# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_wk133a
_database_code_depnum_ccdc_archive 'CCDC 1040186'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H14 B F19 N2'
_chemical_formula_weight         810.27

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.9506(5)
_cell_length_b                   19.9674(9)
_cell_length_c                   15.2675(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.711(2)
_cell_angle_gamma                90.00
_cell_volume                     3122.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            75746
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.40
_reflns_number_total             7800
_reflns_number_gt                6547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0692P)²+4.8626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7800
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8885(2) -0.01695(12) 0.24516(18) 0.0293(5) Uani 1 1 d . . .
C2 C 0.7530(2) -0.00844(10) 0.24650(16) 0.0222(4) Uani 1 1 d . . .
C3 C 0.6459(2) -0.02975(11) 0.17127(15) 0.0223(4) Uani 1 1 d . . .
H3A H 0.6567 -0.0486 0.1188 0.027 Uiso 1 1 calc R . .
C4 C 0.5224(2) -0.02240(10) 0.17592(14) 0.0212(4) Uani 1 1 d . . .
C5 C 0.4034(2) -0.04506(11) 0.09672(15) 0.0250(4) Uani 1 1 d . . .
C6 C 0.5047(2) 0.00596(10) 0.25387(14) 0.0195(4) Uani 1 1 d . . .
H6A H 0.4210 0.0105 0.2556 0.023 Uiso 1 1 calc R . .
C7 C 0.6125(2) 0.02749(10) 0.32935(14) 0.0188(4) Uani 1 1 d . . .
C8 C 0.6048(2) 0.05845(10) 0.41488(14) 0.0186(4) Uani 1 1 d . . .
C9 C 0.55779(19) 0.12927(10) 0.51034(13) 0.0171(4) Uani 1 1 d . . .
C10 C 0.49965(19) 0.18626(10) 0.53077(13) 0.0162(4) Uani 1 1 d . . .
C11 C 0.39509(19) 0.21865(10) 0.46398(13) 0.0159(4) Uani 1 1 d . . .
C12 C 0.2520(2) 0.23746(10) 0.32143(13) 0.0173(4) Uani 1 1 d . . .
C13 C 0.2452(2) 0.29210(10) 0.37799(14) 0.0197(4) Uani 1 1 d . . .
H13A H 0.1906 0.3291 0.3585 0.024 Uiso 1 1 calc R . .
C14 C 0.3333(2) 0.28134(10) 0.46721(14) 0.0180(4) Uani 1 1 d . . .
C15 C 0.3559(2) 0.32797(11) 0.54801(15) 0.0232(4) Uani 1 1 d . . .
H15A H 0.2994 0.3661 0.5282 0.035 Uiso 1 1 calc R . .
H15B H 0.4452 0.3426 0.5704 0.035 Uiso 1 1 calc R . .
H15C H 0.3377 0.3052 0.5974 0.035 Uiso 1 1 calc R . .
C16 C 0.1761(2) 0.23179(10) 0.22060(14) 0.0186(4) Uani 1 1 d . . .
C17 C 0.1607(2) 0.28943(10) 0.16556(14) 0.0199(4) Uani 1 1 d . . .
H17A H 0.1968 0.3297 0.1933 0.024 Uiso 1 1 calc R . .
C18 C 0.0919(2) 0.28683(11) 0.06989(15) 0.0232(4) Uani 1 1 d . . .
C19 C 0.0781(3) 0.34883(13) 0.01131(16) 0.0310(5) Uani 1 1 d . . .
C20 C 0.0359(2) 0.22735(12) 0.02752(15) 0.0259(5) Uani 1 1 d . . .
H20A H -0.0101 0.2256 -0.0366 0.031 Uiso 1 1 calc R . .
C21 C 0.0497(2) 0.17054(11) 0.08233(16) 0.0242(4) Uani 1 1 d . . .
C22 C -0.0106(3) 0.10531(14) 0.03869(18) 0.0359(6) Uani 1 1 d . . .
C23 C 0.1187(2) 0.17213(11) 0.17786(15) 0.0212(4) Uani 1 1 d . . .
H23A H 0.1267 0.1335 0.2135 0.025 Uiso 1 1 calc R . .
C24 C 0.5627(2) 0.21769(10) 0.62463(13) 0.0186(4) Uani 1 1 d . . .
C25 C 0.5269(2) 0.20218(11) 0.70058(14) 0.0214(4) Uani 1 1 d . . .
C26 C 0.5882(2) 0.23101(13) 0.78740(15) 0.0291(5) Uani 1 1 d . . .
C27 C 0.6881(3) 0.27610(13) 0.79956(16) 0.0340(6) Uani 1 1 d . . .
C28 C 0.7265(3) 0.29224(13) 0.72572(18) 0.0354(6) Uani 1 1 d . . .
C29 C 0.6641(2) 0.26287(12) 0.63944(16) 0.0281(5) Uani 1 1 d . . .
C30 C 0.6693(2) 0.09145(10) 0.56617(14) 0.0195(4) Uani 1 1 d . . .
C31 C 0.6969(2) 0.04783(11) 0.50548(15) 0.0217(4) Uani 1 1 d . . .
H31A H 0.7646 0.0168 0.5216 0.026 Uiso 1 1 calc R . .
C32 C 0.7447(2) 0.09522(12) 0.66914(15) 0.0261(5) Uani 1 1 d . . .
H32A H 0.8141 0.0630 0.6856 0.039 Uiso 1 1 calc R . .
H32B H 0.6876 0.0858 0.7030 0.039 Uiso 1 1 calc R . .
H32C H 0.7806 0.1393 0.6848 0.039 Uiso 1 1 calc R . .
C33 C 0.7372(2) 0.01967(10) 0.32498(15) 0.0216(4) Uani 1 1 d . . .
H33A H 0.8100 0.0334 0.3750 0.026 Uiso 1 1 calc R . .
