# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_erk8890
_database_code_depnum_ccdc_archive 'CCDC 1865543'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H31 B Cl F10 P Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         746.92

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.9107(4)
_cell_length_b                   17.0092(6)
_cell_length_c                   18.4957(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.9540(10)
_cell_angle_gamma                90
_cell_volume                     3399.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.3754
_cell_measurement_theta_max      27.4719
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.129
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528

_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.90
_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            78562
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_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             7216
_reflns_number_gt                5820
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0832
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         7216
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+2.6766P] 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         0.306
_refine_diff_density_min         -0.318
_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'
Si Si 0.0817 0.0704 '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       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (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
B B1 0.59106(18) 0.45518(12) 0.30170(10) 0.0130(4) Uani d . . . 1 . .
C C1 0.46350(16) 0.49961(10) 0.27053(9) 0.0126(3) Uani d . . . 1 . .
Cl Cl1 0.68970(4) 0.52612(3) 0.36517(2) 0.01737(10) Uani d . . . 1 . .
P P1 0.36840(4) 0.58342(3) 0.27249(2) 0.01097(10) Uani d . . . 1 . .
Si Si1 0.30433(4) 0.43844(3) 0.13382(2) 0.01309(11) Uani d . . . 1 . .
C C2 0.37246(16) 0.50155(10) 0.21390(9) 0.0123(3) Uani d . . . 1 . .
C C3 0.14118(17) 0.46976(11) 0.10436(10) 0.0183(4) Uani d . . . 1 . .
H H3A 0.1405 0.5223 0.0825 0.027 Uiso calc U . R 1 . .
H H3B 0.0964 0.471 0.1468 0.027 Uiso calc U . R 1 . .
H H3C 0.1009 0.4324 0.0683 0.027 Uiso calc U . R 1 . .
C C4 0.40011(17) 0.44758(11) 0.05817(9) 0.0186(4) Uani d . . . 1 . .
H H4A 0.4874 0.4394 0.0774 0.028 Uiso calc U . R 1 . .
H H4B 0.3893 0.5002 0.0366 0.028 Uiso calc U . R 1 . .
H H4C 0.3738 0.408 0.0207 0.028 Uiso calc U . R 1 . .
C C5 0.31540(18) 0.33583(10) 0.16921(10) 0.0195(4) Uani d . . . 1 . .
H H5A 0.2817 0.2995 0.1303 0.029 Uiso calc U . R 1 . .
H H5B 0.268 0.3311 0.2103 0.029 Uiso calc U . R 1 . .
H H5C 0.4023 0.3228 0.1856 0.029 Uiso calc U . R 1 . .
C C11 0.41948(16) 0.67939(10) 0.24795(9) 0.0126(3) Uani d . . . 1 . .
C C12 0.46268(16) 0.73134(10) 0.30530(9) 0.0137(4) Uani d . . . 1 . .
C C13 0.48650(16) 0.80905(10) 0.28822(10) 0.0159(4) Uani d . . . 1 . .
H H13 0.5159 0.8441 0.3267 0.019 Uiso calc U . R 1 . .
C C14 0.46887(16) 0.83732(10) 0.21700(10) 0.0161(4) Uani d . . . 1 . .
C C15 0.43408(17) 0.78363(10) 0.16119(9) 0.0162(4) Uani d . . . 1 . .
H H15 0.4264 0.8013 0.112 0.019 Uiso calc U . R 1 . .
C C16 0.41006(16) 0.70500(10) 0.17457(9) 0.0141(4) Uani d . . . 1 . .
C C17 0.48450(18) 0.70610(11) 0.38426(9) 0.0178(4) Uani d . . . 1 . .
H H17A 0.5357 0.7454 0.413 0.027 Uiso calc U . R 1 . .
H H17B 0.527 0.6552 0.3882 0.027 Uiso calc U . R 1 . .
H H17C 0.4049 0.7013 0.4028 0.027 Uiso calc U . R 1 . .
C C18 0.48464(18) 0.92318(10) 0.20072(11) 0.0209(4) Uani d . . . 1 . .
H H18A 0.5103 0.9288 0.1523 0.031 Uiso calc U . R 1 . .
H H18B 0.5479 0.9459 0.2375 0.031 Uiso calc U . R 1 . .
H H18C 0.4059 0.9506 0.2017 0.031 Uiso calc U . R 1 . .
C C19 0.37852(19) 0.65024(11) 0.11031(9) 0.0194(4) Uani d . . . 1 . .
H H19A 0.3741 0.6802 0.0648 0.029 Uiso calc U . R 1 . .
H H19B 0.2984 0.6253 0.1131 0.029 Uiso calc U . R 1 . .
H H19C 0.4426 0.6097 0.1114 0.029 Uiso calc U . R 1 . .
C C21 0.24813(16) 0.59076(10) 0.33014(9) 0.0115(3) Uani d . . . 1 . .
C C22 0.13373(16) 0.62458(10) 0.30004(9) 0.0130(3) Uani d . . . 1 . .
C C23 0.04094(17) 0.63337(10) 0.34400(9) 0.0147(4) Uani d . . . 1 . .
H H23 -0.0361 0.6555 0.3236 0.018 Uiso calc U . R 1 . .
C C24 0.05777(17) 0.61049(10) 0.41727(9) 0.0158(4) Uani d . . . 1 . .
C C25 0.16965(17) 0.57654(10) 0.44532(9) 0.0156(4) Uani d . . . 1 . .
H H25 0.1813 0.5598 0.4948 0.019 Uiso calc U . R 1 . .
C C26 0.26596(16) 0.56597(10) 0.40391(9) 0.0139(4) Uani d . . . 1 . .
C C27 0.10862(17) 0.65212(11) 0.22155(9) 0.0172(4) Uani d . . . 1 . .
H H27A 0.021 0.6659 0.2095 0.026 Uiso calc U . R 1 . .
H H27B 0.129 0.6099 0.1892 0.026 Uiso calc U . R 1 . .
H H27C 0.1597 0.6983 0.2152 0.026 Uiso calc U . R 1 . .
C C28 -0.04203(18) 0.62380(13) 0.46477(10) 0.0246(4) Uani d . . . 1 . .
H H28A -0.0371 0.5829 0.5024 0.037 Uiso calc U . R 1 . .
H H28B -0.1233 0.6217 0.4347 0.037 Uiso calc U . R 1 . .
H H28C -0.0306 0.6755 0.4881 0.037 Uiso calc U . R 1 . .
C C29 0.38409(17) 0.53086(11) 0.44254(9) 0.0177(4) Uani d . . . 1 . .
H H29A 0.4188 0.5657 0.4824 0.027 Uiso calc U . R 1 . .
H H29B 0.4437 0.5247 0.4079 0.027 Uiso calc U . R 1 . .
H H29C 0.3665 0.4793 0.4625 0.027 Uiso calc U . R 1 . .
C C31 0.65878(16) 0.43869(11) 0.22923(9) 0.0152(4) Uani d . . . 1 . .
C C32 0.70159(17) 0.50103(11) 0.19022(9) 0.0173(4) Uani d . . . 1 . .
F F32 0.68686(11) 0.57588(6) 0.21156(6) 0.0246(3) Uani d . . . 1 . .
C C33 0.75897(17) 0.49150(12) 0.12848(10) 0.0213(4) Uani d . . . 1 . .
F F33 0.80273(11) 0.55422(7) 0.09564(6) 0.0316(3) Uani d . . . 1 . .
C C34 0.76978(17) 0.41742(13) 0.10018(10) 0.0226(4) Uani d . . . 1 . .
F F34 0.82477(11) 0.40670(8) 0.04017(6) 0.0324(3) Uani d . . . 1 . .
C C35 0.72502(17) 0.35395(12) 0.13446(10) 0.0200(4) Uani d . . . 1 . .
F F35 0.73366(11) 0.28140(7) 0.10684(6) 0.0297(3) Uani d . . . 1 . .
C C36 0.67264(16) 0.36542(11) 0.19780(9) 0.0159(4) Uani d . . . 1 . .
F F36 0.63251(10) 0.29931(6) 0.22783(6) 0.0214(2) Uani d . . . 1 . .
C C41 0.57433(17) 0.37729(10) 0.35109(9) 0.0142(4) Uani d . . . 1 . .
C C42 0.67893(18) 0.33425(11) 0.38031(10) 0.0183(4) Uani d . . . 1 . .
F F42 0.79113(10) 0.35564(7) 0.36415(6) 0.0254(3) Uani d . . . 1 . .
C C43 0.67601(19) 0.26893(11) 0.42433(10) 0.0214(4) Uani d . . . 1 . .
F F43 0.78078(12) 0.23049(7) 0.45001(6) 0.0335(3) Uani d . . . 1 . .
C C44 0.5638(2) 0.24340(11) 0.44166(9) 0.0215(4) Uani d . . . 1 . .
F F44 0.55792(13) 0.17859(6) 0.48277(6) 0.0315(3) Uani d . . . 1 . .
C C45 0.45801(18) 0.28402(11) 0.41589(9) 0.0187(4) Uani d . . . 1 . .
F F45 0.34825(11) 0.25965(7) 0.43309(6) 0.0280(3) Uani d . . . 1 . .
C C46 0.46465(17) 0.34897(10) 0.37084(9) 0.0155(4) Uani d . . . 1 . .
F F46 0.35516(10) 0.38367(6) 0.34644(6) 0.0206(2) 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 C1 . 1.618(3) ?
B1 C41 . 1.634(3) ?
B1 C31 . 1.642(3) ?
B1 Cl1 . 1.909(2) ?
C1 C2 . 1.340(2) ?
C1 P1 . 1.7666(18) ?
P1 C2 . 1.7687(17) ?
P1 C11 . 1.8032(18) ?
P1 C21 . 1.8060(17) ?
Si1 C5 . 1.8621(18) ?
Si1 C4 . 1.8652(18) ?
Si1 C3 . 1.8657(19) ?
Si1 C2 . 1.8959(17) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C11 C12 . 1.411(2) ?
C11 C16 . 1.415(2) ?
C12 C13 . 1.392(2) ?
C12 C17 . 1.509(2) ?
C13 C14 . 1.391(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.391(3) ?
C14 C18 . 1.506(2) ?
C15 C16 . 1.392(2) ?
C15 H15 . 0.95 ?
C16 C19 . 1.512(2) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C21 C26 . 1.416(2) ?
C21 C22 . 1.416(2) ?
C22 C23 . 1.391(2) ?
C22 C27 . 1.514(2) ?
C23 C24 . 1.397(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.385(3) ?
C24 C28 . 1.508(3) ?
C25 C26 . 1.395(2) ?
C25 H25 . 0.95 ?
C26 C29 . 1.508(2) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C31 C36 . 1.392(3) ?
C31 C32 . 1.399(3) ?
C32 F32 . 1.349(2) ?
C32 C33 . 1.386(3) ?
C33 F33 . 1.347(2) ?
C33 C34 . 1.376(3) ?
C34 F34 . 1.345(2) ?
C34 C35 . 1.375(3) ?
C35 F35 . 1.344(2) ?
C35 C36 . 1.386(2) ?
C36 F36 . 1.354(2) ?
C41 C46 . 1.385(3) ?
C41 C42 . 1.400(3) ?
C42 F42 . 1.350(2) ?
C42 C43 . 1.381(3) ?
C43 F43 . 1.345(2) ?
C43 C44 . 1.378(3) ?
C44 F44 . 1.346(2) ?
C44 C45 . 1.373(3) ?
C45 F45 . 1.346(2) ?
C45 C46 . 1.392(2) ?
C46 F46 . 1.353(2) ?

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
C1 B1 C41 . . 114.88(15) ?
C1 B1 C31 . . 104.53(13) ?
C41 B1 C31 . . 114.57(15) ?
C1 B1 Cl1 . . 107.93(12) ?
C41 B1 Cl1 . . 105.42(11) ?
C31 B1 Cl1 . . 109.33(12) ?
C2 C1 B1 . . 142.92(16) ?
C2 C1 P1 . . 67.81(10) ?
B1 C1 P1 . . 148.02(13) ?
C1 P1 C2 . . 44.56(8) ?
C1 P1 C11 . . 121.50(8) ?
C2 P1 C11 . . 121.58(8) ?
C1 P1 C21 . . 123.01(8) ?
C2 P1 C21 . . 119.87(8) ?
C11 P1 C21 . . 111.17(8) ?
C5 Si1 C4 . . 109.03(9) ?
C5 Si1 C3 . . 112.53(9) ?
C4 Si1 C3 . . 111.60(9) ?
C5 Si1 C2 . . 104.87(8) ?
C4 Si1 C2 . . 109.82(8) ?
C3 Si1 C2 . . 108.76(8) ?
C1 C2 P1 . . 67.63(10) ?
C1 C2 Si1 . . 139.87(14) ?
P1 C2 Si1 . . 152.13(11) ?
Si1 C3 H3A . . 109.5 ?
Si1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
Si1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
Si1 C4 H4A . . 109.5 ?
Si1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
Si1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C12 C11 C16 . . 120.05(16) ?
C12 C11 P1 . . 117.42(12) ?
C16 C11 P1 . . 122.41(13) ?
C13 C12 C11 . . 118.53(16) ?
C13 C12 C17 . . 118.71(15) ?
C11 C12 C17 . . 122.76(16) ?
C14 C13 C12 . . 122.53(16) ?
C14 C13 H13 . . 118.7 ?
C12 C13 H13 . . 118.7 ?
C13 C14 C15 . . 117.63(16) ?
C13 C14 C18 . . 121.35(16) ?
C15 C14 C18 . . 121.02(16) ?
C14 C15 C16 . . 122.53(16) ?
C14 C15 H15 . . 118.7 ?
C16 C15 H15 . . 118.7 ?
C15 C16 C11 . . 118.41(16) ?
C15 C16 C19 . . 118.71(15) ?
C11 C16 C19 . . 122.87(15) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C26 C21 C22 . . 119.72(15) ?
C26 C21 P1 . . 122.30(13) ?
C22 C21 P1 . . 117.96(12) ?
C23 C22 C21 . . 119.13(15) ?
C23 C22 C27 . . 118.51(16) ?
C21 C22 C27 . . 122.36(16) ?
C22 C23 C24 . . 121.88(16) ?
C22 C23 H23 . . 119.1 ?
C24 C23 H23 . . 119.1 ?
C25 C24 C23 . . 118.04(16) ?
C25 C24 C28 . . 120.97(16) ?
C23 C24 C28 . . 120.97(17) ?
C24 C25 C26 . . 122.69(16) ?
C24 C25 H25 . . 118.7 ?
C26 C25 H25 . . 118.7 ?
C25 C26 C21 . . 118.52(16) ?
C25 C26 C29 . . 116.76(15) ?
C21 C26 C29 . . 124.69(16) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C36 C31 C32 . . 113.58(16) ?
C36 C31 B1 . . 125.51(16) ?
C32 C31 B1 . . 120.79(16) ?
F32 C32 C33 . . 115.92(16) ?
F32 C32 C31 . . 120.18(16) ?
C33 C32 C31 . . 123.90(18) ?
F33 C33 C34 . . 119.96(17) ?
F33 C33 C32 . . 120.51(18) ?
C34 C33 C32 . . 119.53(17) ?
F34 C34 C35 . . 120.10(18) ?
F34 C34 C33 . . 120.63(18) ?
C35 C34 C33 . . 119.27(17) ?
F35 C35 C34 . . 119.82(16) ?
F35 C35 C36 . . 120.61(17) ?
C34 C35 C36 . . 119.56(18) ?
F36 C36 C35 . . 115.12(16) ?
F36 C36 C31 . . 120.82(15) ?
C35 C36 C31 . . 124.05(17) ?
C46 C41 C42 . . 113.85(16) ?
C46 C41 B1 . . 126.65(16) ?
C42 C41 B1 . . 119.45(16) ?
F42 C42 C43 . . 116.31(16) ?
F42 C42 C41 . . 119.31(16) ?
C43 C42 C41 . . 124.36(18) ?
F43 C43 C44 . . 120.24(17) ?
F43 C43 C42 . . 120.77(18) ?
C44 C43 C42 . . 118.99(17) ?
F44 C44 C45 . . 120.33(18) ?
F44 C44 C43 . . 120.20(18) ?
C45 C44 C43 . . 119.47(16) ?
F45 C45 C44 . . 119.71(16) ?
F45 C45 C46 . . 120.51(17) ?
C44 C45 C46 . . 119.77(17) ?
F46 C46 C41 . . 121.04(15) ?
F46 C46 C45 . . 115.43(16) ?
C41 C46 C45 . . 123.53(17) ?

