# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mo_20140117bb_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 B F2 N3 O'
_chemical_formula_weight         295.05

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2029(7)
_cell_length_b                   9.4990(9)
_cell_length_c                   19.3231(19)
_cell_angle_alpha                81.1880(10)
_cell_angle_beta                 84.179(2)
_cell_angle_gamma                79.417(2)
_cell_volume                     1280.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3676
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.32

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9537
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.07
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4461
_reflns_number_gt                3570
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1026P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1147(3) 0.1242(2) 0.16401(11) 0.0381(5) Uani 1 1 d . . .
B2 B 0.3152(4) 0.5851(3) 0.33270(12) 0.0487(6) Uani 1 1 d . . .
C1 C 0.0556(3) 0.3035(2) -0.02348(10) 0.0383(5) Uani 1 1 d . . .
C2 C -0.0276(3) 0.3494(2) -0.08688(10) 0.0450(5) Uani 1 1 d . . .
H2 H -0.1341 0.3156 -0.0966 0.054 Uiso 1 1 calc R . .
C3 C 0.0555(4) 0.4478(2) -0.13485(11) 0.0543(6) Uani 1 1 d . . .
H3 H 0.0026 0.4812 -0.1775 0.065 Uiso 1 1 calc R . .
C4 C 0.2140(4) 0.4975(3) -0.12125(12) 0.0578(6) Uani 1 1 d . . .
H4 H 0.2665 0.5627 -0.1550 0.069 Uiso 1 1 calc R . .
C5 C 0.2973(3) 0.4521(2) -0.05806(12) 0.0537(6) Uani 1 1 d . . .
H5 H 0.4045 0.4855 -0.0488 0.064 Uiso 1 1 calc R . .
C6 C 0.2139(3) 0.3550(2) -0.00943(10) 0.0423(5) Uani 1 1 d . . .
C7 C 0.2639(3) 0.2912(2) 0.06269(10) 0.0426(5) Uani 1 1 d . . .
C8 C -0.0592(3) -0.0672(2) 0.22868(10) 0.0454(5) Uani 1 1 d . . .
H8 H 0.0267 -0.0741 0.2624 0.054 Uiso 1 1 calc R . .
C9 C -0.1985(3) -0.1490(2) 0.24152(12) 0.0530(6) Uani 1 1 d . . .
H9 H -0.2066 -0.2116 0.2833 0.064 Uiso 1 1 calc R . .
C10 C -0.3272(3) -0.1386(2) 0.19229(12) 0.0512(5) Uani 1 1 d . . .
H10 H -0.4248 -0.1924 0.2008 0.061 Uiso 1 1 calc R . .
C11 C -0.3096(3) -0.0480(2) 0.13045(11) 0.0444(5) Uani 1 1 d . . .
H11 H -0.3949 -0.0410 0.0965 0.053 Uiso 1 1 calc R . .
C12 C -0.1653(3) 0.03338(19) 0.11824(9) 0.0343(4) Uani 1 1 d . . .
C13 C -0.1381(3) 0.1286(2) 0.05285(10) 0.0369(4) Uani 1 1 d . . .
C14 C 0.0047(3) 0.20569(19) 0.03986(9) 0.0337(4) Uani 1 1 d . . .
C15 C -0.2648(3) 0.1327(2) -0.00014(10) 0.0430(5) Uani 1 1 d . . .
C16 C 0.3601(3) 0.3165(2) 0.39336(10) 0.0379(4) Uani 1 1 d . . .
C17 C 0.4019(3) 0.1700(2) 0.38776(11) 0.0488(5) Uani 1 1 d . . .
H17 H 0.3962 0.1024 0.4279 0.059 Uiso 1 1 calc R . .
C18 C 0.4517(4) 0.1245(3) 0.32347(13) 0.0562(6) Uani 1 1 d . . .
H18 H 0.4790 0.0262 0.3198 0.067 Uiso 1 1 calc R . .
C19 C 0.4610(4) 0.2249(3) 0.26412(12) 0.0564(6) Uani 1 1 d . . .
H19 H 0.4965 0.1961 0.2201 0.068 Uiso 1 1 calc R . .
C20 C 0.4163(3) 0.3680(3) 0.27203(11) 0.0502(5) Uani 1 1 d . . .
