# 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 2019

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1909049'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-07-15 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            'C19 H18 I3 P'
_chemical_formula_weight         658.00

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/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                   17.9211(5)
_cell_length_b                   14.6131(4)
_cell_length_c                   16.2764(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.0800(10)
_cell_angle_gamma                90
_cell_volume                     4245.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9201
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.30

_exptl_crystal_description       tabular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    4.490
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8451
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec ImuS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27921
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7876
_reflns_number_gt                6660
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0366P)²+20.6845P] 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         7876
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.72459(2) 0.62018(3) 0.66176(2) 0.02768(11) Uani 1 1 d . . . . .
I2 I 0.88974(2) 0.60828(3) 0.69899(3) 0.03111(11) Uani 1 1 d . . . . .
I3 I 0.56337(2) 0.63425(3) 0.63076(3) 0.03575(12) Uani 1 1 d . . . . .
I4 I 0.76256(2) 0.38649(3) 0.17322(2) 0.02695(10) Uani 1 1 d . . . . .
I5 I 0.61000(2) 0.39200(3) 0.22493(3) 0.03360(11) Uani 1 1 d . . . . .
I6 I 0.91476(3) 0.37172(3) 0.12502(3) 0.03718(12) Uani 1 1 d . . . . .
P1 P 0.66693(8) 0.89393(10) 0.48040(9) 0.0206(3) Uani 1 1 d . . . . .
P2 P 0.85124(8) 0.39444(9) 0.46802(9) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.6401(3) 0.7967(4) 0.4180(3) 0.0206(12) Uani 1 1 d . . . . .
C2 C 0.5644(4) 0.7759(4) 0.4013(4) 0.0306(14) Uani 1 1 d . . . . .
H2A H 0.5276 0.8113 0.4254 0.037 Uiso 1 1 calc R U . . .
C3 C 0.5429(4) 0.7037(5) 0.3497(4) 0.0359(16) Uani 1 1 d . . . . .
H3A H 0.4912 0.6905 0.3372 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5966(4) 0.6504(4) 0.3160(4) 0.0358(15) Uani 1 1 d . . . . .
H4A H 0.5817 0.5997 0.2819 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6713(4) 0.6707(5) 0.3317(5) 0.0437(18) Uani 1 1 d . . . . .
H5A H 0.7079 0.6344 0.3082 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6932(4) 0.7441(4) 0.3819(4) 0.0353(15) Uani 1 1 d . . . . .
H6A H 0.7448 0.7587 0.3919 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7666(3) 0.8985(4) 0.4963(3) 0.0199(11) Uani 1 1 d . . . . .
C8 C 0.8050(3) 0.8529(4) 0.5633(4) 0.0261(13) Uani 1 1 d . . . . .
H8A H 0.7777 0.8230 0.6030 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8822(3) 0.8516(4) 0.5716(4) 0.0293(13) Uani 1 1 d . . . . .
H9A H 0.9080 0.8218 0.6176 0.035 Uiso 1 1 calc R U . . .
C10 C 0.9228(4) 0.8938(4) 0.5127(4) 0.0296(14) Uani 1 1 d . . . . .
H10A H 0.9760 0.8920 0.5184 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8855(4) 0.9381(5) 0.4465(4) 0.0331(15) Uani 1 1 d . . . . .
H11A H 0.9131 0.9675 0.4069 0.040 Uiso 1 1 calc R U . . .
C12 C 0.8077(3) 0.9400(4) 0.4374(4) 0.0287(14) Uani 1 1 d . . . . .
H12A H 0.7824 0.9696 0.3911 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6307(3) 0.9948(4) 0.4274(3) 0.0205(12) Uani 1 1 d . . . . .
C14 C 0.6108(3) 0.9921(4) 0.3437(4) 0.0262(13) Uani 1 1 d . . . . .
H14A H 0.6158 0.9368 0.3140 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5837(4) 1.0699(4) 0.3030(4) 0.0311(14) Uani 1 1 d . . . . .
H15A H 0.5700 1.0677 0.2453 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5762(3) 1.1513(4) 0.3456(4) 0.0288(13) Uani 1 1 d . . . . .
H16A H 0.5574 1.2046 0.3175 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5967(4) 1.1537(4) 0.4304(4) 0.0319(14) Uani 1 1 d . . . . .
H17A H 0.5918 1.2089 0.4604 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6238(4) 1.0768(4) 0.4703(4) 0.0297(14) Uani 1 1 d . . . . .
H18A H 0.6382 1.0791 0.5278 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6277(4) 0.8855(4) 0.5768(4) 0.0286(13) Uani 1 1 d . . . . .
H19A H 0.5730 0.8830 0.5674 0.043 Uiso 1 1 calc R U . . .
H19B H 0.6461 0.8297 0.6053 0.043 Uiso 1 1 calc R U . . .
H19C H 0.6425 0.9390 0.6107 0.043 Uiso 1 1 calc R U . . .
C20 C 0.7597(3) 0.4033(4) 0.5023(3) 0.0194(11) Uani 1 1 d . . . . .
C21 C 0.7037(3) 0.4502(4) 0.4537(4) 0.0283(13) Uani 1 1 d . . . . .
H21A H 0.7156 0.4821 0.4057 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6312(4) 0.4499(4) 0.4756(4) 0.0329(14) Uani 1 1 d . . . . .
H22A H 0.5937 0.4832 0.4433 0.040 Uiso 1 1 calc R U . . .
C23 C 0.6127(4) 0.4021(4) 0.5437(4) 0.0335(15) Uani 1 1 d . . . . .
H23A H 0.5623 0.4008 0.5574 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6683(4) 0.3555(5) 0.5923(4) 0.0366(16) Uani 1 1 d . . . . .
H24A H 0.6557 0.3233 0.6399 0.044 Uiso 1 1 calc R U . . .
C25 C 0.7416(4) 0.3555(4) 0.5722(4) 0.0291(13) Uani 1 1 d . . . . .
H25A H 0.7793 0.3235 0.6054 0.035 Uiso 1 1 calc R U . . .
C26 C 0.8534(3) 0.2953(4) 0.4031(3) 0.0212(12) Uani 1 1 d . . . . .
C27 C 0.7878(4) 0.2484(4) 0.3788(4) 0.0285(13) Uani 1 1 d . . . . .
H27A H 0.7416 0.2685 0.3969 0.034 Uiso 1 1 calc R U . . .
C28 C 0.7898(4) 0.1725(4) 0.3283(4) 0.0383(16) Uani 1 1 d . . . . .
H28A H 0.7451 0.1396 0.3127 0.046 Uiso 1 1 calc R U . . .
C29 C 0.8562(4) 0.1445(4) 0.3009(4) 0.0343(15) Uani 1 1 d . . . . .
H29A H 0.8572 0.0925 0.2660 0.041 Uiso 1 1 calc R U . . .
C30 C 0.9212(4) 0.1910(5) 0.3234(4) 0.0399(17) Uani 1 1 d . . . . .
H30A H 0.9668 0.1717 0.3032 0.048 Uiso 1 1 calc R U . . .