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
C41 B1 C1 C2 . . . . -89.3(3) ?
C31 B1 C1 C2 . . . . 37.1(3) ?
Cl1 B1 C1 C2 . . . . 153.4(2) ?
C41 B1 C1 P1 . . . . 111.3(2) ?
C31 B1 C1 P1 . . . . -122.3(2) ?
Cl1 B1 C1 P1 . . . . -6.0(3) ?
B1 C1 P1 C2 . . . . 166.8(3) ?
C2 C1 P1 C11 . . . . -104.66(12) ?
B1 C1 P1 C11 . . . . 62.1(3) ?
C2 C1 P1 C21 . . . . 100.76(12) ?
B1 C1 P1 C21 . . . . -92.5(2) ?
B1 C1 C2 P1 . . . . -168.4(3) ?
B1 C1 C2 Si1 . . . . 17.3(4) ?
P1 C1 C2 Si1 . . . . -174.3(2) ?
C11 P1 C2 C1 . . . . 104.48(12) ?
C21 P1 C2 C1 . . . . -108.19(12) ?
C1 P1 C2 Si1 . . . . 172.1(3) ?
C11 P1 C2 Si1 . . . . -83.4(2) ?
C21 P1 C2 Si1 . . . . 63.9(2) ?
C5 Si1 C2 C1 . . . . 36.8(2) ?
C4 Si1 C2 C1 . . . . -80.3(2) ?
C3 Si1 C2 C1 . . . . 157.3(2) ?
C5 Si1 C2 P1 . . . . -131.9(2) ?
C4 Si1 C2 P1 . . . . 111.1(2) ?
C3 Si1 C2 P1 . . . . -11.3(2) ?
C1 P1 C11 C12 . . . . -100.98(15) ?
C2 P1 C11 C12 . . . . -153.82(13) ?
C21 P1 C11 C12 . . . . 56.31(15) ?
C1 P1 C11 C16 . . . . 83.10(16) ?
C2 P1 C11 C16 . . . . 30.27(18) ?
C21 P1 C11 C16 . . . . -119.61(15) ?
C16 C11 C12 C13 . . . . 4.7(3) ?
P1 C11 C12 C13 . . . . -171.28(13) ?
C16 C11 C12 C17 . . . . -175.06(16) ?
P1 C11 C12 C17 . . . . 8.9(2) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
C17 C12 C13 C14 . . . . -179.94(17) ?
C12 C13 C14 C15 . . . . -4.4(3) ?
C12 C13 C14 C18 . . . . 174.55(17) ?
C13 C14 C15 C16 . . . . 3.7(3) ?
C18 C14 C15 C16 . . . . -175.28(17) ?
C14 C15 C16 C11 . . . . 1.1(3) ?
C14 C15 C16 C19 . . . . -177.23(17) ?
C12 C11 C16 C15 . . . . -5.4(3) ?
P1 C11 C16 C15 . . . . 170.41(14) ?
C12 C11 C16 C19 . . . . 172.88(17) ?
P1 C11 C16 C19 . . . . -11.3(2) ?
C1 P1 C21 C26 . . . . 43.47(18) ?
C2 P1 C21 C26 . . . . 96.12(15) ?
C11 P1 C21 C26 . . . . -113.42(15) ?
C1 P1 C21 C22 . . . . -138.22(13) ?
C2 P1 C21 C22 . . . . -85.57(15) ?
C11 P1 C21 C22 . . . . 64.89(15) ?
C26 C21 C22 C23 . . . . 0.5(2) ?
P1 C21 C22 C23 . . . . -177.86(13) ?
C26 C21 C22 C27 . . . . -179.87(16) ?
P1 C21 C22 C27 . . . . 1.8(2) ?
C21 C22 C23 C24 . . . . 0.6(3) ?
C27 C22 C23 C24 . . . . -179.00(16) ?
C22 C23 C24 C25 . . . . -1.6(3) ?
C22 C23 C24 C28 . . . . 177.31(17) ?
C23 C24 C25 C26 . . . . 1.3(3) ?
C28 C24 C25 C26 . . . . -177.51(17) ?
C24 C25 C26 C21 . . . . -0.2(3) ?
C24 C25 C26 C29 . . . . 177.85(16) ?
C22 C21 C26 C25 . . . . -0.7(2) ?
P1 C21 C26 C25 . . . . 177.58(13) ?
C22 C21 C26 C29 . . . . -178.62(16) ?
P1 C21 C26 C29 . . . . -0.3(2) ?
C1 B1 C31 C36 . . . . -109.36(18) ?
C41 B1 C31 C36 . . . . 17.3(2) ?
Cl1 B1 C31 C36 . . . . 135.30(16) ?
C1 B1 C31 C32 . . . . 66.3(2) ?
C41 B1 C31 C32 . . . . -167.07(16) ?
Cl1 B1 C31 C32 . . . . -49.03(19) ?
C36 C31 C32 F32 . . . . 175.71(15) ?
B1 C31 C32 F32 . . . . -0.5(2) ?
C36 C31 C32 C33 . . . . -3.5(3) ?
B1 C31 C32 C33 . . . . -179.68(16) ?
F32 C32 C33 F33 . . . . 3.7(3) ?
C31 C32 C33 F33 . . . . -177.03(16) ?
F32 C32 C33 C34 . . . . -175.50(16) ?
C31 C32 C33 C34 . . . . 3.8(3) ?
F33 C33 C34 F34 . . . . 0.6(3) ?
C32 C33 C34 F34 . . . . 179.81(16) ?
F33 C33 C34 C35 . . . . 179.78(17) ?
C32 C33 C34 C35 . . . . -1.0(3) ?
F34 C34 C35 F35 . . . . -1.6(3) ?
C33 C34 C35 F35 . . . . 179.18(17) ?
F34 C34 C35 C36 . . . . 177.62(16) ?
C33 C34 C35 C36 . . . . -1.6(3) ?
F35 C35 C36 F36 . . . . -0.1(2) ?
C34 C35 C36 F36 . . . . -179.34(16) ?
F35 C35 C36 C31 . . . . -179.07(16) ?
C34 C35 C36 C31 . . . . 1.7(3) ?
C32 C31 C36 F36 . . . . -178.13(15) ?
B1 C31 C36 F36 . . . . -2.2(3) ?
C32 C31 C36 C35 . . . . 0.8(3) ?
B1 C31 C36 C35 . . . . 176.73(17) ?
C1 B1 C41 C46 . . . . -3.2(2) ?
C31 B1 C41 C46 . . . . -124.25(18) ?
Cl1 B1 C41 C46 . . . . 115.51(17) ?
C1 B1 C41 C42 . . . . 179.60(15) ?
C31 B1 C41 C42 . . . . 58.5(2) ?
Cl1 B1 C41 C42 . . . . -61.71(18) ?
C46 C41 C42 F42 . . . . 179.18(15) ?
B1 C41 C42 F42 . . . . -3.3(2) ?
C46 C41 C42 C43 . . . . 0.6(3) ?
B1 C41 C42 C43 . . . . 178.16(17) ?
F42 C42 C43 F43 . . . . 1.1(3) ?
C41 C42 C43 F43 . . . . 179.68(16) ?
F42 C42 C43 C44 . . . . -178.86(16) ?
C41 C42 C43 C44 . . . . -0.2(3) ?
F43 C43 C44 F44 . . . . -1.8(3) ?
C42 C43 C44 F44 . . . . 178.12(16) ?
F43 C43 C44 C45 . . . . 179.02(16) ?
C42 C43 C44 C45 . . . . -1.1(3) ?
F44 C44 C45 F45 . . . . 1.3(3) ?
C43 C44 C45 F45 . . . . -179.52(16) ?
F44 C44 C45 C46 . . . . -177.24(16) ?
C43 C44 C45 C46 . . . . 1.9(3) ?
C42 C41 C46 F46 . . . . -179.33(15) ?
B1 C41 C46 F46 . . . . 3.3(3) ?
C42 C41 C46 C45 . . . . 0.3(3) ?
B1 C41 C46 C45 . . . . -177.02(16) ?
F45 C45 C46 F46 . . . . -0.5(2) ?
C44 C45 C46 F46 . . . . 178.07(15) ?
F45 C45 C46 C41 . . . . 179.86(16) ?
C44 C45 C46 C41 . . . . -1.6(3) ?

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

data_erk9214
_database_code_depnum_ccdc_archive 'CCDC 1865544'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H31 B Br F10 P Si'
_chemical_formula_weight         791.38

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'
Si Si 0.0817 0.0704 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.6668(2)
_cell_length_b                   20.0637(4)
_cell_length_c                   19.4399(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.326(2)
_cell_angle_gamma                90.00
_cell_volume                     3754.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8499
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    1.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9071
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            26502
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6527
_reflns_number_gt                5034
_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 badly disordered half dichloromethane molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program 
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18.) 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 0.000 0.000 0.000 216 49 ' '
2 0.000 0.500 0.500 216 49 ' '
_platon_squeeze_void_probe_radius 1.20

