# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_erk9382
_database_code_depnum_ccdc_archive 'CCDC 1922906'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 B F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         545.22

_chemical_melting_point          ?

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

_cell_length_a                   16.8585(5)
_cell_length_b                   9.6751(3)
_cell_length_c                   15.4623(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.8320(10)
_cell_angle_gamma                90
_cell_volume                     2341.14(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.8237
_cell_measurement_theta_max      68.3640
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.116
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104

_exptl_absorpt_coefficient_mu    1.289
_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  0.80
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(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            36701
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_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             4296
_reflns_number_gt                3652
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1024
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_number_reflns         4296
_refine_ls_number_parameters     343
_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)+(0.0285P)²+2.3339P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.236
_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'
N N 0.0311 0.0180 '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'

_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 0.20666(15) 0.4424(2) 0.35179(16) 0.0218(5) Uani d . . . 1 . .
C C1 0.3440(2) 0.1383(3) 0.2033(2) 0.0549(8) Uani d . . . 1 . .
H H1A 0.3788 0.141 0.2677 0.066 Uiso calc U . R 1 . .
H H1B 0.3343 0.053 0.1706 0.066 Uiso calc U . R 1 . .
C C2 0.30888(17) 0.2531(3) 0.15931(19) 0.0378(6) Uani d . . . 1 . .
H H2 0.2745 0.246 0.0949 0.045 Uiso calc U . R 1 . .
C C3 0.31917(14) 0.3944(2) 0.20310(16) 0.0290(5) Uani d . . . 1 . .
H H3 0.3516 0.3835 0.2716 0.035 Uiso calc U . R 1 . .
C C4 0.23183(14) 0.4546(2) 0.18948(14) 0.0253(4) Uani d . . . 1 . .
C C5 0.18377(13) 0.3898(2) 0.24362(14) 0.0247(4) Uani d . . . 1 . .
H H5A 0.1934 0.2888 0.245 0.03 Uiso calc U . R 1 . .
H H5B 0.122 0.4057 0.2087 0.03 Uiso calc U . R 1 . .
C C6 0.20003(16) 0.5613(2) 0.13194(15) 0.0326(5) Uani d . . . 1 . .
H H6 0.145 0.5937 0.1258 0.039 Uiso calc U . R 1 . .
C C7 0.24385(17) 0.6346(3) 0.07596(17) 0.0390(6) Uani d . . . 1 . .
H H7A 0.2664 0.7244 0.1057 0.047 Uiso calc U . R 1 . .
H H7B 0.2018 0.6534 0.0126 0.047 Uiso calc U . R 1 . .
C C8 0.31665(17) 0.5491(3) 0.06902(17) 0.0371(6) Uani d . . . 1 . .
H H8A 0.3525 0.6073 0.0454 0.044 Uiso calc U . R 1 . .
H H8B 0.2934 0.4721 0.0247 0.044 Uiso calc U . R 1 . .
C C9 0.37086(15) 0.4916(3) 0.16466(17) 0.0336(5) Uani d . . . 1 . .
H H9A 0.3937 0.5692 0.2086 0.04 Uiso calc U . R 1 . .
H H9B 0.42 0.4403 0.1601 0.04 Uiso calc U . R 1 . .
C C11 0.30351(13) 0.4028(2) 0.42586(14) 0.0213(4) Uani d . . . 1 . .
C C12 0.33334(13) 0.2684(2) 0.42747(15) 0.0244(4) Uani d . . . 1 . .
F F12 0.28201(8) 0.17148(12) 0.37088(9) 0.0308(3) Uani d . . . 1 . .
C C13 0.41305(15) 0.2228(2) 0.48539(17) 0.0320(5) Uani d . . . 1 . .
F F13 0.43765(9) 0.09240(15) 0.47961(11) 0.0451(4) Uani d . . . 1 . .
C C14 0.46685(14) 0.3115(3) 0.54985(17) 0.0343(5) Uani d . . . 1 . .
F F14 0.54392(9) 0.26806(18) 0.60864(11) 0.0501(4) Uani d . . . 1 . .
C C15 0.44041(14) 0.4440(3) 0.55504(15) 0.0301(5) Uani d . . . 1 . .
F F15 0.49090(9) 0.53166(16) 0.61976(9) 0.0428(4) Uani d . . . 1 . .
C C16 0.36069(14) 0.4861(2) 0.49421(14) 0.0256(4) Uani d . . . 1 . .
F F16 0.34054(8) 0.61839(13) 0.50670(9) 0.0311(3) Uani d . . . 1 . .
C C21 0.14184(13) 0.3797(2) 0.40062(14) 0.0219(4) Uani d . . . 1 . .
C C22 0.09459(13) 0.2586(2) 0.37373(15) 0.0236(4) Uani d . . . 1 . .
F F22 0.08993(8) 0.18932(13) 0.29577(9) 0.0310(3) Uani d . . . 1 . .
C C23 0.04927(14) 0.1987(2) 0.42269(16) 0.0287(5) Uani d . . . 1 . .
F F23 0.00761(9) 0.07865(14) 0.39220(10) 0.0395(3) Uani d . . . 1 . .
C C24 0.04605(14) 0.2616(2) 0.50040(16) 0.0290(5) Uani d . . . 1 . .
F F24 -0.00034(9) 0.20783(15) 0.54636(10) 0.0390(3) Uani d . . . 1 . .
C C25 0.09049(14) 0.3830(2) 0.53000(15) 0.0276(5) Uani d . . . 1 . .
F F25 0.08798(9) 0.44707(15) 0.60615(9) 0.0385(3) Uani d . . . 1 . .
C C26 0.13753(13) 0.4362(2) 0.48149(14) 0.0243(4) Uani d . . . 1 . .
F F26 0.18255(9) 0.55248(13) 0.51719(9) 0.0324(3) Uani d . . . 1 . .
N N31 0.19537(11) 0.60777(17) 0.34054(11) 0.0217(4) Uani d . . . 1 . .
C C32 0.25753(14) 0.6823(2) 0.32762(15) 0.0256(4) Uani d . . . 1 . .
H H32 0.3092 0.6376 0.3326 0.031 Uiso calc U . R 1 . .
C C33 0.24853(15) 0.8220(2) 0.30733(16) 0.0311(5) Uani d . . . 1 . .
H H33 0.2941 0.8729 0.3005 0.037 Uiso calc U . R 1 . .
C C34 0.17274(16) 0.8864(2) 0.29709(15) 0.0321(5) Uani d . . . 1 . .
H H34 0.1654 0.9824 0.2834 0.038 Uiso calc U . R 1 . .
C C35 0.10740(15) 0.8093(2) 0.30699(15) 0.0297(5) Uani d . . . 1 . .
H H35 0.0542 0.8515 0.299 0.036 Uiso calc U . R 1 . .
C C36 0.12035(13) 0.6706(2) 0.32866(14) 0.0241(4) Uani d . . . 1 . .
H H36 0.0754 0.6179 0.3354 0.029 Uiso calc U . R 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 N31 . 1.613(3) ?
B1 C5 . 1.651(3) ?
B1 C11 . 1.653(3) ?
B1 C21 . 1.657(3) ?
C1 C2 . 1.322(4) ?
C1 H1A . 0.95 ?
C1 H1B . 0.95 ?
C2 C3 . 1.506(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.524(3) ?
C3 C9 . 1.544(3) ?
C3 H3 . 1.0 ?
C4 C6 . 1.337(3) ?
C4 C5 . 1.502(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.508(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.517(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.525(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C11 C12 . 1.391(3) ?
C11 C16 . 1.392(3) ?
C12 F12 . 1.353(2) ?
C12 C13 . 1.381(3) ?
C13 F13 . 1.341(3) ?
C13 C14 . 1.371(4) ?
C14 F14 . 1.346(3) ?
C14 C15 . 1.370(4) ?
C15 F15 . 1.346(3) ?
C15 C16 . 1.385(3) ?
C16 F16 . 1.356(3) ?
C21 C22 . 1.390(3) ?
C21 C26 . 1.391(3) ?
C22 F22 . 1.356(2) ?
C22 C23 . 1.387(3) ?
C23 F23 . 1.349(2) ?
C23 C24 . 1.366(3) ?
C24 F24 . 1.342(2) ?
C24 C25 . 1.377(3) ?
C25 F25 . 1.345(3) ?
C25 C26 . 1.378(3) ?
C26 F26 . 1.355(2) ?
N31 C32 . 1.347(3) ?
N31 C36 . 1.352(3) ?
C32 C33 . 1.383(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.377(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.385(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.382(3) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

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
N31 B1 C5 . . 102.85(16) ?
N31 B1 C11 . . 110.53(16) ?
C5 B1 C11 . . 115.42(17) ?
N31 B1 C21 . . 109.92(17) ?
C5 B1 C21 . . 113.82(17) ?
C11 B1 C21 . . 104.38(16) ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C3 . . 125.2(3) ?
C1 C2 H2 . . 117.4 ?
C3 C2 H2 . . 117.4 ?
C2 C3 C4 . . 109.96(19) ?
C2 C3 C9 . . 111.53(19) ?
C4 C3 C9 . . 111.61(18) ?
C2 C3 H3 . . 107.9 ?
C4 C3 H3 . . 107.9 ?
C9 C3 H3 . . 107.9 ?
C6 C4 C5 . . 121.8(2) ?
C6 C4 C3 . . 121.0(2) ?
C5 C4 C3 . . 117.19(18) ?
C4 C5 B1 . . 117.72(17) ?
C4 C5 H5A . . 107.9 ?
B1 C5 H5A . . 107.9 ?
C4 C5 H5B . . 107.9 ?
B1 C5 H5B . . 107.9 ?
H5A C5 H5B . . 107.2 ?
C4 C6 C7 . . 125.7(2) ?
C4 C6 H6 . . 117.1 ?
C7 C6 H6 . . 117.1 ?
C6 C7 C8 . . 111.5(2) ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C7 C8 C9 . . 109.83(19) ?
C7 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
C7 C8 H8B . . 109.7 ?
C9 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C8 C9 C3 . . 112.0(2) ?
C8 C9 H9A . . 109.2 ?
C3 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C3 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C12 C11 C16 . . 112.58(19) ?
C12 C11 B1 . . 119.08(18) ?
C16 C11 B1 . . 128.20(18) ?
F12 C12 C13 . . 115.59(19) ?
F12 C12 C11 . . 119.76(18) ?
C13 C12 C11 . . 124.6(2) ?
F13 C13 C14 . . 120.0(2) ?
F13 C13 C12 . . 120.5(2) ?
C14 C13 C12 . . 119.5(2) ?
F14 C14 C15 . . 120.4(2) ?
F14 C14 C13 . . 120.5(2) ?
C15 C14 C13 . . 119.1(2) ?
F15 C15 C14 . . 120.3(2) ?
F15 C15 C16 . . 120.4(2) ?
C14 C15 C16 . . 119.4(2) ?
F16 C16 C15 . . 114.35(19) ?
F16 C16 C11 . . 121.00(19) ?
C15 C16 C11 . . 124.6(2) ?
C22 C21 C26 . . 112.59(19) ?
C22 C21 B1 . . 125.00(18) ?
C26 C21 B1 . . 121.98(18) ?
F22 C22 C23 . . 114.66(18) ?
F22 C22 C21 . . 121.31(19) ?
C23 C22 C21 . . 124.02(19) ?
F23 C23 C24 . . 120.4(2) ?
F23 C23 C22 . . 119.3(2) ?
C24 C23 C22 . . 120.3(2) ?
F24 C24 C23 . . 121.0(2) ?
F24 C24 C25 . . 120.5(2) ?
C23 C24 C25 . . 118.5(2) ?
F25 C25 C24 . . 119.58(19) ?
F25 C25 C26 . . 121.1(2) ?
C24 C25 C26 . . 119.3(2) ?
F26 C26 C25 . . 115.90(19) ?
F26 C26 C21 . . 118.94(18) ?
C25 C26 C21 . . 125.2(2) ?
C32 N31 C36 . . 118.63(18) ?
C32 N31 B1 . . 118.70(17) ?
C36 N31 B1 . . 121.80(17) ?
N31 C32 C33 . . 122.1(2) ?
N31 C32 H32 . . 119.0 ?
C33 C32 H32 . . 119.0 ?
C34 C33 C32 . . 119.2(2) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C33 C34 C35 . . 119.1(2) ?
C33 C34 H34 . . 120.5 ?
C35 C34 H34 . . 120.5 ?
C36 C35 C34 . . 119.3(2) ?
C36 C35 H35 . . 120.3 ?
C34 C35 H35 . . 120.3 ?
N31 C36 C35 . . 121.7(2) ?
N31 C36 H36 . . 119.2 ?
C35 C36 H36 . . 119.2 ?

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
C1 C2 C3 C4 . . . . -123.2(3) ?
C1 C2 C3 C9 . . . . 112.5(3) ?
C2 C3 C4 C6 . . . . -109.9(2) ?
C9 C3 C4 C6 . . . . 14.4(3) ?
C2 C3 C4 C5 . . . . 70.4(2) ?
C9 C3 C4 C5 . . . . -165.25(18) ?
C6 C4 C5 B1 . . . . -95.8(3) ?
C3 C4 C5 B1 . . . . 83.8(2) ?
N31 B1 C5 C4 . . . . 53.7(2) ?
C11 B1 C5 C4 . . . . -66.8(2) ?
C21 B1 C5 C4 . . . . 172.54(17) ?
C5 C4 C6 C7 . . . . 179.0(2) ?
C3 C4 C6 C7 . . . . -0.7(4) ?
C4 C6 C7 C8 . . . . 17.0(4) ?
C6 C7 C8 C9 . . . . -46.0(3) ?
C7 C8 C9 C3 . . . . 62.0(3) ?
C2 C3 C9 C8 . . . . 78.6(3) ?
C4 C3 C9 C8 . . . . -44.8(3) ?
N31 B1 C11 C12 . . . . -163.83(18) ?
C5 B1 C11 C12 . . . . -47.7(3) ?
C21 B1 C11 C12 . . . . 78.0(2) ?
N31 B1 C11 C16 . . . . 20.6(3) ?
C5 B1 C11 C16 . . . . 136.7(2) ?
C21 B1 C11 C16 . . . . -97.6(2) ?
C16 C11 C12 F12 . . . . 174.14(18) ?
B1 C11 C12 F12 . . . . -2.1(3) ?
C16 C11 C12 C13 . . . . -4.3(3) ?
B1 C11 C12 C13 . . . . 179.5(2) ?
F12 C12 C13 F13 . . . . 4.1(3) ?
C11 C12 C13 F13 . . . . -177.42(19) ?
F12 C12 C13 C14 . . . . -175.22(19) ?
C11 C12 C13 C14 . . . . 3.3(3) ?
F13 C13 C14 F14 . . . . -1.1(3) ?
C12 C13 C14 F14 . . . . 178.2(2) ?
F13 C13 C14 C15 . . . . -179.6(2) ?
C12 C13 C14 C15 . . . . -0.3(3) ?
F14 C14 C15 F15 . . . . -0.8(3) ?
C13 C14 C15 F15 . . . . 177.8(2) ?
F14 C14 C15 C16 . . . . -179.6(2) ?
C13 C14 C15 C16 . . . . -1.1(3) ?
F15 C15 C16 F16 . . . . 0.0(3) ?
C14 C15 C16 F16 . . . . 178.86(19) ?
F15 C15 C16 C11 . . . . -179.14(19) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C12 C11 C16 F16 . . . . -176.29(18) ?
B1 C11 C16 F16 . . . . -0.5(3) ?
C12 C11 C16 C15 . . . . 2.8(3) ?
B1 C11 C16 C15 . . . . 178.6(2) ?
N31 B1 C21 C22 . . . . 138.5(2) ?
C5 B1 C21 C22 . . . . 23.7(3) ?
C11 B1 C21 C22 . . . . -103.0(2) ?
N31 B1 C21 C26 . . . . -49.6(3) ?
C5 B1 C21 C26 . . . . -164.36(19) ?
C11 B1 C21 C26 . . . . 69.0(2) ?
C26 C21 C22 F22 . . . . 179.06(18) ?
B1 C21 C22 F22 . . . . -8.4(3) ?
C26 C21 C22 C23 . . . . -1.1(3) ?
B1 C21 C22 C23 . . . . 171.5(2) ?
F22 C22 C23 F23 . . . . 1.9(3) ?
C21 C22 C23 F23 . . . . -177.92(19) ?
F22 C22 C23 C24 . . . . -177.32(19) ?
C21 C22 C23 C24 . . . . 2.8(3) ?
F23 C23 C24 F24 . . . . -1.9(3) ?
C22 C23 C24 F24 . . . . 177.3(2) ?
F23 C23 C24 C25 . . . . 179.1(2) ?
C22 C23 C24 C25 . . . . -1.7(3) ?
F24 C24 C25 F25 . . . . 0.7(3) ?
C23 C24 C25 F25 . . . . 179.8(2) ?
F24 C24 C25 C26 . . . . -179.9(2) ?
C23 C24 C25 C26 . . . . -0.9(3) ?
F25 C25 C26 F26 . . . . 2.2(3) ?
C24 C25 C26 F26 . . . . -177.15(19) ?
F25 C25 C26 C21 . . . . -177.9(2) ?
C24 C25 C26 C21 . . . . 2.7(3) ?
C22 C21 C26 F26 . . . . 178.20(18) ?
B1 C21 C26 F26 . . . . 5.4(3) ?
C22 C21 C26 C25 . . . . -1.7(3) ?
B1 C21 C26 C25 . . . . -174.5(2) ?
C5 B1 N31 C32 . . . . -77.1(2) ?
C11 B1 N31 C32 . . . . 46.6(2) ?
C21 B1 N31 C32 . . . . 161.33(17) ?
C5 B1 N31 C36 . . . . 92.0(2) ?
C11 B1 N31 C36 . . . . -144.24(18) ?
C21 B1 N31 C36 . . . . -29.5(2) ?
C36 N31 C32 C33 . . . . 3.3(3) ?
B1 N31 C32 C33 . . . . 172.8(2) ?
N31 C32 C33 C34 . . . . -2.1(3) ?
C32 C33 C34 C35 . . . . -0.3(3) ?
C33 C34 C35 C36 . . . . 1.3(3) ?
C32 N31 C36 C35 . . . . -2.3(3) ?
B1 N31 C36 C35 . . . . -171.43(19) ?
C34 C35 C36 N31 . . . . 0.0(3) ?

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

data_erk9636
_database_code_depnum_ccdc_archive 'CCDC 1957134'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-10-02 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H30 B F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         790.46

_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                   8.3209(3)
_cell_length_b                   11.3190(5)
_cell_length_c                   19.7803(8)
_cell_angle_alpha                99.3990(10)
_cell_angle_beta                 98.0400(10)
_cell_angle_gamma                104.0510(10)
_cell_volume                     1751.34(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8323
_cell_measurement_theta_min      2.3554
_cell_measurement_theta_max      26.6869
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    0.166
_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  0.94
_exptl_absorpt_correction_T_max  0.99

_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 7.3910

_diffrn_reflns_number            31008
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_full        26.78
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;

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

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

_reflns_number_total             7446
_reflns_number_gt                6191
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1107
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_number_reflns         7446
_refine_ls_number_parameters     505
_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)+(0.0335P)²+1.7720P] 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         0.440
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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
P P1 0.54918(7) 0.62111(5) 0.79902(3) 0.01360(13) Uani d . . . 1 . .
B B1 0.6748(3) 0.2740(2) 0.76024(13) 0.0146(5) Uani d . . . 1 . .
C C1 0.6161(3) 0.39224(19) 0.79815(11) 0.0153(4) Uani d . . . 1 . .
H H1A 0.5178 0.3605 0.8195 0.018 Uiso calc U . R 1 . .
H H1B 0.709 0.4442 0.8361 0.018 Uiso calc U . R 1 . .
C C2 0.5684(3) 0.47429(19) 0.74771(11) 0.0141(4) Uani d . . . 1 . .
H H2 0.4537 0.4287 0.7199 0.017 Uiso calc U . R 1 . .
C C3 0.6875(3) 0.5050(2) 0.69373(11) 0.0150(4) Uani d . . . 1 . .
H H3 0.7874 0.5746 0.7191 0.018 Uiso calc U . R 1 . .
C C4 0.7536(3) 0.39545(19) 0.66667(11) 0.0147(4) Uani d . . . 1 . .
C C5 0.8288(3) 0.3395(2) 0.72324(11) 0.0152(4) Uani d . . . 1 . .
H H5A 0.9154 0.405 0.7582 0.018 Uiso calc U . R 1 . .
H H5B 0.8828 0.2767 0.703 0.018 Uiso calc U . R 1 . .
C C6 0.7482(3) 0.3471(2) 0.59984(11) 0.0176(5) Uani d . . . 1 . .
H H6 0.796 0.2789 0.5928 0.021 Uiso calc U . R 1 . .
C C7 0.6790(3) 0.3824(2) 0.53329(12) 0.0223(5) Uani d . . . 1 . .
H H7A 0.7151 0.3366 0.4937 0.027 Uiso calc U . R 1 . .
H H7B 0.5543 0.3552 0.5253 0.027 Uiso calc U . R 1 . .
C C8 0.5927(3) 0.5547(2) 0.63663(12) 0.0185(5) Uani d . . . 1 . .
H H8A 0.493 0.487 0.611 0.022 Uiso calc U . R 1 . .
H H8B 0.5508 0.6226 0.6597 0.022 Uiso calc U . R 1 . .
C C11 0.6933(3) 0.6032(2) 0.58433(11) 0.0161(4) Uani d . . . 1 . .
C C12 0.7380(3) 0.7297(2) 0.58317(12) 0.0201(5) Uani d . . . 1 . .
H H12 0.7086 0.7865 0.617 0.024 Uiso calc U . R 1 . .
C C13 0.8251(3) 0.7741(2) 0.53323(12) 0.0229(5) Uani d . . . 1 . .
H H13 0.8541 0.8604 0.5327 0.027 Uiso calc U . R 1 . .
C C14 0.8687(3) 0.6913(2) 0.48451(12) 0.0241(5) Uani d . . . 1 . .
H H14 0.9298 0.7207 0.4507 0.029 Uiso calc U . R 1 . .
C C15 0.8235(3) 0.5654(2) 0.48493(12) 0.0221(5) Uani d . . . 1 . .
H H15 0.8541 0.5092 0.4512 0.027 Uiso calc U . R 1 . .
C C16 0.7342(3) 0.5196(2) 0.53368(11) 0.0178(5) Uani d . . . 1 . .
C C21 0.7560(3) 0.7294(2) 0.82127(12) 0.0200(5) Uani d . . . 1 . .
C C22 0.8750(3) 0.7095(2) 0.87299(13) 0.0265(5) Uani d . . . 1 . .
H H22 0.8419 0.6457 0.8981 0.032 Uiso calc U . R 1 . .
C C23 1.0407(3) 0.7828(3) 0.88752(15) 0.0356(7) Uani d . . . 1 . .
H H23 1.1212 0.7681 0.9219 0.043 Uiso calc U . R 1 . .
C C24 1.0885(3) 0.8769(3) 0.85213(15) 0.0397(8) Uani d . . . 1 . .
H H24 1.2012 0.9284 0.8631 0.048 Uiso calc U . R 1 . .
C C25 0.9739(3) 0.8966(2) 0.80094(15) 0.0336(7) Uani d . . . 1 . .
H H25 1.0081 0.9617 0.7768 0.04 Uiso calc U . R 1 . .
C C26 0.8080(3) 0.8219(2) 0.78421(13) 0.0241(5) Uani d . . . 1 . .
H H26 0.7307 0.834 0.7476 0.029 Uiso calc U . R 1 . .
C C31 0.3961(3) 0.6825(2) 0.75234(11) 0.0156(4) Uani d . . . 1 . .
C C32 0.4171(3) 0.8099(2) 0.75920(12) 0.0179(5) Uani d . . . 1 . .
H H32 0.5124 0.8671 0.7898 0.021 Uiso calc U . R 1 . .
C C33 0.2987(3) 0.8529(2) 0.72122(12) 0.0228(5) Uani d . . . 1 . .
H H33 0.3143 0.9398 0.7249 0.027 Uiso calc U . R 1 . .
C C34 0.1576(3) 0.7697(2) 0.67793(12) 0.0246(5) Uani d . . . 1 . .
H H34 0.0787 0.7997 0.6508 0.03 Uiso calc U . R 1 . .
C C35 0.1313(3) 0.6435(2) 0.67401(12) 0.0222(5) Uani d . . . 1 . .
H H35 0.0311 0.5871 0.6464 0.027 Uiso calc U . R 1 . .
C C36 0.2508(3) 0.5988(2) 0.71027(12) 0.0196(5) Uani d . . . 1 . .
H H36 0.234 0.5118 0.7066 0.024 Uiso calc U . R 1 . .
C C41 0.4727(3) 0.6022(2) 0.87884(11) 0.0176(5) Uani d . . . 1 . .
C C42 0.5446(3) 0.6903(2) 0.94080(12) 0.0232(5) Uani d . . . 1 . .
H H42 0.6418 0.7562 0.9426 0.028 Uiso calc U . R 1 . .
C C43 0.4731(4) 0.6807(2) 0.99924(13) 0.0291(6) Uani d . . . 1 . .
H H43 0.5226 0.7399 1.0414 0.035 Uiso calc U . R 1 . .
C C44 0.3313(4) 0.5867(3) 0.99724(13) 0.0308(6) Uani d . . . 1 . .
H H44 0.2836 0.5812 1.0379 0.037 Uiso calc U . R 1 . .
C C45 0.2577(3) 0.4999(2) 0.93576(14) 0.0289(6) Uani d . . . 1 . .
H H45 0.1588 0.4356 0.9343 0.035 Uiso calc U . R 1 . .
C C46 0.3281(3) 0.5067(2) 0.87675(12) 0.0226(5) Uani d . . . 1 . .
H H46 0.2784 0.4467 0.8349 0.027 Uiso calc U . R 1 . .
C C51 0.7285(3) 0.20007(19) 0.82151(11) 0.0150(4) Uani d . . . 1 . .
C C52 0.8904(3) 0.1991(2) 0.84973(12) 0.0181(5) Uani d . . . 1 . .
F F52 1.02519(17) 0.25844(13) 0.82530(7) 0.0268(3) Uani d . . . 1 . .
C C53 0.9287(3) 0.1386(2) 0.90308(12) 0.0210(5) Uani d . . . 1 . .
F F53 1.09023(17) 0.14470(13) 0.92797(8) 0.0303(3) Uani d . . . 1 . .
C C54 0.8004(3) 0.0702(2) 0.92914(11) 0.0206(5) Uani d . . . 1 . .
F F54 0.83219(18) 0.00536(13) 0.97811(7) 0.0279(3) Uani d . . . 1 . .
C C55 0.6371(3) 0.0673(2) 0.90352(11) 0.0192(5) Uani d . . . 1 . .
F F55 0.50939(18) 0.00139(13) 0.92852(7) 0.0268(3) Uani d . . . 1 . .
C C56 0.6053(3) 0.1327(2) 0.85193(11) 0.0163(4) Uani d . . . 1 . .
F F56 0.44049(16) 0.12793(13) 0.83159(7) 0.0217(3) Uani d . . . 1 . .
C C61 0.5284(3) 0.17091(19) 0.69812(11) 0.0149(4) Uani d . . . 1 . .
C C62 0.5748(3) 0.0816(2) 0.65369(11) 0.0170(5) Uani d . . . 1 . .
F F62 0.73256(16) 0.06741(12) 0.66676(7) 0.0233(3) Uani d . . . 1 . .
C C63 0.4691(3) 0.0024(2) 0.59494(12) 0.0195(5) Uani d . . . 1 . .
F F63 0.52487(18) -0.07926(12) 0.55348(7) 0.0268(3) Uani d . . . 1 . .
C C64 0.3049(3) 0.0073(2) 0.57911(12) 0.0209(5) Uani d . . . 1 . .
F F64 0.20045(18) -0.06916(13) 0.52210(7) 0.0291(3) Uani d . . . 1 . .
C C65 0.2479(3) 0.0884(2) 0.62297(12) 0.0188(5) Uani d . . . 1 . .
F F65 0.08519(16) 0.08988(13) 0.61037(7) 0.0256(3) Uani d . . . 1 . .
C C66 0.3591(3) 0.16676(19) 0.68080(11) 0.0162(4) Uani d . . . 1 . .
F F66 0.28896(16) 0.24191(12) 0.72163(7) 0.0211(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
P1 C21 . 1.802(2) ?
P1 C31 . 1.808(2) ?
P1 C41 . 1.808(2) ?
P1 C2 . 1.855(2) ?
B1 C1 . 1.639(3) ?
B1 C5 . 1.645(3) ?
B1 C51 . 1.652(3) ?
B1 C61 . 1.667(3) ?
C1 C2 . 1.545(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.579(3) ?
C2 H2 . 1.0 ?
C3 C4 . 1.524(3) ?
C3 C8 . 1.546(3) ?
C3 H3 . 1.0 ?
C4 C6 . 1.336(3) ?
C4 C5 . 1.507(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.515(3) ?
C6 H6 . 0.95 ?
C7 C16 . 1.508(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C11 . 1.509(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C11 C12 . 1.394(3) ?
C11 C16 . 1.399(3) ?
C12 C13 . 1.392(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.381(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.384(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.95 ?
C21 C26 . 1.393(3) ?
C21 C22 . 1.406(3) ?
C22 C23 . 1.389(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.378(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.375(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.394(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C31 C32 . 1.391(3) ?
C31 C36 . 1.399(3) ?
C32 C33 . 1.385(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.384(4) ?
C33 H33 . 0.95 ?
C34 C35 . 1.379(4) ?
C34 H34 . 0.95 ?
C35 C36 . 1.386(3) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C41 C46 . 1.399(3) ?
C41 C42 . 1.400(3) ?
C42 C43 . 1.379(3) ?
C42 H42 . 0.95 ?
C43 C44 . 1.375(4) ?
C43 H43 . 0.95 ?
C44 C45 . 1.389(4) ?
C44 H44 . 0.95 ?
C45 C46 . 1.382(3) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C51 C52 . 1.387(3) ?
C51 C56 . 1.392(3) ?
C52 F52 . 1.354(3) ?
C52 C53 . 1.390(3) ?
C53 F53 . 1.346(3) ?
C53 C54 . 1.374(3) ?
C54 F54 . 1.343(2) ?
C54 C55 . 1.373(3) ?
C55 F55 . 1.347(3) ?
C55 C56 . 1.387(3) ?
C56 F56 . 1.359(3) ?
C61 C66 . 1.390(3) ?
C61 C62 . 1.393(3) ?
C62 F62 . 1.355(3) ?
C62 C63 . 1.385(3) ?
C63 F63 . 1.345(3) ?
C63 C64 . 1.374(3) ?
C64 F64 . 1.348(3) ?
C64 C65 . 1.374(3) ?
C65 F65 . 1.347(3) ?
C65 C66 . 1.387(3) ?
C66 F66 . 1.365(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
C21 P1 C31 . . 112.07(11) ?
C21 P1 C41 . . 108.37(11) ?
C31 P1 C41 . . 103.58(10) ?
C21 P1 C2 . . 107.48(10) ?
C31 P1 C2 . . 112.01(10) ?
C41 P1 C2 . . 113.34(10) ?
C1 B1 C5 . . 103.42(17) ?
C1 B1 C51 . . 107.20(17) ?
C5 B1 C51 . . 115.59(18) ?
C1 B1 C61 . . 115.45(18) ?
C5 B1 C61 . . 107.85(17) ?
C51 B1 C61 . . 107.59(17) ?
C2 C1 B1 . . 113.42(17) ?
C2 C1 H1A . . 108.9 ?
B1 C1 H1A . . 108.9 ?
C2 C1 H1B . . 108.9 ?
B1 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C1 C2 C3 . . 116.87(17) ?
C1 C2 P1 . . 109.17(14) ?
C3 C2 P1 . . 109.60(14) ?
C1 C2 H2 . . 106.9 ?
C3 C2 H2 . . 106.9 ?
P1 C2 H2 . . 106.9 ?
C4 C3 C8 . . 114.89(17) ?
C4 C3 C2 . . 112.15(17) ?
C8 C3 C2 . . 107.95(17) ?
C4 C3 H3 . . 107.2 ?
C8 C3 H3 . . 107.2 ?
C2 C3 H3 . . 107.2 ?
C6 C4 C5 . . 119.7(2) ?
C6 C4 C3 . . 126.3(2) ?
C5 C4 C3 . . 114.02(17) ?
C4 C5 B1 . . 107.62(17) ?
C4 C5 H5A . . 110.2 ?
B1 C5 H5A . . 110.2 ?
C4 C5 H5B . . 110.2 ?
B1 C5 H5B . . 110.2 ?
H5A C5 H5B . . 108.5 ?
C4 C6 C7 . . 131.0(2) ?
C4 C6 H6 . . 114.5 ?
C7 C6 H6 . . 114.5 ?
C16 C7 C6 . . 114.21(18) ?
C16 C7 H7A . . 108.7 ?
C6 C7 H7A . . 108.7 ?
C16 C7 H7B . . 108.7 ?
C6 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C11 C8 C3 . . 115.98(18) ?
C11 C8 H8A . . 108.3 ?
C3 C8 H8A . . 108.3 ?
C11 C8 H8B . . 108.3 ?
C3 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
C12 C11 C16 . . 119.3(2) ?
C12 C11 C8 . . 120.9(2) ?
C16 C11 C8 . . 119.7(2) ?
C13 C12 C11 . . 121.0(2) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C14 C13 C12 . . 119.3(2) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C15 . . 120.0(2) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C16 . . 121.3(2) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C15 C16 C11 . . 119.1(2) ?
C15 C16 C7 . . 121.9(2) ?
C11 C16 C7 . . 119.1(2) ?
C26 C21 C22 . . 118.9(2) ?
C26 C21 P1 . . 122.82(19) ?
C22 C21 P1 . . 117.82(19) ?
C23 C22 C21 . . 120.2(3) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C24 C23 C22 . . 120.1(3) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C25 C24 C23 . . 120.3(3) ?
C25 C24 H24 . . 119.8 ?
C23 C24 H24 . . 119.8 ?
C24 C25 C26 . . 120.5(3) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C21 C26 C25 . . 119.9(3) ?
C21 C26 H26 . . 120.1 ?
C25 C26 H26 . . 120.1 ?
C32 C31 C36 . . 119.8(2) ?
C32 C31 P1 . . 121.62(17) ?
C36 C31 P1 . . 118.58(17) ?
C33 C32 C31 . . 119.7(2) ?
C33 C32 H32 . . 120.1 ?
C31 C32 H32 . . 120.1 ?
C34 C33 C32 . . 120.3(2) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C35 C34 C33 . . 120.2(2) ?
C35 C34 H34 . . 119.9 ?
C33 C34 H34 . . 119.9 ?
C34 C35 C36 . . 120.2(2) ?
C34 C35 H35 . . 119.9 ?
C36 C35 H35 . . 119.9 ?
C35 C36 C31 . . 119.7(2) ?
C35 C36 H36 . . 120.2 ?
C31 C36 H36 . . 120.2 ?
C46 C41 C42 . . 119.6(2) ?
C46 C41 P1 . . 119.41(17) ?
C42 C41 P1 . . 120.58(18) ?
C43 C42 C41 . . 119.5(2) ?
C43 C42 H42 . . 120.2 ?
C41 C42 H42 . . 120.2 ?
C44 C43 C42 . . 120.9(2) ?
C44 C43 H43 . . 119.5 ?
C42 C43 H43 . . 119.5 ?
C43 C44 C45 . . 120.0(2) ?
C43 C44 H44 . . 120.0 ?
C45 C44 H44 . . 120.0 ?
C46 C45 C44 . . 120.1(2) ?
C46 C45 H45 . . 119.9 ?
C44 C45 H45 . . 119.9 ?
C45 C46 C41 . . 119.9(2) ?
C45 C46 H46 . . 120.1 ?
C41 C46 H46 . . 120.1 ?
C52 C51 C56 . . 112.96(19) ?
C52 C51 B1 . . 126.93(19) ?
C56 C51 B1 . . 120.08(19) ?
F52 C52 C51 . . 120.68(19) ?
F52 C52 C53 . . 114.9(2) ?
C51 C52 C53 . . 124.5(2) ?
F53 C53 C54 . . 120.2(2) ?
F53 C53 C52 . . 120.2(2) ?
C54 C53 C52 . . 119.6(2) ?
F54 C54 C55 . . 119.9(2) ?
F54 C54 C53 . . 121.2(2) ?
C55 C54 C53 . . 118.9(2) ?
F55 C55 C54 . . 119.9(2) ?
F55 C55 C56 . . 120.5(2) ?
C54 C55 C56 . . 119.5(2) ?
F56 C56 C55 . . 115.30(19) ?
F56 C56 C51 . . 120.17(19) ?
C55 C56 C51 . . 124.5(2) ?
C66 C61 C62 . . 113.0(2) ?
C66 C61 B1 . . 127.32(19) ?
C62 C61 B1 . . 119.56(19) ?
F62 C62 C63 . . 115.50(19) ?
F62 C62 C61 . . 120.10(19) ?
C63 C62 C61 . . 124.4(2) ?
F63 C63 C64 . . 119.8(2) ?
F63 C63 C62 . . 120.8(2) ?
C64 C63 C62 . . 119.4(2) ?
F64 C64 C65 . . 120.6(2) ?
F64 C64 C63 . . 120.1(2) ?
C65 C64 C63 . . 119.2(2) ?
F65 C65 C64 . . 120.1(2) ?
F65 C65 C66 . . 120.7(2) ?
C64 C65 C66 . . 119.2(2) ?
F66 C66 C65 . . 114.53(19) ?
F66 C66 C61 . . 120.89(19) ?
C65 C66 C61 . . 124.6(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
C5 B1 C1 C2 . . . . 55.1(2) ?
C51 B1 C1 C2 . . . . 177.69(17) ?
C61 B1 C1 C2 . . . . -62.5(2) ?
B1 C1 C2 C3 . . . . -42.9(3) ?
B1 C1 C2 P1 . . . . -167.97(15) ?
C21 P1 C2 C1 . . . . 86.99(17) ?
C31 P1 C2 C1 . . . . -149.48(15) ?
C41 P1 C2 C1 . . . . -32.72(18) ?
C21 P1 C2 C3 . . . . -42.19(17) ?
C31 P1 C2 C3 . . . . 81.33(16) ?
C41 P1 C2 C3 . . . . -161.91(14) ?
C1 C2 C3 C4 . . . . 37.0(3) ?
P1 C2 C3 C4 . . . . 161.79(14) ?
C1 C2 C3 C8 . . . . 164.51(18) ?
P1 C2 C3 C8 . . . . -70.65(19) ?
C8 C3 C4 C6 . . . . 5.6(3) ?
C2 C3 C4 C6 . . . . 129.3(2) ?
C8 C3 C4 C5 . . . . -173.69(18) ?
C2 C3 C4 C5 . . . . -49.9(2) ?
C6 C4 C5 B1 . . . . -111.9(2) ?
C3 C4 C5 B1 . . . . 67.3(2) ?
C1 B1 C5 C4 . . . . -66.2(2) ?
C51 B1 C5 C4 . . . . 176.92(17) ?
C61 B1 C5 C4 . . . . 56.5(2) ?
C5 C4 C6 C7 . . . . 179.0(2) ?
C3 C4 C6 C7 . . . . -0.2(4) ?
C4 C6 C7 C16 . . . . 48.1(4) ?
C4 C3 C8 C11 . . . . -60.7(3) ?
C2 C3 C8 C11 . . . . 173.34(18) ?
C3 C8 C11 C12 . . . . -111.1(2) ?
C3 C8 C11 C16 . . . . 72.6(3) ?
C16 C11 C12 C13 . . . . -1.1(3) ?
C8 C11 C12 C13 . . . . -177.4(2) ?
C11 C12 C13 C14 . . . . -0.5(3) ?
C12 C13 C14 C15 . . . . 1.1(3) ?
C13 C14 C15 C16 . . . . 0.0(4) ?
C14 C15 C16 C11 . . . . -1.6(3) ?
C14 C15 C16 C7 . . . . 177.9(2) ?
C12 C11 C16 C15 . . . . 2.2(3) ?
C8 C11 C16 C15 . . . . 178.5(2) ?
C12 C11 C16 C7 . . . . -177.4(2) ?
C8 C11 C16 C7 . . . . -1.0(3) ?
C6 C7 C16 C15 . . . . 120.5(2) ?
C6 C7 C16 C11 . . . . -59.9(3) ?
C31 P1 C21 C26 . . . . -24.6(2) ?
C41 P1 C21 C26 . . . . -138.28(19) ?
C2 P1 C21 C26 . . . . 98.9(2) ?
C31 P1 C21 C22 . . . . 163.02(17) ?
C41 P1 C21 C22 . . . . 49.3(2) ?
C2 P1 C21 C22 . . . . -73.5(2) ?
C26 C21 C22 C23 . . . . 1.2(3) ?
P1 C21 C22 C23 . . . . 173.88(19) ?
C21 C22 C23 C24 . . . . 1.2(4) ?
C22 C23 C24 C25 . . . . -1.8(4) ?
C23 C24 C25 C26 . . . . 0.0(4) ?
C22 C21 C26 C25 . . . . -2.9(3) ?
P1 C21 C26 C25 . . . . -175.22(18) ?
C24 C25 C26 C21 . . . . 2.3(4) ?
C21 P1 C31 C32 . . . . -25.0(2) ?
C41 P1 C31 C32 . . . . 91.6(2) ?
C2 P1 C31 C32 . . . . -145.89(18) ?
C21 P1 C31 C36 . . . . 157.18(17) ?
C41 P1 C31 C36 . . . . -86.22(19) ?
C2 P1 C31 C36 . . . . 36.3(2) ?
C36 C31 C32 C33 . . . . -3.7(3) ?
P1 C31 C32 C33 . . . . 178.52(17) ?
C31 C32 C33 C34 . . . . 1.6(3) ?
C32 C33 C34 C35 . . . . 2.1(4) ?
C33 C34 C35 C36 . . . . -3.8(4) ?
C34 C35 C36 C31 . . . . 1.7(3) ?
C32 C31 C36 C35 . . . . 2.0(3) ?
P1 C31 C36 C35 . . . . 179.90(17) ?
C21 P1 C41 C46 . . . . -168.76(18) ?
C31 P1 C41 C46 . . . . 72.1(2) ?
C2 P1 C41 C46 . . . . -49.6(2) ?
C21 P1 C41 C42 . . . . 18.7(2) ?
C31 P1 C41 C42 . . . . -100.4(2) ?
C2 P1 C41 C42 . . . . 137.94(18) ?
C46 C41 C42 C43 . . . . 0.9(3) ?
P1 C41 C42 C43 . . . . 173.39(19) ?
C41 C42 C43 C44 . . . . -0.7(4) ?
C42 C43 C44 C45 . . . . -0.1(4) ?
C43 C44 C45 C46 . . . . 0.8(4) ?
C44 C45 C46 C41 . . . . -0.7(4) ?
C42 C41 C46 C45 . . . . -0.2(3) ?
P1 C41 C46 C45 . . . . -172.78(19) ?
C1 B1 C51 C52 . . . . -107.2(2) ?
C5 B1 C51 C52 . . . . 7.5(3) ?
C61 B1 C51 C52 . . . . 128.0(2) ?
C1 B1 C51 C56 . . . . 70.7(2) ?
C5 B1 C51 C56 . . . . -174.62(19) ?
C61 B1 C51 C56 . . . . -54.1(2) ?
C56 C51 C52 F52 . . . . 178.88(19) ?
B1 C51 C52 F52 . . . . -3.1(3) ?
C56 C51 C52 C53 . . . . -0.4(3) ?
B1 C51 C52 C53 . . . . 177.6(2) ?
F52 C52 C53 F53 . . . . 1.8(3) ?
C51 C52 C53 F53 . . . . -178.8(2) ?
F52 C52 C53 C54 . . . . -176.7(2) ?
C51 C52 C53 C54 . . . . 2.6(4) ?
F53 C53 C54 F54 . . . . -2.0(3) ?
C52 C53 C54 F54 . . . . 176.5(2) ?
F53 C53 C54 C55 . . . . 179.0(2) ?
C52 C53 C54 C55 . . . . -2.5(3) ?
F54 C54 C55 F55 . . . . 1.3(3) ?
C53 C54 C55 F55 . . . . -179.7(2) ?
F54 C54 C55 C56 . . . . -178.7(2) ?
C53 C54 C55 C56 . . . . 0.3(3) ?
F55 C55 C56 F56 . . . . 2.2(3) ?
C54 C55 C56 F56 . . . . -177.78(19) ?
F55 C55 C56 C51 . . . . -177.9(2) ?
C54 C55 C56 C51 . . . . 2.1(3) ?
C52 C51 C56 F56 . . . . 177.88(19) ?
B1 C51 C56 F56 . . . . -0.3(3) ?
C52 C51 C56 C55 . . . . -2.0(3) ?
B1 C51 C56 C55 . . . . 179.8(2) ?
C1 B1 C61 C66 . . . . -8.0(3) ?
C5 B1 C61 C66 . . . . -123.0(2) ?
C51 B1 C61 C66 . . . . 111.7(2) ?
C1 B1 C61 C62 . . . . 167.26(19) ?
C5 B1 C61 C62 . . . . 52.2(2) ?
C51 B1 C61 C62 . . . . -73.1(2) ?
C66 C61 C62 F62 . . . . -175.04(18) ?
B1 C61 C62 F62 . . . . 9.1(3) ?
C66 C61 C62 C63 . . . . 4.8(3) ?
B1 C61 C62 C63 . . . . -171.1(2) ?
F62 C62 C63 F63 . . . . -2.1(3) ?
C61 C62 C63 F63 . . . . 178.1(2) ?
F62 C62 C63 C64 . . . . 177.71(19) ?
C61 C62 C63 C64 . . . . -2.1(3) ?
F63 C63 C64 F64 . . . . -0.2(3) ?
C62 C63 C64 F64 . . . . 180.0(2) ?
F63 C63 C64 C65 . . . . 178.0(2) ?
C62 C63 C64 C65 . . . . -1.7(3) ?
F64 C64 C65 F65 . . . . 1.8(3) ?
C63 C64 C65 F65 . . . . -176.5(2) ?
F64 C64 C65 C66 . . . . -179.3(2) ?
C63 C64 C65 C66 . . . . 2.4(3) ?
F65 C65 C66 F66 . . . . 0.0(3) ?
C64 C65 C66 F66 . . . . -178.82(19) ?
F65 C65 C66 C61 . . . . 179.5(2) ?
C64 C65 C66 C61 . . . . 0.7(3) ?
C62 C61 C66 F66 . . . . 175.41(18) ?
B1 C61 C66 F66 . . . . -9.1(3) ?
C62 C61 C66 C65 . . . . -4.0(3) ?
B1 C61 C66 C65 . . . . 171.4(2) ?

