# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_mo_50311aa
_database_code_depnum_ccdc_archive 'CCDC 1426309'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 B2 F18 N O2'
_chemical_formula_weight         807.14

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.704(4)
_cell_length_b                   19.046(5)
_cell_length_c                   13.618(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.145(4)
_cell_angle_gamma                90
_cell_volume                     3396.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4379
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      23.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24631
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7756
_reflns_number_gt                4736
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0734P)²+0.5025P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7756
_refine_ls_number_parameters     524
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.22778(19) 0.84450(13) 0.78158(19) 0.0241(5) Uani 1 1 d . . . . .
H1 H 0.1571(16) 0.8705(10) 0.7869(15) 0.013(5) Uiso 1 1 d . . . . .
B2 B -0.0220(2) 0.76798(14) 0.8640(2) 0.0309(6) Uani 1 1 d . . . . .
N1 N 0.19149(13) 0.76518(9) 0.74868(13) 0.0228(4) Uani 1 1 d . . . . .
O1 O -0.09698(14) 0.74172(10) 0.78359(14) 0.0443(5) Uani 1 1 d . . . . .
O2 O -0.05603(14) 0.79969(10) 0.93609(13) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.12622(17) 0.73051(12) 0.79006(16) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.08859(18) 0.66539(13) 0.75181(19) 0.0341(6) Uani 1 1 d . . . . .
H2 H 0.0430 0.6419 0.7815 0.041 Uiso 1 1 calc R U . . .
C3 C 0.11467(18) 0.63334(12) 0.67229(19) 0.0326(5) Uani 1 1 d . . . . .
C4 C 0.18199(18) 0.66969(12) 0.63235(17) 0.0286(5) Uani 1 1 d . . . . .
H4 H 0.2034 0.6498 0.5782 0.034 Uiso 1 1 calc R U . . .
C5 C 0.21732(17) 0.73372(12) 0.67053(16) 0.0265(5) Uani 1 1 d . . . . .
H5 H 0.2625 0.7577 0.6409 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0718(3) 0.56355(15) 0.6300(3) 0.0546(8) Uani 1 1 d . . . . .
H6A H 0.0355 0.5683 0.5567 0.082 Uiso 1 1 calc R U . . .
H6B H 0.0243 0.5471 0.6666 0.082 Uiso 1 1 calc R U . . .
H6C H 0.1275 0.5296 0.6392 0.082 Uiso 1 1 calc R U . . .
C7 C 0.09509(19) 0.76110(14) 0.87804(18) 0.0345(6) Uani 1 1 d . . . . .
H7A H 0.1259 0.8084 0.8927 0.041 Uiso 1 1 calc R U . . .
H7B H 0.1253 0.7318 0.9395 0.041 Uiso 1 1 calc R U . . .
C8 C -0.19206(19) 0.74486(14) 0.8129(2) 0.0386(6) Uani 1 1 d . . . . .
C9 C -0.1675(2) 0.80392(14) 0.8961(2) 0.0389(6) Uani 1 1 d . . . . .
C10 C -0.2059(2) 0.67297(16) 0.8539(3) 0.0549(8) Uani 1 1 d . . . . .
H10A H -0.2059 0.6374 0.8019 0.082 Uiso 1 1 calc R U . . .
H10B H -0.2709 0.6713 0.8701 0.082 Uiso 1 1 calc R U . . .
H10C H -0.1497 0.6636 0.9163 0.082 Uiso 1 1 calc R U . . .
C11 C -0.2794(2) 0.76159(18) 0.7175(2) 0.0514(7) Uani 1 1 d . . . . .
H11A H -0.2623 0.8033 0.6838 0.077 Uiso 1 1 calc R U . . .
H11B H -0.3416 0.7705 0.7370 0.077 Uiso 1 1 calc R U . . .
H11C H -0.2907 0.7217 0.6700 0.077 Uiso 1 1 calc R U . . .
C12 C -0.2115(3) 0.79185(19) 0.9841(3) 0.0622(9) Uani 1 1 d . . . . .
H12A H -0.1881 0.7464 1.0162 0.093 Uiso 1 1 calc R U . . .
H12B H -0.2863 0.7920 0.9582 0.093 Uiso 1 1 calc R U . . .
H12C H -0.1888 0.8293 1.0351 0.093 Uiso 1 1 calc R U . . .
C13 C -0.1923(3) 0.87744(15) 0.8532(3) 0.0579(8) Uani 1 1 d . . . . .
H13A H -0.1599 0.9119 0.9062 0.087 Uiso 1 1 calc R U . . .
H13B H -0.2665 0.8844 0.8319 0.087 Uiso 1 1 calc R U . . .
H13C H -0.1667 0.8836 0.7938 0.087 Uiso 1 1 calc R U . . .
C14 C 0.30925(16) 0.85345(11) 0.89844(16) 0.0232(5) Uani 1 1 d . . . . .
C15 C 0.37429(17) 0.80312(11) 0.96216(16) 0.0255(5) Uani 1 1 d . . . . .
C16 C 0.43506(17) 0.81885(13) 1.06161(17) 0.0298(5) Uani 1 1 d . . . . .
H16 H 0.4764 0.7831 1.1020 0.036 Uiso 1 1 calc R U . . .
C17 C 0.43605(17) 0.88503(12) 1.10194(18) 0.0305(5) Uani 1 1 d . . . . .
C18 C 0.37356(18) 0.93591(12) 1.04397(18) 0.0315(5) Uani 1 1 d . . . . .
H18 H 0.3733 0.9818 1.0712 0.038 Uiso 1 1 calc R U . . .
C19 C 0.31108(17) 0.92049(12) 0.94608(17) 0.0277(5) Uani 1 1 d . . . . .
C20 C 0.38077(19) 0.72585(12) 0.93781(18) 0.0323(5) Uani 1 1 d . . . . .
C21 C 0.5024(2) 0.90226(15) 1.2076(2) 0.0410(6) Uani 1 1 d . . . . .
C22 C 0.2391(2) 0.97973(12) 0.89824(19) 0.0365(6) Uani 1 1 d . . . . .
C23 C 0.25509(16) 0.88546(11) 0.68462(16) 0.0234(5) Uani 1 1 d . . . . .
C24 C 0.35219(17) 0.90375(11) 0.67636(16) 0.0237(5) Uani 1 1 d . . . . .
C25 C 0.36644(18) 0.94760(12) 0.59927(17) 0.0283(5) Uani 1 1 d . . . . .
H25 H 0.4335 0.9591 0.5981 0.034 Uiso 1 1 calc R U . . .
C26 C 0.2838(2) 0.97385(12) 0.52567(18) 0.0328(5) Uani 1 1 d . . . . .
C27 C 0.18711(19) 0.95574(12) 0.52669(17) 0.0331(6) Uani 1 1 d . . . . .
H27 H 0.1297 0.9727 0.4741 0.040 Uiso 1 1 calc R U . . .
C28 C 0.17211(17) 0.91295(12) 0.60361(17) 0.0280(5) Uani 1 1 d . . . . .
C29 C 0.45092(17) 0.87764(13) 0.75014(18) 0.0297(5) Uani 1 1 d . . . . .
C30 C 0.2979(3) 1.02061(17) 0.4421(2) 0.0504(7) Uani 1 1 d D . . . .
C31 C 0.06101(19) 0.90185(13) 0.5973(2) 0.0361(6) Uani 1 1 d . . . . .
F1 F 0.37117(11) 0.70917(7) 0.84140(10) 0.0367(3) Uani 1 1 d . . . . .
F2 F 0.30600(14) 0.68967(8) 0.96321(13) 0.0532(4) Uani 1 1 d . . . . .
F3 F 0.46769(13) 0.69672(8) 0.99301(13) 0.0597(5) Uani 1 1 d . . . . .
F4 F 0.53138(12) 0.84490(9) 1.26599(11) 0.0518(4) Uani 1 1 d . . . . .
F5 F 0.58867(13) 0.93449(10) 1.20597(13) 0.0612(5) Uani 1 1 d . . . . .
F6 F 0.45667(14) 0.94462(11) 1.25795(13) 0.0682(6) Uani 1 1 d . . . . .
F7 F 0.23129(11) 0.99420(7) 0.80058(10) 0.0378(3) Uani 1 1 d . . . . .
F8 F 0.26708(15) 1.04092(8) 0.94851(12) 0.0585(5) Uani 1 1 d . . . . .
F9 F 0.14366(12) 0.96703(9) 0.90295(13) 0.0539(4) Uani 1 1 d . . . . .
F10 F 0.47745(10) 0.91150(8) 0.84067(10) 0.0395(4) Uani 1 1 d . . . . .
F11 F 0.44668(11) 0.80934(7) 0.77115(12) 0.0421(4) Uani 1 1 d . . . . .
F12 F 0.53020(11) 0.88521(9) 0.71262(12) 0.0471(4) Uani 1 1 d . . . . .
F13 F 0.3884(6) 1.0296(10) 0.4430(11) 0.110(5) Uani 0.53(2) 1 d . U P A 1
F14 F 0.2562(12) 0.9902(7) 0.3492(5) 0.108(4) Uani 0.53(2) 1 d . U P A 1
F15 F 0.2533(14) 1.0792(4) 0.4380(12) 0.111(5) Uani 0.53(2) 1 d . U P A 1
F13' F 0.318(2) 0.9902(6) 0.3705(14) 0.135(6) Uani 0.47(2) 1 d D U P A 2
F14' F 0.2217(8) 1.0614(9) 0.4018(11) 0.114(6) Uani 0.47(2) 1 d D U P A 2
F15' F 0.3727(13) 1.0670(9) 0.4795(10) 0.125(6) Uani 0.47(2) 1 d D U P A 2
F16 F 0.03707(11) 0.83590(8) 0.61525(12) 0.0459(4) Uani 1 1 d . . . . .
F17 F 0.03014(11) 0.94361(9) 0.66138(13) 0.0516(4) Uani 1 1 d . . . . .
F18 F -0.00058(12) 0.91702(9) 0.50277(12) 0.0526(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
B1 N1 1.612(3) . ?
B1 C14 1.661(3) . ?
B1 C23 1.668(3) . ?
B1 H1 1.11(2) . ?
B2 O2 1.348(3) . ?
B2 O1 1.357(3) . ?
B2 C7 1.564(4) . ?
N1 C5 1.356(3) . ?
N1 C1 1.361(3) . ?
O1 C8 1.472(3) . ?
O2 C9 1.465(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.503(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 C6 1.498(4) . ?
C4 C5 1.358(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.512(4) . ?
C8 C11 1.518(4) . ?
C8 C9 1.561(4) . ?
C9 C12 1.511(4) . ?
C9 C13 1.517(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.418(3) . ?
C14 C19 1.429(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.517(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C17 C21 1.495(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C22 1.514(3) . ?
C20 F1 1.319(3) . ?
C20 F3 1.328(3) . ?
C20 F2 1.361(3) . ?
C21 F6 1.330(3) . ?
C21 F5 1.338(3) . ?
C21 F4 1.341(3) . ?
C22 F7 1.331(3) . ?
C22 F8 1.349(3) . ?
C22 F9 1.350(3) . ?
C23 C24 1.412(3) . ?
C23 C28 1.430(3) . ?
C24 C25 1.400(3) . ?
C24 C29 1.512(3) . ?
C25 C26 1.366(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.374(4) . ?
C26 C30 1.502(4) . ?
C27 C28 1.389(3) . ?
C27 H27 0.9500 . ?
C28 C31 1.514(3) . ?
C29 F11 1.337(3) . ?
C29 F12 1.338(3) . ?
C29 F10 1.343(3) . ?
C30 F13' 1.235(10) . ?
C30 F13 1.249(8) . ?
C30 F15 1.265(8) . ?
C30 F14' 1.287(9) . ?
C30 F15' 1.336(9) . ?
C30 F14 1.355(8) . ?
C31 F17 1.338(3) . ?
C31 F16 1.339(3) . ?
C31 F18 1.346(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
N1 B1 C14 115.31(17) . . ?
N1 B1 C23 109.94(17) . . ?
C14 B1 C23 117.77(18) . . ?
N1 B1 H1 103.4(11) . . ?
C14 B1 H1 104.2(10) . . ?
C23 B1 H1 104.3(10) . . ?
O2 B2 O1 114.2(2) . . ?
O2 B2 C7 120.7(2) . . ?
O1 B2 C7 125.0(2) . . ?
C5 N1 C1 117.78(18) . . ?
C5 N1 B1 120.11(18) . . ?
C1 N1 B1 121.76(17) . . ?
B2 O1 C8 106.68(19) . . ?
B2 O2 C9 107.49(19) . . ?
N1 C1 C2 119.8(2) . . ?
N1 C1 C7 121.2(2) . . ?
C2 C1 C7 119.0(2) . . ?
C3 C2 C1 122.5(2) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 116.3(2) . . ?
C2 C3 C6 122.1(2) . . ?
C4 C3 C6 121.6(2) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 123.5(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 B2 117.2(2) . . ?
C1 C7 H7A 108.0 . . ?
B2 C7 H7A 108.0 . . ?
C1 C7 H7B 108.0 . . ?
B2 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
O1 C8 C10 106.3(2) . . ?
O1 C8 C11 108.3(2) . . ?
C10 C8 C11 110.7(2) . . ?
O1 C8 C9 101.94(19) . . ?
C10 C8 C9 114.1(2) . . ?
C11 C8 C9 114.6(2) . . ?
O2 C9 C12 108.2(2) . . ?
O2 C9 C13 106.6(2) . . ?
C12 C9 C13 110.4(2) . . ?
O2 C9 C8 102.05(18) . . ?
C12 C9 C8 114.5(2) . . ?
C13 C9 C8 114.2(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 113.73(19) . . ?
C15 C14 B1 129.83(19) . . ?
C19 C14 B1 116.32(18) . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 C20 111.31(19) . . ?
C14 C15 C20 126.08(19) . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.0(2) . . ?
C16 C17 C21 121.2(2) . . ?
C18 C17 C21 119.8(2) . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 123.3(2) . . ?
C18 C19 C22 113.3(2) . . ?
C14 C19 C22 123.3(2) . . ?
F1 C20 F3 105.81(19) . . ?
F1 C20 F2 105.61(19) . . ?
F3 C20 F2 105.1(2) . . ?
F1 C20 C15 117.14(19) . . ?
F3 C20 C15 112.47(19) . . ?
F2 C20 C15 109.8(2) . . ?
F6 C21 F5 106.5(2) . . ?
F6 C21 F4 106.9(2) . . ?
F5 C21 F4 106.0(2) . . ?
F6 C21 C17 112.6(2) . . ?
F5 C21 C17 112.0(2) . . ?
F4 C21 C17 112.5(2) . . ?
F7 C22 F8 104.8(2) . . ?
F7 C22 F9 106.9(2) . . ?
F8 C22 F9 105.4(2) . . ?
F7 C22 C19 115.8(2) . . ?
F8 C22 C19 112.0(2) . . ?
F9 C22 C19 111.3(2) . . ?
C24 C23 C28 113.7(2) . . ?
C24 C23 B1 127.96(19) . . ?
C28 C23 B1 118.0(2) . . ?
C25 C24 C23 123.4(2) . . ?
C25 C24 C29 113.5(2) . . ?
C23 C24 C29 123.07(19) . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.6(2) . . ?
C25 C26 C30 120.6(2) . . ?
C27 C26 C30 119.7(2) . . ?
C26 C27 C28 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 122.4(2) . . ?
C27 C28 C31 114.1(2) . . ?
C23 C28 C31 123.4(2) . . ?
F11 C29 F12 106.15(19) . . ?
F11 C29 F10 106.73(18) . . ?
F12 C29 F10 105.56(18) . . ?
F11 C29 C24 112.05(18) . . ?
F12 C29 C24 112.28(19) . . ?
F10 C29 C24 113.52(19) . . ?
F13 C30 F15 110.1(8) . . ?
F13' C30 F14' 106.9(9) . . ?
F13' C30 F15' 106.5(8) . . ?
F14' C30 F15' 101.4(7) . . ?
F13 C30 F14 102.3(7) . . ?
F15 C30 F14 105.7(7) . . ?
F13' C30 C26 115.5(6) . . ?
F13 C30 C26 115.0(4) . . ?
F15 C30 C26 112.8(5) . . ?
F14' C30 C26 114.3(6) . . ?
F15' C30 C26 111.0(5) . . ?
F14 C30 C26 109.9(5) . . ?
F17 C31 F16 107.3(2) . . ?
F17 C31 F18 105.4(2) . . ?
F16 C31 F18 104.94(19) . . ?
F17 C31 C28 112.7(2) . . ?
F16 C31 C28 114.7(2) . . ?
