# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

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

data_erk8280
_database_code_depnum_ccdc_archive 'CCDC 1515080'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H35 B F15 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         794.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.898(3)
_cell_length_b                   11.2532(9)
_cell_length_c                   21.7565(19)
_cell_angle_alpha                90
_cell_angle_beta                 105.318(5)
_cell_angle_gamma                90
_cell_volume                     6823.8(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4821
_cell_measurement_theta_min      4.2138
_cell_measurement_theta_max      65.9265
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3248

_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            39592
_diffrn_reflns_av_R_equivalents  0.1569
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_full        65.07
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             5803
_reflns_number_gt                3530
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.1155
_refine_ls_wR_factor_gt          0.2947
_refine_ls_wR_factor_ref         0.3337
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         5803
_refine_ls_number_parameters     486
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1592P)²+65.6657P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.506
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.5734(3) 0.4532(9) 0.3852(5) 0.048(2) Uani d . . . 1 . .
H H2 0.562(3) 0.565(8) 0.385(4) 0.06(2) Uiso d . . . 1 . .
C C1 0.6558(4) 0.0635(8) 0.8479(5) 0.061(2) Uani d . . . 1 . .
H H1A 0.6877 0.0241 0.8648 0.073 Uiso calc U . R 1 . .
P P1 0.62430(7) 0.03005(19) 0.90707(10) 0.0436(5) Uani d . . . 1 . .
H H1 0.602(3) -0.076(8) 0.890(4) 0.06(2) Uiso d . . . 1 . .
C C2 0.6358(4) 0.0036(9) 0.7876(5) 0.072(3) Uani d . . . 1 . .
H H2A 0.603 0.034 0.7684 0.087 Uiso calc U . R 1 . .
H H2B 0.6334 -0.0826 0.7953 0.087 Uiso calc U . R 1 . .
C C3 0.6679(4) 0.0238(9) 0.7395(4) 0.061(2) Uani d . . . 1 . .
H H3A 0.699 -0.0176 0.7553 0.073 Uiso calc U . R 1 . .
H H3B 0.6515 -0.0093 0.6972 0.073 Uiso calc U . R 1 . .
C C4 0.6764(5) 0.1563(11) 0.7336(5) 0.081(3) Uani d . . . 1 . .
H H4A 0.6981 0.1678 0.7057 0.097 Uiso calc U . R 1 . .
H H4B 0.6454 0.1948 0.7126 0.097 Uiso calc U . R 1 . .
C C5 0.6968(4) 0.2149(9) 0.7938(5) 0.062(3) Uani d . . . 1 . .
H H5A 0.6984 0.3014 0.7862 0.075 Uiso calc U . R 1 . .
H H5B 0.7301 0.1861 0.8113 0.075 Uiso calc U . R 1 . .
C C6 0.6686(3) 0.1945(7) 0.8437(4) 0.0429(18) Uani d . . . 1 . .
H H6A 0.6881 0.2218 0.8859 0.051 Uiso calc U . R 1 . .
H H6B 0.6388 0.2423 0.8323 0.051 Uiso calc U . R 1 . .
C C11 0.6646(3) 0.0150(7) 0.9867(4) 0.0464(19) Uani d . . . 1 . .
H H11 0.6457 -0.0251 1.0131 0.056 Uiso calc U . R 1 . .
C C12 0.7079(3) -0.0669(8) 0.9884(5) 0.054(2) Uani d . . . 1 . .
H H12A 0.6961 -0.1449 0.9696 0.064 Uiso calc U . R 1 . .
H H12B 0.7277 -0.0314 0.9624 0.064 Uiso calc U . R 1 . .
C C13 0.7388(3) -0.0851(8) 1.0566(5) 0.061(2) Uani d . . . 1 . .
H H13A 0.7204 -0.1312 1.0809 0.073 Uiso calc U . R 1 . .
H H13B 0.7677 -0.1317 1.0556 0.073 Uiso calc U . R 1 . .
C C14 0.7543(3) 0.0331(8) 1.0902(5) 0.056(2) Uani d . . . 1 . .
H H14A 0.7761 0.0748 1.0692 0.067 Uiso calc U . R 1 . .
H H14B 0.7719 0.0181 1.1351 0.067 Uiso calc U . R 1 . .
C C15 0.7103(3) 0.1118(8) 1.0879(4) 0.053(2) Uani d . . . 1 . .
H H15A 0.6898 0.073 1.112 0.064 Uiso calc U . R 1 . .
H H15B 0.7211 0.1891 1.1085 0.064 Uiso calc U . R 1 . .
C C16 0.6812(3) 0.1327(7) 1.0194(4) 0.051(2) Uani d . . . 1 . .
H H16A 0.653 0.1828 1.019 0.061 Uiso calc U . R 1 . .
H H16B 0.7012 0.1753 0.9958 0.061 Uiso calc U . R 1 . .
C C21 0.5748(3) 0.1294(7) 0.9070(3) 0.0392(17) Uani d . . . 1 . .
H H21 0.588 0.2114 0.9165 0.047 Uiso calc U . R 1 . .
C C22 0.5375(3) 0.1323(8) 0.8425(4) 0.049(2) Uani d . . . 1 . .
H H22A 0.5526 0.1632 0.8098 0.058 Uiso calc U . R 1 . .
H H22B 0.5262 0.0504 0.8302 0.058 Uiso calc U . R 1 . .
C C23 0.4946(3) 0.2103(8) 0.8443(4) 0.050(2) Uani d . . . 1 . .
H H23A 0.4701 0.2046 0.8029 0.06 Uiso calc U . R 1 . .
H H23B 0.5052 0.2941 0.8506 0.06 Uiso calc U . R 1 . .
C C24 0.4720(3) 0.1736(8) 0.8978(4) 0.049(2) Uani d . . . 1 . .
H H24A 0.4457 0.229 0.8993 0.059 Uiso calc U . R 1 . .
H H24B 0.4583 0.0927 0.8895 0.059 Uiso calc U . R 1 . .
C C25 0.5102(3) 0.1756(8) 0.9616(4) 0.0473(19) Uani d . . . 1 . .
H H25A 0.4956 0.1514 0.9959 0.057 Uiso calc U . R 1 . .
H H25B 0.5225 0.2577 0.9707 0.057 Uiso calc U . R 1 . .
C C26 0.5522(3) 0.0921(7) 0.9613(4) 0.0458(19) Uani d . . . 1 . .
H H26A 0.5405 0.0092 0.9546 0.055 Uiso calc U . R 1 . .
H H26B 0.5766 0.0964 1.0028 0.055 Uiso calc U . R 1 . .
C C31 0.6014(3) 0.4319(7) 0.3288(4) 0.0440(18) Uani d . . . 1 . .
C C32 0.5933(3) 0.5105(8) 0.2773(4) 0.052(2) Uani d . . . 1 . .
F F32 0.5606(2) 0.5985(5) 0.2702(2) 0.0689(15) Uani d . . . 1 . .
C C33 0.6175(4) 0.5050(8) 0.2310(4) 0.058(2) Uani d . . . 1 . .
F F33 0.6073(3) 0.5820(5) 0.1812(3) 0.0848(19) Uani d . . . 1 . .
C C34 0.6519(3) 0.4216(9) 0.2347(4) 0.057(2) Uani d . . . 1 . .
F F34 0.6768(3) 0.4152(6) 0.1897(3) 0.092(2) Uani d . . . 1 . .
C C35 0.6626(3) 0.3435(8) 0.2844(4) 0.0461(19) Uani d . . . 1 . .
F F35 0.69681(19) 0.2593(5) 0.2896(3) 0.0670(14) Uani d . . . 1 . .
C C36 0.6376(3) 0.3505(7) 0.3294(3) 0.0398(17) Uani d . . . 1 . .
F F36 0.64765(18) 0.2667(4) 0.3769(2) 0.0561(12) Uani d . . . 1 . .
C C41 0.6101(3) 0.4245(7) 0.4554(4) 0.0440(18) Uani d . . . 1 . .
C C42 0.6428(3) 0.5077(7) 0.4840(4) 0.0450(19) Uani d . . . 1 . .
F F42 0.64483(17) 0.6144(4) 0.4537(2) 0.0573(13) Uani d . . . 1 . .
C C43 0.6758(3) 0.4960(7) 0.5430(4) 0.0442(19) Uani d . . . 1 . .