C31 C 0.9209(4) 0.2660(4) 0.3753(4) 0.0337(15) Uani 1 1 d . . . . .
H31A H 0.9663 0.2972 0.3920 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8712(3) 0.4966(4) 0.4123(3) 0.0200(11) Uani 1 1 d . . . . .
C33 C 0.8970(3) 0.4923(4) 0.3344(4) 0.0272(13) Uani 1 1 d . . . . .
H33A H 0.9029 0.4349 0.3083 0.033 Uiso 1 1 calc R U . . .
C34 C 0.9139(4) 0.5726(5) 0.2955(4) 0.0346(15) Uani 1 1 d . . . . .
H34A H 0.9310 0.5700 0.2420 0.041 Uiso 1 1 calc R U . . .
C35 C 0.9065(4) 0.6558(4) 0.3322(4) 0.0351(15) Uani 1 1 d . . . . .
H35A H 0.9188 0.7101 0.3043 0.042 Uiso 1 1 calc R U . . .
C36 C 0.8813(4) 0.6610(4) 0.4099(4) 0.0311(14) Uani 1 1 d . . . . .
H36A H 0.8762 0.7189 0.4354 0.037 Uiso 1 1 calc R U . . .
C37 C 0.8635(3) 0.5813(4) 0.4505(4) 0.0258(13) Uani 1 1 d . . . . .
H37A H 0.8462 0.5844 0.5039 0.031 Uiso 1 1 calc R U . . .
C38 C 0.9204(4) 0.3850(4) 0.5541(4) 0.0324(14) Uani 1 1 d . . . . .
H38A H 0.9702 0.3802 0.5341 0.049 Uiso 1 1 calc R U . . .
H38B H 0.9183 0.4394 0.5891 0.049 Uiso 1 1 calc R U . . .
H38C H 0.9104 0.3303 0.5862 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I3 2.8960(6) . ?
I1 I2 2.9731(6) . ?
I4 I6 2.9123(6) . ?
I4 I5 2.9320(6) . ?
P1 C19 1.779(6) . ?
P1 C7 1.784(6) . ?
P1 C1 1.788(6) . ?
P1 C13 1.800(6) . ?
P2 C20 1.784(6) . ?
P2 C38 1.792(6) . ?
P2 C26 1.796(6) . ?
P2 C32 1.799(5) . ?
C1 C6 1.393(8) . ?
C1 C2 1.393(8) . ?
C2 C3 1.382(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(10) . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.383(9) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C12 1.398(8) . ?
C7 C8 1.404(8) . ?
C8 C9 1.379(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.396(9) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(9) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(9) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(8) . ?
C13 C18 1.397(8) . ?
C14 C15 1.383(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.390(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.397(9) . ?
C16 H16A 0.9500 . ?
C17 C18 1.365(9) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.397(8) . ?
C20 C21 1.401(8) . ?
C21 C22 1.376(9) . ?
C21 H21A 0.9500 . ?
C22 C23 1.376(9) . ?
C22 H22A 0.9500 . ?
C23 C24 1.396(10) . ?
C23 H23A 0.9500 . ?
C24 C25 1.382(9) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.387(8) . ?
C26 C31 1.396(8) . ?
C27 C28 1.383(9) . ?
C27 H27A 0.9500 . ?
C28 C29 1.370(10) . ?
C28 H28A 0.9500 . ?
C29 C30 1.370(10) . ?
C29 H29A 0.9500 . ?
C30 C31 1.384(9) . ?
C30 H30A 0.9500 . ?
C31 H31A 0.9500 . ?
C32 C33 1.388(8) . ?
C32 C37 1.398(8) . ?
C33 C34 1.380(8) . ?
C33 H33A 0.9500 . ?
C34 C35 1.366(10) . ?
C34 H34A 0.9500 . ?
C35 C36 1.381(10) . ?
C35 H35A 0.9500 . ?
C36 C37 1.390(9) . ?
C36 H36A 0.9500 . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I3 I1 I2 178.146(19) . . ?
I6 I4 I5 177.142(18) . . ?
C19 P1 C7 110.1(3) . . ?
C19 P1 C1 109.8(3) . . ?
C7 P1 C1 109.1(3) . . ?
C19 P1 C13 109.0(3) . . ?
C7 P1 C13 110.7(3) . . ?
C1 P1 C13 108.1(3) . . ?
C20 P2 C38 110.7(3) . . ?
C20 P2 C26 108.1(3) . . ?
C38 P2 C26 110.4(3) . . ?
C20 P2 C32 109.1(3) . . ?
C38 P2 C32 107.7(3) . . ?
C26 P2 C32 110.9(3) . . ?
C6 C1 C2 119.1(5) . . ?
C6 C1 P1 121.3(4) . . ?
C2 C1 P1 119.5(5) . . ?
C3 C2 C1 120.0(6) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.1(6) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 120.3(6) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 119.9(7) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.5(6) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C12 C7 C8 119.2(5) . . ?
C12 C7 P1 119.9(4) . . ?
C8 C7 P1 120.6(4) . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.4(5) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 120.3(6) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C7 120.2(5) . . ?
C11 C12 H12A 119.9 . . ?
C7 C12 H12A 119.9 . . ?
C14 C13 C18 119.5(5) . . ?
C14 C13 P1 120.0(4) . . ?
C18 C13 P1 120.5(4) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.6(6) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C15 C16 C17 119.1(6) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C13 120.8(6) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?
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 119.9(5) . . ?
C25 C20 P2 120.3(4) . . ?
C21 C20 P2 119.5(4) . . ?
C22 C21 C20 119.9(6) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C23 C22 C21 120.7(6) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C24 119.6(6) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C25 C24 C23 120.8(6) . . ?
C25 C24 H24A 119.6 . . ?
C23 C24 H24A 119.6 . . ?
C24 C25 C20 119.2(6) . . ?
C24 C25 H25A 120.4 . . ?
C20 C25 H25A 120.4 . . ?
C27 C26 C31 119.6(6) . . ?
C27 C26 P2 120.3(4) . . ?
C31 C26 P2 120.1(5) . . ?
C28 C27 C26 120.0(6) . . ?
C28 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C29 C28 C27 120.2(6) . . ?
C29 C28 H28A 119.9 . . ?
C27 C28 H28A 119.9 . . ?
C28 C29 C30 120.4(6) . . ?
C28 C29 H29A 119.8 . . ?
C30 C29 H29A 119.8 . . ?
C29 C30 C31 120.5(6) . . ?
C29 C30 H30A 119.8 . . ?
C31 C30 H30A 119.8 . . ?
C30 C31 C26 119.3(6) . . ?
C30 C31 H31A 120.3 . . ?
C26 C31 H31A 120.3 . . ?
C33 C32 C37 120.0(5) . . ?
C33 C32 P2 121.3(4) . . ?
C37 C32 P2 118.6(4) . . ?
C34 C33 C32 119.0(6) . . ?
C34 C33 H33A 120.5 . . ?
C32 C33 H33A 120.5 . . ?
C35 C34 C33 121.5(6) . . ?
C35 C34 H34A 119.2 . . ?
C33 C34 H34A 119.2 . . ?
C34 C35 C36 120.1(6) . . ?
C34 C35 H35A 120.0 . . ?
C36 C35 H35A 120.0 . . ?
C35 C36 C37 119.7(6) . . ?
C35 C36 H36A 120.1 . . ?
C37 C36 H36A 120.1 . . ?
C36 C37 C32 119.7(6) . . ?
C36 C37 H37A 120.2 . . ?
C32 C37 H37A 120.2 . . ?
P2 C38 H38A 109.5 . . ?
P2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
P2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.185