####################################################################### 
# 
# 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_erk9368
_database_code_depnum_ccdc_archive 'CCDC 1922907'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 B F10 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         559.25
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7240(3)
_cell_length_b                   14.9525(4)
_cell_length_c                   16.4897(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2397.57(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      3.9909
_cell_measurement_theta_max      68.2871
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.087
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136

_exptl_absorpt_coefficient_mu    1.274
_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  0.80
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(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            22711
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         68.38
_diffrn_reflns_theta_full        68.38
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17

_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.

The seven membered ring was found disordered over two positions. 
Several restraints (SADI, SAME, ISOR and SIMU) were used in order
to improve refinement stability.
;

_reflns_number_total             4353
_reflns_number_gt                3722
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0946
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         4353
_refine_ls_number_parameters     380
_refine_ls_number_restraints     71
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+1.4028P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1349 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)

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'
N N 0.0311 0.0180 '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'

_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 0.6798(4) 0.3572(3) 0.6836(3) 0.0235(10) Uani d . . . 1.0 . .
C C1 0.3734(6) 0.2061(5) 0.8728(4) 0.073(2) Uani d . . . 1.0 . .
H H1A 0.3649 0.2691 0.8788 0.088 Uiso calc U . R 1.0 . .
H H1B 0.2941 0.1692 0.8761 0.088 Uiso calc U . R 1.0 . .
C C2 0.4920(6) 0.1710(4) 0.8601(3) 0.0512(15) Uani d . . . 1.0 . .
H H2 0.4959 0.1078 0.8544 0.061 Uiso calc U . R 1.0 . .
C C4 0.6946(4) 0.2028(3) 0.7717(3) 0.0263(9) Uani d . . . 1.0 . .
C C5 0.6334(4) 0.2532(3) 0.7010(3) 0.0256(9) Uani d . . . 1.0 . .
H H5A 0.5323 0.2528 0.708 0.031 Uiso calc U . R 1.0 . .
H H5B 0.6537 0.2184 0.6513 0.031 Uiso calc U . R 1.0 . .
C C6 0.7985(5) 0.1455(3) 0.7599(3) 0.0346(10) Uani d . . . 1.0 . .
H H6 0.8323 0.1431 0.7059 0.042 Uiso calc U . R 1.0 . .
C C3 0.6280(5) 0.2226(3) 0.8535(3) 0.0391(12) Uani d U . D 1.0 . .
H H3 0.6033 0.2876 0.8529 0.047 Uiso calc U . R 1.0 A 1
C C7 0.8705(6) 0.0838(4) 0.8190(4) 0.0515(14) Uani d U . D 1.0 . .
H H7A 0.9084 0.0326 0.7883 0.062 Uiso calc U P R 0.822(12) B 1
H H7B 0.9491 0.1165 0.8431 0.062 Uiso calc U P R 0.822(12) B 1
H H7C 0.8242 0.0252 0.8139 0.062 Uiso calc U P R 0.178(12) B 2
H H7D 0.9647 0.0756 0.7976 0.062 Uiso calc U P R 0.178(12) B 2
C C8 0.7841(6) 0.0482(4) 0.8862(4) 0.0381(18) Uani d U P D 0.822(12) B 1
H H8A 0.8314 -0.0043 0.9098 0.046 Uiso calc U P R 0.822(12) B 1
H H8B 0.6961 0.027 0.863 0.046 Uiso calc U P R 0.822(12) B 1
C C9 0.7522(14) 0.1131(8) 0.9540(6) 0.047(3) Uani d U P D 0.822(12) B 1
H H9A 0.8289 0.1121 0.9935 0.056 Uiso calc U P R 0.822(12) B 1
H H9B 0.6684 0.0926 0.9826 0.056 Uiso calc U P R 0.822(12) B 1
C C10 0.7301(11) 0.2094(6) 0.9255(5) 0.042(2) Uani d U P D 0.822(12) B 1
H H10A 0.8204 0.2344 0.9095 0.051 Uiso calc U P R 0.822(12) B 1
H H10B 0.6964 0.2449 0.9722 0.051 Uiso calc U P R 0.822(12) B 1
C C8A 0.886(3) 0.100(3) 0.9067(15) 0.065(12) Uani d U P D 0.178(12) B 2
H H801 0.9532 0.1489 0.914 0.078 Uiso calc U P R 0.178(12) B 2
H H802 0.9272 0.0453 0.931 0.078 Uiso calc U P R 0.178(12) B 2
C C9A 0.757(6) 0.123(4) 0.955(3) 0.048(12) Uani d U P D 0.178(12) B 2
H H901 0.7798 0.1202 1.0132 0.057 Uiso calc U P R 0.178(12) B 2
H H902 0.6869 0.0766 0.9438 0.057 Uiso calc U P R 0.178(12) B 2
C C10A 0.695(5) 0.215(3) 0.9365(19) 0.048(11) Uani d U P D 0.178(12) B 2
H H10C 0.6246 0.2282 0.9783 0.057 Uiso calc U P R 0.178(12) B 2
H H10D 0.7678 0.2606 0.9409 0.057 Uiso calc U P R 0.178(12) B 2
C C11 0.6301(4) 0.4317(3) 0.7512(3) 0.0222(9) Uani d . . . 1.0 . .
C C12 0.4934(4) 0.4308(3) 0.7785(3) 0.0242(9) Uani d . . . 1.0 . .
F F12 0.4037(2) 0.37235(16) 0.74515(17) 0.0338(6) Uani d . . . 1.0 . .
C C13 0.4407(4) 0.4865(3) 0.8370(3) 0.0291(10) Uani d . . . 1.0 . .
F F13 0.3089(3) 0.47692(18) 0.86067(17) 0.0404(7) Uani d . . . 1.0 . .
C C14 0.5222(5) 0.5502(3) 0.8716(3) 0.0306(10) Uani d . . . 1.0 . .
F F14 0.4750(3) 0.60208(17) 0.93191(15) 0.0403(7) Uani d . . . 1.0 . .
C C15 0.6538(5) 0.5596(3) 0.8433(3) 0.0284(10) Uani d . . . 1.0 . .
F F15 0.7342(3) 0.62533(16) 0.87399(17) 0.0394(7) Uani d . . . 1.0 . .
C C16 0.7047(4) 0.5023(3) 0.7848(3) 0.0255(9) Uani d . . . 1.0 . .
F F16 0.8353(2) 0.51833(15) 0.76107(17) 0.0331(6) Uani d . . . 1.0 . .
C C21 0.6239(4) 0.3962(3) 0.5963(2) 0.0210(8) Uani d . . . 1.0 . .
C C22 0.5072(4) 0.3666(3) 0.5557(3) 0.0253(9) Uani d . . . 1.0 . .
F F22 0.4354(2) 0.29489(16) 0.58219(16) 0.0313(6) Uani d . . . 1.0 . .
C C23 0.4539(4) 0.4075(3) 0.4875(3) 0.0283(10) Uani d . . . 1.0 . .
F F23 0.3376(2) 0.37473(18) 0.45367(17) 0.0391(6) Uani d . . . 1.0 . .
C C24 0.5176(4) 0.4796(3) 0.4546(3) 0.0287(10) Uani d . . . 1.0 . .
F F24 0.4684(3) 0.51983(19) 0.38793(16) 0.0432(7) Uani d . . . 1.0 . .
C C25 0.6349(4) 0.5123(3) 0.4914(3) 0.0295(10) Uani d . . . 1.0 . .
F F25 0.6996(3) 0.58324(16) 0.45919(16) 0.0390(7) Uani d . . . 1.0 . .
C C26 0.6841(4) 0.4706(3) 0.5602(3) 0.0243(9) Uani d . . . 1.0 . .
F F26 0.7979(2) 0.50760(15) 0.59344(15) 0.0330(6) Uani d . . . 1.0 . .
N N31 0.8465(3) 0.3484(2) 0.6813(2) 0.0217(7) Uani d . . . 1.0 . .
C C32 0.9174(4) 0.3436(3) 0.7517(3) 0.0257(9) Uani d . . . 1.0 . .
H H32 0.8707 0.3545 0.8013 0.031 Uiso calc U . R 1.0 . .
C C33 1.0554(4) 0.3234(3) 0.7533(3) 0.0320(11) Uani d . . . 1.0 . .
H H33 1.1039 0.3232 0.8034 0.038 Uiso calc U . R 1.0 . .
C C34 1.1229(4) 0.3036(3) 0.6822(3) 0.0327(11) Uani d . . . 1.0 . .
H H34 1.218 0.2891 0.6825 0.039 Uiso calc U . R 1.0 . .
C C35 1.0497(4) 0.3052(3) 0.6102(3) 0.0316(11) Uani d . . . 1.0 . .
H H35 1.0936 0.291 0.5604 0.038 Uiso calc U . R 1.0 . .
C C36 0.9120(4) 0.3276(3) 0.6118(3) 0.0255(9) Uani d . . . 1.0 . .
H H36 0.8618 0.3283 0.5624 0.031 Uiso calc U . R 1.0 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N31 . 1.627(5) ?
B1 C5 . 1.645(6) ?
B1 C21 . 1.646(6) ?
B1 C11 . 1.647(6) ?
C1 C2 . 1.285(8) ?
C1 H1A . 0.95 ?
C1 H1B . 0.95 ?
C2 C3 . 1.535(7) ?
C2 H2 . 0.95 ?
C4 C6 . 1.340(6) ?
C4 C5 . 1.511(6) ?
C4 C3 . 1.524(6) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.514(7) ?
C6 H6 . 0.95 ?
C3 C10A . 1.52(2) ?
C3 C10 . 1.561(8) ?
C3 H3 . 1.0 ?
C7 C8A . 1.47(2) ?
C7 C8 . 1.489(8) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C7 H7C . 0.99 ?
C7 H7D . 0.99 ?
C8 C9 . 1.512(12) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.531(9) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C8A C9A . 1.52(2) ?
C8A H801 . 0.99 ?
C8A H802 . 0.99 ?
C9A C10A . 1.53(2) ?
C9A H901 . 0.99 ?
C9A H902 . 0.99 ?
C10A H10C . 0.99 ?
C10A H10D . 0.99 ?
C11 C16 . 1.395(6) ?
C11 C12 . 1.404(5) ?
C12 F12 . 1.351(5) ?
C12 C13 . 1.374(6) ?
C13 F13 . 1.347(5) ?
C13 C14 . 1.364(6) ?
C14 F14 . 1.342(5) ?
C14 C15 . 1.370(6) ?
C15 F15 . 1.353(5) ?
C15 C16 . 1.383(6) ?
C16 F16 . 1.350(4) ?
C21 C22 . 1.390(6) ?
C21 C26 . 1.391(5) ?
C22 F22 . 1.352(5) ?
C22 C23 . 1.381(6) ?
C23 F23 . 1.353(5) ?
C23 C24 . 1.356(6) ?
C24 F24 . 1.342(5) ?
C24 C25 . 1.381(6) ?
C25 F25 . 1.343(5) ?
C25 C26 . 1.380(6) ?
C26 F26 . 1.353(5) ?
N31 C36 . 1.348(5) ?
N31 C32 . 1.352(5) ?
C32 C33 . 1.376(5) ?
C32 H32 . 0.95 ?
C33 C34 . 1.376(7) ?
C33 H33 . 0.95 ?
C34 C35 . 1.384(7) ?
C34 H34 . 0.95 ?
C35 C36 . 1.381(6) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

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
N31 B1 C5 . . 101.6(3) ?
N31 B1 C21 . . 109.7(3) ?
C5 B1 C21 . . 113.4(3) ?
N31 B1 C11 . . 111.3(3) ?
C5 B1 C11 . . 116.2(3) ?
C21 B1 C11 . . 104.8(3) ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C3 . . 125.4(6) ?
C1 C2 H2 . . 117.3 ?
C3 C2 H2 . . 117.3 ?
C6 C4 C5 . . 120.2(4) ?
C6 C4 C3 . . 125.0(4) ?
C5 C4 C3 . . 114.8(4) ?
C4 C5 B1 . . 119.9(3) ?
C4 C5 H5A . . 107.4 ?
B1 C5 H5A . . 107.4 ?
C4 C5 H5B . . 107.4 ?
B1 C5 H5B . . 107.4 ?
H5A C5 H5B . . 106.9 ?
C4 C6 C7 . . 130.1(5) ?
C4 C6 H6 . . 114.9 ?
C7 C6 H6 . . 114.9 ?
C10A C3 C4 . . 126.9(17) ?
C10A C3 C2 . . 105.(2) ?
C4 C3 C2 . . 109.3(4) ?
C4 C3 C10 . . 112.2(5) ?
C2 C3 C10 . . 115.4(5) ?
C4 C3 H3 . . 106.4 ?
C2 C3 H3 . . 106.4 ?
C10 C3 H3 . . 106.4 ?
C8A C7 C6 . . 125.7(14) ?
C8 C7 C6 . . 115.9(4) ?
C8 C7 H7A . . 108.3 ?
C6 C7 H7A . . 108.3 ?
C8 C7 H7B . . 108.3 ?
C6 C7 H7B . . 108.3 ?
H7A C7 H7B . . 107.4 ?
C8A C7 H7C . . 105.9 ?
C6 C7 H7C . . 105.9 ?
C8A C7 H7D . . 105.9 ?
C6 C7 H7D . . 105.9 ?
H7C C7 H7D . . 106.2 ?
C7 C8 C9 . . 115.9(6) ?
C7 C8 H8A . . 108.3 ?
C9 C8 H8A . . 108.3 ?
C7 C8 H8B . . 108.3 ?
C9 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
C8 C9 C10 . . 113.9(7) ?
C8 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
C8 C9 H9B . . 108.8 ?
C10 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
C9 C10 C3 . . 116.2(8) ?
C9 C10 H10A . . 108.2 ?
C3 C10 H10A . . 108.2 ?
C9 C10 H10B . . 108.2 ?
C3 C10 H10B . . 108.2 ?
H10A C10 H10B . . 107.4 ?
C7 C8A C9A . . 117.(3) ?
C7 C8A H801 . . 107.9 ?
C9A C8A H801 . . 107.9 ?
C7 C8A H802 . . 107.9 ?
C9A C8A H802 . . 107.9 ?
H801 C8A H802 . . 107.2 ?
C8A C9A C10A . . 116.(3) ?
C8A C9A H901 . . 108.4 ?
C10A C9A H901 . . 108.4 ?
C8A C9A H902 . . 108.4 ?
C10A C9A H902 . . 108.4 ?
H901 C9A H902 . . 107.5 ?
C3 C10A C9A . . 115.(3) ?
C3 C10A H10C . . 108.6 ?
C9A C10A H10C . . 108.6 ?
C3 C10A H10D . . 108.6 ?
C9A C10A H10D . . 108.6 ?
H10C C10A H10D . . 107.6 ?
C16 C11 C12 . . 111.9(4) ?
C16 C11 B1 . . 128.8(3) ?
C12 C11 B1 . . 119.2(3) ?
F12 C12 C13 . . 115.9(4) ?
F12 C12 C11 . . 119.1(4) ?
C13 C12 C11 . . 124.9(4) ?
F13 C13 C14 . . 120.4(4) ?
F13 C13 C12 . . 119.6(4) ?
C14 C13 C12 . . 120.0(4) ?
F14 C14 C13 . . 121.0(4) ?
F14 C14 C15 . . 120.8(4) ?
C13 C14 C15 . . 118.2(4) ?
F15 C15 C14 . . 119.2(4) ?
F15 C15 C16 . . 120.3(4) ?
C14 C15 C16 . . 120.5(4) ?
F16 C16 C15 . . 115.4(4) ?
F16 C16 C11 . . 120.6(4) ?
C15 C16 C11 . . 124.1(4) ?
C22 C21 C26 . . 113.1(4) ?
C22 C21 B1 . . 125.3(4) ?
C26 C21 B1 . . 121.3(3) ?
F22 C22 C23 . . 114.8(4) ?
F22 C22 C21 . . 121.3(4) ?
C23 C22 C21 . . 123.9(4) ?
F23 C23 C24 . . 120.3(4) ?
F23 C23 C22 . . 119.3(4) ?
C24 C23 C22 . . 120.4(4) ?
F24 C24 C23 . . 121.4(4) ?
F24 C24 C25 . . 119.7(4) ?
C23 C24 C25 . . 118.9(4) ?
F25 C25 C26 . . 121.3(4) ?
F25 C25 C24 . . 119.5(4) ?
C26 C25 C24 . . 119.2(4) ?
F26 C26 C25 . . 115.6(4) ?
F26 C26 C21 . . 119.8(4) ?
C25 C26 C21 . . 124.6(4) ?
C36 N31 C32 . . 118.4(3) ?
C36 N31 B1 . . 120.6(3) ?
C32 N31 B1 . . 119.5(3) ?
N31 C32 C33 . . 121.8(4) ?
N31 C32 H32 . . 119.1 ?
C33 C32 H32 . . 119.1 ?
C32 C33 C34 . . 119.7(4) ?
C32 C33 H33 . . 120.2 ?
C34 C33 H33 . . 120.2 ?
C33 C34 C35 . . 118.8(4) ?
C33 C34 H34 . . 120.6 ?
C35 C34 H34 . . 120.6 ?
C36 C35 C34 . . 119.1(4) ?
C36 C35 H35 . . 120.4 ?
C34 C35 H35 . . 120.4 ?
N31 C36 C35 . . 122.0(4) ?
N31 C36 H36 . . 119.0 ?
C35 C36 H36 . . 119.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C4 C5 B1 . . . . -99.4(5) ?
C3 C4 C5 B1 . . . . 81.1(5) ?
N31 B1 C5 C4 . . . . 52.7(5) ?
C21 B1 C5 C4 . . . . 170.3(3) ?
C11 B1 C5 C4 . . . . -68.2(5) ?
C5 C4 C6 C7 . . . . -175.9(5) ?
C3 C4 C6 C7 . . . . 3.6(8) ?
C6 C4 C3 C10A . . . . 27.(3) ?
C5 C4 C3 C10A . . . . -154.(2) ?
C6 C4 C3 C2 . . . . -101.0(5) ?
C5 C4 C3 C2 . . . . 78.4(5) ?
C6 C4 C3 C10 . . . . 28.4(7) ?
C5 C4 C3 C10 . . . . -152.1(5) ?
C1 C2 C3 C10A . . . . 98.5(16) ?
C1 C2 C3 C4 . . . . -122.4(7) ?
C1 C2 C3 C10 . . . . 109.9(7) ?
C4 C6 C7 C8A . . . . -29.(2) ?
C4 C6 C7 C8 . . . . 31.5(8) ?
C6 C7 C8 C9 . . . . -75.7(8) ?
C7 C8 C9 C10 . . . . 36.3(13) ?
C8 C9 C10 C3 . . . . 49.7(13) ?
C4 C3 C10 C9 . . . . -80.4(9) ?
C2 C3 C10 C9 . . . . 45.8(9) ?
C6 C7 C8A C9A . . . . 51.(4) ?
C7 C8A C9A C10A . . . . -69.(6) ?
C4 C3 C10A C9A . . . . -55.(4) ?
C2 C3 C10A C9A . . . . 75.(4) ?
C8A C9A C10A C3 . . . . 70.(6) ?
N31 B1 C11 C16 . . . . 21.6(6) ?
C5 B1 C11 C16 . . . . 137.1(4) ?
C21 B1 C11 C16 . . . . -96.9(5) ?
N31 B1 C11 C12 . . . . -162.0(4) ?
C5 B1 C11 C12 . . . . -46.4(5) ?
C21 B1 C11 C12 . . . . 79.5(4) ?
C16 C11 C12 F12 . . . . 173.1(4) ?
B1 C11 C12 F12 . . . . -4.0(6) ?
C16 C11 C12 C13 . . . . -5.9(6) ?
B1 C11 C12 C13 . . . . 177.1(4) ?
F12 C12 C13 F13 . . . . 3.7(6) ?
C11 C12 C13 F13 . . . . -177.3(4) ?
F12 C12 C13 C14 . . . . -177.2(4) ?
C11 C12 C13 C14 . . . . 1.7(7) ?
F13 C13 C14 F14 . . . . 2.7(6) ?
C12 C13 C14 F14 . . . . -176.3(4) ?
F13 C13 C14 C15 . . . . -177.5(4) ?
C12 C13 C14 C15 . . . . 3.5(6) ?
F14 C14 C15 F15 . . . . -3.5(6) ?
C13 C14 C15 F15 . . . . 176.7(4) ?
F14 C14 C15 C16 . . . . 175.9(4) ?
C13 C14 C15 C16 . . . . -4.0(6) ?
F15 C15 C16 F16 . . . . -1.2(6) ?
C14 C15 C16 F16 . . . . 179.5(4) ?
F15 C15 C16 C11 . . . . 178.6(4) ?
C14 C15 C16 C11 . . . . -0.7(6) ?
C12 C11 C16 F16 . . . . -174.9(4) ?
B1 C11 C16 F16 . . . . 1.8(6) ?
C12 C11 C16 C15 . . . . 5.3(6) ?
B1 C11 C16 C15 . . . . -178.0(4) ?
N31 B1 C21 C22 . . . . 139.1(4) ?
C5 B1 C21 C22 . . . . 26.4(6) ?
C11 B1 C21 C22 . . . . -101.3(4) ?
N31 B1 C21 C26 . . . . -47.9(5) ?
C5 B1 C21 C26 . . . . -160.7(4) ?
C11 B1 C21 C26 . . . . 71.7(4) ?
C26 C21 C22 F22 . . . . 180.0(3) ?
B1 C21 C22 F22 . . . . -6.6(6) ?
C26 C21 C22 C23 . . . . -1.4(6) ?
B1 C21 C22 C23 . . . . 172.1(4) ?
F22 C22 C23 F23 . . . . 0.5(5) ?
C21 C22 C23 F23 . . . . -178.2(4) ?
F22 C22 C23 C24 . . . . -179.4(4) ?
C21 C22 C23 C24 . . . . 1.9(7) ?
F23 C23 C24 F24 . . . . -0.5(6) ?
C22 C23 C24 F24 . . . . 179.3(4) ?
F23 C23 C24 C25 . . . . 178.9(4) ?
C22 C23 C24 C25 . . . . -1.2(6) ?
F24 C24 C25 F25 . . . . -1.0(6) ?
C23 C24 C25 F25 . . . . 179.5(4) ?
F24 C24 C25 C26 . . . . 179.7(4) ?
C23 C24 C25 C26 . . . . 0.2(6) ?
F25 C25 C26 F26 . . . . 1.9(6) ?
C24 C25 C26 F26 . . . . -178.8(4) ?
F25 C25 C26 C21 . . . . -179.1(4) ?
C24 C25 C26 C21 . . . . 0.3(6) ?
C22 C21 C26 F26 . . . . 179.4(3) ?
B1 C21 C26 F26 . . . . 5.6(6) ?
C22 C21 C26 C25 . . . . 0.3(6) ?
B1 C21 C26 C25 . . . . -173.4(4) ?
C5 B1 N31 C36 . . . . 87.0(4) ?
C21 B1 N31 C36 . . . . -33.2(5) ?
C11 B1 N31 C36 . . . . -148.7(4) ?
C5 B1 N31 C32 . . . . -79.3(4) ?
C21 B1 N31 C32 . . . . 160.5(3) ?
C11 B1 N31 C32 . . . . 45.0(5) ?
C36 N31 C32 C33 . . . . 4.0(6) ?
B1 N31 C32 C33 . . . . 170.6(4) ?
N31 C32 C33 C34 . . . . -2.9(6) ?
C32 C33 C34 C35 . . . . 0.5(6) ?
C33 C34 C35 C36 . . . . 0.8(7) ?
C32 N31 C36 C35 . . . . -2.7(6) ?
B1 N31 C36 C35 . . . . -169.1(4) ?
C34 C35 C36 N31 . . . . 0.3(6) ?

