# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

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

data_erk9199
_audit_block_doi                 10.5517/ccdc.csd.cc2210jp
_database_code_depnum_ccdc_archive 'CCDC 1907601'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H7 B F10'
_chemical_formula_iupac          ?
_chemical_formula_weight         460.08
_chemical_absolute_configuration .

_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                   7.4242(2)
_cell_length_b                   10.8667(3)
_cell_length_c                   21.4824(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1733.13(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8958
_cell_measurement_theta_min      4.1158
_cell_measurement_theta_max      66.7422
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912

_exptl_absorpt_coefficient_mu    1.596
_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  0.90

_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            15707
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_theta_min         4.56
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;

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

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

_reflns_number_total             3068
_reflns_number_gt                2948
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0579
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     289
_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)+(0.0231P)²+0.5549P] 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         0.158
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using xxx quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)

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 0.7725(3) 0.5917(2) 0.71469(10) 0.0191(5) Uani d . . . 1 . .
H H1A 0.6625 0.6176 0.7372 0.023 Uiso calc U . R 1 . .
H H1B 0.8647 0.5666 0.7454 0.023 Uiso calc U . R 1 . .
C C2 0.7316(3) 0.4881(2) 0.67039(10) 0.0172(5) Uani d . . . 1 . .
C C3 0.7697(3) 0.5290(2) 0.61091(10) 0.0182(5) Uani d . . . 1 . .
H H3 0.7519 0.4818 0.5742 0.022 Uiso calc U . R 1 . .
C C4 0.8404(3) 0.6533(2) 0.61201(10) 0.0174(5) Uani d . . . 1 . .
C C5 0.9026(3) 0.7287(2) 0.56404(11) 0.0210(5) Uani d . . . 1 . .
H H5 0.9018 0.7011 0.5221 0.025 Uiso calc U . R 1 . .
C C6 0.9658(3) 0.8452(2) 0.57914(11) 0.0236(5) Uani d . . . 1 . .
H H6 1.011 0.8974 0.5473 0.028 Uiso calc U . R 1 . .
C C7 0.9633(3) 0.8861(2) 0.64084(12) 0.0229(5) Uani d . . . 1 . .
H H7 1.0052 0.9666 0.6502 0.028 Uiso calc U . R 1 . .
C C8 0.9007(3) 0.8116(2) 0.68864(11) 0.0206(5) Uani d . . . 1 . .
H H8 0.8985 0.8405 0.7304 0.025 Uiso calc U . R 1 . .
C C9 0.8415(3) 0.6936(2) 0.67419(10) 0.0170(4) Uani d . . . 1 . .
B B1 0.6810(3) 0.3552(2) 0.68367(12) 0.0168(5) Uani d . . . 1 . .
C C11 0.6575(3) 0.2633(2) 0.62661(10) 0.0171(5) Uani d . . . 1 . .
F F12 0.96617(18) 0.27126(13) 0.59941(7) 0.0275(3) Uani d . . . 1 . .
C C12 0.7987(3) 0.2286(2) 0.58811(10) 0.0193(5) Uani d . . . 1 . .
F F13 0.9199(2) 0.11454(12) 0.50390(6) 0.0286(3) Uani d . . . 1 . .
C C13 0.7787(3) 0.1467(2) 0.53940(10) 0.0206(5) Uani d . . . 1 . .
F F14 0.5901(2) 0.01709(13) 0.48089(6) 0.0323(4) Uani d . . . 1 . .
C C14 0.6107(4) 0.0972(2) 0.52764(10) 0.0228(5) Uani d . . . 1 . .
F F15 0.3040(2) 0.08020(14) 0.55316(7) 0.0336(4) Uani d . . . 1 . .
C C15 0.4674(3) 0.1286(2) 0.56454(11) 0.0221(5) Uani d . . . 1 . .
F F16 0.34883(18) 0.23837(13) 0.64884(6) 0.0261(3) Uani d . . . 1 . .
C C16 0.4926(3) 0.2098(2) 0.61319(10) 0.0178(5) Uani d . . . 1 . .
C C21 0.6597(3) 0.2969(2) 0.75050(10) 0.0160(5) Uani d . . . 1 . .
F F22 0.81681(18) 0.11684(11) 0.71891(6) 0.0218(3) Uani d . . . 1 . .
C C22 0.7277(3) 0.1794(2) 0.76359(10) 0.0171(4) Uani d . . . 1 . .
F F23 0.78572(19) 0.01096(12) 0.83018(6) 0.0254(3) Uani d . . . 1 . .
C C23 0.7162(3) 0.1235(2) 0.82085(11) 0.0182(5) Uani d . . . 1 . .
F F24 0.6221(2) 0.13338(13) 0.92550(6) 0.0255(3) Uani d . . . 1 . .
C C24 0.6347(3) 0.1849(2) 0.86940(10) 0.0188(5) Uani d . . . 1 . .
F F25 0.48392(19) 0.36059(12) 0.90631(6) 0.0237(3) Uani d . . . 1 . .
C C25 0.5648(3) 0.3014(2) 0.85930(10) 0.0173(5) Uani d . . . 1 . .
F F26 0.50142(18) 0.46571(11) 0.79396(6) 0.0212(3) Uani d . . . 1 . .
C C26 0.5775(3) 0.35448(19) 0.80122(10) 0.0165(5) 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 C9 . 1.499(3) ?
C1 C2 . 1.505(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.382(3) ?
C2 B1 . 1.519(3) ?
C3 C4 . 1.450(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.396(3) ?
C4 C9 . 1.406(3) ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.398(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.388(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.390(3) ?
C8 H8 . 0.95 ?
B1 C21 . 1.577(3) ?
B1 C11 . 1.590(3) ?
C11 C16 . 1.385(3) ?
C11 C12 . 1.388(3) ?
F12 C12 . 1.349(3) ?
C12 C13 . 1.381(3) ?
F13 C13 . 1.343(3) ?
C13 C14 . 1.381(4) ?
F14 C14 . 1.338(3) ?
C14 C15 . 1.370(4) ?
F15 C15 . 1.344(3) ?
C15 C16 . 1.381(3) ?
F16 C16 . 1.350(3) ?
C21 C26 . 1.397(3) ?
C21 C22 . 1.401(3) ?
F22 C22 . 1.349(3) ?
C22 C23 . 1.375(3) ?
F23 C23 . 1.342(3) ?
C23 C24 . 1.378(3) ?
F24 C24 . 1.332(3) ?
C24 C25 . 1.385(3) ?
F25 C25 . 1.339(3) ?
C25 C26 . 1.378(3) ?
F26 C26 . 1.343(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
C9 C1 C2 . . 104.75(18) ?
C9 C1 H1A . . 110.8 ?
C2 C1 H1A . . 110.8 ?
C9 C1 H1B . . 110.8 ?
C2 C1 H1B . . 110.8 ?
H1A C1 H1B . . 108.9 ?
C3 C2 C1 . . 107.64(19) ?
C3 C2 B1 . . 122.0(2) ?
C1 C2 B1 . . 130.0(2) ?
C2 C3 C4 . . 111.00(19) ?
C2 C3 H3 . . 124.5 ?
C4 C3 H3 . . 124.5 ?
C5 C4 C9 . . 121.1(2) ?
C5 C4 C3 . . 131.0(2) ?
C9 C4 C3 . . 108.0(2) ?
C6 C5 C4 . . 118.4(2) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C7 . . 120.5(2) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 121.3(2) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C7 C8 C9 . . 118.6(2) ?
C7 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
C8 C9 C4 . . 120.1(2) ?
C8 C9 C1 . . 131.3(2) ?
C4 C9 C1 . . 108.6(2) ?
C2 B1 C21 . . 125.3(2) ?
C2 B1 C11 . . 118.62(19) ?
C21 B1 C11 . . 116.0(2) ?
C16 C11 C12 . . 115.4(2) ?
C16 C11 B1 . . 121.4(2) ?
C12 C11 B1 . . 123.2(2) ?
F12 C12 C13 . . 117.2(2) ?
F12 C12 C11 . . 119.7(2) ?
C13 C12 C11 . . 123.0(2) ?
F13 C13 C12 . . 120.9(2) ?
F13 C13 C14 . . 120.0(2) ?
C12 C13 C14 . . 119.1(2) ?
F14 C14 C15 . . 120.5(2) ?
F14 C14 C13 . . 119.6(2) ?
C15 C14 C13 . . 119.9(2) ?
F15 C15 C14 . . 119.9(2) ?
F15 C15 C16 . . 120.7(2) ?
C14 C15 C16 . . 119.5(2) ?
F16 C16 C15 . . 118.0(2) ?
F16 C16 C11 . . 118.96(19) ?
C15 C16 C11 . . 123.1(2) ?
C26 C21 C22 . . 114.16(19) ?
C26 C21 B1 . . 125.0(2) ?
C22 C21 B1 . . 120.8(2) ?
F22 C22 C23 . . 116.39(19) ?
F22 C22 C21 . . 119.52(19) ?
C23 C22 C21 . . 124.0(2) ?
F23 C23 C22 . . 120.8(2) ?
F23 C23 C24 . . 119.8(2) ?
C22 C23 C24 . . 119.4(2) ?
F24 C24 C23 . . 120.8(2) ?
F24 C24 C25 . . 120.0(2) ?
C23 C24 C25 . . 119.2(2) ?
F25 C25 C26 . . 120.8(2) ?
F25 C25 C24 . . 119.2(2) ?
C26 C25 C24 . . 119.9(2) ?
F26 C26 C25 . . 116.92(19) ?
F26 C26 C21 . . 119.77(19) ?
C25 C26 C21 . . 123.3(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
C9 C1 C2 C3 . . . . -1.3(2) ?
C9 C1 C2 B1 . . . . 171.2(2) ?
C1 C2 C3 C4 . . . . 2.0(3) ?
B1 C2 C3 C4 . . . . -171.2(2) ?
C2 C3 C4 C5 . . . . 177.3(2) ?
C2 C3 C4 C9 . . . . -1.9(3) ?
C9 C4 C5 C6 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . -179.2(2) ?
C4 C5 C6 C7 . . . . -1.3(4) ?
C5 C6 C7 C8 . . . . 1.0(4) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C7 C8 C9 C4 . . . . -1.9(3) ?
C7 C8 C9 C1 . . . . 178.0(2) ?
C5 C4 C9 C8 . . . . 1.7(3) ?
C3 C4 C9 C8 . . . . -179.0(2) ?
C5 C4 C9 C1 . . . . -178.3(2) ?
C3 C4 C9 C1 . . . . 1.0(3) ?
C2 C1 C9 C8 . . . . -179.8(2) ?
C2 C1 C9 C4 . . . . 0.1(3) ?
C3 C2 B1 C21 . . . . 171.8(2) ?
C1 C2 B1 C21 . . . . 0.2(4) ?
C3 C2 B1 C11 . . . . -4.6(3) ?
C1 C2 B1 C11 . . . . -176.1(2) ?
C2 B1 C11 C16 . . . . -116.0(2) ?
C21 B1 C11 C16 . . . . 67.3(3) ?
C2 B1 C11 C12 . . . . 65.7(3) ?
C21 B1 C11 C12 . . . . -110.9(2) ?
C16 C11 C12 F12 . . . . -176.83(19) ?
B1 C11 C12 F12 . . . . 1.5(3) ?
C16 C11 C12 C13 . . . . 0.2(3) ?
B1 C11 C12 C13 . . . . 178.6(2) ?
F12 C12 C13 F13 . . . . -2.0(3) ?
C11 C12 C13 F13 . . . . -179.1(2) ?
F12 C12 C13 C14 . . . . 177.6(2) ?
C11 C12 C13 C14 . . . . 0.5(3) ?
F13 C13 C14 F14 . . . . 0.1(3) ?
C12 C13 C14 F14 . . . . -179.5(2) ?
F13 C13 C14 C15 . . . . 179.0(2) ?
C12 C13 C14 C15 . . . . -0.6(3) ?
F14 C14 C15 F15 . . . . -1.0(3) ?
C13 C14 C15 F15 . . . . -179.9(2) ?
F14 C14 C15 C16 . . . . 178.88(19) ?
C13 C14 C15 C16 . . . . 0.1(3) ?
F15 C15 C16 F16 . . . . 0.3(3) ?
C14 C15 C16 F16 . . . . -179.7(2) ?
F15 C15 C16 C11 . . . . -179.4(2) ?
C14 C15 C16 C11 . . . . 0.7(3) ?
C12 C11 C16 F16 . . . . 179.55(18) ?
B1 C11 C16 F16 . . . . 1.2(3) ?
C12 C11 C16 C15 . . . . -0.8(3) ?
B1 C11 C16 C15 . . . . -179.2(2) ?
C2 B1 C21 C26 . . . . 41.2(3) ?
C11 B1 C21 C26 . . . . -142.4(2) ?
C2 B1 C21 C22 . . . . -137.7(2) ?
C11 B1 C21 C22 . . . . 38.7(3) ?
C26 C21 C22 F22 . . . . -177.19(19) ?
B1 C21 C22 F22 . . . . 1.8(3) ?
C26 C21 C22 C23 . . . . 0.1(3) ?
B1 C21 C22 C23 . . . . 179.1(2) ?
F22 C22 C23 F23 . . . . -2.1(3) ?
C21 C22 C23 F23 . . . . -179.5(2) ?
F22 C22 C23 C24 . . . . 176.84(19) ?
C21 C22 C23 C24 . . . . -0.5(3) ?
F23 C23 C24 F24 . . . . -0.8(3) ?
C22 C23 C24 F24 . . . . -179.8(2) ?
F23 C23 C24 C25 . . . . 179.5(2) ?
C22 C23 C24 C25 . . . . 0.5(3) ?
F24 C24 C25 F25 . . . . -0.4(3) ?
C23 C24 C25 F25 . . . . 179.3(2) ?
F24 C24 C25 C26 . . . . -179.8(2) ?
C23 C24 C25 C26 . . . . -0.1(3) ?
F25 C25 C26 F26 . . . . -1.7(3) ?
C24 C25 C26 F26 . . . . 177.69(19) ?
F25 C25 C26 C21 . . . . -179.7(2) ?
C24 C25 C26 C21 . . . . -0.4(3) ?
C22 C21 C26 F26 . . . . -177.64(18) ?
B1 C21 C26 F26 . . . . 3.4(3) ?
C22 C21 C26 C25 . . . . 0.4(3) ?
B1 C21 C26 C25 . . . . -178.6(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_erk9249
_audit_block_doi                 10.5517/ccdc.csd.cc2210pv
_database_code_depnum_ccdc_archive 'CCDC 1907606'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H10 B2 F20'
_chemical_formula_iupac          ?
_chemical_formula_weight         880.09
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   16.3020(4)
_cell_length_b                   31.6317(11)
_cell_length_c                   6.8859(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.0370(10)
_cell_angle_gamma                90
_cell_volume                     3444.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3370
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1736

_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

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

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12523
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_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.

Refined as a 2-component inversion twin.

The hydrogens at C10 atom were refined freely.

One C6F5 group is disordered over two positions. Several restraints (SADI,
SAME, ISOR and SIMU) were used in order to improve refinement stability.
;

_reflns_number_total             5579
_reflns_number_gt                4058
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1623
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.131
_refine_ls_number_reflns         5579
_refine_ls_number_parameters     659
_refine_ls_number_restraints     340
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+19.5099P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(17)

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'

_computing_data_collection       
;
Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-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
C C1 0.3726(6) 0.0634(3) 0.3470(18) 0.041(3) Uani d . . . 1.0 . .
H H1A 0.4019 0.0589 0.2384 0.049 Uiso calc U . R 1.0 . .
H H1B 0.4114 0.0558 0.4766 0.049 Uiso calc U . R 1.0 . .
C C2 0.3420(6) 0.1087(3) 0.3488(16) 0.040(2) Uani d . . . 1.0 . .
C C3 0.2558(6) 0.1083(3) 0.3095(16) 0.040(3) Uani d . . . 1.0 . .
H H3 0.2216 0.1328 0.301 0.048 Uiso calc U . R 1.0 . .
C C4 0.2236(6) 0.0659(3) 0.2827(15) 0.037(2) Uani d . . . 1.0 . .
C C5 0.2925(6) 0.0379(3) 0.3112(15) 0.033(2) Uani d . . . 1.0 . .
C C6 0.1402(6) 0.0511(3) 0.2435(16) 0.035(2) Uani d . . . 1.0 . .
H H6 0.0934 0.0699 0.2245 0.042 Uiso calc U . R 1.0 . .
C C7 0.2820(6) -0.0060(3) 0.3029(14) 0.033(2) Uani d . . . 1.0 . .
C C8 0.3506(6) -0.0372(3) 0.3296(16) 0.040(3) Uani d . . . 1.0 . .
H H8 0.3338 -0.066 0.3228 0.048 Uiso calc U . R 1.0 . .
C C9 0.4319(6) -0.0303(3) 0.3615(16) 0.038(2) Uani d . . . 1.0 . .
C C10 0.5133(7) -0.0279(4) 0.393(2) 0.055(3) Uani d . . . 1.0 . .
H H10A 0.553(7) -0.025(3) 0.517(16) 0.04(3) Uiso d . . . 1.0 . .
H H10B 0.542(6) -0.021(3) 0.282(17) 0.05(3) Uiso d . . . 1.0 . .
B B1 0.3955(8) 0.1489(4) 0.384(2) 0.047(3) Uani d . . D 1.0 . .
C C11 0.4944(8) 0.1476(8) 0.403(3) 0.039(5) Uani d U P D 0.70(2) A 1
C C12 0.5526(9) 0.1648(7) 0.561(3) 0.048(5) Uani d U P D 0.70(2) A 1
F F12 0.5254(10) 0.1802(6) 0.718(2) 0.063(4) Uani d U P D 0.70(2) A 1
C C13 0.6370(8) 0.1677(6) 0.571(3) 0.051(5) Uani d U P D 0.70(2) A 1
F F13 0.6904(7) 0.1850(5) 0.731(3) 0.086(5) Uani d U P D 0.70(2) A 1
C C14 0.6660(8) 0.1531(6) 0.413(3) 0.047(4) Uani d U P D 0.70(2) A 1
F F14 0.7496(6) 0.1563(5) 0.422(3) 0.080(5) Uani d U P D 0.70(2) A 1
C C15 0.6116(10) 0.1362(6) 0.247(3) 0.044(4) Uani d U P D 0.70(2) A 1
F F15 0.6408(9) 0.1228(4) 0.091(3) 0.079(5) Uani d U P D 0.70(2) A 1
C C16 0.5283(10) 0.1344(7) 0.252(3) 0.053(5) Uani d U P D 0.70(2) A 1
F F16 0.4768(12) 0.1190(6) 0.081(3) 0.066(5) Uani d U P D 0.70(2) A 1
C C11B 0.4871(15) 0.1483(19) 0.346(6) 0.033(10) Uani d U P D 0.30(2) A 2
C C12B 0.5548(16) 0.163(2) 0.489(6) 0.060(12) Uani d U P D 0.30(2) A 2
F F12B 0.540(3) 0.172(2) 0.670(6) 0.091(14) Uani d U P D 0.30(2) A 2
C C13B 0.6374(17) 0.1603(17) 0.481(6) 0.052(9) Uani d U P D 0.30(2) A 2
F F13B 0.700(2) 0.1707(17) 0.637(6) 0.117(15) Uani d U P D 0.30(2) A 2
C C14B 0.6520(16) 0.1425(14) 0.312(6) 0.041(9) Uani d U P D 0.30(2) A 2
F F14B 0.7332(17) 0.1420(12) 0.299(6) 0.080(11) Uani d U P D 0.30(2) A 2
C C15B 0.5883(17) 0.1319(15) 0.151(6) 0.053(10) Uani d U P D 0.30(2) A 2
F F15B 0.603(2) 0.1165(14) -0.020(6) 0.100(12) Uani d U P D 0.30(2) A 2
C C16B 0.5084(17) 0.1333(17) 0.182(6) 0.040(10) Uani d U P D 0.30(2) A 2
F F16B 0.446(2) 0.1222(15) 0.022(6) 0.061(10) Uani d U P D 0.30(2) A 2
C C21 0.3602(6) 0.1932(4) 0.4295(19) 0.047(3) Uani d . . . 1.0 . .
C C22 0.3212(7) 0.2002(4) 0.585(2) 0.056(3) Uani d . . . 1.0 . .
F F22 0.3053(5) 0.1674(3) 0.6965(13) 0.078(2) Uani d . . . 1.0 . .
C C23 0.3020(7) 0.2403(5) 0.635(2) 0.068(4) Uani d . . . 1.0 . .
F F23 0.2673(5) 0.2459(3) 0.7936(14) 0.098(3) Uani d . . . 1.0 . .
C C24 0.3202(8) 0.2738(5) 0.534(3) 0.076(5) Uani d . . . 1.0 . .
F F24 0.3013(5) 0.3133(3) 0.5832(18) 0.110(4) Uani d . . . 1.0 . .
C C25 0.3554(8) 0.2688(4) 0.372(2) 0.067(4) Uani d . . . 1.0 . .
F F25 0.3729(5) 0.3020(2) 0.2705(17) 0.096(3) Uani d . . . 1.0 . .
C C26 0.3753(7) 0.2286(4) 0.3265(19) 0.051(3) Uani d . . . 1.0 . .
C C1A 0.1648(6) -0.0651(3) 0.2488(15) 0.033(2) Uani d . . . 1.0 . .
H H101 0.1852 -0.0802 0.3773 0.04 Uiso calc U . R 1.0 . .
H H102 0.1819 -0.081 0.1414 0.04 Uiso calc U . R 1.0 . .
C C2A 0.0692(6) -0.0590(3) 0.2007(15) 0.035(2) Uani d . . . 1.0 . .
C C3A 0.0525(6) -0.0173(3) 0.1965(15) 0.038(3) Uani d . . . 1.0 . .
H H3A -0.0028 -0.0056 0.1721 0.046 Uiso calc U . R 1.0 . .
C C4A 0.1295(6) 0.0078(3) 0.2338(15) 0.032(2) Uani d . . . 1.0 . .
C C5A 0.1980(6) -0.0208(3) 0.2621(15) 0.033(2) Uani d . . . 1.0 . .
B B1A 0.0017(7) -0.0932(4) 0.1540(18) 0.033(3) Uani d . . . 1.0 . .
C C11A 0.0253(6) -0.1414(3) 0.1501(18) 0.040(2) Uani d . . . 1.0 . .
F F12A -0.0338(5) -0.1447(3) -0.1941(12) 0.078(2) Uani d . . . 1.0 . .
C C12A 0.0069(7) -0.1645(4) -0.025(2) 0.057(3) Uani d . . . 1.0 . .
F F13A 0.0083(6) -0.2265(3) -0.2125(14) 0.097(3) Uani d . . . 1.0 . .
C C13A 0.0269(7) -0.2060(4) -0.035(2) 0.061(4) Uani d . . . 1.0 . .
F F14A 0.0889(5) -0.2679(2) 0.1252(14) 0.084(3) Uani d . . . 1.0 . .
C C14A 0.0691(7) -0.2268(4) 0.132(2) 0.058(3) Uani d . . . 1.0 . .
F F15A 0.1282(5) -0.2258(3) 0.4821(14) 0.084(3) Uani d . . . 1.0 . .
C C15A 0.0895(7) -0.2063(4) 0.315(2) 0.058(3) Uani d . . . 1.0 . .
F F16A 0.0893(5) -0.1436(2) 0.4969(11) 0.066(2) Uani d . . . 1.0 . .
C C16A 0.0682(7) -0.1633(4) 0.3171(18) 0.045(3) Uani d . . . 1.0 . .
C C21A -0.0944(6) -0.0799(3) 0.1041(17) 0.038(2) Uani d . . . 1.0 . .
F F22A -0.0972(4) -0.0515(2) -0.2122(12) 0.069(2) Uani d . . . 1.0 . .
C C22A -0.1382(7) -0.0604(4) -0.0679(18) 0.048(3) Uani d . . . 1.0 . .
F F23A -0.2607(5) -0.0297(3) -0.2754(14) 0.094(3) Uani d . . . 1.0 . .
C C23A -0.2221(8) -0.0487(4) -0.102(2) 0.063(4) Uani d . . . 1.0 . .
C C24A -0.2656(7) -0.0573(4) 0.039(3) 0.065(4) Uani d . . . 1.0 . .
F F24A -0.3469(4) -0.0459(3) 0.0071(17) 0.097(3) Uani d U . . 1.0 . .
F F25A -0.2678(5) -0.0837(3) 0.3507(15) 0.099(3) Uani d U . . 1.0 . .
C C25A -0.2266(8) -0.0761(4) 0.212(2) 0.063(4) Uani d . . . 1.0 . .
F F26 0.4123(4) 0.2241(2) 0.1748(13) 0.067(2) Uani d . . . 1.0 . .
F F26A -0.1039(5) -0.1061(3) 0.4139(11) 0.070(2) Uani d . . . 1.0 . .
C C26A -0.1414(7) -0.0875(4) 0.2397(19) 0.048(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
C1 C5 . 1.502(12) ?
C1 C2 . 1.519(15) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.364(14) ?
C2 B1 . 1.528(17) ?
C3 C4 . 1.433(14) ?
C3 H3 . 0.95 ?
C4 C6 . 1.401(13) ?
C4 C5 . 1.407(14) ?
C5 C7 . 1.399(14) ?
C6 C4A . 1.380(14) ?
C6 H6 . 0.95 ?
C7 C5A . 1.409(13) ?
C7 C8 . 1.470(13) ?
C8 C9 . 1.309(14) ?
C8 H8 . 0.95 ?
C9 C10 . 1.293(15) ?
C10 H10A . 0.93(11) ?
C10 H10B . 1.01(11) ?
B1 C21 . 1.575(17) ?
B1 C11B . 1.58(2) ?
B1 C11 . 1.587(18) ?
C11 C16 . 1.35(2) ?
C11 C12 . 1.370(17) ?
C12 F12 . 1.357(18) ?
C12 C13 . 1.363(16) ?
C13 F13 . 1.341(17) ?
C13 C14 . 1.366(16) ?
C14 F14 . 1.353(14) ?
C14 C15 . 1.374(17) ?
C15 F15 . 1.344(15) ?
C15 C16 . 1.368(16) ?
C16 F16 . 1.362(17) ?
C11B C16B . 1.34(3) ?
C11B C12B . 1.37(2) ?
C12B F12B . 1.35(2) ?
C12B C13B . 1.36(2) ?
C13B F13B . 1.34(2) ?
C13B C14B . 1.36(2) ?
C14B F14B . 1.35(2) ?
C14B C15B . 1.36(2) ?
C15B F15B . 1.35(2) ?
C15B C16B . 1.37(2) ?
C16B F16B . 1.35(2) ?
C21 C26 . 1.379(17) ?
C21 C22 . 1.388(16) ?
C22 F22 . 1.353(15) ?
C22 C23 . 1.373(18) ?
C23 C24 . 1.34(2) ?
C23 F23 . 1.355(15) ?
C24 F24 . 1.349(15) ?
C24 C25 . 1.39(2) ?
C25 F25 . 1.329(16) ?
C25 C26 . 1.367(16) ?
C26 F26 . 1.335(13) ?
C1A C5A . 1.497(13) ?
C1A C2A . 1.524(13) ?
C1A H101 . 0.99 ?
C1A H102 . 0.99 ?
C2A C3A . 1.349(14) ?
C2A B1A . 1.520(15) ?
C3A C4A . 1.455(13) ?
C3A H3A . 0.95 ?
C4A C5A . 1.413(13) ?
B1A C11A . 1.573(16) ?
B1A C21A . 1.577(15) ?
C11A C12A . 1.377(16) ?
C11A C16A . 1.379(16) ?
F12A C12A . 1.348(14) ?
C12A C13A . 1.359(16) ?
F13A C13A . 1.351(14) ?
C13A C14A . 1.359(18) ?
F14A C14A . 1.346(13) ?
C14A C15A . 1.384(18) ?
F15A C15A . 1.321(14) ?
C15A C16A . 1.407(17) ?
F16A C16A . 1.354(13) ?
C21A C26A . 1.365(15) ?
C21A C22A . 1.373(15) ?
F22A C22A . 1.355(13) ?
C22A C23A . 1.380(16) ?
F23A C23A . 1.347(15) ?
C23A C24A . 1.36(2) ?
C24A F24A . 1.340(13) ?
C24A C25A . 1.35(2) ?
F25A C25A . 1.315(15) ?
C25A C26A . 1.403(16) ?
F26A C26A . 1.342(14) ?