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1909050'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br0.83 I2.17 P'
_chemical_formula_weight         619.06

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'
Br Br -0.2901 2.4595 '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                   14.4120(7)
_cell_length_b                   16.5445(9)
_cell_length_c                   17.5295(9)
_cell_angle_alpha                92.457(2)
_cell_angle_beta                 91.538(2)
_cell_angle_gamma                90.460(2)
_cell_volume                     4174.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9146
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      26.36

_exptl_crystal_description       tabular
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_F_000             2329
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    4.928
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8137
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            122521
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.680
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             15506
_reflns_number_gt                11669
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0218P)²+23.8190P] 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         15506
_refine_ls_number_parameters     837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.37100(3) 0.35467(2) 0.70785(3) 0.03552(11) Uani 1 1 d . . . . .
Br2 Br 0.39673(4) 0.40696(4) 0.86166(4) 0.0510(3) Uani 0.638(6) 1 d . . P . .
I2 I 0.39673(4) 0.40696(4) 0.86166(4) 0.0510(3) Uani 0.362(6) 1 d . . P . .
I3 I 0.35928(3) 0.31278(3) 0.54895(3) 0.0453(2) Uani 0.714(6) 1 d . . P . .
Br3 Br 0.35928(3) 0.31278(3) 0.54895(3) 0.0453(2) Uani 0.286(6) 1 d . . P . .
I4 I 0.87854(3) 0.35982(2) 0.76806(2) 0.03522(11) Uani 1 1 d . . . . .
Br5 Br 0.89251(4) 0.40423(4) 0.61641(4) 0.0585(3) Uani 0.631(6) 1 d . . P . .
I5 I 0.89251(4) 0.40423(4) 0.61641(4) 0.0585(3) Uani 0.369(6) 1 d . . P . .
I6 I 0.87949(3) 0.31985(3) 0.92361(3) 0.0426(2) Uani 0.714(6) 1 d . . P . .
Br6 Br 0.87949(3) 0.31985(3) 0.92361(3) 0.0426(2) Uani 0.286(6) 1 d . . P . .
I7 I 0.34846(3) 0.12496(2) 0.21367(2) 0.03403(11) Uani 1 1 d . . . . .
Br8 Br 0.35330(4) 0.09861(3) 0.05435(3) 0.0463(2) Uani 0.430(6) 1 d . . P . .
I8 I 0.35330(4) 0.09861(3) 0.05435(3) 0.0463(2) Uani 0.570(6) 1 d . . P . .
I9 I 0.34759(3) 0.16648(3) 0.37490(3) 0.04036(19) Uani 0.709(5) 1 d . . P . .
Br9 Br 0.34759(3) 0.16648(3) 0.37490(3) 0.04036(19) Uani 0.291(5) 1 d . . P . .
I10 I 0.15924(3) -0.14259(2) 0.75420(3) 0.03683(11) Uani 1 1 d . . . . .
Br11 Br 0.13968(4) -0.09444(4) 0.60195(4) 0.0536(2) Uani 0.471(6) 1 d . . P . .
I11 I 0.13968(4) -0.09444(4) 0.60195(4) 0.0536(2) Uani 0.529(6) 1 d . . P . .
I12 I 0.16854(3) -0.18436(3) 0.90983(3) 0.0467(2) Uani 0.720(6) 1 d . . P . .
Br12 Br 0.16854(3) -0.18436(3) 0.90983(3) 0.0467(2) Uani 0.280(6) 1 d . . P . .
P1 P 0.12465(10) -0.06260(9) 0.33970(9) 0.0271(3) Uani 1 1 d . . . . .
P2 P 0.38365(9) 0.05774(8) 0.81603(9) 0.0252(3) Uani 1 1 d . . . . .
P3 P 0.66054(10) 0.55625(9) 0.84593(9) 0.0278(3) Uani 1 1 d . . . . .
P4 P 1.15579(10) 0.56082(9) 0.65904(9) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.0234(4) -0.1240(3) 0.3528(3) 0.0271(13) Uani 1 1 d . . . . .
C7 C 0.2272(4) -0.1185(3) 0.3602(3) 0.0282(13) Uani 1 1 d . . . . .
C20 C 0.3749(4) 0.0390(3) 0.7156(3) 0.0268(12) Uani 1 1 d . . . . .
C33 C 0.2919(4) 0.1954(3) 0.8677(3) 0.0292(13) Uani 1 1 d . . . . .
H33A H 0.349687 0.222790 0.864049 0.035 Uiso 1 1 calc R U . . .
C40 C 0.8488(4) 0.5730(4) 0.8790(4) 0.0370(15) Uani 1 1 d . . . . .
H40A H 0.852337 0.516486 0.867630 0.044 Uiso 1 1 calc R U . . .
C39 C 0.7633(4) 0.6122(3) 0.8739(3) 0.0279(13) Uani 1 1 d . . . . .
C14 C 0.0746(4) 0.0355(4) 0.2241(4) 0.0400(16) Uani 1 1 d . . . . .
H14A H 0.045642 0.068022 0.262452 0.048 Uiso 1 1 calc R U . . .
C2 C -0.0137(4) -0.1708(4) 0.2923(3) 0.0323(14) Uani 1 1 d . . . . .
H2A H 0.012600 -0.168993 0.243254 0.039 Uiso 1 1 calc R U . . .
C4 C -0.1299(4) -0.2216(4) 0.3739(4) 0.0366(15) Uani 1 1 d . . . . .
H4A H -0.182190 -0.255349 0.381268 0.044 Uiso 1 1 calc R U . . .
C58 C 1.1652(4) 0.5336(3) 0.7560(3) 0.0279(13) Uani 1 1 d . . . . .
C64 C 1.2565(4) 0.6182(3) 0.6342(3) 0.0291(13) Uani 1 1 d . . . . .
C37 C 0.2000(4) 0.0729(4) 0.8545(4) 0.0341(14) Uani 1 1 d . . . . .
H37A H 0.194494 0.016856 0.840995 0.041 Uiso 1 1 calc R U . . .
C60 C 1.1161(4) 0.4499(4) 0.8560(4) 0.0388(15) Uani 1 1 d . . . . .
H60A H 1.083593 0.403719 0.872143 0.047 Uiso 1 1 calc R U . . .
C26 C 0.4868(3) 0.1166(3) 0.8374(3) 0.0252(12) Uani 1 1 d . . . . .
C13 C 0.1238(4) -0.0323(3) 0.2434(3) 0.0289(13) Uani 1 1 d . . . . .
C68 C 1.4195(4) 0.6228(4) 0.6126(4) 0.0439(16) Uani 1 1 d . . . . .
H68A H 1.478113 0.596959 0.611353 0.053 Uiso 1 1 calc R U . . .
C21 C 0.3295(4) 0.0924(4) 0.6694(4) 0.0369(15) Uani 1 1 d . . . . .
H21A H 0.298036 0.137414 0.691612 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3011(4) -0.2393(4) 0.4017(4) 0.0437(16) Uani 1 1 d . . . . .
H11A H 0.297252 -0.294094 0.415609 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1663(5) -0.0790(4) 0.1874(4) 0.0453(17) Uani 1 1 d . . . . .
H18A H 0.200078 -0.125736 0.200435 0.054 Uiso 1 1 calc R U . . .
C3 C -0.0900(4) -0.2205(4) 0.3036(4) 0.0399(16) Uani 1 1 d . . . . .
H3A H -0.114721 -0.253937 0.262403 0.048 Uiso 1 1 calc R U . . .
C27 C 0.5382(4) 0.1049(4) 0.9042(4) 0.0380(15) Uani 1 1 d . . . . .
H27A H 0.519728 0.064576 0.937857 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4198(4) -0.0388(3) 0.6024(4) 0.0342(14) Uani 1 1 d . . . . .
H24A H 0.450338 -0.084166 0.579815 0.041 Uiso 1 1 calc R U . . .
C32 C 0.2847(4) 0.1132(3) 0.8485(3) 0.0278(13) Uani 1 1 d . . . . .