H20 H 0.4206 0.4365 0.2322 0.060 Uiso 1 1 calc R . .
C21 C 0.2202(3) 0.7561(2) 0.42801(12) 0.0506(5) Uani 1 1 d . . .
C22 C 0.1870(3) 0.7346(2) 0.50528(11) 0.0466(5) Uani 1 1 d . . .
C23 C 0.1373(4) 0.8353(3) 0.55192(14) 0.0611(6) Uani 1 1 d . . .
H23 H 0.1238 0.9339 0.5361 0.073 Uiso 1 1 calc R . .
C24 C 0.1086(4) 0.7854(3) 0.62208(14) 0.0631(7) Uani 1 1 d . . .
H24 H 0.0746 0.8511 0.6541 0.076 Uiso 1 1 calc R . .
C25 C 0.1297(3) 0.6389(3) 0.64563(12) 0.0593(6) Uani 1 1 d . . .
H25 H 0.1082 0.6077 0.6933 0.071 Uiso 1 1 calc R . .
C26 C 0.1826(3) 0.5370(2) 0.59933(11) 0.0493(5) Uani 1 1 d . . .
H26 H 0.1985 0.4384 0.6154 0.059 Uiso 1 1 calc R . .
C27 C 0.2106(3) 0.5873(2) 0.52886(10) 0.0395(5) Uani 1 1 d . . .
C28 C 0.2654(3) 0.5132(2) 0.46609(10) 0.0374(4) Uani 1 1 d . . .
C29 C 0.3068(3) 0.3703(2) 0.46059(10) 0.0374(4) Uani 1 1 d . . .
C30 C 0.3001(3) 0.2643(2) 0.52153(11) 0.0482(5) Uani 1 1 d . . .
F1 F 0.27930(17) 0.03747(14) 0.18366(6) 0.0537(4) Uani 1 1 d . . .
F2 F 0.0499(2) 0.22143(13) 0.21119(6) 0.0540(4) Uani 1 1 d . . .
F3 F 0.4704(2) 0.64198(16) 0.30187(7) 0.0738(5) Uani 1 1 d . . .
F4 F 0.1630(2) 0.63170(16) 0.29299(7) 0.0763(5) Uani 1 1 d . . .
N1 N 0.1314(2) 0.20149(17) 0.08883(8) 0.0370(4) Uani 1 1 d . . .
N2 N -0.0423(2) 0.02424(17) 0.16804(8) 0.0365(4) Uani 1 1 d . . .
N3 N -0.3644(3) 0.1336(2) -0.04209(11) 0.0660(6) Uani 1 1 d . . .
N4 N 0.3667(2) 0.41426(18) 0.33465(8) 0.0399(4) Uani 1 1 d . . .
N5 N 0.2698(3) 0.61567(17) 0.40816(9) 0.0430(4) Uani 1 1 d . . .
N6 N 0.2963(4) 0.1766(2) 0.56877(10) 0.0755(7) Uani 1 1 d . . .
O1 O 0.3902(2) 0.31140(19) 0.09472(8) 0.0589(4) Uani 1 1 d . . .
O2 O 0.2072(3) 0.86683(17) 0.38779(9) 0.0731(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 F1 1.366(3) . ?
B1 F2 1.384(2) . ?
B1 N1 1.528(3) . ?
B1 N2 1.594(3) . ?
B2 F4 1.370(3) . ?
B2 F3 1.373(3) . ?
B2 N5 1.522(3) . ?
B2 N4 1.592(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.393(3) . ?
C1 C14 1.477(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(3) . ?
C7 O1 1.209(2) . ?
C7 N1 1.401(3) . ?
C8 N2 1.357(3) . ?
C8 C9 1.359(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.356(2) . ?
C12 C13 1.455(3) . ?
C13 C14 1.351(3) . ?
C13 C15 1.431(3) . ?
C14 N1 1.371(2) . ?
C15 N3 1.134(3) . ?
C16 N4 1.354(2) . ?
C16 C17 1.387(3) . ?
C16 C29 1.458(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(3) . ?
C19 H19 0.9300 . ?
C20 N4 1.342(3) . ?
C20 H20 0.9300 . ?
C21 O2 1.203(2) . ?
C21 N5 1.417(3) . ?
C21 C22 1.477(3) . ?
