
F7 F 0.59828(12) 0.64229(16) 0.55774(10) 0.0315(4) Uani 1 1 d . . . . .
F8 F 0.67061(11) 0.83985(17) 0.54538(11) 0.0305(4) Uani 1 1 d . . . . .
C1 C 1.02235(17) 0.8192(2) 0.70458(14) 0.0121(5) Uani 1 1 d . . . . .
C2 C 1.05021(18) 0.8518(2) 0.65083(15) 0.0157(6) Uani 1 1 d . . . . .
H2A H 1.0166 0.8984 0.6115 0.019 Uiso 1 1 calc R U . . .
C3 C 1.12730(18) 0.8158(2) 0.65493(16) 0.0183(6) Uani 1 1 d . . . . .
H3A H 1.1464 0.8374 0.6182 0.022 Uiso 1 1 calc R U . . .
C4 C 1.17634(18) 0.7482(2) 0.71291(16) 0.0180(6) Uani 1 1 d . . . . .
H4A H 1.2288 0.7226 0.7154 0.022 Uiso 1 1 calc R U . . .
C5 C 1.14926(18) 0.7178(2) 0.76722(16) 0.0178(6) Uani 1 1 d . . . . .
H5A H 1.1837 0.6732 0.8073 0.021 Uiso 1 1 calc R U . . .
C6 C 1.07220(17) 0.7523(2) 0.76314(15) 0.0145(5) Uani 1 1 d . . . . .
H6A H 1.0533 0.7305 0.8000 0.017 Uiso 1 1 calc R U . . .
C7 C 0.92023(17) 0.9094(2) 0.77976(14) 0.0120(5) Uani 1 1 d . . . . .
C8 C 0.98993(17) 0.9673(2) 0.82689(14) 0.0140(5) Uani 1 1 d . . . . .
H8A H 1.0388 0.9691 0.8172 0.017 Uiso 1 1 calc R U . . .
C9 C 0.98783(18) 1.0224(2) 0.88794(15) 0.0174(6) Uani 1 1 d . . . . .
H9A H 1.0353 1.0618 0.9200 0.021 Uiso 1 1 calc R U . . .
C10 C 0.91651(19) 1.0200(2) 0.90207(15) 0.0175(6) Uani 1 1 d . . . . .
H10A H 0.9150 1.0580 0.9437 0.021 Uiso 1 1 calc R U . . .
C11 C 0.84738(19) 0.9621(2) 0.85540(16) 0.0187(6) Uani 1 1 d . . . . .
H11A H 0.7988 0.9604 0.8655 0.022 Uiso 1 1 calc R U . . .
C12 C 0.84816(17) 0.9070(2) 0.79430(16) 0.0159(6) Uani 1 1 d . . . . .
H12A H 0.8004 0.8678 0.7625 0.019 Uiso 1 1 calc R U . . .
C13 C 0.86079(16) 0.7201(2) 0.67297(15) 0.0121(5) Uani 1 1 d . . . . .
C14 C 0.82679(17) 0.6861(2) 0.59993(15) 0.0165(6) Uani 1 1 d . . . . .
H14A H 0.8308 0.7351 0.5633 0.020 Uiso 1 1 calc R U . . .
C15 C 0.78733(19) 0.5809(3) 0.58146(16) 0.0219(6) Uani 1 1 d . . . . .
H15A H 0.7640 0.5578 0.5320 0.026 Uiso 1 1 calc R U . . .
C16 C 0.78164(18) 0.5092(2) 0.63473(17) 0.0199(6) Uani 1 1 d . . . . .
H16A H 0.7547 0.4369 0.6217 0.024 Uiso 1 1 calc R U . . .
C17 C 0.81510(17) 0.5424(2) 0.70714(16) 0.0171(6) Uani 1 1 d . . . . .
H17A H 0.8105 0.4932 0.7434 0.021 Uiso 1 1 calc R U . . .
C18 C 0.85526(17) 0.6475(2) 0.72658(15) 0.0136(5) Uani 1 1 d . . . . .
H18A H 0.8789 0.6699 0.7762 0.016 Uiso 1 1 calc R U . . .
C19 C 0.87331(19) 0.9551(2) 0.62624(15) 0.0170(6) Uani 1 1 d . . . . .