F F43 0.70642(17) 0.5841(4) 0.5667(2) 0.0546(12) Uani d . . . 1 . .
C C44 0.6762(3) 0.3929(7) 0.5781(3) 0.0412(18) Uani d . . . 1 . .
F F44 0.70797(16) 0.3796(4) 0.6346(2) 0.0548(12) Uani d . . . 1 . .
C C45 0.6436(3) 0.3067(7) 0.5522(4) 0.0432(18) Uani d . . . 1 . .
F F45 0.64204(17) 0.2051(4) 0.5848(2) 0.0564(12) Uani d . . . 1 . .
C C46 0.6124(3) 0.3231(8) 0.4917(4) 0.049(2) Uani d . . . 1 . .
F F46 0.58251(16) 0.2287(4) 0.4695(2) 0.0522(12) Uani d . . . 1 . .
C C51 0.5236(3) 0.3735(7) 0.3756(4) 0.0441(19) Uani d . . . 1 . .
C C52 0.5110(3) 0.2719(8) 0.3418(4) 0.051(2) Uani d . . . 1 . .
F F52 0.54317(16) 0.2202(4) 0.3136(3) 0.0593(13) Uani d . . . 1 . .
C C53 0.4697(3) 0.2122(8) 0.3370(5) 0.055(2) Uani d . . . 1 . .
F F53 0.46019(18) 0.1066(4) 0.3048(3) 0.0671(15) Uani d . . . 1 . .
C C54 0.4379(3) 0.2553(8) 0.3668(4) 0.054(2) Uani d . . . 1 . .
F F54 0.3958(2) 0.1926(6) 0.3626(3) 0.0816(18) Uani d . . . 1 . .
C C55 0.4443(3) 0.3581(9) 0.3983(5) 0.058(2) Uani d . . . 1 . .
F F55 0.4138(2) 0.4000(6) 0.4288(3) 0.0831(18) Uani d . . . 1 . .
C C56 0.4894(4) 0.4201(8) 0.4025(4) 0.057(2) Uani d . . . 1 . .
F F56 0.49507(19) 0.5210(5) 0.4353(2) 0.0665(14) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C41 . 1.646(12) ?
B1 C31 . 1.658(12) ?
B1 C51 . 1.661(12) ?
B1 H2 . 1.29(9) ?
C1 C2 . 1.452(14) ?
C1 C6 . 1.529(12) ?
C1 P1 . 1.802(9) ?
C1 H1A . 1.0 ?
P1 C21 . 1.817(8) ?
P1 C11 . 1.821(9) ?
P1 H1 . 1.35(9) ?
C2 C3 . 1.589(12) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.522(15) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.446(14) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.537(11) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C11 C16 . 1.520(11) ?
C11 C12 . 1.545(11) ?
C11 H11 . 1.0 ?
C12 C13 . 1.529(13) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.526(13) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.539(12) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.525(12) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C22 . 1.527(11) ?
C21 C26 . 1.549(10) ?
C21 H21 . 1.0 ?
C22 C23 . 1.527(12) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.535(11) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.528(12) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.535(11) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C31 C36 . 1.387(11) ?
C31 C32 . 1.397(12) ?
C32 F32 . 1.348(10) ?
C32 C33 . 1.373(13) ?
C33 C34 . 1.353(13) ?
C33 F33 . 1.357(10) ?
C34 C35 . 1.363(12) ?
C34 F34 . 1.364(10) ?
C35 F35 . 1.353(9) ?
C35 C36 . 1.363(11) ?
C36 F36 . 1.372(8) ?
C41 C42 . 1.358(12) ?
C41 C46 . 1.379(12) ?
C42 F42 . 1.379(9) ?
C42 C43 . 1.388(11) ?
C43 F43 . 1.339(9) ?
C43 C44 . 1.388(11) ?
C44 F44 . 1.334(8) ?
C44 C45 . 1.364(11) ?
C45 F45 . 1.353(9) ?
C45 C46 . 1.398(12) ?
C46 F46 . 1.374(9) ?
C51 C52 . 1.355(12) ?
C51 C56 . 1.379(12) ?
C52 C53 . 1.350(12) ?
C52 F52 . 1.371(10) ?
C53 C54 . 1.348(13) ?
C53 F53 . 1.371(10) ?
C54 C55 . 1.332(14) ?
C54 F54 . 1.388(10) ?
C55 F55 . 1.323(10) ?
C55 C56 . 1.459(14) ?
C56 F56 . 1.329(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C41 B1 C31 . . 109.6(7) ?
C41 B1 C51 . . 109.6(7) ?
C31 B1 C51 . . 113.9(7) ?
C41 B1 H2 . . 107.(4) ?
C31 B1 H2 . . 108.(4) ?
C51 B1 H2 . . 109.(4) ?
C2 C1 C6 . . 116.0(8) ?
C2 C1 P1 . . 113.1(7) ?
C6 C1 P1 . . 114.8(6) ?
C2 C1 H1A . . 103.6 ?
C6 C1 H1A . . 103.6 ?
P1 C1 H1A . . 103.6 ?
C1 P1 C21 . . 114.7(4) ?
C1 P1 C11 . . 112.4(4) ?
C21 P1 C11 . . 111.3(4) ?
C1 P1 H1 . . 106.(4) ?
C21 P1 H1 . . 103.(4) ?
C11 P1 H1 . . 108.(4) ?
C1 C2 C3 . . 111.4(8) ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 109.4(8) ?
C4 C3 H3A . . 109.8 ?
C2 C3 H3A . . 109.8 ?
C4 C3 H3B . . 109.8 ?
C2 C3 H3B . . 109.8 ?
H3A C3 H3B . . 108.3 ?
C5 C4 C3 . . 114.0(9) ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C6 . . 113.9(8) ?
C4 C5 H5A . . 108.8 ?
C6 C5 H5A . . 108.8 ?
C4 C5 H5B . . 108.8 ?
C6 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
C1 C6 C5 . . 111.6(7) ?
C1 C6 H6A . . 109.3 ?
C5 C6 H6A . . 109.3 ?
C1 C6 H6B . . 109.3 ?
C5 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C16 C11 C12 . . 110.8(7) ?
C16 C11 P1 . . 114.1(6) ?
C12 C11 P1 . . 112.9(6) ?
C16 C11 H11 . . 106.2 ?
C12 C11 H11 . . 106.2 ?
P1 C11 H11 . . 106.2 ?
C13 C12 C11 . . 111.5(7) ?
C13 C12 H12A . . 109.3 ?
C11 C12 H12A . . 109.3 ?
C13 C12 H12B . . 109.3 ?
C11 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C12 . . 111.7(8) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C15 . . 110.6(7) ?
C13 C14 H14A . . 109.5 ?
C15 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
C15 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C16 C15 C14 . . 110.9(7) ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15B . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C11 C16 C15 . . 110.4(7) ?
C11 C16 H16A . . 109.6 ?
C15 C16 H16A . . 109.6 ?
C11 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C22 C21 C26 . . 111.6(6) ?
C22 C21 P1 . . 112.2(5) ?
C26 C21 P1 . . 108.9(5) ?
C22 C21 H21 . . 108.0 ?
C26 C21 H21 . . 108.0 ?
P1 C21 H21 . . 108.0 ?
C23 C22 C21 . . 111.7(6) ?
C23 C22 H22A . . 109.3 ?
C21 C22 H22A . . 109.3 ?
C23 C22 H22B . . 109.3 ?
C21 C22 H22B . . 109.3 ?
H22A C22 H22B . . 108.0 ?
C22 C23 C24 . . 112.0(7) ?
C22 C23 H23A . . 109.2 ?
C24 C23 H23A . . 109.2 ?
C22 C23 H23B . . 109.2 ?
C24 C23 H23B . . 109.2 ?
H23A C23 H23B . . 107.9 ?
C25 C24 C23 . . 109.5(6) ?
C25 C24 H24A . . 109.8 ?
C23 C24 H24A . . 109.8 ?
C25 C24 H24B . . 109.8 ?
C23 C24 H24B . . 109.8 ?
H24A C24 H24B . . 108.2 ?
C24 C25 C26 . . 111.6(7) ?
C24 C25 H25A . . 109.3 ?
C26 C25 H25A . . 109.3 ?
C24 C25 H25B . . 109.3 ?
C26 C25 H25B . . 109.3 ?
H25A C25 H25B . . 108.0 ?
C25 C26 C21 . . 109.3(6) ?
C25 C26 H26A . . 109.8 ?