F1 F 0.9493(2) -0.06703(13) 0.2984(2) 0.0893(10) Uani 1 1 d . . .
F2 F 0.95910(19) 0.03653(10) 0.26792(19) 0.0709(7) Uani 1 1 d . . .
F3 F 0.8890(2) -0.03624(13) 0.16141(16) 0.0701(7) Uani 1 1 d . . .
F4 F 0.43260(17) -0.07882(10) 0.03156(11) 0.0477(5) Uani 1 1 d . . .
F5 F 0.32921(18) 0.00646(8) 0.05324(12) 0.0484(5) Uani 1 1 d . . .
F6 F 0.32869(16) -0.08484(9) 0.12624(11) 0.0401(4) Uani 1 1 d . . .
F7 F -0.02620(19) 0.38500(9) 0.00828(13) 0.0519(5) Uani 1 1 d . . .
F8 F 0.18123(19) 0.38882(9) 0.04325(12) 0.0533(5) Uani 1 1 d . . .
F9 F 0.0612(2) 0.33496(9) -0.07758(11) 0.0497(5) Uani 1 1 d . . .
F10 F 0.0673(2) 0.05363(9) 0.07429(16) 0.0627(6) Uani 1 1 d . . .
F11 F -0.0402(2) 0.10556(10) -0.05413(12) 0.0570(5) Uani 1 1 d . . .
F12 F -0.12136(18) 0.09307(10) 0.05299(13) 0.0525(5) Uani 1 1 d . . .
F13 F 0.29919(12) 0.07765(6) 0.32302(9) 0.0224(3) Uani 1 1 d . . .
F14 F 0.41621(13) 0.14276(6) 0.25831(8) 0.0217(3) Uani 1 1 d . . .
F15 F 0.43237(14) 0.15726(8) 0.69046(10) 0.0330(3) Uani 1 1 d . . .
F16 F 0.55080(18) 0.21542(10) 0.85899(10) 0.0458(4) Uani 1 1 d . . .
F17 F 0.74724(19) 0.30416(10) 0.88330(11) 0.0532(5) Uani 1 1 d . . .
F18 F 0.8240(2) 0.33567(10) 0.73757(14) 0.0605(6) Uani 1 1 d . . .
F19 F 0.70414(18) 0.27897(9) 0.56887(11) 0.0456(4) Uani 1 1 d . . .
N1 N 0.51864(16) 0.10596(8) 0.41810(11) 0.0162(3) Uani 1 1 d . . .
N2 N 0.34175(16) 0.19294(8) 0.37326(11) 0.0159(3) Uani 1 1 d . . .
B1 B 0.3913(2) 0.12855(11) 0.33892(15) 0.0163(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F2 1.292(3) . ?
C1 F1 1.312(3) . ?
C1 F3 1.337(3) . ?
C1 C2 1.501(3) . ?
C2 C3 1.386(3) . ?
C2 C33 1.388(3) . ?
C3 C4 1.387(3) . ?
C3 H3A 0.9300 . ?
C4 C6 1.392(3) . ?
C4 C5 1.500(3) . ?
C5 F6 1.329(3) . ?
C5 F4 1.331(3) . ?
C5 F5 1.333(3) . ?
C6 C7 1.395(3) . ?
C6 H6A 0.9300 . ?
C7 C33 1.399(3) . ?
C7 C8 1.474(3) . ?
C8 N1 1.351(3) . ?
C8 C31 1.410(3) . ?
C9 C10 1.392(3) . ?
C9 N1 1.399(2) . ?
C9 C30 1.432(3) . ?
C10 C11 1.394(3) . ?
C10 C24 1.491(3) . ?
C11 N2 1.397(2) . ?
C11 C14 1.432(3) . ?
C12 N2 1.354(3) . ?
C12 C13 1.410(3) . ?
C12 C16 1.472(3) . ?
C13 C14 1.380(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.495(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C23 1.397(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.388(3) . ?
C17 H17A 0.9300 . ?
C18 C20 1.387(3) . ?
C18 C19 1.503(3) . ?
C19 F8 1.327(3) . ?
C19 F9 1.332(3) . ?
C19 F7 1.339(3) . ?
C20 C21 1.386(3) . ?
C20 H20A 0.9300 . ?
C21 C23 1.385(3) . ?
C21 C22 1.505(3) . ?
C22 F10 1.326(3) . ?
C22 F12 1.329(3) . ?
C22 F11 1.337(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.384(3) . ?
C24 C29 1.386(3) . ?
C25 F15 1.337(3) . ?
C25 C26 1.382(3) . ?
C26 F16 1.333(3) . ?
C26 C27 1.377(4) . ?
C27 F17 1.335(3) . ?
C27 C28 1.374(4) . ?
C28 F18 1.337(3) . ?
C28 C29 1.382(3) . ?
C29 F19 1.338(3) . ?
C30 C31 1.381(3) . ?
C30 C32 1.497(3) . ?
C31 H31A 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9300 . ?
F13 B1 1.391(3) . ?
F14 B1 1.381(2) . ?
N1 B1 1.555(3) . ?
N2 B1 1.557(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C1 F1 109.8(3) . . ?
F2 C1 F3 106.9(2) . . ?
F1 C1 F3 101.5(2) . . ?
F2 C1 C2 113.8(2) . . ?
F1 C1 C2 111.5(2) . . ?
F3 C1 C2 112.6(2) . . ?
C3 C2 C33 120.8(2) . . ?
C3 C2 C1 120.3(2) . . ?
C33 C2 C1 118.9(2) . . ?
C2 C3 C4 118.63(19) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 C6 121.4(2) . . ?
C3 C4 C5 120.77(19) . . ?
C6 C4 C5 117.9(2) . . ?
F6 C5 F4 106.88(19) . . ?