F18 C31 C28 111.2(2) . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50320a
_database_code_depnum_ccdc_archive 'CCDC 1426310'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H12 B F18 N'
_chemical_formula_weight         679.17

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_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'
'-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                   25.046(3)
_cell_length_b                   11.9756(16)
_cell_length_c                   17.580(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.011(2)
_cell_angle_gamma                90
_cell_volume                     5192.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6108
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      26.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17796
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         27.134
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5663
_reflns_number_gt                4210
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1023P)²+2.2251P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5663
_refine_ls_number_parameters     435
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.16004(9) 0.4486(2) 0.14235(13) 0.0257(5) Uani 1 1 d . . . . .
N1 N 0.22600(7) 0.45689(15) 0.14684(10) 0.0285(4) Uani 1 1 d . . . . .
F1 F 0.05492(5) 0.51007(11) 0.08194(8) 0.0383(3) Uani 1 1 d . . . . .
F2 F -0.01296(5) 0.40176(12) 0.07677(9) 0.0427(4) Uani 1 1 d . . . . .
F3 F 0.02584(6) 0.46625(13) 0.18567(8) 0.0447(4) Uani 1 1 d . . . . .
F4 F 0.05484(7) -0.04031(15) 0.20101(12) 0.0684(5) Uani 1 1 d . . . . .
F5 F -0.01414(8) 0.03217(18) 0.1335(2) 0.1301(14) Uani 1 1 d . U . . .
F6 F 0.04434(12) -0.05361(18) 0.07950(15) 0.1043(9) Uani 1 1 d . . . . .
F7 F 0.22600(6) 0.25449(13) 0.06947(9) 0.0477(4) Uani 1 1 d . . . . .
F8 F 0.24729(6) 0.22973(12) 0.19194(9) 0.0425(4) Uani 1 1 d . . . . .
F9 F 0.22303(7) 0.09102(13) 0.11821(10) 0.0531(4) Uani 1 1 d . . . . .
F10 F 0.10793(6) 0.71538(12) 0.07515(8) 0.0438(4) Uani 1 1 d . . . . .
F11 F 0.14855(7) 0.82724(11) 0.16103(9) 0.0479(4) Uani 1 1 d . . . . .
F12 F 0.19297(6) 0.69422(12) 0.12119(8) 0.0420(4) Uani 1 1 d . . . . .
F13 F 0.0322(8) 0.7863(13) 0.3451(4) 0.121(5) Uani 0.60(2) 1 d . U P A 1
F14 F 0.0473(3) 0.6531(6) 0.4252(5) 0.065(2) Uani 0.60(2) 1 d . U P A 1
F15 F 0.1045(5) 0.7768(9) 0.4255(5) 0.083(3) Uani 0.60(2) 1 d D . P A 1
F13' F 0.0856(7) 0.8130(10) 0.3960(14) 0.091(5) Uani 0.40(2) 1 d D U P A 2
F14' F 0.0137(3) 0.7391(14) 0.3404(7) 0.082(3) Uani 0.40(2) 1 d D U P A 2
F15' F 0.0564(6) 0.6605(10) 0.4368(6) 0.076(4) Uani 0.40(2) 1 d D U P A 2
F16 F 0.17010(7) 0.37076(12) 0.39016(7) 0.0455(4) Uani 1 1 d . . . . .
F17 F 0.11583(6) 0.29217(11) 0.29838(8) 0.0435(4) Uani 1 1 d . . . . .
F18 F 0.19714(6) 0.33382(12) 0.28443(7) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.16030(9) 0.4886(2) 0.05132(12) 0.0303(5) Uani 1 1 d . . . . .
H1A H 0.1472 0.4310 0.0121 0.036 Uiso 1 1 calc R U . . .
H1B H 0.1427 0.5616 0.0375 0.036 Uiso 1 1 calc R U . . .
C2 C 0.22042(9) 0.49410(19) 0.07363(12) 0.0304(5) Uani 1 1 d . . . . .
C3 C 0.26419(9) 0.5304(2) 0.04236(14) 0.0362(5) Uani 1 1 d . . . . .
H3 H 0.2599 0.5543 -0.0099 0.043 Uiso 1 1 calc R U . . .
C4 C 0.31486(10) 0.5309(2) 0.08956(15) 0.0390(6) Uani 1 1 d . . . . .
C5 C 0.31912(10) 0.4940(2) 0.16582(15) 0.0402(6) Uani 1 1 d . . . . .
H5 H 0.3535 0.4940 0.1987 0.048 Uiso 1 1 calc R U . . .
C6 C 0.27423(9) 0.4578(2) 0.19393(14) 0.0350(5) Uani 1 1 d . . . . .
H6 H 0.2773 0.4338 0.2460 0.042 Uiso 1 1 calc R U . . .
C7 C 0.36397(11) 0.5713(3) 0.0588(2) 0.0554(7) Uani 1 1 d . . . . .
H7A H 0.3811 0.5081 0.0369 0.083 Uiso 1 1 calc R U . . .
H7B H 0.3899 0.6045 0.1009 0.083 Uiso 1 1 calc R U . . .
H7C H 0.3529 0.6274 0.0186 0.083 Uiso 1 1 calc R U . . .
C8 C 0.12924(9) 0.32576(17) 0.13708(11) 0.0259(4) Uani 1 1 d . . . . .
C9 C 0.07175(9) 0.32330(19) 0.12852(12) 0.0292(5) Uani 1 1 d . . . . .
C10 C 0.04256(10) 0.2247(2) 0.12796(14) 0.0374(5) Uani 1 1 d . . . . .
H10 H 0.0042 0.2274 0.1236 0.045 Uiso 1 1 calc R U . . .
C11 C 0.06843(10) 0.1235(2) 0.13369(16) 0.0420(6) Uani 1 1 d . . . . .
C12 C 0.12352(10) 0.1202(2) 0.13428(14) 0.0369(5) Uani 1 1 d . . . . .
H12 H 0.1414 0.0503 0.1341 0.044 Uiso 1 1 calc R U . . .
C13 C 0.15298(9) 0.21795(18) 0.13519(12) 0.0298(5) Uani 1 1 d . . . . .
C14 C 0.03580(9) 0.42580(19) 0.11853(13) 0.0313(5) Uani 1 1 d . . . . .
C15 C 0.03760(12) 0.0169(2) 0.1357(2) 0.0598(9) Uani 1 1 d . . . . .
C16 C 0.21210(10) 0.1996(2) 0.12942(14) 0.0366(5) Uani 1 1 d . . . . .
C17 C 0.14322(8) 0.52983(17) 0.21180(12) 0.0255(4) Uani 1 1 d . . . . .
C18 C 0.13102(9) 0.64587(18) 0.20441(12) 0.0291(5) Uani 1 1 d . . . . .
C19 C 0.10642(10) 0.70418(19) 0.25654(14) 0.0337(5) Uani 1 1 d . . . . .
H19 H 0.0976 0.7807 0.2475 0.040 Uiso 1 1 calc R U . . .
C20 C 0.09451(9) 0.65228(19) 0.32186(13) 0.0322(5) Uani 1 1 d . . . . .
C21 C 0.11101(9) 0.54417(18) 0.33711(12) 0.0294(5) Uani 1 1 d . . . . .
H21 H 0.1054 0.5091 0.3836 0.035 Uiso 1 1 calc R U . . .
C22 C 0.13610(9) 0.48555(18) 0.28394(12) 0.0267(4) Uani 1 1 d . . . . .
C23 C 0.14489(10) 0.71815(19) 0.14001(14) 0.0356(5) Uani 1 1 d . . . . .
C24 C 0.06605(12) 0.7160(2) 0.37676(16) 0.0464(7) Uani 1 1 d D . . . .
C25 C 0.15460(10) 0.37106(19) 0.31273(12) 0.0317(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.643(3) . ?
B1 C8 1.657(3) . ?
B1 C17 1.671(3) . ?
B1 C1 1.671(3) . ?
N1 C6 1.341(3) . ?
N1 C2 1.346(3) . ?
F1 C14 1.330(3) . ?
F2 C14 1.342(3) . ?
F3 C14 1.339(3) . ?
F4 C15 1.341(4) . ?
F5 C15 1.302(4) . ?
F6 C15 1.333(4) . ?
F7 C16 1.339(3) . ?
F8 C16 1.334(3) . ?
F9 C16 1.350(3) . ?
F10 C23 1.338(3) . ?
F11 C23 1.356(3) . ?
F12 C23 1.334(3) . ?
F13 C24 1.254(7) . ?
F14 C24 1.285(6) . ?
F15 C24 1.380(8) . ?
F13' C24 1.282(8) . ?
F14' C24 1.382(8) . ?
F15' C24 1.305(9) . ?
F16 C25 1.349(2) . ?
F17 C25 1.347(3) . ?
F18 C25 1.329(3) . ?
C1 C2 1.490(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.390(4) . ?
C4 C5 1.398(4) . ?
C4 C7 1.507(3) . ?
C5 C6 1.374(3) . ?
C8 C9 1.422(3) . ?
C8 C13 1.424(3) . ?
C9 C10 1.388(3) . ?
C9 C14 1.514(3) . ?
C10 C11 1.369(4) . ?
C11 C12 1.379(4) . ?
C11 C15 1.496(4) . ?
C12 C13 1.382(3) . ?
C13 C16 1.517(3) . ?
C17 C22 1.414(3) . ?
C17 C18 1.424(3) . ?
C18 C19 1.380(3) . ?
C18 C23 1.513(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.371(3) . ?
C20 C24 1.504(3) . ?
C21 C22 1.402(3) . ?
C22 C25 1.506(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
N1 B1 C8 120.70(17) . . ?
N1 B1 C17 108.01(16) . . ?
C8 B1 C17 112.56(16) . . ?
N1 B1 C1 81.81(14) . . ?
C8 B1 C1 106.25(17) . . ?
C17 B1 C1 125.21(18) . . ?
C6 N1 C2 121.35(19) . . ?
C6 N1 B1 145.16(18) . . ?
C2 N1 B1 92.15(16) . . ?
C2 C1 B1 86.13(16) . . ?
N1 C2 C3 121.8(2) . . ?
N1 C2 C1 99.75(17) . . ?
C3 C2 C1 138.2(2) . . ?
C2 C3 C4 118.0(2) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 C7 120.3(2) . . ?
C5 C4 C7 121.0(2) . . ?
C6 C5 C4 120.9(2) . . ?
N1 C6 C5 119.1(2) . . ?
C9 C8 C13 113.45(19) . . ?
C9 C8 B1 118.53(18) . . ?
C13 C8 B1 127.90(19) . . ?
C10 C9 C8 122.7(2) . . ?
C10 C9 C14 112.8(2) . . ?
C8 C9 C14 124.5(2) . . ?
C11 C10 C9 120.7(2) . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 C15 121.2(2) . . ?
C12 C11 C15 119.7(2) . . ?
C11 C12 C13 120.5(2) . . ?
C12 C13 C8 122.9(2) . . ?
C12 C13 C16 113.7(2) . . ?
C8 C13 C16 123.3(2) . . ?
F1 C14 F3 106.84(19) . . ?
F1 C14 F2 105.55(17) . . ?
F3 C14 F2 105.58(17) . . ?
F1 C14 C9 114.49(17) . . ?
F3 C14 C9 112.91(18) . . ?
F2 C14 C9 110.83(19) . . ?
F5 C15 F6 108.7(3) . . ?
F5 C15 F4 105.6(3) . . ?
F6 C15 F4 104.4(2) . . ?
F5 C15 C11 113.2(3) . . ?
F6 C15 C11 113.0(3) . . ?
F4 C15 C11 111.4(2) . . ?
F8 C16 F7 106.9(2) . . ?
F8 C16 F9 105.02(19) . . ?
F7 C16 F9 105.72(18) . . ?
F8 C16 C13 114.74(19) . . ?
F7 C16 C13 111.8(2) . . ?
F9 C16 C13 112.0(2) . . ?
C22 C17 C18 112.92(18) . . ?
C22 C17 B1 121.61(18) . . ?
C18 C17 B1 125.34(18) . . ?
C19 C18 C17 123.1(2) . . ?
C19 C18 C23 113.2(2) . . ?
C17 C18 C23 123.59(19) . . ?
C18 C19 C20 120.6(2) . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 C24 120.9(2) . . ?
C19 C20 C24 120.0(2) . . ?
C20 C21 C22 119.8(2) . . ?
C21 C22 C17 123.4(2) . . ?
C21 C22 C25 112.27(18) . . ?
C17 C22 C25 124.29(18) . . ?
F12 C23 F10 107.7(2) . . ?
F12 C23 F11 104.68(18) . . ?
F10 C23 F11 105.07(18) . . ?
F12 C23 C18 113.41(19) . . ?
F10 C23 C18 114.11(19) . . ?
F11 C23 C18 111.14(19) . . ?
F13 C24 F14 113.1(8) . . ?
F13' C24 F15' 111.3(9) . . ?
F13 C24 F15 105.4(6) . . ?
F14 C24 F15 101.2(5) . . ?
F13' C24 F14' 103.2(8) . . ?
F15' C24 F14' 100.5(7) . . ?
F13 C24 C20 114.5(4) . . ?
F13' C24 C20 115.3(5) . . ?
F14 C24 C20 113.3(4) . . ?
F15' C24 C20 115.8(5) . . ?
F15 C24 C20 108.0(5) . . ?
F14' C24 C20 108.8(5) . . ?
F18 C25 F17 107.06(18) . . ?
F18 C25 F16 105.56(18) . . ?
F17 C25 F16 105.00(17) . . ?
F18 C25 C22 113.54(18) . . ?
F17 C25 C22 113.94(19) . . ?
F16 C25 C22 111.05(17) . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50504b
_database_code_depnum_ccdc_archive 'CCDC 1426311'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H12 B F18 N'
_chemical_formula_weight         679.17

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.439(3)
_cell_length_b                   9.2610(16)
_cell_length_c                   16.952(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.127(3)
_cell_angle_gamma                90
_cell_volume                     2554.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8588
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.35

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17723
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         27.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5761
_reflns_number_gt                4740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0787P)²+1.0372P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5761
_refine_ls_number_parameters     454
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.47669(11) 0.37141(19) 0.17638(10) 0.0211(3) Uani 1 1 d . . . . .
N1 N 0.50926(8) 0.20288(15) 0.19292(8) 0.0226(3) Uani 1 1 d . . . . .
F1 F 0.64388(6) 0.35909(12) 0.28133(7) 0.0360(3) Uani 1 1 d . . . . .
F2 F 0.65151(7) 0.58465(13) 0.24890(7) 0.0405(3) Uani 1 1 d . . . . .
F3 F 0.67755(7) 0.51818(15) 0.37090(7) 0.0460(3) Uani 1 1 d . . . . .
F4 F 0.38835(10) 0.67150(17) 0.51256(8) 0.0614(4) Uani 1 1 d . . . . .
F7 F 0.31789(6) 0.28359(12) 0.21705(7) 0.0367(3) Uani 1 1 d . . . . .
F8 F 0.26727(8) 0.37264(18) 0.31494(9) 0.0624(4) Uani 1 1 d . . . . .
F9 F 0.26574(7) 0.49655(16) 0.20793(10) 0.0557(4) Uani 1 1 d . . . . .
F10 F 0.50722(7) 0.65802(11) 0.14617(7) 0.0385(3) Uani 1 1 d . . . . .
F11 F 0.42240(9) 0.79543(12) 0.07474(8) 0.0496(3) Uani 1 1 d . . . . .
F12 F 0.39865(8) 0.73135(13) 0.19054(8) 0.0472(3) Uani 1 1 d . . . . .
F5 F 0.5139(3) 0.7137(9) 0.5269(2) 0.0646(16) Uani 0.61(2) 1 d . U P A 1
F6 F 0.4349(10) 0.8520(4) 0.4531(3) 0.080(3) Uani 0.61(2) 1 d . U P A 1
F13 F 0.2246(6) 0.6152(11) -0.1333(5) 0.092(3) Uani 0.590(13) 1 d . U P B 1
F14 F 0.1512(3) 0.4399(6) -0.1045(4) 0.075(2) Uani 0.590(13) 1 d . U P B 1
F15 F 0.1478(4) 0.6297(8) -0.0427(5) 0.118(3) Uani 0.590(13) 1 d . U P B 1
F5' F 0.4992(6) 0.792(3) 0.4988(13) 0.107(8) Uani 0.39(2) 1 d . U P A 2
F6' F 0.3850(11) 0.8458(8) 0.4344(7) 0.068(3) Uani 0.39(2) 1 d . U P A 2
F13' F 0.1850(12) 0.4317(11) -0.1364(9) 0.166(6) Uani 0.410(13) 1 d D U P B 2
F14' F 0.1339(4) 0.565(2) -0.0576(7) 0.134(6) Uani 0.410(13) 1 d D U P B 2
F15' F 0.2133(8) 0.6483(13) -0.1204(9) 0.100(5) Uani 0.410(13) 1 d D U P B 2
F16 F 0.35962(7) 0.08406(11) 0.12676(7) 0.0343(3) Uani 1 1 d . . . . .