####################################################################### 
# 
# 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_erk9502
_database_code_depnum_ccdc_archive 'CCDC 1922913'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H38 B Cl2 F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         893.44

_chemical_melting_point          ?

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

_cell_length_a                   11.6050(3)
_cell_length_b                   20.1373(4)
_cell_length_c                   17.8823(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.818(2)
_cell_angle_gamma                90
_cell_volume                     4074.83(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6466
_cell_measurement_theta_min      3.3528
_cell_measurement_theta_max      65.9582
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1832

_exptl_absorpt_coefficient_mu    2.507
_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  0.71
_exptl_absorpt_correction_T_max  0.86

_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            46629
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_theta_min         3.91
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_full        66.67
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21

_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.

One dichloromethane molecule and one CH=CH2 group are 
disordered over two positions. Several restraints (SADI,
SAME, ISOR and SIMU) were used in order to improve refinement
stability.
;

_reflns_number_total             7186
_reflns_number_gt                5465
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1472
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         7186
_refine_ls_number_parameters     588
_refine_ls_number_restraints     88
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0968P)²+0.0115P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.395
_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'
Cl Cl 0.3639 0.7018 '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
P P1 0.31171(5) 0.34845(3) 0.78863(4) 0.02480(17) Uani d . . . 1.0 . .
B B1 0.3098(2) 0.56760(13) 0.75910(17) 0.0255(6) Uani d . . . 1.0 . .
C C3 0.2893(2) 0.55540(13) 0.54010(15) 0.0307(6) Uani d . . D 1.0 . .
H H3 0.3753 0.5663 0.5565 0.037 Uiso calc U P R 0.849(13) A 1
H H3A 0.3759 0.5647 0.5554 0.037 Uiso calc U P R 0.151(13) A 2
C C2 0.2782(10) 0.4936(6) 0.4902(8) 0.036(2) Uani d U P D 0.849(13) A 1
H H2 0.2029 0.4856 0.4577 0.043 Uiso calc U P R 0.849(13) A 1
C C1 0.3604(4) 0.4504(2) 0.4871(3) 0.0489(15) Uani d U P D 0.849(13) A 1
H H1A 0.4374 0.4558 0.5184 0.059 Uiso calc U P R 0.849(13) A 1
H H1B 0.3433 0.4133 0.4535 0.059 Uiso calc U P R 0.849(13) A 1
C C2A 0.270(5) 0.497(4) 0.485(5) 0.037(10) Uani d U P D 0.151(13) A 2
H H2A 0.2018 0.4702 0.4817 0.045 Uiso calc U P R 0.151(13) A 2
C C1A 0.344(2) 0.4832(17) 0.4422(18) 0.065(9) Uani d U P D 0.151(13) A 2
H H1C 0.4124 0.5098 0.445 0.078 Uiso calc U P R 0.151(13) A 2
H H1D 0.3296 0.4464 0.4082 0.078 Uiso calc U P R 0.151(13) A 2
C C4 0.2418(2) 0.54509(12) 0.61372(15) 0.0269(5) Uani d . . . 1.0 . .
C C5 0.2740(2) 0.60229(12) 0.67301(15) 0.0273(5) Uani d . . . 1.0 . .
H H5A 0.2058 0.6325 0.6697 0.033 Uiso calc U . R 1.0 . .
H H5B 0.3414 0.6282 0.6629 0.033 Uiso calc U . R 1.0 . .
C C6 0.1050(2) 0.53746(12) 0.59324(15) 0.0276(5) Uani d . . . 1.0 . .
H H6 0.0866 0.4959 0.5623 0.033 Uiso calc U . R 1.0 . .
C C7 0.0442(2) 0.59479(13) 0.54335(15) 0.0311(6) Uani d . . . 1.0 . .
H H7A -0.0413 0.5851 0.527 0.037 Uiso calc U . R 1.0 . .
H H7B 0.0533 0.6359 0.5745 0.037 Uiso calc U . R 1.0 . .
C C8 0.0941(2) 0.60649(14) 0.47242(16) 0.0351(6) Uani d . . . 1.0 . .
H H8A 0.0741 0.5683 0.4371 0.042 Uiso calc U . R 1.0 . .
H H8B 0.0576 0.6468 0.4453 0.042 Uiso calc U . R 1.0 . .
C C9 0.2278(2) 0.61509(13) 0.49436(16) 0.0343(6) Uani d . . . 1.0 . .
H H9A 0.247 0.6559 0.5255 0.041 Uiso calc U . R 1.0 . .
H H9B 0.2582 0.6206 0.4472 0.041 Uiso calc U . R 1.0 . .
C C10 0.0616(2) 0.52739(12) 0.66633(15) 0.0268(5) Uani d . . . 1.0 . .
C C11 0.1311(2) 0.47739(12) 0.72180(15) 0.0272(5) Uani d . . . 1.0 . .
H H11A 0.1123 0.4321 0.7011 0.033 Uiso calc U . R 1.0 . .
H H11B 0.1063 0.4804 0.7712 0.033 Uiso calc U . R 1.0 . .
C C12 0.2662(2) 0.48845(12) 0.73626(15) 0.0258(5) Uani d . . . 1.0 . .
C C13 0.2973(2) 0.48344(12) 0.65730(15) 0.0274(5) Uani d . . . 1.0 . .
H H13A 0.3841 0.4833 0.6625 0.033 Uiso calc U . R 1.0 . .
H H13B 0.264 0.4424 0.6304 0.033 Uiso calc U . R 1.0 . .
C C14 -0.0293(2) 0.55909(12) 0.68348(16) 0.0312(6) Uani d . . . 1.0 . .
H H14A -0.051 0.5505 0.7307 0.037 Uiso calc U . R 1.0 . .
H H14B -0.0727 0.5904 0.6485 0.037 Uiso calc U . R 1.0 . .
C C15 0.3356(2) 0.43797(11) 0.79375(14) 0.0249(5) Uani d . . . 1.0 . .
H H15A 0.3253 0.4519 0.845 0.03 Uiso calc U . R 1.0 . .
H H15B 0.42 0.4449 0.7938 0.03 Uiso calc U . R 1.0 . .
C C21 0.2419(2) 0.60821(12) 0.81811(15) 0.0263(5) Uani d . . . 1.0 . .
C C22 0.1835(2) 0.58136(12) 0.87088(15) 0.0272(5) Uani d . . . 1.0 . .
F F22 0.18939(12) 0.51546(7) 0.88671(8) 0.0307(3) Uani d . . . 1.0 . .
C C23 0.1181(2) 0.61739(13) 0.91282(15) 0.0312(6) Uani d . . . 1.0 . .
F F23 0.06454(14) 0.58655(8) 0.96265(9) 0.0397(4) Uani d . . . 1.0 . .
C C24 0.1103(2) 0.68510(14) 0.90466(16) 0.0331(6) Uani d . . . 1.0 . .
F F24 0.04904(15) 0.72145(8) 0.94528(10) 0.0449(4) Uani d . . . 1.0 . .
C C25 0.1709(2) 0.71543(12) 0.85606(15) 0.0319(6) Uani d . . . 1.0 . .
F F25 0.16764(14) 0.78195(7) 0.84851(9) 0.0404(4) Uani d . . . 1.0 . .
C C26 0.2358(2) 0.67717(12) 0.81547(14) 0.0277(5) Uani d . . . 1.0 . .
F F26 0.29511(13) 0.71184(7) 0.77100(9) 0.0332(3) Uani d . . . 1.0 . .
C C31 0.4558(2) 0.57160(11) 0.79870(15) 0.0261(5) Uani d . . . 1.0 . .
F F32 0.42655(12) 0.54629(7) 0.92329(8) 0.0324(3) Uani d . . . 1.0 . .
C C32 0.4999(2) 0.56482(12) 0.87762(15) 0.0280(5) Uani d . . . 1.0 . .
F F33 0.64954(14) 0.56764(9) 0.99167(9) 0.0442(4) Uani d . . . 1.0 . .
C C33 0.6160(2) 0.57505(14) 0.91547(16) 0.0336(6) Uani d . . . 1.0 . .
F F34 0.81092(13) 0.60369(9) 0.90888(11) 0.0495(5) Uani d . . . 1.0 . .
C C34 0.6982(2) 0.59285(14) 0.87379(18) 0.0367(6) Uani d . . . 1.0 . .
F F35 0.74024(13) 0.61421(9) 0.75339(11) 0.0446(4) Uani d . . . 1.0 . .
C C35 0.6616(2) 0.59819(13) 0.79580(17) 0.0337(6) Uani d . . . 1.0 . .
F F36 0.52211(13) 0.59038(8) 0.68280(9) 0.0355(4) Uani d . . . 1.0 . .
C C36 0.5444(2) 0.58661(12) 0.76009(15) 0.0288(5) Uani d . . . 1.0 . .
C C41 0.1772(2) 0.32249(12) 0.81524(15) 0.0266(5) Uani d . . . 1.0 . .
C C42 0.1398(2) 0.35735(13) 0.87250(15) 0.0314(6) Uani d . . . 1.0 . .
H H42 0.1793 0.397 0.8926 0.038 Uiso calc U . R 1.0 . .
C C43 0.0449(3) 0.33434(14) 0.90032(17) 0.0374(6) Uani d . . . 1.0 . .
H H43 0.0198 0.358 0.9398 0.045 Uiso calc U . R 1.0 . .
C C44 -0.0137(2) 0.27666(14) 0.87065(17) 0.0364(6) Uani d . . . 1.0 . .
H H44 -0.0799 0.2615 0.8889 0.044 Uiso calc U . R 1.0 . .
C C45 0.0249(2) 0.24144(14) 0.81436(16) 0.0350(6) Uani d . . . 1.0 . .
H H45 -0.0144 0.2017 0.7946 0.042 Uiso calc U . R 1.0 . .
C C46 0.1203(2) 0.26380(13) 0.78659(15) 0.0302(5) Uani d . . . 1.0 . .
H H46 0.1468 0.2393 0.7482 0.036 Uiso calc U . R 1.0 . .
C C51 0.3176(2) 0.31051(12) 0.69859(15) 0.0285(5) Uani d . . . 1.0 . .
C C52 0.2182(2) 0.30933(13) 0.63769(15) 0.0308(6) Uani d . . . 1.0 . .
H H52 0.1462 0.3286 0.6438 0.037 Uiso calc U . R 1.0 . .
C C53 0.2246(2) 0.28032(13) 0.56888(16) 0.0348(6) Uani d . . . 1.0 . .
H H53 0.1572 0.2801 0.5275 0.042 Uiso calc U . R 1.0 . .
C C54 0.3294(3) 0.25143(15) 0.56019(17) 0.0406(7) Uani d . . . 1.0 . .
H H54 0.3336 0.231 0.5129 0.049 Uiso calc U . R 1.0 . .
C C55 0.4279(3) 0.25228(15) 0.62011(17) 0.0415(7) Uani d . . . 1.0 . .
H H55 0.4994 0.2324 0.6138 0.05 Uiso calc U . R 1.0 . .
C C56 0.4231(2) 0.28171(14) 0.68900(16) 0.0344(6) Uani d . . . 1.0 . .
H H56 0.4913 0.2824 0.7298 0.041 Uiso calc U . R 1.0 . .
C C61 0.4292(2) 0.31338(12) 0.86186(15) 0.0289(5) Uani d . . . 1.0 . .
C C62 0.4323(2) 0.24455(13) 0.87210(16) 0.0333(6) Uani d . . . 1.0 . .
H H62 0.377 0.2171 0.8388 0.04 Uiso calc U . R 1.0 . .
C C63 0.5156(2) 0.21654(14) 0.93071(17) 0.0370(6) Uani d . . . 1.0 . .
H H63 0.5187 0.1697 0.9372 0.044 Uiso calc U . R 1.0 . .
C C64 0.5946(3) 0.25659(15) 0.97988(17) 0.0419(7) Uani d . . . 1.0 . .
H H64 0.6514 0.2371 1.0205 0.05 Uiso calc U . R 1.0 . .
C C65 0.5919(3) 0.32401(15) 0.97079(18) 0.0440(7) Uani d . . . 1.0 . .
H H65 0.6468 0.3512 1.0048 0.053 Uiso calc U . R 1.0 . .
C C66 0.5086(2) 0.35281(14) 0.91155(18) 0.0395(7) Uani d . . . 1.0 . .
H H66 0.5064 0.3997 0.9053 0.047 Uiso calc U . R 1.0 . .
C C71 0.7803(7) 0.4260(5) 0.7311(6) 0.086(2) Uani d U P D 0.680(10) B 1
H H71C 0.801 0.4604 0.6967 0.104 Uiso calc U P R 0.680(10) B 1
H H71D 0.8245 0.3853 0.7241 0.104 Uiso calc U P R 0.680(10) B 1
Cl Cl1 0.8304(2) 0.45330(10) 0.82693(16) 0.0827(10) Uani d U P D 0.680(10) B 1
Cl Cl2 0.6304(3) 0.4092(2) 0.7015(3) 0.0963(13) Uani d U P D 0.680(10) B 1
C C71A 0.7856(14) 0.4067(10) 0.7596(8) 0.081(5) Uani d U P D 0.320(10) B 2
H H71A 0.8048 0.359 0.7569 0.097 Uiso calc U P R 0.320(10) B 2
H H71B 0.8474 0.4332 0.7429 0.097 Uiso calc U P R 0.320(10) B 2
Cl Cl1A 0.7760(13) 0.4281(7) 0.8503(5) 0.173(5) Uani d U P D 0.320(10) B 2
Cl Cl2A 0.6448(9) 0.4242(7) 0.7015(5) 0.121(3) Uani d U P D 0.320(10) B 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C51 . 1.797(3) ?
P1 C41 . 1.807(3) ?
P1 C61 . 1.811(3) ?
P1 C15 . 1.823(2) ?
B1 C5 . 1.657(4) ?
B1 C21 . 1.665(4) ?
B1 C31 . 1.687(3) ?
B1 C12 . 1.695(3) ?
C3 C2A . 1.515(18) ?
C3 C2 . 1.520(5) ?
C3 C9 . 1.538(4) ?
C3 C4 . 1.550(4) ?
C3 H3 . 1.0 ?
C3 H3A . 1.0 ?
C2 C1 . 1.301(13) ?
C2 H2 . 0.95 ?
C1 H1A . 0.95 ?
C1 H1B . 0.95 ?
C2A C1A . 1.30(2) ?
C2A H2A . 0.95 ?
C1A H1C . 0.95 ?
C1A H1D . 0.95 ?
C4 C13 . 1.530(4) ?
C4 C5 . 1.554(3) ?
C4 C6 . 1.556(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C10 . 1.515(4) ?
C6 C7 . 1.532(4) ?
C6 H6 . 1.0 ?
C7 C8 . 1.525(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.523(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C14 . 1.325(4) ?
C10 C11 . 1.514(4) ?
C11 C12 . 1.547(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.537(4) ?
C12 C15 . 1.540(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.95 ?
C14 H14B . 0.95 ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C21 C22 . 1.388(4) ?
C21 C26 . 1.391(4) ?
C22 F22 . 1.356(3) ?
C22 C23 . 1.385(4) ?
C23 F23 . 1.346(3) ?
C23 C24 . 1.372(4) ?
C24 F24 . 1.341(3) ?
C24 C25 . 1.376(4) ?
C25 F25 . 1.346(3) ?
C25 C26 . 1.389(4) ?
C26 F26 . 1.355(3) ?
C31 C36 . 1.393(4) ?
C31 C32 . 1.397(4) ?
F32 C32 . 1.356(3) ?
C32 C33 . 1.383(4) ?
F33 C33 . 1.340(3) ?
C33 C34 . 1.382(4) ?
F34 C34 . 1.337(3) ?
C34 C35 . 1.369(4) ?
F35 C35 . 1.349(3) ?
C35 C36 . 1.388(4) ?
F36 C36 . 1.351(3) ?
C41 C42 . 1.388(4) ?
C41 C46 . 1.395(4) ?
C42 C43 . 1.385(4) ?
C42 H42 . 0.95 ?
C43 C44 . 1.390(4) ?
C43 H43 . 0.95 ?
C44 C45 . 1.384(4) ?
C44 H44 . 0.95 ?
C45 C46 . 1.385(4) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C51 C56 . 1.399(4) ?
C51 C52 . 1.400(4) ?
C52 C53 . 1.379(4) ?
C52 H52 . 0.95 ?
C53 C54 . 1.388(4) ?
C53 H53 . 0.95 ?
C54 C55 . 1.382(4) ?
C54 H54 . 0.95 ?
C55 C56 . 1.379(4) ?
C55 H55 . 0.95 ?
C56 H56 . 0.95 ?
C61 C66 . 1.380(4) ?
C61 C62 . 1.398(4) ?
C62 C63 . 1.379(4) ?
C62 H62 . 0.95 ?
C63 C64 . 1.380(4) ?
C63 H63 . 0.95 ?
C64 C65 . 1.367(4) ?
C64 H64 . 0.95 ?
C65 C66 . 1.393(4) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
C71 Cl2 . 1.736(7) ?
C71 Cl1 . 1.770(8) ?
C71 H71C . 0.99 ?
C71 H71D . 0.99 ?
C71A Cl1A . 1.707(13) ?
C71A Cl2A . 1.766(13) ?
C71A H71A . 0.99 ?
C71A H71B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C51 P1 C41 . . 108.66(12) ?
C51 P1 C61 . . 108.04(12) ?
C41 P1 C61 . . 104.64(12) ?
C51 P1 C15 . . 115.45(11) ?
C41 P1 C15 . . 113.78(11) ?
C61 P1 C15 . . 105.52(12) ?
C5 B1 C21 . . 108.98(19) ?
C5 B1 C31 . . 113.0(2) ?
C21 B1 C31 . . 106.45(19) ?
C5 B1 C12 . . 99.94(19) ?
C21 B1 C12 . . 117.2(2) ?
C31 B1 C12 . . 111.39(19) ?
C2A C3 C9 . . 106.(4) ?
C2 C3 C9 . . 111.1(8) ?
C2A C3 C4 . . 115.(3) ?
C2 C3 C4 . . 112.9(5) ?
C9 C3 C4 . . 110.2(2) ?
C2 C3 H3 . . 107.5 ?
C9 C3 H3 . . 107.5 ?
C4 C3 H3 . . 107.5 ?
C2A C3 H3A . . 108.6 ?
C9 C3 H3A . . 108.6 ?
C4 C3 H3A . . 108.6 ?
C1 C2 C3 . . 127.3(9) ?
C1 C2 H2 . . 116.3 ?
C3 C2 H2 . . 116.3 ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1A C2A C3 . . 122.(3) ?
C1A C2A H2A . . 119.1 ?
C3 C2A H2A . . 119.1 ?
C2A C1A H1C . . 120.0 ?
C2A C1A H1D . . 120.0 ?
H1C C1A H1D . . 120.0 ?
C13 C4 C3 . . 110.6(2) ?
C13 C4 C5 . . 104.10(19) ?
C3 C4 C5 . . 113.8(2) ?
C13 C4 C6 . . 109.4(2) ?
C3 C4 C6 . . 110.5(2) ?
C5 C4 C6 . . 108.20(19) ?
C4 C5 B1 . . 107.10(19) ?
C4 C5 H5A . . 110.3 ?
B1 C5 H5A . . 110.3 ?
C4 C5 H5B . . 110.3 ?
B1 C5 H5B . . 110.3 ?
H5A C5 H5B . . 108.5 ?
C10 C6 C7 . . 113.9(2) ?
C10 C6 C4 . . 109.1(2) ?
C7 C6 C4 . . 112.1(2) ?
C10 C6 H6 . . 107.1 ?
C7 C6 H6 . . 107.1 ?
C4 C6 H6 . . 107.1 ?
C8 C7 C6 . . 113.0(2) ?
C8 C7 H7A . . 109.0 ?
C6 C7 H7A . . 109.0 ?
C8 C7 H7B . . 109.0 ?
C6 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 110.8(2) ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C8 C9 C3 . . 112.0(2) ?
C8 C9 H9A . . 109.2 ?
C3 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C3 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C14 C10 C11 . . 120.3(2) ?
C14 C10 C6 . . 124.7(2) ?
C11 C10 C6 . . 115.0(2) ?
C10 C11 C12 . . 112.7(2) ?
C10 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
C10 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C13 C12 C15 . . 112.0(2) ?
C13 C12 C11 . . 105.9(2) ?
C15 C12 C11 . . 112.1(2) ?
C13 C12 B1 . . 99.46(19) ?
C15 C12 B1 . . 112.1(2) ?
C11 C12 B1 . . 114.41(19) ?
C4 C13 C12 . . 104.86(19) ?
C4 C13 H13A . . 110.8 ?
C12 C13 H13A . . 110.8 ?
C4 C13 H13B . . 110.8 ?
C12 C13 H13B . . 110.8 ?
H13A C13 H13B . . 108.9 ?
C10 C14 H14A . . 120.0 ?
C10 C14 H14B . . 120.0 ?
H14A C14 H14B . . 120.0 ?
C12 C15 P1 . . 124.63(17) ?
C12 C15 H15A . . 106.2 ?
P1 C15 H15A . . 106.2 ?
C12 C15 H15B . . 106.2 ?
P1 C15 H15B . . 106.2 ?
H15A C15 H15B . . 106.4 ?
C22 C21 C26 . . 112.5(2) ?
C22 C21 B1 . . 127.6(2) ?
C26 C21 B1 . . 119.8(2) ?
F22 C22 C23 . . 114.1(2) ?
F22 C22 C21 . . 120.9(2) ?
C23 C22 C21 . . 125.0(2) ?
F23 C23 C24 . . 120.0(2) ?
F23 C23 C22 . . 120.4(2) ?
C24 C23 C22 . . 119.6(2) ?
F24 C24 C23 . . 121.0(2) ?
F24 C24 C25 . . 120.4(2) ?
C23 C24 C25 . . 118.5(2) ?
F25 C25 C24 . . 119.9(2) ?
F25 C25 C26 . . 120.4(2) ?
C24 C25 C26 . . 119.7(2) ?
F26 C26 C25 . . 115.2(2) ?
F26 C26 C21 . . 120.4(2) ?
C25 C26 C21 . . 124.4(2) ?
C36 C31 C32 . . 112.1(2) ?
C36 C31 B1 . . 125.8(2) ?
C32 C31 B1 . . 121.9(2) ?
F32 C32 C33 . . 114.8(2) ?
F32 C32 C31 . . 119.8(2) ?
C33 C32 C31 . . 125.3(2) ?
F33 C33 C34 . . 119.9(2) ?
F33 C33 C32 . . 120.8(2) ?
C34 C33 C32 . . 119.3(3) ?
F34 C34 C35 . . 121.0(3) ?
F34 C34 C33 . . 120.6(3) ?
C35 C34 C33 . . 118.3(2) ?
F35 C35 C34 . . 119.7(2) ?
F35 C35 C36 . . 119.8(3) ?
C34 C35 C36 . . 120.4(3) ?
F36 C36 C35 . . 114.0(2) ?
F36 C36 C31 . . 121.6(2) ?
C35 C36 C31 . . 124.3(3) ?
C42 C41 C46 . . 119.9(2) ?
C42 C41 P1 . . 118.53(19) ?
C46 C41 P1 . . 121.00(19) ?
C43 C42 C41 . . 120.0(2) ?
C43 C42 H42 . . 120.0 ?
C41 C42 H42 . . 120.0 ?
C42 C43 C44 . . 120.2(3) ?
C42 C43 H43 . . 119.9 ?
C44 C43 H43 . . 119.9 ?
C45 C44 C43 . . 119.7(3) ?
C45 C44 H44 . . 120.1 ?
C43 C44 H44 . . 120.1 ?
C44 C45 C46 . . 120.5(3) ?
C44 C45 H45 . . 119.8 ?
C46 C45 H45 . . 119.8 ?
C45 C46 C41 . . 119.7(2) ?
C45 C46 H46 . . 120.2 ?
C41 C46 H46 . . 120.2 ?
C56 C51 C52 . . 119.3(2) ?
C56 C51 P1 . . 119.6(2) ?
C52 C51 P1 . . 121.04(19) ?
C53 C52 C51 . . 120.2(2) ?
C53 C52 H52 . . 119.9 ?
C51 C52 H52 . . 119.9 ?
C52 C53 C54 . . 119.9(3) ?
C52 C53 H53 . . 120.0 ?
C54 C53 H53 . . 120.0 ?
C55 C54 C53 . . 120.1(3) ?
C55 C54 H54 . . 119.9 ?
C53 C54 H54 . . 119.9 ?
C56 C55 C54 . . 120.5(3) ?
C56 C55 H55 . . 119.7 ?
C54 C55 H55 . . 119.7 ?
C55 C56 C51 . . 119.8(3) ?
C55 C56 H56 . . 120.1 ?
C51 C56 H56 . . 120.1 ?
C66 C61 C62 . . 119.5(2) ?
C66 C61 P1 . . 121.9(2) ?
C62 C61 P1 . . 118.3(2) ?
C63 C62 C61 . . 119.9(3) ?
C63 C62 H62 . . 120.1 ?
C61 C62 H62 . . 120.1 ?
C62 C63 C64 . . 120.0(3) ?
C62 C63 H63 . . 120.0 ?
C64 C63 H63 . . 120.0 ?
C65 C64 C63 . . 120.7(3) ?
C65 C64 H64 . . 119.7 ?
C63 C64 H64 . . 119.7 ?
C64 C65 C66 . . 119.9(3) ?
C64 C65 H65 . . 120.1 ?
C66 C65 H65 . . 120.1 ?
C61 C66 C65 . . 120.1(3) ?
C61 C66 H66 . . 119.9 ?
C65 C66 H66 . . 119.9 ?
Cl2 C71 Cl1 . . 116.5(5) ?
Cl2 C71 H71C . . 108.2 ?
Cl1 C71 H71C . . 108.2 ?
Cl2 C71 H71D . . 108.2 ?
Cl1 C71 H71D . . 108.2 ?
H71C C71 H71D . . 107.3 ?
Cl1A C71A Cl2A . . 105.1(9) ?
Cl1A C71A H71A . . 110.7 ?
Cl2A C71A H71A . . 110.7 ?
Cl1A C71A H71B . . 110.7 ?
Cl2A C71A H71B . . 110.7 ?
H71A C71A H71B . . 108.8 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C3 C2 C1 . . . . 136.7(13) ?
C4 C3 C2 C1 . . . . -98.9(11) ?
C9 C3 C2A C1A . . . . 90.(9) ?
C4 C3 C2A C1A . . . . -148.(8) ?
C2A C3 C4 C13 . . . . 57.(4) ?
C2 C3 C4 C13 . . . . 51.9(7) ?
C9 C3 C4 C13 . . . . 176.8(2) ?
C2A C3 C4 C5 . . . . 174.(4) ?
C2 C3 C4 C5 . . . . 168.7(7) ?
C9 C3 C4 C5 . . . . -66.4(3) ?
C2A C3 C4 C6 . . . . -64.(4) ?
C2 C3 C4 C6 . . . . -69.4(7) ?
C9 C3 C4 C6 . . . . 55.5(3) ?
C13 C4 C5 B1 . . . . -18.9(2) ?
C3 C4 C5 B1 . . . . -139.4(2) ?
C6 C4 C5 B1 . . . . 97.4(2) ?
C21 B1 C5 C4 . . . . -133.7(2) ?
C31 B1 C5 C4 . . . . 108.1(2) ?
C12 B1 C5 C4 . . . . -10.3(2) ?
C13 C4 C6 C10 . . . . 57.9(3) ?
C3 C4 C6 C10 . . . . 179.9(2) ?
C5 C4 C6 C10 . . . . -54.9(3) ?
C13 C4 C6 C7 . . . . -175.0(2) ?
C3 C4 C6 C7 . . . . -53.0(3) ?
C5 C4 C6 C7 . . . . 72.2(3) ?
C10 C6 C7 C8 . . . . 176.8(2) ?
C4 C6 C7 C8 . . . . 52.3(3) ?
C6 C7 C8 C9 . . . . -53.3(3) ?
C7 C8 C9 C3 . . . . 56.4(3) ?
C2A C3 C9 C8 . . . . 66.6(14) ?
C2 C3 C9 C8 . . . . 67.8(4) ?
C4 C3 C9 C8 . . . . -58.1(3) ?
C7 C6 C10 C14 . . . . 7.3(3) ?
C4 C6 C10 C14 . . . . 133.4(3) ?
C7 C6 C10 C11 . . . . -172.1(2) ?
C4 C6 C10 C11 . . . . -46.0(3) ?
C14 C10 C11 C12 . . . . -131.3(2) ?
C6 C10 C11 C12 . . . . 48.2(3) ?
C10 C11 C12 C13 . . . . -58.5(3) ?
C10 C11 C12 C15 . . . . 179.1(2) ?
C10 C11 C12 B1 . . . . 50.0(3) ?
C5 B1 C12 C13 . . . . 35.3(2) ?
C21 B1 C12 C13 . . . . 152.8(2) ?
C31 B1 C12 C13 . . . . -84.4(2) ?
C5 B1 C12 C15 . . . . 153.90(19) ?
C21 B1 C12 C15 . . . . -88.6(3) ?
C31 B1 C12 C15 . . . . 34.2(3) ?
C5 B1 C12 C11 . . . . -77.0(2) ?
C21 B1 C12 C11 . . . . 40.5(3) ?
C31 B1 C12 C11 . . . . 163.3(2) ?
C3 C4 C13 C12 . . . . 167.17(19) ?
C5 C4 C13 C12 . . . . 44.6(2) ?
C6 C4 C13 C12 . . . . -70.9(2) ?
C15 C12 C13 C4 . . . . -168.59(19) ?
C11 C12 C13 C4 . . . . 68.9(2) ?
B1 C12 C13 C4 . . . . -50.0(2) ?
C13 C12 C15 P1 . . . . -70.1(3) ?
C11 C12 C15 P1 . . . . 48.8(3) ?
B1 C12 C15 P1 . . . . 179.11(17) ?
C51 P1 C15 C12 . . . . 53.4(2) ?
C41 P1 C15 C12 . . . . -73.3(2) ?
C61 P1 C15 C12 . . . . 172.6(2) ?
C5 B1 C21 C22 . . . . 135.9(2) ?
C31 B1 C21 C22 . . . . -101.9(3) ?
C12 B1 C21 C22 . . . . 23.5(4) ?
C5 B1 C21 C26 . . . . -41.5(3) ?
C31 B1 C21 C26 . . . . 80.7(3) ?
C12 B1 C21 C26 . . . . -154.0(2) ?
C26 C21 C22 F22 . . . . -173.7(2) ?
B1 C21 C22 F22 . . . . 8.7(4) ?
C26 C21 C22 C23 . . . . 4.7(4) ?
B1 C21 C22 C23 . . . . -172.9(2) ?
F22 C22 C23 F23 . . . . -1.6(3) ?
C21 C22 C23 F23 . . . . 179.9(2) ?
F22 C22 C23 C24 . . . . 176.9(2) ?
C21 C22 C23 C24 . . . . -1.6(4) ?
F23 C23 C24 F24 . . . . -0.6(4) ?
C22 C23 C24 F24 . . . . -179.0(2) ?
F23 C23 C24 C25 . . . . 176.8(2) ?
C22 C23 C24 C25 . . . . -1.7(4) ?
F24 C24 C25 F25 . . . . -0.8(4) ?
C23 C24 C25 F25 . . . . -178.2(2) ?
F24 C24 C25 C26 . . . . 178.8(2) ?
C23 C24 C25 C26 . . . . 1.4(4) ?
F25 C25 C26 F26 . . . . 1.5(3) ?
C24 C25 C26 F26 . . . . -178.1(2) ?
F25 C25 C26 C21 . . . . -178.3(2) ?
C24 C25 C26 C21 . . . . 2.1(4) ?
C22 C21 C26 F26 . . . . 175.3(2) ?
B1 C21 C26 F26 . . . . -6.9(3) ?
C22 C21 C26 C25 . . . . -4.9(4) ?
B1 C21 C26 C25 . . . . 172.9(2) ?
C5 B1 C31 C36 . . . . -15.1(3) ?
C21 B1 C31 C36 . . . . -134.7(2) ?
C12 B1 C31 C36 . . . . 96.5(3) ?
C5 B1 C31 C32 . . . . 159.7(2) ?
C21 B1 C31 C32 . . . . 40.1(3) ?
C12 B1 C31 C32 . . . . -88.7(3) ?
C36 C31 C32 F32 . . . . -176.1(2) ?
B1 C31 C32 F32 . . . . 8.5(3) ?
C36 C31 C32 C33 . . . . 3.4(4) ?
B1 C31 C32 C33 . . . . -172.1(2) ?
F32 C32 C33 F33 . . . . -0.9(4) ?
C31 C32 C33 F33 . . . . 179.6(2) ?
F32 C32 C33 C34 . . . . 178.8(2) ?
C31 C32 C33 C34 . . . . -0.7(4) ?
F33 C33 C34 F34 . . . . -0.9(4) ?
C32 C33 C34 F34 . . . . 179.4(2) ?
F33 C33 C34 C35 . . . . 178.2(2) ?
C32 C33 C34 C35 . . . . -1.5(4) ?
F34 C34 C35 F35 . . . . 0.4(4) ?
C33 C34 C35 F35 . . . . -178.7(2) ?
F34 C34 C35 C36 . . . . 179.8(2) ?
C33 C34 C35 C36 . . . . 0.7(4) ?
F35 C35 C36 F36 . . . . 2.5(3) ?
C34 C35 C36 F36 . . . . -176.9(2) ?
F35 C35 C36 C31 . . . . -178.2(2) ?
C34 C35 C36 C31 . . . . 2.4(4) ?
C32 C31 C36 F36 . . . . 175.0(2) ?
B1 C31 C36 F36 . . . . -9.7(4) ?
C32 C31 C36 C35 . . . . -4.2(4) ?
B1 C31 C36 C35 . . . . 171.0(2) ?
C51 P1 C41 C42 . . . . -164.8(2) ?
C61 P1 C41 C42 . . . . 79.9(2) ?
C15 P1 C41 C42 . . . . -34.7(2) ?
C51 P1 C41 C46 . . . . 23.5(2) ?
C61 P1 C41 C46 . . . . -91.7(2) ?
C15 P1 C41 C46 . . . . 153.6(2) ?
C46 C41 C42 C43 . . . . -0.9(4) ?
P1 C41 C42 C43 . . . . -172.7(2) ?
C41 C42 C43 C44 . . . . -0.5(4) ?
C42 C43 C44 C45 . . . . 1.5(4) ?
C43 C44 C45 C46 . . . . -1.0(4) ?
C44 C45 C46 C41 . . . . -0.5(4) ?
C42 C41 C46 C45 . . . . 1.4(4) ?
P1 C41 C46 C45 . . . . 173.0(2) ?
C41 P1 C51 C56 . . . . -135.2(2) ?
C61 P1 C51 C56 . . . . -22.2(2) ?
C15 P1 C51 C56 . . . . 95.6(2) ?
C41 P1 C51 C52 . . . . 44.8(2) ?
C61 P1 C51 C52 . . . . 157.8(2) ?
C15 P1 C51 C52 . . . . -84.4(2) ?
C56 C51 C52 C53 . . . . -0.3(4) ?
P1 C51 C52 C53 . . . . 179.7(2) ?
C51 C52 C53 C54 . . . . 0.8(4) ?
C52 C53 C54 C55 . . . . -0.7(4) ?
C53 C54 C55 C56 . . . . 0.0(5) ?
C54 C55 C56 C51 . . . . 0.5(4) ?
C52 C51 C56 C55 . . . . -0.3(4) ?
P1 C51 C56 C55 . . . . 179.7(2) ?
C51 P1 C61 C66 . . . . 128.7(2) ?
C41 P1 C61 C66 . . . . -115.6(2) ?
C15 P1 C61 C66 . . . . 4.7(3) ?
C51 P1 C61 C62 . . . . -57.0(2) ?
C41 P1 C61 C62 . . . . 58.6(2) ?
C15 P1 C61 C62 . . . . 179.0(2) ?
C66 C61 C62 C63 . . . . -1.2(4) ?
P1 C61 C62 C63 . . . . -175.6(2) ?
C61 C62 C63 C64 . . . . 1.1(4) ?
C62 C63 C64 C65 . . . . -0.6(5) ?
C63 C64 C65 C66 . . . . 0.2(5) ?
C62 C61 C66 C65 . . . . 0.8(4) ?
P1 C61 C66 C65 . . . . 175.0(2) ?
C64 C65 C66 C61 . . . . -0.3(5) ?