F6 C5 F5 106.8(2) . . ?
F4 C5 F5 106.49(19) . . ?
F6 C5 C4 111.75(18) . . ?
F4 C5 C4 112.7(2) . . ?
F5 C5 C4 111.80(18) . . ?
C4 C6 C7 119.9(2) . . ?
C4 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C6 C7 C33 118.80(19) . . ?
C6 C7 C8 124.35(19) . . ?
C33 C7 C8 116.85(19) . . ?
N1 C8 C31 109.65(17) . . ?
N1 C8 C7 125.90(18) . . ?
C31 C8 C7 124.10(18) . . ?
C10 C9 N1 119.72(17) . . ?
C10 C9 C30 131.21(18) . . ?
N1 C9 C30 108.48(17) . . ?
C9 C10 C11 122.53(17) . . ?
C9 C10 C24 117.80(17) . . ?
C11 C10 C24 119.27(18) . . ?
C10 C11 N2 120.14(17) . . ?
C10 C11 C14 131.01(18) . . ?
N2 C11 C14 108.57(17) . . ?
N2 C12 C13 109.58(17) . . ?
N2 C12 C16 125.82(18) . . ?
C13 C12 C16 124.57(18) . . ?
C14 C13 C12 108.30(18) . . ?
C14 C13 H13A 125.8 . . ?
C12 C13 H13A 125.8 . . ?
C13 C14 C11 106.03(17) . . ?
C13 C14 C15 124.87(19) . . ?
C11 C14 C15 129.09(18) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C16 C17 118.82(19) . . ?
C23 C16 C12 123.26(19) . . ?
C17 C16 C12 117.92(18) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C20 C18 C17 120.6(2) . . ?
C20 C18 C19 119.53(19) . . ?
C17 C18 C19 119.9(2) . . ?
F8 C19 F9 107.1(2) . . ?
F8 C19 F7 107.0(2) . . ?
F9 C19 F7 105.51(19) . . ?
F8 C19 C18 112.56(19) . . ?
F9 C19 C18 112.5(2) . . ?
F7 C19 C18 111.7(2) . . ?
C21 C20 C18 118.90(19) . . ?
C21 C20 H20A 120.5 . . ?
C18 C20 H20A 120.5 . . ?
C23 C21 C20 121.3(2) . . ?
C23 C21 C22 118.4(2) . . ?
C20 C21 C22 120.3(2) . . ?
F10 C22 F12 106.3(2) . . ?
F10 C22 F11 108.5(2) . . ?
F12 C22 F11 106.3(2) . . ?
F10 C22 C21 112.0(2) . . ?
F12 C22 C21 111.7(2) . . ?
F11 C22 C21 111.7(2) . . ?
C21 C23 C16 119.9(2) . . ?
C21 C23 H23A 120.0 . . ?
C16 C23 H23A 120.0 . . ?
C25 C24 C29 117.18(19) . . ?
C25 C24 C10 122.63(19) . . ?
C29 C24 C10 120.16(19) . . ?
F15 C25 C26 119.0(2) . . ?
F15 C25 C24 119.36(19) . . ?
C26 C25 C24 121.7(2) . . ?
F16 C26 C27 120.1(2) . . ?
F16 C26 C25 120.2(2) . . ?
C27 C26 C25 119.7(2) . . ?
F17 C27 C28 120.1(3) . . ?
F17 C27 C26 119.8(3) . . ?
C28 C27 C26 120.1(2) . . ?
F18 C28 C27 120.2(2) . . ?
F18 C28 C29 120.4(3) . . ?
C27 C28 C29 119.4(2) . . ?
F19 C29 C28 118.2(2) . . ?
F19 C29 C24 119.8(2) . . ?
C28 C29 C24 122.0(2) . . ?
C31 C30 C9 106.03(17) . . ?
C31 C30 C32 124.47(19) . . ?
C9 C30 C32 129.49(19) . . ?
C30 C31 C8 108.23(18) . . ?
C30 C31 H31A 125.9 . . ?
C8 C31 H31A 125.9 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C2 C33 C7 120.5(2) . . ?
C2 C33 H33A 119.7 . . ?
C7 C33 H33A 119.7 . . ?
C8 N1 C9 107.51(16) . . ?
C8 N1 B1 128.41(16) . . ?
C9 N1 B1 123.90(16) . . ?
C12 N2 C11 107.51(16) . . ?
C12 N2 B1 127.80(16) . . ?
C11 N2 B1 124.34(16) . . ?
F14 B1 F13 110.74(16) . . ?
F14 B1 N1 110.30(17) . . ?
F13 B1 N1 108.63(16) . . ?
F14 B1 N2 109.43(16) . . ?
F13 B1 N2 110.16(17) . . ?
N1 B1 N2 107.53(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C1 C2 C3 131.5(3) . . . . ?
F1 C1 C2 C3 -103.7(3) . . . . ?
F3 C1 C2 C3 9.6(3) . . . . ?
F2 C1 C2 C33 -49.9(3) . . . . ?
F1 C1 C2 C33 74.9(3) . . . . ?
F3 C1 C2 C33 -171.8(2) . . . . ?
C33 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 178.6(2) . . . . ?
C2 C3 C4 C6 0.3(3) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 F6 128.2(2) . . . . ?
C6 C4 C5 F6 -51.7(3) . . . . ?
C3 C4 C5 F4 7.8(3) . . . . ?
C6 C4 C5 F4 -172.0(2) . . . . ?
C3 C4 C5 F5 -112.1(2) . . . . ?
C6 C4 C5 F5 68.0(3) . . . . ?
C3 C4 C6 C7 -0.1(3) . . . . ?
C5 C4 C6 C7 179.73(19) . . . . ?
C4 C6 C7 C33 -0.3(3) . . . . ?
C4 C6 C7 C8 179.66(19) . . . . ?