F17 F 0.31109(8) 0.07392(13) 0.00376(8) 0.0458(3) Uani 1 1 d . . . . .
F18 F 0.43976(7) 0.11196(12) 0.03777(7) 0.0379(3) Uani 1 1 d . . . . .
C1 C 0.56943(10) 0.22217(18) 0.14710(10) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.62403(11) 0.1128(2) 0.13560(12) 0.0337(4) Uani 1 1 d . . . . .
H2 H 0.6650 0.1255 0.1018 0.040 Uiso 1 1 calc R U . . .
C3 C 0.61623(12) -0.0158(2) 0.17556(13) 0.0382(4) Uani 1 1 d . . . . .
H3 H 0.6512 -0.0948 0.1681 0.046 Uiso 1 1 calc R U . . .
C4 C 0.55796(12) -0.02968(19) 0.22613(11) 0.0340(4) Uani 1 1 d . . . . .
H4 H 0.5547 -0.1175 0.2545 0.041 Uiso 1 1 calc R U . . .
C5 C 0.50383(10) 0.08183(18) 0.23653(10) 0.0272(3) Uani 1 1 d . . . . .
C6 C 0.55712(10) 0.37703(18) 0.12555(10) 0.0253(3) Uani 1 1 d . . . . .
H6A H 0.5423 0.3950 0.0677 0.030 Uiso 1 1 calc R U . . .
H6B H 0.6023 0.4412 0.1492 0.030 Uiso 1 1 calc R U . . .
C7 C 0.44500(13) 0.0722(2) 0.29555(12) 0.0377(4) Uani 1 1 d . . . . .
H7A H 0.4420 0.1658 0.3220 0.057 Uiso 1 1 calc R U . . .
H7B H 0.4638 -0.0016 0.3354 0.057 Uiso 1 1 calc R U . . .
H7C H 0.3905 0.0461 0.2681 0.057 Uiso 1 1 calc R U . . .
C8 C 0.46998(10) 0.45207(17) 0.26297(9) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.53760(10) 0.51445(18) 0.31332(10) 0.0258(3) Uani 1 1 d . . . . .
C10 C 0.52832(12) 0.6014(2) 0.37869(11) 0.0329(4) Uani 1 1 d . . . . .
H10 H 0.5754 0.6440 0.4088 0.039 Uiso 1 1 calc R U . . .
C11 C 0.45219(13) 0.6262(2) 0.39992(11) 0.0368(4) Uani 1 1 d . . . . .
C12 C 0.38500(12) 0.5586(2) 0.35777(12) 0.0370(4) Uani 1 1 d . . . . .
H12 H 0.3322 0.5713 0.3735 0.044 Uiso 1 1 calc R U . . .
C13 C 0.39370(10) 0.47196(19) 0.29246(11) 0.0285(4) Uani 1 1 d . . . . .
C14 C 0.62679(11) 0.4935(2) 0.30253(11) 0.0312(4) Uani 1 1 d . . . . .
C15 C 0.44147(17) 0.7221(3) 0.46878(14) 0.0537(6) Uani 1 1 d . . . . .
C16 C 0.31204(11) 0.4057(2) 0.25736(13) 0.0368(4) Uani 1 1 d . . . . .
C17 C 0.39813(9) 0.40663(17) 0.10590(9) 0.0228(3) Uani 1 1 d . . . . .
C18 C 0.37949(10) 0.55410(18) 0.08695(10) 0.0271(3) Uani 1 1 d . . . . .
C19 C 0.31441(11) 0.5962(2) 0.02968(12) 0.0337(4) Uani 1 1 d . . . . .
H19 H 0.3020 0.6958 0.0218 0.040 Uiso 1 1 calc R U . . .
C20 C 0.26805(11) 0.4940(2) -0.01549(12) 0.0353(4) Uani 1 1 d . . . . .
C21 C 0.28781(11) 0.3499(2) -0.00478(11) 0.0318(4) Uani 1 1 d . . . . .
H21 H 0.2583 0.2794 -0.0380 0.038 Uiso 1 1 calc R U . . .
C22 C 0.35060(10) 0.30703(19) 0.05433(10) 0.0257(3) Uani 1 1 d . . . . .
C23 C 0.42728(12) 0.68287(19) 0.12515(12) 0.0326(4) Uani 1 1 d . . . . .
C24 C 0.19973(14) 0.5395(3) -0.07864(16) 0.0534(6) Uani 1 1 d D . . . .
C25 C 0.36566(11) 0.1453(2) 0.05675(10) 0.0295(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
B1 N1 1.661(2) . ?
B1 C17 1.663(2) . ?
B1 C8 1.664(2) . ?
B1 C6 1.678(2) . ?
N1 C5 1.353(2) . ?
N1 C1 1.353(2) . ?
F1 C14 1.336(2) . ?
F2 C14 1.345(2) . ?
F3 C14 1.349(2) . ?
F4 C15 1.310(3) . ?
F7 C16 1.332(2) . ?
F8 C16 1.338(2) . ?
F9 C16 1.345(3) . ?
F10 C23 1.332(2) . ?
F11 C23 1.343(2) . ?
F12 C23 1.341(2) . ?
F5 C15 1.437(6) . ?
F6 C15 1.234(5) . ?
F13 C24 1.274(6) . ?
F14 C24 1.257(5) . ?
F15 C24 1.395(7) . ?
F5' C15 1.202(7) . ?
F6' C15 1.537(13) . ?
F13' C24 1.394(8) . ?
F14' C24 1.211(8) . ?
F15' C24 1.270(9) . ?
F16 C25 1.332(2) . ?
F17 C25 1.3495(19) . ?
F18 C25 1.339(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.487(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.391(3) . ?
C5 C7 1.489(3) . ?
C8 C9 1.425(2) . ?
C8 C13 1.426(2) . ?
C9 C10 1.396(2) . ?
C9 C14 1.515(2) . ?
C10 C11 1.370(3) . ?
C11 C12 1.378(3) . ?
C11 C15 1.497(3) . ?
C12 C13 1.391(3) . ?
C13 C16 1.519(2) . ?
C17 C22 1.426(2) . ?
C17 C18 1.426(2) . ?
C18 C19 1.395(2) . ?
C18 C23 1.521(3) . ?
C19 C20 1.378(3) . ?
C20 C21 1.379(3) . ?
C20 C24 1.498(3) . ?
C21 C22 1.391(2) . ?
C22 C25 1.518(2) . ?

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
N1 B1 C17 120.31(12) . . ?
N1 B1 C8 109.44(12) . . ?
C17 B1 C8 113.83(13) . . ?
N1 B1 C6 81.79(11) . . ?
C17 B1 C6 102.31(12) . . ?
C8 B1 C6 126.46(13) . . ?
C5 N1 C1 122.22(14) . . ?
C5 N1 B1 145.73(14) . . ?
C1 N1 B1 91.34(12) . . ?
N1 C1 C2 121.67(17) . . ?
N1 C1 C6 100.56(13) . . ?
C2 C1 C6 137.65(17) . . ?
C1 C2 C3 116.95(18) . . ?
C4 C3 C2 120.31(17) . . ?
C3 C4 C5 121.52(17) . . ?
N1 C5 C4 116.96(17) . . ?
N1 C5 C7 121.06(16) . . ?
C4 C5 C7 121.92(17) . . ?
C1 C6 B1 86.19(12) . . ?
C9 C8 C13 112.82(14) . . ?
C9 C8 B1 124.53(13) . . ?
C13 C8 B1 122.57(14) . . ?
C10 C9 C8 123.10(15) . . ?
C10 C9 C14 112.71(15) . . ?
C8 C9 C14 124.19(15) . . ?
C11 C10 C9 120.78(17) . . ?
C10 C11 C12 118.88(17) . . ?
C10 C11 C15 121.12(19) . . ?
C12 C11 C15 119.98(19) . . ?
C11 C12 C13 120.64(17) . . ?
C12 C13 C8 123.23(16) . . ?
C12 C13 C16 111.12(15) . . ?
C8 C13 C16 125.64(15) . . ?
F1 C14 F2 107.93(15) . . ?
F1 C14 F3 105.13(15) . . ?
F2 C14 F3 105.36(14) . . ?
F1 C14 C9 113.32(14) . . ?
F2 C14 C9 113.02(15) . . ?
F3 C14 C9 111.48(15) . . ?
F5' C15 F4 120.2(10) . . ?
F6 C15 F4 115.2(6) . . ?
F6 C15 F5 103.8(5) . . ?
F4 C15 F5 98.4(3) . . ?
F5' C15 C11 118.5(4) . . ?
F6 C15 C11 115.3(3) . . ?
F4 C15 C11 113.02(19) . . ?
F5 C15 C11 109.0(3) . . ?
F5' C15 F6' 99.0(9) . . ?
F4 C15 F6' 93.8(4) . . ?
C11 C15 F6' 106.1(5) . . ?
F7 C16 F8 105.49(16) . . ?
F7 C16 F9 106.68(16) . . ?
F8 C16 F9 106.04(16) . . ?
F7 C16 C13 114.85(15) . . ?
F8 C16 C13 110.70(17) . . ?
F9 C16 C13 112.47(17) . . ?
C22 C17 C18 113.56(15) . . ?
C22 C17 B1 128.05(14) . . ?
C18 C17 B1 118.03(14) . . ?
C19 C18 C17 122.93(16) . . ?
C19 C18 C23 112.11(15) . . ?
C17 C18 C23 124.96(15) . . ?
C20 C19 C18 120.29(17) . . ?
C19 C20 C21 119.35(16) . . ?
C19 C20 C24 120.23(19) . . ?
C21 C20 C24 120.34(19) . . ?
C20 C21 C22 120.53(17) . . ?
C21 C22 C17 122.93(16) . . ?
C21 C22 C25 113.76(15) . . ?
C17 C22 C25 123.28(15) . . ?
F10 C23 F12 106.55(16) . . ?
F10 C23 F11 105.80(15) . . ?
F12 C23 F11 105.64(15) . . ?
F10 C23 C18 114.14(14) . . ?
F12 C23 C18 113.18(16) . . ?
F11 C23 C18 110.90(15) . . ?
F14' C24 F15' 104.1(8) . . ?
F14 C24 F13 113.8(5) . . ?
F14 C24 F15 101.2(4) . . ?
F13 C24 F15 105.5(6) . . ?
F14' C24 F13' 105.9(8) . . ?
F15' C24 F13' 101.7(9) . . ?
F14' C24 C20 117.1(5) . . ?
F14 C24 C20 114.7(3) . . ?
F15' C24 C20 116.7(6) . . ?
F13 C24 C20 112.9(4) . . ?
F15 C24 C20 107.4(3) . . ?
F13' C24 C20 109.8(4) . . ?
F16 C25 F18 107.51(14) . . ?
F16 C25 F17 104.96(15) . . ?
F18 C25 F17 105.59(14) . . ?
F16 C25 C22 114.33(14) . . ?
F18 C25 C22 111.81(15) . . ?
F17 C25 C22 112.02(14) . . ?

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
C17 B1 N1 C5 -94.0(2) . . . . ?
C8 B1 N1 C5 40.7(3) . . . . ?
C6 B1 N1 C5 166.5(2) . . . . ?
C17 B1 N1 C1 97.07(15) . . . . ?
C8 B1 N1 C1 -128.30(13) . . . . ?
C6 B1 N1 C1 -2.44(11) . . . . ?
C5 N1 C1 C2 6.9(2) . . . . ?
B1 N1 C1 C2 179.54(16) . . . . ?
C5 N1 C1 C6 -169.91(14) . . . . ?
B1 N1 C1 C6 2.77(13) . . . . ?
N1 C1 C2 C3 -2.3(3) . . . . ?
C6 C1 C2 C3 172.95(19) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C1 N1 C5 C4 -6.5(2) . . . . ?
B1 N1 C5 C4 -173.41(19) . . . . ?
C1 N1 C5 C7 170.77(16) . . . . ?
B1 N1 C5 C7 3.8(3) . . . . ?
C3 C4 C5 N1 2.0(3) . . . . ?
C3 C4 C5 C7 -175.24(17) . . . . ?
N1 C1 C6 B1 -2.75(13) . . . . ?
C2 C1 C6 B1 -178.7(2) . . . . ?
N1 B1 C6 C1 2.22(10) . . . . ?
C17 B1 C6 C1 -117.15(13) . . . . ?
C8 B1 C6 C1 110.37(16) . . . . ?
N1 B1 C8 C9 81.53(18) . . . . ?
C17 B1 C8 C9 -140.66(16) . . . . ?
C6 B1 C8 C9 -12.6(2) . . . . ?
N1 B1 C8 C13 -101.72(17) . . . . ?
C17 B1 C8 C13 36.1(2) . . . . ?
C6 B1 C8 C13 164.12(16) . . . . ?
C13 C8 C9 C10 -7.8(2) . . . . ?
B1 C8 C9 C10 169.22(16) . . . . ?
C13 C8 C9 C14 171.78(16) . . . . ?
B1 C8 C9 C14 -11.2(3) . . . . ?
C8 C9 C10 C11 2.9(3) . . . . ?
C14 C9 C10 C11 -176.71(18) . . . . ?
C9 C10 C11 C12 2.8(3) . . . . ?
C9 C10 C11 C15 -178.6(2) . . . . ?
C10 C11 C12 C13 -2.9(3) . . . . ?
C15 C11 C12 C13 178.5(2) . . . . ?
C11 C12 C13 C8 -2.7(3) . . . . ?
C11 C12 C13 C16 178.25(19) . . . . ?
C9 C8 C13 C12 7.7(3) . . . . ?
B1 C8 C13 C12 -169.38(17) . . . . ?
C9 C8 C13 C16 -173.40(18) . . . . ?
B1 C8 C13 C16 9.5(3) . . . . ?
C10 C9 C14 F1 140.01(16) . . . . ?
C8 C9 C14 F1 -39.6(2) . . . . ?
C10 C9 C14 F2 -96.81(18) . . . . ?
C8 C9 C14 F2 83.6(2) . . . . ?
C10 C9 C14 F3 21.6(2) . . . . ?
C8 C9 C14 F3 -157.98(16) . . . . ?
C10 C11 C15 F5' 9.6(18) . . . . ?
C12 C11 C15 F5' -171.8(18) . . . . ?
C10 C11 C15 F6 85.6(9) . . . . ?
C12 C11 C15 F6 -95.8(9) . . . . ?
C10 C11 C15 F4 -138.9(2) . . . . ?
C12 C11 C15 F4 39.7(3) . . . . ?
C10 C11 C15 F5 -30.6(4) . . . . ?
C12 C11 C15 F5 148.0(3) . . . . ?
C10 C11 C15 F6' 119.7(6) . . . . ?
C12 C11 C15 F6' -61.8(6) . . . . ?
C12 C13 C16 F7 -155.44(18) . . . . ?
C8 C13 C16 F7 25.5(3) . . . . ?
C12 C13 C16 F8 -36.1(2) . . . . ?
C8 C13 C16 F8 144.86(18) . . . . ?
C12 C13 C16 F9 82.3(2) . . . . ?
C8 C13 C16 F9 -96.7(2) . . . . ?
N1 B1 C17 C22 0.7(2) . . . . ?
C8 B1 C17 C22 -132.12(16) . . . . ?
C6 B1 C17 C22 88.30(18) . . . . ?
N1 B1 C17 C18 -171.91(14) . . . . ?
C8 B1 C17 C18 55.28(19) . . . . ?
C6 B1 C17 C18 -84.30(16) . . . . ?
C22 C17 C18 C19 7.2(2) . . . . ?
B1 C17 C18 C19 -179.13(16) . . . . ?
C22 C17 C18 C23 -172.24(16) . . . . ?
B1 C17 C18 C23 1.4(2) . . . . ?
C17 C18 C19 C20 -4.5(3) . . . . ?
C23 C18 C19 C20 175.06(17) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C18 C19 C20 C24 -178.2(2) . . . . ?
C19 C20 C21 C22 4.0(3) . . . . ?
C24 C20 C21 C22 -179.30(19) . . . . ?
C20 C21 C22 C17 -0.7(3) . . . . ?
C20 C21 C22 C25 -178.64(17) . . . . ?
C18 C17 C22 C21 -4.7(2) . . . . ?
B1 C17 C22 C21 -177.54(16) . . . . ?
C18 C17 C22 C25 173.07(16) . . . . ?
B1 C17 C22 C25 0.2(3) . . . . ?
C19 C18 C23 F10 -147.27(17) . . . . ?
C17 C18 C23 F10 32.2(3) . . . . ?
C19 C18 C23 F12 90.62(19) . . . . ?
C17 C18 C23 F12 -89.9(2) . . . . ?
C19 C18 C23 F11 -27.9(2) . . . . ?
C17 C18 C23 F11 151.62(16) . . . . ?