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 C1 C2 . . 103.5(8) ?
C5 C1 H1A . . 111.1 ?
C2 C1 H1A . . 111.1 ?
C5 C1 H1B . . 111.1 ?
C2 C1 H1B . . 111.1 ?
H1A C1 H1B . . 109.0 ?
C3 C2 C1 . . 108.3(9) ?
C3 C2 B1 . . 124.1(10) ?
C1 C2 B1 . . 127.6(9) ?
C2 C3 C4 . . 111.2(10) ?
C2 C3 H3 . . 124.4 ?
C4 C3 H3 . . 124.4 ?
C6 C4 C5 . . 121.4(10) ?
C6 C4 C3 . . 130.2(10) ?
C5 C4 C3 . . 108.4(8) ?
C7 C5 C4 . . 122.3(8) ?
C7 C5 C1 . . 129.2(9) ?
C4 C5 C1 . . 108.5(9) ?
C4A C6 C4 . . 116.5(9) ?
C4A C6 H6 . . 121.8 ?
C4 C6 H6 . . 121.8 ?
C5 C7 C5A . . 116.2(8) ?
C5 C7 C8 . . 125.5(8) ?
C5A C7 C8 . . 118.4(9) ?
C9 C8 C7 . . 128.2(10) ?
C9 C8 H8 . . 115.9 ?
C7 C8 H8 . . 115.9 ?
C10 C9 C8 . . 173.8(12) ?
C9 C10 H10A . . 127.(7) ?
C9 C10 H10B . . 122.(6) ?
H10A C10 H10B . . 109.(9) ?
C2 B1 C21 . . 123.4(10) ?
C2 B1 C11B . . 119.(2) ?
C21 B1 C11B . . 117.(2) ?
C2 B1 C11 . . 121.4(13) ?
C21 B1 C11 . . 114.8(13) ?
C16 C11 C12 . . 113.3(14) ?
C16 C11 B1 . . 122.8(14) ?
C12 C11 B1 . . 123.3(15) ?
F12 C12 C13 . . 117.0(15) ?
F12 C12 C11 . . 118.5(13) ?
C13 C12 C11 . . 124.5(15) ?
F13 C13 C12 . . 121.1(15) ?
F13 C13 C14 . . 120.5(14) ?
C12 C13 C14 . . 118.3(14) ?
F14 C14 C13 . . 118.6(15) ?
F14 C14 C15 . . 120.4(15) ?
C13 C14 C15 . . 121.0(12) ?
F15 C15 C16 . . 123.6(15) ?
F15 C15 C14 . . 120.4(14) ?
C16 C15 C14 . . 116.1(14) ?
C11 C16 F16 . . 119.5(14) ?
C11 C16 C15 . . 126.8(16) ?
F16 C16 C15 . . 113.6(16) ?
C16B C11B C12B . . 113.(2) ?
C16B C11B B1 . . 126.(2) ?
C12B C11B B1 . . 120.(2) ?
F12B C12B C13B . . 117.(3) ?
F12B C12B C11B . . 116.(3) ?
C13B C12B C11B . . 125.(3) ?
F13B C13B C14B . . 122.(3) ?
F13B C13B C12B . . 121.(3) ?
C14B C13B C12B . . 116.(2) ?
F14B C14B C13B . . 116.(3) ?
F14B C14B C15B . . 121.(3) ?
C13B C14B C15B . . 123.(2) ?
F15B C15B C14B . . 123.(3) ?
F15B C15B C16B . . 122.(3) ?
C14B C15B C16B . . 115.(2) ?
C11B C16B F16B . . 119.(2) ?
C11B C16B C15B . . 126.(3) ?
F16B C16B C15B . . 115.(3) ?
C26 C21 C22 . . 116.1(11) ?
C26 C21 B1 . . 120.1(11) ?
C22 C21 B1 . . 123.5(12) ?
F22 C22 C23 . . 118.5(13) ?
F22 C22 C21 . . 120.1(11) ?
C23 C22 C21 . . 121.2(13) ?
C24 C23 F23 . . 120.3(14) ?
C24 C23 C22 . . 120.4(13) ?
F23 C23 C22 . . 119.3(15) ?
C23 C24 F24 . . 120.6(15) ?
C23 C24 C25 . . 121.1(13) ?
F24 C24 C25 . . 118.2(15) ?
F25 C25 C26 . . 121.5(13) ?
F25 C25 C24 . . 121.1(13) ?
C26 C25 C24 . . 117.3(14) ?
F26 C26 C25 . . 117.1(11) ?
F26 C26 C21 . . 119.1(10) ?
C25 C26 C21 . . 123.8(12) ?
C5A C1A C2A . . 103.4(8) ?
C5A C1A H101 . . 111.1 ?
C2A C1A H101 . . 111.1 ?
C5A C1A H102 . . 111.1 ?
C2A C1A H102 . . 111.1 ?
H101 C1A H102 . . 109.0 ?
C3A C2A B1A . . 124.1(9) ?
C3A C2A C1A . . 108.5(9) ?
B1A C2A C1A . . 127.3(9) ?
C2A C3A C4A . . 111.7(9) ?
C2A C3A H3A . . 124.2 ?
C4A C3A H3A . . 124.2 ?
C6 C4A C5A . . 122.9(8) ?
C6 C4A C3A . . 130.0(9) ?
C5A C4A C3A . . 107.1(9) ?
C7 C5A C4A . . 120.8(9) ?
C7 C5A C1A . . 130.0(9) ?
C4A C5A C1A . . 109.2(8) ?
C2A B1A C11A . . 121.6(9) ?
C2A B1A C21A . . 119.1(9) ?
C11A B1A C21A . . 119.3(8) ?
C12A C11A C16A . . 114.9(11) ?
C12A C11A B1A . . 121.8(10) ?
C16A C11A B1A . . 123.3(10) ?
F12A C12A C13A . . 118.4(12) ?
F12A C12A C11A . . 117.9(11) ?
C13A C12A C11A . . 123.7(12) ?
F13A C13A C14A . . 119.3(12) ?
F13A C13A C12A . . 120.6(13) ?
C14A C13A C12A . . 120.0(12) ?
F14A C14A C13A . . 121.0(13) ?
F14A C14A C15A . . 118.5(13) ?
C13A C14A C15A . . 120.4(12) ?
F15A C15A C14A . . 122.2(13) ?
F15A C15A C16A . . 120.7(13) ?
C14A C15A C16A . . 117.1(12) ?
F16A C16A C11A . . 119.8(11) ?
F16A C16A C15A . . 116.4(11) ?
C11A C16A C15A . . 123.7(12) ?
C26A C21A C22A . . 114.1(10) ?
C26A C21A B1A . . 119.7(10) ?
C22A C21A B1A . . 126.1(10) ?
F22A C22A C21A . . 118.7(10) ?
F22A C22A C23A . . 117.6(11) ?
C21A C22A C23A . . 123.7(12) ?
F23A C23A C24A . . 120.6(12) ?
F23A C23A C22A . . 120.1(14) ?
C24A C23A C22A . . 119.3(13) ?
F24A C24A C25A . . 120.0(14) ?
F24A C24A C23A . . 119.6(14) ?
C25A C24A C23A . . 120.4(11) ?
F25A C25A C24A . . 120.6(12) ?
F25A C25A C26A . . 121.2(14) ?
C24A C25A C26A . . 118.2(13) ?
F26A C26A C21A . . 118.6(10) ?
F26A C26A C25A . . 117.1(11) ?
C21A C26A C25A . . 124.3(12) ?

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 C1 C2 C3 . . . . -2.5(12) ?
C5 C1 C2 B1 . . . . 178.3(11) ?
C1 C2 C3 C4 . . . . 0.7(12) ?
B1 C2 C3 C4 . . . . 179.9(10) ?
C2 C3 C4 C6 . . . . 178.9(11) ?
C2 C3 C4 C5 . . . . 1.5(12) ?
C6 C4 C5 C7 . . . . -0.3(15) ?
C3 C4 C5 C7 . . . . 177.4(9) ?
C6 C4 C5 C1 . . . . 179.2(10) ?
C3 C4 C5 C1 . . . . -3.2(11) ?
C2 C1 C5 C7 . . . . -177.2(10) ?
C2 C1 C5 C4 . . . . 3.4(11) ?
C5 C4 C6 C4A . . . . -0.2(15) ?
C3 C4 C6 C4A . . . . -177.3(10) ?
C4 C5 C7 C5A . . . . 0.7(14) ?
C1 C5 C7 C5A . . . . -178.6(10) ?
C4 C5 C7 C8 . . . . 179.5(9) ?
C1 C5 C7 C8 . . . . 0.2(17) ?
C5 C7 C8 C9 . . . . -1.3(18) ?
C5A C7 C8 C9 . . . . 177.5(11) ?
C3 C2 B1 C21 . . . . 14.8(19) ?
C1 C2 B1 C21 . . . . -166.2(11) ?
C3 C2 B1 C11B . . . . -156.(2) ?
C1 C2 B1 C11B . . . . 23.(3) ?
C3 C2 B1 C11 . . . . -172.4(13) ?
C1 C2 B1 C11 . . . . 7.(2) ?
C2 B1 C11 C16 . . . . 62.(3) ?
C21 B1 C11 C16 . . . . -125.(2) ?
C2 B1 C11 C12 . . . . -127.(2) ?
C21 B1 C11 C12 . . . . 46.(3) ?
C16 C11 C12 F12 . . . . 178.(2) ?
B1 C11 C12 F12 . . . . 6.(4) ?
C16 C11 C12 C13 . . . . -2.(4) ?
B1 C11 C12 C13 . . . . -173.(2) ?
F12 C12 C13 F13 . . . . 0.(3) ?
C11 C12 C13 F13 . . . . -180.(2) ?
F12 C12 C13 C14 . . . . -179.(2) ?
C11 C12 C13 C14 . . . . 1.(3) ?
F13 C13 C14 F14 . . . . 0.(3) ?
C12 C13 C14 F14 . . . . 179.4(19) ?
F13 C13 C14 C15 . . . . -178.6(18) ?
C12 C13 C14 C15 . . . . 1.(3) ?
F14 C14 C15 F15 . . . . 0.(3) ?
C13 C14 C15 F15 . . . . 178.7(17) ?
F14 C14 C15 C16 . . . . -180.0(18) ?
C13 C14 C15 C16 . . . . -1.(3) ?
C12 C11 C16 F16 . . . . -176.(2) ?
B1 C11 C16 F16 . . . . -4.(4) ?
C12 C11 C16 C15 . . . . 1.(4) ?
B1 C11 C16 C15 . . . . 173.(2) ?
F15 C15 C16 C11 . . . . -179.(2) ?
C14 C15 C16 C11 . . . . 0.(3) ?
F15 C15 C16 F16 . . . . -2.(3) ?
C14 C15 C16 F16 . . . . 177.4(19) ?
C2 B1 C11B C16B . . . . 49.(7) ?
C21 B1 C11B C16B . . . . -123.(5) ?
C2 B1 C11B C12B . . . . -130.(5) ?
C21 B1 C11B C12B . . . . 58.(6) ?
C16B C11B C12B F12B . . . . -169.(6) ?
B1 C11B C12B F12B . . . . 10.(9) ?
C16B C11B C12B C13B . . . . -6.(10) ?
B1 C11B C12B C13B . . . . 173.(5) ?
F12B C12B C13B F13B . . . . -9.(9) ?
C11B C12B C13B F13B . . . . -171.(6) ?
F12B C12B C13B C14B . . . . 165.(6) ?
C11B C12B C13B C14B . . . . 3.(10) ?
F13B C13B C14B F14B . . . . -10.(8) ?
C12B C13B C14B F14B . . . . 176.(5) ?
F13B C13B C14B C15B . . . . -180.(5) ?
C12B C13B C14B C15B . . . . 6.(8) ?
F14B C14B C15B F15B . . . . 7.(7) ?
C13B C14B C15B F15B . . . . 176.(5) ?
F14B C14B C15B C16B . . . . 180.(4) ?
C13B C14B C15B C16B . . . . -11.(8) ?
C12B C11B C16B F16B . . . . -173.(6) ?
B1 C11B C16B F16B . . . . 9.(9) ?
C12B C11B C16B C15B . . . . 0.(9) ?
B1 C11B C16B C15B . . . . -178.(5) ?
F15B C15B C16B C11B . . . . -179.(6) ?
C14B C15B C16B C11B . . . . 8.(9) ?
F15B C15B C16B F16B . . . . -6.(8) ?
C14B C15B C16B F16B . . . . -179.(5) ?
C2 B1 C21 C26 . . . . -132.0(12) ?
C11B B1 C21 C26 . . . . 39.(2) ?
C11 B1 C21 C26 . . . . 54.8(18) ?
C2 B1 C21 C22 . . . . 55.0(18) ?
C11B B1 C21 C22 . . . . -133.(2) ?
C11 B1 C21 C22 . . . . -118.2(15) ?
C26 C21 C22 F22 . . . . -178.7(10) ?
B1 C21 C22 F22 . . . . -5.5(17) ?
C26 C21 C22 C23 . . . . -2.3(17) ?
B1 C21 C22 C23 . . . . 170.9(11) ?
F22 C22 C23 C24 . . . . 177.0(12) ?
C21 C22 C23 C24 . . . . 0.5(19) ?
F22 C22 C23 F23 . . . . -0.7(17) ?
C21 C22 C23 F23 . . . . -177.1(11) ?
F23 C23 C24 F24 . . . . -3.(2) ?
C22 C23 C24 F24 . . . . 179.8(11) ?
F23 C23 C24 C25 . . . . -179.7(12) ?
C22 C23 C24 C25 . . . . 3.(2) ?
C23 C24 C25 F25 . . . . 179.5(12) ?
F24 C24 C25 F25 . . . . 2.(2) ?
C23 C24 C25 C26 . . . . -3.8(19) ?
F24 C24 C25 C26 . . . . 179.0(11) ?
F25 C25 C26 F26 . . . . -0.7(18) ?
C24 C25 C26 F26 . . . . -177.4(11) ?
F25 C25 C26 C21 . . . . 178.5(12) ?
C24 C25 C26 C21 . . . . 1.9(18) ?
C22 C21 C26 F26 . . . . -179.7(10) ?
B1 C21 C26 F26 . . . . 6.9(16) ?
C22 C21 C26 C25 . . . . 1.1(17) ?
B1 C21 C26 C25 . . . . -172.4(11) ?
C5A C1A C2A C3A . . . . -2.2(10) ?
C5A C1A C2A B1A . . . . 174.9(10) ?
B1A C2A C3A C4A . . . . -175.9(9) ?
C1A C2A C3A C4A . . . . 1.3(11) ?
C4 C6 C4A C5A . . . . 0.2(15) ?
C4 C6 C4A C3A . . . . 179.9(10) ?
C2A C3A C4A C6 . . . . -179.5(10) ?
C2A C3A C4A C5A . . . . 0.2(12) ?
C5 C7 C5A C4A . . . . -0.6(14) ?
C8 C7 C5A C4A . . . . -179.6(9) ?
C5 C7 C5A C1A . . . . -178.0(10) ?
C8 C7 C5A C1A . . . . 3.0(16) ?
C6 C4A C5A C7 . . . . 0.2(15) ?
C3A C4A C5A C7 . . . . -179.6(9) ?
C6 C4A C5A C1A . . . . 178.1(10) ?
C3A C4A C5A C1A . . . . -1.7(11) ?
C2A C1A C5A C7 . . . . 180.0(10) ?
C2A C1A C5A C4A . . . . 2.4(10) ?
C3A C2A B1A C11A . . . . 176.6(10) ?
C1A C2A B1A C11A . . . . -0.1(16) ?
C3A C2A B1A C21A . . . . -2.1(16) ?
C1A C2A B1A C21A . . . . -178.9(9) ?
C2A B1A C11A C12A . . . . -112.7(12) ?
C21A B1A C11A C12A . . . . 66.0(14) ?
C2A B1A C11A C16A . . . . 64.9(14) ?
C21A B1A C11A C16A . . . . -116.3(12) ?
C16A C11A C12A F12A . . . . -178.9(10) ?
B1A C11A C12A F12A . . . . -1.1(16) ?
C16A C11A C12A C13A . . . . 1.4(17) ?
B1A C11A C12A C13A . . . . 179.2(11) ?
F12A C12A C13A F13A . . . . 1.6(19) ?
C11A C12A C13A F13A . . . . -178.8(11) ?
F12A C12A C13A C14A . . . . 179.0(11) ?
C11A C12A C13A C14A . . . . -1.(2) ?
F13A C13A C14A F14A . . . . -3.2(19) ?
C12A C13A C14A F14A . . . . 179.4(11) ?
F13A C13A C14A C15A . . . . 179.5(12) ?
C12A C13A C14A C15A . . . . 2.1(19) ?
F14A C14A C15A F15A . . . . 0.6(17) ?
C13A C14A C15A F15A . . . . 178.0(12) ?
F14A C14A C15A C16A . . . . 179.7(11) ?
C13A C14A C15A C16A . . . . -2.9(17) ?
C12A C11A C16A F16A . . . . -179.8(9) ?
B1A C11A C16A F16A . . . . 2.5(15) ?
C12A C11A C16A C15A . . . . -2.4(16) ?
B1A C11A C16A C15A . . . . 179.8(10) ?
F15A C15A C16A F16A . . . . -0.3(16) ?
C14A C15A C16A F16A . . . . -179.4(10) ?
F15A C15A C16A C11A . . . . -177.7(10) ?
C14A C15A C16A C11A . . . . 3.2(17) ?
C2A B1A C21A C26A . . . . -108.2(12) ?
C11A B1A C21A C26A . . . . 73.0(14) ?
C2A B1A C21A C22A . . . . 71.3(15) ?
C11A B1A C21A C22A . . . . -107.5(13) ?
C26A C21A C22A F22A . . . . -179.9(10) ?
B1A C21A C22A F22A . . . . 0.6(17) ?
C26A C21A C22A C23A . . . . 0.7(16) ?
B1A C21A C22A C23A . . . . -178.9(10) ?
F22A C22A C23A F23A . . . . 0.6(17) ?
C21A C22A C23A F23A . . . . -180.0(11) ?
F22A C22A C23A C24A . . . . 179.8(11) ?
C21A C22A C23A C24A . . . . -0.8(18) ?
F23A C23A C24A F24A . . . . -1.3(19) ?
C22A C23A C24A F24A . . . . 179.6(11) ?
F23A C23A C24A C25A . . . . -179.5(12) ?
C22A C23A C24A C25A . . . . 1.(2) ?
F24A C24A C25A F25A . . . . 0.(2) ?
C23A C24A C25A F25A . . . . 178.7(12) ?
F24A C24A C25A C26A . . . . -179.9(11) ?
C23A C24A C25A C26A . . . . -2.(2) ?
C22A C21A C26A F26A . . . . -179.2(10) ?
B1A C21A C26A F26A . . . . 0.4(15) ?
C22A C21A C26A C25A . . . . -1.1(16) ?
B1A C21A C26A C25A . . . . 178.4(11) ?
F25A C25A C26A F26A . . . . -0.6(18) ?
C24A C25A C26A F26A . . . . 179.7(12) ?
F25A C25A C26A C21A . . . . -178.7(11) ?
C24A C25A C26A C21A . . . . 2.(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_erk9187
_audit_block_doi                 10.5517/ccdc.csd.cc2210kq
_database_code_depnum_ccdc_archive 'CCDC 1907602'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H9 B F10'
_chemical_formula_iupac          ?
_chemical_formula_weight         474.10
_chemical_absolute_configuration .