_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)+(0.0268P)²+7.6636P] 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         6527
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12204(4) 0.64089(2) 0.854345(19) 0.04085(13) Uani 1 1 d . . .
P1 P 0.57492(10) 0.70374(5) 0.85835(4) 0.0272(2) Uani 1 1 d . . .
Si1 Si 0.34228(11) 0.79470(6) 0.95137(5) 0.0355(3) Uani 1 1 d . . .
B1 B 0.2738(4) 0.6612(2) 0.7865(2) 0.0299(9) Uani 1 1 d . . .
C1 C 0.3938(4) 0.69874(19) 0.83514(16) 0.0273(8) Uani 1 1 d . . .
C2 C 0.4244(4) 0.73516(19) 0.89162(17) 0.0285(8) Uani 1 1 d . . .
C3 C 0.4795(5) 0.8525(2) 0.9883(2) 0.0494(11) Uani 1 1 d . . .
H3A H 0.5265 0.8726 0.9509 0.074 Uiso 1 1 calc R . .
H3B H 0.5472 0.8277 1.0192 0.074 Uiso 1 1 calc R . .
H3C H 0.4373 0.8876 1.0145 0.074 Uiso 1 1 calc R . .
C4 C 0.2604(5) 0.7496(2) 1.0204(2) 0.0521(12) Uani 1 1 d . . .
H4A H 0.2061 0.7810 1.0456 0.078 Uiso 1 1 calc R . .
H4B H 0.3328 0.7294 1.0524 0.078 Uiso 1 1 calc R . .
H4C H 0.1992 0.7147 0.9997 0.078 Uiso 1 1 calc R . .
C5 C 0.2062(4) 0.8393(2) 0.8962(2) 0.0518(12) Uani 1 1 d . . .
H5A H 0.1417 0.8069 0.8731 0.078 Uiso 1 1 calc R . .
H5B H 0.2494 0.8655 0.8614 0.078 Uiso 1 1 calc R . .
H5C H 0.1553 0.8691 0.9248 0.078 Uiso 1 1 calc R . .
C11 C 0.6817(3) 0.7644(2) 0.81942(17) 0.0284(8) Uani 1 1 d . . .
C12 C 0.6614(4) 0.7809(2) 0.74862(18) 0.0308(8) Uani 1 1 d . . .
C13 C 0.7349(4) 0.8350(2) 0.7259(2) 0.0390(10) Uani 1 1 d . . .
H13 H 0.7230 0.8463 0.6782 0.047 Uiso 1 1 calc R . .
C14 C 0.8245(4) 0.8733(2) 0.7694(2) 0.0396(10) Uani 1 1 d . . .
C15 C 0.8449(4) 0.8538(2) 0.8382(2) 0.0386(9) Uani 1 1 d . . .
H15 H 0.9077 0.8787 0.8687 0.046 Uiso 1 1 calc R . .
C16 C 0.7779(4) 0.8001(2) 0.86400(18) 0.0339(9) Uani 1 1 d . . .
C17 C 0.5712(4) 0.7415(2) 0.69582(18) 0.0382(10) Uani 1 1 d . . .
H17A H 0.5144 0.7722 0.6659 0.057 Uiso 1 1 calc R . .
H17B H 0.5106 0.7118 0.7194 0.057 Uiso 1 1 calc R . .
H17C H 0.6301 0.7150 0.6678 0.057 Uiso 1 1 calc R . .
C18 C 0.8978(5) 0.9335(2) 0.7440(3) 0.0516(12) Uani 1 1 d . . .
H18A H 0.8655 0.9736 0.7664 0.077 Uiso 1 1 calc R . .
H18B H 0.8772 0.9375 0.6938 0.077 Uiso 1 1 calc R . .
H18C H 0.9982 0.9286 0.7551 0.077 Uiso 1 1 calc R . .
C19 C 0.8139(4) 0.7804(2) 0.93869(19) 0.0446(11) Uani 1 1 d . . .
H19A H 0.8659 0.8165 0.9631 0.067 Uiso 1 1 calc R . .
H19B H 0.8709 0.7399 0.9407 0.067 Uiso 1 1 calc R . .
H19C H 0.7283 0.7719 0.9606 0.067 Uiso 1 1 calc R . .
C21 C 0.6644(4) 0.63248(19) 0.89662(17) 0.0287(8) Uani 1 1 d . . .
C22 C 0.7425(4) 0.59269(19) 0.85464(17) 0.0298(8) Uani 1 1 d . . .
C23 C 0.8047(4) 0.5357(2) 0.88262(19) 0.0384(9) Uani 1 1 d . . .
H23 H 0.8596 0.5096 0.8548 0.046 Uiso 1 1 calc R . .
C24 C 0.7905(5) 0.5150(2) 0.9498(2) 0.0434(10) Uani 1 1 d . . .
C25 C 0.7122(5) 0.5552(2) 0.98982(19) 0.0440(10) Uani 1 1 d . . .
H25 H 0.7015 0.5421 1.0360 0.053 Uiso 1 1 calc R . .
C26 C 0.6496(4) 0.6132(2) 0.96519(18) 0.0367(9) Uani 1 1 d . . .
C27 C 0.7575(4) 0.6093(2) 0.77982(17) 0.0342(9) Uani 1 1 d . . .
H27A H 0.8111 0.5743 0.7594 0.051 Uiso 1 1 calc R . .
H27B H 0.8057 0.6521 0.7771 0.051 Uiso 1 1 calc R . .
H27C H 0.6652 0.6124 0.7545 0.051 Uiso 1 1 calc R . .
C28 C 0.8526(6) 0.4510(2) 0.9781(2) 0.0690(16) Uani 1 1 d . . .
H28A H 0.8706 0.4545 1.0284 0.103 Uiso 1 1 calc R . .
H28B H 0.9401 0.4425 0.9578 0.103 Uiso 1 1 calc R . .
H28C H 0.7878 0.4143 0.9664 0.103 Uiso 1 1 calc R . .
C29 C 0.5634(5) 0.6511(2) 1.0129(2) 0.0538(12) Uani 1 1 d . . .
H29A H 0.5700 0.6293 1.0582 0.081 Uiso 1 1 calc R . .
H29B H 0.4662 0.6518 0.9934 0.081 Uiso 1 1 calc R . .
H29C H 0.5980 0.6969 1.0181 0.081 Uiso 1 1 calc R . .
C31 C 0.1896(4) 0.7081(2) 0.72857(17) 0.0304(8) Uani 1 1 d . . .
F32 F 0.3249(2) 0.80580(11) 0.75276(11) 0.0419(6) Uani 1 1 d . . .
C32 C 0.2137(4) 0.7759(2) 0.71881(18) 0.0334(9) Uani 1 1 d . . .
F33 F 0.1657(3) 0.88046(13) 0.66785(13) 0.0595(7) Uani 1 1 d . . .
C33 C 0.1322(4) 0.8159(2) 0.6741(2) 0.0396(10) Uani 1 1 d . . .
F34 F -0.0641(3) 0.82781(15) 0.59361(13) 0.0628(8) Uani 1 1 d . . .
C34 C 0.0175(4) 0.7907(3) 0.6381(2) 0.0454(11) Uani 1 1 d . . .
F35 F -0.1251(2) 0.69695(15) 0.60847(12) 0.0577(7) Uani 1 1 d . . .
C35 C -0.0133(4) 0.7236(2) 0.64499(18) 0.0403(10) Uani 1 1 d . . .
F36 F 0.0402(2) 0.61876(12) 0.69240(11) 0.0425(6) Uani 1 1 d . . .
C36 C 0.0727(4) 0.6838(2) 0.68889(18) 0.0344(9) Uani 1 1 d . . .
C41 C 0.3371(4) 0.59217(19) 0.75944(18) 0.0306(8) Uani 1 1 d . . .
F42 F 0.3104(2) 0.61966(12) 0.63978(10) 0.0421(6) Uani 1 1 d . . .
C42 C 0.3542(4) 0.5770(2) 0.69083(18) 0.0340(9) Uani 1 1 d . . .
F43 F 0.4263(3) 0.50787(13) 0.60225(12) 0.0616(8) Uani 1 1 d . . .
C43 C 0.4156(5) 0.5190(2) 0.6701(2) 0.0419(10) Uani 1 1 d . . .
F44 F 0.5275(3) 0.41751(13) 0.69805(14) 0.0604(7) Uani 1 1 d . . .
C44 C 0.4675(4) 0.4736(2) 0.7176(2) 0.0423(10) Uani 1 1 d . . .
F45 F 0.5071(3) 0.44205(13) 0.83462(13) 0.0545(7) Uani 1 1 d . . .
C45 C 0.4571(4) 0.4860(2) 0.7870(2) 0.0401(10) Uani 1 1 d . . .
F46 F 0.3868(2) 0.55260(12) 0.87424(10) 0.0430(6) Uani 1 1 d . . .
C46 C 0.3929(4) 0.5438(2) 0.80532(18) 0.0337(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.102(4) . ?
P1 C2 1.762(4) . ?
P1 C1 1.770(4) . ?
P1 C21 1.796(4) . ?
P1 C11 1.806(4) . ?
Si1 C5 1.849(5) . ?
Si1 C4 1.855(4) . ?
Si1 C3 1.856(4) . ?
Si1 C2 1.892(4) . ?
B1 C1 1.614(5) . ?
B1 C41 1.620(6) . ?
B1 C31 1.627(6) . ?
C1 C2 1.329(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 C16 1.407(5) . ?
C11 C12 1.412(5) . ?
C12 C13 1.392(5) . ?
C12 C17 1.507(5) . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(6) . ?
C14 C18 1.507(5) . ?
C15 C16 1.376(6) . ?
C15 H15 0.9500 . ?
C16 C19 1.514(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C26 1.408(5) . ?
C21 C22 1.410(5) . ?
C22 C23 1.380(5) . ?
C22 C27 1.512(5) . ?
C23 C24 1.390(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(6) . ?
C24 C28 1.500(6) . ?
C25 C26 1.377(6) . ?
C25 H25 0.9500 . ?
C26 C29 1.510(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C36 1.395(5) . ?
C31 C32 1.396(5) . ?
F32 C32 1.349(4) . ?
C32 C33 1.375(5) . ?
F33 C33 1.344(5) . ?
C33 C34 1.353(6) . ?
F34 C34 1.341(5) . ?
C34 C35 1.388(6) . ?
F35 C35 1.348(5) . ?
C35 C36 1.388(6) . ?
F36 C36 1.345(5) . ?
C41 C46 1.393(5) . ?
C41 C42 1.393(5) . ?
F42 C42 1.349(4) . ?
C42 C43 1.382(5) . ?
F43 C43 1.352(4) . ?
C43 C44 1.360(6) . ?
F44 C44 1.338(5) . ?
C44 C45 1.385(6) . ?
F45 C45 1.335(4) . ?
C45 C46 1.377(6) . ?
F46 C46 1.358(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 P1 C1 44.21(16) . . ?
C2 P1 C21 120.97(16) . . ?
C1 P1 C21 119.15(18) . . ?
C2 P1 C11 115.84(17) . . ?
C1 P1 C11 121.44(17) . . ?
C21 P1 C11 115.98(17) . . ?
C5 Si1 C4 109.1(2) . . ?
C5 Si1 C3 111.5(2) . . ?
C4 Si1 C3 111.2(2) . . ?
C5 Si1 C2 105.43(18) . . ?
C4 Si1 C2 111.60(19) . . ?
C3 Si1 C2 107.85(18) . . ?
C1 B1 C41 108.5(3) . . ?
C1 B1 C31 114.9(3) . . ?
C41 B1 C31 116.7(3) . . ?
C1 B1 Br1 103.2(2) . . ?
C41 B1 Br1 110.2(3) . . ?
C31 B1 Br1 102.3(2) . . ?
C2 C1 B1 146.5(3) . . ?
C2 C1 P1 67.6(2) . . ?
B1 C1 P1 144.7(3) . . ?
C1 C2 P1 68.2(2) . . ?
C1 C2 Si1 141.3(3) . . ?
P1 C2 Si1 149.2(2) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C11 C12 120.3(3) . . ?
C16 C11 P1 117.1(3) . . ?
C12 C11 P1 122.3(3) . . ?
C13 C12 C11 117.7(4) . . ?
C13 C12 C17 118.2(3) . . ?
C11 C12 C17 124.1(3) . . ?
C14 C13 C12 123.2(4) . . ?
C14 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C13 C14 C15 117.2(4) . . ?
C13 C14 C18 122.1(4) . . ?
C15 C14 C18 120.8(4) . . ?
C16 C15 C14 122.8(4) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C15 C16 C11 118.7(3) . . ?
C15 C16 C19 118.7(4) . . ?
C11 C16 C19 122.5(4) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C21 C22 120.0(3) . . ?
C26 C21 P1 121.6(3) . . ?
C22 C21 P1 118.3(3) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 C27 119.0(3) . . ?
C21 C22 C27 122.4(3) . . ?
C22 C23 C24 122.7(4) . . ?
C22 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C23 C24 C25 117.3(4) . . ?
C23 C24 C28 121.9(4) . . ?
C25 C24 C28 120.8(4) . . ?
C26 C25 C24 122.7(4) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C21 118.8(4) . . ?
C25 C26 C29 117.5(3) . . ?
C21 C26 C29 123.6(4) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C36 C31 C32 113.7(3) . . ?
C36 C31 B1 120.5(4) . . ?
C32 C31 B1 125.4(3) . . ?
F32 C32 C33 115.7(4) . . ?
F32 C32 C31 120.2(3) . . ?
C33 C32 C31 124.1(4) . . ?
F33 C33 C34 120.4(4) . . ?
F33 C33 C32 119.4(4) . . ?
C34 C33 C32 120.3(4) . . ?
F34 C34 C33 122.1(4) . . ?
F34 C34 C35 118.8(4) . . ?
C33 C34 C35 119.0(4) . . ?
F35 C35 C34 120.2(4) . . ?
F35 C35 C36 120.0(4) . . ?
C34 C35 C36 119.7(4) . . ?
F36 C36 C35 117.4(4) . . ?
F36 C36 C31 119.5(4) . . ?
C35 C36 C31 123.1(4) . . ?
C46 C41 C42 112.7(3) . . ?
C46 C41 B1 121.6(3) . . ?
C42 C41 B1 125.4(3) . . ?
F42 C42 C43 115.7(3) . . ?
F42 C42 C41 120.5(3) . . ?
C43 C42 C41 123.8(4) . . ?
F43 C43 C44 119.7(4) . . ?
F43 C43 C42 119.8(4) . . ?
C44 C43 C42 120.5(4) . . ?
F44 C44 C43 120.9(4) . . ?
F44 C44 C45 120.1(4) . . ?
C43 C44 C45 119.1(4) . . ?
F45 C45 C46 121.3(4) . . ?
F45 C45 C44 120.1(4) . . ?
C46 C45 C44 118.5(4) . . ?
F46 C46 C45 115.2(3) . . ?
F46 C46 C41 119.4(3) . . ?
C45 C46 C41 125.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C41 B1 C1 C2 -141.8(6) . . . . ?
C31 B1 C1 C2 85.5(7) . . . . ?
Br1 B1 C1 C2 -25.0(7) . . . . ?
C41 B1 C1 P1 18.0(6) . . . . ?
C31 B1 C1 P1 -114.7(5) . . . . ?
Br1 B1 C1 P1 134.8(4) . . . . ?
C21 P1 C1 C2 105.8(2) . . . . ?
C11 P1 C1 C2 -96.0(3) . . . . ?
C2 P1 C1 B1 -168.1(6) . . . . ?
C21 P1 C1 B1 -62.3(5) . . . . ?
C11 P1 C1 B1 95.9(5) . . . . ?
B1 C1 C2 P1 167.5(6) . . . . ?
B1 C1 C2 Si1 -23.9(9) . . . . ?
P1 C1 C2 Si1 168.6(4) . . . . ?
C21 P1 C2 C1 -101.4(3) . . . . ?
C11 P1 C2 C1 109.5(2) . . . . ?
C1 P1 C2 Si1 -166.0(5) . . . . ?
C21 P1 C2 Si1 92.6(4) . . . . ?
C11 P1 C2 Si1 -56.6(5) . . . . ?
C5 Si1 C2 C1 -31.7(5) . . . . ?
C4 Si1 C2 C1 86.6(5) . . . . ?
C3 Si1 C2 C1 -151.0(5) . . . . ?
C5 Si1 C2 P1 127.3(4) . . . . ?
C4 Si1 C2 P1 -114.4(4) . . . . ?
C3 Si1 C2 P1 8.0(5) . . . . ?
C2 P1 C11 C16 83.9(3) . . . . ?
C1 P1 C11 C16 134.3(3) . . . . ?
C21 P1 C11 C16 -66.8(3) . . . . ?
C2 P1 C11 C12 -89.8(3) . . . . ?
C1 P1 C11 C12 -39.4(4) . . . . ?
C21 P1 C11 C12 119.5(3) . . . . ?
C16 C11 C12 C13 -2.8(5) . . . . ?
P1 C11 C12 C13 170.6(3) . . . . ?
C16 C11 C12 C17 173.9(4) . . . . ?
P1 C11 C12 C17 -12.7(5) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C17 C12 C13 C14 -177.7(4) . . . . ?
C12 C13 C14 C15 3.0(6) . . . . ?
C12 C13 C14 C18 -177.2(4) . . . . ?
C13 C14 C15 C16 -1.6(6) . . . . ?
C18 C14 C15 C16 178.5(4) . . . . ?
C14 C15 C16 C11 -1.9(6) . . . . ?
C14 C15 C16 C19 176.3(4) . . . . ?
C12 C11 C16 C15 4.1(5) . . . . ?
P1 C11 C16 C15 -169.6(3) . . . . ?
C12 C11 C16 C19 -174.0(4) . . . . ?
P1 C11 C16 C19 12.3(5) . . . . ?
C2 P1 C21 C26 -21.8(4) . . . . ?
C1 P1 C21 C26 -73.3(4) . . . . ?
C11 P1 C21 C26 127.3(3) . . . . ?
C2 P1 C21 C22 153.5(3) . . . . ?
C1 P1 C21 C22 102.0(3) . . . . ?
C11 P1 C21 C22 -57.4(3) . . . . ?
C26 C21 C22 C23 -0.9(5) . . . . ?
P1 C21 C22 C23 -176.3(3) . . . . ?
C26 C21 C22 C27 177.6(4) . . . . ?
P1 C21 C22 C27 2.3(5) . . . . ?
C21 C22 C23 C24 1.8(6) . . . . ?
C27 C22 C23 C24 -176.8(4) . . . . ?
C22 C23 C24 C25 -1.5(6) . . . . ?
C22 C23 C24 C28 176.6(4) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C28 C24 C25 C26 -177.9(5) . . . . ?
C24 C25 C26 C21 0.5(7) . . . . ?
C24 C25 C26 C29 177.9(4) . . . . ?
C22 C21 C26 C25 -0.2(6) . . . . ?
P1 C21 C26 C25 175.0(3) . . . . ?
C22 C21 C26 C29 -177.5(4) . . . . ?
P1 C21 C26 C29 -2.3(6) . . . . ?
C1 B1 C31 C36 -172.2(3) . . . . ?
C41 B1 C31 C36 59.1(4) . . . . ?
Br1 B1 C31 C36 -61.3(4) . . . . ?
C1 B1 C31 C32 0.0(5) . . . . ?
C41 B1 C31 C32 -128.7(4) . . . . ?
Br1 B1 C31 C32 111.0(3) . . . . ?
C36 C31 C32 F32 -178.6(3) . . . . ?
B1 C31 C32 F32 8.7(5) . . . . ?
C36 C31 C32 C33 -0.6(5) . . . . ?
B1 C31 C32 C33 -173.3(3) . . . . ?
F32 C32 C33 F33 -1.0(5) . . . . ?
C31 C32 C33 F33 -179.0(3) . . . . ?
F32 C32 C33 C34 -179.4(3) . . . . ?
C31 C32 C33 C34 2.5(6) . . . . ?
F33 C33 C34 F34 2.1(6) . . . . ?
C32 C33 C34 F34 -179.4(3) . . . . ?
F33 C33 C34 C35 179.2(3) . . . . ?
C32 C33 C34 C35 -2.4(6) . . . . ?
F34 C34 C35 F35 -1.3(5) . . . . ?
C33 C34 C35 F35 -178.4(3) . . . . ?
F34 C34 C35 C36 177.7(3) . . . . ?
C33 C34 C35 C36 0.6(6) . . . . ?
F35 C35 C36 F36 0.6(5) . . . . ?
C34 C35 C36 F36 -178.4(3) . . . . ?
F35 C35 C36 C31 -179.6(3) . . . . ?
C34 C35 C36 C31 1.4(5) . . . . ?
C32 C31 C36 F36 178.4(3) . . . . ?
B1 C31 C36 F36 -8.5(5) . . . . ?
C32 C31 C36 C35 -1.4(5) . . . . ?
B1 C31 C36 C35 171.7(3) . . . . ?
C1 B1 C41 C46 57.8(4) . . . . ?
C31 B1 C41 C46 -170.4(3) . . . . ?
Br1 B1 C41 C46 -54.4(4) . . . . ?
C1 B1 C41 C42 -115.8(4) . . . . ?
C31 B1 C41 C42 15.9(5) . . . . ?
Br1 B1 C41 C42 131.9(3) . . . . ?
C46 C41 C42 F42 -177.7(3) . . . . ?
B1 C41 C42 F42 -3.6(6) . . . . ?
C46 C41 C42 C43 2.2(6) . . . . ?
B1 C41 C42 C43 176.3(4) . . . . ?
F42 C42 C43 F43 -1.0(6) . . . . ?
C41 C42 C43 F43 179.1(4) . . . . ?
F42 C42 C43 C44 177.8(4) . . . . ?
C41 C42 C43 C44 -2.1(7) . . . . ?
F43 C43 C44 F44 -0.9(7) . . . . ?
C42 C43 C44 F44 -179.7(4) . . . . ?
F43 C43 C44 C45 179.3(4) . . . . ?
C42 C43 C44 C45 0.5(7) . . . . ?
F44 C44 C45 F45 0.1(6) . . . . ?
C43 C44 C45 F45 179.9(4) . . . . ?
F44 C44 C45 C46 -179.1(4) . . . . ?
C43 C44 C45 C46 0.7(6) . . . . ?
F45 C45 C46 F46 1.0(5) . . . . ?
C44 C45 C46 F46 -179.9(3) . . . . ?
F45 C45 C46 C41 -179.6(4) . . . . ?
C44 C45 C46 C41 -0.5(6) . . . . ?
C42 C41 C46 F46 178.5(3) . . . . ?
B1 C41 C46 F46 4.1(5) . . . . ?
C42 C41 C46 C45 -0.9(6) . . . . ?
B1 C41 C46 C45 -175.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_erk9235
_database_code_depnum_ccdc_archive 'CCDC 1865546'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 B Cl F10 P'
_chemical_formula_weight         626.69