C19 C20 C24 F14' -83.9(11) . . . . ?
C21 C20 C24 F14' 99.4(11) . . . . ?
C19 C20 C24 F14 -165.9(5) . . . . ?
C21 C20 C24 F14 17.4(5) . . . . ?
C19 C20 C24 F15' 40.4(10) . . . . ?
C21 C20 C24 F15' -136.3(9) . . . . ?
C19 C20 C24 F13 61.6(7) . . . . ?
C21 C20 C24 F13 -115.1(6) . . . . ?
C19 C20 C24 F15 -54.3(5) . . . . ?
C21 C20 C24 F15 129.0(5) . . . . ?
C19 C20 C24 F13' 155.3(11) . . . . ?
C21 C20 C24 F13' -21.4(11) . . . . ?
C21 C22 C25 F16 -123.18(16) . . . . ?
C17 C22 C25 F16 58.9(2) . . . . ?
C21 C22 C25 F18 114.37(17) . . . . ?
C17 C22 C25 F18 -63.6(2) . . . . ?
C21 C22 C25 F17 -3.9(2) . . . . ?
C17 C22 C25 F17 178.14(16) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50515b
_database_code_depnum_ccdc_archive 'CCDC 1426313'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H14 B F18 N'
_chemical_formula_weight         681.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7459(12)
_cell_length_b                   15.848(2)
_cell_length_c                   19.209(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.085(2)
_cell_angle_gamma                90
_cell_volume                     2662.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6028
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18864
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.666
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6067
_reflns_number_gt                4662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0608P)²+1.1036P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6067
_refine_ls_number_parameters     468
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.004
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.06585(15) 0.40554(9) 0.19569(7) 0.0223(3) Uani 1 1 d . . . . .
B1 B 0.0997(2) 0.49969(11) 0.22458(9) 0.0213(4) Uani 1 1 d . . . . .
H1 H -0.013(2) 0.5288(11) 0.2215(9) 0.017(4) Uiso 1 1 d . . . . .
F1 F 0.08949(13) 0.67589(6) 0.24467(5) 0.0350(3) Uani 1 1 d . . . . .
F2 F -0.11993(12) 0.63856(8) 0.29336(6) 0.0400(3) Uani 1 1 d . . . . .
F3 F 0.03205(14) 0.72619(7) 0.34363(6) 0.0425(3) Uani 1 1 d . . . . .
F7 F 0.31190(16) 0.34776(8) 0.26934(7) 0.0521(3) Uani 1 1 d . . . . .
F8 F 0.3450(2) 0.31688(9) 0.37604(8) 0.0773(6) Uani 1 1 d . . . . .
F9 F 0.1230(2) 0.30634(8) 0.32869(8) 0.0651(4) Uani 1 1 d . . . . .
F10 F -0.12063(12) 0.62321(8) 0.13179(6) 0.0413(3) Uani 1 1 d . . . . .
F11 F -0.08912(13) 0.58874(9) 0.02564(6) 0.0451(3) Uani 1 1 d . . . . .
F12 F -0.10794(12) 0.49262(7) 0.10227(6) 0.0366(3) Uani 1 1 d . . . . .
F4 F 0.1800(6) 0.4944(4) 0.5694(2) 0.081(2) Uani 0.602(14) 1 d D U P A 1
F5 F 0.3914(5) 0.5373(5) 0.5436(2) 0.0705(14) Uani 0.602(14) 1 d D U P A 1
F6 F 0.2147(16) 0.6258(3) 0.5499(3) 0.112(4) Uani 0.602(14) 1 d D U P A 1
F13 F 0.421(2) 0.6153(10) -0.0672(5) 0.158(6) Uani 0.477(12) 1 d . U P B 1
F14 F 0.3847(9) 0.7350(6) -0.0269(6) 0.120(4) Uani 0.477(12) 1 d . U P B 1
F15 F 0.5778(6) 0.6735(9) -0.0015(4) 0.099(4) Uani 0.477(12) 1 d D U P B 1
F13' F 0.3656(6) 0.6500(7) -0.0692(3) 0.092(3) Uani 0.523(12) 1 d D U P B 2
F14' F 0.488(2) 0.7291(6) -0.0033(3) 0.159(6) Uani 0.523(12) 1 d D U P B 2
F15' F 0.5686(8) 0.6086(9) -0.0232(4) 0.117(3) Uani 0.523(12) 1 d D U P B 2
F4' F 0.2215(17) 0.4860(4) 0.5688(4) 0.105(4) Uani 0.398(14) 1 d D U P A 2
F5' F 0.3578(13) 0.5910(12) 0.5426(4) 0.109(5) Uani 0.398(14) 1 d D U P A 2
F6' F 0.1206(9) 0.5994(7) 0.5555(3) 0.072(2) Uani 0.398(14) 1 d D U P A 2
F16 F 0.40790(15) 0.60795(11) 0.28392(7) 0.0601(4) Uani 1 1 d . . . . .
F17 F 0.46245(15) 0.48127(11) 0.25565(8) 0.0633(4) Uani 1 1 d . . . . .
F18 F 0.60278(13) 0.58269(12) 0.22192(7) 0.0666(5) Uani 1 1 d . . . . .
C1 C -0.06564(19) 0.36518(11) 0.21108(9) 0.0271(4) Uani 1 1 d . . . . .
C2 C -0.1070(2) 0.29231(12) 0.17545(10) 0.0322(4) Uani 1 1 d . . . . .
H2 H -0.1990 0.2644 0.1873 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0185(2) 0.25908(12) 0.12330(9) 0.0318(4) Uani 1 1 d . . . . .
C4 C 0.1185(2) 0.29975(11) 0.11054(9) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.1856 0.2782 0.0765 0.037 Uiso 1 1 calc R U . . .
C5 C 0.15688(19) 0.37095(11) 0.14701(9) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.2518 0.3974 0.1378 0.031 Uiso 1 1 calc R U . . .
C6 C -0.1689(2) 0.40080(13) 0.26515(11) 0.0402(5) Uani 1 1 d . . . . .
H6A H -0.1091 0.4136 0.3075 0.060 Uiso 1 1 calc R U . . .
H6B H -0.2484 0.3595 0.2759 0.060 Uiso 1 1 calc R U . . .
H6C H -0.2168 0.4526 0.2474 0.060 Uiso 1 1 calc R U . . .
C7 C -0.0682(3) 0.18294(14) 0.08210(12) 0.0469(5) Uani 1 1 d . . . . .
H7A H -0.1663 0.1625 0.0993 0.070 Uiso 1 1 calc R U . . .
H7B H 0.0089 0.1384 0.0872 0.070 Uiso 1 1 calc R U . . .
H7C H -0.0797 0.1982 0.0328 0.070 Uiso 1 1 calc R U . . .
C8 C 0.14686(17) 0.50601(10) 0.30823(8) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.10946(18) 0.58261(11) 0.34258(8) 0.0242(3) Uani 1 1 d . . . . .
C10 C 0.1381(2) 0.59701(12) 0.41281(9) 0.0289(4) Uani 1 1 d . . . . .
H10 H 0.1116 0.6496 0.4329 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2051(2) 0.53517(12) 0.45345(9) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.2399(2) 0.45859(12) 0.42397(9) 0.0336(4) Uani 1 1 d . . . . .
H12 H 0.2838 0.4152 0.4520 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2115(2) 0.44413(11) 0.35327(9) 0.0283(4) Uani 1 1 d . . . . .
C14 C 0.0293(2) 0.65472(11) 0.30531(9) 0.0293(4) Uani 1 1 d . . . . .
C15 C 0.2388(3) 0.55093(15) 0.52917(10) 0.0462(5) Uani 1 1 d D . . . .
C16 C 0.2487(3) 0.35468(13) 0.33103(11) 0.0433(5) Uani 1 1 d . . . . .
C17 C 0.20230(18) 0.54892(10) 0.16482(8) 0.0216(3) Uani 1 1 d . . . . .
C18 C 0.12579(19) 0.57320(11) 0.10178(8) 0.0248(3) Uani 1 1 d . . . . .
C19 C 0.2018(2) 0.60729(12) 0.04551(9) 0.0321(4) Uani 1 1 d . . . . .
H19 H 0.1463 0.6215 0.0041 0.038 Uiso 1 1 calc R U . . .
C20 C 0.3574(2) 0.62055(13) 0.04954(10) 0.0356(4) Uani 1 1 d . . . . .
C21 C 0.4359(2) 0.60389(12) 0.11070(10) 0.0316(4) Uani 1 1 d . . . . .
H21 H 0.5422 0.6158 0.1146 0.038 Uiso 1 1 calc R U . . .
C22 C 0.35939(19) 0.56953(11) 0.16679(9) 0.0259(3) Uani 1 1 d . . . . .
C23 C -0.0468(2) 0.56889(12) 0.09148(9) 0.0305(4) Uani 1 1 d . . . . .
C24 C 0.4396(3) 0.6562(2) -0.01166(13) 0.0591(7) Uani 1 1 d D . . . .
C25 C 0.4571(2) 0.55950(15) 0.23160(11) 0.0414(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.353(2) . ?
N1 C5 1.355(2) . ?
N1 B1 1.617(2) . ?
B1 C8 1.655(2) . ?
B1 C17 1.665(2) . ?
B1 H1 1.085(17) . ?
F1 C14 1.331(2) . ?
F2 C14 1.345(2) . ?
F3 C14 1.351(2) . ?
F7 C16 1.322(3) . ?
F8 C16 1.337(2) . ?
F9 C16 1.340(3) . ?
F10 C23 1.333(2) . ?
F11 C23 1.348(2) . ?
F12 C23 1.339(2) . ?
F4 C15 1.296(5) . ?
F5 C15 1.375(5) . ?
F6 C15 1.270(4) . ?
F13 C24 1.256(9) . ?
F14 C24 1.368(7) . ?
F15 C24 1.251(5) . ?
F13' C24 1.273(5) . ?
F14' C24 1.240(6) . ?
F15' C24 1.378(6) . ?
F4' C15 1.290(7) . ?
F5' C15 1.242(6) . ?
F6' C15 1.391(6) . ?
F16 C25 1.342(3) . ?
F17 C25 1.324(3) . ?
F18 C25 1.343(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.500(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 C7 1.503(3) . ?
C4 C5 1.367(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.418(2) . ?
C8 C9 1.423(2) . ?
C9 C10 1.386(2) . ?
C9 C14 1.514(2) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C11 C15 1.500(3) . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C16 1.518(3) . ?
C17 C22 1.412(2) . ?
C17 C18 1.425(2) . ?
C18 C19 1.389(2) . ?
C18 C23 1.520(2) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(3) . ?
C20 C24 1.500(3) . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C25 1.505(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
C1 N1 C5 118.18(15) . . ?
C1 N1 B1 120.78(13) . . ?
C5 N1 B1 120.26(13) . . ?
N1 B1 C8 115.44(13) . . ?
N1 B1 C17 107.06(12) . . ?
C8 B1 C17 120.90(13) . . ?
N1 B1 H1 102.3(9) . . ?
C8 B1 H1 103.7(9) . . ?
C17 B1 H1 105.2(9) . . ?
N1 C1 C2 120.03(16) . . ?
N1 C1 C6 119.92(16) . . ?
C2 C1 C6 120.03(16) . . ?
C3 C2 C1 122.05(16) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 116.68(16) . . ?
C2 C3 C7 121.83(18) . . ?
C4 C3 C7 121.50(18) . . ?
C5 C4 C3 119.84(17) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 123.09(16) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 113.55(14) . . ?
C13 C8 B1 129.78(15) . . ?
C9 C8 B1 116.53(14) . . ?
C10 C9 C8 123.55(16) . . ?
C10 C9 C14 114.18(15) . . ?
C8 C9 C14 122.24(14) . . ?
C11 C10 C9 120.12(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.32(16) . . ?
C12 C11 C15 120.33(18) . . ?
C10 C11 C15 120.35(18) . . ?
C11 C12 C13 120.58(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 122.82(16) . . ?
C12 C13 C16 113.09(16) . . ?
C8 C13 C16 124.02(16) . . ?
F1 C14 F2 107.30(14) . . ?
F1 C14 F3 105.20(14) . . ?
F2 C14 F3 105.08(14) . . ?
F1 C14 C9 114.63(14) . . ?
F2 C14 C9 112.10(15) . . ?
F3 C14 C9 111.84(14) . . ?
F5' C15 F4' 113.1(7) . . ?
F6 C15 F4 112.9(5) . . ?
F6 C15 F5 104.5(4) . . ?
F4 C15 F5 99.6(3) . . ?
F5' C15 F6' 105.5(6) . . ?
F4' C15 F6' 97.4(5) . . ?
F5' C15 C11 115.8(4) . . ?
F6 C15 C11 115.4(2) . . ?
F4' C15 C11 114.6(4) . . ?
F4 C15 C11 112.9(3) . . ?
F5 C15 C11 110.0(3) . . ?
F6' C15 C11 108.1(3) . . ?
F7 C16 F8 105.89(18) . . ?
F7 C16 F9 106.20(18) . . ?
F8 C16 F9 105.78(18) . . ?
F7 C16 C13 115.18(17) . . ?
F8 C16 C13 111.87(17) . . ?
F9 C16 C13 111.28(18) . . ?
C22 C17 C18 113.65(14) . . ?
C22 C17 B1 128.83(14) . . ?
C18 C17 B1 117.51(13) . . ?
C19 C18 C17 122.85(15) . . ?
C19 C18 C23 113.87(15) . . ?
C17 C18 C23 123.19(14) . . ?
C20 C19 C18 120.14(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.71(16) . . ?
C21 C20 C24 120.19(18) . . ?
C19 C20 C24 120.06(18) . . ?
C20 C21 C22 119.82(16) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 123.53(16) . . ?
C21 C22 C25 114.11(15) . . ?
C17 C22 C25 122.31(15) . . ?
F10 C23 F12 107.10(14) . . ?
F10 C23 F11 105.48(15) . . ?
F12 C23 F11 104.63(14) . . ?
F10 C23 C18 112.70(15) . . ?
F12 C23 C18 114.75(15) . . ?
F11 C23 C18 111.45(14) . . ?
F15 C24 F13 111.0(6) . . ?
F14' C24 F13' 110.4(6) . . ?
F15 C24 F14 99.6(5) . . ?
F13 C24 F14 104.4(7) . . ?
F14' C24 F15' 104.7(6) . . ?
F13' C24 F15' 102.9(5) . . ?
F14' C24 C20 114.6(4) . . ?
F15 C24 C20 115.8(3) . . ?
F13 C24 C20 114.4(5) . . ?
F13' C24 C20 114.1(3) . . ?
F14 C24 C20 109.9(3) . . ?
F15' C24 C20 109.0(3) . . ?
F17 C25 F16 106.53(17) . . ?
F17 C25 F18 106.09(17) . . ?
F16 C25 F18 105.40(18) . . ?
F17 C25 C22 113.81(18) . . ?
F16 C25 C22 111.97(17) . . ?
F18 C25 C22 112.45(16) . . ?

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
C1 N1 B1 C8 74.59(19) . . . . ?
C5 N1 B1 C8 -115.77(16) . . . . ?
C1 N1 B1 C17 -147.60(14) . . . . ?
C5 N1 B1 C17 22.04(19) . . . . ?
C5 N1 C1 C2 -2.5(2) . . . . ?
B1 N1 C1 C2 167.34(15) . . . . ?
C5 N1 C1 C6 179.38(17) . . . . ?
B1 N1 C1 C6 -10.8(2) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
C6 C1 C2 C3 177.37(18) . . . . ?
C1 C2 C3 C4 3.2(3) . . . . ?
C1 C2 C3 C7 -176.46(18) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C7 C3 C4 C5 177.18(18) . . . . ?
C1 N1 C5 C4 3.3(2) . . . . ?
B1 N1 C5 C4 -166.63(16) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
N1 B1 C8 C13 23.7(2) . . . . ?
C17 B1 C8 C13 -107.9(2) . . . . ?
N1 B1 C8 C9 -151.83(14) . . . . ?
C17 B1 C8 C9 76.60(19) . . . . ?
C13 C8 C9 C10 2.2(2) . . . . ?
B1 C8 C9 C10 178.47(15) . . . . ?
C13 C8 C9 C14 -175.65(15) . . . . ?
B1 C8 C9 C14 0.6(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C14 C9 C10 C11 177.44(16) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C9 C10 C11 C15 178.95(18) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C15 C11 C12 C13 -178.78(18) . . . . ?
C11 C12 C13 C8 0.2(3) . . . . ?
C11 C12 C13 C16 -176.70(18) . . . . ?
C9 C8 C13 C12 -2.0(2) . . . . ?
B1 C8 C13 C12 -177.67(17) . . . . ?
C9 C8 C13 C16 174.57(18) . . . . ?