_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'

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

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

_cell_length_a                   7.3604(4)
_cell_length_b                   11.9863(7)
_cell_length_c                   21.4524(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1892.62(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9270
_cell_measurement_theta_min      2.5482
_cell_measurement_theta_max      25.7963
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.073
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    0.165
_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  0.91
_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 10.4167

_diffrn_reflns_number            39378
_diffrn_reflns_av_R_equivalents  0.1184
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

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

The borylindene unit is disordered over two positions. Several
restraints (SADI, SAME, ISOR and SIMU) were used in order to 
improve refinement stability.
;


_reflns_number_total             3336
_reflns_number_gt                2793
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1095
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.129
_refine_ls_number_reflns         3336
_refine_ls_number_parameters     391
_refine_ls_number_restraints     257
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.0928P] 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         0.216
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(4)

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'

_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 0.6772(8) 0.6663(5) 0.3122(3) 0.0212(14) Uani d . . D 1.0 . .
C C1 0.780(3) 0.4956(13) 0.3838(8) 0.021(4) Uani d U P D 0.625(9) A 1
H H1A 0.8834 0.5368 0.4022 0.025 Uiso calc U P R 0.625(9) A 1
H H1B 0.6762 0.4979 0.4133 0.025 Uiso calc U P R 0.625(9) A 1
C C2 0.727(4) 0.5443(11) 0.3208(11) 0.021(4) Uani d U P D 0.625(9) A 1
C C3 0.769(3) 0.4642(13) 0.2766(8) 0.017(4) Uani d U P D 0.625(9) A 1
H H3 0.7626 0.4769 0.233 0.02 Uiso calc U P R 0.625(9) A 1
C C4 0.8245(16) 0.3610(8) 0.3031(5) 0.017(3) Uani d U P D 0.625(9) A 1
C C5 0.8687(12) 0.2573(7) 0.2772(5) 0.020(2) Uani d U P D 0.625(9) A 1
H H5 0.8625 0.2455 0.2335 0.024 Uiso calc U P R 0.625(9) A 1
C C6 0.9217(11) 0.1726(7) 0.3170(4) 0.018(2) Uani d U P D 0.625(9) A 1
H H6 0.9486 0.1015 0.2999 0.022 Uiso calc U P R 0.625(9) A 1
C C7 0.937(2) 0.1874(10) 0.3821(6) 0.021(3) Uani d U P D 0.625(9) A 1
C C10 1.0037(16) 0.0933(8) 0.4225(5) 0.041(3) Uani d U P D 0.625(9) A 1
H H10A 1.1079 0.1186 0.4472 0.062 Uiso calc U P R 0.625(9) A 1
H H10B 1.0406 0.0305 0.3962 0.062 Uiso calc U P R 0.625(9) A 1
H H10C 0.9059 0.0695 0.4505 0.062 Uiso calc U P R 0.625(9) A 1
C C8 0.8916(13) 0.2916(8) 0.4082(5) 0.024(2) Uani d U P D 0.625(9) A 1
H H8 0.9011 0.3034 0.4519 0.029 Uiso calc U P R 0.625(9) A 1
C C9 0.8318(17) 0.3775(9) 0.3689(6) 0.017(3) Uani d U P D 0.625(9) A 1
C C1A 0.754(5) 0.451(2) 0.2871(12) 0.020(7) Uani d U P D 0.375(9) A 2
H H101 0.6346 0.431 0.2687 0.024 Uiso calc U P R 0.375(9) A 2
H H102 0.8405 0.467 0.253 0.024 Uiso calc U P R 0.375(9) A 2
C C2A 0.736(7) 0.5492(18) 0.3309(16) 0.017(7) Uani d U P D 0.375(9) A 2
C C3A 0.746(4) 0.505(2) 0.3914(13) 0.016(6) Uani d U P D 0.375(9) A 2
H H3A 0.7072 0.5438 0.4278 0.019 Uiso calc U P R 0.375(9) A 2
C C4A 0.820(4) 0.3972(16) 0.3914(9) 0.031(6) Uani d U P D 0.375(9) A 2
C C5A 0.871(2) 0.3272(13) 0.4407(8) 0.033(4) Uani d U P D 0.375(9) A 2
H H5A 0.8671 0.3513 0.4829 0.04 Uiso calc U P R 0.375(9) A 2
C C6A 0.930(2) 0.2193(14) 0.4244(9) 0.033(5) Uani d U P D 0.375(9) A 2
H H6A 0.9739 0.1716 0.4564 0.039 Uiso calc U P R 0.375(9) A 2
C C7A 0.928(4) 0.1790(15) 0.3630(10) 0.019(6) Uani d U P D 0.375(9) A 2
C C10A 0.977(3) 0.0589(13) 0.3501(8) 0.041(5) Uani d U P D 0.375(9) A 2
H H10D 1.0699 0.0345 0.38 0.062 Uiso calc U P R 0.375(9) A 2
H H10E 1.0253 0.0525 0.3076 0.062 Uiso calc U P R 0.375(9) A 2
H H10F 0.869 0.012 0.3543 0.062 Uiso calc U P R 0.375(9) A 2
C C8A 0.873(2) 0.2491(12) 0.3144(9) 0.026(4) Uani d U P D 0.375(9) A 2
H H8A 0.8699 0.2227 0.2727 0.031 Uiso calc U P R 0.375(9) A 2
C C9A 0.823(3) 0.3579(13) 0.3283(8) 0.009(4) Uani d U P D 0.375(9) A 2
C C11 0.6459(8) 0.7187(5) 0.2457(3) 0.0235(13) Uani d . . . 1.0 . .
C C12 0.5664(7) 0.6638(5) 0.1959(3) 0.0283(14) Uani d . . . 1.0 . .
F F12 0.4885(5) 0.5621(3) 0.20337(17) 0.0348(9) Uani d . . . 1.0 . .
C C13 0.5559(8) 0.7084(6) 0.1362(3) 0.0341(16) Uani d . . . 1.0 . .
F F13 0.4834(5) 0.6485(4) 0.08903(17) 0.0496(11) Uani d . . . 1.0 . .
C C14 0.6229(9) 0.8131(7) 0.1251(3) 0.0409(18) Uani d . . . 1.0 . .
F F14 0.6148(6) 0.8559(4) 0.06741(18) 0.0607(13) Uani d . . . 1.0 . .
C C15 0.6956(9) 0.8728(6) 0.1732(3) 0.0360(17) Uani d . . . 1.0 . .
F F15 0.7630(5) 0.9773(3) 0.16332(19) 0.0489(11) Uani d . . . 1.0 . .
C C16 0.7076(8) 0.8258(5) 0.2312(3) 0.0300(15) Uani d . . . 1.0 . .
F F16 0.7909(5) 0.8879(3) 0.27628(16) 0.0352(9) Uani d . . . 1.0 . .
C C21 0.6652(8) 0.7488(4) 0.3708(3) 0.0226(13) Uani d . . . 1.0 . .
C C22 0.5050(8) 0.8046(5) 0.3863(3) 0.0269(14) Uani d . . . 1.0 . .
F F22 0.3562(4) 0.7881(3) 0.35072(17) 0.0386(9) Uani d . . . 1.0 . .
C C23 0.4924(9) 0.8749(5) 0.4362(3) 0.0312(15) Uani d . . . 1.0 . .
F F23 0.3314(5) 0.9260(3) 0.44886(19) 0.0526(11) Uani d . . . 1.0 . .
C C24 0.6395(10) 0.8958(5) 0.4721(3) 0.0332(16) Uani d . . . 1.0 . .
F F24 0.6284(6) 0.9665(3) 0.52157(18) 0.0503(11) Uani d . . . 1.0 . .
C C25 0.7999(9) 0.8430(5) 0.4598(3) 0.0288(14) Uani d . . . 1.0 . .
F F25 0.9473(5) 0.8634(3) 0.49563(18) 0.0433(10) Uani d . . . 1.0 . .
C C26 0.8107(8) 0.7723(5) 0.4097(3) 0.0271(14) Uani d . . . 1.0 . .
F F26 0.9753(4) 0.7266(3) 0.39669(18) 0.0350(9) 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
B1 C2 . 1.519(12) ?
B1 C2A . 1.524(16) ?
B1 C11 . 1.577(9) ?
B1 C21 . 1.602(8) ?
C1 C9 . 1.501(18) ?
C1 C2 . 1.52(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.39(3) ?
C3 C4 . 1.420(15) ?
C3 H3 . 0.95 ?
C4 C5 . 1.400(11) ?
C4 C9 . 1.426(14) ?
C5 C6 . 1.383(11) ?
C5 H5 . 0.95 ?
C6 C7 . 1.412(13) ?
C6 H6 . 0.95 ?
C7 C8 . 1.409(13) ?
C7 C10 . 1.505(13) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C8 C9 . 1.401(12) ?
C8 H8 . 0.95 ?
C1A C9A . 1.51(2) ?
C1A C2A . 1.52(3) ?
C1A H101 . 0.99 ?
C1A H102 . 0.99 ?
C2A C3A . 1.40(4) ?
C3A C4A . 1.405(19) ?
C3A H3A . 0.95 ?
C4A C5A . 1.403(16) ?
C4A C9A . 1.434(19) ?
C5A C6A . 1.408(16) ?
C5A H5A . 0.95 ?
C6A C7A . 1.402(17) ?
C6A H6A . 0.95 ?
C7A C8A . 1.399(16) ?
C7A C10A . 1.510(19) ?
C10A H10D . 0.98 ?
C10A H10E . 0.98 ?
C10A H10F . 0.98 ?
C8A C9A . 1.385(16) ?
C8A H8A . 0.95 ?
C11 C12 . 1.384(8) ?
C11 C16 . 1.398(8) ?
C12 F12 . 1.357(7) ?
C12 C13 . 1.390(9) ?
C13 F13 . 1.351(8) ?
C13 C14 . 1.369(10) ?
C14 F14 . 1.341(7) ?
C14 C15 . 1.365(10) ?
C15 F15 . 1.365(8) ?
C15 C16 . 1.367(8) ?
C16 F16 . 1.366(7) ?
C21 C26 . 1.387(8) ?
C21 C22 . 1.396(8) ?
C22 F22 . 1.350(7) ?
C22 C23 . 1.364(9) ?
C23 C24 . 1.352(9) ?
C23 F23 . 1.362(7) ?
C24 F24 . 1.361(7) ?
C24 C25 . 1.365(9) ?
C25 F25 . 1.351(7) ?
C25 C26 . 1.371(8) ?
C26 F26 . 1.358(7) ?

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 B1 C11 . . 121.9(10) ?
C2A B1 C11 . . 130.3(14) ?
C2 B1 C21 . . 120.9(10) ?
C2A B1 C21 . . 112.2(14) ?
C11 B1 C21 . . 117.2(5) ?
C9 C1 C2 . . 103.7(13) ?
C9 C1 H1A . . 111.0 ?
C2 C1 H1A . . 111.0 ?
C9 C1 H1B . . 111.0 ?
C2 C1 H1B . . 111.0 ?
H1A C1 H1B . . 109.0 ?
C3 C2 B1 . . 129.7(17) ?
C3 C2 C1 . . 106.5(10) ?
B1 C2 C1 . . 122.5(16) ?
C2 C3 C4 . . 113.3(14) ?
C2 C3 H3 . . 123.4 ?
C4 C3 H3 . . 123.4 ?
C5 C4 C3 . . 132.9(11) ?
C5 C4 C9 . . 120.5(10) ?
C3 C4 C9 . . 106.6(11) ?
C6 C5 C4 . . 118.1(9) ?
C6 C5 H5 . . 120.9 ?
C4 C5 H5 . . 120.9 ?
C5 C6 C7 . . 122.8(9) ?
C5 C6 H6 . . 118.6 ?
C7 C6 H6 . . 118.6 ?
C8 C7 C6 . . 119.0(9) ?
C8 C7 C10 . . 120.9(10) ?
C6 C7 C10 . . 120.1(10) ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C8 C7 . . 119.1(10) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C4 . . 120.3(10) ?
C8 C9 C1 . . 130.2(12) ?
C4 C9 C1 . . 109.4(10) ?
C9A C1A C2A . . 103.9(18) ?
C9A C1A H101 . . 111.0 ?
C2A C1A H101 . . 111.0 ?
C9A C1A H102 . . 111.0 ?
C2A C1A H102 . . 111.0 ?
H101 C1A H102 . . 109.0 ?
C3A C2A C1A . . 106.1(15) ?
C3A C2A B1 . . 127.(2) ?
C1A C2A B1 . . 125.(2) ?
C2A C3A C4A . . 111.(2) ?
C2A C3A H3A . . 124.3 ?
C4A C3A H3A . . 124.3 ?
C5A C4A C3A . . 131.0(19) ?
C5A C4A C9A . . 120.7(16) ?
C3A C4A C9A . . 108.1(17) ?
C4A C5A C6A . . 116.4(16) ?
C4A C5A H5A . . 121.8 ?
C6A C5A H5A . . 121.8 ?
C7A C6A C5A . . 123.1(16) ?
C7A C6A H6A . . 118.5 ?
C5A C6A H6A . . 118.5 ?
C8A C7A C6A . . 119.8(15) ?
C8A C7A C10A . . 120.4(16) ?
C6A C7A C10A . . 119.8(16) ?
C7A C10A H10D . . 109.5 ?
C7A C10A H10E . . 109.5 ?
H10D C10A H10E . . 109.5 ?
C7A C10A H10F . . 109.5 ?
H10D C10A H10F . . 109.5 ?
H10E C10A H10F . . 109.5 ?
C9A C8A C7A . . 118.8(15) ?
C9A C8A H8A . . 120.6 ?
C7A C8A H8A . . 120.6 ?
C8A C9A C4A . . 121.1(16) ?
C8A C9A C1A . . 131.1(17) ?
C4A C9A C1A . . 107.7(15) ?
C12 C11 C16 . . 113.7(6) ?
C12 C11 B1 . . 124.9(5) ?
C16 C11 B1 . . 121.3(5) ?
F12 C12 C11 . . 121.0(6) ?
F12 C12 C13 . . 115.5(6) ?
C11 C12 C13 . . 123.5(6) ?
F13 C13 C14 . . 119.9(6) ?
F13 C13 C12 . . 120.5(6) ?
C14 C13 C12 . . 119.6(7) ?
F14 C14 C15 . . 121.0(7) ?
F14 C14 C13 . . 119.7(7) ?
C15 C14 C13 . . 119.3(6) ?
F15 C15 C14 . . 120.4(6) ?
F15 C15 C16 . . 119.7(7) ?
C14 C15 C16 . . 119.8(6) ?
F16 C16 C15 . . 116.7(6) ?
F16 C16 C11 . . 119.3(5) ?
C15 C16 C11 . . 124.0(6) ?
C26 C21 C22 . . 114.3(5) ?
C26 C21 B1 . . 123.7(5) ?
C22 C21 B1 . . 122.0(5) ?
F22 C22 C23 . . 118.7(5) ?
F22 C22 C21 . . 118.7(5) ?
C23 C22 C21 . . 122.7(6) ?
C24 C23 F23 . . 120.0(6) ?
C24 C23 C22 . . 120.4(6) ?
F23 C23 C22 . . 119.6(6) ?
C23 C24 F24 . . 120.8(6) ?
C23 C24 C25 . . 119.8(6) ?
F24 C24 C25 . . 119.4(6) ?
F25 C25 C24 . . 120.0(5) ?
F25 C25 C26 . . 120.7(6) ?
C24 C25 C26 . . 119.2(6) ?
F26 C26 C25 . . 117.5(5) ?
F26 C26 C21 . . 118.9(5) ?
C25 C26 C21 . . 123.5(6) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 B1 C2 C3 . . . . 7.(4) ?
C21 B1 C2 C3 . . . . -170.(2) ?
C11 B1 C2 C1 . . . . 172.4(17) ?
C21 B1 C2 C1 . . . . -4.(3) ?
C9 C1 C2 C3 . . . . -7.(3) ?
C9 C1 C2 B1 . . . . -175.(2) ?
B1 C2 C3 C4 . . . . 175.(2) ?
C1 C2 C3 C4 . . . . 7.(3) ?
C2 C3 C4 C5 . . . . 175.7(18) ?
C2 C3 C4 C9 . . . . -5.(2) ?
C3 C4 C5 C6 . . . . 178.7(16) ?
C9 C4 C5 C6 . . . . -0.9(16) ?
C4 C5 C6 C7 . . . . -1.7(16) ?
C5 C6 C7 C8 . . . . 2.(2) ?
C5 C6 C7 C10 . . . . -177.3(11) ?
C6 C7 C8 C9 . . . . 0.(2) ?
C10 C7 C8 C9 . . . . 179.5(12) ?
C7 C8 C9 C4 . . . . -2.5(18) ?
C7 C8 C9 C1 . . . . -178.2(16) ?
C5 C4 C9 C8 . . . . 3.1(18) ?
C3 C4 C9 C8 . . . . -176.7(13) ?
C5 C4 C9 C1 . . . . 179.5(12) ?
C3 C4 C9 C1 . . . . -0.2(18) ?
C2 C1 C9 C8 . . . . -179.7(17) ?
C2 C1 C9 C4 . . . . 4.(2) ?
C9A C1A C2A C3A . . . . -15.(4) ?
C9A C1A C2A B1 . . . . 178.(3) ?
C11 B1 C2A C3A . . . . -174.(3) ?
C21 B1 C2A C3A . . . . 13.(5) ?
C11 B1 C2A C1A . . . . -9.(6) ?
C21 B1 C2A C1A . . . . 177.(4) ?
C1A C2A C3A C4A . . . . 18.(5) ?
B1 C2A C3A C4A . . . . -175.(4) ?
C2A C3A C4A C5A . . . . 172.(3) ?
C2A C3A C4A C9A . . . . -13.(4) ?
C3A C4A C5A C6A . . . . 176.(3) ?
C9A C4A C5A C6A . . . . 2.(3) ?
C4A C5A C6A C7A . . . . -4.(3) ?
C5A C6A C7A C8A . . . . 3.(4) ?
C5A C6A C7A C10A . . . . -175.(2) ?
C6A C7A C8A C9A . . . . 0.(4) ?
C10A C7A C8A C9A . . . . 178.(2) ?
C7A C8A C9A C4A . . . . -3.(3) ?
C7A C8A C9A C1A . . . . -178.(3) ?
C5A C4A C9A C8A . . . . 2.(4) ?
C3A C4A C9A C8A . . . . -174.(2) ?
C5A C4A C9A C1A . . . . 178.(2) ?
C3A C4A C9A C1A . . . . 2.(3) ?
C2A C1A C9A C8A . . . . -177.(3) ?
C2A C1A C9A C4A . . . . 8.(4) ?
C2 B1 C11 C12 . . . . 35.9(16) ?
C2A B1 C11 C12 . . . . 39.(3) ?
C21 B1 C11 C12 . . . . -147.3(6) ?
C2 B1 C11 C16 . . . . -140.5(15) ?
C2A B1 C11 C16 . . . . -137.(3) ?
C21 B1 C11 C16 . . . . 36.3(8) ?
C16 C11 C12 F12 . . . . -175.5(5) ?
B1 C11 C12 F12 . . . . 7.9(9) ?
C16 C11 C12 C13 . . . . 2.8(8) ?
B1 C11 C12 C13 . . . . -173.8(5) ?
F12 C12 C13 F13 . . . . -4.5(8) ?
C11 C12 C13 F13 . . . . 177.1(5) ?
F12 C12 C13 C14 . . . . 176.8(5) ?
C11 C12 C13 C14 . . . . -1.5(9) ?
F13 C13 C14 F14 . . . . 0.6(9) ?
C12 C13 C14 F14 . . . . 179.3(5) ?
F13 C13 C14 C15 . . . . 179.9(6) ?
C12 C13 C14 C15 . . . . -1.4(9) ?
F14 C14 C15 F15 . . . . -0.6(9) ?
C13 C14 C15 F15 . . . . -179.9(5) ?
F14 C14 C15 C16 . . . . -177.9(5) ?
C13 C14 C15 C16 . . . . 2.8(9) ?
F15 C15 C16 F16 . . . . -0.9(8) ?
C14 C15 C16 F16 . . . . 176.5(5) ?
F15 C15 C16 C11 . . . . -178.8(5) ?
C14 C15 C16 C11 . . . . -1.4(9) ?
C12 C11 C16 F16 . . . . -179.2(5) ?
B1 C11 C16 F16 . . . . -2.4(8) ?
C12 C11 C16 C15 . . . . -1.3(8) ?
B1 C11 C16 C15 . . . . 175.4(6) ?
C2 B1 C21 C26 . . . . 60.9(16) ?
C2A B1 C21 C26 . . . . 59.(2) ?
C11 B1 C21 C26 . . . . -115.9(6) ?
C2 B1 C21 C22 . . . . -120.0(15) ?
C2A B1 C21 C22 . . . . -122.(2) ?
C11 B1 C21 C22 . . . . 63.2(7) ?
C26 C21 C22 F22 . . . . 179.3(5) ?
B1 C21 C22 F22 . . . . 0.1(8) ?
C26 C21 C22 C23 . . . . -1.0(8) ?
B1 C21 C22 C23 . . . . 179.8(5) ?
F22 C22 C23 C24 . . . . -178.4(6) ?
C21 C22 C23 C24 . . . . 1.8(9) ?
F22 C22 C23 F23 . . . . 0.2(8) ?
C21 C22 C23 F23 . . . . -179.5(5) ?
F23 C23 C24 F24 . . . . 0.8(9) ?
C22 C23 C24 F24 . . . . 179.4(5) ?
F23 C23 C24 C25 . . . . 179.0(5) ?
C22 C23 C24 C25 . . . . -2.4(9) ?
C23 C24 C25 F25 . . . . -179.9(5) ?
F24 C24 C25 F25 . . . . -1.7(9) ?
C23 C24 C25 C26 . . . . 2.2(9) ?
F24 C24 C25 C26 . . . . -179.6(5) ?
F25 C25 C26 F26 . . . . -1.8(8) ?
C24 C25 C26 F26 . . . . 176.1(5) ?
F25 C25 C26 C21 . . . . -179.3(5) ?
C24 C25 C26 C21 . . . . -1.4(9) ?
C22 C21 C26 F26 . . . . -176.7(5) ?
B1 C21 C26 F26 . . . . 2.5(8) ?
C22 C21 C26 C25 . . . . 0.8(8) ?
B1 C21 C26 C25 . . . . 180.0(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_erk9217
_audit_block_doi                 10.5517/ccdc.csd.cc2210lr
_database_code_depnum_ccdc_archive 'CCDC 1907603'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H6 B F11'
_chemical_formula_iupac          ?
_chemical_formula_weight         478.07
_chemical_absolute_configuration .