C22 C27 1.388(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.478(3) . ?
C28 C29 1.353(3) . ?
C28 N5 1.368(2) . ?
C29 C30 1.431(3) . ?
C30 N6 1.139(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
F1 B1 F2 110.66(16) . . ?
F1 B1 N1 113.02(18) . . ?
F2 B1 N1 111.31(16) . . ?
F1 B1 N2 107.74(16) . . ?
F2 B1 N2 106.27(16) . . ?
N1 B1 N2 107.48(15) . . ?
F4 B2 F3 110.93(18) . . ?
F4 B2 N5 112.2(2) . . ?
F3 B2 N5 111.6(2) . . ?
F4 B2 N4 107.0(2) . . ?
F3 B2 N4 107.25(19) . . ?
N5 B2 N4 107.49(16) . . ?
C6 C1 C2 121.1(2) . . ?
C6 C1 C14 106.55(17) . . ?
C2 C1 C14 132.32(19) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 C7 130.1(2) . . ?
C1 C6 C7 108.40(18) . . ?
O1 C7 N1 125.12(18) . . ?
O1 C7 C6 128.7(2) . . ?
N1 C7 C6 106.21(17) . . ?
N2 C8 C9 121.8(2) . . ?
N2 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N2 C12 C11 119.77(17) . . ?
N2 C12 C13 117.83(17) . . ?
C11 C12 C13 122.40(18) . . ?
C14 C13 C15 120.06(17) . . ?
C14 C13 C12 122.81(17) . . ?
C15 C13 C12 117.06(17) . . ?
C13 C14 N1 121.58(16) . . ?
C13 C14 C1 129.90(17) . . ?
N1 C14 C1 108.51(16) . . ?
N3 C15 C13 178.9(2) . . ?
N4 C16 C17 119.47(19) . . ?
N4 C16 C29 118.18(17) . . ?
C17 C16 C29 122.34(18) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 117.9(2) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
N4 C20 C19 123.0(2) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
O2 C21 N5 124.8(2) . . ?
O2 C21 C22 129.3(2) . . ?
N5 C21 C22 105.84(17) . . ?
C27 C22 C23 121.0(2) . . ?
C27 C22 C21 108.79(18) . . ?
C23 C22 C21 130.2(2) . . ?
C24 C23 C22 118.2(2) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 120.9(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C26 121.3(2) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C27 C26 C25 117.7(2) . . ?
C27 C26 H26 121.1 . . ?
C25 C26 H26 121.1 . . ?
C26 C27 C22 120.8(2) . . ?
C26 C27 C28 132.63(19) . . ?
C22 C27 C28 106.56(17) . . ?
C29 C28 N5 121.40(18) . . ?
C29 C28 C27 130.10(18) . . ?
N5 C28 C27 108.50(16) . . ?
C28 C29 C30 120.82(18) . . ?
C28 C29 C16 122.40(17) . . ?
C30 C29 C16 116.78(17) . . ?
N6 C30 C29 177.9(2) . . ?
C14 N1 C7 110.32(15) . . ?
C14 N1 B1 124.27(16) . . ?
C7 N1 B1 125.03(16) . . ?
C12 N2 C8 119.49(17) . . ?
C12 N2 B1 124.56(15) . . ?
C8 N2 B1 115.75(16) . . ?
C20 N4 C16 119.55(18) . . ?
C20 N4 B2 115.41(17) . . ?
C16 N4 B2 125.02(17) . . ?
C28 N5 C21 110.28(17) . . ?
C28 N5 B2 125.42(17) . . ?
C21 N5 B2 124.28(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
C14 C1 C2 C3 177.69(19) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C14 C1 C6 C5 -179.03(18) . . . . ?
C2 C1 C6 C7 177.74(17) . . . . ?
C14 C1 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 O1 0.2(4) . . . . ?
C1 C6 C7 O1 -178.4(2) . . . . ?
C5 C6 C7 N1 179.1(2) . . . . ?
C1 C6 C7 N1 0.5(2) . . . . ?
N2 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 N2 -0.7(3) . . . . ?
C10 C11 C12 C13 178.56(18) . . . . ?
N2 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C14 -178.45(18) . . . . ?
N2 C12 C13 C15 177.69(16) . . . . ?
C11 C12 C13 C15 -1.6(3) . . . . ?