C21 C26 H26A . . 109.8 ?
C25 C26 H26B . . 109.8 ?
C21 C26 H26B . . 109.8 ?
H26A C26 H26B . . 108.3 ?
C36 C31 C32 . . 113.1(7) ?
C36 C31 B1 . . 127.1(7) ?
C32 C31 B1 . . 119.3(7) ?
F32 C32 C33 . . 115.2(8) ?
F32 C32 C31 . . 121.5(8) ?
C33 C32 C31 . . 123.3(8) ?
C34 C33 F33 . . 119.6(8) ?
C34 C33 C32 . . 119.7(8) ?
F33 C33 C32 . . 120.7(9) ?
C33 C34 C35 . . 120.3(8) ?
C33 C34 F34 . . 120.8(8) ?
C35 C34 F34 . . 119.0(9) ?
F35 C35 C34 . . 121.7(7) ?
F35 C35 C36 . . 119.6(7) ?
C34 C35 C36 . . 118.7(7) ?
C35 C36 F36 . . 117.0(7) ?
C35 C36 C31 . . 124.9(7) ?
F36 C36 C31 . . 118.0(7) ?
C42 C41 C46 . . 112.7(7) ?
C42 C41 B1 . . 119.3(7) ?
C46 C41 B1 . . 128.0(7) ?
C41 C42 F42 . . 119.6(7) ?
C41 C42 C43 . . 125.7(8) ?
F42 C42 C43 . . 114.8(7) ?
F43 C43 C44 . . 120.0(7) ?
F43 C43 C42 . . 120.6(7) ?
C44 C43 C42 . . 119.5(7) ?
F44 C44 C45 . . 122.2(7) ?
F44 C44 C43 . . 120.3(7) ?
C45 C44 C43 . . 117.5(7) ?
F45 C45 C44 . . 120.0(7) ?
F45 C45 C46 . . 120.1(7) ?
C44 C45 C46 . . 119.9(7) ?
F46 C46 C41 . . 120.5(7) ?
F46 C46 C45 . . 114.8(8) ?
C41 C46 C45 . . 124.7(8) ?
C52 C51 C56 . . 115.5(8) ?
C52 C51 B1 . . 128.6(7) ?
C56 C51 B1 . . 115.8(7) ?
C53 C52 C51 . . 124.5(8) ?
C53 C52 F52 . . 116.4(8) ?
C51 C52 F52 . . 119.0(7) ?
C54 C53 C52 . . 119.1(9) ?
C54 C53 F53 . . 119.2(8) ?
C52 C53 F53 . . 121.7(8) ?
C55 C54 C53 . . 122.6(8) ?
C55 C54 F54 . . 118.5(8) ?
C53 C54 F54 . . 118.9(9) ?
F55 C55 C54 . . 123.1(9) ?
F55 C55 C56 . . 120.1(9) ?
C54 C55 C56 . . 116.7(8) ?
F56 C56 C51 . . 123.6(9) ?
F56 C56 C55 . . 115.1(8) ?
C51 C56 C55 . . 121.3(8) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 P1 C21 . . . . -89.6(9) ?
C6 C1 P1 C21 . . . . 46.6(9) ?
C2 C1 P1 C11 . . . . 141.8(8) ?
C6 C1 P1 C11 . . . . -81.9(8) ?
C6 C1 C2 C3 . . . . 50.6(12) ?
P1 C1 C2 C3 . . . . -173.7(7) ?
C1 C2 C3 C4 . . . . -52.6(13) ?
C2 C3 C4 C5 . . . . 54.9(13) ?
C3 C4 C5 C6 . . . . -53.4(13) ?
C2 C1 C6 C5 . . . . -47.0(12) ?
P1 C1 C6 C5 . . . . 178.1(7) ?
C4 C5 C6 C1 . . . . 46.8(12) ?
C1 P1 C11 C16 . . . . 79.1(7) ?
C21 P1 C11 C16 . . . . -51.2(7) ?
C1 P1 C11 C12 . . . . -48.5(7) ?
C21 P1 C11 C12 . . . . -178.8(6) ?
C16 C11 C12 C13 . . . . 55.1(10) ?
P1 C11 C12 C13 . . . . -175.6(6) ?
C11 C12 C13 C14 . . . . -53.8(10) ?
C12 C13 C14 C15 . . . . 54.6(10) ?
C13 C14 C15 C16 . . . . -57.0(10) ?
C12 C11 C16 C15 . . . . -57.4(9) ?
P1 C11 C16 C15 . . . . 174.0(6) ?
C14 C15 C16 C11 . . . . 58.7(10) ?
C1 P1 C21 C22 . . . . 57.5(7) ?
C11 P1 C21 C22 . . . . -173.4(5) ?
C1 P1 C21 C26 . . . . -178.4(6) ?
C11 P1 C21 C26 . . . . -49.3(6) ?
C26 C21 C22 C23 . . . . 54.0(9) ?
P1 C21 C22 C23 . . . . 176.6(6) ?
C21 C22 C23 C24 . . . . -54.2(9) ?
C22 C23 C24 C25 . . . . 55.9(9) ?
C23 C24 C25 C26 . . . . -58.6(9) ?
C24 C25 C26 C21 . . . . 58.4(9) ?
C22 C21 C26 C25 . . . . -55.6(9) ?
P1 C21 C26 C25 . . . . -180.0(6) ?
C41 B1 C31 C36 . . . . 31.3(11) ?
C51 B1 C31 C36 . . . . -92.0(10) ?
C41 B1 C31 C32 . . . . -140.6(8) ?
C51 B1 C31 C32 . . . . 96.2(9) ?
C36 C31 C32 F32 . . . . -177.6(7) ?
B1 C31 C32 F32 . . . . -4.7(12) ?
C36 C31 C32 C33 . . . . 2.1(12) ?
B1 C31 C32 C33 . . . . 175.1(8) ?
F32 C32 C33 C34 . . . . 178.4(8) ?
C31 C32 C33 C34 . . . . -1.3(14) ?
F32 C32 C33 F33 . . . . -1.9(12) ?
C31 C32 C33 F33 . . . . 178.4(8) ?
F33 C33 C34 C35 . . . . -180.0(9) ?
C32 C33 C34 C35 . . . . -0.2(14) ?
F33 C33 C34 F34 . . . . 1.1(14) ?
C32 C33 C34 F34 . . . . -179.2(8) ?
C33 C34 C35 F35 . . . . -179.8(8) ?
F34 C34 C35 F35 . . . . -0.8(13) ?
C33 C34 C35 C36 . . . . 0.8(14) ?
F34 C34 C35 C36 . . . . 179.8(8) ?
F35 C35 C36 F36 . . . . -2.7(11) ?
C34 C35 C36 F36 . . . . 176.7(8) ?
F35 C35 C36 C31 . . . . -179.2(7) ?
C34 C35 C36 C31 . . . . 0.1(13) ?
C32 C31 C36 C35 . . . . -1.5(12) ?
B1 C31 C36 C35 . . . . -173.8(8) ?
C32 C31 C36 F36 . . . . -178.1(7) ?
B1 C31 C36 F36 . . . . 9.7(12) ?
C31 B1 C41 C42 . . . . 80.1(9) ?
C51 B1 C41 C42 . . . . -154.2(7) ?
C31 B1 C41 C46 . . . . -100.8(9) ?
C51 B1 C41 C46 . . . . 24.9(11) ?
C46 C41 C42 F42 . . . . -179.7(7) ?
B1 C41 C42 F42 . . . . -0.5(11) ?
C46 C41 C42 C43 . . . . 0.5(12) ?
B1 C41 C42 C43 . . . . 179.7(8) ?
C41 C42 C43 F43 . . . . 180.0(7) ?
F42 C42 C43 F43 . . . . 0.1(11) ?
C41 C42 C43 C44 . . . . -1.4(12) ?
F42 C42 C43 C44 . . . . 178.8(6) ?
F43 C43 C44 F44 . . . . -2.0(10) ?
C42 C43 C44 F44 . . . . 179.3(7) ?
F43 C43 C44 C45 . . . . 178.9(7) ?
C42 C43 C44 C45 . . . . 0.2(11) ?
F44 C44 C45 F45 . . . . 1.8(11) ?
C43 C44 C45 F45 . . . . -179.1(6) ?
F44 C44 C45 C46 . . . . -177.4(7) ?
C43 C44 C45 C46 . . . . 1.7(11) ?
C42 C41 C46 F46 . . . . -178.8(7) ?
B1 C41 C46 F46 . . . . 2.1(12) ?
C42 C41 C46 C45 . . . . 1.7(11) ?
B1 C41 C46 C45 . . . . -177.5(8) ?
F45 C45 C46 F46 . . . . -1.6(10) ?
C44 C45 C46 F46 . . . . 177.6(6) ?
F45 C45 C46 C41 . . . . 178.0(7) ?
C44 C45 C46 C41 . . . . -2.8(12) ?
C41 B1 C51 C52 . . . . -101.2(10) ?
C31 B1 C51 C52 . . . . 22.0(12) ?
C41 B1 C51 C56 . . . . 82.9(9) ?
C31 B1 C51 C56 . . . . -153.9(7) ?
C56 C51 C52 C53 . . . . -4.6(13) ?
B1 C51 C52 C53 . . . . 179.5(9) ?
C56 C51 C52 F52 . . . . 180.0(7) ?
B1 C51 C52 F52 . . . . 4.1(13) ?
C51 C52 C53 C54 . . . . 0.9(14) ?
F52 C52 C53 C54 . . . . 176.4(8) ?
C51 C52 C53 F53 . . . . -176.5(8) ?
F52 C52 C53 F53 . . . . -1.0(13) ?
C52 C53 C54 C55 . . . . 3.4(14) ?
F53 C53 C54 C55 . . . . -179.1(8) ?
C52 C53 C54 F54 . . . . -178.9(8) ?
F53 C53 C54 F54 . . . . -1.5(12) ?
C53 C54 C55 F55 . . . . -178.5(9) ?
F54 C54 C55 F55 . . . . 3.8(14) ?
C53 C54 C55 C56 . . . . -3.4(14) ?
F54 C54 C55 C56 . . . . 179.0(7) ?
C52 C51 C56 F56 . . . . -177.7(8) ?
B1 C51 C56 F56 . . . . -1.3(12) ?
C52 C51 C56 C55 . . . . 4.4(12) ?
B1 C51 C56 C55 . . . . -179.1(8) ?
F55 C55 C56 F56 . . . . -3.4(12) ?
C54 C55 C56 F56 . . . . -178.7(8) ?
F55 C55 C56 C51 . . . . 174.6(8) ?
C54 C55 C56 C51 . . . . -0.6(13) ?