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   9.2115(2)
_cell_length_b                   22.0031(5)
_cell_length_c                   14.1968(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.690(1)
_cell_angle_gamma                90.00
_cell_volume                     2851.55(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4482
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            13796
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4909
_reflns_number_gt                3453
_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    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP-SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_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. 
;

_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)+(0.0000P)²+8.8340P] 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         4909
_refine_ls_number_parameters     476
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.156
_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
P1 P 0.89197(14) 0.25164(6) 0.83353(9) 0.0317(3) Uani 1 1 d . . .
Cl1 Cl 1.21133(16) 0.26886(6) 0.69799(10) 0.0500(4) Uani 1 1 d . A .
C1 C 1.0183(5) 0.3111(2) 0.8199(3) 0.0294(11) Uani 1 1 d . A .
C2 C 0.9520(5) 0.3163(2) 0.8976(3) 0.0273(10) Uani 1 1 d . . .
C3 C 0.9418(5) 0.3525(2) 0.9825(3) 0.0286(10) Uani 1 1 d . . .
C4 C 0.8432(5) 0.3365(2) 1.0439(3) 0.0340(11) Uani 1 1 d . . .
H4 H 0.7814 0.3022 1.0299 0.041 Uiso 1 1 calc R . .
C5 C 0.8340(6) 0.3701(2) 1.1257(4) 0.0421(13) Uani 1 1 d . . .
H5 H 0.7653 0.3590 1.1669 0.051 Uiso 1 1 calc R . .
C6 C 0.9245(6) 0.4197(2) 1.1471(4) 0.0452(14) Uani 1 1 d . . .
H6 H 0.9188 0.4426 1.2033 0.054 Uiso 1 1 calc R . .
C7 C 1.0240(6) 0.4358(2) 1.0860(4) 0.0442(13) Uani 1 1 d . . .
H7 H 1.0865 0.4698 1.1005 0.053 Uiso 1 1 calc R . .
C8 C 1.0325(5) 0.4028(2) 1.0048(3) 0.0366(12) Uani 1 1 d . . .
H8 H 1.1006 0.4143 0.9634 0.044 Uiso 1 1 calc R . .
C9 C 0.7098(6) 0.2545(3) 0.7614(4) 0.0464(14) Uani 1 1 d . . .
C10 C 0.6666(6) 0.3202(3) 0.7495(5) 0.070(2) Uani 1 1 d . . .
H10A H 0.5670 0.3231 0.7154 0.105 Uiso 1 1 calc R . .
H10B H 0.7348 0.3412 0.7132 0.105 Uiso 1 1 calc R . .
H10C H 0.6698 0.3392 0.8122 0.105 Uiso 1 1 calc R . .
C11 C 0.7216(8) 0.2269(4) 0.6635(4) 0.085(2) Uani 1 1 d . . .
H11A H 0.6274 0.2309 0.6228 0.128 Uiso 1 1 calc R . .
H11B H 0.7475 0.1838 0.6708 0.128 Uiso 1 1 calc R . .
H11C H 0.7975 0.2483 0.6343 0.128 Uiso 1 1 calc R . .
C12 C 0.5980(7) 0.2195(4) 0.8107(5) 0.092(3) Uani 1 1 d . . .
H12A H 0.5960 0.2361 0.8746 0.139 Uiso 1 1 calc R . .
H12B H 0.6255 0.1765 0.8154 0.139 Uiso 1 1 calc R . .
H12C H 0.5007 0.2236 0.7737 0.139 Uiso 1 1 calc R . .
C13 C 0.9635(6) 0.1772(2) 0.8776(4) 0.0431(13) Uani 1 1 d . . .
C14 C 0.9590(10) 0.1310(3) 0.7978(5) 0.091(3) Uani 1 1 d . . .
H14A H 1.0156 0.1463 0.7490 0.137 Uiso 1 1 calc R . .
H14B H 0.8572 0.1243 0.7696 0.137 Uiso 1 1 calc R . .
H14C H 1.0014 0.0926 0.8231 0.137 Uiso 1 1 calc R . .
C15 C 0.8786(8) 0.1536(3) 0.9560(5) 0.077(2) Uani 1 1 d . . .
H15A H 0.7798 0.1415 0.9280 0.115 Uiso 1 1 calc R . .
H15B H 0.8719 0.1858 1.0029 0.115 Uiso 1 1 calc R . .
H15C H 0.9299 0.1185 0.9873 0.115 Uiso 1 1 calc R . .
C16 C 1.1218(7) 0.1869(3) 0.9215(5) 0.073(2) Uani 1 1 d . . .
H16A H 1.1624 0.1485 0.9482 0.110 Uiso 1 1 calc R . .
H16B H 1.1256 0.2174 0.9720 0.110 Uiso 1 1 calc R . .
H16C H 1.1793 0.2010 0.8724 0.110 Uiso 1 1 calc R . .
C31 C 1.0294(5) 0.3794(2) 0.6702(3) 0.0369(12) Uani 1 1 d . A .
F32 F 0.9703(4) 0.44107(13) 0.7953(2) 0.0590(10) Uani 1 1 d . . .
C32 C 0.9568(6) 0.4292(2) 0.7011(4) 0.0431(13) Uani 1 1 d . . .
F33 F 0.8087(5) 0.51713(16) 0.6795(3) 0.0878(14) Uani 1 1 d . . .
C33 C 0.8719(7) 0.4699(3) 0.6430(4) 0.0563(16) Uani 1 1 d . . .
F34 F 0.7757(4) 0.49904(19) 0.4884(3) 0.0908(14) Uani 1 1 d . . .
C34 C 0.8569(7) 0.4605(3) 0.5467(5) 0.0603(18) Uani 1 1 d . . .
F35 F 0.9130(4) 0.4042(2) 0.4169(2) 0.0931(15) Uani 1 1 d . . .
C35 C 0.9244(7) 0.4131(3) 0.5120(4) 0.0582(18) Uani 1 1 d . . .
F36 F 1.0655(4) 0.3258(2) 0.5300(2) 0.0813(12) Uani 1 1 d . . .
C36 C 1.0072(6) 0.3721(3) 0.5722(4) 0.0507(15) Uani 1 1 d . . .
B1 B 1.1281(6) 0.3374(2) 0.7513(4) 0.0331(13) Uani 1 1 d D . .
C41 C 1.2570(18) 0.3790(7) 0.8140(10) 0.029(5) Uani 0.533(16) 1 d PDU A 1
F42 F 1.2680(10) 0.4569(5) 0.7011(7) 0.063(3) Uani 0.533(16) 1 d PDU A 1
C42 C 1.3208(13) 0.4314(5) 0.7848(8) 0.039(3) Uani 0.533(16) 1 d PDU A 1
F43 F 1.4918(11) 0.5117(4) 0.8051(8) 0.079(3) Uani 0.533(16) 1 d PDU A 1
C43 C 1.4370(14) 0.4611(5) 0.8368(9) 0.049(4) Uani 0.533(16) 1 d PDU A 1
F44 F 1.6155(12) 0.4663(6) 0.9745(8) 0.056(3) Uani 0.533(16) 1 d PDU A 1
C44 C 1.5025(18) 0.4399(7) 0.9207(10) 0.040(4) Uani 0.533(16) 1 d PDU A 1
F45 F 1.4954(14) 0.3812(6) 1.0429(7) 0.067(3) Uani 0.533(16) 1 d PDU A 1
C45 C 1.442(4) 0.3899(14) 0.9534(15) 0.045(6) Uani 0.533(16) 1 d PDU A 1
F46 F 1.2747(14) 0.3170(6) 0.9508(8) 0.052(3) Uani 0.533(16) 1 d PDU A 1
C46 C 1.328(3) 0.3613(12) 0.9013(14) 0.037(5) Uani 0.533(16) 1 d PDU A 1
C41A C 1.2768(19) 0.3708(8) 0.8038(10) 0.022(4) Uani 0.467(16) 1 d PDU A 2
F42A F 1.3067(10) 0.4290(6) 0.6679(7) 0.062(3) Uani 0.467(16) 1 d PDU A 2
C42A C 1.3480(13) 0.4163(6) 0.7609(9) 0.039(4) Uani 0.467(16) 1 d PDU A 2
F43A F 1.5315(11) 0.4897(5) 0.7568(10) 0.082(4) Uani 0.467(16) 1 d PDU A 2
C43A C 1.4655(13) 0.4479(6) 0.8073(10) 0.039(4) Uani 0.467(16) 1 d PDU A 2
F44A F 1.6284(17) 0.4668(8) 0.9399(11) 0.078(4) Uani 0.467(16) 1 d PDU A 2
C44A C 1.512(2) 0.4326(10) 0.9009(11) 0.057(6) Uani 0.467(16) 1 d PDU A 2
F45A F 1.5050(13) 0.3565(5) 1.0308(7) 0.049(3) Uani 0.467(16) 1 d PDU A 2
C45A C 1.452(4) 0.3853(16) 0.9468(18) 0.045(6) Uani 0.467(16) 1 d PDU A 2
F46A F 1.2920(15) 0.3007(5) 0.9294(9) 0.040(3) Uani 0.467(16) 1 d PDU A 2
C46A C 1.335(4) 0.3548(13) 0.8949(17) 0.037(6) Uani 0.467(16) 1 d PDU A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C2 1.739(4) . ?
P1 C1 1.779(5) . ?
P1 C13 1.843(5) . ?
P1 C9 1.846(5) . ?
Cl1 B1 1.895(6) . ?
C1 C2 1.336(6) . ?
C1 B1 1.603(7) . ?
C2 C3 1.456(6) . ?
C3 C4 1.386(6) . ?
C3 C8 1.398(6) . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(7) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.503(8) . ?
C9 C12 1.529(8) . ?
C9 C11 1.533(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(8) . ?
C13 C16 1.522(8) . ?
C13 C15 1.534(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C31 C32 1.386(7) . ?
C31 C36 1.389(7) . ?
C31 B1 1.650(7) . ?
F32 C32 1.352(6) . ?
C32 C33 1.385(7) . ?
F33 C33 1.330(7) . ?
C33 C34 1.371(8) . ?
F34 C34 1.341(6) . ?
C34 C35 1.342(9) . ?
F35 C35 1.353(6) . ?
C35 C36 1.397(8) . ?
F36 C36 1.330(7) . ?
B1 C41A 1.643(11) . ?
B1 C41 1.661(11) . ?
C41 C46 1.377(11) . ?
C41 C42 1.382(10) . ?
F42 C42 1.345(10) . ?
C42 C43 1.380(10) . ?
F43 C43 1.327(10) . ?
C43 C44 1.344(11) . ?
F44 C44 1.339(10) . ?
C44 C45 1.344(11) . ?
F45 C45 1.314(11) . ?
C45 C46 1.356(11) . ?
F46 C46 1.333(11) . ?
C41A C46A 1.378(12) . ?
C41A C42A 1.382(11) . ?
F42A C42A 1.354(10) . ?
C42A C43A 1.377(11) . ?
F43A C43A 1.360(11) . ?
C43A C44A 1.383(12) . ?
F44A C44A 1.365(12) . ?
C44A C45A 1.380(12) . ?
F45A C45A 1.381(12) . ?
C45A C46A 1.392(11) . ?
F46A C46A 1.367(12) . ?