C45 C 0.6616(4) 0.5296(3) 0.7464(3) 0.0265(12) Uani 1 1 d . . . . .
C30 C 0.5911(4) 0.2232(4) 0.8075(4) 0.0428(17) Uani 1 1 d . . . . .
H30A H 0.609573 0.264060 0.774411 0.051 Uiso 1 1 calc R U . . .
C65 C 1.2486(4) 0.6972(4) 0.6137(4) 0.0353(14) Uani 1 1 d . . . . .
H65A H 1.189611 0.722436 0.612627 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4203(4) -0.0278(3) 0.6804(3) 0.0303(13) Uani 1 1 d . . . . .
H25A H 0.451607 -0.065386 0.711245 0.036 Uiso 1 1 calc R U . . .
C59 C 1.1167(4) 0.4661(3) 0.7799(4) 0.0349(14) Uani 1 1 d . . . . .
H59A H 1.084187 0.431452 0.743532 0.042 Uiso 1 1 calc R U . . .
C46 C 0.7114(5) 0.5746(4) 0.6978(4) 0.0475(18) Uani 1 1 d . . . . .
H46A H 0.750032 0.617670 0.717852 0.057 Uiso 1 1 calc R U . . .
C76 C 1.1484(4) 0.4726(4) 0.5962(4) 0.0392(15) Uani 1 1 d . . . . .
H76A H 1.143338 0.488987 0.543164 0.059 Uiso 1 1 calc R U . . .
H76B H 1.204343 0.440047 0.602934 0.059 Uiso 1 1 calc R U . . .
H76C H 1.093643 0.440504 0.608008 0.059 Uiso 1 1 calc R U . . .
C38 C 0.3888(4) -0.0359(3) 0.8638(3) 0.0308(13) Uani 1 1 d . . . . .
H38A H 0.393630 -0.024777 0.919141 0.046 Uiso 1 1 calc R U . . .
H38B H 0.332468 -0.067838 0.851267 0.046 Uiso 1 1 calc R U . . .
H38C H 0.443258 -0.066393 0.847126 0.046 Uiso 1 1 calc R U . . .
C42 C 0.9228(4) 0.6975(4) 0.9158(4) 0.0389(15) Uani 1 1 d . . . . .
H42A H 0.977583 0.727264 0.930474 0.047 Uiso 1 1 calc R U . . .
C52 C 0.5181(4) 0.6570(4) 0.8051(4) 0.0499(18) Uani 1 1 d . . . . .
H52A H 0.537729 0.649288 0.754067 0.060 Uiso 1 1 calc R U . . .
C47 C 0.7059(5) 0.5581(5) 0.6206(4) 0.062(2) Uani 1 1 d . . . . .
H47A H 0.740714 0.589882 0.587563 0.074 Uiso 1 1 calc R U . . .
C61 C 1.1625(4) 0.5005(4) 0.9095(4) 0.0390(15) Uani 1 1 d . . . . .
H61A H 1.161433 0.489238 0.962173 0.047 Uiso 1 1 calc R U . . .
C41 C 0.9277(4) 0.6163(4) 0.9005(4) 0.0416(16) Uani 1 1 d . . . . .
H41A H 0.985635 0.589541 0.904608 0.050 Uiso 1 1 calc R U . . .
C71 C 1.0162(4) 0.6621(4) 0.7103(4) 0.0381(15) Uani 1 1 d . . . . .
H71A H 1.044834 0.658862 0.759512 0.046 Uiso 1 1 calc R U . . .
C36 C 0.1242(4) 0.1153(4) 0.8804(4) 0.0386(15) Uani 1 1 d . . . . .
H36A H 0.066603 0.088080 0.885444 0.046 Uiso 1 1 calc R U . . .
C63 C 1.2118(4) 0.5839(4) 0.8100(4) 0.0367(15) Uani 1 1 d . . . . .
H63A H 1.244675 0.629953 0.794092 0.044 Uiso 1 1 calc R U . . .
C53 C 0.4443(5) 0.7077(5) 0.8219(6) 0.073(3) Uani 1 1 d . . . . .
H53A H 0.413068 0.734352 0.781910 0.087 Uiso 1 1 calc R U . . .
C69 C 1.3424(4) 0.5807(4) 0.6335(4) 0.0398(15) Uani 1 1 d . . . . .
H69A H 1.347835 0.526078 0.647514 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3924(4) -0.1223(4) 0.3796(4) 0.0397(15) Uani 1 1 d . . . . .
H9A H 0.451225 -0.096117 0.379058 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3135(4) -0.0810(4) 0.3592(4) 0.0355(14) Uani 1 1 d . . . . .
H8A H 0.318289 -0.026630 0.344397 0.043 Uiso 1 1 calc R U . . .
C66 C 1.3268(4) 0.7396(4) 0.5947(4) 0.0430(16) Uani 1 1 d . . . . .
H66A H 1.322000 0.794800 0.582573 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2208(4) -0.1985(4) 0.3823(3) 0.0340(14) Uani 1 1 d . . . . .
H12A H 0.162045 -0.224603 0.384139 0.041 Uiso 1 1 calc R U . . .
C70 C 1.0530(4) 0.6204(3) 0.6478(3) 0.0277(13) Uani 1 1 d . . . . .
C44 C 0.7601(4) 0.6948(3) 0.8902(3) 0.0328(14) Uani 1 1 d . . . . .
H44A H 0.702434 0.722137 0.887252 0.039 Uiso 1 1 calc R U . . .
C34 C 0.2148(4) 0.2374(4) 0.8921(4) 0.0375(15) Uani 1 1 d . . . . .
H34A H 0.218967 0.293890 0.904238 0.045 Uiso 1 1 calc R U . . .
C6 C -0.0166(4) -0.1248(4) 0.4235(4) 0.0407(16) Uani 1 1 d . . . . .
H6A H 0.008450 -0.092246 0.465156 0.049 Uiso 1 1 calc R U . . .
C31 C 0.5133(4) 0.1761(3) 0.7891(4) 0.0353(14) Uani 1 1 d . . . . .
H31A H 0.478208 0.184571 0.743554 0.042 Uiso 1 1 calc R U . . .
C57 C 0.6553(4) 0.4677(4) 0.9007(4) 0.0404(16) Uani 1 1 d . . . . .
H57A H 0.709819 0.434224 0.890634 0.061 Uiso 1 1 calc R U . . .
H57B H 0.654492 0.483579 0.955145 0.061 Uiso 1 1 calc R U . . .
H57C H 0.598830 0.436760 0.886221 0.061 Uiso 1 1 calc R U . . .
C35 C 0.1315(4) 0.1964(4) 0.8988(3) 0.0368(15) Uani 1 1 d . . . . .
H35A H 0.078656 0.224916 0.916340 0.044 Uiso 1 1 calc R U . . .
C50 C 0.6060(4) 0.4662(3) 0.7160(4) 0.0361(15) Uani 1 1 d . . . . .
H50A H 0.571370 0.433957 0.748802 0.043 Uiso 1 1 calc R U . . .
C72 C 0.9369(4) 0.7088(4) 0.7004(4) 0.0453(17) Uani 1 1 d . . . . .
H72A H 0.911680 0.737871 0.742836 0.054 Uiso 1 1 calc R U . . .
C62 C 1.2107(4) 0.5676(4) 0.8861(4) 0.0415(16) Uani 1 1 d . . . . .
H62A H 1.242941 0.602189 0.922705 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3299(4) 0.0804(4) 0.5901(4) 0.0398(15) Uani 1 1 d . . . . .
H22A H 0.298531 0.117411 0.558652 0.048 Uiso 1 1 calc R U . . .
C73 C 0.8955(5) 0.7127(4) 0.6296(4) 0.0465(18) Uani 1 1 d . . . . .
H73A H 0.841649 0.744675 0.622957 0.056 Uiso 1 1 calc R U . . .
C55 C 0.4616(7) 0.6818(5) 0.9538(7) 0.092(4) Uani 1 1 d . . . . .
H55A H 0.442635 0.691128 1.004902 0.110 Uiso 1 1 calc R U . . .
C48 C 0.6499(5) 0.4955(5) 0.5903(4) 0.0514(19) Uani 1 1 d . . . . .
H48A H 0.645676 0.484442 0.536639 0.062 Uiso 1 1 calc R U . . .
C49 C 0.6016(4) 0.4505(4) 0.6383(4) 0.0427(16) Uani 1 1 d . . . . .
H49A H 0.563747 0.407108 0.617905 0.051 Uiso 1 1 calc R U . . .
C56 C 0.5343(6) 0.6304(5) 0.9382(5) 0.069(2) Uani 1 1 d . . . . .
H56A H 0.565203 0.603721 0.978379 0.082 Uiso 1 1 calc R U . . .
C10 C 0.3863(4) -0.2014(4) 0.4008(4) 0.0428(16) Uani 1 1 d . . . . .
H10A H 0.440818 -0.229658 0.414850 0.051 Uiso 1 1 calc R U . . .
C51 C 0.5621(4) 0.6181(3) 0.8633(4) 0.0337(14) Uani 1 1 d . . . . .
C5 C -0.0939(5) -0.1738(4) 0.4330(4) 0.0457(17) Uani 1 1 d . . . . .
H5A H -0.122066 -0.174040 0.481364 0.055 Uiso 1 1 calc R U . . .
C67 C 1.4119(4) 0.7024(4) 0.5933(4) 0.0459(17) Uani 1 1 d . . . . .
H67A H 1.465267 0.731640 0.579123 0.055 Uiso 1 1 calc R U . . .