B1 C8 C13 C16 -1.1(3) . . . . ?
C10 C9 C14 F1 133.65(16) . . . . ?
C8 C9 C14 F1 -48.3(2) . . . . ?
C10 C9 C14 F2 -103.72(17) . . . . ?
C8 C9 C14 F2 74.34(19) . . . . ?
C10 C9 C14 F3 14.0(2) . . . . ?
C8 C9 C14 F3 -167.93(15) . . . . ?
C12 C11 C15 F5' 99.3(12) . . . . ?
C10 C11 C15 F5' -81.1(12) . . . . ?
C12 C11 C15 F6 174.1(8) . . . . ?
C10 C11 C15 F6 -6.2(8) . . . . ?
C12 C11 C15 F4' -35.2(7) . . . . ?
C10 C11 C15 F4' 144.4(7) . . . . ?
C12 C11 C15 F4 -53.9(4) . . . . ?
C10 C11 C15 F4 125.7(4) . . . . ?
C12 C11 C15 F5 56.3(4) . . . . ?
C10 C11 C15 F5 -124.1(4) . . . . ?
C12 C11 C15 F6' -142.6(5) . . . . ?
C10 C11 C15 F6' 37.0(6) . . . . ?
C12 C13 C16 F7 -141.31(18) . . . . ?
C8 C13 C16 F7 41.8(3) . . . . ?
C12 C13 C16 F8 -20.3(3) . . . . ?
C8 C13 C16 F8 162.76(19) . . . . ?
C12 C13 C16 F9 97.8(2) . . . . ?
C8 C13 C16 F9 -79.2(2) . . . . ?
N1 B1 C17 C22 -106.40(18) . . . . ?
C8 B1 C17 C22 28.6(2) . . . . ?
N1 B1 C17 C18 72.30(17) . . . . ?
C8 B1 C17 C18 -152.67(15) . . . . ?
C22 C17 C18 C19 5.2(2) . . . . ?
B1 C17 C18 C19 -173.69(16) . . . . ?
C22 C17 C18 C23 -171.19(16) . . . . ?
B1 C17 C18 C23 9.9(2) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
C23 C18 C19 C20 175.41(18) . . . . ?
C18 C19 C20 C21 -3.3(3) . . . . ?
C18 C19 C20 C24 179.1(2) . . . . ?
C19 C20 C21 C22 3.5(3) . . . . ?
C24 C20 C21 C22 -178.9(2) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
C20 C21 C22 C25 -176.49(19) . . . . ?
C18 C17 C22 C21 -5.0(2) . . . . ?
B1 C17 C22 C21 173.71(17) . . . . ?
C18 C17 C22 C25 172.17(17) . . . . ?
B1 C17 C22 C25 -9.1(3) . . . . ?
C19 C18 C23 F10 -110.02(18) . . . . ?
C17 C18 C23 F10 66.7(2) . . . . ?
C19 C18 C23 F12 127.04(17) . . . . ?
C17 C18 C23 F12 -56.3(2) . . . . ?
C19 C18 C23 F11 8.4(2) . . . . ?
C17 C18 C23 F11 -174.95(16) . . . . ?
C21 C20 C24 F14' -67.3(11) . . . . ?
C19 C20 C24 F14' 110.3(11) . . . . ?
C21 C20 C24 F15 -4.0(9) . . . . ?
C19 C20 C24 F15 173.6(8) . . . . ?
C21 C20 C24 F13 127.0(11) . . . . ?
C19 C20 C24 F13 -55.4(11) . . . . ?
C21 C20 C24 F13' 164.0(6) . . . . ?
C19 C20 C24 F13' -18.3(7) . . . . ?
C21 C20 C24 F14 -115.9(7) . . . . ?
C19 C20 C24 F14 61.7(7) . . . . ?
C21 C20 C24 F15' 49.7(7) . . . . ?
C19 C20 C24 F15' -132.7(7) . . . . ?
C21 C22 C25 F17 -123.26(18) . . . . ?
C17 C22 C25 F17 59.3(2) . . . . ?
C21 C22 C25 F16 115.86(18) . . . . ?
C17 C22 C25 F16 -61.6(2) . . . . ?
C21 C22 C25 F18 -2.6(3) . . . . ?
C17 C22 C25 F18 179.96(18) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50609a
_database_code_depnum_ccdc_archive 'CCDC 1426315'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H23 B2 F18 N O2'
_chemical_formula_weight         805.12

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.8508(16)
_cell_length_b                   11.638(2)
_cell_length_c                   17.057(3)
_cell_angle_alpha                92.540(3)
_cell_angle_beta                 90.638(3)
_cell_angle_gamma                106.369(3)
_cell_volume                     1683.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    4154
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.94

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10930
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.826
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6514
_reflns_number_gt                4886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1071P)²+0.7354P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6514
_refine_ls_number_parameters     520
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1828
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.3606(3) -0.1184(2) 0.23218(16) 0.0298(5) Uani 1 1 d . . . . .
B2 B 0.7001(3) 0.2063(2) 0.22431(15) 0.0271(5) Uani 1 1 d . . . . .
O1 O 0.3075(2) -0.07880(16) 0.29924(10) 0.0387(4) Uani 1 1 d . . . . .
O2 O 0.4125(2) -0.21579(15) 0.23683(10) 0.0393(4) Uani 1 1 d . . . . .
N1 N 0.3566(2) -0.05828(17) 0.15666(11) 0.0290(4) Uani 1 1 d . . . . .
F1 F 1.0377(2) 0.3902(2) 0.19100(12) 0.0745(6) Uani 1 1 d . U . . .
F2 F 0.9367(2) 0.26617(19) 0.10063(19) 0.1027(10) Uani 1 1 d . U . . .
F3 F 1.0388(2) 0.4494(2) 0.07761(15) 0.0868(8) Uani 1 1 d . U . . .
F4 F 0.6815(3) 0.73870(15) 0.11944(12) 0.0748(6) Uani 1 1 d . . . . .
F5 F 0.6775(3) 0.65400(19) 0.00597(12) 0.0832(7) Uani 1 1 d . . . . .
F6 F 0.4651(3) 0.63775(19) 0.06631(15) 0.0832(7) Uani 1 1 d . . . . .
F7 F 0.3431(2) 0.37551(15) 0.28302(11) 0.0543(5) Uani 1 1 d . . . . .
F8 F 0.27254(19) 0.24665(17) 0.18680(12) 0.0618(5) Uani 1 1 d . . . . .
F9 F 0.4047(2) 0.21179(15) 0.28342(11) 0.0534(5) Uani 1 1 d . . . . .
F10 F 1.05498(19) 0.00464(16) 0.21925(10) 0.0545(5) Uani 1 1 d . . . . .
F11 F 0.8106(2) -0.07030(15) 0.24205(12) 0.0590(5) Uani 1 1 d . . . . .
F12 F 0.8837(2) 0.05580(18) 0.15308(9) 0.0587(5) Uani 1 1 d . . . . .
F13 F 1.3174(10) 0.2016(14) 0.4480(6) 0.114(5) Uani 0.519(11) 1 d D U P A 1
F14 F 1.1979(14) 0.2921(9) 0.5281(5) 0.111(5) Uani 0.519(11) 1 d D U P A 1
F15 F 1.1308(8) 0.1063(8) 0.5137(5) 0.096(2) Uani 0.519(11) 1 d D U P A 1
F13' F 1.3054(10) 0.3346(7) 0.4715(7) 0.111(4) Uani 0.481(11) 1 d D U P A 2
F14' F 1.1496(9) 0.2030(19) 0.5351(3) 0.125(6) Uani 0.481(11) 1 d D U P A 2
F15' F 1.2904(14) 0.1600(13) 0.4492(7) 0.114(5) Uani 0.481(11) 1 d D U P A 2
F16 F 0.6400(2) 0.35541(19) 0.36231(11) 0.0635(5) Uani 1 1 d . . . . .
F17 F 0.8314(3) 0.4534(2) 0.43716(11) 0.0797(7) Uani 1 1 d . . . . .
F18 F 0.8357(2) 0.48144(15) 0.31422(12) 0.0616(5) Uani 1 1 d . . . . .
C1 C 0.2374(3) -0.1072(2) 0.10200(14) 0.0352(5) Uani 1 1 d . . . . .
C2 C 0.2266(3) -0.0485(2) 0.03633(15) 0.0419(6) Uani 1 1 d . . . . .
H2 H 0.1448 -0.0810 -0.0008 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3383(3) 0.0610(2) 0.02410(15) 0.0412(6) Uani 1 1 d . . . . .
H3 H 0.3307 0.1018 -0.0215 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4570(3) 0.1090(2) 0.07710(14) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.5311 0.1823 0.0677 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4707(3) 0.04957(19) 0.14690(13) 0.0281(5) Uani 1 1 d . . . . .
C6 C 0.5934(3) 0.0875(2) 0.20382(14) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.6094 0.0259 0.2338 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1234(3) -0.2246(3) 0.11943(18) 0.0501(7) Uani 1 1 d . . . . .
H7A H 0.0448 -0.2491 0.0773 0.075 Uiso 1 1 calc R U . . .
H7B H 0.0722 -0.2161 0.1684 0.075 Uiso 1 1 calc R U . . .
H7C H 0.1794 -0.2848 0.1238 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3580(4) -0.1444(3) 0.36162(16) 0.0442(6) Uani 1 1 d . . . . .
C9 C 0.3767(3) -0.2581(2) 0.31603(17) 0.0436(6) Uani 1 1 d . . . . .
C10 C 0.5122(4) -0.0627(3) 0.39594(17) 0.0539(8) Uani 1 1 d . . . . .
H10A H 0.5933 -0.0534 0.3571 0.081 Uiso 1 1 calc R U . . .
H10B H 0.5430 -0.0977 0.4419 0.081 Uiso 1 1 calc R U . . .
H10C H 0.4985 0.0151 0.4108 0.081 Uiso 1 1 calc R U . . .
C11 C 0.2339(5) -0.1668(4) 0.4240(2) 0.0751(11) Uani 1 1 d . . . . .
H11A H 0.2313 -0.0910 0.4491 0.113 Uiso 1 1 calc R U . . .
H11B H 0.2592 -0.2172 0.4629 0.113 Uiso 1 1 calc R U . . .
H11C H 0.1317 -0.2067 0.3998 0.113 Uiso 1 1 calc R U . . .
C12 C 0.5105(4) -0.3036(3) 0.3452(2) 0.0600(9) Uani 1 1 d . . . . .
H12A H 0.5122 -0.3751 0.3142 0.090 Uiso 1 1 calc R U . . .
H12B H 0.4953 -0.3225 0.3999 0.090 Uiso 1 1 calc R U . . .
H12C H 0.6096 -0.2422 0.3401 0.090 Uiso 1 1 calc R U . . .
C13 C 0.2257(5) -0.3607(3) 0.3078(2) 0.0721(11) Uani 1 1 d . . . . .
H13A H 0.1376 -0.3290 0.2974 0.108 Uiso 1 1 calc R U . . .
H13B H 0.2086 -0.4030 0.3561 0.108 Uiso 1 1 calc R U . . .
H13C H 0.2346 -0.4155 0.2648 0.108 Uiso 1 1 calc R U . . .
C14 C 0.6775(3) 0.3253(2) 0.18611(13) 0.0274(5) Uani 1 1 d . . . . .
C15 C 0.7933(3) 0.4004(2) 0.14001(14) 0.0307(5) Uani 1 1 d . . . . .
C16 C 0.7715(3) 0.4996(2) 0.10406(14) 0.0368(6) Uani 1 1 d . . . . .
H16 H 0.8515 0.5461 0.0735 0.044 Uiso 1 1 calc R U . . .
C17 C 0.6330(3) 0.5298(2) 0.11315(15) 0.0384(6) Uani 1 1 d . . . . .
C18 C 0.5166(3) 0.4611(2) 0.15787(15) 0.0377(6) Uani 1 1 d . . . . .
H18 H 0.4223 0.4821 0.1646 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5369(3) 0.3606(2) 0.19339(14) 0.0316(5) Uani 1 1 d . . . . .
C20 C 0.9495(3) 0.3756(2) 0.12642(16) 0.0376(6) Uani 1 1 d . . . . .
C21 C 0.6149(4) 0.6399(3) 0.07654(17) 0.0504(7) Uani 1 1 d . . . . .
C22 C 0.3919(3) 0.2966(2) 0.23756(17) 0.0386(6) Uani 1 1 d . . . . .
C23 C 0.8388(3) 0.2141(2) 0.28948(13) 0.0273(5) Uani 1 1 d . . . . .
C24 C 0.9292(3) 0.1311(2) 0.28775(13) 0.0295(5) Uani 1 1 d . . . . .
C25 C 1.0410(3) 0.1310(2) 0.34601(15) 0.0372(6) Uani 1 1 d . . . . .
H25 H 1.0966 0.0730 0.3430 0.045 Uiso 1 1 calc R U . . .
C26 C 1.0706(3) 0.2145(3) 0.40754(15) 0.0425(6) Uani 1 1 d . . . . .
C27 C 0.9902(3) 0.3004(2) 0.41112(15) 0.0392(6) Uani 1 1 d . . . . .
H27 H 1.0124 0.3596 0.4523 0.047 Uiso 1 1 calc R U . . .
C28 C 0.8764(3) 0.2996(2) 0.35400(14) 0.0318(5) Uani 1 1 d . . . . .
C29 C 0.9176(3) 0.0322(2) 0.22500(15) 0.0369(6) Uani 1 1 d . . . . .
C30 C 1.1907(4) 0.2149(4) 0.4704(2) 0.0685(11) Uani 1 1 d D . . . .
C31 C 0.7950(4) 0.3966(3) 0.36608(16) 0.0447(6) 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
B1 O2 1.342(3) . ?
B1 O1 1.352(3) . ?
B1 N1 1.498(3) . ?
B2 C6 1.463(3) . ?
B2 C14 1.617(3) . ?
B2 C23 1.628(3) . ?
O1 C8 1.472(3) . ?
O2 C9 1.466(3) . ?
N1 C1 1.378(3) . ?
N1 C5 1.389(3) . ?
F1 C20 1.319(3) . ?
F2 C20 1.302(3) . ?
F3 C20 1.323(3) . ?
F4 C21 1.319(3) . ?
F5 C21 1.328(4) . ?
F6 C21 1.329(4) . ?
F7 C22 1.341(3) . ?
F8 C22 1.339(3) . ?
F9 C22 1.315(3) . ?
F10 C29 1.346(3) . ?
F11 C29 1.343(3) . ?
F12 C29 1.319(3) . ?
F13 C30 1.236(8) . ?
F14 C30 1.292(6) . ?
F15 C30 1.462(7) . ?
F13' C30 1.474(8) . ?
F14' C30 1.168(6) . ?
F15' C30 1.273(9) . ?
F16 C31 1.319(3) . ?
F17 C31 1.346(3) . ?
F18 C31 1.331(4) . ?
C1 C2 1.354(4) . ?
C1 C7 1.496(4) . ?
C2 C3 1.401(4) . ?
C3 C4 1.355(4) . ?
C4 C5 1.424(3) . ?
C5 C6 1.409(3) . ?
C8 C11 1.515(4) . ?
C8 C10 1.520(4) . ?
C8 C9 1.556(4) . ?
C9 C12 1.514(4) . ?
C9 C13 1.520(4) . ?
C14 C15 1.417(3) . ?
C14 C19 1.421(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.508(4) . ?
C16 C17 1.376(4) . ?
C17 C18 1.375(4) . ?
C17 C21 1.497(4) . ?
C18 C19 1.395(3) . ?
C19 C22 1.517(3) . ?
C23 C24 1.417(3) . ?
C23 C28 1.421(3) . ?
C24 C25 1.395(3) . ?
C24 C29 1.517(3) . ?
C25 C26 1.369(4) . ?
C26 C27 1.380(4) . ?
C26 C30 1.500(4) . ?
C27 C28 1.391(3) . ?
C28 C31 1.510(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O1 116.4(2) . . ?
O2 B1 N1 122.3(2) . . ?
O1 B1 N1 121.3(2) . . ?
C6 B2 C14 121.5(2) . . ?
C6 B2 C23 117.1(2) . . ?
C14 B2 C23 121.43(19) . . ?
B1 O1 C8 104.93(19) . . ?
B1 O2 C9 106.1(2) . . ?
C1 N1 C5 122.7(2) . . ?
C1 N1 B1 119.7(2) . . ?
C5 N1 B1 117.54(18) . . ?
C2 C1 N1 119.9(2) . . ?
C2 C1 C7 122.9(2) . . ?
N1 C1 C7 117.2(2) . . ?
C1 C2 C3 119.6(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 120.8(2) . . ?
N1 C5 C6 118.0(2) . . ?
N1 C5 C4 116.2(2) . . ?
C6 C5 C4 125.7(2) . . ?
C5 C6 B2 131.1(2) . . ?