####################################################################### 
# 
# 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_erk9509
_database_code_depnum_ccdc_archive 'CCDC 1922912'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H38 B Cl2 F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         893.44

_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                   11.1982(12)
_cell_length_b                   11.5411(13)
_cell_length_c                   16.5533(16)
_cell_angle_alpha                96.789(6)
_cell_angle_beta                 96.943(7)
_cell_angle_gamma                106.576(7)
_cell_volume                     2009.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3179
_cell_measurement_theta_min      4.0490
_cell_measurement_theta_max      66.5372
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             916

_exptl_absorpt_coefficient_mu    2.543
_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  0.79
_exptl_absorpt_correction_T_max  0.95

_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            24246
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_full        67.21
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_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             6850
_reflns_number_gt                4461
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1685
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_number_reflns         6850
_refine_ls_number_parameters     542
_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)+(0.0730P)²+0.6795P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.520
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0011(2)

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'
Cl Cl 0.3639 0.7018 '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
P P1 0.29341(10) 0.27507(9) 0.21225(6) 0.0249(3) Uani d . . . 1 . .
B B1 0.6710(4) 0.3470(4) 0.3003(3) 0.0234(10) Uani d . . . 1 . .
C C1 0.5441(5) 0.3668(5) -0.0447(3) 0.0466(13) Uani d . . . 1 . .
H H1A 0.5671 0.4481 -0.0158 0.056 Uiso calc U . R 1 . .
H H1B 0.485 0.3432 -0.0944 0.056 Uiso calc U . R 1 . .
C C2 0.5935(4) 0.2875(4) -0.0160(2) 0.0347(10) Uani d . . . 1 . .
H H2 0.5681 0.207 -0.0466 0.042 Uiso calc U . R 1 . .
C C3 0.6880(4) 0.3139(4) 0.0621(2) 0.0324(10) Uani d . . . 1 . .
H H3 0.7187 0.4047 0.0797 0.039 Uiso calc U . R 1 . .
C C4 0.6301(4) 0.2560(3) 0.1343(2) 0.0239(9) Uani d . . . 1 . .
C C5 0.7229(4) 0.2999(3) 0.2179(2) 0.0271(9) Uani d . . . 1 . .
H H5A 0.7957 0.3675 0.2097 0.033 Uiso calc U . R 1 . .
H H5B 0.7556 0.2315 0.2299 0.033 Uiso calc U . R 1 . .
C C6 0.5911(4) 0.1134(3) 0.1104(2) 0.0272(9) Uani d . . . 1 . .
H H6 0.5292 0.0921 0.058 0.033 Uiso calc U . R 1 . .
C C7 0.7028(4) 0.0696(4) 0.0903(3) 0.0349(11) Uani d . . . 1 . .
H H7A 0.7652 0.0851 0.1412 0.042 Uiso calc U . R 1 . .
H H7B 0.6724 -0.0199 0.0708 0.042 Uiso calc U . R 1 . .
C C8 0.7673(4) 0.1335(4) 0.0249(3) 0.0365(11) Uani d . . . 1 . .
H H8A 0.8444 0.1096 0.0193 0.044 Uiso calc U . R 1 . .
H H8B 0.71 0.1053 -0.0287 0.044 Uiso calc U . R 1 . .
C C9 0.8031(4) 0.2722(4) 0.0447(3) 0.0374(11) Uani d . . . 1 . .
H H9A 0.8366 0.3085 -0.0023 0.045 Uiso calc U . R 1 . .
H H9B 0.8705 0.3021 0.0936 0.045 Uiso calc U . R 1 . .
C C10 0.5207(4) 0.0531(4) 0.1733(3) 0.0310(10) Uani d . . . 1 . .
C C11 0.4035(4) 0.0894(3) 0.1833(2) 0.0285(10) Uani d . . . 1 . .
H H11A 0.3613 0.0476 0.2257 0.034 Uiso calc U . R 1 . .
H H11B 0.3439 0.0642 0.1306 0.034 Uiso calc U . R 1 . .
C C12 0.4404(4) 0.2314(3) 0.2096(2) 0.0254(9) Uani d . . . 1 . .
C C13 0.5095(4) 0.2922(3) 0.1442(2) 0.0268(9) Uani d . . . 1 . .
H H13A 0.5325 0.3823 0.1595 0.032 Uiso calc U . R 1 . .
H H13B 0.4519 0.2685 0.0906 0.032 Uiso calc U . R 1 . .
C C14 0.5553(5) -0.0234(4) 0.2184(3) 0.0393(11) Uani d . . . 1 . .
H H14A 0.6303 -0.0439 0.2119 0.047 Uiso calc U . R 1 . .
H H14B 0.5049 -0.0576 0.257 0.047 Uiso calc U . R 1 . .
C C15 0.5205(4) 0.2671(3) 0.2973(2) 0.0255(9) Uani d . . . 1 . .
H H15A 0.5176 0.1914 0.3206 0.031 Uiso calc U . R 1 . .
H H15B 0.4815 0.316 0.333 0.031 Uiso calc U . R 1 . .
C C21 0.6844(4) 0.4958(3) 0.3200(2) 0.0245(9) Uani d . . . 1 . .
C C22 0.7275(4) 0.5859(3) 0.2723(2) 0.0261(9) Uani d . . . 1 . .
F F22 0.7585(2) 0.5581(2) 0.19702(13) 0.0325(6) Uani d . . . 1 . .
C C23 0.7408(4) 0.7091(3) 0.2943(2) 0.0298(10) Uani d . . . 1 . .
F F23 0.7829(2) 0.7903(2) 0.24388(15) 0.0380(6) Uani d . . . 1 . .
C C24 0.7108(4) 0.7495(3) 0.3694(3) 0.0297(10) Uani d . . . 1 . .
F F24 0.7214(2) 0.8688(2) 0.39079(15) 0.0382(6) Uani d . . . 1 . .
C C25 0.6676(4) 0.6648(4) 0.4184(2) 0.0296(10) Uani d . . . 1 . .
F F25 0.6351(2) 0.7018(2) 0.49135(14) 0.0359(6) Uani d . . . 1 . .
C C26 0.6549(4) 0.5434(4) 0.3937(2) 0.0273(9) Uani d . . . 1 . .
F F26 0.6114(2) 0.4670(2) 0.44687(13) 0.0311(6) Uani d . . . 1 . .
C C31 0.7622(4) 0.3224(3) 0.3807(2) 0.0264(9) Uani d . . . 1 . .
C C32 0.7271(4) 0.2492(4) 0.4393(2) 0.0276(9) Uani d . . . 1 . .
F F32 0.6022(2) 0.1954(2) 0.44388(14) 0.0394(6) Uani d . . . 1 . .
C C33 0.8086(5) 0.2250(4) 0.5000(2) 0.0352(11) Uani d . . . 1 . .
F F33 0.7632(3) 0.1527(3) 0.55540(16) 0.0486(7) Uani d . . . 1 . .
C C34 0.9355(4) 0.2781(4) 0.5065(2) 0.0325(10) Uani d . . . 1 . .
F F34 1.0163(2) 0.2556(3) 0.56481(15) 0.0502(8) Uani d . . . 1 . .
C C35 0.9779(4) 0.3548(4) 0.4521(2) 0.0322(10) Uani d . . . 1 . .
F F35 1.1031(2) 0.4098(3) 0.45785(15) 0.0442(7) Uani d . . . 1 . .
C C36 0.8925(4) 0.3753(4) 0.3921(2) 0.0295(10) Uani d . . . 1 . .
F F36 0.9436(2) 0.4539(2) 0.34179(14) 0.0359(6) Uani d . . . 1 . .
C C41 0.1842(4) 0.1820(3) 0.2674(2) 0.0259(9) Uani d . . . 1 . .
C C42 0.0546(4) 0.1638(4) 0.2465(3) 0.0350(10) Uani d . . . 1 . .
H H42 0.0244 0.1947 0.2001 0.042 Uiso calc U . R 1 . .
C C43 -0.0298(4) 0.1017(4) 0.2924(3) 0.0421(12) Uani d . . . 1 . .
H H43 -0.1176 0.0905 0.2778 0.05 Uiso calc U . R 1 . .
C C44 0.0135(5) 0.0558(4) 0.3600(3) 0.0400(11) Uani d . . . 1 . .
H H44 -0.0446 0.0119 0.3913 0.048 Uiso calc U . R 1 . .
C C45 0.1412(4) 0.0739(4) 0.3819(3) 0.0330(10) Uani d . . . 1 . .
H H45 0.1708 0.0427 0.4283 0.04 Uiso calc U . R 1 . .
C C46 0.2262(4) 0.1371(3) 0.3365(2) 0.0260(9) Uani d . . . 1 . .
H H46 0.314 0.15 0.3524 0.031 Uiso calc U . R 1 . .
C C51 0.2108(4) 0.2612(4) 0.1084(2) 0.0260(9) Uani d . . . 1 . .
C C52 0.1636(4) 0.1460(4) 0.0597(3) 0.0347(11) Uani d . . . 1 . .
H H52 0.1674 0.0752 0.0825 0.042 Uiso calc U . R 1 . .
C C53 0.1111(4) 0.1350(4) -0.0220(3) 0.0420(12) Uani d . . . 1 . .
H H53 0.08 0.0565 -0.0553 0.05 Uiso calc U . R 1 . .
C C54 0.1037(4) 0.2365(5) -0.0553(3) 0.0424(12) Uani d . . . 1 . .
H H54 0.0696 0.2282 -0.1118 0.051 Uiso calc U . R 1 . .
C C55 0.1451(4) 0.3499(4) -0.0073(3) 0.0433(12) Uani d . . . 1 . .
H H55 0.1366 0.4195 -0.03 0.052 Uiso calc U . R 1 . .
C C56 0.1995(4) 0.3628(4) 0.0745(3) 0.0327(10) Uani d . . . 1 . .
H H56 0.2291 0.4417 0.1075 0.039 Uiso calc U . R 1 . .
C C61 0.3326(4) 0.4324(3) 0.2615(2) 0.0281(10) Uani d . . . 1 . .
C C62 0.2936(4) 0.4573(4) 0.3370(2) 0.0314(10) Uani d . . . 1 . .
H H62 0.2491 0.3921 0.3624 0.038 Uiso calc U . R 1 . .
C C63 0.3202(4) 0.5770(4) 0.3746(2) 0.0339(10) Uani d . . . 1 . .
H H63 0.2945 0.5936 0.4262 0.041 Uiso calc U . R 1 . .
C C64 0.3834(4) 0.6731(4) 0.3383(2) 0.0329(10) Uani d . . . 1 . .
H H64 0.4004 0.7552 0.3644 0.039 Uiso calc U . R 1 . .
C C65 0.4219(4) 0.6486(4) 0.2635(3) 0.0331(10) Uani d . . . 1 . .
H H65 0.4648 0.7143 0.2378 0.04 Uiso calc U . R 1 . .
C C66 0.3981(4) 0.5290(4) 0.2260(2) 0.0306(10) Uani d . . . 1 . .
H H66 0.427 0.5128 0.1754 0.037 Uiso calc U . R 1 . .
C C71 0.0789(5) 0.6793(4) 0.2505(3) 0.0438(12) Uani d . . . 1 . .
H H71A 0.1209 0.6616 0.3017 0.053 Uiso calc U . R 1 . .
H H71B -0.0038 0.6878 0.2606 0.053 Uiso calc U . R 1 . .
Cl Cl1 0.17222(13) 0.81779(11) 0.22677(9) 0.0623(4) Uani d . . . 1 . .
Cl Cl2 0.05483(12) 0.55693(11) 0.17043(7) 0.0480(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
P1 C41 . 1.799(4) ?
P1 C61 . 1.806(4) ?
P1 C51 . 1.818(4) ?
P1 C12 . 1.858(4) ?
B1 C5 . 1.640(6) ?
B1 C15 . 1.667(6) ?
B1 C21 . 1.669(6) ?
B1 C31 . 1.680(6) ?
C1 C2 . 1.302(6) ?
C1 H1A . 0.95 ?
C1 H1B . 0.95 ?
C2 C3 . 1.509(6) ?
C2 H2 . 0.95 ?
C3 C9 . 1.545(6) ?
C3 C4 . 1.558(5) ?
C3 H3 . 1.0 ?
C4 C13 . 1.544(5) ?
C4 C5 . 1.561(5) ?
C4 C6 . 1.565(5) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C10 . 1.500(6) ?
C6 C7 . 1.534(6) ?
C6 H6 . 1.0 ?
C7 C8 . 1.520(6) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.520(6) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C14 . 1.328(6) ?
C10 C11 . 1.509(6) ?
C11 C12 . 1.564(5) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.528(5) ?
C12 C15 . 1.555(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.95 ?
C14 H14B . 0.95 ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C21 C22 . 1.391(5) ?
C21 C26 . 1.394(5) ?
C22 F22 . 1.360(4) ?
C22 C23 . 1.386(5) ?
C23 F23 . 1.351(4) ?
C23 C24 . 1.388(6) ?
C24 F24 . 1.348(4) ?
C24 C25 . 1.365(6) ?
C25 F25 . 1.358(4) ?
C25 C26 . 1.374(5) ?
C26 F26 . 1.353(4) ?
C31 C32 . 1.380(5) ?
C31 C36 . 1.391(6) ?
C32 F32 . 1.375(5) ?
C32 C33 . 1.383(5) ?
C33 F33 . 1.359(5) ?
C33 C34 . 1.363(6) ?
C34 F34 . 1.342(4) ?
C34 C35 . 1.367(6) ?
C35 F35 . 1.350(5) ?
C35 C36 . 1.383(6) ?
C36 F36 . 1.357(5) ?
C41 C46 . 1.395(5) ?
C41 C42 . 1.399(6) ?
C42 C43 . 1.379(6) ?
C42 H42 . 0.95 ?
C43 C44 . 1.387(6) ?
C43 H43 . 0.95 ?
C44 C45 . 1.381(6) ?
C44 H44 . 0.95 ?
C45 C46 . 1.382(6) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C51 C56 . 1.389(5) ?
C51 C52 . 1.392(6) ?
C52 C53 . 1.384(6) ?
C52 H52 . 0.95 ?
C53 C54 . 1.371(6) ?
C53 H53 . 0.95 ?
C54 C55 . 1.370(7) ?
C54 H54 . 0.95 ?
C55 C56 . 1.388(6) ?
C55 H55 . 0.95 ?
C56 H56 . 0.95 ?
C61 C66 . 1.385(6) ?
C61 C62 . 1.398(6) ?
C62 C63 . 1.379(6) ?
C62 H62 . 0.95 ?
C63 C64 . 1.380(6) ?
C63 H63 . 0.95 ?
C64 C65 . 1.383(6) ?
C64 H64 . 0.95 ?
C65 C66 . 1.382(5) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
C71 Cl2 . 1.755(5) ?
C71 Cl1 . 1.760(5) ?
C71 H71A . 0.99 ?
C71 H71B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C41 P1 C61 . . 107.83(19) ?
C41 P1 C51 . . 107.06(18) ?
C61 P1 C51 . . 108.31(18) ?
C41 P1 C12 . . 113.32(18) ?
C61 P1 C12 . . 109.52(19) ?
C51 P1 C12 . . 110.62(17) ?
C5 B1 C15 . . 110.3(3) ?
C5 B1 C21 . . 117.3(3) ?
C15 B1 C21 . . 108.3(3) ?
C5 B1 C31 . . 105.8(3) ?
C15 B1 C31 . . 110.3(3) ?
C21 B1 C31 . . 104.7(3) ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C3 . . 124.9(4) ?
C1 C2 H2 . . 117.6 ?
C3 C2 H2 . . 117.6 ?
C2 C3 C9 . . 110.0(3) ?
C2 C3 C4 . . 113.1(4) ?
C9 C3 C4 . . 111.1(3) ?
C2 C3 H3 . . 107.5 ?
C9 C3 H3 . . 107.5 ?
C4 C3 H3 . . 107.5 ?
C13 C4 C3 . . 108.7(3) ?
C13 C4 C5 . . 108.6(3) ?
C3 C4 C5 . . 112.5(3) ?
C13 C4 C6 . . 108.1(3) ?
C3 C4 C6 . . 108.0(3) ?
C5 C4 C6 . . 110.8(3) ?
C4 C5 B1 . . 118.9(3) ?
C4 C5 H5A . . 107.6 ?
B1 C5 H5A . . 107.6 ?
C4 C5 H5B . . 107.6 ?
B1 C5 H5B . . 107.6 ?
H5A C5 H5B . . 107.0 ?
C10 C6 C7 . . 115.8(3) ?
C10 C6 C4 . . 110.1(3) ?
C7 C6 C4 . . 111.9(3) ?
C10 C6 H6 . . 106.1 ?
C7 C6 H6 . . 106.1 ?
C4 C6 H6 . . 106.1 ?
C8 C7 C6 . . 112.4(4) ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7B . . 109.1 ?
C6 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
C9 C8 C7 . . 113.0(3) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C3 . . 111.1(4) ?
C8 C9 H9A . . 109.4 ?
C3 C9 H9A . . 109.4 ?
C8 C9 H9B . . 109.4 ?
C3 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C14 C10 C6 . . 125.5(4) ?
C14 C10 C11 . . 121.3(4) ?
C6 C10 C11 . . 113.2(3) ?
C10 C11 C12 . . 109.5(3) ?
C10 C11 H11A . . 109.8 ?
C12 C11 H11A . . 109.8 ?
C10 C11 H11B . . 109.8 ?
C12 C11 H11B . . 109.8 ?
H11A C11 H11B . . 108.2 ?
C13 C12 C15 . . 113.5(3) ?
C13 C12 C11 . . 108.1(3) ?
C15 C12 C11 . . 108.9(3) ?
C13 C12 P1 . . 108.6(3) ?
C15 C12 P1 . . 109.1(3) ?
C11 C12 P1 . . 108.6(3) ?
C12 C13 C4 . . 112.5(3) ?
C12 C13 H13A . . 109.1 ?
C4 C13 H13A . . 109.1 ?
C12 C13 H13B . . 109.1 ?
C4 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C10 C14 H14A . . 120.0 ?
C10 C14 H14B . . 120.0 ?
H14A C14 H14B . . 120.0 ?
C12 C15 B1 . . 114.3(3) ?
C12 C15 H15A . . 108.7 ?
B1 C15 H15A . . 108.7 ?
C12 C15 H15B . . 108.7 ?
B1 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C22 C21 C26 . . 112.1(3) ?
C22 C21 B1 . . 128.1(3) ?
C26 C21 B1 . . 119.7(3) ?
F22 C22 C23 . . 113.6(4) ?
F22 C22 C21 . . 121.4(3) ?
C23 C22 C21 . . 124.9(4) ?
F23 C23 C22 . . 121.0(4) ?
F23 C23 C24 . . 119.6(3) ?
C22 C23 C24 . . 119.4(4) ?
F24 C24 C25 . . 122.0(4) ?
F24 C24 C23 . . 119.9(4) ?
C25 C24 C23 . . 118.1(3) ?
F25 C25 C24 . . 119.1(3) ?
F25 C25 C26 . . 120.4(4) ?
C24 C25 C26 . . 120.4(4) ?
F26 C26 C25 . . 115.8(4) ?
F26 C26 C21 . . 119.2(3) ?
C25 C26 C21 . . 125.0(4) ?
C32 C31 C36 . . 111.4(4) ?
C32 C31 B1 . . 128.8(4) ?
C36 C31 B1 . . 119.7(4) ?
F32 C32 C31 . . 121.4(3) ?
F32 C32 C33 . . 112.9(4) ?
C31 C32 C33 . . 125.7(4) ?
F33 C33 C34 . . 119.6(4) ?
F33 C33 C32 . . 120.6(4) ?
C34 C33 C32 . . 119.7(4) ?
F34 C34 C33 . . 120.7(4) ?
F34 C34 C35 . . 121.1(4) ?
C33 C34 C35 . . 118.2(4) ?
F35 C35 C34 . . 119.4(4) ?
F35 C35 C36 . . 120.7(4) ?
C34 C35 C36 . . 119.9(4) ?
F36 C36 C35 . . 115.4(4) ?
F36 C36 C31 . . 119.5(3) ?
C35 C36 C31 . . 125.1(4) ?
C46 C41 C42 . . 118.4(4) ?
C46 C41 P1 . . 121.4(3) ?
C42 C41 P1 . . 119.9(3) ?
C43 C42 C41 . . 120.9(4) ?
C43 C42 H42 . . 119.6 ?
C41 C42 H42 . . 119.6 ?
C42 C43 C44 . . 119.9(4) ?
C42 C43 H43 . . 120.0 ?
C44 C43 H43 . . 120.0 ?
C45 C44 C43 . . 119.9(4) ?
C45 C44 H44 . . 120.0 ?
C43 C44 H44 . . 120.0 ?
C44 C45 C46 . . 120.3(4) ?
C44 C45 H45 . . 119.8 ?
C46 C45 H45 . . 119.8 ?
C45 C46 C41 . . 120.5(4) ?
C45 C46 H46 . . 119.7 ?
C41 C46 H46 . . 119.7 ?
C56 C51 C52 . . 118.9(4) ?
C56 C51 P1 . . 122.0(3) ?
C52 C51 P1 . . 119.0(3) ?
C53 C52 C51 . . 119.8(4) ?
C53 C52 H52 . . 120.1 ?
C51 C52 H52 . . 120.1 ?
C54 C53 C52 . . 120.6(4) ?
C54 C53 H53 . . 119.7 ?
C52 C53 H53 . . 119.7 ?
C55 C54 C53 . . 120.3(4) ?
C55 C54 H54 . . 119.9 ?
C53 C54 H54 . . 119.9 ?
C54 C55 C56 . . 119.9(4) ?
C54 C55 H55 . . 120.0 ?
C56 C55 H55 . . 120.0 ?
C55 C56 C51 . . 120.4(4) ?
C55 C56 H56 . . 119.8 ?
C51 C56 H56 . . 119.8 ?
C66 C61 C62 . . 119.1(4) ?
C66 C61 P1 . . 122.0(3) ?
C62 C61 P1 . . 118.9(3) ?
C63 C62 C61 . . 119.7(4) ?
C63 C62 H62 . . 120.2 ?
C61 C62 H62 . . 120.2 ?
C62 C63 C64 . . 121.0(4) ?
C62 C63 H63 . . 119.5 ?
C64 C63 H63 . . 119.5 ?
C63 C64 C65 . . 119.4(4) ?
C63 C64 H64 . . 120.3 ?
C65 C64 H64 . . 120.3 ?
C66 C65 C64 . . 120.2(4) ?
C66 C65 H65 . . 119.9 ?
C64 C65 H65 . . 119.9 ?
C65 C66 C61 . . 120.6(4) ?
C65 C66 H66 . . 119.7 ?
C61 C66 H66 . . 119.7 ?
Cl2 C71 Cl1 . . 111.5(3) ?
Cl2 C71 H71A . . 109.3 ?
Cl1 C71 H71A . . 109.3 ?
Cl2 C71 H71B . . 109.3 ?
Cl1 C71 H71B . . 109.3 ?
H71A C71 H71B . . 108.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C9 . . . . -129.0(5) ?
C1 C2 C3 C4 . . . . 106.1(5) ?
C2 C3 C4 C13 . . . . -51.2(4) ?
C9 C3 C4 C13 . . . . -175.4(3) ?
C2 C3 C4 C5 . . . . -171.4(3) ?
C9 C3 C4 C5 . . . . 64.3(4) ?
C2 C3 C4 C6 . . . . 65.9(4) ?
C9 C3 C4 C6 . . . . -58.4(4) ?
C13 C4 C5 B1 . . . . 11.6(5) ?
C3 C4 C5 B1 . . . . 132.0(4) ?
C6 C4 C5 B1 . . . . -106.9(4) ?
C15 B1 C5 C4 . . . . 34.4(5) ?
C21 B1 C5 C4 . . . . -90.1(4) ?
C31 B1 C5 C4 . . . . 153.6(3) ?
C13 C4 C6 C10 . . . . -55.7(4) ?
C3 C4 C6 C10 . . . . -173.2(3) ?
C5 C4 C6 C10 . . . . 63.1(4) ?
C13 C4 C6 C7 . . . . 174.0(3) ?
C3 C4 C6 C7 . . . . 56.5(4) ?
C5 C4 C6 C7 . . . . -67.1(4) ?
C10 C6 C7 C8 . . . . 178.9(3) ?
C4 C6 C7 C8 . . . . -53.8(4) ?
C6 C7 C8 C9 . . . . 51.8(5) ?
C7 C8 C9 C3 . . . . -53.4(5) ?
C2 C3 C9 C8 . . . . -68.4(5) ?
C4 C3 C9 C8 . . . . 57.6(4) ?
C7 C6 C10 C14 . . . . 7.7(6) ?
C4 C6 C10 C14 . . . . -120.5(4) ?
C7 C6 C10 C11 . . . . -173.5(3) ?
C4 C6 C10 C11 . . . . 58.4(4) ?
C14 C10 C11 C12 . . . . 119.9(4) ?
C6 C10 C11 C12 . . . . -59.0(4) ?
C10 C11 C12 C13 . . . . 57.3(4) ?
C10 C11 C12 C15 . . . . -66.3(4) ?
C10 C11 C12 P1 . . . . 175.0(3) ?
C41 P1 C12 C13 . . . . 165.7(2) ?
C61 P1 C12 C13 . . . . -73.9(3) ?
C51 P1 C12 C13 . . . . 45.4(3) ?
C41 P1 C12 C15 . . . . -70.2(3) ?
C61 P1 C12 C15 . . . . 50.3(3) ?
C51 P1 C12 C15 . . . . 169.6(3) ?
C41 P1 C12 C11 . . . . 48.4(3) ?
C61 P1 C12 C11 . . . . 168.8(3) ?
C51 P1 C12 C11 . . . . -71.9(3) ?
C15 C12 C13 C4 . . . . 61.4(4) ?
C11 C12 C13 C4 . . . . -59.5(4) ?
P1 C12 C13 C4 . . . . -177.1(2) ?
C3 C4 C13 C12 . . . . 175.7(3) ?
C5 C4 C13 C12 . . . . -61.7(4) ?
C6 C4 C13 C12 . . . . 58.6(4) ?
C13 C12 C15 B1 . . . . -8.6(4) ?
C11 C12 C15 B1 . . . . 111.8(4) ?
P1 C12 C15 B1 . . . . -129.8(3) ?
C5 B1 C15 C12 . . . . -35.6(4) ?
C21 B1 C15 C12 . . . . 93.9(4) ?
C31 B1 C15 C12 . . . . -152.1(3) ?
C5 B1 C21 C22 . . . . 4.4(6) ?
C15 B1 C21 C22 . . . . -121.1(4) ?
C31 B1 C21 C22 . . . . 121.2(4) ?
C5 B1 C21 C26 . . . . -172.9(3) ?
C15 B1 C21 C26 . . . . 61.6(4) ?
C31 B1 C21 C26 . . . . -56.1(5) ?
C26 C21 C22 F22 . . . . -178.4(3) ?
B1 C21 C22 F22 . . . . 4.1(6) ?
C26 C21 C22 C23 . . . . 0.2(6) ?
B1 C21 C22 C23 . . . . -177.3(4) ?
F22 C22 C23 F23 . . . . -0.9(5) ?
C21 C22 C23 F23 . . . . -179.6(4) ?
F22 C22 C23 C24 . . . . 179.2(3) ?
C21 C22 C23 C24 . . . . 0.6(6) ?
F23 C23 C24 F24 . . . . 1.3(6) ?
C22 C23 C24 F24 . . . . -178.9(4) ?
F23 C23 C24 C25 . . . . 179.5(4) ?
C22 C23 C24 C25 . . . . -0.7(6) ?
F24 C24 C25 F25 . . . . -0.4(6) ?
C23 C24 C25 F25 . . . . -178.6(3) ?
F24 C24 C25 C26 . . . . 178.3(4) ?
C23 C24 C25 C26 . . . . 0.1(6) ?
F25 C25 C26 F26 . . . . -1.3(5) ?
C24 C25 C26 F26 . . . . 180.0(3) ?
F25 C25 C26 C21 . . . . 179.4(4) ?
C24 C25 C26 C21 . . . . 0.7(7) ?
C22 C21 C26 F26 . . . . 179.9(3) ?
B1 C21 C26 F26 . . . . -2.4(5) ?
C22 C21 C26 C25 . . . . -0.8(6) ?
B1 C21 C26 C25 . . . . 176.9(4) ?
C5 B1 C31 C32 . . . . -119.4(4) ?
C15 B1 C31 C32 . . . . -0.2(6) ?
C21 B1 C31 C32 . . . . 116.1(4) ?
C5 B1 C31 C36 . . . . 57.3(4) ?
C15 B1 C31 C36 . . . . 176.6(3) ?
C21 B1 C31 C36 . . . . -67.1(4) ?
C36 C31 C32 F32 . . . . 174.8(3) ?
B1 C31 C32 F32 . . . . -8.3(6) ?
C36 C31 C32 C33 . . . . -2.8(6) ?
B1 C31 C32 C33 . . . . 174.2(4) ?
F32 C32 C33 F33 . . . . 1.3(5) ?
C31 C32 C33 F33 . . . . 179.0(4) ?
F32 C32 C33 C34 . . . . -176.1(4) ?
C31 C32 C33 C34 . . . . 1.7(7) ?
F33 C33 C34 F34 . . . . 2.9(6) ?
C32 C33 C34 F34 . . . . -179.8(4) ?
F33 C33 C34 C35 . . . . -177.1(4) ?
C32 C33 C34 C35 . . . . 0.3(6) ?
F34 C34 C35 F35 . . . . -0.8(6) ?
C33 C34 C35 F35 . . . . 179.2(4) ?
F34 C34 C35 C36 . . . . 179.3(4) ?
C33 C34 C35 C36 . . . . -0.7(6) ?
F35 C35 C36 F36 . . . . -0.7(6) ?
C34 C35 C36 F36 . . . . 179.2(3) ?
F35 C35 C36 C31 . . . . 179.5(4) ?
C34 C35 C36 C31 . . . . -0.7(6) ?
C32 C31 C36 F36 . . . . -177.6(3) ?
B1 C31 C36 F36 . . . . 5.1(5) ?
C32 C31 C36 C35 . . . . 2.2(6) ?
B1 C31 C36 C35 . . . . -175.0(4) ?
C61 P1 C41 C46 . . . . -86.7(3) ?
C51 P1 C41 C46 . . . . 156.9(3) ?
C12 P1 C41 C46 . . . . 34.7(4) ?
C61 P1 C41 C42 . . . . 86.7(3) ?
C51 P1 C41 C42 . . . . -29.7(4) ?
C12 P1 C41 C42 . . . . -151.9(3) ?
C46 C41 C42 C43 . . . . -0.8(6) ?
P1 C41 C42 C43 . . . . -174.4(3) ?
C41 C42 C43 C44 . . . . -0.4(7) ?
C42 C43 C44 C45 . . . . 0.9(7) ?
C43 C44 C45 C46 . . . . -0.3(6) ?
C44 C45 C46 C41 . . . . -0.9(6) ?
C42 C41 C46 C45 . . . . 1.4(6) ?
P1 C41 C46 C45 . . . . 174.9(3) ?
C41 P1 C51 C56 . . . . 123.7(4) ?
C61 P1 C51 C56 . . . . 7.7(4) ?
C12 P1 C51 C56 . . . . -112.4(4) ?
C41 P1 C51 C52 . . . . -59.9(4) ?
C61 P1 C51 C52 . . . . -175.9(3) ?
C12 P1 C51 C52 . . . . 64.0(4) ?
C56 C51 C52 C53 . . . . 2.6(7) ?
P1 C51 C52 C53 . . . . -173.9(3) ?
C51 C52 C53 C54 . . . . -0.9(7) ?
C52 C53 C54 C55 . . . . -1.8(8) ?
C53 C54 C55 C56 . . . . 2.6(8) ?
C54 C55 C56 C51 . . . . -0.8(7) ?
C52 C51 C56 C55 . . . . -1.8(7) ?
P1 C51 C56 C55 . . . . 174.6(3) ?
C41 P1 C61 C66 . . . . -169.2(3) ?
C51 P1 C61 C66 . . . . -53.7(4) ?
C12 P1 C61 C66 . . . . 67.1(4) ?
C41 P1 C61 C62 . . . . 9.7(4) ?
C51 P1 C61 C62 . . . . 125.3(3) ?
C12 P1 C61 C62 . . . . -114.0(3) ?
C66 C61 C62 C63 . . . . 0.4(6) ?
P1 C61 C62 C63 . . . . -178.5(3) ?
C61 C62 C63 C64 . . . . 0.8(6) ?
C62 C63 C64 C65 . . . . -0.7(6) ?
C63 C64 C65 C66 . . . . -0.6(6) ?
C64 C65 C66 C61 . . . . 1.9(6) ?
C62 C61 C66 C65 . . . . -1.7(6) ?
P1 C61 C66 C65 . . . . 177.2(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_erk9369
_database_code_depnum_ccdc_archive 'CCDC 1922909'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H28 B F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         728.39

_chemical_melting_point          ?