C54 C 0.4166(5) 0.7195(5) 0.8946(7) 0.080(3) Uani 1 1 d . . . . .
H54A H 0.365693 0.753998 0.905102 0.096 Uiso 1 1 calc R U . . .
C43 C 0.8391(4) 0.7371(4) 0.9103(4) 0.0401(15) Uani 1 1 d . . . . .
H43A H 0.836633 0.793918 0.920536 0.048 Uiso 1 1 calc R U . . .
C74 C 0.9309(6) 0.6710(4) 0.5683(5) 0.059(2) Uani 1 1 d . . . . .
H74A H 0.900954 0.673406 0.519547 0.071 Uiso 1 1 calc R U . . .
C23 C 0.3756(4) 0.0148(4) 0.5568(4) 0.0374(15) Uani 1 1 d . . . . .
H23A H 0.376278 0.007291 0.502755 0.045 Uiso 1 1 calc R U . . .
C75 C 1.0105(5) 0.6251(4) 0.5769(4) 0.0490(18) Uani 1 1 d . . . . .
H75A H 1.035478 0.597023 0.533878 0.059 Uiso 1 1 calc R U . . .
C29 C 0.6415(4) 0.2111(4) 0.8735(4) 0.0489(19) Uani 1 1 d . . . . .
H29A H 0.694682 0.243867 0.885877 0.059 Uiso 1 1 calc R U . . .
C28 C 0.6161(4) 0.1521(4) 0.9217(4) 0.0493(18) Uani 1 1 d . . . . .
H28A H 0.651937 0.143776 0.966934 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0679(4) 0.0555(4) 0.1487(5) 0.0506(19) Uani 1 1 d . . . . .
H15A H 0.033028 0.101424 0.134862 0.061 Uiso 1 1 calc R U . . .
C19 C 0.1234(4) 0.0246(4) 0.4032(4) 0.0390(15) Uani 1 1 d . . . . .
H19A H 0.123917 0.007658 0.456087 0.059 Uiso 1 1 calc R U . . .
H19B H 0.178414 0.058182 0.395318 0.059 Uiso 1 1 calc R U . . .
H19C H 0.067339 0.055914 0.393050 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1592(5) -0.0573(5) 0.1129(4) 0.055(2) Uani 1 1 d . . . . .
H17A H 0.188232 -0.089254 0.074216 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1109(5) 0.0099(5) 0.0937(4) 0.053(2) Uani 1 1 d . . . . .
H16A H 0.107222 0.024865 0.041991 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.8103(8) . ?
I1 I3 2.8416(7) . ?
I3 I9 3.8116(7) . ?
I4 I5 2.8001(8) . ?
I4 I6 2.8329(7) . ?
I6 I12 3.8307(8) 2_657 ?
I7 I8 2.8109(7) . ?
I7 I9 2.8801(7) . ?
I10 I11 2.8254(8) . ?
I10 I12 2.8428(7) . ?
P1 C13 1.781(6) . ?
P1 C19 1.785(6) . ?
P1 C7 1.786(6) . ?
P1 C1 1.798(5) . ?
P2 C20 1.775(6) . ?
P2 C32 1.793(5) . ?
P2 C26 1.793(5) . ?
P2 C38 1.794(6) . ?
P3 C51 1.780(6) . ?
P3 C45 1.781(6) . ?
P3 C39 1.787(6) . ?
P3 C57 1.788(6) . ?
P4 C58 1.779(6) . ?
P4 C76 1.792(6) . ?
P4 C70 1.797(6) . ?
P4 C64 1.801(6) . ?
C1 C2 1.379(8) . ?
C1 C6 1.380(8) . ?
C7 C8 1.386(8) . ?
C7 C12 1.398(8) . ?
C20 C21 1.382(8) . ?
C20 C25 1.415(7) . ?
C33 C34 1.383(8) . ?
C33 C32 1.390(8) . ?
C33 H33A 0.9500 . ?
C40 C41 1.374(8) . ?
C40 C39 1.399(8) . ?
C40 H40A 0.9500 . ?
C39 C44 1.386(8) . ?
C14 C15 1.378(9) . ?
C14 C13 1.382(8) . ?
C14 H14A 0.9500 . ?
C2 C3 1.392(8) . ?
C2 H2A 0.9500 . ?
C4 C5 1.364(9) . ?
C4 C3 1.374(9) . ?
C4 H4A 0.9500 . ?
C58 C63 1.388(8) . ?
C58 C59 1.399(8) . ?
C64 C65 1.375(8) . ?
C64 C69 1.390(8) . ?
C37 C36 1.378(8) . ?
C37 C32 1.396(8) . ?
C37 H37A 0.9500 . ?
C60 C59 1.372(9) . ?
C60 C61 1.385(9) . ?
C60 H60A 0.9500 . ?
C26 C31 1.384(8) . ?
C26 C27 1.390(8) . ?
C13 C18 1.381(8) . ?
C68 C69 1.372(8) . ?
C68 C67 1.379(9) . ?
C68 H68A 0.9500 . ?
C21 C22 1.395(9) . ?
C21 H21A 0.9500 . ?
C11 C10 1.374(9) . ?
C11 C12 1.386(8) . ?
C11 H11A 0.9500 . ?
C18 C17 1.371(9) . ?
C18 H18A 0.9500 . ?
C3 H3A 0.9500 . ?
C27 C28 1.383(9) . ?
C27 H27A 0.9500 . ?
C24 C23 1.370(8) . ?
C24 C25 1.372(8) . ?
C24 H24A 0.9500 . ?
C45 C46 1.369(8) . ?
C45 C50 1.393(8) . ?
C30 C29 1.373(10) . ?
C30 C31 1.383(8) . ?
C30 H30A 0.9500 . ?
C65 C66 1.379(8) . ?
C65 H65A 0.9500 . ?
C25 H25A 0.9500 . ?
C59 H59A 0.9500 . ?
C46 C47 1.369(9) . ?
C46 H46A 0.9500 . ?
C76 H76A 0.9800 . ?
C76 H76B 0.9800 . ?
C76 H76C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C42 C41 1.363(9) . ?
C42 C43 1.380(9) . ?
C42 H42A 0.9500 . ?
C52 C51 1.372(9) . ?
C52 C53 1.389(10) . ?
C52 H52A 0.9500 . ?
C47 C48 1.387(10) . ?
C47 H47A 0.9500 . ?
C61 C62 1.387(9) . ?
C61 H61A 0.9500 . ?
C41 H41A 0.9500 . ?
C71 C70 1.389(8) . ?
C71 C72 1.396(9) . ?
C71 H71A 0.9500 . ?
C36 C35 1.369(9) . ?
C36 H36A 0.9500 . ?
C63 C62 1.374(9) . ?
C63 H63A 0.9500 . ?
C53 C54 1.352(13) . ?
C53 H53A 0.9500 . ?
C69 H69A 0.9500 . ?
C9 C8 1.377(8) . ?
C9 C10 1.379(9) . ?
C9 H9A 0.9500 . ?
C8 H8A 0.9500 . ?
C66 C67 1.375(9) . ?
C66 H66A 0.9500 . ?
C12 H12A 0.9500 . ?
C70 C75 1.377(8) . ?
C44 C43 1.362(8) . ?
C44 H44A 0.9500 . ?
C34 C35 1.385(8) . ?
C34 H34A 0.9500 . ?
C6 C5 1.390(9) . ?
C6 H6A 0.9500 . ?
C31 H31A 0.9500 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C35 H35A 0.9500 . ?
C50 C49 1.376(9) . ?
C50 H50A 0.9500 . ?
C72 C73 1.367(10) . ?
C72 H72A 0.9500 . ?
C62 H62A 0.9500 . ?
C22 C23 1.390(9) . ?
C22 H22A 0.9500 . ?
C73 C74 1.364(10) . ?
C73 H73A 0.9500 . ?
C55 C56 1.379(11) . ?
C55 C54 1.384(14) . ?
C55 H55A 0.9500 . ?
C48 C49 1.350(10) . ?
C48 H48A 0.9500 . ?
C49 H49A 0.9500 . ?
C56 C51 1.391(10) . ?
C56 H56A 0.9500 . ?
C10 H10A 0.9500 . ?
C5 H5A 0.9500 . ?
C67 H67A 0.9500 . ?
C54 H54A 0.9500 . ?
C43 H43A 0.9500 . ?
C74 C75 1.389(10) . ?
C74 H74A 0.9500 . ?
C23 H23A 0.9500 . ?
C75 H75A 0.9500 . ?
C29 C28 1.372(10) . ?
C29 H29A 0.9500 . ?
C28 H28A 0.9500 . ?
C15 C16 1.364(10) . ?
C15 H15A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 C16 1.366(10) . ?
C17 H17A 0.9500 . ?
C16 H16A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 I1 I3 174.29(2) . . ?
I1 I3 I9 154.72(2) . . ?
I5 I4 I6 175.28(2) . . ?
I4 I6 I12 154.88(2) . 2_657 ?
I8 I7 I9 175.01(2) . . ?
I7 I9 I3 154.246(19) . . ?
I11 I10 I12 176.14(2) . . ?
I10 I12 I6 154.25(2) . 2_657 ?
C13 P1 C19 109.8(3) . . ?
C13 P1 C7 110.2(3) . . ?
C19 P1 C7 108.3(3) . . ?
C13 P1 C1 108.5(3) . . ?
C19 P1 C1 109.9(3) . . ?
C7 P1 C1 110.1(3) . . ?
C20 P2 C32 110.2(3) . . ?
C20 P2 C26 108.2(3) . . ?
C32 P2 C26 109.2(3) . . ?
C20 P2 C38 110.3(3) . . ?
C32 P2 C38 108.8(3) . . ?
C26 P2 C38 110.2(3) . . ?
C51 P3 C45 108.2(3) . . ?
C51 P3 C39 109.0(3) . . ?
C45 P3 C39 110.0(3) . . ?
C51 P3 C57 110.3(3) . . ?
C45 P3 C57 110.7(3) . . ?
C39 P3 C57 108.7(3) . . ?