O1 C8 C11 108.1(3) . . ?
O1 C8 C10 106.5(2) . . ?
C11 C8 C10 109.7(3) . . ?
O1 C8 C9 102.5(2) . . ?
C11 C8 C9 115.6(3) . . ?
C10 C8 C9 113.6(3) . . ?
O2 C9 C12 108.4(3) . . ?
O2 C9 C13 106.1(2) . . ?
C12 C9 C13 110.0(3) . . ?
O2 C9 C8 102.4(2) . . ?
C12 C9 C8 115.0(2) . . ?
C13 C9 C8 114.1(3) . . ?
C15 C14 C19 114.3(2) . . ?
C15 C14 B2 123.0(2) . . ?
C19 C14 B2 122.7(2) . . ?
C16 C15 C14 123.1(2) . . ?
C16 C15 C20 115.8(2) . . ?
C14 C15 C20 121.1(2) . . ?
C17 C16 C15 120.1(2) . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 C21 121.4(3) . . ?
C16 C17 C21 119.1(3) . . ?
C17 C18 C19 120.7(2) . . ?
C18 C19 C14 122.2(2) . . ?
C18 C19 C22 111.5(2) . . ?
C14 C19 C22 126.3(2) . . ?
F2 C20 F1 104.6(3) . . ?
F2 C20 F3 108.0(2) . . ?
F1 C20 F3 103.9(2) . . ?
F2 C20 C15 113.6(2) . . ?
F1 C20 C15 112.9(2) . . ?
F3 C20 C15 113.0(2) . . ?
F4 C21 F5 107.0(3) . . ?
F4 C21 F6 106.0(3) . . ?
F5 C21 F6 105.8(3) . . ?
F4 C21 C17 112.5(2) . . ?
F5 C21 C17 112.3(3) . . ?
F6 C21 C17 112.7(3) . . ?
F9 C22 F8 106.7(2) . . ?
F9 C22 F7 106.2(2) . . ?
F8 C22 F7 105.7(2) . . ?
F9 C22 C19 117.3(2) . . ?
F8 C22 C19 109.9(2) . . ?
F7 C22 C19 110.3(2) . . ?
C24 C23 C28 114.1(2) . . ?
C24 C23 B2 121.8(2) . . ?
C28 C23 B2 124.1(2) . . ?
C25 C24 C23 122.7(2) . . ?
C25 C24 C29 111.6(2) . . ?
C23 C24 C29 125.7(2) . . ?
C26 C25 C24 120.6(2) . . ?
C25 C26 C27 119.5(2) . . ?
C25 C26 C30 120.8(3) . . ?
C27 C26 C30 119.7(3) . . ?
C26 C27 C28 120.2(2) . . ?
C27 C28 C23 122.9(2) . . ?
C27 C28 C31 114.7(2) . . ?
C23 C28 C31 122.4(2) . . ?
F12 C29 F11 106.7(2) . . ?
F12 C29 F10 104.8(2) . . ?
F11 C29 F10 105.4(2) . . ?
F12 C29 C24 116.2(2) . . ?
F11 C29 C24 112.0(2) . . ?
F10 C29 C24 110.9(2) . . ?
F14' C30 F15' 115.7(9) . . ?
F13 C30 F14 116.6(7) . . ?
F13 C30 F15 100.6(7) . . ?
F14 C30 F15 97.7(6) . . ?
F14' C30 F13' 104.8(8) . . ?
F15' C30 F13' 94.2(7) . . ?
F14' C30 C26 118.5(4) . . ?
F13 C30 C26 116.5(5) . . ?
F15' C30 C26 113.5(6) . . ?
F14 C30 C26 114.4(4) . . ?
F15 C30 C26 107.5(4) . . ?
F13' C30 C26 106.0(4) . . ?
F16 C31 F18 106.9(2) . . ?
F16 C31 F17 106.1(2) . . ?
F18 C31 F17 105.9(2) . . ?
F16 C31 C28 113.1(2) . . ?
F18 C31 C28 113.0(2) . . ?
F17 C31 C28 111.3(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 B1 O1 C8 12.1(3) . . . . ?
N1 B1 O1 C8 -169.6(2) . . . . ?
O1 B1 O2 C9 6.4(3) . . . . ?
N1 B1 O2 C9 -171.8(2) . . . . ?
O2 B1 N1 C1 78.4(3) . . . . ?
O1 B1 N1 C1 -99.8(3) . . . . ?
O2 B1 N1 C5 -105.1(3) . . . . ?
O1 B1 N1 C5 76.7(3) . . . . ?
C5 N1 C1 C2 -1.3(4) . . . . ?
B1 N1 C1 C2 175.0(2) . . . . ?
C5 N1 C1 C7 179.3(2) . . . . ?
B1 N1 C1 C7 -4.3(3) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
C7 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C1 N1 C5 C6 -175.8(2) . . . . ?
B1 N1 C5 C6 7.8(3) . . . . ?
C1 N1 C5 C4 0.9(3) . . . . ?
B1 N1 C5 C4 -175.5(2) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C3 C4 C5 C6 176.4(2) . . . . ?
N1 C5 C6 B2 -159.2(2) . . . . ?
C4 C5 C6 B2 24.4(4) . . . . ?
C14 B2 C6 C5 7.1(4) . . . . ?
C23 B2 C6 C5 -175.0(2) . . . . ?
B1 O1 C8 C11 -146.4(3) . . . . ?
B1 O1 C8 C10 95.7(2) . . . . ?
B1 O1 C8 C9 -23.8(3) . . . . ?
B1 O2 C9 C12 -142.7(2) . . . . ?
B1 O2 C9 C13 99.1(3) . . . . ?
B1 O2 C9 C8 -20.8(3) . . . . ?
O1 C8 C9 O2 27.1(3) . . . . ?
C11 C8 C9 O2 144.4(3) . . . . ?
C10 C8 C9 O2 -87.4(3) . . . . ?
O1 C8 C9 C12 144.4(3) . . . . ?
C11 C8 C9 C12 -98.2(4) . . . . ?
C10 C8 C9 C12 29.9(3) . . . . ?
O1 C8 C9 C13 -87.0(3) . . . . ?
C11 C8 C9 C13 30.3(4) . . . . ?
C10 C8 C9 C13 158.4(3) . . . . ?
C6 B2 C14 C15 -119.0(3) . . . . ?
C23 B2 C14 C15 63.1(3) . . . . ?
C6 B2 C14 C19 58.3(3) . . . . ?
C23 B2 C14 C19 -119.6(2) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
B2 C14 C15 C16 176.9(2) . . . . ?
C19 C14 C15 C20 180.0(2) . . . . ?
B2 C14 C15 C20 -2.5(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C20 C15 C16 C17 -179.8(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C15 C16 C17 C21 177.5(2) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C21 C17 C18 C19 -178.2(2) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C17 C18 C19 C22 -178.3(2) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
B2 C14 C19 C18 -177.7(2) . . . . ?
C15 C14 C19 C22 178.7(2) . . . . ?
B2 C14 C19 C22 1.2(4) . . . . ?
C16 C15 C20 F2 -127.5(3) . . . . ?
C14 C15 C20 F2 51.9(3) . . . . ?
C16 C15 C20 F1 113.6(3) . . . . ?
C14 C15 C20 F1 -67.0(3) . . . . ?
C16 C15 C20 F3 -3.9(3) . . . . ?
C14 C15 C20 F3 175.5(2) . . . . ?
C18 C17 C21 F4 96.0(3) . . . . ?
C16 C17 C21 F4 -81.6(3) . . . . ?
C18 C17 C21 F5 -143.1(3) . . . . ?
C16 C17 C21 F5 39.3(4) . . . . ?
C18 C17 C21 F6 -23.8(4) . . . . ?
C16 C17 C21 F6 158.6(3) . . . . ?
C18 C19 C22 F9 -169.8(2) . . . . ?
C14 C19 C22 F9 11.2(4) . . . . ?
C18 C19 C22 F8 68.2(3) . . . . ?
C14 C19 C22 F8 -110.8(3) . . . . ?
C18 C19 C22 F7 -48.0(3) . . . . ?
C14 C19 C22 F7 133.0(2) . . . . ?
C6 B2 C23 C24 44.0(3) . . . . ?
C14 B2 C23 C24 -138.0(2) . . . . ?
C6 B2 C23 C28 -133.4(2) . . . . ?
C14 B2 C23 C28 44.5(3) . . . . ?
C28 C23 C24 C25 2.3(3) . . . . ?
B2 C23 C24 C25 -175.4(2) . . . . ?
C28 C23 C24 C29 -178.4(2) . . . . ?
B2 C23 C24 C29 3.9(3) . . . . ?
C23 C24 C25 C26 -1.4(4) . . . . ?
C29 C24 C25 C26 179.2(2) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C24 C25 C26 C30 -180.0(3) . . . . ?
C25 C26 C27 C28 2.1(4) . . . . ?
C30 C26 C27 C28 -178.8(3) . . . . ?
C26 C27 C28 C23 -1.1(4) . . . . ?
C26 C27 C28 C31 178.6(3) . . . . ?
C24 C23 C28 C27 -1.0(3) . . . . ?
B2 C23 C28 C27 176.6(2) . . . . ?
C24 C23 C28 C31 179.3(2) . . . . ?
B2 C23 C28 C31 -3.1(4) . . . . ?
C25 C24 C29 F12 -147.2(2) . . . . ?
C23 C24 C29 F12 33.5(3) . . . . ?
C25 C24 C29 F11 89.8(2) . . . . ?
C23 C24 C29 F11 -89.5(3) . . . . ?
C25 C24 C29 F10 -27.6(3) . . . . ?
C23 C24 C29 F10 153.0(2) . . . . ?
C25 C26 C30 F14' -120.2(12) . . . . ?
C27 C26 C30 F14' 60.7(13) . . . . ?
C25 C26 C30 F13 44.5(9) . . . . ?
C27 C26 C30 F13 -134.6(8) . . . . ?
C25 C26 C30 F15' 20.6(10) . . . . ?
C27 C26 C30 F15' -158.5(9) . . . . ?
C25 C26 C30 F14 -174.7(8) . . . . ?
C27 C26 C30 F14 6.2(9) . . . . ?
C25 C26 C30 F15 -67.4(6) . . . . ?
C27 C26 C30 F15 113.5(5) . . . . ?
C25 C26 C30 F13' 122.6(6) . . . . ?
C27 C26 C30 F13' -56.5(7) . . . . ?
C27 C28 C31 F16 -129.3(2) . . . . ?
C23 C28 C31 F16 50.4(3) . . . . ?
C27 C28 C31 F18 109.0(3) . . . . ?
C23 C28 C31 F18 -71.3(3) . . . . ?
C27 C28 C31 F17 -10.0(4) . . . . ?
C23 C28 C31 F17 169.8(2) . . . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50609b
_database_code_depnum_ccdc_archive 'CCDC 1426316'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 B F18 N'
_chemical_formula_weight         689.24

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_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'
'-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                   22.306(6)
_cell_length_b                   11.447(3)
_cell_length_c                   22.092(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.469(5)
_cell_angle_gamma                90
_cell_volume                     5593(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3463
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      23.67

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             2768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19797
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6427
_reflns_number_gt                3049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1709P)²+2.1195P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6427
_refine_ls_number_parameters     509
_refine_ls_number_restraints     185
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.3054
_refine_ls_wR_factor_gt          0.2420
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.006
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8487(2) 0.8614(4) 0.3330(2) 0.0630(11) Uani 1 1 d D . . . .
C1 C 0.86014(19) 0.9697(3) 0.38190(16) 0.0605(10) Uani 1 1 d . . . . .
C2 C 0.8108(2) 1.0313(4) 0.40320(17) 0.0726(12) Uani 1 1 d . . . . .
C3 C 0.8196(3) 1.1234(5) 0.44406(19) 0.0877(17) Uani 1 1 d . . . . .
H3 H 0.7860 1.1617 0.4566 0.105 Uiso 1 1 calc R U . . .
C4 C 0.8766(3) 1.1589(4) 0.46622(19) 0.0839(16) Uani 1 1 d . . . . .
C5 C 0.9255(2) 1.1096(3) 0.44580(17) 0.0703(12) Uani 1 1 d . . . . .
H5 H 0.9646 1.1367 0.4598 0.084 Uiso 1 1 calc R U . . .
C6 C 0.9171(2) 1.0173(3) 0.40341(17) 0.0626(11) Uani 1 1 d . . . . .
C7 C 0.7464(3) 1.0018(8) 0.3805(2) 0.111(2) Uani 1 1 d . U . . .
C8 C 0.8833(4) 1.2581(6) 0.5103(3) 0.114(2) Uani 1 1 d D U . . .
C9 C 0.9737(2) 0.9743(4) 0.3809(2) 0.0679(11) Uani 1 1 d . . . . .
C10 C 0.88600(15) 0.7389(3) 0.34496(15) 0.0498(8) Uani 1 1 d . . . . .
C11 C 0.90663(15) 0.6774(3) 0.29557(15) 0.0519(8) Uani 1 1 d . . . . .
C12 C 0.93849(17) 0.5739(3) 0.30330(18) 0.0597(9) Uani 1 1 d . . . . .
H12 H 0.9502 0.5355 0.2691 0.072 Uiso 1 1 calc R U . . .
C13 C 0.95317(19) 0.5266(3) 0.36022(19) 0.0644(10) Uani 1 1 d . . . . .
C14 C 0.93182(19) 0.5789(3) 0.40911(18) 0.0641(10) Uani 1 1 d . . . . .
H14 H 0.9400 0.5453 0.4481 0.077 Uiso 1 1 calc R U . . .
C15 C 0.89815(16) 0.6816(3) 0.40126(16) 0.0556(9) Uani 1 1 d . . . . .
C16 C 0.89299(19) 0.7191(4) 0.23080(17) 0.0630(10) Uani 1 1 d . . . . .
C17 C 0.9889(3) 0.4159(4) 0.3681(3) 0.0944(16) Uani 1 1 d D . . . .
C18 C 0.8756(2) 0.7258(4) 0.45812(18) 0.0684(11) Uani 1 1 d . . . . .
F1 F 0.72794(16) 0.8952(6) 0.39499(19) 0.1466(17) Uani 1 1 d . . . . .
F2 F 0.70756(17) 1.0756(5) 0.40212(16) 0.170(2) Uani 1 1 d . U . . .
F3 F 0.73300(14) 1.0107(4) 0.31931(12) 0.1228(14) Uani 1 1 d . . . . .
F4 F 0.9562(12) 1.305(3) 0.5209(16) 0.069(8) Uani 0.157(17) 1 d . U P A 1
F5 F 0.8236(16) 1.321(3) 0.4923(16) 0.108(10) Uani 0.157(17) 1 d . U P A 1
F6 F 0.8872(7) 1.2451(19) 0.5685(9) 0.046(6) Uani 0.157(17) 1 d . U P A 1
F13 F 0.9521(3) 0.3225(4) 0.3606(4) 0.128(3) Uani 0.773(14) 1 d . U P B 1
F14 F 1.0245(5) 0.4004(6) 0.3255(5) 0.145(4) Uani 0.773(14) 1 d . U P B 1
F15 F 1.0183(6) 0.4032(9) 0.4210(4) 0.179(6) Uani 0.773(14) 1 d . U P B 1
F4' F 0.8548(5) 1.3547(6) 0.4930(3) 0.118(3) Uani 0.843(17) 1 d D U P A 2
F5' F 0.9364(6) 1.2946(9) 0.5237(4) 0.162(4) Uani 0.843(17) 1 d D U P A 2
F6' F 0.8630(7) 1.2252(7) 0.5627(3) 0.173(4) Uani 0.843(17) 1 d D U P A 2
F13' F 0.9855(11) 0.3660(16) 0.4203(10) 0.121(11) Uani 0.227(14) 1 d D U P B 2
F14' F 1.0477(6) 0.4418(17) 0.3756(16) 0.118(9) Uani 0.227(14) 1 d D U P B 2
F15' F 0.9808(18) 0.340(3) 0.3247(14) 0.198(15) Uani 0.227(14) 1 d D U P B 2
F7 F 1.02087(17) 1.0381(3) 0.4001(2) 0.1571(19) Uani 1 1 d . U . . .
F8 F 0.98934(13) 0.8696(3) 0.3979(2) 0.1217(13) Uani 1 1 d . U . . .
F9 F 0.97000(18) 0.9670(5) 0.32282(16) 0.170(2) Uani 1 1 d . U . . .
F10 F 0.83430(12) 0.7395(3) 0.21392(10) 0.0872(8) Uani 1 1 d . . . . .
F11 F 0.92216(14) 0.8169(2) 0.21876(11) 0.0895(8) Uani 1 1 d . . . . .
F12 F 0.90825(13) 0.6398(2) 0.19108(10) 0.0864(8) Uani 1 1 d . . . . .