####################################################################### 
# 
# 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_erk7932
_database_code_depnum_ccdc_archive 'CCDC 1515082'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H33 B F15 O2 P S'
_chemical_formula_weight         856.46

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9369(2)
_cell_length_b                   12.6020(2)
_cell_length_c                   15.7611(4)
_cell_angle_alpha                90.384(1)
_cell_angle_beta                 97.992(1)
_cell_angle_gamma                111.759(2)
_cell_volume                     1993.92(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5107
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18732
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6810
_reflns_number_gt                5755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

 A disordered half hexane molecule was found in the asymmetrical unit
 and could not be satisfactorily refined. The program SQUEEZE (A. L. Spek
 J. Appl. Cryst., 2003, 36, 7-13) was therefore used to remove 
 mathematically the effect of the solvent.
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule.  
 
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.011 0.000 0.000 222 50 ' '

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0322P)²+2.1357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         6810
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13644(7) 0.45569(5) 0.37325(4) 0.03855(17) Uani 1 1 d . . .
O1 O 0.0367(2) 0.42625(18) 0.42949(14) 0.0602(6) Uani 1 1 d . . .
P1 P 0.11800(6) 0.60530(5) 0.30087(4) 0.03251(16) Uani 1 1 d . . .
C1 C -0.0547(2) 0.5919(2) 0.27237(17) 0.0393(6) Uani 1 1 d . . .
H1 H -0.0532 0.6636 0.2464 0.047 Uiso 1 1 calc R . .
B1 B 0.1136(3) 0.2600(2) 0.28850(17) 0.0310(6) Uani 1 1 d . . .
O2 O 0.08757(16) 0.37228(14) 0.29094(10) 0.0335(4) Uani 1 1 d . . .
C2 C -0.1309(3) 0.4939(3) 0.20409(18) 0.0458(7) Uani 1 1 d . . .
H2A H -0.0854 0.5064 0.1536 0.055 Uiso 1 1 calc R . .
H2B H -0.1322 0.4214 0.2268 0.055 Uiso 1 1 calc R . .
C3 C -0.2736(3) 0.4869(3) 0.1779(2) 0.0578(8) Uani 1 1 d . . .
H3A H -0.2723 0.5567 0.1504 0.069 Uiso 1 1 calc R . .
H3B H -0.3217 0.4218 0.1362 0.069 Uiso 1 1 calc R . .
C4 C -0.3452(3) 0.4731(3) 0.2546(2) 0.0557(8) Uani 1 1 d . . .
H4A H -0.3535 0.4000 0.2792 0.067 Uiso 1 1 calc R . .
H4B H -0.4352 0.4719 0.2363 0.067 Uiso 1 1 calc R . .
C5 C -0.2711(3) 0.5700(3) 0.3222(2) 0.0583(8) Uani 1 1 d . . .
H5A H -0.3179 0.5571 0.3721 0.070 Uiso 1 1 calc R . .
H5B H -0.2705 0.6421 0.2991 0.070 Uiso 1 1 calc R . .
C6 C -0.1274(3) 0.5798(3) 0.3506(2) 0.0541(8) Uani 1 1 d . . .
H6A H -0.1274 0.5115 0.3800 0.065 Uiso 1 1 calc R . .
H6B H -0.0807 0.6466 0.3911 0.065 Uiso 1 1 calc R . .
C11 C 0.2216(2) 0.7319(2) 0.37186(16) 0.0376(6) Uani 1 1 d . . .
H11 H 0.3146 0.7472 0.3637 0.045 Uiso 1 1 calc R . .
C12 C 0.2176(3) 0.7157(3) 0.46742(18) 0.0542(8) Uani 1 1 d . . .
H12A H 0.1281 0.7031 0.4799 0.065 Uiso 1 1 calc R . .
H12B H 0.2378 0.6482 0.4830 0.065 Uiso 1 1 calc R . .
C13 C 0.3190(3) 0.8213(3) 0.5202(2) 0.0567(8) Uani 1 1 d . . .
H13A H 0.3116 0.8118 0.5812 0.068 Uiso 1 1 calc R . .
H13B H 0.4090 0.8285 0.5125 0.068 Uiso 1 1 calc R . .
C14 C 0.2978(3) 0.9296(3) 0.4942(2) 0.0634(9) Uani 1 1 d . . .
H14A H 0.2124 0.9265 0.5087 0.076 Uiso 1 1 calc R . .
H14B H 0.3684 0.9958 0.5266 0.076 Uiso 1 1 calc R . .
C15 C 0.2986(4) 0.9446(3) 0.4000(2) 0.0709(10) Uani 1 1 d . . .
H15A H 0.3876 0.9569 0.3866 0.085 Uiso 1 1 calc R . .
H15B H 0.2789 1.0125 0.3851 0.085 Uiso 1 1 calc R . .
C16 C 0.1956(3) 0.8394(2) 0.3459(2) 0.0593(8) Uani 1 1 d . . .
H16A H 0.1056 0.8309 0.3550 0.071 Uiso 1 1 calc R . .
H16B H 0.2017 0.8498 0.2849 0.071 Uiso 1 1 calc R . .
C21 C 0.1903(2) 0.6038(2) 0.20377(16) 0.0353(5) Uani 1 1 d . . .
H21 H 0.1446 0.5255 0.1763 0.042 Uiso 1 1 calc R . .
C22 C 0.1675(3) 0.6849(3) 0.13699(19) 0.0535(8) Uani 1 1 d . . .
H22A H 0.0729 0.6734 0.1261 0.064 Uiso 1 1 calc R . .
H22B H 0.2185 0.7646 0.1583 0.064 Uiso 1 1 calc R . .
C23 C 0.2124(3) 0.6600(4) 0.0542(2) 0.0659(9) Uani 1 1 d . . .
H23A H 0.1593 0.5808 0.0324 0.079 Uiso 1 1 calc R . .
H23B H 0.1975 0.7109 0.0107 0.079 Uiso 1 1 calc R . .
C24 C 0.3591(3) 0.6775(3) 0.06971(19) 0.0595(8) Uani 1 1 d . . .
H24A H 0.3845 0.6574 0.0164 0.071 Uiso 1 1 calc R . .
H24B H 0.4125 0.7584 0.0860 0.071 Uiso 1 1 calc R . .
C25 C 0.3886(3) 0.6049(3) 0.13989(19) 0.0514(7) Uani 1 1 d . . .
H25A H 0.4850 0.6239 0.1520 0.062 Uiso 1 1 calc R . .
H25B H 0.3460 0.5239 0.1198 0.062 Uiso 1 1 calc R . .
C26 C 0.3388(2) 0.6235(2) 0.22231(17) 0.0398(6) Uani 1 1 d . . .
H26A H 0.3897 0.7018 0.2468 0.048 Uiso 1 1 calc R . .
H26B H 0.3525 0.5705 0.2643 0.048 Uiso 1 1 calc R . .
C31 C 0.2036(2) 0.2565(2) 0.38050(15) 0.0315(5) Uani 1 1 d . . .
F32 F 0.02717(16) 0.11809(15) 0.43941(10) 0.0566(5) Uani 1 1 d . . .
C32 C 0.1561(3) 0.1890(2) 0.44649(16) 0.0380(6) Uani 1 1 d . . .
F33 F 0.1789(2) 0.12126(16) 0.58518(11) 0.0649(5) Uani 1 1 d . . .
C33 C 0.2330(3) 0.1887(2) 0.52399(17) 0.0437(6) Uani 1 1 d . . .
F34 F 0.44046(19) 0.25896(18) 0.61271(11) 0.0682(5) Uani 1 1 d . . .
C34 C 0.3642(3) 0.2592(3) 0.53805(17) 0.0460(7) Uani 1 1 d . . .
F35 F 0.54530(15) 0.40276(16) 0.49105(12) 0.0642(5) Uani 1 1 d . . .
C35 C 0.4173(2) 0.3307(2) 0.47659(18) 0.0422(6) Uani 1 1 d . . .
F36 F 0.39302(14) 0.40539(13) 0.34422(10) 0.0462(4) Uani 1 1 d . . .
C36 C 0.3366(2) 0.3291(2) 0.40091(16) 0.0353(5) Uani 1 1 d . . .
C41 C -0.0278(2) 0.1489(2) 0.26998(15) 0.0350(5) Uani 1 1 d . . .
C42 C -0.1549(3) 0.1478(2) 0.26795(19) 0.0474(7) Uani 1 1 d . . .
F42 F -0.17514(17) 0.24415(17) 0.28554(15) 0.0702(5) Uani 1 1 d . . .
F43 F -0.38947(18) 0.0551(2) 0.24866(17) 0.0959(8) Uani 1 1 d . . .
C43 C -0.2688(3) 0.0495(3) 0.2494(2) 0.0606(9) Uani 1 1 d . . .
F44 F -0.3682(2) -0.14872(19) 0.21324(15) 0.0967(8) Uani 1 1 d . . .
C44 C -0.2581(3) -0.0527(3) 0.2313(2) 0.0630(10) Uani 1 1 d . . .
F45 F -0.1225(2) -0.15700(15) 0.21708(14) 0.0833(7) Uani 1 1 d . . .
C45 C -0.1346(3) -0.0566(2) 0.23309(19) 0.0558(8) Uani 1 1 d . . .
F46 F 0.09458(17) 0.03168(13) 0.25572(12) 0.0561(4) Uani 1 1 d . . .
C46 C -0.0243(3) 0.0422(2) 0.25246(16) 0.0427(6) Uani 1 1 d . . .
C51 C 0.1862(2) 0.2655(2) 0.20326(15) 0.0320(5) Uani 1 1 d . . .
F52 F 0.35784(16) 0.20247(14) 0.26273(10) 0.0504(4) Uani 1 1 d . . .
C52 C 0.2973(3) 0.2398(2) 0.19518(17) 0.0399(6) Uani 1 1 d . . .
F53 F 0.46073(18) 0.22179(18) 0.11887(12) 0.0686(5) Uani 1 1 d . . .
C53 C 0.3527(3) 0.2475(3) 0.12104(19) 0.0479(7) Uani 1 1 d . . .
F54 F 0.3466(2) 0.2875(2) -0.02526(12) 0.0763(6) Uani 1 1 d . . .
C54 C 0.2950(3) 0.2804(3) 0.04800(18) 0.0507(7) Uani 1 1 d . . .
F55 F 0.12438(18) 0.33411(17) -0.02063(10) 0.0640(5) Uani 1 1 d . . .
C55 C 0.1834(3) 0.3034(2) 0.05082(17) 0.0446(6) Uani 1 1 d . . .
F56 F 0.01840(14) 0.31644(13) 0.12253(9) 0.0444(4) Uani 1 1 d . . .
C56 C 0.1317(2) 0.2951(2) 0.12623(16) 0.0357(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
S1 O1 1.445(2) . ?
S1 O2 1.5639(17) . ?
S1 P1 2.2679(9) . ?
P1 C21 1.821(3) . ?
P1 C1 1.824(2) . ?
P1 C11 1.834(3) . ?
C1 C2 1.532(4) . ?
C1 C6 1.537(4) . ?
C1 H1 0.9900 . ?
B1 O2 1.545(3) . ?
B1 C51 1.643(4) . ?
B1 C41 1.643(3) . ?
B1 C31 1.646(3) . ?
C2 C3 1.527(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.531(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C11 C12 1.526(4) . ?
C11 C16 1.531(4) . ?
C11 H11 0.9900 . ?
C12 C13 1.526(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.516(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.498(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.537(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C21 C22 1.531(4) . ?
C21 C26 1.534(3) . ?
C21 H21 0.9900 . ?
C22 C23 1.526(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.520(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.516(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 C26 1.526(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C31 C32 1.382(3) . ?
C31 C36 1.391(3) . ?
F32 C32 1.349(3) . ?
C32 C33 1.384(4) . ?
F33 C33 1.341(3) . ?
C33 C34 1.365(4) . ?
F34 C34 1.345(3) . ?
C34 C35 1.366(4) . ?
F35 C35 1.342(3) . ?
C35 C36 1.377(4) . ?
F36 C36 1.352(3) . ?
C41 C42 1.382(4) . ?
C41 C46 1.386(4) . ?
C42 F42 1.346(3) . ?
C42 C43 1.386(4) . ?
F43 C43 1.346(4) . ?
C43 C44 1.367(5) . ?
F44 C44 1.348(3) . ?
C44 C45 1.367(5) . ?
F45 C45 1.346(4) . ?
C45 C46 1.370(4) . ?
F46 C46 1.349(3) . ?
C51 C52 1.390(3) . ?
C51 C56 1.392(3) . ?
F52 C52 1.354(3) . ?
C52 C53 1.377(4) . ?
F53 C53 1.340(3) . ?
C53 C54 1.376(4) . ?