C58 P4 C76 110.9(3) . . ?
C58 P4 C70 108.1(3) . . ?
C76 P4 C70 109.8(3) . . ?
C58 P4 C64 110.3(3) . . ?
C76 P4 C64 107.7(3) . . ?
C70 P4 C64 110.1(3) . . ?
C2 C1 C6 120.3(5) . . ?
C2 C1 P1 119.8(4) . . ?
C6 C1 P1 120.0(5) . . ?
C8 C7 C12 119.4(5) . . ?
C8 C7 P1 120.0(4) . . ?
C12 C7 P1 120.4(4) . . ?
C21 C20 C25 118.3(5) . . ?
C21 C20 P2 120.8(4) . . ?
C25 C20 P2 120.8(4) . . ?
C34 C33 C32 120.0(5) . . ?
C34 C33 H33A 120.0 . . ?
C32 C33 H33A 120.0 . . ?
C41 C40 C39 120.1(6) . . ?
C41 C40 H40A 120.0 . . ?
C39 C40 H40A 120.0 . . ?
C44 C39 C40 118.9(5) . . ?
C44 C39 P3 120.8(4) . . ?
C40 C39 P3 120.2(4) . . ?
C15 C14 C13 119.3(6) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C63 C58 C59 119.3(6) . . ?
C63 C58 P4 120.4(4) . . ?
C59 C58 P4 119.9(4) . . ?
C65 C64 C69 120.1(5) . . ?
C65 C64 P4 120.8(4) . . ?
C69 C64 P4 119.1(4) . . ?
C36 C37 C32 119.4(6) . . ?
C36 C37 H37A 120.3 . . ?
C32 C37 H37A 120.3 . . ?
C59 C60 C61 120.4(6) . . ?
C59 C60 H60A 119.8 . . ?
C61 C60 H60A 119.8 . . ?
C31 C26 C27 119.9(5) . . ?
C31 C26 P2 120.1(4) . . ?
C27 C26 P2 120.0(4) . . ?
C18 C13 C14 120.1(6) . . ?
C18 C13 P1 120.6(4) . . ?
C14 C13 P1 119.2(5) . . ?
C69 C68 C67 120.0(6) . . ?
C69 C68 H68A 120.0 . . ?
C67 C68 H68A 120.0 . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C10 C11 C12 120.7(6) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C17 C18 C13 119.4(6) . . ?
C17 C18 H18A 120.3 . . ?
C13 C18 H18A 120.3 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C28 C27 C26 119.9(6) . . ?
C28 C27 H27A 120.1 . . ?
C26 C27 H27A 120.1 . . ?
C23 C24 C25 120.7(5) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C33 C32 C37 119.9(5) . . ?
C33 C32 P2 120.7(4) . . ?
C37 C32 P2 119.4(4) . . ?
C46 C45 C50 118.9(6) . . ?
C46 C45 P3 120.7(5) . . ?
C50 C45 P3 120.3(5) . . ?
C29 C30 C31 120.1(6) . . ?
C29 C30 H30A 120.0 . . ?
C31 C30 H30A 120.0 . . ?
C64 C65 C66 119.5(6) . . ?
C64 C65 H65A 120.2 . . ?
C66 C65 H65A 120.2 . . ?
C24 C25 C20 120.9(5) . . ?
C24 C25 H25A 119.6 . . ?
C20 C25 H25A 119.6 . . ?
C60 C59 C58 119.9(6) . . ?
C60 C59 H59A 120.1 . . ?
C58 C59 H59A 120.1 . . ?
C45 C46 C47 120.5(6) . . ?
C45 C46 H46A 119.7 . . ?
C47 C46 H46A 119.7 . . ?
P4 C76 H76A 109.5 . . ?
P4 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
P4 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
P2 C38 H38A 109.5 . . ?
P2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
P2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C41 C42 C43 120.7(6) . . ?
C41 C42 H42A 119.7 . . ?
C43 C42 H42A 119.7 . . ?
C51 C52 C53 119.2(8) . . ?
C51 C52 H52A 120.4 . . ?
C53 C52 H52A 120.4 . . ?
C46 C47 C48 120.7(7) . . ?
C46 C47 H47A 119.7 . . ?
C48 C47 H47A 119.7 . . ?
C60 C61 C62 120.0(6) . . ?
C60 C61 H61A 120.0 . . ?
C62 C61 H61A 120.0 . . ?
C42 C41 C40 119.9(6) . . ?
C42 C41 H41A 120.0 . . ?
C40 C41 H41A 120.0 . . ?
C70 C71 C72 119.7(6) . . ?
C70 C71 H71A 120.2 . . ?
C72 C71 H71A 120.2 . . ?
C35 C36 C37 120.5(6) . . ?
C35 C36 H36A 119.8 . . ?
C37 C36 H36A 119.8 . . ?
C62 C63 C58 120.6(6) . . ?
C62 C63 H63A 119.7 . . ?
C58 C63 H63A 119.7 . . ?
C54 C53 C52 120.7(9) . . ?
C54 C53 H53A 119.6 . . ?
C52 C53 H53A 119.6 . . ?
C68 C69 C64 119.9(6) . . ?
C68 C69 H69A 120.1 . . ?
C64 C69 H69A 120.1 . . ?
C8 C9 C10 120.3(6) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C67 C66 C65 120.5(6) . . ?
C67 C66 H66A 119.8 . . ?
C65 C66 H66A 119.8 . . ?
C11 C12 C7 119.4(5) . . ?
C11 C12 H12A 120.3 . . ?
C7 C12 H12A 120.3 . . ?
C75 C70 C71 119.6(6) . . ?
C75 C70 P4 120.0(5) . . ?
C71 C70 P4 120.4(5) . . ?
C43 C44 C39 120.3(6) . . ?
C43 C44 H44A 119.8 . . ?
C39 C44 H44A 119.8 . . ?
C33 C34 C35 119.4(6) . . ?
C33 C34 H34A 120.3 . . ?
C35 C34 H34A 120.3 . . ?
C1 C6 C5 119.2(6) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C30 C31 C26 119.7(6) . . ?
C30 C31 H31A 120.2 . . ?
C26 C31 H31A 120.2 . . ?
P3 C57 H57A 109.5 . . ?
P3 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
P3 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C36 C35 C34 120.9(6) . . ?
C36 C35 H35A 119.6 . . ?
C34 C35 H35A 119.6 . . ?
C49 C50 C45 119.7(6) . . ?
C49 C50 H50A 120.1 . . ?
C45 C50 H50A 120.1 . . ?
C73 C72 C71 119.9(7) . . ?
C73 C72 H72A 120.0 . . ?
C71 C72 H72A 120.0 . . ?
C63 C62 C61 119.9(6) . . ?
C63 C62 H62A 120.1 . . ?
C61 C62 H62A 120.1 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C74 C73 C72 120.5(7) . . ?
C74 C73 H73A 119.7 . . ?
C72 C73 H73A 119.7 . . ?
C56 C55 C54 119.6(9) . . ?
C56 C55 H55A 120.2 . . ?
C54 C55 H55A 120.2 . . ?
C49 C48 C47 118.8(7) . . ?
C49 C48 H48A 120.6 . . ?
C47 C48 H48A 120.6 . . ?
C48 C49 C50 121.4(6) . . ?
C48 C49 H49A 119.3 . . ?
C50 C49 H49A 119.3 . . ?
C55 C56 C51 119.6(9) . . ?
C55 C56 H56A 120.2 . . ?
C51 C56 H56A 120.2 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C52 C51 C56 120.4(6) . . ?
C52 C51 P3 121.2(5) . . ?
C56 C51 P3 118.3(6) . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C66 C67 C68 119.9(6) . . ?
C66 C67 H67A 120.0 . . ?
C68 C67 H67A 120.0 . . ?
C53 C54 C55 120.6(8) . . ?
C53 C54 H54A 119.7 . . ?
C55 C54 H54A 119.7 . . ?
C44 C43 C42 120.1(6) . . ?
C44 C43 H43A 120.0 . . ?
C42 C43 H43A 120.0 . . ?
C73 C74 C75 120.4(7) . . ?
C73 C74 H74A 119.8 . . ?
C75 C74 H74A 119.8 . . ?
C24 C23 C22 119.5(6) . . ?
C24 C23 H23A 120.3 . . ?
C22 C23 H23A 120.3 . . ?
C70 C75 C74 119.9(7) . . ?
C70 C75 H75A 120.0 . . ?
C74 C75 H75A 120.0 . . ?
C28 C29 C30 120.8(6) . . ?
C28 C29 H29A 119.6 . . ?
C30 C29 H29A 119.6 . . ?
C29 C28 C27 119.7(7) . . ?
C29 C28 H28A 120.1 . . ?
C27 C28 H28A 120.1 . . ?
C16 C15 C14 120.5(6) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
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 . . ?
C16 C17 C18 120.7(7) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C15 C16 C17 120.1(7) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?