H19A H 0.8721 0.9248 0.5800 0.025 Uiso 1 1 calc R U . . .
H19B H 0.8168 0.9714 0.6219 0.025 Uiso 1 1 calc R U . . .
H19C H 0.9059 1.0262 0.6383 0.025 Uiso 1 1 calc R U . . .
C20 C 0.45112(17) 0.5425(2) 0.65273(14) 0.0136(5) Uani 1 1 d . . . . .
C21 C 0.45834(17) 0.4264(2) 0.67308(14) 0.0141(5) Uani 1 1 d . . . . .
C22 C 0.53610(18) 0.3830(2) 0.71392(15) 0.0152(6) Uani 1 1 d . . . . .
C23 C 0.60582(17) 0.4511(3) 0.73388(15) 0.0177(6) Uani 1 1 d . . . . .
C24 C 0.59887(17) 0.5646(3) 0.71235(15) 0.0168(6) Uani 1 1 d . . . . .
C25 C 0.52166(17) 0.6093(2) 0.67223(15) 0.0139(5) Uani 1 1 d . . . . .
C26 C 0.54853(19) 0.9044(2) 0.45033(16) 0.0175(6) Uani 1 1 d . . . . .
C27 C 0.46695(19) 0.8825(2) 0.40558(15) 0.0168(6) Uani 1 1 d . . . . .
C28 C 0.43139(19) 0.7796(3) 0.41293(16) 0.0200(6) Uani 1 1 d . . . . .
C29 C 0.4746(2) 0.6986(2) 0.46361(17) 0.0212(6) Uani 1 1 d . . . . .
C30 C 0.5553(2) 0.7208(3) 0.50854(16) 0.0208(6) Uani 1 1 d . . . . .
C31 C 0.59115(19) 0.8226(3) 0.50176(17) 0.0206(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9027(3) . ?
I1 I3 2.9348(3) . ?
I1 I1 4.7852(4) 3_576 ?
I1 I2 4.8968(3) 3_576 ?
I2 I5 3.6689(3) 3_566 ?
I2 I6 4.3622(3) 1_455 ?
I2 I3 4.7693(3) 3_576 ?
I2 I1 4.8968(3) 3_576 ?
I3 I4 3.4565(3) . ?
I3 I6 4.2651(3) 3_676 ?
I3 I2 4.7693(3) 3_576 ?
I4 C20 2.097(3) . ?
I4 C25 2.999(3) . ?
I4 C21 3.095(3) . ?
I4 F4 3.1249(16) . ?
I4 I5 3.6997(3) . ?
I4 I6 4.0224(3) 3_676 ?
I4 I7 4.5558(3) 4_576 ?
I5 C21 2.095(3) . ?
I5 C22 3.009(3) . ?
I5 C20 3.093(3) . ?
I5 F1 3.1401(17) . ?
I5 F3 3.4246(18) 2_646 ?
I5 I2 3.6688(3) 3_566 ?
I5 I7 4.0469(3) 4_576 ?
I6 C26 2.088(3) . ?
I6 C31 2.993(3) . ?
I6 C27 3.085(3) . ?
I6 F8 3.109(2) . ?
I6 I7 3.6998(4) . ?
I6 I4 4.0224(3) 3_676 ?
I6 I3 4.2651(3) 3_676 ?
I6 I2 4.3623(3) 1_655 ?
I7 C27 2.087(3) . ?
I7 C28 2.990(3) . ?
I7 C26 3.077(3) . ?
I7 F5 3.1242(19) . ?
I7 I5 4.0470(3) 4_575 ?
I7 I4 4.5558(3) 4_575 ?
I7 I6 4.7249(4) 3_676 ?
P1 C19 1.789(3) . ?
P1 C7 1.791(3) . ?
P1 C13 1.793(3) . ?
P1 C1 1.794(3) . ?
F1 C22 1.343(3) . ?
F2 C23 1.336(3) . ?
F3 C24 1.332(3) . ?
F3 I5 3.4246(18) 2_656 ?
F4 C25 1.341(3) . ?
F5 C28 1.350(4) . ?
F6 C29 1.339(3) . ?
F7 C30 1.340(3) . ?
F8 C31 1.344(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.388(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.395(4) . ?