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

_cell_length_a                   12.2953(3)
_cell_length_b                   14.3056(3)
_cell_length_c                   20.8746(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.3000(10)
_cell_angle_gamma                90
_cell_volume                     3612.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      3.6538
_cell_measurement_theta_max      66.7066
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488

_exptl_absorpt_coefficient_mu    1.376
_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  0.85

_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            52800
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         66.76
_diffrn_reflns_theta_full        66.76
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_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.

A badly disordered half solvent molecule (probably half
dichloromethane molecule mixed with half pentane 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.
;

_reflns_number_total             6392
_reflns_number_gt                5636
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0909
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_number_reflns         6392
_refine_ls_number_parameters     460
_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)+(0.0418P)²+2.5012P] 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         0.380
_refine_diff_density_min         -0.383
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       '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
B B1 0.27923(15) 0.25521(13) 0.50546(8) 0.0156(4) Uani d . . . 1 . .
C C1 0.35029(13) 0.33736(11) 0.54983(8) 0.0153(3) Uani d . . . 1 . .
H H1A 0.4158 0.3084 0.5771 0.018 Uiso calc U . R 1 . .
H H1B 0.3773 0.3825 0.5203 0.018 Uiso calc U . R 1 . .
P P1 0.37274(3) 0.48666(3) 0.63662(2) 0.01399(10) Uani d . . . 1 . .
C C2 0.28487(13) 0.39151(11) 0.59481(8) 0.0148(3) Uani d . . . 1 . .
H H2 0.2687 0.3471 0.6289 0.018 Uiso calc U . R 1 . .
C C3 0.17203(13) 0.42923(11) 0.55735(8) 0.0166(3) Uani d . . . 1 . .
H H3 0.1894 0.4755 0.5247 0.02 Uiso calc U . R 1 . .
C C4 0.10852(13) 0.34952(11) 0.51919(8) 0.0169(3) Uani d . . . 1 . .
C C5 0.16510(13) 0.30569(12) 0.46888(8) 0.0173(3) Uani d . . . 1 . .
H H5A 0.1827 0.3541 0.4384 0.021 Uiso calc U . R 1 . .
H H5B 0.1159 0.2588 0.4436 0.021 Uiso calc U . R 1 . .
C C6 0.01072(14) 0.32086(13) 0.53078(8) 0.0216(4) Uani d . . . 1 . .
H H6 -0.0252 0.2722 0.504 0.026 Uiso calc U . R 1 . .
C C7 -0.04749(14) 0.35895(14) 0.58255(9) 0.0274(4) Uani d . . . 1 . .
H H7A -0.0806 0.3069 0.6037 0.033 Uiso calc U . R 1 . .
H H7B -0.1078 0.4012 0.5625 0.033 Uiso calc U . R 1 . .
C C8 0.03333(14) 0.41221(14) 0.63333(9) 0.0248(4) Uani d . . . 1 . .
H H8A 0.0837 0.3677 0.6602 0.03 Uiso calc U . R 1 . .
H H8B -0.0077 0.447 0.6624 0.03 Uiso calc U . R 1 . .
C C9 0.10017(14) 0.48022(12) 0.59967(8) 0.0205(4) Uani d . . . 1 . .
H H9A 0.1484 0.518 0.633 0.025 Uiso calc U . R 1 . .
H H9B 0.0491 0.5234 0.572 0.025 Uiso calc U . R 1 . .
C C11 0.36011(13) 0.21464(11) 0.45590(8) 0.0158(3) Uani d . . . 1 . .
C C12 0.44974(13) 0.15681(12) 0.47955(8) 0.0168(3) Uani d . . . 1 . .
F F12 0.47293(8) 0.13558(7) 0.54371(4) 0.0221(2) Uani d . . . 1 . .
C C13 0.52124(13) 0.11913(12) 0.44239(8) 0.0191(3) Uani d . . . 1 . .
F F13 0.60483(8) 0.06303(7) 0.46957(5) 0.0250(2) Uani d . . . 1 . .
C C14 0.50945(14) 0.14261(12) 0.37758(8) 0.0215(4) Uani d . . . 1 . .
F F14 0.57998(9) 0.10961(8) 0.34071(5) 0.0296(2) Uani d . . . 1 . .
C C15 0.42486(15) 0.20156(12) 0.35157(8) 0.0204(4) Uani d . . . 1 . .
F F15 0.41157(9) 0.22675(8) 0.28822(5) 0.0288(2) Uani d . . . 1 . .
C C16 0.35193(13) 0.23393(11) 0.38997(8) 0.0172(3) Uani d . . . 1 . .
F F16 0.26883(8) 0.28783(7) 0.35803(4) 0.0231(2) Uani d . . . 1 . .
C C21 0.24594(13) 0.16323(11) 0.54677(8) 0.0166(3) Uani d . . . 1 . .
F F22 0.34170(9) 0.20767(7) 0.65251(5) 0.0290(2) Uani d . . . 1 . .
C C22 0.27565(15) 0.14679(12) 0.61317(8) 0.0215(4) Uani d . . . 1 . .
F F23 0.27929(14) 0.05942(9) 0.70966(6) 0.0548(4) Uani d . . . 1 . .
C C23 0.24621(18) 0.06875(14) 0.64492(9) 0.0315(4) Uani d . . . 1 . .
F F24 0.15377(12) -0.07653(8) 0.63983(7) 0.0493(4) Uani d . . . 1 . .
C C24 0.18344(18) 0.00044(13) 0.60976(10) 0.0323(5) Uani d . . . 1 . .
F F25 0.09782(9) -0.05866(7) 0.50789(6) 0.0342(3) Uani d . . . 1 . .
C C25 0.15410(15) 0.01041(12) 0.54336(10) 0.0248(4) Uani d . . . 1 . .
F F26 0.15475(8) 0.09348(7) 0.44826(5) 0.0264(2) Uani d . . . 1 . .
C C26 0.18489(14) 0.09030(12) 0.51395(8) 0.0192(3) Uani d . . . 1 . .
C C31 0.35050(13) 0.51152(12) 0.71826(8) 0.0174(3) Uani d . . . 1 . .
C C32 0.41728(14) 0.58024(12) 0.75337(8) 0.0220(4) Uani d . . . 1 . .
H H32 0.4691 0.6138 0.7335 0.026 Uiso calc U . R 1 . .
C C33 0.40739(16) 0.59909(13) 0.81711(9) 0.0265(4) Uani d . . . 1 . .
H H33 0.452 0.6461 0.8409 0.032 Uiso calc U . R 1 . .
C C34 0.33243(15) 0.54948(14) 0.84641(8) 0.0271(4) Uani d . . . 1 . .
H H34 0.326 0.5626 0.8902 0.033 Uiso calc U . R 1 . .
C C35 0.26728(15) 0.48123(13) 0.81206(9) 0.0247(4) Uani d . . . 1 . .
H H35 0.2161 0.4475 0.8323 0.03 Uiso calc U . R 1 . .
C C36 0.27618(14) 0.46152(12) 0.74796(8) 0.0198(3) Uani d . . . 1 . .
H H36 0.2317 0.4141 0.7246 0.024 Uiso calc U . R 1 . .
C C41 0.34823(13) 0.59148(11) 0.58837(8) 0.0176(3) Uani d . . . 1 . .
C C42 0.28619(14) 0.66450(12) 0.60792(9) 0.0215(4) Uani d . . . 1 . .
H H42 0.2657 0.6634 0.6497 0.026 Uiso calc U . R 1 . .
C C43 0.25465(15) 0.73870(12) 0.56592(9) 0.0261(4) Uani d . . . 1 . .
H H43 0.2119 0.7882 0.579 0.031 Uiso calc U . R 1 . .
C C44 0.28486(15) 0.74137(12) 0.50523(9) 0.0262(4) Uani d . . . 1 . .
H H44 0.2618 0.792 0.4766 0.031 Uiso calc U . R 1 . .
C C45 0.34862(14) 0.67046(12) 0.48609(9) 0.0231(4) Uani d . . . 1 . .
H H45 0.3711 0.6734 0.4449 0.028 Uiso calc U . R 1 . .
C C46 0.37970(14) 0.59496(12) 0.52717(8) 0.0200(4) Uani d . . . 1 . .
H H46 0.4223 0.5457 0.5137 0.024 Uiso calc U . R 1 . .
C C51 0.51760(13) 0.45548(11) 0.64874(7) 0.0151(3) Uani d . . . 1 . .
C C52 0.59794(14) 0.51358(12) 0.63071(8) 0.0179(3) Uani d . . . 1 . .
H H52 0.5772 0.5698 0.6075 0.021 Uiso calc U . R 1 . .
C C53 0.70889(14) 0.48865(12) 0.64705(8) 0.0194(3) Uani d . . . 1 . .
H H53 0.7638 0.5275 0.6342 0.023 Uiso calc U . R 1 . .
C C54 0.73963(13) 0.40797(12) 0.68178(8) 0.0191(3) Uani d . . . 1 . .
H H54 0.8156 0.3919 0.6932 0.023 Uiso calc U . R 1 . .
C C55 0.65958(14) 0.34997(12) 0.70018(8) 0.0187(3) Uani d . . . 1 . .
H H55 0.6809 0.2943 0.7239 0.022 Uiso calc U . R 1 . .
C C56 0.54899(13) 0.37355(12) 0.68384(8) 0.0176(3) Uani d . . . 1 . .
H H56 0.4943 0.3341 0.6965 0.021 Uiso calc U . R 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 C5 . 1.640(2) ?
B1 C1 . 1.647(2) ?
B1 C11 . 1.663(2) ?
B1 C21 . 1.664(2) ?
C1 C2 . 1.549(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
P1 C41 . 1.8014(17) ?
P1 C31 . 1.8091(16) ?
P1 C51 . 1.8094(16) ?
P1 C2 . 1.8560(16) ?
C2 C3 . 1.562(2) ?
C2 H2 . 1.0 ?
C3 C4 . 1.524(2) ?
C3 C9 . 1.540(2) ?
C3 H3 . 1.0 ?
C4 C6 . 1.333(2) ?
C4 C5 . 1.497(2) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.501(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.522(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.524(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C11 C16 . 1.390(2) ?
C11 C12 . 1.396(2) ?
C12 F12 . 1.3529(18) ?
C12 C13 . 1.382(2) ?
C13 F13 . 1.3468(19) ?
C13 C14 . 1.376(2) ?
C14 F14 . 1.3438(19) ?
C14 C15 . 1.373(3) ?
C15 F15 . 1.3522(19) ?
C15 C16 . 1.385(2) ?
C16 F16 . 1.3562(19) ?
C21 C22 . 1.389(2) ?
C21 C26 . 1.392(2) ?
F22 C22 . 1.362(2) ?
C22 C23 . 1.379(3) ?
F23 C23 . 1.346(2) ?
C23 C24 . 1.374(3) ?
F24 C24 . 1.350(2) ?
C24 C25 . 1.376(3) ?
F25 C25 . 1.349(2) ?
C25 C26 . 1.382(3) ?
F26 C26 . 1.3558(19) ?
C31 C36 . 1.390(2) ?
C31 C32 . 1.401(2) ?
C32 C33 . 1.384(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.389(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.380(3) ?
C34 H34 . 0.95 ?
C35 C36 . 1.391(2) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C41 C42 . 1.397(2) ?
C41 C46 . 1.400(2) ?
C42 C43 . 1.387(3) ?
C42 H42 . 0.95 ?
C43 C44 . 1.383(3) ?
C43 H43 . 0.95 ?
C44 C45 . 1.384(3) ?
C44 H44 . 0.95 ?
C45 C46 . 1.390(2) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
C51 C52 . 1.393(2) ?
C51 C56 . 1.399(2) ?
C52 C53 . 1.392(2) ?
C52 H52 . 0.95 ?
C53 C54 . 1.379(2) ?
C53 H53 . 0.95 ?
C54 C55 . 1.393(2) ?
C54 H54 . 0.95 ?
C55 C56 . 1.383(2) ?
C55 H55 . 0.95 ?
C56 H56 . 0.95 ?

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
C5 B1 C1 . . 105.74(13) ?
C5 B1 C11 . . 114.90(13) ?
C1 B1 C11 . . 106.43(13) ?
C5 B1 C21 . . 108.68(13) ?
C1 B1 C21 . . 115.32(13) ?
C11 B1 C21 . . 106.05(13) ?
C2 C1 B1 . . 114.64(13) ?
C2 C1 H1A . . 108.6 ?
B1 C1 H1A . . 108.6 ?
C2 C1 H1B . . 108.6 ?
B1 C1 H1B . . 108.6 ?
H1A C1 H1B . . 107.6 ?
C41 P1 C31 . . 108.95(8) ?
C41 P1 C51 . . 110.21(8) ?
C31 P1 C51 . . 103.15(7) ?
C41 P1 C2 . . 108.81(7) ?
C31 P1 C2 . . 114.45(8) ?
C51 P1 C2 . . 111.14(7) ?
C1 C2 C3 . . 112.36(13) ?
C1 C2 P1 . . 109.28(10) ?
C3 C2 P1 . . 111.86(11) ?
C1 C2 H2 . . 107.7 ?
C3 C2 H2 . . 107.7 ?
P1 C2 H2 . . 107.7 ?
C4 C3 C9 . . 111.18(13) ?
C4 C3 C2 . . 109.24(13) ?
C9 C3 C2 . . 115.21(13) ?
C4 C3 H3 . . 106.9 ?
C9 C3 H3 . . 106.9 ?
C2 C3 H3 . . 106.9 ?
C6 C4 C5 . . 123.09(15) ?
C6 C4 C3 . . 122.00(15) ?
C5 C4 C3 . . 114.90(14) ?
C4 C5 B1 . . 108.90(13) ?
C4 C5 H5A . . 109.9 ?
B1 C5 H5A . . 109.9 ?
C4 C5 H5B . . 109.9 ?
B1 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
C4 C6 C7 . . 125.50(16) ?
C4 C6 H6 . . 117.2 ?
C7 C6 H6 . . 117.2 ?
C6 C7 C8 . . 110.32(14) ?
C6 C7 H7A . . 109.6 ?
C8 C7 H7A . . 109.6 ?
C6 C7 H7B . . 109.6 ?
C8 C7 H7B . . 109.6 ?
H7A C7 H7B . . 108.1 ?
C7 C8 C9 . . 109.72(15) ?
C7 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
C7 C8 H8B . . 109.7 ?
C9 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C8 C9 C3 . . 111.97(14) ?
C8 C9 H9A . . 109.2 ?
C3 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C3 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C16 C11 C12 . . 112.39(15) ?
C16 C11 B1 . . 126.98(14) ?
C12 C11 B1 . . 120.60(14) ?
F12 C12 C13 . . 115.18(14) ?
F12 C12 C11 . . 119.77(14) ?
C13 C12 C11 . . 125.03(15) ?
F13 C13 C14 . . 119.86(15) ?
F13 C13 C12 . . 120.67(15) ?
C14 C13 C12 . . 119.41(16) ?
F14 C14 C15 . . 120.66(15) ?
F14 C14 C13 . . 120.80(16) ?
C15 C14 C13 . . 118.54(15) ?
F15 C15 C14 . . 120.06(15) ?
F15 C15 C16 . . 119.96(15) ?
C14 C15 C16 . . 119.97(15) ?
F16 C16 C15 . . 114.49(14) ?
F16 C16 C11 . . 120.97(14) ?
C15 C16 C11 . . 124.55(16) ?
C22 C21 C26 . . 112.75(15) ?
C22 C21 B1 . . 127.30(15) ?
C26 C21 B1 . . 119.91(14) ?
F22 C22 C23 . . 114.04(15) ?
F22 C22 C21 . . 121.03(15) ?
C23 C22 C21 . . 124.88(17) ?
F23 C23 C24 . . 120.39(17) ?
F23 C23 C22 . . 120.29(18) ?
C24 C23 C22 . . 119.32(17) ?
F24 C24 C23 . . 120.31(18) ?
F24 C24 C25 . . 120.61(18) ?
C23 C24 C25 . . 119.06(17) ?
F25 C25 C24 . . 119.56(16) ?
F25 C25 C26 . . 121.09(17) ?
C24 C25 C26 . . 119.33(17) ?
F26 C26 C25 . . 115.46(15) ?
F26 C26 C21 . . 119.90(15) ?
C25 C26 C21 . . 124.60(16) ?
C36 C31 C32 . . 119.88(15) ?
C36 C31 P1 . . 122.75(13) ?
C32 C31 P1 . . 117.23(13) ?
C33 C32 C31 . . 119.71(17) ?
C33 C32 H32 . . 120.1 ?
C31 C32 H32 . . 120.1 ?
C32 C33 C34 . . 120.20(17) ?
C32 C33 H33 . . 119.9 ?
C34 C33 H33 . . 119.9 ?
C35 C34 C33 . . 120.14(16) ?
C35 C34 H34 . . 119.9 ?
C33 C34 H34 . . 119.9 ?
C34 C35 C36 . . 120.35(17) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C31 C36 C35 . . 119.71(16) ?
C31 C36 H36 . . 120.1 ?
C35 C36 H36 . . 120.1 ?
C42 C41 C46 . . 119.62(16) ?
C42 C41 P1 . . 120.32(13) ?
C46 C41 P1 . . 119.58(13) ?
C43 C42 C41 . . 119.55(17) ?
C43 C42 H42 . . 120.2 ?
C41 C42 H42 . . 120.2 ?
C44 C43 C42 . . 120.64(17) ?
C44 C43 H43 . . 119.7 ?
C42 C43 H43 . . 119.7 ?
C43 C44 C45 . . 120.20(17) ?
C43 C44 H44 . . 119.9 ?
C45 C44 H44 . . 119.9 ?
C44 C45 C46 . . 119.93(17) ?
C44 C45 H45 . . 120.0 ?
C46 C45 H45 . . 120.0 ?
C45 C46 C41 . . 120.02(17) ?
C45 C46 H46 . . 120.0 ?
C41 C46 H46 . . 120.0 ?
C52 C51 C56 . . 119.90(15) ?
C52 C51 P1 . . 122.88(13) ?
C56 C51 P1 . . 116.88(12) ?
C53 C52 C51 . . 119.48(15) ?
C53 C52 H52 . . 120.3 ?
C51 C52 H52 . . 120.3 ?
C54 C53 C52 . . 120.50(15) ?
C54 C53 H53 . . 119.8 ?
C52 C53 H53 . . 119.8 ?
C53 C54 C55 . . 120.18(15) ?
C53 C54 H54 . . 119.9 ?
C55 C54 H54 . . 119.9 ?
C56 C55 C54 . . 119.92(16) ?
C56 C55 H55 . . 120.0 ?
C54 C55 H55 . . 120.0 ?
C55 C56 C51 . . 120.02(15) ?
C55 C56 H56 . . 120.0 ?
C51 C56 H56 . . 120.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 B1 C1 C2 . . . . 51.48(17) ?
C11 B1 C1 C2 . . . . 174.11(13) ?
C21 B1 C1 C2 . . . . -68.62(18) ?
B1 C1 C2 C3 . . . . -51.08(18) ?
B1 C1 C2 P1 . . . . -175.86(11) ?
C41 P1 C2 C1 . . . . 91.54(12) ?
C31 P1 C2 C1 . . . . -146.33(10) ?
C51 P1 C2 C1 . . . . -29.99(13) ?
C41 P1 C2 C3 . . . . -33.53(13) ?
C31 P1 C2 C3 . . . . 88.59(12) ?
C51 P1 C2 C3 . . . . -155.07(11) ?
C1 C2 C3 C4 . . . . 51.51(17) ?
P1 C2 C3 C4 . . . . 174.86(11) ?
C1 C2 C3 C9 . . . . 177.47(13) ?
P1 C2 C3 C9 . . . . -59.18(16) ?
C9 C3 C4 C6 . . . . -10.1(2) ?
C2 C3 C4 C6 . . . . 118.15(17) ?
C9 C3 C4 C5 . . . . 170.74(14) ?
C2 C3 C4 C5 . . . . -61.02(17) ?
C6 C4 C5 B1 . . . . -114.42(18) ?
C3 C4 C5 B1 . . . . 64.75(17) ?
C1 B1 C5 C4 . . . . -55.58(16) ?
C11 B1 C5 C4 . . . . -172.62(13) ?
C21 B1 C5 C4 . . . . 68.78(16) ?
C5 C4 C6 C7 . . . . 176.97(16) ?
C3 C4 C6 C7 . . . . -2.1(3) ?
C4 C6 C7 C8 . . . . -17.7(3) ?
C6 C7 C8 C9 . . . . 48.6(2) ?
C7 C8 C9 C3 . . . . -63.26(18) ?
C4 C3 C9 C8 . . . . 42.26(18) ?
C2 C3 C9 C8 . . . . -82.70(17) ?
C5 B1 C11 C16 . . . . 12.9(2) ?
C1 B1 C11 C16 . . . . -103.76(18) ?
C21 B1 C11 C16 . . . . 132.95(16) ?
C5 B1 C11 C12 . . . . -169.22(14) ?
C1 B1 C11 C12 . . . . 74.12(18) ?
C21 B1 C11 C12 . . . . -49.16(19) ?
C16 C11 C12 F12 . . . . 176.35(14) ?
B1 C11 C12 F12 . . . . -1.8(2) ?
C16 C11 C12 C13 . . . . -2.3(2) ?
B1 C11 C12 C13 . . . . 179.58(15) ?
F12 C12 C13 F13 . . . . 2.1(2) ?
C11 C12 C13 F13 . . . . -179.21(14) ?
F12 C12 C13 C14 . . . . -175.06(14) ?
C11 C12 C13 C14 . . . . 3.6(3) ?
F13 C13 C14 F14 . . . . 0.5(2) ?
C12 C13 C14 F14 . . . . 177.74(15) ?
F13 C13 C14 C15 . . . . -178.60(15) ?
C12 C13 C14 C15 . . . . -1.4(2) ?
F14 C14 C15 F15 . . . . 0.2(2) ?
C13 C14 C15 F15 . . . . 179.37(15) ?
F14 C14 C15 C16 . . . . 179.10(15) ?
C13 C14 C15 C16 . . . . -1.8(2) ?
F15 C15 C16 F16 . . . . 2.0(2) ?
C14 C15 C16 F16 . . . . -176.88(14) ?
F15 C15 C16 C11 . . . . -177.94(15) ?
C14 C15 C16 C11 . . . . 3.2(3) ?
C12 C11 C16 F16 . . . . 178.91(14) ?
B1 C11 C16 F16 . . . . -3.1(2) ?
C12 C11 C16 C15 . . . . -1.2(2) ?
B1 C11 C16 C15 . . . . 176.86(15) ?
C5 B1 C21 C22 . . . . -121.67(17) ?
C1 B1 C21 C22 . . . . -3.2(2) ?
C11 B1 C21 C22 . . . . 114.30(18) ?
C5 B1 C21 C26 . . . . 60.85(19) ?
C1 B1 C21 C26 . . . . 179.33(14) ?
C11 B1 C21 C26 . . . . -63.18(18) ?
C26 C21 C22 F22 . . . . 175.68(15) ?
B1 C21 C22 F22 . . . . -1.9(3) ?
C26 C21 C22 C23 . . . . -1.9(3) ?
B1 C21 C22 C23 . . . . -179.56(17) ?
F22 C22 C23 F23 . . . . 2.3(3) ?
C21 C22 C23 F23 . . . . -179.97(18) ?
F22 C22 C23 C24 . . . . -177.32(17) ?
C21 C22 C23 C24 . . . . 0.4(3) ?
F23 C23 C24 F24 . . . . 0.4(3) ?
C22 C23 C24 F24 . . . . 179.95(18) ?
F23 C23 C24 C25 . . . . -177.77(19) ?
C22 C23 C24 C25 . . . . 1.8(3) ?
F24 C24 C25 F25 . . . . -1.9(3) ?
C23 C24 C25 F25 . . . . 176.27(17) ?
F24 C24 C25 C26 . . . . 179.50(17) ?
C23 C24 C25 C26 . . . . -2.4(3) ?
F25 C25 C26 F26 . . . . 0.0(2) ?
C24 C25 C26 F26 . . . . 178.59(16) ?
F25 C25 C26 C21 . . . . -177.86(15) ?
C24 C25 C26 C21 . . . . 0.8(3) ?
C22 C21 C26 F26 . . . . -176.42(14) ?
B1 C21 C26 F26 . . . . 1.4(2) ?
C22 C21 C26 C25 . . . . 1.3(2) ?
B1 C21 C26 C25 . . . . 179.15(16) ?
C41 P1 C31 C36 . . . . 123.95(14) ?
C51 P1 C31 C36 . . . . -118.97(14) ?
C2 P1 C31 C36 . . . . 1.90(17) ?
C41 P1 C31 C32 . . . . -60.31(15) ?
C51 P1 C31 C32 . . . . 56.77(14) ?
C2 P1 C31 C32 . . . . 177.64(12) ?
C36 C31 C32 C33 . . . . -1.2(3) ?
P1 C31 C32 C33 . . . . -177.03(13) ?
C31 C32 C33 C34 . . . . 0.7(3) ?
C32 C33 C34 C35 . . . . -0.1(3) ?
C33 C34 C35 C36 . . . . 0.1(3) ?
C32 C31 C36 C35 . . . . 1.1(2) ?
P1 C31 C36 C35 . . . . 176.75(13) ?
C34 C35 C36 C31 . . . . -0.6(3) ?
C31 P1 C41 C42 . . . . -19.72(15) ?
C51 P1 C41 C42 . . . . -132.22(13) ?
C2 P1 C41 C42 . . . . 105.68(14) ?
C31 P1 C41 C46 . . . . 168.21(13) ?
C51 P1 C41 C46 . . . . 55.71(15) ?
C2 P1 C41 C46 . . . . -66.39(14) ?
C46 C41 C42 C43 . . . . 1.3(2) ?
P1 C41 C42 C43 . . . . -170.79(13) ?
C41 C42 C43 C44 . . . . -0.6(3) ?
C42 C43 C44 C45 . . . . -1.0(3) ?
C43 C44 C45 C46 . . . . 1.9(3) ?
C44 C45 C46 C41 . . . . -1.2(2) ?
C42 C41 C46 C45 . . . . -0.4(2) ?
P1 C41 C46 C45 . . . . 171.72(12) ?
C41 P1 C51 C52 . . . . 8.56(16) ?
C31 P1 C51 C52 . . . . -107.63(14) ?
C2 P1 C51 C52 . . . . 129.28(14) ?
C41 P1 C51 C56 . . . . -178.12(12) ?
C31 P1 C51 C56 . . . . 65.69(14) ?
C2 P1 C51 C56 . . . . -57.40(14) ?
C56 C51 C52 C53 . . . . 1.0(2) ?
P1 C51 C52 C53 . . . . 174.08(12) ?
C51 C52 C53 C54 . . . . -1.1(2) ?
C52 C53 C54 C55 . . . . 0.8(2) ?
C53 C54 C55 C56 . . . . -0.3(2) ?
C54 C55 C56 C51 . . . . 0.2(2) ?
C52 C51 C56 C55 . . . . -0.5(2) ?
P1 C51 C56 C55 . . . . -174.01(12) ?


####################################################################### 
# 
# 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_erk9518
_database_code_depnum_ccdc_archive 'CCDC 1922911'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 B F10'
_chemical_formula_iupac          ?
_chemical_formula_weight         546.25

_chemical_melting_point          ?

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

_cell_length_a                   6.4255(4)
_cell_length_b                   17.4610(10)
_cell_length_c                   21.2763(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.037(4)
_cell_angle_gamma                90
_cell_volume                     2377.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      3.2800
_cell_measurement_theta_max      66.6604
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    1.255
_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  0.77
_exptl_absorpt_correction_T_max  0.92

_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            11802
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_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             4116
_reflns_number_gt                3248
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1007
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     343
_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)+(0.0423P)²+0.7890P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.215
_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'

_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
C C1 0.1689(3) 0.02424(12) 0.66741(12) 0.0304(5) Uani d . . . 1 . .
H H1A 0.1789 0.0261 0.6232 0.036 Uiso calc U . R 1 . .
H H1B 0.0653 -0.0067 0.6841 0.036 Uiso calc U . R 1 . .
C C2 0.2983(3) 0.06442(11) 0.70559(10) 0.0235(4) Uani d . . . 1 . .
H H2 0.284 0.0612 0.7496 0.028 Uiso calc U . R 1 . .
C C3 0.4679(3) 0.11526(10) 0.68428(9) 0.0193(4) Uani d . . . 1 . .
H H3 0.4565 0.1136 0.6371 0.023 Uiso calc U . R 1 . .
C C4 0.4497(3) 0.20103(10) 0.70368(9) 0.0178(4) Uani d . . . 1 . .
C C5 0.6010(3) 0.25290(10) 0.66936(9) 0.0185(4) Uani d . . . 1 . .
H H5A 0.6171 0.3009 0.694 0.022 Uiso calc U . R 1 . .
H H5B 0.7389 0.2272 0.6736 0.022 Uiso calc U . R 1 . .
C C6 0.5020(3) 0.20901(11) 0.77669(9) 0.0200(4) Uani d . . . 1 . .
H H6 0.3981 0.1768 0.797 0.024 Uiso calc U . R 1 . .
C C7 0.7176(3) 0.17642(11) 0.79775(9) 0.0234(5) Uani d . . . 1 . .
H H7A 0.7428 0.1805 0.8442 0.028 Uiso calc U . R 1 . .
H H7B 0.8258 0.207 0.7788 0.028 Uiso calc U . R 1 . .
C C8 0.7362(3) 0.09267(12) 0.77816(10) 0.0259(5) Uani d . . . 1 . .
H H8A 0.8805 0.0746 0.7898 0.031 Uiso calc U . R 1 . .
H H8B 0.6403 0.0611 0.8013 0.031 Uiso calc U . R 1 . .
C C9 0.6835(3) 0.08215(11) 0.70739(9) 0.0220(4) Uani d . . . 1 . .
H H9A 0.6858 0.0268 0.6972 0.026 Uiso calc U . R 1 . .
H H9B 0.792 0.1076 0.6845 0.026 Uiso calc U . R 1 . .
C C10 0.4680(3) 0.29089(11) 0.79736(9) 0.0229(4) Uani d . . . 1 . .
C C11 0.2524(3) 0.32211(12) 0.77802(11) 0.0293(5) Uani d . . . 1 . .
H H11A 0.1493 0.2964 0.8028 0.035 Uiso calc U . R 1 . .
H H11B 0.2493 0.3776 0.7875 0.035 Uiso calc U . R 1 . .
C C12 0.1926(3) 0.30981(11) 0.70855(11) 0.0262(5) Uani d . . . 1 . .
C C13 0.2228(3) 0.22852(11) 0.68777(10) 0.0218(4) Uani d . . . 1 . .
H H13A 0.1869 0.2247 0.6417 0.026 Uiso calc U . R 1 . .
H H13B 0.1267 0.1946 0.7088 0.026 Uiso calc U . R 1 . .
C C14 0.6130(4) 0.33406(12) 0.82789(10) 0.0286(5) Uani d . . . 1 . .
H H14A 0.5824 0.3856 0.838 0.034 Uiso calc U . R 1 . .
H H14B 0.7477 0.3135 0.8397 0.034 Uiso calc U . R 1 . .
C C15 0.1286(4) 0.36594(12) 0.66975(12) 0.0338(5) Uani d . . . 1 . .
H H15A 0.0988 0.3559 0.626 0.041 Uiso calc U . R 1 . .
H H15B 0.1124 0.4162 0.6856 0.041 Uiso calc U . R 1 . .
B B1 0.5596(4) 0.27678(13) 0.59899(11) 0.0202(5) Uani d . . . 1 . .
C C21 0.4754(3) 0.21565(11) 0.54681(9) 0.0225(4) Uani d . . . 1 . .
F F22 0.7981(2) 0.15021(7) 0.55959(6) 0.0319(3) Uani d . . . 1 . .
C C22 0.6025(4) 0.15616(11) 0.53078(9) 0.0253(5) Uani d . . . 1 . .
F F23 0.6700(3) 0.04602(7) 0.47102(6) 0.0445(4) Uani d . . . 1 . .
C C23 0.5400(4) 0.10223(12) 0.48513(10) 0.0319(6) Uani d . . . 1 . .
F F24 0.2783(3) 0.05392(8) 0.41170(6) 0.0513(4) Uani d . . . 1 . .
C C24 0.3423(4) 0.10655(13) 0.45495(10) 0.0350(6) Uani d . . . 1 . .
F F25 0.0186(2) 0.17059(8) 0.43884(6) 0.0473(4) Uani d . . . 1 . .
C C25 0.2111(4) 0.16522(13) 0.46895(10) 0.0320(5) Uani d . . . 1 . .
F F26 0.1479(2) 0.27614(7) 0.52580(6) 0.0343(3) Uani d . . . 1 . .
C C26 0.2803(4) 0.21876(11) 0.51398(10) 0.0267(5) Uani d . . . 1 . .
C C31 0.6259(3) 0.35746(11) 0.57403(9) 0.0190(4) Uani d . . . 1 . .
F F32 0.6746(2) 0.30974(6) 0.47105(5) 0.0293(3) Uani d . . . 1 . .
C C32 0.6787(3) 0.36840(11) 0.51171(9) 0.0212(4) Uani d . . . 1 . .
F F33 0.7860(2) 0.44479(7) 0.42855(5) 0.0306(3) Uani d . . . 1 . .
C C33 0.7387(3) 0.43781(11) 0.48855(9) 0.0228(4) Uani d . . . 1 . .
F F34 0.8010(2) 0.56921(6) 0.50481(6) 0.0293(3) Uani d . . . 1 . .
C C34 0.7485(3) 0.50130(11) 0.52718(9) 0.0216(4) Uani d . . . 1 . .
F F35 0.7102(2) 0.55615(6) 0.62611(6) 0.0307(3) Uani d . . . 1 . .
C C35 0.7012(3) 0.49406(11) 0.58879(9) 0.0215(4) Uani d . . . 1 . .
F F36 0.5966(2) 0.42304(6) 0.67146(5) 0.0266(3) Uani d . . . 1 . .
C C36 0.6424(3) 0.42403(11) 0.61100(9) 0.0196(4) 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
C1 C2 . 1.313(3) ?
C1 H1A . 0.95 ?
C1 H1B . 0.95 ?
C2 C3 . 1.506(3) ?
C2 H2 . 0.95 ?
C3 C9 . 1.542(3) ?
C3 C4 . 1.561(2) ?
C3 H3 . 1.0 ?
C4 C13 . 1.544(3) ?
C4 C5 . 1.557(3) ?
C4 C6 . 1.566(3) ?
C5 B1 . 1.554(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C10 . 1.517(3) ?
C6 C7 . 1.528(3) ?
C6 H6 . 1.0 ?
C7 C8 . 1.528(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.525(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C14 . 1.324(3) ?
C10 C11 . 1.512(3) ?
C11 C12 . 1.509(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C15 . 1.324(3) ?
C12 C13 . 1.504(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.95 ?
C14 H14B . 0.95 ?
C15 H15A . 0.95 ?
C15 H15B . 0.95 ?
B1 C31 . 1.577(3) ?
B1 C21 . 1.600(3) ?
C21 C26 . 1.381(3) ?
C21 C22 . 1.383(3) ?
F22 C22 . 1.353(3) ?
C22 C23 . 1.387(3) ?
F23 C23 . 1.340(3) ?
C23 C24 . 1.374(4) ?
F24 C24 . 1.339(2) ?
C24 C25 . 1.376(4) ?
F25 C25 . 1.345(3) ?
C25 C26 . 1.384(3) ?
F26 C26 . 1.352(3) ?
C31 C36 . 1.402(3) ?
C31 C32 . 1.410(3) ?
F32 C32 . 1.340(2) ?
C32 C33 . 1.376(3) ?
F33 C33 . 1.343(2) ?
C33 C34 . 1.378(3) ?
F34 C34 . 1.332(2) ?
C34 C35 . 1.377(3) ?
F35 C35 . 1.342(2) ?
C35 C36 . 1.376(3) ?
F36 C36 . 1.344(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
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C3 . . 124.4(2) ?
C1 C2 H2 . . 117.8 ?
C3 C2 H2 . . 117.8 ?
C2 C3 C9 . . 109.68(16) ?
C2 C3 C4 . . 114.41(16) ?
C9 C3 C4 . . 111.20(15) ?
C2 C3 H3 . . 107.1 ?
C9 C3 H3 . . 107.1 ?
C4 C3 H3 . . 107.1 ?
C13 C4 C5 . . 109.44(15) ?
C13 C4 C3 . . 109.35(15) ?
C5 C4 C3 . . 111.71(15) ?
C13 C4 C6 . . 107.81(15) ?
C5 C4 C6 . . 108.98(15) ?
C3 C4 C6 . . 109.46(15) ?
B1 C5 C4 . . 123.15(17) ?
B1 C5 H5A . . 106.5 ?
C4 C5 H5A . . 106.5 ?
B1 C5 H5B . . 106.5 ?
C4 C5 H5B . . 106.5 ?
H5A C5 H5B . . 106.5 ?
C10 C6 C7 . . 114.56(17) ?
C10 C6 C4 . . 110.33(15) ?
C7 C6 C4 . . 111.57(16) ?
C10 C6 H6 . . 106.6 ?
C7 C6 H6 . . 106.6 ?
C4 C6 H6 . . 106.6 ?
C6 C7 C8 . . 111.54(17) ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
C9 C8 C7 . . 111.63(16) ?
C9 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
C9 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 108.0 ?
C8 C9 C3 . . 112.65(16) ?
C8 C9 H9A . . 109.1 ?
C3 C9 H9A . . 109.1 ?
C8 C9 H9B . . 109.1 ?
C3 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C14 C10 C11 . . 121.13(19) ?
C14 C10 C6 . . 124.5(2) ?
C11 C10 C6 . . 114.36(17) ?
C12 C11 C10 . . 111.32(17) ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C15 C12 C13 . . 123.8(2) ?
C15 C12 C11 . . 122.95(19) ?
C13 C12 C11 . . 113.20(18) ?
C12 C13 C4 . . 111.85(16) ?
C12 C13 H13A . . 109.2 ?
C4 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C4 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C10 C14 H14A . . 120.0 ?
C10 C14 H14B . . 120.0 ?
H14A C14 H14B . . 120.0 ?
C12 C15 H15A . . 120.0 ?
C12 C15 H15B . . 120.0 ?
H15A C15 H15B . . 120.0 ?
C5 B1 C31 . . 122.38(17) ?
C5 B1 C21 . . 120.56(17) ?
C31 B1 C21 . . 116.55(17) ?
C26 C21 C22 . . 115.74(18) ?
C26 C21 B1 . . 124.14(18) ?
C22 C21 B1 . . 120.10(19) ?
F22 C22 C21 . . 119.42(18) ?
F22 C22 C23 . . 117.8(2) ?
C21 C22 C23 . . 122.8(2) ?
F23 C23 C24 . . 120.3(2) ?
F23 C23 C22 . . 120.4(2) ?
C24 C23 C22 . . 119.3(2) ?
F24 C24 C23 . . 119.9(2) ?
F24 C24 C25 . . 120.2(2) ?
C23 C24 C25 . . 119.90(19) ?
F25 C25 C24 . . 120.3(2) ?
F25 C25 C26 . . 120.6(2) ?
C24 C25 C26 . . 119.1(2) ?
F26 C26 C21 . . 119.54(18) ?
F26 C26 C25 . . 117.4(2) ?
C21 C26 C25 . . 123.1(2) ?
C36 C31 C32 . . 113.74(17) ?
C36 C31 B1 . . 124.10(17) ?
C32 C31 B1 . . 122.15(17) ?
F32 C32 C33 . . 115.62(17) ?
F32 C32 C31 . . 120.72(17) ?
C33 C32 C31 . . 123.65(18) ?
F33 C33 C32 . . 120.93(18) ?
F33 C33 C34 . . 119.44(17) ?
C32 C33 C34 . . 119.63(18) ?
F34 C34 C35 . . 120.38(17) ?
F34 C34 C33 . . 120.17(18) ?
C35 C34 C33 . . 119.44(17) ?
F35 C35 C36 . . 120.90(18) ?
F35 C35 C34 . . 119.18(17) ?
C36 C35 C34 . . 119.92(17) ?
F36 C36 C35 . . 115.46(16) ?
F36 C36 C31 . . 120.93(17) ?
C35 C36 C31 . . 123.60(18) ?