C6 C7 C8 N1 -43.8(3) . . . . ?
C33 C7 C8 N1 136.1(2) . . . . ?
C6 C7 C8 C31 143.7(2) . . . . ?
C33 C7 C8 C31 -36.4(3) . . . . ?
N1 C9 C10 C11 5.5(3) . . . . ?
C30 C9 C10 C11 175.6(2) . . . . ?
N1 C9 C10 C24 -167.19(18) . . . . ?
C30 C9 C10 C24 3.0(3) . . . . ?
C9 C10 C11 N2 2.1(3) . . . . ?
C24 C10 C11 N2 174.68(17) . . . . ?
C9 C10 C11 C14 -171.0(2) . . . . ?
C24 C10 C11 C14 1.5(3) . . . . ?
N2 C12 C13 C14 0.2(2) . . . . ?
C16 C12 C13 C14 -177.55(19) . . . . ?
C12 C13 C14 C11 0.2(2) . . . . ?
C12 C13 C14 C15 179.9(2) . . . . ?
C10 C11 C14 C13 173.2(2) . . . . ?
N2 C11 C14 C13 -0.6(2) . . . . ?
C10 C11 C14 C15 -6.4(4) . . . . ?
N2 C11 C14 C15 179.8(2) . . . . ?
N2 C12 C16 C23 43.3(3) . . . . ?
C13 C12 C16 C23 -139.3(2) . . . . ?
N2 C12 C16 C17 -137.2(2) . . . . ?
C13 C12 C16 C17 40.2(3) . . . . ?
C23 C16 C17 C18 -1.4(3) . . . . ?
C12 C16 C17 C18 179.00(19) . . . . ?
C16 C17 C18 C20 0.9(3) . . . . ?
C16 C17 C18 C19 -178.9(2) . . . . ?
C20 C18 C19 F8 -147.2(2) . . . . ?
C17 C18 C19 F8 32.5(3) . . . . ?
C20 C18 C19 F9 -26.2(3) . . . . ?
C17 C18 C19 F9 153.6(2) . . . . ?
C20 C18 C19 F7 92.3(3) . . . . ?
C17 C18 C19 F7 -87.9(3) . . . . ?
C17 C18 C20 C21 0.1(3) . . . . ?
C19 C18 C20 C21 179.8(2) . . . . ?
C18 C20 C21 C23 -0.4(3) . . . . ?
C18 C20 C21 C22 179.6(2) . . . . ?
C23 C21 C22 F10 -40.1(3) . . . . ?
C20 C21 C22 F10 139.9(3) . . . . ?
C23 C21 C22 F12 79.0(3) . . . . ?
C20 C21 C22 F12 -101.0(3) . . . . ?
C23 C21 C22 F11 -162.0(2) . . . . ?
C20 C21 C22 F11 18.0(3) . . . . ?
C20 C21 C23 C16 -0.2(3) . . . . ?
C22 C21 C23 C16 179.8(2) . . . . ?
C17 C16 C23 C21 1.1(3) . . . . ?
C12 C16 C23 C21 -179.4(2) . . . . ?
C9 C10 C24 C25 -93.1(2) . . . . ?
C11 C10 C24 C25 94.0(2) . . . . ?
C9 C10 C24 C29 84.8(3) . . . . ?
C11 C10 C24 C29 -88.1(3) . . . . ?
C29 C24 C25 F15 -177.9(2) . . . . ?
C10 C24 C25 F15 0.1(3) . . . . ?
C29 C24 C25 C26 0.8(3) . . . . ?
C10 C24 C25 C26 178.8(2) . . . . ?
F15 C25 C26 F16 -1.8(3) . . . . ?
C24 C25 C26 F16 179.5(2) . . . . ?
F15 C25 C26 C27 178.3(2) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
F16 C26 C27 F17 0.0(3) . . . . ?
C25 C26 C27 F17 179.8(2) . . . . ?
F16 C26 C27 C28 -179.9(2) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
F17 C27 C28 F18 0.6(4) . . . . ?
C26 C27 C28 F18 -179.6(2) . . . . ?
F17 C27 C28 C29 -179.8(2) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
F18 C28 C29 F19 0.2(4) . . . . ?
C27 C28 C29 F19 -179.4(2) . . . . ?
F18 C28 C29 C24 -180.0(2) . . . . ?
C27 C28 C29 C24 0.4(4) . . . . ?
C25 C24 C29 F19 179.0(2) . . . . ?
C10 C24 C29 F19 1.0(3) . . . . ?
C25 C24 C29 C28 -0.8(4) . . . . ?
C10 C24 C29 C28 -178.9(2) . . . . ?
C10 C9 C30 C31 -169.1(2) . . . . ?
N1 C9 C30 C31 1.9(2) . . . . ?
C10 C9 C30 C32 11.3(4) . . . . ?
N1 C9 C30 C32 -177.7(2) . . . . ?
C9 C30 C31 C8 -0.1(2) . . . . ?
C32 C30 C31 C8 179.5(2) . . . . ?
N1 C8 C31 C30 -1.8(2) . . . . ?
C7 C8 C31 C30 171.8(2) . . . . ?
C3 C2 C33 C7 -0.5(3) . . . . ?
C1 C2 C33 C7 -179.1(2) . . . . ?
C6 C7 C33 C2 0.6(3) . . . . ?
C8 C7 C33 C2 -179.36(19) . . . . ?
C31 C8 N1 C9 2.9(2) . . . . ?
C7 C8 N1 C9 -170.47(19) . . . . ?
C31 C8 N1 B1 -172.16(19) . . . . ?
C7 C8 N1 B1 14.4(3) . . . . ?
C10 C9 N1 C8 169.21(18) . . . . ?
C30 C9 N1 C8 -3.0(2) . . . . ?
C10 C9 N1 B1 -15.4(3) . . . . ?