C15 C13 C14 N1 -178.40(17) . . . . ?
C12 C13 C14 N1 -1.6(3) . . . . ?
C15 C13 C14 C1 1.5(3) . . . . ?
C12 C13 C14 C1 178.32(17) . . . . ?
C6 C1 C14 C13 180.00(19) . . . . ?
C2 C1 C14 C13 2.3(4) . . . . ?
C6 C1 C14 N1 -0.1(2) . . . . ?
C2 C1 C14 N1 -177.80(19) . . . . ?
C14 C13 C15 N3 120(12) . . . . ?
C12 C13 C15 N3 -57(12) . . . . ?
N4 C16 C17 C18 0.8(3) . . . . ?
C29 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 N4 0.9(3) . . . . ?
O2 C21 C22 C27 177.2(2) . . . . ?
N5 C21 C22 C27 -1.8(2) . . . . ?
O2 C21 C22 C23 -1.9(4) . . . . ?
N5 C21 C22 C23 179.1(2) . . . . ?
C27 C22 C23 C24 -1.2(4) . . . . ?
C21 C22 C23 C24 177.8(2) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C25 C26 C27 C22 0.1(3) . . . . ?
C25 C26 C27 C28 -179.8(2) . . . . ?
C23 C22 C27 C26 1.0(3) . . . . ?
C21 C22 C27 C26 -178.23(19) . . . . ?
C23 C22 C27 C28 -179.1(2) . . . . ?
C21 C22 C27 C28 1.7(2) . . . . ?
C26 C27 C28 C29 -1.0(4) . . . . ?
C22 C27 C28 C29 179.1(2) . . . . ?
C26 C27 C28 N5 179.0(2) . . . . ?
C22 C27 C28 N5 -0.9(2) . . . . ?
N5 C28 C29 C30 -179.49(18) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
N5 C28 C29 C16 0.6(3) . . . . ?
C27 C28 C29 C16 -179.47(17) . . . . ?
N4 C16 C29 C28 -0.4(3) . . . . ?
C17 C16 C29 C28 -179.8(2) . . . . ?
N4 C16 C29 C30 179.64(18) . . . . ?
C17 C16 C29 C30 0.3(3) . . . . ?
C28 C29 C30 N6 179(100) . . . . ?
C16 C29 C30 N6 -1(7) . . . . ?
C13 C14 N1 C7 -179.63(17) . . . . ?
C1 C14 N1 C7 0.4(2) . . . . ?
C13 C14 N1 B1 -6.5(3) . . . . ?
C1 C14 N1 B1 173.60(16) . . . . ?
O1 C7 N1 C14 178.4(2) . . . . ?
C6 C7 N1 C14 -0.6(2) . . . . ?
O1 C7 N1 B1 5.3(3) . . . . ?
C6 C7 N1 B1 -173.71(17) . . . . ?
F1 B1 N1 C14 131.40(19) . . . . ?
F2 B1 N1 C14 -103.3(2) . . . . ?
N2 B1 N1 C14 12.7(2) . . . . ?
F1 B1 N1 C7 -56.4(3) . . . . ?
F2 B1 N1 C7 68.8(2) . . . . ?
N2 B1 N1 C7 -175.17(16) . . . . ?
C11 C12 N2 C8 1.6(3) . . . . ?
C13 C12 N2 C8 -177.71(17) . . . . ?
C11 C12 N2 B1 -172.98(17) . . . . ?
C13 C12 N2 B1 7.7(3) . . . . ?
C9 C8 N2 C12 -1.0(3) . . . . ?
C9 C8 N2 B1 174.05(19) . . . . ?
F1 B1 N2 C12 -135.58(17) . . . . ?
F2 B1 N2 C12 105.78(19) . . . . ?
N1 B1 N2 C12 -13.5(2) . . . . ?
F1 B1 N2 C8 49.7(2) . . . . ?
F2 B1 N2 C8 -68.9(2) . . . . ?
N1 B1 N2 C8 171.78(16) . . . . ?
C19 C20 N4 C16 0.2(3) . . . . ?
C19 C20 N4 B2 -178.6(2) . . . . ?
C17 C16 N4 C20 -1.0(3) . . . . ?
C29 C16 N4 C20 179.64(17) . . . . ?