_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                   7.4593(3)
_cell_length_b                   10.9446(4)
_cell_length_c                   21.4005(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.12(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7034
_cell_measurement_theta_min      4.1316
_cell_measurement_theta_max      68.2248
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    1.697
_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  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(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            16290
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;

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

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

The borylindene unit is disordered over two positions. Several
restraints (SADI, SAME, ISOR and SIMU) were used in order to 
improve refinement stability.
;

_reflns_number_total             3060
_reflns_number_gt                2523
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1458
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.126
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     389
_refine_ls_number_restraints     269
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+1.6155P] 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         0.313
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 820 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(16)

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    '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 0.6858(12) 0.3535(9) 0.3161(4) 0.0271(19) Uani d . . D 1.0 . .
C C1 0.778(2) 0.5911(10) 0.2849(5) 0.022(2) Uani d U P D 0.850(11) A 1
H H1A 0.6668 0.6177 0.2633 0.026 Uiso calc U P R 0.850(11) A 1
H H1B 0.8684 0.5688 0.2532 0.026 Uiso calc U P R 0.850(11) A 1
C C2 0.740(2) 0.4849(10) 0.3281(6) 0.023(3) Uani d U P D 0.850(11) A 1
C C3 0.778(3) 0.5219(12) 0.3878(6) 0.024(3) Uani d U P D 0.850(11) A 1
H H3 0.7601 0.4727 0.4238 0.029 Uiso calc U P R 0.850(11) A 1
C C4 0.847(4) 0.6436(14) 0.3891(6) 0.023(3) Uani d U P D 0.850(11) A 1
C C5 0.9065(15) 0.7197(9) 0.4379(5) 0.024(2) Uani d U P D 0.850(11) A 1
H H5 0.9011 0.6917 0.4799 0.029 Uiso calc U P R 0.850(11) A 1
C C6 0.9727(14) 0.8342(9) 0.4251(4) 0.026(2) Uani d U P D 0.850(11) A 1
H H6 1.0176 0.8843 0.4578 0.031 Uiso calc U P R 0.850(11) A 1
C C7 0.9733(13) 0.8758(8) 0.3640(5) 0.025(2) Uani d U P D 0.850(11) A 1
F F1 1.0408(7) 0.9881(5) 0.3518(2) 0.0307(16) Uani d U P D 0.850(11) A 1
C C8 0.9089(15) 0.8075(9) 0.3138(5) 0.023(2) Uani d U P D 0.850(11) A 1
H H8 0.9072 0.8391 0.2724 0.027 Uiso calc U P R 0.850(11) A 1
C C9 0.847(3) 0.6904(11) 0.3277(6) 0.024(3) Uani d U P D 0.850(11) A 1
C C1A 0.775(19) 0.526(6) 0.399(2) 0.022(14) Uani d U P D 0.150(11) A 2
H H1C 0.8718 0.474 0.4164 0.026 Uiso calc U P R 0.150(11) A 2
H H1D 0.6737 0.5286 0.4289 0.026 Uiso calc U P R 0.150(11) A 2
C C2A 0.716(14) 0.483(4) 0.335(3) 0.023(14) Uani d U P D 0.150(11) A 2
C C3A 0.779(13) 0.561(4) 0.290(2) 0.018(13) Uani d U P D 0.150(11) A 2
H H3A 0.7812 0.5444 0.2468 0.022 Uiso calc U P R 0.150(11) A 2
C C4A 0.839(14) 0.670(4) 0.318(2) 0.012(13) Uani d U P D 0.150(11) A 2
C C5A 0.881(9) 0.788(4) 0.297(2) 0.021(12) Uani d U P D 0.150(11) A 2
H H5A 0.8665 0.8076 0.2536 0.025 Uiso calc U P R 0.150(11) A 2
C C6A 0.946(7) 0.875(4) 0.3382(18) 0.019(11) Uani d U P D 0.150(11) A 2
H H6A 0.9694 0.9558 0.3245 0.023 Uiso calc U P R 0.150(11) A 2
C C7A 0.974(9) 0.842(4) 0.4000(18) 0.024(10) Uani d U P D 0.150(11) A 2
F F1A 1.033(5) 0.921(3) 0.4430(15) 0.048(11) Uani d U P D 0.150(11) A 2
C C8A 0.941(10) 0.726(4) 0.424(2) 0.028(14) Uani d U P D 0.150(11) A 2
H H8A 0.9818 0.6999 0.4641 0.033 Uiso calc U P R 0.150(11) A 2
C C9A 0.843(18) 0.654(6) 0.383(2) 0.010(13) Uani d U P D 0.150(11) A 2
C C11 0.6586(10) 0.2949(7) 0.2479(3) 0.0238(17) Uani d . . . 1.0 . .
C C12 0.5737(10) 0.3543(7) 0.1986(4) 0.0265(17) Uani d . . . 1.0 . .
F F12 0.5006(6) 0.4649(4) 0.2067(2) 0.0302(10) Uani d . . . 1.0 . .
C C13 0.5571(10) 0.3022(7) 0.1404(3) 0.0260(16) Uani d . . . 1.0 . .
F F13 0.4722(6) 0.3622(4) 0.09375(19) 0.0314(11) Uani d . . . 1.0 . .
C C14 0.6192(11) 0.1858(7) 0.1290(4) 0.0278(17) Uani d . . . 1.0 . .
F F14 0.6037(6) 0.1367(5) 0.07244(19) 0.0337(11) Uani d . . . 1.0 . .
C C15 0.7038(11) 0.1232(7) 0.1767(4) 0.0271(17) Uani d . . . 1.0 . .
F F15 0.7698(6) 0.0117(4) 0.1664(2) 0.0342(11) Uani d . . . 1.0 . .
C C16 0.7205(10) 0.1789(7) 0.2339(4) 0.0253(16) Uani d . . . 1.0 . .
F F16 0.8107(6) 0.1140(4) 0.2776(2) 0.0299(10) Uani d . . . 1.0 . .
C C21 0.6667(10) 0.2614(7) 0.3727(3) 0.0260(17) Uani d . . . 1.0 . .
C C22 0.5060(10) 0.2078(7) 0.3881(3) 0.0241(16) Uani d . . . 1.0 . .
F F22 0.3580(6) 0.2352(5) 0.3535(2) 0.0349(11) Uani d . . . 1.0 . .
C C23 0.4833(11) 0.1294(8) 0.4376(4) 0.0288(17) Uani d . . . 1.0 . .
F F23 0.3223(6) 0.0812(5) 0.4513(2) 0.0406(13) Uani d . . . 1.0 . .
C C24 0.6308(13) 0.0991(7) 0.4730(4) 0.0311(19) Uani d . . . 1.0 . .
F F24 0.6140(7) 0.0200(4) 0.5207(2) 0.0389(12) Uani d . . . 1.0 . .
C C25 0.7952(11) 0.1463(8) 0.4593(3) 0.0272(17) Uani d . . . 1.0 . .
F F25 0.9387(6) 0.1146(4) 0.4937(2) 0.0391(12) Uani d . . . 1.0 . .
C C26 0.8129(10) 0.2259(8) 0.4098(4) 0.0287(18) Uani d . . . 1.0 . .
F F26 0.9761(6) 0.2701(4) 0.3966(2) 0.0390(12) 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
B1 C2A . 1.49(3) ?
B1 C2 . 1.517(13) ?
B1 C21 . 1.582(12) ?
B1 C11 . 1.606(11) ?
C1 C2 . 1.511(16) ?
C1 C9 . 1.514(16) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.369(16) ?
C3 C4 . 1.428(12) ?
C3 H3 . 0.95 ?
C4 C5 . 1.409(12) ?
C4 C9 . 1.411(13) ?
C5 C6 . 1.375(12) ?
C5 H5 . 0.95 ?
C6 C7 . 1.383(11) ?
C6 H6 . 0.95 ?
C7 F1 . 1.354(11) ?
C7 C8 . 1.395(12) ?
C8 C9 . 1.393(12) ?
C8 H8 . 0.95 ?
C1A C2A . 1.51(3) ?
C1A C9A . 1.52(3) ?
C1A H1C . 0.99 ?
C1A H1D . 0.99 ?
C2A C3A . 1.37(3) ?
C3A C4A . 1.40(2) ?
C3A H3A . 0.95 ?
C4A C5A . 1.40(2) ?
C4A C9A . 1.42(3) ?
C5A C6A . 1.39(2) ?
C5A H5A . 0.95 ?
C6A C7A . 1.38(2) ?
C6A H6A . 0.95 ?
C7A F1A . 1.33(3) ?
C7A C8A . 1.39(2) ?
C8A C9A . 1.39(2) ?
C8A H8A . 0.95 ?
C11 C16 . 1.383(11) ?
C11 C12 . 1.392(10) ?
C12 F12 . 1.339(9) ?
C12 C13 . 1.375(11) ?
C13 F13 . 1.353(9) ?
C13 C14 . 1.378(12) ?
C14 F14 . 1.329(9) ?
C14 C15 . 1.382(12) ?
C15 F15 . 1.334(9) ?
C15 C16 . 1.375(11) ?
C16 F16 . 1.353(9) ?
C21 C22 . 1.374(11) ?
C21 C26 . 1.404(11) ?
C22 F22 . 1.362(9) ?
C22 C23 . 1.374(11) ?
C23 F23 . 1.344(9) ?
C23 C24 . 1.376(12) ?
C24 F24 . 1.344(9) ?
C24 C25 . 1.363(12) ?
C25 F25 . 1.344(9) ?
C25 C26 . 1.377(11) ?
C26 F26 . 1.340(9) ?

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
C2A B1 C21 . . 114.(2) ?
C2 B1 C21 . . 119.9(9) ?
C2A B1 C11 . . 130.(2) ?
C2 B1 C11 . . 124.5(9) ?
C21 B1 C11 . . 115.5(7) ?
C2 C1 C9 . . 104.2(8) ?
C2 C1 H1A . . 110.9 ?
C9 C1 H1A . . 110.9 ?
C2 C1 H1B . . 110.9 ?
C9 C1 H1B . . 110.9 ?
H1A C1 H1B . . 108.9 ?
C3 C2 C1 . . 107.8(8) ?
C3 C2 B1 . . 119.5(11) ?
C1 C2 B1 . . 132.5(10) ?
C2 C3 C4 . . 111.6(10) ?
C2 C3 H3 . . 124.2 ?
C4 C3 H3 . . 124.2 ?
C5 C4 C9 . . 118.4(11) ?
C5 C4 C3 . . 132.9(12) ?
C9 C4 C3 . . 108.8(10) ?
C6 C5 C4 . . 120.3(10) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 119.3(9) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
F1 C7 C6 . . 118.8(9) ?
F1 C7 C8 . . 117.7(8) ?
C6 C7 C8 . . 123.4(9) ?
C9 C8 C7 . . 116.2(9) ?
C9 C8 H8 . . 121.9 ?
C7 C8 H8 . . 121.9 ?
C8 C9 C4 . . 122.3(12) ?
C8 C9 C1 . . 130.2(10) ?
C4 C9 C1 . . 107.5(9) ?
C2A C1A C9A . . 100.(2) ?
C2A C1A H1C . . 111.7 ?
C9A C1A H1C . . 111.7 ?
C2A C1A H1D . . 111.7 ?
C9A C1A H1D . . 111.7 ?
H1C C1A H1D . . 109.4 ?
C3A C2A B1 . . 117.(4) ?
C3A C2A C1A . . 110.(3) ?
B1 C2A C1A . . 126.(5) ?
C2A C3A C4A . . 110.(3) ?
C2A C3A H3A . . 124.9 ?
C4A C3A H3A . . 124.9 ?
C5A C4A C3A . . 136.(3) ?
C5A C4A C9A . . 116.(3) ?
C3A C4A C9A . . 108.(3) ?
C6A C5A C4A . . 120.(3) ?
C6A C5A H5A . . 120.1 ?
C4A C5A H5A . . 120.1 ?
C7A C6A C5A . . 119.(3) ?
C7A C6A H6A . . 120.4 ?
C5A C6A H6A . . 120.4 ?
F1A C7A C6A . . 123.(3) ?
F1A C7A C8A . . 113.(3) ?
C6A C7A C8A . . 124.(3) ?
C9A C8A C7A . . 112.(3) ?
C9A C8A H8A . . 123.8 ?
C7A C8A H8A . . 123.8 ?
C8A C9A C4A . . 124.(4) ?
C8A C9A C1A . . 124.(4) ?
C4A C9A C1A . . 109.(3) ?
C16 C11 C12 . . 114.6(7) ?
C16 C11 B1 . . 121.4(7) ?
C12 C11 B1 . . 124.0(7) ?
F12 C12 C13 . . 117.1(7) ?
F12 C12 C11 . . 120.6(7) ?
C13 C12 C11 . . 122.3(7) ?
F13 C13 C12 . . 120.6(7) ?
F13 C13 C14 . . 118.3(7) ?
C12 C13 C14 . . 121.0(7) ?
F14 C14 C13 . . 120.5(7) ?
F14 C14 C15 . . 120.8(7) ?
C13 C14 C15 . . 118.7(7) ?
F15 C15 C16 . . 121.3(7) ?
F15 C15 C14 . . 120.1(7) ?
C16 C15 C14 . . 118.7(7) ?
F16 C16 C15 . . 115.3(7) ?
F16 C16 C11 . . 119.9(7) ?
C15 C16 C11 . . 124.7(7) ?
C22 C21 C26 . . 115.1(7) ?
C22 C21 B1 . . 122.3(7) ?
C26 C21 B1 . . 122.7(7) ?
F22 C22 C23 . . 117.1(7) ?
F22 C22 C21 . . 118.9(6) ?
C23 C22 C21 . . 124.0(7) ?
F23 C23 C22 . . 121.6(7) ?
F23 C23 C24 . . 120.0(7) ?
C22 C23 C24 . . 118.4(8) ?
F24 C24 C25 . . 119.4(8) ?
F24 C24 C23 . . 119.9(8) ?
C25 C24 C23 . . 120.7(7) ?
F25 C25 C24 . . 120.1(7) ?
F25 C25 C26 . . 120.5(7) ?
C24 C25 C26 . . 119.4(7) ?
F26 C26 C25 . . 118.5(7) ?
F26 C26 C21 . . 119.1(7) ?
C25 C26 C21 . . 122.4(7) ?

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 C1 C2 C3 . . . . 2.0(19) ?
C9 C1 C2 B1 . . . . -173.1(16) ?
C21 B1 C2 C3 . . . . 2.(2) ?
C11 B1 C2 C3 . . . . -173.2(14) ?
C21 B1 C2 C1 . . . . 176.6(14) ?
C11 B1 C2 C1 . . . . 1.(2) ?
C1 C2 C3 C4 . . . . -3.(2) ?
B1 C2 C3 C4 . . . . 173.0(19) ?
C2 C3 C4 C5 . . . . -179.(3) ?
C2 C3 C4 C9 . . . . 3.(3) ?
C9 C4 C5 C6 . . . . -3.(3) ?
C3 C4 C5 C6 . . . . 178.(3) ?
C4 C5 C6 C7 . . . . 3.(2) ?
C5 C6 C7 F1 . . . . -179.2(9) ?
C5 C6 C7 C8 . . . . 0.3(17) ?
F1 C7 C8 C9 . . . . 177.4(12) ?
C6 C7 C8 C9 . . . . -2.1(18) ?
C7 C8 C9 C4 . . . . 1.(3) ?
C7 C8 C9 C1 . . . . -176.8(16) ?
C5 C4 C9 C8 . . . . 2.(3) ?
C3 C4 C9 C8 . . . . -179.(2) ?
C5 C4 C9 C1 . . . . 180.(2) ?
C3 C4 C9 C1 . . . . -1.(3) ?
C2 C1 C9 C8 . . . . 177.6(18) ?
C2 C1 C9 C4 . . . . -1.(2) ?
C21 B1 C2A C3A . . . . 164.(7) ?
C11 B1 C2A C3A . . . . -20.(11) ?
C21 B1 C2A C1A . . . . 16.(11) ?
C11 B1 C2A C1A . . . . -168.(7) ?
C9A C1A C2A C3A . . . . 12.(12) ?
C9A C1A C2A B1 . . . . 162.(9) ?
B1 C2A C3A C4A . . . . -167.(8) ?
C1A C2A C3A C4A . . . . -14.(12) ?
C2A C3A C4A C5A . . . . -165.(12) ?
C2A C3A C4A C9A . . . . 10.(13) ?
C3A C4A C5A C6A . . . . -177.(11) ?
C9A C4A C5A C6A . . . . 8.(13) ?
C4A C5A C6A C7A . . . . 3.(11) ?
C5A C6A C7A F1A . . . . -179.(6) ?
C5A C6A C7A C8A . . . . -1.(12) ?
F1A C7A C8A C9A . . . . 166.(8) ?
C6A C7A C8A C9A . . . . -12.(12) ?
C7A C8A C9A C4A . . . . 25.(15) ?
C7A C8A C9A C1A . . . . -175.(11) ?
C5A C4A C9A C8A . . . . -23.(17) ?
C3A C4A C9A C8A . . . . 161.(11) ?
C5A C4A C9A C1A . . . . 174.(11) ?
C3A C4A C9A C1A . . . . -2.(14) ?
C2A C1A C9A C8A . . . . -168.(11) ?
C2A C1A C9A C4A . . . . -6.(13) ?
C2A B1 C11 C16 . . . . 146.(5) ?
C2 B1 C11 C16 . . . . 138.0(11) ?
C21 B1 C11 C16 . . . . -37.4(11) ?
C2A B1 C11 C12 . . . . -33.(5) ?
C2 B1 C11 C12 . . . . -41.7(14) ?
C21 B1 C11 C12 . . . . 142.9(8) ?
C16 C11 C12 F12 . . . . 177.0(7) ?
B1 C11 C12 F12 . . . . -3.2(12) ?
C16 C11 C12 C13 . . . . -1.5(11) ?
B1 C11 C12 C13 . . . . 178.3(7) ?
F12 C12 C13 F13 . . . . 0.8(11) ?
C11 C12 C13 F13 . . . . 179.4(7) ?
F12 C12 C13 C14 . . . . -176.2(7) ?
C11 C12 C13 C14 . . . . 2.3(12) ?
F13 C13 C14 F14 . . . . 3.4(11) ?
C12 C13 C14 F14 . . . . -179.5(7) ?
F13 C13 C14 C15 . . . . -179.1(7) ?
C12 C13 C14 C15 . . . . -2.0(11) ?
F14 C14 C15 F15 . . . . -0.5(11) ?
C13 C14 C15 F15 . . . . -178.1(7) ?
F14 C14 C15 C16 . . . . 178.4(7) ?
C13 C14 C15 C16 . . . . 0.9(11) ?
F15 C15 C16 F16 . . . . 1.3(11) ?
C14 C15 C16 F16 . . . . -177.6(7) ?
F15 C15 C16 C11 . . . . 178.8(7) ?
C14 C15 C16 C11 . . . . -0.1(12) ?
C12 C11 C16 F16 . . . . 177.7(6) ?
B1 C11 C16 F16 . . . . -2.0(11) ?
C12 C11 C16 C15 . . . . 0.4(11) ?
B1 C11 C16 C15 . . . . -179.4(7) ?
C2A B1 C21 C22 . . . . 109.(4) ?
C2 B1 C21 C22 . . . . 116.8(11) ?
C11 B1 C21 C22 . . . . -67.5(10) ?
C2A B1 C21 C26 . . . . -72.(4) ?
C2 B1 C21 C26 . . . . -64.9(13) ?
C11 B1 C21 C26 . . . . 110.8(9) ?
C26 C21 C22 F22 . . . . -178.6(7) ?
B1 C21 C22 F22 . . . . -0.2(11) ?
C26 C21 C22 C23 . . . . 2.9(12) ?
B1 C21 C22 C23 . . . . -178.7(8) ?
F22 C22 C23 F23 . . . . 0.2(11) ?
C21 C22 C23 F23 . . . . 178.7(7) ?
F22 C22 C23 C24 . . . . 179.4(7) ?
C21 C22 C23 C24 . . . . -2.1(12) ?
F23 C23 C24 F24 . . . . 1.0(12) ?
C22 C23 C24 F24 . . . . -178.2(7) ?
F23 C23 C24 C25 . . . . 179.4(7) ?
C22 C23 C24 C25 . . . . 0.2(12) ?
F24 C24 C25 F25 . . . . -0.6(12) ?
C23 C24 C25 F25 . . . . -179.0(7) ?
F24 C24 C25 C26 . . . . 179.0(7) ?
C23 C24 C25 C26 . . . . 0.6(12) ?
F25 C25 C26 F26 . . . . 0.4(12) ?
C24 C25 C26 F26 . . . . -179.2(7) ?
F25 C25 C26 C21 . . . . 180.0(8) ?
C24 C25 C26 C21 . . . . 0.4(13) ?
C22 C21 C26 F26 . . . . 177.6(7) ?
B1 C21 C26 F26 . . . . -0.8(12) ?
C22 C21 C26 C25 . . . . -2.0(12) ?
B1 C21 C26 C25 . . . . 179.6(8) ?