F54 C54 1.343(3) . ?
C54 C55 1.361(4) . ?
F55 C55 1.350(3) . ?
C55 C56 1.374(4) . ?
F56 C56 1.356(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 110.83(12) . . ?
O1 S1 P1 106.27(9) . . ?
O2 S1 P1 93.42(7) . . ?
C21 P1 C1 109.74(12) . . ?
C21 P1 C11 110.54(12) . . ?
C1 P1 C11 113.85(12) . . ?
C21 P1 S1 105.44(9) . . ?
C1 P1 S1 112.38(9) . . ?
C11 P1 S1 104.49(9) . . ?
C2 C1 C6 111.3(2) . . ?
C2 C1 P1 111.18(18) . . ?
C6 C1 P1 112.93(19) . . ?
C2 C1 H1 107.0 . . ?
C6 C1 H1 107.0 . . ?
P1 C1 H1 107.0 . . ?
O2 B1 C51 104.47(19) . . ?
O2 B1 C41 110.52(19) . . ?
C51 B1 C41 106.13(19) . . ?
O2 B1 C31 107.61(18) . . ?
C51 B1 C31 115.37(19) . . ?
C41 B1 C31 112.5(2) . . ?
B1 O2 S1 121.21(14) . . ?
C3 C2 C1 110.7(2) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.2(2) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.0(2) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 112.0(3) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C1 110.1(2) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C12 C11 C16 111.0(2) . . ?
C12 C11 P1 114.85(19) . . ?
C16 C11 P1 112.73(18) . . ?
C12 C11 H11 105.8 . . ?
C16 C11 H11 105.8 . . ?
P1 C11 H11 105.8 . . ?
C13 C12 C11 110.1(2) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.7(3) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 111.8(3) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 111.5(3) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C11 C16 C15 109.7(2) . . ?
C11 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C11 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C22 C21 C26 110.0(2) . . ?
C22 C21 P1 114.73(19) . . ?
C26 C21 P1 112.90(17) . . ?
C22 C21 H21 106.2 . . ?
C26 C21 H21 106.2 . . ?
P1 C21 H21 106.2 . . ?
C23 C22 C21 108.7(3) . . ?
C23 C22 H22A 110.0 . . ?
C21 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 110.8(3) . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C23 111.6(3) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 111.9(2) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C21 110.3(2) . . ?
C25 C26 H26A 109.6 . . ?
C21 C26 H26A 109.6 . . ?
C25 C26 H26B 109.6 . . ?
C21 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C32 C31 C36 113.2(2) . . ?
C32 C31 B1 125.0(2) . . ?
C36 C31 B1 121.7(2) . . ?
F32 C32 C31 121.1(2) . . ?
F32 C32 C33 114.8(2) . . ?
C31 C32 C33 124.2(2) . . ?
F33 C33 C34 120.3(2) . . ?
F33 C33 C32 120.5(3) . . ?
C34 C33 C32 119.2(3) . . ?
F34 C34 C33 119.9(3) . . ?
F34 C34 C35 120.2(3) . . ?
C33 C34 C35 119.9(2) . . ?
F35 C35 C34 120.2(2) . . ?
F35 C35 C36 120.9(3) . . ?
C34 C35 C36 118.8(2) . . ?
F36 C36 C35 116.2(2) . . ?
F36 C36 C31 119.2(2) . . ?
C35 C36 C31 124.6(2) . . ?
C42 C41 C46 113.8(2) . . ?
C42 C41 B1 127.6(2) . . ?
C46 C41 B1 118.6(2) . . ?
F42 C42 C41 121.1(2) . . ?
F42 C42 C43 115.6(3) . . ?
C41 C42 C43 123.3(3) . . ?
F43 C43 C44 120.3(3) . . ?
F43 C43 C42 119.9(3) . . ?
C44 C43 C42 119.8(3) . . ?
F44 C44 C43 120.3(3) . . ?
F44 C44 C45 120.4(3) . . ?
C43 C44 C45 119.3(3) . . ?
F45 C45 C44 120.0(3) . . ?
F45 C45 C46 120.9(3) . . ?
C44 C45 C46 119.2(3) . . ?
F46 C46 C45 116.2(3) . . ?
F46 C46 C41 119.2(2) . . ?
C45 C46 C41 124.6(3) . . ?
C52 C51 C56 112.4(2) . . ?
C52 C51 B1 128.3(2) . . ?
C56 C51 B1 119.2(2) . . ?
F52 C52 C53 115.2(2) . . ?
F52 C52 C51 120.2(2) . . ?
C53 C52 C51 124.6(2) . . ?
F53 C53 C54 119.7(3) . . ?
F53 C53 C52 120.8(3) . . ?
C54 C53 C52 119.4(2) . . ?
F54 C54 C55 120.6(3) . . ?
F54 C54 C53 120.5(3) . . ?
C55 C54 C53 118.9(2) . . ?
F55 C55 C54 119.6(2) . . ?
F55 C55 C56 120.6(3) . . ?
C54 C55 C56 119.8(2) . . ?
F56 C56 C55 115.7(2) . . ?
F56 C56 C51 119.5(2) . . ?
C55 C56 C51 124.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 P1 C21 -157.49(13) . . . . ?
O2 S1 P1 C21 -44.63(11) . . . . ?
O1 S1 P1 C1 -37.98(14) . . . . ?
O2 S1 P1 C1 74.88(12) . . . . ?
O1 S1 P1 C11 85.94(14) . . . . ?
O2 S1 P1 C11 -161.20(11) . . . . ?
C21 P1 C1 C2 48.1(2) . . . . ?
C11 P1 C1 C2 172.54(19) . . . . ?
S1 P1 C1 C2 -68.9(2) . . . . ?
C21 P1 C1 C6 174.0(2) . . . . ?
C11 P1 C1 C6 -61.5(2) . . . . ?
S1 P1 C1 C6 57.0(2) . . . . ?
C51 B1 O2 S1 -126.68(16) . . . . ?
C41 B1 O2 S1 119.56(18) . . . . ?
C31 B1 O2 S1 -3.6(2) . . . . ?
O1 S1 O2 B1 -89.18(19) . . . . ?
P1 S1 O2 B1 161.97(16) . . . . ?
C6 C1 C2 C3 55.6(3) . . . . ?
P1 C1 C2 C3 -177.5(2) . . . . ?
C1 C2 C3 C4 -56.6(4) . . . . ?
C2 C3 C4 C5 56.9(4) . . . . ?
C3 C4 C5 C6 -56.6(4) . . . . ?
C4 C5 C6 C1 55.1(4) . . . . ?
C2 C1 C6 C5 -54.6(3) . . . . ?
P1 C1 C6 C5 179.5(2) . . . . ?
C21 P1 C11 C12 -149.9(2) . . . . ?
C1 P1 C11 C12 86.0(2) . . . . ?
S1 P1 C11 C12 -37.0(2) . . . . ?
C21 P1 C11 C16 81.6(2) . . . . ?
C1 P1 C11 C16 -42.5(3) . . . . ?
S1 P1 C11 C16 -165.4(2) . . . . ?
C16 C11 C12 C13 -57.2(3) . . . . ?
P1 C11 C12 C13 173.5(2) . . . . ?
C11 C12 C13 C14 55.4(4) . . . . ?
C12 C13 C14 C15 -55.0(4) . . . . ?
C13 C14 C15 C16 55.3(4) . . . . ?
C12 C11 C16 C15 57.4(4) . . . . ?
P1 C11 C16 C15 -172.2(2) . . . . ?
C14 C15 C16 C11 -56.3(4) . . . . ?
C1 P1 C21 C22 48.7(2) . . . . ?
C11 P1 C21 C22 -77.7(2) . . . . ?
S1 P1 C21 C22 169.93(18) . . . . ?
C1 P1 C21 C26 175.82(18) . . . . ?
C11 P1 C21 C26 49.4(2) . . . . ?
S1 P1 C21 C26 -62.94(19) . . . . ?
C26 C21 C22 C23 60.8(3) . . . . ?
P1 C21 C22 C23 -170.6(2) . . . . ?
C21 C22 C23 C24 -59.7(4) . . . . ?
C22 C23 C24 C25 56.3(4) . . . . ?
C23 C24 C25 C26 -53.4(4) . . . . ?
C24 C25 C26 C21 54.3(3) . . . . ?
C22 C21 C26 C25 -58.3(3) . . . . ?
P1 C21 C26 C25 172.13(19) . . . . ?
O2 B1 C31 C32 104.8(3) . . . . ?
C51 B1 C31 C32 -139.0(2) . . . . ?
C41 B1 C31 C32 -17.1(3) . . . . ?
O2 B1 C31 C36 -70.9(3) . . . . ?
C51 B1 C31 C36 45.2(3) . . . . ?
C41 B1 C31 C36 167.1(2) . . . . ?
C36 C31 C32 F32 176.4(2) . . . . ?
B1 C31 C32 F32 0.3(4) . . . . ?
C36 C31 C32 C33 -2.8(4) . . . . ?
B1 C31 C32 C33 -178.9(2) . . . . ?
F32 C32 C33 F33 0.1(4) . . . . ?
C31 C32 C33 F33 179.4(2) . . . . ?
F32 C32 C33 C34 -178.8(2) . . . . ?
C31 C32 C33 C34 0.5(4) . . . . ?
F33 C33 C34 F34 1.8(4) . . . . ?
C32 C33 C34 F34 -179.3(2) . . . . ?
F33 C33 C34 C35 -177.6(3) . . . . ?
C32 C33 C34 C35 1.3(4) . . . . ?
F34 C34 C35 F35 -1.4(4) . . . . ?
C33 C34 C35 F35 178.0(2) . . . . ?
F34 C34 C35 C36 -179.9(2) . . . . ?
C33 C34 C35 C36 -0.5(4) . . . . ?
F35 C35 C36 F36 -1.4(4) . . . . ?
C34 C35 C36 F36 177.0(2) . . . . ?
F35 C35 C36 C31 179.3(2) . . . . ?
C34 C35 C36 C31 -2.2(4) . . . . ?
C32 C31 C36 F36 -175.5(2) . . . . ?
B1 C31 C36 F36 0.8(3) . . . . ?
C32 C31 C36 C35 3.7(4) . . . . ?
B1 C31 C36 C35 180.0(2) . . . . ?
O2 B1 C41 C42 -8.5(3) . . . . ?
C51 B1 C41 C42 -121.2(3) . . . . ?
C31 B1 C41 C42 111.8(3) . . . . ?
O2 B1 C41 C46 170.2(2) . . . . ?
C51 B1 C41 C46 57.5(3) . . . . ?
C31 B1 C41 C46 -69.5(3) . . . . ?
C46 C41 C42 F42 178.4(3) . . . . ?
B1 C41 C42 F42 -2.8(4) . . . . ?
C46 C41 C42 C43 -0.5(4) . . . . ?
B1 C41 C42 C43 178.2(3) . . . . ?
F42 C42 C43 F43 1.0(4) . . . . ?
C41 C42 C43 F43 180.0(3) . . . . ?
F42 C42 C43 C44 -179.5(3) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
F43 C43 C44 F44 -0.5(5) . . . . ?
C42 C43 C44 F44 -180.0(3) . . . . ?
F43 C43 C44 C45 -179.5(3) . . . . ?
C42 C43 C44 C45 1.0(5) . . . . ?
F44 C44 C45 F45 -0.3(5) . . . . ?
C43 C44 C45 F45 178.7(3) . . . . ?
F44 C44 C45 C46 -179.4(3) . . . . ?
C43 C44 C45 C46 -0.4(5) . . . . ?
F45 C45 C46 F46 -1.1(4) . . . . ?
C44 C45 C46 F46 178.0(3) . . . . ?
F45 C45 C46 C41 -179.8(3) . . . . ?
C44 C45 C46 C41 -0.8(4) . . . . ?
C42 C41 C46 F46 -177.6(2) . . . . ?
B1 C41 C46 F46 3.6(3) . . . . ?
C42 C41 C46 C45 1.2(4) . . . . ?
B1 C41 C46 C45 -177.7(3) . . . . ?
O2 B1 C51 C52 135.3(2) . . . . ?
C41 B1 C51 C52 -107.9(3) . . . . ?
C31 B1 C51 C52 17.3(3) . . . . ?
O2 B1 C51 C56 -47.3(3) . . . . ?
C41 B1 C51 C56 69.5(3) . . . . ?
C31 B1 C51 C56 -165.3(2) . . . . ?
C56 C51 C52 F52 -176.0(2) . . . . ?
B1 C51 C52 F52 1.6(4) . . . . ?
C56 C51 C52 C53 3.0(4) . . . . ?
B1 C51 C52 C53 -179.5(2) . . . . ?
F52 C52 C53 F53 -1.5(4) . . . . ?
C51 C52 C53 F53 179.5(2) . . . . ?
F52 C52 C53 C54 177.5(3) . . . . ?
C51 C52 C53 C54 -1.5(4) . . . . ?
F53 C53 C54 F54 -0.3(4) . . . . ?
C52 C53 C54 F54 -179.4(3) . . . . ?
F53 C53 C54 C55 178.3(3) . . . . ?
C52 C53 C54 C55 -0.7(4) . . . . ?
F54 C54 C55 F55 -0.3(4) . . . . ?
C53 C54 C55 F55 -179.0(3) . . . . ?
F54 C54 C55 C56 179.7(3) . . . . ?
C53 C54 C55 C56 1.0(4) . . . . ?
F55 C55 C56 F56 1.7(4) . . . . ?
C54 C55 C56 F56 -178.3(2) . . . . ?
F55 C55 C56 C51 -179.2(2) . . . . ?
C54 C55 C56 C51 0.8(4) . . . . ?
C52 C51 C56 F56 176.4(2) . . . . ?
B1 C51 C56 F56 -1.4(3) . . . . ?
C52 C51 C56 C55 -2.7(4) . . . . ?
B1 C51 C56 C55 179.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047