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
C2 P1 C1 44.6(2) . . ?
C2 P1 C13 118.4(2) . . ?
C1 P1 C13 118.8(2) . . ?
C2 P1 C9 117.7(2) . . ?
C1 P1 C9 118.3(2) . . ?
C13 P1 C9 118.4(3) . . ?
C2 C1 B1 150.0(4) . . ?
C2 C1 P1 66.1(3) . . ?
B1 C1 P1 143.8(3) . . ?
C1 C2 C3 144.8(4) . . ?
C1 C2 P1 69.3(3) . . ?
C3 C2 P1 145.9(4) . . ?
C4 C3 C8 118.7(4) . . ?
C4 C3 C2 120.1(4) . . ?
C8 C3 C2 121.2(4) . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C12 110.5(6) . . ?
C10 C9 C11 109.2(5) . . ?
C12 C9 C11 110.5(6) . . ?
C10 C9 P1 107.6(4) . . ?
C12 C9 P1 110.3(4) . . ?
C11 C9 P1 108.7(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C16 109.1(5) . . ?
C14 C13 C15 110.5(5) . . ?
C16 C13 C15 107.7(5) . . ?
C14 C13 P1 111.6(4) . . ?
C16 C13 P1 107.1(4) . . ?
C15 C13 P1 110.7(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C32 C31 C36 113.3(5) . . ?
C32 C31 B1 117.8(4) . . ?
C36 C31 B1 128.9(5) . . ?
F32 C32 C33 115.8(5) . . ?
F32 C32 C31 118.7(4) . . ?
C33 C32 C31 125.5(5) . . ?
F33 C33 C34 121.0(6) . . ?
F33 C33 C32 121.0(5) . . ?
C34 C33 C32 118.0(6) . . ?
F34 C34 C35 120.8(6) . . ?
F34 C34 C33 119.6(7) . . ?
C35 C34 C33 119.6(6) . . ?
C34 C35 F35 120.0(6) . . ?
C34 C35 C36 121.3(5) . . ?
F35 C35 C36 118.7(7) . . ?
F36 C36 C31 121.6(5) . . ?
F36 C36 C35 116.1(5) . . ?
C31 C36 C35 122.3(6) . . ?
C1 B1 C41A 116.2(7) . . ?
C1 B1 C31 107.0(4) . . ?
C41A B1 C31 114.5(6) . . ?
C1 B1 C41 109.7(7) . . ?
C41A B1 C41 10.7(16) . . ?
C31 B1 C41 110.7(6) . . ?
C1 B1 Cl1 106.1(3) . . ?
C41A B1 Cl1 100.4(9) . . ?
C31 B1 Cl1 112.4(3) . . ?
C41 B1 Cl1 110.8(9) . . ?
C46 C41 C42 109.7(9) . . ?
C46 C41 B1 123.0(9) . . ?
C42 C41 B1 126.9(9) . . ?
F42 C42 C43 115.9(8) . . ?
F42 C42 C41 119.7(8) . . ?
C43 C42 C41 124.3(9) . . ?
F43 C43 C44 116.5(9) . . ?
F43 C43 C42 121.3(9) . . ?
C44 C43 C42 122.2(9) . . ?
F44 C44 C45 119.1(10) . . ?
F44 C44 C43 125.3(10) . . ?
C45 C44 C43 115.6(9) . . ?
F45 C45 C44 109.5(11) . . ?
F45 C45 C46 128.5(12) . . ?
C44 C45 C46 121.3(10) . . ?
F46 C46 C45 111.4(10) . . ?
F46 C46 C41 121.3(11) . . ?
C45 C46 C41 126.7(10) . . ?
C46A C41A C42A 116.7(10) . . ?
C46A C41A B1 120.6(9) . . ?
C42A C41A B1 122.7(9) . . ?
F42A C42A C43A 117.5(9) . . ?
F42A C42A C41A 119.5(9) . . ?
C43A C42A C41A 122.9(9) . . ?
F43A C43A C42A 117.9(10) . . ?
F43A C43A C44A 124.7(10) . . ?
C42A C43A C44A 117.3(10) . . ?
F44A C44A C45A 124.5(12) . . ?
F44A C44A C43A 112.4(11) . . ?
C45A C44A C43A 123.0(11) . . ?
C44A C45A F45A 129.5(13) . . ?
C44A C45A C46A 116.3(11) . . ?
F45A C45A C46A 113.2(11) . . ?
F46A C46A C41A 117.5(12) . . ?
F46A C46A C45A 118.2(11) . . ?
C41A C46A C45A 123.4(11) . . ?

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
C13 P1 C1 C2 -102.4(3) . . . . ?
C9 P1 C1 C2 101.9(3) . . . . ?
C2 P1 C1 B1 -177.3(7) . . . . ?
C13 P1 C1 B1 80.2(6) . . . . ?
C9 P1 C1 B1 -75.4(6) . . . . ?
B1 C1 C2 C3 -5.0(14) . . . . ?
P1 C1 C2 C3 178.2(7) . . . . ?
B1 C1 C2 P1 176.8(9) . . . . ?
C13 P1 C2 C1 103.4(3) . . . . ?
C9 P1 C2 C1 -103.3(3) . . . . ?
C1 P1 C2 C3 -178.1(8) . . . . ?
C13 P1 C2 C3 -74.7(7) . . . . ?
C9 P1 C2 C3 78.6(7) . . . . ?
C1 C2 C3 C4 178.5(6) . . . . ?
P1 C2 C3 C4 -4.6(9) . . . . ?
C1 C2 C3 C8 -2.9(10) . . . . ?
P1 C2 C3 C8 174.1(5) . . . . ?
C8 C3 C4 C5 0.4(7) . . . . ?
C2 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C4 C5 C6 C7 0.4(8) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C6 C7 C8 C3 -0.3(8) . . . . ?
C4 C3 C8 C7 0.0(7) . . . . ?
C2 C3 C8 C7 -178.6(5) . . . . ?
C2 P1 C9 C10 16.9(5) . . . . ?
C1 P1 C9 C10 -34.0(5) . . . . ?
C13 P1 C9 C10 170.2(4) . . . . ?
C2 P1 C9 C12 -103.8(5) . . . . ?
C1 P1 C9 C12 -154.7(5) . . . . ?
C13 P1 C9 C12 49.5(6) . . . . ?
C2 P1 C9 C11 135.0(4) . . . . ?
C1 P1 C9 C11 84.1(5) . . . . ?
C13 P1 C9 C11 -71.7(5) . . . . ?
C2 P1 C13 C14 -154.4(4) . . . . ?
C1 P1 C13 C14 -103.2(5) . . . . ?
C9 P1 C13 C14 52.5(5) . . . . ?
C2 P1 C13 C16 -35.1(5) . . . . ?
C1 P1 C13 C16 16.1(5) . . . . ?
C9 P1 C13 C16 171.8(4) . . . . ?
C2 P1 C13 C15 82.0(5) . . . . ?
C1 P1 C13 C15 133.3(4) . . . . ?
C9 P1 C13 C15 -71.1(5) . . . . ?
C36 C31 C32 F32 -179.9(5) . . . . ?
B1 C31 C32 F32 0.0(7) . . . . ?
C36 C31 C32 C33 -1.3(8) . . . . ?
B1 C31 C32 C33 178.7(5) . . . . ?
F32 C32 C33 F33 -0.1(8) . . . . ?
C31 C32 C33 F33 -178.8(5) . . . . ?
F32 C32 C33 C34 178.9(5) . . . . ?
C31 C32 C33 C34 0.3(9) . . . . ?
F33 C33 C34 F34 -0.8(9) . . . . ?
C32 C33 C34 F34 -179.9(5) . . . . ?
F33 C33 C34 C35 178.7(6) . . . . ?
C32 C33 C34 C35 -0.3(9) . . . . ?
F34 C34 C35 F35 1.1(9) . . . . ?
C33 C34 C35 F35 -178.5(5) . . . . ?
F34 C34 C35 C36 -178.9(5) . . . . ?
C33 C34 C35 C36 1.5(9) . . . . ?
C32 C31 C36 F36 -178.4(5) . . . . ?
B1 C31 C36 F36 1.7(9) . . . . ?
C32 C31 C36 C35 2.5(8) . . . . ?
B1 C31 C36 C35 -177.5(5) . . . . ?
C34 C35 C36 F36 178.1(5) . . . . ?
F35 C35 C36 F36 -2.0(8) . . . . ?
C34 C35 C36 C31 -2.7(9) . . . . ?
F35 C35 C36 C31 177.2(5) . . . . ?
C2 C1 B1 C41A 38.6(13) . . . . ?
P1 C1 B1 C41A -146.3(10) . . . . ?
C2 C1 B1 C31 -90.7(9) . . . . ?
P1 C1 B1 C31 84.4(6) . . . . ?
C2 C1 B1 C41 29.4(12) . . . . ?
P1 C1 B1 C41 -155.5(9) . . . . ?
C2 C1 B1 Cl1 149.1(7) . . . . ?
P1 C1 B1 Cl1 -35.8(7) . . . . ?
C32 C31 B1 C1 60.8(6) . . . . ?
C36 C31 B1 C1 -119.2(5) . . . . ?
C32 C31 B1 C41A -69.5(11) . . . . ?
C36 C31 B1 C41A 110.5(11) . . . . ?
C32 C31 B1 C41 -58.7(10) . . . . ?
C36 C31 B1 C41 121.3(10) . . . . ?
C32 C31 B1 Cl1 176.9(4) . . . . ?
C36 C31 B1 Cl1 -3.2(7) . . . . ?
C1 B1 C41 C46 44(3) . . . . ?
C41A B1 C41 C46 -86(5) . . . . ?
C31 B1 C41 C46 161(3) . . . . ?
Cl1 B1 C41 C46 -73(3) . . . . ?
C1 B1 C41 C42 -144.0(17) . . . . ?
C41A B1 C41 C42 87(4) . . . . ?
C31 B1 C41 C42 -26(2) . . . . ?
Cl1 B1 C41 C42 99.1(19) . . . . ?
C46 C41 C42 F42 -180(2) . . . . ?
B1 C41 C42 F42 7(3) . . . . ?
C46 C41 C42 C43 -1(3) . . . . ?
B1 C41 C42 C43 -173.8(14) . . . . ?
F42 C42 C43 F43 0(2) . . . . ?
C41 C42 C43 F43 -179.0(16) . . . . ?
F42 C42 C43 C44 -178.5(15) . . . . ?
C41 C42 C43 C44 2(3) . . . . ?
F43 C43 C44 F44 1(3) . . . . ?
C42 C43 C44 F44 179.9(17) . . . . ?
F43 C43 C44 C45 177(3) . . . . ?
C42 C43 C44 C45 -4(3) . . . . ?
F44 C44 C45 F45 9(5) . . . . ?
C43 C44 C45 F45 -167(2) . . . . ?
F44 C44 C45 C46 -180(3) . . . . ?
C43 C44 C45 C46 4(5) . . . . ?
F45 C45 C46 F46 -4(6) . . . . ?
C44 C45 C46 F46 -173(4) . . . . ?
F45 C45 C46 C41 167(4) . . . . ?
C44 C45 C46 C41 -2(7) . . . . ?
C42 C41 C46 F46 171(3) . . . . ?
B1 C41 C46 F46 -16(5) . . . . ?
C42 C41 C46 C45 1(5) . . . . ?
B1 C41 C46 C45 174(4) . . . . ?
C1 B1 C41A C46A 27(3) . . . . ?
C31 B1 C41A C46A 153(3) . . . . ?
C41 B1 C41A C46A 82(4) . . . . ?
Cl1 B1 C41A C46A -87(3) . . . . ?
C1 B1 C41A C42A -151.9(16) . . . . ?
C31 B1 C41A C42A -26(2) . . . . ?
C41 B1 C41A C42A -97(4) . . . . ?
Cl1 B1 C41A C42A 94.3(19) . . . . ?
C46A C41A C42A F42A 172(3) . . . . ?
B1 C41A C42A F42A -9(3) . . . . ?
C46A C41A C42A C43A -5(4) . . . . ?
B1 C41A C42A C43A 174.5(15) . . . . ?
F42A C42A C43A F43A 0(2) . . . . ?
C41A C42A C43A F43A 177.0(17) . . . . ?
F42A C42A C43A C44A -176.9(17) . . . . ?
C41A C42A C43A C44A 0(3) . . . . ?
F43A C43A C44A F44A 3(3) . . . . ?
C42A C43A C44A F44A -179.7(17) . . . . ?
F43A C43A C44A C45A -173(3) . . . . ?
C42A C43A C44A C45A 4(4) . . . . ?
F44A C44A C45A F45A -11(7) . . . . ?
C43A C44A C45A F45A 165(4) . . . . ?
F44A C44A C45A C46A -179(4) . . . . ?
C43A C44A C45A C46A -3(6) . . . . ?
C42A C41A C46A F46A -163(3) . . . . ?
B1 C41A C46A F46A 17(5) . . . . ?
C42A C41A C46A C45A 6(6) . . . . ?
B1 C41A C46A C45A -173(4) . . . . ?
C44A C45A C46A F46A 167(4) . . . . ?
F45A C45A C46A F46A -3(6) . . . . ?
C44A C45A C46A C41A -2(7) . . . . ?
F45A C45A C46A C41A -172(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_erk9236
_database_code_depnum_ccdc_archive 'CCDC 1865545'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39.50 H35 B Br F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         821.36

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5895(3)
_cell_length_b                   10.8563(3)
_cell_length_c                   18.7360(5)
_cell_angle_alpha                82.3630(10)
_cell_angle_beta                 76.1530(10)
_cell_angle_gamma                76.8730(10)
_cell_volume                     1837.99(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      4.6758
_cell_measurement_theta_max      66.6946
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             834

_exptl_absorpt_coefficient_mu    2.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.93

_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  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24093
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_theta_min         4.68
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_full        66.69
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_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             6361
_reflns_number_gt                5558
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0833
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         6361
_refine_ls_number_parameters     515
_refine_ls_number_restraints     57
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.6136P] 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         0.360
_refine_diff_density_min         -0.324
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