F16 F 0.82058(12) 0.7731(3) 0.44852(11) 0.0912(9) Uani 1 1 d . . . . .
F17 F 0.87232(15) 0.6415(3) 0.49974(11) 0.0963(9) Uani 1 1 d . . . . .
F18 F 0.91116(13) 0.8090(3) 0.48702(11) 0.0860(8) Uani 1 1 d . . . . .
N1 N 0.2037(2) 0.0406(4) 0.29428(15) 0.0844(12) Uani 0.504(13) 1 d D . P C 1
H1C H 0.2183 0.0514 0.2547 0.101 Uiso 0.504(13) 1 calc R U P C 1
H1D H 0.1746 -0.0239 0.2897 0.101 Uiso 0.504(13) 1 calc R U P C 1
C19 C 0.2579(5) 0.0029(12) 0.3410(4) 0.079(3) Uani 0.504(13) 1 d D U P C 1
H19 H 0.2858 0.0693 0.3512 0.094 Uiso 0.504(13) 1 calc R U P C 1
C20 C 0.2275(6) -0.0317(14) 0.3957(5) 0.092(4) Uani 0.504(13) 1 d . U P C 1
H20A H 0.2579 -0.0574 0.4290 0.110 Uiso 0.504(13) 1 calc R U P C 1
H20B H 0.1994 -0.0965 0.3848 0.110 Uiso 0.504(13) 1 calc R U P C 1
C21 C 0.1893(3) 0.0852(8) 0.4184(2) 0.130(3) Uani 0.504(13) 1 d . . P C 1
H21A H 0.1693 0.0670 0.4542 0.156 Uiso 0.504(13) 1 calc R U P C 1
H21B H 0.2158 0.1530 0.4273 0.156 Uiso 0.504(13) 1 calc R U P C 1
C22 C 0.1437(6) 0.1042(13) 0.3614(7) 0.100(4) Uani 0.504(13) 1 d D U P C 1
H22A H 0.1213 0.0315 0.3516 0.120 Uiso 0.504(13) 1 calc R U P C 1
H22B H 0.1146 0.1641 0.3701 0.120 Uiso 0.504(13) 1 calc R U P C 1
C23 C 0.1730(6) 0.1412(10) 0.3072(5) 0.085(3) Uani 0.504(13) 1 d D U P C 1
H23 H 0.2011 0.2075 0.3172 0.102 Uiso 0.504(13) 1 calc R U P C 1
C24 C 0.2884(3) -0.0917(7) 0.3223(3) 0.112(2) Uani 0.504(13) 1 d . U P C 1
H24A H 0.2598 -0.1471 0.3019 0.168 Uiso 0.504(13) 1 calc R U P C 1
H24B H 0.3113 -0.1286 0.3575 0.168 Uiso 0.504(13) 1 calc R U P C 1
H24C H 0.3159 -0.0661 0.2943 0.168 Uiso 0.504(13) 1 calc R U P C 1
C25 C 0.1215(4) 0.1734(7) 0.2566(3) 0.147(3) Uani 0.504(13) 1 d . U P C 1
H25A H 0.1382 0.1901 0.2192 0.221 Uiso 0.504(13) 1 calc R U P C 1
H25B H 0.1004 0.2418 0.2689 0.221 Uiso 0.504(13) 1 calc R U P C 1
H25C H 0.0934 0.1086 0.2500 0.221 Uiso 0.504(13) 1 calc R U P C 1
N1' N 0.2037(2) 0.0406(4) 0.29428(15) 0.0844(12) Uani 0.496(13) 1 d D . P C 2
H1'1 H 0.1941 -0.0070 0.2574 0.101 Uiso 0.496(13) 1 calc R U P C 2
H1'2 H 0.2330 0.1007 0.2864 0.101 Uiso 0.496(13) 1 calc R U P C 2
C19' C 0.2286(6) -0.0349(10) 0.3481(4) 0.067(3) Uani 0.496(13) 1 d . U P C 2
H19' H 0.1994 -0.0966 0.3557 0.081 Uiso 0.496(13) 1 calc R U P C 2
C20' C 0.2439(7) 0.0410(16) 0.4037(5) 0.101(4) Uani 0.496(13) 1 d . U P C 2
H20C H 0.2643 -0.0049 0.4377 0.121 Uiso 0.496(13) 1 calc R U P C 2
H20D H 0.2706 0.1050 0.3949 0.121 Uiso 0.496(13) 1 calc R U P C 2
C21' C 0.1893(3) 0.0852(8) 0.4184(2) 0.130(3) Uani 0.496(13) 1 d . . P C 2
H21C H 0.1969 0.1238 0.4583 0.156 Uiso 0.496(13) 1 calc R U P C 2
H21D H 0.1618 0.0197 0.4224 0.156 Uiso 0.496(13) 1 calc R U P C 2
C22' C 0.1576(6) 0.1733(13) 0.3712(5) 0.091(4) Uani 0.496(13) 1 d D U P C 2
H22C H 0.1208 0.2050 0.3849 0.110 Uiso 0.496(13) 1 calc R U P C 2
H22D H 0.1847 0.2379 0.3643 0.110 Uiso 0.496(13) 1 calc R U P C 2
C23' C 0.1426(5) 0.1001(11) 0.3140(5) 0.073(3) Uani 0.496(13) 1 d D U P C 2
H23' H 0.1123 0.0395 0.3202 0.088 Uiso 0.496(13) 1 calc R U P C 2
C24' C 0.2884(3) -0.0917(7) 0.3223(3) 0.112(2) Uani 0.496(13) 1 d . . P C 2
H24D H 0.2796 -0.1713 0.3091 0.168 Uiso 0.496(13) 1 calc R U P C 2
H24E H 0.3224 -0.0914 0.3546 0.168 Uiso 0.496(13) 1 calc R U P C 2
H24F H 0.2985 -0.0456 0.2882 0.168 Uiso 0.496(13) 1 calc R U P C 2
C25' C 0.1215(4) 0.1734(7) 0.2566(3) 0.147(3) Uani 0.496(13) 1 d . . P C 2
H25D H 0.0777 0.1792 0.2512 0.221 Uiso 0.496(13) 1 calc R U P C 2
H25E H 0.1345 0.1361 0.2211 0.221 Uiso 0.496(13) 1 calc R U P C 2
H25F H 0.1389 0.2510 0.2614 0.221 Uiso 0.496(13) 1 calc R U P C 2
H1A H 0.8630(16) 0.907(3) 0.2881(16) 0.071(11) Uiso 1 1 d . . . . .
H1B H 0.7996(10) 0.837(3) 0.3266(17) 0.066(11) Uiso 1 1 d 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
B1 C10 1.635(6) . ?
B1 C1 1.642(6) . ?
B1 H1A 1.20(3) . ?
B1 H1B 1.121(19) . ?
C1 C6 1.408(6) . ?
C1 C2 1.437(5) . ?
C2 C3 1.385(7) . ?
C2 C7 1.497(9) . ?
C3 C4 1.365(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.355(7) . ?
C4 C8 1.490(8) . ?
C5 C6 1.407(6) . ?
C5 H5 0.9400 . ?
C6 C9 1.497(6) . ?
C7 F1 1.341(9) . ?
C7 F2 1.342(6) . ?
C7 F3 1.349(5) . ?
C8 F5' 1.254(12) . ?
C8 F6 1.29(2) . ?
C8 F4' 1.308(7) . ?
C8 F6' 1.350(9) . ?
C8 F5 1.52(3) . ?
C8 F4 1.70(3) . ?
C9 F9 1.279(5) . ?
C9 F8 1.291(5) . ?
C9 F7 1.306(5) . ?
C10 C15 1.401(5) . ?
C10 C11 1.425(5) . ?
C11 C12 1.380(5) . ?
C11 C16 1.502(5) . ?
C12 C13 1.369(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.373(6) . ?
C13 C17 1.495(7) . ?
C14 C15 1.393(6) . ?
C14 H14 0.9400 . ?
C15 C18 1.501(6) . ?
C16 F10 1.334(5) . ?
C16 F12 1.337(4) . ?
C16 F11 1.338(5) . ?
C17 F15 1.272(8) . ?
C17 F15' 1.287(16) . ?
C17 F13' 1.300(14) . ?
C17 F14 1.318(9) . ?
C17 F14' 1.334(14) . ?
C17 F13 1.345(8) . ?
C18 F16 1.333(5) . ?
C18 F17 1.342(4) . ?
C18 F18 1.346(5) . ?
N1 C23 1.388(12) . ?
N1 C19 1.545(10) . ?
N1 H1C 0.9800 . ?
N1 H1D 0.9800 . ?
C19 C24 1.371(13) . ?
C19 C20 1.513(16) . ?
C19 H19 0.9900 . ?
C20 C21 1.696(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.528(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.499(14) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C25 1.541(14) . ?
C23 H23 0.9900 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C19' C20' 1.506(16) . ?
C19' H19' 0.9900 . ?
C20' H20C 0.9800 . ?
C20' H20D 0.9800 . ?
C22' C23' 1.517(13) . ?
C22' H22C 0.9800 . ?
C22' H22D 0.9800 . ?
C23' H23' 0.9900 . ?

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
C10 B1 C1 120.5(3) . . ?
C10 B1 H1A 108.6(17) . . ?
C1 B1 H1A 100.6(18) . . ?
C10 B1 H1B 106(2) . . ?
C1 B1 H1B 110(2) . . ?
H1A B1 H1B 111(3) . . ?
C6 C1 C2 113.3(4) . . ?
C6 C1 B1 124.8(3) . . ?
C2 C1 B1 121.7(4) . . ?
C3 C2 C1 122.5(5) . . ?
C3 C2 C7 116.0(4) . . ?
C1 C2 C7 121.4(4) . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 C8 121.2(6) . . ?
C3 C4 C8 118.1(5) . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 123.4(4) . . ?
C5 C6 C9 115.1(4) . . ?
C1 C6 C9 121.5(3) . . ?
F1 C7 F2 104.8(6) . . ?
F1 C7 F3 105.9(7) . . ?
F2 C7 F3 103.9(4) . . ?
F1 C7 C2 115.9(4) . . ?
F2 C7 C2 112.0(6) . . ?
F3 C7 C2 113.4(5) . . ?
F5' C8 F4' 101.3(9) . . ?
F5' C8 F6' 107.6(9) . . ?
F4' C8 F6' 106.4(6) . . ?
F5' C8 C4 114.8(6) . . ?
F6 C8 C4 123.6(11) . . ?
F4' C8 C4 116.7(6) . . ?
F6' C8 C4 109.4(7) . . ?
F6 C8 F5 105.0(17) . . ?
C4 C8 F5 100.4(11) . . ?
F6 C8 F4 87.7(14) . . ?
C4 C8 F4 110.1(15) . . ?
F5 C8 F4 132(2) . . ?
F9 C9 F8 102.2(4) . . ?
F9 C9 F7 107.8(4) . . ?
F8 C9 F7 104.4(4) . . ?
F9 C9 C6 114.0(4) . . ?
F8 C9 C6 114.7(4) . . ?
F7 C9 C6 112.7(4) . . ?
C15 C10 C11 113.8(3) . . ?
C15 C10 B1 125.5(3) . . ?
C11 C10 B1 120.6(3) . . ?
C12 C11 C10 122.8(3) . . ?
C12 C11 C16 115.4(3) . . ?
C10 C11 C16 121.8(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 118.9(4) . . ?
C12 C13 C17 120.1(4) . . ?
C14 C13 C17 120.9(4) . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 123.0(3) . . ?
C14 C15 C18 114.5(3) . . ?
C10 C15 C18 122.5(4) . . ?
F10 C16 F12 105.1(3) . . ?
F10 C16 F11 106.4(3) . . ?
F12 C16 F11 105.4(3) . . ?
F10 C16 C11 113.1(3) . . ?
F12 C16 C11 111.8(3) . . ?
F11 C16 C11 114.3(3) . . ?
F15' C17 F13' 110.2(18) . . ?
F15 C17 F14 110.7(8) . . ?
F15' C17 F14' 106.4(16) . . ?
F13' C17 F14' 99.0(12) . . ?
F15 C17 F13 104.8(8) . . ?
F14 C17 F13 102.7(7) . . ?
F15 C17 C13 114.0(6) . . ?
F15' C17 C13 117.7(14) . . ?
F13' C17 C13 112.6(11) . . ?
F14 C17 C13 113.2(5) . . ?
F14' C17 C13 109.1(9) . . ?
F13 C17 C13 110.6(5) . . ?
F16 C18 F17 105.7(3) . . ?
F16 C18 F18 105.2(4) . . ?
F17 C18 F18 105.4(3) . . ?
F16 C18 C15 114.0(3) . . ?
F17 C18 C15 112.6(4) . . ?
F18 C18 C15 113.3(3) . . ?
C23 N1 C19 117.2(7) . . ?
C23 N1 H1C 108.0 . . ?
C19 N1 H1C 108.0 . . ?
C23 N1 H1D 108.0 . . ?
C19 N1 H1D 108.0 . . ?
H1C N1 H1D 107.2 . . ?
C24 C19 C20 109.0(12) . . ?
C24 C19 N1 113.3(8) . . ?
C20 C19 N1 102.4(9) . . ?
C24 C19 H19 110.6 . . ?
C20 C19 H19 110.6 . . ?
N1 C19 H19 110.6 . . ?
C19 C20 C21 108.9(10) . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20B 109.9 . . ?
C21 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C20 100.1(8) . . ?
C22 C21 H21A 111.8 . . ?
C20 C21 H21A 111.8 . . ?
C22 C21 H21B 111.8 . . ?
C20 C21 H21B 111.8 . . ?
H21A C21 H21B 109.5 . . ?
C23 C22 C21 112.7(10) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
N1 C23 C22 102.0(10) . . ?
N1 C23 C25 113.0(7) . . ?
C22 C23 C25 106.6(12) . . ?
N1 C23 H23 111.6 . . ?
C22 C23 H23 111.6 . . ?
C25 C23 H23 111.6 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20' C19' H19' 110.9 . . ?
C19' C20' H20C 110.4 . . ?
C19' C20' H20D 110.4 . . ?
H20C C20' H20D 108.6 . . ?
C23' C22' H22C 111.1 . . ?
C23' C22' H22D 111.1 . . ?
H22C C22' H22D 109.0 . . ?
C22' C23' H23' 110.7 . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_mo_50618a
_database_code_depnum_ccdc_archive 'CCDC 1426317'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H14 B F18 N'
_chemical_formula_weight         681.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.187(2)
_cell_length_b                   12.091(2)
_cell_length_c                   17.222(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.411(3)
_cell_angle_gamma                90
_cell_volume                     2573.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6000
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.26

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18047
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5827
_reflns_number_gt                4332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_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. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1016P)²+0.9742P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5827
_refine_ls_number_parameters     440
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4652(2) 0.87416(18) 0.24034(14) 0.0260(5) Uani 1 1 d . . . . .
H1 H 0.3783(19) 0.8696(18) 0.2256(14) 0.022(5) Uiso 1 1 d . . . . .
N1 N 0.51213(14) 0.79910(14) 0.32488(10) 0.0258(4) Uani 1 1 d . . . . .
F1 F 0.41590(13) 0.70968(12) -0.13540(8) 0.0459(4) Uani 1 1 d . . . . .
F2 F 0.43800(13) 0.55033(11) -0.07858(9) 0.0430(4) Uani 1 1 d . . . . .
F3 F 0.57651(13) 0.64804(15) -0.07355(9) 0.0520(4) Uani 1 1 d . . . . .
F4 F 0.28551(14) 0.58151(13) 0.11955(9) 0.0514(4) Uani 1 1 d . . . . .
F5 F 0.24023(12) 0.74605(14) 0.13895(10) 0.0493(4) Uani 1 1 d . . . . .
F6 F 0.36175(12) 0.65862(12) 0.23620(8) 0.0417(4) Uani 1 1 d . . . . .
F7 F 0.68468(15) 0.95505(15) 0.09217(12) 0.0617(5) Uani 1 1 d . . . . .
F8 F 0.67750(12) 0.95678(12) 0.21403(10) 0.0449(4) Uani 1 1 d . . . . .
F9 F 0.55967(14) 1.04566(11) 0.11626(11) 0.0511(4) Uani 1 1 d . . . . .
F10 F 0.26447(15) 1.13274(13) 0.08553(11) 0.0611(5) Uani 1 1 d . . . . .
F11 F 0.32940(12) 0.97172(12) 0.08692(8) 0.0423(4) Uani 1 1 d . . . . .
F12 F 0.23183(12) 1.00696(15) 0.16095(10) 0.0529(4) Uani 1 1 d . . . . .