C7 C12 1.403(4) . ?
C8 C9 1.390(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.395(4) . ?
C13 C14 1.402(4) . ?
C14 C15 1.383(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.384(4) . ?
C20 C21 1.400(4) . ?
C21 C22 1.387(4) . ?
C22 C23 1.381(4) . ?
C23 C24 1.377(4) . ?
C24 C25 1.382(4) . ?
C26 C31 1.387(4) . ?
C26 C27 1.388(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.375(4) . ?
C29 C30 1.378(5) . ?
C30 C31 1.371(4) . ?

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
I2 I1 I3 178.669(8) . . ?
I2 I1 I1 74.669(6) . 3_576 ?
I3 I1 I1 104.827(7) . 3_576 ?
I2 I1 I2 109.536(6) . 3_576 ?
I3 I1 I2 69.968(6) . 3_576 ?
I1 I1 I2 34.868(4) 3_576 3_576 ?
I1 I2 I5 126.405(8) . 3_566 ?
I1 I2 I6 159.708(7) . 1_455 ?
I5 I2 I6 70.804(6) 3_566 1_455 ?
I1 I2 I3 105.773(7) . 3_576 ?
I5 I2 I3 126.076(6) 3_566 3_576 ?
I6 I2 I3 55.473(4) 1_455 3_576 ?
I1 I2 I1 70.464(6) . 3_576 ?
I5 I2 I1 159.334(6) 3_566 3_576 ?
I6 I2 I1 90.567(6) 1_455 3_576 ?
I3 I2 I1 35.318(4) 3_576 3_576 ?
I1 I3 I4 142.729(8) . . ?
I1 I3 I6 131.619(8) . 3_676 ?
I4 I3 I6 61.744(6) . 3_676 ?
I1 I3 I2 74.714(6) . 3_576 ?
I4 I3 I2 101.344(6) . 3_576 ?
I6 I3 I2 57.418(5) 3_676 3_576 ?
C20 I4 C25 24.15(9) . . ?
C20 I4 C21 22.22(9) . . ?
C25 I4 C21 46.36(7) . . ?
C20 I4 F4 49.33(8) . . ?
C25 I4 F4 25.19(6) . . ?
C21 I4 F4 71.55(6) . . ?
C20 I4 I3 169.11(7) . . ?
C25 I4 I3 150.61(5) . . ?
C21 I4 I3 158.86(5) . . ?
F4 I4 I3 126.27(3) . . ?
C20 I4 I5 56.70(8) . . ?
C25 I4 I5 80.84(5) . . ?
C21 I4 I5 34.48(5) . . ?
F4 I4 I5 106.01(3) . . ?
I3 I4 I5 126.062(7) . . ?
C20 I4 I6 107.30(8) . 3_676 ?
C25 I4 I6 83.17(5) . 3_676 ?
C21 I4 I6 129.50(5) . 3_676 ?
F4 I4 I6 57.98(3) . 3_676 ?
I3 I4 I6 69.063(6) . 3_676 ?
I5 I4 I6 163.767(7) . 3_676 ?
C20 I4 I7 60.85(7) . 4_576 ?
C25 I4 I7 71.90(5) . 4_576 ?
C21 I4 I7 54.70(5) . 4_576 ?
F4 I4 I7 86.68(3) . 4_576 ?
I3 I4 I7 130.015(7) . 4_576 ?
I5 I4 I7 57.593(5) . 4_576 ?
I6 I4 I7 119.447(6) 3_676 4_576 ?
C21 I5 C22 24.00(9) . . ?
C21 I5 C20 22.26(9) . . ?
C22 I5 C20 46.25(7) . . ?
C21 I5 F1 49.12(8) . . ?
C22 I5 F1 25.12(6) . . ?
C20 I5 F1 71.37(6) . . ?
C21 I5 F3 121.48(8) . 2_646 ?
C22 I5 F3 103.28(6) . 2_646 ?
C20 I5 F3 135.36(6) . 2_646 ?
F1 I5 F3 83.29(4) . 2_646 ?
C21 I5 I2 175.38(7) . 3_566 ?
C22 I5 I2 157.67(5) . 3_566 ?
C20 I5 I2 155.41(5) . 3_566 ?