C17 C16 N4 B2 177.7(2) . . . . ?
C29 C16 N4 B2 -1.7(3) . . . . ?
F4 B2 N4 C20 61.1(2) . . . . ?
F3 B2 N4 C20 -57.9(2) . . . . ?
N5 B2 N4 C20 -178.12(17) . . . . ?
F4 B2 N4 C16 -117.6(2) . . . . ?
F3 B2 N4 C16 123.4(2) . . . . ?
N5 B2 N4 C16 3.2(3) . . . . ?
C29 C28 N5 C21 179.72(19) . . . . ?
C27 C28 N5 C21 -0.3(2) . . . . ?
C29 C28 N5 B2 1.5(3) . . . . ?
C27 C28 N5 B2 -178.47(19) . . . . ?
O2 C21 N5 C28 -177.8(2) . . . . ?
C22 C21 N5 C28 1.2(2) . . . . ?
O2 C21 N5 B2 0.4(4) . . . . ?
C22 C21 N5 B2 179.5(2) . . . . ?
F4 B2 N5 C28 114.3(2) . . . . ?
F3 B2 N5 C28 -120.4(2) . . . . ?
N4 B2 N5 C28 -3.1(3) . . . . ?
F4 B2 N5 C21 -63.7(3) . . . . ?
F3 B2 N5 C21 61.6(3) . . . . ?
N4 B2 N5 C21 178.97(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 997092'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_20140204dd_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H10 B F2 N3 O'
_chemical_formula_weight         345.11

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   6.4067(6)
_cell_length_b                   7.2419(7)
_cell_length_c                   32.409(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1503.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5604
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.88

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8432
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2662
_reflns_number_gt                2584
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.2659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_number_reflns         2662
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1394(3) 0.2177(3) 0.80621(5) 0.0343(4) Uani 1 1 d . . .
C1 C 0.5046(2) -0.2718(2) 0.94334(4) 0.0327(3) Uani 1 1 d . . .
C2 C 0.6485(3) -0.3336(2) 0.97352(5) 0.0380(4) Uani 1 1 d . . .
H2 H 0.7712 -0.2679 0.9779 0.046 Uiso 1 1 calc R . .
C3 C 0.6094(3) -0.4880(2) 0.99623(5) 0.0429(4) Uani 1 1 d . . .
H3 H 0.7029 -0.5238 1.0167 0.051 Uiso 1 1 calc R . .
C4 C 0.4294(3) -0.5937(2) 0.98909(5) 0.0477(4) Uani 1 1 d . . .
H4 H 0.4049 -0.6992 1.0047 0.057 Uiso 1 1 calc R . .
C5 C 0.2902(3) -0.5423(2) 0.95939(5) 0.0429(4) Uani 1 1 d . . .
H5 H 0.1734 -0.6153 0.9544 0.052 Uiso 1 1 calc R . .
C6 C 0.3214(2) -0.3796(2) 0.93612(4) 0.0350(3) Uani 1 1 d . . .
C7 C 0.1735(2) -0.3176(2) 0.90673(5) 0.0373(4) Uani 1 1 d . . .
H7 H 0.0538 -0.3861 0.9013 0.045 Uiso 1 1 calc R . .
C8 C 0.2100(2) -0.1557(2) 0.88654(5) 0.0339(3) Uani 1 1 d . . .
C9 C 0.3910(2) -0.0481(2) 0.89350(4) 0.0303(3) Uani 1 1 d . . .
C10 C 0.5379(2) -0.1050(2) 0.92123(4) 0.0328(3) Uani 1 1 d . . .
H10 H 0.6581 -0.0356 0.9256 0.039 Uiso 1 1 calc R . .
C11 C 0.3758(2) 0.1121(2) 0.86565(4) 0.0289(3) Uani 1 1 d . . .
C12 C 0.5043(2) 0.2605(2) 0.86099(4) 0.0297(3) Uani 1 1 d . . .
C13 C 0.4587(2) 0.4108(2) 0.83246(4) 0.0285(3) Uani 1 1 d . . .
C14 C 0.5806(2) 0.5692(2) 0.82967(5) 0.0344(3) Uani 1 1 d . . .
H14 H 0.6988 0.5812 0.8461 0.041 Uiso 1 1 calc R . .