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
C1 C2 C3 C9 . . . . -113.5(2) ?
C1 C2 C3 C4 . . . . 120.8(2) ?
C2 C3 C4 C13 . . . . -47.4(2) ?
C9 C3 C4 C13 . . . . -172.29(16) ?
C2 C3 C4 C5 . . . . -168.67(16) ?
C9 C3 C4 C5 . . . . 66.4(2) ?
C2 C3 C4 C6 . . . . 70.5(2) ?
C9 C3 C4 C6 . . . . -54.4(2) ?
C13 C4 C5 B1 . . . . -45.3(2) ?
C3 C4 C5 B1 . . . . 75.9(2) ?
C6 C4 C5 B1 . . . . -163.00(17) ?
C13 C4 C6 C10 . . . . -56.5(2) ?
C5 C4 C6 C10 . . . . 62.2(2) ?
C3 C4 C6 C10 . . . . -175.37(16) ?
C13 C4 C6 C7 . . . . 174.95(15) ?
C5 C4 C6 C7 . . . . -66.4(2) ?
C3 C4 C6 C7 . . . . 56.1(2) ?
C10 C6 C7 C8 . . . . 177.08(16) ?
C4 C6 C7 C8 . . . . -56.7(2) ?
C6 C7 C8 C9 . . . . 54.9(2) ?
C7 C8 C9 C3 . . . . -54.0(2) ?
C2 C3 C9 C8 . . . . -73.1(2) ?
C4 C3 C9 C8 . . . . 54.4(2) ?
C7 C6 C10 C14 . . . . 3.9(3) ?
C4 C6 C10 C14 . . . . -123.0(2) ?
C7 C6 C10 C11 . . . . -178.33(18) ?
C4 C6 C10 C11 . . . . 54.8(2) ?
C14 C10 C11 C12 . . . . 127.1(2) ?
C6 C10 C11 C12 . . . . -50.7(2) ?
C10 C11 C12 C15 . . . . -126.6(2) ?
C10 C11 C12 C13 . . . . 50.7(2) ?
C15 C12 C13 C4 . . . . 120.9(2) ?
C11 C12 C13 C4 . . . . -56.5(2) ?
C5 C4 C13 C12 . . . . -60.3(2) ?
C3 C4 C13 C12 . . . . 177.00(16) ?
C6 C4 C13 C12 . . . . 58.1(2) ?
C4 C5 B1 C31 . . . . 145.56(19) ?
C4 C5 B1 C21 . . . . -43.0(3) ?
C5 B1 C21 C26 . . . . 113.4(2) ?
C31 B1 C21 C26 . . . . -74.6(3) ?
C5 B1 C21 C22 . . . . -68.4(3) ?
C31 B1 C21 C22 . . . . 103.5(2) ?
C26 C21 C22 F22 . . . . 178.28(18) ?
B1 C21 C22 F22 . . . . 0.0(3) ?
C26 C21 C22 C23 . . . . -0.5(3) ?
B1 C21 C22 C23 . . . . -178.78(19) ?
F22 C22 C23 F23 . . . . 0.6(3) ?
C21 C22 C23 F23 . . . . 179.45(19) ?
F22 C22 C23 C24 . . . . 179.98(19) ?
C21 C22 C23 C24 . . . . -1.2(3) ?
F23 C23 C24 F24 . . . . 0.7(3) ?
C22 C23 C24 F24 . . . . -178.62(18) ?
F23 C23 C24 C25 . . . . -178.86(18) ?
C22 C23 C24 C25 . . . . 1.8(3) ?
F24 C24 C25 F25 . . . . -0.7(3) ?
C23 C24 C25 F25 . . . . 178.9(2) ?
F24 C24 C25 C26 . . . . 179.75(19) ?
C23 C24 C25 C26 . . . . -0.7(3) ?
C22 C21 C26 F26 . . . . -178.59(17) ?
B1 C21 C26 F26 . . . . -0.4(3) ?
C22 C21 C26 C25 . . . . 1.7(3) ?
B1 C21 C26 C25 . . . . 179.90(19) ?
F25 C25 C26 F26 . . . . -0.4(3) ?
C24 C25 C26 F26 . . . . 179.13(19) ?
F25 C25 C26 C21 . . . . 179.30(19) ?
C24 C25 C26 C21 . . . . -1.2(3) ?
C5 B1 C31 C36 . . . . -28.2(3) ?
C21 B1 C31 C36 . . . . 159.98(19) ?
C5 B1 C31 C32 . . . . 150.5(2) ?
C21 B1 C31 C32 . . . . -21.3(3) ?
C36 C31 C32 F32 . . . . 178.69(18) ?
B1 C31 C32 F32 . . . . -0.1(3) ?
C36 C31 C32 C33 . . . . -0.7(3) ?
B1 C31 C32 C33 . . . . -179.51(19) ?
F32 C32 C33 F33 . . . . 1.0(3) ?
C31 C32 C33 F33 . . . . -179.59(18) ?
F32 C32 C33 C34 . . . . -179.66(18) ?
C31 C32 C33 C34 . . . . -0.2(3) ?
F33 C33 C34 F34 . . . . 1.1(3) ?
C32 C33 C34 F34 . . . . -178.23(18) ?
F33 C33 C34 C35 . . . . -179.62(18) ?
C32 C33 C34 C35 . . . . 1.0(3) ?
F34 C34 C35 F35 . . . . -0.5(3) ?
C33 C34 C35 F35 . . . . -179.72(18) ?
F34 C34 C35 C36 . . . . 178.45(18) ?
C33 C34 C35 C36 . . . . -0.8(3) ?
F35 C35 C36 F36 . . . . -0.2(3) ?
C34 C35 C36 F36 . . . . -179.11(18) ?
F35 C35 C36 C31 . . . . 178.68(18) ?
C34 C35 C36 C31 . . . . -0.2(3) ?
C32 C31 C36 F36 . . . . 179.76(17) ?
B1 C31 C36 F36 . . . . -1.5(3) ?
C32 C31 C36 C35 . . . . 0.9(3) ?
B1 C31 C36 C35 . . . . 179.72(19) ?

####################################################################### 
# 
# 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_erk9381
_database_code_depnum_ccdc_archive 'CCDC 1922910'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H30 B F10 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         742.42

_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                   12.4783(5)
_cell_length_b                   15.7635(6)
_cell_length_c                   20.7617(7)
_cell_angle_alpha                102.312(2)
_cell_angle_beta                 93.184(2)
_cell_angle_gamma                112.263(2)
_cell_volume                     3650.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8015
_cell_measurement_theta_min      3.1316
_cell_measurement_theta_max      66.5922
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520

_exptl_absorpt_coefficient_mu    1.372
_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  0.75
_exptl_absorpt_correction_T_max  0.90

_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            57658
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_full        66.95
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24

_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.

A badly disordered mixture of dichloromethane and pentane solvens were 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 molecules. 

Part of the seven membered ring is disordered over two positions.  Several restraints (SADI, SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_reflns_number_total             12835
_reflns_number_gt                9341
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1227
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         12835
_refine_ls_number_parameters     956
_refine_ls_number_restraints     35
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²] 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         0.383
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       '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
P P1A 0.45560(5) 0.28834(4) 0.06521(3) 0.01916(14) Uani d . . . 1.0 . .
P P1B -0.03455(5) 0.71869(4) 0.64642(3) 0.01898(14) Uani d . . . 1.0 . .
B B1A 0.7709(2) 0.4984(2) 0.19056(14) 0.0223(6) Uani d . . . 1.0 . .
B B1B 0.3285(3) 0.8685(2) 0.71318(14) 0.0218(6) Uani d . . . 1.0 . .
C C1A 0.6375(2) 0.44806(17) 0.14546(12) 0.0252(6) Uani d . . . 1.0 . .
H H101 0.5785 0.4477 0.1755 0.03 Uiso calc U . R 1.0 . .
H H102 0.6324 0.486 0.114 0.03 Uiso calc U . R 1.0 . .
C C2A 0.6097(2) 0.34623(17) 0.10619(12) 0.0214(5) Uani d . . . 1.0 . .
H H2A 0.6189 0.3106 0.1391 0.026 Uiso calc U . R 1.0 . .
C C3A 0.6995(2) 0.34487(17) 0.05761(12) 0.0232(5) Uani d . . . 1.0 . .
H H3A 0.6939 0.3847 0.027 0.028 Uiso calc U . R 1.0 . .
C C4A 0.8241(2) 0.39310(18) 0.09661(12) 0.0236(6) Uani d . . . 1.0 . .
C C5A 0.8362(2) 0.42536(18) 0.17138(12) 0.0241(6) Uani d . . . 1.0 . .
H H501 0.9201 0.4577 0.1908 0.029 Uiso calc U . R 1.0 . .
H H502 0.8001 0.3699 0.1899 0.029 Uiso calc U . R 1.0 . .
C C6A 0.9154(2) 0.4093(2) 0.06444(13) 0.0361(7) Uani d . . D 1.0 . .
H H6A 0.9904 0.4347 0.0908 0.043 Uiso calc U P R 0.843(7) A 1
H H6C 0.9822 0.4649 0.0861 0.043 Uiso calc U P R 0.157(7) A 2
C C9A 0.7191(2) 0.2484(2) -0.05366(13) 0.0344(7) Uani d . . D 1.0 . .
H H901 0.6899 0.2879 -0.0746 0.041 Uiso calc U P R 0.843(7) A 1
H H902 0.6852 0.1833 -0.0831 0.041 Uiso calc U P R 0.843(7) A 1
H H921 0.6549 0.2452 -0.0856 0.041 Uiso calc U P R 0.157(7) A 2
H H922 0.7334 0.1903 -0.0697 0.041 Uiso calc U P R 0.157(7) A 2
C C7A 0.9120(3) 0.3910(3) -0.01139(16) 0.0312(10) Uani d U P D 0.843(7) A 1
H H701 0.8708 0.4264 -0.0283 0.037 Uiso calc U P R 0.843(7) A 1
H H702 0.9933 0.4164 -0.0211 0.037 Uiso calc U P R 0.843(7) A 1
C C8A 0.8521(3) 0.2873(3) -0.04908(16) 0.0304(10) Uani d U P D 0.843(7) A 1
H H801 0.882 0.2495 -0.0265 0.036 Uiso calc U P R 0.843(7) A 1
H H802 0.8728 0.2798 -0.0947 0.036 Uiso calc U P R 0.843(7) A 1
C C7C 0.9328(14) 0.3537(13) -0.0021(7) 0.027(5) Uani d U P D 0.157(7) A 2
H H721 1.0101 0.3897 -0.0138 0.033 Uiso calc U P R 0.157(7) A 2
H H722 0.9305 0.2918 0.0022 0.033 Uiso calc U P R 0.157(7) A 2
C C8C 0.8363(13) 0.3386(13) -0.0564(8) 0.034(5) Uani d U P D 0.157(7) A 2
H H821 0.8619 0.3272 -0.1005 0.041 Uiso calc U P R 0.157(7) A 2
H H822 0.8193 0.3961 -0.0501 0.041 Uiso calc U P R 0.157(7) A 2
C C10A 0.6764(2) 0.24609(18) 0.01314(12) 0.0258(6) Uani d . . . 1.0 . .
H H10A 0.7156 0.2153 0.0372 0.031 Uiso calc U . R 1.0 . .
H H10B 0.5912 0.2068 0.0054 0.031 Uiso calc U . R 1.0 . .
C C11A 0.7455(2) 0.51870(17) 0.26926(12) 0.0216(5) Uani d . . . 1.0 . .
C C12A 0.6825(2) 0.57422(17) 0.28839(12) 0.0216(5) Uani d . . . 1.0 . .
C C13A 0.6528(2) 0.59491(18) 0.35076(12) 0.0248(6) Uani d . . . 1.0 . .
C C14A 0.6859(2) 0.55949(19) 0.39989(13) 0.0286(6) Uani d . . . 1.0 . .
C C15A 0.7490(2) 0.50402(19) 0.38428(13) 0.0263(6) Uani d . . . 1.0 . .
C C16A 0.7760(2) 0.48569(17) 0.32097(12) 0.0229(5) Uani d . . . 1.0 . .
C C21A 0.8527(2) 0.60362(18) 0.17858(11) 0.0213(5) Uani d . . . 1.0 . .
C C22A 0.8410(2) 0.63551(18) 0.12253(12) 0.0244(6) Uani d . . . 1.0 . .
C C23A 0.9010(2) 0.7267(2) 0.11745(13) 0.0297(6) Uani d . . . 1.0 . .
C C24A 0.9805(2) 0.79322(19) 0.17033(14) 0.0298(6) Uani d . . . 1.0 . .
C C25A 1.0020(2) 0.76484(19) 0.22628(12) 0.0285(6) Uani d . . . 1.0 . .
C C26A 0.9398(2) 0.67243(18) 0.22819(12) 0.0242(6) Uani d . . . 1.0 . .
C C31A 0.4406(2) 0.28214(17) -0.02284(11) 0.0205(5) Uani d . . . 1.0 . .
C C32A 0.4880(2) 0.36409(18) -0.04556(12) 0.0228(5) Uani d . . . 1.0 . .
H H32A 0.5296 0.4239 -0.0148 0.027 Uiso calc U . R 1.0 . .
C C33A 0.4737(2) 0.35749(19) -0.11354(13) 0.0273(6) Uani d . . . 1.0 . .
H H33A 0.5054 0.4131 -0.1291 0.033 Uiso calc U . R 1.0 . .
C C34A 0.4139(3) 0.2710(2) -0.15867(13) 0.0322(7) Uani d . . . 1.0 . .
H H34A 0.4041 0.2673 -0.205 0.039 Uiso calc U . R 1.0 . .
C C35A 0.3680(3) 0.1894(2) -0.13633(13) 0.0343(7) Uani d . . . 1.0 . .
H H35A 0.3278 0.1297 -0.1675 0.041 Uiso calc U . R 1.0 . .
C C36A 0.3808(2) 0.19483(18) -0.06899(12) 0.0264(6) Uani d . . . 1.0 . .
H H36A 0.3487 0.1388 -0.0539 0.032 Uiso calc U . R 1.0 . .
C C41A 0.3824(2) 0.16973(17) 0.07522(11) 0.0213(5) Uani d . . . 1.0 . .
C C42A 0.4403(2) 0.11094(18) 0.07842(12) 0.0268(6) Uani d . . . 1.0 . .
H H42A 0.5225 0.1341 0.0784 0.032 Uiso calc U . R 1.0 . .
C C43A 0.3787(2) 0.01822(18) 0.08169(13) 0.0297(6) Uani d . . . 1.0 . .
H H43A 0.4182 -0.0227 0.0822 0.036 Uiso calc U . R 1.0 . .
C C44A 0.2595(2) -0.01442(19) 0.08417(12) 0.0286(6) Uani d . . . 1.0 . .
H H44A 0.2175 -0.0775 0.0871 0.034 Uiso calc U . R 1.0 . .
C C45A 0.2014(2) 0.04441(18) 0.08235(12) 0.0279(6) Uani d . . . 1.0 . .
H H45A 0.1198 0.0219 0.0845 0.034 Uiso calc U . R 1.0 . .
C C46A 0.2618(2) 0.13591(18) 0.07735(12) 0.0252(6) Uani d . . . 1.0 . .
H H46A 0.2215 0.1759 0.0753 0.03 Uiso calc U . R 1.0 . .
C C51A 0.3728(2) 0.35302(17) 0.10307(12) 0.0204(5) Uani d . . . 1.0 . .
C C52A 0.3139(2) 0.38918(18) 0.06502(12) 0.0231(5) Uani d . . . 1.0 . .
H H52A 0.3156 0.379 0.0184 0.028 Uiso calc U . R 1.0 . .
C C53A 0.2526(2) 0.44006(19) 0.09512(13) 0.0283(6) Uani d . . . 1.0 . .
H H53A 0.2111 0.4637 0.0689 0.034 Uiso calc U . R 1.0 . .
C C54A 0.2517(2) 0.45645(18) 0.16319(13) 0.0279(6) Uani d . . . 1.0 . .
H H54A 0.2114 0.4928 0.1839 0.033 Uiso calc U . R 1.0 . .
C C55A 0.3094(2) 0.41996(18) 0.20114(12) 0.0265(6) Uani d . . . 1.0 . .
H H55A 0.3089 0.4315 0.2479 0.032 Uiso calc U . R 1.0 . .
C C56A 0.3680(2) 0.36662(17) 0.17106(12) 0.0243(6) Uani d . . . 1.0 . .
H H56A 0.4049 0.3394 0.1969 0.029 Uiso calc U . R 1.0 . .
C C1B 0.1962(2) 0.84630(17) 0.67757(12) 0.0214(5) Uani d . . . 1.0 . .
H H111 0.1816 0.9049 0.6876 0.026 Uiso calc U . R 1.0 . .
H H112 0.1898 0.8244 0.6286 0.026 Uiso calc U . R 1.0 . .
C C2B 0.1042(2) 0.76913(17) 0.70386(11) 0.0197(5) Uani d . . . 1.0 . .
H H2B 0.1321 0.7178 0.7054 0.024 Uiso calc U . R 1.0 . .
C C3B 0.0937(2) 0.81573(17) 0.77560(11) 0.0196(5) Uani d . . . 1.0 . .
H H3B 0.0565 0.8609 0.7717 0.024 Uiso calc U . R 1.0 . .
C C4B 0.2165(2) 0.87461(17) 0.81477(11) 0.0196(5) Uani d . . . 1.0 . .
C C5B 0.3129(2) 0.85074(17) 0.78801(11) 0.0212(5) Uani d . . . 1.0 . .
H H511 0.2959 0.7835 0.786 0.025 Uiso calc U . R 1.0 . .
H H512 0.3872 0.8902 0.8187 0.025 Uiso calc U . R 1.0 . .
C C6B 0.2304(2) 0.94017(18) 0.87106(12) 0.0244(6) Uani d . . . 1.0 . .
H H6B 0.3081 0.9772 0.8935 0.029 Uiso calc U . R 1.0 . .
C C7B 0.1333(2) 0.96018(18) 0.90184(13) 0.0282(6) Uani d . . . 1.0 . .
H H711 0.0875 0.975 0.8687 0.034 Uiso calc U . R 1.0 . .
H H712 0.1677 1.0164 0.9403 0.034 Uiso calc U . R 1.0 . .
C C8B 0.0513(2) 0.87575(18) 0.92532(12) 0.0261(6) Uani d . . . 1.0 . .
H H811 0.0992 0.8511 0.9492 0.031 Uiso calc U . R 1.0 . .
H H812 0.0059 0.8982 0.9573 0.031 Uiso calc U . R 1.0 . .
C C9B -0.0340(2) 0.79499(18) 0.86877(12) 0.0253(6) Uani d . . . 1.0 . .
H H911 -0.0845 0.8196 0.847 0.03 Uiso calc U . R 1.0 . .
H H912 -0.0854 0.7454 0.8887 0.03 Uiso calc U . R 1.0 . .
C C10B 0.0184(2) 0.74791(17) 0.81468(12) 0.0230(5) Uani d . . . 1.0 . .
H H10C -0.0461 0.6946 0.783 0.028 Uiso calc U . R 1.0 . .
H H10D 0.0673 0.7213 0.8356 0.028 Uiso calc U . R 1.0 . .
C C11B 0.3842(2) 0.79915(17) 0.66745(12) 0.0214(5) Uani d . . . 1.0 . .
C C12B 0.3898(2) 0.79644(19) 0.60047(12) 0.0257(6) Uani d . . . 1.0 . .
C C13B 0.4365(2) 0.7435(2) 0.55853(12) 0.0332(7) Uani d . . . 1.0 . .
C C14B 0.4847(2) 0.6897(2) 0.58371(13) 0.0342(7) Uani d . . . 1.0 . .
C C15B 0.4845(2) 0.69046(19) 0.64965(13) 0.0271(6) Uani d . . . 1.0 . .
C C16B 0.4362(2) 0.74383(18) 0.68932(12) 0.0231(5) Uani d . . . 1.0 . .
C C21B 0.4235(2) 0.97853(17) 0.71843(11) 0.0210(5) Uani d . . . 1.0 . .
C C22B 0.4059(2) 1.0483(2) 0.69411(14) 0.0305(6) Uani d . . . 1.0 . .
C C23B 0.4894(3) 1.1395(2) 0.70295(15) 0.0354(7) Uani d . . . 1.0 . .
C C24B 0.5982(2) 1.16606(19) 0.73806(14) 0.0328(6) Uani d . . . 1.0 . .
C C25B 0.6226(2) 1.10021(19) 0.76229(12) 0.0268(6) Uani d . . . 1.0 . .
C C26B 0.5374(2) 1.00940(18) 0.75116(11) 0.0217(5) Uani d . . . 1.0 . .
C C31B -0.1034(2) 0.80109(17) 0.66233(12) 0.0215(5) Uani d . . . 1.0 . .
C C32B -0.0568(2) 0.88649(18) 0.64401(13) 0.0273(6) Uani d . . . 1.0 . .
H H32B 0.0057 0.8982 0.6185 0.033 Uiso calc U . R 1.0 . .
C C33B -0.1023(2) 0.95438(19) 0.66322(14) 0.0342(7) Uani d . . . 1.0 . .
H H33B -0.0711 1.0124 0.6505 0.041 Uiso calc U . R 1.0 . .
C C34B -0.1930(2) 0.9377(2) 0.70089(14) 0.0345(7) Uani d . . . 1.0 . .
H H34B -0.2243 0.9841 0.7136 0.041 Uiso calc U . R 1.0 . .
C C35B -0.2384(2) 0.85335(19) 0.72001(13) 0.0297(6) Uani d . . . 1.0 . .
H H35B -0.2999 0.8423 0.7463 0.036 Uiso calc U . R 1.0 . .
C C36B -0.1938(2) 0.78540(18) 0.70080(12) 0.0244(6) Uani d . . . 1.0 . .
H H36B -0.2249 0.7277 0.7139 0.029 Uiso calc U . R 1.0 . .
C C41B -0.1371(2) 0.60290(17) 0.64994(11) 0.0211(5) Uani d . . . 1.0 . .
C C42B -0.1070(2) 0.54550(18) 0.68256(11) 0.0225(5) Uani d . . . 1.0 . .
H H42B -0.0313 0.5684 0.7078 0.027 Uiso calc U . R 1.0 . .
C C43B -0.1875(2) 0.45431(18) 0.67836(12) 0.0251(6) Uani d . . . 1.0 . .
H H43B -0.1667 0.415 0.7009 0.03 Uiso calc U . R 1.0 . .
C C44B -0.2982(2) 0.41994(19) 0.64154(13) 0.0294(6) Uani d . . . 1.0 . .
H H44B -0.3533 0.3578 0.6395 0.035 Uiso calc U . R 1.0 . .
C C45B -0.3279(2) 0.47651(19) 0.60783(12) 0.0279(6) Uani d . . . 1.0 . .
H H45B -0.4032 0.4527 0.582 0.033 Uiso calc U . R 1.0 . .
C C46B -0.2482(2) 0.56803(18) 0.61157(12) 0.0246(6) Uani d . . . 1.0 . .
H H46B -0.2687 0.6067 0.5883 0.03 Uiso calc U . R 1.0 . .
C C51B -0.0026(2) 0.69955(17) 0.56213(12) 0.0218(5) Uani d . . . 1.0 . .
C C52B -0.0463(2) 0.73067(19) 0.51322(12) 0.0277(6) Uani d . . . 1.0 . .
H H52B -0.0948 0.7644 0.5232 0.033 Uiso calc U . R 1.0 . .
C C53B -0.0184(3) 0.7119(2) 0.44951(13) 0.0365(7) Uani d . . . 1.0 . .
H H53B -0.0471 0.7337 0.4158 0.044 Uiso calc U . R 1.0 . .
C C54B 0.0509(3) 0.6620(2) 0.43466(13) 0.0348(7) Uani d . . . 1.0 . .
H H54B 0.0701 0.6499 0.3909 0.042 Uiso calc U . R 1.0 . .
C C55B 0.0925(2) 0.6294(2) 0.48325(12) 0.0307(6) Uani d . . . 1.0 . .
H H55B 0.1393 0.5943 0.4727 0.037 Uiso calc U . R 1.0 . .
C C56B 0.0660(2) 0.64789(18) 0.54680(12) 0.0264(6) Uani d . . . 1.0 . .
H H56B 0.0944 0.6255 0.5802 0.032 Uiso calc U . R 1.0 . .
F F12A 0.64741(13) 0.61288(10) 0.24317(7) 0.0289(3) Uani d . . . 1.0 . .
F F13A 0.59208(13) 0.64966(11) 0.36507(7) 0.0335(4) Uani d . . . 1.0 . .
F F14A 0.65915(15) 0.57879(13) 0.46150(7) 0.0409(4) Uani d . . . 1.0 . .
F F15A 0.78342(14) 0.47016(12) 0.43217(7) 0.0351(4) Uani d . . . 1.0 . .
F F16A 0.84033(13) 0.43180(10) 0.31149(7) 0.0287(3) Uani d . . . 1.0 . .
F F22A 0.76765(13) 0.57449(11) 0.06619(7) 0.0363(4) Uani d . . . 1.0 . .
F F23A 0.88284(15) 0.75165(12) 0.06073(8) 0.0455(5) Uani d . . . 1.0 . .
F F24A 1.03865(15) 0.88255(11) 0.16623(8) 0.0423(4) Uani d . . . 1.0 . .
F F25A 1.08111(14) 0.82735(11) 0.27871(7) 0.0426(4) Uani d . . . 1.0 . .
F F26A 0.96918(13) 0.65106(11) 0.28497(7) 0.0377(4) Uani d . . . 1.0 . .
F F12B 0.34878(13) 0.85083(12) 0.57235(7) 0.0336(4) Uani d . . . 1.0 . .
F F13B 0.43665(16) 0.74468(14) 0.49387(7) 0.0480(5) Uani d . . . 1.0 . .
F F14B 0.53104(16) 0.63764(14) 0.54450(8) 0.0498(5) Uani d . . . 1.0 . .
F F15B 0.53294(13) 0.63891(11) 0.67551(8) 0.0349(4) Uani d . . . 1.0 . .
F F16B 0.44548(13) 0.74145(10) 0.75470(7) 0.0281(3) Uani d . . . 1.0 . .
F F22B 0.30222(14) 1.02994(12) 0.65775(9) 0.0468(5) Uani d . . . 1.0 . .
F F23B 0.46462(16) 1.20320(12) 0.67740(10) 0.0540(5) Uani d . . . 1.0 . .
F F24B 0.68007(15) 1.25523(11) 0.74794(9) 0.0465(5) Uani d . . . 1.0 . .
F F25B 0.72976(12) 1.12361(11) 0.79550(7) 0.0334(4) Uani d . . . 1.0 . .
F F26B 0.57106(12) 0.94751(10) 0.77387(7) 0.0259(3) Uani d . . . 1.0 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1A C31A . 1.805(2) ?
P1A C41A . 1.807(2) ?
P1A C51A . 1.808(3) ?
P1A C2A . 1.847(2) ?
P1B C31B . 1.797(3) ?
P1B C51B . 1.804(2) ?
P1B C41B . 1.809(3) ?
P1B C2B . 1.837(2) ?
B1A C5A . 1.643(4) ?
B1A C21A . 1.666(4) ?
B1A C11A . 1.668(4) ?
B1A C1A . 1.669(4) ?
B1B C5B . 1.645(4) ?
B1B C1B . 1.647(4) ?
B1B C21B . 1.665(4) ?
B1B C11B . 1.668(4) ?
C1A C2A . 1.533(3) ?
C1A H101 . 0.99 ?
C1A H102 . 0.99 ?
C2A C3A . 1.552(3) ?
C2A H2A . 1.0 ?
C3A C4A . 1.534(3) ?
C3A C10A . 1.542(3) ?
C3A H3A . 1.0 ?
C4A C6A . 1.321(4) ?
C4A C5A . 1.507(3) ?
C5A H501 . 0.99 ?
C5A H502 . 0.99 ?
C6A C7A . 1.534(4) ?
C6A C7C . 1.545(14) ?
C6A H6A . 0.95 ?
C6A H6C . 0.95 ?
C9A C10A . 1.516(4) ?
C9A C8A . 1.525(4) ?
C9A C8C . 1.622(14) ?
C9A H901 . 0.99 ?
C9A H902 . 0.99 ?
C9A H921 . 0.99 ?
C9A H922 . 0.99 ?
C7A C8A . 1.519(5) ?
C7A H701 . 0.99 ?
C7A H702 . 0.99 ?
C8A H801 . 0.99 ?
C8A H802 . 0.99 ?
C7C C8C . 1.514(16) ?
C7C H721 . 0.99 ?
C7C H722 . 0.99 ?
C8C H821 . 0.99 ?
C8C H822 . 0.99 ?
C10A H10A . 0.99 ?
C10A H10B . 0.99 ?
C11A C16A . 1.383(3) ?
C11A C12A . 1.396(3) ?
C12A F12A . 1.358(3) ?
C12A C13A . 1.373(3) ?
C13A F13A . 1.349(3) ?
C13A C14A . 1.376(4) ?
C14A F14A . 1.341(3) ?
C14A C15A . 1.385(4) ?
C15A F15A . 1.346(3) ?
C15A C16A . 1.373(4) ?
C16A F16A . 1.366(3) ?
C21A C22A . 1.384(3) ?
C21A C26A . 1.387(3) ?
C22A F22A . 1.366(3) ?
C22A C23A . 1.377(4) ?
C23A F23A . 1.352(3) ?
C23A C24A . 1.374(4) ?
C24A F24A . 1.342(3) ?
C24A C25A . 1.378(4) ?
C25A F25A . 1.348(3) ?
C25A C26A . 1.377(4) ?
C26A F26A . 1.361(3) ?
C31A C36A . 1.396(3) ?
C31A C32A . 1.397(3) ?
C32A C33A . 1.389(3) ?
C32A H32A . 0.95 ?
C33A C34A . 1.378(4) ?
C33A H33A . 0.95 ?
C34A C35A . 1.387(4) ?
C34A H34A . 0.95 ?
C35A C36A . 1.379(4) ?
C35A H35A . 0.95 ?
C36A H36A . 0.95 ?
C41A C42A . 1.383(4) ?
C41A C46A . 1.400(4) ?
C42A C43A . 1.389(3) ?
C42A H42A . 0.95 ?
C43A C44A . 1.386(4) ?
C43A H43A . 0.95 ?
C44A C45A . 1.381(4) ?
C44A H44A . 0.95 ?
C45A C46A . 1.381(3) ?
C45A H45A . 0.95 ?
C46A H46A . 0.95 ?
C51A C56A . 1.390(3) ?
C51A C52A . 1.391(3) ?
C52A C53A . 1.387(4) ?
C52A H52A . 0.95 ?
C53A C54A . 1.383(4) ?
C53A H53A . 0.95 ?
C54A C55A . 1.384(4) ?
C54A H54A . 0.95 ?
C55A C56A . 1.387(4) ?
C55A H55A . 0.95 ?
C56A H56A . 0.95 ?
C1B C2B . 1.546(3) ?
C1B H111 . 0.99 ?
C1B H112 . 0.99 ?
C2B C3B . 1.550(3) ?
C2B H2B . 1.0 ?
C3B C4B . 1.527(3) ?
C3B C10B . 1.542(3) ?
C3B H3B . 1.0 ?
C4B C6B . 1.338(3) ?
C4B C5B . 1.492(3) ?
C5B H511 . 0.99 ?
C5B H512 . 0.99 ?
C6B C7B . 1.505(3) ?
C6B H6B . 0.95 ?
C7B C8B . 1.535(3) ?
C7B H711 . 0.99 ?
C7B H712 . 0.99 ?
C8B C9B . 1.526(3) ?
C8B H811 . 0.99 ?
C8B H812 . 0.99 ?
C9B C10B . 1.528(3) ?
C9B H911 . 0.99 ?
C9B H912 . 0.99 ?
C10B H10C . 0.99 ?
C10B H10D . 0.99 ?
C11B C12B . 1.389(3) ?
C11B C16B . 1.398(4) ?
C12B F12B . 1.360(3) ?
C12B C13B . 1.382(4) ?
C13B F13B . 1.347(3) ?
C13B C14B . 1.376(4) ?
C14B F14B . 1.341(3) ?
C14B C15B . 1.367(4) ?
C15B F15B . 1.355(3) ?
C15B C16B . 1.376(4) ?
C16B F16B . 1.366(3) ?
C21B C22B . 1.385(4) ?
C21B C26B . 1.395(3) ?
C22B F22B . 1.357(3) ?
C22B C23B . 1.385(4) ?
C23B F23B . 1.353(3) ?
C23B C24B . 1.371(4) ?
C24B F24B . 1.352(3) ?
C24B C25B . 1.367(4) ?
C25B F25B . 1.347(3) ?
C25B C26B . 1.383(3) ?
C26B F26B . 1.355(3) ?
C31B C36B . 1.394(3) ?
C31B C32B . 1.395(3) ?
C32B C33B . 1.389(4) ?
C32B H32B . 0.95 ?
C33B C34B . 1.387(4) ?
C33B H33B . 0.95 ?
C34B C35B . 1.387(4) ?
C34B H34B . 0.95 ?
C35B C36B . 1.382(4) ?
C35B H35B . 0.95 ?
C36B H36B . 0.95 ?
C41B C42B . 1.382(3) ?
C41B C46B . 1.404(3) ?
C42B C43B . 1.388(3) ?
C42B H42B . 0.95 ?
C43B C44B . 1.387(4) ?
C43B H43B . 0.95 ?
C44B C45B . 1.382(4) ?
C44B H44B . 0.95 ?
C45B C46B . 1.390(4) ?
C45B H45B . 0.95 ?
C46B H46B . 0.95 ?
C51B C52B . 1.387(3) ?
C51B C56B . 1.395(4) ?
C52B C53B . 1.386(4) ?
C52B H52B . 0.95 ?
C53B C54B . 1.380(4) ?
C53B H53B . 0.95 ?
C54B C55B . 1.384(4) ?
C54B H54B . 0.95 ?
C55B C56B . 1.376(4) ?
C55B H55B . 0.95 ?
C56B H56B . 0.95 ?