F1 I5 I2 132.77(3) . 3_566 ?
F3 I5 I2 62.89(3) 2_646 3_566 ?
C21 I5 I4 56.77(8) . . ?
C22 I5 I4 80.76(5) . . ?
C20 I5 I4 34.52(5) . . ?
F1 I5 I4 105.87(3) . . ?
F3 I5 I4 141.36(3) 2_646 . ?
I2 I5 I4 121.212(7) 3_566 . ?
C21 I5 I7 66.62(7) . 4_576 ?
C22 I5 I7 70.91(5) . 4_576 ?
C20 I5 I7 66.21(5) . 4_576 ?
F1 I5 I7 78.93(3) . 4_576 ?
F3 I5 I7 73.37(3) 2_646 4_576 ?
I2 I5 I7 117.289(6) 3_566 4_576 ?
I4 I5 I7 71.887(6) . 4_576 ?
C26 I6 C31 24.29(10) . . ?
C26 I6 C27 21.94(10) . . ?
C31 I6 C27 46.21(8) . . ?
C26 I6 F8 49.64(9) . . ?
C31 I6 F8 25.36(7) . . ?
C27 I6 F8 71.57(6) . . ?
C26 I6 I7 56.26(8) . . ?
C31 I6 I7 80.54(6) . . ?
C27 I6 I7 34.34(5) . . ?
F8 I6 I7 105.90(4) . . ?
C26 I6 I4 160.50(8) . 3_676 ?
C31 I6 I4 167.69(6) . 3_676 ?
C27 I6 I4 140.46(5) . 3_676 ?
F8 I6 I4 145.72(4) . 3_676 ?
I7 I6 I4 106.759(7) . 3_676 ?
C26 I6 I3 147.36(9) . 3_676 ?
C31 I6 I3 123.22(6) . 3_676 ?
C27 I6 I3 169.09(5) . 3_676 ?
F8 I6 I3 97.89(4) . 3_676 ?
I7 I6 I3 155.940(7) . 3_676 ?
I4 I6 I3 49.194(4) 3_676 3_676 ?
C26 I6 I2 98.40(8) . 1_655 ?
C31 I6 I2 83.32(6) . 1_655 ?
C27 I6 I2 110.20(5) . 1_655 ?
F8 I6 I2 69.08(4) . 1_655 ?
I7 I6 I2 124.903(7) . 1_655 ?
I4 I6 I2 99.795(6) 3_676 1_655 ?
I3 I6 I2 67.109(6) 3_676 1_655 ?
C27 I7 C28 24.20(10) . . ?
C27 I7 C26 22.15(10) . . ?
C28 I7 C26 46.34(8) . . ?
C27 I7 F5 49.59(9) . . ?
C28 I7 F5 25.40(7) . . ?
C26 I7 F5 71.74(6) . . ?
C27 I7 I6 56.48(8) . . ?
C28 I7 I6 80.66(6) . . ?
C26 I7 I6 34.35(5) . . ?
F5 I7 I6 106.04(4) . . ?
C27 I7 I5 149.61(8) . 4_575 ?
C28 I7 I5 153.78(6) . 4_575 ?
C26 I7 I5 134.10(5) . 4_575 ?
F5 I7 I5 139.88(4) . 4_575 ?
I6 I7 I5 103.637(7) . 4_575 ?
C27 I7 I4 114.04(8) . 4_575 ?
C28 I7 I4 104.14(6) . 4_575 ?
C26 I7 I4 119.40(5) . 4_575 ?
F5 I7 I4 91.66(4) . 4_575 ?
I6 I7 I4 116.761(7) . 4_575 ?
I5 I7 I4 50.520(5) 4_575 4_575 ?
C27 I7 I6 54.59(8) . 3_676 ?
C28 I7 I6 54.22(6) . 3_676 ?
C26 I7 I6 61.18(5) . 3_676 ?
F5 I7 I6 61.25(4) . 3_676 ?
I6 I7 I6 79.918(7) . 3_676 ?
I5 I7 I6 151.746(6) 4_575 3_676 ?
I4 I7 I6 152.085(7) 4_575 3_676 ?
C19 P1 C7 108.17(13) . . ?
C19 P1 C13 109.32(13) . . ?