_refine_diff_density_max         0.877
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1909053'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br3 P'
_chemical_formula_weight         517.03

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   10.6889(7)
_cell_length_b                   15.2647(11)
_cell_length_c                   12.2973(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.394(2)
_cell_angle_gamma                90
_cell_volume                     1966.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      26.36

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    6.231
_shelx_estimated_absorpt_T_min   0.254
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21914
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.302
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3642
_reflns_number_gt                2866
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0133P)²+5.5162P] 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         3642
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34419(4) 0.23913(3) 0.55896(3) 0.02213(11) Uani 1 1 d . . . . .
Br2 Br 0.19659(5) 0.37052(3) 0.54095(5) 0.04668(16) Uani 1 1 d . . . . .
Br3 Br 0.49179(4) 0.10793(3) 0.57566(4) 0.02699(12) Uani 1 1 d . . . . .
P1 P 0.23358(9) 0.66175(7) 0.60042(8) 0.0155(2) Uani 1 1 d . . . . .
C1 C 0.1933(4) 0.7735(2) 0.6201(3) 0.0176(8) Uani 1 1 d . . . . .
C2 C 0.2819(4) 0.8390(3) 0.6130(3) 0.0223(9) Uani 1 1 d . . . . .
H2 H 0.366584 0.823830 0.607292 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2471(4) 0.9261(3) 0.6141(4) 0.0293(10) Uani 1 1 d . . . . .
H3 H 0.307439 0.970726 0.608719 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1244(4) 0.9480(3) 0.6231(4) 0.0325(11) Uani 1 1 d . . . . .
H4 H 0.100284 1.007857 0.624173 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0367(4) 0.8833(3) 0.6305(4) 0.0367(12) Uani 1 1 d . . . . .
H5 H -0.047520 0.898827 0.637220 0.044 Uiso 1 1 calc R U . . .
C6 C 0.0701(4) 0.7964(3) 0.6283(4) 0.0283(10) Uani 1 1 d . . . . .
H6 H 0.008807 0.752073 0.632394 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3942(4) 0.6407(3) 0.6690(3) 0.0195(9) Uani 1 1 d . . . . .
C8 C 0.4405(4) 0.6759(3) 0.7733(3) 0.0227(9) Uani 1 1 d . . . . .
H8 H 0.389529 0.715036 0.805974 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5611(4) 0.6534(3) 0.8292(3) 0.0288(10) Uani 1 1 d . . . . .
H9 H 0.592779 0.677107 0.900823 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6362(4) 0.5971(3) 0.7823(4) 0.0337(11) Uani 1 1 d . . . . .
H10 H 0.719705 0.582656 0.820985 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5900(4) 0.5619(4) 0.6797(4) 0.0421(13) Uani 1 1 d . . . . .
H11 H 0.641219 0.522523 0.647648 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4696(4) 0.5834(3) 0.6228(4) 0.0363(12) Uani 1 1 d . . . . .
H12 H 0.438222 0.558778 0.551733 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2182(3) 0.6420(2) 0.4545(3) 0.0154(8) Uani 1 1 d . . . . .
C14 C 0.1255(4) 0.5881(3) 0.3972(3) 0.0223(9) Uani 1 1 d . . . . .
H14 H 0.071492 0.556271 0.435753 0.027 Uiso 1 1 calc R U . . .
C15 C 0.1106(4) 0.5801(3) 0.2834(3) 0.0275(10) Uani 1 1 d . . . . .
H15 H 0.046500 0.542571 0.243939 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1881(4) 0.6262(3) 0.2270(4) 0.0313(11) Uani 1 1 d . . . . .
H16 H 0.177659 0.620286 0.148801 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2810(4) 0.6809(3) 0.2841(4) 0.0340(11) Uani 1 1 d . . . . .
H17 H 0.333908 0.713361 0.245054 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2971(4) 0.6886(3) 0.3977(3) 0.0268(10) Uani 1 1 d . . . . .
H18 H 0.361969 0.725587 0.437154 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1288(4) 0.5917(3) 0.6567(3) 0.0214(9) Uani 1 1 d . . . . .
H19A H 0.040462 0.602992 0.619324 0.032 Uiso 1 1 calc R U . . .
H19B H 0.150384 0.530439 0.645414 0.032 Uiso 1 1 calc R U . . .
H19C H 0.137891 0.603268 0.736272 0.032 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Br3 2.5326(6) . ?
Br1 Br2 2.5342(6) . ?
P1 C19 1.784(4) . ?
P1 C7 1.786(4) . ?
P1 C1 1.788(4) . ?
P1 C13 1.795(4) . ?
C1 C6 1.385(5) . ?
C1 C2 1.392(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.386(6) . ?
C7 C8 1.388(5) . ?
C8 C9 1.379(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.371(5) . ?
C13 C18 1.391(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br3 Br1 Br2 179.63(2) . . ?
C19 P1 C7 109.15(19) . . ?
C19 P1 C1 109.46(19) . . ?
C7 P1 C1 110.00(18) . . ?
C19 P1 C13 110.31(18) . . ?
C7 P1 C13 109.36(18) . . ?
C1 P1 C13 108.55(18) . . ?
C6 C1 C2 119.5(4) . . ?
C6 C1 P1 120.5(3) . . ?
C2 C1 P1 119.5(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 119.5(4) . . ?
C12 C7 P1 120.2(3) . . ?
C8 C7 P1 120.1(3) . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 119.8(4) . . ?
C14 C13 P1 121.9(3) . . ?
C18 C13 P1 118.1(3) . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
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 . . ?