C30 C9 N1 B1 172.38(18) . . . . ?
C13 C12 N2 C11 -0.6(2) . . . . ?
C16 C12 N2 C11 177.15(19) . . . . ?
C13 C12 N2 B1 -174.06(18) . . . . ?
C16 C12 N2 B1 3.7(3) . . . . ?
C10 C11 N2 C12 -173.84(18) . . . . ?
C14 C11 N2 C12 0.7(2) . . . . ?
C10 C11 N2 B1 -0.1(3) . . . . ?
C14 C11 N2 B1 174.48(17) . . . . ?
C8 N1 B1 F14 -50.8(3) . . . . ?
C9 N1 B1 F14 134.80(18) . . . . ?
C8 N1 B1 F13 70.7(2) . . . . ?
C9 N1 B1 F13 -103.7(2) . . . . ?
C8 N1 B1 N2 -170.09(18) . . . . ?
C9 N1 B1 N2 15.5(2) . . . . ?
C12 N2 B1 F14 44.8(3) . . . . ?
C11 N2 B1 F14 -127.63(19) . . . . ?
C12 N2 B1 F13 -77.1(2) . . . . ?
C11 N2 B1 F13 110.4(2) . . . . ?
C12 N2 B1 N1 164.66(18) . . . . ?
C11 N2 B1 N1 -7.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_wk134
_database_code_depnum_ccdc_archive 'CCDC 1040187'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H16 B F13 N2'
_chemical_formula_weight         674.27

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.3337(12)
_cell_length_b                   9.9719(16)
_cell_length_c                   10.1280(16)
_cell_angle_alpha                93.269(5)
_cell_angle_beta                 99.210(5)
_cell_angle_gamma                110.524(4)
_cell_volume                     679.57(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.74

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3236
_exptl_absorpt_correction_T_max  0.4593
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4958
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         27.38
_reflns_number_total             4958
_reflns_number_gt                4889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0862P)²+1.0453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_number_reflns         4958
_refine_ls_number_parameters     425
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1747
_refine_ls_wR_factor_gt          0.1738
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2949(8) 0.3738(7) -0.5690(6) 0.0523(13) Uani 1 1 d . . .
C2 C 0.1340(7) 0.2502(5) -0.6552(4) 0.0402(11) Uani 1 1 d . . .
C3 C 0.1761(8) 0.1366(6) -0.7063(5) 0.0451(12) Uani 1 1 d . . .
H3A H 0.3035 0.1354 -0.6839 0.054 Uiso 1 1 calc R . .
C4 C 0.0252(7) 0.0208(5) -0.7935(5) 0.0397(10) Uani 1 1 d . . .
H4A H 0.0564 -0.0513 -0.8358 0.048 Uiso 1 1 calc R . .
C5 C -0.1631(7) 0.0154(5) -0.8149(4) 0.0328(9) Uani 1 1 d . . .
C6 C -0.3216(6) -0.1115(4) -0.8967(4) 0.0271(8) Uani 1 1 d . . .
C7 C -0.6107(6) -0.2896(4) -0.9705(4) 0.0277(8) Uani 1 1 d . . .
C8 C -0.8064(6) -0.3762(3) -0.9620(4) 0.0234(7) Uani 1 1 d . . .
C9 C -0.8922(6) -0.3623(4) -0.8553(4) 0.0260(8) Uani 1 1 d . . .
C10 C -0.8942(6) -0.2650(4) -0.6506(4) 0.0272(8) Uani 1 1 d . . .
C11 C -1.0936(5) -0.3635(4) -0.7061(4) 0.0240(7) Uani 1 1 d . . .
H11A H -1.2035 -0.3827 -0.6653 0.029 Uiso 1 1 calc R . .
C12 C -1.0895(6) -0.4237(4) -0.8315(4) 0.0254(8) Uani 1 1 d . . .
C13 C -1.2718(7) -0.5378(5) -0.9204(5) 0.0384(10) Uani 1 1 d . . .
H13A H -1.3834 -0.5565 -0.8764 0.058 Uiso 1 1 calc R . .
H13B H -1.2467 -0.6251 -0.9357 0.058 Uiso 1 1 calc R . .
H13C H -1.3002 -0.5036 -1.0052 0.058 Uiso 1 1 calc R . .
C14 C -0.8347(6) -0.1792(4) -0.5153(4) 0.0245(8) Uani 1 1 d . . .
C15 C -0.6555(8) -0.1602(5) -0.4333(5) 0.0416(11) Uani 1 1 d . . .
H15A H -0.5735 -0.2055 -0.4597 0.050 Uiso 1 1 calc R . .
C16 C -0.5999(7) -0.0734(5) -0.3119(5) 0.0377(10) Uani 1 1 d . . .
H16A H -0.4786 -0.0577 -0.2562 0.045 Uiso 1 1 calc R . .
C17 C -0.7322(7) -0.0070(5) -0.2722(5) 0.0398(10) Uani 1 1 d . . .
C18 C -0.6715(6) 0.0843(5) -0.1437(5) 0.0373(10) Uani 1 1 d . . .
C19 C -0.9065(7) -0.0259(5) -0.3559(5) 0.0414(11) Uani 1 1 d . . .
H19A H -0.9890 0.0197 -0.3309 0.050 Uiso 1 1 calc R . .
C20 C -0.9614(8) -0.1133(6) -0.4786(4) 0.0448(12) Uani 1 1 d . . .
H20A H -1.0812 -0.1276 -0.5354 0.054 Uiso 1 1 calc R . .
C21 C -0.9277(6) -0.4827(5) -1.0787(4) 0.0272(8) Uani 1 1 d . . .
C22 C -1.0093(6) -0.4428(4) -1.1964(4) 0.0273(8) Uani 1 1 d . . .