####################################################################### 
# 
# 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_erk9457
_audit_block_doi                 10.5517/ccdc.csd.cc2210nt
_database_code_depnum_ccdc_archive 'CCDC 1907605'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H24 B3 F30 N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         1461.31

_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                   18.2599(7)
_cell_length_b                   26.5169(9)
_cell_length_c                   13.8464(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.1620(10)
_cell_angle_gamma                90
_cell_volume                     6677.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9531
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2904

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

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

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            27433
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_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.

Four C6F5 groups are disordered over two positions. Several restraints
(SADI, SAME, ISOR and SIMU) were used in order to improve refinement
stability.

Two badly disordered dichloromethane molecules 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.
;

_reflns_number_total             11481
_reflns_number_gt                6701
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1889
_refine_ls_R_factor_gt           0.1224
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2599
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.119
_refine_ls_number_reflns         11481
_refine_ls_number_parameters     1302
_refine_ls_number_restraints     1264
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+36.7323P] 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         1.028
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0016(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 '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'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-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
N N1A 0.7632(4) 0.2973(2) 1.3533(5) 0.0426(16) Uani d . . . 1.0 . .
N N1B 0.7968(3) 0.5285(2) 0.7021(5) 0.0452(16) Uani d . . . 1.0 . .
N N1C 0.3757(3) 0.3928(2) 0.8491(5) 0.0398(15) Uani d . . . 1.0 . .
B B1A 0.7736(5) 0.3589(3) 1.3531(6) 0.038(2) Uani d . . . 1.0 . .
C C2A 0.7525(4) 0.3725(2) 1.2411(6) 0.0366(17) Uani d . . . 1.0 . .
C C3A 0.7878(4) 0.3981(3) 1.1751(5) 0.0351(17) Uani d . . . 1.0 . .
H H3A 0.8363 0.411 1.1869 0.042 Uiso calc U . R 1.0 . .
C C4A 0.7424(4) 0.4038(2) 1.0828(5) 0.0344(17) Uani d . . . 1.0 . .
C C5A 0.6753(4) 0.3786(2) 1.0931(5) 0.0332(16) Uani d . . . 1.0 . .
C C1A 0.6793(4) 0.3547(3) 1.1907(5) 0.0379(18) Uani d . . . 1.0 . .
H H1A 0.6783 0.3174 1.1851 0.045 Uiso calc U . R 1.0 . .
H H1B 0.6378 0.3657 1.2269 0.045 Uiso calc U . R 1.0 . .
C C11A 0.8576(4) 0.3736(3) 1.3955(5) 0.0365(17) Uani d . . . 1.0 . .
C C12A 0.9105(4) 0.3418(3) 1.4462(6) 0.046(2) Uani d . . . 1.0 . .
C C13A 0.9794(4) 0.3568(3) 1.4786(6) 0.053(2) Uani d . . . 1.0 . .
C C14A 1.0003(4) 0.4058(4) 1.4669(6) 0.054(2) Uani d . . . 1.0 . .
C C15A 0.9518(5) 0.4387(3) 1.4192(6) 0.052(2) Uani d . . . 1.0 . .
C C16A 0.8820(4) 0.4227(3) 1.3874(5) 0.0413(18) Uani d . . . 1.0 . .
C C21A 0.7182(4) 0.3848(3) 1.4273(6) 0.0410(18) Uani d . . . 1.0 . .
C C22A 0.7192(4) 0.3709(3) 1.5239(6) 0.0428(19) Uani d . . . 1.0 . .
C C23A 0.6749(5) 0.3908(3) 1.5895(6) 0.050(2) Uani d . . . 1.0 . .
C C24A 0.6266(5) 0.4291(3) 1.5598(6) 0.052(2) Uani d . . . 1.0 . .
C C25A 0.6246(4) 0.4459(3) 1.4659(6) 0.047(2) Uani d . . . 1.0 . .
C C26A 0.6698(4) 0.4248(3) 1.4022(5) 0.0393(18) Uani d . . . 1.0 . .
C C31A 0.7095(4) 0.2722(3) 1.3962(6) 0.049(2) Uani d . . . 1.0 . .
H H31A 0.6754 0.2909 1.4301 0.059 Uiso calc U . R 1.0 . .
C C32A 0.7035(6) 0.2209(3) 1.3913(7) 0.067(3) Uani d . . . 1.0 . .
H H32A 0.6669 0.2039 1.4236 0.08 Uiso calc U . R 1.0 . .
C C33A 0.7513(6) 0.1937(3) 1.3391(7) 0.066(3) Uani d . . . 1.0 . .
H H33A 0.7483 0.158 1.3361 0.079 Uiso calc U . R 1.0 . .
C C34A 0.8031(5) 0.2190(3) 1.2918(7) 0.061(3) Uani d . . . 1.0 . .
H H34A 0.8355 0.2011 1.2543 0.074 Uiso calc U . R 1.0 . .
C C35A 0.8075(5) 0.2709(3) 1.2995(6) 0.054(2) Uani d . . . 1.0 . .
H H35A 0.8427 0.2885 1.2658 0.065 Uiso calc U . R 1.0 . .
F F12A 0.8930(3) 0.29349(17) 1.4648(4) 0.0643(14) Uani d . . . 1.0 . .
F F13A 1.0261(3) 0.3242(2) 1.5260(4) 0.0789(17) Uani d . . . 1.0 . .
F F14A 1.0690(3) 0.4210(2) 1.4993(4) 0.0768(16) Uani d . . . 1.0 . .
F F15A 0.9720(3) 0.48703(19) 1.4047(4) 0.0693(15) Uani d . . . 1.0 . .
F F16A 0.8358(3) 0.45836(15) 1.3467(3) 0.0511(12) Uani d . . . 1.0 . .
F F22A 0.7660(3) 0.33389(17) 1.5579(3) 0.0543(12) Uani d . . . 1.0 . .
F F23A 0.6780(3) 0.3739(2) 1.6811(3) 0.0690(15) Uani d . . . 1.0 . .
F F24A 0.5832(3) 0.4497(2) 1.6232(4) 0.0750(16) Uani d . . . 1.0 . .
F F25A 0.5790(3) 0.48371(18) 1.4373(4) 0.0680(14) Uani d . . . 1.0 . .
F F26A 0.6643(2) 0.44489(16) 1.3127(3) 0.0512(12) Uani d . . . 1.0 . .
C C2B 0.7900(4) 0.4809(3) 0.8686(6) 0.0412(18) Uani d . . . 1.0 . .
C C3B 0.7220(4) 0.4633(3) 0.8449(5) 0.0415(18) Uani d . . . 1.0 . .
H H3B 0.6933 0.4705 0.7858 0.05 Uiso calc U . R 1.0 . .
C C4B 0.6979(4) 0.4313(3) 0.9228(5) 0.0347(17) Uani d . . . 1.0 . .
C C5B 0.7530(4) 0.4304(2) 0.9989(5) 0.0307(16) Uani d . . . 1.0 . .
C C1B 0.8162(4) 0.4609(3) 0.9696(5) 0.0387(18) Uani d . . . 1.0 . .
H H1C 0.8606 0.4396 0.9673 0.046 Uiso calc U . R 1.0 . .
H H1D 0.8277 0.489 1.0155 0.046 Uiso calc U . R 1.0 . .
B B1B 0.8416(5) 0.5137(4) 0.8060(7) 0.043(2) Uani d . . D 1.0 . .
C C11B 0.8677(6) 0.5696(3) 0.8531(8) 0.042(3) Uani d U P D 0.772(18) A 1
C C12B 0.8353(5) 0.5940(3) 0.9250(7) 0.046(3) Uani d U P D 0.772(18) A 1
F F12B 0.7788(6) 0.5728(4) 0.9677(9) 0.055(3) Uani d U P D 0.772(18) A 1
C C13B 0.8565(8) 0.6404(4) 0.9608(9) 0.061(4) Uani d U P D 0.772(18) A 1
F F13B 0.8224(8) 0.6621(5) 1.0336(9) 0.080(4) Uani d U P D 0.772(18) A 1
C C14B 0.9119(9) 0.6653(5) 0.9217(11) 0.079(4) Uani d U P D 0.772(18) A 1
F F14B 0.9309(8) 0.7117(3) 0.9548(9) 0.122(5) Uani d U P D 0.772(18) A 1
C C15B 0.9456(8) 0.6438(4) 0.8480(10) 0.071(4) Uani d U P D 0.772(18) A 1
F F15B 0.9999(8) 0.6684(4) 0.8071(9) 0.122(5) Uani d U P D 0.772(18) A 1
C C16B 0.9223(8) 0.5973(4) 0.8155(9) 0.055(3) Uani d U P D 0.772(18) A 1
F F16B 0.9555(6) 0.5785(3) 0.7390(7) 0.071(3) Uani d U P D 0.772(18) A 1
C C11E 0.8484(19) 0.5742(7) 0.837(2) 0.056(10) Uani d U P D 0.228(18) A 2
C C12E 0.8183(18) 0.5964(9) 0.913(2) 0.059(9) Uani d U P D 0.228(18) A 2
F F12E 0.772(2) 0.5713(18) 0.967(3) 0.090(17) Uani d U P D 0.228(18) A 2
C C13E 0.833(2) 0.6450(10) 0.942(3) 0.056(9) Uani d U P D 0.228(18) A 2
F F13E 0.802(2) 0.6649(16) 1.019(3) 0.067(12) Uani d U P D 0.228(18) A 2
C C14E 0.879(2) 0.6741(11) 0.893(3) 0.077(10) Uani d U P D 0.228(18) A 2
F F14E 0.888(3) 0.7237(11) 0.915(3) 0.140(18) Uani d U P D 0.228(18) A 2
C C15E 0.909(2) 0.6545(10) 0.814(3) 0.071(9) Uani d U P D 0.228(18) A 2
F F15E 0.956(2) 0.6818(13) 0.765(3) 0.135(17) Uani d U P D 0.228(18) A 2
C C16E 0.893(2) 0.6057(9) 0.789(3) 0.061(9) Uani d U P D 0.228(18) A 2
F F16E 0.925(2) 0.5869(14) 0.711(2) 0.107(14) Uani d U P D 0.228(18) A 2
C C21B 0.9109(4) 0.4762(3) 0.7894(5) 0.0429(19) Uani d U . D 1.0 . .
C C22B 0.9820(4) 0.4773(4) 0.8347(6) 0.046(3) Uani d U P D 0.82(2) B 1
F F22B 1.0041(4) 0.5178(4) 0.8912(7) 0.060(2) Uani d U P D 0.82(2) B 1
C C23B 1.0346(5) 0.4413(5) 0.8272(9) 0.047(3) Uani d U P D 0.82(2) B 1
F F23B 1.1031(3) 0.4478(5) 0.8709(7) 0.076(3) Uani d U P D 0.82(2) B 1
C C24B 1.0185(5) 0.3984(5) 0.7760(9) 0.055(3) Uani d U P D 0.82(2) B 1
F F24B 1.0713(4) 0.3636(4) 0.7668(8) 0.080(3) Uani d U P D 0.82(2) B 1
C C25B 0.9483(5) 0.3933(4) 0.7314(9) 0.047(3) Uani d U P D 0.82(2) B 1
F F25B 0.9300(6) 0.3504(3) 0.6815(9) 0.061(3) Uani d U P D 0.82(2) B 1
C C26B 0.8972(5) 0.4312(4) 0.7394(11) 0.041(3) Uani d U P D 0.82(2) B 1
F F26B 0.8297(6) 0.4220(6) 0.6937(12) 0.066(5) Uani d U P D 0.82(2) B 1
C C22E 0.9822(8) 0.4910(11) 0.812(2) 0.041(9) Uani d U P D 0.18(2) B 2
F F22E 0.997(2) 0.5353(13) 0.858(3) 0.072(12) Uani d U P D 0.18(2) B 2
C C23E 1.0400(12) 0.4591(13) 0.801(2) 0.037(9) Uani d U P D 0.18(2) B 2
F F23E 1.1083(13) 0.4734(17) 0.837(3) 0.071(11) Uani d U P D 0.18(2) B 2
C C24E 1.0273(16) 0.4137(14) 0.756(3) 0.047(10) Uani d U P D 0.18(2) B 2
F F24E 1.083(2) 0.3821(17) 0.743(4) 0.098(16) Uani d U P D 0.18(2) B 2
C C25E 0.9575(16) 0.4013(14) 0.718(4) 0.051(10) Uani d U P D 0.18(2) B 2
F F25E 0.944(3) 0.3556(15) 0.676(5) 0.081(17) Uani d U P D 0.18(2) B 2
C C26E 0.9007(15) 0.4337(15) 0.733(4) 0.045(10) Uani d U P D 0.18(2) B 2
F F26E 0.8328(15) 0.4185(17) 0.697(3) 0.019(10) Uani d U P D 0.18(2) B 2
C C31B 0.7313(4) 0.5517(3) 0.7063(7) 0.052(2) Uani d . . . 1.0 . .
H H31B 0.7138 0.5583 0.7677 0.062 Uiso calc U . R 1.0 . .
C C32B 0.6894(5) 0.5661(3) 0.6228(7) 0.056(2) Uani d . . . 1.0 . .
H H32B 0.6437 0.5827 0.6272 0.068 Uiso calc U . R 1.0 . .
C C33B 0.7133(5) 0.5564(3) 0.5338(7) 0.059(2) Uani d . . . 1.0 . .
H H33B 0.6844 0.565 0.4757 0.071 Uiso calc U . R 1.0 . .
C C34B 0.7810(5) 0.5336(3) 0.5316(7) 0.060(2) Uani d . . . 1.0 . .
H H34B 0.7996 0.5268 0.471 0.071 Uiso calc U . R 1.0 . .
C C35B 0.8219(5) 0.5207(3) 0.6159(6) 0.049(2) Uani d . . . 1.0 . .
H H35B 0.869 0.5058 0.6128 0.059 Uiso calc U . R 1.0 . .
C C2C 0.5120(4) 0.3674(3) 0.9136(6) 0.0415(19) Uani d . . . 1.0 . .
C C3C 0.5468(4) 0.3565(3) 1.0014(6) 0.0395(18) Uani d . . . 1.0 . .
H H3C 0.5262 0.3362 1.0486 0.047 Uiso calc U . R 1.0 . .
C C4C 0.6204(4) 0.3798(2) 1.0157(5) 0.0326(16) Uani d . . . 1.0 . .
C C5C 0.6312(4) 0.4062(3) 0.9300(5) 0.0340(17) Uani d . . . 1.0 . .
C C1C 0.5647(4) 0.3989(3) 0.8599(6) 0.0445(19) Uani d . . . 1.0 . .
H H1E 0.5779 0.3812 0.801 0.053 Uiso calc U . R 1.0 . .
H H1F 0.5423 0.4318 0.8407 0.053 Uiso calc U . R 1.0 . .
C C11C 0.4564(4) 0.3319(3) 0.7501(6) 0.048(2) Uani d U . D 1.0 . .
C C12C 0.4429(8) 0.3611(5) 0.6662(9) 0.049(6) Uani d U P D 0.51(3) C 1
F F12C 0.3954(12) 0.4000(8) 0.6688(18) 0.093(9) Uani d U P D 0.51(3) C 1
C C13C 0.4726(10) 0.3553(8) 0.5784(11) 0.046(5) Uani d U P D 0.51(3) C 1
F F13C 0.4584(14) 0.3876(8) 0.5038(12) 0.071(5) Uani d U P D 0.51(3) C 1
C C14C 0.5221(10) 0.3171(8) 0.5646(12) 0.047(5) Uani d U P D 0.51(3) C 1
F F14C 0.5518(9) 0.3098(8) 0.4805(12) 0.066(5) Uani d U P D 0.51(3) C 1
C C15C 0.5392(9) 0.2860(7) 0.6434(14) 0.041(5) Uani d U P D 0.51(3) C 1
F F15C 0.5897(8) 0.2497(7) 0.6350(15) 0.068(5) Uani d U P D 0.51(3) C 1
C C16C 0.5102(10) 0.2950(6) 0.7310(12) 0.036(4) Uani d U P D 0.51(3) C 1
F F16C 0.5345(10) 0.2642(7) 0.8052(14) 0.050(4) Uani d U P D 0.51(3) C 1
C C12F 0.4469(8) 0.3595(5) 0.6665(10) 0.051(7) Uani d U P D 0.49(3) C 2
F F12F 0.4055(10) 0.4021(5) 0.6604(12) 0.034(4) Uani d U P D 0.49(3) C 2
C C13F 0.4763(10) 0.3431(7) 0.5836(12) 0.053(6) Uani d U P D 0.49(3) C 2
F F13F 0.4608(16) 0.3696(9) 0.5018(13) 0.073(6) Uani d U P D 0.49(3) C 2
C C14F 0.5203(11) 0.3005(8) 0.5873(14) 0.048(5) Uani d U P D 0.49(3) C 2
F F14F 0.5512(10) 0.2878(8) 0.5064(14) 0.068(5) Uani d U P D 0.49(3) C 2
C C15F 0.5332(11) 0.2740(7) 0.6727(16) 0.046(5) Uani d U P D 0.49(3) C 2
F F15F 0.5784(10) 0.2339(7) 0.6741(17) 0.074(5) Uani d U P D 0.49(3) C 2
C C16F 0.4991(13) 0.2880(7) 0.7541(14) 0.047(5) Uani d U P D 0.49(3) C 2
F F16F 0.5190(12) 0.2635(8) 0.8379(15) 0.066(6) Uani d U P D 0.49(3) C 2
B B1C 0.4362(5) 0.3475(3) 0.8595(7) 0.041(2) Uani d . . D 1.0 . .
C C21C 0.3915(9) 0.3088(5) 0.9312(12) 0.041(5) Uani d U P D 0.531(18) D 1
C C22C 0.3675(7) 0.3236(6) 1.0183(11) 0.048(5) Uani d U P D 0.531(18) D 1
F F22C 0.3797(10) 0.3717(6) 1.0467(14) 0.052(4) Uani d U P D 0.531(18) D 1
C C23C 0.3309(11) 0.2954(6) 1.0835(14) 0.057(5) Uani d U P D 0.531(18) D 1
F F23C 0.3089(11) 0.3162(7) 1.1649(13) 0.098(6) Uani d U P D 0.531(18) D 1
C C24C 0.3174(9) 0.2455(6) 1.0618(13) 0.051(4) Uani d U P D 0.531(18) D 1
F F24C 0.2812(9) 0.2162(6) 1.1212(15) 0.101(6) Uani d U P D 0.531(18) D 1
C C25C 0.3379(10) 0.2264(5) 0.9756(14) 0.051(4) Uani d U P D 0.531(18) D 1
F F25C 0.3235(9) 0.1781(4) 0.9511(14) 0.098(5) Uani d U P D 0.531(18) D 1
C C26C 0.3708(10) 0.2574(6) 0.9119(13) 0.047(4) Uani d U P D 0.531(18) D 1
F F26C 0.3841(12) 0.2374(7) 0.8263(13) 0.076(5) Uani d U P D 0.531(18) D 1
C C21F 0.3980(11) 0.3010(6) 0.9119(13) 0.047(6) Uani d U P D 0.469(18) D 2
C C22F 0.3748(9) 0.3109(6) 1.0013(12) 0.050(5) Uani d U P D 0.469(18) D 2
F F22F 0.3884(13) 0.3559(7) 1.0443(18) 0.074(6) Uani d U P D 0.469(18) D 2
C C23F 0.3362(12) 0.2786(7) 1.0562(14) 0.057(5) Uani d U P D 0.469(18) D 2
F F23F 0.3130(12) 0.2936(8) 1.1406(12) 0.091(6) Uani d U P D 0.469(18) D 2
C C24F 0.3208(10) 0.2320(6) 1.0175(14) 0.041(5) Uani d U P D 0.469(18) D 2
F F24F 0.2866(10) 0.1979(7) 1.0692(15) 0.097(6) Uani d U P D 0.469(18) D 2
C C25F 0.3414(11) 0.2190(6) 0.9277(14) 0.052(5) Uani d U P D 0.469(18) D 2
F F25F 0.3241(10) 0.1741(5) 0.8865(17) 0.100(6) Uani d U P D 0.469(18) D 2
C C26F 0.3786(13) 0.2528(6) 0.8759(16) 0.046(5) Uani d U P D 0.469(18) D 2
F F26F 0.3949(12) 0.2401(7) 0.7856(15) 0.072(5) Uani d U P D 0.469(18) D 2
C C31C 0.3898(5) 0.4391(3) 0.8841(6) 0.046(2) Uani d . . . 1.0 . .
H H31C 0.4363 0.4456 0.9182 0.056 Uiso calc U . R 1.0 . .
C C32C 0.3394(5) 0.4780(3) 0.8725(6) 0.050(2) Uani d . . . 1.0 . .
H H32C 0.3507 0.5105 0.8986 0.06 Uiso calc U . R 1.0 . .
C C33C 0.2731(5) 0.4685(3) 0.8227(7) 0.055(2) Uani d . . . 1.0 . .
H H33C 0.2385 0.4951 0.8109 0.066 Uiso calc U . R 1.0 . .
C C34C 0.2557(4) 0.4202(3) 0.7893(6) 0.053(2) Uani d . . . 1.0 . .
H H34C 0.2085 0.4128 0.758 0.063 Uiso calc U . R 1.0 . .
C C35C 0.3092(4) 0.3833(3) 0.8029(6) 0.0450(19) Uani d . . . 1.0 . .
H H35C 0.2986 0.3503 0.7789 0.054 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
N1A C35A . 1.344(10) ?
N1A C31A . 1.365(9) ?
N1A B1A . 1.645(10) ?
N1B C35B . 1.332(10) ?
N1B C31B . 1.351(10) ?
N1B B1B . 1.637(11) ?
N1C C31C . 1.337(9) ?
N1C C35C . 1.345(9) ?
N1C B1C . 1.628(10) ?
B1A C2A . 1.605(11) ?
B1A C11A . 1.640(11) ?
B1A C21A . 1.653(11) ?
C2A C3A . 1.348(10) ?
C2A C1A . 1.527(10) ?
C3A C4A . 1.467(10) ?
C3A H3A . 0.95 ?
C4A C5B . 1.389(9) ?
C4A C5A . 1.413(9) ?
C5A C4C . 1.400(9) ?
C5A C1A . 1.489(10) ?
C1A H1A . 0.99 ?
C1A H1B . 0.99 ?
C11A C16A . 1.384(10) ?
C11A C12A . 1.420(10) ?
C12A F12A . 1.351(8) ?
C12A C13A . 1.357(11) ?
C13A F13A . 1.344(9) ?