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
C31A P1A C41A . . 108.00(11) ?
C31A P1A C51A . . 107.70(11) ?
C41A P1A C51A . . 105.23(11) ?
C31A P1A C2A . . 112.76(11) ?
C41A P1A C2A . . 112.71(11) ?
C51A P1A C2A . . 110.06(11) ?
C31B P1B C51B . . 111.57(11) ?
C31B P1B C41B . . 109.33(12) ?
C51B P1B C41B . . 103.47(11) ?
C31B P1B C2B . . 107.91(11) ?
C51B P1B C2B . . 108.35(11) ?
C41B P1B C2B . . 116.21(11) ?
C5A B1A C21A . . 109.9(2) ?
C5A B1A C11A . . 115.2(2) ?
C21A B1A C11A . . 106.34(19) ?
C5A B1A C1A . . 107.9(2) ?
C21A B1A C1A . . 113.5(2) ?
C11A B1A C1A . . 104.0(2) ?
C5B B1B C1B . . 105.5(2) ?
C5B B1B C21B . . 110.6(2) ?
C1B B1B C21B . . 112.7(2) ?
C5B B1B C11B . . 113.1(2) ?
C1B B1B C11B . . 110.4(2) ?
C21B B1B C11B . . 104.8(2) ?
C2A C1A B1A . . 111.7(2) ?
C2A C1A H101 . . 109.3 ?
B1A C1A H101 . . 109.3 ?
C2A C1A H102 . . 109.3 ?
B1A C1A H102 . . 109.3 ?
H101 C1A H102 . . 107.9 ?
C1A C2A C3A . . 110.4(2) ?
C1A C2A P1A . . 110.31(17) ?
C3A C2A P1A . . 113.88(16) ?
C1A C2A H2A . . 107.3 ?
C3A C2A H2A . . 107.3 ?
P1A C2A H2A . . 107.3 ?
C4A C3A C10A . . 111.5(2) ?
C4A C3A C2A . . 109.72(19) ?
C10A C3A C2A . . 114.8(2) ?
C4A C3A H3A . . 106.8 ?
C10A C3A H3A . . 106.8 ?
C2A C3A H3A . . 106.8 ?
C6A C4A C5A . . 122.7(2) ?
C6A C4A C3A . . 120.1(2) ?
C5A C4A C3A . . 117.1(2) ?
C4A C5A B1A . . 109.2(2) ?
C4A C5A H501 . . 109.8 ?
B1A C5A H501 . . 109.8 ?
C4A C5A H502 . . 109.8 ?
B1A C5A H502 . . 109.8 ?
H501 C5A H502 . . 108.3 ?
C4A C6A C7A . . 126.3(3) ?
C4A C6A C7C . . 131.4(7) ?
C4A C6A H6A . . 116.8 ?
C7A C6A H6A . . 116.8 ?
C4A C6A H6C . . 114.3 ?
C7C C6A H6C . . 114.3 ?
C10A C9A C8A . . 113.8(2) ?
C10A C9A C8C . . 117.6(6) ?
C10A C9A H901 . . 108.8 ?
C8A C9A H901 . . 108.8 ?
C10A C9A H902 . . 108.8 ?
C8A C9A H902 . . 108.8 ?
H901 C9A H902 . . 107.7 ?
C10A C9A H921 . . 107.9 ?
C8C C9A H921 . . 107.9 ?
C10A C9A H922 . . 107.9 ?
C8C C9A H922 . . 107.9 ?
H921 C9A H922 . . 107.2 ?
C8A C7A C6A . . 114.4(3) ?
C8A C7A H701 . . 108.7 ?
C6A C7A H701 . . 108.7 ?
C8A C7A H702 . . 108.7 ?
C6A C7A H702 . . 108.7 ?
H701 C7A H702 . . 107.6 ?
C7A C8A C9A . . 112.9(3) ?
C7A C8A H801 . . 109.0 ?
C9A C8A H801 . . 109.0 ?
C7A C8A H802 . . 109.0 ?
C9A C8A H802 . . 109.0 ?
H801 C8A H802 . . 107.8 ?
C8C C7C C6A . . 109.1(13) ?
C8C C7C H721 . . 109.9 ?
C6A C7C H721 . . 109.9 ?
C8C C7C H722 . . 109.9 ?
C6A C7C H722 . . 109.9 ?
H721 C7C H722 . . 108.3 ?
C7C C8C C9A . . 109.7(12) ?
C7C C8C H821 . . 109.7 ?
C9A C8C H821 . . 109.7 ?
C7C C8C H822 . . 109.7 ?
C9A C8C H822 . . 109.7 ?
H821 C8C H822 . . 108.2 ?
C9A C10A C3A . . 113.7(2) ?
C9A C10A H10A . . 108.8 ?
C3A C10A H10A . . 108.8 ?
C9A C10A H10B . . 108.8 ?
C3A C10A H10B . . 108.8 ?
H10A C10A H10B . . 107.7 ?
C16A C11A C12A . . 112.2(2) ?
C16A C11A B1A . . 129.0(2) ?
C12A C11A B1A . . 118.9(2) ?
F12A C12A C13A . . 115.6(2) ?
F12A C12A C11A . . 119.1(2) ?
C13A C12A C11A . . 125.2(2) ?
F13A C13A C12A . . 121.3(2) ?
F13A C13A C14A . . 119.1(2) ?
C12A C13A C14A . . 119.5(2) ?
F14A C14A C13A . . 121.2(2) ?
F14A C14A C15A . . 120.6(2) ?
C13A C14A C15A . . 118.2(2) ?
F15A C15A C16A . . 121.6(2) ?
F15A C15A C14A . . 118.8(2) ?
C16A C15A C14A . . 119.6(2) ?
F16A C16A C15A . . 114.7(2) ?
F16A C16A C11A . . 120.1(2) ?
C15A C16A C11A . . 125.2(2) ?
C22A C21A C26A . . 112.1(2) ?
C22A C21A B1A . . 126.6(2) ?
C26A C21A B1A . . 121.3(2) ?
F22A C22A C23A . . 114.9(2) ?
F22A C22A C21A . . 120.2(2) ?
C23A C22A C21A . . 124.8(2) ?
F23A C23A C24A . . 119.5(2) ?
F23A C23A C22A . . 120.6(2) ?
C24A C23A C22A . . 119.9(2) ?
F24A C24A C23A . . 120.5(2) ?
F24A C24A C25A . . 121.2(2) ?
C23A C24A C25A . . 118.3(2) ?
F25A C25A C26A . . 120.8(2) ?
F25A C25A C24A . . 120.2(2) ?
C26A C25A C24A . . 119.0(2) ?
F26A C26A C25A . . 114.4(2) ?
F26A C26A C21A . . 120.0(2) ?
C25A C26A C21A . . 125.6(2) ?
C36A C31A C32A . . 119.3(2) ?
C36A C31A P1A . . 119.95(19) ?
C32A C31A P1A . . 120.71(19) ?
C33A C32A C31A . . 119.5(2) ?
C33A C32A H32A . . 120.2 ?
C31A C32A H32A . . 120.2 ?
C34A C33A C32A . . 120.7(2) ?
C34A C33A H33A . . 119.7 ?
C32A C33A H33A . . 119.7 ?
C33A C34A C35A . . 119.9(2) ?
C33A C34A H34A . . 120.0 ?
C35A C34A H34A . . 120.0 ?
C36A C35A C34A . . 120.1(3) ?
C36A C35A H35A . . 120.0 ?
C34A C35A H35A . . 120.0 ?
C35A C36A C31A . . 120.4(2) ?
C35A C36A H36A . . 119.8 ?
C31A C36A H36A . . 119.8 ?
C42A C41A C46A . . 119.5(2) ?
C42A C41A P1A . . 122.42(19) ?
C46A C41A P1A . . 118.08(19) ?
C41A C42A C43A . . 120.3(2) ?
C41A C42A H42A . . 119.9 ?
C43A C42A H42A . . 119.9 ?
C44A C43A C42A . . 119.8(3) ?
C44A C43A H43A . . 120.1 ?
C42A C43A H43A . . 120.1 ?
C45A C44A C43A . . 120.3(2) ?
C45A C44A H44A . . 119.9 ?
C43A C44A H44A . . 119.9 ?
C44A C45A C46A . . 120.0(3) ?
C44A C45A H45A . . 120.0 ?
C46A C45A H45A . . 120.0 ?
C45A C46A C41A . . 120.1(2) ?
C45A C46A H46A . . 119.9 ?
C41A C46A H46A . . 119.9 ?
C56A C51A C52A . . 119.7(2) ?
C56A C51A P1A . . 119.49(19) ?
C52A C51A P1A . . 120.85(18) ?
C53A C52A C51A . . 120.1(2) ?
C53A C52A H52A . . 120.0 ?
C51A C52A H52A . . 120.0 ?
C54A C53A C52A . . 120.1(2) ?
C54A C53A H53A . . 120.0 ?
C52A C53A H53A . . 120.0 ?
C53A C54A C55A . . 120.0(2) ?
C53A C54A H54A . . 120.0 ?
C55A C54A H54A . . 120.0 ?
C54A C55A C56A . . 120.2(2) ?
C54A C55A H55A . . 119.9 ?
C56A C55A H55A . . 119.9 ?
C55A C56A C51A . . 119.9(2) ?
C55A C56A H56A . . 120.0 ?
C51A C56A H56A . . 120.0 ?
C2B C1B B1B . . 109.65(19) ?
C2B C1B H111 . . 109.7 ?
B1B C1B H111 . . 109.7 ?
C2B C1B H112 . . 109.7 ?
B1B C1B H112 . . 109.7 ?
H111 C1B H112 . . 108.2 ?
C1B C2B C3B . . 107.69(19) ?
C1B C2B P1B . . 108.89(15) ?
C3B C2B P1B . . 113.13(16) ?
C1B C2B H2B . . 109.0 ?
C3B C2B H2B . . 109.0 ?
P1B C2B H2B . . 109.0 ?
C4B C3B C10B . . 110.46(19) ?
C4B C3B C2B . . 109.00(19) ?
C10B C3B C2B . . 116.1(2) ?
C4B C3B H3B . . 107.0 ?
C10B C3B H3B . . 107.0 ?
C2B C3B H3B . . 107.0 ?
C6B C4B C5B . . 124.5(2) ?
C6B C4B C3B . . 119.3(2) ?
C5B C4B C3B . . 116.2(2) ?
C4B C5B B1B . . 111.8(2) ?
C4B C5B H511 . . 109.3 ?
B1B C5B H511 . . 109.3 ?
C4B C5B H512 . . 109.3 ?
B1B C5B H512 . . 109.3 ?
H511 C5B H512 . . 107.9 ?
C4B C6B C7B . . 125.4(2) ?
C4B C6B H6B . . 117.3 ?
C7B C6B H6B . . 117.3 ?
C6B C7B C8B . . 111.9(2) ?
C6B C7B H711 . . 109.2 ?
C8B C7B H711 . . 109.2 ?
C6B C7B H712 . . 109.2 ?
C8B C7B H712 . . 109.2 ?
H711 C7B H712 . . 107.9 ?
C9B C8B C7B . . 113.7(2) ?
C9B C8B H811 . . 108.8 ?
C7B C8B H811 . . 108.8 ?
C9B C8B H812 . . 108.8 ?
C7B C8B H812 . . 108.8 ?
H811 C8B H812 . . 107.7 ?
C8B C9B C10B . . 117.3(2) ?
C8B C9B H911 . . 108.0 ?
C10B C9B H911 . . 108.0 ?
C8B C9B H912 . . 108.0 ?
C10B C9B H912 . . 108.0 ?
H911 C9B H912 . . 107.2 ?
C9B C10B C3B . . 113.7(2) ?
C9B C10B H10C . . 108.8 ?
C3B C10B H10C . . 108.8 ?
C9B C10B H10D . . 108.8 ?
C3B C10B H10D . . 108.8 ?
H10C C10B H10D . . 107.7 ?
C12B C11B C16B . . 111.8(2) ?
C12B C11B B1B . . 120.6(2) ?
C16B C11B B1B . . 127.4(2) ?
F12B C12B C13B . . 115.4(2) ?
F12B C12B C11B . . 119.1(2) ?
C13B C12B C11B . . 125.4(2) ?
F13B C13B C14B . . 119.8(2) ?
F13B C13B C12B . . 121.0(3) ?
C14B C13B C12B . . 119.2(2) ?
F14B C14B C15B . . 120.5(3) ?
F14B C14B C13B . . 120.8(2) ?
C15B C14B C13B . . 118.7(2) ?
F15B C15B C14B . . 119.5(2) ?
F15B C15B C16B . . 120.5(2) ?
C14B C15B C16B . . 120.0(2) ?
F16B C16B C15B . . 114.4(2) ?
F16B C16B C11B . . 120.7(2) ?
C15B C16B C11B . . 124.9(2) ?
C22B C21B C26B . . 112.2(2) ?
C22B C21B B1B . . 128.6(2) ?
C26B C21B B1B . . 119.2(2) ?
F22B C22B C23B . . 114.6(2) ?
F22B C22B C21B . . 120.8(2) ?
C23B C22B C21B . . 124.5(2) ?
F23B C23B C24B . . 119.3(3) ?
F23B C23B C22B . . 120.6(3) ?
C24B C23B C22B . . 120.0(3) ?
F24B C24B C25B . . 120.7(3) ?
F24B C24B C23B . . 120.7(3) ?
C25B C24B C23B . . 118.6(3) ?
F25B C25B C24B . . 119.9(2) ?
F25B C25B C26B . . 120.6(2) ?
C24B C25B C26B . . 119.5(2) ?
F26B C26B C25B . . 115.5(2) ?
F26B C26B C21B . . 119.5(2) ?
C25B C26B C21B . . 125.1(2) ?
C36B C31B C32B . . 119.6(2) ?
C36B C31B P1B . . 119.70(19) ?
C32B C31B P1B . . 120.13(19) ?
C33B C32B C31B . . 119.7(3) ?
C33B C32B H32B . . 120.1 ?
C31B C32B H32B . . 120.1 ?
C34B C33B C32B . . 120.2(3) ?
C34B C33B H33B . . 119.9 ?
C32B C33B H33B . . 119.9 ?
C33B C34B C35B . . 120.2(3) ?
C33B C34B H34B . . 119.9 ?
C35B C34B H34B . . 119.9 ?
C36B C35B C34B . . 119.8(3) ?
C36B C35B H35B . . 120.1 ?
C34B C35B H35B . . 120.1 ?
C35B C36B C31B . . 120.4(2) ?
C35B C36B H36B . . 119.8 ?
C31B C36B H36B . . 119.8 ?
C42B C41B C46B . . 119.9(2) ?
C42B C41B P1B . . 123.11(19) ?
C46B C41B P1B . . 116.71(19) ?
C41B C42B C43B . . 119.8(2) ?
C41B C42B H42B . . 120.1 ?
C43B C42B H42B . . 120.1 ?
C44B C43B C42B . . 120.6(2) ?
C44B C43B H43B . . 119.7 ?
C42B C43B H43B . . 119.7 ?
C45B C44B C43B . . 119.7(2) ?
C45B C44B H44B . . 120.2 ?
C43B C44B H44B . . 120.2 ?
C44B C45B C46B . . 120.4(2) ?
C44B C45B H45B . . 119.8 ?
C46B C45B H45B . . 119.8 ?
C45B C46B C41B . . 119.6(2) ?
C45B C46B H46B . . 120.2 ?
C41B C46B H46B . . 120.2 ?
C52B C51B C56B . . 120.3(2) ?
C52B C51B P1B . . 123.0(2) ?
C56B C51B P1B . . 116.70(19) ?
C53B C52B C51B . . 119.1(2) ?
C53B C52B H52B . . 120.4 ?
C51B C52B H52B . . 120.4 ?
C54B C53B C52B . . 120.5(3) ?
C54B C53B H53B . . 119.7 ?
C52B C53B H53B . . 119.7 ?
C53B C54B C55B . . 120.2(2) ?
C53B C54B H54B . . 119.9 ?
C55B C54B H54B . . 119.9 ?
C56B C55B C54B . . 120.0(3) ?
C56B C55B H55B . . 120.0 ?
C54B C55B H55B . . 120.0 ?
C55B C56B C51B . . 119.9(2) ?
C55B C56B H56B . . 120.1 ?
C51B C56B H56B . . 120.1 ?

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
C5A B1A C1A C2A . . . . 6.4(3) ?
C21A B1A C1A C2A . . . . 128.4(2) ?
C11A B1A C1A C2A . . . . -116.4(2) ?
B1A C1A C2A C3A . . . . -60.1(3) ?
B1A C1A C2A P1A . . . . 173.15(17) ?
C31A P1A C2A C1A . . . . 102.74(18) ?
C41A P1A C2A C1A . . . . -134.66(17) ?
C51A P1A C2A C1A . . . . -17.5(2) ?
C31A P1A C2A C3A . . . . -22.0(2) ?
C41A P1A C2A C3A . . . . 100.57(19) ?
C51A P1A C2A C3A . . . . -142.31(17) ?
C1A C2A C3A C4A . . . . 56.2(3) ?
P1A C2A C3A C4A . . . . -179.12(16) ?
C1A C2A C3A C10A . . . . -177.4(2) ?
P1A C2A C3A C10A . . . . -52.6(3) ?
C10A C3A C4A C6A . . . . 59.1(3) ?
C2A C3A C4A C6A . . . . -172.6(3) ?
C10A C3A C4A C5A . . . . -124.4(2) ?
C2A C3A C4A C5A . . . . 3.9(3) ?
C6A C4A C5A B1A . . . . 119.4(3) ?
C3A C4A C5A B1A . . . . -57.0(3) ?
C21A B1A C5A C4A . . . . -75.2(2) ?
C11A B1A C5A C4A . . . . 164.8(2) ?
C1A B1A C5A C4A . . . . 49.1(3) ?
C5A C4A C6A C7A . . . . -171.5(3) ?
C3A C4A C6A C7A . . . . 4.8(5) ?
C5A C4A C6A C7C . . . . 151.1(10) ?
C3A C4A C6A C7C . . . . -32.6(11) ?
C4A C6A C7A C8A . . . . -64.8(5) ?
C6A C7A C8A C9A . . . . 74.4(4) ?
C10A C9A C8A C7A . . . . -65.1(4) ?
C4A C6A C7C C8C . . . . 53.7(18) ?
C6A C7C C8C C9A . . . . -81.8(17) ?
C10A C9A C8C C7C . . . . 50.7(16) ?
C8A C9A C10A C3A . . . . 71.8(3) ?
C8C C9A C10A C3A . . . . 33.4(9) ?
C4A C3A C10A C9A . . . . -83.8(3) ?
C2A C3A C10A C9A . . . . 150.7(2) ?
C5A B1A C11A C16A . . . . 3.0(4) ?
C21A B1A C11A C16A . . . . -119.0(3) ?
C1A B1A C11A C16A . . . . 120.8(3) ?
C5A B1A C11A C12A . . . . -175.2(2) ?
C21A B1A C11A C12A . . . . 62.8(3) ?
C1A B1A C11A C12A . . . . -57.4(3) ?
C16A C11A C12A F12A . . . . 179.2(2) ?
B1A C11A C12A F12A . . . . -2.4(3) ?
C16A C11A C12A C13A . . . . 0.0(4) ?
B1A C11A C12A C13A . . . . 178.4(2) ?
F12A C12A C13A F13A . . . . 0.4(4) ?
C11A C12A C13A F13A . . . . 179.7(2) ?
F12A C12A C13A C14A . . . . -179.3(2) ?
C11A C12A C13A C14A . . . . -0.1(4) ?
F13A C13A C14A F14A . . . . -0.2(4) ?
C12A C13A C14A F14A . . . . 179.5(2) ?
F13A C13A C14A C15A . . . . -179.5(2) ?
C12A C13A C14A C15A . . . . 0.3(4) ?
F14A C14A C15A F15A . . . . -0.3(4) ?
C13A C14A C15A F15A . . . . 179.0(2) ?
F14A C14A C15A C16A . . . . -179.6(2) ?
C13A C14A C15A C16A . . . . -0.3(4) ?
F15A C15A C16A F16A . . . . -0.5(4) ?
C14A C15A C16A F16A . . . . 178.8(2) ?
F15A C15A C16A C11A . . . . -179.1(2) ?
C14A C15A C16A C11A . . . . 0.2(4) ?
C12A C11A C16A F16A . . . . -178.6(2) ?
B1A C11A C16A F16A . . . . 3.2(4) ?
C12A C11A C16A C15A . . . . 0.0(4) ?
B1A C11A C16A C15A . . . . -178.3(2) ?
C5A B1A C21A C22A . . . . 96.2(3) ?
C11A B1A C21A C22A . . . . -138.5(2) ?
C1A B1A C21A C22A . . . . -24.7(4) ?
C5A B1A C21A C26A . . . . -87.1(3) ?
C11A B1A C21A C26A . . . . 38.2(3) ?
C1A B1A C21A C26A . . . . 152.0(2) ?
C26A C21A C22A F22A . . . . 173.5(2) ?
B1A C21A C22A F22A . . . . -9.6(4) ?
C26A C21A C22A C23A . . . . -5.0(4) ?
B1A C21A C22A C23A . . . . 171.9(3) ?
F22A C22A C23A F23A . . . . 2.2(4) ?
C21A C22A C23A F23A . . . . -179.3(2) ?
F22A C22A C23A C24A . . . . -177.6(2) ?
C21A C22A C23A C24A . . . . 1.0(4) ?
F23A C23A C24A F24A . . . . 0.9(4) ?
C22A C23A C24A F24A . . . . -179.3(2) ?
F23A C23A C24A C25A . . . . -176.6(2) ?
C22A C23A C24A C25A . . . . 3.1(4) ?
F24A C24A C25A F25A . . . . 1.1(4) ?
C23A C24A C25A F25A . . . . 178.6(2) ?
F24A C24A C25A C26A . . . . 179.8(2) ?
C23A C24A C25A C26A . . . . -2.7(4) ?
F25A C25A C26A F26A . . . . -2.6(4) ?
C24A C25A C26A F26A . . . . 178.7(2) ?
F25A C25A C26A C21A . . . . 176.7(2) ?
C24A C25A C26A C21A . . . . -2.0(4) ?
C22A C21A C26A F26A . . . . -175.2(2) ?
B1A C21A C26A F26A . . . . 7.7(4) ?
C22A C21A C26A C25A . . . . 5.6(4) ?
B1A C21A C26A C25A . . . . -171.6(3) ?
C41A P1A C31A C36A . . . . -0.5(2) ?
C51A P1A C31A C36A . . . . -113.6(2) ?
C2A P1A C31A C36A . . . . 124.7(2) ?
C41A P1A C31A C32A . . . . 179.3(2) ?
C51A P1A C31A C32A . . . . 66.1(2) ?
C2A P1A C31A C32A . . . . -55.5(2) ?
C36A C31A C32A C33A . . . . 0.7(4) ?
P1A C31A C32A C33A . . . . -179.03(19) ?
C31A C32A C33A C34A . . . . -0.3(4) ?
C32A C33A C34A C35A . . . . -0.4(4) ?
C33A C34A C35A C36A . . . . 0.9(4) ?
C34A C35A C36A C31A . . . . -0.5(4) ?
C32A C31A C36A C35A . . . . -0.3(4) ?
P1A C31A C36A C35A . . . . 179.5(2) ?
C31A P1A C41A C42A . . . . 92.2(2) ?
C51A P1A C41A C42A . . . . -153.0(2) ?
C2A P1A C41A C42A . . . . -33.0(2) ?
C31A P1A C41A C46A . . . . -85.5(2) ?
C51A P1A C41A C46A . . . . 29.3(2) ?
C2A P1A C41A C46A . . . . 149.29(18) ?
C46A C41A C42A C43A . . . . 1.9(4) ?
P1A C41A C42A C43A . . . . -175.71(19) ?
C41A C42A C43A C44A . . . . -2.3(4) ?
C42A C43A C44A C45A . . . . 1.0(4) ?
C43A C44A C45A C46A . . . . 0.7(4) ?
C44A C45A C46A C41A . . . . -1.1(4) ?
C42A C41A C46A C45A . . . . -0.2(4) ?
P1A C41A C46A C45A . . . . 177.51(19) ?
C31A P1A C51A C56A . . . . 178.89(19) ?
C41A P1A C51A C56A . . . . 63.9(2) ?
C2A P1A C51A C56A . . . . -57.8(2) ?
C31A P1A C51A C52A . . . . -1.0(2) ?
C41A P1A C51A C52A . . . . -116.1(2) ?
C2A P1A C51A C52A . . . . 122.3(2) ?
C56A C51A C52A C53A . . . . 1.2(4) ?
P1A C51A C52A C53A . . . . -178.85(19) ?
C51A C52A C53A C54A . . . . 1.2(4) ?
C52A C53A C54A C55A . . . . -1.7(4) ?
C53A C54A C55A C56A . . . . -0.2(4) ?
C54A C55A C56A C51A . . . . 2.6(4) ?
C52A C51A C56A C55A . . . . -3.1(4) ?
P1A C51A C56A C55A . . . . 176.96(19) ?
C5B B1B C1B C2B . . . . -31.5(3) ?
C21B B1B C1B C2B . . . . -152.2(2) ?
C11B B1B C1B C2B . . . . 91.0(2) ?
B1B C1B C2B C3B . . . . 74.7(2) ?
B1B C1B C2B P1B . . . . -162.24(17) ?
C31B P1B C2B C1B . . . . -77.55(18) ?
C51B P1B C2B C1B . . . . 43.4(2) ?
C41B P1B C2B C1B . . . . 159.30(16) ?
C31B P1B C2B C3B . . . . 42.15(19) ?
C51B P1B C2B C3B . . . . 163.09(16) ?
C41B P1B C2B C3B . . . . -81.00(19) ?
C1B C2B C3B C4B . . . . -46.7(2) ?
P1B C2B C3B C4B . . . . -167.06(16) ?
C1B C2B C3B C10B . . . . -172.1(2) ?
P1B C2B C3B C10B . . . . 67.5(2) ?
C10B C3B C4B C6B . . . . -68.8(3) ?
C2B C3B C4B C6B . . . . 162.6(2) ?
C10B C3B C4B C5B . . . . 108.6(2) ?
C2B C3B C4B C5B . . . . -20.1(3) ?
C6B C4B C5B B1B . . . . -120.3(3) ?
C3B C4B C5B B1B . . . . 62.5(3) ?
C1B B1B C5B C4B . . . . -31.9(3) ?
C21B B1B C5B C4B . . . . 90.3(2) ?
C11B B1B C5B C4B . . . . -152.6(2) ?
C5B C4B C6B C7B . . . . -174.9(2) ?
C3B C4B C6B C7B . . . . 2.2(4) ?
C4B C6B C7B C8B . . . . 65.1(3) ?
C6B C7B C8B C9B . . . . -76.6(3) ?
C7B C8B C9B C10B . . . . 60.4(3) ?
C8B C9B C10B C3B . . . . -62.0(3) ?
C4B C3B C10B C9B . . . . 81.1(3) ?
C2B C3B C10B C9B . . . . -154.2(2) ?
C5B B1B C11B C12B . . . . 172.1(2) ?
C1B B1B C11B C12B . . . . 54.2(3) ?
C21B B1B C11B C12B . . . . -67.5(3) ?
C5B B1B C11B C16B . . . . -12.5(4) ?
C1B B1B C11B C16B . . . . -130.4(3) ?
C21B B1B C11B C16B . . . . 107.9(3) ?
C16B C11B C12B F12B . . . . -176.4(2) ?
B1B C11B C12B F12B . . . . -0.3(4) ?
C16B C11B C12B C13B . . . . 2.3(4) ?
B1B C11B C12B C13B . . . . 178.4(2) ?
F12B C12B C13B F13B . . . . -2.1(4) ?
C11B C12B C13B F13B . . . . 179.1(2) ?
F12B C12B C13B C14B . . . . 177.2(2) ?
C11B C12B C13B C14B . . . . -1.6(4) ?
F13B C13B C14B F14B . . . . -0.6(4) ?
C12B C13B C14B F14B . . . . -179.9(3) ?
F13B C13B C14B C15B . . . . 179.4(2) ?
C12B C13B C14B C15B . . . . 0.1(4) ?
F14B C14B C15B F15B . . . . 0.8(4) ?
C13B C14B C15B F15B . . . . -179.1(2) ?
F14B C14B C15B C16B . . . . -179.7(2) ?
C13B C14B C15B C16B . . . . 0.4(4) ?
F15B C15B C16B F16B . . . . 1.9(3) ?
C14B C15B C16B F16B . . . . -177.6(2) ?
F15B C15B C16B C11B . . . . -179.9(2) ?
C14B C15B C16B C11B . . . . 0.6(4) ?
C12B C11B C16B F16B . . . . 176.3(2) ?
B1B C11B C16B F16B . . . . 0.6(4) ?
C12B C11B C16B C15B . . . . -1.8(4) ?
B1B C11B C16B C15B . . . . -177.6(2) ?
C5B B1B C21B C22B . . . . -121.5(3) ?
C1B B1B C21B C22B . . . . -3.7(4) ?
C11B B1B C21B C22B . . . . 116.3(3) ?
C5B B1B C21B C26B . . . . 58.3(3) ?
C1B B1B C21B C26B . . . . 176.1(2) ?
C11B B1B C21B C26B . . . . -63.9(3) ?
C26B C21B C22B F22B . . . . 176.6(2) ?
B1B C21B C22B F22B . . . . -3.6(4) ?
C26B C21B C22B C23B . . . . -2.2(4) ?
B1B C21B C22B C23B . . . . 177.6(3) ?
F22B C22B C23B F23B . . . . 1.1(4) ?
C21B C22B C23B F23B . . . . 180.0(3) ?
F22B C22B C23B C24B . . . . -179.1(3) ?
C21B C22B C23B C24B . . . . -0.2(5) ?
F23B C23B C24B F24B . . . . 0.8(4) ?
C22B C23B C24B F24B . . . . -179.0(3) ?
F23B C23B C24B C25B . . . . -178.6(3) ?
C22B C23B C24B C25B . . . . 1.6(4) ?
F24B C24B C25B F25B . . . . -1.1(4) ?
C23B C24B C25B F25B . . . . 178.3(2) ?
F24B C24B C25B C26B . . . . -179.7(2) ?
C23B C24B C25B C26B . . . . -0.3(4) ?
F25B C25B C26B F26B . . . . -2.0(3) ?
C24B C25B C26B F26B . . . . 176.7(2) ?
F25B C25B C26B C21B . . . . 178.8(2) ?
C24B C25B C26B C21B . . . . -2.5(4) ?
C22B C21B C26B F26B . . . . -175.5(2) ?
B1B C21B C26B F26B . . . . 4.6(3) ?
C22B C21B C26B C25B . . . . 3.7(4) ?
B1B C21B C26B C25B . . . . -176.2(2) ?
C51B P1B C31B C36B . . . . 140.77(19) ?
C41B P1B C31B C36B . . . . 26.9(2) ?
C2B P1B C31B C36B . . . . -100.3(2) ?
C51B P1B C31B C32B . . . . -47.7(2) ?
C41B P1B C31B C32B . . . . -161.58(19) ?
C2B P1B C31B C32B . . . . 71.2(2) ?
C36B C31B C32B C33B . . . . -1.1(4) ?
P1B C31B C32B C33B . . . . -172.6(2) ?
C31B C32B C33B C34B . . . . 0.5(4) ?
C32B C33B C34B C35B . . . . 0.5(4) ?
C33B C34B C35B C36B . . . . -0.7(4) ?
C34B C35B C36B C31B . . . . 0.1(4) ?
C32B C31B C36B C35B . . . . 0.9(4) ?
P1B C31B C36B C35B . . . . 172.42(19) ?
C31B P1B C41B C42B . . . . -135.7(2) ?
C51B P1B C41B C42B . . . . 105.4(2) ?
C2B P1B C41B C42B . . . . -13.3(3) ?
C31B P1B C41B C46B . . . . 51.0(2) ?
C51B P1B C41B C46B . . . . -68.0(2) ?
C2B P1B C41B C46B . . . . 173.38(18) ?
C46B C41B C42B C43B . . . . -1.3(4) ?
P1B C41B C42B C43B . . . . -174.49(18) ?
C41B C42B C43B C44B . . . . 0.1(4) ?
C42B C43B C44B C45B . . . . 1.1(4) ?
C43B C44B C45B C46B . . . . -1.1(4) ?
C44B C45B C46B C41B . . . . -0.1(4) ?
C42B C41B C46B C45B . . . . 1.3(4) ?
P1B C41B C46B C45B . . . . 174.90(19) ?
C31B P1B C51B C52B . . . . -11.4(3) ?
C41B P1B C51B C52B . . . . 106.0(2) ?
C2B P1B C51B C52B . . . . -130.0(2) ?
C31B P1B C51B C56B . . . . 170.95(19) ?
C41B P1B C51B C56B . . . . -71.6(2) ?
C2B P1B C51B C56B . . . . 52.3(2) ?
C56B C51B C52B C53B . . . . -1.7(4) ?
P1B C51B C52B C53B . . . . -179.3(2) ?
C51B C52B C53B C54B . . . . 0.8(4) ?
C52B C53B C54B C55B . . . . 0.5(5) ?
C53B C54B C55B C56B . . . . -0.8(5) ?
C54B C55B C56B C51B . . . . -0.1(4) ?
C52B C51B C56B C55B . . . . 1.4(4) ?
P1B C51B C56B C55B . . . . 179.1(2) ?