F13 F 0.4163(10) 1.4185(6) 0.2491(5) 0.074(3) Uani 0.55(3) 1 d D U P A 1
F14 F 0.5007(11) 1.3923(8) 0.3744(7) 0.060(2) Uani 0.55(3) 1 d D U P A 1
F15 F 0.5823(11) 1.4121(11) 0.2893(10) 0.083(3) Uani 0.55(3) 1 d D U P A 1
F13' F 0.4054(8) 1.4127(10) 0.2814(19) 0.111(6) Uani 0.45(3) 1 d D U P A 2
F14' F 0.550(2) 1.3876(10) 0.3866(8) 0.074(4) Uani 0.45(3) 1 d . U P A 2
F15' F 0.5626(15) 1.4189(13) 0.2718(9) 0.084(5) Uani 0.45(3) 1 d D U P A 2
F16 F 0.62947(18) 0.96639(16) 0.45162(10) 0.0702(6) Uani 1 1 d . . . . .
F17 F 0.70252(11) 0.91371(11) 0.36417(9) 0.0441(4) Uani 1 1 d . . . . .
F18 F 0.74668(15) 1.06798(15) 0.42610(15) 0.0891(8) Uani 1 1 d . U . . .
C1 C 0.4590(2) 0.80985(19) 0.38016(13) 0.0333(5) Uani 1 1 d . . . . .
C2 C 0.3708(2) 0.8936(2) 0.36726(16) 0.0445(6) Uani 1 1 d . . . . .
H2A H 0.3994 0.9677 0.3644 0.067 Uiso 1 1 calc R U . . .
H2B H 0.3440 0.8902 0.4136 0.067 Uiso 1 1 calc R U . . .
H2C H 0.3115 0.8775 0.3154 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4853(2) 0.7431(2) 0.44983(15) 0.0434(6) Uani 1 1 d . . . . .
H3 H 0.4475 0.7517 0.4874 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5656(2) 0.6643(2) 0.46527(16) 0.0460(6) Uani 1 1 d . . . . .
H4 H 0.5841 0.6189 0.5132 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6179(2) 0.65338(19) 0.40972(15) 0.0383(5) Uani 1 1 d . . . . .
H5 H 0.6729 0.5991 0.4189 0.046 Uiso 1 1 calc R U . . .
C6 C 0.59185(17) 0.72050(17) 0.34011(13) 0.0286(4) Uani 1 1 d . . . . .
C7 C 0.65338(19) 0.70073(19) 0.28276(14) 0.0346(5) Uani 1 1 d . . . . .
H7A H 0.6104 0.6539 0.2366 0.052 Uiso 1 1 calc R U . . .
H7B H 0.7220 0.6638 0.3130 0.052 Uiso 1 1 calc R U . . .
H7C H 0.6680 0.7716 0.2612 0.052 Uiso 1 1 calc R U . . .
C8 C 0.47874(16) 0.81592(16) 0.15764(12) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.41043(16) 0.72411(16) 0.12194(12) 0.0245(4) Uani 1 1 d . . . . .
C10 C 0.32600(19) 0.67855(19) 0.15519(13) 0.0323(5) Uani 1 1 d . . . . .
C11 C 0.41108(18) 0.67038(17) 0.05034(12) 0.0273(4) Uani 1 1 d . . . . .
H11 H 0.3650 0.6087 0.0296 0.033 Uiso 1 1 calc R U . . .
C12 C 0.47808(17) 0.70638(17) 0.00983(12) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.47724(19) 0.65335(18) -0.06902(13) 0.0316(5) Uani 1 1 d . . . . .
C14 C 0.54347(18) 0.79713(17) 0.03979(13) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.5888 0.8234 0.0114 0.034 Uiso 1 1 calc R U . . .
C15 C 0.54329(17) 0.85034(16) 0.11143(13) 0.0262(4) Uani 1 1 d . . . . .
C16 C 0.6161(2) 0.95077(18) 0.13396(15) 0.0355(5) Uani 1 1 d . . . . .
C17 C 0.48875(17) 1.00931(17) 0.25860(12) 0.0271(4) Uani 1 1 d . . . . .
C18 C 0.40878(18) 1.08365(17) 0.20825(13) 0.0289(4) Uani 1 1 d . . . . .
C19 C 0.31044(19) 1.04722(19) 0.13651(15) 0.0360(5) Uani 1 1 d . . . . .
C20 C 0.4114(2) 1.19767(17) 0.22268(14) 0.0322(5) Uani 1 1 d . . . . .
H20 H 0.3552 1.2435 0.1881 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4946(2) 1.24363(17) 0.28665(15) 0.0333(5) Uani 1 1 d . . . . .
C22 C 0.5002(2) 1.36616(19) 0.30240(17) 0.0418(6) Uani 1 1 d D . . . .
C23 C 0.5753(2) 1.17629(18) 0.33677(14) 0.0345(5) Uani 1 1 d . . . . .
H23 H 0.6335 1.2077 0.3808 0.041 Uiso 1 1 calc R U . . .
C24 C 0.57224(18) 1.06214(18) 0.32337(14) 0.0315(5) Uani 1 1 d . . . . .
C25 C 0.6630(2) 1.0024(2) 0.38949(17) 0.0481(7) 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
B1 N1 1.643(3) . ?
B1 C8 1.653(3) . ?
B1 C17 1.672(3) . ?
B1 H1 1.09(2) . ?
N1 C1 1.371(3) . ?
N1 C6 1.373(3) . ?
F1 C13 1.334(3) . ?
F2 C13 1.337(3) . ?
F3 C13 1.340(3) . ?
F4 C10 1.345(3) . ?
F5 C10 1.343(3) . ?
F6 C10 1.330(2) . ?
F7 C16 1.339(3) . ?
F8 C16 1.336(3) . ?
F9 C16 1.344(3) . ?
F10 C19 1.355(3) . ?
F11 C19 1.332(3) . ?
F12 C19 1.339(3) . ?
F13 C22 1.326(8) . ?
F14 C22 1.278(9) . ?
F15 C22 1.304(8) . ?
F13' C22 1.302(9) . ?
F14' C22 1.393(14) . ?
F15' C22 1.289(11) . ?
F16 C25 1.364(4) . ?
F17 C25 1.330(3) . ?
F18 C25 1.326(3) . ?
C1 C3 1.386(3) . ?
C1 C2 1.498(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C15 1.415(3) . ?
C8 C9 1.427(3) . ?
C9 C11 1.396(3) . ?
C9 C10 1.522(3) . ?
C11 C12 1.374(3) . ?
C11 H11 0.9500 . ?
C12 C14 1.380(3) . ?
C12 C13 1.498(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.512(3) . ?
C17 C24 1.417(3) . ?
C17 C18 1.426(3) . ?
C18 C20 1.399(3) . ?
C18 C19 1.512(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9500 . ?
C21 C23 1.378(3) . ?
C21 C22 1.503(3) . ?
C23 C24 1.398(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.517(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
N1 B1 C8 114.06(16) . . ?
N1 B1 C17 112.66(16) . . ?
C8 B1 C17 120.63(17) . . ?
N1 B1 H1 102.7(12) . . ?
C8 B1 H1 101.5(12) . . ?
C17 B1 H1 101.8(12) . . ?
C1 N1 C6 118.41(18) . . ?
C1 N1 B1 115.94(17) . . ?
C6 N1 B1 125.34(17) . . ?
N1 C1 C3 120.8(2) . . ?
N1 C1 C2 121.3(2) . . ?
C3 C1 C2 117.9(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C1 C3 H3 119.6 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 C7 122.59(18) . . ?
C5 C6 C7 116.58(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C8 C9 113.56(17) . . ?
C15 C8 B1 128.74(18) . . ?
C9 C8 B1 117.45(17) . . ?
C11 C9 C8 123.03(18) . . ?
C11 C9 C10 113.23(18) . . ?
C8 C9 C10 123.67(17) . . ?
F6 C10 F5 107.07(18) . . ?
F6 C10 F4 105.05(17) . . ?
F5 C10 F4 105.28(19) . . ?
F6 C10 C9 114.98(18) . . ?
F5 C10 C9 112.04(18) . . ?
F4 C10 C9 111.72(17) . . ?
C12 C11 C9 120.28(19) . . ?
C12 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C11 C12 C14 119.40(19) . . ?
C11 C12 C13 121.47(19) . . ?
C14 C12 C13 119.04(19) . . ?
F1 C13 F2 106.09(18) . . ?
F1 C13 F3 106.70(18) . . ?
F2 C13 F3 106.99(18) . . ?
F1 C13 C12 111.64(18) . . ?
F2 C13 C12 112.99(18) . . ?
F3 C13 C12 112.01(19) . . ?
C12 C14 C15 120.33(19) . . ?
C12 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C8 123.34(19) . . ?
C14 C15 C16 113.65(19) . . ?
C8 C15 C16 122.99(19) . . ?
F8 C16 F7 105.9(2) . . ?
F8 C16 F9 106.03(19) . . ?
F7 C16 F9 105.65(19) . . ?
F8 C16 C15 114.24(19) . . ?
F7 C16 C15 112.37(19) . . ?
F9 C16 C15 112.1(2) . . ?
C24 C17 C18 113.66(18) . . ?
C24 C17 B1 129.11(18) . . ?
C18 C17 B1 116.87(18) . . ?
C20 C18 C17 123.1(2) . . ?
C20 C18 C19 113.15(19) . . ?
C17 C18 C19 123.71(18) . . ?
F11 C19 F12 106.9(2) . . ?
F11 C19 F10 104.42(19) . . ?
F12 C19 F10 105.11(19) . . ?
F11 C19 C18 115.12(19) . . ?
F12 C19 C18 112.74(19) . . ?
F10 C19 C18 111.69(19) . . ?
C21 C20 C18 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C18 C20 H20 119.9 . . ?
C20 C21 C23 119.4(2) . . ?
C20 C21 C22 121.3(2) . . ?
C23 C21 C22 119.4(2) . . ?
F15' C22 F13' 111.1(12) . . ?
F14 C22 F15 109.8(7) . . ?
F14 C22 F13 105.9(5) . . ?
F15 C22 F13 102.7(8) . . ?
F15' C22 F14' 101.3(9) . . ?
F13' C22 F14' 105.6(7) . . ?
F14 C22 C21 113.7(5) . . ?
F15' C22 C21 114.3(8) . . ?
F13' C22 C21 113.2(6) . . ?
F15 C22 C21 112.3(6) . . ?
F13 C22 C21 111.6(4) . . ?
F14' C22 C21 110.3(5) . . ?
C21 C23 C24 120.6(2) . . ?
C21 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C17 123.0(2) . . ?
C23 C24 C25 112.1(2) . . ?
C17 C24 C25 124.70(19) . . ?
F18 C25 F17 106.4(2) . . ?
F18 C25 F16 105.2(2) . . ?
F17 C25 F16 105.8(2) . . ?
F18 C25 C24 112.3(2) . . ?
F17 C25 C24 115.8(2) . . ?
F16 C25 C24 110.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 B1 N1 C1 -147.83(19) . . . . ?
C17 B1 N1 C1 69.9(2) . . . . ?
C8 B1 N1 C6 25.6(3) . . . . ?
C17 B1 N1 C6 -116.7(2) . . . . ?
C6 N1 C1 C3 0.1(3) . . . . ?
B1 N1 C1 C3 174.0(2) . . . . ?
C6 N1 C1 C2 -179.7(2) . . . . ?
B1 N1 C1 C2 -5.8(3) . . . . ?
N1 C1 C3 C4 0.1(4) . . . . ?
C2 C1 C3 C4 179.9(3) . . . . ?
C1 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C1 N1 C6 C5 0.1(3) . . . . ?
B1 N1 C6 C5 -173.2(2) . . . . ?
C1 N1 C6 C7 178.9(2) . . . . ?
B1 N1 C6 C7 5.6(3) . . . . ?
C4 C5 C6 N1 -0.5(4) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
N1 B1 C8 C15 -114.1(2) . . . . ?
C17 B1 C8 C15 24.9(3) . . . . ?
N1 B1 C8 C9 72.0(2) . . . . ?
C17 B1 C8 C9 -148.96(19) . . . . ?
C15 C8 C9 C11 2.8(3) . . . . ?
B1 C8 C9 C11 177.55(19) . . . . ?
C15 C8 C9 C10 -174.06(19) . . . . ?
B1 C8 C9 C10 0.7(3) . . . . ?
C11 C9 C10 F6 132.8(2) . . . . ?
C8 C9 C10 F6 -50.0(3) . . . . ?
C11 C9 C10 F5 -104.6(2) . . . . ?
C8 C9 C10 F5 72.5(3) . . . . ?
C11 C9 C10 F4 13.2(3) . . . . ?
C8 C9 C10 F4 -169.62(19) . . . . ?
C8 C9 C11 C12 -1.2(3) . . . . ?
C10 C9 C11 C12 175.95(19) . . . . ?
C9 C11 C12 C14 -1.0(3) . . . . ?
C9 C11 C12 C13 -177.4(2) . . . . ?
C11 C12 C13 F1 97.2(2) . . . . ?
C14 C12 C13 F1 -79.3(3) . . . . ?
C11 C12 C13 F2 -22.3(3) . . . . ?
C14 C12 C13 F2 161.26(19) . . . . ?
C11 C12 C13 F3 -143.2(2) . . . . ?
C14 C12 C13 F3 40.3(3) . . . . ?
C11 C12 C14 C15 1.4(3) . . . . ?
C13 C12 C14 C15 177.9(2) . . . . ?
C12 C14 C15 C8 0.5(3) . . . . ?
C12 C14 C15 C16 -177.8(2) . . . . ?
C9 C8 C15 C14 -2.4(3) . . . . ?
B1 C8 C15 C14 -176.5(2) . . . . ?
C9 C8 C15 C16 175.6(2) . . . . ?
B1 C8 C15 C16 1.6(3) . . . . ?
C14 C15 C16 F8 -134.7(2) . . . . ?
C8 C15 C16 F8 47.0(3) . . . . ?
C14 C15 C16 F7 -14.1(3) . . . . ?
C8 C15 C16 F7 167.7(2) . . . . ?
C14 C15 C16 F9 104.7(2) . . . . ?
C8 C15 C16 F9 -73.6(3) . . . . ?
N1 B1 C17 C24 26.5(3) . . . . ?
C8 B1 C17 C24 -113.0(3) . . . . ?
N1 B1 C17 C18 -146.09(18) . . . . ?
C8 B1 C17 C18 74.4(3) . . . . ?
C24 C17 C18 C20 -1.4(3) . . . . ?
B1 C17 C18 C20 172.4(2) . . . . ?
C24 C17 C18 C19 -178.6(2) . . . . ?
B1 C17 C18 C19 -4.9(3) . . . . ?
C20 C18 C19 F11 138.6(2) . . . . ?
C17 C18 C19 F11 -44.0(3) . . . . ?
C20 C18 C19 F12 -98.4(2) . . . . ?
C17 C18 C19 F12 79.1(3) . . . . ?
C20 C18 C19 F10 19.7(3) . . . . ?
C17 C18 C19 F10 -162.8(2) . . . . ?
C17 C18 C20 C21 1.4(3) . . . . ?
C19 C18 C20 C21 178.9(2) . . . . ?
C18 C20 C21 C23 -0.4(3) . . . . ?
C18 C20 C21 C22 178.9(2) . . . . ?
C20 C21 C22 F14 120.9(7) . . . . ?
C23 C21 C22 F14 -59.9(7) . . . . ?
C20 C21 C22 F15' -97.7(10) . . . . ?
C23 C21 C22 F15' 81.5(10) . . . . ?
C20 C21 C22 F13' 30.9(16) . . . . ?
C23 C21 C22 F13' -149.9(15) . . . . ?
C20 C21 C22 F15 -113.6(9) . . . . ?
C23 C21 C22 F15 65.6(9) . . . . ?
C20 C21 C22 F13 1.1(7) . . . . ?
C23 C21 C22 F13 -179.7(6) . . . . ?
C20 C21 C22 F14' 149.0(11) . . . . ?
C23 C21 C22 F14' -31.8(11) . . . . ?
C20 C21 C23 C24 -0.6(3) . . . . ?
C22 C21 C23 C24 -179.8(2) . . . . ?
C21 C23 C24 C17 0.6(4) . . . . ?
C21 C23 C24 C25 -175.1(2) . . . . ?
C18 C17 C24 C23 0.4(3) . . . . ?
B1 C17 C24 C23 -172.4(2) . . . . ?
C18 C17 C24 C25 175.5(2) . . . . ?
B1 C17 C24 C25 2.8(4) . . . . ?
C23 C24 C25 F18 -23.9(3) . . . . ?
C17 C24 C25 F18 160.5(2) . . . . ?
C23 C24 C25 F17 -146.3(2) . . . . ?
C17 C24 C25 F17 38.1(4) . . . . ?
C23 C24 C25 F16 93.4(3) . . . . ?
C17 C24 C25 F16 -82.3(3) . . . . ?

_refine_diff_density_max         0.668
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-2