C13A C14A . 1.366(12) ?
C14A F14A . 1.355(9) ?
C14A C15A . 1.370(12) ?
C15A F15A . 1.353(9) ?
C15A C16A . 1.376(11) ?
C16A F16A . 1.355(8) ?
C21A C22A . 1.386(10) ?
C21A C26A . 1.402(10) ?
C22A F22A . 1.358(8) ?
C22A C23A . 1.375(11) ?
C23A F23A . 1.341(9) ?
C23A C24A . 1.384(11) ?
C24A F24A . 1.350(9) ?
C24A C25A . 1.372(11) ?
C25A F25A . 1.339(9) ?
C25A C26A . 1.380(10) ?
C26A F26A . 1.345(8) ?
C31A C32A . 1.368(11) ?
C31A H31A . 0.95 ?
C32A C33A . 1.384(13) ?
C32A H32A . 0.95 ?
C33A C34A . 1.373(13) ?
C33A H33A . 0.95 ?
C34A C35A . 1.382(11) ?
C34A H34A . 0.95 ?
C35A H35A . 0.95 ?
C2B C3B . 1.339(10) ?
C2B C1B . 1.532(10) ?
C2B B1B . 1.594(11) ?
C3B C4B . 1.472(10) ?
C3B H3B . 0.95 ?
C4B C5B . 1.390(9) ?
C4B C5C . 1.399(9) ?
C5B C1B . 1.495(9) ?
C1B H1C . 0.99 ?
C1B H1D . 0.99 ?
B1B C21B . 1.642(12) ?
B1B C11E . 1.664(19) ?
B1B C11B . 1.673(13) ?
C11B C12B . 1.366(10) ?
C11B C16B . 1.378(12) ?
C12B F12B . 1.355(9) ?
C12B C13B . 1.370(10) ?
C13B F13B . 1.360(10) ?
C13B C14B . 1.360(11) ?
C14B F14B . 1.349(10) ?
C14B C15B . 1.362(11) ?
C15B F15B . 1.355(10) ?
C15B C16B . 1.366(11) ?
C16B F16B . 1.362(10) ?
C11E C12E . 1.363(14) ?
C11E C16E . 1.382(19) ?
C12E F12E . 1.356(15) ?
C12E C13E . 1.368(14) ?
C13E F13E . 1.357(15) ?
C13E C14E . 1.364(14) ?
C14E F14E . 1.354(15) ?
C14E C15E . 1.364(14) ?
C15E F15E . 1.356(15) ?
C15E C16E . 1.364(14) ?
C16E F16E . 1.358(15) ?
C21B C22E . 1.371(14) ?
C21B C26E . 1.376(18) ?
C21B C26B . 1.390(11) ?
C21B C22B . 1.391(9) ?
C22B C23B . 1.365(10) ?
C22B F22B . 1.368(9) ?
C23B F23B . 1.350(9) ?
C23B C24B . 1.357(10) ?
C24B F24B . 1.351(9) ?
C24B C25B . 1.379(10) ?
C25B F25B . 1.358(9) ?
C25B C26B . 1.381(10) ?
C26B F26B . 1.356(9) ?
C22E F22E . 1.352(15) ?
C22E C23E . 1.371(14) ?
C23E F23E . 1.352(15) ?
C23E C24E . 1.368(14) ?
C24E F24E . 1.349(15) ?
C24E C25E . 1.376(14) ?
C25E F25E . 1.354(15) ?
C25E C26E . 1.375(14) ?
C26E F26E . 1.352(15) ?
C31B C32B . 1.382(11) ?
C31B H31B . 0.95 ?
C32B C33B . 1.369(12) ?
C32B H32B . 0.95 ?
C33B C34B . 1.378(12) ?
C33B H33B . 0.95 ?
C34B C35B . 1.372(11) ?
C34B H34B . 0.95 ?
C35B H35B . 0.95 ?
C2C C3C . 1.351(10) ?
C2C C1C . 1.520(10) ?
C2C B1C . 1.602(11) ?
C3C C4C . 1.476(9) ?
C3C H3C . 0.95 ?
C4C C5C . 1.407(9) ?
C5C C1C . 1.496(10) ?
C1C H1E . 0.99 ?
C1C H1F . 0.99 ?
C11C C12F . 1.368(12) ?
C11C C16F . 1.399(15) ?
C11C C12C . 1.399(12) ?
C11C C16C . 1.427(13) ?
C11C B1C . 1.645(12) ?
C12C F12C . 1.352(12) ?
C12C C13C . 1.384(12) ?
C13C F13C . 1.348(13) ?
C13C C14C . 1.383(12) ?
C14C F14C . 1.342(12) ?
C14C C15C . 1.382(13) ?
C15C F15C . 1.345(12) ?
C15C C16C . 1.388(12) ?
C16C F16C . 1.355(12) ?
C12F F12F . 1.359(12) ?
C12F C13F . 1.381(12) ?
C13F F13F . 1.343(13) ?
C13F C14F . 1.384(13) ?
C14F F14F . 1.342(12) ?
C14F C15F . 1.377(13) ?
C15F F15F . 1.346(12) ?
C15F C16F . 1.386(13) ?
C16F F16F . 1.351(13) ?
B1C C21F . 1.620(15) ?
B1C C21C . 1.687(14) ?
C21C C22C . 1.377(13) ?
C21C C26C . 1.433(16) ?
C22C F22C . 1.349(13) ?
C22C C23C . 1.390(13) ?
C23C F23C . 1.348(14) ?
C23C C24C . 1.374(13) ?
C24C F24C . 1.348(12) ?
C24C C25C . 1.379(13) ?
C25C F25C . 1.345(13) ?
C25C C26C . 1.382(13) ?
C26C F26C . 1.341(13) ?
C21F C22F . 1.369(14) ?
C21F C26F . 1.405(17) ?
C22F F22F . 1.347(14) ?
C22F C23F . 1.380(13) ?
C23F F23F . 1.338(14) ?
C23F C24F . 1.366(13) ?
C24F F24F . 1.342(13) ?
C24F C25F . 1.376(13) ?
C25F F25F . 1.344(13) ?
C25F C26F . 1.367(13) ?
C26F F26F . 1.353(14) ?
C31C C32C . 1.382(11) ?
C31C H31C . 0.95 ?
C32C C33C . 1.362(12) ?
C32C H32C . 0.95 ?
C33C C34C . 1.389(11) ?
C33C H33C . 0.95 ?
C34C C35C . 1.385(11) ?
C34C H34C . 0.95 ?
C35C H35C . 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
C35A N1A C31A . . 118.7(7) ?
C35A N1A B1A . . 116.2(6) ?
C31A N1A B1A . . 124.9(6) ?
C35B N1B C31B . . 119.1(7) ?
C35B N1B B1B . . 124.4(7) ?
C31B N1B B1B . . 116.4(7) ?
C31C N1C C35C . . 118.7(7) ?
C31C N1C B1C . . 122.6(7) ?
C35C N1C B1C . . 118.7(6) ?
C2A B1A C11A . . 115.3(6) ?
C2A B1A N1A . . 101.9(6) ?
C11A B1A N1A . . 109.9(6) ?
C2A B1A C21A . . 113.6(6) ?
C11A B1A C21A . . 106.5(6) ?
N1A B1A C21A . . 109.6(6) ?
C3A C2A C1A . . 107.3(6) ?
C3A C2A B1A . . 132.9(7) ?
C1A C2A B1A . . 119.7(6) ?
C2A C3A C4A . . 112.0(6) ?
C2A C3A H3A . . 124.0 ?
C4A C3A H3A . . 124.0 ?
C5B C4A C5A . . 120.8(7) ?
C5B C4A C3A . . 132.1(7) ?
C5A C4A C3A . . 106.9(6) ?
C4C C5A C4A . . 118.7(6) ?
C4C C5A C1A . . 132.6(6) ?
C4A C5A C1A . . 108.7(6) ?
C5A C1A C2A . . 104.6(6) ?
C5A C1A H1A . . 110.8 ?
C2A C1A H1A . . 110.8 ?
C5A C1A H1B . . 110.8 ?
C2A C1A H1B . . 110.8 ?
H1A C1A H1B . . 108.9 ?
C16A C11A C12A . . 112.9(7) ?
C16A C11A B1A . . 119.5(6) ?
C12A C11A B1A . . 127.5(6) ?
F12A C12A C13A . . 116.3(7) ?
F12A C12A C11A . . 119.7(7) ?
C13A C12A C11A . . 124.0(7) ?
F13A C13A C12A . . 120.0(8) ?
F13A C13A C14A . . 119.9(8) ?
C12A C13A C14A . . 120.0(8) ?
F14A C14A C13A . . 120.3(8) ?
F14A C14A C15A . . 120.5(8) ?
C13A C14A C15A . . 119.2(8) ?
F15A C15A C14A . . 120.1(8) ?
F15A C15A C16A . . 120.0(8) ?
C14A C15A C16A . . 119.8(8) ?
F16A C16A C15A . . 116.2(7) ?
F16A C16A C11A . . 119.8(7) ?
C15A C16A C11A . . 124.0(7) ?
C22A C21A C26A . . 113.1(7) ?
C22A C21A B1A . . 122.2(7) ?
C26A C21A B1A . . 124.5(7) ?
F22A C22A C23A . . 115.9(7) ?
F22A C22A C21A . . 118.7(7) ?
C23A C22A C21A . . 125.3(7) ?
F23A C23A C22A . . 121.3(8) ?
F23A C23A C24A . . 119.9(7) ?
C22A C23A C24A . . 118.8(7) ?
F24A C24A C25A . . 121.2(8) ?
F24A C24A C23A . . 119.9(8) ?
C25A C24A C23A . . 118.9(7) ?
F25A C25A C24A . . 119.1(7) ?
F25A C25A C26A . . 120.5(7) ?
C24A C25A C26A . . 120.4(7) ?
F26A C26A C25A . . 115.3(6) ?
F26A C26A C21A . . 121.4(7) ?
C25A C26A C21A . . 123.3(7) ?
N1A C31A C32A . . 121.4(8) ?
N1A C31A H31A . . 119.3 ?
C32A C31A H31A . . 119.3 ?
C31A C32A C33A . . 119.5(9) ?
C31A C32A H32A . . 120.2 ?
C33A C32A H32A . . 120.2 ?
C34A C33A C32A . . 119.2(8) ?
C34A C33A H33A . . 120.4 ?
C32A C33A H33A . . 120.4 ?
C33A C34A C35A . . 119.2(9) ?
C33A C34A H34A . . 120.4 ?
C35A C34A H34A . . 120.4 ?
N1A C35A C34A . . 121.8(8) ?
N1A C35A H35A . . 119.1 ?
C34A C35A H35A . . 119.1 ?
C3B C2B C1B . . 108.1(6) ?
C3B C2B B1B . . 129.5(7) ?
C1B C2B B1B . . 122.3(7) ?
C2B C3B C4B . . 110.7(7) ?
C2B C3B H3B . . 124.7 ?
C4B C3B H3B . . 124.7 ?
C5B C4B C5C . . 120.9(6) ?
C5B C4B C3B . . 108.7(6) ?
C5C C4B C3B . . 130.3(7) ?
C4A C5B C4B . . 119.8(6) ?
C4A C5B C1B . . 132.1(7) ?
C4B C5B C1B . . 108.1(6) ?
C5B C1B C2B . . 104.4(6) ?
C5B C1B H1C . . 110.9 ?
C2B C1B H1C . . 110.9 ?
C5B C1B H1D . . 110.9 ?
C2B C1B H1D . . 110.9 ?
H1C C1B H1D . . 108.9 ?
C2B B1B N1B . . 109.7(6) ?
C2B B1B C21B . . 104.2(6) ?
N1B B1B C21B . . 110.6(7) ?
C2B B1B C11E . . 114.9(11) ?
N1B B1B C11E . . 90.9(14) ?
C21B B1B C11E . . 125.4(13) ?
C2B B1B C11B . . 115.7(7) ?
N1B B1B C11B . . 103.4(7) ?
C21B B1B C11B . . 113.3(7) ?
C12B C11B C16B . . 113.6(8) ?
C12B C11B B1B . . 125.2(8) ?
C16B C11B B1B . . 121.1(8) ?
F12B C12B C11B . . 121.3(8) ?
F12B C12B C13B . . 114.6(8) ?
C11B C12B C13B . . 124.1(8) ?
F13B C13B C14B . . 119.8(10) ?
F13B C13B C12B . . 121.0(9) ?
C14B C13B C12B . . 119.3(9) ?
F14B C14B C13B . . 119.0(10) ?
F14B C14B C15B . . 121.2(10) ?
C13B C14B C15B . . 119.8(9) ?
F15B C15B C14B . . 120.5(9) ?
F15B C15B C16B . . 121.0(10) ?
C14B C15B C16B . . 118.5(9) ?
F16B C16B C15B . . 116.2(9) ?
F16B C16B C11B . . 119.1(8) ?
C15B C16B C11B . . 124.7(9) ?
C12E C11E C16E . . 114.2(17) ?
C12E C11E B1B . . 126.1(17) ?
C16E C11E B1B . . 119.5(16) ?
F12E C12E C11E . . 122.(2) ?
F12E C12E C13E . . 115.(2) ?
C11E C12E C13E . . 123.3(18) ?
F13E C13E C14E . . 119.(2) ?
F13E C13E C12E . . 121.(2) ?
C14E C13E C12E . . 120.1(18) ?
F14E C14E C13E . . 120.(2) ?
F14E C14E C15E . . 120.(2) ?
C13E C14E C15E . . 119.2(18) ?
F15E C15E C16E . . 120.(2) ?
F15E C15E C14E . . 121.(2) ?
C16E C15E C14E . . 118.6(18) ?
F16E C16E C15E . . 117.(2) ?
F16E C16E C11E . . 118.(2) ?
C15E C16E C11E . . 124.5(18) ?
C22E C21B C26E . . 116.3(17) ?
C26B C21B C22B . . 111.2(8) ?
C22E C21B B1B . . 121.5(12) ?
C26E C21B B1B . . 120.7(12) ?
C26B C21B B1B . . 118.9(7) ?
C22B C21B B1B . . 128.6(7) ?
C23B C22B F22B . . 114.8(8) ?
C23B C22B C21B . . 125.9(8) ?
F22B C22B C21B . . 119.3(8) ?
F23B C23B C24B . . 119.3(8) ?
F23B C23B C22B . . 120.4(8) ?
C24B C23B C22B . . 120.3(8) ?
F24B C24B C23B . . 119.9(8) ?
F24B C24B C25B . . 122.3(8) ?
C23B C24B C25B . . 117.7(8) ?
F25B C25B C24B . . 119.1(8) ?
F25B C25B C26B . . 120.9(8) ?
C24B C25B C26B . . 120.0(8) ?
F26B C26B C25B . . 115.0(9) ?
F26B C26B C21B . . 120.1(9) ?
C25B C26B C21B . . 124.9(8) ?
F22E C22E C23E . . 117.7(19) ?
F22E C22E C21B . . 120.(2) ?
C23E C22E C21B . . 121.5(17) ?
F23E C23E C24E . . 122.(2) ?
F23E C23E C22E . . 118.8(19) ?
C24E C23E C22E . . 119.6(17) ?
F24E C24E C23E . . 121.(2) ?
F24E C24E C25E . . 119.(2) ?
C23E C24E C25E . . 120.0(18) ?
F25E C25E C26E . . 121.(2) ?
F25E C25E C24E . . 120.(2) ?
C26E C25E C24E . . 118.6(18) ?
F26E C26E C25E . . 116.(2) ?
F26E C26E C21B . . 121.(2) ?
C25E C26E C21B . . 122.1(18) ?
N1B C31B C32B . . 121.0(8) ?
N1B C31B H31B . . 119.5 ?
C32B C31B H31B . . 119.5 ?
C33B C32B C31B . . 120.2(8) ?
C33B C32B H32B . . 119.9 ?
C31B C32B H32B . . 119.9 ?
C32B C33B C34B . . 117.5(8) ?
C32B C33B H33B . . 121.2 ?
C34B C33B H33B . . 121.2 ?
C35B C34B C33B . . 120.8(9) ?
C35B C34B H34B . . 119.6 ?
C33B C34B H34B . . 119.6 ?
N1B C35B C34B . . 121.3(8) ?
N1B C35B H35B . . 119.4 ?
C34B C35B H35B . . 119.4 ?
C3C C2C C1C . . 106.8(7) ?
C3C C2C B1C . . 131.8(7) ?
C1C C2C B1C . . 120.8(7) ?
C2C C3C C4C . . 112.4(7) ?
C2C C3C H3C . . 123.8 ?
C4C C3C H3C . . 123.8 ?
C5A C4C C5C . . 120.8(6) ?
C5A C4C C3C . . 132.4(7) ?
C5C C4C C3C . . 106.8(6) ?
C4B C5C C4C . . 119.0(6) ?
C4B C5C C1C . . 132.5(6) ?
C4C C5C C1C . . 108.4(6) ?
C5C C1C C2C . . 105.4(6) ?
C5C C1C H1E . . 110.7 ?
C2C C1C H1E . . 110.7 ?
C5C C1C H1F . . 110.7 ?
C2C C1C H1F . . 110.7 ?
H1E C1C H1F . . 108.8 ?
C12F C11C C16F . . 120.5(11) ?
C12C C11C C16C . . 107.3(11) ?
C12F C11C B1C . . 128.5(9) ?
C16F C11C B1C . . 110.1(10) ?
C12C C11C B1C . . 126.0(9) ?
C16C C11C B1C . . 124.0(9) ?
F12C C12C C13C . . 114.3(14) ?
F12C C12C C11C . . 117.8(14) ?
C13C C12C C11C . . 128.0(13) ?
F13C C13C C14C . . 116.3(13) ?
F13C C13C C12C . . 122.7(14) ?
C14C C13C C12C . . 121.0(12) ?
F14C C14C C15C . . 121.2(12) ?
F14C C14C C13C . . 123.1(13) ?
C15C C14C C13C . . 115.7(11) ?
F15C C15C C14C . . 117.9(12) ?
F15C C15C C16C . . 121.2(13) ?
C14C C15C C16C . . 120.6(11) ?
F16C C16C C15C . . 115.7(12) ?
F16C C16C C11C . . 117.1(12) ?
C15C C16C C11C . . 127.1(11) ?
F12F C12F C11C . . 121.8(12) ?
F12F C12F C13F . . 117.8(12) ?
C11C C12F C13F . . 120.3(12) ?
F13F C13F C12F . . 117.9(14) ?
F13F C13F C14F . . 122.5(14) ?
C12F C13F C14F . . 119.6(13) ?
F14F C14F C15F . . 122.5(14) ?
F14F C14F C13F . . 117.3(14) ?
C15F C14F C13F . . 120.1(12) ?
F15F C15F C14F . . 118.2(13) ?
F15F C15F C16F . . 121.4(14) ?
C14F C15F C16F . . 120.5(11) ?
F16F C16F C15F . . 117.6(13) ?
F16F C16F C11C . . 122.7(14) ?
C15F C16F C11C . . 118.7(12) ?
C2C B1C C21F . . 115.4(9) ?
C2C B1C N1C . . 110.5(6) ?
C21F B1C N1C . . 106.6(9) ?
C2C B1C C11C . . 104.8(7) ?
C21F B1C C11C . . 111.2(9) ?
N1C B1C C11C . . 108.1(6) ?
C2C B1C C21C . . 111.6(8) ?
N1C B1C C21C . . 98.1(8) ?
C11C B1C C21C . . 123.3(8) ?
C22C C21C C26C . . 109.5(12) ?
C22C C21C B1C . . 123.4(11) ?
C26C C21C B1C . . 127.0(12) ?
F22C C22C C21C . . 117.9(13) ?
F22C C22C C23C . . 113.3(13) ?
C21C C22C C23C . . 128.8(13) ?
F23C C23C C24C . . 121.0(13) ?
F23C C23C C22C . . 121.4(13) ?
C24C C23C C22C . . 117.6(13) ?
F24C C24C C23C . . 120.7(13) ?
F24C C24C C25C . . 120.1(14) ?
C23C C24C C25C . . 119.1(11) ?
F25C C25C C24C . . 120.4(13) ?
F25C C25C C26C . . 119.4(13) ?
C24C C25C C26C . . 120.1(12) ?
F26C C26C C25C . . 116.9(14) ?
F26C C26C C21C . . 118.4(13) ?
C25C C26C C21C . . 124.7(13) ?
C22F C21F C26F . . 114.1(13) ?
C22F C21F B1C . . 116.0(12) ?
C26F C21F B1C . . 129.7(14) ?
F22F C22F C21F . . 120.8(15) ?
F22F C22F C23F . . 112.8(16) ?
C21F C22F C23F . . 126.4(14) ?
F23F C23F C24F . . 122.7(14) ?
F23F C23F C22F . . 121.0(14) ?
C24F C23F C22F . . 116.3(13) ?
F24F C24F C23F . . 119.3(15) ?
F24F C24F C25F . . 119.4(15) ?
C23F C24F C25F . . 121.3(12) ?
F25F C25F C26F . . 117.9(14) ?
F25F C25F C24F . . 122.2(14) ?
C26F C25F C24F . . 119.9(13) ?
F26F C26F C25F . . 118.8(15) ?
F26F C26F C21F . . 119.0(14) ?
C25F C26F C21F . . 122.1(14) ?
N1C C31C C32C . . 122.6(8) ?
N1C C31C H31C . . 118.7 ?
C32C C31C H31C . . 118.7 ?
C33C C32C C31C . . 118.2(8) ?
C33C C32C H32C . . 120.9 ?
C31C C32C H32C . . 120.9 ?
C32C C33C C34C . . 120.4(8) ?
C32C C33C H33C . . 119.8 ?
C34C C33C H33C . . 119.8 ?
C35C C34C C33C . . 118.0(8) ?
C35C C34C H34C . . 121.0 ?
C33C C34C H34C . . 121.0 ?
N1C C35C C34C . . 121.9(7) ?
N1C C35C H35C . . 119.0 ?
C34C C35C H35C . . 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
C35A N1A B1A C2A . . . . 62.4(8) ?
C31A N1A B1A C2A . . . . -111.4(8) ?
C35A N1A B1A C11A . . . . -60.3(9) ?
C31A N1A B1A C11A . . . . 125.9(8) ?
C35A N1A B1A C21A . . . . -177.0(7) ?
C31A N1A B1A C21A . . . . 9.2(10) ?
C11A B1A C2A C3A . . . . -7.2(12) ?
N1A B1A C2A C3A . . . . -126.1(8) ?
C21A B1A C2A C3A . . . . 116.1(9) ?
C11A B1A C2A C1A . . . . 172.3(6) ?
N1A B1A C2A C1A . . . . 53.4(8) ?
C21A B1A C2A C1A . . . . -64.4(8) ?
C1A C2A C3A C4A . . . . 5.0(8) ?
B1A C2A C3A C4A . . . . -175.5(7) ?
C2A C3A C4A C5B . . . . 173.6(7) ?
C2A C3A C4A C5A . . . . -1.5(8) ?
C5B C4A C5A C4C . . . . 2.0(10) ?
C3A C4A C5A C4C . . . . 177.8(6) ?
C5B C4A C5A C1A . . . . -178.6(6) ?
C3A C4A C5A C1A . . . . -2.8(8) ?
C4C C5A C1A C2A . . . . -175.2(7) ?
C4A C5A C1A C2A . . . . 5.6(7) ?
C3A C2A C1A C5A . . . . -6.4(8) ?
B1A C2A C1A C5A . . . . 174.0(6) ?
C2A B1A C11A C16A . . . . 55.1(9) ?
N1A B1A C11A C16A . . . . 169.6(6) ?
C21A B1A C11A C16A . . . . -71.8(8) ?
C2A B1A C11A C12A . . . . -128.2(8) ?
N1A B1A C11A C12A . . . . -13.7(11) ?
C21A B1A C11A C12A . . . . 104.8(8) ?
C16A C11A C12A F12A . . . . 176.1(7) ?
B1A C11A C12A F12A . . . . -0.7(12) ?
C16A C11A C12A C13A . . . . -3.5(12) ?
B1A C11A C12A C13A . . . . 179.7(8) ?
F12A C12A C13A F13A . . . . 0.3(12) ?
C11A C12A C13A F13A . . . . 180.0(8) ?
F12A C12A C13A C14A . . . . -176.8(8) ?
C11A C12A C13A C14A . . . . 2.9(14) ?
F13A C13A C14A F14A . . . . 2.8(13) ?
C12A C13A C14A F14A . . . . 179.9(8) ?
F13A C13A C14A C15A . . . . -179.4(8) ?
C12A C13A C14A C15A . . . . -2.3(14) ?
F14A C14A C15A F15A . . . . -0.6(12) ?
C13A C14A C15A F15A . . . . -178.4(8) ?