#=============================================================================
#  end of cif data for "erk7932" (compound 5)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

####################################################################### 
# 
# 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_erk8194
_database_code_depnum_ccdc_archive 'CCDC 1515081'
_audit_update_record             
;
2016-11-04 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H37 B Cl4 F15 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         962.25

_chemical_melting_point          ?

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

_cell_length_a                   20.8497(8)
_cell_length_b                   16.0333(6)
_cell_length_c                   23.8954(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7988.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      2.4814
_cell_measurement_theta_max      27.5050
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3904

_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            194744
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;

_reflns_number_total             8145
_reflns_number_gt                6970
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1073
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         8145
_refine_ls_number_parameters     560
_refine_ls_number_restraints     49
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+13.1298P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.742
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.73783(2) 0.34224(3) 0.37818(2) 0.00941(11) Uani d . . . 1.0 . .
B B1 0.51933(10) 0.62096(13) 0.38160(9) 0.0107(4) Uani d . . . 1.0 . .
F F1 0.52949(5) 0.67975(7) 0.33784(5) 0.0146(2) Uani d . . . 1.0 . .
C C1 0.81541(9) 0.39458(11) 0.37265(8) 0.0118(4) Uani d . . . 1.0 . .
H H1 0.8172 0.4187 0.3341 0.014 Uiso calc U . R 1.0 . .
C C2 0.87299(9) 0.33438(12) 0.37719(9) 0.0157(4) Uani d . . . 1.0 . .
H H2A 0.8758 0.3117 0.4157 0.019 Uiso calc U . R 1.0 . .
H H2B 0.8673 0.2871 0.351 0.019 Uiso calc U . R 1.0 . .
C C3 0.93454(10) 0.38194(13) 0.36291(9) 0.0191(4) Uani d . . . 1.0 . .
H H3A 0.9718 0.344 0.3668 0.023 Uiso calc U . R 1.0 . .
H H3B 0.9326 0.4008 0.3235 0.023 Uiso calc U . R 1.0 . .
C C4 0.94389(10) 0.45728(14) 0.40098(10) 0.0225(5) Uani d . . . 1.0 . .
H H4A 0.9827 0.4882 0.3893 0.027 Uiso calc U . R 1.0 . .
H H4B 0.9504 0.4381 0.44 0.027 Uiso calc U . R 1.0 . .
C C5 0.88567(10) 0.51549(13) 0.39856(9) 0.0190(4) Uani d . . . 1.0 . .
H H5A 0.8918 0.5621 0.4252 0.023 Uiso calc U . R 1.0 . .
H H5B 0.8819 0.5393 0.3605 0.023 Uiso calc U . R 1.0 . .
C C6 0.82394(10) 0.46862(12) 0.41323(9) 0.0160(4) Uani d . . . 1.0 . .
H H6A 0.7867 0.5067 0.4102 0.019 Uiso calc U . R 1.0 . .
H H6B 0.8263 0.4479 0.4522 0.019 Uiso calc U . R 1.0 . .
C C11 0.72396(9) 0.27718(12) 0.31692(8) 0.0125(4) Uani d . . . 1.0 . .
H H11 0.7595 0.2355 0.3147 0.015 Uiso calc U . R 1.0 . .
C C12 0.72457(11) 0.32861(13) 0.26250(8) 0.0197(4) Uani d . . . 1.0 . .
H H12A 0.6913 0.3725 0.2645 0.024 Uiso calc U . R 1.0 . .
H H12B 0.7668 0.3561 0.2581 0.024 Uiso calc U . R 1.0 . .
C C13 0.71173(12) 0.27205(14) 0.21184(9) 0.0251(5) Uani d . . . 1.0 . .
H H13A 0.7109 0.3063 0.1774 0.03 Uiso calc U . R 1.0 . .
H H13B 0.747 0.2311 0.2082 0.03 Uiso calc U . R 1.0 . .
C C14 0.64869(12) 0.22599(14) 0.21754(9) 0.0236(5) Uani d . . . 1.0 . .
H H14A 0.6427 0.1885 0.185 0.028 Uiso calc U . R 1.0 . .
H H14B 0.6129 0.2666 0.2179 0.028 Uiso calc U . R 1.0 . .
C C15 0.64766(11) 0.17498(13) 0.27146(9) 0.0211(4) Uani d . . . 1.0 . .
H H15A 0.6806 0.1307 0.2692 0.025 Uiso calc U . R 1.0 . .
H H15B 0.6053 0.1477 0.2754 0.025 Uiso calc U . R 1.0 . .
C C16 0.66043(10) 0.22906(13) 0.32295(8) 0.0167(4) Uani d . . . 1.0 . .
H H16A 0.6623 0.1932 0.3567 0.02 Uiso calc U . R 1.0 . .
H H16B 0.6247 0.2691 0.3279 0.02 Uiso calc U . R 1.0 . .
C C21 0.72990(9) 0.27735(12) 0.44059(8) 0.0124(4) Uani d . . . 1.0 . .
H H21 0.6839 0.2596 0.4416 0.015 Uiso calc U . R 1.0 . .
C C22 0.76918(10) 0.19580(12) 0.43929(8) 0.0148(4) Uani d . . . 1.0 . .
H H22A 0.761 0.1654 0.404 0.018 Uiso calc U . R 1.0 . .
H H22B 0.8156 0.2085 0.4415 0.018 Uiso calc U . R 1.0 . .
C C23 0.74901(10) 0.14232(12) 0.48938(8) 0.0171(4) Uani d . . . 1.0 . .
H H23A 0.7035 0.126 0.485 0.021 Uiso calc U . R 1.0 . .
H H23B 0.7751 0.0907 0.4899 0.021 Uiso calc U . R 1.0 . .
C C24 0.75728(11) 0.18798(14) 0.54484(9) 0.0219(5) Uani d . . . 1.0 . .
H H24A 0.8035 0.1981 0.5516 0.026 Uiso calc U . R 1.0 . .
H H24B 0.741 0.1525 0.5756 0.026 Uiso calc U . R 1.0 . .
C C25 0.72151(11) 0.27116(13) 0.54513(9) 0.0206(4) Uani d . . . 1.0 . .
H H25A 0.731 0.3012 0.5804 0.025 Uiso calc U . R 1.0 . .
H H25B 0.6748 0.2606 0.5437 0.025 Uiso calc U . R 1.0 . .
C C26 0.74112(10) 0.32543(12) 0.49525(8) 0.0158(4) Uani d . . . 1.0 . .
H H26A 0.787 0.3407 0.4985 0.019 Uiso calc U . R 1.0 . .
H H26B 0.7155 0.3774 0.4951 0.019 Uiso calc U . R 1.0 . .
C C31 0.57719(9) 0.55073(11) 0.38049(8) 0.0104(4) Uani d . . . 1.0 . .
C C32 0.57159(9) 0.47534(12) 0.40843(8) 0.0113(4) Uani d . . . 1.0 . .
F F32 0.51872(5) 0.46048(7) 0.43938(5) 0.0170(2) Uani d . . . 1.0 . .
C C33 0.61710(9) 0.41295(11) 0.40765(8) 0.0112(4) Uani d . . . 1.0 . .
F F33 0.60301(5) 0.34192(7) 0.43516(5) 0.0161(2) Uani d . . . 1.0 . .
C C34 0.67500(9) 0.42150(11) 0.37891(8) 0.0104(4) Uani d . . . 1.0 . .
C C35 0.68066(9) 0.49652(12) 0.34935(8) 0.0114(4) Uani d . . . 1.0 . .
F F35 0.73316(5) 0.51152(7) 0.31770(5) 0.0164(2) Uani d . . . 1.0 . .
C C36 0.63407(9) 0.55752(11) 0.35056(8) 0.0107(4) Uani d . . . 1.0 . .
F F36 0.64739(5) 0.62719(7) 0.32068(5) 0.0161(2) Uani d . . . 1.0 . .
C C41 0.51670(9) 0.67494(11) 0.44045(8) 0.0116(4) Uani d . . . 1.0 . .
C C42 0.47446(9) 0.74220(12) 0.44302(8) 0.0137(4) Uani d . . . 1.0 . .
F F42 0.43533(5) 0.75861(7) 0.39929(5) 0.0178(2) Uani d . . . 1.0 . .
C C43 0.46783(10) 0.79382(12) 0.48884(9) 0.0176(4) Uani d . . . 1.0 . .
F F43 0.42550(6) 0.85730(8) 0.48831(6) 0.0272(3) Uani d . . . 1.0 . .
C C44 0.50391(10) 0.77849(13) 0.53614(9) 0.0200(4) Uani d . . . 1.0 . .
F F44 0.49595(7) 0.82567(9) 0.58221(6) 0.0318(3) Uani d . . . 1.0 . .
C C45 0.54623(10) 0.71273(13) 0.53625(8) 0.0182(4) Uani d . . . 1.0 . .
F F45 0.58020(7) 0.69582(9) 0.58249(5) 0.0275(3) Uani d . . . 1.0 . .
C C46 0.55207(9) 0.66342(12) 0.48890(8) 0.0138(4) Uani d . . . 1.0 . .
F F46 0.59463(6) 0.60001(7) 0.49297(5) 0.0177(2) Uani d . . . 1.0 . .
C C51 0.45092(9) 0.57224(11) 0.36917(8) 0.0119(4) Uani d . . . 1.0 . .
C C52 0.40120(9) 0.55859(11) 0.40706(8) 0.0128(4) Uani d . . . 1.0 . .
F F52 0.40625(6) 0.58330(7) 0.46066(5) 0.0174(2) Uani d . . . 1.0 . .