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
Br Br1 0.27872(2) 0.35171(2) 0.82401(2) 0.02311(8) Uani d . . . 1 . .
P P1 0.75490(6) 0.41281(5) 0.77605(3) 0.01536(12) Uani d . . . 1 . .
C C1 0.5860(2) 0.3828(2) 0.76615(10) 0.0175(4) Uani d . . . 1 . .
C C2 0.5877(2) 0.5061(2) 0.75847(10) 0.0172(4) Uani d . . . 1 . .
C C3 0.5008(2) 0.6340(2) 0.73560(11) 0.0200(4) Uani d . . . 1 . .
C C4 0.4235(3) 0.6120(2) 0.67647(12) 0.0264(5) Uani d . . . 1 . .
H H4A 0.3625 0.6922 0.6616 0.04 Uiso calc U . R 1 . .
H H4B 0.3615 0.5497 0.6968 0.04 Uiso calc U . R 1 . .
H H4C 0.4972 0.58 0.6335 0.04 Uiso calc U . R 1 . .
C C5 0.3814(3) 0.6901(2) 0.80037(13) 0.0307(5) Uani d . . . 1 . .
H H5A 0.4276 0.7152 0.836 0.046 Uiso calc U . R 1 . .
H H5B 0.3239 0.6263 0.8245 0.046 Uiso calc U . R 1 . .
H H5C 0.3167 0.7647 0.7818 0.046 Uiso calc U . R 1 . .
C C6 0.6023(3) 0.7267(2) 0.70292(13) 0.0270(5) Uani d . . . 1 . .
H H6A 0.6472 0.7444 0.7412 0.041 Uiso calc U . R 1 . .
H H6B 0.5455 0.8059 0.684 0.041 Uiso calc U . R 1 . .
H H6C 0.6792 0.6892 0.6625 0.041 Uiso calc U . R 1 . .
C C11 0.8063(2) 0.3867(2) 0.86482(10) 0.0175(4) Uani d . . . 1 . .
C C12 0.9106(2) 0.2767(2) 0.87823(11) 0.0202(4) Uani d . . . 1 . .
C C13 0.9555(2) 0.2592(2) 0.94471(11) 0.0219(5) Uani d . . . 1 . .
H H13 1.0251 0.1849 0.9543 0.026 Uiso calc U . R 1 . .
C C14 0.9021(2) 0.3464(2) 0.99783(11) 0.0225(5) Uani d . . . 1 . .
C C15 0.7957(2) 0.4513(2) 0.98437(11) 0.0225(5) Uani d . . . 1 . .
H H15 0.7556 0.5101 1.0209 0.027 Uiso calc U . R 1 . .
C C16 0.7457(2) 0.4734(2) 0.91911(11) 0.0200(4) Uani d . . . 1 . .
C C17 0.9753(2) 0.1756(2) 0.82450(12) 0.0228(5) Uani d . . . 1 . .
H H17A 1.0415 0.2088 0.7817 0.034 Uiso calc U . R 1 . .
H H17B 0.8962 0.1513 0.8083 0.034 Uiso calc U . R 1 . .
H H17C 1.0301 0.1011 0.8488 0.034 Uiso calc U . R 1 . .
C C18 0.9595(3) 0.3267(3) 1.06763(12) 0.0304(5) Uani d . . . 1 . .
H H18A 0.9147 0.3996 1.0969 0.046 Uiso calc U . R 1 . .
H H18B 1.0662 0.3184 1.055 0.046 Uiso calc U . R 1 . .
H H18C 0.9347 0.2493 1.0963 0.046 Uiso calc U . R 1 . .
C C19 0.6279(3) 0.5879(2) 0.90980(11) 0.0246(5) Uani d . . . 1 . .
H H19A 0.535 0.5612 0.9142 0.037 Uiso calc U . R 1 . .
H H19B 0.6549 0.6324 0.8611 0.037 Uiso calc U . R 1 . .
H H19C 0.6169 0.6449 0.9481 0.037 Uiso calc U . R 1 . .
C C21 0.9113(2) 0.4027(2) 0.69890(10) 0.0170(4) Uani d . . . 1 . .
C C22 0.9453(2) 0.3092(2) 0.64858(11) 0.0185(4) Uani d . . . 1 . .
C C23 1.0524(2) 0.3212(2) 0.58443(11) 0.0216(5) Uani d . . . 1 . .
H H23 1.0755 0.2591 0.5499 0.026 Uiso calc U . R 1 . .
C C24 1.1263(2) 0.4206(2) 0.56942(11) 0.0223(5) Uani d . . . 1 . .
C C25 1.0978(2) 0.5071(2) 0.62228(11) 0.0214(5) Uani d . . . 1 . .
H H25 1.1519 0.5729 0.6138 0.026 Uiso calc U . R 1 . .
C C26 0.9924(2) 0.4996(2) 0.68708(11) 0.0195(4) Uani d . . . 1 . .
C C27 0.8792(2) 0.1925(2) 0.66101(11) 0.0218(5) Uani d . . . 1 . .
H H27A 0.8562 0.1774 0.6151 0.033 Uiso calc U . R 1 . .
H H27B 0.7892 0.2054 0.6996 0.033 Uiso calc U . R 1 . .
H H27C 0.9494 0.1191 0.6764 0.033 Uiso calc U . R 1 . .
C C28 1.2336(3) 0.4361(2) 0.49680(12) 0.0293(5) Uani d . . . 1 . .
H H28A 1.2783 0.3525 0.4784 0.044 Uiso calc U . R 1 . .
H H28B 1.3103 0.4764 0.504 0.044 Uiso calc U . R 1 . .
H H28C 1.1818 0.4892 0.4609 0.044 Uiso calc U . R 1 . .
C C29 0.9719(2) 0.5938(2) 0.74357(12) 0.0224(5) Uani d . . . 1 . .
H H29A 1.0057 0.5494 0.7873 0.034 Uiso calc U . R 1 . .
H H29B 0.8678 0.6336 0.7576 0.034 Uiso calc U . R 1 . .
H H29C 1.029 0.6593 0.7223 0.034 Uiso calc U . R 1 . .
B B1 0.4959(3) 0.2709(2) 0.77527(12) 0.0185(5) Uani d . . . 1 . .
C C31 0.5615(2) 0.1607(2) 0.83361(11) 0.0181(4) Uani d . . . 1 . .
F F32 0.65421(14) -0.00199(11) 0.75039(7) 0.0243(3) Uani d . . . 1 . .
C C32 0.6355(2) 0.0385(2) 0.81802(11) 0.0200(4) Uani d . . . 1 . .
F F33 0.76983(15) -0.16584(12) 0.84806(8) 0.0313(3) Uani d . . . 1 . .
C C33 0.6979(2) -0.0495(2) 0.86814(12) 0.0233(5) Uani d . . . 1 . .
F F34 0.74614(16) -0.10175(13) 0.98756(7) 0.0346(3) Uani d . . . 1 . .
C C34 0.6889(2) -0.0170(2) 0.93795(12) 0.0243(5) Uani d . . . 1 . .
F F35 0.61118(15) 0.13813(13) 1.02363(7) 0.0313(3) Uani d . . . 1 . .
C C35 0.6193(2) 0.1040(2) 0.95618(11) 0.0232(5) Uani d . . . 1 . .
F F36 0.49762(14) 0.30693(12) 0.92549(6) 0.0242(3) Uani d . . . 1 . .
C C36 0.5594(2) 0.1891(2) 0.90433(11) 0.0199(4) Uani d . . . 1 . .
C C41 0.4810(2) 0.2236(2) 0.69925(12) 0.0207(5) Uani d . . . 1 . .
F F42 0.34304(15) 0.07347(13) 0.76588(7) 0.0293(3) Uani d . . . 1 . .
C C42 0.3998(2) 0.1317(2) 0.70077(12) 0.0239(5) Uani d . . . 1 . .
F F43 0.29076(17) 0.00614(14) 0.64441(9) 0.0413(4) Uani d . . . 1 . .
C C43 0.3722(3) 0.0942(2) 0.63863(14) 0.0290(5) Uani d . . . 1 . .
F F44 0.40237(18) 0.11440(15) 0.50875(8) 0.0422(4) Uani d . . . 1 . .
C C44 0.4295(3) 0.1475(2) 0.56989(13) 0.0302(6) Uani d . . . 1 . .
F F45 0.57407(16) 0.28739(14) 0.49832(7) 0.0335(3) Uani d . . . 1 . .
C C45 0.5141(3) 0.2360(2) 0.56491(12) 0.0255(5) Uani d . . . 1 . .
F F46 0.62098(14) 0.36047(12) 0.61768(6) 0.0246(3) Uani d . . . 1 . .
C C46 0.5371(2) 0.2727(2) 0.62861(12) 0.0200(4) Uani d . . . 1 . .
C C51 -0.0127(6) -0.0388(5) 0.5259(3) 0.0306(11) Uani d U P D 0.5 A -1
C C54 0.0735(9) 0.1191(17) 0.3991(9) 0.032(4) Uani d U P D 0.5 A -1
H H54 0.1033 0.1699 0.3551 0.038 Uiso calc U P R 0.5 A -1
C C52 -0.1141(11) 0.0341(18) 0.4878(8) 0.032(3) Uani d U P D 0.5 A -1
H H52 -0.2146 0.0296 0.5047 0.039 Uiso calc U P R 0.5 A -1
C C53 -0.0730(6) 0.1132(5) 0.4259(3) 0.0324(11) Uani d U P D 0.5 A -1
H H53 -0.1454 0.1638 0.4015 0.039 Uiso calc U P R 0.5 A -1
C C55 0.1754(6) 0.0493(5) 0.4379(2) 0.0307(11) Uani d U P D 0.5 A -1
H H55 0.2757 0.0545 0.4214 0.037 Uiso calc U P R 0.5 A -1
C C56 0.1327(9) -0.0281(17) 0.5006(8) 0.028(3) Uani d U P D 0.5 A -1
H H56 0.2041 -0.0747 0.5267 0.034 Uiso calc U P R 0.5 A -1
C C57 -0.0569(13) -0.1260(19) 0.5919(9) 0.045(4) Uani d U P . 0.5 A -1
H H57A -0.1587 -0.0935 0.6164 0.067 Uiso calc U P R 0.5 A -1
H H57B 0.0073 -0.1312 0.6262 0.067 Uiso calc U P R 0.5 A -1
H H57C -0.0483 -0.2107 0.5764 0.067 Uiso calc U P R 0.5 A -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
Br1 B1 . 2.101(2) ?
P1 C2 . 1.770(2) ?
P1 C1 . 1.779(2) ?
P1 C21 . 1.811(2) ?
P1 C11 . 1.815(2) ?
C1 C2 . 1.331(3) ?
C1 B1 . 1.613(3) ?
C2 C3 . 1.514(3) ?
C3 C6 . 1.526(3) ?
C3 C5 . 1.539(3) ?
C3 C4 . 1.542(3) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C11 C16 . 1.408(3) ?
C11 C12 . 1.409(3) ?
C12 C13 . 1.389(3) ?
C12 C17 . 1.513(3) ?
C13 C14 . 1.391(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.387(3) ?
C14 C18 . 1.508(3) ?
C15 C16 . 1.390(3) ?
C15 H15 . 0.95 ?
C16 C19 . 1.500(3) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C21 C22 . 1.408(3) ?
C21 C26 . 1.411(3) ?
C22 C23 . 1.395(3) ?
C22 C27 . 1.508(3) ?
C23 C24 . 1.385(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.392(3) ?
C24 C28 . 1.512(3) ?
C25 C26 . 1.388(3) ?
C25 H25 . 0.95 ?
C26 C29 . 1.517(3) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
B1 C41 . 1.624(3) ?
B1 C31 . 1.631(3) ?
C31 C32 . 1.388(3) ?
C31 C36 . 1.394(3) ?
F32 C32 . 1.354(2) ?
C32 C33 . 1.386(3) ?
F33 C33 . 1.349(3) ?
C33 C34 . 1.377(3) ?
F34 C34 . 1.341(2) ?
C34 C35 . 1.378(3) ?
F35 C35 . 1.343(2) ?
C35 C36 . 1.384(3) ?
F36 C36 . 1.350(2) ?
C41 C46 . 1.388(3) ?
C41 C42 . 1.392(3) ?
F42 C42 . 1.348(3) ?
C42 C43 . 1.383(3) ?
F43 C43 . 1.344(3) ?
C43 C44 . 1.379(4) ?
F44 C44 . 1.343(3) ?
C44 C45 . 1.372(4) ?
F45 C45 . 1.348(3) ?
C45 C46 . 1.387(3) ?
F46 C46 . 1.347(3) ?
C51 C52 . 1.383(6) ?
C51 C56 . 1.387(6) ?
C51 C57 . 1.491(15) ?
C54 C55 . 1.384(8) ?
C54 C53 . 1.388(8) ?
C54 H54 . 0.95 ?
C52 C53 . 1.382(7) ?
C52 H52 . 0.95 ?
C53 H53 . 0.95 ?
C55 C56 . 1.384(6) ?
C55 H55 . 0.95 ?
C56 H56 . 0.95 ?
C57 H57A . 0.98 ?
C57 H57B . 0.98 ?
C57 H57C . 0.98 ?