C15 C 0.5274(2) 0.7081(2) 0.80279(5) 0.0389(4) Uani 1 1 d . . .
H15 H 0.6094 0.8137 0.8009 0.047 Uiso 1 1 calc R . .
C16 C 0.3516(3) 0.6898(2) 0.77854(5) 0.0444(4) Uani 1 1 d . . .
H16 H 0.3132 0.7829 0.7603 0.053 Uiso 1 1 calc R . .
C17 C 0.2357(3) 0.5335(2) 0.78185(5) 0.0412(4) Uani 1 1 d . . .
H17 H 0.1176 0.5210 0.7654 0.049 Uiso 1 1 calc R . .
C18 C 0.6870(2) 0.2770(2) 0.88623(5) 0.0340(3) Uani 1 1 d . . .
C19 C 0.0854(2) -0.0649(2) 0.85395(5) 0.0370(4) Uani 1 1 d . . .
F1 F 0.18157(17) 0.12870(14) 0.76937(3) 0.0513(3) Uani 1 1 d . . .
F2 F -0.06386(13) 0.27551(15) 0.80686(3) 0.0521(3) Uani 1 1 d . . .
N1 N 0.8317(2) 0.2907(2) 0.90669(5) 0.0498(4) Uani 1 1 d . . .
N2 N 0.28551(18) 0.39485(18) 0.80824(4) 0.0327(3) Uani 1 1 d . . .
N3 N 0.19605(19) 0.09552(18) 0.84270(4) 0.0327(3) Uani 1 1 d . . .
O1 O -0.07765(19) -0.11314(19) 0.83883(4) 0.0558(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 F2 1.368(2) . ?
B1 F1 1.383(2) . ?
B1 N3 1.521(2) . ?
B1 N2 1.589(2) . ?
C1 C2 1.417(2) . ?
C1 C10 1.421(2) . ?
C1 C6 1.429(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(2) . ?
C7 C8 1.363(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(2) . ?
C8 C19 1.478(2) . ?
C9 C10 1.365(2) . ?
C9 C11 1.473(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(2) . ?
C11 N3 1.3763(18) . ?
C12 C18 1.433(2) . ?
C12 C13 1.4575(19) . ?
C13 N2 1.3640(18) . ?
C13 C14 1.391(2) . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(2) . ?
C16 H16 0.9300 . ?
C17 N2 1.357(2) . ?
C17 H17 0.9300 . ?
C18 N1 1.144(2) . ?
C19 O1 1.2059(19) . ?
C19 N3 1.409(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
F2 B1 F1 109.97(13) . . ?
F2 B1 N3 113.15(14) . . ?
F1 B1 N3 110.70(13) . . ?
F2 B1 N2 108.24(13) . . ?
F1 B1 N2 107.27(12) . . ?
N3 B1 N2 107.27(11) . . ?
C2 C1 C10 121.27(14) . . ?
C2 C1 C6 118.35(14) . . ?
C10 C1 C6 120.37(13) . . ?
C3 C2 C1 120.85(16) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.66(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.35(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.75(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 121.90(15) . . ?
C5 C6 C1 118.98(14) . . ?
C7 C6 C1 119.09(14) . . ?
C8 C7 C6 118.74(15) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 122.54(14) . . ?
C7 C8 C19 129.30(15) . . ?
C9 C8 C19 108.12(13) . . ?
C10 C9 C8 120.25(14) . . ?
C10 C9 C11 133.34(13) . . ?
C8 C9 C11 106.40(12) . . ?
C9 C10 C1 119.00(14) . . ?
C9 C10 H10 120.5 . . ?
C1 C10 H10 120.5 . . ?
C12 C11 N3 120.98(13) . . ?
C12 C11 C9 130.52(13) . . ?
N3 C11 C9 108.49(12) . . ?
C11 C12 C18 119.73(13) . . ?
C11 C12 C13 122.58(13) . . ?
C18 C12 C13 117.62(12) . . ?
N2 C13 C14 119.29(13) . . ?
N2 C13 C12 117.69(13) . . ?
C14 C13 C12 123.00(13) . . ?
C15 C14 C13 120.40(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.59(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.77(15) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
N2 C17 C16 122.53(14) . . ?
N2 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
N1 C18 C12 179.32(17) . . ?
O1 C19 N3 124.74(15) . . ?