C C53 0.34444(10) 0.51931(12) 0.39303(9) 0.0163(4) Uani d . . . 1.0 . .
F F53 0.29774(6) 0.50905(8) 0.43121(5) 0.0237(3) Uani d . . . 1.0 . .
C C54 0.33504(10) 0.49125(13) 0.33926(9) 0.0191(4) Uani d . . . 1.0 . .
F F54 0.27968(6) 0.45375(9) 0.32527(6) 0.0295(3) Uani d . . . 1.0 . .
C C55 0.38288(11) 0.50171(13) 0.30060(9) 0.0185(4) Uani d . . . 1.0 . .
F F55 0.37390(7) 0.47445(8) 0.24786(5) 0.0269(3) Uani d . . . 1.0 . .
C C56 0.43924(10) 0.54132(12) 0.31587(8) 0.0151(4) Uani d . . . 1.0 . .
F F56 0.48433(6) 0.54920(8) 0.27558(5) 0.0218(3) Uani d . . . 1.0 . .
C C71 0.6304(2) 0.4745(3) 0.12624(18) 0.0442(13) Uani d U P D 0.670(6) A 1
H H71A 0.6756 0.4563 0.1303 0.053 Uiso calc U P R 0.670(6) A 1
H H71B 0.6052 0.4253 0.1144 0.053 Uiso calc U P R 0.670(6) A 1
Cl Cl1 0.60260(17) 0.5070(3) 0.19153(10) 0.0924(13) Uani d U P D 0.670(6) A 1
Cl Cl2 0.62685(9) 0.5467(2) 0.07484(9) 0.0763(8) Uani d U P D 0.670(6) A 1
C C71A 0.6506(15) 0.5597(17) 0.1713(9) 0.225(16) Uani d U P D 0.330(6) A 2
H H71C 0.6404 0.6082 0.1952 0.27 Uiso calc U P R 0.330(6) A 2
H H71D 0.6952 0.5424 0.1793 0.27 Uiso calc U P R 0.330(6) A 2
Cl Cl1A 0.6450(4) 0.5877(5) 0.1043(5) 0.140(4) Uani d U P D 0.330(6) A 2
Cl Cl2A 0.6003(3) 0.4803(7) 0.1872(3) 0.122(3) Uani d U P D 0.330(6) A 2
C C72 0.53813(14) 0.75008(19) 0.21522(12) 0.0407(7) Uani d . . . 1.0 . .
H H72A 0.5257 0.7244 0.2513 0.049 Uiso calc U . R 1.0 . .
H H72B 0.5272 0.7104 0.1849 0.049 Uiso calc U . R 1.0 . .
Cl Cl3 0.62127(4) 0.76878(5) 0.21486(3) 0.04610(18) Uani d . . . 1.0 . .
Cl Cl4 0.49491(3) 0.84367(5) 0.20558(4) 0.04753(19) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C11 . 1.8207(19) ?
P1 C34 . 1.8252(18) ?
P1 C21 . 1.8259(19) ?
P1 C1 . 1.8269(19) ?
B1 F1 . 1.424(2) ?
B1 C31 . 1.651(3) ?
B1 C41 . 1.652(3) ?
B1 C51 . 1.653(3) ?
C1 C6 . 1.543(3) ?
C1 C2 . 1.544(3) ?
C1 H1 . 1.0 ?
C2 C3 . 1.531(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.525(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.532(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.531(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C11 C16 . 1.540(3) ?
C11 C12 . 1.540(3) ?
C11 H11 . 1.0 ?
C12 C13 . 1.536(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.514(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.526(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.528(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C26 . 1.535(3) ?
C21 C22 . 1.543(3) ?
C21 H21 . 1.0 ?
C22 C23 . 1.531(3) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.524(3) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.528(3) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.531(3) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C31 C32 . 1.386(3) ?
C31 C36 . 1.389(3) ?
C32 F32 . 1.349(2) ?
C32 C33 . 1.379(3) ?
C33 F33 . 1.347(2) ?
C33 C34 . 1.396(3) ?
C34 C35 . 1.400(3) ?
C35 F35 . 1.352(2) ?
C35 C36 . 1.379(3) ?
C36 F36 . 1.354(2) ?
C41 C46 . 1.385(3) ?
C41 C42 . 1.394(3) ?
C42 F42 . 1.352(2) ?
C42 C43 . 1.379(3) ?
C43 F43 . 1.347(2) ?
C43 C44 . 1.380(3) ?
C44 F44 . 1.346(2) ?
C44 C45 . 1.375(3) ?
C45 F45 . 1.340(2) ?
C45 C46 . 1.386(3) ?
C46 F46 . 1.353(2) ?
C51 C56 . 1.388(3) ?
C51 C52 . 1.394(3) ?
C52 F52 . 1.345(2) ?
C52 C53 . 1.382(3) ?
C53 F53 . 1.344(2) ?
C53 C54 . 1.375(3) ?
C54 F54 . 1.344(2) ?
C54 C55 . 1.370(3) ?
C55 F55 . 1.347(2) ?
C55 C56 . 1.385(3) ?
C56 F56 . 1.351(2) ?
C71 Cl2 . 1.690(5) ?
C71 Cl1 . 1.744(5) ?
C71 H71A . 0.99 ?
C71 H71B . 0.99 ?
C71A Cl1A . 1.665(16) ?
C71A Cl2A . 1.692(16) ?
C71A H71C . 0.99 ?
C71A H71D . 0.99 ?
C72 Cl3 . 1.759(3) ?
C72 Cl4 . 1.766(3) ?
C72 H72A . 0.99 ?
C72 H72B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 P1 C34 . . 107.01(9) ?
C11 P1 C21 . . 108.41(9) ?
C34 P1 C21 . . 108.90(9) ?
C11 P1 C1 . . 110.23(9) ?
C34 P1 C1 . . 108.44(9) ?
C21 P1 C1 . . 113.64(9) ?
F1 B1 C31 . . 109.33(15) ?
F1 B1 C41 . . 106.47(15) ?
C31 B1 C41 . . 113.29(15) ?
F1 B1 C51 . . 108.02(15) ?
C31 B1 C51 . . 107.78(15) ?
C41 B1 C51 . . 111.82(15) ?
C6 C1 C2 . . 110.31(16) ?
C6 C1 P1 . . 114.21(13) ?
C2 C1 P1 . . 113.33(13) ?
C6 C1 H1 . . 106.1 ?
C2 C1 H1 . . 106.1 ?
P1 C1 H1 . . 106.1 ?
C3 C2 C1 . . 108.94(15) ?
C3 C2 H2A . . 109.9 ?
C1 C2 H2A . . 109.9 ?
C3 C2 H2B . . 109.9 ?
C1 C2 H2B . . 109.9 ?
H2A C2 H2B . . 108.3 ?
C4 C3 C2 . . 111.63(17) ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
C3 C4 C5 . . 111.03(17) ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C4 . . 110.99(17) ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5B . . 109.4 ?
C4 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C5 C6 C1 . . 109.31(16) ?
C5 C6 H6A . . 109.8 ?
C1 C6 H6A . . 109.8 ?
C5 C6 H6B . . 109.8 ?
C1 C6 H6B . . 109.8 ?
H6A C6 H6B . . 108.3 ?
C16 C11 C12 . . 110.76(16) ?
C16 C11 P1 . . 110.40(13) ?
C12 C11 P1 . . 111.77(13) ?
C16 C11 H11 . . 107.9 ?
C12 C11 H11 . . 107.9 ?
P1 C11 H11 . . 107.9 ?
C13 C12 C11 . . 110.36(17) ?
C13 C12 H12A . . 109.6 ?
C11 C12 H12A . . 109.6 ?
C13 C12 H12B . . 109.6 ?
C11 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C14 C13 C12 . . 111.62(18) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 110.47(18) ?
C13 C14 H14A . . 109.6 ?
C15 C14 H14A . . 109.6 ?
C13 C14 H14B . . 109.6 ?
C15 C14 H14B . . 109.6 ?
H14A C14 H14B . . 108.1 ?
C14 C15 C16 . . 111.90(17) ?
C14 C15 H15A . . 109.2 ?
C16 C15 H15A . . 109.2 ?
C14 C15 H15B . . 109.2 ?
C16 C15 H15B . . 109.2 ?
H15A C15 H15B . . 107.9 ?
C15 C16 C11 . . 111.02(17) ?
C15 C16 H16A . . 109.4 ?
C11 C16 H16A . . 109.4 ?
C15 C16 H16B . . 109.4 ?
C11 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C26 C21 C22 . . 111.22(16) ?
C26 C21 P1 . . 113.28(13) ?
C22 C21 P1 . . 114.73(13) ?
C26 C21 H21 . . 105.6 ?
C22 C21 H21 . . 105.6 ?
P1 C21 H21 . . 105.6 ?
C23 C22 C21 . . 108.23(16) ?
C23 C22 H22A . . 110.1 ?
C21 C22 H22A . . 110.1 ?
C23 C22 H22B . . 110.1 ?
C21 C22 H22B . . 110.1 ?
H22A C22 H22B . . 108.4 ?
C24 C23 C22 . . 112.32(17) ?
C24 C23 H23A . . 109.1 ?
C22 C23 H23A . . 109.1 ?
C24 C23 H23B . . 109.1 ?
C22 C23 H23B . . 109.1 ?
H23A C23 H23B . . 107.9 ?
C23 C24 C25 . . 111.59(17) ?
C23 C24 H24A . . 109.3 ?
C25 C24 H24A . . 109.3 ?
C23 C24 H24B . . 109.3 ?
C25 C24 H24B . . 109.3 ?
H24A C24 H24B . . 108.0 ?
C24 C25 C26 . . 111.23(17) ?
C24 C25 H25A . . 109.4 ?
C26 C25 H25A . . 109.4 ?
C24 C25 H25B . . 109.4 ?
C26 C25 H25B . . 109.4 ?
H25A C25 H25B . . 108.0 ?
C25 C26 C21 . . 109.66(16) ?
C25 C26 H26A . . 109.7 ?
C21 C26 H26A . . 109.7 ?
C25 C26 H26B . . 109.7 ?
C21 C26 H26B . . 109.7 ?
H26A C26 H26B . . 108.2 ?
C32 C31 C36 . . 112.86(17) ?
C32 C31 B1 . . 121.72(16) ?
C36 C31 B1 . . 125.36(16) ?
F32 C32 C33 . . 116.22(16) ?
F32 C32 C31 . . 119.15(16) ?
C33 C32 C31 . . 124.62(17) ?
F33 C33 C32 . . 117.16(16) ?
F33 C33 C34 . . 120.78(16) ?