####################################################################### 
# 
# 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_erk9360
_database_code_depnum_ccdc_archive 'CCDC 1922908'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H24 B2 F20 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         970.26

_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                   9.0564(10)
_cell_length_b                   10.3497(9)
_cell_length_c                   21.915(2)
_cell_angle_alpha                91.873(6)
_cell_angle_beta                 96.630(7)
_cell_angle_gamma                96.996(6)
_cell_volume                     2022.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3416
_cell_measurement_theta_min      4.0662
_cell_measurement_theta_max      64.1799
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972

_exptl_absorpt_coefficient_mu    1.411
_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  0.82
_exptl_absorpt_correction_T_max  0.97

_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            30895
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_full        66.94
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_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.

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.
;

_reflns_number_total             7137
_reflns_number_gt                4021
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1703
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_number_reflns         7137
_refine_ls_number_parameters     605
_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)+(0.0665P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0024(3)

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'
N N 0.0311 0.0180 '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'

_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
B B1 0.2410(6) 0.4526(5) 0.1686(2) 0.0374(11) Uani d . . . 1 . .
C C1 0.7945(5) 0.6864(4) 0.28989(19) 0.0348(10) Uani d . . . 1 . .
H H1A 0.8444 0.7736 0.2818 0.042 Uiso calc U . R 1 . .
H H1B 0.8192 0.6233 0.2588 0.042 Uiso calc U . R 1 . .
B B2 0.8592(5) 0.6464(5) 0.3580(2) 0.0342(11) Uani d . . . 1 . .
C C2 0.6248(5) 0.6887(4) 0.28287(19) 0.0366(10) Uani d . . . 1 . .
H H2A 0.6038 0.7666 0.3062 0.044 Uiso calc U . R 1 . .
H H2B 0.5783 0.6111 0.3021 0.044 Uiso calc U . R 1 . .
C C3 0.5479(5) 0.6907(4) 0.21609(19) 0.0361(10) Uani d . . . 1 . .
H H3 0.5679 0.6104 0.1934 0.043 Uiso calc U . R 1 . .
C C4 0.3790(5) 0.6820(4) 0.21731(19) 0.0368(10) Uani d . . . 1 . .
C C5 0.2990(5) 0.5519(4) 0.2292(2) 0.0399(10) Uani d . . . 1 . .
H H5A 0.2109 0.5663 0.2502 0.048 Uiso calc U . R 1 . .
H H5B 0.3666 0.5077 0.258 0.048 Uiso calc U . R 1 . .
C C6 0.3086(5) 0.7874(4) 0.2099(2) 0.0425(11) Uani d . . . 1 . .
H H6 0.2043 0.7777 0.2133 0.051 Uiso calc U . R 1 . .
C C7 0.3817(6) 0.9213(5) 0.1965(2) 0.0497(12) Uani d . . . 1 . .
H H7A 0.35 0.987 0.2244 0.06 Uiso calc U . R 1 . .
H H7B 0.3462 0.9411 0.1538 0.06 Uiso calc U . R 1 . .
C C8 0.5528(5) 0.9323(5) 0.2044(2) 0.0487(12) Uani d . . . 1 . .
H H8A 0.5939 1.0065 0.1815 0.058 Uiso calc U . R 1 . .
H H8B 0.5914 0.9491 0.2485 0.058 Uiso calc U . R 1 . .
C C9 0.6039(5) 0.8073(4) 0.1808(2) 0.0438(11) Uani d . . . 1 . .
H H9A 0.7148 0.8174 0.1847 0.053 Uiso calc U . R 1 . .
H H9B 0.5661 0.7915 0.1366 0.053 Uiso calc U . R 1 . .
C C11 0.3740(5) 0.4091(4) 0.12904(19) 0.0374(10) Uani d . . . 1 . .
C C12 0.4972(5) 0.3604(4) 0.15982(19) 0.0384(10) Uani d . . . 1 . .
F F12 0.5082(3) 0.3541(3) 0.22182(11) 0.0453(6) Uani d . . . 1 . .
C C13 0.6096(5) 0.3140(4) 0.1321(2) 0.0419(11) Uani d . . . 1 . .
F F13 0.7268(3) 0.2717(3) 0.16646(13) 0.0538(7) Uani d . . . 1 . .
C C14 0.6048(5) 0.3114(5) 0.0699(2) 0.0503(12) Uani d . . . 1 . .
F F14 0.7147(3) 0.2676(3) 0.04189(14) 0.0648(8) Uani d . . . 1 . .
C C15 0.4844(6) 0.3534(5) 0.0360(2) 0.0457(11) Uani d . . . 1 . .
F F15 0.4738(3) 0.3472(3) -0.02621(12) 0.0570(8) Uani d . . . 1 . .
C C16 0.3726(5) 0.4016(4) 0.0653(2) 0.0406(11) Uani d . . . 1 . .
F F16 0.2601(3) 0.4397(3) 0.02680(11) 0.0470(7) Uani d . . . 1 . .
C C21 0.1528(4) 0.3099(4) 0.18430(19) 0.0351(10) Uani d . . . 1 . .
C C22 0.1640(5) 0.2522(4) 0.2407(2) 0.0394(10) Uani d . . . 1 . .
F F22 0.2368(3) 0.3177(3) 0.29175(11) 0.0499(7) Uani d . . . 1 . .
C C23 0.1046(5) 0.1261(4) 0.2494(2) 0.0417(11) Uani d . . . 1 . .
F F23 0.1220(3) 0.0755(3) 0.30463(12) 0.0565(8) Uani d . . . 1 . .
C C24 0.0280(5) 0.0501(4) 0.2003(2) 0.0432(11) Uani d . . . 1 . .
F F24 -0.0283(3) -0.0732(3) 0.20807(14) 0.0586(8) Uani d . . . 1 . .
C C25 0.0107(5) 0.1015(5) 0.1433(2) 0.0481(12) Uani d . . . 1 . .
F F25 -0.0640(3) 0.0289(3) 0.09467(14) 0.0606(8) Uani d . . . 1 . .
C C26 0.0741(5) 0.2275(4) 0.1365(2) 0.0394(11) Uani d . . . 1 . .
F F26 0.0578(3) 0.2713(2) 0.07857(12) 0.0497(7) Uani d . . . 1 . .
N N31 0.1253(4) 0.5329(3) 0.12927(16) 0.0351(8) Uani d . . . 1 . .
C C32 0.1750(5) 0.6313(4) 0.09487(19) 0.0390(10) Uani d . . . 1 . .
H H32 0.2773 0.6423 0.0879 0.047 Uiso calc U . R 1 . .
C C33 0.0804(5) 0.7172(4) 0.0693(2) 0.0416(11) Uani d . . . 1 . .
H H33 0.1172 0.7843 0.0444 0.05 Uiso calc U . R 1 . .
C C34 -0.0653(5) 0.7036(5) 0.0805(2) 0.0451(11) Uani d . . . 1 . .
H H34 -0.1317 0.7608 0.0634 0.054 Uiso calc U . R 1 . .
C C35 -0.1155(5) 0.6048(4) 0.1175(2) 0.0413(11) Uani d . . . 1 . .
H H35 -0.2163 0.5947 0.1264 0.05 Uiso calc U . R 1 . .
C C36 -0.0196(5) 0.5235(4) 0.1405(2) 0.0401(11) Uani d . . . 1 . .
H H36 -0.0554 0.4565 0.1657 0.048 Uiso calc U . R 1 . .
C C41 0.8397(5) 0.7467(4) 0.41600(19) 0.0339(10) Uani d . . . 1 . .
C C42 0.8125(5) 0.8758(4) 0.4115(2) 0.0376(10) Uani d . . . 1 . .
F F42 0.7949(3) 0.9293(2) 0.35616(11) 0.0469(7) Uani d . . . 1 . .
C C43 0.8061(5) 0.9577(4) 0.4617(2) 0.0420(11) Uani d . . . 1 . .
F F43 0.7797(4) 1.0829(3) 0.45337(13) 0.0598(8) Uani d . . . 1 . .
C C44 0.8289(5) 0.9162(5) 0.5198(2) 0.0454(11) Uani d . . . 1 . .
F F44 0.8250(4) 0.9957(3) 0.56880(12) 0.0594(8) Uani d . . . 1 . .
C C45 0.8625(5) 0.7909(4) 0.5274(2) 0.0402(11) Uani d . . . 1 . .
F F45 0.8917(3) 0.7477(3) 0.58464(11) 0.0518(7) Uani d . . . 1 . .
C C46 0.8680(5) 0.7127(4) 0.47641(19) 0.0344(10) Uani d . . . 1 . .
F F46 0.9055(3) 0.5915(2) 0.48794(10) 0.0407(6) Uani d . . . 1 . .
C C51 0.7830(4) 0.4935(4) 0.36446(19) 0.0348(10) Uani d . . . 1 . .
C C52 0.8181(5) 0.3921(4) 0.32803(19) 0.0342(10) Uani d . . . 1 . .
F F52 0.9310(3) 0.4161(2) 0.29143(11) 0.0419(6) Uani d . . . 1 . .
C C53 0.7469(5) 0.2658(4) 0.3236(2) 0.0404(11) Uani d . . . 1 . .
F F53 0.7896(3) 0.1752(2) 0.28633(12) 0.0475(7) Uani d . . . 1 . .
C C54 0.6271(5) 0.2351(4) 0.3562(2) 0.0400(11) Uani d . . . 1 . .
F F54 0.5517(3) 0.1152(2) 0.35091(13) 0.0518(7) Uani d . . . 1 . .
C C55 0.5876(5) 0.3300(4) 0.3939(2) 0.0402(11) Uani d . . . 1 . .
F F55 0.4729(3) 0.3012(3) 0.42705(13) 0.0514(7) Uani d . . . 1 . .
C C56 0.6640(5) 0.4540(4) 0.39722(19) 0.0348(10) Uani d . . . 1 . .
F F56 0.6136(3) 0.5409(2) 0.43531(11) 0.0416(6) Uani d . . . 1 . .
N N61 1.0418(4) 0.6530(3) 0.36481(15) 0.0332(8) Uani d . . . 1 . .
C C62 1.1203(5) 0.7626(4) 0.34763(19) 0.0364(10) Uani d . . . 1 . .
H H62 1.0681 0.8251 0.3263 0.044 Uiso calc U . R 1 . .
C C63 1.2744(5) 0.7860(4) 0.3602(2) 0.0399(10) Uani d . . . 1 . .
H H63 1.3277 0.8632 0.3474 0.048 Uiso calc U . R 1 . .
C C64 1.3498(5) 0.6959(4) 0.3916(2) 0.0412(11) Uani d . . . 1 . .
H H64 1.4556 0.7111 0.4017 0.049 Uiso calc U . R 1 . .
C C65 1.2693(5) 0.5830(5) 0.4084(2) 0.0425(11) Uani d . . . 1 . .
H H65 1.3193 0.5188 0.4293 0.051 Uiso calc U . R 1 . .
C C66 1.1166(5) 0.5649(4) 0.39438(19) 0.0367(10) Uani d . . . 1 . .
H H66 1.0618 0.4872 0.406 0.044 Uiso calc U . R 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 N31 . 1.607(6) ?
B1 C5 . 1.648(7) ?
B1 C21 . 1.657(7) ?
B1 C11 . 1.659(6) ?
C1 C2 . 1.530(6) ?
C1 B2 . 1.625(6) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
B2 N61 . 1.636(6) ?
B2 C41 . 1.653(6) ?
B2 C51 . 1.665(6) ?
C2 C3 . 1.548(6) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C9 . 1.522(6) ?
C3 C4 . 1.525(6) ?
C3 H3 . 1.0 ?
C4 C6 . 1.334(6) ?
C4 C5 . 1.495(6) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.514(6) ?
C6 H6 . 0.95 ?
C7 C8 . 1.530(7) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.521(6) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C11 C12 . 1.393(6) ?
C11 C16 . 1.394(6) ?
C12 F12 . 1.355(5) ?
C12 C13 . 1.371(6) ?
C13 F13 . 1.355(5) ?
C13 C14 . 1.359(7) ?
C14 F14 . 1.343(5) ?
C14 C15 . 1.371(7) ?
C15 F15 . 1.354(5) ?
C15 C16 . 1.392(6) ?
C16 F16 . 1.352(5) ?
C21 C22 . 1.389(6) ?
C21 C26 . 1.399(6) ?
C22 F22 . 1.348(5) ?
C22 C23 . 1.378(6) ?
C23 F23 . 1.335(5) ?
C23 C24 . 1.377(7) ?
C24 F24 . 1.340(5) ?
C24 C25 . 1.372(7) ?
C25 F25 . 1.348(5) ?
C25 C26 . 1.379(6) ?
C26 F26 . 1.359(5) ?
N31 C32 . 1.351(5) ?
N31 C36 . 1.355(5) ?
C32 C33 . 1.394(6) ?
C32 H32 . 0.95 ?
C33 C34 . 1.362(6) ?
C33 H33 . 0.95 ?
C34 C35 . 1.391(6) ?
C34 H34 . 0.95 ?
C35 C36 . 1.349(6) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C41 C46 . 1.384(6) ?
C41 C42 . 1.393(6) ?
C42 F42 . 1.350(5) ?
C42 C43 . 1.379(6) ?
C43 C44 . 1.357(6) ?
C43 F43 . 1.361(5) ?
C44 F44 . 1.338(5) ?
C44 C45 . 1.378(6) ?
C45 F45 . 1.354(5) ?
C45 C46 . 1.367(6) ?
C46 F46 . 1.363(5) ?
C51 C52 . 1.387(6) ?
C51 C56 . 1.391(6) ?
C52 F52 . 1.375(5) ?
C52 C53 . 1.381(6) ?
C53 F53 . 1.345(5) ?
C53 C54 . 1.377(6) ?
C54 F54 . 1.337(5) ?
C54 C55 . 1.369(6) ?
C55 F55 . 1.345(5) ?
C55 C56 . 1.378(6) ?
C56 F56 . 1.361(5) ?
N61 C66 . 1.341(5) ?
N61 C62 . 1.351(5) ?
C62 C63 . 1.382(6) ?
C62 H62 . 0.95 ?
C63 C64 . 1.377(6) ?
C63 H63 . 0.95 ?
C64 C65 . 1.383(6) ?
C64 H64 . 0.95 ?
C65 C66 . 1.370(6) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?

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
N31 B1 C5 . . 102.1(4) ?
N31 B1 C21 . . 109.4(3) ?
C5 B1 C21 . . 114.5(4) ?
N31 B1 C11 . . 113.0(4) ?
C5 B1 C11 . . 115.8(4) ?
C21 B1 C11 . . 102.3(4) ?
C2 C1 B2 . . 112.4(3) ?
C2 C1 H1A . . 109.1 ?
B2 C1 H1A . . 109.1 ?
C2 C1 H1B . . 109.1 ?
B2 C1 H1B . . 109.1 ?
H1A C1 H1B . . 107.9 ?
C1 B2 N61 . . 110.8(3) ?
C1 B2 C41 . . 116.3(4) ?
N61 B2 C41 . . 100.4(3) ?
C1 B2 C51 . . 105.6(3) ?
N61 B2 C51 . . 109.6(3) ?
C41 B2 C51 . . 114.1(4) ?
C1 C2 C3 . . 115.8(4) ?
C1 C2 H2A . . 108.3 ?
C3 C2 H2A . . 108.3 ?
C1 C2 H2B . . 108.3 ?
C3 C2 H2B . . 108.3 ?
H2A C2 H2B . . 107.4 ?
C9 C3 C4 . . 110.6(4) ?
C9 C3 C2 . . 114.8(4) ?
C4 C3 C2 . . 108.8(3) ?
C9 C3 H3 . . 107.5 ?
C4 C3 H3 . . 107.5 ?
C2 C3 H3 . . 107.5 ?
C6 C4 C5 . . 122.4(4) ?
C6 C4 C3 . . 120.8(4) ?
C5 C4 C3 . . 116.8(4) ?
C4 C5 B1 . . 116.4(4) ?
C4 C5 H5A . . 108.2 ?
B1 C5 H5A . . 108.2 ?
C4 C5 H5B . . 108.2 ?
B1 C5 H5B . . 108.2 ?
H5A C5 H5B . . 107.3 ?
C4 C6 C7 . . 125.3(4) ?
C4 C6 H6 . . 117.4 ?
C7 C6 H6 . . 117.4 ?
C6 C7 C8 . . 112.7(4) ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 110.4(4) ?
C9 C8 H8A . . 109.6 ?
C7 C8 H8A . . 109.6 ?
C9 C8 H8B . . 109.6 ?
C7 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
C8 C9 C3 . . 111.7(4) ?
C8 C9 H9A . . 109.3 ?
C3 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
C3 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
C12 C11 C16 . . 112.6(4) ?
C12 C11 B1 . . 119.4(4) ?
C16 C11 B1 . . 127.6(4) ?
F12 C12 C13 . . 115.9(4) ?
F12 C12 C11 . . 119.0(4) ?
C13 C12 C11 . . 125.0(4) ?
F13 C13 C14 . . 119.6(4) ?
F13 C13 C12 . . 120.3(4) ?
C14 C13 C12 . . 120.1(4) ?
F14 C14 C13 . . 120.9(4) ?
F14 C14 C15 . . 120.5(4) ?
C13 C14 C15 . . 118.5(4) ?
F15 C15 C14 . . 119.8(4) ?
F15 C15 C16 . . 120.0(4) ?
C14 C15 C16 . . 120.2(4) ?
F16 C16 C15 . . 114.4(4) ?
F16 C16 C11 . . 122.1(4) ?
C15 C16 C11 . . 123.5(4) ?
C22 C21 C26 . . 113.4(4) ?
C22 C21 B1 . . 126.3(4) ?
C26 C21 B1 . . 119.7(4) ?
F22 C22 C23 . . 114.8(4) ?
F22 C22 C21 . . 121.3(4) ?
C23 C22 C21 . . 123.9(4) ?
F23 C23 C24 . . 119.4(4) ?
F23 C23 C22 . . 120.9(4) ?
C24 C23 C22 . . 119.7(4) ?
F24 C24 C25 . . 120.4(4) ?
F24 C24 C23 . . 120.1(4) ?
C25 C24 C23 . . 119.5(4) ?
F25 C25 C24 . . 120.5(4) ?
F25 C25 C26 . . 120.6(4) ?
C24 C25 C26 . . 118.9(4) ?
F26 C26 C25 . . 116.2(4) ?
F26 C26 C21 . . 119.3(4) ?
C25 C26 C21 . . 124.5(4) ?
C32 N31 C36 . . 117.4(4) ?
C32 N31 B1 . . 120.8(4) ?
C36 N31 B1 . . 120.2(4) ?
N31 C32 C33 . . 121.9(4) ?
N31 C32 H32 . . 119.1 ?
C33 C32 H32 . . 119.1 ?
C34 C33 C32 . . 119.2(4) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C33 C34 C35 . . 119.0(4) ?
C33 C34 H34 . . 120.5 ?
C35 C34 H34 . . 120.5 ?
C36 C35 C34 . . 119.4(4) ?
C36 C35 H35 . . 120.3 ?
C34 C35 H35 . . 120.3 ?
C35 C36 N31 . . 123.1(4) ?
C35 C36 H36 . . 118.4 ?
N31 C36 H36 . . 118.4 ?
C46 C41 C42 . . 112.4(4) ?
C46 C41 B2 . . 121.4(4) ?
C42 C41 B2 . . 125.8(4) ?
F42 C42 C43 . . 115.8(4) ?
F42 C42 C41 . . 120.7(4) ?
C43 C42 C41 . . 123.4(4) ?
C44 C43 F43 . . 119.2(4) ?
C44 C43 C42 . . 121.0(4) ?
F43 C43 C42 . . 119.8(4) ?
F44 C44 C43 . . 121.3(4) ?
F44 C44 C45 . . 120.3(4) ?
C43 C44 C45 . . 118.3(4) ?
F45 C45 C46 . . 121.0(4) ?
F45 C45 C44 . . 120.0(4) ?
C46 C45 C44 . . 119.0(4) ?
F46 C46 C45 . . 115.2(4) ?
F46 C46 C41 . . 119.0(4) ?
C45 C46 C41 . . 125.8(4) ?
C52 C51 C56 . . 111.9(4) ?
C52 C51 B2 . . 121.2(4) ?
C56 C51 B2 . . 126.1(4) ?
F52 C52 C53 . . 115.1(4) ?
F52 C52 C51 . . 119.1(4) ?
C53 C52 C51 . . 125.7(4) ?
F53 C53 C54 . . 120.4(4) ?
F53 C53 C52 . . 120.7(4) ?
C54 C53 C52 . . 118.9(4) ?
F54 C54 C55 . . 121.1(4) ?
F54 C54 C53 . . 120.4(4) ?
C55 C54 C53 . . 118.5(4) ?
F55 C55 C54 . . 119.4(4) ?
F55 C55 C56 . . 120.5(4) ?
C54 C55 C56 . . 120.1(4) ?
F56 C56 C55 . . 115.0(4) ?
F56 C56 C51 . . 120.2(4) ?
C55 C56 C51 . . 124.8(4) ?
C66 N61 C62 . . 118.7(4) ?
C66 N61 B2 . . 123.1(3) ?
C62 N61 B2 . . 117.4(3) ?
N61 C62 C63 . . 121.7(4) ?
N61 C62 H62 . . 119.2 ?
C63 C62 H62 . . 119.2 ?
C64 C63 C62 . . 119.1(4) ?
C64 C63 H63 . . 120.4 ?
C62 C63 H63 . . 120.4 ?
C63 C64 C65 . . 119.0(4) ?
C63 C64 H64 . . 120.5 ?
C65 C64 H64 . . 120.5 ?
C66 C65 C64 . . 119.2(4) ?
C66 C65 H65 . . 120.4 ?
C64 C65 H65 . . 120.4 ?
N61 C66 C65 . . 122.2(4) ?
N61 C66 H66 . . 118.9 ?
C65 C66 H66 . . 118.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 B2 N61 . . . . -176.8(3) ?
C2 C1 B2 C41 . . . . -63.1(5) ?
C2 C1 B2 C51 . . . . 64.6(4) ?
B2 C1 C2 C3 . . . . -164.9(4) ?
C1 C2 C3 C9 . . . . -60.0(5) ?
C1 C2 C3 C4 . . . . 175.6(4) ?
C9 C3 C4 C6 . . . . -23.5(6) ?
C2 C3 C4 C6 . . . . 103.4(5) ?
C9 C3 C4 C5 . . . . 158.5(4) ?
C2 C3 C4 C5 . . . . -74.6(5) ?
C6 C4 C5 B1 . . . . 94.2(5) ?
C3 C4 C5 B1 . . . . -87.8(5) ?
N31 B1 C5 C4 . . . . -61.8(5) ?
C21 B1 C5 C4 . . . . -179.9(4) ?
C11 B1 C5 C4 . . . . 61.4(5) ?
C5 C4 C6 C7 . . . . -178.7(4) ?
C3 C4 C6 C7 . . . . 3.4(7) ?
C4 C6 C7 C8 . . . . -11.2(7) ?
C6 C7 C8 C9 . . . . 38.8(6) ?
C7 C8 C9 C3 . . . . -61.2(5) ?
C4 C3 C9 C8 . . . . 52.2(5) ?
C2 C3 C9 C8 . . . . -71.3(5) ?
N31 B1 C11 C12 . . . . 168.3(4) ?
C5 B1 C11 C12 . . . . 50.9(6) ?
C21 B1 C11 C12 . . . . -74.2(5) ?
N31 B1 C11 C16 . . . . -19.1(7) ?
C5 B1 C11 C16 . . . . -136.5(5) ?
C21 B1 C11 C16 . . . . 98.3(5) ?
C16 C11 C12 F12 . . . . -175.9(4) ?
B1 C11 C12 F12 . . . . -2.3(6) ?
C16 C11 C12 C13 . . . . 2.3(7) ?
B1 C11 C12 C13 . . . . 175.9(4) ?
F12 C12 C13 F13 . . . . -3.4(6) ?
C11 C12 C13 F13 . . . . 178.4(4) ?
F12 C12 C13 C14 . . . . 177.3(4) ?
C11 C12 C13 C14 . . . . -1.0(7) ?
F13 C13 C14 F14 . . . . -0.1(7) ?
C12 C13 C14 F14 . . . . 179.2(4) ?
F13 C13 C14 C15 . . . . 179.3(4) ?
C12 C13 C14 C15 . . . . -1.3(7) ?
F14 C14 C15 F15 . . . . 2.0(7) ?
C13 C14 C15 F15 . . . . -177.5(4) ?
F14 C14 C15 C16 . . . . -178.5(4) ?
C13 C14 C15 C16 . . . . 2.1(7) ?
F15 C15 C16 F16 . . . . -0.4(6) ?
C14 C15 C16 F16 . . . . -180.0(4) ?
F15 C15 C16 C11 . . . . 178.9(4) ?
C14 C15 C16 C11 . . . . -0.7(8) ?
C12 C11 C16 F16 . . . . 177.8(4) ?
B1 C11 C16 F16 . . . . 4.8(7) ?
C12 C11 C16 C15 . . . . -1.4(7) ?
B1 C11 C16 C15 . . . . -174.4(4) ?
N31 B1 C21 C22 . . . . -135.3(4) ?
C5 B1 C21 C22 . . . . -21.4(6) ?
C11 B1 C21 C22 . . . . 104.6(5) ?
N31 B1 C21 C26 . . . . 54.1(5) ?
C5 B1 C21 C26 . . . . 168.0(4) ?
C11 B1 C21 C26 . . . . -66.0(5) ?
C26 C21 C22 F22 . . . . 179.7(4) ?
B1 C21 C22 F22 . . . . 8.6(7) ?
C26 C21 C22 C23 . . . . 0.3(6) ?
B1 C21 C22 C23 . . . . -170.8(4) ?
F22 C22 C23 F23 . . . . -0.9(6) ?
C21 C22 C23 F23 . . . . 178.5(4) ?
F22 C22 C23 C24 . . . . -179.8(4) ?
C21 C22 C23 C24 . . . . -0.4(7) ?
F23 C23 C24 F24 . . . . 0.1(7) ?
C22 C23 C24 F24 . . . . 179.1(4) ?
F23 C23 C24 C25 . . . . -179.6(4) ?
C22 C23 C24 C25 . . . . -0.6(7) ?
F24 C24 C25 F25 . . . . 0.4(7) ?
C23 C24 C25 F25 . . . . -179.9(4) ?
F24 C24 C25 C26 . . . . -178.0(4) ?
C23 C24 C25 C26 . . . . 1.7(7) ?
F25 C25 C26 F26 . . . . -0.8(6) ?
C24 C25 C26 F26 . . . . 177.7(4) ?
F25 C25 C26 C21 . . . . 179.7(4) ?
C24 C25 C26 C21 . . . . -1.9(7) ?
C22 C21 C26 F26 . . . . -178.7(4) ?
B1 C21 C26 F26 . . . . -6.9(6) ?
C22 C21 C26 C25 . . . . 0.8(6) ?
B1 C21 C26 C25 . . . . 172.6(4) ?
C5 B1 N31 C32 . . . . 79.0(5) ?
C21 B1 N31 C32 . . . . -159.4(4) ?
C11 B1 N31 C32 . . . . -46.1(5) ?
C5 B1 N31 C36 . . . . -86.2(5) ?
C21 B1 N31 C36 . . . . 35.5(5) ?
C11 B1 N31 C36 . . . . 148.8(4) ?
C36 N31 C32 C33 . . . . -2.8(6) ?
B1 N31 C32 C33 . . . . -168.3(4) ?
N31 C32 C33 C34 . . . . 1.6(7) ?
C32 C33 C34 C35 . . . . 0.4(7) ?
C33 C34 C35 C36 . . . . -1.1(7) ?
C34 C35 C36 N31 . . . . -0.1(7) ?
C32 N31 C36 C35 . . . . 2.0(6) ?
B1 N31 C36 C35 . . . . 167.6(4) ?
C1 B2 C41 C46 . . . . 169.4(4) ?
N61 B2 C41 C46 . . . . -71.0(5) ?
C51 B2 C41 C46 . . . . 46.0(5) ?
C1 B2 C41 C42 . . . . -18.7(6) ?
N61 B2 C41 C42 . . . . 100.8(4) ?
C51 B2 C41 C42 . . . . -142.2(4) ?
C46 C41 C42 F42 . . . . 174.5(4) ?
B2 C41 C42 F42 . . . . 2.1(7) ?
C46 C41 C42 C43 . . . . -3.5(6) ?
B2 C41 C42 C43 . . . . -175.9(4) ?
F42 C42 C43 C44 . . . . -177.0(4) ?
C41 C42 C43 C44 . . . . 1.1(7) ?
F42 C42 C43 F43 . . . . 1.5(6) ?
C41 C42 C43 F43 . . . . 179.6(4) ?
F43 C43 C44 F44 . . . . 0.5(7) ?
C42 C43 C44 F44 . . . . 179.0(4) ?
F43 C43 C44 C45 . . . . -176.9(4) ?
C42 C43 C44 C45 . . . . 1.6(7) ?
F44 C44 C45 F45 . . . . 0.1(7) ?
C43 C44 C45 F45 . . . . 177.5(4) ?
F44 C44 C45 C46 . . . . -179.0(4) ?
C43 C44 C45 C46 . . . . -1.5(7) ?
F45 C45 C46 F46 . . . . -0.5(6) ?
C44 C45 C46 F46 . . . . 178.5(4) ?
F45 C45 C46 C41 . . . . 179.7(4) ?
C44 C45 C46 C41 . . . . -1.3(7) ?
C42 C41 C46 F46 . . . . -176.1(4) ?
B2 C41 C46 F46 . . . . -3.3(6) ?
C42 C41 C46 C45 . . . . 3.7(6) ?
B2 C41 C46 C45 . . . . 176.5(4) ?
C1 B2 C51 C52 . . . . 66.0(5) ?
N61 B2 C51 C52 . . . . -53.4(5) ?
C41 B2 C51 C52 . . . . -165.0(4) ?
C1 B2 C51 C56 . . . . -102.9(5) ?
N61 B2 C51 C56 . . . . 137.7(4) ?
C41 B2 C51 C56 . . . . 26.1(6) ?
C56 C51 C52 F52 . . . . 178.3(4) ?
B2 C51 C52 F52 . . . . 8.0(6) ?
C56 C51 C52 C53 . . . . -0.3(6) ?
B2 C51 C52 C53 . . . . -170.6(4) ?
F52 C52 C53 F53 . . . . 0.9(6) ?
C51 C52 C53 F53 . . . . 179.5(4) ?
F52 C52 C53 C54 . . . . -176.5(4) ?
C51 C52 C53 C54 . . . . 2.1(7) ?
F53 C53 C54 F54 . . . . -0.2(7) ?
C52 C53 C54 F54 . . . . 177.1(4) ?
F53 C53 C54 C55 . . . . 179.7(4) ?
C52 C53 C54 C55 . . . . -2.9(7) ?
F54 C54 C55 F55 . . . . 1.4(7) ?
C53 C54 C55 F55 . . . . -178.6(4) ?
F54 C54 C55 C56 . . . . -178.0(4) ?
C53 C54 C55 C56 . . . . 2.0(7) ?
F55 C55 C56 F56 . . . . -0.5(6) ?
C54 C55 C56 F56 . . . . 179.0(4) ?
F55 C55 C56 C51 . . . . -179.5(4) ?
C54 C55 C56 C51 . . . . -0.1(7) ?
C52 C51 C56 F56 . . . . -179.8(4) ?
B2 C51 C56 F56 . . . . -10.0(6) ?
C52 C51 C56 C55 . . . . -0.8(6) ?
B2 C51 C56 C55 . . . . 169.0(4) ?
C1 B2 N61 C66 . . . . -140.2(4) ?
C41 B2 N61 C66 . . . . 96.3(4) ?
C51 B2 N61 C66 . . . . -24.0(5) ?
C1 B2 N61 C62 . . . . 49.7(5) ?
C41 B2 N61 C62 . . . . -73.7(4) ?
C51 B2 N61 C62 . . . . 165.9(3) ?
C66 N61 C62 C63 . . . . -0.6(6) ?
B2 N61 C62 C63 . . . . 170.0(4) ?
N61 C62 C63 C64 . . . . -0.7(7) ?
C62 C63 C64 C65 . . . . 1.6(7) ?
C63 C64 C65 C66 . . . . -1.3(7) ?
C62 N61 C66 C65 . . . . 0.8(6) ?
B2 N61 C66 C65 . . . . -169.1(4) ?
C64 C65 C66 N61 . . . . 0.1(7) ?