_refine_diff_density_max         0.824
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1909051'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br1.78 I1.22 P'
_chemical_formula_weight         574.13

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'
Br Br -0.2901 2.4595 '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                   8.6136(9)
_cell_length_b                   15.0989(14)
_cell_length_c                   15.6608(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.018(4)
_cell_angle_gamma                90
_cell_volume                     2025.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9430
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.24

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_F_000             1095
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    5.506
_shelx_estimated_absorpt_T_min   0.400
_shelx_estimated_absorpt_T_max   0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec ImuS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58325
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.591
_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             4196
_reflns_number_gt                3845
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0170P)²+1.2980P] 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         4196
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0414
_refine_ls_wR_factor_gt          0.0403
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.06271(2) 0.45975(2) 0.71111(2) 0.02085(5) Uani 1 1 d . . . . .
Br2 Br 0.90553(2) 0.51269(2) 0.84231(2) 0.03167(8) Uani 0.784(2) 1 d . . P . .
I2 I 0.90553(2) 0.51269(2) 0.84231(2) 0.03167(8) Uani 0.216(2) 1 d . . P . .
Br3 Br 1.22436(3) 0.40346(2) 0.57700(2) 0.02696(6) Uani 1 1 d . . . . .
P1 P 0.55081(6) 0.63960(3) 0.67586(3) 0.01545(10) Uani 1 1 d . . . . .
C1 C 0.4550(2) 0.61606(13) 0.76949(13) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.4861(2) 0.53709(13) 0.81461(14) 0.0206(4) Uani 1 1 d . . . . .
H2 H 0.556951 0.495256 0.795179 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4136(3) 0.51991(14) 0.88774(14) 0.0253(5) Uani 1 1 d . . . . .
H3 H 0.433795 0.465977 0.918117 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3119(3) 0.58107(15) 0.91653(14) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.263031 0.569211 0.966967 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2805(3) 0.65972(15) 0.87229(15) 0.0290(5) Uani 1 1 d . . . . .
H5 H 0.210190 0.701467 0.892316 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3518(2) 0.67729(14) 0.79892(14) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.330448 0.731147 0.768598 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4187(2) 0.69910(13) 0.60031(12) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.2908(2) 0.65522(15) 0.55717(13) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.276017 0.593643 0.565811 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1854(3) 0.70260(16) 0.50153(14) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.098179 0.673448 0.471726 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2077(3) 0.79259(16) 0.48953(14) 0.0310(5) Uani 1 1 d . . . . .
H10 H 0.134945 0.824820 0.451710 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3337(3) 0.83555(15) 0.53169(15) 0.0324(5) Uani 1 1 d . . . . .
H11 H 0.347614 0.897152 0.522796 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4407(3) 0.78938(14) 0.58722(14) 0.0245(5) Uani 1 1 d . . . . .
H12 H 0.528314 0.819033 0.616089 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7213(2) 0.70607(13) 0.70405(13) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.7361(3) 0.75325(14) 0.78018(13) 0.0230(4) Uani 1 1 d . . . . .
H14 H 0.654921 0.751696 0.816796 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8699(3) 0.80296(14) 0.80311(15) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.880871 0.834372 0.855959 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9857(2) 0.80677(14) 0.74997(15) 0.0272(5) Uani 1 1 d . . . . .
H16 H 1.076157 0.841602 0.765339 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9711(3) 0.7603(2) 0.67446(19) 0.0465(7) Uani 1 1 d . . . . .
H17 H 1.052199 0.762790 0.637838 0.056 Uiso 1 1 calc R U . . .
C18 C 0.8389(3) 0.70953(19) 0.65079(17) 0.0398(6) Uani 1 1 d . . . . .
H18 H 0.829707 0.677444 0.598323 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6056(2) 0.53812(13) 0.62853(14) 0.0218(4) Uani 1 1 d . . . . .
H19A H 0.513267 0.500403 0.616577 0.033 Uiso 1 1 calc R U . . .
H19B H 0.683232 0.507522 0.668237 0.033 Uiso 1 1 calc R U . . .
H19C H 0.650269 0.550788 0.574809 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Br2 2.6975(3) . ?
I1 Br3 2.7723(3) . ?
P1 C19 1.787(2) . ?
P1 C1 1.792(2) . ?
P1 C7 1.794(2) . ?
P1 C13 1.795(2) . ?
C1 C6 1.394(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.394(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.379(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.369(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 I1 Br3 179.369(8) . . ?
C19 P1 C1 109.49(10) . . ?
C19 P1 C7 109.42(10) . . ?
C1 P1 C7 108.91(9) . . ?
C19 P1 C13 109.68(10) . . ?
C1 P1 C13 110.16(9) . . ?
C7 P1 C13 109.15(9) . . ?
C6 C1 C2 119.60(19) . . ?
C6 C1 P1 120.23(15) . . ?
C2 C1 P1 120.16(15) . . ?
C3 C2 C1 119.88(19) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.08(19) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C12 C7 C8 120.31(19) . . ?
C12 C7 P1 119.99(16) . . ?
C8 C7 P1 119.66(15) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C18 C13 C14 119.63(19) . . ?
C18 C13 P1 120.42(16) . . ?
C14 C13 P1 119.94(15) . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 119.5(2) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 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 . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1909052'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br2.14 I0.86 P'
_chemical_formula_weight         557.56

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'
Br Br -0.2901 2.4595 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   10.8305(8)
_cell_length_b                   15.5357(12)
_cell_length_c                   12.3762(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.654(2)
_cell_angle_gamma                90
_cell_volume                     2039.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.42

_exptl_crystal_description       tabular
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_F_000             1070
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    5.625
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8302
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24244
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.609
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3771
_reflns_number_gt                3092
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0236P)²+3.9568P] 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         3771
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.34527(2) 0.24253(2) 0.55699(2) 0.02490(10) Uani 0.864(5) 1 d . . P . .
Br1 Br 0.34527(2) 0.24253(2) 0.55699(2) 0.02490(10) Uani 0.136(5) 1 d . . P . .
Br2 Br 0.18976(5) 0.37973(3) 0.53808(5) 0.05912(18) Uani 1 1 d . . . . .
Br3 Br 0.50088(4) 0.10468(3) 0.57726(3) 0.03107(13) Uani 1 1 d . . . . .
P1 P 0.23249(9) 0.66415(6) 0.59943(7) 0.0213(2) Uani 1 1 d . . . . .
C1 C 0.1939(3) 0.7746(2) 0.6181(3) 0.0239(8) Uani 1 1 d . . . . .
C2 C 0.2821(4) 0.8387(2) 0.6136(3) 0.0293(9) Uani 1 1 d . . . . .
H2 H 0.365838 0.823535 0.609065 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2484(4) 0.9244(3) 0.6157(3) 0.0383(10) Uani 1 1 d . . . . .
H3 H 0.308527 0.968152 0.611631 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1270(4) 0.9462(3) 0.6238(3) 0.0393(11) Uani 1 1 d . . . . .
H4 H 0.104120 1.005125 0.626221 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0392(4) 0.8833(3) 0.6285(4) 0.0431(11) Uani 1 1 d . . . . .
H5 H -0.044026 0.898917 0.634209 0.052 Uiso 1 1 calc R U . . .
C6 C 0.0712(4) 0.7973(3) 0.6249(3) 0.0322(9) Uani 1 1 d . . . . .
H6 H 0.009828 0.753953 0.627072 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3914(3) 0.6423(2) 0.6671(3) 0.0235(8) Uani 1 1 d . . . . .
C8 C 0.4395(4) 0.6776(3) 0.7698(3) 0.0288(9) Uani 1 1 d . . . . .
H8 H 0.391123 0.717759 0.801662 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5589(4) 0.6537(3) 0.8259(3) 0.0363(10) Uani 1 1 d . . . . .
H9 H 0.591807 0.677121 0.896761 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6295(4) 0.5966(3) 0.7793(4) 0.0417(11) Uani 1 1 d . . . . .
H10 H 0.711581 0.581266 0.817760 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5822(4) 0.5612(3) 0.6773(4) 0.0507(13) Uani 1 1 d . . . . .
H11 H 0.631103 0.521195 0.645755 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4638(4) 0.5843(3) 0.6212(3) 0.0420(11) Uani 1 1 d . . . . .
H12 H 0.431386 0.560373 0.550505 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2152(3) 0.6438(2) 0.4543(3) 0.0209(8) Uani 1 1 d . . . . .
C14 C 0.1255(4) 0.5870(3) 0.4000(3) 0.0299(9) Uani 1 1 d . . . . .
H14 H 0.073545 0.555943 0.439744 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1121(4) 0.5756(3) 0.2872(3) 0.0367(10) Uani 1 1 d . . . . .
H15 H 0.051389 0.536030 0.249796 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1855(4) 0.6208(3) 0.2292(3) 0.0343(10) Uani 1 1 d . . . . .
H16 H 0.175095 0.612785 0.151789 0.041 Uiso 1 1 calc R U . . .
C17 C 0.2749(4) 0.6782(3) 0.2831(3) 0.0361(10) Uani 1 1 d . . . . .
H17 H 0.325570 0.709778 0.242671 0.043 Uiso 1 1 calc R U . . .
C18 C 0.2904(4) 0.6896(3) 0.3958(3) 0.0315(9) Uani 1 1 d . . . . .
H18 H 0.352179 0.728496 0.433180 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1303(4) 0.5958(2) 0.6572(3) 0.0279(9) Uani 1 1 d . . . . .
H19A H 0.042635 0.607003 0.620940 0.042 Uiso 1 1 calc R U . . .
H19B H 0.151052 0.535519 0.645957 0.042 Uiso 1 1 calc R U . . .
H19C H 0.141018 0.607434 0.736363 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Br2 2.6973(5) . ?
I1 Br3 2.7053(5) . ?
Br2 C14 3.645(4) . ?
Br3 Br3 3.7712(9) 3_656 ?
P1 C19 1.784(4) . ?
P1 C7 1.788(4) . ?
P1 C1 1.792(4) . ?
P1 C13 1.795(3) . ?
C1 C2 1.388(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.383(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(5) . ?
C7 C12 1.389(5) . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 C18 1.389(5) . ?
C14 C15 1.386(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 I1 Br3 179.621(19) . . ?
I1 Br2 C14 142.68(6) . . ?
I1 Br3 Br3 134.15(2) . 3_656 ?
C19 P1 C7 108.40(18) . . ?
C19 P1 C1 109.75(18) . . ?
C7 P1 C1 110.44(17) . . ?
C19 P1 C13 110.38(17) . . ?
C7 P1 C13 109.37(16) . . ?
C1 P1 C13 108.51(16) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 P1 120.0(3) . . ?
C6 C1 P1 120.0(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.6(3) . . ?
C8 C7 P1 120.2(3) . . ?
C12 C7 P1 120.1(3) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.5(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C14 C13 C18 120.1(3) . . ?
C14 C13 P1 121.3(3) . . ?
C18 C13 P1 118.5(3) . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 Br2 106.7(2) . . ?
C15 C14 Br2 109.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
Br2 C14 H14 52.1 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 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 . . ?

_refine_diff_density_max         1.011
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.097