C23 C -1.1224(7) -0.5435(6) -1.3083(5) 0.0405(11) Uani 1 1 d . . .
C24 C -1.1573(6) -0.6896(5) -1.2986(4) 0.0333(9) Uani 1 1 d . . .
C25 C -1.0830(7) -0.7339(5) -1.1837(5) 0.0367(10) Uani 1 1 d . . .
C26 C -0.9643(6) -0.6278(4) -1.0748(3) 0.0231(7) Uani 1 1 d . . .
C27 C -0.4878(6) -0.2907(4) -1.0665(4) 0.0252(8) Uani 1 1 d . . .
C28 C -0.3096(7) -0.1818(4) -1.0186(4) 0.0281(8) Uani 1 1 d . . .
H28A H -0.1991 -0.1579 -1.0592 0.034 Uiso 1 1 calc R . .
C29 C -0.5413(6) -0.3903(5) -1.1952(4) 0.0289(8) Uani 1 1 d . . .
H29A H -0.4299 -0.3662 -1.2398 0.043 Uiso 1 1 calc R . .
H29B H -0.6519 -0.3803 -1.2530 0.043 Uiso 1 1 calc R . .
H29C H -0.5763 -0.4881 -1.1753 0.043 Uiso 1 1 calc R . .
C30 C -0.2073(7) 0.1315(5) -0.7684(5) 0.0390(10) Uani 1 1 d . . .
H30A H -0.3356 0.1312 -0.7898 0.047 Uiso 1 1 calc R . .
C31 C -0.0531(7) 0.2510(5) -0.6874(4) 0.0367(10) Uani 1 1 d . . .
H31A H -0.0801 0.3303 -0.6563 0.044 Uiso 1 1 calc R . .
F1 F 0.2321(7) 0.4800(4) -0.5296(5) 0.0871(14) Uani 1 1 d . . .
F2 F 0.4455(7) 0.4305(5) -0.6266(4) 0.0934(16) Uani 1 1 d . . .
F3 F 0.3612(7) 0.3357(5) -0.4532(4) 0.0800(12) Uani 1 1 d . . .
F4 F -0.6758(6) 0.2180(4) -0.1573(4) 0.0686(10) Uani 1 1 d . . .
F5 F -0.7872(6) 0.0283(5) -0.0600(3) 0.0701(11) Uani 1 1 d . . .
F6 F -0.4866(5) 0.1088(4) -0.0767(3) 0.0648(10) Uani 1 1 d . . .
F7 F -0.5221(4) -0.0366(3) -0.6716(3) 0.0512(8) Uani 1 1 d . . .
F8 F -0.4362(4) -0.2314(4) -0.6376(3) 0.0512(7) Uani 1 1 d . . .
F9 F -0.9791(4) -0.3041(3) -1.2044(3) 0.0459(7) Uani 1 1 d . . .
F10 F -1.1903(5) -0.4993(4) -1.4179(3) 0.0605(9) Uani 1 1 d . . .
F11 F -1.2649(5) -0.7844(4) -1.4032(3) 0.0587(9) Uani 1 1 d . . .
F12 F -1.1223(4) -0.8718(3) -1.1772(3) 0.0518(8) Uani 1 1 d . . .
F13 F -0.8946(4) -0.6771(3) -0.9663(3) 0.0401(6) Uani 1 1 d . . .
N1 N -0.5018(5) -0.1784(3) -0.8682(3) 0.0250(7) Uani 1 1 d . . .
N2 N -0.7781(5) -0.2662(3) -0.7398(3) 0.0275(7) Uani 1 1 d . . .
B1 B -0.5543(8) -0.1727(6) -0.7253(5) 0.0396(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F2 1.299(7) . ?
C1 F3 1.324(7) . ?
C1 F1 1.358(7) . ?
C1 C2 1.484(7) . ?
C2 C31 1.361(7) . ?
C2 C3 1.370(8) . ?
C3 C4 1.419(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.344(7) . ?
C4 H4A 0.9300 . ?
C5 C30 1.384(7) . ?
C5 C6 1.476(6) . ?
C6 N1 1.342(5) . ?
C6 C28 1.415(5) . ?
C7 N1 1.387(5) . ?
C7 C8 1.411(6) . ?
C7 C27 1.430(6) . ?
C8 C9 1.358(6) . ?
C8 C21 1.474(5) . ?
C9 N2 1.409(5) . ?
C9 C12 1.426(6) . ?
C10 N2 1.339(5) . ?
C10 C11 1.444(5) . ?
C10 C14 1.488(5) . ?
C11 C12 1.383(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.525(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.382(7) . ?
C14 C20 1.395(7) . ?
C15 C16 1.378(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.444(7) . ?
C16 H16A 0.9300 . ?
C17 C19 1.362(7) . ?
C17 C18 1.455(6) . ?
C18 F5 1.304(6) . ?
C18 F6 1.347(5) . ?
C18 F4 1.360(6) . ?
C19 C20 1.392(7) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C26 1.381(6) . ?
C21 C22 1.389(5) . ?
C22 F9 1.332(5) . ?
C22 C23 1.402(6) . ?
C23 F10 1.307(6) . ?
C23 C24 1.400(7) . ?
C24 F11 1.317(5) . ?
C24 C25 1.368(7) . ?
C25 F12 1.310(5) . ?
C25 C26 1.417(6) . ?
C26 F13 1.330(4) . ?
C27 C28 1.366(6) . ?
C27 C29 1.502(5) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.421(7) . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9300 . ?
F7 B1 1.357(7) . ?
F8 B1 1.432(7) . ?
N1 B1 1.560(6) . ?
N2 B1 1.555(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C1 F3 107.7(5) . . ?
F2 C1 F1 108.2(5) . . ?
F3 C1 F1 103.1(5) . . ?
F2 C1 C2 112.8(5) . . ?