C32 C33 C34 . . 122.05(17) ?
C33 C34 C35 . . 113.93(16) ?
C33 C34 P1 . . 123.86(14) ?
C35 C34 P1 . . 122.20(14) ?
F35 C35 C36 . . 117.12(16) ?
F35 C35 C34 . . 120.23(16) ?
C36 C35 C34 . . 122.66(17) ?
F36 C36 C35 . . 115.44(16) ?
F36 C36 C31 . . 120.73(16) ?
C35 C36 C31 . . 123.82(17) ?
C46 C41 C42 . . 113.75(17) ?
C46 C41 B1 . . 128.60(17) ?
C42 C41 B1 . . 117.63(17) ?
F42 C42 C43 . . 115.88(17) ?
F42 C42 C41 . . 119.87(17) ?
C43 C42 C41 . . 124.23(19) ?
F43 C43 C42 . . 120.76(19) ?
F43 C43 C44 . . 119.96(18) ?
C42 C43 C44 . . 119.26(19) ?
F44 C44 C45 . . 120.6(2) ?
F44 C44 C43 . . 120.18(19) ?
C45 C44 C43 . . 119.22(19) ?
F45 C45 C44 . . 119.73(19) ?
F45 C45 C46 . . 120.76(19) ?
C44 C45 C46 . . 119.49(19) ?
F46 C46 C41 . . 120.63(17) ?
F46 C46 C45 . . 115.32(17) ?
C41 C46 C45 . . 124.03(18) ?
C56 C51 C52 . . 114.17(18) ?
C56 C51 B1 . . 119.00(17) ?
C52 C51 B1 . . 126.82(17) ?
F52 C52 C53 . . 115.62(17) ?
F52 C52 C51 . . 120.95(17) ?
C53 C52 C51 . . 123.43(18) ?
F53 C53 C54 . . 119.39(18) ?
F53 C53 C52 . . 120.75(18) ?
C54 C53 C52 . . 119.86(19) ?
F54 C54 C55 . . 120.82(19) ?
F54 C54 C53 . . 120.09(19) ?
C55 C54 C53 . . 119.09(19) ?
F55 C55 C54 . . 119.35(19) ?
F55 C55 C56 . . 120.88(19) ?
C54 C55 C56 . . 119.76(19) ?
F56 C56 C55 . . 116.45(17) ?
F56 C56 C51 . . 119.88(18) ?
C55 C56 C51 . . 123.67(19) ?
Cl2 C71 Cl1 . . 115.5(3) ?
Cl2 C71 H71A . . 108.4 ?
Cl1 C71 H71A . . 108.4 ?
Cl2 C71 H71B . . 108.4 ?
Cl1 C71 H71B . . 108.4 ?
H71A C71 H71B . . 107.5 ?
Cl1A C71A Cl2A . . 112.1(13) ?
Cl1A C71A H71C . . 109.2 ?
Cl2A C71A H71C . . 109.2 ?
Cl1A C71A H71D . . 109.2 ?
Cl2A C71A H71D . . 109.2 ?
H71C C71A H71D . . 107.9 ?
Cl3 C72 Cl4 . . 110.94(15) ?
Cl3 C72 H72A . . 109.5 ?
Cl4 C72 H72A . . 109.5 ?
Cl3 C72 H72B . . 109.5 ?
Cl4 C72 H72B . . 109.5 ?
H72A C72 H72B . . 108.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 P1 C1 C6 . . . . 163.98(14) ?
C34 P1 C1 C6 . . . . 47.14(16) ?
C21 P1 C1 C6 . . . . -74.10(16) ?
C11 P1 C1 C2 . . . . -68.55(16) ?
C34 P1 C1 C2 . . . . 174.60(14) ?
C21 P1 C1 C2 . . . . 53.36(16) ?
C6 C1 C2 C3 . . . . -59.3(2) ?
P1 C1 C2 C3 . . . . 171.18(14) ?
C1 C2 C3 C4 . . . . 57.4(2) ?
C2 C3 C4 C5 . . . . -56.1(2) ?
C3 C4 C5 C6 . . . . 55.9(2) ?
C4 C5 C6 C1 . . . . -57.6(2) ?
C2 C1 C6 C5 . . . . 59.8(2) ?
P1 C1 C6 C5 . . . . -171.21(14) ?
C34 P1 C11 C16 . . . . -65.51(15) ?
C21 P1 C11 C16 . . . . 51.80(15) ?
C1 P1 C11 C16 . . . . 176.76(13) ?
C34 P1 C11 C12 . . . . 58.24(16) ?
C21 P1 C11 C12 . . . . 175.56(14) ?
C1 P1 C11 C12 . . . . -59.48(16) ?
C16 C11 C12 C13 . . . . -55.6(2) ?
P1 C11 C12 C13 . . . . -179.15(15) ?
C11 C12 C13 C14 . . . . 57.2(3) ?
C12 C13 C14 C15 . . . . -56.9(3) ?
C13 C14 C15 C16 . . . . 56.0(3) ?
C14 C15 C16 C11 . . . . -55.3(2) ?
C12 C11 C16 C15 . . . . 54.9(2) ?
P1 C11 C16 C15 . . . . 179.25(14) ?
C11 P1 C21 C26 . . . . 179.58(14) ?
C34 P1 C21 C26 . . . . -64.32(16) ?
C1 P1 C21 C26 . . . . 56.66(16) ?
C11 P1 C21 C22 . . . . 50.38(16) ?
C34 P1 C21 C22 . . . . 166.48(13) ?
C1 P1 C21 C22 . . . . -72.53(16) ?
C26 C21 C22 C23 . . . . 59.0(2) ?
P1 C21 C22 C23 . . . . -170.76(14) ?
C21 C22 C23 C24 . . . . -56.6(2) ?
C22 C23 C24 C25 . . . . 55.2(2) ?
C23 C24 C25 C26 . . . . -54.2(2) ?
C24 C25 C26 C21 . . . . 56.1(2) ?
C22 C21 C26 C25 . . . . -59.5(2) ?
P1 C21 C26 C25 . . . . 169.57(14) ?
F1 B1 C31 C32 . . . . -163.56(17) ?
C41 B1 C31 C32 . . . . 77.9(2) ?
C51 B1 C31 C32 . . . . -46.4(2) ?
F1 B1 C31 C36 . . . . 13.3(3) ?
C41 B1 C31 C36 . . . . -105.2(2) ?
C51 B1 C31 C36 . . . . 130.52(19) ?
C36 C31 C32 F32 . . . . 179.76(16) ?
B1 C31 C32 F32 . . . . -3.0(3) ?
C36 C31 C32 C33 . . . . 0.4(3) ?
B1 C31 C32 C33 . . . . 177.70(18) ?
F32 C32 C33 F33 . . . . 3.4(3) ?
C31 C32 C33 F33 . . . . -177.22(17) ?
F32 C32 C33 C34 . . . . -177.71(17) ?
C31 C32 C33 C34 . . . . 1.6(3) ?
F33 C33 C34 C35 . . . . 175.87(16) ?
C32 C33 C34 C35 . . . . -2.9(3) ?
F33 C33 C34 P1 . . . . -3.1(3) ?
C32 C33 C34 P1 . . . . 178.13(15) ?
C11 P1 C34 C33 . . . . 92.81(17) ?
C21 P1 C34 C33 . . . . -24.18(19) ?
C1 P1 C34 C33 . . . . -148.30(16) ?
C11 P1 C34 C35 . . . . -86.04(17) ?
C21 P1 C34 C35 . . . . 156.97(16) ?
C1 P1 C34 C35 . . . . 32.85(18) ?
C33 C34 C35 F35 . . . . -177.19(16) ?
P1 C34 C35 F35 . . . . 1.8(3) ?
C33 C34 C35 C36 . . . . 2.4(3) ?
P1 C34 C35 C36 . . . . -178.62(15) ?
F35 C35 C36 F36 . . . . -1.7(2) ?
C34 C35 C36 F36 . . . . 178.64(17) ?
F35 C35 C36 C31 . . . . 179.11(17) ?
C34 C35 C36 C31 . . . . -0.5(3) ?
C32 C31 C36 F36 . . . . 179.91(16) ?
B1 C31 C36 F36 . . . . 2.8(3) ?
C32 C31 C36 C35 . . . . -1.0(3) ?
B1 C31 C36 C35 . . . . -178.12(18) ?
F1 B1 C41 C46 . . . . -126.5(2) ?
C31 B1 C41 C46 . . . . -6.3(3) ?
C51 B1 C41 C46 . . . . 115.7(2) ?
F1 B1 C41 C42 . . . . 52.5(2) ?
C31 B1 C41 C42 . . . . 172.69(16) ?
C51 B1 C41 C42 . . . . -65.3(2) ?
C46 C41 C42 F42 . . . . -177.61(16) ?
B1 C41 C42 F42 . . . . 3.2(3) ?
C46 C41 C42 C43 . . . . 0.4(3) ?
B1 C41 C42 C43 . . . . -178.76(18) ?
F42 C42 C43 F43 . . . . -1.4(3) ?
C41 C42 C43 F43 . . . . -179.46(18) ?
F42 C42 C43 C44 . . . . 176.88(18) ?
C41 C42 C43 C44 . . . . -1.2(3) ?
F43 C43 C44 F44 . . . . 1.4(3) ?
C42 C43 C44 F44 . . . . -176.84(18) ?
F43 C43 C44 C45 . . . . 179.08(18) ?
C42 C43 C44 C45 . . . . 0.8(3) ?
F44 C44 C45 F45 . . . . -0.5(3) ?
C43 C44 C45 F45 . . . . -178.14(19) ?
F44 C44 C45 C46 . . . . 177.94(18) ?
C43 C44 C45 C46 . . . . 0.3(3) ?
C42 C41 C46 F46 . . . . 179.27(16) ?
B1 C41 C46 F46 . . . . -1.7(3) ?
C42 C41 C46 C45 . . . . 0.8(3) ?
B1 C41 C46 C45 . . . . 179.84(19) ?
F45 C45 C46 F46 . . . . -1.3(3) ?
C44 C45 C46 F46 . . . . -179.71(18) ?
F45 C45 C46 C41 . . . . 177.26(18) ?
C44 C45 C46 C41 . . . . -1.2(3) ?
F1 B1 C51 C56 . . . . 47.5(2) ?
C31 B1 C51 C56 . . . . -70.5(2) ?
C41 B1 C51 C56 . . . . 164.37(16) ?
F1 B1 C51 C52 . . . . -131.70(19) ?
C31 B1 C51 C52 . . . . 110.3(2) ?
C41 B1 C51 C52 . . . . -14.9(3) ?
C56 C51 C52 F52 . . . . 178.42(16) ?
B1 C51 C52 F52 . . . . -2.3(3) ?
C56 C51 C52 C53 . . . . -1.3(3) ?
B1 C51 C52 C53 . . . . 178.02(18) ?
F52 C52 C53 F53 . . . . 1.3(3) ?
C51 C52 C53 F53 . . . . -178.96(17) ?
F52 C52 C53 C54 . . . . -179.51(18) ?
C51 C52 C53 C54 . . . . 0.2(3) ?
F53 C53 C54 F54 . . . . -0.2(3) ?
C52 C53 C54 F54 . . . . -179.34(18) ?
F53 C53 C54 C55 . . . . -179.83(18) ?
C52 C53 C54 C55 . . . . 1.0(3) ?
F54 C54 C55 F55 . . . . 0.4(3) ?
C53 C54 C55 F55 . . . . -179.91(19) ?
F54 C54 C55 C56 . . . . 179.32(19) ?
C53 C54 C55 C56 . . . . -1.0(3) ?
F55 C55 C56 F56 . . . . -1.3(3) ?
C54 C55 C56 F56 . . . . 179.83(18) ?
F55 C55 C56 C51 . . . . 178.71(18) ?
C54 C55 C56 C51 . . . . -0.1(3) ?
C52 C51 C56 F56 . . . . -178.73(16) ?
B1 C51 C56 F56 . . . . 1.9(3) ?
C52 C51 C56 C55 . . . . 1.2(3) ?
B1 C51 C56 C55 . . . . -178.09(18) ?