C7 P1 C13 111.34(13) . . ?
C19 P1 C1 110.13(14) . . ?
C7 P1 C1 110.18(13) . . ?
C13 P1 C1 107.70(12) . . ?
C22 F1 I5 71.97(14) . . ?
C24 F3 I5 102.03(15) . 2_656 ?
C25 F4 I4 72.15(14) . . ?
C28 F5 I7 71.76(15) . . ?
C31 F8 I6 72.48(16) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 P1 121.1(2) . . ?
C6 C1 P1 118.4(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C8 C7 C12 119.8(3) . . ?
C8 C7 P1 120.1(2) . . ?
C12 C7 P1 119.8(2) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C7 119.3(3) . . ?
C11 C12 H12A 120.3 . . ?
C7 C12 H12A 120.3 . . ?
C18 C13 C14 120.0(3) . . ?
C18 C13 P1 121.0(2) . . ?
C14 C13 P1 118.7(2) . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 119.7(3) . . ?
C17 C18 H18A 120.2 . . ?
C13 C18 H18A 120.2 . . ?
P1 C19 H19A 109.5 . . ?
P1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.2(3) . . ?
C25 C20 I4 117.5(2) . . ?
C21 C20 I4 123.3(2) . . ?
C25 C20 I5 153.67(19) . . ?
C21 C20 I5 34.52(14) . . ?
I4 C20 I5 88.79(9) . . ?
C22 C21 C20 118.7(3) . . ?
C22 C21 I5 118.1(2) . . ?
C20 C21 I5 123.2(2) . . ?
C22 C21 I4 153.1(2) . . ?
C20 C21 I4 34.49(14) . . ?
I5 C21 I4 88.75(9) . . ?
F1 C22 C23 117.7(2) . . ?
F1 C22 C21 120.8(3) . . ?
C23 C22 C21 121.5(3) . . ?
F1 C22 I5 82.91(15) . . ?
C23 C22 I5 159.4(2) . . ?
C21 C22 I5 37.89(14) . . ?
F2 C23 C24 120.1(3) . . ?
F2 C23 C22 120.1(3) . . ?
C24 C23 C22 119.8(3) . . ?
F3 C24 C23 120.5(3) . . ?
F3 C24 C25 120.2(3) . . ?
C23 C24 C25 119.3(3) . . ?
F4 C25 C24 117.5(2) . . ?
F4 C25 C20 120.9(2) . . ?
C24 C25 C20 121.6(3) . . ?
F4 C25 I4 82.66(14) . . ?
C24 C25 I4 159.8(2) . . ?
C20 C25 I4 38.31(14) . . ?
C31 C26 C27 118.6(3) . . ?
C31 C26 I6 117.5(2) . . ?
C27 C26 I6 123.9(2) . . ?
C31 C26 I7 153.1(2) . . ?
C27 C26 I7 34.54(14) . . ?
I6 C26 I7 89.39(10) . . ?
C28 C27 C26 119.1(3) . . ?
C28 C27 I7 117.6(2) . . ?
C26 C27 I7 123.3(2) . . ?
C28 C27 I6 153.1(2) . . ?
C26 C27 I6 34.19(14) . . ?
I7 C27 I6 89.18(9) . . ?
F5 C28 C29 117.1(3) . . ?
F5 C28 C27 121.1(3) . . ?
C29 C28 C27 121.8(3) . . ?
F5 C28 I7 82.85(16) . . ?
C29 C28 I7 160.0(2) . . ?
C27 C28 I7 38.22(15) . . ?
F6 C29 C28 120.5(3) . . ?
F6 C29 C30 120.4(3) . . ?
C28 C29 C30 119.1(3) . . ?
F7 C30 C31 120.6(3) . . ?
F7 C30 C29 119.8(3) . . ?
C31 C30 C29 119.6(3) . . ?
F8 C31 C30 117.8(3) . . ?
F8 C31 C26 120.4(3) . . ?
C30 C31 C26 121.8(3) . . ?
F8 C31 I6 82.16(16) . . ?
C30 C31 I6 159.8(2) . . ?
C26 C31 I6 38.25(15) . . ?

_refine_diff_density_max         1.088
_refine_diff_density_min         -1.593
_refine_diff_density_rms         0.137