F14A C14A C15A C16A . . . . -179.5(7) ?
C13A C14A C15A C16A . . . . 2.7(13) ?
F15A C15A C16A F16A . . . . -3.2(11) ?
C14A C15A C16A F16A . . . . 175.7(7) ?
F15A C15A C16A C11A . . . . 177.3(7) ?
C14A C15A C16A C11A . . . . -3.8(13) ?
C12A C11A C16A F16A . . . . -175.5(6) ?
B1A C11A C16A F16A . . . . 1.6(11) ?
C12A C11A C16A C15A . . . . 4.0(11) ?
B1A C11A C16A C15A . . . . -178.9(7) ?
C2A B1A C21A C22A . . . . 168.7(7) ?
C11A B1A C21A C22A . . . . -63.4(9) ?
N1A B1A C21A C22A . . . . 55.4(9) ?
C2A B1A C21A C26A . . . . -15.9(10) ?
C11A B1A C21A C26A . . . . 112.1(8) ?
N1A B1A C21A C26A . . . . -129.2(7) ?
C26A C21A C22A F22A . . . . -177.5(6) ?
B1A C21A C22A F22A . . . . -1.6(11) ?
C26A C21A C22A C23A . . . . 4.1(11) ?
B1A C21A C22A C23A . . . . 179.9(7) ?
F22A C22A C23A F23A . . . . -0.6(11) ?
C21A C22A C23A F23A . . . . 177.9(7) ?
F22A C22A C23A C24A . . . . 179.2(7) ?
C21A C22A C23A C24A . . . . -2.4(13) ?
F23A C23A C24A F24A . . . . 0.6(12) ?
C22A C23A C24A F24A . . . . -179.2(7) ?
F23A C23A C24A C25A . . . . 179.7(8) ?
C22A C23A C24A C25A . . . . 0.0(12) ?
F24A C24A C25A F25A . . . . 0.5(12) ?
C23A C24A C25A F25A . . . . -178.6(7) ?
F24A C24A C25A C26A . . . . 179.4(7) ?
C23A C24A C25A C26A . . . . 0.3(13) ?
F25A C25A C26A F26A . . . . 0.2(11) ?
C24A C25A C26A F26A . . . . -178.7(7) ?
F25A C25A C26A C21A . . . . -179.3(7) ?
C24A C25A C26A C21A . . . . 1.7(13) ?
C22A C21A C26A F26A . . . . 176.8(7) ?
B1A C21A C26A F26A . . . . 1.0(11) ?
C22A C21A C26A C25A . . . . -3.7(11) ?
B1A C21A C26A C25A . . . . -179.5(7) ?
C35A N1A C31A C32A . . . . 4.9(12) ?
B1A N1A C31A C32A . . . . 178.6(8) ?
N1A C31A C32A C33A . . . . -2.3(14) ?
C31A C32A C33A C34A . . . . -1.0(15) ?
C32A C33A C34A C35A . . . . 1.6(14) ?
C31A N1A C35A C34A . . . . -4.3(12) ?
B1A N1A C35A C34A . . . . -178.5(8) ?
C33A C34A C35A N1A . . . . 1.1(14) ?
C1B C2B C3B C4B . . . . -0.6(8) ?
B1B C2B C3B C4B . . . . 175.4(7) ?
C2B C3B C4B C5B . . . . 1.8(9) ?
C2B C3B C4B C5C . . . . 178.5(7) ?
C5A C4A C5B C4B . . . . -1.9(10) ?
C3A C4A C5B C4B . . . . -176.5(7) ?
C5A C4A C5B C1B . . . . 178.4(7) ?
C3A C4A C5B C1B . . . . 3.9(13) ?
C5C C4B C5B C4A . . . . 1.0(10) ?
C3B C4B C5B C4A . . . . 178.1(6) ?
C5C C4B C5B C1B . . . . -179.3(6) ?
C3B C4B C5B C1B . . . . -2.2(8) ?
C4A C5B C1B C2B . . . . -178.5(7) ?
C4B C5B C1B C2B . . . . 1.8(7) ?
C3B C2B C1B C5B . . . . -0.7(8) ?
B1B C2B C1B C5B . . . . -177.1(7) ?
C3B C2B B1B N1B . . . . 4.2(12) ?
C1B C2B B1B N1B . . . . 179.7(6) ?
C3B C2B B1B C21B . . . . -114.3(9) ?
C1B C2B B1B C21B . . . . 61.2(9) ?
C3B C2B B1B C11E . . . . 104.7(17) ?
C1B C2B B1B C11E . . . . -79.7(17) ?
C3B C2B B1B C11B . . . . 120.6(9) ?
C1B C2B B1B C11B . . . . -63.9(10) ?
C35B N1B B1B C2B . . . . -128.0(8) ?
C31B N1B B1B C2B . . . . 54.2(9) ?
C35B N1B B1B C21B . . . . -13.6(10) ?
C31B N1B B1B C21B . . . . 168.6(6) ?
C35B N1B B1B C11E . . . . 115.1(12) ?
C31B N1B B1B C11E . . . . -62.7(12) ?
C35B N1B B1B C11B . . . . 108.0(8) ?
C31B N1B B1B C11B . . . . -69.8(8) ?
C2B B1B C11B C12B . . . . -16.9(12) ?
N1B B1B C11B C12B . . . . 103.0(9) ?
C21B B1B C11B C12B . . . . -137.2(8) ?
C2B B1B C11B C16B . . . . 168.2(10) ?
N1B B1B C11B C16B . . . . -71.9(12) ?
C21B B1B C11B C16B . . . . 47.9(13) ?
C16B C11B C12B F12B . . . . 177.7(9) ?
B1B C11B C12B F12B . . . . 2.5(11) ?
C16B C11B C12B C13B . . . . -3.0(14) ?
B1B C11B C12B C13B . . . . -178.3(11) ?
F12B C12B C13B F13B . . . . 0.3(17) ?
C11B C12B C13B F13B . . . . -179.0(11) ?
F12B C12B C13B C14B . . . . -178.8(12) ?
C11B C12B C13B C14B . . . . 1.9(18) ?
F13B C13B C14B F14B . . . . -1.(2) ?
C12B C13B C14B F14B . . . . 177.8(13) ?
F13B C13B C14B C15B . . . . -179.3(15) ?
C12B C13B C14B C15B . . . . 0.(2) ?
F14B C14B C15B F15B . . . . 1.(3) ?
C13B C14B C15B F15B . . . . 178.8(15) ?
F14B C14B C15B C16B . . . . -178.0(14) ?
C13B C14B C15B C16B . . . . 0.(2) ?
F15B C15B C16B F16B . . . . -2.(2) ?
C14B C15B C16B F16B . . . . 177.2(14) ?
F15B C15B C16B C11B . . . . 179.8(14) ?
C14B C15B C16B C11B . . . . -1.(2) ?
C12B C11B C16B F16B . . . . -175.7(10) ?
B1B C11B C16B F16B . . . . -0.3(17) ?
C12B C11B C16B C15B . . . . 2.8(18) ?
B1B C11B C16B C15B . . . . 178.3(12) ?
C2B B1B C11E C12E . . . . 4.(2) ?
N1B B1B C11E C12E . . . . 116.6(18) ?
C21B B1B C11E C12E . . . . -127.2(16) ?
C2B B1B C11E C16E . . . . 179.(2) ?
N1B B1B C11E C16E . . . . -69.(3) ?
C21B B1B C11E C16E . . . . 47.(3) ?
C16E C11E C12E F12E . . . . 179.(2) ?
B1B C11E C12E F12E . . . . -7.(3) ?
C16E C11E C12E C13E . . . . -3.(3) ?
B1B C11E C12E C13E . . . . 172.(4) ?
F12E C12E C13E F13E . . . . -1.(5) ?
C11E C12E C13E F13E . . . . -179.(3) ?
F12E C12E C13E C14E . . . . -180.(3) ?
C11E C12E C13E C14E . . . . 1.(5) ?
F13E C13E C14E F14E . . . . -6.(7) ?
C12E C13E C14E F14E . . . . 173.(4) ?
F13E C13E C14E C15E . . . . -178.(4) ?
C12E C13E C14E C15E . . . . 1.(6) ?
F14E C14E C15E F15E . . . . 10.(7) ?
C13E C14E C15E F15E . . . . -178.(4) ?
F14E C14E C15E C16E . . . . -174.(4) ?
C13E C14E C15E C16E . . . . -2.(6) ?
F15E C15E C16E F16E . . . . -3.(6) ?
C14E C15E C16E F16E . . . . -179.(4) ?
F15E C15E C16E C11E . . . . 176.(4) ?
C14E C15E C16E C11E . . . . 0.(6) ?
C12E C11E C16E F16E . . . . -179.(3) ?
B1B C11E C16E F16E . . . . 6.(5) ?
C12E C11E C16E C15E . . . . 2.(5) ?
B1B C11E C16E C15E . . . . -173.(4) ?
C2B B1B C21B C22E . . . . -127.0(19) ?
N1B B1B C21B C22E . . . . 115.2(19) ?
C11E B1B C21B C22E . . . . 8.(2) ?
C2B B1B C21B C26E . . . . 68.(4) ?
N1B B1B C21B C26E . . . . -50.(4) ?
C11E B1B C21B C26E . . . . -157.(4) ?
C2B B1B C21B C26B . . . . 61.6(11) ?
N1B B1B C21B C26B . . . . -56.3(11) ?
C11B B1B C21B C26B . . . . -171.8(10) ?
C2B B1B C21B C22B . . . . -104.3(8) ?
N1B B1B C21B C22B . . . . 137.9(7) ?
C11B B1B C21B C22B . . . . 22.4(11) ?
C26B C21B C22B C23B . . . . 4.2(12) ?
B1B C21B C22B C23B . . . . 170.9(9) ?
C26B C21B C22B F22B . . . . -177.0(8) ?
B1B C21B C22B F22B . . . . -10.3(9) ?
F22B C22B C23B F23B . . . . -2.1(12) ?
C21B C22B C23B F23B . . . . 176.7(8) ?
F22B C22B C23B C24B . . . . 177.6(9) ?
C21B C22B C23B C24B . . . . -3.5(15) ?
F23B C23B C24B F24B . . . . -2.0(17) ?
C22B C23B C24B F24B . . . . 178.3(10) ?
F23B C23B C24B C25B . . . . -179.3(11) ?
C22B C23B C24B C25B . . . . 1.0(17) ?
F24B C24B C25B F25B . . . . 4.3(19) ?
C23B C24B C25B F25B . . . . -178.5(11) ?
F24B C24B C25B C26B . . . . -176.9(12) ?
C23B C24B C25B C26B . . . . 0.3(19) ?
F25B C25B C26B F26B . . . . 0.(2) ?
C24B C25B C26B F26B . . . . -179.2(13) ?
F25B C25B C26B C21B . . . . 179.5(12) ?
C24B C25B C26B C21B . . . . 1.(2) ?
C22B C21B C26B F26B . . . . 177.2(12) ?
B1B C21B C26B F26B . . . . 9.0(18) ?
C22B C21B C26B C25B . . . . -2.8(17) ?
B1B C21B C26B C25B . . . . -170.9(12) ?
C26E C21B C22E F22E . . . . 173.(3) ?
B1B C21B C22E F22E . . . . 6.5(19) ?
C26E C21B C22E C23E . . . . -16.(5) ?
B1B C21B C22E C23E . . . . 177.9(13) ?
F22E C22E C23E F23E . . . . 0.(2) ?
C21B C22E C23E F23E . . . . -172.(3) ?
F22E C22E C23E C24E . . . . 179.(2) ?
C21B C22E C23E C24E . . . . 8.(3) ?
F23E C23E C24E F24E . . . . -2.(5) ?
C22E C23E C24E F24E . . . . 179.(3) ?
F23E C23E C24E C25E . . . . -178.(4) ?
C22E C23E C24E C25E . . . . 3.(5) ?
F24E C24E C25E F25E . . . . 7.(7) ?
C23E C24E C25E F25E . . . . -177.(4) ?
F24E C24E C25E C26E . . . . 179.(5) ?
C23E C24E C25E C26E . . . . -4.(7) ?
F25E C25E C26E F26E . . . . -4.(8) ?
C24E C25E C26E F26E . . . . -177.(5) ?
F25E C25E C26E C21B . . . . 168.(5) ?
C24E C25E C26E C21B . . . . -4.(8) ?
C22E C21B C26E F26E . . . . -173.(4) ?
B1B C21B C26E F26E . . . . -7.(7) ?
C22E C21B C26E C25E . . . . 14.(7) ?
B1B C21B C26E C25E . . . . -179.(4) ?
C35B N1B C31B C32B . . . . 1.8(11) ?
B1B N1B C31B C32B . . . . 179.7(7) ?
N1B C31B C32B C33B . . . . 0.8(12) ?
C31B C32B C33B C34B . . . . -2.0(13) ?
C32B C33B C34B C35B . . . . 0.9(13) ?
C31B N1B C35B C34B . . . . -3.0(12) ?
B1B N1B C35B C34B . . . . 179.3(7) ?
C33B C34B C35B N1B . . . . 1.7(13) ?
C1C C2C C3C C4C . . . . 1.9(9) ?
B1C C2C C3C C4C . . . . 173.2(7) ?
C4A C5A C4C C5C . . . . -1.3(10) ?
C1A C5A C4C C5C . . . . 179.5(7) ?
C4A C5A C4C C3C . . . . 177.5(7) ?
C1A C5A C4C C3C . . . . -1.7(13) ?
C2C C3C C4C C5A . . . . -179.5(7) ?
C2C C3C C4C C5C . . . . -0.5(8) ?
C5B C4B C5C C4C . . . . -0.2(10) ?
C3B C4B C5C C4C . . . . -176.6(7) ?
C5B C4B C5C C1C . . . . -177.1(7) ?
C3B C4B C5C C1C . . . . 6.6(13) ?
C5A C4C C5C C4B . . . . 0.4(10) ?
C3C C4C C5C C4B . . . . -178.7(6) ?
C5A C4C C5C C1C . . . . 177.9(6) ?
C3C C4C C5C C1C . . . . -1.1(8) ?
C4B C5C C1C C2C . . . . 179.3(7) ?
C4C C5C C1C C2C . . . . 2.2(8) ?
C3C C2C C1C C5C . . . . -2.5(8) ?
B1C C2C C1C C5C . . . . -175.0(6) ?
C16C C11C C12C F12C . . . . -177.6(11) ?
B1C C11C C12C F12C . . . . -15.6(9) ?
C16C C11C C12C C13C . . . . 2.4(18) ?
B1C C11C C12C C13C . . . . 164.4(14) ?
F12C C12C C13C F13C . . . . 4.(2) ?
C11C C12C C13C F13C . . . . -176.4(17) ?
F12C C12C C13C C14C . . . . -179.9(15) ?
C11C C12C C13C C14C . . . . 0.(3) ?
F13C C13C C14C F14C . . . . -4.(3) ?
C12C C13C C14C F14C . . . . 179.5(17) ?
F13C C13C C14C C15C . . . . 176.6(19) ?
C12C C13C C14C C15C . . . . 0.(3) ?
F14C C14C C15C F15C . . . . 3.(3) ?
C13C C14C C15C F15C . . . . -176.9(18) ?
F14C C14C C15C C16C . . . . 177.6(19) ?
C13C C14C C15C C16C . . . . -3.(3) ?
F15C C15C C16C F16C . . . . -2.(3) ?
C14C C15C C16C F16C . . . . -175.7(19) ?
F15C C15C C16C C11C . . . . -179.8(17) ?
C14C C15C C16C C11C . . . . 6.(3) ?
C12C C11C C16C F16C . . . . 176.4(16) ?
B1C C11C C16C F16C . . . . 14.(2) ?
C12C C11C C16C C15C . . . . -6.(2) ?
B1C C11C C16C C15C . . . . -168.0(16) ?
C16F C11C C12F F12F . . . . 179.7(13) ?
B1C C11C C12F F12F . . . . -12.4(14) ?
C16F C11C C12F C13F . . . . 3.(2) ?
B1C C11C C12F C13F . . . . 171.2(10) ?
F12F C12F C13F F13F . . . . -1.4(18) ?
C11C C12F C13F F13F . . . . 175.2(18) ?
F12F C12F C13F C14F . . . . 178.5(14) ?
C11C C12F C13F C14F . . . . -4.9(19) ?
F13F C13F C14F F14F . . . . 4.(3) ?
C12F C13F C14F F14F . . . . -176.0(15) ?
F13F C13F C14F C15F . . . . -179.(2) ?
C12F C13F C14F C15F . . . . 1.(3) ?
F14F C14F C15F F15F . . . . 0.(3) ?
C13F C14F C15F F15F . . . . -177.6(18) ?
F14F C14F C15F C16F . . . . -179.(2) ?
C13F C14F C15F C16F . . . . 4.(3) ?
F15F C15F C16F F16F . . . . 7.(3) ?
C14F C15F C16F F16F . . . . -174.(2) ?
F15F C15F C16F C11C . . . . 176.0(18) ?
C14F C15F C16F C11C . . . . -5.(3) ?
C12F C11C C16F F16F . . . . 170.1(19) ?
B1C C11C C16F F16F . . . . 0.(3) ?
C12F C11C C16F C15F . . . . 2.(3) ?
B1C C11C C16F C15F . . . . -168.1(17) ?
C3C C2C B1C C21F . . . . -8.8(14) ?
C1C C2C B1C C21F . . . . 161.5(10) ?
C3C C2C B1C N1C . . . . 112.2(9) ?
C1C C2C B1C N1C . . . . -77.5(9) ?
C3C C2C B1C C11C . . . . -131.5(9) ?
C1C C2C B1C C11C . . . . 38.8(9) ?
C3C C2C B1C C21C . . . . 4.2(13) ?
C1C C2C B1C C21C . . . . 174.5(9) ?
C31C N1C B1C C2C . . . . -1.3(10) ?
C35C N1C B1C C2C . . . . 178.1(7) ?
C31C N1C B1C C21F . . . . 124.8(10) ?
C35C N1C B1C C21F . . . . -55.8(11) ?
C31C N1C B1C C11C . . . . -115.5(8) ?
C35C N1C B1C C11C . . . . 63.9(9) ?
C31C N1C B1C C21C . . . . 115.4(9) ?
C35C N1C B1C C21C . . . . -65.1(9) ?
C12F C11C B1C C2C . . . . -97.5(12) ?
C16F C11C B1C C2C . . . . 71.5(14) ?
C12C C11C B1C C2C . . . . -100.0(9) ?
C16C C11C B1C C2C . . . . 59.1(14) ?
C12F C11C B1C C21F . . . . 137.1(13) ?
C16F C11C B1C C21F . . . . -53.9(16) ?
C12F C11C B1C N1C . . . . 20.4(13) ?
C16F C11C B1C N1C . . . . -170.7(13) ?
C12C C11C B1C N1C . . . . 17.9(11) ?
C16C C11C B1C N1C . . . . 177.0(12) ?
C12C C11C B1C C21C . . . . 131.0(11) ?
C16C C11C B1C C21C . . . . -69.9(16) ?
C2C B1C C21C C22C . . . . 61.0(13) ?
N1C B1C C21C C22C . . . . -54.8(12) ?
C11C B1C C21C C22C . . . . -172.8(9) ?
C2C B1C C21C C26C . . . . -120.8(16) ?
N1C B1C C21C C26C . . . . 123.4(16) ?
C11C B1C C21C C26C . . . . 5.(2) ?
C26C C21C C22C F22C . . . . -177.6(11) ?
B1C C21C C22C F22C . . . . 0.9(14) ?
C26C C21C C22C C23C . . . . 2.0(18) ?
B1C C21C C22C C23C . . . . -179.5(17) ?
F22C C22C C23C F23C . . . . 2.(2) ?
C21C C22C C23C F23C . . . . -177.8(15) ?
F22C C22C C23C C24C . . . . -178.6(15) ?
C21C C22C C23C C24C . . . . 2.(3) ?
F23C C23C C24C F24C . . . . 1.(3) ?
C22C C23C C24C F24C . . . . -179.0(16) ?
F23C C23C C24C C25C . . . . 177.1(19) ?
C22C C23C C24C C25C . . . . -2.(3) ?
F24C C24C C25C F25C . . . . -1.(3) ?
C23C C24C C25C F25C . . . . -178.1(18) ?
F24C C24C C25C C26C . . . . 175.8(18) ?
C23C C24C C25C C26C . . . . -1.(3) ?
F25C C25C C26C F26C . . . . 2.(3) ?
C24C C25C C26C F26C . . . . -174.9(19) ?
F25C C25C C26C C21C . . . . -177.5(18) ?
C24C C25C C26C C21C . . . . 5.(3) ?
C22C C21C C26C F26C . . . . 174.6(15) ?
B1C C21C C26C F26C . . . . -4.(3) ?
C22C C21C C26C C25C . . . . -5.(2) ?
B1C C21C C26C C25C . . . . 176.1(17) ?
C2C B1C C21F C22F . . . . 64.6(14) ?
N1C B1C C21F C22F . . . . -58.4(13) ?
C11C B1C C21F C22F . . . . -176.1(9) ?
C2C B1C C21F C26F . . . . -122.(2) ?
N1C B1C C21F C26F . . . . 115.(2) ?
C11C B1C C21F C26F . . . . -3.(2) ?
C26F C21F C22F F22F . . . . -178.9(14) ?
B1C C21F C22F F22F . . . . -4.7(15) ?
C26F C21F C22F C23F . . . . 1.(2) ?
B1C C21F C22F C23F . . . . 174.9(18) ?
F22F C22F C23F F23F . . . . 3.(2) ?
C21F C22F C23F F23F . . . . -176.5(16) ?
F22F C22F C23F C24F . . . . -179.6(16) ?
C21F C22F C23F C24F . . . . 1.(3) ?
F23F C23F C24F F24F . . . . -6.(3) ?
C22F C23F C24F F24F . . . . 176.7(18) ?
F23F C23F C24F C25F . . . . 176.(2) ?
C22F C23F C24F C25F . . . . -1.(3) ?
F24F C24F C25F F25F . . . . 5.(3) ?
C23F C24F C25F F25F . . . . -177.(2) ?
F24F C24F C25F C26F . . . . -178.(2) ?
C23F C24F C25F C26F . . . . 0.(3) ?
F25F C25F C26F F26F . . . . 1.(3) ?
C24F C25F C26F F26F . . . . -177.(2) ?
F25F C25F C26F C21F . . . . 179.(2) ?
C24F C25F C26F C21F . . . . 1.(3) ?
C22F C21F C26F F26F . . . . 176.0(18) ?
B1C C21F C26F F26F . . . . 3.(3) ?
C22F C21F C26F C25F . . . . -2.(3) ?
B1C C21F C26F C25F . . . . -174.9(19) ?
C35C N1C C31C C32C . . . . -1.6(12) ?
B1C N1C C31C C32C . . . . 177.8(7) ?
N1C C31C C32C C33C . . . . -0.5(12) ?
C31C C32C C33C C34C . . . . 3.3(13) ?
C32C C33C C34C C35C . . . . -3.9(13) ?
C31C N1C C35C C34C . . . . 1.0(12) ?
B1C N1C C35C C34C . . . . -178.4(7) ?
C33C C34C C35C N1C . . . . 1.7(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_erk9216
_audit_block_doi                 10.5517/ccdc.csd.cc2210ms
_database_code_depnum_ccdc_archive 'CCDC 1907604'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9CC04199K 2019
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H11 B F10'
_chemical_formula_iupac          ?
_chemical_formula_weight         536.17