O1 C19 C8 128.98(16) . . ?
N3 C19 C8 106.28(12) . . ?
C17 N2 C13 119.43(13) . . ?
C17 N2 B1 115.63(12) . . ?
C13 N2 B1 124.83(12) . . ?
C11 N3 C19 110.69(12) . . ?
C11 N3 B1 124.67(12) . . ?
C19 N3 B1 124.12(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 176.19(15) . . . . ?
C6 C1 C2 C3 -2.5(2) . . . . ?
C1 C2 C3 C4 2.6(2) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C4 C5 C6 C7 -176.36(16) . . . . ?
C4 C5 C6 C1 1.8(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C10 C1 C6 C5 -178.35(15) . . . . ?
C2 C1 C6 C7 178.54(14) . . . . ?
C10 C1 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 C8 177.50(15) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C6 C7 C8 C19 177.82(16) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C19 C8 C9 C10 -177.55(14) . . . . ?
C7 C8 C9 C11 178.85(14) . . . . ?
C19 C8 C9 C11 1.17(16) . . . . ?
C8 C9 C10 C1 -0.9(2) . . . . ?
C11 C9 C10 C1 -179.25(15) . . . . ?
C2 C1 C10 C9 -177.71(14) . . . . ?
C6 C1 C10 C9 1.0(2) . . . . ?
C10 C9 C11 C12 -4.1(3) . . . . ?
C8 C9 C11 C12 177.43(15) . . . . ?
C10 C9 C11 N3 176.96(16) . . . . ?
C8 C9 C11 N3 -1.51(16) . . . . ?
N3 C11 C12 C18 178.05(13) . . . . ?
C9 C11 C12 C18 -0.8(2) . . . . ?
N3 C11 C12 C13 1.2(2) . . . . ?
C9 C11 C12 C13 -177.65(14) . . . . ?
C11 C12 C13 N2 -3.5(2) . . . . ?
C18 C12 C13 N2 179.61(13) . . . . ?
C11 C12 C13 C14 175.12(14) . . . . ?
C18 C12 C13 C14 -1.8(2) . . . . ?
N2 C13 C14 C15 -0.1(2) . . . . ?
C12 C13 C14 C15 -178.63(14) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 N2 0.3(3) . . . . ?
C11 C12 C18 N1 -78(17) . . . . ?
C13 C12 C18 N1 99(17) . . . . ?
C7 C8 C19 O1 1.6(3) . . . . ?
C9 C8 C19 O1 179.10(17) . . . . ?
C7 C8 C19 N3 -177.92(15) . . . . ?
C9 C8 C19 N3 -0.44(17) . . . . ?
C16 C17 N2 C13 -0.3(2) . . . . ?
C16 C17 N2 B1 -176.75(16) . . . . ?
C14 C13 N2 C17 0.1(2) . . . . ?
C12 C13 N2 C17 178.76(14) . . . . ?
C14 C13 N2 B1 176.26(14) . . . . ?
C12 C13 N2 B1 -5.1(2) . . . . ?
F2 B1 N2 C17 -47.73(18) . . . . ?
F1 B1 N2 C17 70.90(17) . . . . ?
N3 B1 N2 C17 -170.14(13) . . . . ?
F2 B1 N2 C13 136.01(14) . . . . ?
F1 B1 N2 C13 -105.37(16) . . . . ?
N3 B1 N2 C13 13.6(2) . . . . ?
C12 C11 N3 C19 -177.78(14) . . . . ?
C9 C11 N3 C19 1.28(16) . . . . ?
C12 C11 N3 B1 10.2(2) . . . . ?
C9 C11 N3 B1 -170.76(13) . . . . ?
O1 C19 N3 C11 179.90(16) . . . . ?
C8 C19 N3 C11 -0.54(17) . . . . ?
O1 C19 N3 B1 -8.0(2) . . . . ?
C8 C19 N3 B1 171.55(14) . . . . ?
F2 B1 N3 C11 -135.35(15) . . . . ?
F1 B1 N3 C11 100.68(16) . . . . ?
N2 B1 N3 C11 -16.0(2) . . . . ?
F2 B1 N3 C19 53.6(2) . . . . ?
F1 B1 N3 C19 -70.32(18) . . . . ?
N2 B1 N3 C19 172.95(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 997093'