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
C2 P1 C1 . . 44.05(10) ?
C2 P1 C21 . . 116.06(9) ?
C1 P1 C21 . . 120.53(9) ?
C2 P1 C11 . . 125.17(9) ?
C1 P1 C11 . . 121.34(9) ?
C21 P1 C11 . . 113.03(9) ?
C2 C1 B1 . . 149.4(2) ?
C2 C1 P1 . . 67.61(13) ?
B1 C1 P1 . . 142.24(16) ?
C1 C2 C3 . . 141.7(2) ?
C1 C2 P1 . . 68.34(13) ?
C3 C2 P1 . . 149.06(17) ?
C2 C3 C6 . . 110.68(18) ?
C2 C3 C5 . . 111.87(17) ?
C6 C3 C5 . . 110.11(19) ?
C2 C3 C4 . . 106.89(17) ?
C6 C3 C4 . . 109.46(18) ?
C5 C3 C4 . . 107.71(19) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C16 C11 C12 . . 120.26(19) ?
C16 C11 P1 . . 121.62(16) ?
C12 C11 P1 . . 118.13(15) ?
C13 C12 C11 . . 118.40(19) ?
C13 C12 C17 . . 117.99(19) ?
C11 C12 C17 . . 123.61(19) ?
C12 C13 C14 . . 122.4(2) ?
C12 C13 H13 . . 118.8 ?
C14 C13 H13 . . 118.8 ?
C15 C14 C13 . . 118.0(2) ?
C15 C14 C18 . . 121.4(2) ?
C13 C14 C18 . . 120.6(2) ?
C14 C15 C16 . . 122.1(2) ?
C14 C15 H15 . . 118.9 ?
C16 C15 H15 . . 118.9 ?
C15 C16 C11 . . 118.7(2) ?
C15 C16 C19 . . 118.61(19) ?
C11 C16 C19 . . 122.65(19) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C22 C21 C26 . . 120.30(18) ?
C22 C21 P1 . . 122.44(16) ?
C26 C21 P1 . . 117.06(15) ?
C23 C22 C21 . . 118.2(2) ?
C23 C22 C27 . . 117.30(18) ?
C21 C22 C27 . . 124.39(18) ?
C24 C23 C22 . . 122.2(2) ?
C24 C23 H23 . . 118.9 ?
C22 C23 H23 . . 118.9 ?
C23 C24 C25 . . 118.46(19) ?
C23 C24 C28 . . 120.7(2) ?
C25 C24 C28 . . 120.8(2) ?
C26 C25 C24 . . 121.7(2) ?
C26 C25 H25 . . 119.2 ?
C24 C25 H25 . . 119.2 ?
C25 C26 C21 . . 118.84(19) ?
C25 C26 C29 . . 118.7(2) ?
C21 C26 C29 . . 122.45(18) ?
C22 C27 H27A . . 109.5 ?
C22 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C22 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C24 C28 H28A . . 109.5 ?
C24 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C24 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C26 C29 H29A . . 109.5 ?
C26 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C26 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C1 B1 C41 . . 116.05(17) ?
C1 B1 C31 . . 106.64(17) ?
C41 B1 C31 . . 116.16(18) ?
C1 B1 Br1 . . 105.22(14) ?
C41 B1 Br1 . . 103.36(14) ?
C31 B1 Br1 . . 108.64(14) ?
C32 C31 C36 . . 113.57(19) ?
C32 C31 B1 . . 125.89(18) ?
C36 C31 B1 . . 120.23(18) ?
F32 C32 C33 . . 115.12(19) ?
F32 C32 C31 . . 121.00(18) ?
C33 C32 C31 . . 123.86(19) ?
F33 C33 C34 . . 120.1(2) ?
F33 C33 C32 . . 120.00(19) ?
C34 C33 C32 . . 119.9(2) ?
F34 C34 C33 . . 120.6(2) ?
F34 C34 C35 . . 120.5(2) ?
C33 C34 C35 . . 118.9(2) ?
F35 C35 C34 . . 119.8(2) ?
F35 C35 C36 . . 120.8(2) ?
C34 C35 C36 . . 119.4(2) ?
F36 C36 C35 . . 115.81(18) ?
F36 C36 C31 . . 119.81(19) ?
C35 C36 C31 . . 124.4(2) ?
C46 C41 C42 . . 113.7(2) ?
C46 C41 B1 . . 125.4(2) ?
C42 C41 B1 . . 120.79(19) ?
F42 C42 C43 . . 116.2(2) ?
F42 C42 C41 . . 119.69(19) ?
C43 C42 C41 . . 124.1(2) ?
F43 C43 C44 . . 119.6(2) ?
F43 C43 C42 . . 120.8(2) ?
C44 C43 C42 . . 119.6(2) ?
F44 C44 C45 . . 120.3(2) ?
F44 C44 C43 . . 120.8(2) ?
C45 C44 C43 . . 118.9(2) ?
F45 C45 C44 . . 120.1(2) ?
F45 C45 C46 . . 120.1(2) ?
C44 C45 C46 . . 119.8(2) ?
F46 C46 C45 . . 115.10(19) ?
F46 C46 C41 . . 120.97(19) ?
C45 C46 C41 . . 123.9(2) ?
C52 C51 C56 . . 117.6(5) ?
C52 C51 C57 . . 121.6(7) ?
C56 C51 C57 . . 120.8(6) ?
C55 C54 C53 . . 118.5(9) ?
C55 C54 H54 . . 120.8 ?
C53 C54 H54 . . 120.8 ?
C53 C52 C51 . . 121.7(7) ?
C53 C52 H52 . . 119.1 ?
C51 C52 H52 . . 119.1 ?
C52 C53 C54 . . 120.2(7) ?
C52 C53 H53 . . 119.9 ?
C54 C53 H53 . . 119.9 ?
C56 C55 C54 . . 120.7(7) ?
C56 C55 H55 . . 119.6 ?
C54 C55 H55 . . 119.6 ?
C55 C56 C51 . . 121.2(6) ?
C55 C56 H56 . . 119.4 ?
C51 C56 H56 . . 119.4 ?
C51 C57 H57A . . 109.5 ?
C51 C57 H57B . . 109.5 ?
H57A C57 H57B . . 109.5 ?
C51 C57 H57C . . 109.5 ?
H57A C57 H57C . . 109.5 ?
H57B C57 H57C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 P1 C1 C2 . . . . -97.12(14) ?
C11 P1 C1 C2 . . . . 109.91(13) ?
C2 P1 C1 B1 . . . . -171.5(3) ?
C21 P1 C1 B1 . . . . 91.3(2) ?
C11 P1 C1 B1 . . . . -61.6(3) ?
B1 C1 C2 C3 . . . . -19.5(5) ?
P1 C1 C2 C3 . . . . 170.7(3) ?
B1 C1 C2 P1 . . . . 169.8(4) ?
C21 P1 C2 C1 . . . . 107.93(13) ?
C11 P1 C2 C1 . . . . -100.76(14) ?
C1 P1 C2 C3 . . . . -168.7(3) ?
C21 P1 C2 C3 . . . . -60.8(3) ?
C11 P1 C2 C3 . . . . 90.5(3) ?
C1 C2 C3 C6 . . . . -150.4(3) ?
P1 C2 C3 C6 . . . . 12.5(4) ?
C1 C2 C3 C5 . . . . 86.4(3) ?
P1 C2 C3 C5 . . . . -110.7(3) ?
C1 C2 C3 C4 . . . . -31.3(3) ?
P1 C2 C3 C4 . . . . 131.7(3) ?
C2 P1 C11 C16 . . . . -24.5(2) ?
C1 P1 C11 C16 . . . . -77.7(2) ?
C21 P1 C11 C16 . . . . 127.51(18) ?
C2 P1 C11 C12 . . . . 155.98(16) ?
C1 P1 C11 C12 . . . . 102.87(18) ?
C21 P1 C11 C12 . . . . -51.96(19) ?
C16 C11 C12 C13 . . . . -2.4(3) ?
P1 C11 C12 C13 . . . . 177.05(16) ?
C16 C11 C12 C17 . . . . 176.8(2) ?
P1 C11 C12 C17 . . . . -3.7(3) ?
C11 C12 C13 C14 . . . . -0.5(3) ?
C17 C12 C13 C14 . . . . -179.8(2) ?
C12 C13 C14 C15 . . . . 2.9(3) ?
C12 C13 C14 C18 . . . . -177.0(2) ?
C13 C14 C15 C16 . . . . -2.3(3) ?
C18 C14 C15 C16 . . . . 177.5(2) ?
C14 C15 C16 C11 . . . . -0.5(3) ?
C14 C15 C16 C19 . . . . 178.7(2) ?
C12 C11 C16 C15 . . . . 2.9(3) ?
P1 C11 C16 C15 . . . . -176.53(16) ?
C12 C11 C16 C19 . . . . -176.2(2) ?
P1 C11 C16 C19 . . . . 4.3(3) ?
C2 P1 C21 C22 . . . . -88.64(19) ?
C1 P1 C21 C22 . . . . -38.5(2) ?
C11 P1 C21 C22 . . . . 116.59(18) ?
C2 P1 C21 C26 . . . . 86.13(18) ?
C1 P1 C21 C26 . . . . 136.31(16) ?
C11 P1 C21 C26 . . . . -68.63(18) ?
C26 C21 C22 C23 . . . . -5.1(3) ?
P1 C21 C22 C23 . . . . 169.55(15) ?
C26 C21 C22 C27 . . . . 171.6(2) ?
P1 C21 C22 C27 . . . . -13.8(3) ?
C21 C22 C23 C24 . . . . 0.6(3) ?
C27 C22 C23 C24 . . . . -176.3(2) ?
C22 C23 C24 C25 . . . . 3.6(3) ?
C22 C23 C24 C28 . . . . -175.4(2) ?
C23 C24 C25 C26 . . . . -3.5(3) ?
C28 C24 C25 C26 . . . . 175.5(2) ?
C24 C25 C26 C21 . . . . -0.8(3) ?
C24 C25 C26 C29 . . . . 177.4(2) ?
C22 C21 C26 C25 . . . . 5.2(3) ?
P1 C21 C26 C25 . . . . -169.74(16) ?
C22 C21 C26 C29 . . . . -173.01(19) ?
P1 C21 C26 C29 . . . . 12.1(3) ?
C2 C1 B1 C41 . . . . 87.5(4) ?
P1 C1 B1 C41 . . . . -108.0(2) ?
C2 C1 B1 C31 . . . . -141.3(3) ?
P1 C1 B1 C31 . . . . 23.1(3) ?
C2 C1 B1 Br1 . . . . -26.1(4) ?
P1 C1 B1 Br1 . . . . 138.40(19) ?
C1 B1 C31 C32 . . . . -115.4(2) ?
C41 B1 C31 C32 . . . . 15.8(3) ?
Br1 B1 C31 C32 . . . . 131.69(19) ?
C1 B1 C31 C36 . . . . 57.8(2) ?
C41 B1 C31 C36 . . . . -171.09(19) ?
Br1 B1 C31 C36 . . . . -55.2(2) ?
C36 C31 C32 F32 . . . . -176.53(19) ?
B1 C31 C32 F32 . . . . -3.0(3) ?
C36 C31 C32 C33 . . . . 2.0(3) ?
B1 C31 C32 C33 . . . . 175.5(2) ?
F32 C32 C33 F33 . . . . -0.5(3) ?
C31 C32 C33 F33 . . . . -179.1(2) ?
F32 C32 C33 C34 . . . . 178.2(2) ?
C31 C32 C33 C34 . . . . -0.4(3) ?
F33 C33 C34 F34 . . . . -2.6(3) ?
C32 C33 C34 F34 . . . . 178.7(2) ?
F33 C33 C34 C35 . . . . 177.7(2) ?
C32 C33 C34 C35 . . . . -1.0(3) ?
F34 C34 C35 F35 . . . . 1.3(3) ?
C33 C34 C35 F35 . . . . -179.0(2) ?
F34 C34 C35 C36 . . . . -179.1(2) ?
C33 C34 C35 C36 . . . . 0.5(3) ?
F35 C35 C36 F36 . . . . 1.7(3) ?
C34 C35 C36 F36 . . . . -177.79(19) ?
F35 C35 C36 C31 . . . . -179.1(2) ?
C34 C35 C36 C31 . . . . 1.4(3) ?
C32 C31 C36 F36 . . . . 176.61(18) ?
B1 C31 C36 F36 . . . . 2.7(3) ?
C32 C31 C36 C35 . . . . -2.5(3) ?
B1 C31 C36 C35 . . . . -176.5(2) ?
C1 B1 C41 C46 . . . . -0.9(3) ?
C31 B1 C41 C46 . . . . -127.5(2) ?
Br1 B1 C41 C46 . . . . 113.7(2) ?
C1 B1 C41 C42 . . . . -176.99(19) ?
C31 B1 C41 C42 . . . . 56.5(3) ?
Br1 B1 C41 C42 . . . . -62.4(2) ?
C46 C41 C42 F42 . . . . 177.90(19) ?
B1 C41 C42 F42 . . . . -5.6(3) ?
C46 C41 C42 C43 . . . . -2.0(3) ?
B1 C41 C42 C43 . . . . 174.5(2) ?
F42 C42 C43 F43 . . . . 1.2(3) ?
C41 C42 C43 F43 . . . . -178.9(2) ?
F42 C42 C43 C44 . . . . -178.5(2) ?
C41 C42 C43 C44 . . . . 1.3(4) ?
F43 C43 C44 F44 . . . . 1.4(4) ?
C42 C43 C44 F44 . . . . -178.9(2) ?
F43 C43 C44 C45 . . . . -179.1(2) ?
C42 C43 C44 C45 . . . . 0.7(4) ?
F44 C44 C45 F45 . . . . -1.9(3) ?
C43 C44 C45 F45 . . . . 178.5(2) ?
F44 C44 C45 C46 . . . . 177.7(2) ?
C43 C44 C45 C46 . . . . -1.8(3) ?
F45 C45 C46 F46 . . . . 0.0(3) ?
C44 C45 C46 F46 . . . . -179.63(19) ?
F45 C45 C46 C41 . . . . -179.2(2) ?
C44 C45 C46 C41 . . . . 1.1(3) ?
C42 C41 C46 F46 . . . . -178.48(18) ?
B1 C41 C46 F46 . . . . 5.2(3) ?
C42 C41 C46 C45 . . . . 0.7(3) ?
B1 C41 C46 C45 . . . . -175.5(2) ?
C56 C51 C52 C53 . . . . 1.(3) ?
C57 C51 C52 C53 . . . . -178.8(16) ?
C51 C52 C53 C54 . . . . 2.(3) ?
C55 C54 C53 C52 . . . . -3.(2) ?
C53 C54 C55 C56 . . . . 2.(2) ?
C54 C55 C56 C51 . . . . 1.(3) ?
C52 C51 C56 C55 . . . . -2.(3) ?
C57 C51 C56 C55 . . . . 177.8(16) ?

####################################################################### 
# 
# 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_erk9221
_database_code_depnum_ccdc_archive 'CCDC 1865547'
_audit_update_record             
;
2018-09-03 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 B Br F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         671.15

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.9577(2)
_cell_length_b                   18.6647(5)
_cell_length_c                   16.5940(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.4580(10)
_cell_angle_gamma                90
_cell_volume                     2773.50(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9794
_cell_measurement_theta_min      3.5647
_cell_measurement_theta_max      72.1240
_cell_measurement_temperature    105.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.046
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