_chemical_melting_point          ?

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

_cell_length_a                   27.821(2)
_cell_length_b                   7.5444(6)
_cell_length_c                   20.4229(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4286.6(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6523
_cell_measurement_theta_min      4.3297
_cell_measurement_theta_max      66.5979
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2144

_exptl_absorpt_coefficient_mu    1.392
_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  0.90

_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            40458
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_theta_min         5.37
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_full        66.78
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_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             3786
_reflns_number_gt                3037
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0877
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         3786
_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)+(0.0395P)²+2.1254P] 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         0.216
_refine_diff_density_min         -0.227
_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
B B1 0.63269(7) 0.6921(3) 0.51539(10) 0.0194(5) Uani d . . . 1 . .
C C1 0.68590(6) 0.6069(3) 0.40805(9) 0.0194(4) Uani d . . . 1 . .
H H1A 0.6619 0.5324 0.3851 0.023 Uiso calc U . R 1 . .
H H1B 0.6852 0.7278 0.3892 0.023 Uiso calc U . R 1 . .
C C2 0.67619(6) 0.6113(2) 0.48135(9) 0.0190(4) Uani d . . . 1 . .
C C3 0.71555(6) 0.5418(2) 0.51257(9) 0.0194(4) Uani d . . . 1 . .
H H3 0.7183 0.529 0.5587 0.023 Uiso calc U . R 1 . .
C C4 0.75232(7) 0.4906(2) 0.46652(9) 0.0189(4) Uani d . . . 1 . .
C C5 0.79734(6) 0.4115(3) 0.47478(9) 0.0201(4) Uani d . . . 1 . .
H H5 0.8096 0.3898 0.5174 0.024 Uiso calc U . R 1 . .
C C6 0.82378(7) 0.3653(2) 0.42015(9) 0.0193(4) Uani d . . . 1 . .
H H6 0.8541 0.3092 0.4259 0.023 Uiso calc U . R 1 . .
C C7 0.80715(6) 0.3989(2) 0.35616(9) 0.0186(4) Uani d . . . 1 . .
C C8 0.76263(6) 0.4837(2) 0.34870(9) 0.0198(4) Uani d . . . 1 . .
H H8 0.7511 0.5113 0.3061 0.024 Uiso calc U . R 1 . .
C C9 0.73546(6) 0.5275(2) 0.40320(9) 0.0179(4) Uani d . . . 1 . .
C C10 0.83499(7) 0.3379(2) 0.29791(9) 0.0196(4) Uani d . . . 1 . .
C C11 0.88281(7) 0.2807(3) 0.30327(10) 0.0252(4) Uani d . . . 1 . .
H H11 0.8982 0.2848 0.3448 0.03 Uiso calc U . R 1 . .
C C12 0.90825(7) 0.2184(3) 0.24972(10) 0.0290(5) Uani d . . . 1 . .
H H12 0.9405 0.1792 0.255 0.035 Uiso calc U . R 1 . .
C C13 0.88701(7) 0.2131(3) 0.18857(10) 0.0281(5) Uani d . . . 1 . .
H H13 0.9044 0.1708 0.1517 0.034 Uiso calc U . R 1 . .
C C14 0.83984(7) 0.2703(3) 0.18177(10) 0.0293(5) Uani d . . . 1 . .
H H14 0.8249 0.2674 0.14 0.035 Uiso calc U . R 1 . .
C C15 0.81431(7) 0.3320(3) 0.23574(10) 0.0251(4) Uani d . . . 1 . .
H H15 0.7821 0.3708 0.2301 0.03 Uiso calc U . R 1 . .
C C21 0.59017(6) 0.7788(3) 0.47459(9) 0.0184(4) Uani d . . . 1 . .
C C22 0.56587(6) 0.6938(3) 0.42432(9) 0.0200(4) Uani d . . . 1 . .
F F22 0.57590(4) 0.52332(14) 0.41073(5) 0.0249(3) Uani d . . . 1 . .
C C23 0.53084(6) 0.7747(3) 0.38691(9) 0.0229(4) Uani d . . . 1 . .
F F23 0.50895(4) 0.68740(16) 0.33818(5) 0.0310(3) Uani d . . . 1 . .
C C24 0.51927(7) 0.9488(3) 0.39860(10) 0.0246(4) Uani d . . . 1 . .
F F24 0.48613(4) 1.03127(17) 0.36203(6) 0.0350(3) Uani d . . . 1 . .
C C25 0.54187(7) 1.0391(3) 0.44890(10) 0.0234(4) Uani d . . . 1 . .
F F25 0.53060(4) 1.20896(15) 0.46084(6) 0.0318(3) Uani d . . . 1 . .
C C26 0.57590(6) 0.9523(3) 0.48596(9) 0.0201(4) Uani d . . . 1 . .
F F26 0.59697(4) 1.04730(14) 0.53439(5) 0.0253(3) Uani d . . . 1 . .
C C31 0.62828(6) 0.7027(2) 0.59234(9) 0.0193(4) Uani d . . . 1 . .
C C32 0.58682(6) 0.6432(3) 0.62383(9) 0.0195(4) Uani d . . . 1 . .
F F32 0.55152(4) 0.56910(15) 0.58783(5) 0.0261(3) Uani d . . . 1 . .
C C33 0.57978(7) 0.6545(3) 0.69078(9) 0.0211(4) Uani d . . . 1 . .
F F33 0.53897(4) 0.59803(16) 0.71845(5) 0.0287(3) Uani d . . . 1 . .
C C34 0.61557(7) 0.7255(3) 0.72899(9) 0.0220(4) Uani d . . . 1 . .
F F34 0.61016(4) 0.73663(16) 0.79392(5) 0.0298(3) Uani d . . . 1 . .
C C35 0.65735(7) 0.7859(3) 0.70043(9) 0.0211(4) Uani d . . . 1 . .
F F35 0.69222(4) 0.85594(17) 0.73802(5) 0.0325(3) Uani d . . . 1 . .
C C36 0.66279(6) 0.7749(3) 0.63354(9) 0.0203(4) Uani d . . . 1 . .
F F36 0.70350(4) 0.84571(16) 0.60847(5) 0.0275(3) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C2 . 1.523(3) ?
B1 C31 . 1.578(3) ?
B1 C21 . 1.588(3) ?
C1 C9 . 1.507(3) ?
C1 C2 . 1.522(2) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.371(3) ?
C3 C4 . 1.442(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.398(3) ?
C4 C9 . 1.404(3) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.409(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.402(3) ?
C7 C10 . 1.492(3) ?
C8 C9 . 1.385(3) ?
C8 H8 . 0.95 ?
C10 C15 . 1.395(3) ?
C10 C11 . 1.403(3) ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.389(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.391(3) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C21 C22 . 1.386(3) ?
C21 C26 . 1.387(3) ?
C22 F22 . 1.345(2) ?
C22 C23 . 1.381(3) ?
C23 F23 . 1.340(2) ?
C23 C24 . 1.374(3) ?
C24 F24 . 1.340(2) ?
C24 C25 . 1.383(3) ?
C25 F25 . 1.342(2) ?
C25 C26 . 1.378(3) ?
C26 F26 . 1.355(2) ?
C31 C36 . 1.388(3) ?
C31 C32 . 1.395(3) ?
C32 F32 . 1.348(2) ?
C32 C33 . 1.384(3) ?
C33 F33 . 1.338(2) ?
C33 C34 . 1.374(3) ?
C34 F34 . 1.337(2) ?
C34 C35 . 1.378(3) ?
C35 F35 . 1.345(2) ?
C35 C36 . 1.377(3) ?
C36 F36 . 1.353(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 B1 C31 . . 122.45(17) ?
C2 B1 C21 . . 121.15(17) ?
C31 B1 C21 . . 116.34(16) ?
C9 C1 C2 . . 103.63(15) ?
C9 C1 H1A . . 111.0 ?
C2 C1 H1A . . 111.0 ?
C9 C1 H1B . . 111.0 ?
C2 C1 H1B . . 111.0 ?
H1A C1 H1B . . 109.0 ?
C3 C2 C1 . . 107.90(16) ?
C3 C2 B1 . . 125.13(17) ?
C1 C2 B1 . . 126.79(16) ?
C2 C3 C4 . . 111.45(16) ?
C2 C3 H3 . . 124.3 ?
C4 C3 H3 . . 124.3 ?
C5 C4 C9 . . 119.69(17) ?
C5 C4 C3 . . 132.18(17) ?
C9 C4 C3 . . 108.10(16) ?
C6 C5 C4 . . 119.19(17) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C7 . . 121.92(17) ?
C5 C6 H6 . . 119.0 ?
C7 C6 H6 . . 119.0 ?
C8 C7 C6 . . 118.21(17) ?
C8 C7 C10 . . 120.84(17) ?
C6 C7 C10 . . 120.88(17) ?
C9 C8 C7 . . 120.23(17) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C4 . . 120.71(17) ?
C8 C9 C1 . . 130.31(17) ?
C4 C9 C1 . . 108.91(15) ?
C15 C10 C11 . . 116.90(18) ?
C15 C10 C7 . . 121.43(17) ?
C11 C10 C7 . . 121.66(17) ?
C12 C11 C10 . . 121.83(18) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C13 C12 C11 . . 120.34(19) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 119.02(19) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C13 C14 C15 . . 120.48(19) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C10 . . 121.42(18) ?
C14 C15 H15 . . 119.3 ?
C10 C15 H15 . . 119.3 ?
C22 C21 C26 . . 114.87(17) ?
C22 C21 B1 . . 124.15(17) ?
C26 C21 B1 . . 120.93(17) ?
F22 C22 C23 . . 117.06(17) ?
F22 C22 C21 . . 119.59(16) ?
C23 C22 C21 . . 123.34(18) ?
F23 C23 C24 . . 119.53(17) ?
F23 C23 C22 . . 120.98(18) ?
C24 C23 C22 . . 119.47(18) ?
F24 C24 C23 . . 120.55(18) ?
F24 C24 C25 . . 119.89(18) ?
C23 C24 C25 . . 119.56(17) ?
F25 C25 C26 . . 120.98(18) ?
F25 C25 C24 . . 119.92(17) ?
C26 C25 C24 . . 119.10(18) ?
F26 C26 C25 . . 116.55(17) ?
F26 C26 C21 . . 119.83(16) ?
C25 C26 C21 . . 123.58(18) ?
C36 C31 C32 . . 114.76(17) ?
C36 C31 B1 . . 124.74(16) ?
C32 C31 B1 . . 120.46(16) ?
F32 C32 C33 . . 117.46(16) ?
F32 C32 C31 . . 118.98(16) ?
C33 C32 C31 . . 123.56(17) ?
F33 C33 C34 . . 119.94(17) ?
F33 C33 C32 . . 121.19(17) ?
C34 C33 C32 . . 118.87(17) ?
F34 C34 C33 . . 120.42(17) ?
F34 C34 C35 . . 119.60(17) ?
C33 C34 C35 . . 119.98(17) ?
F35 C35 C36 . . 120.70(16) ?
F35 C35 C34 . . 119.77(16) ?
C36 C35 C34 . . 119.52(17) ?
F36 C36 C35 . . 116.34(16) ?
F36 C36 C31 . . 120.30(16) ?
C35 C36 C31 . . 123.31(17) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . -0.3(2) ?
C9 C1 C2 B1 . . . . 174.92(18) ?
C31 B1 C2 C3 . . . . -0.5(3) ?
C21 B1 C2 C3 . . . . 176.57(18) ?
C31 B1 C2 C1 . . . . -174.97(18) ?
C21 B1 C2 C1 . . . . 2.1(3) ?
C1 C2 C3 C4 . . . . 0.5(2) ?
B1 C2 C3 C4 . . . . -174.79(18) ?
C2 C3 C4 C5 . . . . -178.3(2) ?
C2 C3 C4 C9 . . . . -0.6(2) ?
C9 C4 C5 C6 . . . . -2.3(3) ?
C3 C4 C5 C6 . . . . 175.20(19) ?
C4 C5 C6 C7 . . . . 1.4(3) ?
C5 C6 C7 C8 . . . . 0.8(3) ?
C5 C6 C7 C10 . . . . -176.26(17) ?
C6 C7 C8 C9 . . . . -2.0(3) ?
C10 C7 C8 C9 . . . . 175.05(17) ?
C7 C8 C9 C4 . . . . 1.1(3) ?
C7 C8 C9 C1 . . . . -175.55(18) ?
C5 C4 C9 C8 . . . . 1.1(3) ?
C3 C4 C9 C8 . . . . -176.95(17) ?
C5 C4 C9 C1 . . . . 178.38(16) ?
C3 C4 C9 C1 . . . . 0.3(2) ?
C2 C1 C9 C8 . . . . 176.92(19) ?
C2 C1 C9 C4 . . . . 0.0(2) ?
C8 C7 C10 C15 . . . . -12.3(3) ?
C6 C7 C10 C15 . . . . 164.67(18) ?
C8 C7 C10 C11 . . . . 168.93(18) ?
C6 C7 C10 C11 . . . . -14.1(3) ?
C15 C10 C11 C12 . . . . -1.0(3) ?
C7 C10 C11 C12 . . . . 177.81(19) ?
C10 C11 C12 C13 . . . . 0.8(3) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . -0.1(3) ?
C13 C14 C15 C10 . . . . -0.1(3) ?
C11 C10 C15 C14 . . . . 0.7(3) ?
C7 C10 C15 C14 . . . . -178.16(19) ?
C2 B1 C21 C22 . . . . 53.0(3) ?
C31 B1 C21 C22 . . . . -129.71(19) ?
C2 B1 C21 C26 . . . . -124.5(2) ?
C31 B1 C21 C26 . . . . 52.8(2) ?
C26 C21 C22 F22 . . . . -177.85(15) ?
B1 C21 C22 F22 . . . . 4.5(3) ?
C26 C21 C22 C23 . . . . 1.5(3) ?
B1 C21 C22 C23 . . . . -176.19(18) ?
F22 C22 C23 F23 . . . . -1.7(3) ?
C21 C22 C23 F23 . . . . 178.95(16) ?
F22 C22 C23 C24 . . . . -179.82(16) ?
C21 C22 C23 C24 . . . . 0.9(3) ?
F23 C23 C24 F24 . . . . 0.5(3) ?
C22 C23 C24 F24 . . . . 178.58(16) ?
F23 C23 C24 C25 . . . . -179.99(17) ?
C22 C23 C24 C25 . . . . -1.9(3) ?
F24 C24 C25 F25 . . . . -0.1(3) ?
C23 C24 C25 F25 . . . . -179.67(17) ?
F24 C24 C25 C26 . . . . -179.93(17) ?
C23 C24 C25 C26 . . . . 0.5(3) ?
F25 C25 C26 F26 . . . . 0.0(3) ?
C24 C25 C26 F26 . . . . 179.78(16) ?
F25 C25 C26 C21 . . . . -177.82(16) ?
C24 C25 C26 C21 . . . . 2.0(3) ?
C22 C21 C26 F26 . . . . 179.39(15) ?
B1 C21 C26 F26 . . . . -2.9(3) ?
C22 C21 C26 C25 . . . . -2.9(3) ?
B1 C21 C26 C25 . . . . 174.83(17) ?
C2 B1 C31 C36 . . . . 52.5(3) ?
C21 B1 C31 C36 . . . . -124.7(2) ?
C2 B1 C31 C32 . . . . -129.9(2) ?
C21 B1 C31 C32 . . . . 52.9(3) ?
C36 C31 C32 F32 . . . . -179.21(16) ?
B1 C31 C32 F32 . . . . 3.0(3) ?
C36 C31 C32 C33 . . . . 0.2(3) ?
B1 C31 C32 C33 . . . . -177.54(18) ?
F32 C32 C33 F33 . . . . -1.7(3) ?
C31 C32 C33 F33 . . . . 178.89(17) ?
F32 C32 C33 C34 . . . . 178.47(17) ?
C31 C32 C33 C34 . . . . -1.0(3) ?
F33 C33 C34 F34 . . . . 0.8(3) ?
C32 C33 C34 F34 . . . . -179.28(17) ?
F33 C33 C34 C35 . . . . -179.14(17) ?
C32 C33 C34 C35 . . . . 0.7(3) ?
F34 C34 C35 F35 . . . . -0.2(3) ?
C33 C34 C35 F35 . . . . 179.74(17) ?
F34 C34 C35 C36 . . . . -179.77(17) ?
C33 C34 C35 C36 . . . . 0.2(3) ?
F35 C35 C36 F36 . . . . -3.2(3) ?
C34 C35 C36 F36 . . . . 176.37(17) ?
F35 C35 C36 C31 . . . . 179.46(18) ?
C34 C35 C36 C31 . . . . -1.0(3) ?
C32 C31 C36 F36 . . . . -176.51(16) ?
B1 C31 C36 F36 . . . . 1.2(3) ?
C32 C31 C36 C35 . . . . 0.8(3) ?
B1 C31 C36 C35 . . . . 178.44(19) ?