F3 C1 C2 111.6(5) . . ?
F1 C1 C2 112.7(5) . . ?
C31 C2 C3 119.9(4) . . ?
C31 C2 C1 120.6(5) . . ?
C3 C2 C1 119.5(5) . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C30 120.5(4) . . ?
C4 C5 C6 119.5(4) . . ?
C30 C5 C6 119.9(4) . . ?
N1 C6 C28 108.7(4) . . ?
N1 C6 C5 125.5(3) . . ?
C28 C6 C5 125.8(4) . . ?
N1 C7 C8 118.8(4) . . ?
N1 C7 C27 107.9(4) . . ?
C8 C7 C27 133.3(4) . . ?
C9 C8 C7 123.7(4) . . ?
C9 C8 C21 118.2(3) . . ?
C7 C8 C21 118.0(3) . . ?
C8 C9 N2 119.6(4) . . ?
C8 C9 C12 133.4(4) . . ?
N2 C9 C12 106.9(3) . . ?
N2 C10 C11 108.9(3) . . ?
N2 C10 C14 127.4(4) . . ?
C11 C10 C14 123.8(4) . . ?
C12 C11 C10 106.8(3) . . ?
C12 C11 H11A 126.6 . . ?
C10 C11 H11A 126.6 . . ?
C11 C12 C9 108.1(3) . . ?
C11 C12 C13 122.6(4) . . ?
C9 C12 C13 129.3(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C20 121.9(4) . . ?
C15 C14 C10 120.6(4) . . ?
C20 C14 C10 117.3(4) . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 119.2(4) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
C19 C17 C16 120.4(4) . . ?
C19 C17 C18 121.0(4) . . ?
C16 C17 C18 118.5(4) . . ?
F5 C18 F6 105.1(4) . . ?
F5 C18 F4 107.3(4) . . ?
F6 C18 F4 104.5(4) . . ?
F5 C18 C17 111.3(4) . . ?
F6 C18 C17 115.8(4) . . ?
F4 C18 C17 112.2(4) . . ?
C17 C19 C20 120.1(5) . . ?
C17 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C19 C20 C14 119.2(4) . . ?
C19 C20 H20A 120.4 . . ?
C14 C20 H20A 120.4 . . ?
C26 C21 C22 117.1(3) . . ?
C26 C21 C8 120.6(3) . . ?
C22 C21 C8 122.3(4) . . ?
F9 C22 C21 119.2(3) . . ?
F9 C22 C23 118.3(4) . . ?
C21 C22 C23 122.4(4) . . ?
F10 C23 C24 122.1(4) . . ?
F10 C23 C22 119.7(4) . . ?
C24 C23 C22 118.2(4) . . ?
F11 C24 C25 120.4(4) . . ?
F11 C24 C23 118.3(4) . . ?
C25 C24 C23 121.3(4) . . ?
F12 C25 C24 119.6(4) . . ?
F12 C25 C26 122.0(4) . . ?
C24 C25 C26 118.4(4) . . ?
F13 C26 C21 121.8(3) . . ?
F13 C26 C25 115.7(3) . . ?
C21 C26 C25 122.4(3) . . ?
C28 C27 C7 106.4(3) . . ?
C28 C27 C29 126.1(4) . . ?
C7 C27 C29 127.6(4) . . ?
C27 C28 C6 108.4(4) . . ?
C27 C28 H28A 125.8 . . ?
C6 C28 H28A 125.8 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C5 C30 C31 118.8(4) . . ?
C5 C30 H30A 120.6 . . ?
C31 C30 H30A 120.6 . . ?
C2 C31 C30 120.4(4) . . ?
C2 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C6 N1 C7 108.6(3) . . ?
C6 N1 B1 125.1(3) . . ?
C7 N1 B1 122.8(4) . . ?
C10 N2 C9 109.4(3) . . ?
C10 N2 B1 126.8(3) . . ?
C9 N2 B1 123.7(3) . . ?
F7 B1 F8 108.9(4) . . ?
F7 B1 N2 108.9(4) . . ?
F8 B1 N2 110.1(4) . . ?
F7 B1 N1 112.7(4) . . ?
F8 B1 N1 108.9(4) . . ?
N2 B1 N1 107.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C1 C2 C31 -122.9(6) . . . . ?
F3 C1 C2 C31 115.6(5) . . . . ?
F1 C1 C2 C31 0.1(7) . . . . ?
F2 C1 C2 C3 55.0(7) . . . . ?
F3 C1 C2 C3 -66.6(7) . . . . ?
F1 C1 C2 C3 178.0(5) . . . . ?
C31 C2 C3 C4 0.5(7) . . . . ?
C1 C2 C3 C4 -177.3(4) . . . . ?
C2 C3 C4 C5 -6.8(7) . . . . ?
C3 C4 C5 C30 9.2(6) . . . . ?
C3 C4 C5 C6 -175.0(4) . . . . ?
C4 C5 C6 N1 137.7(4) . . . . ?
C30 C5 C6 N1 -46.5(6) . . . . ?
C4 C5 C6 C28 -43.0(6) . . . . ?
C30 C5 C6 C28 132.8(4) . . . . ?
N1 C7 C8 C9 -3.6(5) . . . . ?
C27 C7 C8 C9 175.3(4) . . . . ?
N1 C7 C8 C21 173.0(3) . . . . ?
C27 C7 C8 C21 -8.0(6) . . . . ?
C7 C8 C9 N2 -6.1(5) . . . . ?
C21 C8 C9 N2 177.2(3) . . . . ?
C7 C8 C9 C12 171.2(4) . . . . ?
C21 C8 C9 C12 -5.4(6) . . . . ?
N2 C10 C11 C12 0.4(4) . . . . ?
C14 C10 C11 C12 -179.2(3) . . . . ?
C10 C11 C12 C9 -1.0(4) . . . . ?