_exptl_absorpt_coefficient_mu    3.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      105.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_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            46108
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         72.39
_diffrn_reflns_theta_full        72.39
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_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             5453
_reflns_number_gt                4799
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0792
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_number_reflns         5453
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+2.1158P] 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         0.378
_refine_diff_density_min         -0.419
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (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
B B1 0.7054(3) 0.47571(13) 0.26282(15) 0.0191(5) Uani d . . . 1 . .
Br Br1 0.58861(3) 0.48494(2) 0.36996(2) 0.02473(8) Uani d . . . 1 . .
P P1 0.94330(6) 0.36761(3) 0.34552(3) 0.01631(12) Uani d . . . 1 . .
C C1 0.8141(2) 0.40761(11) 0.27574(13) 0.0175(4) Uani d . . . 1 . .
C C2 0.8812(2) 0.34963(11) 0.24732(13) 0.0177(4) Uani d . . . 1 . .
C C3 0.8993(2) 0.30078(12) 0.17970(13) 0.0193(4) Uani d . . . 1 . .
C C4 0.9730(3) 0.23563(12) 0.19286(15) 0.0240(5) Uani d . . . 1 . .
H H4 1.0095 0.2236 0.2454 0.029 Uiso calc U . R 1 . .
C C5 0.9928(3) 0.18854(13) 0.12944(17) 0.0309(6) Uani d . . . 1 . .
H H5 1.0412 0.1439 0.1387 0.037 Uiso calc U . R 1 . .
C C6 0.9419(3) 0.20658(14) 0.05269(16) 0.0311(6) Uani d . . . 1 . .
H H6 0.9562 0.1744 0.0092 0.037 Uiso calc U . R 1 . .
C C7 0.8704(3) 0.27126(14) 0.03902(15) 0.0281(5) Uani d . . . 1 . .
H H7 0.837 0.2836 -0.014 0.034 Uiso calc U . R 1 . .
C C8 0.8471(3) 0.31833(12) 0.10231(14) 0.0228(5) Uani d . . . 1 . .
H H8 0.7959 0.3622 0.0929 0.027 Uiso calc U . R 1 . .
C C11 1.1364(2) 0.40362(12) 0.35616(13) 0.0191(4) Uani d . . . 1 . .
C C12 1.1570(3) 0.45954(13) 0.29014(16) 0.0290(5) Uani d . . . 1 . .
H H12A 1.091 0.5004 0.2996 0.043 Uiso calc U . R 1 . .
H H12B 1.1321 0.4383 0.2375 0.043 Uiso calc U . R 1 . .
H H12C 1.261 0.4758 0.291 0.043 Uiso calc U . R 1 . .
C C13 1.1636(3) 0.43697(16) 0.43931(16) 0.0352(6) Uani d . . . 1 . .
H H13A 1.1537 0.4001 0.4808 0.053 Uiso calc U . R 1 . .
H H13B 1.0902 0.475 0.4479 0.053 Uiso calc U . R 1 . .
H H13C 1.2645 0.4573 0.4426 0.053 Uiso calc U . R 1 . .
C C14 1.2472(3) 0.34244(13) 0.34246(15) 0.0257(5) Uani d . . . 1 . .
H H14A 1.3494 0.3611 0.3459 0.039 Uiso calc U . R 1 . .
H H14B 1.2285 0.3216 0.289 0.039 Uiso calc U . R 1 . .
H H14C 1.2346 0.3055 0.3837 0.039 Uiso calc U . R 1 . .
C C21 0.8693(3) 0.31016(13) 0.42729(14) 0.0231(5) Uani d . . . 1 . .
C C22 0.8302(3) 0.35663(14) 0.50048(14) 0.0275(5) Uani d . . . 1 . .
H H22A 0.7583 0.3936 0.4837 0.041 Uiso calc U . R 1 . .
H H22B 0.921 0.3794 0.5224 0.041 Uiso calc U . R 1 . .
H H22C 0.7863 0.3264 0.542 0.041 Uiso calc U . R 1 . .
C C23 0.9853(3) 0.25346(14) 0.45260(16) 0.0311(6) Uani d . . . 1 . .
H H23A 0.9421 0.221 0.4922 0.047 Uiso calc U . R 1 . .
H H23B 1.0734 0.2771 0.4766 0.047 Uiso calc U . R 1 . .
H H23C 1.0145 0.226 0.4052 0.047 Uiso calc U . R 1 . .
C C24 0.7288(3) 0.27400(14) 0.39231(15) 0.0292(5) Uani d . . . 1 . .
H H24A 0.7551 0.2446 0.3459 0.044 Uiso calc U . R 1 . .
H H24B 0.6565 0.3107 0.3751 0.044 Uiso calc U . R 1 . .
H H24C 0.6847 0.2436 0.4335 0.044 Uiso calc U . R 1 . .
C C31 0.8164(3) 0.54300(12) 0.24542(14) 0.0218(5) Uani d . . . 1 . .
C C32 0.8629(3) 0.59785(13) 0.29658(16) 0.0274(5) Uani d . . . 1 . .
F F32 0.81123(18) 0.60416(8) 0.37140(9) 0.0373(4) Uani d . . . 1 . .
C C33 0.9679(3) 0.64886(13) 0.27560(18) 0.0361(6) Uani d . . . 1 . .
F F33 1.0085(2) 0.69984(9) 0.32865(12) 0.0533(5) Uani d . . . 1 . .
C C34 1.0320(3) 0.64567(15) 0.20189(19) 0.0420(7) Uani d . . . 1 . .
F F34 1.1363(2) 0.69374(11) 0.18123(13) 0.0663(6) Uani d . . . 1 . .
C C35 0.9913(3) 0.59197(15) 0.14840(17) 0.0352(6) Uani d . . . 1 . .
F F35 1.0548(2) 0.58768(10) 0.07627(11) 0.0518(5) Uani d . . . 1 . .
C C36 0.8868(3) 0.54248(12) 0.17154(15) 0.0253(5) Uani d . . . 1 . .
F F36 0.85564(16) 0.48975(8) 0.11827(8) 0.0297(3) Uani d . . . 1 . .
C C41 0.5750(2) 0.46498(12) 0.19415(13) 0.0200(4) Uani d . . . 1 . .
C C42 0.5179(3) 0.51996(13) 0.14569(15) 0.0264(5) Uani d . . . 1 . .
F F42 0.57285(17) 0.58719(8) 0.15277(11) 0.0389(4) Uani d . . . 1 . .
C C43 0.4044(3) 0.51088(15) 0.08861(16) 0.0318(6) Uani d . . . 1 . .
F F43 0.36010(19) 0.56645(10) 0.04197(11) 0.0479(4) Uani d . . . 1 . .
C C44 0.3382(3) 0.44502(15) 0.07924(15) 0.0311(6) Uani d . . . 1 . .
F F44 0.22752(19) 0.43452(10) 0.02483(10) 0.0460(4) Uani d . . . 1 . .
C C45 0.3869(3) 0.38886(13) 0.12706(14) 0.0243(5) Uani d . . . 1 . .
F F45 0.31949(16) 0.32494(8) 0.12042(9) 0.0316(3) Uani d . . . 1 . .
C C46 0.5027(2) 0.39971(12) 0.18221(13) 0.0201(4) Uani d . . . 1 . .
F F46 0.54368(15) 0.34273(7) 0.22750(8) 0.0241(3) 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 C1 . 1.612(3) ?
B1 C41 . 1.624(3) ?
B1 C31 . 1.632(3) ?
B1 Br1 . 2.093(2) ?
P1 C2 . 1.741(2) ?
P1 C1 . 1.780(2) ?
P1 C11 . 1.860(2) ?
P1 C21 . 1.864(2) ?
C1 C2 . 1.330(3) ?
C2 C3 . 1.458(3) ?
C3 C8 . 1.395(3) ?
C3 C4 . 1.398(3) ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.383(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.383(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C11 C12 . 1.528(3) ?
C11 C13 . 1.528(3) ?
C11 C14 . 1.534(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C21 C24 . 1.530(3) ?
C21 C23 . 1.534(3) ?
C21 C22 . 1.540(3) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C31 C32 . 1.387(3) ?
C31 C36 . 1.393(3) ?
C32 F32 . 1.341(3) ?
C32 C33 . 1.389(4) ?
C33 F33 . 1.340(3) ?
C33 C34 . 1.365(5) ?
C34 F34 . 1.346(3) ?
C34 C35 . 1.382(4) ?
C35 F35 . 1.341(3) ?
C35 C36 . 1.377(3) ?
C36 F36 . 1.347(3) ?
C41 C46 . 1.392(3) ?
C41 C42 . 1.393(3) ?
C42 F42 . 1.352(3) ?
C42 C43 . 1.382(4) ?
C43 F43 . 1.348(3) ?
C43 C44 . 1.372(4) ?
C44 F44 . 1.338(3) ?
C44 C45 . 1.379(4) ?
C45 F45 . 1.340(3) ?
C45 C46 . 1.381(3) ?
C46 F46 . 1.348(3) ?

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
C1 B1 C41 . . 114.68(19) ?
C1 B1 C31 . . 105.19(18) ?
C41 B1 C31 . . 113.66(19) ?
C1 B1 Br1 . . 105.38(15) ?
C41 B1 Br1 . . 103.87(14) ?
C31 B1 Br1 . . 114.01(16) ?
C2 P1 C1 . . 44.36(10) ?
C2 P1 C11 . . 115.65(10) ?
C1 P1 C11 . . 119.85(10) ?
C2 P1 C21 . . 117.34(11) ?
C1 P1 C21 . . 118.51(10) ?
C11 P1 C21 . . 119.06(10) ?
C2 C1 B1 . . 150.6(2) ?
C2 C1 P1 . . 66.26(13) ?
B1 C1 P1 . . 142.90(17) ?
C1 C2 C3 . . 147.3(2) ?
C1 C2 P1 . . 69.38(14) ?
C3 C2 P1 . . 143.27(17) ?
C8 C3 C4 . . 119.6(2) ?
C8 C3 C2 . . 121.4(2) ?
C4 C3 C2 . . 119.0(2) ?
C5 C4 C3 . . 120.1(2) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.0(2) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C7 C6 C5 . . 120.3(2) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 120.4(2) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C7 C8 C3 . . 119.6(2) ?
C7 C8 H8 . . 120.2 ?
C3 C8 H8 . . 120.2 ?
C12 C11 C13 . . 110.5(2) ?
C12 C11 C14 . . 108.18(19) ?
C13 C11 C14 . . 110.4(2) ?
C12 C11 P1 . . 107.92(15) ?
C13 C11 P1 . . 111.09(16) ?
C14 C11 P1 . . 108.71(15) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C24 C21 C23 . . 110.2(2) ?
C24 C21 C22 . . 110.24(19) ?
C23 C21 C22 . . 109.8(2) ?
C24 C21 P1 . . 106.38(16) ?
C23 C21 P1 . . 110.19(16) ?
C22 C21 P1 . . 110.02(16) ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C21 C24 H24A . . 109.5 ?
C21 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C21 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C32 C31 C36 . . 114.1(2) ?
C32 C31 B1 . . 129.4(2) ?
C36 C31 B1 . . 116.2(2) ?
F32 C32 C31 . . 121.7(2) ?
F32 C32 C33 . . 115.1(2) ?
C31 C32 C33 . . 123.2(3) ?
F33 C33 C34 . . 120.4(3) ?
F33 C33 C32 . . 119.7(3) ?
C34 C33 C32 . . 119.8(3) ?
F34 C34 C33 . . 120.6(3) ?
F34 C34 C35 . . 119.6(3) ?
C33 C34 C35 . . 119.8(2) ?
F35 C35 C36 . . 121.1(3) ?
F35 C35 C34 . . 120.4(2) ?
C36 C35 C34 . . 118.5(3) ?
F36 C36 C35 . . 116.0(2) ?
F36 C36 C31 . . 119.4(2) ?
C35 C36 C31 . . 124.6(2) ?
C46 C41 C42 . . 113.6(2) ?
C46 C41 B1 . . 122.1(2) ?
C42 C41 B1 . . 124.1(2) ?
F42 C42 C43 . . 115.7(2) ?
F42 C42 C41 . . 120.4(2) ?
C43 C42 C41 . . 123.9(2) ?
F43 C43 C44 . . 120.3(2) ?
F43 C43 C42 . . 120.0(2) ?
C44 C43 C42 . . 119.7(2) ?
F44 C44 C43 . . 121.2(2) ?
F44 C44 C45 . . 119.7(2) ?
C43 C44 C45 . . 119.1(2) ?
F45 C45 C44 . . 119.6(2) ?
F45 C45 C46 . . 121.0(2) ?
C44 C45 C46 . . 119.4(2) ?
F46 C46 C45 . . 116.3(2) ?
F46 C46 C41 . . 119.5(2) ?
C45 C46 C41 . . 124.2(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C41 B1 C1 C2 . . . . 29.2(5) ?
C31 B1 C1 C2 . . . . -96.4(4) ?
Br1 B1 C1 C2 . . . . 142.8(4) ?
C41 B1 C1 P1 . . . . -160.3(2) ?
C31 B1 C1 P1 . . . . 74.1(3) ?
Br1 B1 C1 P1 . . . . -46.7(3) ?
C11 P1 C1 C2 . . . . 97.29(15) ?
C21 P1 C1 C2 . . . . -101.07(15) ?
C2 P1 C1 B1 . . . . -174.9(3) ?
C11 P1 C1 B1 . . . . -77.6(3) ?
C21 P1 C1 B1 . . . . 84.0(3) ?
B1 C1 C2 C3 . . . . -5.2(7) ?
P1 C1 C2 C3 . . . . -179.0(4) ?
B1 C1 C2 P1 . . . . 173.7(4) ?
C11 P1 C2 C1 . . . . -107.39(14) ?
C21 P1 C2 C1 . . . . 103.88(15) ?
C1 P1 C2 C3 . . . . 179.1(3) ?
C11 P1 C2 C3 . . . . 71.7(3) ?
C21 P1 C2 C3 . . . . -77.0(3) ?
C1 C2 C3 C8 . . . . 14.3(5) ?
P1 C2 C3 C8 . . . . -164.1(2) ?
C1 C2 C3 C4 . . . . -166.9(3) ?
P1 C2 C3 C4 . . . . 14.7(4) ?
C8 C3 C4 C5 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . -179.4(2) ?
C3 C4 C5 C6 . . . . 1.2(4) ?
C4 C5 C6 C7 . . . . -0.5(4) ?
C5 C6 C7 C8 . . . . -0.8(4) ?
C6 C7 C8 C3 . . . . 1.4(3) ?
C4 C3 C8 C7 . . . . -0.7(3) ?
C2 C3 C8 C7 . . . . 178.1(2) ?
C2 P1 C11 C12 . . . . 42.62(19) ?
C1 P1 C11 C12 . . . . -7.7(2) ?
C21 P1 C11 C12 . . . . -169.21(16) ?
C2 P1 C11 C13 . . . . 163.88(17) ?
C1 P1 C11 C13 . . . . 113.58(19) ?
C21 P1 C11 C13 . . . . -48.0(2) ?
C2 P1 C11 C14 . . . . -74.49(18) ?
C1 P1 C11 C14 . . . . -124.78(16) ?
C21 P1 C11 C14 . . . . 73.68(18) ?
C2 P1 C21 C24 . . . . -18.1(2) ?
C1 P1 C21 C24 . . . . 32.4(2) ?
C11 P1 C21 C24 . . . . -165.77(15) ?
C2 P1 C21 C23 . . . . 101.27(19) ?
C1 P1 C21 C23 . . . . 151.84(17) ?
C11 P1 C21 C23 . . . . -46.4(2) ?
C2 P1 C21 C22 . . . . -137.52(16) ?
C1 P1 C21 C22 . . . . -86.95(19) ?
C11 P1 C21 C22 . . . . 74.84(19) ?
C1 B1 C31 C32 . . . . -102.6(3) ?
C41 B1 C31 C32 . . . . 131.1(2) ?
Br1 B1 C31 C32 . . . . 12.3(3) ?
C1 B1 C31 C36 . . . . 70.5(2) ?
C41 B1 C31 C36 . . . . -55.8(3) ?
Br1 B1 C31 C36 . . . . -174.60(17) ?
C36 C31 C32 F32 . . . . -177.0(2) ?
B1 C31 C32 F32 . . . . -3.7(4) ?
C36 C31 C32 C33 . . . . 1.4(3) ?
B1 C31 C32 C33 . . . . 174.6(2) ?
F32 C32 C33 F33 . . . . -0.8(3) ?
C31 C32 C33 F33 . . . . -179.3(2) ?
F32 C32 C33 C34 . . . . 177.5(2) ?
C31 C32 C33 C34 . . . . -0.9(4) ?
F33 C33 C34 F34 . . . . -0.3(4) ?
C32 C33 C34 F34 . . . . -178.6(3) ?
F33 C33 C34 C35 . . . . 178.7(3) ?
C32 C33 C34 C35 . . . . 0.4(4) ?
F34 C34 C35 F35 . . . . -0.1(4) ?
C33 C34 C35 F35 . . . . -179.1(3) ?
F34 C34 C35 C36 . . . . 178.6(3) ?
C33 C34 C35 C36 . . . . -0.4(4) ?
F35 C35 C36 F36 . . . . 1.2(4) ?
C34 C35 C36 F36 . . . . -177.5(2) ?
F35 C35 C36 C31 . . . . 179.7(2) ?
C34 C35 C36 C31 . . . . 1.0(4) ?
C32 C31 C36 F36 . . . . 177.0(2) ?
B1 C31 C36 F36 . . . . 2.9(3) ?
C32 C31 C36 C35 . . . . -1.4(4) ?
B1 C31 C36 C35 . . . . -175.6(2) ?
C1 B1 C41 C46 . . . . 36.8(3) ?
C31 B1 C41 C46 . . . . 157.9(2) ?
Br1 B1 C41 C46 . . . . -77.7(2) ?
C1 B1 C41 C42 . . . . -147.6(2) ?
C31 B1 C41 C42 . . . . -26.5(3) ?
Br1 B1 C41 C42 . . . . 98.0(2) ?
C46 C41 C42 F42 . . . . 177.3(2) ?
B1 C41 C42 F42 . . . . 1.4(4) ?
C46 C41 C42 C43 . . . . -2.4(3) ?
B1 C41 C42 C43 . . . . -178.4(2) ?
F42 C42 C43 F43 . . . . 2.9(4) ?
C41 C42 C43 F43 . . . . -177.3(2) ?
F42 C42 C43 C44 . . . . -177.6(2) ?
C41 C42 C43 C44 . . . . 2.1(4) ?
F43 C43 C44 F44 . . . . -0.9(4) ?
C42 C43 C44 F44 . . . . 179.7(2) ?
F43 C43 C44 C45 . . . . 179.2(2) ?
C42 C43 C44 C45 . . . . -0.2(4) ?
F44 C44 C45 F45 . . . . -2.2(4) ?
C43 C44 C45 F45 . . . . 177.7(2) ?
F44 C44 C45 C46 . . . . 179.0(2) ?
C43 C44 C45 C46 . . . . -1.1(4) ?
F45 C45 C46 F46 . . . . 0.6(3) ?
C44 C45 C46 F46 . . . . 179.4(2) ?
F45 C45 C46 C41 . . . . -178.1(2) ?
C44 C45 C46 C41 . . . . 0.7(4) ?
C42 C41 C46 F46 . . . . -177.64(19) ?
B1 C41 C46 F46 . . . . -1.6(3) ?
C42 C41 C46 C45 . . . . 1.0(3) ?
B1 C41 C46 C45 . . . . 177.1(2) ?