C10 C11 C12 C13 177.9(4) . . . . ?
C8 C9 C12 C11 -176.5(4) . . . . ?
N2 C9 C12 C11 1.1(4) . . . . ?
C8 C9 C12 C13 4.8(7) . . . . ?
N2 C9 C12 C13 -177.6(4) . . . . ?
N2 C10 C14 C15 -39.6(6) . . . . ?
C11 C10 C14 C15 140.0(4) . . . . ?
N2 C10 C14 C20 137.1(5) . . . . ?
C11 C10 C14 C20 -43.3(6) . . . . ?
C20 C14 C15 C16 -0.2(7) . . . . ?
C10 C14 C15 C16 176.3(4) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C15 C16 C17 C19 -2.3(7) . . . . ?
C15 C16 C17 C18 179.9(4) . . . . ?
C19 C17 C18 F5 67.7(6) . . . . ?
C16 C17 C18 F5 -114.6(5) . . . . ?
C19 C17 C18 F6 -172.4(5) . . . . ?
C16 C17 C18 F6 5.3(7) . . . . ?
C19 C17 C18 F4 -52.6(6) . . . . ?
C16 C17 C18 F4 125.2(5) . . . . ?
C16 C17 C19 C20 2.1(8) . . . . ?
C18 C17 C19 C20 179.8(5) . . . . ?
C17 C19 C20 C14 -0.9(8) . . . . ?
C15 C14 C20 C19 0.0(7) . . . . ?
C10 C14 C20 C19 -176.7(4) . . . . ?
C9 C8 C21 C26 -78.0(5) . . . . ?
C7 C8 C21 C26 105.1(4) . . . . ?
C9 C8 C21 C22 102.1(4) . . . . ?
C7 C8 C21 C22 -74.7(5) . . . . ?
C26 C21 C22 F9 179.5(4) . . . . ?
C8 C21 C22 F9 -0.6(6) . . . . ?
C26 C21 C22 C23 -0.8(6) . . . . ?
C8 C21 C22 C23 179.1(4) . . . . ?
F9 C22 C23 F10 1.8(6) . . . . ?
C21 C22 C23 F10 -177.9(4) . . . . ?
F9 C22 C23 C24 -178.7(4) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
F10 C23 C24 F11 -1.1(7) . . . . ?
C22 C23 C24 F11 179.4(4) . . . . ?
F10 C23 C24 C25 179.2(4) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
F11 C24 C25 F12 -1.2(6) . . . . ?
C23 C24 C25 F12 178.5(4) . . . . ?
F11 C24 C25 C26 178.6(4) . . . . ?
C23 C24 C25 C26 -1.7(6) . . . . ?
C22 C21 C26 F13 -179.3(3) . . . . ?
C8 C21 C26 F13 0.8(6) . . . . ?
C22 C21 C26 C25 -1.3(6) . . . . ?
C8 C21 C26 C25 178.8(4) . . . . ?
F12 C25 C26 F13 0.4(6) . . . . ?
C24 C25 C26 F13 -179.3(4) . . . . ?
F12 C25 C26 C21 -177.7(4) . . . . ?
C24 C25 C26 C21 2.6(6) . . . . ?
N1 C7 C27 C28 0.5(4) . . . . ?
C8 C7 C27 C28 -178.5(4) . . . . ?
N1 C7 C27 C29 -179.2(4) . . . . ?
C8 C7 C27 C29 1.8(7) . . . . ?
C7 C27 C28 C6 -1.3(4) . . . . ?
C29 C27 C28 C6 178.4(4) . . . . ?
N1 C6 C28 C27 1.7(4) . . . . ?
C5 C6 C28 C27 -177.7(4) . . . . ?
C4 C5 C30 C31 -5.6(6) . . . . ?
C6 C5 C30 C31 178.7(4) . . . . ?
C3 C2 C31 C30 3.1(7) . . . . ?
C1 C2 C31 C30 -179.1(4) . . . . ?
C5 C30 C31 C2 -0.7(6) . . . . ?
C28 C6 N1 C7 -1.3(4) . . . . ?
C5 C6 N1 C7 178.1(4) . . . . ?
C28 C6 N1 B1 157.9(4) . . . . ?
C5 C6 N1 B1 -22.7(6) . . . . ?
C8 C7 N1 C6 179.7(3) . . . . ?
C27 C7 N1 C6 0.5(4) . . . . ?
C8 C7 N1 B1 19.9(6) . . . . ?
C27 C7 N1 B1 -159.3(4) . . . . ?
C11 C10 N2 C9 0.3(4) . . . . ?
C14 C10 N2 C9 179.9(3) . . . . ?
C11 C10 N2 B1 177.5(4) . . . . ?
C14 C10 N2 B1 -2.9(7) . . . . ?
C8 C9 N2 C10 177.1(3) . . . . ?
C12 C9 N2 C10 -0.9(4) . . . . ?
C8 C9 N2 B1 -0.2(6) . . . . ?
C12 C9 N2 B1 -178.2(4) . . . . ?
C10 N2 B1 F7 -41.3(6) . . . . ?
C9 N2 B1 F7 135.6(4) . . . . ?
C10 N2 B1 F8 78.1(5) . . . . ?
C9 N2 B1 F8 -105.1(4) . . . . ?
C10 N2 B1 N1 -163.6(4) . . . . ?
C9 N2 B1 N1 13.3(6) . . . . ?
C6 N1 B1 F7 60.5(6) . . . . ?
C7 N1 B1 F7 -143.1(4) . . . . ?
C6 N1 B1 F8 -60.5(6) . . . . ?
C7 N1 B1 F8 95.9(5) . . . . ?
C6 N1 B1 N2 -179.6(4) . . . . ?
C7 N1 B1 N2 -23.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.38
_diffrn_measured_fraction_theta_full 0.882
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091
